32789 Zip Code FL 1/3 Acre Real Estate, Homes for Sale

J Kronenberger Sub SubDv. ⋅ 32789 Zip Code

This expansive .32-acre lot (13,732 sq ft) offers exceptional potential for either a brand-new custom build or a renovation with room to expand. Ideally located in the heart of Winter Park, the property sits across the street from several grand estates on the Winter Park Chain of Lakes, offering both prestige and endless possibilities. The existing 1960’s residence features original wood floors, a generous living area, and a split-bedroom layout—ready for updates or thoughtful expansion. With ample space, you can reimagine the home to suit your lifestyle or design a stunning new construction. Adding to its appeal, the property is within a short stroll to Kraft Azalea Gardens, the Winter Park YMCA, Phelps Park and just a little over a mile from Downtown Winter Park’s shops, dining, and cultural venues. This home is sold AS IS.

901 Palmer Avenue, Winter Park

$1,350,000

5 Beds ⋅ 3 Baths ⋅ Forest Hills SubDv. ⋅ 32789 Zip Code

Amazing opportunity in the Forest Hills subdivision in the heart of Historic Winter Park! As you enter this charming 4 bedroom home you’re welcomed by a spacious dining room that flows seamlessly into the large family room with fireplace, custom built-in shelving and storage cupboards, crown moulding and views over the rear yard and patio, perfect for relaxing or entertaining. To the front of the home, enjoy a bright and expansive kitchen/family space featuring upgraded appliances including a Sub-Zero refrigerator and built-in coffee maker, stone countertops, and ample room for casual dining and lounging. The private primary suite includes its own bathroom, while three additional generously sized bedrooms share well-appointed bathrooms. Hardwood floors, charming details, and mature landscaping add timeless appeal. Set on a tree-lined street with a circular driveway, just minutes from Park Avenue, Rollins College, and top-rated schools, this is your chance to create your dream home in one of Winter Park’s most coveted neighborhoods!

130 W Kings Way, Winter Park

$1,095,000

3 Beds ⋅ 4 Baths ⋅ Lake Knowles Terrace SubDv. ⋅ 32789 Zip Code

Located in the coveted Tree Streets just a block and a half from Lake Knowles, this timeless Mediterranean home offers three bedrooms, three and a half bathrooms, and just under 2,000 square feet of beautifully finished living space framed by mature magnolias and manicured hedges. A brick driveway leads to a two-car garage with carriage-style doors, while a covered entry showcases a solid arched wood front door with classic peep hole, setting the tone for the craftsmanship inside. Step through the entry and discover a hidden laundry room with dark wood cabinetry, marble countertops, subway tile backsplash, and front-loading washer and dryer, along with a sophisticated powder bath featuring a floating marble-topped sink, wall-mounted chrome faucet, integrated mirror lighting, and detailed molding. Just beyond is a flexible room that functions as a dining room or formal living space, and through the next doorway the home opens to a large kitchen and great room designed for everyday living and entertaining. The kitchen combines dark wood perimeter cabinetry with accent glass fronts, a creamy white island with storage on both sides, marble countertops, and stainless appliances including a GE Monogram gas cooktop with vent hood, convection oven, refrigerator, dishwasher, and LG under-counter microwave, all anchored by a deep single-barrel undermount sink with extendable faucet. The great room features a gas fireplace with mosaic tile surround, clerestory windows, extensive crown molding, and hardwood floors, with new Anderson French doors that open to the private backyard where brick decking frames a cocktail pool with water features by Signature Landscape, surrounded by mature greenery and magnolias. The primary suite, tucked on the back right wing, also enjoys French doors to the pool terrace and includes new carpet, a customized floor-to-ceiling walk-in closet, and a bath with travertine floors, sunken glass-enclosed shower with built-in shelving, creamy white vanity topped with marble, satin nickel fixtures, dual Kohler undermount sinks, and mirrored walls with crown molding. Upstairs, two spacious bedrooms each feature ensuite baths and customized closets—the front with a built-in desk, marble chicklet tile flooring, creamy cabinetry, and tub/shower combo, the second with a walk-in closet and a bath finished with travertine flooring, a slightly larger vanity with consistent cream cabinetry, marble top, and glass-enclosed shower. Additional highlights include hidden storage under the stairs, unique iron stair railing, 8’ solid wood interior doors, 10’ ceilings, and block construction, while recent updates such as an Italian tile roof (2020), newer garage door and opener, and new HVAC air handler provide peace of mind. Just a short walk to the YMCA, Phelps Park, and Interlachen Country Club, 1450 Chestnut Avenue combines Mediterranean charm, thoughtful updates, and a sought-after Winter Park location for a lock and leave lifestyle with ease.

1450 Chestnut Avenue, Winter Park

$1,590,000

4 Beds ⋅ 4 Baths ⋅ Dixie Terrace SubDv. ⋅ 32789 Zip Code

HUGE PRICE IMPROVEMENT-MOTIVATED SELLER-Discover this stunning, custom-built home nestled on a tranquil, tree-lined street just steps from all the charm of Winter Park’s renowned Park Avenue. Located in a peaceful neighborhood, this elegant residence combines sophisticated craftsmanship with luxury features throughout its expansive 2,860 square feet of thoughtfully designed living space. Relax on the charming front covered porch, the perfect spot to enjoy your morning coffee. Step inside to find meticulous attention to detail—from stunning wide white oak floors to exquisite custom millwork and soaring ceilings that create an airy, welcoming atmosphere. The chef-inspired kitchen is the heart of the home, featuring an abundance of custom solid-wood cabinets, gleaming quartz countertops, and a large island with seating for four. A generous walk-in pantry with custom shelving and top-of-the-line Thermador stainless steel appliances—including a 6-burner gas stove, double oven, and deep farm sink—make meal preparation and entertaining effortless. Adjacent to the kitchen, a charming dining area is perfect for memorable dinners, while the adjoining family room boasts a soaring cathedral ceiling, a natural gas fireplace with a custom stone mantel, and large windows that flood the space with natural light. A cozy private den offers an ideal retreat for work or relaxation. On the opposite side of the first floor, you'll find a guest suite with a private bath, two additional bedrooms with custom closets, a stylish full bath, and a laundry room with ample storage and a utility sink. The spacious mudroom, accessible from the two-car garage, provides practical storage with built-in cabinets and hooks. Upstairs, the luxurious primary suite features a spa-inspired bathroom with double sinks, custom Restoration Hardware cabinetry, elegant lighting, and a large walk-in shower. A peaceful sitting area and a walk-in closet with custom shelving create a perfect private retreat. Additionally, an upstairs loft offers versatile space ideal for a home office, gym, or additional quiet area. Outside, enjoy a private backyard oasis designed for relaxation and entertainment. Highlights include a “Michael Phelps Chilly Goat” hot/cold tub combo, outdoor TV, and speakers—creating your personal weekend paradise. Additional amenities include a large two-car garage, solid-core doors, crown molding, wide base moldings, dual tankless water heaters, fully-owned solar panels (reducing energy costs), a water softener and purifier, new exterior paint (2023), professionally installed closet shelving (2023), and professionally landscaped gardens. Flooded with natural light and warmth, this exceptional home offers a cozy yet elegant atmosphere. Zoned for top-tier schools—including Winter Park High School—and conveniently located near Lake Highland, Trinity Prep, the Winter Park YMCA, Racquet Club, and Interlachen Country Club, it’s ideal for a vibrant Florida lifestyle. Walkable to Winter Park’s renowned shopping and dining destination, don’t miss the opportunity to make this exquisite property your new home! AVAILABLE BY APPOINTMENT ONLY

1166 Oaks Boulevard, Winter Park

$1,475,000

5 Beds ⋅ 4 Baths ⋅ Dixie Terrace SubDv. ⋅ 32789 Zip Code

Welcome to this updated and architecturally unique 5-bedroom, 3.5-bathroom custom home, offering 3,292 square feet of luxury living in the heart of Winter Park. Step inside and you’re immediately greeted by gleaming porcelain tile floors, smooth modern non-textured walls, and soaring ceilings that create a light and airy feel. The spacious living room features custom wall details, crown molding, an elegant wine cellar with glass wall, and expansive high windows that flood the home with natural light. Glass accents continue throughout with an updated staircase and second-level glass wall, adding a sleek, modern touch. To the left, discover a rare double-primary suite layout. A converted study now serves as a second primary bedroom, connected by a hallway with two walk-in closets. The shared spa-style primary bath includes dual vanities, a hot tub, and a glass shower. The suite on the west side enjoys private access to the pool area. Both bedrooms have tray ceilings with crown molding. The open dining area flows seamlessly into the kitchen, which showcases a natural gas range with pot filler, a large island with seating, pendant lights, granite counters, stainless steel appliances, and a unique indoor-outdoor service window that opens to the summer kitchen. The first floor is completed with a third bedroom (currently used as a home office), a full bath, and a laundry room. Ascend the glass-accented staircase to the second floor, where you’ll find a versatile dining/bonus room with porcelain tile flooring and tray ceiling, a kitchenette and a balcony overlooking the pool. Two additional bedrooms, a full bathroom, and a spacious storage closet complete the upstairs. The outdoor space has been completely reimagined for entertainment and relaxation. Enjoy a heated pool and spa with water features and stonework, outdoor shower, summer kitchen with bar seating, pergola, artificial turf, and plenty of yard space. The backyard is fully fenced and includes a storage building with a half bath. A whole-home 24kW Generac generator provides peace of mind. Additional highlights include a two-car garage, a carport for extra parking, and a prime location just minutes from Park Avenue’s upscale shopping and dining, Whole Foods, and easy access to major highways. This exceptional Winter Park home blends custom design, modern updates, and outdoor luxury. Schedule your private tour today.

1453 Lyndale Boulevard, Winter Park

$4,150,000

4 Beds ⋅ 6 Baths ⋅ Palmer Ave Lakeside Prop SubDv. ⋅ 32789 Zip Code

Welcome to 702 Via Bella, an impressive 2025 English cottage estate by Floridian Custom Homes that captures the essence of timeless architecture exemplifying elegance and artisan craftsmanship. In one of Winter Park’s desirable residential corridors, warmth and beauty abound in this four-bedroom, six-bath residence spanning 3,720 square feet or air conditioned and 4,535 square feet total under roof, offering layered living, artisanal materials, and a modern infrastructure. Upon entry through a solid mahogany front door, warmth and beauty abounds with Botticino limestone flooring enhanced by a textured finish, extensive custom millwork, and an abundance of open concept living areas. Coffered ceilings and recessed WAC lighting create a gallery-like ambiance, enhanced by natural light from insulated casement windows. The central living space integrates with the dining area and designer kitchen, which features custom cabinetry by Grit & Grain, leathered Taj Mahal quartzite surfaces, and chef-grade appliances: a La Cornue 43-inch gas range with McGurken hood, Thermador 30-inch refrigerator and freezer columns, and Bosch dishwasher. The kitchen transitions into a walk-in pantry with cabinetry, quartzite, dual refrigeration drawers, and a dedicated ice maker. An oversized mudroom, finished with hardwood built-ins, offers expanded storage and functionality. The first-floor primary suite is privately positioned in its own wing and finished with wide-plank European white oak flooring by Forrest Accents, a walk-in closet with textured built-in systems, and a spa bath with natural stone countertops, Rohl polished nickel fixtures, a marble-tiled floor and shower, and a frameless glass enclosure. All doors are solid core with Emtek hardware. The library, near the front of the home, offers a quiet retreat with matching oak floors and custom casements. A solid wood staircase leads to the second level living areas including a lounge flex space. There are three additional bedroom suites, each with en-suite baths, which offer porcelain flooring, frameless glass shower doors, brushed quartz and dolomite vanities, decorative lighting, and built-in closet systems. Additional features include CAT-5/6 wiring, Sonos-integrated speakers, lighting automation via the Lutron RA-3 smart system, and pre-wired home security with digital camera ports at key access points. Thoughtfully placed access points from the primary suite and kitchen wing lead to a fully enclosed backyard retreat, where mature landscape design by Signature Landscape frames a private outdoor living sanctuary. A Roman-inspired cabana with grand ceilings and exposed beams anchors the outdoor entertaining space, flanked by a fully tiled ($50,000 upgrade) saltwater pool featuring therapy jets, LED-lit bubblers, a dual-skimmer system, automated controls via a Jandy heat pump, and a Paramount self-cleaning system. Clay brick pavers and landscape lighting define the walkways as well as front entry driveway. This home was constructed with stem wall foundation, concrete block first-floor exterior walls, and 2-by-6 second-floor framing for structural performance along with spray foam and sound mat insulation between floors ensure comfort and acoustic separation. Finished in a palette of clay brick and hand-troweled stucco, the home is crowned with architectural tile shingles and custom metal accents. Eight-inch half-round gutters, aluminum downspouts and engineered drainage ensure long-term performance.

702 Via Bella, Winter Park

$630,000

3 Beds ⋅ 2 Baths ⋅ Bungalow Park SubDv. ⋅ 32789 Zip Code

Welcome home to this charming 3-bedroom, 2-bath Mediterranean bungalow perfectly situated on a quiet brick street in the heart of Winter Park. You’ll feel tucked away from it all, yet you’re just blocks from restaurants, city parks & tennis courts, grocery shopping, Park Avenue, and Rollins College. Step inside to a warm and inviting atmosphere featuring 9-foot ceilings, a desirable split-bedroom layout, and an open great room that seamlessly blends the kitchen, dining, and living areas. Beautiful hardwood parquet floors add timeless character throughout. The primary suite offers a relaxing retreat with a deep soaking tub, separate shower, and windows overlooking the backyard. A convenient interior utility room doubles as a practical workspace with a built-in desk, perfect for paying bills or setting up a family computer center. Additional highlights: Top-rated Winter Park schools: Audubon K–8 & Winter Park High School and strong Four-Point: Tile Roof (2012), A/C (2021), Water Heater (2020), Electrical & Plumbing (2012). Easy access to I-4 for quick trips west to Downtown Orlando, the attractions, Tampa & I-75, or east to the beaches & I-95. This Winter Park gem combines charm, comfort, and convenience — the perfect place to call home.

1015 Bungalow Avenue, Winter Park

$837,500

2 Beds ⋅ 2 Baths ⋅ Park West Condo SubDv. ⋅ 32789 Zip Code

A unique opportunity to own this Winter Park luxury corner condominium unit in the gated Park West community. Resting on the corner of New York Avenue and Carolina, with direct second-floor balcony views of Central Park and Park Avenue, and proximity to the quintessential Winter Park experience. Designed by nationally renowned Soco Interiors, a turnkey opportunity that adds ease to the lock-and-go lifestyle. Designer touches and quiet elegance blend to create this California casual interior that was meticulously designed and appointed with function and comfort at the forefront. Open dining and living spaces with balconies on each side make hosting a breeze. A marble-framed fireplace and beautiful wide-plank white oak floors add warmth and charm to this special place. The modern gourmet kitchen is highly functioning for family dinner or entertaining guests. White clean-lined custom cabinetry, gold accent hardware, quartz surfaces and solid quartz backsplash add to the seamless design. A fabulously designed scullery with designer tile floor includes a dedicated laundry/pantry, ample storage and additional counter space for a morning bar. The primary bedroom has ample space and beautiful light with access to one of the two balconies, custom-organized closet and a bath that is appointed with modern finishes such as marble floors/shower and fantastic tropical palm wallpaper that is so chic and fun. An additional large private bedroom suite is inviting and makes it easy to entertain guests for the weekend. Fresh striped wallpaper and organic selections finish out the custom second bath. This pristine unit is in a great building in Park West overlooking Central Park. On a prime corner, with one balcony facing the park and the other overlooking the tennis courts and pool. Elevators throughout and meticulously maintained, all in security of a gated community, Park West has always delivered for decades. Call us for a private showing.

200 Carolina Avenue Unit 201, Winter Park

$1,250,000

3 Beds ⋅ 3 Baths ⋅ Ellno Willo SubDv. ⋅ 32789 Zip Code

Amazing opportunity in the heart of Historic Winter Park! This charming home is full of potential and ready for your personal touch. Whether you're looking to renovate, restore, or re-imagine, this property offers a rare chance to create your dream home in one of Central Florida’s most sought-after neighborhoods. Enjoy tree-lined streets, top-rated schools, and close proximity to Park Avenue, Rollins College, and all that Winter Park has to offer. Don’t miss this unique opportunity to invest in a premier location!

1621 Hillcrest Avenue, Winter Park

$1,100,000

3 Beds ⋅ 3 Baths ⋅ Fairbanks Park SubDv. ⋅ 32789 Zip Code

Welcome home! Nestled in the heart of Winter Park this 3-bedroom, 2.5 bathroom residence offers a perfect blend of convenience, energy efficiency, and refined comfort. From the moment you enter, you'll be captivated by high ceilings and crown molding for a spacious and refined feel. The kitchen is a chef's dream featuring granite countertops, stainless steel appliances, a gas range and upgraded plumbing fixtures. Enjoy cozy evenings in the living room by the new gas fireplace or relax outside by the cocktail pool, perfect for entertaining and enjoying the Florida sunshine in a tropical setting. The primary suite includes a private balcony with serene views of Lake Midget park. The spacious master bathroom is a true oasis with a soaking tub and rainfall shower. Powered blackout roller shades in the primary suite and downstairs living area ensure restful sleep and complete privacy. Closet systems throughout the home add a layer of organization and luxury. Recent upgrades to the home include a new roof with architectural shingles (2023), energy efficient Pella Impervia windows (2024), an updated air conditioning/heat pump system (2022) and full flake epoxy garage floors with ultra quiet garage door openers. Enjoy low utility bills and energy efficiency with dual-zone A/C, tankless hot water system, R40 attic insulation & foamed block walls. Easy access to I-4 and just minutes from iconic Park Avenue, Downtown Orlando, Rollins College and Baldwin Park. Shopping, numerous restaurants and bars, tennis facilities, multiple parks and city facilities are just a short walk or drive away. Whether you're looking for the perfect place to call home or a stunning Winter Park retreat, this home delivers unmatched quality, location, and lifestyle.

930 S Kentucky Avenue, Winter Park

$475,000

4 Beds ⋅ 2 Baths ⋅ Sylvan Heights SubDv. ⋅ 32789 Zip Code

PROPERTY AS-IS - Perfect for a fix-and-flip or new construction. Nestled in the heart of Winter Park’s coveted 32789 ZIP code, this stunning new possibility offers the epitome of luxury living in one of Central Florida’s most coveted neighborhoods. The current structure is being approved for demolition, and the 30-day public notice has been completed. This Prime Location is perfect for Investment or dream-home Lifestyle Potential. Buyer to verify all facts independently.

1740 Anzle Avenue, Winter Park

$429,999

3 Beds ⋅ 2 Baths ⋅ Sells Terrace SubDv. ⋅ 32789 Zip Code

Discover this beautifully updated 3-bedroom, 2-bathroom home in Winter Park, perfectly positioned to enjoy the best of both Winter Park and College Park living! From the moment you arrive, you’ll notice the professionally landscaped front and backyard (2022) with upgraded irrigation, gutters, and a spacious, durable back deck (2021). Step inside to find an inviting floor plan featuring crown molding, wood flooring, abundant natural light, and thoughtful updates throughout. The large living room with a cozy window bench flows seamlessly into the modernized kitchen, complete with granite countertops, wood cabinets, stainless steel appliances (including a double oven), and a custom-built island that conveys. Off the kitchen, you’ll find a convenient indoor laundry room and a versatile bonus/family room currently serving as a dining and entertainment space. This room boasts shiplap accents, updated lighting, tile floors, a mini split (2023), and backyard access. The primary suite overlooks the backyard and offers dual closets plus a renovated en-suite bathroom with a walk-in shower and dual-sink vanity. The additional bedrooms are spacious and bright, with the second bathroom also completely remodeled. Enjoy your private backyard oasis, perfect for relaxing or entertaining—grill on the deck, play cornhole, or simply unwind. Major updates include: Hot Water Heater (2024), AC (2023), Mini Split (2023), Re-Landscaping & Irrigation (2022), Spray Foam Attic Insulation in Florida Room(2022), Gutters (2021), Replumbed (2020), Roof (2016). This home is truly a charmer—move-in ready and waiting for its next owner! Schedule your private tour today.

105 Conrad Court, Winter Park

$502,000

3 Beds ⋅ 2 Baths ⋅ Lake Forest Park SubDv. ⋅ 32789 Zip Code

CHARMING 3 BEDROOM, 2 BATH IN THE HEART OF WINTER PARK! This home is located in a highly desirable neighborhood, ideally positioned between Baldwin Park, Audubon Park, Mills 50, and Park Avenue. Just steps from Blue Jacket Park, you’ll enjoy morning walks, weekend picnics, and easy access to the shopping, dining, and entertainment that make Winter Park so special. With so much potential, you can move right in, remodel to your taste, or build a custom home—just as many neighbors have already done. The property features comfortable living spaces, a bright kitchen, a large screened-in sun room, and a spacious backyard perfect for outdoor gatherings or future customization. Whether you’re looking to settle into a vibrant community or invest in a highly sought-after area, this home is a fantastic opportunity you won’t want to miss!

2308 Mulbry Drive, Winter Park

$382,575

2 Beds ⋅ 1 Baths ⋅ Albert Lee Ridge Add 02 SubDv. ⋅ 32789 Zip Code

Welcome to 1001 Early Ave—a beautifully updated 2-bedroom, 1-bath home that perfectly balances timeless character with contemporary style. Nestled on a spacious 7,405 sq ft lot, this 1,222 sq ft gem invites you in with parquet floors, decorator tile, and abundant natural light. The expanded kitchen is a showstopper, featuring stainless steel appliances, granite countertops, a wine cooler, and sleek wood and glass accents—ideal for both everyday cooking and weekend entertaining. The renovated bathroom offers spa-like serenity with a glass bowl sink and modern finishes. Step outside to your private oasis: a sparkling pool with a tranquil water feature, a tiki-style cabana, and a paver patio designed for unforgettable gatherings. The circular driveway and garage with a service door add convenience and curb appeal. The septic system was replaced in 2019, serviced in 2024 and roof replaced 2021. Located minutes from Whole Foods, Winter Park Village, the Enzian Theater, and the vibrant 17-92 corridor, this home offers unbeatable access to shopping, dining, and entertainment. With easy access to I-4 and College Park, your commute and weekend plans just got easier. Whether you're a first-time buyer, downsizer, or investor, this home is a rare find in one of Central Florida’s most desirable neighborhoods. Don’t miss your chance to own a slice of Winter Park paradise.

1001 Early Avenue, Winter Park

$1,700,000

Cloister Grove Sub SubDv. ⋅ 32789 Zip Code

Arguably one of the top streets in Winter Park, this Via Capri lot is level, lovely, and large. Phil Kean has designed a lovely home for the property, but for those that might be looking for something somewhat different PKDG would be happy to design and build a home to your specifications, or simply sell the property as is.

1181 Via Capri, Winter Park

$2,078,500

5 Beds ⋅ 4 Baths ⋅ Palmer Ave Lakeside Prop SubDv. ⋅ 32789 Zip Code

Tucked away on a quiet cul-de-sac lined with multi-million-dollar estates, this Winter Park residence offers an enviable blend of privacy, lifestyle, and location. Less than a mile from Park Avenue, the Winter Park 9 Golf Course, and the Racquet Club, this address puts you at the center of the city’s most coveted amenities. A deeded greenbelt easement to Lake Osceola—just 100 yards from the front door—provides effortless access for boating, kayaking, or paddle boarding on the Winter Park Chain of Lakes. The two-story brick home spans 4,328sf with 4 bedrooms, 4 baths, and a 2-car garage. Inside, character and craftsmanship shine with brick archways, custom millwork, tongue-and-groove ceilings, and two wood-burning fireplaces. The gourmet kitchen features Thermador appliances, marble counters, and a walnut-topped island, while the expansive primary suite boasts a private screened patio, a fully built-out oversized walk-in closet, and a spa-like bath. Two bonus rooms upstairs provide flexible space for work or play, while updated systems—including a 2018 roof, three HVAC units, dual-pane windows, updated drainage, whole house generator, mosquito misting system, whole house alarm, and smart home upgrades—ensure comfort and peace of mind. Equally impressive are the grounds. The front garden is graced with jasmine, mature oaks, and manicured plantings, while a Chicago brick horseshoe driveway easily accommodates six or more cars. Out back, a private retreat unfolds with a lagoon-style saltwater pool and spa surrounded by flagstone decking, a summer kitchen, covered patio with fans and lighting, and a dedicated pool bath. Living here is about more than a home—it’s about lifestyle. With gardens and stunning architecture at every turn, culture, shopping, and dining just minutes away, and lake access at your fingertips, this property offers a rare opportunity to experience the very best of Winter Park.

715 Via Bella, Winter Park

$750,000

2 Beds ⋅ 2 Baths ⋅ Cloisters Condo SubDv. ⋅ 32789 Zip Code

Experience refined Winter Park living in this stunning 2-bedroom, 2-bath pied-a-terre in the Cloisters condominium. Perfectly situated in the heart of town, this residence offers serene lake and pool views, a deeded parking space, and effortless access to the upscale boutiques and renowned dining of Park Avenue. Thoughtfully designed interiors feature luxe furnishings and accessories curated by SMRS Design, blending timeless elegance with modern comfort. Whether enjoying your morning coffee by the water or entertaining in style, this home captures the best of Winter Park’s coveted lifestyle.

100 S Interlachen Avenue Unit 203D, Winter Park

$771,000

3 Beds ⋅ 2 Baths ⋅ Orwin Manor Westminster Sec SubDv. ⋅ 32789 Zip Code

You know it's going to be a winner when the primary walk-in-closet, alone, is 8'x10'! This beautiful Orwin Manor home has it all: 3 bedrooms, 2 bathrooms, and indoor laundry room, updated kitchen and baths, a detached 1 car garage, flex space for a playroom or office, and incredible systems updates like a 2018 roof, 2020 water heater, and 2022 HVAC. Once you get past the beautiful curb appeal, you'll step into a multifunctional living space with options for living and dining. You'll appreciate the split plan layout with two secondary bedrooms in one hallway and an expansive primary suite in the back of the home. All of the bedrooms have freshly cleaned carpet and the living spaces in the home are a versatile engineered hardwood. The kitchen, complete with dry bar and wine storage, is in the middle of the home making for easy entertaining and it's filled with convenient storage! Out back, enjoy the well-maintained yard space and 1 car garage for parking and/or storage. The location is ideal, as it's centrally located to the best of both Winter Park and Orlando. Less than a mile from Foxtail Coffee and Kelly's Ice Cream on Orange Ave, 1.5 miles from Rollins College, less than 2 miles from Publix, and so much more.

1340 Pelham Road, Winter Park

$2,144,000

4 Beds ⋅ 4 Baths ⋅ Pennsylvania Place SubDv. ⋅ 32789 Zip Code

Wonderful home in sought-after Pennsylvania Place. Newer roof (2019), HVAC and Water Heaters

1077 N. Pennsylvania Ave, Winter Park

$3,965,000

4 Beds ⋅ 5 Baths ⋅ Valencia Terrace SubDv. ⋅ 32789 Zip Code

Conveniently situated near the Winter Park Country Club, this contemporary masterpiece, built by premier builder Z Properties, offers the ideal mix of style, comfort, and modern living. Meticulously maintained with great inspection. Completed in 2021, the residence has 4,181 square feet of thoughtfully designed living space, including four bedrooms each with a private ensuite bath and an additional powder room. A 412-square-foot casita with a wet bar and private entrance completes its functionality by providing extra flexibility, perfect for guests, extended family, workspace or workout area. The interiors showcase timeless design with high ceilings, glass walls, and carefully curated finishes. The chef’s kitchen and butler’s pantry pair handcrafted cabinetry and stone surfaces with professional-grade appliances, flowing seamlessly into open living and dining spaces designed for both everyday living and entertaining. Outdoors, a 65-foot lap pool anchors the private backyard retreat, complemented by a covered lanai, marine-grade summer kitchen, fireplace lounge, tree garden and lush landscaping. Solid block construction, advanced state-of-the-art home systems, and a climate-controlled two-car garage with an extended hidden driveway highlight the home’s privacy, quality, and convenience. With a distinct European vibe under canopy trees and cobblestone streets in the desirable Valencia Terrace neighborhood, this home is just moments from Park Avenue’s boutiques, fine dining, Rollins College, the Farmers’ Market, and the Morse Museum. Zoned for top-rated Winter Park schools, it offers both luxury and practicality in one of Central Florida’s most sought-after communities.

1161 Valencia Avenue, Winter Park

$1,740,000

3 Beds ⋅ 3 Baths ⋅ Morseland Sub SubDv. ⋅ 32789 Zip Code

Welcome to the timeless charm of Beloit Avenue, one of Winter Park’s most desired streets. This classic and elegant 3-bedroom, 2.5-bath residence offers nearly 3,000 square feet of thoughtfully designed living all on one level. Just two blocks from Park Avenue and a short stroll to the Winter Park Golf Course, the location is truly unmatched. Inside, high ceilings, detailed crown molding, hardwood floors, and an open kitchen create an inviting and livable flow. The screened patio extends the living space outdoors, offering a perfect setting to enjoy Florida living year-round. A private brick paver alley exclusive to Beloit homeowners provides access to a spacious two-car garage complete with built-in workbench and attic storage. Combining charm, convenience, and elegance, this traditional home is a rare find in the very heart of Winter Park.

443 Beloit Avenue, Winter Park

$956,809

4 Beds ⋅ 4 Baths ⋅ Karolina On Killarney SubDv. ⋅ 32789 Zip Code

Pre-Construction. To be built. Experience a life where timeless craftsmanship meets modern convenience in the heart of Winter Park. This brand-new 4-bedroom, 3.5-bath, 2,662 sq. ft. home is situated on a 6,748 sq. ft. lot and is a meticulously designed modern Craftsman, blending rich architectural details with functional, contemporary living. One of three consecutive custom builds — each with its own distinctive architecture and character — this residence offers a rare combination of individuality and neighborhood harmony. Perfectly located just 6 minutes from Park Avenue’s boutique shopping and dining, and within close reach of top-rated hospitals, it places you at the center of Winter Park’s most sought-after amenities. This property is ideal for designing your forever home. Pricing reflects the starting point, with a variety of upgrade options available to further personalize finishes and features. The adjacent homes, including 1835 Karolina Ave and parcel 21, are also available in the desirable 32789 zip code.

Lot #20 Karolina Ave, Winter Park

$1,063,303

4 Beds ⋅ 4 Baths ⋅ Karolina On Killarney SubDv. ⋅ 32789 Zip Code

Pre-Construction. To be built. Experience the best of Winter Park living at 1835 Karolina Ave — one of only three brand-new, custom-built homes on this highly coveted block. This beautiful 4-bedroom, 3.5-bath Prairie elevation home offers 2,662 sq. ft. of thoughtfully designed living space on a 6,748 sq. ft. lot. It combines distinctive architectural character with a prime location—only 6 minutes to Park Avenue’s vibrant shopping and dining scene, and close to top-rated hospitals. This home presents a rare opportunity to design in one of Winter Park’s most desirable neighborhoods. Pricing reflects the starting point, with a range of upgrade options available to further personalize finishes and features. Two additional custom homes, each with unique elevations and thoughtfully designed floor plans, are available right next door parcel 20 and 21. Don’t miss your chance to secure a prime homesite in the desirable 32789 zip code, where location and lifestyle meet. Contact us today for more information or to have your questions answered.

1835 Karolina Ave, Winter Park

$970,000

3 Beds ⋅ 2 Baths ⋅ Charmont SubDv. ⋅ 32789 Zip Code

Winter Park Home.

207 E Kings Way, Winter Park

$1,770,000

3 Beds ⋅ 4 Baths ⋅ Park Grove SubDv. ⋅ 32789 Zip Code

Welcome to this picturesque 3 bedroom, 4 bath pool home nestled in the highly sought-after neighborhood of Park Grove. Overflowing with charm and character, this naturally light-filled home features white oak hardwood floors and plantation shutters throughout. Upon entry, a formal living room with a cozy wood-burning fireplace greets you, offering serene views of the sparkling heated pool and lush backyard oasis. The elegant formal dining room leads to a chef's kitchen adorned with marble countertops, wood cabinetry, a spacious island with seating, and top-of-the-line appliances. A well-appointed wet bar adds to the home's entertainment appeal, while an informal dining space flows seamlessly into the expansive family room, where floor-to-ceiling windows invite the beauty of the outdoors in. Step outside to a covered porch and summer kitchen- perfect for hosting. Enjoy al fresco dining under the shade of a covered pergola or relax by the glistening pool in complete privacy. The home features two secondary bedrooms, each with its own en-suite bath, and a full guest bath off the hallway. The primary suite is a true retreat, offering a private sitting area, his-and-hers closets, and a luxurious bath with dual vanities and a large walk-in shower. Located just minutes from the vibrant shops and fine dining of Park Avenue in downtown Winter Park, and zoned for top-rated schools- this home is an exceptional opportunity you won't want to miss!

690 Williams Drive, Winter Park

$1,150,000

4 Beds ⋅ 3 Baths ⋅ Virginia Heights Rep SubDv. ⋅ 32789 Zip Code

One or more photo(s) has been virtually staged. This beautiful 4-bedroom, 3-bathroom home in Winter Park's sought-after Virginia Heights neighborhood offers 3,204 square feet of comfortable living space on a private 0.21-acre lot. The property underwent extensive addition and renovation in 2020, featuring stunning wood floors throughout and a spacious kitchen complete with a bar, center island, and wine fridge. The home's character shines through unique details like authentic New Orleans 100-year-old ironwork on the staircase, adding historical charm to this modern residence. The main floor flows seamlessly, while upstairs you'll find three bedrooms. A large game room provides flexible space that could easily serve as an in-law suite. Recent updates ensure worry-free living with new drywall, insulation, electrical, and plumbing systems installed. The roof was replaced in 2021, and the home features three newer air conditioning units plus water heaters that are just 2-4 years old. A new sewer line to the street was installed in 2009. Outside, you'll discover a well-designed courtyard leading to an amazing pool and backyard perfect for entertaining or relaxing. The property includes a gas line and plenty of parking space. The location offers the best of Winter Park living. You're just steps from Lake Virginia with exclusive access to College Point, a secluded deeded lakefront area reserved for Virginia Heights residents only. This beautiful lakefront spot overlooks Rollins College and includes a dock for launching kayaks or canoes. Daily conveniences are nearby with Park Avenue's shops and restaurants within walking distance. The home provides quick access to downtown Winter Park, Winter Park Village, US 17-92, and Mead Botanical Garden. Families will appreciate the proximity to highly-rated Audubon K-8 and Winter Park High School, both just moments away. This property perfectly combines privacy, luxury, and convenience in one of Winter Park's most desirable neighborhoods.

1213 Richmond Road, Winter Park

$600,000

3 Beds ⋅ 2 Baths ⋅ Orangewood Park SubDv. ⋅ 32789 Zip Code

In the heart of the Audubon Park Garden District you will find this updated mid-century modern home on a .17 acre homesite. A brick-paver driveway and front patio provide lots of curb appeal. Stepping inside you are greeted by warm bamboo flooring and tons of natural light thanks to updated windows (2013) throughout. The split floor-plan features 3 bedrooms and 2 bathrooms, both updated with newer tile and vanities. A 3-ton HVAC unit (2020) as well as a mini-split and ceiling fans keep the home comfortable throughout the Florida summer. When it's cooler, enjoy lounging in your fenced-in backyard on your rear lanai, accessible via a charming brick-paver path. Other notable features include upgraded kitchen cabinets, stainless LG appliances, blinds throughout and recessed lighting. An enclosed utility room provides tons of extra storage and convenience. The location of this home is less than 10 minutes to Park Avenue and just 2 blocks from Corrine Drive and all the wonderful shops and restaurants in Audubon Park. Enjoy walking to the East End Market to pick up some gourmet cheese, fresh baked bread and coffee on a Saturday morning! The highly desirable and award winning Audubon Park K8 School is also a mere 4 blocks away. The adjacent Baldwin Park neighborhood offers a plethora of parks, playgrounds, shopping, grocery and boutiques for your enjoyment. This home is also zoned for Winter Park High School, arguably one of the best high schools in the Orange County Public School district. The average home sale price in this neighborhood is $1.1 million, don't wait to become a part of this vibrant neighborhood. Schedule a showing today!

2812 Woodside Avenue, Winter Park

$1,168,000

3 Beds ⋅ 3 Baths ⋅ Golfview Heights SubDv. ⋅ 32789 Zip Code

Experience the epitome of modern luxury living—where location, design, and comfort converge in perfect harmony. This newly constructed modern farmhouse offers 3 bedrooms, 2.5 bathrooms, and 2,242 square feet of living space, thoughtfully designed to elevate everyday living. Upon entering, the grand foyer welcomes you with minimalist elegance, setting the tone for the entire home. The open-concept layout seamlessly blends spacious living areas, making them ideal for both relaxation and entertaining. Soft, cozy materials throughout the home create a warm, inviting atmosphere—every surface crafted to feel gentle and refined. The designer kitchen is a culinary centerpiece, featuring custom cabinetry, quartz countertops, high-end appliances, and a sleek island perfect for gatherings. The adjoining living room is bright and airy, anchored by an electric fireplace and enhanced by a striking custom bar wall with exposed brick, built-in shelving, and dual wine refrigerators. A dedicated office and a formal dining room on the main level provide functional flexibility for work and gatherings. The artful centerpiece of the home—the floating staircase—is framed by soaring windows and illuminated by a sculptural chandelier, making a bold architectural statement. Upstairs, the primary suite offers a true retreat with a spacious walk-in closet and a spa-like bath featuring dual vanities, a glass-enclosed double shower, and matte black fixtures. Two guest bedrooms and a dedicated laundry room with a stackable washer and dryer complete the upper level. Step outside to a professionally landscaped yard with a pavered semi-circular driveway and expansive green space, all set on a desirable corner lot. Nestled on a quiet, tree-lined street just minutes from Park Avenue, this home offers the best of Winter Park living. Zoned for A+ rated schools and conveniently located near Winter Park Hospital, Rollins College, fine dining, shopping, museums, and major highways—this is luxury living with lifestyle in mind. Schedule your private showing today and make this exceptional residence your own.

1785 Hollywood Avenue, Winter Park

$164,000

2 Beds ⋅ 1 Baths ⋅ Lakeside Manor Apts Condo SubDv. ⋅ 32789 Zip Code

Welcome to life on Lake Killarney, one of Winter Park’s most sought-after lakefront communities! This charming 2-bedroom, 1-bathroom condo offers an unbeatable location and resort-style amenities—perfect for those seeking the true Florida lifestyle.Enjoy direct access to Lake Killarney, where residents can take advantage of boat slips available at a low cost on a first-come, first-serve basis, as well as a private boat launch, a brand-new dock with covered over-water seating, a lakeside pool, and a clubhouse. The beautifully manicured green spaces and quiet courtyard areas create a peaceful, community-oriented atmosphere.Inside, this move-in ready unit has been freshly painted throughout and features new carpeting. The kitchen has been tastefully refreshed and offers plenty of cabinet space. An assigned parking space is located just steps from the unit, and there's an on-site laundry facility plus a private storage unit for added convenience.Tucked away yet close to it all, you’re just minutes from the shops and restaurants of Winter Park, with easy access to I-4 and other major roadways. Residents love living here—units don’t come available often, so don’t miss your chance to call this lakeside gem home!

2500 Lee Rd Unit 219, Winter Park

$385,000

3 Beds ⋅ 2 Baths ⋅ Shores Lake Killarney Sec 02 SubDv. ⋅ 32789 Zip Code

Charming Winter Park Block Home with Deeded Access to Lake Killarney – Solid, Updated Systems & Priced for Your Personal Touch! Welcome to this well-built 3-bedroom, 2-bath cement block home in one of Winter Park’s most desirable and established neighborhoods. . . . . . Built in 1954 and lovingly cared by the same owner for almost 40 years, this home offers strong bones, a functional layout, and major system updates already completed—including roof (2019), AC (2019), re-piping (2005), window replacement (2010), and custom paver driveway (2005). . . . . . The kitchen was updated in 2008 and offers a great starting point for further personalization. This home is priced to reflect the need for cosmetic updates, giving buyers the opportunity to renovate and style the home to their taste, without worrying about costly behind-the-walls repairs. . . . . . Whether you're a first-time buyer, investor, or someone looking to downsize into a home you can make your own, this property is full of potential. The layout is warm and inviting, with plenty of natural light and the timeless durability of concrete block construction. . . . . . Located just minutes from top-rated schools, parks, shopping, dining, and major roadways, this home is perfectly positioned for convenience and community. . . . . . A wonderful opportunity to own in Winter Park—move in now, update at your pace, and build equity as you go!

259 Blossom Lane, Winter Park

$1,875,000

4 Beds ⋅ 5 Baths ⋅ Conwill Estates SubDv. ⋅ 32789 Zip Code

Timeless Elegance Meets Modern Comfort in Sought-After Tree Streets Welcome to this thoughtfully designed, custom-built residence in the coveted Tree Streets community of Winter Park. Boasting 4 bedrooms, 4.5 bathrooms, and over 3,300 square feet of meticulously curated living space, this one-of-a-kind home perfectly blends craftsmanship, comfort, and style. At the heart of the home, the chef-inspired kitchen showcases premium Thermador appliances, a gas range, and custom cabinetry that soars to 10-foot ceilings. The spacious butler’s pantry and built-in breakfast nook flow seamlessly into an inviting great room with custom built-ins—ideal for both everyday living and elegant entertaining. Nearby, the formal dining room features a striking drop ceiling, setting the stage for unforgettable gatherings. Designed for everyday convenience and privacy, the first floor includes both a comfortable guest suite and a luxurious primary suite, which features elegant wood beams accenting the ceiling and creates a warm, sophisticated retreat. Throughout the home, beautiful white oak floors add warmth and character, complementing the timeless design and enhancing the flow between each thoughtfully crafted space. Enjoy effortless indoor-outdoor living with an expansive covered lanai featuring a built-in summer kitchen and phantom screens, all overlooking a stunning pool and spa embraced by lush landscaping. A dedicated pool bath ensures convenience for guests enjoying the outdoor oasis. Inside, thoughtful features abound: a stylish mudroom with built-in storage, a large utility room with cabinetry and sink, and a conditioned mechanical room offering smart storage solutions. Upstairs, discover a spacious loft perfect for a media room or play area, accompanied by two generously sized bedrooms each with ensuite baths and ample closets. The Stratford-style front porch invites neighborly chats, while the private backyard provides a serene retreat. Designer-selected finishes and custom touches are evident throughout, highlighting the home's timeless elegance and modern functionality. Ideally situated just minutes from Park Avenue, residents will enjoy effortless access to fine dining, boutique shopping, charming cafes, museums, and the vibrant cultural heart of Winter Park. A rare offering that combines luxurious design, exceptional craftsmanship, and the warm character only a custom-built home can provide—this residence truly stands out in the Tree Streets.

1752 Chestnut Avenue, Winter Park

$1,050,000

3 Beds ⋅ 2 Baths ⋅ Charmont SubDv. ⋅ 32789 Zip Code

Incredible location in the heart of Winter Park, situated on an oversized lot, on a brick street, close to Park Avenue.

2250 Forrest Road, Winter Park

$2,200,000

3 Beds ⋅ 4 Baths ⋅ Lake Knowles Terrace SubDv. ⋅ 32789 Zip Code

Exuding timeless charm and Southern elegance, this gorgeous Charleston-style residence sits on a large lot overlooking the tranquil waters of Lake Knowles. Framed by a picturesque brick street lined with beautiful homes, the property boasts striking curb appeal, a 32-foot second-story porch with breathtaking sunset views, and classic architectural details that invite you in at every turn. A charming brick firepit area in the front yard offers a spot to gather on cool evenings while taking in peaceful lake vistas. Thoughtfully renovated, the home seamlessly blends modern comforts with preserved character, including gleaming hardwood floors, French doors, and a welcoming, light-filled layout. The front living room is anchored by the home’s original 1954 wood-burning fireplace, a timeless centerpiece flanked by built-in shelving. It's a spot to curl up with a good book, open all three sets of French doors, and enjoy the crisp air and sparkling views of Lake Knowles. Whether you're sipping cocktails on a winter evening or coffee on a quiet morning, the space offers a special setting. For over 50 years, residents have gathered to admire the beloved Lake Knowles Christmas tree, its colorful lights casting a magical glow across the water—just one of many traditions that make this location so cherished. A family room flows into the dining room, where French doors lead to a charming brick patio for effortless indoor-outdoor entertaining. The chef’s kitchen is a dream, featuring top-of-the-line appliances, a generous island with seating, a walk-in pantry, and a stylish dry bar that connects to the kitchen and living room. The first-floor primary suite offers a serene retreat with French doors opening to the patio, dual closets (including a walk-in), and a luxurious bath with a large glass shower, dual sinks, and a private water closet. Upstairs, two additional bedrooms and a cozy den or TV room provide inviting spaces for family and guests. The third bedroom includes a spacious walk-in closet and an en-suite bath, while the second-story porch offers an idyllic vantage point for sunset views over the lake. Outside, the backyard is an oasis with a sprawling lawn, mature landscaping, and plenty of room to add a pool. Just a short bike ride from Park Avenue’s boutiques, fine dining and Central Park, the home is also minutes from the weekly Farmer’s Market, top-rated schools, and major roadways for easy access to downtown Orlando, international and executive airports, and leading hospitals.

1554 Lake Knowles Circle, Winter Park

$825,000

3 Beds ⋅ 4 Baths ⋅ Lake Knowles Terrace SubDv. ⋅ 32789 Zip Code

BUYER GOT COLD FEET= YOUR OPPORTUNITY! Welcome to 1421 Sunset Drive – A Turnkey Gem in the Heart of Olde Winter Park! This is a rare opportunity to own a beautifully updated home on one of Olde Winter Park’s most charming, brick-lined, tree-canopied streets. Just steps from serene Lake Knowles and Lake Wilbar, and minutes from the vibrant dining, shopping, and cultural experiences of Park Avenue, this 3-bedroom, 3.5-bathroom residence offers the perfect blend of classic charm and modern convenience. Enjoy a low-maintenance lifestyle with eco-friendly landscaping and a thoughtfully designed floor plan featuring two spacious primary suites — one upstairs and one down — each with its own updated bathroom. Inside, the home boasts tall vaulted ceilings, warm wood plank LVT flooring, a cozy wood-burning fireplace, and multiple inviting living areas. The kitchen is a standout with sleek cabinetry, granite countertops, and stainless steel appliances, ideal for both daily living and entertaining. Step outside to enjoy Trex decking on both front and rear patios, a fenced backyard for privacy, and a convenient laundry/mudroom entry from the garage. Additional highlights include a standing seam metal roof, attached garage, and access to top-rated Winter Park schools. The home is also located near the YMCA, Interlachen Country Club, Winter Park Racquet Club, Rollins College, UCF, and AdventHealth Winter Park. This home is move-in ready and offers the very best of Winter Park living — schedule your private showing today!

1421 Sunset Drive, Winter Park

$410,000

4 Beds ⋅ 3 Baths ⋅ Justamere Camp Rep SubDv. ⋅ 32789 Zip Code

One or more photo(s) has been virtually staged. A rare gem nestled in one of Winter Park’s most secluded subdivisions—just 25 homes tucked into a quiet, tree-lined enclave. This block-built mid-century home offers four bedrooms, three baths, and sits proudly on a spacious double lot. Inside, travertine floors add timeless elegance, while oversized windows flood the space with natural light—perfect for highlighting your design vision. Whether you’re leaning into sleek modern style or restoring vintage charm, this blank canvas is primed for your passionate transformation. A renovation ready treasure with solid bones and undeniable potential. Enjoy a Winter Park address at a fraction of the cost—with no HOA, you have the freedom to renovate, rent, or reinvent without limitations. Located just 10 minutes from Park Avenue’s upscale shops and restaurants, with top-rated schools nearby and quick access to I-4 for effortless commuting. This is your opportunity to craft something extraordinary in one of Central Florida’s most coveted locations. Easy to show! Call for your private tour today!

2464 Lotafun Avenue, Winter Park

$715,000

4 Beds ⋅ 4 Baths ⋅ Swoope Park SubDv. ⋅ 32789 Zip Code

Located within the private enclave of 400 West—an exclusive 9-residence community just steps from Park Avenue—this contemporary townhome offers a rare blend of quality construction, refined interiors & exceptional walkability. From the moment you step inside—whether through the private garage or along the garden-style front path—you’re met with a bright open-concept main floor that blends comfort, functionality & clean design. Clean-lined finishes include large-format porcelain tile, level 5 drywall, tall contemporary baseboards & designer lighting that elevate the functionality & style of the main floor. The kitchen anchors the space w/ flat-panel high-gloss white cabinetry, sleek chrome pulls, quartz counters & a suite of stainless-steel appliances including a Whirlpool French door refrigerator w/ bottom freezer, LG slide-in range w/ glass cooktop & built-in microwave & Frigidaire dishwasher. A newly installed pull-down faucet, deep undermount double bowl sink, generous cabinet storage & motorized Lutron-enabled window shades on the front-facing living room window & entry door provide functional use & elevate the design. A stylish powder bath, under-stair storage & direct access to the garage complete the main floor. The rear-entry garage features alleyway access, a storage closet & built-ins for added convenience. Upstairs, two primary-sized suites span the second level, each w/ engineered wood flooring & floor-to-ceiling windows or glass doors that fill the rooms w/ natural light. Spa-inspired en-suite bathrooms feature large-format porcelain tile, frameless glass shower enclosures, wall-to-wall mirrors, matte white vanities, solid surface counters, undermount sinks & chrome fixtures. The primary bath includes an extended double-sink vanity, private water closet & a built-in shower bench & storage niche. Beyond the bath is a spacious walk-in closet. A full laundry room is also located on this level, featuring a Samsung washer & dryer set w/ overhead storage. The third level offers two additional bedrooms or flex rooms—each w/ walk-in closets—connected by a shared Jack-&-Jill bath, making this space ideal for guest suites, a home office, gym or creative studio. Recent upgrades include a full interior repaint (2025), blackout shades, Pico-controlled Lutron motorized shades, professionally cleaned carpet, tile & grout. Smart home features include a Nest thermostat & Ring doorbell. Systems & mechanicals upgrades include a newer Trane HVAC condenser (2023), Whirlpool fridge (2018), Samsung washer/dryer (2022) & recently replaced garbage disposal & kitchen faucet (2024). The HVAC system was fully serviced in 2025 & all fans, lighting, drains & toilets have been checked & are in excellent working order. Built in 2014 w/ concrete block construction on both floors, level 5 drywall & a metal roof, this fee-simple townhome offers low-maintenance peace of mind. HOA dues of $400/month include exterior maintenance & landscaping. Guest parking is available on-site as well as along Swoope. This home delivers the rare combination of timeless quality & modern convenience. Thoughtfully designed across three levels, it offers flexibility, privacy & low-maintenance living—all in a quiet 9-residence community where everything Winter Park has to offer is just steps away. Whether you’re looking for a full-time residence or a lock-&-leave lifestyle, this is an exceptional opportunity to own a turnkey property in the heart of Winter Park.

438 W Swoope Avenue, Winter Park

$637,500

3 Beds ⋅ 3 Baths ⋅ Mc Intyre Place Condo SubDv. ⋅ 32789 Zip Code

Back on Market- Buyer Financing fell through--Beautiful Winter Park townhome that feels like a single-family residence. Situated on a private lane with no through-traffic. Ten-minute walk to Park Avenue and Rollins, five-minute walk to Lake Virginia. This exquisite end-unit is part of a sought-after 10-unit community. Three Bedrooms and two and a half Baths, volume ceilings, pristine travertine marble floors and an abundance of natural light throughout. Enjoy green outlooks through every window. Eat-in kitchen with quartz countertops, separate coffee bar, and stainless-steel appliances. Formal dining room (or flex room) overlooking a patio/atrium. French doors expand the home onto two separate private and peaceful garden patios showcasing meticulous landscaping (with nighttime lighting), marble pavers and one with an updated screen enclosure. An upstairs master suite offers generous closet space with a skylit dressing area and bath with double sinks, soaking tub and walk-in shower. Jack & Jill Bath creates the perfect ensuite guest bedroom. Additional features include wood-burning fireplace, custom plantation shutters, and attached 2-car garage with ample built-in storage. Newer Roof (2021), HVAC (2024), Kitchen Cabinets renovated (2024), New Stove/Oven (2024), Exterior and Interior Paint (2025). Call and come see it!

595 Huntington Avenue Unit 4, Winter Park

$630,000

4 Beds ⋅ 3 Baths ⋅ Flamingo Shores SubDv. ⋅ 32789 Zip Code

RENOVATED and MOVE-IN READY in WINTER PARK 32789 with DEEDED LAKE ACCESS! Located on a fully fenced ¼-acre corner lot, this 4-bed, 3-bath charmer offers private access to Lake Killarney, a rare find. Step onto the welcoming front porch and into a home filled with character, upgrades, and natural light. The open layout flows effortlessly through spacious living areas and a beautifully updated kitchen with modern finishes. Wood-look flooring, custom millwork, neutral tones, and designer lighting elevate the space. Enjoy a SPLIT FLOOR PLAN with 4 spacious bedrooms, including a large primary suite and a guest room with its own ensuite. The screened lanai and private backyard create the perfect outdoor retreat. Extras include a fireplace, two car attached garage and no HOA! This is a dream location just 1 mile to Trader Joe’s, 1.5 miles to Park Avenue, and minutes to I-4, Rollins College, shopping, dining, and more. Don’t miss your chance to live in the heart of Winter Park. Schedule your private tour today!

1792 Killarney Drive, Winter Park

$465,000

2 Beds ⋅ 3 Baths ⋅ Killarney Bay Condo SubDv. ⋅ 32789 Zip Code

SUPERB LOCATION! Don’t miss out on this beautifully updated 2 bedroom 2.5 bath 2-story condo in Killarney Bay. Upon entering, you immediately notice the charm and character of this impeccably maintained condo. Recent updates include a fully renovated screened porch including floor, screen enclosure and roof, new sliding doors and windows, new refrigerator, new dishwasher, newly painted interior and recently installed closet organization systems. The kitchen with solid wood cabinets, stainless steel appliances, granite countertops and counter seating is open to the dining/family room combo featuring a cozy corner fireplace. The flex space in the front of the condo can serve as a formal dining room, home office or art studio with generous shelves that span an entire wall of the room. Convenient downstairs laundry room with storage and half bath with access to additional storage under the stairs. Wood tile floors, plantation shutters, ceiling fans and vaulted ceilings in the upstairs bedrooms. Wood plank flooring on the staircase. Generous upstairs hall closet! Two master suites both with spacious walk-in closets and en suite bathrooms. The front bedroom features a balcony with a sitting area and alcove for a tv or desk and the back bedroom presents as a quiet, private retreat with extra closet space. The recently renovated screened porch overlooking the manicured landscape is the perfect place to relax and unwind. Two assigned parking spaces, one covered and located in front of the condo. Outdoor closet located on screened porch. Community pool and dock and view of Lake Killarney. Kayaks and paddleboard storage available. Walkable to Winter Park Village, Trader Joes and a variety of restaurants and shopping along the 17-92 corridor. Easy access to I.4 via Fairbanks or Lee Rds. You simply cannot beat this location! Call today to schedule your showing!

130 Killarney Bay Court Unit 5-3, Winter Park

$580,000

3 Beds ⋅ 3 Baths ⋅ Arbors/Aragon SubDv. ⋅ 32789 Zip Code

Nestled in a peaceful enclave near Park Avenue in Winter Park, this inviting 3 bedroom, 3 bathroom, 1,701 SF townhome offers classic Florida living with modern comforts. A welcoming entry opens to bamboo wood flooring that flows through the main living areas. The living room and adjacent dining space connect seamlessly to the gorgeous kitchen, featuring 42" wood cabinets, stainless appliances, granite countertops, and a breakfast bar, ideal for casual mornings or entertaining guests. Upstairs, the light-filled primary suite offers a peaceful retreat with double-vanity sinks, a garden tub with separate shower, a generous walk-in closet, and a private balcony. Two additional well-sized bedrooms and a hall bathroom provide space for family, guests, or a home office. The home rests on a corner lot with lush landscaping, a cozy front porch, and a 2 car garage. Step outside to discover a fully fenced backyard, perfectly sized for al fresco dining, gardening, or to enjoy a morning coffee in the Florida sunshine. Located just minutes from A-rated Winter Park schools, and close to Winter Park’s shops, restaurants, golf courses, and cultural attractions, this home offers an exceptional blend of convenience and community.

915 Aragon Avenue, Winter Park

$510,000

3 Beds ⋅ 2 Baths ⋅ Northwood Terrace SubDv. ⋅ 32789 Zip Code

Off market Sale

2804 Mulford Avenue, Winter Park

$610,000

3 Beds ⋅ 4 Baths ⋅ Na SubDv. ⋅ 32789 Zip Code

Welcome to 1620 Howell Branch Road—a beautifully reimagined 3-bedroom, 3-bath home that effortlessly blends timeless character with modern convenience. Thoughtfully remodeled from top to bottom, this residence retains much of its original architectural charm while offering the benefits of a full renovation. This gem is in the heart if Winter Park and allows all the amazing benefits of the community and top rated schools! Step inside to find spacious living areas, designer finishes, and a seamless flow that’s perfect for both everyday living and entertaining. The bright and airy layout extends into a lovely enclosed Florida room, offering the perfect retreat to enjoy your morning coffee or unwind in the evening breeze. Outside, you'll find a detached structure with its own full bath—ideal as a mother-in-law suite, guest house, home office, or workshop, giving you flexible space for whatever your lifestyle needs. While the home sits on a main road, it offers exceptional privacy and security, thanks to a fully fenced perimeter, an electronic front gate, and a rear gate providing easy access to the quiet neighborhood behind—great for walking, biking, or even extra guest parking. (Directly accessible on Verona Trail, through back yard gate) This unique property offers the rare combination of historic character and modern upgrades, with the peace of mind that comes from a full renovation. Conveniently located in Winter Park, you’re just minutes from top-rated schools, shops, parks, and dining. Don't miss this one-of-a-kind opportunity—schedule your showing today!

1620 Howell Branch Road, Winter Park

$425,000

Karolina On Killarney SubDv. ⋅ 32789 Zip Code

A Double Lot Near Lake Killarney! This bungalow nestled on a generous 0.32-acre lot—one of the largest in the neighborhood—just one block from scenic Lake Killarney is perfect for something NEW. With a spacious backyard, mature landscaping, and even a shuffleboard court, this property offers a rare opportunity to create your very own backyard retreat. There's room to add a pool, a pickleball court, or simply enjoy the expansive green space as is. The same homeowner for 26 years because of the love for the home and neighborhood understands that it's time for someone else to fall in love. Located just minutes from Park Avenue, College Park, and Downtown Orlando, with easy access to I-4, 17-92, and a host of restaurants and shops, you'll enjoy both serenity and connectivity. Lots like this don’t come along often—drive by today and imagine the possibilities!

1871 Staunton Avenue, Winter Park

$1,390,000

4 Beds ⋅ 5 Baths ⋅ Killarney Estates SubDv. ⋅ 32789 Zip Code

Under Construction. Renderings available soon. Brand-new custom construction on coveted Lakeview Avenue marries classic Winter Park charm with crisp, contemporary living. Behind its inviting façade you’ll find an airy two-story layout featuring four bedrooms and 4 ½ baths, including a full en-suite guest retreat on the main level. Three additional bedrooms share the upper floor with a bright loft that easily flexes as a playroom, office, or second lounge.The heart of the home is a chef-ready kitchen outfitted for serious cooking—double wall ovens, a dedicated cooktop, and generous countertop space—anchored by a spacious walk-in pantry and a convenient mudroom drop zone to keep daily life organized. Just beyond, a soaring great room centers on a built-in fireplace, while wide sliders open to a covered rear porch perfect for year-round alfresco dining. Upstairs, every bedroom enjoys direct or semi-private bath access, giving the residence the feel of four private suites, and a dedicated laundry room means no hauling baskets downstairs. Practical perks abound: an oversized two-car garage for gear and golf carts, impact-rated construction engineered to the latest Florida wind code, and full pre-wire rough-ins ready for your preferred appliance and lighting packages. All this sits minutes from Park Avenue’s dining and boutique shopping, Rollins College, and Winter Park’s famous chain of lakes. Schedule your private tour and discover the fresh, low-maintenance lifestyle waiting for you in one of Central Florida’s most sought-after neighborhoods. Final design and features subject to change.

525 Lakeview Avenue, Winter Park

$1,390,000

4 Beds ⋅ 5 Baths ⋅ Killarney Estates SubDv. ⋅ 32789 Zip Code

Under contract-accepting backup offers. MOVE-IN READY! Construction Completed! Brand-new custom construction on coveted Lakeview Avenue marries classic Winter Park charm with crisp, contemporary living. Behind its inviting façade you’ll find an airy two-story layout featuring four bedrooms and 4 ½ baths, including a full en-suite guest retreat on the main level. Three additional bedrooms share the upper floor with a bright loft that easily flexes as a playroom, office, or second lounge. The heart of the home is a chef-ready kitchen outfitted for serious cooking—double wall ovens, a dedicated cooktop, and generous countertop space—anchored by a spacious walk-in pantry and a convenient mudroom drop zone to keep daily life organized. Just beyond, a soaring great room centers on a built-in fireplace, while wide sliders open to a covered rear porch perfect for year-round alfresco dining. Upstairs, every bedroom enjoys direct or semi-private bath access, giving the residence the feel of four private suites, and a dedicated laundry room means no hauling baskets downstairs. Practical perks abound: an oversized two-car garage for gear and golf carts, impact-rated construction engineered to the latest Florida wind code, and full pre-wire rough-ins ready for your preferred appliance and lighting packages. All this sits minutes from Park Avenue’s dining and boutique shopping, Rollins College, and Winter Park’s famous chain of lakes. Schedule your private tour and discover the fresh, low-maintenance lifestyle waiting for you in one of Central Florida’s most sought-after neighborhoods. There is a pool company the buyers my call on directly if the buyer requires a pool Mike Inspire Pools

501 Lakeview Avenue, Winter Park

$1,565,000

4 Beds ⋅ 3 Baths ⋅ Virginia Heights SubDv. ⋅ 32789 Zip Code

Experience the charm and comfort of this one-story, Key West-style pool home, nestled on a brick-lined street and canopied by majestic oaks in the highly sought-after Virginia Heights neighborhood. Within true walking distance of Rollins College and Park Avenue, and in the Audubon K-8 school district, this home was thoughtfully designed for everyday living and entertaining. The 2,662 SF home features a split-bedroom floorplan with 3 bedrooms, 3 en-suite bathrooms, a private home office (or a 4th bedroom), cozy living room with a wood fireplace piped for gas, dining room with a built-in lighted bar, a large family room, and a 400 SF covered lanai overlooking the pool & backyard paradise. The oversized primary suite is truly a retreat, with a sitting area plus a cozy window bench spanning a wall of windows with built-in cabinetry and shelves for ample storage. A mirrored barn door slides open to reveal a custom-designed spa bath, renovated down to studs in 2021. An absolute stunner, the primary bath features a large, zero-entry marble shower, mahogany-topped custom-crafted vanity, maple board-and-batten walls, brass fixtures, cypress vaulted ceilings, and windows overlooking the sparkling pool, with convenient top-down bottom-up privacy shades. Enjoy 2 walk-in closets, plus a third closet at the primary suite entrance that offers easy-access housing for the home’s AV equipment. The sunny family room, lined with built-ins and a custom-designed “wall of books,” extends to the back of the home. French doors with hidden screens open to the private backyard oasis, showcasing a travertine lanai, lagoon-style pool, and travertine deck surrounded by palms and lush tropical landscaping. At the heart of the home sits the kitchen with Thermador appliances— gas cooktop, built-in oven, convection oven/microwave, and dishwasher— and a breakfast bar, plus a brand new vent hood framed by a new marble backsplash, and new under-cabinet and pendant lighting. Both secondary bedrooms have French doors that open to the covered lanai, while the rear left bedroom offers a private, en-suite bathroom renovated in 2021, wrapped in marble and brass with coil-heated floors and a custom Kohler air-jet soaking tub. Other conveniences include a whole-house sound system with speakers in every room as well as the rear lanai, and a custom laundry room (renovated in 2021) that leads to a 2-car garage with built-in storage. Virginia Heights is truly a special neighborhood, offering residents deeded access to a private lakefront park that's just a 3-minute walk from this home. This hidden park was deeded to the property owners of Virginia Heights in 1922, and includes a dock on College Point directly across from Rollins College, canoe/kayak racks, tables for airy picnics in the lake breeze, and a sprawling green lawn where neighbors gather for social events, holiday parties, or just to enjoy the lake view. A part of the beloved culture and history of Winter Park, this unique property is just minutes from Rollins, the shops and restaurants of Park Avenue, and all the lively bustle of downtown Winter Park. Recent upgrades include a complete replumb and new gas water heater (July 2025), a partial roof replacement (all new flat roof), landscape clean-up/refresh, fresh paint inside and out, and all new lighting and ceiling fans throughout. Ask for list of improvements and a floorplan!

1450 Glencoe Road, Winter Park

$245,900

3 Beds ⋅ 4 Baths ⋅ Sandalwood Creek Condo Ph 13 SubDv. ⋅ 32789 Zip Code

Your Dream Home Awaits in Winter Park! 3 Beds 3.5 baths! Discover the perfect blend of comfort and convenience in the heart of Winter Park at Sandlewood Creek! This charming townhome-style condo offers a rare opportunity to own a piece of paradise with no neighbors above or below, ensuring a peaceful living environment. Plus, enjoy a very low HOA! Key Features: Financing Made Easy: FHA, VA, and DPA approved, welcoming a wide range of buyers. Spacious Living: OVER 1,100 sq. ft. with an open floorplan, tile flooring, a large kitchen, and a convenient half-bath. Full sized washer dryer located inside. Private Retreat: A patio perfect for relaxation or entertaining. Community Perks: A sparkling pool and well-maintained grounds for a low-maintenance lifestyle. Prime Location: Minutes from Park Avenue, Downtown Maitland, and top shopping and dining spots. Zoned for top-rated schools: Dommerich Elementary, Maitland Middle, and Winter Park High. This move-in ready home is a rare find in Winter Park, offering unbeatable value. Don’t miss your chance to make your dreams a reality!

195 Sandlewood Trail Unit 2, Winter Park

$1,300,000

4 Beds ⋅ 3 Baths ⋅ Dixie Terrace SubDv. ⋅ 32789 Zip Code

One or more photo(s) has been virtually staged. As you enter this renovated 4-bedroom, 2.5-bathroom home within the city limits of Winter Park, you're immediately welcomed by a bright, open living and dining area anchored by a stunning wet bar, complete with sink, cabinetry, ice maker, and floating shelves. All completed with light modern porcelain tile flooring. To your right, the kitchen makes a bold statement with dramatic 4.5-inch thick countertops, waterfall-edge island, oversized farm sink, and high-end appliances including a Thermador induction stove and Whirlpool double oven, microwave, dishwasher, and fridge/freezer. Custom soft-close cabinetry blends seamlessly into the open layout, offering style and serious storage. Just beyond the hurricane rated sliding glass doors, you'll find a covered lanai and spacious yard with a mix of grass and artificial turf, ideal for entertaining, relaxing, or adding a future pool. The primary suite is tucked away on the left side of the home, offering peace and privacy. It features soft lighting, remote-controlled shades, and two walk-in closets with built-ins. The spa-like en-suite bathroom combines wood and stone textures, a floating dual-sink vanity, and a large walk-in rain shower, all designed with modern feel. Two additional bedrooms and a full bathroom are located down the same hallway, separated from the main living space by modern barn doors, perfect for creating a private wing for family or guests. On the opposite side of the home, a fourth bedroom makes a perfect office or guest suite. A nearby half bath opens to the outside, making it an ideal future pool bath. The laundry room is equipped with LG Signature washer and dryer, a drying closet, sink, and built-in storage. Adjacent to the laundry area is a stylish mudroom with custom built-ins to keep everything organized. Both the attached 2-car garage and carport make parking effortless. The garage is climate-controlled with a split AC unit and finished with sleek epoxy flooring, perfect for a gym, workshop, or additional storage. The garage is also equipped with EV charging capabilities. Set on a generous 0.33-acre corner lot, this property offers extra outdoor space, privacy, and potential, whether for a future pool, garden, or entertaining area. Additional upgrades include a whole-house Generac generator, a tankless water heater with softener and filtration system, hurricane-rated windows and sliding doors, new roof (2021), updated plumbing and electrical (2022), and two new AC systems (2022). Non-textured walls and ceilings, smart lighting, and clean, minimalist finishes round out the home’s modern aesthetic. Every detail of this home has been carefully curated to deliver a lifestyle of comfort, style, and function, a true modern retreat in the heart of Winter Park. This home is located just a short drive away from Park Avenue and its many restaurants and other businesses. Conveniently located close to major highways for easy commuting, schedule your private tour today.

1371 Lyndale Boulevard, Winter Park

$475,000

Winter Park Village SubDv. ⋅ 32789 Zip Code

?? Land for Sale – Build Your Dream Home in Winter Park! Just minutes from Park Avenue! Discover the perfect opportunity to build your custom home in one of Central Florida’s most desirable neighborhoods! This prime homesite is nestled among newly built luxury residences and offers the ideal canvas for your future home. The owner has already completed the heavy lifting — the previous structure has been professionally demolished, the septic tank removed, and the lot is cleared and ready to build. Highlights: Prime Winter Park location, Minutes to Park Avenue dining, shopping & events, Surrounded by high-end, newly constructed homes, ready for your builder! Opportunities like this in Winter Park are rare — don’t miss your chance to create something truly special

1414 Bessmor Road, Winter Park

$4,772,500

4 Beds ⋅ 5 Baths ⋅ Sicilian Shores Rep 02 SubDv. ⋅ 32789 Zip Code

An architectural gem in the heart of the Vias, this one-of-a-kind modern, custom residence masterfully crafted in 2019 by renowned builder Z Properties, Inc. Rarely does a single-story home of this caliber and scale become available combined with being on one of the best addresses in all of Winter Park! Offering nearly 4,900 square feet of refined living space under air (which includes a noteworthy 551-square-foot lanai, fully finished and separate zone air-conditioning) encompassing over 5,400 square feet total under roof, all tastefully designed with an emphasis on clean lines, organic textures and exceptional indoor-outdoor flow. Beyond its striking curb appeal, the home opens to reveal expansive living spaces grounded by wide-plank hardwood floors and bathed in natural light from soaring cathedral ceilings and oversized windows. A seamless open layout connects the living and dining areas with a central gathering area anchored by a sleek linear gas fireplace. Award-winning chef-designed kitchen is framed by a dramatic wall of glass and features premium Wolf and Sub-Zero appliances, including an eight-burner gas cooktop, integrated refrigerator, double built-in ovens, Miele coffee system, warming drawer, Scotsman ice maker, high-level custom cabinetry and more, flanked by dual wine columns. The primary retreat is in its wing, complete with a 20-by-10-foot custom walk-in closet and a spa-inspired bath with a soaking tub and oversized walk-in shower featuring multiple shower heads. The home's most captivating element is the fully enclosed, air-conditioned 29-by-17-foot lanai, accessible through disappearing glass doors that create a seamless transition from indoors to out. This sophisticated outdoor living space includes a full summer kitchen, alfresco dining area, lounge with gas fireplace and motorized screens for further flexible utilization. Just beyond, a heated lap pool is framed by lush bamboo landscaping, creating a serene and secluded outdoor living environment. Another special feature is a secluded casita, which offers an ideal space for guests or multigenerational living. Two additional bedrooms with en suites, each with walk-in closets, complete the three-way split flexible bedroom layout along with a well-appointed utility/mud room entry off the oversized two-car garage. Ideally near Winter Park Racquet Club, Interlachen Country Club and accessible to Park Avenue, this exceptional residence also offers an extraordinary blend of modern design, luxurious functionality and premier location. Winter Park living at its finest!

765 Via Lugano, Winter Park

$819,000

2 Beds ⋅ 2 Baths ⋅ Trotters Rep SubDv. ⋅ 32789 Zip Code

Fully renovated 1926 historic Winter Park bungalow with separate cottage in the heart of the Winter Park Historic District. Ideally located within a short distance to Park Avenue, Rollins College and the Winter Park Chain of Lakes community dock, just minutes from the Winter Park 9-hole Golf Course. Exceptional full home remodel by Z Properties in 2020 including a gourmet kitchen, shiplap walls with hidden doors and hidden primary bedroom entry, plus additional updates in 2024. The separate cottage is under air and can be used for a personal gym, golf simulator, home office, guest suite, additional storage or more. Schedule your showing to embrace the modern elegance and historic charm.

734 Maryland Ave, Winter Park

$1,300,000

4 Beds ⋅ 3 Baths ⋅ Ardmore SubDv. ⋅ 32789 Zip Code

One or more photo(s) has been virtually staged. An extraordinary opportunity to own a beautifully renovated home on a prestigious tree-lined street in Winter Park’s 32789. Set on a desirable 13,500 square foot (90 × 150) lot with no HOA and bordering the prestigious Windsong community, this prime property offers the freedom to live comfortably now, expand over time, or build new. This 4-bedroom, 3-bathroom block and brick home has been fully renovated with wide plank flooring and tile, a stunning light-filled kitchen with Café appliances and quartz countertops, Carrara marble bathrooms, and a primary suite featuring a walk-in shower built with a Schluter system. Bathed in natural light, the sunroom serves as an additional living or flex space, with a row of French doors opening to the pool and patio. A screened-in lanai overlooks a remarkable backyard, sparkling pool and spa surrounded by lush landscaping, creating a perfect setting for entertaining, relaxing, or letting pets play. All new ductwork, interior and exterior paint, and a clean, natural aesthetic throughout make the home move-in ready. Sidewalks invite morning strolls to Lake Mizell and scenic walks or bike rides through the neighboring Windsong community and winding shaded brick streets. Zoned for great schools including Brookshire Elementary, Glenridge Middle, and Winter Park High, and close to wonderful private schools such as Park Maitland, Trinity Prep, Lake Highland Prep, and more. Just minutes from Park Avenue’s shops and dining and close to Baldwin Park. Whether you love it as it is or envision building a custom estate on this .31-acre lot, 1500 Mizell Ave offers a rare chance to own a legacy property in one of Winter Park’s most coveted neighborhoods. The location is superb.

1500 Mizell Avenue, Winter Park

$1,277,000

3 Beds ⋅ 4 Baths ⋅ Parklando SubDv. ⋅ 32789 Zip Code

Welcome to a truly exceptional residence nestled on a quiet, tree-lined street in one of Winter Park’s most desirable neighborhoods. This custom-built gem offers a blend of elegance, craftsmanship, and resort-style comfort, featuring 3 bedrooms, 3.5 baths, and 2,595 square feet of thoughtfully designed living space. As you enter, you'll be immediately drawn to the tranquil, resort-like ambiance created by the centerpiece of the home: a screened-in courtyard with a heated saltwater pool and spa, perfect for relaxing or entertaining year-round. Adjacent to this serene space is a private guest casita complete with a full bath and separate entrance, ideal for in-laws, visitors, or an independent-minded teen. Step into the main house, and you will be immediately captivated by the 15-foot Frank Lloyd Wright-inspired rock wall in the stunning Living Room. The 12-foot ceilings give the space a seemingly endless light and airy feel. Overlooking the great room is a fully equipped chef-inspired kitchen where creating meals will be a breeze with an abundance of cabinets, gleaming quartz counter tops, a large prep island,14 foot breakfast bar and newer top-of-the-line LG SS appliances, and a GE Profile cook top — ensuring that entertaining and meal prep are effortless. There is also a large dining room that can fit more than a large dinner party or family holiday gathering. Also, tucked away on the opposite side of the first floor is a guest suite, featuring a spa-inspired bath with beautiful cabinetry, exquisite tile work, and a large walk-in shower. Plus, the large laundry room with an abundance of storage and a utility sink to round out the main floor of this stunning home. Upstairs is the elegant private owner’s retreat, which also enjoys a quiet sitting area and an expansive custom walk-in closet. The spa-like bath will not disappoint with its large soaking tub, separate stall shower, and dual sinks with contemporary cabinetry and elegant tile throughout. Additional amenities include a large 2-car garage with an EV 30 amp outlet, plus an oversized over 300 square foot separate flex space that would make an excellent home office, home gym, or craft/hobby space. The home features tons of storage space, custom automated blinds with remotes, blackout blinds, a new AC unit, new lighting, new exterior paint, and a tankless water heater. This remarkable home is flooded with natural light and ambiance, with many floor-to-ceiling windows, while exuding a warm and cozy atmosphere. Zoned for some of the best public schools in the area, including Audubon K-8 and Winter Park HS, and conveniently located near Audubon Park/Corrine Drive shopping and restaurants, and of course easy access to Winter Park's Park Ave with its fine restaurants and shopping, and also close proximity to Blue Jacket Park/Baldwin Park, Downtown Orlando, Leu Gardens, the Mills 50 District and Rollins College. Don't miss your opportunity to own this exquisite Winter Park retreat, a perfect blend of luxury, privacy, and location. Florida living at its finest!

2728 Eastern Parkway, Winter Park

$940,000

4 Beds ⋅ 3 Baths ⋅ Karolina On Killarney SubDv. ⋅ 32789 Zip Code

Biscayne Bay, a recent Parade of Homes winner, is one of the latest custom builds by the trusted team at Konkol Custom Homes—and it’s ready for its very first owner. Set in a prime Winter Park location, this two-story home offers clean lines, high-end finishes, and a layout that fits real life. With just over 2,600 square feet under air, the home features 4 bedrooms and 3 full bathrooms. The 4th bedroom is located downstairs and works beautifully as a dedicated office. Upstairs, a spacious bonus room offers flexibility for a home gym, theater, large office, or guest suite. Throughout the home, you’ll find wide-plank white oak flooring, matching stair treads, tall baseboards, and cohesive, streamlined trim details. The kitchen is crisp and functional, with white cabinetry, quartz counters, tile backsplash, and well-chosen finishes. The primary suite includes a walk-in closet system and a bathroom that checks all the boxes—soaking tub, oversized shower, and double vanities. Out back, enjoy a generous covered porch, landscaping that offers privacy with a natural bamboo hedge, and a future-ready pool plan already in place. High style, low maintenance living—all just five minutes from Park Avenue, walkable to Lake Killarney, close to Dubsdread, and under 2 miles to AdventHealth. Biscayne Bay is a polished, move-in ready opportunity in the heart of Winter Park.

1840 Biscayne Drive, Winter Park

$458,000

3 Beds ⋅ 1 Baths ⋅ Bungalow Park SubDv. ⋅ 32789 Zip Code

One or more photo(s) has been virtually staged. Location, Location, Location! Nestled in the heart of highly sought-after Winter Park, this charming 3 bedroom home offers the perfect blend of vintage character and modern updates. Just steps away from Park Avenue, Hannibal Square, and the city’s historic district, you’ll enjoy walkable access to upscale shopping, fine dining, and everything Winter Park is known for. Step inside to a light-filled, spacious living room featuring beautiful wood flooring and timeless charm. The separate dining room also boasts wood floors and a large picture window, perfect for hosting intimate dinners or enjoying family meals. The kitchen retains some of its original charm while offering new stainless-steel appliances and ample cabinetry. One of the standout features of this home is the expansive bonus room formerly the garage highlighted by decorative wood beams and endless possibilities for a home office, studio, or entertainment space. The private, fenced backyard is ideal for outdoor living, with plenty of room for gatherings, BBQs, or relaxing under the stars. Situated on R-2 zoning, this property also presents additional future potential in one of Central Florida’s most desirable neighborhoods. Don’t miss the opportunity to own a home in one of Winter Park’s most iconic and walkable locations!!!

955 Minnesota Avenue, Winter Park

$5,225,000

3 Beds ⋅ 4 Baths ⋅ Galloway Place Rep SubDv. ⋅ 32789 Zip Code

An architectural triumph, this one-of-a-kind modern masterpiece was custom designed and built in 2023 by the award-winning Z Properties and is ideally sited on the shores of Lake Osceola, part of the Winter Park Chain of Lakes. Radiating bold sophistication and contemporary elegance, the residence is a curated work of art, where floor-to-ceiling glass walls and striking steel windows and doors flood the interiors with natural light and deliver unobstructed panoramic lake views from nearly every room. Enter through a dramatic 12-foot glass pivot door into a 21-foot-long art gallery foyer adorned with a sculptural linear chandelier and Venetian plaster walls and ceilings that lend a soft, refined texture. The open-concept living spaces are accentuated by terrazzo floors, 12-foot ceilings, and thoughtful spatial design—including a great room with a sitting area and dining space, a separate media room concealed behind custom 12-foot decorative doors, and a sleek galley-style kitchen outfitted with fully integrated Miele appliances and a secondary glass pivot door for seamless indoor-outdoor flow. Ascending one of two custom staircases, the second floor features warm hardwood floors and a showstopping primary suite that feels suspended above the lake, backyard and pool. This serene retreat offers an all-glass shower, spa-inspired soaking tub, beautifully finished bath cabinetry, and an upholstered wall that subtly conceals a walk-in closet and built-in storage. A second bedroom suite offers an inspired use of space with clever screen walls for privacy and flexibility. Detached from the main home, a third bedroom suite doubles as a guest house, home office, or gym, complete with an en-suite bath, custom built-ins and a wet bar. Outside, the terraced backyard is a tranquil oasis with a saltwater pool and spa, turf lawn for year-round perfection, dual staircases leading to a sundeck and a private, covered boat dock crowned by a glass-enclosed studio mirroring the home’s signature design. Bamboo privacy walls, soaring palms, and a Banyan tree imported from South Florida create a lush and artful landscape. The two-car garage includes epoxy flooring and dual EV charging stations. A singular residence in every sense, this home blends innovative architecture, luxurious finishes and thoughtful design into a rare offering unlike anything else in Winter Park. Built by Z Properties, celebrated in Florida Design and numerous design publications, this is a home for those who appreciate beauty, intention and the art of living well.

1333 Alberta Drive, Winter Park

$1,005,000

2 Beds ⋅ 1 Baths ⋅ Charmont SubDv. ⋅ 32789 Zip Code

Entered for sold data purposes only

361 E Kings Way, Winter Park

$980,000

3 Beds ⋅ 3 Baths ⋅ Lake Knowles Terrace SubDv. ⋅ 32789 Zip Code

Nestled in the desirable Tree Streets of Winter Park, this stunning Mid-Century Modern residence offers timeless style, thoughtful updates, and effortless indoor-outdoor living. With over 2,100 square feet of beautifully designed space, this 3-bedroom, 2.5-bath home delivers modern functionality with elegant character—just minutes from the heart of Park Avenue. Inside, you'll find an open floor plan with engineered hardwood flooring, high ceilings, crown molding, and abundant natural light. The kitchen is a chef’s dream, featuring a convection oven, cooktop, range hood, and brand-new appliances—ideal for both daily living and entertaining. A wet bar with wine fridge, cozy sunroom, and custom closets in all three bedrooms elevate the home’s comfort and convenience. The primary suite is located upstairs, offering privacy and retreat. The backyard is a true Florida oasis, complete with a newly resurfaced saltwater pool, expansive artificial turf, a custom putting green, and a deck with a retractable awning—all within a fully fenced yard designed for privacy and year-round enjoyment. Additional upgrades include a new roof (2020), updated A/C system (2021), garage storage solutions, and lush front landscaping. With no HOA, a 2-car garage, and extended driveway parking for 4+ vehicles, this home offers both style and flexibility in one of Winter Park’s most coveted neighborhoods. A rare opportunity to own a turnkey home in a prime location—schedule your private showing today.

1610 Chestnut Avenue, Winter Park

$775,000

2 Beds ⋅ 2 Baths ⋅ Cloisters Condo SubDv. ⋅ 32789 Zip Code

Welcome to The Cloisters—a prestigious lakefront community nestled in the heart of Winter Park, perfectly positioned between the timeless charm of Park Avenue and the serene beauty of Lake Osceola. This fully furnished second-floor residence has been meticulously redesigned and renovated to maximize both space and style, offering the comfort of a thoughtfully designed home, enhanced by luxurious, designer-selected finishes throughout. Step inside to discover a beautifully appointed interior featuring high-end touches. The kitchen is a true showpiece, boasting custom wood cabinetry with artistic wood detailing, granite countertops, full counter-to-cabinet backsplashes, and top-tier appliances including a Wolf cooktop and oven, Fisher & Paykel dishwasher, Liebherr wine cooler, and Sub-Zero refrigerator. The expansive kitchen island comfortably seats four, with a sleek, integrated extension that effortlessly accommodates up to seven—perfect for entertaining in style. The open-concept living area flows seamlessly to a spacious private balcony, offering tranquil views of the heated pool, putting green, lush landscaping, and the shimmering waters of Lake Osceola—ideal for a morning coffee or year-round entertaining. The primary suite is a serene retreat, featuring blackout blinds, a Sleep Number smart bed with dual temperature controls, and custom floor-to-ceiling built-ins with integrated lighting, display shelving, and a dedicated vanity area. Additional built-in cabinetry lines the hallway leading to the en-suite bathroom, providing ample space for jewelry, shoes, and wardrobe essentials. The second bedroom is designed for versatility, with a wall-to-wall built-in home office setup overlooking a beautiful resort-style view, along with its own matching floor-to-ceiling built-ins for display and storage. Both bathrooms have been tastefully reimagined with new vanities, granite countertops, upgraded shower enclosures and hardware, and stylish lighting and mirrors. The primary bath includes additional custom built-ins for optimal storage and organization. Throughout the home, fresh paint and luxury vinyl flooring create a clean, modern aesthetic. Additional features include an in-unit washer and dryer tucked behind a custom wood door, a built-in safe, and a new A/C unit installed in 2024. The residence also includes a deeded covered-parking space and a private storage unit. The Cloisters community offers a wealth of amenities, including an onsite property manager, ample guest parking, elevators, a heated pool, onsite laundry facilities, a putting green, private lake access, a dock, and boat slips available via resident lottery. Residents also enjoy two fitness centers with one dry sauna and a recently updated clubhouse with a full kitchen and bath—ideal for private gatherings. Just a short stroll from the boutiques, restaurants, and cultural attractions of Park Avenue, and Rollins College, this fully renovated, turnkey residence presents a rare opportunity to enjoy the ultimate blend of location, luxury, and lifestyle. Realtor/owner is a licensed Florida real estate broker.

100 S Interlachen Avenue Unit 204D, Winter Park

$312,000

3 Beds ⋅ 2 Baths ⋅ Stansbury Estates SubDv. ⋅ 32789 Zip Code

$5K SELLER CONCESSION TOWARDS BUYER'S CLOSING COSTS AND PRE-PAIDS!!! Charming, Fully Renovated Bungalow in the Heart of Winter Park! Welcome to this beautifully upgraded bungalow that makes every square foot count! Nestled perfectly between Winter Park and College Park, this fully renovated gem blends modern upgrades with timeless charm. From the moment you arrive, the custom-built front pergola and all-new paver driveway invite you in with style. Step inside to discover a cozy yet efficient layout filled with thoughtful details: barn doors, built-ins, a cabinet pantry, and a linen closet in the guest bath that add character and storage throughout. The brand-new kitchen is compact but packed with quality—featuring granite countertops, stainless steel appliances, and custom cabinetry that maximizes function and charm. The spacious primary suite offers a walk-in closet and an en-suite bath with a very large walk-in shower. Other unique features include a charming barn door to separate the laundry area from the guest bath, optimizing flow and privacy, an extended and brand new paver driveway, along with a beautiful custom fence and storage sheds that provides added storage. This charming bungalow has been designed to live larger than its footprint. Don’t miss your chance to own this thoughtfully designed home in one of Central Florida’s most desirable locations!

1921 Dartmouth Avenue, Winter Park

$1,575,000

4 Beds ⋅ 4 Baths ⋅ Sylvan Lake Shores SubDv. ⋅ 32789 Zip Code

Beautiful Sylvan Lake Shores Mediterranean home. Ideally located in quintessential Old Winter Park with its tree lined, brick streets that surround Lake Mizell. This 4 bedroom 3 ½ bath, plus office home features timeless architectural features such as classic wide molding, repeated archways and a custom ironwork stairway. The soaring 10 foot ceilings accentuate the classic feel of this elegant home. The designer inspired kitchen features custom cabinets and spacious pantry. The spa like master suite is located on the first floor and has an en-suite bath and custom designed closet. Just recently completed, the luxurious master bath has an inviting soaking tub and separate, relaxing rain shower. The executive office is located on the first floor. Up the custom staircase are three bedrooms including a private guest room with its own en-suite bath. The open floor plan is perfect for entertaining with multiple, solid wood French doors surrounding the welcoming back yard pool with cooling fountains. Outside, a custom awning shades the patio as you relax by the pool. There is a convenient pool bath as well. This bright and sunny home is in a prime location of Winter Park with an easy walk or bike to Park Avenue with its upscale restaurants, stores and Rollins College. Excellent Winter Park Schools. This amazing move in ready home is an excellent opportunity to live in the heart of Winter Park and enjoy Central Florida living.

1394 Grove Terrace, Winter Park

$3,975,000

4 Beds ⋅ 6 Baths ⋅ Cloister Grove Sub SubDv. ⋅ 32789 Zip Code

In the heart of Winter Park, 1150 Via Salerno is a newly completed Mediterranean-minimalist residence that blends architectural refinement with organic warmth. Now offered at a compelling new price, the home presents a rare opportunity to experience architecturally distinctive new construction in the Vias neighborhood. Conceived, developed & designed by Steve & Jodie Konold of Scout & Co., the 3,850-sf residence offers 4 beds & 5.5 baths, w/ a layout thoughtfully arranged to provide the intentional privacy of a luxury retreat. Beyond its terraced walkway—envisioned in collaboration w/ architect Cynde Norris—French antique gates open to a native-planted entry garden, creating a soft transition to the interior. A glass foyer featuring a woven rattan chandelier, sourced & designed in London, leads to a sculptural stairwell positioned just off the main living spaces. The great room includes soaring ceilings, a sleek, custom plaster fireplace & walls of glass doors & windows. Ten-inch baseboards meet level 5 drywall in a clean reveal, paired w/ micro-crete flooring on the main level & wide-plank European oak upstairs. The kitchen is appointed w/ a Thermador dual-fuel range, matching plaster hood, full refrigerator & freezer columns & a large island with seating topped in honed black quartzite. The surrounding cabinetry features hand-carved V-groove panels w/ soft-close hardware & integrated pullout storage. Caesarstone surfaces line the perimeter while steel-and-glass open shelving w/ a sculptural black sconce balances the composition. A vintage chandelier from Prize Home & Garden sourced in Round Top completes the room. The main floor primary suite is accessed through antique doors that open to a light-filled gallery overlooking the rear courtyard & pool. The primary bath features an extended vanity w/ dual sinks, matte black fixtures, a freestanding tub, walk-in shower w/ built-in bench & separate water closet. On the mezzanine level, the powder bath makes a dramatic statement w/ a floating black quartzite trough sink paired w/ a handwoven mirror. Across the hall, the laundry room blends beauty w/ utility w/ custom cabinetry, matching quartzite surfaces, matte black fixtures & a side-by-side front-load washer & dryer. A nearby bedroom suite is marked by an antique door entry. Each guest bedroom features an en-suite bath introduced by a hand-painted tile threshold, complemented by designer lighting, distinctive mirrors & continuous European oak flooring. The rooftop terrace is accessed from the second-floor hallway. The detached casita opens to the pool courtyard through accordion glass doors on two walls & includes a woven rattan chandelier & a full bath—ideal as a studio, gym or office. Other outdoor spaces include 2 garden courtyards, a heated saltwater pool & a newly constructed outdoor kitchen designed to accommodate a built-in grill & Big Green Egg. A spacious gravel courtyard is ideal for dining or relaxing and is enveloped by mature bamboo that creates exceptional privacy. Additional features include a lower-level two-car garage, storage closet, 3 HVAC systems, Rinnai tankless water heater, Sierra Pacific windows, customized closets, solid core doors, 6” round gutters & a Barcelona barrel tile roof. Thoughtfully designed & beautifully executed, 1150 Via Salerno offers a refined lifestyle within one of Winter Park’s most exclusive enclaves.

1150 Via Salerno, Winter Park

$1,607,160

4 Beds ⋅ 3 Baths ⋅ Lake Knowles Terrace SubDv. ⋅ 32789 Zip Code

An extraordinary home, built in 2018 by Lazarus, is on a quaint cobblestone street in the exclusive Tree Streets of Winter Park. Contemporary transitional design has many details and has been beautifully maintained and upgraded. A four-bedroom, three-bath pool home stretches over 2,800 square feet with natural light filling the spaces through expansive windows. The home offers open concept living in the main gathering room as well as dedicated dining and office/or guest rooms. Fantastic kitchen with custom double cabinetry to the ceiling features an abundance of storage and generous workspace, a large center island with quartz counters, with a stylish waterfall edge and subway glass tile backsplash. Top of the line appliances include Kitchen Aid and Bosch and a Viking 48-inch gas range, microwave drawer and kitchen are rounded out with a butler's pantry/bar area with built-in wine refrigerator that blends the kitchen to dining. Kitchen is open to the living room with a gas fireplace finished with sleek tile extending to ceiling and vaulted ceiling with wood detail all opens to outdoor living under a covered porch with tongue and groove ceiling and sparkling pool. The main level owner’s retreat has two large walk-in closets, and serene bath with double sinks, soaking tub and custom tiled walk-in shower with seamless glass. An additional guest room/study on the first floor has a private bath while upstairs you’ll find two oversized bedrooms and a second bonus/family room. Other details include frosted glass garage door, hardwood pre-engineered wood floors, home recently painted, Phillip Jeffries Wallpaper in dining, designer Restoration Hardware and Pottery Barn Fixtures, professional designed landscaping with architectural outdoor lighting, recessed lighting package, upgraded insulation and energy-efficient tankless water heaters contribute to lower energy bills, 10-foot ceilings, 8-foot doors, custom tile work and beautiful crown moldings. In walking distance to Phelps Park and YMCA, close to hospital, Park Avenue, great shops and restaurants as well as Rollins College. Schools are the best with Lakemont Elementary, Maitland Middle and Winter Park high schools.

1541 Chestnut Avenue, Winter Park

$750,000

2 Beds ⋅ 2 Baths ⋅ Osceola Summit SubDv. ⋅ 32789 Zip Code

Location, location, location! Whether you're ready to build your dream home or simply want to enjoy life in Central Florida’s most prestigious neighborhood at an unbeatable value, this delightful mid-century 2-bedroom, 2-bathroom home offers endless possibilities. Lot size is approximately 130 ft X 78 ft. Perfectly positioned just minutes from Park Avenue, Rollins College, and Lake Osceola, this home places you at the center of luxury Winter Park living—enjoy boutique shopping, fine dining, scenic strolls, or morning paddle boarding just steps from your door. Inside, you'll find a bright and open floor plan filled with natural light and timeless charm. A front den/office with white tile flooring and timeless tongue and groove ceiling offers you space that is not only stylish but functional—ideal for working from home or relaxing with a book. The open living/dining area features stylish wood flooring, large windows, and a ceiling fan for year-round comfort. This unique layout offers 2 primary suites offering plenty of privacy. Head to the fully fenced back yard and concrete patio which provides a private retreat for entertaining or relaxing outdoors. You will find yourself in the heart of it all with close proximity shops, restaurants, schools, universities and major airports. An added hidden bonus is your access to Lake Osceola through 2 parks and walkway ramp, where you can enjoy a beautiful sunset or paddle board/kayak ride. With vintage character, and incredible location with lake access at the end of the street, this Winter Park gem is not to be missed!

311 Cortland Avenue, Winter Park

$1,725,000

5 Beds ⋅ 5 Baths ⋅ Kenilworth Shores Sec 06 SubDv. ⋅ 32789 Zip Code

WINTER PARK FIVE BEDROOM POOL HOME - Discover luxurious living in the heart of Winter Park! Crafted with exquisite attention to detail, this 5-bedroom, 4.5-bathroom pool residence showcases absolute perfection and modern elegance. Built in 2018 by David Weekley Homes, the property boasts a captivating stone façade and a private backyard oasis featuring a saltwater, heated pool and spa with water feature, and ambient lighting — an entertainer’s dream. Inside, soaring ceilings, gleaming wood floors, expansive picture windows, and an abundance of natural light create an inviting and sophisticated atmosphere. The gourmet kitchen is a chef’s paradise, with white maple cabinetry, Quartz countertops, a breakfast island, and stainless-steel gas appliances. The open floor plan seamlessly connects the kitchen, great room, and outdoor living spaces, perfect for hosting friends and family. Located on the first-floor, the spacious primary suite includes a spa-inspired bathroom, while a dedicated home office and guest suite offer comfort and versatility. Upstairs, discover three additional bedrooms, two full bathrooms, and a versatile loft space. Step outside to the wrap-around porch overlooking meticulously landscaped gardens, creating a serene and private outdoor retreat. Located just minutes from Park Avenue, Rollins College, and Advent Health Winter Park, this exceptional residence offers convenient access to top shopping, dining, and cultural attractions. Zoned for the highly sought-after Brookshire School District, this is your chance to experience elevated living in one of Winter Park’s most coveted neighborhoods. Schedule your private showing today and make this exquisite property your new home.

617 Worthington Drive, Winter Park

$2,575,000

5 Beds ⋅ 6 Baths ⋅ Fontainebleau SubDv. ⋅ 32789 Zip Code

Discover luxury living in this custom Austin Homes 5 bedroom, 5 and one half bath transitional style home that offers a blend of modern and traditional elements coupled with a highly desirable Winter Park location. This residence boasts a sought-after open floor plan with 12-foot ceilings, wide plank wood flooring and truly exceptional detailed finishes throughout. You will feel instantly at home as you pass through the fully enclosed front yard and enter through the double door entrance from the covered wrap-around front porch. The open-concept design seamlessly connect the dining room and family rooms as you make your way to the kitchen area complete with Wolf & Sub-Zero stainless-steel appliances, double islands, Wellborn custom cabinetry, and private Butler's Pantry with new washer/dryer. The gourmet kitchen opens to the spacious family room where you will find a built-in fireplace with custom millwork, recessed lighting, and beautiful French doors that open fully to the outside entertainment/living area. The split floor plan is perfect for the family and as you find your way throughout the remainder of the home, you will be impressed by the designer window treatments, plantation shutters, built-in speaker system, high-quality upgraded light fixtures, and private pool bath. The main floor includes a spacious primary retreat with a large walk-in closet and private French doors leading to the pool area. The spa-like bathroom includes a stand-along soaking tub, dual sink with stone counters and generous walk-in shower. The formal dining room and en-suite guest bedroom complete the first level. Upstairs are 3 spacious bedroom suites with full baths, a generous bonus/media room with built-in desk, and a second upstairs laundry room with hook ups. You will enjoy Florida living while relaxing on your covered lanai complete with retractable screens and summer kitchen overlooking the saltwater sparkling pool/spa with new pool heater and fully enclosed kid friendly yard. Upgrades include: Control 4, new electronic driveway entry gate, whole house interior and exterior painting, Jeld Wen solid core interior doors, hardwood floors throughout the first floor & bonus room, custom closet systems in all closets, rare 3-car garage, vinyl insulated windows, core fill & block walls, high density spray foam insulation in ceilings, R13 in frame walls, Carrier 15-Seer AC dual systems with UV filtration, and two Rinnai gas tankless water heaters, whole house water filtration. This pristine residence is situated on an oversized corner lot and it truly timeless, move-in ready, and only ½ mile to the Winter Park Raquet Club and 2 miles to famed Park Avenue to enjoy incredible dining and boutique shopping. Call now for your private tour!

1341 Place Picardy, Winter Park

$1,785,000

3 Beds ⋅ 3 Baths ⋅ Temple Estates SubDv. ⋅ 32789 Zip Code

This elegant one story home is located in highly desirable Winter Park on an oversized .28 acre lot with mature and lush landscaping and NO HOA. It has 10' ceilings and an open floor plan combining kitchen, dining, and living rooms with gorgeous wood floors and plenty of natural light overlooking the secluded & screened salt water pool with cascading water features, gas heated spa, and covered lanai. This home has a warm and welcoming atmosphere perfect for entertaining family & friends. The gourmet kitchen features an induction cook top, built in convection & microwave oven, stainless steel refrigerator, vented stainless steel hood system, wine refrigerator, bar station, and pantry. It also has custom designed kitchen cabinetry with abundant storage and pull out shelving plus a big island with designer pendant lights and eat in area for a large table and chairs. The laundry room next to the master bedroom has cabinetry and a sink. Adjacent to the living room is a room that could be used as a office or workout room AND a big multi functional room with half bathroom also overlooking the pool area. Sliders from the living room and the multi functional room are pocket sliders which really open up the home in cooler weather ! The huge master suite also opens to the pool and has his and hers walk in closets with built in custom closet organizers and the master bathroom has dual sinks, whirlpool garden tub, and big walk in shower. In addition, there are two guest bedrooms that share a hall bathroom. The backyard is fenced and very private and peaceful with a gravel walkway with low voltage lighting that leads to an arbor with a swing for an outdoor gathering or reflection. Other upgrades includes Plantation shutters, motorized shades on sliding doors, whole house built in audio system, and security system. Roof was installed in 2019 and new pool pump. Steps away is Phelps Park with playground, tennis and pickleball courts and the YMCA is nearby. Park Avenue and Downtown Winter Park with plenty of fine dining and upscale shopping options are a bike ride away or short drive !

1640 Mayfield Avenue, Winter Park

$3,600,000

5 Beds ⋅ 7 Baths ⋅ Forest Hills SubDv. ⋅ 32789 Zip Code

Discover premier Winter Park luxury real estate at 1820 Glencoe Road—a stunning Dutch West Indies–inspired custom home built by FG Schaub Custom Homes. Ideally located minutes from Park Avenue, Rollins College, and downtown Winter Park, this residence offers the perfect blend of coastal architecture and modern Florida luxury living. With 4,055 sqft. of thoughtfully designed space, this Winter Park pool home features 5 bedrooms, 5 full bathrooms, 2 half baths, and a private home office. A grand entryway opens to a bright, open-concept interior with expansive Andersen windows that enhance indoor-outdoor flow—an essential feature for Florida homes. The chef’s kitchen is a standout, equipped with Wolf and Sub-Zero appliances, custom cabinetry, quartz countertops, and an oversized island ideal for entertaining. The great room offers seamless living with a wet bar, wine column, and elegant tiled electric fireplace. The first-floor primary suite serves as a private retreat with a spa-style bathroom that includes dual vanities, a soaking tub, glass-enclosed walk-in shower, towel warmer, and custom walk-in closet. A guest suite with a walk-in closet and en-suite bathroom, dining area, and main laundry room complete the first level. Upstairs, you’ll find a dedicated office, activity room, powder bath, secondary stackable laundry, and 3 spacious ensuite bedrooms—each with generous walk-in closets and ceiling fans. Designed for year-round indoor-outdoor living, the transitional room features a full summer kitchen with grill, hood vent, refrigerator, retractable screen, mini-split A/C, and an additional powder bath. Step into your private backyard oasis with a resort-style pool, spa, fire pit, outdoor shower, Travertine pool deck, and lush tropical landscaping—perfect for relaxing or entertaining. Additional features include security cameras, surround sound, an oversized 2-car garage with EV charging port, epoxy floors, LED lighting, a paver driveway with extra parking, standing seam metal roof, privacy fencing, and professional landscaping. Located in one of Winter Park’s most desirable neighborhoods and zoned for Audubon K-8 / Winter Park High School. Schedule your private tour today. **Builder is offering up to $30,000 in buyer incentives toward window treatments with an acceptable offer.**

1820 Glencoe Road, Winter Park

$2,125,000

2 Beds ⋅ 3 Baths ⋅ Landmark Winter Park SubDv. ⋅ 32789 Zip Code

When you enter through the secure and elegant wrought iron gates and walk into in the private central courtyard, you'll feel the sophistication of The Landmark Winter Park. Take the elevator to the second floor and your private entrance balcony overlooking the courtyard. Inside, this spacious corner unit you'll find 2 bedrooms, 3 full bathrooms and a spacious media room/office. From the foyer look through the large dining and living room space to windows overlooking shady Morse Boulevard. This unit lives large with the floor plan nicely splitting the primary suite, second bedroom and media room/office for maximum comfort and privacy. And perhaps most impressive of all is the large, bright kitchen with huge center island, loads of counter space and storage, Sub Zero refrigerator, KitchenAid 6-burner gas range and wine cooler. Twelve-foot ceilings and large windows throughout add to to the spacious, luxurious feeling. The massive primary suite is truly a retreat, with French doors opening onto the private balcony from the bedroom, large spa-inspired bathroom and fully built-out walk-in closet. Bedroom two, on the other side of the condo also has a walk-in closet and a generous bathroom with step-in shower. The office/media room is large and private, completely separate from the bedrooms, with direct access to the third bathroom. Laundry/utility room with rear exit door is away from the living space and has lots of storage. Two dedicated parking spaces in the secure underground garage, and each unit has its own climate controlled storage space for bicycles and other large items. The Landmark Building is Winter Park's premiere address. Luxury, privacy and proximity to all Park Avenue is known for, including boutique shopping, cafes and fine dining, as well as Central Park and Rollins College with many events and programs throughout the year. Easy access to Central Florida's highways, and SunRail station just steps away. Luxury living in Winter Park, it is here in The Landmark.

140 E Morse Boulevard Unit C, Winter Park

$439,900

3 Beds ⋅ 2 Baths ⋅ Lake Bell Terrace SubDv. ⋅ 32789 Zip Code

One or more photo(s) has been virtually staged. ***BUY THIS HOME WITH AN FHA INTEREST RATE OF 5.375% WHEN USING THE SELLER'S PREFERRED LENDER*** You will fall in love with this mid-century Winter Park home across from Lake Bell in charming Lake Bell Terrace. This home offers 3 Bedrooms, 1 spa-like bathroom, and an en-suite half bath, a family room, living room, dining room, and a laundry room. Some of the renovations include a full kitchen redesign with fresh double-stacked white cabinetry, quartz countertops, stainless steel appliances, and sleek over-range hood. There are hardwood floors throughout the main living areas in the home & a hip hexagonal dark floor tile in the kitchen and dining room. Some of the upgrades include: a water softener system, whole house re-plumb 2021, energy efficient windows 2018/2019, A/C system (new condenser coil) A/C UV sanitation light 2019, upgraded electrical in 2023, and fresh insulation in the attic throughout the home. The spacious fenced-in backyard offers a beautiful hardscape area with a fire pit and a stunning pergola ideal for an outdoor lounge area or summer kitchen. As a bonus, the garden includes an avocado tree, ginkgo, young Anna, and pink lady apple trees, smoke bush, and lime trees. You won’t find a home better situated than this, conveniently located just one mile from I-4, this home offers easy access for your daily commute or a quick drive to catch your favorite Orlando Magic or Orlando City game. Downtown Orlando is just 12 minutes away and only 6 minutes to downtown Winter Park to enjoy all the fine dining and luxurious amenities. As for the Theme Parks, you are 35 minutes away from Disney World, Epic Universe/Universal, and less than an hour away from the nearest beach. Welcome home!

1945 Bering Avenue, Winter Park

$530,000

3 Beds ⋅ 2 Baths ⋅ Shores Lake Killarney SubDv. ⋅ 32789 Zip Code

Welcome to this beautiful home in highly sought-after Winter Park! This 3 bedroom 2 bath home in the desirable Shores of Lake Killarney will capture your attention for sure. It is well maintained and immaculately kept. Kitchen has plenty of cabinet and counter space, granite counter tops and tiled backsplash. The screened patio is cedar with stone flooring and has plenty of space to entertain! Open Mediterranean style patio is tucked in the back corner of the property. Circular, brick paved front driveway provides a nice touch on this corner lot. This home has a lot of space and is in a neighborhood with no HOA restrictions. You have plenty of room for entertaining and plenty of space to add a pool! It is within close proximity to shopping, restaurants, Sanford International Airport, the 417 and I-4. Deeded Lake Access to Lake Killarney. This seller is motivated so bring your offers!

212 Blossom Lane, Winter Park

$1,800,000

5 Beds ⋅ 6 Baths ⋅ Lake Knowles Terrace Add 02 SubDv. ⋅ 32789 Zip Code

Welcome to this beautifully crafted 5 bedroom, 5.1 bathroom traditional single-family home offering over 4,100 SF of living space. Ideally located on a tree-lined street with Winter Park’s signature brick roads, this home sits in one of the area’s most sought-after neighborhoods. Just minutes from the Winter Park Racquet Club in the Vias, Park Avenue shops and dining, YMCA, top hospitals, and excellent public and private schools, it offers the best of Winter Park living. A charming front porch leads into a thoughtfully designed interior that blends classic style with modern functionality. To the right of the foyer is a private office with built-in shelving and glass pocket door, while the left opens to a formal dining room with a tray ceiling, chandelier, and ambient lighting. The spacious living room features a gas fireplace, beamed ceiling, crown molding, and built-in shelving, with French doors that open to the screened lanai for seamless indoor-outdoor living. The chef’s kitchen offers ample cabinetry, expansive countertops, a center island with secondary sink, walk-in pantry, and a breakfast nook with more French doors to the lanai. On the main floor, the primary suite includes a spa-inspired bath with double vanities, garden tub, and multiple closets. A guest suite also on the first floor includes a private bath, beverage fridge, and coffee station. A full laundry room and butler’s pantry with wine fridge complete the first level. Upstairs features a large loft with built-in cabinetry, under-cabinet lighting, and a beverage fridge. A built-in desk and cabinets line the hallway for study or work space. Two bedrooms share a Jack and Jill bath, and a third has access to a nearby full bath. A second laundry room, currently used as an office, adds flexibility. Step outside to a private backyard oasis with a screened lanai, sparkling pool, outdoor kitchen, mature landscaping, and full pool bathroom. With a new roof (2023), commercial grade water heater (2022), fresh exterior paint (2024) and many upgrades, this home offers turnkey living in one of Winter Park’s finest communities.

1355 Hibiscus Avenue, Winter Park

$699,000

3 Beds ⋅ 2 Baths ⋅ Lakeview Terrace SubDv. ⋅ 32789 Zip Code

Rare find in Winter Park! This charming one-story pool home offers three bedrooms, two full baths, high ceilings, and an open floor plan—all at an incredible price point. The updated kitchen features gas appliances, a center island, breakfast bar, and a separate beverage fridge. Wood-look tile flooring runs throughout the home for a cohesive, modern feel. The spacious primary suite features French doors that open to a private patio with pool access. The en suite bathroom is oversized, with a large walk-in shower and double vanities. The garage has been temporarily enclosed and is air-conditioned, offering flexible bonus space that can easily be converted back. The home’s nearly 1,700 square feet do not include this additional area. Located just minutes from top-rated Winter Park schools, shopping, and dining. Don’t miss this opportunity!

1891 Bryan Avenue, Winter Park

$675,000

3 Beds ⋅ 2 Baths ⋅ Fontainebleau SubDv. ⋅ 32789 Zip Code

LOCATION! LOCATION! LOCATION! EXPECT TO BE IMPRESSED IN THIS CHARMER LOCATED IN THE HEART OF WINTER PARK! Welcoming you and guests is an attractive curb appeal with walkways and pretty landscaping located on a nicely sized lot all fenced in for privacy. Sit back and relax in this easy, carefree, low maintenance home, desirably located in a peaceful & established community close to major highways. Breathe in some fresh air and walk to Park Avenue known for lots of shopping and delicious restaurants or open your front door & you’re invited into plenty of space to enjoy everyday living & entertaining in this generously sized 3 bedroom, 2 bath pool home offering 1,442 sq. ft. The charming kitchen delivers good looks with an eat in kitchen nook, plenty of storage and access to your outdoor patio made easy for grilling or relaxing. The family room open to the kitchen is light and bright allowing natural light in and creating a cozy atmosphere. Indoor and outdoor space combine perfectly, inviting you to enjoy delightful views and savor Florida living at its very best. Walk through the doors, sit on your enclosed porch, have a glass of wine and listen to the birds. Set on a generously sized homesite, this private backyard is bigger than most, offering a sparkling pool and plenty of room to throw a football & build a swing set. Thoughtfully set far from the busy family area, you'll find a nicely sized master suite with a walk in closet. Extra features include; a newer roof (2022) including new soffits and gutters! A thoughtful layout ensures that everyone will have their own personal space. COME SEE THIS CHARMING HOME LOVINGLY MAINTAINED AND MAKE IT YOURS TODAY!

2190 Temple Drive, Winter Park

$790,000

2 Beds ⋅ 2 Baths ⋅ Dixie Terrace SubDv. ⋅ 32789 Zip Code

The inviting bungalow at 1217 Kenwood Ave is located just a few houses off famed Park Avenue and steps from the Winter Park Village, which is fresh off a $50 million transformation and includes popular bars and restaurants, a movie theater and shopping. The home was fully renovated in 2018 with updates to the HVAC, electrical, plumbing, flooring, subflooring, interiors, and a new roof- offering modern functionality with classic charm. The kitchen features rich navy cabinetry, gold hardware, quartz countertops, a gas range with hood, and a tankless water heater. Since 2021, the home has seen additional upgrades including custom roller shades (shade store), a new sprinkler system, enhanced landscaping with decorative rockwork, paver installation, and fresh sod. Improvements also include new interior and exterior lighting, a porch fan, garage and laundry shelving, and a recently serviced A/C system. The spacious backyard offers room for a pool and is already plumbed for a future outdoor kitchen. Enjoy rear entry access from Denning via a two-car garage. Don’t miss this rare opportunity in one of Winter Park’s most walkable locations!

1217 Kenwood Avenue, Winter Park

$355,000

3 Beds ⋅ 2 Baths ⋅ Park Green SubDv. ⋅ 32789 Zip Code

Charming One-Story Townhome in Prime Winter Park Location! Welcome to this adorable detached 3-bedroom, 2-bath townhome with a spacious 2-car garage, tucked away in the heart of Winter Park (32789). Just minutes from Winter Park Village, Fleming’s, and the boutiques and dining of Park Avenue, this home blends low-maintenance living with unbeatable convenience. Step inside to find a bright, open layout and peace of mind with recent updates, including a new roof (2021), re-piping (2023), and AC system (2016). The single-story design offers ease and comfort, whether you’re looking for a primary residence or a winter retreat. The community features a refreshing pool and clubhouse, and the HOA covers cable and internet—making day-to-day living even easier. Don’t miss this rare opportunity to enjoy the charm and convenience of Winter Park in a move-in-ready home!

1117 Park Green Place, Winter Park

$420,000

3 Beds ⋅ 2 Baths ⋅ Howell Heights SubDv. ⋅ 32789 Zip Code

Beautifully Updated 3 Bedroom, 2 Bath Pool Home in Desirable Winter Park! Welcome to your dream home! This spacious one story gem features 3 bedrooms, 2 full baths, and a private POOL, perfect for enjoying Florida living year round. Step inside to find brand NEW LUXURY VINYL PLANK flooring and FRESH INTERIOR PAINT throughout, giving the home a modern and move-in ready feel. The open layout offers plenty of room to relax or entertain, and the enclosed porch provides a versatile space. The kitchen is a chef's delight with GRANITE countertops and ample cabinet space. Outside, enjoy a large FENCED yard, ideal for pets, play, or gardening. Located in a highly sought after Winter Park neighborhood, this home is just minutes from top-rated schools, shopping, dining, parks, and more. Don't miss this incredible opportunity, schedule your showing today!

2809 Sanbina Street, Winter Park

$2,037,500

5 Beds ⋅ 5 Baths ⋅ Conwill Estates SubDv. ⋅ 32789 Zip Code

Price Reduced to sell. An exceptional custom home by award-winning Davila Homes, perfectly blending modern design and functionality. Located in sought-after Conwill Estates, just minutes from Park Avenue, this 5-bed, 4.5-bath residence features volume ceilings, floor-to-ceiling bronze sliding doors, and a seamless indoor-outdoor living experience. The chef’s kitchen showcases waterfall quartz countertops, Sub-Zero & Wolf appliances, a large island, walk-in pantry, and opens to the living area with phantom screens and views of the resort-style gas-heated pool, fire pit, and a brand-new outdoor kitchen, perfect for entertaining. A first-floor owner’s suite offers pool views, private terrace, motorized shades, spa bath with soaking tub, and expansive shower. Upstairs you'll find 4 en-suite bedrooms, a bonus room with wet bar, wine fridge, 2nd laundry, and balcony overlooking the backyard. Additional upgrades include Summer Kitchen, surround sound, gas fireplace, upstairs & downstairs laundry, private well for irrigation, generator, new HVAC system for downstairs (2025), new water heater (2025), and air-conditioned garage with tiled floors (not included in living SF). This home has been impeccably maintained and is in pristine condition, aluminum roof is a plus. — it truly feels like new. From the moment you step inside, you’ll fall in love with its elegance and charm.

1781 Pine Avenue, Winter Park

$999,999

4 Beds ⋅ 3 Baths ⋅ Timberlane SubDv. ⋅ 32789 Zip Code

Welcome to 2112 Fosgate Drive, a beautifully updated home nestled on a quiet, tree-lined street in Winter Park. With 4 bedrooms, 3 bathrooms, and just under 2,400 square feet, this residence offers a thoughtful layout with plenty of space to fit your lifestyle. Fully remodeled in 2018, it’s move-in ready with a blend of charm and modern comfort. Step inside and you’ll be welcomed by real hardwood floors and a bright, open floor plan that flows easily from room to room. The kitchen is a true highlight, featuring marble countertops and backsplash, stainless steel appliances—including a double oven—and a separate beverage fridge. It’s perfect for everyday meals or entertaining guests. The home’s three-way split layout offers privacy and flexibility. The spacious owner’s suite includes a fully renovated bathroom and a generous walk-in closet with built-in shelving. A guest en-suite provides an ideal setup for visitors or a home office, while two additional bedrooms share an updated bath and are tucked away for peace and quiet. Out back, you’ll find an oversized backyard anchored by a spacious covered patio with brick pavers and motorized screens—perfect for entertaining or relaxing while little ones play. Additional features include new designer interior doors, plantation shutters, insulated windows, and newer soffits and roof. Ideally located near Blue Jacket Park, East End Market, and zoned for highly rated Audubon K-8 and Winter Park High, this home offers the best of Winter Park living. Don’t miss your chance to make it yours!

2112 Fosgate Drive, Winter Park

$1,595,000

5 Beds ⋅ 5 Baths ⋅ Lawndale SubDv. ⋅ 32789 Zip Code

Experience the charm and elegance of Winter Park living in this beautifully designed 5-bedroom, 4.5-bath home offering 3,267 square feet of thoughtfully crafted space. This residence combines timeless architectural character with modern functionality, From the moment you enter, you’re welcomed by warm natural light, the first floor features an office with an open and inviting layout, and high-quality finishes throughout. Enjoy a spacious kitchen and a generous living and dining area, perfect for entertaining and relaxing, creating a warm and inviting atmosphere. The sliding glass door leads to the refreshing Swimming Pool, Summer Kitchen, a serene retreat for relaxation and entertaining. Following the wooden staircase to the second floor, this home features a spacious primary master suite, offering privacy, convenience, and ease of living. The Pool, the detached two-car garage, and the charming private flex suite are the perfect balance of elegance and comfort. Located just minutes from the heart of Park Avenue Winter Park, downtown Orlando, and fine dining, boutique shopping, museums, and local cafés.

1733 Harmon Avenue, Winter Park

$705,000

3 Beds ⋅ 2 Baths ⋅ Winter Park Heights SubDv. ⋅ 32789 Zip Code

Vintage house with close proximity to Park Avenue surronded by newely constructed homes on a scenic brick street. A creative designer would find this vintage house a great project with a newly constructed roof to save the time. This winter park corner lot is highly sought after for its location and its potential.

1730 Oneco Avenue, Winter Park

$1,270,000

4 Beds ⋅ 4 Baths ⋅ Fontainebleau SubDv. ⋅ 32789 Zip Code

Seller is including a premium home warranty giving buyers peace of mind with coverage on HVAC, plumbing, appliances & more so you can move in with confidence! Experience the charm and elegance of Winter Park living in this beautifully designed 4-bedroom, 3.5-bath home offering 3,604 square feet of thoughtfully crafted space. Built in 2014, this residence combines timeless architectural character with modern functionality, all nestled on a quiet, tree-lined street in one of Central Florida’s most sought-after neighborhoods. From the moment you enter, you’re welcomed by warm natural light, an open and inviting layout, and high-quality finishes throughout. Enjoy a spacious chef’s kitchen, generous living and dining areas, and a private primary suite perfect for both entertaining and relaxing. The detached two-car garage and charming outdoor space add to the home’s appeal and functionality. This home features a spacious primary master suite located on the first floor, offering privacy, convenience, and ease of living. Located just minutes from the heart of Park Avenue, you’re steps from some of Winter Park’s most beloved spots—fine dining, boutique shopping, museums, and local cafés. Nearby favorites include The Ravenous Pig, Hillstone, Boca, Ava MediterrAegean, and the world-renowned Winter Park Farmers’ Market. With easy access to I-4, 17-92, and Semoran Blvd, commuting to downtown Orlando, Maitland, or the airport is a breeze. Call to set your appointment to view this lovely home!

2401 Lafayette Avenue, Winter Park

$560,000

2 Beds ⋅ 1 Baths ⋅ Blk C Pt Rep 02 SubDv. ⋅ 32789 Zip Code

A rare find in Winter Park: A charming Bungalow with 3-Car Garage (24x36) and detached finished Shed (10x14) for office & or additional Storage! Walking distance to Mead Gardens and the new Seven Oaks Park. Convenient to Rollins College, Park Avenue and Winter Park Village, featuring multiple local eateries and restaurants. Just one mile to Hospital, Science Center and Museum. Easy access to 17/92, I-4 and 408 Expressway. New Roofs (2022), Sewage Pipes Relined (2024), Hot Water Tank (2021) and Home Air Conditioner (2020). Don't miss this hidden gem in beautiful Winter Park, Florida. Submit all offers on "As Is" contract with proof of funds attached. All information is deemed to be correct. Buyer and buyer's agent should verify all prior to submission.

1339 Orchid Avenue, Winter Park

$916,000

3 Beds ⋅ 3 Baths ⋅ Kenilworth Shores Sec 06 SubDv. ⋅ 32789 Zip Code

Nestled in the heart of Winter Park in one of the area’s most sought-after neighborhoods, this professionally designed and fully renovated 3-bedroom, 2.5-bathroom home offers luxurious living with timeless modern style. Step inside to an open-concept layout featuring a gourmet kitchen outfitted with custom cabinetry, stunning quartz countertops, GE Café appliances, a Thermador drawer-style microwave, Brizo faucets, a coordinating pot filler above the stove, and designer light fixtures—perfect for both entertaining and everyday living. Adjacent to the kitchen, a custom wine and coffee bar with floating shelves seamlessly blends style and functionality. For dog lovers the home even includes a whimsical “Doggie Bistro,” complete with its own pot filler, making it a breeze to refill water bowls! This meticulously maintained single-story home offers abundant storage, including generous bedroom closets, attic access, and garage overhead storage. Additional space is available in the backyard shed and the oversized two-car garage with built-in storage. Bathrooms have been completely remodeled with premium finishes, high-end vanities, and designer fixtures that combine elegance and functionality. The powder room near the main living space adds the perfect touch of sophistication and convenience. The front living room features a wood-burning fireplace and a large picture window that fills the space with natural light. Step outside to your private, fully fenced backyard, shaded by a canopy of fragrant jasmine and serenaded by the sounds of local peacocks. With ample space for relaxing or entertaining, the yard also offers a perfect canvas for a future pool. No detail has been overlooked. Recent upgrades include: New roof (2019), new A/C unit (2023), Blow-in insulation, sprinkler system, home water softener, PGT energy-efficient windows (2019), custom pergola with screen, original refinished hardwood floors throughout the main living spaces and bedrooms. Garage auto carpet to create multi-use space. Located just minutes from downtown Winter Park, top-rated schools, award-winning restaurants, scenic parks, and the popular Cady Way Trail, this home offers the best of Central Florida living. With easy access to downtown Orlando, major highways (408, 417, I-4), Disney attractions, and Orlando International Airport. The neighborhood continues to evolve, with many homes being replaced by larger custom homes valued at over $3 million. This is a rare opportunity to own a turn-key home in a highly desirable community!

609 Langholm Drive, Winter Park

$435,000

2 Beds ⋅ 2 Baths ⋅ Klusman Place Condo Or 5980/3320 SubDv. ⋅ 32789 Zip Code

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693 Minnesota Avenue Unit 693, Winter Park

$145,000

1 Beds ⋅ 1 Baths ⋅ Lakeside Manor Apts Condo SubDv. ⋅ 32789 Zip Code

Reasons you'll love this condo: convenient, cozy and quiet, you can't beat this community for its location and tranquil setting on Lake Killarney. Add to that the brand new air conditioning system (2025), hot water heater (2025) and fresh paint throughout (2025) and you'll see why this unit is for you. Step into the unit through the brand new front door (2025) and you are in the generous living room with dining space. The tidy kitchen with matching all white appliances is clean as a whistle. You'll love the large utility is where you'll find the air conditioner, hot water heater and plenty of shelving. The bathroom has new vanity (2025), mirror and light fixture (2025), and newer toilet. You'll find the bedroom spacious with a large double closet. Ceiling fans in living and bedroom. Location in the community is handy, with assigned parking space just steps away and easy access to the quiet courtyard. You'll love the lakefront outdoor space including pool, club house, tons of manicured green space, over-water covered seating on the new dock, boat launch and slips. Close to shopping and dining in Winter Park, easy access to highways. This community is everything people come to Florida to find!

2500 Lee Road Unit 243, Winter Park

$199,000

2 Beds ⋅ 1 Baths ⋅ Aragon Condo SubDv. ⋅ 32789 Zip Code

Welcome to this beautifully updated second-floor corner unit nestled within the sought-after Aragon Condominium community in the heart of Winter Park. This bright and airy two-bedroom, one-bath home offers a perfect blend of comfort, style, and convenience. Step inside to discover freshly painted interiors and elegant laminate flooring that flows seamlessly throughout the space. The galley-style kitchen offers a functional layout and opens to a spacious living and dining area—ideal for both relaxed evenings at home and entertaining guests. Natural light fills the open-concept living space, while the cozy front patio invites you to enjoy your morning coffee or unwind at the end of the day. Both bedrooms are generously sized with pool view and feature built-in closets for easy organization, while a hallway closet adds extra storage for linens or household essentials. The bathroom features modern finishes and thoughtful design, with a shower and tub. The Aragon community offers a host of amenities designed for easy living, including a tranquil central courtyard, a sparkling community pool, on-site laundry facilities, and ample parking with both assigned and guest spaces. Located in one of Winter Park’s most vibrant neighborhoods, this condo is just steps from shopping centers, grocery stores, restaurants, and retail boutiques. With quick access to I-4 and nearby parks, it offers both a peaceful retreat and a connected urban lifestyle. Whether you’re a first-time buyer, downsizing, or searching for an ideal investment opportunity, this delightful home provides the perfect combination of charm, location, and livability.

851 Miles Avenue Unit 8, Winter Park

$530,000

3 Beds ⋅ 2 Baths ⋅ Lake Killarney Condo SubDv. ⋅ 32789 Zip Code

Experience luxury lakefront living in this stunning and truly unique 3-bedroom, 2-bathroom second-floor condo. This expansive 1,875 SF residence blends modern European design with artistic detail. Designed by a local artist in collaboration with a local architect, every element of this home reflects thoughtful craftsmanship and sophistication. The condo features newer plumbing, electrical wiring, and two new HVAC units that were installed in 2024. Natural light pours in through generous windows, enhancing the open-concept layout that seamlessly connects the dining room, living room, and kitchen. The living room is a welcoming space with built-in shelving, views of the lake, and a walk-in closet that is a useful utility closet. The kitchen is both functional and striking, featuring German textured glass cabinetry, granite countertops, and stainless steel appliances. A show-stopping in-kitchen dining table crafted from high-gloss peacock blue lava stone and French marble serves as a stunning focal point. The primary bedroom offers a walk-in closet, a peaceful sitting area with lake views, and a serene en-suite bathroom complete with a soaking tub. The second bedroom also enjoys lake views and a sitting area, while the third bedroom includes an antique English armoire that serves as a closet. Natural bamboo flooring runs throughout the home, adding warmth and style. The unit is accessed by a private staircase that leads you to your secluded lakefront retreat. The community features include; a very nice swimming pool that was just redone, clubhouse, and recreational areas. This unit includes two dedicated parking spaces and access to a private community boat launch. Annual boat slip rentals are available for $900, and the lake even permits seaplane landings—perfect for those seeking both adventure and tranquility. Located just a short walk from Trader Joe’s, the Winter Park Library, and Hillstone Restaurant, this condo combines quiet lakefront living with unbeatable proximity to shopping, dining, and entertainment. Just minutes from downtown Winter Park, this is a rare opportunity to own a one-of-a-kind home in an exceptional setting.

151 N Orlando Avenue Unit 212, Winter Park

$1,175,000

3 Beds ⋅ 2 Baths ⋅ College Place Rep SubDv. ⋅ 32789 Zip Code

Charming 1925 Craftsman with Spanish-Style Guest Apartment in Winter Park's College Quarter. Nestled in the heart of the historic College Quarter, this beautifully preserved 1925 Craftsman home offers timeless character, modern livability, and a rare bonus: a separate Spanish/Moorish-style garage apartment with its own unique architectural flair. The main house features 3 bedrooms, 2 bathrooms, and 1,867 square feet of inviting living space. Classic elements like original heart of pine floors and period finishes can easily blend in well with additional interior updating. Although the house has the history, the flow of the layout works well with today’s modern living and entertaining style. Additionally, just behind the main home, is a 504-square-foot garage apartment which offers a living space, kitchenette, bedroom and bathroom. It has striking interior details, such as hand-hewn pecky cypress beams, heavy plaster work, keyhole shaped doors and hand-wrought ironwork and a cozy fireplace. The apartment space is —a perfect guest retreat, income-producing rental, or private home office. The property also comes with deeded lake access to scenic Lake Virginia, part of the coveted Winter Park Chain of Lakes. The proximity to downtown Winter Park is just a short stroll, through tree-lined brick streets to Park Avenue’s shops and restaurants, as well as Rollins College, which is just a street away. Whether you're seeking historic character, walkable charm, or lakeside living, this unique Winter Park property delivers it all! 4-Point inspection was completed, please see attachments for survey and for home details.

835 Antonette Avenue, Winter Park

$3,020,000

5 Beds ⋅ 6 Baths ⋅ Forest Hills SubDv. ⋅ 32789 Zip Code

Award-winning Phil Kean design on a prominent corner lot in the heart of Winter Park, just minutes from Baldwin Park, Park Avenue, and East End Market—home to Michelin-rated dining and upscale retail. This 5-bed, 5.5-bath residence delivers clean lines, smart design, and seamless indoor-outdoor flow. Recognized with multiple honors, including the 2015 Parade of Homes 1st Place Award for Custom Homes, the American Residential Design Award from the AIBD, and the prestigious 2015 Aurora Awards, this home reflects the highest level of architectural achievement. A retractable Nanowall opens to a private outdoor escape with a heated saltwater pool, summer kitchen, fireplace, motorized screens, and mature bamboo landscape. Two driveways and a freshly laid zoysia lawn add presence to the front approach. Inside, 10’ ceilings and a fluid open plan frame the chef’s kitchen—finished with waterfall quartz, touch-close cabinetry, and Thermador appliances including a steam oven, induction cooktop, and 98-bottle wine cooler. The media room includes surround sound, a motorized screen, and a second retractable wall to the pool. Smart home controls manage lighting, security, Sonos, and cameras with ease. The guest suite offers a Murphy bed and private bath. The primary features a fireplace, spa-style bath, and custom closet. All bedrooms include en-suite baths. Additional highlights: whole-house generator, water filtration, foam insulation, sweep-in vacuum, and an EV-ready garage with custom storage.

1820 Englewood Road, Winter Park

$705,000

3 Beds ⋅ 2 Baths ⋅ Charmont SubDv. ⋅ 32789 Zip Code

Unlock the potential of this charming 3-bedroom, 2-bathroom home—ideal for renovation or building your custom dream residence. Nestled among a mix of beautifully preserved historic homes and stunning new construction, this property is located in one of Central Florida’s most sought-after neighborhoods. The home features classic terracotta tile flooring, two cozy wood-burning fireplaces—one in the inviting living room and another in the spacious primary suite—and a detached workshop perfect for hobbies or additional storage. Enjoy the best of both convenience and lifestyle just minutes from vibrant Park Avenue’s boutiques and restaurants, Downtown Orlando, Baldwin Park, and an array of local parks and recreation. Don’t miss this rare opportunity to create something truly special in the heart of Olde Winter Park!

1840 Laurel Road, Winter Park

$1,000,000

4 Beds ⋅ 4 Baths ⋅ Winter Park Village SubDv. ⋅ 32789 Zip Code

Welcome to 2607 Lafayette Avenue – a stunning custom-built residence nestled in one of Winter Park’s most desirable neighborhoods. This beautifully crafted home offers 4 spacious bedrooms, 3.5 bathrooms, and 2,770 square feet of refined living space designed for modern comfort and effortless entertaining. Step inside to discover an open-concept layout that seamlessly connects the kitchen, dining, and living areas. The kitchen features brand-new appliances, quartz countertops, shaker-style cabinetry, a classic subway tile backsplash, and a large island ideal for gathering. Elegant new light fixtures and a built-in wet bar elevate the space with a touch of sophistication. The first-floor primary suite is a serene retreat, offering two closets and a well-appointed en-suite bathroom complete with a soaking tub and separate walk-in shower. Upstairs, a spacious loft opens to a walk-out balcony and is accompanied by three additional bedrooms and two full bathrooms – perfect for family and guests. Storage is abundant with three walk-in closets, a double closet, and a convenient under-stair space. Additional highlights include a two-car garage with an epoxy floor, a screened patio for year-round enjoyment, and a fenced backyard oasis ideal for relaxation or entertaining. Freshly painted and surrounded by all-new professional landscaping with an irrigation system, this home offers exceptional curb appeal. Located just minutes from Park Avenue’s shopping and dining, Rollins College, the Winter Park Chain of Lakes, and zoned for A-rated Dommerich Elementary, Maitland Middle, and Winter Park High School—this property blends luxury, location, and lifestyle.

2607 Lafayette Avenue, Winter Park

$228,000

1 Beds ⋅ 1 Baths ⋅ Karolina On Killarney SubDv. ⋅ 32789 Zip Code

This cozy 1-bedroom, 1-bath bungalow is your ticket into one of Winter Park’s most desirable neighborhoods—just steps from beautiful Lake Killarney and surrounded by some of the city’s best dining, shopping, and entertainment. Whether you’re looking for a charming personal retreat, a smart investment, or a renovation project with serious upside, this property delivers with its unbeatable location and potential. Sitting on one of the larger lots on the street and with no HOA to restrict your vision. What makes this opportunity truly special is the walkable lifestyle—Trader Joe’s, Winter Park Village, Park Avenue, Dubsdread Golf Course, and a full menu of local restaurants and shops are all just minutes away. Quick access to I-4 puts downtown Orlando, nearby attractions, and work commutes easily within reach, yet you’re tucked away in a serene, scenic pocket of town where lake breezes and neighborhood charm still reign. Homes in this area are rarely available at this price, making it a golden chance to get into a sought-after location and bring your dream renovation to life. Don’t miss the opportunity to own a slice of Winter Park with character, convenience, and curb appeal just waiting to be unlocked. Please allow up to 72 hours for a response. DO NOT SUBMIT OFFERS SITE UNSEEN!

1979 Staunton Avenue, Winter Park

$965,000

3 Beds ⋅ 4 Baths ⋅ Mondrian/Winter Park Twnhms SubDv. ⋅ 32789 Zip Code

Don’t miss out on the final new construction unit available - act fast! Discover unparalleled luxury at Mondrian Winter Park, where contemporary design meets the tranquil beauty of Lake Killarney. We are excited to share that this is the LAST corner unit of a highly coveted floor plan in our exclusive community of just 30 modern townhomes along the serene shoreline. Each residence features exquisite finishes, stunning storefront-style windows, and soaring ceilings just shy of 11 feet, allowing natural light to fill the interiors. This brand-new townhome combines contemporary aesthetics with charming brownstone elements, showcasing a unique layout designed for convenience and privacy. The main living space is beautifully situated on the second level, allowing for a seamless flow between the modern kitchen, dining room, and great room. Retreat to the stylish primary bedroom located at the back of the home, where you’ll find a spa-inspired bathroom complete with two walk-in closets, a cozy sitting area, designer tile, a frameless glass shower, and a private water closet—all thoughtfully crafted for ultimate comfort. Our smart split bedroom design includes two additional bedrooms with en suites on the first level, delivering ample space and flexibility for your lifestyle. A full-size laundry room adds to the functionality and elegance of your new home. Step onto the rooftop oasis featuring an outdoor kitchen, a pergola, a hot tub spa, and breathtaking open sky views, creating the perfect setting for relaxation and entertainment. Nestled in picturesque Winter Park, just north of downtown Orlando, residents can enjoy lakeside living with access to a private boat slip, community kayaks, and a beautiful lakefront pavilion. Whether you’re in search of serene relaxation or vibrant entertainment, this prime location offers proximity to top-tier dining, shopping, and recreational amenities for a lifestyle of unmatched convenience and luxury. Seize this incredible opportunity before it’s gone—your dream home on Lake Killarney awaits!

1760 Mondrian Circle, Winter Park

$325,000

3 Beds ⋅ 3 Baths ⋅ Winter Park Gardens Condo SubDv. ⋅ 32789 Zip Code

CLICK ON VIRTUAL TOUR to get an overview of the complex. HUGE PRICE REDUCTION!!!!......Discover a RARE opportunity to own a 3 BEDROOM 2.5 BATH unit at beautiful Winter Park Gardens. One of only seven 3 BEDROOM units so infrequently available. Located on the second floor. Enjoy stunning floor to ceiling views of lush landscaping, walking paths, pond, and the expansive 8.1-acre gardens in your tropical sunroom. Located in a vibrant 55+ community that welcomes younger owners, this prime location is within walking distance of Rollins College, Orange Ave, Mead Gardens, and downtown Park Ave. Don’t miss out on the serene, sought-after lifestyle Winter Park Gardens offers—call today to make it yours!

700 Melrose Ave Unit C22, Winter Park

$800,000

3 Beds ⋅ 4 Baths ⋅ Lake Knowles Terrace Add 02 SubDv. ⋅ 32789 Zip Code

Fantastic Lake Knowles Terrace community close to The Via's, Downtown Winter Park and I-4 road access. Lots of possibilities to restore this 1940 classic home or create your own brand new structure . This property offers so much potential in Winter Park's premier and sought after location. Call today for your private tour !!

1823 Sunset Drive, Winter Park

$1,300,000

4 Beds ⋅ 4 Baths ⋅ Comstock Park SubDv. ⋅ 32789 Zip Code

**DON'T LET THIS OPPORTUNITY PASS YOU BY, BACK ON MARKET DUE TO BUYERS FINANCING.** Luxurious Retreat in the Heart of Winter Park’s Premier Neighborhood – Minutes from Park Ave! Discover timeless elegance in this stunning 4-bedroom, 3.5-bathroom home offering 2,953 square feet of thoughtfully designed living space. Nestled on tree-lined streets in one of Winter Park’s most coveted areas, surrounded by multi-million-dollar estates and just moments from the Winter Park Chain of Lakes, this home defines luxury living. Step through the impressive cut beveled glass double front doors into an interior filled with natural light, featuring hardwood floors, crown molding, recessed lighting, and blinds and Roman shades throughout. Formal living and dining rooms provide an elegant backdrop for entertaining, while the fireplace in the family room adds a cozy touch. Sliding French doors and two sets of large sliders seamlessly extend the living space to the private pool area. A sunroom (added in 2024) with a mini split system offers additional space to relax and unwind. Enjoy modern upgrades including a monitored security system, intercom system, reverse osmosis water filtration, and a water softener system. The gourmet kitchen is a chef’s dream with custom wood cabinetry, wavy tiled backsplash, granite countertops, stainless appliances including a newer refrigerator (2024) and newer dishwasher (2022), a gas stove, and two pantries, including a walk-in pantry. The breakfast nook and breakfast bar with seating for three creates plenty of space for gathering. Retreat to the luxurious primary suite with wood floors, a large walk-in closet, and a spa-like ensuite bathroom featuring double split vanities, a garden soaking tub, a large tiled shower, and a private water closet. Enjoy your own private backyard paradise on a .26-acre lot with a resort-style in-ground pool (2021), waterfall feature, sun shelf, lush landscaping, and irrigation system. An electronic front gate provides peace of mind for security as you're guided to a paved driveway and parking pad with a 2-car garage to complete this exceptional property. All this in a highly sought-after location, just minutes from Park Avenue’s high end shops and fine dining restaurants, Rollins College/Dinky Dock public boat ramp, Winter Park 9 Golf Club, Winter Park Racquet Club, Interlachen Country Club, Winter Park YMCA and WP Phelps Park and playground and so much more! Don’t miss your chance to own a piece of Winter Park’s finest! Schedule your private tour today. (Roof: 2019, HVAC 2017, Mini Splits (2) 2024, Electrical 2004, Plumbing 2004)

1420 Palmer Avenue, Winter Park

$490,000

3 Beds ⋅ 2 Baths ⋅ Glencoe Sub SubDv. ⋅ 32789 Zip Code

3-Bed, 2-Bath Home in Prime Winter Park Location! Steps away from paddleboarding, kayaking or fishing on beautiful Lake Killarney! Welcome to your new home nestled in one of Winter Park’s most desirable areas—with easy access to I-4. This beautifully maintained 3-bedroom, 2-bathroom residence offers the perfect blend of comfort, convenience, and style. Features a bright, open floor plan with spacious living areas, and plenty of natural light. Modern kitchen complete with stainless steel appliances, quartz countertops, and ample cabinet space—perfect for both casual meals and entertaining. The primary suite offers a private retreat with an en suite and generous closet space, while the two additional bedrooms are ideal for family, guests, or a home office. Enjoy outdoor living with a fenced-in backyard, oversized lot, and ample room to create your ideal outdoor oasis. No HOA! ROOF & AC REPLACED 2022. Located just minutes from Park Avenue shopping and dining, Winter park village, Rollins College, and downtown Orlando. This home is perfect for those seeking convenience without compromising on charm. Don’t miss this opportunity to own a move-in-ready gem in the heart of Winter Park. Schedule your private showing today!

240 Cambridge Boulevard, Winter Park

$675,000

2 Beds ⋅ 2 Baths ⋅ Lake Knowles Terrace SubDv. ⋅ 32789 Zip Code

Attention builders and investors! Here’s your chance to own a prime property in the coveted Tree Streets of Winter Park, one of Central Florida’s most desirable neighborhoods. Whether you’re looking for immediate rental income or planning to build your dream home in the future, this opportunity is not to be missed! Tucked away just minutes from Phelps Park, the Winter Park YMCA, Lake Knowles, and top-rated Lakemont Elementary, this home is ideally located for both convenience and lifestyle. Enjoy peaceful neighborhood strolls, bike rides to the boutiques and cafés of Park Avenue, or weekend outings at the Winter Park Farmers’ Market. Living here means being immersed in the charm and culture that makes Winter Park so special—historic homes, scenic lakes, a vibrant arts scene, and a strong sense of community. Step inside to find a well-maintained home full of character. Original hardwood floors bring warmth and timeless appeal to the living areas and bedrooms. A versatile bonus room offers endless possibilities—use it as a home office, playroom, gym, or cozy den. Outside, the backyard is made for Florida living, with a screened-in patio perfect for al fresco dining and a spacious yard ideal for gardening, entertaining, or weekend fun. Whether you're investing, living in, or planning to build new, this property offers exceptional potential in a premier location. Don’t miss your chance to become part of the Winter Park lifestyle!

1511 Chestnut Avenue, Winter Park

$530,000

2 Beds ⋅ 1 Baths ⋅ Winter Park Village SubDv. ⋅ 32789 Zip Code

Investor / Builder special!! Prime land opportunity located just minutes from Park Avenue. Don't miss your chance to build your custom home in this highly desirable area, surrounded by multi-million dollar homes. Value is in the land. Schedule your showing today!

2525 Lafayette Avenue, Winter Park

32789 Zip Code 1/3 Acre Real Estate & Homes

Browse All 32789 Zip Code FL 1/3 Acre Properties for Sale