32789 Zip Code FL Real Estate, Homes with No HOA Fee for Sale

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

On one of Winter Park’s most scenic brick-lined streets, this exceptional two-story residence commands attention on a spacious corner lot, blending timeless architectural elegance with modern luxury. Built in 2016 by the highly regarded Rex-Tibbs Development & Construction, the home showcases quality craftsmanship throughout, from its striking curb appeal to its impeccably appointed interiors. A three-car side-entry garage, air-conditioned and offering generous storage, is connected to the home via a covered walkway, adding functionality and charm. Inside, beautiful wood floors extend seamlessly throughout the entire home, including all bedrooms, creating a warm, cohesive atmosphere. The main level offers an elegant formal dining room and a flexible front room that can serve as a home office, library or formal living area. The heart of the home is the expansive family room, anchored by a gas fireplace and illuminated by natural light through large sliding glass doors that open to the lanai and pool. Overlooking the family room, the open-concept kitchen is a culinary dream, featuring a Wolf six-burner gas range with double ovens, Sub-Zero refrigerator, abundant cabinetry and expansive counter space, ideal for everyday living and entertaining. The first-floor primary suite is a retreat, with French doors leading directly to the pool area, a luxurious spa-style bath, and a custom 14-by-10-foot walk-in closet designed for maximum organization and style. A secondary primary suite, also on the main level, includes a generous walk-in closet and a private en-suite bath, offering flexibility for guests or multigenerational living. Upstairs, the home continues to impress with a spacious recreation/game room, a separate bonus room and three additional bedrooms, all of which feature en-suite baths and walk-in closets, ensuring comfort and privacy for family and visitors alike. Step outside to experience resort-style living at its finest. The covered lanai is equipped with a fully outfitted summer kitchen, including a built-in grill, while the pool area is a showstopper, complete with a dramatic gas fire display, tranquil waterfall, ambient lighting, and a lush wall of bamboo that enhances privacy and lends a tropical ambiance. A separate outdoor cabana with TV and seating area offers a place to unwind or entertain in style. Beyond the home, the location is unbeatable. In one of Winter Park’s most desirable neighborhoods, you’re just minutes from the upscale shops, fine dining and cultural attractions of Park Avenue. The home is also conveniently close to top-rated public and private schools, premier medical facilities and major transportation hubs, including the Orlando Executive Airport and Orlando International Airport, ensuring ease of access for business and leisure travel alike. This remarkable property offers the ultimate in refined living, combining luxury, comfort and convenience in one of Central Florida’s sought-after communities.

2171 Forrest Road, Winter Park

$2,440,000

4 Beds ⋅ 5 Baths ⋅ Winter Park Heights SubDv. ⋅ 32789 Zip Code

One lucky Buyer's gain is this Seller's bittersweet goodbye. A job relocation has these homeowners leaving behind a home they absolutely love, and now, you can make 1700 Palm Ave. yours! Modern sophistication and everyday functionality come together seamlessly in this exceptional Winter Park residence. With 3,770 square feet of thoughtfully designed living space, this 4-bedroom, 4.1-bath home offers a fantastic floorplan featuring a first-floor primary suite, private office, and a striking two-story great room filled with soft natural light from the south-facing backyard. Upstairs, a generous loft/bonus room accompanies three en-suite bedrooms, including a second suite designed as an alternate primary, complete with a private balcony, dual walk-in closets, and a dedicated water closet. The smart three-way split bedroom configuration enhances privacy and flexibility, while the first-floor primary suite features two large walk-in closets and a stackable washer and dryer for added convenience. The open-concept layout flows effortlessly to the covered lanai, complete with electronic roll-down screens, two beverage refrigerators, and a gas grill—overlooking a sleek saltwater pool framed by gray and white marble pavers. Tall sliding glass doors stack to create a seamless indoor-outdoor living experience, perfect for entertaining. Lush, mature podocarpus hedges and Japanese blueberry trees line the perimeter, offering a private and polished backdrop. The chef’s kitchen is outfitted with top-of-the-line Viking appliances, a gas cooktop, quartz countertops, and a walk-in pantry. A spacious island with a beverage fridge and generous storage complements the adjacent dining area, which comfortably seats eight, with room to expand for larger gatherings. Custom electronic roller shades add privacy and a clean, modern aesthetic, electronic/rechargeable blinds throughout the first floor and matching manual blinds upstairs. Wide-plank oak floors extend throughout the main level and up the architectural floating staircase. The oversized garage is equally well-appointed, featuring two storage closets and a built-in rack system. Ideally located just minutes from Winter Park’s renowned shops and dining on Park Avenue. The home is zoned for top-rated WP schools, including Winter Park High, Maitland Middle, and Lakemont Elementary. Looking to join a tennis league or spend afternoons on the golf course? This home is surrounded by both public and private clubs for social and athletic enjoyment. 1700 Palm Ave. delivers fabulous living in one of Central Florida’s most coveted neighborhoods.

1700 Palm Avenue, Winter Park

$2,700,000

4 Beds ⋅ 3 Baths ⋅ J Kronenberger Sub SubDv. ⋅ 32789 Zip Code

Exquisite, Luxury Listing in the Heart of Winter Park! Stunning, single-story residence, customized and remodeled by Phil Kean Design Group. Open and spacious, 2,600 + SF interior layout which boasts 4 bedrooms, 3 full baths, a home office, living/dining spaces, a chef’s kitchen, and more. Throughout the home are beautiful hardwood floors, beam and coffered ceilings, plantation shutters, French doors, oversized picture windows, and designer accents. The gourmet kitchen features a large island with bar top seating, stone counters, marble tile backsplash, stainless steel appliances, WOLF gas range, SUBZERO refrigerator, dual drawer dishwasher, and walk-in pantry. French doors off the kitchen and living room open to seamlessly blend indoor and outdoor living, leading to a covered lanai that overlooks the meticulously landscaped backyard which includes a relaxing 8-jet spa, trellis garden, grill area, and turf greenspace. The home’s floorplan offers a desirable split-bedroom layout. The primary bedroom has a generously sized en suite with dual sinks, walk-in shower, and walk-in closet with built-in dressers. Each of the other 3 guest rooms are comfortably sized and feature ample closet space. Located just a short drive, walk, or bike ride from Park Avenue, this impeccable home is close to both Interlachen Country Club, the Winter Park Racquet Club, nearby shops and dining, Advent Health, and is zoned for the A-rated Lakemont/Maitland/WPHS school district.

1020 Mayfield Avenue, Winter Park

$430,000

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

Welcome to this beautifully maintained 3-bedroom, 2-bathroom home located in the heart of charming Winter Park! From the moment you step inside, you'll be greeted by an abundance of natural light that fills the space and highlights the beautifully polished terrazzo flooring and fresh interior paint throughout. The open and airy layout creates an inviting atmosphere perfect for both relaxing and entertaining. The kitchen is a true standout—fully remodeled in 2020 and updated with brand-new appliances in 2023. It features a unique and warm aesthetic with Mexican tile countertops and backsplash that add a cozy, artistic touch. The guest bathroom carries a similar charm, also updated in 2020 with a distinct Mexican flair. The spacious primary suite offers a walk-in closet and a beautifully updated en-suite bathroom, complete with a walk-in shower renovated in 2023. Step outside to your fully fenced-in backyard—ideal for pets, outdoor gatherings, or simply enjoying the Florida sunshine. You’ll also find two sheds for additional storage space. Major updates include: New roof (2022) Drain field (2023) Sprinkler system (2023) HVAC system (2024) Water heater (2020) AC ducts (2020) New washer Backyard fence (2023) Brand new LVP flooring in the sunroom (2024) This home truly has it all—charm, character, and modern updates in a fantastic location. Don’t miss your chance to call it yours!

2743 Sanbina Street, Winter Park

$1,800,000

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

Modern living in Central Florida’s desirable Winter Park, this residence offers an elegant balance of refined design, elevated finishes and seamless indoor-outdoor living. Completed in 2021 and impeccably maintained, this two-story home features four generously sized bedrooms, a sun-filled private office, three-and-a-half baths, and an oversized two-car garage, equipped with EV charging, on a quarter acre close to dining, shopping, parks and entertainment. The exterior’s clean architectural profile creates striking curb appeal, while inside, a soaring foyer leads to an open-concept interior appointed with wide-plank hardwood flooring, designer lighting fixtures, custom window treatments, closed-circuit surveillance cameras and a premium integrated surround sound system. The expansive living and dining areas connect effortlessly with a sleek chef’s kitchen featuring professional-grade stainless steel gas appliances, full-height cabinetry and an oversized center island designed for entertaining in the heart of the home. Glass doors at the rear of the house open to a covered lanai and private backyard sanctuary complete with custom pavers, a resort-style graduated-entry pool, mature landscaping and fully fenced, ideal for entertaining or peaceful everyday enjoyment. A grand double-door entry to your first-floor primary suite offers tranquil pool views and a spa-inspired bath with a freestanding soaking tub, zero-entry shower, dual vanities and a custom walk-in closet with integrated storage systems and a private laundry station. Upstairs, three generously sized bedrooms, two elegantly appointed baths, a spacious laundry room and a versatile loft provide privacy and flexibility for guests and the whole family. In Winter Park just moments from A-rated schools, dining, boutiques and including East End Market and Baldwin Park offer additional access to artisan eateries, local shops and parks, this home has it all. Experience the elegance and lifestyle this home offers and reach out today to arrange your private showing.

2813 Northwood Boulevard, Winter Park

$520,000

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

***Premier Land Opportunity on Lafayette Avenue, Winter Park, FL** Take advantage of an exceptional opportunity to own a prime piece of land in the highly desirable area of Winter Park, FL. This 7,734 sq. ft. lot on Lafayette Avenue offers an unparalleled chance to build the custom home of your dreams in one of Central Florida's most sought-after neighborhoods. With generous dimensions and favorable R-1A zoning, this lot is ideal for constructing a spacious custom home. Prospective builders can fully utilize the lot's potential, creating a luxurious residence tailored to modern trends and requirements. Winter Park is a vibrant community known for its rich history and lively present. The area has seen a home appreciation of 23% over the last two years, making it an excellent investment opportunity. It offers the perfect setting for both growing families and professionals seeking a blend of comfort and convenience. Winter Park residents enjoy various amenities, including access to top-notch schools, abundant parks, and a dynamic downtown area filled with shops, Michelin-star restaurants, and cultural venues. The location is also ideal for those looking for a safe, walkable community. Don’t miss this chance to collaborate with our preferred custom home builders to bring your vision to life. Your future of luxury living in Winter Park awaits on Lafayette Avenue. --

2507 Lafayette Avenue, Winter Park

$8,900,000

8 Beds ⋅ 9 Baths ⋅ Green Oaks Rep 02 SubDv. ⋅ 32789 Zip Code

Discover an extraordinary lifestyle at this one-of-a-kind estate, elegantly situated on the shores of Lake Maitland in the distinguished Winter Park area. This remarkable property is unlike any other in the market, seamlessly blending sophisticated Mediterranean and Spanish architectural elements to create a serene and inviting retreat. Upon entering through the stately steel gates, you are welcomed by a picturesque, tree-lined driveway that leads to a formal motor court, enveloped in lush, mature landscaping that ensures complete privacy. Spanning an expansive 2.10 acres with an impressive 217 feet of lake frontage, this estate offers a breathtaking park-like setting that is perfect for both relaxation and vibrant entertaining. The primary residence encompasses six generously sized bedrooms and 6.5 luxurious baths, featuring exquisite traditional custom details and an abundance of elegant living space. Outside, indulge in the stunning waterside rose garden and pavilion, alongside an expansive pool designed for year-round enjoyment and perfect for hosting guests. This estate also boasts a delightful gatehouse, which includes a one-bedroom, one-bath suite and a dedicated two-car garage, providing an ideal retreat for visitors. Additionally, a separate lake house, constructed in 2004, features richly hued wooden vaulted ceilings, a cozy stone fireplace, and a generously sized covered porch that spans the length of the home showcasing spectacular views of the water and gardens. This property transcends the notion of a mere home; it embodies a truly unique lifestyle. Whether you desire serene lakeside tranquility or a sumptuous entertainer's haven, this exceptional offering presents an unmatched opportunity to own a slice of paradise in Winter Park. As you step through the grand double-door entry of the main residence, you are enveloped in elegance and comfort. This thoughtfully designed home balances functionality with style, featuring dual office suites, a game room, and ample storage space throughout, catering to the demands of modern living. The awe-inspiring 22.5-foot ceilings in the grand foyer and dining room create an impressive ambiance, illuminated by uniquely designed windows that flood the space with natural light. The smartly designed floor plan ensures both privacy and convenience, with the primary suite thoughtfully positioned in a secluded area of the home, while an additional main-level bedroom provides flexibility for guests or family. The expansive kitchen is a culinary dream, boasting a spacious island, breakfast bar, a walk-in pantry, and a gas cook range, all seamlessly connected to a cozy dinette area. Upstairs, you’ll find four additional bedrooms and three beautifully renovated bathrooms that prioritize comfort and space. Step outside to an oversized screened and covered lanai, complete with multiple skylights that invite the beauty of the outdoors inside, perfect for relaxation or entertaining. Enjoy captivating views of the pool area, rose garden with Tea House, and tranquil lake, creating an idyllic backdrop for both peaceful moments and lively gatherings. This main residence is a sophisticated blend of luxury and practicality, designed for those who truly appreciate the finer things in life. Don’t miss this rare opportunity to claim this stunning residence as your own—schedule a private showing today to experience the unparalleled elegance and uniqueness of this extraordinary estate!

2001 Bett Mar Lane, Winter Park

$900,000

4 Beds ⋅ 4 Baths ⋅ Cloisters Condo SubDv. ⋅ 32789 Zip Code

Indulge in serene lakefront living from the comfort of two private balconies, each offering views of both the pool and the lake. This expansive, combined residence boasts the most generous square footage of any single unit within The Cloisters. Thoughtfully connected by an interior passthrough, it presents an ideal layout for elegant multi-generational living. Each wing of the home features two spacious bedrooms, two pristine full bathrooms, and a fully appointed kitchen. The property includes two dedicated parking spaces—one thoughtfully equipped with an electric vehicle charging station. Residents enjoy an enviable array of amenities: lakeside seating, private docks, kayak storage, and boat slips exclusively available for lease to residents; well-appointed fitness facilities; secure indoor bicycle storage; and a newly renovated clubhouse complete with a full kitchen, lending library, putting green, outdoor grill station, and a stunning circular pool. All of this is supported by a professional on-site management and custodial team, nestled amid meticulously maintained grounds in a truly exceptional location. This is a rare opportunity to transform the community’s largest residence into a bespoke dream home. Priced to accommodate your vision for renovation.

100 S Interlachen Avenue Unit 304, Winter Park

$360,200

3 Beds ⋅ 2 Baths ⋅ Fairview Heights Rep SubDv. ⋅ 32789 Zip Code

Welcome to this delightful 3-bedroom, 2-bathroom home nestled in the heart of sought-after Winter Park! Bursting with character and charm, this property features original hardwood floors that add warmth and timeless appeal, along with a cozy antique wood-burning stove that brings a touch of rustic elegance to the living space. Plus, an updated bathroom is perfect for visitors. Set on a large lot (.28 acres), the expansive backyard offers endless possibilities, complete with a large outdoor storage shed, detached garage, and a carport combo—perfect for extra storage, a workshop, or even could be reimagined as an accessory dwelling unit. The roof was updated in 2018, offering peace of mind for years to come. Plus, a bonus room can easily be used as an office or for storage. Conveniently located near I-4, this home offers easy access to Orlando’s world-renowned theme parks, stunning Florida beaches, and all the dining, shopping, and entertainment Winter Park is known for. Whether you're a family searching for a great starter home or an investor seeking valuable property in a high-demand area, this home offers incredible potential to make it your own. Don’t miss the opportunity to own a piece of Winter Park charm!

320 Granada Drive, Winter Park

$1,450,000

2 Beds ⋅ 1 Baths ⋅ Virginia Heights SubDv. ⋅ 32789 Zip Code

Sold for Data Purposes Only.

141 W Lake Sue Avenue, Winter Park

$600,000

3 Beds ⋅ 3 Baths ⋅ Lake Knowles Terrace 2nd Add SubDv. ⋅ 32789 Zip Code

Value is in the land.

1550 Palm Avenue, Winter Park

$1,550,000

Cloister Grove Sub SubDv. ⋅ 32789 Zip Code

This is your chance to create the home of your dreams in one of Winter Park’s most sought-after neighborhoods. Situated on an oversized 80 x 180 lot (0.30 acres), this property offers ample space and endless potential. The existing structure has already been removed, making way for a seamless building process.Enjoy a walkable lifestyle with the Winter Park Racquet Club just steps away and the renowned Interlachen Country Club a short drive down the road. Take a leisurely stroll to Park Avenue, home to some of the area’s best restaurants, boutiques, and cultural attractions.Don’t miss this rare opportunity to build your custom home in the pristine and highly desirable Via neighborhood of Winter Park.

1181 Via Capri, Winter Park

$479,000

4 Beds ⋅ 2 Baths ⋅ Lawndale SubDv. ⋅ 32789 Zip Code

Property being sold for lot value. 100 x 140. Zoned R2.

2011 Harmon Avenue, Winter Park

$645,000

3 Beds ⋅ 3 Baths ⋅ Trotters Rep SubDv. ⋅ 32789 Zip Code

Welcome to 796 McIntyre Avenue, Winter Park, FL 32789. This stunning and serene retreat is the ideal place to call home, perfectly situated on a tree-lined brick street within walking distance to Rollins College and all that Park Avenue has to offer. A charming driveway leads to your two-car garage and private front entrance. Upon entering, you'll be greeted by a bright and airy townhome that will instantly impress. The living room features a wood-burning fireplace, soaring ceilings with high windows, and is surrounded by two peaceful patios, bringing in abundant natural light. The updated kitchen offers modern cabinetry, an open breakfast bar, and a delightful eat-in area that opens to a patio. The formal dining room, currently used as a home office, provides access to the second patio, ideal for al fresco dining. Upstairs, you'll find an AMAZING 23x12 primary bedroom with a spacious 20x8 ensuite bathroom. Two guest suites with a Jack-and-Jill bathroom complete the second floor. The owner has meticulously maintained this lovely home, with new patio decks in 2018, a new HVAC, water heater, washer/dryer in 2019, new ceiling fans and refrigerator in 2020, and a new roof and skylights in 2021. Zoned for Audubon K-8 and Winter Park High School. Welcome home!

796 Mcintyre Avenue, Winter Park

$1,450,000

6 Beds ⋅ 5 Baths ⋅ J Kronenberger SubDv. ⋅ 32789 Zip Code

Welcome to your private slice of paradise—a beautifully renovated home with a brand new 2024 pied-à-terre guest retreat, nestled just steps from the iconic Kraft Azalea Garden on the shores of Lake Maitland, and walking distance to the renowned boutiques and dining of Park Avenue. Positioned on a beautiful 0.30-acre lot, this residence is enveloped with manicured landscaping, meandering brick pathways, and outdoor living spaces designed for effortless entertaining. This home captivates with exceptional curb appeal—complete with vibrant florals, a stately new blue front door, and architectural charm. The total square footage is 3784sf with the main home 5 bedrooms/4 bathrooms and 3304sf; the guest retreat is 1 bedroom/1 bathroom with 480sf. Recent updates include new flooring, fresh interior and exterior paint, a renovated kitchen, three new bathroom renovations, almost all new windows, and numerous decorative touches like new crown molding and plantation shutters. The heart of the home features a spacious open-concept layout ideal for entertaining. The living room with an updated gas fireplace flows into the kitchen, which boasts new Bosch appliances, bar seating, a walk-in pantry, and a charming picture window with garden views. The elegant dining space, with 11-foot ceilings and a wall of windows, frames the picturesque backyard. The first floor offers three bedrooms and two full bathrooms, including an en-suite, as well as an office. The second floor includes two large bedroom suites with high ceilings and a laundry room. The upstairs luxurious primary suite impresses with a tray ceiling, cozy fireplace, dual walk-in closets, and a renovated bathroom with granite dual vanities, a freestanding soaking tub, and an oversized walk-in shower. The secondary suite includes its own walk-in closet, spacious bath with double vanities, and a large climate-controlled storage area for ultimate flexibility. Features include French doors, hardwood floors, custom built-ins, crown molding, and plantation shutters throughout. But the crown jewel of the property is the brand-new 2024 detached pied-à-terre—a versatile studio suite with a full bedroom and bathroom, a refreshment area, and a private balcony with tranquil views, ideal as a guest house, executive office, fitness studio, or artist’s retreat. Outdoor living is a dream with a screened brick patio beneath a beamed ceiling, a charming open-air terrace, an enchanting fountain, and complete privacy thanks to a 6-foot concrete wall surrounding the grounds. With ample space to add a custom pool, the possibilities are endless. Located just steps from the 5-acre Kraft Azalea Garden with lakefront trails and a fishing dock, and a short stroll to Park Avenue to enjoy a scenic boat tour or one of the many museums—this is a truly exceptional offering in one of Winter Park’s most sought-after enclaves.

1299 Harding Street, Winter Park

$482,500

3 Beds ⋅ 1 Baths ⋅ Carver Town First Addition SubDv. ⋅ 32789 Zip Code

Bungalow with metal roof approximately one block from Winter Park mall. Considered an excellent location.

710 W Swoope Avenue W, Winter Park

$440,000

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

WINTER PARK 32789 - Mid Century design. Unique neighborhood - walk to shopping, restaurants, entertainment. 3/1.5 Bath with large Florida Room. 2 Car Carport.

3019 Northwood Boulevard, Winter Park

$569,000

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

Welcome home to timeless beauty in the heart of highly sought-after ORWIN MANOR! Imagine living the Winter Park lifestyle where you can stroll to Foxtail Coffee, Publix, Einstein Bagels and other establishments. Jump in the car and you're just minutes from well-known Park Avenue which offers the perfect blend of charm and sophistication—with its tree-lined streets, boutique shopping, art galleries, fine dining, and open-air cafés. Once you step inside this 3-bedroom, 2-bath mid-century charmer, you'll feel the warmth and love of a home that has been truly cared for including a BRAND NEW ROOF. The heart of this home is a stunning open kitchen that’s sure to inspire envy—featuring soaring white cabinetry with glowing underlighting, a sleek gas cooktop, wall oven, and a show-stopping 9-foot quartz island perfect for gathering with friends and family. French doors open to a backyard that feels like a hidden retreat—lined with fruit trees and anchored by a covered, pavered patio perfect for lazy afternoons or lively evenings under twinkle lights. There's even a detached 2 car garage. Original parquet floors bring timeless charm, while the indoor laundry room and walk-in closet add modern-day ease to this vintage gem. Enjoy an easy commute to downtown and quick access to I-4. This is the home you've been waiting for. Call for your private showing today!

1368 Devon Rd, Winter Park

$792,500

3 Beds ⋅ 3 Baths ⋅ Casa Jardin Condo SubDv. ⋅ 32789 Zip Code

Nestled within the tranquil confines of the Virginia Heights neighborhood lies a truly exceptional property that blends luxury, practicality, and location. Boasting three bedrooms and two and a half bathrooms, this residence offers a refined living experience with exclusive access to a private lakefront park—a serene retreat for relaxing or enjoying nature. Recently updated with brand-new luxury vinyl plank flooring throughout, the interior exudes sophistication, from the chef’s kitchen with custom wood cabinetry, granite countertops, and a walk-in butler’s pantry to the thoughtfully designed living spaces illuminated by designer lighting and anchored by an elegant spiral staircase with decorative wrought iron. Residents will appreciate the convenience of walking to the Winter Park Tennis Center, Park Avenue, Azalea Playground Park, and the vibrant Orange Avenue shops and dining. The home also features a private south-facing screened atrium ideal for entertaining or quiet mornings, as well as a spacious rooftop terrace with a heated and cooled bonus room offering endless flexibility. Tucked away from the street for added privacy, the building has recently undergone significant upgrades including a fresh exterior paint job and a brand-new roof. Casa Jardin also provides easy access to Lake Virginia, with amenities like paddle board and kayak storage racks that enhance the active Winter Park lifestyle. This home is a rare opportunity to enjoy elegance, convenience, and tranquility all in one coveted location.

1276 S Pennsylvania Avenue Unit 12, Winter Park

$1,335,000

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

Under Construction. New Construction in the Heart of Winter Park by Nautilus Homes - Introducing an exceptional opportunity to own a brand-new luxury residence by award-winning builder Nautilus Homes, ideally situated between Orlando Avenue and Orange Avenue—just moments from Winter Park’s renowned shops, dining, and cultural attractions. This thoughtfully designed 4-bedroom, 4-bath estate with a private office/den seamlessly blends timeless elegance with elevated modern living. Spanning over 4,000 square feet under roof, every inch of this custom home showcases the finest craftsmanship and luxury finishes. Step inside to be greeted by Creme Brûlée wide-plank wood flooring throughout, setting a warm and inviting tone. The heart of the home is the chef’s kitchen, featuring custom ceiling-height cabinetry, a handcrafted wood range hood, and a stunning Kit-Kat tile backsplash in the adjoining butler’s pantry, perfectly positioned between the kitchen and formal dining room. Entertain effortlessly with a built-in wine and coffee bar just off the expansive living room. The floor plan offers versatility and privacy with one en-suite bedroom and a dedicated office on the main level, while upstairs you'll find three generously sized bedroom suites, each with walk-in closets and refined finishes. Retreat to the primary suite's spa-inspired bathroom, a true sanctuary with a soaking tub, an oversized 9-foot walk-in shower featuring dual sprayers, a frameless glass enclosure, and linear drainage for a sleek, seamless look. Luxury new construction in this coveted Winter Park location at $337 per square foot is virtually unheard of. Don’t miss your opportunity to own a statement home that offers both sophistication and lifestyle. Private tours available by appointment.

1077 Minnesota Avenue, Winter Park

$760,000

3 Beds ⋅ 1 Baths ⋅ Lake Forest Park SubDv. ⋅ 32789 Zip Code

Amazing opportunity to build your dream home in Winter Park.

2838 Wright Avenue, Winter Park

$259,000

2 Beds ⋅ 2 Baths ⋅ Mead Garden SubDv. ⋅ 32789 Zip Code

LOCATION LOCATION!! Now is your chance to own this STUNNING NEWLY RENOVATED 2 bed / 2 full bath FIRST FLOOR condo in the highly desirable MEAD GARDEN COMMUNITY within WALKING/BIKING DISTANCE to Rollins College and the Park Ave Area! This unit was recently renovated to include it's own DEDICATED LAUNDRY CLOSET! (2024) WASHER/DRYER COMBO INCLUDED! NEW ROOF (2022) NEW WATER HEATER (2024) This beautiful condo features an OPEN CONCEPT floor plan with lots of NATURAL LIGHT and UPDATED FINISHES! The bright and airy kitchen features UPGRADED QUARTZ COUNTERTOPS and STAINLESS STEEL APPLIANCES. New DOUBLE PANE & LOW-E WINDOWS (2021) Step through the SLIDING GLASS DOORS out onto your SCREENED PATIO offering GORGEOUS VIEWS of the COURTYARD GARDEN or take a dip in the HEATED COMMUNITY POOL just steps away. FRESHLY PAINTED INTERIOR! There is also a LAUNDRY FACILITY located next to the pool. The community offers DEDICATED BIKE STORAGE, as well as a 3 cubit feet STORAGE AREA FOR EACH UNIT. Each unit has an ASSIGNED PARKING SPACE plus plenty of VISITOR PARKING AVAILABLE! With MEAD GARDENS RIGHT BEHIND THE COMPLEX, you’ll have access to some of the BEST WALKING PATHS in Winter Park. CONVENIENTLY LOCATED between Trader Joe's, Winter Park Village, Ivanhoe Row, and Mills restaurants, and just a short distance to Park Avenue, Winter Park Tennis Center, Seven Oaks Park, and Rollins College. Cats are allowed! This condo won't last long, so call to schedule your private showing today!

1250 S Denning Drive Unit 111, Winter Park

$328,000

3 Beds ⋅ 3 Baths ⋅ Winter Park Oaks SubDv. ⋅ 32789 Zip Code

Welcome home to this beautifully maintained 3-bedroom, 2.5-bath residence in the highly desirable Winter Park Oaks community, featuring 1,500 sq. ft. of inviting living space ideal for both comfort and entertaining. The thoughtfully designed two-story layout includes an open-concept main level with a spacious kitchen flowing effortlessly into a bright family room, convenient downstairs half bath, and easy-care tile and laminate flooring throughout. Upstairs you’ll find all bedrooms, providing a peaceful separation between living and sleeping areas, including a primary suite with private bath and two additional bedrooms sharing another full bath. Recent updates add significant value, including a newer roof (2020) and a brand-new HVAC system (2024). Enjoy ample outdoor living on a generous lot with a fully fenced backyard, plus added convenience from the attached one-car garage housing the washer and dryer. Perfectly situated, this home offers quick access to Winter Park Village, Park Avenue, dining, shopping, and major highways. Don’t miss this exceptional opportunity—schedule your private showing today!

156 Oak Grove Road, Winter Park

$610,000

3 Beds ⋅ 2 Baths ⋅ Capens Add SubDv. ⋅ 32789 Zip Code

Winter Park Beauty located just blocks from the renowned Park Avenue. You will be impressed upon entering the front door of this Recently and Fully Updated 3 Bedroom, 2 Bathroom home while noticing the Open Floor Plan highlighted by gorgeous Porcelain Wood Plank Tile throughout. The expansive windows and contemporary color scheme create a bright and airy atmosphere. The updated kitchen and bathrooms further enhance the modern and welcoming ambience. Other updates from 2022 include the Roof, A/C, Recessed LED Lighting, Electrical, Plumbing, Water Heater, Windows/Doors and more. Sitting on an impressive .21 Acre lot that is fully fenced with a Well for Irrigation, there is plenty of room to create your private backyard oasis. Enjoy easy access to a plethora of options for Shopping, Dining, Movies and Groceries available on Park Ave., the Newly Refreshed Winter Park Village or Hanibal Square. Request your private showing today and make the move to Winter Park.

843 W Swoope Avenue, Winter Park

$1,375,000

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

This home is a charming and meticulously maintained single-story family home nestled on a quiet street located on an expansive beautifully landscaped lot. As you enter, you're greeted by a private office with French doors to the left, and to the right, a cozy family room featuring a decorative fireplace. The open concept living and dining areas overlook the backyard, creating a perfect flow for gatherings. The kitchen, which also overlooks the backyard, features granite countertops, wood cabinetry, and under cabinetry lighting. The home boasts beautiful bamboo flooring throughout most of the living spaces and it has been thoughtfully designed with crown molding and baseboards throughout. A split floor plan offers privacy with the primary suite located on one side of the home. The stunning master bathroom, remodeled in 2024, features a large soaking tub, dual vanities and a walk-in shower. Enjoy the massive walk-in closet with custom built-ins. The primary retreat boasts vaulted wood plank ceilings and French doors which open to the pool area, creating a true retreat. On the opposite side of the home, you’ll find three additional bedrooms, all with built-in closets. The largest of these bedrooms has an ensuite bath, while the other two share a bath with a tub and shower combo. There is also a convenient half-bath off the family room, perfect for guests. The home sits on a spacious, over quarter acre lot, offering a massive backyard oasis complete with a saltwater pool, spa, and a covered patio area perfect for entertaining. The backyard is an entertainer’s dream with a summer kitchen, bar fridge, sink, and wood plank ceiling over the covered patio. The fully fenced yard offers plenty of space for outdoor activities. Additional updates include a 2021 roof, 2021 a/c for primary bedroom, 2024 a/c for main house and exterior paint in 2022, primary retreat and wing added in 2013. The home is located within a highly sought-after Winter Park neighborhood. It's walking distance to Phelps Park and just a short drive to the charming shops and dining on Park Avenue.

1633 Pine Avenue, Winter Park

$575,000

2 Beds ⋅ 1 Baths ⋅ Dixie Terrace SubDv. ⋅ 32789 Zip Code

This charming “old Florida” bungalow in the heart of Winter Park offers the perfect blend of comfort and convenience, nestled in a prime location on a brick lined street just moments from world-class shopping and dining on famous Park Avenue. In addition, it is a short walk to both The Winter Park Village and Whole Foods. The warm and inviting interior of this home exudes character with original hardwood flooring in the spacious living room as well as both bedrooms. The hall bathroom has been updated with a new vanity, granite countertop, and marble tile. The well-appointed kitchen has Italian travertine flooring, Shaker-style 42" wood cabinets, granite countertops with an under-mount sink bowl, and beautiful stainless-steel appliances. Just off the kitchen is a cozy dining room which is perfect for family gatherings. New roof in (2021) and a 1 car garage! The property is zoned for top rated Lakemont Elementary, Maitland Middle, and Winter Park High School. Surrounded by Muti-Million Dollar homes this is a rare opportunity to move in now and wait for future appreciation, add on, or maximize the value of the land and build your dream home. The homes proximity to The Winter Park Cultural Corridor which includes Rollins College, The Morse Museum, The Scenic Boat Tour, and The Farmer’s Market make this a most sought-after location. Schedule your private showing today!

1230 N Denning Drive, Winter Park

$2,935,000

5 Beds ⋅ 6 Baths ⋅ Gibbs Sub SubDv. ⋅ 32789 Zip Code

One of Winter Park’s iconic and cherished homes, just a short distance from Park Avenue. On one of the most picturesque, brick-lined streets in downtown Winter Park, this extraordinary residence is a rare opportunity to own a piece of the city’s rich architectural history, fully reimagined with modern elegance and thoughtful design. On the same city block as the Alfond Inn and a two-block stroll to the world-renowned Park Avenue, this home offers not only luxurious living but an unparalleled lifestyle in one of Central Florida’s sought-after communities. Park Avenue is the heartbeat of Winter Park, a tree-lined promenade brimming with charm, home to award-winning restaurants, boutique shopping, art galleries and cultural landmarks. Residents and visitors alike are drawn to its timeless ambiance, where the rhythm of the day flows from morning coffee at a corner café to evening dinners under twinkling lights. Whether enjoying “Movies in the Park,” seasonal art festivals, the lively Winter Park Farmers’ Market or beloved holiday parades, living here means having a front-row seat to all of Winter Park’s treasured traditions. Originally built in the 1930s, this five-bedroom, 5.5-bath home has been meticulously renovated in recent years to preserve its historic character while seamlessly incorporating every modern convenience. From the moment you enter, you’re greeted by gleaming hardwood floors, classic architectural details and a warm, inviting atmosphere. The gracious living room centers around a charming fireplace, flanked by two sets of French doors that lead to a cozy sunroom, ideal for morning coffee or afternoon reading. A formal dining room provides an elegant setting for entertaining, while the open-concept kitchen and family room encompass a blend of functionality and style. The kitchen is a showpiece, featuring a large 15-foot Soma quartz island and countertops and marble backsplash, handcrafted cabinetry, top-of-the-line Wolf and Sub-Zero appliances, and a custom wet bar with under-counter wine refrigerator. It’s a space designed for gatherings, large or small. The expansive and private primary suite is on the main level and features a walk-in closet with custom built-ins and a luxurious en-suite bath with dual sinks and a marble/glass shower. Upstairs, you’ll find three additional bedroom suites, including one that could easily serve as a second primary suite, complete with French doors leading to a covered balcony. Each bedroom offers its own en-suite bath, hardwood floors and thoughtfully designed closet space with built-ins. A spacious first-floor laundry room offers ample storage, while the detached two-car garage includes a beautifully renovated first-floor guest cottage. Complete with a kitchenette, full bath, and cedar-lined walk-in closet, it’s the ideal space for guests, a home office or extended family. Surrounded by lush landscaping and a charming circular driveway, this home radiates curb appeal and classic Winter Park style. Whether you're walking to Park Avenue for dinner, enjoying a leisurely afternoon in Central Park, or simply soaking in the historic beauty of your neighborhood, this home places you at the center of it all. This is more than just a home, it’s a lifestyle and a rare chance to own one of Winter Park’s rare downtown area treasured properties.

266 Chase Avenue, Winter Park

$550,000

4 Beds ⋅ 3 Baths ⋅ Dommerich Hills Fourth Add SubDv. ⋅ 32789 Zip Code

Location, Charm, and Potential! Presenting a rare opportunity to own a home in one of Winter Park's most prestigious zip codes, offering the perfect blend of classic elegance and future potential. This 4-bedroom, 2.5-bathroom pool home is ready for your personal touch and vision. Nestled on a large corner lot in a highly sought-after neighborhood, this home features timeless charm and all the structural bones you need to create your dream living space. As you approach the home via the charming brick-paved walkway, step inside to a welcoming foyer. The spacious formal living room is bright and inviting, showcasing a marble wood-burning fireplace and French doors that lead out to the backyard—perfect for entertaining. Adjacent to the living room, the formal dining room offers ample space for large gatherings and dinner parties. The kitchen provides plenty of storage and potential to become a chef’s paradise, with generous cabinetry and counter space. Overlooking the cozy family room with parquet flooring, the space is ideal for relaxing, watching movies, or enjoying family game night. The bedrooms offer privacy and comfort, with the primary suite serving as a peaceful retreat. The spacious primary bedroom features ample closet space and an ensuite bathroom with double sinks, a private water closet, and a walk-in shower. Additional highlights include hurricane windows installed just five years ago, offering peace of mind and letting natural light flood the space. Timeless terrazzo flooring can be found throughout the home. The backyard is a private oasis, with mature landscaping and a well-maintained pool—perfect for relaxing or entertaining guests. Located just minutes from Winter Park’s renowned Park Avenue, with its upscale shops and dining, this home is an exceptional find. Don’t miss out on the chance to invest in a home with incredible potential in one of Winter Park’s most desirable neighborhoods! ROOF - 3/2025 (brand new!), HVAC 2010, ELECTRICAL - 2022 **WE ARE ACCEPTING ANY AND ALL OFFERS THROUGH 9AM MONDAY APRIL 7, 2025.***

2906 Rapidan Trail, Winter Park

$1,250,000

5 Beds ⋅ 6 Baths ⋅ Galloway Place Rep SubDv. ⋅ 32789 Zip Code

Discover luxurious lakeside living in prestigious Winter Park, where this extensively updated pool home offers the perfect blend of sophisticated main residence and private guest cottage. Just minutes from Park Avenue's renowned shopping and dining, this property provides coveted access to Lake Osceola, creating an ideal setting for the Florida lifestyle. The main residence showcases elegant living spaces, including a grand room with hardwood floors and a welcoming fireplace. The gourmet kitchen is a chef's dream, featuring premium Wolf and Sub-Zero appliances, gleaming granite countertops, and a distinctive bead-board center island that opens to a spacious family room. A wall of French doors in the formal dining room creates seamless indoor-outdoor flow to the screened pool and spa area. The thoughtful floor plan includes a downstairs master suite with custom walk-in closet, dual-sink bathroom, and versatile 13x12 flex space. Two additional en-suite bedrooms upstairs provide comfortable accommodations for family or guests. The separate guest cottage adds tremendous value with two bedrooms, a full kitchen, and bathroom – perfect for long-term guests or home office. Recent updates ensure peace of mind: new roof (2025), two new AC units (2023), complete replumbing (2015), and updated electrical. The property offers abundant parking with a two-car garage plus an additional one-car garage with full bath. Located in Winter Park's prestigious school district, this home represents the perfect combination of luxury, convenience, and long-term value.

1370 Alberta Drive, Winter Park

$3,845,000

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

Lake Maitland Custom built home.

2020 Venetian Way, Winter Park

$1,885,000

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

Stunning new Winter Park residence.

2144 Sycamore Drive, Winter Park

$1,295,000

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

Nestled in one of the most sought-after locations, the “Tree Streets” of Winter Park. 1601 Chestnut Avenue is a stunning Modern European Cottage-style home, built in 2017, that masterfully blends classic charm with modern finishes. Offering over 2,800 square feet, this pool home includes: four bedrooms, three full baths, and an over-sized loft. Step inside to hard wood flooring, complemented by upgraded baseboards and crown molding throughout. The formal dining room, also functional as a formal seating area, or office space, is complete with a pass-through bar, flows seamlessly into a chef’s kitchen—featuring a Viking appliance package, a 48” gas range, quartz countertops, an extended bar-top island, and floor-to-ceiling cabinetry. The white cabinetry is solid wood, soft-closing and includes custom pull-outs. The island comfortably seats 5 barstools, and flows seamlessly into the breakfast nook. The great room is a true showpiece, with a stone gas fireplace and a stunning 12 foot tongue-and-groove wood ceiling. Natural light floods the space from the large sliding glass door, and windows to the vaulted ceiling, adding to the open concept floor plan and how spacious it feels. The first-floor primary suite, is situated at the back right of the home, with direct lanai access, and large picture windows overlooking the private pool. The hallway to the en-suite includes dual walk-in closets, with solid wood built-ins. The en-suite features a water closet, an oversized two-sided walk-in shower, and a vanity with dual sinks and quartz countertops. Step outside to the lanai, where a beach-entry pool and spacious covered lanai, complete with the same vaulted tongue and groove ceiling as seen inside. This continuous feature is a statement in the home. The lanai is finished with a travertine deck and gas line hookup. Rock landscaped beds, lush landscaping and a fully fenced yard, complete the back yard, making the perfect space to entertain. The main level also features a guest bedroom and full bathroom, with a frameless glass shower. Next to this bedroom is also access to the two-car garage and a conveniently positioned laundry room. Upstairs, a bonus room with vaulted ceilings (22’ x 14’) provides endless possibilities—ideal for a home theater, office, or playroom. Two additional bedrooms and a full bath complete the second level. Both bedrooms offer walk-in closets. The full bathroom includes a large vanity with quartz countertops, and a tub and shower combination. Additional features of this home, include: newly installed lighting fixtures throughout, a paver driveway, covered front porch, and a two-car garage. The two-car garage was recently finished with custom flooring and custom built-ins to maximize the functionality and storage space in the garage. This exceptional home is just moments from Park Avenue, Winter Park Village, Whole Foods, and beautiful neighborhood parks and lakes. A location like no other, call today to schedule your private tour.

1601 Chestnut Avenue, Winter Park

$1,025,000

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

Welcome to your Winter Park dream home—a modern farmhouse masterpiece blending timeless design with contemporary comforts. Built in 2019, this single-family home offers four spacious bedrooms, two and a half baths, and luxurious finishes you'll cherish for years. Nestled between the highly coveted areas and school zones of College Park and Winter Park, this property is an opportunity you can't miss. Step into the foyer, leading to a bright, open-concept living space and a kitchen that’s designed to impress. Featuring quartz countertops, sleek stainless appliances, shaker cabinetry, and a wine fridge, this kitchen is perfect for both everyday living and entertaining. The living area transitions smoothly into the expansive fenced backyard, complete with ample space for a future pool. Upstairs, you'll find all four bedrooms, including the stunning primary suite with hardwood floors, a custom walk-in closet, and a spa-like bathroom with dual sinks. A versatile loft, laundry room, and additional full bathroom complete the second floor. Enhancing its charm are plantation shutters throughout and proximity to the serene Dubsdread Golf Course—a perfect spot for morning jogs or evening strolls. Enjoy the ease of accessing all that College Park and Winter Park have to offer, as well as convenient commuting via Interstate-4. There is no HOA in this community. This home is available immediately.

2680 Oglesby Avenue, Winter Park

$840,000

4 Beds ⋅ 3 Baths ⋅ Killarney Estates SubDv. ⋅ 32789 Zip Code

Location! Location! Location! A modern, newer build in a perfect location in the heart of Winter Park with views of Lake Killarney. This 4 bedroom, 3 full bath property is ready for you to call it home. Upon entering, you'll be welcomed with tall ceilings, gorgeous dark hardwood floors and a formal dining room to your left. Towards the rear of the home, you'll find a spacious great room and an open gourmet kitchen- perfect for entertaining. No expense was spared for the chef in the family- custom cabinetry with under cabinet lighting, stainless steel appliances, quartz countertops and a hidden walk in pantry. Around the corner, you'll find a full bed and bath on the first floor, perfect for guests or older parents. Upstairs are the remaining primary bed + 2 other beds and a full bath. The primary suite has ample room for a king sized bed, a HUGE walk in closet, drop zone space, and a gorgeous bath suite featuring a separate soaking tub and walk in shower. The best part of this home is it's location. Winter Park Village, Hillstone, Mills District, Park Ave and access to the I-4 are all a skip and hop away. Easy to see. Call/Text for a private showing today.

440 Shoreview Avenue, Winter Park

$292,000

3 Beds ⋅ 1 Baths ⋅ Dubsdread Heights SubDv. ⋅ 32789 Zip Code

Cute one-story Craftsman bungalow in the Dubsdread area of College Park. This home has great potential to shine—bring your tools and make it your own since the price is right. Step through the front door into your charming Florida Room, filled with natural light. The inviting family room features a wood-burning fireplace and what appears to be original oak wood flooring. The kitchen has a traditional feel—light and bright with painted cabinets. The garage is in the backyard, and a long driveway provides you and your guests with plenty of parking space. You can enjoy the backyard from the covered back porch. This home will need some repairs or renovations, as it has aged over time. If you're looking to build, this homesite is 50 feet wide by 140 feet deep. The location is close to Aloma in Winter Park, making it easy to access all the hotspots in Winter Park, College Park, Dubsdread Golf Course, and AdventHealth Hospital. A great opportunity for first-time buyers, builders, or investors looking to buy smart and improve the asset.

712 Baffie Avenue, Winter Park

$799,000

Parklando 03 SubDv. ⋅ 32789 Zip Code

Amazing opportunity to build your dream home in Winter Park. A tremendous location with just a short stroll to East End Market and all the shops and restaurants Corrine Drive has to offer! Zoned for the Audubon K-8 school that you can also walk to! This lot is over a 1/4 of an acre and is tucked away at the end of a dead end street for privacy. This is one you don't want to miss!

2320 Janice Avenue, Winter Park

$2,300,000

4 Beds ⋅ 4 Baths ⋅ Lake Forest Park SubDv. ⋅ 32789 Zip Code

PRESENTING THE NEWEST WINTER PARK RESIDENCE BUILT BY M. LAHR HOMES! Just completed, this stunning custom level home has come together perfectly with design and finish features that have to be seen in person to be truly appreciated. The combination of a fantastic floor plan that integrates perfectly with the expansive covered outdoor patio/pool/spa/outdoor space makes this house feel nothing less than a resort. This entire outdoor area is an incredible natural four (4) season extension of the interior living space! The home boasts an unparalleled combination of function, elegance and aesthetics. Simply....more detailed, functional, and higher quality than typical Winter Park new construction. The prominent, timeless, and elegant features of this home's exterior are the first taste of the professional design and the experience continues once entering and touring this home and property. Please see floor plans included in photos and CLICK ON TOUR LINK FOR A COMPREHENSIVE VIDEO WALK THROUGH TOUR. Located in a great Winter Park location in the highly desirable Audubon K-8/Winter Park High School District. Minutes to DT Orlando, Baldwin Park, DT Winter Park, WP Park Ave. Shopping, Winter Park Village, Advent Health Village, Orlando Regional Medical Center, Lake Highland Prep., and more. One of Central Florida's most dynamic areas! You will not find a better opportunity to secure a recently completed, highly detailed, unique luxury home in the WP area that offers the feel, presentation, and function of 2814 Parkland Drive.

2814 Parkland Drive, Winter Park

$2,220,000

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

Contemporary Lakefront Estate in Winter Park! Nestled along the serene shores of Lake Berry, this spacious single-story, 4-bedroom, 3-bathroom home offers a perfect blend of comfort and natural beauty. With expansive living spaces bathed in natural light, this home invites you to experience relaxed lakefront living at its finest. Offering over 2,600 sf of luxurious living space, the open-concept layout allows for an expansive great room with large sliding doors that frame breathtaking lake views and create an airy and inviting atmosphere. Recently updated to include enhanced finishes that compliment the homes modern aesthetic, the neutral tile floors, vaulted ceilings and glass tile fireplace reflect the home’s cool tones. A sophisticated kitchen with white cabinetry and granite counters is a chef’s dream with its large island and high-end Viking appliances and gas-range. An oversized primary suite overlooks the water and has a private en suite with a double-sink vanity, step-in shower, and walk-in closet. With a coveted split-bedroom layout, 3 guest bedrooms, each comfortably sized, and with ample closet space, and two full baths are located at the opposite side of the home. Step outside to your private oasis, where a sparkling pool awaits. The backyard is well-suited for enjoying Florida’s sunny weather year-round and for hosting gatherings with friends and family. The fenced yard keeps the backyard nice and private, while also providing unobstructed views of Lake Berry. A docks with covered boathouse and lift is perfect for storing a boat or wave runner or jet skis. Located within one of Winter Park’s quiet and charming neighborhoods, this home offers an incredible opportunity to live on one of Winter Park’s pristine waterways and is just a short distance to Park Avenue, Baldwin Park, Advent Health, Rollins College, and many other nearby businesses. Zoned for the Brookshire/Glendridge/WPHS school district and within 15 mins of Orlando’s top private schools. Don’t miss the opportunity to tour this home – schedule your showing today.

673 Balmoral Road, Winter Park

$1,810,000

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

Experience modern luxury in this stunning custom-built residence by LunDev Custom Homes, positioned in the heart of Winter Park. Built in 2015, this contemporary home offers four bedrooms, 3.5 baths and 3,440 heated square feet, seamlessly blending elegant design with state-of-the-art smart home technology. The first-floor primary suite is a serene retreat featuring a spacious walk-in closet and a spa-like en-suite bath with dual sinks, a glass-enclosed shower, a separate soaking tub and a private water closet. The formal living room is highlighted by French doors opening to a beautifully designed side yard with low-maintenance artificial turf, creating an indoor-outdoor flow. At the heart of the home, the open-concept kitchen is a chef’s dream, boasting a large island that overlooks the dining and family rooms, ideal for everyday living and entertaining. A dramatic wall of glass doors seamlessly extends the living space to the covered lanai, complete with motorized screens for year-round enjoyment. Recent upgrades, including fresh interior and exterior paint, Philips Hue smart lighting, smart wall switches and new smart locks, enhance style and convenience. Step outside to your private resort-style oasis, where a sparkling pool, built-in gas grill, ceramic Coyote Asado smoker and pergola-covered seating area set the stage for unforgettable gatherings. An outdoor shower and a lush Vistafolia artificial green wall system, illuminated by Philips Hue backlighting, add to the ambiance. A covered walkway connects the home to a detached two-car garage, offering functionality and architectural charm. Upstairs, a versatile bonus room/loft with gym flooring provides endless possibilities, accompanied by three additional bedrooms, two featuring walk-in closets and one with dual closets and an en-suite bath. Additional enhancements include a Ring security system, a new pool filter and skimmer, and upgraded front yard landscaping, ensuring this home is move-in ready. Just minutes from downtown Winter Park’s Park Avenue, Baldwin Park Village Center, and premier dining and shopping, with easy access to downtown Orlando and Orlando International Airport, this residence offers the ideal balance of luxury, comfort and convenience. Don’t miss this opportunity and schedule your private showing today!

1970 Laurel Road, Winter Park

$235,000

1 Beds ⋅ 1 Baths ⋅ Winter Park Gardens Condo SubDv. ⋅ 32789 Zip Code

Welcome to your serene retreat in the highly desirable Winter Park Gardens community. This beautifully renovated second-floor 1-bedroom, 1-bathroom condo offers an exceptional living experience with modern upgrades and a prime location less than a mile from Park Avenue and Orlando Avenue. Step inside to discover luxury vinyl flooring throughout the entry, living space, and kitchen, complemented by granite countertops, a double oven, a custom-built pantry, and pull-out drawers for added convenience. The open-concept living space extends into a Florida sunroom with floor-to-ceiling sliding windows that double as sliding doors, allowing fresh air to flow through your home. Whether you're in the living room, kitchen, or bedroom, you'll enjoy breathtaking views overlooking the oasis of the lushly landscaped courtyard, pool, tranquil community pond, and beautiful trees. Further down the hall, you'll find new carpeting in the primary bedroom, along with upgraded plantation shutters to the window. Storage is a breeze with custom closets throughout, including a stunning primary closet hidden behind bi-fold doors, offering ample, organized space for all your belongings, along with an elegant entrance hallway closet and a spacious linen closet. The renovated bathroom features a walk-in shower with handicap assistance, thoughtfully designed for ease of use and comfort. Nestled on over 8 acres of meticulously maintained grounds, Winter Park Gardens is a vibrant 55+ community. Residents enjoy a resort-style pool, clubhouse, and lighted walking paths winding through the lush gardens and a bridge overlooking the serene pond views. With assigned parking and ample guest spaces, convenience is never an issue. This prime location places you just minutes from Rollins College, Azalea Tennis Center, and Mead Botanical Gardens, while Downtown Orlando, Baldwin Park, and major highways provide easy access to everything in Central Florida. Additionally, you’ll find an array of top-tier local shops and restaurants nearby, as well as convenient everyday services such as hair salons, grocery stores, and more—all just moments from your doorstep.

700 Melrose Avenue Unit L-23, Winter Park

$3,600,000

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

Nestled on a sprawling 0.89-acre estate, this luxurious home offers the perfect balance of privacy and convenience, just moments from the vibrant downtown Winter Park. A rare gem, this 1935 James Gamble Rogers masterpiece blends Old World charm with European influences, creating an inviting, character-rich ambiance. The main home features 3 bedrooms, 2 1/2 bathrooms, and 3,908 square feet of elegant living space, complemented by a 1-bedroom, 1-bathroom guest cottage, adding 406 square feet, for a total of 4,314 square feet. Accessed via a long, secluded driveway, this estate seamlessly blends indoor and outdoor living with lush gardens, expansive courtyards, and tranquil patios. Inside, arched doorways, reclaimed doors, and rounded stucco walls evoke a Santa Barbara Mediterranean feel. The kitchen is outfitted with stainless steel appliances, granite countertops, and a butler’s pantry—ideal for entertaining. The formal dining room opens to a living room with a curved barrel ceiling, a fireplace, and French doors leading to a garden patio. A sunlit sunroom offers panoramic garden and pool views, perfect for relaxation. The expansive downstairs owner's suite features vaulted ceilings, French doors to the patio, a cozy fireplace, and a lavish marble bath with a Jacuzzi tub, double sinks, and a dressing area with custom cabinetry and two large walk-in closets. Upstairs, two bedrooms share a beautifully renovated marble bath. The detached 2-car garage is adjacent to the laundry room, while the guest house offers a studio layout with terra-cotta floors, a kitchenette, a full bath, and French doors overlooking the pool. The backyard is an oasis of tranquility with a stunning resort-style pool, an expansive patio, and lush landscaping, providing ultimate privacy. This home offers the best of both worlds: a rare opportunity to own a piece of Winter Park history, yet lovingly maintained with modern updates and conveniences throughout.

851 Georgia Avenue, Winter Park

$375,000

2 Beds ⋅ 1 Baths ⋅ Olympia Heights Annex SubDv. ⋅ 32789 Zip Code

Come build your dream home on this oversized single family corner lot (62.5 by 141.5) in Winter Park Florida with amazing views of Dubsdread Golf Course hole 6. Located just a short drive or walk away from all your favorite shops and restaurants (Agave Azul, Publix, Tap Room, Black Bean Deli) Convenient access to I-4 making it easy to get around the greater Orlando area. Less than a minute drive to Park Maitland School and zoned Princeton Elementary School. The existing single family structure is being offered as is and the owner has no previous information on the home. Demolition date is now scheduled for 4/24/2025. 20k impact fee credit/verify exact when pulling new permit

2259 Minnesota Avenue, Winter Park

$2,594,550

3 Beds ⋅ 3 Baths ⋅ Sylvan Lake Shores SubDv. ⋅ 32789 Zip Code

Experience modern elegance in this stunning Lake Sylvan estate with breathtaking lake views and seamless indoor-outdoor living. The open-concept design features a gourmet kitchen (renovated 2023) with quartzite countertops, a wet bar, and luxe appliances. French doors, a custom gas fireplace, and designer lighting add refined charm to the living room. Step outside to nearly 1500 sqft of additional living space on the lake featuring a heated pool, spa, covered patio with gas fireplace, summer kitchen and lakeside firepit. With three bedrooms and a versatile office (easily a fourth), this home adapts to your needs. The first-floor primary suite opens to the pool, while an upstairs primary suite has dual custom closets, a spa-like bath, and a private flex space. Upgrades include a new roof with gutters and gutter guards (2022), new water heaters (2023), interior paint (2021) exterior paint (2023), water filtration, system, dual propane tanks, security system, plantation shutters, and three AC units. The above garage attic is accessible by staircase and can easily be enclosed to make a 5th bedroom, game room or flex space. This lakefront sanctuary offers privacy, sophistication, and modern convenience plus is located just minutes from Park Avenue's charming shops and restaurants. Don’t miss the opportunity to make this lake front home yours. Schedule your private showing today!

254 Sylvan Boulevard, Winter Park

$520,000

3 Beds ⋅ 2 Baths ⋅ Orange Grove Sub SubDv. ⋅ 32789 Zip Code

Under contract. Listing agent is the owner.

1810 Taylor Ave, Winter Park

$850,000

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

Stunning fully remodeled Winter Park bungalow featuring a 500 square foot detached guest house. This charming residence is perfectly positioned on a rare oversized .41-acre double lot and has been completely transformed, offering a harmonious blend of modern luxury and timeless elegance. The main house features 4 bedrooms and 2.5 baths while the guest house features a living room, bedroom, kitchenette, and a full bathroom. Step inside and you are immediately greeted by a bright, spacious open floor plan. Designed for effortless entertaining, this home features a sleek modern wet bar complete with an under counter ice maker, additional dishwasher, and wine fridge! The gourmet kitchen is a true masterpiece, featuring top-of-the-line stainless steel appliances, upgraded countertops, a walk-in pantry, a large butcher block center island, tile backsplash, and loads of custom cabinetry. There is even a pass-through window to a bar area on the covered lanai. The luxurious primary suite provides a serene escape, designed as a private retreat where you can unwind in ultimate comfort. It boasts an impressive closet and a spa-inspired en-suite bath, complete with a freestanding soaking tub, dual vanities, and a spacious walk-in shower. Outside, the home continues to impress with its private backyard oasis provided by the rare double lot. A sparkling screened in pool, set against lush landscaping, serves as the centerpiece of the expansive patio area. In addition, the beautifully landscaped yard holds a custom fire pit, elevated covered wooden lanai and garden boxes to create the perfect setting for relaxation and gatherings. There is also a spacious covered deck, and a large storage shed. Last but not least, your guest will love the privacy provided by the detached guest house overlooking the pool. Jump on your golf cart and within minutes you’re transported to Park Ave, with its amazing shops, fine dining, and everything else that Winter Park has to offer. Don't miss the opportunity to make this unique Winter Park home yours!

1832 Magnolia Avenue, Winter Park

$2,910,000

4 Beds ⋅ 6 Baths ⋅ Stonehurst Estates SubDv. ⋅ 32789 Zip Code

Set on a sprawling half-acre, surrounded by meticulously manicured landscaping, this custom-built traditional estate exemplifies refined luxury, modern convenience, and an unparalleled lifestyle. The red brick façade, covered porches with glass doors, and gated side porte-cochere set a timeless tone, while two-story fluted columns add stately elegance. Inside, classic architectural details merge with modern design, highlighted by two-story coffered ceilings, intricate millwork, and expansive windows and French doors that flood the home with natural light. Thoughtfully designed for both entertaining and everyday living, the gourmet kitchen includes a 6-burner Viking gas cooktop, double dishwashers and sinks, a paneled refrigerator and separate full-sized freezer, a walk-in pantry, and an oversized island with breakfast bar seating. The first floor features a private primary retreat, two powder rooms, a workstation/mudroom accessible off the porte-cochere, and one of two laundry rooms. Upstairs offers three spacious bedroom suites with walk-in closets, a versatile bonus room, and a second laundry room. Embrace the Florida lifestyle from a two-story covered brick patio with a built-in gas grill, overlooking the private, fenced-in backyard oasis and breathtaking saltwater pool and heated spa, all elevated by a three-tier fountain and fire pit area, and wrapped in lush landscaping; this outdoor space is truly magical and not easily replicated in Winter Park! A circular driveway provides ample parking, while a gated side drive leads to an oversized, detached three-car garage with a bonus room above—ideal for a gym or studio. This particularly grand, wide street in the City of Winter Park is something truly special. Ideally located near Baldwin Park, Corrine Drive, and Park Avenue, and zoned for highly regarded Audubon K-8, this estate is more than a home—it’s a statement in timeless elegance. *Ask for a list of improvements, the floorplan and click on the virtual tour!

1911 Stonehurst Road, Winter Park

$540,000

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

Situated in a prime location, this condominium presents an excellent opportunity for customization and renovation. Sold as-is, this residence offers a spacious layout with ample potential to reimagine its interiors to suit modern living. Positioned within The Cloisters sought-after community, residents enjoy access to desirable amenities and a convenient setting near shopping, dining, and local attractions. A rare chance to transform and tailor a space to individual preferences.

100 S Interlachen Avenue Unit 415, Winter Park

$1,395,000

Comstock Park SubDv. ⋅ 32789 Zip Code

AMAZING opportunity to build your new home in this phenomenal neighborhood! The existing home is a tear-down and the value of the property lies in the expansive 13,441 sf (.31 Acre) lot. With this tremendous 100 ft wide lot, the property affords any new buyer ample space to build their dream home. Plus, the locale is ideal...Tucked away on a charming, quiet brick street, the property is an easy stroll to Phelps Park and the Y. Plus, you are a short ride to Downtown Park Avenue's shops and restaurants. This is an opportunity not to be missed! SOLD AS-IS.

1560 Lakehurst Avenue, Winter Park

$825,000

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

Discover modern living at its finest in this stunning contemporary home in the heart of Winter Park! Built in 2020, this spacious four-bedroom, 2.5-bath residence offers over 2,500 square feet of beautifully designed living space ideal for families of all sizes. The first floor features a bright, open-concept kitchen with sleek finishes, a large island and ample storage, seamlessly flowing into a spacious living area, and ideal for family gatherings and entertaining. Upstairs, the luxurious primary suite offers a private retreat with a large en-suite bath, while three additional bedrooms provide plenty of space for guests, or a home office. At top of the stairs, you'll find a versatile loft space, ideal for a playroom, media area or additional lounge. Step outside to enjoy the expansive backyard, complete with a large privacy fence, offering plenty of space for families and pets to play or to host outdoor gatherings. This home is in a prime location, only a short distance to Dubsdread Golf Course. It’s also just minutes from Park Avenue, College Park and downtown Orlando, offering easy access to dining, shopping and entertainment. Plus, with quick access to Interstate 4, commuting anywhere in Central Florida is effortless. This home is a rare find. Don’t miss your chance to make it yours, schedule your showing today.

705 Baffie Avenue, Winter Park

$412,000

2 Beds ⋅ 2 Baths ⋅ Andalucia Apts SubDv. ⋅ 32789 Zip Code

Location, Location, Location - downtown Winter Park condo for under $500K! This dramatic 2 bedroom - 2 Bath ground floor unit is located on corner of Swoop and Interlachen, steps from the Winter Park 9 Golf Course and Park Avenue! Beautiful views, glassed in porch overlooking stunning landscape. This unit offers high ceilings, open, updated kitchen to living areas, sunroom (enclosed porch) large primary suite and guest room. Two full baths. Large utility room. Designer lighting. Open floor plan, light and bright! A/C 2018. The charming Andalucia complex, which consists of only 20 units, offers access to a lovely covered patio downstairs, an elevator, courtyard, and a community laundry room. The community also provides a private storage room for this unit. The roof was replaced in 2024. The exterior was painted, and new gates were installed in 2018. One covered parking space is included. Additional guest parking is available in the rear. The condo fee covers water, sewer, Spectrum WiFi and cable TV, landscaping and exterior maintenance, garbage, insurance on the exterior building, and reserves. Please note: No pets or rentals allowed. Call today for your private viewing of this special unit.

535 N Interlachen Avenue Unit 107, Winter Park

$3,200,000

5 Beds ⋅ 5 Baths ⋅ Kenilworth Shores Sec 01 SubDv. ⋅ 32789 Zip Code

Located in the heart of Winter Park this exquisite modern residence built by Vimaro Homes features almost 5,000 square feet of luxury living space. As you step through the glass front doors, you’re immediately greeted by the grandeur of the marble entry floors and custom archways, setting the tone for the exceptional finishes throughout this stunning home. From the gorgeous wood floors laid in a herring bone pattern, to the designer light fixtures, arched doorways, and beautiful mill work, no expense was spared in the construction of this remarkable residence. The chef’s kitchen features exquisite custom cabinetry, marble countertops, a massive butler’s pantry, top of the line appliances including a ILVE Nostalgie range, and a wine cellar. The great room features a wall of glass that opens to the spacious covered lanai blending the indoor and outdoor spaces. The primary bedroom suite overlooks the private back yard and features a spa bath that would rival even the most prominent spas. Last but not least there is a massive walk in closet with separate his and hers sections, and a washer and dryer. Additional features include a first-floor game room, home office, formal dining room, a second floor loft area, 4 additional bedrooms, and second floor laundry room. Situated on a spacious lot, this property features a circular driveway, and a large, fenced yard with mature landscaping, perfect for outdoor activities and entertaining. The highlight of this home is the inviting pool, providing a refreshing oasis for those hot summer days. Jump on your golf cart and within minutes you’re transported to Park Ave, with its amazing shops, fine dining, and everything else that Winter Park has to offer. Don’t miss your opportunity to own this stunning Winter Park home crafted by renowned builder Vimaro Homes.

1833 Loch Berry Road, Winter Park

$580,000

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

Discover the perfect blend of classic charm and modern potential in this delightful single-family home with endless possibilities, nestled in a prime Winter Park location! This inviting fully fenced home features a comfortable layout with 3 bedrooms and 1 bathroom in the main living area. An exciting attached addition has a separate entrance leading to a spacious 4th bedroom and 2nd bathroom, providing incredible flexibility for your lifestyle. Imagine the possibilities: a private in-law suite, a dedicated home office, or a fantastic game/play room – the choice is yours! This blank slate is ready for your personal touches and creative vision, allowing you to transform it into your dream home. Step inside to find a light-filled interior boasting higher ceilings in the living and dining rooms, creating an airy and welcoming atmosphere.Natural sunlight streams through the windows, highlighting the durable and updated laminate flooring – no carpet here! The kitchen is equipped with newer appliances and classic wood cabinets, ready for your culinary adventures. Recent updates include a new AC unit (2024) ensuring year-round comfort, and a roof that’s only 10 years old, providing peace of mind. Outside, a generously sized, fully fenced yard offers the perfect setting for gatherings, barbecues, and outdoor enjoyment. Don't miss this incredible opportunity to own a versatile and well-located home, walking distance to Baldwin Park, access to top-rated schools, premier shopping, and major roadways. This is your opportunity to own a piece of Winter Park paradise, combining a sought-after location with versatile living options. Don't miss out and schedule your private tour today!

3006 Northwood Boulevard, Winter Park

$478,000

2 Beds ⋅ 2 Baths ⋅ Fairbanks Shores 4th Add SubDv. ⋅ 32789 Zip Code

FSBO

2877 Euston Road, Winter Park

$1,500,000

4 Beds ⋅ 3 Baths ⋅ Conwill Estates SubDv. ⋅ 32789 Zip Code

Nestled in the heart of Winter Park, this stunning 4-bedroom, 3-bathroom pool home offers the perfect balance of elegance and convenience. Just minutes from shopping, fantastic dining, popular Phelps Park, the YMCA, the renowned Interlachen Country Club, and the lively Park Avenue, this location has it all. As you approach, a charming front porch shaded by majestic oak trees welcomes you home. Step inside to discover a beautifully designed main floor, featuring a formal dining room, a versatile office space, and a kitchen that effortlessly flows into the family room. The kitchen is every chef’s dream, with gorgeous granite countertops, premium stainless steel appliances, a large breakfast bar, and a cozy breakfast nook. From here, enjoy stunning views of the lagoon-style pool, making meal prep a breeze. The family room, complete with custom built-in shelving and French doors, opens up to a screened-in lanai, offering the perfect space for relaxation or entertaining. The spacious primary suite on the main floor is a true sanctuary, featuring a walk-in closet, a luxurious soaking tub, dual sinks, and a spacious shower. Large windows provide beautiful views of the pool and tranquil backyard. A generously sized laundry room, a full bathroom, and a flexible room complete the main floor. The flexible room, conveniently located just off the kitchen, could serve as a guest room or playroom. Upstairs, you'll find three spacious bedrooms and a Jack and Jill bathroom with a soaking tub, separate shower, and dual sinks. The third bedroom can easily function as a bonus room, depending on your needs. Entertain in style in the private, peaceful backyard, where the lagoon-style pool and spa with a rock feature and waterfall from the spa create a serene ambiance. The screened-in lanai is the perfect spot to sip your morning coffee or unwind with a glass of wine while enjoying nature’s beauty. Plus, with top-rated Winter Park Schools, this home offers everything you need!

1741 Pine Avenue, Winter Park

$1,800,000

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

Under Construction. Modern elegance and timeless sophistication define 1682 Arbor Park Dr, a meticulously crafted new construction home in the heart of Winter Park, FL. Spanning 2,950 square feet, this 4-bedroom, 3.5-bathroom residence also features a dedicated office and a conditioned attic that can be used as a fifth bedroom, offering flexible living space to accommodate a variety of needs. The gourmet kitchen is a standout feature, boasting Thermador appliances, custom cabinetry, and an expansive island, making it ideal for both daily use and entertaining. Included appliances are a 36” gas range, microwave drawer, 36” refrigerator, and dishwasher. Flowing effortlessly into the living and dining areas, the home is bathed in natural light, enhancing its modern yet warm aesthetic. The primary suite, located on the second floor, offers a spa-like retreat with dual vanities, a soaking tub, and a walk-in shower. Also on the second floor are bedrooms three, four, and a conditioned attic space, which serves as an optional fifth bedroom. The first floor includes bedroom two and a dedicated office, offering privacy and convenience. The outdoor living spaces have been thoughtfully curated to provide the ultimate in relaxation and entertainment, featuring a private pool surrounded by lush, manicured landscaping. A separate, elegantly appointed pool cabana further enhances the home’s allure, creating an idyllic space for leisure or hosting guests in style. Located just moments from Park Avenue, this home offers unrivaled access to Winter Park’s finest boutique shopping, gourmet dining, and the vibrant lifestyle for which the area is known. Utilities include electricity, water, sewer, and gas connection. 1682 Arbor Park Dr is a rare opportunity to experience the pinnacle of luxury living, where modern sophistication and timeless charm come together to create an exceptional residence. Please note: Images shown are renderings and are for illustrative purposes only. Final construction details, finishes, and features may vary.

1682 Arbor Park Drive, Winter Park

$130,000

2 Beds ⋅ 1 Baths ⋅ Waterfall Cove SubDv. ⋅ 32789 Zip Code

SPECIAL FINANCING AVAILABLE! First Horizon Home Start w/ Diversity Grant available for this home while funds last. This grant funds up to 100% LTV, no PMI, Minimum borrower contribution of $500, and diversity grant of $8,000 (with no repayment) for an affordable home in a prime location? This budget-friendly 2-bedroom, 1-bath condo is move-in ready! Freshly painted ceilings, walls, trim, doors, and even a refreshed bathtub and tile give the space a bright and updated feel. Step out onto the shaded back deck, where a beautiful tree provides the perfect spot to unwind and enjoy Florida’s amazing weather or take a short walk to the community pool and club house. You can’t beat this location! With easy access to I-4, commuting is a breeze—whether you're heading to downtown Orlando, the beaches on either coast, two international airports, or world-famous attractions like Disney, Universal, SeaWorld, Legoland, and more. Don’t miss out on this opportunity! Call today to schedule your showing.

1695 Lee Road Unit E205, Winter Park

$3,550,000

3 Beds ⋅ 5 Baths ⋅ Osceola Shores Sec 03 SubDv. ⋅ 32789 Zip Code

This single-story home offers serene lakefront living with approximately 95 feet of prime water frontage on beautiful Lake Osceola. Whether you enjoy watersports, boating, or simply relaxing by the water, this property can provide the true joy of lakefront living. The grandfathered boat dock provides a rare opportunity for transformation, perfect for customizing your ideal lakeside retreat. The home boasts breathtaking lake views from the primary retreat, family room, dining room, and Florida room, providing a seamless connection to nature. Upon entering, you're greeted by a spacious living room that flows effortlessly into the family room. Adjacent to the living room is a formal dining room, ideal for entertaining guests. The expansive primary retreat has dual closets. Across from the primary, a generously sized bedroom features its own ensuite bathroom. The kitchen, located off the dining room, also captures stunning views of the lake, making it a delightful space. An additional bedroom with an ensuite bathroom provides privacy and comfort, while a half bath is conveniently located near this bedroom. A second half bathroom is situated in the garage. A recent update includes a new roof installed in 2022. The property spans .61 acres, providing plenty of room for future development. Located on one of Winter Park's most beautiful streets, this home is just a short walk from the charming shops and restaurants of Park Avenue and Rollins College. Experience the best of lakeside living and the vibrant Winter Park community from this stunning property. Opportunity awaits the buyer of this gorgeous property!

443 Lakewood Drive, Winter Park

$205,000

3 Beds ⋅ 2 Baths ⋅ Waterfall Cove At Winter Park SubDv. ⋅ 32789 Zip Code

This property located in a peaceful community IN WINTER PARK. and easy access to FL I-4 , short drive distance to Rollins College, UCF, Valencia college, Hospitals, shopping center, restaurants and Orlando Theme Park. This unit located on the second floor, it has 3 bedrooms 2, bathrooms, open floor plan. The community amenities include a large pool with lounge chairs, playground and gazebo. This property can be leased. You must see for any possibilities come and check for yourself. Registered owner is brother of the realtor. SELLER MIGHT HOLD FIRST MORTGAGE WITH A GOOD DOWN PAYMENT.

1695 Lee Road Unit C202, Winter Park

$367,500

3 Beds ⋅ 2 Baths ⋅ Karolina On Killarney SubDv. ⋅ 32789 Zip Code

One or more photo(s) has been virtually staged. An awesome home for young professionals or family or great rental for an Investor! Fantastic location! Welcome to this charming 3-bedroom, 2-bathroom Winter Park home. The combination of original wood floors and plaster walls keep the integrity of the home. An updated kitchen with gorgeous cabinets and granite countertops with space for 3 bar stools and NEW APPLIANCES adds a perfect blend of charm and modern convenience. The interior has been freshly painted. The bathroom was renovated to maintain the character of the home. The large living room is filled with light, and the additional versatile family room can be used as a home office, dining room, or exercise space. There are two nice sized bedrooms on the main floor and the upstairs bonus room includes a bedroom an ensuite bathroom and air conditioned attic space for storage. It could also be a great man cave, office or teenager private space. The beautiful totally fenced treed backyard and one-car garage with a workshop area and its own toilet, along with a carport, add to the home's appeal. The seller is offering a two year home warranty! Conveniently located near I-4, Park Avenue, Winter Park Village, Dubsdread Golf Course, restaurants and shopping and downtown Orlando

1975 Staunton Avenue, Winter Park

$4,100,000

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

Welcome home to this one-of-a-kind custom-designed and built home by Ferrarini Custom Homes, Inc. in February 2024. This singular mid-century modern home is like no other in Winter Park. Boasting an ideal location just steps from Phelps Park as well as only 1.5 miles from Park Avenue makes it the ideal home for the most discerning buyer. Custom features abound in this stunning 4582 sq. ft. masterpiece, including white oak floors, beams, and wood details in most rooms, 5 BRs, and 4.5 BAs. The first floor features a primary suite and guest suite as well as an office, great room, dedicated bar, dining area, and exquisite kitchen with a secret pass-through door to the scullery. The second level boasts three generously sized bedrooms and two baths. Cable wire railing, stone, wood inlay details, custom front door, oversized lanai with summer kitchen, outdoor fireplace, huge pool with firepit and separate firepit conversation area, the list goes on and on... This unique lot is a rare find in Winter Park - oversized in both width and depth with dimensions of 155’ deep and 143’ wide. The interior features over 6600 square feet under roof and a 4-car garage with a work-bench area included. The outdoor area features a 34-foot patio with a built-in gas grill, gas fireplace, and large-format porcelain pavers. The remote screen provides you with ease of access to your custom-designed pool with pebbletec, an outdoor shower, and a firepit nestled amongst the landscaping. The rear yard is completely irrigated and includes a well for irrigation to keep water expenses down significantly. The custom-designed pool is large for Winter Park, featuring a lounging shelf as well as a 10’ fire feature and swim-out. The massive deck is adorned with wood-like porcelain pavers with a porcelain coping. Smart home features in this home include wireless controls for audio, a/c, garage doors, pool equipment, lighting, and exterior cameras. Additionally there is upgraded spray foam insulation, gas appliances (water heaters, fireplaces, washer, range), and an elevation featuring Cultured stone, Hardi Siding, and a Jeldwyn 10’ front entry door. Herringbone pavers lead you from the cobblestone street to the magnificent front entry. Buyers will enjoy the extensive landscaping and privacy hedges. The landscaping is mature for a brand-new home! Privacy abounds everywhere in this home. Custom landscape lighting adds to the estate feel of this home. The gourmet kitchen features all Wolf and Sub-zero appliances, which include a Wolf range, Wolf 2cd oven, steam oven, Sharp microwave, Cove dishwasher with custom wood panel, a Sub-zero Refrigerator with custom panel, and a Sub-zero Freezer also with a custom panel. Disguised between the refrigerator and freezer is a secret hidden door to the scullery. Exotic countertops abound throughout the house. Quartzite like you have never seen before is evident in the kitchen and bar. Antolini Italian marble that was specially treated with “Zerocare Plus” can be found on the kitchen counters and kitchen backsplash. Custom cabinetry throughout the house, featuring white oak. Additional appliances include 3 beverage refrigerators, 1 wine refrigerator, ice maker, and a secondary 36” refrigerator. Every detail has been thought-out and implemented for you in this breathtaking home! Do not wait - the work has been done for you with NO waiting time for new construction. This elegant home will not last!

1691 Chestnut Avenue, Winter Park

$4,500,000

6 Beds ⋅ 6 Baths ⋅ Killarney Point SubDv. ⋅ 32789 Zip Code

"The Point House" on lake Killarney. Rarely available oasis, this spectacular lake front residence is positioned on a peninsula with .90 acres and over 440+ feet of lake frontage with unobstructed lake views to the south, west and east. Constructed in 2012, this home features 6,000 living square footage (3,977 on the 1st level / 1,950 on the 2nd level), 4,000 sq. ft. of outdoor space, elevator, infinity pool, boat house and tennis court. Main level offers 35 x 32 great room w/kitchen and dining, a separate dining area, 36 x 20 family room with bar/wine room, 4 bedrooms/ 3.5 baths, laundry room and 4 multi slider panel doors that open to wrap around patio with outdoor kitchen. 2nd floor offers a 2nd laundry room, lofted library, guest bedroom and primary bedroom with suite/lounge/built in wet bar and additional 4 multi slide panel doors that open to a wrap around balcony. Experience the serenity and tranquility of old Florida under the majestic cypress trees beaming with wildlife/eagles/beavers and the ever changing landscape from sunrise to sunset.

2118 Lake Drive, Winter Park

$640,000

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

Welcome to this beautifully designed home in Winter Park! This residence features an open floor plan, modern finishes, and a spacious two-car garage. The home includes tile flooring throughout the living areas, quartz countertops, upgraded light fixtures, and premium appliances. $64,900 in recent upgrades add tremendous value, including a $30,000 lanai, plantation shutters, custom blinds on sliding doors, a storage shed, privacy fencing, upgraded switches and dimmers, and custom cabinetry. The laundry room includes a butcher block folding table for added convenience. With a 2023 roof, HVAC, electrical, and plumbing systems, this home is ready for immediate occupancy. Located just minutes from Park Avenue, offering a variety of shopping, dining, and entertainment options in Winter Park. Contact us today to schedule a showing!

2739 Riddle Drive, Winter Park

$2,800,000

3 Beds ⋅ 4 Baths ⋅ Trovillion Condo SubDv. ⋅ 32789 Zip Code

Discover the pinnacle of luxury and privacy in this stunning Villa Siena penthouse residence, perfectly positioned in the charming brick-lined streets of Winter Park. While nestled in the heart of the city's vibrant dining, shopping, and cultural scene, this exclusive retreat offers unparalleled tranquility and seclusion. Designed for those who appreciate sophistication, this secured building boasts lavish amenities that extend your living space beyond the walls of your penthouse. Host guests in the elegant resident lounge, complete with a bar for entertaining, marvel at rocket launches from the spectacular rooftop terrace, or take advantage of the private conference room, ideal for high-level meetings or remote work. Stay active in the state-of-the-art exercise room, offering convenience and wellness steps from your front door. With private, secured covered parking and concierge-level service, every detail has been designed to elevate your lifestyle. Inside, refined elegance meets cutting-edge technology—custom millwork, exquisite tile work, and smart-home automation blend seamlessly with high-end video conferencing capabilities. Expansive living spaces, soaring ceilings, and generous room sizes create an inviting atmosphere, while every bedroom features a spa-like ensuite and a private balcony to take in the beauty of Winter Park. Enjoy world-class restaurants, boutique shopping, and lively events at the park, all just steps from your front door. With the nearby train station providing effortless access to Orlando and even Miami, your next adventure is always within reach. This penthouse is a rare opportunity—luxury, location, and lifestyle converge in perfect harmony. Schedule your private tour today!

315 E New England Avenue Unit 30, Winter Park

$5,400,000

5 Beds ⋅ 9 Baths ⋅ J Kronenberger Sub SubDv. ⋅ 32789 Zip Code

Extraordinary Waterfront Neoclassical Italian Estate situated on a prime .72-acre corner lot in one of Winter Park's most sought-after locations. This 7,916 SF property includes a main residence of over 7,100 SF, a detached guest house, and a poolside catering suite. The private covered boat dock is located just steps away, across the street, in the historic Kraft Azalea Garden, providing direct lake access with boat and personal watercraft storage on Lake Maitland, without the upkeep of a waterfront backyard. Inside, fresh neutral interiors and beautiful landscaping frame elegant arrival and living spaces. The thoughtful layout offers 5 bedrooms and 5 full plus 4 half baths, including a 550 SF guest house. Expansive entertaining areas flow seamlessly into a private courtyard with a heated pool and spa, covered dining, an outdoor grill, a wood-burning fireplace, and multiple terraces. Highlights include a grand primary suite with dual bathrooms and closets, a two-story wardrobe with an office in one of the primary closets, an impressive entertainment room, and a gourmet kitchen outfitted with Viking appliances, a newly replaced double oven, and a trash compactor. For large-scale entertaining, the detached pool house doubles as a catering suite with prep sink, refrigerator, and wall-to-wall storage. Built by renowned builder Charles Clayton and designed by Marc-Michaels, the home is a masterpiece of solid block construction and timeless detail featuring imported Parisian fireplaces, solid marble columns, both marble and travertine floors, and Venetian plaster walls. A new barrel tile roof (2023) adds lasting value and peace of mind. Ideally located across from Kraft Azalea Garden and near Rollins College, the estate offers a rare combination of waterfront tranquility and walkable access to Park Avenue’s world-class dining, boutiques, and museums. The Winter Park Racquet Club is also just a short golf cart ride away. A rare opportunity to acquire a legacy property with major aesthetic updates already completed and future equity positioned for growth.

1400 Alabama Drive, Winter Park

$535,000

4 Beds ⋅ 2 Baths ⋅ Orwin Manor Stratford Sec SubDv. ⋅ 32789 Zip Code

Welcome to your dream home nestled in the highly sought-after College Park district of Winter Park! This charming residence seamlessly blends history with modern upgrades, offering a perfect balance of comfort and convenience. Step inside to discover a beautifully updated kitchen featuring elegant granite countertops, ideal for both casual meals and entertaining guests. The home now boasts 1,795 heated square feet, thanks to a thoughtful garage conversion. The previous owner transformed the garage into a spacious primary bedroom with an en-suite bath, complete with central air conditioning and an additional mini-split AC unit for added comfort. The home also features an electronic gate access carport, ensuring secure and easy parking, while the expansive, fully fenced backyard provides a private oasis for relaxation or gatherings. Imagine enjoying your morning coffee or hosting weekend barbecues in this serene outdoor space. Location is everything, and this home delivers! Just a stone's throw away from Trader Joe's, you'll have easy access to popular shopping and dining options. Plus, with its proximity to downtown Orlando and local attractions, you'll never be far from the vibrant lifestyle that this area offers. Don't miss the opportunity to own a piece of history with all the modern comforts you desire. Schedule your showing today and experience the charm and convenience of this exceptional College Park home!

1531 Norfolk Avenue, Winter Park

$260,000

2 Beds ⋅ 2 Baths ⋅ Winter Park Gardens Condo SubDv. ⋅ 32789 Zip Code

This spacious 2-bedroom, 2-bathroom condo awaits you in a vibrant community. The mid-century modern complex offers the convenience of a community pool, on-site laundry, and picturesque pond views while being centrally located near Downtown Orlando, Downtown Winter Park, and Mead Gardens. Embrace a comfortable and active lifestyle in this desirable residence

700 Melrose Avenue Unit B-4, Winter Park

$1,400,000

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

Welcome to this masterfully renovated Winter Park residence, where modern luxury meets timeless comfort in coveted Timberlane Shores. The heart of this home is a chef's dream kitchen, featuring a professional WOLF range, custom two-tone cabinetry in rich wood and sophisticated navy blue, and premium stone countertops that extend to a generous entertainment island. Gleaming terrazzo floors flow seamlessly through the open-concept living spaces, where abundant windows frame views of the lush gardens and flood the home with natural light. The thoughtfully designed floor plan incorporates two distinct living areas - one integrated with the kitchen for casual gatherings, and a separate space with soaring vaulted ceilings and custom built-ins perfect for formal entertaining or quiet evenings. The primary retreat offers a private sanctuary with vaulted ceilings, spa-like ensuite bath, and walk-in closet, while three additional bedroom suites provide comfortable accommodations for family or guests. Step outside to discover multiple outdoor living spaces, including a patio ideal for al fresco dining and a spacious backyard with mature landscaping and room for a future pool. Located in one of Orlando's most sought after neighborhoods, this turnkey home offers access to top-rated schools including Audubon K-8 and Winter Park High School. This is more than a house - it's an invitation to experience the refined Winter Park lifestyle you've been dreaming of.

1750 Winchester Drive, Winter Park

$649,000

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

Charming pool home zoned for Audubon K-8 and Winter Park High, tucked behind a private courtyard with artificial turf that feels like your own little secret garden. Vaulted ceilings with tongue-and-groove details add warmth and character to the living and dining areas. The eat-in kitchen features a large passthrough window overlooking the great room, perfect for entertaining. The bright Florida room brings in natural light and opens to the screened-in patio and pool—ready for relaxing weekends. The primary suite offers sliding glass doors to the patio, a walk-in closet, and an en-suite bathroom. Two additional bedrooms share a hall bath with an updated vanity and a shower/tub combo. Outside, the screened patio and pool create a private oasis, with a low-maintenance yard offering potential for customization. Additional features include a two-car garage, plantation shutters throughout, 2021 roof, 2018 AC, and whole-house re-plumbed in 2004. Conveniently located minutes from Park Avenue, Baldwin Park, and Winter Park's dining and shopping scene. Call today to schedule your private showing!

721 Glenridge Way, Winter Park

$1,265,000

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

Data entry only.

420 Sylvan Drive, Winter Park

$1,395,000

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

Welcome to your new home in Timberlane Shores. This one-story ranch offers a delightful living experience. The generously sized master suite features a spacious bath and walk-in closet. The split floor plan ensures privacy, with three well-appointed rooms on the opposite side of the house. Wood floors throughout, granite counters in the kitchen and bathrooms. Kitchen features soft touch cabinets and stainless-steel appliances. Step outside and immerse yourself in the serene surroundings, with an expansive front and back yard adorned with well-kept lawns. The backyard oasis features a refreshing pool, offering a private escape. This home is perfect for entertaining, making it an ideal space for hosting gatherings with friends. Located in a sought-after school district, this neighborhood offers an exceptional educational environment.

1771 Winchester Drive, Winter Park

$586,500

3 Beds ⋅ 1 Baths ⋅ Lake Forest Park SubDv. ⋅ 32789 Zip Code

.

2361 Mulbry Drive, Winter Park

$4,273,211

4 Beds ⋅ 5 Baths ⋅ Virginia Heights SubDv. ⋅ 32789 Zip Code

Steeped in history and masterfully reimagined, this 1926 Winter Park estate blends architectural provenance with modern refinement. Thoughtfully restored by E2 Homes, the residence honors its past while offering contemporary sophistication. Unlike many historic properties, it is free from preservation restrictions, allowing for seamless enhancements. On the shores of Lake Virginia along the desirable Winter Park Chain of Lakes, this 3,181-square-foot estate features four bedrooms, three full baths and two half baths, with three bedrooms in main house plus detached one-bedroom guest cottage. The second-floor primary suite is a private retreat with a Juliet balcony, dual closets and an elegantly appointed bath with an expansive dual-sink vanity, a separate water closet, and a washroom with a shower-tub combination. A Jack and Jill bath, adorned with Maharam wallpaper, serves the additional upstairs bedrooms. The Poliform TWELVE kitchen showcases European craftsmanship with Gaggenau and Sub-Zero appliances, sleek Italian cabinetry, and natural basalt countertops. The formal dining room, framed by arched windows and French doors, opens to a vine-covered courtyard, while the sunroom offers uninterrupted lake views. A fireplace in the living room, flanked by custom built-ins, adds warmth to the home’s contemporary aesthetic. Beyond its striking interiors, the estate is an architectural rarity, featuring original woodwork by Gene Leedy, a key figure in the Sarasota School of Architecture. The home is crowned with sought-after Ludowici-Celadon Imperial roof tiles. Poliform built-ins extend throughout, including a dedicated upstairs office/library. An integration of art and architecture, the property features site-specific installations by acclaimed artist Matt Olson. His No Separation project finds a compelling continuation here, with a sculptural installation of galvanized steel surrounding a crepe myrtle, accompanied by a matching bike rack. The entryway, designed by Olson’s firm OOIEE and inspired by Sol LeWitt, makes a striking first impression. Designed for seamless indoor-outdoor living, the estate’s exterior spaces are as refined as its interiors. A covered deck overlooks a heated saltwater pool and spa, while a custom cedar hot tub blends into the landscape. A wood-clad pergola shelters the outdoor kitchen, featuring a Röshults system with a professional-grade grill, sink and storage. The boathouse includes a partial bath, creating a waterfront sanctuary. A Sonos-integrated sound system extends from the main house to the patio, guesthouse and boathouse, ensuring a seamless sensory experience. The detached guesthouse is a private retreat with a full bedroom, bath, kitchenette and Poliform built-ins. Floor-to-ceiling windows frame manicured grounds and lake views, while a private covered porch provides a tranquil space for relaxation. Every detail has been meticulously curated, from designer lighting to motorized roller shades and a wood-burning fireplace anchoring the living room. A private wine library enhances the home’s sophisticated appeal. Meticulously maintained by E2 Concierge services, the residence undergoes routine wellness checks and meticulous upkeep. A distinctive home of this caliber is rarely available, a residence where history, architecture and art converge in harmony. This is a once-in-a-lifetime opportunity to own one of Winter Park’s architecturally and artistically significant properties.

1336 College Point, Winter Park

$799,000

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

A pristine location to build the home of your dreams in the heart of the Tree Streets of Winter Park. Elm is a quiet tree-lined street providing tranquility while providing the lifestyle Winter Park is known for. Elm is a block from Phelps Park, a short walk to YMCA, Interlachen Country Club and Winter Park Racquet Club. The lot is roughly 75 by 122 feet and among multimillion-dollar homes. Home to the best schools, zoned for Lakemont, Maitland Middle and Winter Park High. Homes on this street don’t come up often. Call us for a private showing.

Winter Park

$340,000

Winter Park SubDv. ⋅ 32789 Zip Code

Unleash your imagination and seize the opportunity of a lifetime with this incredible vacant lot in the heart of Winter Park! This gem is priced to sell and is just two blocks away from the vibrant Hannibal Square. Imagine crafting your dream home on this prime piece of land, where every day can be filled with adventure and excitement! You’ll find yourself mere steps from the best attractions Winter Park has to offer. Stroll over to delightful bars, mouthwatering restaurants, and charming shops along Hannibal Square and Park Avenue. Enjoy the stunning parks, fascinating museums, and picturesque chain of lakes that make Winter Park truly special. Plus, you’re right in time for the Winter Park Art Festival—no more stressing about parking! And don’t forget about the must-visit Sunday farmers' market for fresh produce! This location also keeps you close to Rollins College, the New Winter Park Library, Trader Joe's, and even the lovely Sunrail and Amtrak train station. When it’s time to venture further out, enjoy quick access to I-4 for easy trips to the beach, exploring the new Universal's Epic Universe Park or magical time at Disney World. With exciting renovations and new constructions popping up all around, now is a fantastic time to get involved in this thriving community! Don’t miss your chance to transform this vacant lot into your personal paradise! Act fast—this opportunity won’t last long!

829 W New England Avenue, Winter Park

$610,000

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

Welcome to 2812 Mulford Avenue. This updated 3 bedroom and 2 bath home is located perfectly in Winter Park. Walking distance to East End Market, close to Rollins College, steps from Baldwin Park, 1 mile from Mills 50 area, and close to Mead Gardens, Leu Gardens and Loch Haven Park. The neighborhood is quiet with low traffic, oversized lots, and NO HOA, yet surrounded by amazing schools, local coffee shops, incredible restaurants & bars, and world-class shopping. The home itself is completely move-in ready, offering an amazing kitchen and is open to the formal living room/dining room. This open space connects to the den, which is an oversized room that leads to the expansive backyard with a great patio deck for entertaining, and convenient storage shed. The living room also connects via french doors to a great flex space that could morph into a homework station, home office, or new laundry room. Welcome Home!

2812 Mulford Avenue, Winter Park

$1,835,000

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

A timeless masterpiece, this 1935 English Cottage, designed by the renowned Gamble Rogers, stands as a testament to classic elegance and enduring craftsmanship. Nestled on nearly half an acre in one of Winter Park’s most coveted neighborhoods, this home has been thoughtfully updated with modern luxuries while preserving its original charm. Inside, warm Heart of Pine floors, beadboard vaulted ceilings, restored period hardware, and custom built-ins create an inviting ambiance. Spacious formal and casual living areas include a dining room, separate living and family rooms, an office, and a versatile flex space. The expanded and renovated kitchen is a chef’s dream, now featuring marble countertops, custom white cabinetry, a Wolf gas range, stainless steel appliances, a built-in Miele espresso machine, and a farmhouse sink. The thoughtful redesign includes a custom range hood, a new ventilation system, and an integrated refrigerator/freezer drawer in the island. The first-floor primary suite is a private retreat with serene backyard views, two walk-in closets, and a bathroom with dual vanities, a clawfoot tub, and a separate shower. Upstairs, two bedrooms share a charming bathroom. Outside, a lushly landscaped backyard offers an idyllic escape with a newly installed pool heater (2023), a restored koi pond, and extensive hardscape additions. A covered porch and a newly added summer kitchen with plumbing make this home an entertainer’s paradise. The fully fenced property is surrounded by mature landscaping, refreshed with new perennials and heirloom camellias. Additional recent upgrades include a new roof (2021), restored siding, new gutters with leaf guards, and a new irrigation system. A detached guest house with a sitting area and loft provides the perfect private space for visitors. Located just minutes from Park Avenue, downtown Orlando, and zoned for the sought-after Audubon Park K-8 and Winter Park High School, this home embodies the perfect blend of historic elegance and modern convenience.

160 Glenridge Way, Winter Park

$2,250,000

4 Beds ⋅ 6 Baths ⋅ Shores Lake Killarney Sec 02 SubDv. ⋅ 32789 Zip Code

Nestled along the serene shores of Lake Killarney, one of Winter Park's best-kept secrets Lake Killarney is one of Winter Park's largest freshwater spring-fed lakes (240 acres) this stunning lakefront home offers breathtaking views and direct water access. Featuring a private boat lift, dock, and spacious outdoor entertaining areas, this property is perfect for boating enthusiasts and nature lovers alike, including boat, canoe, kayak, ski, fish, windsurf or jet ski on this pristine lake. Come early for your appointment and drive the entire quaint neighborhood and see why this neighborhood for lakefront living is so sought after. Where else can you boat and dock at Trader Joe's, Hillstone's Restaurant, some of Winter Park's most desirable shopping and restaurant establishments? The home is located just minutes from Park Ave., I-4, Rollins College, Winter Park Village, Winter Park's Ravaudage and ALL OF Winter Park's restaurants and shopping!! Inside, you’ll find an open-concept layout with high ceilings, large windows, and modern finishes. The gourmet kitchen boasts stainless steel appliances, quartz countertops, and an extra-large island, ideal for entertaining. The home boasts 4 bedrooms, 4 full baths, 2 half baths, 3694 square feet of living space, with 2 primary suites including a spa-like bathroom and a private deck overlooking the lake view; A 3-car garage with a gym area and sauna, an outdoor kitchen and a boat dock with an electric boatlift. Don’t miss this rare opportunity to own a slice of paradise on Lake Killarney! Contact us today to schedule a private tour.

301 Rippling Lane, Winter Park

$835,000

4 Beds ⋅ 2 Baths ⋅ Kenilworth Shores Sec 06 SubDv. ⋅ 32789 Zip Code

Completely remodeled, coastal-inspired home is located in the highly sought-after Winter Park neighborhood of Kenilworth Shores in Winter Park 32789. Minutes from the world-renowned Park Avenue and upscale shopping, dining, parks, community events, Sunrail and more lifestyle. The home is zoned for some of Winter Park's most desirable schools, including Brookshire Elementary, Glenridge Middle, and Winter Park High School. This home is a true gem, meticulously and completely remodeled for a coastal feel that blends modern elegance with comfort. Featuring 4 spacious bedrooms + office, the residence is designed to impress. The entry showcases a custom, German-made solid front door that opens into a bright, airy living space with engineered wood floors throughout. The raised ceilings enhance the sense of openness, complemented by beautiful wood beams that add character to the home. A shiplap-clad eat-in area creates a charming focal point, while the kitchen is equipped with premium Badger Woodworks self-closing cabinetry, gorgeous granite countertops, and new appliances including espresso bar and wine fridge. No detail has been overlooked in this home, with recent upgrades including a new HVAC system and ductwork in 2024, as well as completely updated plumbing, windows, and light fixtures. Replumbed with Pex piping in 2015. The walls have been professionally retextured, and the home also offers the convenience of an interior laundry room and brand new barn door. Outside, the covered porch provides the perfect space for entertaining, with the hot tub conveys for relaxation. The outdoor bar showcases a custom millwork bar with a grill, kegerator, and fountain, ideal for hosting gatherings. A shed on a concrete slab and a workshop area in the garage offer ample storage and workspace. The property is fully fenced, ensuring privacy and security. 625 Worthington home is located in the heart of Winter Park, home to Rollins College, one of America's top-ranked liberal arts colleges. With its prime location, luxury finishes, and family-friendly neighborhood, this home offers an exceptional living experience in one of Central Florida’s most desirable areas. With the neighborhood rapidly evolving, many homes around this property are being torn down to make way for new, custom-built estates, including expansive 4,000 square foot homes valued at over $3 million.

625 Worthington Drive, Winter Park

$2,495,000

5 Beds ⋅ 4 Baths ⋅ Cortland Park SubDv. ⋅ 32789 Zip Code

Welcome to this beautifully renovated century home on one of the most picturesque brick streets in Olde Winter Park. Take a leisurely stroll down to Lake Mizell or enjoy the views from its large front patio. This classic pool home is filled with charm, natural light and is designed for easy entertaining. The spacious layout offers multiple rooms for every occasion, including a bright sunroom, cozy living room with a fireplace, and a large welcoming family room. The gourmet kitchen features custom wood cabinets, quartzite counters, a convenient office nook and an adjoining breakfast room, while the formal dining room boasts elegant moldings and built-in corner cabinets. A secret basement presents options for additional storage or a wine cellar. The second floor features a generously- sized master suite, two additional bedrooms, two updated baths, and a versatile nursery or bonus room, perfect for a study or home office. The property includes a detached two-car garage and a charming guest house with a bedroom, bath, and loft area. Newly renovated resort back yard includes heated salt water pool and spa, multiple seating areas, complete with gas hookups for fire pit and outdoor kitchen and a maintenance-free travertine and turf pool scape. You’ll love the inviting ambiance of both this home and its vibrant Winter Park location.

140 Cortland Avenue, Winter Park

$4,950,000

5 Beds ⋅ 7 Baths ⋅ Comstock Park SubDv. ⋅ 32789 Zip Code

New Hamptons-style residence offering a seamless blend of elegance and modern sophistication. A gated entrance opening to a circular driveway and motor court, set the stage for enjoying this exceptional estate. As you enter home, an impressive 2-story foyer with a glass-paneled staircase wraps around a temperature-controlled wine room and a transparent glass elevator, effortlessly connecting all levels including an expansive third-floor multi-purpose space. Designed for contemporary living, the thoughtfully curated floor plan features a spacious open concept kitchen/gathering room along with the dining area enjoy a wall of glass doors and picture window overlooking an expansive lanai, and serene backyard with a sparkling pool and spa. The main residence offers 4 bedrooms, private home office, and multiple flex spaces, complemented by a detached pool cabana that serves as a 5th guest retreat or versatile use building. The gourmet kitchen is an entertainer’s dream, featuring dual 10-foot stone islands, a 60-inch Wolf range, dual 36-inch Sub-Zero refrigerator and freezer columns, a warming drawer, beverage center and a 146-bottle Sub-Zero dual-zone wine cooler. A separate pantry kitchen is equipped with a Dacor induction cooktop, convection oven, additional refrigerator, microwave, dishwasher and ample cabinetry, ideal for catering and meal preparation. The 1st-level primary suite is a tranquil retreat, offering a sitting area, an all-marble bath with a glass-enclosed shower, multiple body sprays, a soaking tub, and French doors leading to a secluded Zen garden with an outdoor shower and fountain. There is also a hidden private home office near the front of home. The second level hosts 3 additional en-suite bedrooms, a generous lounge area, bar, and a well-appointed laundry room with extra storage cabinetry. As noted previously, there is also a unique 3rd level accessible by a staircase or elevator. The outdoor living is elevated with a spacious lanai featuring motorized screens, a gas fireplace, dining space, and a summer kitchen with a 54-inch Coyote wood and gas grill, plus a separate burner beneath a remote-controlled louvered roof. There is also a detached cabana perfectly suited for a guest suite, fitness studio, additional office or game room, complete with a full bath, mini kitchen, and washer/dryer. Crafted with meticulous attention to detail, this home showcases Anderson windows, 10-foot solid doors, high-end lighting, plumbing and electrical fixtures, custom cabinetry built-ins, as well as Trane HVAC systems, ensuring quality and comfort... Lush landscaping, including magnolia trees, bamboo and cypress, surrounds the property, creating a private sanctuary. An attached side-entry garage features a powered car lift providing space for up to three vehicles. Ideally near Interlachen Country Club, Winter Park Racquet Club, Phelps Park/YMCA, and renowned Park Avenue. Note: Partial staging by RH and the furniture package can be purchased separately...

1660 Palmer Avenue, Winter Park

$411,250

2 Beds ⋅ 1 Baths ⋅ Dubsdread Heights SubDv. ⋅ 32789 Zip Code

Welcome to this beautifully maintained Winter Park gem, offering exceptional curb appeal and bursting with charm, character and timeless style. Located in the highly desirable Dubsdread Heights neighborhood, bordering Little Lake Fairview and the Dubsdread Golf Course, this home places you just minutes from the boutique shops, dining options and festivals of Park Avenue, with easy access to I-4. As you step inside, you're greeted by a bright sunroom with warm, stylish Saltillo tile flooring which seamlessly flows into the spacious living room featuring stunning Red Oak hardwood floors. The eat-in kitchen boasts sleek quartz countertops, modern cabinets with crown molding, a built-in pantry with convenient slide-out drawers and newer appliances. This home has been thoughtfully updated with double-paned windows, a 2018 roof replacement and updated plumbing, ensuring peace of mind for years to come. Both bedrooms are generous in size and feature Red Oak wood flooring and modern ceiling fans, with a full bath conveniently situated in between that retains timeless charm with original custom tiling, a pedestal sink, and shower/tub combo. The private, fully fenced backyard is a true tropical retreat, perfect for relaxation or entertaining guests. The recently replaced wood deck with sail awnings and a concrete patio create ideal spaces to enjoy Florida's year-round beauty. A charming brick paver walkway leads to a separate laundry and storage shed, with additional cabinets and space to meet your storage needs. This home has gutters installed along with a rain barrel designed to capture and conserve water for your landscaping watering needs. Kitchen appliances, washer, dryer and lawn mower, edger, and blower are all included in sale. Combining the perfect blend of modern updates and original character, this home is a must-see in the heart of Winter Park!

767 Baffie Avenue, Winter Park

$480,000

3 Beds ⋅ 3 Baths ⋅ Killarney Circle SubDv. ⋅ 32789 Zip Code

NO HOA! Beautifully Remodeled Home with Expansive Garden in Winter Park Welcome to this charming and fully remodeled two-story, 3-bedroom, 3-bathroom home nestled in the heart of Winter Park. Offering a blend of modern upgrades and historic charm, this property is surrounded by a vibrant community with easy access to top destinations. Prime Location: 5 minutes to Whole Foods and Trader Joe’s 8 minutes to Downtown Orlando via I-4 (Exits 87 & 88) Surrounded by Winter Park’s historic charm Private library with an excellent book collection Weekly Farmers’ Market just minutes away Extensively Renovated in 2019: New Roof, New Windows, New A/C New Electrical Wiring & Plumbing New Driveway & Fully Fenced Yard with Entry Gate New Porch & Open-Concept Kitchen Versatile Living Space: This single-family home offers flexible living arrangements and can also function as a duplex: Downstairs: 1 bed, 1 bath, spacious living room with modern kitchen combo Upstairs: 2 beds, 2 baths, large family room, and a covered porch with scenic views Outdoor space on the porch for entertaining All permits are available on the Orange County Property Permit website for complete peace of mind. Don't miss this rare opportunity to own a beautifully updated home with endless potential in a highly desirable location! Contact us today for a private showing.

423 Ololu Drive, Winter Park

$1,180,000

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

Charming One-Story Home in the Heart of Winter Park with an incredible pool area. Nestled in the heart of Winter Park, this elegant one-story home features a classic brick circular driveway and a welcoming covered front porch. Inside, the original hardwood floors add warmth and character to this four-bedroom, four-bathroom residence plus an exquisite detached home-office room , located in the beautiful outdoor patio area. This fifth bedroom offers a versatility that could be used as an office or a cozy den. The spacious living and dining area boasts high vaulted ceilings and a wood-burning fireplace, creating the perfect atmosphere for entertaining. The open floor plan seamlessly connects each space, offering both style and functionality. The primary suite is a peaceful retreat, with French doors opening to the pool area, a large walk-in closet, and an en-suite bathroom featuring a glass tile shower. Step outside into your private oasis, where the brick patio, wood trellis, and sparkling pool with water features create a serene escape. The oversized 95 x 150 lot is shaded by mature oak trees, with paved walkways enhancing the peaceful ambiance. Additional House Benefits include: Remodeled living room ; Original wood fireplace ; New AC (2021) ; Tankless water heater 2021 ; Dual masters ; 4 full baths ; Insulated 2 car garage with exAC Garage ; New vinyl flooring ; Remodeled office / guest room with built-in cabinets ; Heated swimming pool ; Renovated backyard with artificial grass and summer kitchen (outdoor furniture negotiable) ; New detached office space w/ air conditioning ; Outdoor ambient lighting ; New alarm system ; All appliances will stay ; Extended Kitchen Island ; New sprinkler system ; Outdoor shed storage; Acclimate Attic ; New PVC Wood Deck ; Water filtration system in the kitchen ; Underground gas line for stovetop, water heater, and pool heater Located just minutes from Windsong, Park Avenue, Baldwin Park, top-rated schools (Brookshire, Glenridge, WPHS), parks, dining, and shopping, this home offers both charm and convenience.

181 N Phelps Avenue, Winter Park

$1,075,000

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

Step into this stunning one-story Spanish Mediterranean home, beautifully renovated in 2006 by renowned E2 Homes. Offering four bedrooms and three baths, this thoughtfully designed residence seamlessly blends timeless charm with modern comforts. The inviting living room features a cozy gas fireplace, setting a warm tone for the home. A formal dining room connects to the spacious kitchen through a convenient butler’s pantry. Designed for the chef at heart, the kitchen boasts a large island with a gas range and hood, abundant cabinetry, and generous counter space, along with a breakfast nook that overlooks the family room. Beautiful brand new (May 2025) Silestone countertops in kitchen, butler's pantry, office/study & laundry room, making each space light & bright. French doors open from the family room to a covered lanai, creating a space for indoor-outdoor living. A dedicated office/study or flex space leads to the private primary suite. The primary bedroom has its own set of French doors opening to the lanai and includes a custom walk-in closet. The primary bath is a serene retreat with dual sinks, a large soaking tub and a walk-in shower. The second bedroom enjoys an en-suite bath, while two additional bedrooms feature custom closet systems for maximum organization. The large fenced backyard offers ample space for a future pool, providing endless possibilities for outdoor enjoyment. Close proximity to the shopping and dining district of Park Avenue in downtown Winter Park, this remarkable home offers the ideal blend of comfort, convenience and style. ***NOTE: all interior walls recently painted neutral soft white... also, this home has accessible elements to it, including a handicapped ramp in garage.

1690 Oneco Avenue, Winter Park

$430,000

3 Beds ⋅ 2 Baths ⋅ Fairbanks Shores Sixth Add SubDv. ⋅ 32789 Zip Code

Discover a true slice of paradise just minutes from downtown Orlando, nestled along the serene shores of Lake Fair. This meticulously maintained 3-bedroom, 2-bathroom home, built in 1958, reflects an era when craftsmanship and attention to detail were paramount. The moment you step through the front door, you’ll be captivated by the original pine floors, gleaming with character and charm. Straight ahead, a massive living room invites you to unwind, complete with a Yamaha surround sound system—perfect for movie nights or entertaining. To your left, the spacious dining room and kitchen boast a 9-foot solid surface island with a farmhouse sink, 42" quiet-close cabinets, and a real tile backsplash (no peel-and-stick here!). The bathrooms have been beautifully renovated, offering a touch of modern luxury while maintaining the home's timeless appeal. The primary suite is a true retreat, featuring plantation shutters that add elegance and privacy. Step outside to a lush, tropical oasis where palms and landscaping create an ultra-private setting—ideal for cozy evenings around a firepit or swaying in a hammock with a gentle lake breeze. A 20x10 screened porch overlooks the lake, providing a perfect spot for morning coffee or unwinding at sunset. Adjacent to the kitchen, the laundry room is conveniently located just outside the side door. The enormous 2-car carport offers ample coverage for your vehicles, keeping them protected from the elements after a trip to the store. And for fishing enthusiasts? The seller has reeled in 5 lb. bass right from the backyard! Beyond this stunning home, the location is unbeatable. You're just minutes from the vibrant dining and shopping scene of Winter Park, home to award-winning restaurants, charming boutiques, and cultural hotspots like the Winter Park Farmers’ Market and Park Avenue. Downtown Orlando is a short drive away, offering easy access to the city's best entertainment, including Lake Eola Park, where you can enjoy fireworks, swan boat rides, concerts, and year-round festivals like the Orlando Film Festival and the Spring Fiesta in the Park. For nature lovers, this home is just minutes from Leu Gardens, a breathtaking 50-acre botanical garden featuring stunning tropical plants, butterfly gardens, and scenic walking trails. It also hosts outdoor movie nights, educational workshops, and seasonal events like the Dazzling Nights light festival. Also nearby is Mead Botanical Garden, a 47-acre nature preserve in Winter Park, offering hiking trails, butterfly gardens, a boardwalk, and even a community garden. It’s the perfect place for birdwatching, photography, or a peaceful escape into nature. Don’t miss the chance to own this lakefront gem—a perfect blend of historic charm, modern upgrades, and an unbeatable location. Schedule your private tour today!

328 Lake Fair Lane, Winter Park

$380,000

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

Winter Park location with access to Lake Killarney & walking distance to Trader Joes & Winter Park Village. Renovated 2 bedroom 2.5 bath 2 story condo with Pool & lake view amenities. Gorgeous wood floors throughout, Granite counters, Stainless Steele appliances , Soft close cabinets & glass tile backsplash. Inside Laundry room with Washer/Dryer included. Under stair storage. Wood burning Fire place, Bar sink, Ceiling Fans, Both bedrooms have large walk-in closets and the primary has a walk out balcony patio. The Primary bath offers double shower heads & double vanity. Outside Storage closet & Enclosed screen patio. The pool is set with majestic sunset views of the lake where you can fish off the dock or kayak the lake. HOA updates include repaved asphalt parking & exterior paint, dock repainted & pool sealant in 2020. Fees include exterior maintenance, pool, dock & trash.

350 Killarney Bay Court Unit 5, Winter Park

$905,000

3 Beds ⋅ 3 Baths ⋅ Kenilworth Shores Sec 02 SubDv. ⋅ 32789 Zip Code

Welcome to 533 Balmoral Road, a beautifully updated mid-century modern gem nestled in the desirable Kenilworth Shores neighborhood of Winter Park. This 3-bedroom, 3-bathroom residence, spanning 1,900 square feet, offers a harmonious blend of classic design and contemporary upgrades. As you step inside, you'll be greeted by an open-concept layout that seamlessly connects the living area and kitchen, with a wood burning fire place creating an inviting space perfect for both relaxation and entertaining. The heart of the home is its modernized kitchen, featuring sleek cabinetry, quartz countertops, and stainless steel appliances, catering to the needs of today's discerning homeowner. One of the standout features of this home is the unique central courtyard, visible from the main living areas, providing a serene outdoor retreat and flooding the interior with natural light. The thoughtful design ensures a seamless indoor-outdoor living experience, ideal for Florida's pleasant climate. The private quarters include three generously sized bedrooms. Two of these boast en suite bathrooms, offering added convenience and privacy, while the third bedroom is serviced by a well-appointed hall bath. An additional bonus room could be used as an office, dining, sunroom or whatever you desire. Each space has been thoughtfully designed to provide comfort and style. Situated in the heart of Winter Park, this property offers more than just a beautiful home and lush landscaping. Residents will appreciate the proximity to top-rated schools, picturesque parks, and the vibrant local dining and shopping scenes. The community's tree-lined streets and friendly atmosphere make it a sought-after location for families and professionals alike. Experience the perfect blend of mid-century charm and modern amenities at 533 Balmoral Road—a place you'll be proud to call home. Upgrades include: New Paint & Finishes, Modernized Bathrooms (New vanities and a renovated master shower) Custom Master Closet, New Interior Doors and windows, New Upgraded HVAC System (2021), Tankless gas hot water heater, Roof (2020), HVAC (2021) Exterior Stone Façade, Updated Landscaping & Outdoor Living spaces (Lanai, pergola, and firepit) irrigation, New Front Door & Exterior Lighting, Solar Panels (paid off) Security System Ready (Wired for easy setup) Upgraded Laundry Room (Added storage, tile, and cabinetry)

533 Balmoral Road, Winter Park

$987,500

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

Charming Spanish-Style Bungalow with Private Oasis in the Heart of Winter Park. Step into the elegance of Old Florida with this exquisite Spanish-style bungalow, nestled in Winter Park. Offering the perfect blend of historic charm and modern luxury, this 4-bedroom, 2.5-bath retreat is a hidden gem surrounded by lush, mature landscaping, creating a private sanctuary just minutes from the best Winter Park has to offer. From the moment you arrive, you’ll be captivated by the stunning curb appeal, featured on the front cover of Home & Garden magazine. The beautifully maintained exterior, with its 2023 terracotta-styled flat roof sets the stage for what lies within. Inside, timeless character meets contemporary upgrades. French terracotta flooring, antique hardware, and neutral warm tones create an inviting atmosphere, while thoughtful renovations ensure every modern convenience is at your fingertips. The kitchen is a chef’s dream, boasting vanilla quartz countertops with gold flecks, beautifully complementing the bronze accents and upgraded appliances. The open-concept design seamlessly connects the kitchen, dining, and living area ideal for entertaining. For more intimate gatherings, unwind in the spacious family room or soak in the natural light from the attached sunroom, which overlooks the lush backyard retreat. Step outside to a tranquil space perfect for morning coffee or evening cocktails, all while enjoying the peaceful sounds of nature. The pool and jacuzzi (new heater installed in 2021) add a touch of resort-style living, surrounded by meticulously curated landscaping with extensive landscape lighting (2022) that enhances the homes enchanting ambiance. Situated in a vibrant, walkable neighborhood known for its tree-lined streets and friendly atmosphere, this home is just a short stroll to Lake Knowles, the YMCA, and Phelps Park. Bring your golf cart and enjoy easy access to Interlachen Golf & Country Club or the Winter Park Racquet Club. Plus, you’re less than a mile from the newly renovated Winter Park Hospital and just minutes from Park Ave world-class dining and shopping. Top-rated schools: Zoned for Lakemont Elementary, Maitland Middle, and Winter Park High School. This rare, character-filled home offers a perfect blend of privacy, luxury, and location. Don’t miss your chance to own a piece of Winter Parks most desirable neighborhood!

1585 Chestnut Avenue, Winter Park

$635,000

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

Fresh, modern and move-in ready. This pristine, first-floor condo is located in historic downtown Winter Park at the coveted Cloisters Condominiums. Professionally designed and remodeled in 2021, this two-bedroom, two-bathroom unit includes an open floor plan with marble tile throughout and a screened patio with built-in planters and mature garden views. The large, open kitchen includes a family-sized island with seating and storage, stone countertops, new cabinetry and stainless-steel appliances, and Clearly® water filtration system. Timeless features include southern plantation shutters, wainscoting and hand-carved ceiling fans in every room, plus spa-inspired bathrooms, custom closets and plenty of storage, and a full-sized Bosch washer and dryer. The frosted glass barn door glides shut for your master suite retreat overlooking internal garden courtyard. Unit comes with assigned covered parking and air-conditioned storage closet. The Cloisters lifestyle boasts lakefront seating, docks, kayak storage and boat slips; workout rooms, Swedish dry sauna and inside bike storage; a newly remodeled club house with full kitchen, lending library, putting green, grill station and pool; professional on-site management and custodial staff—all set within established landscaping for unparalleled leisure. Unit 111 is light, bright and quiet. Being on the ground floor, this unit is perfect for those with a pet. Offered at under $700K with optional turnkey package available. Welcome home.

100 S Interlachen Avenue Unit 111, Winter Park

$750,000

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

VALUE IS IN THE LAND. LOT IS 90 X 150+- GREAT OPPORTUNITY TO BUILD YOUR DREAM HOUSE IN 32789. HOUSE NEEDS EVERYTHING AND WILL BE DIFFICULT TO GET INSURANCE. LOCATED ON PRIVATE, DEAD END STREET. CLOSE TO YMCA, PHELPS PARK, INTERLACHEN CC. GREAT WP SCHOOLS. SURVEY AVAILABLE IN ATTACHMENTS.

1811 Oneco Avenue, Winter Park

$429,000

2 Beds ⋅ 2 Baths ⋅ Karolina On Killarney SubDv. ⋅ 32789 Zip Code

ATTENTION INVESTORS!!! DIAMOND LOCATION!! THIS IS THE MOST WONDERFUL OPORTUNITY FOR BUYING YOUR DREAM DUPLEX WITH 1 BED 1 BATH ON EACH OF TWO FLOORS IN THE MOST DISERABLE AREA FOR LIVING CALLED WINTER PARK IN THE 32789 ZIDE CODE. NO HOA NEITHER CDD. IT IS LOCATED JUST MINUTES FROM PARK AVE., ROLLING COLLEGE, AND TONE OF RESTAURANTS!! EACH UNIT HAS 1 BED 1 BATH WITH ITS COZY KITCHEN, AND NICE FAMILY ROOM. THIS DUPLEX HAS A ENORMEOUS POTENTIAL INCOME. GREAT SCHOOLS!!, NEAR TO HIGH-WAYS!! RIGHT PRICE!! IT WILL NOT LAST LONG!!

441 Clay Street, Winter Park

$1,645,000

Kenilworth Shores Sec 06 SubDv. ⋅ 32789 Zip Code

Lakefront Lot. Build your dream home on a rare available Lot on Lake Berry. Establish your legacy at this beautiful Winter Park location. A short walk to Baldwin Park or a short bike ride to Park Avenue. The Current home needs to be demolished as the value is in the Land. There is a total of 1.14 acres with roughly .6 acres of uplands with direct waterfront. Build your own dock to your liking. No survey is available. All measurements are approximate and have been obtained through the OCPA map system. Please click on the Virtual Tour to see arial drone shots and much more.

681 Balmoral Road, Winter Park

$1,877,500

5 Beds ⋅ 6 Baths ⋅ Orwin Manor Westminster Sec SubDv. ⋅ 32789 Zip Code

Nestled in the highly sought-after Orwin Manor neighborhood of Winter Park, this stunning Spanish Revival home at 1446 Berkshire Ave, offers a luxurious lifestyle with unparalleled proximity to Winter Park’s finest amenities including Historic Park Avenue and Rollins College. Located on a tree-lined street, this residence exudes timeless elegance, complemented by a circular driveway that leads you to its impressive facade. The home has been thoughtfully updated with fresh interior and exterior paint, along with the addition of three new HVAC systems, ensuring modern comfort throughout. Boasting over 4,000 square feet of living space, the home features five generously sized bedrooms, including a second-floor Primary Suite that offers both luxury and privacy. The suite is complete with a private sitting area, a terrace overlooking the lushly landscaped grounds, and a spa-like bath with dual sinks, jetted tub, and a walk-in shower. A spacious walk-in closet provides ample storage space and custom built-ins. In addition to the three bedrooms, the second-floor features a spearate bonus room that is perfect for a private office, or could be converted to an in-law/guest suite, adding versatile living space to the property. The chef’s kitchen is a culinary dream, featuring solid wood 42” cabinetry, elegant granite countertops and a new subway tile backsplash. Adding to the Kitchen's functionality and sophistication are Copper prep and main sinks, Wolf Natural Gas Range, dual dishwashers, under counter ice maker and a walk-in pantry, A separate casual dining space and an island/breakfast bar seamlessly open into the family room, creating an ideal setting for everyday living and entertaining. Off the Kitchen and family room is a full guest bathroom with built in desk area and a multifunctional game room that could convert to a 6th bedroom. Outside, the private oasis is designed for both relaxation and entertainment. A resort-style pool with tranquil fountains serves as the centerpiece, while a beautifully crafted Spanish styled privacy wall, accented with lighting and peaceful bamboo, offers a serene atmosphere. Enjoy the cooler evening relaxing around the piped natural gas fire pit. Enjoy the expansive Cabana area includes a summer kitchen, as well as dedicated seating and dining areas, all overlooking the pool and lush landscaping. With its prime Winter Park location, exceptional privacy, and resort-style amenities, this remarkable home offers the perfect blend of style, comfort, and convenience in one of Winter Park’s most desirable neighborhoods.

1446 Berkshire Avenue, Winter Park

$685,000

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

Experience a lifestyle of refined sophistication and effortless tranquility at The Cloisters Condominium, ideally between Park Avenue and the serene shores of Lake Osceola. This exquisitely remodeled residence offers a seamless blend of timeless elegance and thoughtful design. Set on the second floor, this sun-drenched retreat is bathed in natural light from its northeast-facing sunroom, where expansive windows frame picturesque views of the lush gardens and pool, creating an inviting ambiance throughout the living space. Rich wood floors flow gracefully through the open layout, enhancing the home’s warm and sophisticated character. The primary suite is a private haven, featuring custom-built cabinetry and drawers, a dressing area with abundant closet space and a beautifully updated en-suite bath. A dedicated laundry closet with a built-in washer and dryer adds everyday convenience. The second bedroom offers a custom-built office setup and dual access from the hall and living area, providing effortless versatility as a bedroom, sitting room or private study. The Cloisters offers an array of exclusive amenities designed to elevate everyday living. Guest parking is immediately below the unit in the forward parking circle, as well as along Morse Boulevard, ensuring seamless accessibility for visitors. Additional perks include an assigned covered parking space near the elevator, a dock with boat slips available for lease, two well-appointed fitness rooms, and a beautifully redesigned community space featuring a newly remodeled kitchen and bath. Just steps from the vibrant energy of Park Avenue, this exceptional home provides unparalleled access to fine dining, boutique shopping, cultural attractions, fitness centers and the distinguished Rollins College. Every detail has been carefully curated to create an extraordinary living experience in the heart of Winter Park. Seize this rare opportunity to own a desirable residence at The Cloisters, schedule your private tour today and embrace a home where elegance meets effortless living.

100 S Interlachen Avenue Unit 203, Winter Park

$1,100,000

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

Luxury is a lifestyle, and this Winter Park modern bungalow on a cobblestone street is full of natural light, clean lines and crisp open spaces. Three bedrooms and 2.5 baths in the main house, this home has been thoughtfully renovated with style and beckons the green of an outdoor lifestyle. Over 2,400 square feet in main house and the garage was converted to an additional dwelling unit, adding an additional 400 square feet or so, current use is a studio, can easily transform to a guest house, mother-in-law suite or back to a garage, whatever function fits your needs. Front motor court can accommodate lots of vehicles, easy in and out and includes electric car charging station. The kitchen is open to the gathering room with spacious volume ceilings. Home was recently renovated with stainless appliances, including a Thermador gas range, clean-line cabinets with glass door accents, Cambria Gold quartz countertops, counter seating, a farmhouse sink and gorgeous window to the outside. Main living space is anchored by warm wood floors, with marble floors in bedrooms, all generous in size, with fresh light walls and an extensive lighting package throughout. All baths are updated with marble-influenced accents and gold finishes. Primary suite enjoys sleek authentic Carrera marble seamlessly throughout with walk-in closet for great organization. A luxurious bath retreat showcases a soaking tub, dual sinks and a chic open shower with a frosted window. The natural light in this home adds to the beauty in all spaces. Glass slider doors invite you to the outdoor oasis with an expansive covered pergola, cover is waterproof with the Hercules roof system. Lush greenery and mature landscape and majestic oaks round out the space and topped off with an upscale bar for making entertainment simple. This home was extensively renovated including roof and gutters, re-pipe, newer air conditioners, electrical panels, gas tankless water heater, parking motor court, professional landscape and landscape lighting, the additional separate studio recently updated, paved courtyard, bistro lighting and more. Location is paramount near Winter Park Racquet Club, terrific schools, zoned for Winter Park High, close to Park Avenue, fantastic shopping and restaurants. A great investment opportunity to live among the finest homes in Winter Park and in well-established neighborhood providing a lifestyle like no other.

1932 Temple Drive, Winter Park

$520,000

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

Welcome Home to Orwin Manor – Where Historic Charm Meets Modern Comfort! Nestled in the heart of Winter Park’s highly sought-after Orwin Manor, this 1926 historic gem is brimming with character and thoughtfully updated for today’s lifestyle. Priced below a recent appraisal, this four-bedroom, three-bath home showcases original hardwood floors, a brand-new roof (2024), and reinforced crawl space floor joists, preserving its timeless beauty. Zoned R2, this property offers incredible flexibility with an in-law suite and a detached ADU (Accessory Dwelling Unit) featuring its own private entrance and bathroom—perfect for multi-generational living, a home office, or income-producing rental potential. Step inside to find modern upgrades, including all-new windows, a new irrigation system, a freshly paved driveway, a new water heater, interior paint, granite kitchen countertops, and remodeled bathrooms. Plus, enjoy peace of mind with a transferable termite bond and a recently serviced A/C. Beyond your front door, enjoy a prime location just minutes from Rollins College, boat tours, art festivals, farmers markets, and charming local coffee shops. With easy access to I-4, 1792, Maitland, and downtown Orlando, you’re perfectly positioned for both work and play. Located near top-rated schools like UCF, Rollins College, and Stetson, and just a short drive to world-renowned beaches and theme parks, this home offers endless possibilities. Don’t miss out on this rare opportunity—schedule your private showing today!

1481 Harmon Avenue, Winter Park

$230,000

2 Beds ⋅ 2 Baths ⋅ Chateaux Du Lac SubDv. ⋅ 32789 Zip Code

Waterfront Community on beautiful Lake Killarney. Enjoy breathtaking sunsets on Community deck! Private Boat Ramp on this Skiable Lake, limited Boat parking on property. 2 Bedroom 2 Bath second floor Unit has been meticulously maintained by Winter Resident. Furniture purchased in 2020. Many Updates to Unit include new windows and window treatments, 2024 new Hot Water Heater, Baths redone in 2018-2019, New Appliances within last 5 years. Spacious Room Sizes, Private Balcony. Perfect location! Easy walk to Shopping, Restaurants, Movie Theater, close to Park Avenue and Farmers Market, minutes to I-4. One of Winter Park's best kept secrets! Don't miss this opportunity to view and own in this lovely community!

1500 Gay Road Unit 10C, Winter Park

$3,295,000

4 Beds ⋅ 6 Baths ⋅ Charmont SubDv. ⋅ 32789 Zip Code

Stunning turnkey luxury home in one of the sought-after neighborhoods of Winter Park. Experience unparalleled luxury in this breathtaking four-bedroom, six-bath estate built in 2020, offering over 4,300 square feet of exquisitely designed living space. Every bedroom is a private retreat with its en-suite bath, and the home is adorned with designer finishes and exceptional craftsmanship throughout. Step into the expansive great room, a versatile space that seamlessly blends formal and casual living, featuring a glass-enclosed temperature-controlled wine room, a gas fireplace and a chic dry bar. The chef’s kitchen is a culinary dream, showcasing a massive quartz island, top-of-the-line Thermador six-burner plus griddle gas range with double ovens, a separate freezer and refrigerator, beverage refrigerator, and a spacious walk-in butler’s pantry with a built-in convection microwave and warming drawer. The primary suite is a sanctuary of luxury, featuring dual spa-like baths, a stunning soaking tub, a steam shower, a smart toilet, custom-designed dressing rooms and a hidden safe room. French doors lead to a private lanai with a seating area, an outdoor tub and a serene open-air shower. Upstairs, a spacious 23-by-15-foot family room connects three additional bedroom suites, each with its private bath. One of the bedrooms features a hidden passageway to a 12-by-7-foot bonus room, ideal as a playroom, private media space or climate-controlled storage. Designed for seamless indoor-outdoor living, a 21-by-20-foot covered lanai with a gas fireplace and motorized screens extends from the kitchen and great room via folding glass doors. The two outdoor retreats include a sun-soaked pool deck, built-in grill, firepit, turf lawn, built-in trampoline and basketball court. Additional highlights include a drop-zone off the two-car garage for added convenience. On a charming brick-lined street, this home offers prime access to Park Avenue’s premier dining and shopping, downtown Orlando, major hospitals and Orlando International Airport just 25 minutes away. A rare opportunity to own a turnkey masterpiece that offers the ideal balance of comfort style, and exceptional entertainment spaces.

100 E Rockwood Way, Winter Park

$3,130,000

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

Exquisite Winter Park residence built by Davila Homes, where luxury meets functionality. This impressive home features 5 spacious bedrooms, 5.5 beautifully designed bathrooms, and a generous 4,188 square feet of meticulously crafted living space. As you step through the glass front doors, you’re immediately greeted by the grandeur of beautiful hardwood floors and the high ceilings. The chef-inspired kitchen boasts quartz countertops, custom cabinetry, and top-of-the-line Thermador Appliances, perfect for the chef in the family. The open-concept living, dining, and kitchen areas flow seamlessly, creating an inviting atmosphere for everyday living and entertaining. The primary bedroom suite offers a peaceful retreat with a separate sitting area and massive glass sliding doors with views of the pool and back yard. The spa bath features a wet room with a large walk-in shower and freestanding tub, there is also a spacious walk in closet, and dual vanities with custom cabinetry and quartz countertops. On the second floor you will find three additional bedrooms, each with its own private bathroom, and a massive bonus room with a secret hidden playroom for the little ones. Outside, the home continues to impress with a full covered lanai with retractable screen, ideal for relaxing and enjoying Florida’s beautiful weather. There is also a full summer kitchen, a sparkling pool with a hot tub, and ample backyard space with lush landscaping. Jump on your golf cart and within minutes you’re transported to Park Ave, with its amazing shops, fine dining, and everything else that Winter Park features. Schedule your private showing today and experience the epitome of luxury Winter Park living.

210 E Lake Sue Avenue, Winter Park

$1,555,000

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

Iconic Winter Park treasure! Welcome home to 817 Antonette, an architecturally inviting residence that exudes quality and charm. This thoughtfully designed home boasts detailed moldings and millwork, wood floors, high ceilings, and beautiful oversized windows throughout. A grand foyer leads to a central gallery with an atrium and a custom-designed bannister, while a unique glass ceiling allows for an abundance of natural light. Perfect for entertaining, the home features a large dining room and a chef's kitchen equipped with professional-style appliances, a walk-in pantry, and a built-in banquette. The spacious family room, complete with a fireplace, has French doors that open to a charming outdoor terrace. The versatile floor plan incorporates both formal spaces and options for a home office, nursery, or music room. The main home includes four bedrooms and three baths. The upstairs primary suite is a luxurious retreat, offering a spa-like bath, an oversized closet with built-ins, and a separate room perfect for an office or nursery. The large secondary bedrooms have walk-in closets and are connected by a Jack and Jill bath. Your guests will appreciate the detached apartment, which offers privacy with a full bath, kitchen, and separate courtyard—ideal as a fifth bedroom. Situated on one of Winter Park’s most charming brick streets in the historic College Quarter, this home is just a short stroll to a private neighborhood dock on Lake Virginia. Walk to Park Avenue’s shops and restaurants, Rollins College, the farmer's market, and the Sunrail station. The home celebrates its Federalist architecture with precise and thoughtful details while seamlessly integrating modern amenities. Additional features include an oversized side-entry two-car garage, a new roof installed in 2022, and many windows replaced in 2020. This property is zoned for top-rated schools, including Audubon K-8 and Winter Park High School. Don't miss the opportunity to schedule a private viewing of this unique, one-of-a-kind treasure!

817 Antonette Avenue, Winter Park

32789 Zip Code Real Estate & Homes with No HOA Fee

Advanced Search

Map Search

Home Valuation

Browse All 32789 Zip Code FL Properties with No HOA Fee for Sale