32789 Zip Code FL Just Listed (7 Days) Real Estate, Homes, Condos for Sale

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

Welcome to Park West — an exclusive, gated enclave ideally situated just moments from the vibrant heart of downtown Winter Park. This impeccably maintained 3-bedroom, 2-bathroom residence with a versatile den offers an exceptional combination of elegance, comfort, and convenience. The den, currently utilized as a private home office, can easily serve as a third bedroom to accommodate your needs. The open-concept living and dining areas are highlighted by a traditional decorative fireplace, providing a warm and inviting ambiance for everyday living or entertaining. The spacious primary suite features a private en-suite bath with a walk-in shower and an expansive walk-in closet, while the second bedroom is located adjacent to the hallway bath, which includes a tub/shower combination. A dedicated laundry room with built-in shelving and generous storage is a rare and valuable amenity in condominium living. Residents of Park West enjoy access to an array of premier community features, including a clubhouse, swimming pool, and tennis/pickleball courts — all within the privacy and security of a gated setting. Best of all, this exceptional property is just a short stroll to the boutiques and dining of Park Avenue, world-class museums, Central Park, the SunRail station, and the Winter Park Golf Course. This is a rare opportunity to own a spacious, well-appointed condo in one of Winter Parks most sought-after neighborhoods.

300 Carolina Avenue Unit 304, Winter Park

$420,000

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

Your Opportunity is Here! Renovate this duplex and begin renting both sides or live in one and rent the other! Fenced yard, septic tank and large carport.

1618 Indiana Avenue, Winter Park

$780,000

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

Experience unparalleled sophistication and tranquility with this extraordinary two-bedroom, two-bath condominium, boasting one of the rare and coveted water views in The Cloisters. Nestled on the serene shores of Lake Osceola, this residence offers a unique opportunity to enjoy stunning lake vistas that are available in only a small number of units within the complex. Spanning 1,351 square feet, this haven of light and serenity is designed to accentuate its breathtaking views. The primary suite is a harmonious retreat featuring an en-suite bath, a spacious dressing area with ample closet space, and potential for an added washer and dryer, ensuring both comfort and convenience. The separate kitchen opens to a generous living and dining area, offering picturesque views of glistening Lake Osceola – perfect for intimate gatherings or quiet evenings at home. More than just a place to call home, this condominium is a gateway to a lifestyle of elegance and ease. Exclusive amenities such as covered parking with a dedicated space conveniently close to the elevator, enhance the living experience. Additionally, boat docks, a gym, and an elegant community room within the complex provide leisure options. Managed expertly by FirstService Residential, this property promises a seamless and harmonious living experience. Located just steps from the vibrant shopping and dining of Park Avenue, the charm of Winter Park Village, nearby fitness centers, and the intellectual allure of Rollins College, this home places you at the center of Winter Park's most coveted attractions. Embrace the rare opportunity to own a unit with one of the most desirable water views in The Cloisters. Schedule your private viewing today and discover how this exceptional residence can become your canvas for an extraordinary life.

106 S Interlachen Avenue Unit 317, Winter Park

$2,550,000

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

1440 Place Picardy, Winter Park, FL Custom-Built Elegance with Timeless Finishes A custom-built residence completed in 2008 that blends classic craftsmanship with luxurious, modern living. From the moment you step inside, the superior millwork, solid hardwood floors, and elegant design details make a lasting impression. The gourmet kitchen is a chef’s dream, featuring marble countertops, an oversized gas range, and premium DCS and Sub-Zero appliances. It opens seamlessly to a warm and inviting living area, complete with custom built-ins and a cozy gas fireplace—perfect for entertaining or quiet evenings at home. The spacious primary suite is located on the main floor and boasts generous walk-in closets and a versatile adjoining room, ideal for a home office, nursery, or private retreat. Upstairs, you'll find three expansive bedrooms, three full bathrooms, and a versatile bonus room—perfect for guests, hobbies, or a playroom. Lovingly maintained, this home received a new roof in 2021 and features high-quality windows and doors throughout, bathing every room in natural light. No detail was overlooked. Step outside to your private, beautifully landscaped backyard, which includes a second gas fireplace and a detached flex room—currently used as a gym, but easily converted into a private office or studio space. The oversized three-car side-entry garage offers abundant storage and includes a Tesla charger—ideal for electric vehicle owners. Nestled on a peaceful street, this home is just minutes from everything Winter Park has to offer and is located within the highly sought-after Dommerich, Maitland, and Winter Park school zones. Don’t miss this rare opportunity to own a truly exceptional home in one of Central Florida’s most desirable communities.

1400 Place Picardy, Winter Park

$675,000

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

Nestled in Winter Park one of Central Florida’s most picturesque and established neighborhoods, this beautifully updated 3-bedroom, 2-bathroom residence with a 2-car garage is where timeless charm meets modern, effortless living. Zoned for top-rated Audubon Park K–8 and Winter Park High School, this residence offers both high-end living and lasting value in a truly special location. Inside, you'll find a thoughtfully designed split floorplan with rich travertine floors, arched architectural details, and wood-framed windows that add warmth and timeless character. The primary room boast two walk-in-closets with custom built ins & gas fireplace visible from primary suite & dinning room. What you don’t see at first glance is the over $50,000 in premium upgrades that make this home truly turnkey. From the new roof (2024) and high-efficiency 19 SEER Goodman HVAC (2023) to the instant gas water heater, new garage door and mounting system (2024), fresh exterior paint (2024), and interior paint just completed (May 2025), no detail has been overlooked. Even the gutters and downspouts have been replaced and buried to protect your investment while maintaining the home’s clean aesthetic. The backyard is a true retreat, having undergone a $20,000 professional transformation in 2022 with elegant pavers, a custom pergola, a full irrigation system, and lush, private landscaping—perfect for hosting or unwinding outdoors. Beyond the property lines, this location is simply unbeatable. Zoned for Audubon Park K–8 and Winter Park High School, you’re not just buying a home — you’re investing in one of Orlando’s most sought-after school districts. You’re also minutes from East End Market, Baldwin Park, Leu Gardens, and the best dining, boutiques, and parks the city has to offer. This home is more than just upgraded — it’s elevated. A rare blend of thoughtful design, architectural charm, and everyday convenience, all set in a storybook neighborhood that you’ll love coming home to.Schedule your private tour today.

2602 Winter Park Road, Winter Park

$900,000

5 Beds ⋅ 3 Baths ⋅ Dommerich Estates SubDv. ⋅ 32789 Zip Code

One or more photo(s) has been virtually staged. Seller may consider buyer concessions if made in an offer ~ Welcome to this exceptional –FULLY UPGRADED / POOL HOME– in the highly sought-after Dommerich Estates, where timeless style meets modern design on a spacious .31 ACRE CONSERVATION LOT with serene WOODED VIEWS! Major updates set this home apart; enjoy year round outdoor living with a large lanai featuring motorized retractable screens (2025), a new poolside pergola (2025) and a beautifully resurfaced pool with a sun shelf, new pool deck, and retaining wall (2022). Inside you will find CUSTOM CLOSETS (2025), new PLANTATION SHUTTERS and blinds (2025), FRESH PAINT (2025), an UPDATED ELECTRIC PANEL (2024) and SOLAR PANELS (Owned!) for maximum efficiency. This home also delivers DOUBLE PANE WINDOWS (2020), a NEWER ROOF (2020), WATER HEATER (2019), and a shed for additional outdoor storage was added just this year. Step into a light filled flowing OPEN CONCEPT layout and explore a home designed for both everyday living and entertaining. The heart of the home is the gorgeous CHEF’S KITCHEN, offering the perfect blend of cabinet and drawer storage, open shelving, UPGRADED STAINLESS STEEL APPLIANCES (that include a double wall oven!), sleek countertops, a striking subway tile backsplash and accent wall, and a generous ISLAND with breakfast bar seating. The adjacent dining area boasts a stunning BUILT-IN BAR, ideal for hosting! Throughout the home you will be delighted to find WOOD LOOK TILE and WOOD LAMINATE FLOORING, upgraded light fixtures and fans, elegant crown molding and thoughtful designer touches that elevate every space. The seamless indoor/outdoor flow leads to your private BACKYARD OASIS where you can lounge by the pool, relax under the pergola or gather with guests under the lanai while enjoying the peaceful conservation views. Additional highlights include a CIRCULAR DRIVEWAY, lush landscaping, and fabulous CURB APPEAL. Located in Winter Park with NO HOA this home gives you access to TOP-RATED SCHOOLS and unparalleled convenience being just off Howell Branch Road with easy access to SR 436. You are just minutes away from shopping, dining, parks, and several lakes - all while enjoying the privacy and quiet luxury of this remarkable home. Call today to schedule your tour!

3011 Temple Trail, Winter Park

$3,100,000

5 Beds ⋅ 6 Baths ⋅ Park Grove SubDv. ⋅ 32789 Zip Code

Introducing a stunning brand-new custom home by Butler Ridge Development, located in the highly desirable Park Grove neighborhood—strolling distance to Winter Park’s famed Park Avenue. This home offers timeless elegance, modern luxury, and walkable access to top-tier dining, shopping, and culture. From the inviting circular drive and professionally designed landscaping by Joe Knight, including a signature front palm that sets the tone for this elegant Florida property, every exterior detail makes a statement. Step through the inviting entry into an airy and sun-drenched interior featuring soaring ceilings, wide-plank white oak floors, oversized picture windows, and beautiful crown molding throughout. Inside, a sophisticated office with custom built-ins welcomes you, alongside a thoughtfully designed guest suite with a luxurious bathroom with roll-in shower, soft white finishes, and a custom walk-in closet—ideal for extended family or visitors. The heart of the home is a soaring great room with 14'8" ceilings, a sleek fireplace, and a full wall of sliding glass doors overlooking the resort-style backyard. Entertain with ease in the open-concept living, dining, and chef’s kitchen—complete with a dramatic waterfall island, premium Thermador appliances (including four freezer drawers and diamond ice), dual-fuel range ovens with 6-burner gas cooktop, a 3rd oven + convection microwave, and expansive custom pantry. Adjacent mudroom and decorative laundry room. The first-floor primary suite is a tranquil retreat, featuring pool access, spa bath with soaking tub, separate shower with multiple sprayers, dual vanities, and a spacious custom walk-in closet. Upstairs, a loft-style bonus room complements the smart split-plan layout with 3 additional bedroom suites, walk-ins, and ample storage. Enjoy the best of Florida living in the beautifully landscaped backyard. Designed for both relaxation and entertaining, the outdoor living space includes a saltwater pool with elegant fountain feature, marble pavers, summer kitchen with built-in grill, sink, and beverage fridge, an outdoor bathroom, and ample grassy area for play or pets. 3-Car garage. Located within the highly desirable Dommerich Elementary, Maitland Middle, and Winter Park High School zones, and just minutes from downtown Winter Park, this home offers walkability, elegance, and convenience—wrapped into one exceptional property.

731 Williams Drive, Winter Park

$535,000

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

The Cloisters, one of Winter Park's established and sought-after communities features an ornate architectural design complemented by lush landscaping and an inviting entryway. This fourth-floor two-bedroom, one-bathroom condominium offers approximately 901 square feet with a spacious and modern living experience. Upon entering this residence, you are greeted with a bright and open living area accentuated by abundant wide-plank oak hardwood flooring and complete with features such as crown molding, a Nest thermostat, recessed lighting, and plantation shutters. The primary bedroom provides ample space and natural lighting, while the updated kitchen boasts modern finishes, including new quartz countertops & backsplash, stainless steel appliances, and an induction oven. The bathroom has been upgraded with Kohler fixtures and porcelain tile. For added convenience, the home includes an in-unit washer and dryer, as well as a balcony providing access to the scenic views and spacious grounds. The electrical panel box has been updated, along with new electrical outlets throughout. Residents can enjoy the community's numerous amenities, including a heated pool, hosting events in the renovated social room with a full kitchen, boat dock, and putting green, all set against the tranquil backdrop of Lake Osceola. The association dues include cable TV, building insurance, internet, maintenance (grounds, exterior, pool), on-site management, sewer, trash collection and water, providing a maintenance-free lifestyle. Additional highlights include an assigned covered parking space, storage room and a lakefront seating area. This sophisticated condominium creates a welcoming and refined atmosphere, making this an ideal residence. The location is conveniently located within walking distance to the vibrant Park Avenue, offering access to boutique shopping, dining, Rollins College and the renowned Morse Museum.

100 S Interlachen Avenue Unit 410F, Winter Park

$1,685,000

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

Sold Data Only

1871 Winchester Drive, Winter Park

$2,495,000

5 Beds ⋅ 6 Baths ⋅ Winter Park Heights SubDv. ⋅ 32789 Zip Code

This Fabulous transitional 5 bedroom pool home is perfect for family living & entertaining & just minutes from downtown Winter Park's shopping, entertainment & dining on Park Avenue. Floor plan is ideal w/ 2 bedroom suites downstairs plus office/flex space. Meticulously constructed by Austin Homes, modern & traditional elements blend together w/ its open layout & clean lines. Main floor features a gourmet kitchen w/ Wolf, Sub Zero & Cove stainless appliances, large island, soft close custom wood cabinets & spacious walk-in pantry w/ coffee center/dry bar. This amazing kitchen opens to the family room, exquisite ceiling detail & French doors. The spacious master retreat has a generous walk-in closet. Master bath has a tub, dual vanities & separate shower. Office features a beautiful decorative ceiling design. Private guest suite, laundry & powder bath complete the 1st floor. Upstairs are 3 bedroom suites, a bonus rm, 2nd laundry & a finished walk-in attic. Step outside & relax on your covered lanai w/ summer kitchen or cool off in the sparkling pool/spa w/ sun shelf & heated spa flanked by a large cabana w/ fireplace. Back yard is beautifully landscaped & fenced for privacy. Relax in your private hot tub enclave with television. Amenities include: granite & quartz counter tops, Level 4 smooth finish walls & ceilings, hardwood floors in all main living areas, custom closet systems, brick paved driveway, PGT vinyl Low E insulated windows, core fill & block walls, high density spray foam insulation in ceilings, R13 in walls, Trane 16 Seer variable speed AC dual systems & 2 tankless water heaters.

1690 Palm Avenue, Winter Park

$765,000

3 Beds ⋅ 3 Baths ⋅ Canton Ave Cottages 1 SubDv. ⋅ 32789 Zip Code

BACK ON MARKET WITH NEW PRICE DUE TO BUYERS CASH PURCHASE DEFAULT!!!Rare find in the heart of Historic West Winter Park - Newer 2017 solid built David Weekley home now available! This modern designed chic home offers energy efficient features with luxury design. Walk into the home and be impressed by the voluminous ceilings and 8' door frames adorned with ceiling crown molding. This unique home design offers ultimate privacy with all bedrooms on the lower floor while the living/entertaining space is upstairs. Windows throughout the home filtrate a natural light that compliment the wooden floors. Upstairs you'll find the living space large and inviting. The chef's kitchen is spacious with abundant cabinetry and offers all stainless-steel Jenn Air appliances. The commercial style gas cooktop offers a wall mounted kettle water feature along with a flat surface griddle and is topped with a deco canopy range hood. The built-in bottom mount refrigerator is complimented alongside the programmable electric oven and convection/microwave. Center kitchen island doubles as dining space with room for four or there's room for a dining table. Solid wood cabinets are topped with glass doors to display stylish dinnerware. Dual pantry sliders with pull out drawers adjoin the wine refrigerator (Jenn Air of course) with additional cabinets. The Great Room's sliding glass doors welcomes you outside to the expansive maintenance free Hardee board deck. The deck is pre-plumbed for both water and gas to complete your grilling needs. The luxurious primary bedroom offers a tray ceiling and large walk-in closet. Venture into the impeccable primary bath and enjoy the huge walk in shower with built-in bench seat and overhead rain and wall mount shower heads. The additional two bedrooms share a bathroom accessible by each side but has a separate door to shower and toilet. The downstairs enormous laundry room is complete with a sink and additional cabinets. You'll find the garage oversized and can be described as 2.5 car size with epoxy coated flooring and an EV charger. Water Softner system stays - easy to use! There's an additional parking pad for your guests. The home is completely fenced and has energy efficient dual tankless gas water heaters and is prewired for 5.1 Surround sound audio. Best part of this small brick paved urban planned community - HOA pays for landscaping maintenance, plant replacement, mulch and sprinkler repair and you're connected to a natural gas utility service. Walk to the best shopping and dining available in Central Florida - Park Ave. and Winter Park Village. The Sunrail and Amtrak train depot is only 6 blocks away with Rollins College right around the corner. Easy commute to Downtown Orlando, Full Sail University and the Orlando International Airport. Best value in 32789 zip code!!! Call today for your showing.

441 N Capen Avenue, Winter Park

$1,199,000

3 Beds ⋅ 3 Baths ⋅ Maitland Shores First Add SubDv. ⋅ 32789 Zip Code

Modern Midcentury Retreat with Luxe Upgrades & Private Community Lake Access This meticulously renovated 3-bed, 2.5-bath midcentury home blends timeless design with high-end contemporary finishes. Reimagined in 2021, it features an open floorplan highlighted by terrazzo flooring, quartz accent walls, and a cozy family room with bamboo floor and a gas fireplace. The sleek, chef-inspired kitchen showcases Italian Cento Per Cento wall tile, Thermador appliances including a 6-burner gas cooktop, double wall ovens (rotisserie + convection/steam), dual-zone wine fridge, Delorean-style cabinetry, and custom island lighting. A built-in pantry with pull-out shelving, cutlery storage, and a hydraulic lift mixer stand add both function and flair. Retreat to the Phil Kean-designed primary suite complete with king bed, nightstands, electric blinds, and integrated closet system. The ensuite spa bath features a Jacuzzi tub with high volume filler, separate high-pressure shower with steam, Robern vanity, and inset medicine cabinet to hide charging toothbrushes. Additional features include a 2-car garage with insulated door and interior storage, whole-house reverse osmosis water filtration, and a private backyard oasis with a saltwater pool and 10 x 15 cabana. Bring your boat and enjoy exclusive canal access to Lake Maitland!

2525 Venetian Way, Winter Park

$646,000

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

Welcome to this delightful 1,600 sqft home in one of Winter Park's most coveted neighborhoods. This three-bedroom, two-bathroom home blends classic charm with modern updates. Roof replaced 2023,A/C replaced 2021, double pane windows installed 2020. The beautifully updated kitchen features newer appliances and opens to a cozy living area with a character-rich wood-burning fireplace. The versatile 23'x11' living and dining area offers multiple configuration options, perfect for entertaining or creating dedicated spaces for different activities. A welcoming brick paver courtyard with charming arbor overhead creates a picturesque entrance. French doors open to a covered patio, perfect for outdoor living. Situated in a well-established neighborhood with new custom-built homes, this property balances mature community charm with contemporary design influences. The location is unbeatable – within easy walking distance to highly-rated Audubon Park K-8 school, the thriving Audubon Park Garden District restaurants, and unique boutique shopping. Just minutes away, you'll find Baldwin Park Village Center with it's Michelin Star rated restaurants, the vibrant Mills/50 District, and the iconic Park Avenue experience. This exceptional home offers the quintessential Winter Park lifestyle in a location that combines established neighborhood character with exciting urban accessibility.

2711 Parkland Drive, Winter Park

$1,635,000

4 Beds ⋅ 5 Baths ⋅ Acreage SubDv. ⋅ 32789 Zip Code

Get Busy Living the Winter Park lifestyle in this custom 4-bedroom, 4.5-bathroom pool home tucked away at the end of a 150-foot private drive with gate. Designed with comfortable yet sophisticated living space, this home is perfect for those seeking a serene retreat for both everyday living and entertainment. The heart of the home is the sizable kitchen, boasting a gas stove, high-end appliances, and a truly unique island crafted from reclaimed wood with a solid concrete countertop — a perfect blend of rustic charm and modern design. The primary retreat is conveniently located on the first floor, featuring a spa-like bathroom complete with a soaking tub and a spacious walk-in shower. Upstairs, you'll find two additional ensuite bedrooms with the 4th bedroom that doubles as a home office complete with built-in desk and murphy bed. A generously sized bonus room/living area upstairs provides additional flexibility for a media room, playroom, or home office. Outdoors, the professionally designed and illuminated landscaping sets a warm, welcoming tone which includes a spectacular 12' x 40' salt-filtered heated pool surrounded by a luxurious travertine deck with fire-pit. Close proximity to all the charm and amenities Winter Park has to offer. This exceptional home offers privacy, elegance, and thoughtful design at every turn. Call today for an easy showing!

2402.5 Temple Drive, Winter Park

$217,500

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

Welcome to this beautifully maintained 2-bedroom, 2-bath condo in the serene community of Mead Gardens. This second-floor unit offers the ease of single-level living once inside, featuring an open-concept layout filled with natural light. The updated kitchen (2016) boasts stylish tile flooring that mimics hardwood, granite countertops, a farmhouse sink, and stainless-steel appliances, all overlooking the spacious great room. One of the property's standout features is the spacious private balcony overlooking the lush beauty Mead Gardens. The balcony offers privacy and tranquility as there are no rear neighbors. The primary suite offers a peaceful garden view, an ensuite bath with walk-in shower and a single vanity. The second bedroom features sliding doors to the front entry and has easy access to a full guest bathroom with a tub/shower combo. Residents enjoy access to a sparkling community pool, laundry facilities, and mailboxes just steps away. Enjoy this prime Winter Park location, located just minutes from Park Avenue and Rollins College.

1250 S Denning Drive Unit 230, Winter Park

$1,115,000

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

Endless Potential in the Heart of Park North! Just steps from the charm and energy of Winter Park’s Park Avenue—where boutique cafés, fine dining, art galleries, museums, Central Park, and the Winter Park 9 Golf Course await—this rare Park North gem offers the ultimate opportunity to create your dream home. Nestled at the end of a peaceful cul-de-sac, this expansive .38-acre lot (16,534 SF) is a true find in one of Winter Park’s most desirable neighborhoods. Whether you're looking to build new or renovate the existing residence, the possibilities here are limitless. The current single-story block home spans nearly 3,100 square feet, with strong bones and a layout designed for easy living. Inside you’ll find oversized rooms, a cozy fireplace, a spacious eat-in kitchen, an indoor laundry room, private office off the primary suite, and a 2-car garage. Recent updates—new roof (2023), updated electrical panel (2023), one A/C (2019) and modernized windows and doors—set the stage for your vision to come to life. Natural light fills the home, and the beautifully landscaped backyard offers a serene retreat with a private patio, rear privacy wall, and metal fencing—ideal for both everyday relaxation and stylish entertaining. Located in the coveted Winter Park school district, this is a rare chance to invest in a premium property with endless upside. Whether you choose to reimagine the existing home or build brand new, this is a canvas just waiting for your personal touch. Schedule your private showing today and explore the possibilities! ** SURVEY AVAILABLE IN ATTACHMENTS **

309 Park North Court, Winter Park

$1,002,000

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

Welcome home to this beautifully upgraded gem nestled in the heart of Winter Park. This move-in-ready home sits on a quiet street, offering easy access to major highways, top-rated schools, upscale dining, shopping, and Central Florida’s best attractions. No detail has been overlooked in this full renovation. The custom kitchen is a chef’s dream—featuring quartz countertops, an oversized island with built-in drawers and cabinets, brand new high-end appliances, a cooktop vented through the roof, and a stylish backsplash. The layout includes a custom office/library space, redesigned laundry room with tailored cabinetry, and thoughtfully added storage throughout. You'll love the engineered wood floors in the bedrooms and modern tile in the kitchen, bathrooms, and laundry, all with matching grout and designer finishes. Upgrades include: - Dave Lennox Signature Collection A/C system - All-new Renewal by Andersen windows and doors - Upgraded garage door and rail system - Vivint security system with 5 outdoor cameras - Custom gutters with Leaf Filter protection - New pool filter, skimmers, and lids/ Pool heater and cooler - Completely remodeled bathrooms with new tile, vanities, showers, and fixtures - Smart light switches, USB/USB-C outlets, and designer light fixtures inside & out Freshly painted inside and partially outside, this home also features a brand new USPS-approved mailbox, visible house number signage, and privacy-enhancing white vinyl fencing on both sides. This home isn’t just a house, it’s a complete lifestyle upgrade in one of Winter Park’s most desirable neighborhoods. Schedule your private tour today! **Sellers will contribute $3,000 to a buyers closing costs with an accepted full price offer**

1265 Park Pointe Lane, Winter Park

$1,050,000

4 Beds ⋅ 4 Baths ⋅ Dommerich Cove SubDv. ⋅ 32789 Zip Code

A RARE Winter Park Estate Blending TIMELESS CRAFTSMANSHIP with MODERN FLEXIBILITY & RESORT-STYLE Living comes to market for the FIRST TIME. 2923 Cove Trail is nestled between the best of Winter Park & Maitland. Masterly created by the renowned Charlie Clayton it blends unmatched craftsmanship with modern design & flexibility craved by you, today’s discerning buyer. REIMAGINED in 2011 this 4-bedroom, 4-bath home features WHITE OAK FLOORS, SOLID WOOD CABINETS, CARRERA MARBLE & TRAVERTINE finishes, along side preserved architectural details like SKIP TROWEL CEILINGS & CROWN MOLDING. Updates fashioned TWO PRIMARY SUITES offering ultimate privacy & flexibility.These SPLIT PLAN suites pack personality. The first provides a POOL VIEW, large WALK-IN CLOSET & SHOWER, while the second basks in the PRIVACY of its own SCREENED GARDEN PATIO & access to a COZY FLEX ROOM with BUILT-INS. Whether used as a SERENITY ROOM, craft space, or restyled into a KITCHENETTE this space adds rare flexibility. Flexibility & MULTIGENERATIONAL living in a ONE STORY home aren’t the only rarities you’ll marvel over. A LARGE SEPARATE OFFICE with PRIVATE EXTERIOR ENTRANCE provides an ideal location for professionals to consult with clients or social media influencers & podcasters to ply their trades. Imagine the freedom & peace of mind you’ll gain not having to worry about traffic while also freeing your business from overhead & lease costs. When the workday ends, entertaining begins & other shiny facets of this home sparkle. A 2,500-BOTTLE CLIMATE-CONTROLLED WINE CELLAR sets the stage for unforgettable gatherings. Whether selecting a vintage for a romantic dinner, indulging guests with formal tastings or kicking back for a relaxed evening you’re sure to savor these moments especially when you move the party outdoors to your PAVERED PATIO adjoining the cool blue waters of your 18x36 RESORT-STYLE POOL all tucked within the PRIVACY of lush 8-foot WALLS. Don’t forget the patio is plumbed for an OUTDOOR BBQ & the pool for SOLAR HEAT when you’re ready to add them.The outdoors isn’t the only place you & your guests will gravitate to. Indoors, enjoy seamless FLOW between the SUNROOM, LIVING room, & FAMILY rooms. BUILT-IN SPEAKERS & STEREO SYSTEMS effortlessly deliver music to your ears. FIREPLACES in both living areas add warmth & ambiance for every season. Some properties claim to have a CHEF'S KITCHEN. This one delivers. Beyond the aesthetic updates, your cooking talents will flourish as you pivot between the island PREP SINK, professional grade 6-BURNER GAS COOKTOP with POT FILLER exceptional overhead VENT, BUILT IN OVENS & stainless steel FRENCH DOOR REFRIGERATOR. For those extra busy celebrations, just around the corner in the laundry room a complement of CABINETS,2ND FULL FREEZER & 2nd REFRIGERATOR await your handiwork while the WASHER & DRYER stand ready for tidying. There’s so much more, but here are a few more highlights:IMPACT-RESISTANT WINDOWS, a PARTIAL HOME GENERATOR, IRRIGATION ON WELL, owned SECURITY SYSTEM & 3 BUILT-IN SAFES— all contributing to your long-term comfort & the home’s efficiency. There’s NO DOUBT this property DELIVERS UNMATCHED VALUE, & QUALITY in one of Winter Park’s MOST DESIRABLE neighborhoods. Homes of this CALIBER RARELY COME TO MARKET— AND WHEN THEY DO THEY DON'T LAST. SCHEDULE your private showing TODAY. This is more than a home — IT'S the LIFESTYLE UPGRADE You've been WAITING FOR. *CLICK on Virtual tour link for 3D Walk Through.*

2923 Cove Trail, Winter Park

$1,050,000

3 Beds ⋅ 4 Baths ⋅ Canton Ave Cottages 1 SubDv. ⋅ 32789 Zip Code

Welcome to your dream home in the heart of beautiful Winter Park, Florida! Just a short stroll to iconic Park Avenue and Winter Park Village, this stunning modern Craftsman by David Weekley Homes perfectly blends luxury, comfort, and convenience. The thoughtfully designed floor plan features a downstairs primary suite, rich hardwood flooring, and sliding barn doors opening to a versatile dining room or home office. The heart of the home is the gourmet all-white kitchen, showcasing Cambria quartz countertops, a large center island, and top-of-the-line JennAir appliances—ideal for both everyday living and entertaining. Perfect Lock & Leave Living! Enjoy effortless living in this beautifully maintained neighborhood, ideal for those seeking a low-maintenance lifestyle. With all lawn care included, you can spend more time doing what you love—whether that's traveling, entertaining, or simply relaxing. Just lock the door and go—peace of mind comes standard. Located in the vibrant community of Winter Park—home to Rollins College, Michelin-starred restaurants, charming local boutiques, parks, and a lively farmers market—you’ll also love being just minutes from Winter Park Village for shopping, dining, and entertainment. Don't miss this rare opportunity to own a modern gem in one of Central Florida’s most sought-after neighborhoods!

795 W Canton Avenue, Winter Park

$2,435,000

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

Welcome to a one-of-a-kind, custom-designed residence offering the perfect blend of modern sophistication, thoughtful functionality, and resort-style amenities. Designed by Origins Residential Design and meticulously constructed by Native Homes, this 5-bedroom, 5.5-bathroom showplace is located in one of Winter Park’s most sought-after neighborhoods—just minutes from Park Avenue, Baldwin Park, and top-rated schools. This exceptional home was built in 2019 and features a flexible, open-concept layout that exudes comfort and luxury. The spacious main living areas are drenched in natural light and designed for seamless entertaining and everyday ease. The split-bedroom floorplan offers five generously sized en-suite bedrooms, each with its own private bath—no shared walls between any bedrooms ensure total peace and privacy for all. Two bedrooms are located on the first floor, including the lavish downstairs primary suite with a spa-inspired bathroom featuring a soaking tub, oversized dual vanities, frameless glass shower, and an enormous custom-designed walk-in closet. The heart of the home is the chef’s dream kitchen, masterfully laid out with distinct zones for cooking and gathering. Highlights include a gas cooktop, Thermador appliances, huge quartz-topped island, 42” cabinets, a cozy coffee and juicing nook, an oversized walk-in pantry, and a striking design that marries stainless steel with warm brass accents. Just off the kitchen, a separate beverage zone includes a built-in wine fridge, making entertaining effortless. No detail has been overlooked—from the White Oak hardwood flooring and marble inlay floors, to the suspended ceilings, solid Shaker-style interior doors, 7” milled baseboards, and designer light fixtures throughout. Modern conveniences include pre-wired surround sound, recessed lighting, dimmable lighting with frameless switch plates, custom framed mirrors, new Kohler bath fixtures, and a whole-house water filtration system. Restoration Hardware sheer drapes ($20K), remote-operated Shade Store treatments Enjoy seamless indoor-outdoor living in the resort-style backyard retreat. The ultra high-end, zero-edge saltwater pool and spa feature Aqua Pearl interior finish, glass mosaics, and are fully smartphone-controlled, including lighting, jets, and both gas spa and pool heaters. Entertain under the covered outdoor patio complete with an Artisan grill, new neutral-toned accent walls, and outdoor kitchen—all surrounded by sandblasted Carrara marble pavers, remote-controlled vanishing screens, and a full privacy fence with Podocarpus hedge. Extensive professional landscaping includes fresh sod, tilled and leveled topsoil, blooming flower bushes, and river rock side paths. The backyard also features new turf, a dedicated dog run, and completely upgraded irrigation for optimal efficiency. Oversized 2-car garage, tile roof, gutter guards, security system with cameras, new washer/dryer, and professional landscaping with upgraded irrigation. Quiet zone near hospitals, attracting medical professionals. Electrical lines to be buried within few months and very strong internet. Minutes to Baldwin Park, Park Avenue, restaurants, shopping, Wellness Center, and scenic trails. Zoned for top-rated Winter Park schools (Brookshire, Glenridge, Winter Park High) and near private schools- Lake Highland Prep, Park Maitland, Geneva School and more

1795 Greenwich Avenue, Winter Park

$632,100

2 Beds ⋅ 2 Baths ⋅ Village Winterset Inc SubDv. ⋅ 32789 Zip Code

This beautifully updated 2-bedroom, 2-bathroom corner unit is located in the highly desirable Winterset Condominiums on East Canton Avenue, just one block from Park Avenue in the heart of Winter Park. The unit features hardwood floors, crown molding, plantation shutters, and an open floorplan filled with natural light. The kitchen is fully upgraded with GE stainless steel appliances, a wine fridge, soft-close cabinets, and quartz countertops. Additional highlights include a programmable thermostat, updated lighting and ceiling fans, and a private storage unit on the same floor. Offered fully furnished with designer pieces, the unit also includes an assigned covered parking spot and access to the community’s pool. Winterset is an owner-occupied building; no rentals or pets are permitted. Live the ultimate Winter Park lifestyle - just steps from Rollins College, the Winter Park Golf Course, beautiful lakes, and top-tier dining, shopping, and more. Rarely available - schedule your private showing today!

225 E Canton Avenue Unit 225, Winter Park

$1,042,500

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

Ideally located in the heart of Winter Park, just steps from iconic Park Avenue and around the corner from Winter Park Village, this beautifully renovated 4-bedroom, 3-bath home offers the ultimate in walkable luxury living. Nestled on a charming brick street lined with sidewalks, this residence combines timeless elegance with unbeatable convenience. Inside, enjoy 10’ ceilings, rich wood, custom tray ceilings, and detailed crown molding. The home has been thoughtfully renovated, delivering a fresh, timeless aesthetic throughout. The flexible downstairs bedroom makes a great guest suite, home office, or den. Upstairs, the stunning primary suite is a true retreat, complete with French doors to a private covered patio, a walk-in closet, and a newly renovated spa-like bath featuring dual vanities, an oversized soaking tub, and a luxurious steam shower. Two additional upstairs bedrooms share a modern, well-appointed bathroom, and a conveniently located laundry room adds to the home’s functional appeal. Step outside and enjoy Florida living at its best with a second covered patio that opens to a spacious, private backyard—a rare find this close to Park Avenue. A paver driveway with extra parking pad leads to a one-car garage. Located in a top-rated school district and are the corner from shops, restaurants, parks, and more, this home offers a lifestyle of comfort, charm, and convenience in one of Winter Park’s most sought-after neighborhoods.

1341 Lyndale Boulevard, Winter Park

$570,000

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

One or more photo(s) has been virtually staged. Tucked away on the tranquil shores of Lake Killarney, this impeccably remodeled two-story residence offers a rare opportunity to enjoy waterfront living with unmatched convenience. Just steps from Hillstone, Trader Joe’s, and Winter Park Village, this 2-bedroom, 2.5-bathroom home is the perfect blend of modern sophistication and timeless charm. Inside, you’ll find a beautifully designed open-concept kitchen ideal for entertaining, two spacious primary suites—each with its own spa-inspired en-suite bathroom—and a bonus office space with sweeping lake views that make working from home feel like a retreat. From top to bottom, every detail has been thoughtfully curated for both comfort and style. Step outside to your private covered patio and soak in postcard-worthy sunsets, or head down to the dock for a quiet moment by the water. The community offers a serene lakeside pool, very low HOA fees, and a laid-back lifestyle just minutes from some of Winter Park’s best shopping and dining. Come discover a one-of-a-kind home where lakefront tranquility meets urban convenience—this is Winter Park's best kept secret.

640 Killarney Bay Court Unit 4, Winter Park

$3,485,000

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

$175,000

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

Under contract-accepting backup offers. This charming two-bedroom, two-bathroom 2nd floor condo offers the perfect blend of comfort and convenience. Featuring tile and luxury vinyl plank flooring throughout, this home provides durability and style for modern living. The HVAC was replaced in 2020 and water, cable and internet are included in the monthly COA fee. Located in a picturesque community ON THE SHORES OF A SKI LAKE, residents will enjoy access to boat slips (based on availability, charge is $30/month), a boat ramp, a sparkling pool, a welcoming clubhouse, and mature landscaping that enhances the serene environment. Outdoor enthusiasts will appreciate the multiple barbeque grills and tables, ideal for courtyard or lakeside dining. Additional amenities include two on-site laundry rooms, on-site storage, and convenient proximity to key destinations. COA approval is required. The application fee is $85.00. Situated in Winter Park, the community is less than 10 minutes from Winter Park Village, Maitland, and Downtown Winter Park, about 10 minutes from College Park, and approximately 15 minutes from Downtown Orlando and Lake Mary. This prime location ensures easy access to shopping, dining, entertainment, and the vibrant city lifestyle.

2500 Lee Road Unit 208, Winter Park

$260,000

2 Beds ⋅ 1 Baths ⋅ Lake Killarney Condo SubDv. ⋅ 32789 Zip Code

Fantastic 2 bed/ 1 bath - first floor condo in cool, mid-century building on Lake Killarney. This home is next to Trader Joes, Hillstone's and across the street from Winter Park Village! Lakefront Winter Park Condo Community Ground Floor Remodeled 2 Bedroom 1 Bath Condo, Remodeled Kitchen and Bath, Includes Washer Dryer Inside Unit. Wood Look Laminate and Tile Floors. Lake Front Amenities, Boat Launch, Pool, Shuffleboard, Park Like Setting on Lake Killarney. This property also has Fitness and Recreation Facilities Onsite. Across the street from Winter Park Village for all your shopping & dining needs. Just a few minutes to Park Avenue and I4.

151 N Orlando Avenue Unit 115, 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

$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

$1,942,000

5 Beds ⋅ 5 Baths ⋅ Park Grove SubDv. ⋅ 32789 Zip Code

One or more photo(s) has been virtually staged. Five-bedroom, 3900+ sq ft pool home with 3 car garage on a large corner lot in the sought -after Park Grove neighborhood near Lake Maitland and Park Avenue. Great Room consists of a Family Room area with a wood-burning fireplace and tray ceilings and a Sun Room area with bay windows and french doors overlooking the pool deck. Kitchen bordering the spacious Great Room Area, features a cooking island and custom teak counters with a closet pantry and an extra 7’ x 5’ storage area/dry bar and is adjacent to a butler pantry and laundry room. The luxurious Primary Suite, that opens to its own deck over the back yard and pool deck, features a coffered ceiling, a very large walk-in closet as well as additional closet space. The large Primary Bath contains dual vanities, whirlpool tub, and separate shower. The Second Bedroom Suite includes an en-suite bathroom, built in shelves and a corner window niche for make-up or a reading/work area. Bonus Room with bay windows, built in shelves/entertainment center and dual closets has been utilized as an extra bedroom or as a gaming area. The Living Room, with a wood burning fireplace, is adjacent to the entry foyer and opens to the Dining Room featuring bay windows that could also serve as a sizable and elegant office area. The entire home features recently finished wood floors. 3-zone central HVAC system and dual pane – energy efficient windows and updated, blown-in insulation in attic will keep you comfortable all year round. Recent roof update. Near the Park Avenue Downtown District - Imagine a downtown where history, art, and nature blend seamlessly, creating a vibrant and welcoming community. Here, the past meets the present in every shop, event, and stroll down the Avenue. Residents feel a deep sense of pride and belonging, while visitors are drawn to the charm and warmth that define our town.

1394 Stewart Street, 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

$243,800

2 Beds ⋅ 3 Baths ⋅ Sandalwood Creek Condo Ph 04 SubDv. ⋅ 32789 Zip Code

One or more photo(s) has been virtually staged. Dreams Do Come True! FHA, VA, and DPA approved, making it a smart choice for a wide range of buyers. Welcome to your next home in the heart of 32789—Winter Park’s hidden gem, Sandlewood Creek! This rare townhome-style condo offers unbeatable value in a prime location with NO neighbors above or below and a LOW HOA. Step inside and enjoy nearly 1,000 sq. ft. of comfortable living space with an open floorplan, tile flooring downstairs, a large kitchen, and a convenient half-bath and laundry area with washer and dryer included. The 2021 Lennox HVAC system keeps things cool and efficient year-round. Upstairs, you'll find two spacious bedrooms with plush carpeting, and two full bathrooms, making this home as practical as it is inviting. Step outside to your private fenced patio—perfect for relaxing or entertaining. The Sandlewood Creek community is well-maintained and features a sparkling pool for your enjoyment, all while offering a low-maintenance lifestyle. Located just minutes from Park Avenue, Downtown Maitland, and top-tier shopping, dining, and entertainment, this home is also zoned for Dommerich Elementary, Maitland Middle, and Winter Park High—some of the most sought-after schools in the area. Affordable, move-in ready, and packed with value, this is a rare find in Winter Park you don’t want to miss!

255 Sandlewood Trail, 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

$417,100

2 Beds ⋅ 2 Baths ⋅ Lake Virginia Condo SubDv. ⋅ 32789 Zip Code

One or more photo(s) has been virtually staged. Beautifully Renovated Lakefront Condo with Partial Lake Virginia & Downtown Views. Located just minutes from Park Avenue and Rollins College, this fully renovated condo offers stylish, maintenance-free living with partial views of Lake Virginia and the downtown skyline. The open-concept layout features a brand-new kitchen with quartz countertops, stainless steel Samsung appliances, recessed lighting, and an oversized island with bar seating. The spacious primary suite includes a private dressing area, three closets (including a walk-in with custom storage), and a beautifully updated en-suite bath with dual sinks and a walk-in shower. The guest bedroom has generous closet space and is served by a renovated bath with a soaking tub/shower combo. Three additional hallway closets also has exceptional storage. Additional updates include new central A/C, new hot water heater, new flooring throughout, and an in-unit washer and dryer. Community amenities include: a lakefront pool and hot tub, boat dock, fitness center, kayak storage, fire pit, bike storage, elevator, and reserved covered parking. Don’t miss this rare opportunity to own a modernized lakefront unit in one of Winter Park’s most desirable locations!

690 Osceola Avenue Unit 502, 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

$420,000

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

Welcome to 1228 Park Green Place in beautiful Winter Park! This updated 3-bedroom, 2-bathroom home effortlessly combines modern style and everyday comfort in one of Central Florida’s most desirable communities. Inside, you’ll find updated LVP flooring throughout the main living areas with a beauitful fireplace. The kitchen offers ample storage and is complemented by a separate wet bar area—perfect for entertaining guests. The open layout flows into a spacious private patio, ideal for outdoor dining or relaxing. The primary suite has its own private access to the patio, and complemented by its spacious bathroom that is beautifully renovated with sleek, contemporary finishes. One of the bedrooms features a dedicated AC splitter unit and is currently used as a custom wine room—an excellent option for wine lovers or anyone needing a flexible space. Just minutes from top-rated Winter Park schools, shopping, dining, and major highways, this move-in-ready home offers both convenience and charm in a prime location.

1228 Park Green Place, 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

$2,625,000

4 Beds ⋅ 6 Baths ⋅ Virginia & Morse Brownstones SubDv. ⋅ 32789 Zip Code

Step into luxury with this stunning three-story townhouse featuring an elevator and abundant natural light. A breathtaking staircase elegantly wraps around a magnificent chandelier, creating a striking focal point from the first floor to the third. The first floor boasts a chef's kitchen with high-end cabinets, top-of-the-line appliances, and premium flooring. The second floor offers four elegant main suites, each designed for comfort and privacy. The third floor is home to the impressive main suite, located next to the rooftop terrace, which includes a gazebo and jacuzzi. This home is equipped with an internal vacuum system and a state-of-the-art Pelican water filtration system for ultimate convenience and water quality. A charming backyard garden, a two-car garage, and a prime location within walking distance to top restaurants, parks, and farmer's market complete this exquisite property- ideal for stylish buyers seeking a vibrant lifestyle.

141 N Virginia 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

$770,000

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

Welcome to The Mondrian Winter Park, where modern elegance meets serene waterfront living! This extraordinary community features 30 sleek townhomes nestled alongside the tranquil shores of enchanting Lake Killarney. Step inside and be captivated by the exquisite finishes that define this remarkable residence—a true testament to quality and sophistication. Upon entering, you’ll find a palette of fresh interior paint and contemporary flooring that sets the tone for stylish living. Revel in the comfort of privacy shades, chic lighting fixtures, and ceiling fans that create an atmosphere of calm and relaxation. The kitchen is a gourmet's delight, boasting a natural gas cooktop and a dedicated wine refrigerator, providing the perfect backdrop for memorable gatherings. Unwind in the opulent master suite, complete with a stunning walk-in glass shower, a private water closet, and ample closet space to accommodate your wardrobe. Your very own retreat awaits on the expansive rooftop terrace, where you can enjoy treetop vistas, a charming pergola, and a spacious lounge area—ideal for hosting soirées or indulging in quiet stargazing. With soaring 10'6" ceilings and oversized storefront-style windows, natural light pours into the living space, creating an uplifting and inviting ambiance. Each of the three generously sized bedrooms features its own bathroom, ensuring privacy and comfort for family and guests alike. Perfectly positioned just north of downtown Orlando, this luxury enclave offers a lifestyle like no other. Bask in breathtaking views of Lake Killarney from the newly constructed dock, or find tranquility at the lakeside pavilion as the sun sets. If you’re drawn to aquatic adventures, a private boat slip is available for purchase, allowing you to glide across the lake to Trader Joe’s or savor a meal at Shake Shack. For outdoor enthusiasts, the community’s kayak and paddleboard racks provide effortless access to fishing, exercising, or simply soaking up the peaceful surroundings. Explore Winter Park Village for an array of shopping and fine dining experiences and immerse yourself in local culture at the vibrant Farmer’s Market and the acclaimed Enzian Theater. Welcome to The Mondrian Winter Park—a harmonious blend of luxury, comfort, and the promise of adventure at every turn. Your new home is waiting!

1816 Mondrian Circle, 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

$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

$362,500

1 Beds ⋅ 1 Baths ⋅ Phillips Circle Rep SubDv. ⋅ 32789 Zip Code

Priced to sell!! Motivated Seller. Outstanding structural integrity, no big assessments ahead! Whispering Waters passed its structural integrity inspection and reserves study with flying colors—earning compliments for the quality and care of the buildings. This is a very well-managed community, and the $1,054 monthly HOA covers nearly everything, including electricity! The only exception is cable and internet, making this an incredible value with true peace of mind. Tucked away just two blocks from Park Avenue, this one bedroom, one bathroom corner unit places you in the heart of downtown Winter Park—steps from acclaimed restaurants, charming shops, and the iconic boat tour on Lake Osceola. Situated on the second floor of Building 6 with convenient elevator access, this light filled condo has brand new carpet in the living areas and bedroom, creating a fresh and cozy feel. The kitchen features granite countertops, a built-in oven, glass cooktop, stainless steel refrigerator, and recently painted blue, solid wood cabinetry that adds a fun pop of color to the space. A dedicated dining area is located just off the kitchen and includes sliding glass doors that open to a small private balcony overlooking Morse Blvd—perfect for enjoying your morning coffee. Off the living room, an enclosed sunroom offers bonus living space with abundant natural light, motorized custom blinds, and upgraded windows for improved energy efficiency and sound insulation. The oversized bedroom offers space for a sitting area and features motorized shades for added comfort and privacy. A convenient door allows you to close off the bedroom —ideal for when guests are visiting and need access to the bathroom without entering the bedroom. The unit also comes with one assigned parking space in the garage, additional storage, and the peace of mind that HOA covers electric, water, sewer, trash, building insurance, pool maintenance, landscaping, and on-site management. Whispering Waters is a lakefront community on beautiful Lake Osceola, with water access available to residents—bring your kayak, soak in the serene views, or enjoy a sunset by the water. Whether you're seeking a full-time residence or a part-time getaway, this home offers effortless, low-maintenance living—just lock and leave. Bonus: Since the current owner is under 55, the next buyer can be too (only 85% of residents need to meet the 55+ age requirement). Call today to schedule your private showing!

311 E Morse Boulevard Unit 6-7, 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

$1,305,000

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

Back on the market at no fault of the seller. Step into the charm of old Florida with this stunning historic home in the heart of Winter Park's exclusive Sevilla neighborhood. Built in 1973 by Charles Clayton, this beautifully preserved residence seamlessly blends timeless elegance with modern comforts. Featuring original hardwood floors, intricate crown molding, and a cozy wood-burning fireplace, every detail reflects meticulous craftsmanship and a timeless aesthetic. The updated gourmet kitchen boasts high-end appliances while maintaining its classic appeal. Nestled on a tree-lined brick street, the home sits on a lushly landscaped lot with a spacious backyard, including a 64,000 gallon custom pool, perfect for enjoying Florida's warm evenings. Just minutes from Park Avenue's boutiques, restaurants, and within walking distance of A-rated schools, this rare gem offers the perfect blend of history, luxury, and location. Don't miss your chance to own a piece of Winter Park's rich heritage!

1600 Barcelona Way, 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

$1,850,000

5 Beds ⋅ 5 Baths ⋅ Windsong Elizabeths Walk 43/81 SubDv. ⋅ 32789 Zip Code

This Mediterranean-style, Windsong pool home is sure to check every box, with a 3-car garage, screened rear patio, heated spa and pool, and an ideal, 3-way split-bedroom floorplan on the 1st floor. The large kitchen sits at the heart of the home with a dinette showcasing pool views, an island with a gas cooktop, and a breakfast bar overlooking the sunny family room. Separate living and dining rooms off the foyer offer flexibility and additional space to entertain with ease. To the left of the foyer, enjoy a large, private office with a storage closet. Just past the office, the Primary Suite is situated on one end of the home for optimal privacy and features his and hers walk-in closets, a renovated bathroom, and access to the screened rear patio. At the other end of the home, a secondary bedroom with a full en-suite bathroom makes a great guest or in-law suite, while 2 additional bedrooms, a full hall bath, storage closet, and spacious laundry room complete the 1st floor. Upstairs, the private bonus room, complete with a walk-in closet and full en-suite bathroom, makes a perfect 5th bedroom. French doors from the family room, living room, and Primary bedroom all lead to a screened rear patio that overlooks a fully-fenced backyard where lush landscaping wraps around the resort-style heated pool and spa with water features. In addition to the massive driveway and expanded parking pad, the oversized 3-car garage provides extra parking and storage space. As one of the most coveted neighborhoods in Winter Park, Windsong offers countless amenities, including private lake access for residents. This premium location is just steps from Baldwin Park, East End Market, the Corrine Drive corridor, and minutes from downtown Park Avenue.

1627 Elizabeths Walk, Winter Park

$602,500

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

This beautifully updated 3 bedroom, 3 bath home offers a perfect blend of rustic charm and modern convenience in a highly desirable location. The open floor plan is warm and inviting, with stylish finishes and thoughtful updates that make it truly move-in ready. Each bedroom features its own ensuite bath and a spacious walk-in closet, with both upstairs suites offering the flexibility to serve as a primary retreat. Recent improvements include a brand new hot water heater, new refrigerator, an added mini-split in the garage for enhanced comfort, a water softener system, and a recently replaced A/C. The fenced backyard has been upgraded to turf for easy maintenance, complemented by a private deck—perfect for relaxing or entertaining. Two balconies, including one with a view of the Rollins College baseball field, provide additional peaceful retreats. The attached two-car garage offers both convenience and extra security. Located within walking distance of Park Avenue, Rollins College, and Hannibal Square, this home provides easy access to shopping, dining, and entertainment while maintaining a quiet and private feel. A rare opportunity in an unbeatable location—don’t miss it!

777 S Denning Drive Unit B, 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

$939,000

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

Top floor direct lakefront view of this Renovated condominium. Professional pictures coming.

100 S Interlachen Avenue Unit 502D, 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

32789 Zip Code Just Listed (7 Days) Real Estate & Homes

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