Displaying: For Sale
Location: Winter Park
Property Type(s): Single Family
Beds: 4 to 4
Do Not Show Listings
Winter Park - 126 properties found
1516 MILLER AVE, WINTER PARK, FL 32789
$1,549,90024 Days on yellowkey MLS ID: O6412745
0 Days Off yellowkey (back on 6/1/2026)
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3144 Built: 2026 Tax: $4,868 (2025)Community: LawndaleSpa: NoSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$4,868
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: New Construction!!! Escape the hassle of searching endlessly for your dream home in today's competitive market. Embrace the allure of new construction – Nestled in the vibrant Winter Park Grove neighborhood, this modern masterpiece awaits, promising a lifestyle of unparalleled comfort and convenience. Prime Location - Situated just minutes away from the bustling energy of Park Avenue this exceptional residence offers the ultimate in urban living. Explore local cafes, boutique shops, and entertainment venues with ease, all within walking or biking distance from your doorstep. Step inside to discover a world of contemporary elegance, where every detail has been meticulously crafted to perfection. The open floor plan seamlessly blends style and functionality, creating an inviting atmosphere that's perfect for both relaxation and entertainment. Boasting four spacious suites, including a lavish primary retreat on the main level, this home provides unparalleled comfort for you and your guests. Upstairs, two additional suites await, along with a versatile bonus room that can be transformed to suit your lifestyle – whether as a home office, gym, second living room, or fifth bedroom. Indulge your culinary passions in the gourmet kitchen, equipped with top-of-the-line Bosch appliances, including a 36" gas cooktop, built-in microwave, wall oven, French door refrigerator, and a wine fridge. With its sleek design and premium finishes, this kitchen is sure to inspire your inner chef. Step outside to your own private oasis, where a spacious lanai beckons you to unwind in style. Fire up the grill in the fully equipped outdoor kitchen, complete with a grill, sink, and refrigerator, and take a refreshing dip in the sparkling pool – the perfect setting for al fresco gatherings with family and friends. Pictures are of a previous model of the same plan- finishes and specifications are subject to change
Listing is courtesy of: RE/MAX EXCLUSIVE COLLECTION (407-447-2829)
Listing Agent: Kim Griffin (407-314-5033)
607 ELLEN DR, WINTER PARK, FL 32789
$1,449,900247 Days on yellowkey MLS ID: O6354269
REDUCED by $50,000 (3.3%) on 05/23/2026
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2812 Built: 2025Monthly Fee: $76 Tax: $4,224 (2024)Community: Lake Killarney ShoresSpa: NoSingle Family
Taxes:$4,224
Elementary School: Killarney Elem
High School: Edgewater High
Tax Year: 2024
Middle School: College Park Middle
Remarks: NEW PRICE!!! Discover sophisticated modern living at 607 Ellen Drive, a stunning new construction home by the acclaimed Lazarus Homes in the heart of Winter Park. This impeccably designed 2,812-square-foot residence showcases contemporary architecture with clean lines, high ceilings, and an abundance of natural light throughout. The open floor plan seamlessly connects living spaces, creating an ideal setting for both everyday life and elegant entertaining. The chef's kitchen is a true showpiece, featuring top-of-the-line Monogram appliances, a sleek Ruvati sink, built-in oven and microwave, and a professional gas range. Gorgeous Taj Mahal Quartzite countertops provide both beauty and durability, while thoughtful design elements include the option for a full-height wine refrigerator or additional cabinetry to suit your lifestyle. The living room offers a modern ambiance with an electric fireplace and expansive glass sliders that open to a covered lanai overlooking your private pool—perfect for Florida's indoor-outdoor lifestyle. For those who love to entertain, the home has been pre-stubbed for an optional outdoor kitchen. The luxurious first-floor primary suite provides a private retreat with a spa-inspired en suite bath featuring a double sink vanity, walk-in shower, soaking tub, and an oversized walk-in closet complete with custom built-ins and convenient washer and dryer hookups. Upstairs, the home continues to impress with a generous bonus room, a sophisticated loft with glass walls, three additional bedrooms, two full baths, and a second laundry area for ultimate convenience. A dedicated pool bath adds another layer of functionality for poolside enjoyment. Nestled in the desirable Lake Killarney Shores community, this home offers the perfect blend of tranquility and accessibility. Residents enjoy a low HOA, private boat launch access to Lake Killarney, and the convenience of being within walking distance to Winter Park's renowned restaurants, boutiques, and cultural attractions. This is move-in ready modern luxury at its finest.
Listing is courtesy of: KELLY PRICE & COMPANY LLC (407-645-4321)
Listing Agent: Kelly Price (407-645-4321)
2228 HOWARD DR, WINTER PARK, FL 32789
$2,460,00043 Days on yellowkey MLS ID: O6407733
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3294 Built: 2026 Tax: $3,647 (2025)Community: Lake Forest ParkSingle Family
Taxes:$3,647
Remarks: Under Construction. Welcome to 2228 Howard, a designer home that complements the irreplaceable natural beauty surrounding it with a one-of-a-kind façade. This curved street-front home winds around century-old oaks while overlooking Lake Howard, creating the kind of property you will love coming home to. Many rooms inside the home are designed to incorporate the outdoor spaces. These artfully designed exterior areas feel like an extension of the interior, making the home feel even larger and more luxurious. The first floor welcomes you and your guests through the 5’ wide steel pivot door near the private office. The extra-large kitchen, open pantry, and breakfast nook are framed by warm natural oak floor-to-ceiling cabinetry and Thermador appliances while overlooking the exterior raised garden bed. This beautiful kitchen flows seamlessly into the living room, which features a modern floating-hearth fireplace. The living room opens to the outdoor living space, summer kitchen, pool, and hot tub. The primary bathroom has a modern natural feel, featuring a glass sauna room that opens to a private outdoor spa with hot and cold plunge tub. The first-floor laundry room is located just off the two-car garage and includes a drop zone for additional organization. Another bonus feature is the inclusion of two laundry rooms—one on each floor. Upstairs, the kids’ lounge is surrounded by three bedrooms and a secret media room. One bedroom is en-suite, while the other two bedrooms share a common bathroom with dual vanity areas. The exterior of the home utilizes every area like a thoughtfully designed park, creating usable space around every corner. The driveway accommodates several vehicles and includes a side drive for additional parking and storage behind the gate and garage. When you do leave your beautiful home, you are surrounded by the best that Winter Park and Orlando have to offer. This neighborhood is zoned for top-rated schools, where kids walk and ride their bikes to school daily, and is surrounded by amazing parks, restaurants, shops, and nature. Your home can feel like a perfect balance of natural and modern architecture, both inside and out. Call us to see how this home delivers that truly unique feeling.
Listing is courtesy of: COLEDEV REAL ESTATE LLC (407-915-0456)
Listing Agent: Ryan Feely (321-663-1433)
316 BECKETT CT, WINTER PARK, FL 32792
$450,00029 Days on yellowkey MLS ID: O6411108
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1651 Built: 1966 Tax: $2,232 (2025)Community: Winter Park Pines Merrie OaksSingle Family
Taxes:$2,232
Remarks: Opportunity knocks in one of Central Florida’s most sought-after locations! This 4-bedroom, 2-bath home at 316 Beckett Court has been completely demoed and is ready for your vision to come to life. Whether you’re an investor, builder, or buyer looking to create your dream home, this property offers the ultimate clean slate for a full renovation or custom redesign. Situated in highly desirable Winter Park, this property places you in the heart of one of Orlando’s premier communities, known for its tree-lined streets, charm, upscale shopping, dining, and cultural attractions. Enjoy easy access to Downtown Winter Park Historic District and iconic Park Avenue, home to boutique shopping, cafés, restaurants, and vibrant community events, along with the beauty of Central Park and the cultural appeal of The Charles Hosmer Morse Museum of American Art. Winter Park is also home to the prestigious Rollins College, adding to the area’s timeless character and desirability. Bring your contractor, your imagination, and your vision—properties with this kind of potential in Winter Park are rare. Endless possibilities await!
Listing is courtesy of: ITS REALTY (321-437-7363)
Listing Agent: Patrick Westervelt, Llc (407-533-1000)
WINTER PARK, FL 32792
$430,000105 Days on yellowkey MLS ID: S5145631
REDUCED by $10,000 (2.3%) on 04/15/2026
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 1296 Built: 1958 Tax: $4,968 (2025)Community: Winter Park EstatesSingle Family
Taxes:$4,968
Remarks: Updated 4-bedroom, 2-bath home in a premium Winter Park location with NO HOA and a spacious backyard. This home is currently in the final phase of renovation and has already undergone major upgrades, including remodeled bathrooms, updated kitchen, new flooring, upgraded electrical, new AC System and a newer roof. The interior has been thoughtfully modernized, offering a bright open layout ideal for comfortable living and entertaining. The property is being sold in its current condition; exterior improvements will not be completed, giving the future owner the opportunity to finish and customize the exterior to their preference. Conveniently located near shopping, dining, schools, and major roadways.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Arlenys Oviedo (786-803-4342)
4348 STEED TER, WINTER PARK, FL 32792
$824,00048 Days on yellowkey MLS ID: O6406018
0 Days Off yellowkey (back on 5/26/2026)
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3040 Built: 1989Monthly Fee: $29 Tax: $3,652 (2024)Community: Kings CoveSpa: NoSingle Family
Taxes:$3,652
Elementary School: Red Bug Elementary
High School: Lake Howell High
Middle School: Tuskawilla Middle
Remarks: Under contract-accepting backup offers. BELOW APPRAISAL GEM IN WINTER PARK. Welcome to this beautifully and luxuriously updated 4-bedroom, 4-bath pool home located in the highly desirable Kings Cove community of Winter Park. Offering over 3,000 square feet of living space on a spacious 0.31-acre lot, this home blends comfort, functionality, and major system upgrades. The kitchen is designed for both everyday living and entertaining, featuring a gas stove, double oven, warming drawer, extra-large refrigerator, and custom pull-out cabinetry. The oversized island includes an additional sink, built-in microwave, and new (2025) under-counter ice maker. Recent upgrades and improvements include: New roof (2021) New first-floor A/C system (2021) New septic tank (2023) New hot water heater (2025) The primary suite has been thoughtfully updated in 2026, featuring a fully renovated bathroom with dual sinks and in-drawer electrical outlets, along with a custom-designed closet system completed in March 2026. New carpet was installed in April 2026. Additional highlights include a dedicated laundry room with sink and wine storage, a custom pantry with oversized pull-out drawers, built-in entertainment center, and a ceiling-mounted audio system controlled by phone. Step outside to enjoy your private in-ground pool and a quiet, established neighborhood close to top-rated schools, shopping, dining, and major highways. This is a move-in-ready home with major systems already updated and high-end functional upgrades throughout—don’t miss this opportunity.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Renata Dove (407-923-8216)
1780 BRYAN AVE, WINTER PARK, FL 32789
$849,000197 Days on yellowkey MLS ID: O6365369
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1617 Built: 1952 Tax: $7,345 (2024)Community: Lakeview TerraceSingle Family
Taxes:$7,345
Remarks: Build your dream home in one of Winter Park’s most desirable locations. This 66.6’ x 127’ homesite at 1780 Bryan Avenue offers a rare opportunity to secure the last remaining lot of three consecutive new construction parcels. Surrounded by newly built luxury residences, the property provides a clean slate for custom design while maintaining strong future value. The lot’s generous dimensions allow for a spacious floor plan, outdoor living areas, and a private backyard retreat. Situated on a quiet, tree-lined street, yet just minutes from Park Avenue, top-rated schools, dining, and shopping, the location strikes the perfect balance between convenience and neighborhood charm. Opportunities like this are increasingly rare in Winter Park—don’t miss your chance to be part of a growing enclave of new construction homes in a highly sought-after area.
Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)
Listing Agent: Nick Mckee (407-913-0171)
2232 BANCHORY ROAD, WINTER PARK, FL 32792
$1,115,00052 Days on yellowkey MLS ID: O6404702
REDUCED by $45,000 (3.9%) on 05/21/2026
Bed: 4 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 2597 Built: 1966 Tax: $11,186 (2025)Community: Brookshire Heights 4Th AddSingle Family
Taxes:$11,186
Remarks: Step into the Winter Park lifestyle with a fully turnkey home designed to make daily living feel effortless. Set on an oversized corner lot, this fully updated home blends clean design with thoughtful upgrades. Inside, the home is built to bring people together. The open-concept layout flows seamlessly from living to dining to kitchen, anchored by a striking 9-foot Carrera Thassos quartz island. A full KitchenAid black stainless steel appliance suite, generous storage, and refined finishes make this a space that works as well on a busy weekday as it does when hosting a full house. Out back, everything is ready to enjoy. A private, resort-style setting features a saltwater pool with fire bowls, custom lighting, and a dedicated outdoor dining area, all framed by professionally designed landscaping and low-maintenance artificial turf. Beyond the aesthetics, this home delivers real, everyday value. A reverse osmosis system, fully updated electrical and plumbing, a 5-ton air conditioning system, and a metal roof provide peace of mind. An 18.4-kilowatt solar system keeps utility costs remarkably low, with many months producing surplus energy credits. Located in sought-after school zones and just minutes from Cady Way Park, with easy access to Orlando, this is a home where everything has already been considered. No projects, no waiting, just move in and start living. Buyer to assume $75,000 solar panel loan, offset by minimal to near-zero electric costs and ongoing energy credits during high-production months. Utility bills available on request.
Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)
Listing Agent: Kirstie Hines (321-440-7716)
2512 EASTBROOK BLVD, WINTER PARK, FL 32792
$390,00035 Days on yellowkey MLS ID: O6409544
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1607 Built: 1967 Tax: $4,171 (2025)Community: Eastbrook Sub Unit 8Single Family
Taxes:$4,171
Remarks: Welcome to this beautifully maintained 4-bedroom, 2.5-bath home located in highly desirable Seminole County! From the moment you arrive, you'll appreciate the inviting front porch, the perfect place to relax, enjoy conversations with friends, and greet neighbors passing by. Inside, the home features recently painted interiors and new laminate flooring in the bedrooms, creating a fresh and move-in-ready feel. Pride of ownership shines throughout, as this home has been lovingly cared for over the years. Step outside and enjoy the spacious, landscaped backyard complete with a private irrigation well, screened-in porch ideal for morning coffee or evening unwinding, and a charming brick fire pit perfect for cooler Florida nights. There's even an outdoor shower, a unique and convenient touch after gardening or enjoying time outside on warm summer days.
Listing Agent: Joseph Firmin (954-296-8861)
1910 GLENCOE RD, WINTER PARK, FL 32789
$3,290,00052 Days on yellowkey MLS ID: O6403246
2 Days Off yellowkey (back on 5/21/2026)
Bed: 4 Bath: 5.5 Gar: 2 Liv Area Sq Ft: 3788 Built: 2026 Tax: $8,634 (2025)Community: Forest HillsSpa: YesSingle Family
Taxes:$8,634
Elementary School: Audubon Park K8
High School: Winter Park High
Remarks: Under contract-accepting backup offers. 2026 PARADE OF HOMES ENTRY! - Positioned on an expansive corner lot in the heart of Winter Park, this extraordinary new masterpiece is a true architectural statement, delivering a level of craftsmanship and detail that is simply unforgettable. Framed by a massive front yard and a canopy of mature trees, the bold modern façade creates an immediate sense of arrival and sets the tone for what lies within. A grand set of double doors opens to a breathtaking two-story entry, where a dramatic marble mosaic feature establishes the home’s elevated design from the moment you step inside. The main living space is nothing short of stunning, anchored by a sleek electric fireplace and custom built-ins with integrated LED underlighting. At the heart of the home, the chef’s kitchen is a true showpiece, outfitted with Dekton Cosentino countertops, a paneled refrigerator, a full suite of Thermador appliances, and a hidden walk-in pantry. The kitchen flows effortlessly into the dining room which is bathed in natural light from an oversized statement window, making it perfect for hosting at any scale. Designed with versatility and luxury in mind, the home features two primary suites, one on each level. The downstairs primary offers soaring 12-foot ceilings and a serene, spa-like bath wrapped in marble mosaic tile. Upstairs, the main primary suite is a true showstopper, defined by its scale and attention to detail. Dual custom closet systems include an expansive hers closet complete with a dedicated makeup vanity, while the bathroom delivers a resort-caliber experience with stunning marble floors, a freestanding soaking tub, and dual vanities. The upper level continues to impress with a spacious loft designed for both relaxation and entertaining, complete with a custom entertainment center, wet bar, wine fridge, and a full bath. Each additional bedroom is ensuite, offering privacy and comfort for family and guests alike. Outdoor living rivals that of a private resort. A massive covered lanai features a fully equipped summer kitchen with tile backsplash, overlooking an expansive lounging area framed by a wall of glass. The heated pool and spa create the ultimate setting for year-round enjoyment, while the oversized front yard (an incredibly rare find in Winter Park), adds an unmatched sense of space and setting rarely found in this market. Additional features further elevate the home, including a sleek metal roof, striking hex LED lighting in the garage, and curated designer lighting fixtures throughout. Perfectly positioned just moments from Lake Chelton and Virginia Heights Park, with easy access to the boutiques and dining of Park Avenue and the charm of Hannibal Square, this residence offers a lifestyle that is as elevated as the home itself.
Listing is courtesy of: ONE LUXURY INTERNATIONAL LLC (407-312-8003)
Listing Agent: Julie Christensen (407-592-2055)
1347 CHAPMAN CIR, WINTER PARK, FL 32789
$1,395,00041 Days on yellowkey MLS ID: O6408189
0 Days Off yellowkey (back on 5/20/2026)
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2922 Built: 2013Monthly Fee: $268 Tax: $16,875 (2025)Community: Windsong Elizabeths WalkSpa: NoSingle Family
Taxes:$16,875
Elementary School: Brookshire Elem
Middle School: Glenridge Middle
Remarks: Under contract-accepting backup offers. Beautiful Windsong custom home completely reimagined with a sophisticated interior design overhaul that now presents as a true Winter Park boutique luxury residence. This stunning 4 bedroom, 3.5 bath home blends timeless elegance, thoughtful craftsmanship, and warm entertaining spaces in one of the area’s most sought-after neighborhoods. Every room feels intentional and refined, showcasing elegant finishes, designer touches, and a fresh, elevated aesthetic throughout. Recently fully repainted and enhanced with gorgeous new quartz countertops and a crisp white pearl subway tile backsplash, the home now feels both current and timeless while maintaining the charm and character buyers love about Winter Park living. At the heart of the home is a spectacular chef’s kitchen featuring top-of-the-line Viking and Bosch stainless steel appliances, including a Viking gas range with griddle, a large center island with counter seating, stunning cabinetry, and a dramatic 10-foot coffered ceiling. The kitchen flows seamlessly into the inviting family room with gas fireplace and custom window seating, creating the perfect setting for both everyday living and upscale entertaining. Triple French doors open to a generous covered lanai complete with a summer kitchen, built-in grilling station, and beautifully designed outdoor spaces beaming with old-world charm rarely found in newer construction homes. The turf backyard offers easy maintenance while creating a warm and private atmosphere for gatherings year-round. The formal dining room is equally impressive with crown molding, wainscoting, abundant natural light from the oversized bay window, and direct access to a convenient butler’s pantry and dry bar, making hosting effortless. Upstairs, the magnificent owner’s retreat offers oversized walk-in closets and a luxurious spa-inspired bathroom adorned with glorious marble tile work and elegant designer finishes. Two additional generously sized bedrooms share a marble bath and the 4th bedroom is currently shown as an office, with adjacent hall full bath. A downstairs powder room outfitted in new england blue theme is great for guests. Additional luxury features include hardwood flooring, plantation shutters, surround sound, tankless gas water heaters, an electric vehicle charger, oversized two-car garage with high ceilings and level 5 drywall finish, and countless thoughtful upgrades throughout. Located within the highly desirable Windsong community, residents enjoy access to incredible amenities including two resort-style pools, lakefront clubhouse, water park, playground, fishing pier, kayaks, paddleboards, and even a residents-only pontoon boat to explore the Winter Park Chain of Lakes. Just minutes from Park Avenue, Baldwin Park, and top-rated Winter Park schools, this is your opportunity to step directly into the Winter Park home of your dreams—fully upgraded, impeccably styled, and ready now.
Listing is courtesy of: ORLANDO PROPERTY ADVISORS (407-808-3695)
Listing Agent: Justin Pekarek (407-808-3695)
363 N PHELPS AVE, WINTER PARK, FL 32789
$1,249,00063 Days on yellowkey MLS ID: O6401811
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 2871 Built: 1950 Tax: $8,856 (2025)Community: Sylvan ParkSingle Family
Taxes:$8,856
Remarks: This light and bright, single-story, almost 3,000 square foot pool home features a split plan with four full bedrooms and three full baths. Your guests will immediately appreciate the expansive paver driveway, which allows easy, off-street parking. Once inside, they will admire the abundance of natural light provided by the new, large-format windows. Not only do the new windows (2022) illuminate the interior space, but they are also impact-resistant, energy-efficient, noise-reducing, and offer UV protection. The interior renovation was designed with minimal barriers between living areas, creating open, fluid spaces that enhance day-to-day living. The bedroom and bathroom layout is ideal, offering maximum privacy: two large bedrooms share one full bathroom on one side of the house, another bedroom with an en-suite bathroom is at the center, and the primary bedroom and bathroom are on the other side. Wood or natural stone flooring, extensive millwork, vaulted ceilings, new paint, updated lighting fixtures, and new fans enhance the spaces throughout. The kitchen was renovated to include an oversized, under-mount farmhouse sink, commercial-grade faucet, new LED lighting, and quartz countertops with a waterfall edge. The primary suite was updated by a former owner but was renovated by the current owner to add a second walk-in closet with custom organization. All bathrooms received light renovations, ranging from hardware and paint to new fixtures or vanities and countertops. In addition to the visually appealing renovations, the roof was replaced in 2019 and the house was re-plumbed in 2020. The outdoor improvements may be the most valued, as they created endless opportunities for outdoor living and entertaining on the newly constructed deck and enhanced landscape. All of the outdoor living benefits Florida provides are available here. A natural gas line was brought to the house as part of the renovation, allowing for easy future modifications such as a tankless gas-fueled water heater or gas-fueled outdoor grill. Located just one and a half miles from the notable retail stores and restaurants of Park Avenue and within a well-graded public school zone, there is nothing you won’t love about this home or its location.
Listing is courtesy of: CREEGAN GROUP (407-622-1111)
Listing Agent: Chris Creegan (407-622-1111)
WINTER PARK, FL 32789
$1,249,90044 Days on yellowkey MLS ID: O6406381
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2936 Built: 2026 Tax: $3,539 (2025)Community: LawndaleSingle Family
Taxes:$3,539
Remarks: Pre-Construction. To be built. NEW CONSTRUCTION! Introducing an exquisite new construction home in Winter Park Grove, Winter Park's newest community! This residence is carefully curated by SGC Development, a highly respected local builder known for their dedication to quality and craftsmanship. This residence combines luxury living with the utmost convenience, located within walking distance to Publix and a variety of restaurants, and just minutes from vibrant Park Avenue. This light-filled, open-concept design showcases high-end finishes throughout. The chef’s kitchen is a true centerpiece, featuring premium Bosch appliances, a 36-inch gas range, a built-in coffee bar, and a spacious island with ample storage, creating a perfect culinary haven. The main level includes an ensuite bedroom, ideal for guests or a home office. Upstairs, discover two additional guest bedrooms, along with a luxurious primary suite that boasts a large walk-in closet and a spa-inspired bathroom. A versatile media/bonus room completes the upper level, perfect for entertainment or relaxation. Enjoy seamless outdoor living on the covered lanai with a fully equipped summer kitchen—ideal for gatherings and enjoying the Florida sunshine. Don’t miss this rare opportunity to own a thoughtfully designed home in Winter Park Grove, where modern elegance meets an unbeatable location. Schedule your private showing today! The pictures are of a model home with sinilar features
1903 N PARK AVE, WINTER PARK, FL 32789
$1,695,000155 Days on yellowkey MLS ID: O6375766
REDUCED by $100,000 (5.6%) on 05/14/2026
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2807 Built: 2020 Tax: $17,232 (2025)Community: Twin AcresSingle Family
Taxes:$17,232
Elementary School: Lakemont Elem
Middle School: Maitland Middle
Remarks: Completed in 2020, this beautifully designed contemporary residence on North Park Avenue offers refined finishes and seamless indoor-outdoor living just minutes from Park Avenue’s famed shopping and restaurant district as well as the vibrant retail and dining of Winter Park Village and Mills50. Positioned on a prominent corner lot with dual access from N Park Ave and N Denning Drive, the home features floor-to-ceiling glass, a wraparound terrace, and a bold two-story façade. The quartz river rock and concrete drive leads to dual frosted glass garage doors, pre-wired for an EV charger. Inside, a dramatic floating staircase is framed by a 17’ window, anchoring the open-concept living space with views of the private backyard. The modern kitchen includes light gray touch-open cabinetry, soft-close drawers, black stainless appliances, and a Calacatta quartz waterfall island. The outdoor space is designed for entertaining, with a covered lanai, expansive marble terrace, and a mini-pebble pool with sun shelf and water features. Lush podocarpus hedging and a masonry wall provide privacy. The first floor offers a dedicated office and full pool bath. Upstairs features four bedrooms with Italian frameless doors and three European-inspired bathrooms. The primary suite includes a custom walk-in closet and private access to the wraparound terrace overlooking the pool. Surrounded by beautiful tree-lined streets ideal for strolling and golf-cart rides to nearby shops, restaurants, and friends’ homes, this property offers the best of the Winter Park lifestyle. The home is also zoned for top-rated Winter Park schools. A rare modern home in one of Winter Park’s most desirable locations. Call today for your private showing.
814 DENSMORE DR, WINTER PARK, FL 32792
$425,00070 Days on yellowkey MLS ID: O6399773
2 Days Off yellowkey (back on 5/13/2026)
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 1610 Built: 1960 Tax: $5,402 (2025)Community: Winter Park EstatesSingle Family
Taxes:$5,402
Remarks: Under contract-accepting backup offers. Welcome to this charming home situated on a spacious lot in a quiet, established neighborhood in Winter Park. From the moment you arrive, you’ll appreciate the inviting curb appeal, expansive front yard, and peaceful setting that make this property feel like home. Inside, the home offers a light and open layout with a seamless flow between the living, dining, and kitchen spaces—perfect for both everyday living and entertaining. The updated kitchen features modern cabinetry, granite countertops, stainless steel appliances, and a functional layout with bar seating, making it both stylish and practical. The bedrooms are comfortably sized with great natural light, offering flexibility for family, guests, or a home office. The bathrooms have been thoughtfully updated, including a beautifully renovated shower with modern tilework that adds a fresh, clean feel. The Florida room in the back creates a relaxing space for drinking coffee or curling up for a family movie night. Step outside to a generously sized backyard with endless potential—whether you envision creating an outdoor entertaining space, adding a pool, or simply enjoying the open green space. With plenty of room to spread out, this yard offers the kind of flexibility that’s hard to find. Conveniently located near local shopping, dining, and major roadways, this home offers both comfort and accessibility. Zoned for great Winter Park schools. Whether you’re a first-time buyer, investor, or looking to downsize, this property presents an incredible opportunity to own a home with room to make it your own.
Listing is courtesy of: ORANGE SLICE PROPERTIES (863-632-9765)
Listing Agent: Liz Jones (407-619-6345)
770 W WEBSTER AVE, WINTER PARK, FL 32789
$725,000357 Days on yellowkey MLS ID: O6323574
1 Days Off yellowkey (back on 4/11/2026)
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 1008 Built: 1967 Tax: $4,856 (2024)Community: Capens AddSingle Family
Taxes:$4,856
Remarks: Under contract-accepting backup offers. Stop the car! Develop your dream project on this hard to find R-3 lot! Adjacent 75x100 R-3 vacant lot (TAX ID 06-22-30-1168-02-023) on the south side to be purchased simultaneously, for a total of 75x200 or 15,000sq/ft. Next to the proposed Winter Park Commons project, walk to Winter Park Village, Hannibal Square, WP9 and Park Ave for top shopping, dining and entertainment. Don’t miss this unique opportunity! PROPERTY SOLD AS-IS. VALUE IS IN THE LAND. NO REPAIRS.
Listing Agent: Lisa Gould (407-721-7612)
Lot #21 KAROLINA AVE, WINTER PARK, FL 32789
$944,890104 Days on yellowkey MLS ID: O6387812
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2662 Built: 2025 Tax: $2,207 (2024)Community: Karolina On KillarneySingle Family
Taxes:$2,207
Remarks: Pre-Construction. To be built. This is your final opportunity to build a custom home in one of Winter Park’s most sought-after pockets. Set on a 6,748 sq ft lot, this brand-new 4-bedroom, 3.5-bath residence offers 2,662 sq ft of thoughtfully designed living space, blending clean modern architecture with the comfort and functionality today’s buyers expect. Crisp lines, open-concept living, and intentional design create a home that feels both elevated and livable. What makes this opportunity truly unique: this is the last remaining homesite within a curated collection of three custom builds—each thoughtfully designed with its own architectural identity, yet unified in creating a refined, cohesive streetscape. The other two homes are already underway, making this your only chance to secure a position in this limited offering. Located just 6 minutes from Park Avenue, you’re moments from Winter Park’s best—boutique shopping, award-winning dining, and everyday conveniences—while also being close to top-rated hospitals and major thoroughfares. Offered as a custom build, this home allows you to tailor finishes, selections, and details to match your vision. Pricing reflects the base build, with upgrade options available to create a fully personalized end product. With new construction opportunities in 32789 at this price point becoming increasingly scarce, offerings like this are few and far between—especially with the ability to fully customize your home from the ground up.
Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)
Listing Agent: Vinny Lay (407-756-4255)
1131 WILDMEADOW RUN, WINTER PARK, FL 32792
$825,00093 Days on yellowkey MLS ID: O6392218
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2589 Built: 2020Monthly Fee: $165 Tax: $5,312 (2024)Community: Meadows At Hawks CrestSingle Family
Taxes:$5,312
Elementary School: Eastbrook Elementary
Middle School: Sanford Middle
Remarks: Winter Park - Located in the gated community of Hawks Crest, this 4-bedroom, 3.5-bath home offers 2,589 square feet of well-designed living space on a premium pond-view lot. Built in 2020, the home features a downstairs primary suite, open-concept living area, and a versatile upstairs loft. Additional highlights include a tile roof, modern finishes, a screened-in patio for outdoor living, and access to community amenities. This home combines location, layout, and value in a beautiful Winter Park gated communities.
Listing is courtesy of: BECK REALTY LLC (407-256-6369)
Listing Agent: Joann Beck (407-256-6369)
2627 AMBERGATE RD, WINTER PARK, FL 32792
$510,0001199 Days on yellowkey MLS ID: O6093816
Bed: 4 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 1805 Built: 1959 Tax: $4,750 (2022)Community: Winter Park EstatesSingle Family
Taxes:$4,750
Tax Year: 2022
Remarks: Price Reduced !! This beautiful and remodeled home is turnkey and ready to move in! Investors -- You will love the cash flow upside with this property. Updated Roof, AC, Exterior Paint, Patio, Garage, Driveway, Fence, Sprinkler System, Lighting, Flooring, Kitchen, and much more. You will enjoy entertaining your guests with this large saltwater pool with cabana, as well as yard space for your pets. Save money with No HOA, in a nice mature community. Smart home comes a split floor plan, and kitchen has a large island with granite countertops. Home features an extended driveway with room for a Small boat, Jet ski or RV. *All information is intended to be accurate but is not guaranteed.
Listing is courtesy of: COLDWELL BANKER REALTY (407-647-1211)
Listing Agent: Ryan Minadie (407-765-9990)
501 LAKEVIEW AVE, WINTER PARK, FL 32789
$1,390,000342 Days on yellowkey MLS ID: O6325192
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3253 Built: 2026 Tax: $2,820 (2024)Community: Killarney EstatesSingle Family
Taxes:$2,820
Remarks: MOVE-IN READY! Construction Completed! Brand-new custom construction on coveted Lakeview Avenue marries classic Winter Park charm with crisp, contemporary living. Behind its inviting façade you’ll find an airy two-story layout featuring four bedrooms and 4 ½ baths, including a full en-suite guest retreat on the main level. Three additional bedrooms share the upper floor with a bright loft that easily flexes as a playroom, office, or second lounge. The heart of the home is a chef-ready kitchen outfitted for serious cooking—double wall ovens, a dedicated cooktop, and generous countertop space—anchored by a spacious walk-in pantry and a convenient mudroom drop zone to keep daily life organized. Just beyond, a soaring great room centers on a built-in fireplace, while wide sliders open to a covered rear porch perfect for year-round alfresco dining. Upstairs, every bedroom enjoys direct or semi-private bath access, giving the residence the feel of four private suites, and a dedicated laundry room means no hauling baskets downstairs. Practical perks abound: an oversized two-car garage for gear and golf carts, impact-rated construction engineered to the latest Florida wind code, and full pre-wire rough-ins ready for your preferred appliance and lighting packages. All this sits minutes from Park Avenue’s dining and boutique shopping, Rollins College, and Winter Park’s famous chain of lakes. Schedule your private tour and discover the fresh, low-maintenance lifestyle waiting for you in one of Central Florida’s most sought-after neighborhoods.
Listing is courtesy of: COLDWELL BANKER RESIDENTIAL RE (407-647-1211)
Listing Agent: Marie Helen Ledbetter (407-286-4363)
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