Location: Winter Park
Do Not Show Listings
246 PALMER AVE, WINTER PARK, FL 32789
$1,500,00045 Days on yellowkey MLS ID: O6388115
0 Days Off yellowkey (back on 3/14/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 2281 Built: 1948Community: Robert Dhu Macdonald ParkSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:
Elementary School: None
High School: None
Tax Year:
Middle School: None
Remarks: Under contract-accepting backup offers. Welcome to 246 Palmer Avenue! Build your dream home or live in this charming home As-Is. Situated on a 14,252 sq.ft (0.33) corner lot on a beautiful brick street in the heart of Winter Park, this charming cottage offers timeless character, thoughtful updates, and a highly desirable location just minutes from Park Avenue, Rollins College, and the Winter Park Chain of Lakes. This well-maintained home features a layout with warm and inviting living spaces and abundant natural light. The original front door faces Palmer Avenue, while a later addition created the day-to-day entrance along Old England Avenue. Two separate living areas provide versatility for both relaxing and entertaining, and both the family room and the original living room, currently used as an office, feature wood-burning fireplaces. Just off the family room, a screened porch overlooks the lap pool and backyard, creating an easy connection between indoor and outdoor living. The dining room is lined with built-in bookcases, one of several thoughtful details found throughout the home. The kitchen enjoys views of the backyard and opens to a breakfast area with built-in cabinetry and French doors leading outside. A walk-in pantry adds practical storage. Off the original living room, an enclosed sunroom with original tile and additional built-ins offers a cozy space for reading, working, or unwinding. The primary bedroom opens to the backyard through French doors and includes built-in drawers in addition to closet storage. Its bath features a pedestal sink and clawfoot tub. A second bedroom is located across the home with access to a bathroom off the hallway, providing comfort and privacy for guests or family. Recent updates include a 2014 roof, gas water heater (2022), HVAC systems (2022 and 2023), and updated plumbing and electrical panels. A sprinkler system adds convenience for maintaining the grounds. This is a rare opportunity to build your dream home or enjoy this charming property as-is, ideally located just a couple of blocks from Park Avenue.
Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)
Listing Agent: Wendy Williams Crumit (321-356-8590)
1120 PRESERVE POINT DR, WINTER PARK, FL 32789
$8,950,000202 Days on yellowkey MLS ID: O6350054
Bed: 7 Bath: 10.0 Liv Area Sq Ft: 11255 Built: 2009Community: Windsong-Preserve PointSingle Family
Remarks: In the exclusive community of Windsong on Lake Berry, this magnificent 1.6-acre gated Mediterranean estate is a private oasis. With over 11,000 square feet of living area and a beautifully landscaped lakefront lot, this residence offers an exceptional blend of elegance, charm and privacy rarely found in Winter Park. The home features seven spacious bedrooms and nine full and two half baths. Entertain in the all-glass conservatory, dedicated theater room with motorized seating and a fully equipped game room. Modern conveniences throughout including gas-powered generators, an elevator and dumbwaiter. Two above-garage apartments provide ideal accommodations for guests and family. Outdoors, enjoy an expansive covered lanai, infinity edge pool and spa, boat dock with jet ski lift, and a summer kitchen complete with wood-burning fireplace, gas grill, refrigerator and icemaker, all overlooking the beautifully landscaped yard and lake. With its private gated entrance, this home is a one-of-a-kind opportunity to enjoy all the amenities Winter Park and Windsong have to offer.
Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)
Listing Agent: Hal George (407-832-8751)
5647 GARDEN GROVE, WINTER PARK, FL 32792
$350,00058 Days on yellowkey MLS ID: O6377980
0 Days Off yellowkey (back on 3/25/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1310 Built: 1986Community: Garden GroveSingle Family
Remarks: PRICE ADJUSTMENT! Welcome to this beautifully maintained 3-bedroom, 2-bath home for sale in Winter Park located in the highly sought-after Garden Grove community. Situated on a generously sized lot, this property offers the perfect blend of comfort, functionality, and outdoor living, with plenty of room to add a pool and create your own private backyard retreat. Inside, you’ll love the spacious split-bedroom floor plan designed for both privacy and everyday convenience. Ceramic tile flooring throughout adds style and easy maintenance, while the open family and dining room combination creates a warm and inviting space for relaxing or entertaining. A charming wood-burning fireplace adds character and comfort, making this home feel cozy and welcoming. The updated kitchen is a standout feature, opening seamlessly to the dining area and offering granite countertops, new cabinetry, and a convenient breakfast bar that is perfect for casual dining or hosting guests. Sliding glass doors lead directly to the expansive fenced backyard, making indoor-outdoor living easy and enjoyable. The oversized backyard is one of this home’s biggest attractions. Whether you envision weekend barbecues, a play area for pets, lush gardening, or extra space for your RV, boat, or recreational vehicles, this property offers flexibility that is hard to find in Winter Park. With room for a pool, the possibilities are endless. Major improvements include a roof replaced in 2019, giving buyers added peace of mind. Conveniently located near shopping, dining, parks, and major roadways, this Winter Park home offers space, value, and versatility in one of the area’s most established and desirable neighborhoods. If you are searching for a home with a large fenced yard, updated kitchen, split floor plan, and room for all your toys, this Garden Grove gem is a must-see.
Listing is courtesy of: WATSON REALTY CORP (407-323-3200)
Listing Agent: Carla Robles (407-462-2347)
2922 REEF KNOT PL, WINTER PARK, FL 32792
$1,149,000322 Days on yellowkey MLS ID: O6316445
Bed: 4 Bath: 3.5 Liv Area Sq Ft: 3153 Built: 2019Community: Lake Florence PreserveSingle Family
Remarks: One or more photo(s) has been virtually staged. Incredible Value!!! Major price reduction! Private Lakefront Living! Move-in Ready! Wake up to water views, quiet mornings and the kind of lifestyle that rarely becomes available in the Winter Park/Howell Branch area. Set along the shores of a private ski lake- Lake Florence, this single-level lakefront residence offers a serene retreat within an intimate gated enclave of just 28 homes. A setting that feels private and peaceful that is increasingly hard to find. Designed for both everyday comfort and effortless entertaining, the thoughtfully planned 4-bedroom, 3.5-bath layout includes a dedicated office, formal dining room and a desirable three-way split floor plan that provides flexibility and privacy for today’s lifestyle. At the heart of the home, the gourmet kitchen blends beauty and function with quartz countertops, a substantial center island, natural gas cooktop, 42" solid wood cabinetry, walk-in pantry, and a generous butler’s pantry—perfect for hosting or simply enjoying the flow of daily living. Rich wood flooring carries throughout the home connecting the kitchen seamlessly to the light-filled family room and casual dinette area. The primary suite is a true lakefront sanctuary featuring peaceful water views, two walk-in closets and a spa-inspired bath with dual sinks and an oversized shower with dual shower heads. Many upgrades are to be found through out this home such as an extra oversized storage closet, crown molding, custom mud room off of the laundry room, high ceilings, tray accents and abundant natural light to enhance the home’s relaxed, refined feel. Outdoors, the property transforms into a private lakefront escape. Enjoy sweeping water views, a sparkling pool and spa, custom rock waterfall, screened-in lanai and a fully fenced yard framed by tall privacy hedges and mature trees—ideal for quiet evenings or weekend gatherings. Direct lake frontage and access to a nearby community dock complete the lifestyle experience. A three-car garage with a separate AC wall unit offers added versatility—perfect for a workshop, home gym, or additional storage. Thoughtfully positioned, this home represents a rare opportunity to own a lakefront retreat that delivers serenity, lifestyle and value—all within close proximity to shopping, dining and top-rated schools in a prime location!
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: Ellen Bessette (407-496-0076)
3114 HEARTLEAF PL, WINTER PARK, FL 32792
$699,90036 Days on yellowkey MLS ID: S5146048
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 2702 Built: 1999Community: Lost CreekSingle Family
Remarks: Tucked away on a rare and breathtaking .96-acre homesite, this one-of-a-kind property in Lost Creek offers a setting that feels more like a private nature retreat than a suburban neighborhood. Surrounded by protected wooded conservation land and stretching back to the serene Howell Creek, this home delivers unmatched privacy, beauty, and a daily connection to nature. From the moment you arrive, you’ll notice the peaceful ambiance—towering trees, lush greenery, and the soothing backdrop of untouched landscape. Inside, the home features a spacious and inviting layout with approximately 4 bedrooms and 3 bathrooms, designed for both comfortable living and effortless entertaining. Large windows frame picturesque views of the wooded backdrop, filling the home with natural light and bringing the outdoors in. The kitchen flows seamlessly into the main living areas, while the split floor plan offers privacy for the primary suite, complete with tranquil views of the conservation area. Step outside to your backyard oasis where you can unwind, host gatherings, or simply enjoy the sights and sounds of nature along Howell Creek. Opportunities like this are incredibly rare—nearly an acre of protected land, no rear neighbors, and a location just minutes from everything Winter Park has to offer. Experience the perfect balance of privacy, space, and convenience in this truly special home.
Listing is courtesy of: CHAMPION HOMES (863-420-0007)
Listing Agent: Nadia Kurakin (509-981-9819)
1137 OAKS BLVD, WINTER PARK, FL 32789
$634,90080 Days on yellowkey MLS ID: O6379388
0 Days Off yellowkey (back on 3/21/2026)
Bed: 2 Bath: 1.5 Liv Area Sq Ft: 1149 Built: 1958Community: Dixie TerraceSingle Family
Remarks: Under contract-accepting backup offers. Charming Mid-Century Winter Park bungalow with tremendous potential * Not ready to build a new home but would like to have that option someday? This property provides the unique opportunity of being move-in ready and not overvalued for the neighborhood * The majority of the homes on this quiet tree lined street are brand new or recently built. There is value in being one of the only remaining homesites to be rebuilt * Ready to either owner-occupy or lease ($2,095 per month lease just completed) while you take the appropriate amount of time to create your custom plans. Step inside to find beautiful, exposed hardwood floors with timeless warmth and elegance, while the updated kitchen and baths ensure the home is move-in ready for your convenience. The large, fenced backyard offers plenty of room for outdoor living, providing the perfect spot to relax or entertain * The carport features a laundry/storage area, adding even more functionality to the property * House has a durable metal roof, further enhancing its appeal and longevity. For those looking to create a custom masterpiece, the existing structure offers the option for redevelopment, allowing you to build a home that perfectly suits your vision * Owner painted the exterior, replaced the microwave and hot water heater last year * Located just off N Park Avenue and a short distance from Winter Park's main attractions, you'll enjoy proximity to Downtown Winter Park, Winter Park Farmers Market, Whole Foods, Winter Park Village, and Rollins College. Shopping, dining, and entertainment are all just moments away, making this an unbeatable location * Don’t miss the chance to make this rare find your own! Currently zoned for Lakemont Elementary, Maitland Middle and Winter Park High School *
Listing is courtesy of: RE/MAX 200 REALTY (407-629-6330)
Listing Agent: David Gallup (407-629-6330)
2222 MARSH SEDGE LN, WINTER PARK, FL 32792
$764,900263 Days on yellowkey MLS ID: O6333145
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 2192 Built: 2019Community: Preserve At Hawks CrestSingle Family
Remarks: Welcome to your dream Home! This stunning and elegant single-story home, built by Meritage Homes in the gated community of Hawk's Crest in Winter Park, includes numerous upgrades. This is the Pomelo model, equipped with an upgraded kitchen package that includes built-in double ovens and a stainless steel range hood. Beautiful quartz countertops feature an oversized kitchen island with excellent space for family gatherings. Other features include a walk-in pantry and fantastic lighting. The luxurious kitchen integrates with the dining and living areas. The dining area is enhanced by a screened-in deck overlooking a pond. The backyard features a new, large, extended patio for entertaining. The master bedroom has an ensuite bathroom with a double vanity, a small closet, and a large walk-in closet that can be customized for a future owner. The home also comes with new gutters. Other amenities in the Hawk's Crest community include a resort-style pool with a clubhouse, a splash pad, a fitness center, barbecue grills, playgrounds, a dog park, and a community fishing pier with views and access to beautiful Lake Howell. Nearby, you'll find shops, restaurants, and specialty physicians such as Kelly's Ice Cream, Foxtail Coffee, Sobol, Winter Park Pediatric Dentistry, and the Park Maitland Preschool Campus, along with excellent schools in the area. Enjoy a short drive to Downtown Winter Park, with its extensive dining and shopping options. Hawk's Crest is also very close to Rollins College and UCF. Schedule your private tour today!
Listing is courtesy of: LA ROSA REALTY LLC (321-939-3748)
Listing Agent: Carmen Molina (321-331-5679)
1427 LAKE FLORENCE WAY, WINTER PARK, FL 32792
$675,000157 Days on yellowkey MLS ID: TB8449992
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 2193 Built: 2019Community: Lake Florence PreserveSingle Family
Remarks: Welcome to this beautifully maintained, Stunning Better-Than-New 6-Year-Old Custom Home in Gated Lake Florence Preserve, one-owner custom home that truly has it all. From the moment you enter, you’ll appreciate the exceptional quality and craftsmanship, including upgraded 8' interior doors, 10-foot ceilings, crown molding, and elegant tray ceilings throughout—even in the primary suite. One of the home’s most impressive features is the expansive 16-foot pocket sliding glass door that creates a seamless indoor–outdoor connection, making your private backyard oasis feel like a natural extension of your living space. Step into the custom heated pool with built-in spa, finished in luxurious PebbleTec, and enjoy the tranquil waterfall cascading from the spa into the pool. The entire screened-in lanai is surrounded by lush landscaping and enhanced by a striking outdoor LED lighting system. The fully fenced backyard overlooks a generous greenspace that enhances privacy and creates an ideal setting for pets, entertaining, or unwinding. TV wall mounts are already installed inside and on the lanai, ideal for watching the game or unwinding by the pool. The upgraded kitchen is a chef’s dream, featuring premium finishes and a gas stove, while the open-concept living area offers an inviting space for everyday living and entertaining. All bedrooms feature recently upgraded flooring, and the primary suite includes a large walk-in closet and a spa-like bathroom with a luxurious rain shower head. The home is outfitted with numerous upgrades for comfort and convenience, including motorized blinds on the sliding glass doors, ceiling fans throughout, dimmer light switches, and a full security system. Fresh interior paint including all doors adds a crisp, updated feel to every room. Practical features include an interior storage room, a tankless water heater, and a full sprinkler system covering both the front and backyard. The home also comes prewired with plumbing, gas, and electric for a future outdoor kitchen, offering excellent potential for expanded outdoor living. The garage is exceptionally functional, featuring a 240V EV outlet, a dedicated golf cart parking space, added shelving, and attic storage for additional organization and convenience.
Listing is courtesy of: COMMUNITY REALTY ASSOCIATES (561-852-1341)
Listing Agent: Douglas Addeo (561-251-3408)
2119 HOWARD DR, WINTER PARK, FL 32789
$850,00040 Days on yellowkey MLS ID: O6390345
0 Days Off yellowkey (back on 3/19/2026)
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 2479 Built: 1962Community: TimberlaneSingle Family
Remarks: Welcome to this charming residence in the heart of sought-after Winter Park. Pride of ownership is evident throughout this home and significant updates include a new roof being installed before closing, HVAC replaced in 2020, updated electrical in 2023 and a plumbing repipe in 2012. The spacious layout provides comfortable living and entertaining with a formal living room, formal dining room and sun-filled Florida room. Storage is plentiful in this house with several spacious closets and a generously sized walk-in closet in the primary bedroom. The primary bath includes a separate make up and vanity space. The property sits at just over a quarter acre and includes a long, brick paver driveway with plenty of parking and a private rear-entry garage. Ideally situated near the best of Winter Park and Audubon Park, residents enjoy convenient access to local dining, shopping, parks, and top-rated schools, including Audubon Park K8 and Winter Park High School. This coveted neighborhood is full of charm and tons of beautiful oak trees. Walk to Fleet Peoples dog park, hop on the 3 mile trail around Lake Baldwin or ride your bike to Park Avenue and the Farmer's Market on the weekends. This is a wonderful opportunity to own a well-cared-for home in one of Central Florida’s most desirable communities. Schedule your private showing today and see how you can make this home yours!
Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)
Listing Agent: Jill Healey (407-797-1420)
1823 MAYWOOD RD, WINTER PARK, FL 32792
$249,90040 Days on yellowkey MLS ID: O6385188
1 Days Off yellowkey (back on 3/19/2026)
Bed: 3 Bath: 1.5 Liv Area Sq Ft: 1232 Built: 1956Community: Tanglewood Sec 3 RepSingle Family
Remarks: Under contract-accepting backup offers. Located in the heart of Winter Park, this property is a prime candidate for redevelopment. Sitting on a ~9,259 sq ft lot, this is an ideal opportunity for builders or investors looking to capitalize on land value in a highly desirable area. The existing structure is a 3 bed, 1.5 bath home, but the true value here is in the lot and location. The seller has already cleared out the interior, making it easy to assess and move forward with your plans.
Listing Agent: Abby Nelson (407-571-1445)
1903 N PARK AVE, WINTER PARK, FL 32789
$1,795,00095 Days on yellowkey MLS ID: O6375766
Bed: 4 Bath: 4.0 Liv Area Sq Ft: 2807 Built: 2020Community: Twin AcresSingle Family
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.
Listing is courtesy of: CREEGAN GROUP (407-622-1111)
Listing Agent: Chris Creegan (407-622-1111)
1780 BRYAN AVE, WINTER PARK, FL 32789
$849,000137 Days on yellowkey MLS ID: O6365369
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 1617 Built: 1952Community: Lakeview TerraceSingle Family
Remarks: Discover a truly unique offering in the heart of Winter Park! This property, located at 1780 Bryan Avenue, is being offered along with the adjoining lots at 1760 and 1770 Bryan Avenue. While available together as a rare collection of three consecutive parcels, each lot is also being sold separately at individual prices, giving buyers the flexibility to purchase one, two, or all three. Together, these lots provide remarkable options for future use: Combine all three to create a spacious 200' x 127' estate lot Split into two 100' x 127' lots Or develop three individual 66.6' x 127' lots Use this premium property to build an estate-like home, design a family compound, or develop all three lots as spec homes—the possibilities are endless. Whether you’re envisioning a dream residence or an investment project, this is a rare chance in one of Winter Park’s most desirable neighborhoods. Ideally located just minutes from Phelps Park, Park Avenue’s shopping and dining, and top-rated schools, this offering combines convenience with exclusivity. Don’t miss the chance to secure one or more of these exceptional parcels in the heart of Winter Park.
Listing Agent: Nick Mckee (407-913-0171)
958 HANOVER AVE, WINTER PARK, FL 32789
$490,000 MLS ID: O6388088
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 1378 Built: 1956Community: Albert Lee Ridge First AddSingle Family
Remarks: Under contract-accepting backup offers. Mother-in-Law suit attached with private entrance on a dead-end street with water view. Welcome to this beautifully remodeled home in the heart of Winter Park, offering the perfect blend of charm, privacy, and convenience. Situated at the end of a quiet street, this unique property provides exceptional privacy while showcasing peaceful views of nearby Lake Wilderness. The main residence features 3 bedrooms and 2 bathrooms, complemented by an attached mother-in-law suite with a full bath and private entrance, making it ideal for multigenerational living, guests, a home office, or potential rental income. Inside, the home has been thoughtfully updated with a fully remodeled kitchen and bathrooms, real hardwood flooring throughout, and a bright open-concept layout designed for comfortable everyday living and entertaining. Additional upgrades include plantation shutters, double-pane windows (2021), and added attic insulation (2023) for improved energy efficiency. Major system updates provide peace of mind with HVAC replaced in 2022 and roof installed in 2018. Step outside to enjoy a screened-in back porch overlooking a spacious fully fenced yard with plenty of room to garden, relax, or entertain. The property is enhanced by maturing fruit trees in both the front and back yard, creating a private and serene outdoor setting. Location is another major highlight. The home offers quick access to Interstate 4, making commuting throughout Central Florida easy. It’s also just 10 minutes from Winter Park Village, where residents enjoy some of the area’s best restaurants, shopping, and a movie theater. Additionally, Winter Park is known for its charming tree-lined streets, beautiful lakes, parks, golf courses, and vibrant cultural scene, including the renowned Park Avenue district, museums, and top-rated dining. This rare property offers privacy, flexibility, and modern updates in one of Central Florida’s most desirable communities.
Listing is courtesy of: AGILE GROUP REALTY (813-569-6294)
Listing Agent: Christopher Lyons (407-230-2210)
1581 FOREST AVE, WINTER PARK, FL 32789
$3,495,000 MLS ID: O6382377
Bed: 4 Bath: 5.0 Liv Area Sq Ft: 4683 Built: 1954Community: Ellno WilloSingle Family
Remarks: Just steps from the charm and energy of Park Avenue, this exceptional Winter Park residence was completely rebuilt in 2018 by renowned custom builder Posada Homes, member of the elite Master Custom Builders Council. Offering a rare blend of modern design, crisp architectural lines, and timeless elegance, on an expansive 0.39-acre lot along one of Winter Park's most picturesque tree-lined streets. The home immediately captivates with its refined architecture and beautifully manicured grounds. Inside, sunlight streams through expansive windows, illuminating hardwood flooring, intricate millwork, and thoughtfully curated finishes that reflect the craftsmanship of a true custom build. Just off the foyer, a hidden wine room provides a sophisticated surprise, perfect for those who love to entertain. At the center of the home is the chef's kitchen designed for both beauty and functionality. Outfitted with premium Thermador appliances, sleek quartz countertops, a generous center island, and custom cabinetry, the kitchen flows effortlessly into the expansive great room where high ceilings, designer lighting, and elegant architectural details create an atmosphere that is both inviting and refined. Tucked away for privacy, the primary suite is positioned just off a luxurious family room featuring custom built-ins and a gas fireplace. The primary suite itself is a true sanctuary, complete with a sitting area, private coffee bar, and a spa-inspired bath featuring dual vanities, a soaking tub, and an oversized walk-in shower. Rarely found in Winter Park, all bedrooms are conveniently located on one level, including two primary suites. The home offers seamless livability without sacrificing architectural interest or sophistication. Upstairs, a private office, half bath, and bonus room provide the perfect space for work, media, recreation, or relaxation. Outdoors, the home transforms into a private resort-style retreat. A covered lanai overlooks the sparkling pool and expansive grounds, creating the ideal setting for entertaining or quiet evenings at home. Adding even more flexibility, a 252-square-foot detached studio currently functions as a gym but could easily become a summer kitchen cabana, guest retreat, or art studio. Located within walking distance of Park Avenue's boutiques, restaurants, and cafés, and just moments from Rollins College and the Winter Park Chain of Lakes, this residence embodies luxury living at its finest. Don't miss this rare opportunity to own one of Winter Park's most outstanding homes.
Listing is courtesy of: ONE LUXURY INTERNATIONAL LLC (407-312-8003)
Listing Agent: Julie Christensen (407-592-2055)
Lot #21 KAROLINA AVE, WINTER PARK, FL 32789
$944,890 MLS ID: O6387812
Bed: 4 Bath: 3.5 Liv Area Sq Ft: 2662 Built: 2025Community: Karolina On KillarneySingle Family
Remarks: Pre-Construction. To be built. Step into a life where charm meets convenience in the heart of Winter Park. This brand-new 4-bedroom, 3.5-bath residence offers 2,662 square feet of thoughtfully designed living space and sits on a 6,748 square foot lot. The home showcases modern architecture with clean lines and the comfort and functionality today’s homeowners desire. This is the final opportunity among three consecutive custom builds—each with its own distinctive architecture and character—creating a rare blend of individuality while maintaining a cohesive neighborhood aesthetic. Located just six minutes from Park Avenue’s renowned boutique shopping and dining, and within close proximity to top-rated hospitals, the home places you at the center of everything that makes Winter Park one of Central Florida’s most desirable communities. The home is offered as a custom build opportunity, allowing buyers to personalize finishes and features to suit their style. Pricing reflects the starting point, with a variety of upgrade options available. The other two custom homes in the collection—1835 Karolina Avenue and Parcel 20—have already begun construction, making this the final chance to secure a newly built home in the highly sought-after 32789 zip code.
Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)
Listing Agent: Vinny Lay (407-756-4255)
2625 SUMMERFIELD RD, WINTER PARK, FL 32792
$724,900 MLS ID: O6384757
Bed: 5 Bath: 3.0 Liv Area Sq Ft: 2199 Built: 1968Community: Golfside Golf Course Sec 01Single Family
Remarks: Under contract-accepting backup offers. Welcome to 2625 Summerfield Rd in Winter Park, FL. A beautifully maintained pool home on one of Winter Park’s most picturesque tree-lined streets. What makes this home so rare? It has 5 bedrooms, 3 full bathrooms, a split floor plan, and a private pool with full screen enclosure in a highly sought-after Winter Park location. That combination is incredibly hard to find in Winter Park, Florida. The split-bedroom floor plan provides privacy and functionality. The spacious primary suite opens directly to the pool and features generous closet space. A convenient Jack and Jill bathroom connects two secondary bedrooms, while a dedicated pool bath adds flexibility for guests and entertaining. New tile flooring throughout most of the home creates a clean, cohesive look. Formal living and dining rooms provide elegant gathering spaces, centered around a charming fireplace focal point. The kitchen offers Corian countertops, warm cabinetry, and a functional breakfast bar overlooking the family room. Sliding glass doors lead to the private pool with full screen enclosure, waterfall feature, and variable speed pump, all surrounded by a fenced yard with mature privacy hedges. Major system updates include a 2022 roof, 2021 water heater, automated hurricane shutters, backup generator, upgraded alarm system, and refreshed attic insulation. Ideally located near Winter Pines Golf Club, Park Avenue dining and shopping, AdventHealth Winter Park, and the Crosby Wellness Center. Enjoy easy access to the Cady Way walking and biking trail, nearby parks, pickleball courts, Rollins College, UCF, Full Sail University, Baldwin Park, and Orlando International Airport. This address reflects the walkable charm, tree-lined beauty, and established character that make Winter Park one of Central Florida’s most admired communities.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Melissa Johnson (407-681-4393)
5233 LAKE HOWELL RD, WINTER PARK, FL 32792
$562,000969 Days on yellowkey MLS ID: O6137445
1 Days Off yellowkey (back on 10/24/2023)
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 1778 Built: 1956 Tax: $4,888 (2022)Community: Tanglewood Sec 3 RepSingle Family
Taxes:$4,888
Elementary School: English Estates Elementary
High School: Lake Howell High
Tax Year: 2022
Middle School: Tuskawilla Middle
Remarks: Under contract-accepting backup offers. NO HOA. Dual Master Suites. One main, and one mother-in-law or guest suite. All single story, no stairs. NEW POOL DECK. NEW POOL PUMP. POOL RESURFACED.NEW ROOF (installation in progress). Totally renovated. NEW HOT WATER HEATER. NEW FLOORS. POOL RESURFACED. NEW POOL DECK. NEW POOL PUMP. NEW ALL TURF BACK LAWN (NO Mowing). NEW PUTTING GREEN (for your backyard golfer). Full Security system. Get ready to relax & have fun enjoying your new home!! Accessible and convenient, with a fabulous all-turf backyard to unwind, entertain, or make fantastic memories with those you love. Your deepwater private pool (that used to have a diving board) is the highlight of this sunny Florida oasis, including a Mini-golf putting green, outdoor dining, and plenty of space to lounge and relax when you're not on the go. Just 14 miles (30 mins) from Orlando International Airport. 20 mins to the Amway Center, Exploria Stadium, and the Dr. Philips Performing Arts Center for MLS soccer games, concerts, conferences, ballet, theater, NBA basketball games, and more. With both the University of Central Florida (UCF) and Valencia Campuses at similar proximity, this property is close to everywhere you want to be. Take the dogs for a walk around Lake Baldwin, just south, or enjoy the beachside dog park there. Ideal for a brisk run, a rejuvenating bike ride, or an invigorating rollerblade the Cady Way Train connects to the Lake Baldwin path, so you can expand your adventurous outings an additional 13 miles, beyond the 2.5 miles that wrap around the quaint peaceful lake. Baldwin Park is the best place to gather or getaway on your day-to-day. Visit the Winter Park Farmers Markets every Saturday, and take a stroll up Park Ave or take a world-class boat tour of the Winter Park Chain of Lakes after a fantastic Sunday Brunch at any of the local restaurants you know and love. Whether you're gathered around the dining room table laughing and playing board games after dinner, or cuddled up on the sofa in your open great room, watching the flickering fire on a brisk winter day, or streaming your favorite binge-worthy show, there is plenty of room for you to live your life in the best possible way. The split-floor plan gifts privacy from the master wing located off the kitchen and convenient to the backyard oasis/pool. The ensuite guest bath is a rare treat for company and residents alike. Kissed with glowing natural light in every room, this well-laid-out functional flow makes it easy to enjoy every tranquil moment your new home offers you. Turn these moments into memories and live your best life daily! POOL RESURFACED. TURN-KEY OPTIONAL (furniture optional in separate private purchase). Ring Camera. Security System. Updated/Renovated Bathrooms. Bright. Open. Airy. Comfortable. Welcoming. Fun. Cozy. Entertaining. Easy. Relaxing. Refreshing. Peaceful. Happy. Inviting. Private. Convenient.
Listing is courtesy of: CADENCE LIFESTYLE REAL ESTATE (877-366-2213)
Listing Agent: Miranda Cady (407-340-7016)
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