Displaying: For Sale
Location: Winter Park
Property Type(s): Single Family
Beds: 4 to 4
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Winter Park - 104 properties found
1090 WILDMEADOW RUN, WINTER PARK, FL 32792
$845,00038 Days on yellowkey MLS ID: O6394208
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2589 Built: 2021Monthly Fee: $243 Tax: $6,258 (2024)Community: Hawks CrestSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$6,258
Elementary School: Eastbrook Elementary
High School: Lake Howell High
Tax Year: 2024
Middle School: Tuskawilla Middle
Remarks: One or more photo(s) has been virtually staged. One or more photo(s) has been virtually staged. This luxurious Modern Style home epitomizes maintenance-free living, featuring a premium state of the art solar system you own outright, paying for your electricity. (Ask to see the bill.) Imagine relaxing on your private, expanded lanai, soaking in the breathtaking sunsets. Your spacious 4-bedroom, 3.5-bathroom home offers premium views of nature, and is just steps away from the community resort clubhouse. With gated access, Hawks Crest residence enjoy an abundance of amenities, including a resort pool and fitness center, sidewalks and playgrounds throughout. And for those seeking adventure, enjoy dock access to Lake Howell, complete with a canoe/kayak launch. Daily, residents can relax and unwind while the management association takes care of all landscaping around the home, ensuring that residents can enjoy true maintenance-free living. The state-of-the-art off-grid solar system is equipped with battery backup with a warranty transferable to new owners. And this home is pre-wired for electric vehicles with room to expand. Excess power produced is sold back to the power company through the “Net Metering” program. Additionally, upgrades include heavy-duty commercial luxurious vinyl wide-plank flooring, two power monitoring systems, a whole-house water softener & filter system, along with 8-foot doors all designed for comfort, convenience and a peaceful home where you can relax. Nestled in this spacious home, you’ll find 20-foot-high ceilings and breathtaking views of the illuminated fountain from various rooms, creating a serene and relaxing atmosphere you’ll enjoy, even from the kitchen sink. And with a winch lift, your chandelier maintenance is a breeze. (Rated up to 200lbs). Uniquely designed, this home was built to withstand extreme weather conditions, featuring concrete/granite tile roof, along with a steel reinforced, concrete-filled block walls and slab, all anchoring to the foundation that uniquely ties everything together, ensuring the utmost strength and safety for your family. Owners have meticulously maintained this home and comes with floor plans, a complete set of blueprints, along with photos & videos of the home during the building process, and even includes documents for all equipment and appliances. The premium solar system comes with a transferable warranty, including scheduled updates like the new power panel, installing in 2026. And yes, this premium solar system is completely paid off and the warranty is transferable to new owners. This home features a split floor plan, with a primary bedroom on the first floor and a second primary bedroom upstairs. Spanning 2,589 square feet, the home also includes an additional 540 square feet of screened-in lanai (18x30), providing a private outdoor space to enjoy sunsets while overlooking the resort water features and landscaping. Schedule a showing for your buyers today!
Listing is courtesy of: BHHS FLORIDA REALTY (352-729-7325)
Listing Agent: Rod Chevalier (352-729-1818)
1800 MAGNOLIA AVE, WINTER PARK, FL 32789
$1,100,00049 Days on yellowkey MLS ID: NS1087637
REDUCED by $47,000 (4.1%) on 04/27/2026
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2431 Built: 1996 Tax: $11,730 (2025)Community: Temple TerraceSpa: NoSingle Family
Taxes:$11,730
Elementary School: Dommerich Elem
High School: Winter Park High
Tax Year: 2025
Middle School: Maitland Middle
Remarks: One or more photo(s) has been virtually staged. NEW PRICE! Experience refined living in this exquisitely renovated custom home, positioned on an oversized corner lot in one of the area’s most peaceful and private neighborhoods. Tucked away at the end of a quiet dead-end street, this residence offers an exceptional blend of craftsmanship, sophistication, and modern comfort. Inside, soaring 10-foot ceilings and a stately wood-burning fireplace set a welcoming tone in the family room. The fully reimagined chef’s kitchen is a true showpiece, featuring solid maple cabinetry, quartz countertops, programmable Bosch stainless steel range and refrigerator and a striking brick backsplash—an elevated space designed for both culinary creativity and effortless entertaining. All three bathrooms have been luxuriously renovated, and new carpeting adds a soft, refined touch throughout all four bedrooms. French doors from the master suite, formal living room, and family room open to a breathtaking screened-in pool retreat. Surrounded by lush tropical landscaping, this private oasis has been thoughtfully upgraded with a new pool pump, a conversion to a sparkling saltwater system, and a beautifully refinished pool deck. An outdoor shower with both hot and cold water adds a resort-level convenience, perfect after a swim or a day in the sun. Every major system has been meticulously updated for peace of mind, including a new programmable HVAC system, a complete replumb of the entire home, all new ductwork, and an upgraded water heater. Additional enhancements—such as fresh interior and exterior paint, a new garage door opener in the over-sized garage and refreshed landscaping — ensure a truly turnkey experience. With its luxurious finishes and meticulous improvements, this residence is ready for the next family to make it their own. This property is located just 2 miles to AdventHealth Winter Park Hospital, less than 10 minutes to Park Ave, and zoned for top-rated schools such as Dommerich Elementary, Maitland Middle, and Winter Park High School. Just minutes from Winter Park’s boutiques, acclaimed restaurants, and the cultural charm of Park Avenue, this home offers a rare opportunity to enjoy elevated living in a setting that’s both secluded and connected. A truly private sanctuary designed for comfort, style, and the best of Florida living.
Listing is courtesy of: FLORIDA REALTY INVESTMENTS (407-207-2220)
Listing Agent: Kathy Summers (407-832-6986)
2052 LEANNE CT, WINTER PARK, FL 32792
$450,00090 Days on yellowkey MLS ID: O6379323
REDUCED by $6,000 (1.3%) on 04/15/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2264 Built: 1969 Tax: $1,581 (2024)Community: Eastbrook Sub Unit 15Spa: NoSingle Family
Taxes:$1,581
Elementary School: None
High School: None
Middle School: None
Remarks: Welcome to 2052 Leanne Ct, a home that exudes warmth and elegance. The living room is graced with a cozy fireplace, perfect for those chilly evenings. The kitchen is a chef's dream, boasting all stainless steel appliances for a sleek, modern look. The primary bedroom is a haven of comfort with double closets for ample storage. The primary bathroom is a sanctuary with double sinks, providing ample space for your morning routine. The fenced-in backyard provides a private outdoor space for relaxation and entertainment. The home has been recently updated with fresh interior and exterior paint, giving it a clean, refreshed look. New flooring throughout the home adds a touch of sophistication and durability. The new appliances ensure efficiency and convenience. Included 100-Day Home Warranty with buyer activation
Listing is courtesy of: OPENDOOR BROKERAGE LLC (480-462-5392)
Listing Agent: Karen Albright (480-462-5392)
2217 SUSSEX RD, WINTER PARK, FL 32792
$520,000164 Days on yellowkey MLS ID: O6362648
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2092 Built: 1968 Tax: $4,939 (2024)Community: Winter Woods Unit 01Spa: NoSingle Family
Taxes:$4,939
Remarks: PRICE REDUCED!!! 4 BEDROOMS with OFFICE POOL HOME. MOTIVATED SELLERS. MOVE IN READY! THIS HOME WILL NOT LAST! COME, SEE AND BRING YOUR OFFERS TODAY! This home boasts a large open concept as you walk in from the front door. Tons of natural lighting. Kitchen equipped with modern appliances, granite counter tops, and lots of cabinets for storage. Woodburning fireplace. Pool view from the masterbedroom. Large covered and with a/c wall unit patio/lanai with a full view of large well maintained pool and fully fenced landscaped backyard, also equipped with separate washing station convenient for many summer funs and gatherings. NO HOA! Highly sought after area. Great schools. Great neighborhood and community. Close to all main roads, highways, shopping, foods. Short drive to all Orlando attractions and beaches.
Listing is courtesy of: PREFERRED REAL ESTATE BROKERS (407-440-4900)
Listing Agent: Thess Hubilla (407-309-1141)
2829 ALOMA, WINTER PARK, FL 32792
$579,0003 Days on yellowkey MLS ID: O6404107
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1821 Built: 1963 Tax: $4,277 (2025)Community: Winter Park EstatesSingle Family
Taxes:$4,277
Remarks: Just Listed – 2829 Aloma Avenue, Winter Park This is the one you’ve been waiting for. A completely remodeled home with a private pool in one of the most desirable areas of Central Florida—all for under $600,000. Enjoy the perfect blend of modern upgrades and unbeatable location, just minutes from top-rated restaurants, shopping, excellent schools, and everything that makes Winter Park so special. 4 Bedrooms + Den 2 Bathroom 1,821 Sq Ft Private Pool (Resurfaced) + New Pump Fully Renovated Homes like this don’t come around often—whether you’re looking for your primary residence or a smart investment, this property checks every box. If you want a home that delivers both lifestyle and location, this is your opportunity. ?? Message me today for more details or to schedule your private showing before it’s gone!
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Roberto Silva (407-493-3683)
1813 HARLAND PARK DR, WINTER PARK, FL 32789
$1,995,0003 Days on yellowkey MLS ID: O6403483
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3551 Built: 2013Monthly Fee: $268 Tax: $23,539 (2025)Community: Windsong-Knowles PlaceSpa: YesSingle Family
Taxes:$23,539
Elementary School: Brookshire Elem
Middle School: Glenridge Middle
Remarks: Nestled within the highly sought-after Windsong community in Winter Park, this thoughtfully designed residence presents the perfect balance of functionality, comfort, and elevated indoor-outdoor living. This move-in ready home is sure to check all the boxes with 2 NEW HVAC units (2025), a downstairs Primary Suite, a convenient 1st floor private office/flex room, 2nd floor loft & bonus room, plus a private backyard oasis complete with a full summer kitchen, covered rear lanai, and saltwater pool with a heated spa. The large, covered front porch welcomes guests into a foyer that opens to a spacious and well-orchestrated floorplan. Just off the entry sits a versatile office/flex space, providing the perfect setting for a private workspace or playroom, while a conveniently located powder bath serves visitors with ease. The foyer unfolds with effortless flow into the heart of the home, where an expansive living room is designed for both everyday living and entertaining. The open-concept kitchen is both functional and refined, featuring a natural gas cooktop, built-in double ovens, and adjacent sunny dinette that overlooks the backyard and pool, creating a casual dining space filled with natural light. On the opposite end of the kitchen, a large walk-in pantry offers tons of storage, and a butler’s pantry/dry bar seamlessly adjoins the large dining room—ideal for hosting gatherings with a polished, intentional flow. At the rear of the living space, expansive stacking glass sliders open to the rear covered lanai, extending the living space outdoors. Enjoy space for dining, lounging, and entertaining with a full summer kitchen that includes a large gas grill, double gas burners, a sink, beverage fridge, and storage cabinets. The backyard beyond creates a true retreat that embodies the Florida lifestyle, where a heated spa overflows into a beautifully designed saltwater pool complete with a sun shelf, all wrapped in travertine decking, tropical landscaping, and a masonry wall for enhanced privacy. Situated at the rear of the home, the well-appointed primary suite offers a quiet escape with generous proportions, dual walk-in closets, and a sensible primary bath with split vanities, a soaking tub, separate shower, and private water closet. The main level continues with exceptional functionality, including a spacious laundry room lined with built-in cabinets for storage, and a 2-car garage with direct access to the side yard and overhead racks for additional storage capacity. Upstairs, a thoughtfully designed 2nd level provides incredible flexibility, featuring a central loft for a reading or study area, a large bonus room that's perfect for a game room or secondary living area, three additional bedrooms - each with walk-in closets, two full bathrooms, and a linen closet, plus an additional storage/media closet. This home is not just a residence—it’s a lifestyle. Windsong residents enjoy access to premier amenities, including multiple community pools, a splash pad, playgrounds, a clubhouse, and 2 community docks providing access to the Winter Park Chain of Lakes via Lake Berry & Lake Mizell. Ideally located just minutes from Park Avenue, Baldwin Park, and the vibrant Corrine Drive corridor, this property offers tranquility and convenience in one of Winter Park’s most desirable neighborhoods.
Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)
Listing Agent: Marystuart Day (407-620-8683)
1565 FOREST AVE, WINTER PARK, FL 32789
$1,750,00020 Days on yellowkey MLS ID: O6398694
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 2163 Built: 1925 Tax: $2,803 (2025)Community: Ellno WilloSingle Family
Taxes:$2,803
Elementary School: Audubon Park K8
Middle School: Audubon Park K-8
Remarks: One or more photo(s) has been virtually staged. Set apart from the ordinary, this historic Winter Park residence offers a rare opportunity to own a home rich in character and authenticity. Homes like this, with timeless architectural detail and enduring charm, rarely come to market, especially in such a premier location just steps from the shores of Lake Virginia. Surrounded by multi million dollar estates, this 4 bedroom, 2 bath home blends classic warmth with everyday livability. Original wood floors, a wood burning fireplace, and thoughtfully designed living spaces reflect a level of craftsmanship and character that simply cannot be replicated. The spacious dining room is perfect for hosting memorable family gatherings, while the updated kitchen with wood cabinetry offers both function and charm. Upstairs, a versatile loft space provides flexibility for a media room, office, or play area, complete with peekaboo views of Lake Virginia that create a subtle connection to the surrounding landscape. Adding to the home’s appeal is a detached 20 x 20 studio flooded with natural light and offering endless possibilities, ideal for an artist’s retreat, home office, gym, or guest space.This is more than a home, it is an opportunity to own a piece of Winter Park’s character and history. Set among some of Winter Park’s most distinguished homes, this property delivers an unbeatable lifestyle, walkable to all that Park Avenue has to offer, surrounded by luxury, and full of potential to enjoy, enhance, or reimagine.
Listing is courtesy of: NORDQUIST & COMPANY INC (407-694-0996)
Listing Agent: Elizabeth Nordquist (407-694-0996)
2015 SUMMERFIELD RD, WINTER PARK, FL 32792
$1,375,000179 Days on yellowkey MLS ID: O6357615
Bed: 4 Bath: 4.0 Gar: 1 Liv Area Sq Ft: 3024 Built: 1957 Tax: $7,243 (2025)Community: Kenilworth Shores Sec 07Spa: NoSingle Family
Taxes:$7,243
Remarks: Experience refined Winter Park living in Kenilworth Shores, a highly sought after neighborhood near Baldwin Park, Lake Baldwin trails, and the dining and boutiques of Park Avenue. This location places you close to Rollins College, Winter Park High, and the cultural center of Winter Park FL. Inside, natural light moves through open living spaces finished with wide porcelain tile floors. The kitchen stands as a sophisticated gathering space with a large quartz island, custom cabinetry, Bosch appliances, and a walk in pantry. The primary suite offers a peaceful retreat with direct access to the pool and a spa inspired bath. A second ensuite bedroom, dedicated office, and generous flex room provide versatility for daily living. The backyard feels like a private resort with a covered outdoor kitchen and a sparkling pool framed by thoughtful landscaping. This property may qualify for a seller funded permanent rate buydown with a participating lender. Equal Housing Opportunity.
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Christina Fata (407-917-8946)
1760 LEGION DR, WINTER PARK, FL 32789
$2,295,00075 Days on yellowkey MLS ID: O6383603
Bed: 4 Bath: 5.5 Gar: 2 Liv Area Sq Ft: 4392 Built: 1964 Tax: $13,622 (2025)Community: Green Oaks RepSingle Family
Taxes:$13,622
Remarks: Winter Park 1964 Charmer! This wonderful ranch is located just minutes to Downtown Orlando as well as Park Ave. With over 4300 sq ft of living space, this, 4 bed/5.5 bath home is in the prime location. Upon entering you'll notice just how light and bright this home shows, to your right you will find a home office space. Rich dark wood, custom cabinetry and dramatic lighting provide the perfect space to start your morning or end your day. To the left of the entry, you will find the large formal living room with 1 of 2 gas fires places located in this home. The bay window lets you take in views of your lush landscaped front yard and fills the space with tons of sunlight. Stepping off the entry you are greeted with a large formal dining room space. Sliders lead to the patio and the unique courtyard patio gives you views of your pool from not only the dining but the primary and family room all with sliders making this the perfect patio for parties, social gatherings and events. Just off the dining room you will find the great room including the breakfast area with built in cabinetry, the family room and the kitchen. The heart of the home is your kitchen, and this space has been designed for the chef of the home. White cabinetry, island, solid surface counter tops, lighting, and a huge walk-in pantry are just a few of the special touches you will find. Stainless steel appliances: Sub-Zero refrigerator, Bosh dishwasher, double oven, and microwave all the tools needs to create amazing meals. The family room's jewelry is the barrel ceiling a special touch you won't find often. Gas fireplace, spacious, Sliders leading to the patio as well as a screened patio area. The family room also includes a wet bar with ice market and wine frig. Just off the living room is the half bath. A separate area off the living could be a mother-in-law suite, she or he cave or the options are endless. a large bonus room includes a full bath which also doubles as the pool bath, sliders leading to a private yard space and a sink area. Upstairs in this area you will also find a full bedroom with vaulted ceilings and a full bath. To the right of the dining room, you will find 2 additional rooms and 2 full baths. The primary suite includes a sitting room with double doors leading to the bedroom, massive suite with bay window and views of the pool. not 1 but 2 full baths and 2 walk in closet because why share when you can have your own. This home also includes 2 tankless heaters, newer roof, well for sprinklers, home generator, skylights, dog run circular driveway custom drapes, auto blinds, freshly painted, artificial turf and so much more. So what are you waiting for?
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: Steven Looper (321-662-3582)
1077 MINNESOTA AVE, WINTER PARK, FL 32789
$1,625,0005 Days on yellowkey MLS ID: O6403223
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3046 Built: 2025 Tax: $1,383 (2025)Community: NaSingle Family
Taxes:$1,383
Remarks: Built in 2025 by Nautilus Homes and lightly lived in, this custom Winter Park residence offers a rare blend of new construction quality, thoughtful owner upgrades, and a highly desirable location between Orlando Avenue and Orange Avenue, just minutes from Park Avenue shopping, dining, and cultural attractions. Set behind mature landscaping and two inviting front porch seating areas, the home delivers over 3,000 square feet of living space, more than 4,000 square feet under roof, 4 bedrooms, 4 full baths, and a dedicated main-level office with a custom door package. More than $100,000 in post-build owner upgrades further enhance the home’s design, function, and everyday livability. Inside, Crème Brûlée wide-plank wood flooring runs throughout the home. Every bedroom features custom-built closets, while Arhaus lighting fixtures and plantation shutters add a refined finish across the interior. The main living area centers around a custom built-in entertainment wall with a vapor fireplace and integrated LED shelf lighting. The chef’s kitchen features ceiling-height custom cabinetry, a handcrafted wood range hood, and an adjoining butler’s pantry finished with Kit-Kat tile between the kitchen and formal dining room. A built-in wine and coffee bar sits just off the main living space, creating an easy flow for entertaining. The layout is both flexible and practical, with one en-suite bedroom and the dedicated office on the main level, plus three additional en-suite bedrooms upstairs. The primary suite includes a spa-inspired bath with soaking tub, oversized 9-foot walk-in shower, dual sprayers, frameless glass enclosure, and linear drainage. Outdoor spaces were designed for easy living, with professional front-yard landscaping, mature tree work, full gutters, and a private low-maintenance backyard retreat featuring artificial turf and decorative rock. The oversized 24x22 two-car garage has been fully built out with custom cabinetry, a full tool wall, overhead storage, and Shark Coating epoxy flooring. Zoned for Audubon Park K-8 and Winter Park High School, and located near Park Avenue, Mead Botanical Garden, and the Winter Park dining corridor. Showings by appointment. Buyer to verify school zoning, room dimensions, square footage and all property details.
Listing is courtesy of: SHAHRAM SONDI + CO. (407-718-6160)
Listing Agent: Shahram Sondi (407-718-6160)
2361 MULBRY DR, WINTER PARK, FL 32789
$2,395,00018 Days on yellowkey MLS ID: O6396840
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3111 Built: 2026 Tax: $6,436 (2025)Community: Lake Forest ParkSingle Family
Taxes:$6,436
Remarks: Casa Noir — Brand new construction custom home selected as a 2026 Parade of Homes showcase in Winter Park. 4 bedrooms. 4 full baths. Dedicated office. Loft. 2-car garage. Approximately 3,200 sq ft living space. Custom finishes done to perfection throughout. Inside, the foyer delivers on every promise made at the curb — soaring exposed oak beams, cascading brass pendants, and a sculpted arched alcove. Warm white oak wood floors begin here and do not stop. Anchoring the great room, the fireplace rises floor to ceiling in natural stone, with the kind of presence that makes everything else arrange itself around it. Custom oak built-ins with backlit shelving flank the space. At the far wall, a glass slider opens the room entirely to the pool beyond — where indoor and outdoor living become one. The kitchen is a destination. Custom white oak cabinetry climbs every wall to the ceiling. A full-height illuminated wine rack column. Glass-front uppers. The quartz island stretches across the heart of the room, dressed in brass pendants above and brass hardware at every pull. A 48-inch Thor gas range beneath a custom cabinet hood with integrated storage. A walk-in pantry connects both. Dining — connected, but defined. A sculptural alabaster chandelier hangs above a backlit arched niche. Easy for everyday. Elevated for hosting. Mudroom with a floating oak bench. Laundry finished in sage green cabinetry, quartz counters, and a matte black sink. Then the primary suite — and Casa Noir reaches its second act. An oak beam tray ceiling. A crystal chandelier on a brass canopy. The bath features floor-to-ceiling stone tile, a freestanding soaking tub, dual brass shower heads, and two independent floating fluted oak vanities, LED-lit at the base. The walk-in closet completes the space — floor-to-ceiling shelving, double hanging zones, and a built-in window seat. The office features moody charcoal walls, exposed oak beams, full-height wainscoting, steel-and-glass double doors, and a walk-in closet that allows it to function as a fifth bedroom when needed. The pool bath includes a fluted oak vanity with LED base lighting, terrazzo flooring, a ribbed tile shower, frameless glass, and brass throughout. Upstairs, a black steel staircase beneath a cascading glass disc chandelier leads to the loft. Three bedrooms follow — the ensuite finished in designer teal mosaic tile with brass fixtures and a frameless glass shower; the remaining two share a Jack-and-Jill bath with dual oak vanities, a herringbone tub surround, and brass throughout. Outside, a tongue-and-groove covered lanai anchors a fully built-in outdoor kitchen. Pavers lead to a crystal blue pool — a spa-resort setting that makes every weekend feel like a getaway without leaving home. Zoned for top-rated Audubon Park K-8 and Winter Park High School. Prime Winter Park location — minutes to Park Avenue, Rollins College, and more. Schedule your showing today.
Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)
Listing Agent: Ahmad Hassan, Pa (718-641-9358)
102 BELL PL, WINTER PARK, FL 32792
$1,399,00020 Days on yellowkey MLS ID: O6398118
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2459 Built: 2025 Tax: $4,224 (2025)Community: Eastgate SubSingle Family
Taxes:$4,224
Remarks: Step into elevated Florida living with this stunning brand-new residence, where modern design meets lasting quality. Constructed with solid block and steel framing for superior durability, this home is quietly nestled on a cul-de-sac in one of Winter Park’s most up-and-coming areas—without the restrictions of an HOA. Just moments from Interlachen Country Club and the charming Lakemont Heights neighborhood, the location offers both prestige and convenience. From the moment you enter through the impressive double doors, you’re welcomed by a light-filled, open-concept design. Soaring 10-foot ceilings and elegant 8-foot doors create an airy, expansive feel, while abundant natural light highlights the home’s sleek, contemporary finishes. At the heart of the home, the chef-inspired kitchen truly shines. Outfitted with luxurious quartz countertops, stainless steel appliances, and a custom LED-lit wine display, it’s designed to impress. The seamless flow into the living and dining spaces—along with views of the backyard—makes it perfect for entertaining or everyday connection. The primary suite is a private sanctuary, offering a spa-like escape with dual vanities, a spacious dual-entry shower, and a freestanding soaking tub designed for relaxation. With three additional bedrooms, a dedicated office, and 3.5 beautifully appointed bathrooms, this thoughtfully designed single-story home provides nearly 2,500 square feet of flexible living space. Outdoors, your personal retreat awaits. Enjoy year-round Florida living on the covered lanai, complete with a built-in summer kitchen and a custom-designed pool—ideal for hosting or unwinding. The fully fenced yard features new vinyl fencing, fresh sod, and an automated sprinkler system for effortless maintenance. Perfectly positioned near Phelps Park, the Winter Park YMCA, Lakemont Elementary, and an array of top-tier shopping and dining destinations, this home delivers the ideal blend of privacy, craftsmanship, and everyday luxury.
Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)
Listing Agent: Nick Mckee (407-913-0171)
2408 LAFAYETTE AVE, WINTER PARK, FL 32789
$1,495,00024 Days on yellowkey MLS ID: O6397694
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2838 Built: 2024 Tax: $3,770 (2024)Community: Winter Park VillageSpa: NoSingle Family
Taxes:$3,770
Remarks: This custom home is nestled in an up-and-coming neighborhood in Winter Park. This stunning home redefines modern living. Designed with an open floor plan, it seamlessly blends spaces to create a harmonious flow, perfect for both entertaining and everyday life. The abundance of windows bathes the interiors in natural light, creating a bright and airy ambiance. The office/study is set apart for quiet pursuits. The chef’s kitchen opens naturally to the great room and boasts a large island, top-of-the-line Thermador appliances, complemented by the sleek quartz countertops that offer both style and functionality. Conveniently equipped with two sets of washers and dryers, this home ensures efficiency and ease for the busiest of households. Retreat to the master suite, where luxury meets serenity. A massive walk-in closet provides ample storage, while the spa-like master bath invites relaxation with its elegant design and premium features. The indoor outdoor flow is easy with the huge set of glass sliders leading to the covered porch equipped with drop down screens. Enjoy the summer kitchen and sparkling pool while entertaining family and friends. This home is a true gem that combines thoughtful details with sophisticated style.
Listing is courtesy of: CORCORAN PREMIER REALTY (407-965-1155)
Listing Agent: Matthew Burks (407-257-5347)
234 DETMAR DR, WINTER PARK, FL 32789
$1,599,00083 Days on yellowkey MLS ID: O6379927
REDUCED by $46,000 (2.8%) on 04/29/2026
Bed: 4 Bath: 5.5 Gar: 1 Liv Area Sq Ft: 3609 Built: 1935 Tax: $13,664 (2025)Community: Osceola Shores Sec 1Spa: NoSingle Family
Taxes:$13,664
Elementary School: Lakemont Elem
Remarks: Nestled behind gates in the heart of Winter park, this enchanting 1930's residence blends historic charm with many recent upgrades. The beautifully renovated kitchen anchors the home, while the downstairs primary suite offers privacy and comfort with an elegant spa inspired bath. The detached one bedroom guest house is perfect for houseguests, a home office or multi-generational living. The main house has a flexible floor plan that includes four bedrooms and four and one half baths, a sunroom ideal for home office, formal dining room, oversized family room and charming sitting area with fireplace. The kitchen is a chef's delight with six burner gas range, large center island, plentiful l space for gatherings and a separate breakfast room. Other notable features include gleaming wood floors, double pane windows offering abundant natural light, adorable laundry room/mud room. French doors from many rooms open to a classic front porch that is a perfect place for relaxing and enjoying picturesque grounds with towering oaks. Step outside to a private heated pool. Detached garage includes Tesla charging station. This gated compound situated on .42 acres is one block from Lake Osceola and a easy walk to Park Avenue.
Listing Agent: Nicole Seybold (407-808-9374)
1611 CHESTNUT AVE, WINTER PARK, FL 32789
$1,100,0004 Days on yellowkey MLS ID: O6402502
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2916 Built: 1973 Tax: $3,590 (2025)Community: Lake Knowles TerraceSingle Family
Taxes:$3,590
Remarks: Situated on arguably the finest brick street in Winter Park, beneath a canopy of live oaks, this fully renovated 4-bedroom, 4-bath home delivers the rarest combination: the soul of an established neighborhood with the bones of new construction. Gutted to the studs and rebuilt with intention, every smajor system is new — electrical, AC, roof, ductwork, drywall. With elevated finishes , like designer tile and quartz countertops as well as new floors and beautifully reimagined kitchen and baths. A second-floor addition adds a sprawling 21 x 24 foot private primary suite and home office, one of the many reasons this an ideal setup for MULTIGENERATIONAL families and those who work from home. A welcoming fireplace, lush mature landscaping, butler's pantry, numerous built ins, custom tile work, and an address minutes from Park Avenue make this one of Winter Park's most compelling offerings. Come imagine the possiblities.
Listing Agent: Olivia Maxwell (407-222-4440)
1660 WALNUT AVE, WINTER PARK, FL 32789
$1,650,0007 Days on yellowkey MLS ID: O6395277
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2249 Built: 2026 Tax: $6,297 (2025)Community: Lake Knowles TerraceSpa: NoSingle Family
Taxes:$6,297
Remarks: Introducing a standout new construction in Winter Park’s coveted Tree Streets! As you arrive the home’s modern façade is complemented by a charming front porch, creating a warm yet striking introduction that feels both inviting and intentional. Inside, the home unfolds with a highly functional floor plan designed to enhance everyday living while still accommodating entertaining with ease. Clean lines, curated finishes, and natural light define the main living spaces, where the kitchen, dining, and living areas flow seamlessly together. The kitchen serves as a true focal point, featuring Calacatta Gioia quartz countertops, custom cabinetry with ample storage, a paneled refrigerator, and a full suite of Thermador appliances. The space transitions naturally into the dining area and living room, where a built-in wet bar with a wine fridge adds an elevated layer of functionality and style. The living room is designed to feel both open and connected, anchored by expansive pocketing sliders that completely open to the outdoor living area. The primary suite is thoughtfully positioned on the main level, serving as a calming retreat, featuring a spa-inspired bathroom with dual vanities, a freestanding soaking tub, and a spacious walk-in shower. Upstairs, three additional bedrooms are generously sized and well laid out, providing flexibility for guests, family, or a secondary living setup. The outdoor living experience is equally impressive, centered around a large covered lanai that offers ample space for al fresco dining and lounging. The spacious pool area is designed to complement the home’s indoor-outdoor lifestyle, creating a private setting that feels both relaxed and elevated. Beyond the home itself, the location is what truly sets this home apart. Situated in the heart of the Tree Streets, you are just a short walk to Phelps Park and the YMCA, minutes from Interlachen Country Club, and only a quick golf cart ride to the shops, dining, and energy of Park Avenue. Homes of this caliber and location are few and far between, making this a standout opportunity in today’s market.
Listing is courtesy of: ONE LUXURY INTERNATIONAL LLC (407-312-8003)
Listing Agent: Christopher Christensen (407-312-8003)
363 N PHELPS AVE, WINTER PARK, FL 32789
$1,249,00011 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)
688 BRECHIN DR, WINTER PARK, FL 32792
$724,9004 Days on yellowkey MLS ID: O6403080
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1599 Built: 1961 Tax: $6,760 (2025)Community: Kenilworth Shores Sec 04Spa: NoSingle Family
Taxes:$6,760
Remarks: Discover one of the sought-after communities in Winter Park, Kenilworth Shores, where mature oak trees frame the streets, spacious parks serve as gathering ground for families and peaceful walking trails weave through the neighborhood. Centrally within arm’s reach of luxury shopping on Park Avenue in Winter Park, stunning lake views and parks in Baldwin Park, and chef-driven local restaurants in Audubon Park. Kenilworth Shores isn't just a location, it's a community, and this four-bedroom, two-bath Florida ranch is your family's invitation to join. At nearly 1,600 square feet, this home provides charm, function and thoughtful design with upgraded LVP flooring flowing throughout the easy layout. Old world brick detailing gives the exterior genuine curb appeal, while a thoughtfully renovated interior delivers a ready-to-move-in home. A gorgeous brick fireplace anchors an open kitchen, family and dining room combination, with loads of natural light and function to entertain in style. The kitchen is outfitted with white shaker custom cabinetry, granite counters, a soft glass tile backsplash, stainless steel appliances and glass pendant lighting over bar seating. A desirable split-bedroom plan provides privacy for guests, while the primary suite opens to the backyard and includes a completely renovated main bath. The flexible fourth bedroom is outfitted with a custom-designed built-in Murphy bed system with flanking closets and storage. Sitting off the primary living area, this bedroom provides options to fit flexible needs such as home office, guest room, playroom or secondary family space. Go into the backyard and experience your personal Florida oasis with a screened covered porch and grand Florida pool to cool off in the heat of summer. The surrounding, spacious yard is adorned with artificial turf (beautiful, durable and effortlessly low maintenance), complete with a putting green that will make this yard the destination for every playdate, summer barbecue or birthday party. Completed upgrades include new roof (2021), resurfaced pool (2021), new irrigation and well (2022), new wood fence (2023), new dishwasher and built-in microwave (2023), HVAC (late 2023), new washer and dryer (2024), and new pool pump motor (2025). The best part of this special neighborhood is the connected community. Zoned for Brookshire Elementary, Glenridge Middle and WP High, some of the best Orange County Schools. Cady Way Park is nearby with a community pool, baseball fields, a playground, pickleball courts, and miles of recreational and bike trails. This location checks all the boxes. Schedule your private showing today.
Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)
Listing Agent: Alison Mosley (407-304-6458)
1981 BLUE RIDGE RD, WINTER PARK, FL 32789
$1,150,0003 Days on yellowkey MLS ID: O6402961
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2750 Built: 1963 Tax: $11,270 (2025)Community: Timberlane ShoresSingle Family
Taxes:$11,270
Remarks: Welcome to 1981 Blue Ridge Rd in Winter Park, a spacious 4-bedroom, 2-bath home featuring an open floorplan, a generous family room, and a layout designed for both comfortable everyday living and easy entertaining. The home offers a well-connected flow between the main living spaces, creating an inviting setting with room to gather, relax, and spread out. Inside, the living room, dining room, and kitchen are arranged in a way that supports an open and functional feel, making the home especially appealing for hosting and daily routines alike. The family room adds valuable extra living space and creates a natural hub for movie nights, casual gatherings, or a second lounge area. The floorplan also shows a sun room extending off the family room, giving the home even more flexibility for relaxing, hobbies, or enjoying a bright bonus space with views of the backyard. The bedroom layout is thoughtfully separated from the main entertaining areas, offering privacy and comfort. The primary suite is positioned apart from the secondary bedrooms and includes its own bath and closet space, creating a peaceful retreat within the home. Three additional bedrooms provide flexibility for guests, a home office, or changing household needs. Outside, the open patio and private yard add to the home’s lifestyle appeal, creating space to enjoy outdoor dining, weekend get-togethers, gardening, or quiet mornings in the Florida sunshine. Together with the interior layout, these outdoor features help make the home feel both versatile and welcoming. Located in Winter Park, the property is set in a highly desirable area known for its established residential feel, attractive surroundings, and convenient access to shopping, dining, parks, and everyday amenities. The neighborhood adds to the home’s appeal by offering both comfort and accessibility in one of Central Florida’s most sought-after locations. **This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.**
Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)
Listing Agent: Thomas Nickley, Jr (407-629-4420)
2922 REEF KNOT PL, WINTER PARK, FL 32792
$1,149,000330 Days on yellowkey MLS ID: O6316445
0 Days Off yellowkey (back on 5/2/2026)
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3153 Built: 2019Monthly Fee: $186 Tax: $10,521 (2024)Community: Lake Florence PreserveSpa: YesSingle Family
Taxes:$10,521
Remarks: Under contract-accepting backup offers. 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 Agent: Ellen Bessette (407-496-0076)
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