Location: Winter Park
Do Not Show Listings
346 S RANGER BLVD, WINTER PARK, FL 32792
$475,000261 Days on yellowkey MLS ID: S5134662
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1592 Built: 1965 Tax: $5,339 (2024)Community: Winter Park PinesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$5,339
Elementary School: Aloma Elem
High School: Winter Park High
Tax Year: 2024
Middle School: Glenridge Middle
Remarks: PRIME LOCATION! Beautiful 3 Bedroom 2 Bathroom home is located in sought after Winter Park Pines with NO HOA and NO CDD. It is situated on a Corner Lot (0.22 Acre) and is a super short distance to the High Rated schools in Winter Park. The interior is extremely well kept with engineered wood floors, crown molding, and a beautiful glass entry door. There is a captivating white-washed stone fireplace and built in shelving for an elegant look in the Family Room. The kitchen has stainless steel appliances, wood cabinets with under cabinet lighting, and bar top seating. Primary Bedroom has a walk-in closet and a glass door shower with tile walls and built-in niches. The Primary bathroom has private access to the screened patio (Florida Room) and spacious backyard. The gated fence opens extra wide for boat, RV or your trailer entry. This entry is very convenient to back any trailer size. For outdoor activities, you just step out of the house and go on a Cady Way Trail for biking, skating, and walking activities. For tennis lovers there are very well kept tennis courts where sport enthusiasts practice their skills in pickleball. Right next to the tennis courts is a playground that offers cozy shaded areas with slopes, swings, and climbing walls. Publix, Costco, Walmart and the post office are all located nearby. For evening promenade the downtown Winter Park, located just a few miles away, offers unique restaurants, cozy coffee shops and bars. To see this amazing 3 bedroom home for sale in Winter Park, call today and schedule a showing! NOTE: Roof - July 2023. HVAC - 2015. No HOA, NO CDD.
Listing is courtesy of: IMPERIAL REALTY OF FLORIDA INC (407-346-4746)
Listing Agent: Tanya Vyushkina (407-346-4746)
739 ROUGHBEARD RD, WINTER PARK, FL 32792
$800,00029 Days on yellowkey MLS ID: O6404545
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2194 Built: 1968 Tax: $6,179 (2025)Community: Winter Park PinesSingle Family
Taxes:$6,179
Tax Year: 2025
Remarks: Welcome to Winter Park Pines, one of Winter Park’s most desirable neighborhoods. This updated 5 bed, 3 bath pool home features a split floor plan, generous room sizes, and wood-plank tile flooring throughout most of the home. Inside, the formal living and dining rooms flow together and overlook the pool through French doors, while the large primary suite offers an en-suite bath, walk-in closet, and its own French doors to the huge covered, insulated patio. The light and bright kitchen includes a large breakfast bar, built-in pantry, and white cabinetry and appliances, and opens to the family room with a wood-burning fireplace and built-in desk. A separate bedroom wing provides four generous guest bedrooms and two full baths, including a Jack-and-Jill setup with walk-in closet, plus a true pool bath with access to the backyard and an inside utility/laundry room. Outdoor living is a highlight, with a fenced backyard, kidney-shaped pool, plenty of deck space, and ample yard beyond the pool so you’re not sacrificing green space. The large covered, insulated patio is ideal for year-round use. Major updates include a new roof (2022), new electric panel and updated outlets (2022), water lines re-piped to CPVC by a previous owner, new fence (2023), new dishwasher (2024), new water heater (2025), newer stove, washer, and dryer, new light fixtures throughout, and bathrooms updated with modern colors and fixtures. The exterior, garage, patio, and pool deck have all been freshly painted, giving the home a clean, move-in ready feel. This is a rare opportunity to own a well-maintained pool home in a prime Winter Park location—just steps from Cady Way Park and Trail and moments from Winter Park Pines Golf Course, with Winter Park High School and the nearby hospital campus within short distance and quick access to downtown Orlando, major highways, both airports, Disney, and Universal.
Listing is courtesy of: SERHANT (786-296-8626)
Listing Agent: John Harbuck (407-538-2841)
1761 LEGION DR, WINTER PARK, FL 32789
$3,270,000355 Days on yellowkey MLS ID: O6302616
REDUCED by $25,000 (0.8%) on 04/15/2026
Bed: 5 Bath: 5.5 Gar: 3 Liv Area Sq Ft: 4955 Built: 2017 Tax: $22,139 (2024)Community: Green Oaks Rep 02Spa: YesSingle Family
Taxes:$22,139
Elementary School: Dommerich Elem
Middle School: Maitland Middle
Remarks: One of the most coveted neighborhoods in all of Winter Park! This custom-built 5-bedroom, 5.5-bath residence was completed in 2017 and first sold in 2018. Lovingly maintained by the original owner and elevated with high-end designer finishes, the home showcases the impeccable vision of renowned designer Ted Maines, who reimagined much of the interior with timeless sophistication. Perfectly positioned on a prime over-sized corner lot, the home blends transitional architecture with modern elegance. Sunlight fills the open layout through expansive sliding doors, creating effortless indoor-outdoor flow. The main living area seamlessly connects a formal living room and spacious dining area to the gourmet kitchen, complete with custom cabinetry, Carrara marble surfaces, and Sub-Zero and Wolf appliances. A cozy family room with fireplace provides a relaxed yet stylish gathering space. The private downstairs primary suite opens directly to the lanai, saltwater pool and features a spa-style bath. A secondary ground floor bedroom is perfect for guests or multigenerational living. Upstairs, enjoy a spacious loft with custom bar, leading to a versatile media room. Three additional en-suite bedrooms complete the second level. Recent enhancements include a full-house generator, a newly added semi-circular driveway that enhances curb appeal and functionality, and three newer A/C units with re-engineered, high-efficiency ductwork to ensure optimal climate control throughout the home. The outdoor living space is equally impressive, offering a saltwater heated pool and spa with cascading waterfall, elegant stone decking, ambient lighting, and a covered summer kitchen—ideal for year-round entertaining. A rare 3-car garage completes this exceptional home. All just moments from the shops, dining, and charm of downtown Winter Park.
Listing is courtesy of: SCANLON REALTY GROUP LLC (305-905-0496)
Listing Agent: Brian Scanlon (305-905-0496)
141 GLENRIDGE WAY, WINTER PARK, FL 32789
$3,250,00067 Days on yellowkey MLS ID: O6393616
1 Days Off yellowkey (back on 5/16/2026)
Bed: 5 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 5243 Built: 2008 Tax: $40,155 (2025)Community: CharmontSingle Family
Taxes:$40,155
Elementary School: Audubon Park K8
Middle School: Audubon Park K-8
Remarks: Under contract-accepting backup offers. Grand Southern charm and architectural elegance define this stately residence in one of Winter Park’s most desirable neighborhoods, set along a quiet brick-lined street just steps from Lake Chelton. Positioned on nearly half an acre, the home spans over 5,200 square feet, offering 5 bedrooms, 4.5 baths, a designated office, a large, versatile media/game room, a 3-car garage, and an expansive lanai with summer kitchen and resort style pool— all brought together in a smart well-planned layout ideal for effortless everyday living and exceptional entertaining. Step inside to a beautifully curated interior where rich architectural detail and livable design come together. Extensive custom millwork—seen in detailed moldings, trim work, and built-ins—adds depth and character throughout. The entry opens to gracious living and dining spaces, complemented by an impressive 550+ bottle temperature-controlled wine room. At the heart of the home, a beautifully appointed Kitchen, featuring white wood cabinetry, a six-burner gas range, an oversized quartz island, and a delightful breakfast nook that seamlessly connects to the family room featuring custom built-ins and fireplace—creating a natural gathering space. Tucked away, the first-floor primary suite offers a spacious sitting area, a beautifully customized closet with dressing area, and a luxurious bath with marble flooring, a large double-head walk-in shower, dual vanities, a free -standing tub, and built-in linen cabinetry—designed as a calming and private sanctuary. The first level also features a private guest bedroom with en-suite bath, creating an ideal setup for friends & family. A generously sized laundry room offers abundant cabinetry and exceptional storage, making everyday tasks feel effortless. Upstairs, three spacious bedrooms and two full baths provide comfortable accommodations, with two bedrooms opening through French doors to the front double balcony—perfect for enjoying peaceful treetop views. The back of the home unfolds around a beautiful pool and spa, with French doors from multiple rooms opening to the lanai and creating a natural indoor-outdoor connection. Retractable screens allow for year-round enjoyment of the well-appointed summer kitchen, making it ideal for both relaxed evenings and easy entertaining. Other notable highlights: a whole house natural gas generator, extensive brick paver driveway & motor court, automated driveway gate, integrated sound system, security cameras and new roof 2024. Lastly, this profound property offers top rated Winter Park schools and easy access to Park Ave, Downtown Orlando, Audubon Park Garden District and Baldwin Park.
Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)
Listing Agent: Mary Colton (407-222-7388)
3054 BLUEBROOK DR, WINTER PARK, FL 32792
$410,00051 Days on yellowkey MLS ID: O6398450
REDUCED by $17,500 (4.1%) on 05/15/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1939 Built: 1973 Tax: $6,422 (2025)Community: Laurel SpgsSingle Family
Taxes:$6,422
Remarks: Just Reduced the Price! "Open the Doors to Your Dreams" of owning an Affordable Home with a pool in Winter Park. The home features a Spacious Kitchen with Upgraded Cabinets, and stone countertops; Primary bedroom suite is amazing. You will love the layout and upgraded primary bathroom; Beautiful Porcelain tile flooring throughout the home; Large family room with fireplace; Large screened back porch/LANAI. And here is an inground pool in the back yard. You will enjoy entertaining in this home featuring a gourmet kitchen with granite countertops, and stainless steel appliances. This property may qualify for Seller Financing (Vendee). If property was built prior to 1978, Lead Based Paint Potentially Exists. Come tour this home today. We expect this one not to be on the market long at this REDUCED price.
Listing is courtesy of: WEATHERSPOON REALTY INC (407-878-4468)
Listing Agent: Eugene Weatherspoon (407-878-4468)
3627 SEAGRAPE DR, WINTER PARK, FL 32792
$339,00031 Days on yellowkey MLS ID: O6403218
0 Days Off yellowkey (back on 5/15/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1233 Built: 1965 Tax: $3,401 (2024)Community: Eastbrook Sub Unit 03Single Family
Taxes:$3,401
Elementary School: None
High School: None
Middle School: None
Remarks: Under contract-accepting backup offers. Welcome to 3627 Seagrape Drive, a move-in ready home for sale in Winter Park featuring NO HOA, an oversized lot, and energy-efficient upgrades in a prime Central Florida location. This 3-bedroom, 2-bath home offers an updated kitchen with granite countertops, stainless steel appliances, tile flooring throughout, crown molding, and indoor laundry for everyday convenience. Major improvements include a 2019 roof and solar panels, helping reduce energy costs. The large backyard provides rare space to expand, entertain, or create your own outdoor retreat. Ideally located just minutes from Costco Wholesale, Park Avenue, dining, shopping, and major highways, this property is perfect for buyers searching Winter Park FL homes for sale with land, updated features, no HOA, and strong long-term value or investment potential.
Listing is courtesy of: RE/MAX TOWN & COUNTRY REALTY (407-695-2066)
Listing Agent: Kelly Sue Stonebreaker (321-228-3974)
1900 WINTER PARK RD, WINTER PARK, FL 32789
$849,90036 Days on yellowkey MLS ID: O6402566
REDUCED by $91,100 (9.7%) on 05/15/2026
Bed: 4 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1511 Built: 1947 Tax: $2,803 (2025)Community: CharmontSingle Family
Taxes:$2,803
Remarks: Positioned in one of Central Florida’s most iconic and sought-after locations, this rare opportunity at 1900 Winter Park Road in Winter Park invites you to create something truly exceptional. Set on a spacious homesite, this property offers the flexibility to renovate, expand, or build your custom dream home from the ground up. Whether you envision a modern architectural masterpiece or a timeless estate, this is your canvas to bring that vision to life. What makes this opportunity even more compelling is the location. Just minutes from the charm and sophistication of Park Avenue, you’ll find yourself surrounded by brick-lined streets, boutique shopping, fine dining, and vibrant cultural experiences. Spend your mornings enjoying coffee at local cafés, your afternoons exploring art galleries, and your evenings dining under the lights of one of Central Florida’s most beloved destinations. Living in Winter Park is more than owning a home—it’s embracing a lifestyle. From the scenic beauty of the Winter Park Chain of Lakes, to the historic elegance of Rollins College, this area blends natural beauty, culture, and community in a way few places can. Residents enjoy: Boat tours and waterfront living along the chain of lakes Weekly farmers markets and local events A thriving arts scene including museums, galleries, and theaters Top-rated dining and boutique retail experiences A true sense of community with timeless charm This is more than just land. This is where vision meets opportunity. This is where your next chapter begins. Build the life you’ve been dreaming of—in the heart of Winter Park
Listing is courtesy of: RE/MAX ASSURED (800-393-8600)
Listing Agent: William Grim, Iii (407-314-9784)
1287 VERDANT GLADE PL, WINTER PARK, FL 32792
$850,00039 Days on yellowkey MLS ID: O6400331
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3020 Built: 2020Monthly Fee: $413 Tax: $6,133 (2025)Community: Meadows At Hawks CrestSingle Family
Taxes:$6,133
Elementary School: Eastbrook Elementary
High School: Lake Howell High
Middle School: Tuskawilla Middle
Remarks: **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.** Welcome to 1287 Verdant Glade Place in Winter Park, a spacious two-story home offering 4 bedrooms, 3 full baths, 1 half bath, and a dedicated office, all thoughtfully arranged within an open floorplan designed for both comfortable living and easy entertaining. Inside, the home feels bright, expansive, and well connected, with generous living areas that flow naturally from one space to the next. The open design creates an inviting setting for everyday routines, gatherings, and holiday hosting, while the separate office adds flexibility for working from home, studying, or creating a quiet retreat. With two primary bedroom suites, a large game room, and an additional loft, there is plenty of space to accommodate guests, a growing household, or changing lifestyle needs. The home also features thoughtful upgrades that elevate both style and function. A gourmet kitchen serves as the heart of the home, complete with quartz countertops, 42-inch cabinetry, and the kind of workspace and storage today’s buyers appreciate. Eight-foot interior doors add to the sense of scale throughout, while details such as a pocket door in the bathroom enhance convenience and flow. Large sliding glass doors open wide to create a seamless connection between the indoor living spaces and the outdoor entertaining area. Step outside to an oversized screened and covered patio that extends the living space and creates a relaxing place to enjoy morning coffee, outdoor dining, or quiet evenings at home. Beyond the patio, the private yard offers even more appeal, with no rear neighbors behind the home for added privacy and a more open feel. The rear eastern exposure welcomes beautiful morning sun, making the backyard setting especially enjoyable at the start of the day. Located in Winter Park, the home benefits from a highly desirable area known for its established residential feel, convenient access to shopping and dining, and close proximity to parks, schools, and major roadways. The neighborhood adds to the home’s appeal by offering a blend of comfort, accessibility, and the everyday convenience that makes Winter Park such a sought-after place to live. With its flexible two-story layout, dual primary suites, game room, loft, gourmet kitchen, oversized patio, and private backyard setting, 1287 Verdant Glade Place delivers the space, upgrades, and lifestyle features buyers are looking for.
Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)
Listing Agent: Thomas Nickley, Jr (407-629-4420)
423 OLOLU DR, WINTER PARK, FL 32789
$549,000145 Days on yellowkey MLS ID: O6369976
REDUCED by $40,000 (6.8%) on 05/14/2026
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 1920 Built: 1981 Tax: $4,030 (2024)Community: Killarney CircleSingle Family
Taxes:$4,030
Elementary School: Killarney Elem
High School: Edgewater High
Middle School: College Park Middle
Remarks: PRICE IMPROVEMENT! Welcome to this beautifully remodeled two story home in one of Winter Park’s most desirable upscale neighborhoods, offering timeless charm, modern upgrades, and no HOA restrictions. Completely renovated in 2019, this property features a newer roof, windows, A/C system, electrical, plumbing, driveway, and a fully fenced yard with a private entry gate, along with fresh exterior & interior repaint completed in 2025. Inside, you will find bright, open living spaces and a modern kitchen designed for both everyday living and entertaining. Upstairs, a spacious family room opens to a covered balcony with serene lake views, creating an ideal space to relax or entertain. The flexible layout also allows for two separate living areas, making it well suited for multi-generational living or rental income. Step outside to enjoy the expansive gated yard with plenty of room for gatherings along with ample parking. Conveniently located just minutes from shopping, dining, Downtown Orlando, Downtown Winter Park, Full Sail University, and Rollins College, this home offers an exceptional location. The seller is offering 1% closing cost Buyer credit with a full price offer. Do not miss this rare opportunity to own a beautifully updated home with endless potential in a highly desirable location. Contact us today to schedule your private showing!
Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)
Listing Agent: Jill Healey (407-797-1420)
WINTER PARK, FL 32789
$1,249,90021 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
Listing is courtesy of: RE/MAX EXCLUSIVE COLLECTION (407-447-2829)
Listing Agent: Kim Griffin (407-314-5033)
2600 EUSTON RD, WINTER PARK, FL 32789
$630,00053 Days on yellowkey MLS ID: O6397890
Bed: 6 Bath: 3.0 Liv Area Sq Ft: 3145 Built: 1951 Tax: $7,446 (2024)Community: Glencoe SubSingle Family
Taxes:$7,446
Remarks: Discover a unique opportunity in the heart of Winter Park, just moments from Lake Killarney. This versatile property offers exceptional potential for multigenerational living, a primary residence with additional income, or a strategic investment. The home features a flexible layout designed to adapt to a variety of needs, with bright living spaces, natural light throughout, and comfortable areas ideal for both everyday living and entertaining. Its design allows for privacy and functionality, making it an attractive option for homeowners and investors alike. Enjoy a spacious outdoor setting surrounded by mature landscaping, perfect for relaxing or hosting gatherings. Recent upgrades add even more value and peace of mind, including solar panels that will be fully paid off at closing, as well as a newer roof and updated air conditioning system, offering efficiency and long-term savings. Ideally located just minutes from Park Avenue, Rollins College, and a wide variety of shopping, dining, and entertainment options. With easy access to major roadways, commuting throughout Central Florida is both quick and convenient. A rare opportunity to own a property with flexibility, location, and strong long-term value in one of the area’s most desirable communities. Schedule your private showing today.
Listing is courtesy of: AROD PARTNERS REALTY (407-627-7621)
Listing Agent: Suheil Flores (407-693-3060)
1903 N PARK AVE, WINTER PARK, FL 32789
$1,695,000132 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
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)
1523 MILLER AVE, WINTER PARK, FL 32789
$1,499,999146 Days on yellowkey MLS ID: O6371649
REDUCED by $50,001 (3.2%) on 05/14/2026
Bed: 5 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3164 Built: 2026 Tax: $3,620 (2025)Community: LawndaleSingle Family
Taxes:$3,620
Remarks: BRAND NEW CONSTRUCTION COMPLETED APRIL 2026, MOVE-IN READY. This 3,164 sqft home at 1523 Miller Ave, Winter Park, FL 32789 combines modern design, high-end finishes, and an unbeatable central location. Featuring 5 bedrooms, 4 full bathrooms, and a private salt-water pool, the home is designed for both everyday comfort and effortless entertaining. The open L-shaped living, kitchen, and dining area is filled with natural light and anchored by a 4-panel grand pocket slider that fully retracts, opening the entire living space to the covered patio for true indoor-outdoor living. The chef’s kitchen overlooks the main living area and flows seamlessly outside to a fully equipped outdoor kitchen with grill, sink, and fridge, complemented by a spacious seating area and pool—ideal for hosting year-round. Additional highlights include a shingle roof with metal accents, a pergola accenting the front of the garage, and clean architectural lines that elevate the curb appeal. The floor plan offers flexibility with generous bedroom sizes and well-appointed full baths, while the backyard retreat centers around the sparkling salt-water pool. Location is a major advantage—2 minutes to I-4, 4 minutes to Mills Avenue, 5 minutes to Park Avenue, 10 minutes to Downtown Orlando, and approximately 20 minutes to Disney, placing dining, shopping, nightlife, and major employers all within easy reach. A rare opportunity to own a brand-new construction home in one of Winter Park’s most connected neighborhoods.
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: Eric Trumble Ii (407-592-8624)
814 DENSMORE DR, WINTER PARK, FL 32792
$425,00047 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)
3330 COLEUS CT, WINTER PARK, FL 32792
$384,900112 Days on yellowkey MLS ID: O6378218
0 Days Off yellowkey (back on 4/1/2026)
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1988 Built: 1968 Tax: $5,410 (2024)Community: Eastbrook Sub Unit 14Single Family
Taxes:$5,410
Remarks: Situated in an established Winter Park neighborhood, this single-family residence offers a functional layout with generous living space designed for everyday comfort. The home features multiple living areas that provide flexibility for daily living, entertaining, or work-from-home needs. Conveniently located near major roadways, public transit, shopping, dining, and surrounding Central Florida destinations, this property offers a balanced blend of accessibility and neighborhood appeal within Seminole County.
Listing is courtesy of: MAINSTAY BROKERAGE LLC (800-583-2914)
Listing Agent: Raquel Littlejohn (470-279-6333)
721 DUNBAR ST, WINTER PARK, FL 32789
$399,99925 Days on yellowkey MLS ID: O6405338
1 Days Off yellowkey (back on 5/13/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1018 Built: 1950 Tax: $5,267 (2025)Community: Carver TownSingle Family
Taxes:$5,267
Remarks: Under contract-accepting backup offers. Welcome to 721 Dunbar St in Winter Park, a 2-bedroom, 2-bath home with a simple layout and plenty of potential. This property offers a comfortable starting point for everyday living and a great opportunity for buyers who want a home they can make their own over time. Inside, the home offers practical living spaces and a layout that works well for daily routines. The two-bedroom, two-bath setup adds flexibility for guests, a home office, or changing needs. The home has a solid foundation for updates, giving the next owner the chance to improve and personalize the space to match their style and preferences. Outside, the property gives you room to enjoy the yard and think about future possibilities. Whether you want to refresh the outdoor space, add your own touches, or simply enjoy the home as it is, there is a lot of opportunity here. Located in Winter Park, the home is close to shopping, dining, parks, and major roads, while still being in an established residential area. The neighborhood adds to the appeal with its convenient location and access to everything that makes Winter Park a popular place to live.
2225 WINTER WOODS BLVD, WINTER PARK, FL 32792
$375,00050 Days on yellowkey MLS ID: O6398734
1 Days Off yellowkey (back on 5/12/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1473 Built: 1968Monthly Fee: $2 Tax: $3,236 (2024)Community: Winter Woods Unit 01Single Family
Taxes:$3,236
Elementary School: English Estates Elementary
Remarks: Under contract-accepting backup offers. MULTIPLE OFFERS RECEIVED, PLEASE SUBMIT YOUR BEST OFFER BY 5PM EST ON MONDAY 5/11/2026. Welcome to this beautifully maintained three-bedroom, two-bathroom home offering nearly 1500 square feet of thoughtfully designed living space on an expansive pie-shaped lot. Featuring a desirable split floor plan, this move-in ready residence combines functional living spaces with tasteful updates throughout, all in a convenient location close to shopping, dining, major roadways, and some of Central Florida’s most sought-after destinations. Inside, fresh interior paint and updated wood-grain laminate and tile flooring create a warm and inviting atmosphere. Multiple living and gathering spaces include a comfortable sitting room, dedicated dining area, and a spacious layout ideal for both everyday living and entertaining. The laundry room offers exceptional storage space and a utility sink, with the washer and dryer included, for added convenience. The kitchen features honey-toned oak cabinetry, black appliances, a closet pantry, and ample workspace for meal preparation and hosting. Privately positioned away from the secondary bedrooms, the primary suite serves as a peaceful retreat with fresh paint, a walk-in closet, ceiling fan, and en-suite bathroom complete with a white single vanity and tiled shower. The updated hall bathroom, renovated in 2021, showcases a contemporary white vanity and tiled tub/shower combination. Step outside to enjoy the oversized fully fenced backyard offering endless opportunities for outdoor living, gardening, pets, or future enhancements. A screened lanai with brand-new screening installed in 2025 provides the perfect spot to relax year-round. Additional exterior improvements include an updated paver driveway and updated garage doors completed in 2024, enhancing both curb appeal and functionality. The two-car garage and mature landscaping complete the exterior package. Ideally located just minutes from everyday conveniences, this home is approximately 10 minutes from the dining, shopping, and charm of Park Avenue in Winter Park, 25 minutes from Orlando International Airport, and offers close proximity to UCF, Full Sail University, and Rollins College. Convenient access to major transportation routes, restaurants, retail stores, and entertainment makes this location as practical as it is desirable. ROOF - 2019 HVAC - 2021 PLUMBING - 2025 ELECTRICAL - 2025
Listing Agent: Amy Turner (407-803-3885)
433 CAROLINA AVE, WINTER PARK, FL 32789
$1,395,00022 Days on yellowkey MLS ID: O6406911
0 Days Off yellowkey (back on 5/11/2026)
Bed: 5 Bath: 3.5 Liv Area Sq Ft: 2771 Built: 2018 Tax: $16,685 (2025)Community: Winter ParkSingle Family
Taxes:$16,685
Elementary School: Brookshire Elem
Remarks: From the boutique address at 433 Carolina Ave, take a stroll down to historic Hannibal Square or to the New England gourmet corridor. On Saturday's mornings, have your breakfast at the Winter Park farmers market and by sunset, enjoy Park Avenue or Winter Park Village. Back home, feel comfortable, extremely comfortable in this casual-chic custom designed home. After a welcoming foyer, a kitchen-bar opens to a large and bright great room fitting dining and living areas. It continues to the back covered veranda and back yard. Still on the first floor, you have a guest suite and an office, conveniently located by the entry door. Up the stairs, a large family room, capable of gathering all the family. In the large master suite balcony, you may have your first coffee in the morning, listening to the early birds. The two other rooms also have balconies to the front of the house. All rooms have closets with shelves, to accommodate your needs. Enjoy finishes like wood floors, large mirrors in bathrooms, quartz counters, crown molding, wide windows and more. This beautiful and modern home is ready for its new residents. It is absolutely gorgeous! Come and visit us. Welcome Home!
Listing is courtesy of: COLDWELL BANKER REALTY (407-647-1211)
Listing Agent: Thomas Bonner (407-401-3748)
40 PALMER AVE, WINTER PARK, FL 32789
$6,950,000113 Days on yellowkey MLS ID: O6380444
Bed: 5 Bath: 5.5 Gar: 4 Liv Area Sq Ft: 5905 Built: 2026 Tax: $12,774 (2024)Community: Robert Dhu Macdonald ParkSpa: YesSingle Family
Taxes:$12,774
Remarks: Under Construction. Opportunities like this rarely present themself, just a eight-minute walk from the iconic shops, restaurants, and cafés of Park Avenue, 40 Palmer represents a rare convergence of architectural significance, uncompromising craftsmanship, and premier Winter Park location. Built by Vimaro Homes, this extraordinary new construction estate is a statement piece that redefines what luxury living looks like in the heart of Winter Park. The exterior architecture is refined yet commanding, with classical influences interpreted through a modern lens, setting the tone for the exceptional level of design and finishes found inside. One of the most remarkable features, and an offering rarely found in Winter Park, is the underground four-car garage. Designed to discreetly accommodate an impressive vehicle collection, the garage is complemented by a striking spiral staircase that rises from the basement through the main living level and continues to the second floor. The family room is nothing short of breathtaking, featuring bespoke millwork with integrated shelving, soft architectural lighting, and a dramatic fireplace wrapped entirely in marble. The kitchen is a culinary showpiece designed for those who expect nothing less than perfection. Calcutta marble countertops cascade across the space, paired with stunning custom cabinetry, and a professional-grade Thermador appliance suite. A dedicated dirty kitchen allows for discreet preparation, while an expansive walk-in pantry ensures effortless hosting and immaculate presentation. The primary bedroom wing features a spa-inspired bathroom finished in rich marble, featuring dual vanities, a freestanding soaking tub and an enormous walk-in closet with a separate washer and dryer. Upstairs, a dedicated laundry room and a spacious secondary living area provide flexibility for family living, guests, or relaxation. The lower level extends the home’s versatility, offering a workshop, dedicated holiday and seasonal storage, and seamless elevator access to the main level of the home. Outdoor living is equally impressive. A large covered exterior lanai with a pool bath and full summer kitchen creates a seamless indoor-outdoor lifestyle, ideal for entertaining year-round. The backyard is truly resort-inspired, featuring a large swimming pool, sunken fire pit, and spa, all set within a private, beautifully secluded outdoor setting. What ultimately sets 40 Palmer apart is not just its design or finishes, but its unmatched combination of luxury and location. Just minutes from Park Ave shopping and restaurants, moments from the famous Winter Park Golf Course, yet privately tucked away, this home offers a lifestyle that is both vibrant and exclusive. A truly rare opportunity to own a part of the exceptional standard of living delivered by Vimaro Homes.
Listing is courtesy of: ONE LUXURY INTERNATIONAL LLC (407-312-8003)
Listing Agent: Julie Christensen (407-592-2055)
1427 LAKE FLORENCE WAY, WINTER PARK, FL 32792
$639,000194 Days on yellowkey MLS ID: TB8449992
1 Days Off yellowkey (back on 5/11/2026)
REDUCED by $36,000 (5.3%) on 05/06/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2193 Built: 2019Monthly Fee: $186 Tax: $5,586 (2024)Community: Lake Florence PreserveSpa: YesSingle Family
Taxes:$5,586
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)
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