Location: Winter Park , 32792
Do Not Show Listings
2008 HOUNDSLAKE DR, WINTER PARK, FL 32792
$490,00045 Days on yellowkey MLS ID: O6414369
REDUCED by $25,000 (4.9%) on 07/20/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2250 Built: 1980 Tax: $5,253 (2025)Community: Cedar RidgeSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$5,253
Elementary School: Eastbrook Elementary
High School: Lake Howell High
Tax Year: 2025
Middle School: Tuskawilla Middle
Remarks: Virtually Staged. Discover space, comfort, and flexibility in this beautifully updated 4-bedroom, 2-bath home in the highly desirable Cedar Ridge community of Winter Park with no HOA. Offering approximately 2,250 square feet of living space, this home also features a versatile flex room ideal as a nursery, home office, guest suite, media room, or private retreat. The 2025 remodeled kitchen offers abundant cabinetry and pantry storage, while the renovated bathrooms feature stylish, modern finishes. Ceramic tile flows throughout most of the home, with warm wood-look flooring in three bedrooms for added comfort. Enjoy peace of mind with major improvements already completed, including a 2024 roof, 2023 whole-home replumbing, and 2023 electrical panel replacement with generator hookup. These significant updates allow you to focus on enjoying your new home instead of tackling major projects. Step outside to an oversized, fully fenced backyard shaded by two magnificent mature oak trees, creating a private setting for relaxing, entertaining, or family gatherings. A side-entry two-car garage adds both curb appeal and everyday convenience. Conveniently located just minutes from Baldwin Park, UCF, shopping, dining, parks, and Seminole County schools, this Cedar Ridge home offers exceptional space, recent major updates, and the convenience of an established Winter Park neighborhood with no HOA.
Listing is courtesy of: MARK SPAIN REAL ESTATE (855-299-7653)
Listing Agent: Nicholas Feinsod (407-607-7485)
316 BECKETT CT, WINTER PARK, FL 32792
$450,00064 Days on yellowkey MLS ID: O6411108
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1651 Built: 1966 Tax: $2,232 (2025)Community: Winter Park Pines Merrie OaksSingle Family
Taxes:$2,232
Elementary School: None
High School: None
Middle School: None
Remarks: Opportunity knocks in one of Central Florida’s most sought-after locations! This 4-bedroom, 2-bath home at 316 Beckett Court has been completely demoed and is ready for your vision to come to life. Whether you’re an investor, builder, or buyer looking to create your dream home, this property offers the ultimate clean slate for a full renovation or custom redesign. Situated in highly desirable Winter Park, this property places you in the heart of one of Orlando’s premier communities, known for its tree-lined streets, charm, upscale shopping, dining, and cultural attractions. Enjoy easy access to Downtown Winter Park Historic District and iconic Park Avenue, home to boutique shopping, cafés, restaurants, and vibrant community events, along with the beauty of Central Park and the cultural appeal of The Charles Hosmer Morse Museum of American Art. Winter Park is also home to the prestigious Rollins College, adding to the area’s timeless character and desirability. Bring your contractor, your imagination, and your vision—properties with this kind of potential in Winter Park are rare. Endless possibilities await!
Listing is courtesy of: VINTAGE REALTY SOLUTIONS (407-421-3949)
Listing Agent: Patrick Westervelt, Llc (407-533-1000)
501 HERITAGE BLVD, WINTER PARK, FL 32792
$458,000139 Days on yellowkey MLS ID: S5145746
REDUCED by $11,000 (2.3%) on 07/20/2026
Bed: 4 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1376 Built: 1966 Tax: $10,434 (2025)Community: Georgetown EstatesSingle Family
Taxes:$10,434
Elementary School: Lakemont Elem
High School: Winter Park High
Middle School: Maitland Middle
Remarks: Welcome to this beautifully remodeled, move-in-ready home in the highly sought-after Winter Park area. This single-story residence features 4 bedrooms and 2 bathrooms, offering a bright, open floor plan with modern finishes designed for both comfort and functionality. A standout feature of this property is its commitment to sustainable living and energy efficiency. Highlights include: - Newer Roof: Installed in 2023 - Radiant Barrier & Blown-In Attic Insulation: Keeps the Florida heat out and significantly lowers cooling costs. - High-Efficiency HVAC: Energy Star rated AC unit ensuring consistent temperatures and peak savings. Step outside to an expansive backyard featuring a private pool, perfect for relaxing or entertaining. This large outdoor space offers endless possibilities for customization, such as a garden or an outdoor kitchen. Located in a quiet, established neighborhood within an A+ rated school zone, this home provides convenient access to top shopping, dining, parks, and major highways. Don't miss this incredible opportunity to own a fully updated turnkey property in one of the most desirable areas of Winter Park.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Bernardo Carrasquel (407-920-4973)
3321 ROYAL ST, WINTER PARK, FL 32792
$280,00011 Days on yellowkey MLS ID: A4700206
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1197 Built: 1982 Tax: $4,462 (2025)Community: Coronation AddSpa: NoHalf Duplex
Taxes:$4,462
Remarks: Turnkey Charm in Winter Park! This beautifully remodeled 3-bedroom, 2-bathroom home offers the perfect blend of style and convenience. Step inside to find durable ceramic tile flooring flowing through a spacious family room, perfect for entertaining. The home features a 1-car garage with a functional laundry area equipped with a washer and dryer tucked neatly in the back, alongside a fantastic outdoor setup. Relax on your open, screened-in patio overlooking a massive, fully fenced backyard. Freshly updated inside and out, this move-in-ready gem is ready for its next owner!
Listing is courtesy of: SAVVY AVENUE, LLC (888-490-1268)
Listing Agent: Moe Mossa (888-490-1268)
2503 TAHOE CIR #2503, WINTER PARK, FL 32792
$250,000119 Days on yellowkey MLS ID: O6395130
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1173 Built: 1981 Tax: $506 (2025)Community: Cedarwood Village 1Condo
Taxes:$506
Elementary School: English Estates Elementary
Remarks: This charming one story condo is located in the desirable Cedarwood Village. This unique home boasts an open layout that is different from many others in the community. The home showcases engineered hardwood floors, skylights and wonderful natural light. The kitchen provides ample cabinet space, granite counters, built-in wine rack and beautiful custom tile work. The kitchen overlooks the dining and living room combo. The living room has 2 skylights and flows right into the delightful Florida room. The Florida room boasts wonderful built-in shelving and a glass door giving access to the backyard. The primary bedroom showcases wonderful built-in cabinets, 2 closets and an ensuite bathroom with a granite counter vanity. The primary bedroom also looks into the Florida room but can be shut off for privacy with a sliding door. The second bedroom is at the front of the home and has access to the guest bathroom with a granite counter vanity. Two assigned parking spaces are directly in front of the home. To top it all off, this home is in close proximity to several restaurants and shops and is an easy drive to downtown Winter Park.
Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)
Listing Agent: Beth Logullo (772-633-0670)
5143 LAZY OAKS DR #5143, WINTER PARK, FL 32792
$275,000107 Days on yellowkey MLS ID: O6398856
REDUCED by $5,000 (1.8%) on 06/29/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1008 Built: 1984 Tax: $668 (2024)Community: Lazy Oaks CondoCondo
Taxes:$668
Tax Year: 2024
Remarks: Quiet Living in the Desirable Lazy Oaks Community of Winter Park. Welcome to the peaceful, well-established community of Lazy Oaks in highly sought-after Winter Park. This hidden gem offers beautifully landscaped grounds, meticulous maintenance, and the added benefit of a low HOA. This lovingly maintained 2-bedroom, 2-bath home features a spacious, thoughtfully designed floor plan with an attached garage. The home is ideally located near top-rated schools, shopping, dining, and provides convenient access to major highways. Inside, you’ll find a neutral color palette complemented by ceramic tile and wood laminate flooring throughout. The efficient kitchen boasts gleaming white countertops, rich wood cabinetry, and a large pantry for ample storage. The expansive great room offers flexible space for both dining and living areas, complete with a cozy wood-burning fireplace—perfect for relaxing or entertaining. Sliding glass doors open to a large, screened private lanai, ideal for morning coffee or evening unwinding. The spacious primary suite features an en suite bath with dual sinks, a large vanity, walk-in shower, and a generous closet. A split-bedroom layout provides added privacy, with a secondary bedroom and additional full bath. Additional highlight: HVAC replaced in 2021. Don’t miss this opportunity to make your home in one of Winter Park’s most charming and convenient communities!
Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)
Listing Agent: Mindy Machock (407-461-1866)
4756 TANGERINE AVE #4756, WINTER PARK, FL 32792
$185,00043 Days on yellowkey MLS ID: R4911483
REDUCED by $10,000 (5.1%) on 07/19/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1058 Built: 1973 Tax: $2,244 (2025)Community: Wrenwood CondoSpa: NoCondo
Taxes:$2,244
Remarks: Discover the potential of this 2-bedroom, 2-bath end-unit condominium located in the desirable Wrenwood Condominium community in Winter Park, Florida. Offering 1,058 square feet of living space, this home presents an excellent opportunity for buyers seeking affordability, convenience, and the chance to add their own personal style. Inside, you'll find ceramic tile flooring throughout, knockdown ceilings, and a functional floor plan designed for comfortable everyday living. All kitchen appliances are included, making your transition even easier. The end-unit location provides additional privacy and natural light while offering pleasant views of the community pool. Built with solid concrete block construction, this condominium offers durability and low-maintenance ownership. The bathrooms could benefit from updating, providing the perfect opportunity for the next owner to customize the home to their own taste and preferences. Whether you're a first-time homebuyer, downsizing, looking for a seasonal residence, or seeking an investment property, this home offers tremendous potential and value. Wrenwood Condominium allows up to two pets, with a maximum weight of 25 pounds each, making it a great option for pet lovers. Conveniently located near shopping, dining, entertainment, major highways, and everything Winter Park and the greater Orlando area have to offer. Don't miss this opportunity to own an affordable Winter Park condominium and create the home you've always envisioned.
Listing is courtesy of: HOME BUYER HELPER REAL ESTATE LLC (407-342-2664)
Listing Agent: Ada Sanchez (407-342-2664)
1418 LONE FEATHER TRL, WINTER PARK, FL 32792
$750,00044 Days on yellowkey MLS ID: O6417341
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2197 Built: 2022Monthly Fee: $244 Tax: $6,224 (2025)Community: Landings At Hawks CrestSingle Family
Taxes:$6,224
Remarks: Nestled within the gated community of Hawks Crest, this meticulously maintained two-story residence showcases over $70,000 in luxurious builder upgrades, blending timeless design, modern comfort, and effortless Florida Living. This stunning home presents an exceptional opportunity to enjoy one of Winter Park's most desirable lifestyle communities. A welcoming entry opens to light-filled interiors where soaring ceilings, elegant finishes and a thoughtfully designed open-concept floor plan create a seamless flow throughout the home. Luxurious white ceramic tile spans the entire first floor, enhancing the home's bright and airy feel while providing both beauty and durability. The gourmet kitchen serves as the centerpiece of the home, featuring upgraded cabinetry, quartz countertops, stainless steel appliances, abundant storage and an expansive peninsula with bar seating. Spacious living areas and generously sized bedrooms provide comfort and flexibility for a variety of lifestyles. Upstairs, plush carpeting creates a warm and inviting retreat, while the primary suite offers a private sanctuary complete with a large walk-in closet and a spa-inspired bath. Additional bedrooms provide ample space for family, guests, a home office or a fitness room. Sliding glass doors extend the living space to a covered lanai, creating an inviting setting for outdoor dining, morning coffee or relaxed evenings enjoying Florida's year-round climate. Residents of Hawks Crest enjoy an exceptional collection of resort-style amenities, including a clubhouse, state-of-the-art fitness center, community pool, playgrounds, dog park, scenic trails and private access to Lake Howell. The community is also conveniently located near local favorites, including Kelly's Ice Cream, Foxtail Coffee and Park Maitland Preschool. Ideally situated just minutes from Park Avenue, downtown Maitland, major highways, and top-rated schools, this exceptional home offers effortless access to Central Florida's finest shopping, dining and cultural attractions. Despite its convenient location, the community maintains a sense of privacy and tranquility.
Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)
Listing Agent: Harif Hazera Llc (407-953-9098)
1090 WILDMEADOW RUN, WINTER PARK, FL 32792
$835,000125 Days on yellowkey MLS ID: O6394208
REDUCED by $10,000 (1.2%) on 06/02/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2589 Built: 2021Monthly Fee: $243 Tax: $6,258 (2024)Community: Hawks CrestSingle Family
Taxes:$6,258
Remarks: One or more photo(s) has been virtually staged. **This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buy-down that reduces the buyer's interest rate and monthly payment.** This luxurious Modern Style home epitomizes maintenance-free living, featuring a premium, state of the art solar system YOU OWN OUTRIGHT, nearly eliminating your cost of electricity. Ask to see the bill. The premium solar system is PAID OFF with a TRANSFERABLE WARRANTY by manufacturer. This off-grid solar system comes with a WHOLE HOUSE BATTERY BACKUP, keeping your lights on when the power goes out. This home already comes wired for electric vehicles with room to expand. Excess power generated is sold back to the power company through the NET METERING program, resulting in credits back to the owners at the end of the year. The solar system also has two power monitoring systems for tracking your energy usage & production, conveniently controlled by your phone and computer. Hawks Crest is your home to community, where residents enjoy gated access into a landscaped resort atmosphere, featuring water fountains throughout, with an abundance of amenities. The clubhouse features a resort pool & kiddie pool, a fitness center, with sidewalks & playgrounds, along with the community’s private dock access to Lake Howell with a canoe/kayak launch. Now imagine, relaxing and enjoying park and pond views from your expansive lanai, soaking in the serene sunsets & manicured landscaping, all from the comfort of your spacious, 4-bedroom 3.5 bath home, including a loft upstairs, all conveniently located just a short distance from the resort clubhouse. Owners can relax and unwind while management handles all landscaping around your home, truly providing you a maintenance-free living lifestyle. Additional upgrades with this home include, commercial grade luxurious vinyl wide-plank flooring, two power monitoring systems, a whole-house water softener & filter system, and two HVAC units, all designed for comfort, convenience, and a very clean home, where you can relax. Nestled in this spacious home, you’ll find 20-foot-high ceilings with awe-inspiring views of the illuminated pond fountain, creating a serene view & relaxing atmosphere you’ll enjoy, even from the kitchen sink. Your chandelier can be lowered 20-feet to the floor for easy maintenance & cleaning, using a winch lift system in the attic.(Rated up to 200 lbs). And even watch the rockets launch at The Cape from the front yard. Uniquely designed, this home was built to withstand extreme weather, featuring a concrete/granite tile roofing system, steel reinforcement, concrete-filled block walls & slab, all anchoring to the foundation, uniquely tying everything together. Meticulously maintained by the owners, this home comes with a complete set of blueprints, along with many photos & videos taken of the home during the building process. Owners even have documents for all equipment & appliances. And the premium solar system comes with a transferable warranty that will keep the lights on when the power is out. This home features a split floor-plan, with a primary bedroom on both the first and second floors. Spanning 2,589 sq.ft., this home offers an additional 540 sq.ft. of screened-in lanai, providing a private outdoor oasis where you’ll find owners enjoying the tranquility of Florida sunsets. Schedule a showing for your buyers today! And…***Remember to see the list of the owners’ upgrades***.
Listing is courtesy of: BHHS FLORIDA REALTY (352-729-7325)
Listing Agent: Rod Chevalier (352-729-1818)
2758 BANCHORY RD, WINTER PARK, FL 32792
$598,000367 Days on yellowkey MLS ID: O6329628
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1539 Built: 1965 Tax: $7,325 (2024)Community: Winter Park PinesSingle Family
Taxes:$7,325
Remarks: Charming Pool Home in Prime Winter Park Location Welcome to 2758 Banchory Road — a true gem nestled in the heart of the desirable Winter Park Pines community. This beautifully maintained 3-bedroom, 2-bath ranch-style home offers the ideal combination of comfort, privacy, and location. With a private swimming pool, lush landscaping, and no direct front neighbors on a quiet cul-de-sac street, this home is perfect for families or anyone seeking tranquility just minutes from city conveniences. Property Highlights Spacious backyard featuring a private pool—perfect for Florida living and entertaining. Fully fenced yard with a storage shed and dedicated area for pets or gardening. Open-concept layout with natural light, mature trees, and charming curb appeal. Located steps from the Cady Way Trail, ideal for biking, jogging, or weekend strolls. Unbeatable Location Just minutes to Downtown Winter Park with boutiques, restaurants, Rollins College, and Park Avenue. Close to Winter Pines Golf Club, Cady Way Park, and public tennis courts. Easy access to Baldwin Park, Full Sail University, Advent Health Winter Park, and the 417 expressway. Top-Rated School Zone Located within the Orange County Public Schools district, this home is zoned for: Aloma Elementary School (PK–5) ~ 0.7 miles Glenridge Middle School (6–8) ~ 1.6 miles Winter Park High School (9–12) ~ 0.6 miles Highly rated with International Baccalaureate (IB) and Advanced Placement (AP) programs Private schools nearby include Trinity Prep, Geneva School, Chesterton Academy, and St. Margaret Mary K–8. Why You’ll Love It Relax and entertain year-round with your private pool and covered patio. Walkable to trails and parks, bikeable to schools, and 10 minutes to Park Avenue. Family-friendly neighborhood with strong community feel and no HOA. A rare combination of location, schools, and lifestyle opportunities. “Solar panel debt is $70k and must be assumed by Buyer". Whether you’re relocating, downsizing, or looking for the perfect place to raise a family, this Winter Park beauty has it all. Schedule your private tour today!
Listing is courtesy of: MR VARGAS PROPERTY MANAGEMENT LLC (407-557-2150)
Listing Agent: Erwin Vargas (407-338-3382)
3282 OAK LAKE PL #3282, WINTER PARK, FL 32792
$154,50091 Days on yellowkey MLS ID: O6403912
0 Days Off yellowkey (back on 7/17/2026)
REDUCED by $15,000 (8.8%) on 05/28/2026
Bed: 2 Bath: 1.5 Liv Area Sq Ft: 990 Built: 1984 Tax: $2,899 (2025)Community: Hidden Oaks Condominium Association, IncCondo
Taxes:$2,899
Remarks: New Price! This beautifully updated 2-story condo offers the perfect blend of style and affordability. Featuring a fresh kitchen, renovated bathroom, and new flooring throughout, this move-in-ready home includes an in-unit washer/dryer for ultimate convenience. As a desirable end unit, you’ll enjoy extra privacy and a peaceful view of the adjacent conservation area. Relax on your private patio, complete with additional outdoor storage. Bonus: Your HOA dues cover water and trash service! This Winter Park steal won’t last—schedule your showing today.
Listing is courtesy of: BUSBY REALTY LLC (407-529-6952)
Listing Agent: Chad Busby (407-529-6952)
1535 LAWNDALE CIR, WINTER PARK, FL 32792
$445,00049 Days on yellowkey MLS ID: C7527235
REDUCED by $5,000 (1.1%) on 07/17/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1676 Built: 1986Monthly Fee: $50 Tax: $5,433 (2025)Community: Country LaneSpa: NoSingle Family
Taxes:$5,433
Remarks: Discover this well maintained 3 bedroom, 2 bathroom home offering 1,676 sq ft of comfortable living space. The home features a spacious layout with inviting living and dining areas that flow seamlessly into the kitchen, creating a great setup for everyday living and entertaining. The primary suite includes a private bathroom and generous closet space, while the additional bedrooms provide flexibility for family, guests, or a home office. Step outside to your own private backyard retreat featuring a pool and fully fenced yard, perfect for relaxing, entertaining, and enjoying the Florida lifestyle. Located in a quiet residential neighborhood, this move-in ready home is easy to show and ready for its next owner.
Listing is courtesy of: SOVEREIGN REAL ESTATE GROUP (305-662-1502)
Listing Agent: Raul Pino (305-662-1502)
2526 PASSAMONTE DR #10F, WINTER PARK, FL 32792
$335,00014 Days on yellowkey MLS ID: O6418710
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1790 Built: 2009Monthly Fee: $402 Tax: $4,769 (2025)Community: Via Lago/Hanging Moss CondoCondo
Taxes:$4,769
Remarks: Great investment opportunity, tenant occupied/income producing Winter Park property in gated community.
Listing is courtesy of: LEGACY CORNERSTONE INC (407-674-5601)
Listing Agent: Kathi Thomas (407-674-5601)
2052 LEANNE CT, WINTER PARK, FL 32792
$440,000177 Days on yellowkey MLS ID: O6379323
0 Days Off yellowkey (back on 7/13/2026)
REDUCED by $5,000 (1.1%) on 06/17/2026
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
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)
1662 TREMONT LN, WINTER PARK, FL 32792
$384,90055 Days on yellowkey MLS ID: O6414180
0 Days Off yellowkey (back on 7/16/2026)
REDUCED by $5,000 (1.3%) on 06/19/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1534 Built: 1986Monthly Fee: $49 Tax: $4,339 (2025)Community: Country LaneSingle Family
Taxes:$4,339
Remarks: Under contract-accepting backup offers. Back on the Market - Buyer Financing fell through. Turnkey and move-in ready! This beautifully updated 3-bedroom, 2-bath home offers modern finishes and an ideal floor plan in a fantastic location! Recent improvements include fresh interior and exterior paint, new flooring throughout, a fully renovated kitchen, and updated bathrooms. Roof (2022) Enjoy comfortable living with thoughtfully updated interiors and flexible living space. The spacious primary suite features an attached bonus room that is perfect for a home office, nursery, fitness space, or private retreat. The community amenities include a playground, tennis courts, and private lake access with a dock, providing plenty of opportunities for recreation and relaxation. Don’t miss this opportunity to own this beautifully updated home with outstanding community amenities and convenient access to everything the area has to offer!
Listing is courtesy of: RESULTS TEAM PROP & INVESTMENT (321-637-3737)
Listing Agent: Susan Heacock
2032 KIMBRACE PL, WINTER PARK, FL 32792
$1,888,88851 Days on yellowkey MLS ID: O6414862
REDUCED by $100,000 (5.0%) on 07/16/2026
Bed: 5 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3382 Built: 2021 Tax: $16,035 (2025)Community: Kenilworth Shores Sec 03Spa: YesSingle Family
Taxes:$16,035
Elementary School: Brookshire Elem
Middle School: Glenridge Middle
Remarks: A PRIVATE RESORT-STYLE SANCTUARY IN THE HEART OF WINTER PARK 5 Bedrooms | 4 Bathrooms | 3,400+ SF|Saltwater Pool & Spa|Minutes to Park Avenue Welcome to a rare offering where luxury, tranquility, and architectural sophistication converge. Nestled in one of Winter Park's most desirable neighborhoods, just minutes from the boutiques, fine dining, and cultural attractions of Park Avenue, this custom Mid-Century Modern residence delivers an extraordinary lifestyle defined by elegance, wellness, and privacy. The home is within the acclaimed Winter Park school district, less than four miles from Trinity Preparatory School, and minutes from Rollins College and the University of Central Florida, placing premier educational opportunities nearby. Thoughtfully designed with a Zen-inspired aesthetic, the home blends clean architectural lines with warm natural elements to create a refined, restorative living experience. From the moment you arrive, a sense of calm surrounds you, offering a peaceful escape while remaining minutes from everything Winter Park offers. Inside, soaring 10-foot ceilings, expansive walls of glass, and wide-plank engineered hardwood flooring create bright, open living spaces filled with natural light. A semi-floating steel staircase with solid white oak treads serves as a dramatic focal point, while designer Restoration Hardware lighting adds warmth and sophistication throughout. The main living area was designed for entertaining. A Dimplex fireplace anchors the great room, complemented by a custom wine bar. At the heart of the home, the chef's kitchen showcases a waterfall island, premium quartz countertops, marble backsplash, double-stacked cabinetry, and a custom pantry. High-end Samsung smart appliances, including a Family Hub refrigerator, WiFi-enabled convection wall oven, Flex Duo cooking system, and 36-inch Bluetooth cooktop, complete this exceptional culinary space. A first-floor guest suite and full bath provide flexibility for visitors, a private executive office, fitness studio, or wellness retreat. The finished two-car garage features epoxy flooring and a modern glass garage door. Upstairs, the primary suite serves as a private sanctuary. The spa-inspired bath features a freestanding soaking tub, dual-entry marble shower with a semi-frameless glass enclosure, dual vanities, and a custom walk-in closet. Beyond the walls of the home lies your own private paradise. Professionally designed by Exotic Landscape Company, the resort-style outdoor living space evokes the serenity of a Balinese retreat. The newly constructed saltwater pool and spa showcase glass tile finishes, mini-pebble surfaces, travertine coping, LED lighting, therapy jets, a cascading waterfall, and smartphone-controlled OmniLogic automation. A custom outdoor stone shower, yoga platform, lush tropical landscaping, and curated hardscapes create an environment dedicated to relaxation and wellness. Additional features include Eufy smart lock technology, Arlo video doorbell, Google Nest thermostat, WiFi-enabled irrigation, smart garage controls, Quality Edge Vesta steel plank siding, and an expanded driveway. Less than ten minutes from Park Avenue, this exceptional residence offers a rare opportunity to own a home that feels more like a private luxury resort. More than a home, it is a sanctuary where timeless design, resort-inspired living, and one of Central Florida's finest educational settings create an unparalleled lifestyle.
Listing is courtesy of: SIMPLICITY: A RE BROKERAGE CO (407-920-6020)
Listing Agent: Robert Sassos (407-920-6020)
758 WARRENTON RD, WINTER PARK, FL 32792
$318,985120 Days on yellowkey MLS ID: O6395298
1 Days Off yellowkey (back on 7/16/2026)
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1196 Built: 1988Monthly Fee: $86 Tax: $3,689 (2025)Community: Winter Park Pines Patio HomesHalf Duplex
Taxes:$3,689
Elementary School: Aloma Elem
Remarks: HOME IS BACK ON THE MARKET AFTER GETTING A BRAND NEW ROOF!!! Tucked away on a quiet cul-de-sac in highly sought-after Winter Park, this beautifully updated three bedroom, two bathroom duplex offers the perfect blend of comfort, style, and location—just steps from Winter Park Pines Golf Club. Once inside you discover open living spaces featuring warm wood flooring throughout the living areas and bedrooms, complemented by vaulted ceilings in the main areas and ceiling fans that enhance the home’s airy feel. The BRAND-NEW kitchen has tile flooring and is not only functional, but beautiful showcasing classic shaker cabinets, sleek quartz countertops, and stainless steel appliances—perfect for both everyday living and entertaining. There are three nice sized bedrooms, all with large closets. The primary bedroom features sliding glass doors that lead directly to the large backyard and open patio. Both bathrooms have been renovated with modern finishes, including BRAND-NEW vanities, countertops, tub/showers, plus durable and stylish luxury vinyl plank flooring. Situated on a generously sized corner lot, the property offers plenty of outdoor space to enjoy, along with a charming paver front patio and the convenience of a one-car garage with opener. You will love the privacy of this end unit on the quiet cul-de-sac. Enjoy the ease of walking to nearby schools and being just moments from golf, shopping, dining, and all that Winter Park has to offer. With low HOA dues and located in a top-rated school district, this is an incredible opportunity in one of Central Florida’s most desirable neighborhoods.
Listing is courtesy of: SUN PROPERTIES, INC. (407-645-5700)
Listing Agent: Andrew Musashe (407-645-5700)
1850 ASTER DR, WINTER PARK, FL 32792
$485,00058 Days on yellowkey MLS ID: TB8513990
REDUCED by $15,000 (3.0%) on 06/13/2026
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1656 Built: 1978 Tax: $1,584 (2025)Community: Garden Lake Estates Unit 1Single Family
Taxes:$1,584
Remarks: Under contract-accepting backup offers. Welcome to the heart of Winter Park. This beautifully maintained 4-bedroom, 2.5-bath pool home offers the perfect blend of warmth, functionality, and charm. From the moment you arrive, the curb appeal is unforgettable. Lush landscaping, mature greenery, and peaceful natural surroundings create a private and inviting setting that immediately feels like home. Inside you'll find an open and welcoming floor plan designed with both everyday living and entertaining in mind. The updated kitchen features stainless steel appliances, a spacious island, abundant cabinet storage, and seamless flow into the main living areas. A formal living area adds flexibility, offering the perfect space for a cozy sitting room, playroom, home office, or additional entertaining area. Natural light throughout the home creates a bright and airy atmosphere. Upstairs, you’ll find all four bedrooms and two full bathrooms, providing privacy and functionality for growing families. The screened-in porch overlooks a stunning backyard retreat complete with a sparkling pool, beautiful landscaping, and no rear neighbors for added privacy. Peaceful, quiet, and surrounded by nature and wildlife, this outdoor space makes it perfect for summer pool days, evening dinners outside, and making lifelong memories.
Listing Agent: Brianna Lalumiere (727-641-3957)
5225 ALBERT DR, WINTER PARK, FL 32792
$435,00017 Days on yellowkey MLS ID: O6424623
0 Days Off yellowkey (back on 7/15/2026)
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1716 Built: 1979 Tax: $4,476 (2025)Community: Wrenwood Unit 3 3Rd AddSingle Family
Taxes:$4,476
Remarks: Move-in-ready Winter Park gem in top-rated Seminole County schools! This 3BR/2BA home features a private split-bedroom layout. The home features laminated wood flooring in all the bedrooms and beutiful tile in the kitchen and bathrooms. Both bathrooms feature newly updated toilets. The expansive eat-in kitchen is a chef's delight, boasting premium granite countertops, solid light maple cabinets with elegant glass upper doors, and a breakfast bar opening to the large family room. Enjoy total peace of mind with extensive 2023 upgrades, including a BRAND NEW ROOF, new electrical panel, new energy-efficient windows, new French doors, and a new garage door for the 2-car garage.The HVAC system was manufactured in 2019 and installed in 2020 Step outside to a massive, fully fenced backyard featuring a large covered lanai with a brand-new aluminum frame and fresh screens—perfect for outdoor entertaining. Truly a turnkey property optimized for insurance savings and modern comfort. Schedule your tour today!
Listing is courtesy of: PREMIUM PROPERTIES R.E SERVICE (407-380-2800)
Listing Agent: Celimar Sierra, Llc (407-731-2678)
639 SAINT JOHNS CT #639, WINTER PARK, FL 32792
$194,90095 Days on yellowkey MLS ID: O6402025
REDUCED by $5,000 (2.5%) on 06/16/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1120 Built: 1981 Tax: $3,077 (2025)Community: Winter Park VillasCondo
Taxes:$3,077
Remarks: Under contract-accepting backup offers. Freshly painted 2 Bedroom/2 Bath townhouse-style condo with no neighbors above or below, backing up to a peaceful pond & community amenities. The upstairs/downstairs split-bedroom floor plan offers privacy - ideal for roommates or families. The bright living area features soaring cathedral ceilings, a corner fireplace, and access to a partially covered patio, perfect for entertaining or BBQs. There's abundant storage throughout, including coat, linen, patio, and under-stair space that could be converted into a small office or workout nook. The kitchen comes fully equipped with all appliances, ample cabinet space, and a breakfast bar, while the dining area overlooks the pond and opens to the patio with an additional storage closet. Upstairs, the primary suite includes an en-suite bath, a large walk-in closet, and corner windows that brings in great natural light. The second bedroom is located downstairs and offers dual closets and a ceiling fan. Updated luxury vinyl flooring runs through most of the home, and there is also an in-unit washer/dryer for convenience. Located in the highly desirable Winter Park Villas community, residents enjoy a wide array of amenities including a sparkling pool, clubhouse with fitness center, tennis courts, car wash station, scenic ponds, pet stations. The HOA provides exceptional value by covering roof & exterior maintenance, lawn service, water, trash, sewer, pest control—ensuring truly low-maintenance living. Conveniently located just minutes from Full Sail University, Rollins & Valencia Colleges, approximately 10 minutes from downtown Winter Park. Top-rated schools nearby, this property is an excellent opportunity for both homeowners & investors. Outdoor enthusiasts will also appreciate easy access to the nearby Cady Way Trail, perfect for walking, jogging, or cycling.
Listing is courtesy of: PLATINUM REALTY GROUP FLORIDA INC (407-270-7378)
Listing Agent: Adam Eisen (407-808-6967)
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