Location: Winter Park
Do Not Show Listings
1624 BARCELONA WAY, WINTER PARK, FL 32789
$2,235,000193 Days on yellowkey MLS ID: O6362124
REDUCED by $15,000 (0.7%) on 05/30/2026
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3818 Built: 1972Monthly Fee: $87 Tax: $12,501 (2024)Community: SevillaSpa: NoSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$12,501
Elementary School: Audubon Park K8
High School: Winter Park High
Tax Year: 2024
Middle School: Audubon Park K-8
Remarks: Totally traditional luxury single-story home is located in the desirable Sevilla neighborhood in Winter Park. Sitting high and dry on approximately a half-acre beautifully landscaped lot. Original home was mostly gutted down to the studs in 2011-2012 and COMPLETELY re-done. Multi-generational potential as this home has a complete attached guesthouse. Interior layout boasts formal living with bay window and tall ceilings, dining room with antiqued mirror set into extensive moldings and trim, plus a library/den with a tongue and groove wood vaulted ceiling and a wall of bookshelves and built-ins. The spacious family room with a white-washed brick, wood-burning fireplace wall and vaulted ceiling is all open to the breakfast area and kitchen. The gourmet kitchen features custom inset cabinet drawers and doors, white marble slab backsplashes, Kohler farmhouse sink and a large island with a deep prep sink. The kitchen is a chef’s delight with a 48-inch Viking gas range, Viking warming drawer, Jenn-Air refrigerator, wine refrigerator and a Bosch dishwasher. The kitchen also has amazing storage and two large pantries. There are a total of four bedrooms (the 4th is currently the living room of the in-law suite suite) and three full baths. Throughout the home are beautiful real ¾-inch-thick and 5-inch-wide plank walnut floors, beam and coffered ceilings, French doors, oversized picture windows and designer accents lighting. French doors off the family room open to seamlessly blend indoor and outdoor living, leading to a covered lanai with travertine stone tile overlooking a resort and entertaining backyard. Huge swimming pool and a 30-by-15-foot pergola with Bistro lighting, which is a wonderful spot to relax, dine and play, all on a tiny pebble surface, like an Italian driveway! French garden fountain, rose garden and synthetic turf for pets make the backyard a haven. The home’s floor plan offers a desirable layout with huge primary bedroom with a generously sized un-suite bath with dual sink counters, amazing Roman walk-in shower, jetted tub with bubblers and two large walk-in closets. Guest wing features a spacious bedroom and bath and the West Wing is a full In-law apartment, including a bedroom, handicapped bath, full kitchen and its living room (which would be easy to be converted back into the 4th bedroom - plans available). Imagine having a wonderful space for in-laws or an adult family member that needs space of their own. Just a short drive or bike ride from Park Avenue, this open and inviting home has easy access to downtown Winter Park, AdventHealth, downtown Orlando and is zoned for A-rated schools. Surround sound through most of the house and CAT 6 wiring throughout. Recent additional remodeling and updating have taken place including all new windows, paint inside and out, as well as a new roof and gutters in 2023. A detailed list of all renovations is available upon request.
Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)
Listing Agent: Jan Walker (407-718-9644)
1832 E CHERYL DR, WINTER PARK, FL 32792
$439,99538 Days on yellowkey MLS ID: O6402209
0 Days Off yellowkey (back on 4/30/2026)
INCREASED by $10,000 (2.3%) on 04/27/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1808 Built: 1983Monthly Fee: $8 Tax: $1,847 (2024)Community: Carolyn EstatesSingle Family
Taxes:$1,847
Elementary School: Red Bug Elementary
High School: Lake Howell High
Middle School: Tuskawilla Middle
Remarks: Under contract-accepting backup offers. Welcome to Carolyn Estates in highly desirable Winter Park—a charming enclave of just 63 homes ideally located near Lake Howell High School. This beautifully renovated residence offers a truly unique floor plan—the only one of its kind in the community. Featuring 4 bedrooms, 2 bathrooms, and a spacious 2-car garage, this home blends comfort with functionality. Enjoy cozy evenings by the wood-burning fireplace or unwind in the screened-in patio, perfect for relaxing or entertaining. Step inside to an inviting open-concept layout highlighted by soaring ceilings and abundant natural light. Renovated in April 2026, this home showcases numerous upgrades, including fresh interior and exterior paint, new sod and lush landscaping, a fully remodeled second bathroom, new convection range and microwave, updated interior door hardware, a complete electrical update, and new lighting and ceiling fans throughout. Additional major improvements include newer windows and hot water heater (2019) and full home replumbing (2022), providing added peace of mind. Seller will provide a $10,000 credit towards a new roof with Full Price Offer. This move-in-ready home combines modern updates with a prime location—schedule your private showing today!
Listing is courtesy of: SELECTIVE REALTY GROUP LLC (407-627-1727)
Listing Agent: Shanon Luiz (407-247-2241)
2500 LEE RD #122, WINTER PARK, FL 32789
$179,00090 Days on yellowkey MLS ID: O6384082
0 Days Off yellowkey (back on 5/2/2026)
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 645 Built: 1969 Tax: $428 (2024)Community: Lakeside Manor Apts CondoCondo
Taxes:$428
Elementary School: Killarney Elem
High School: Edgewater High
Middle School: College Park Middle
Remarks: Under contract-accepting backup offers. PRICE IMPROVEMENT! Welcome home to this updated 1-bedroom 1-bathroom GROUND FLOOR condo, ideally positioned toward the desirable rear of the sought-after Lakeside Manor community. The move-in-ready residence features a spacious, open floor plan enhanced by ceramic tile throughout, elegant crown molding and a thoughtfully updated kitchen complete with modern countertops, soft-close cabinetry, and newer stainless-steel appliances. Additional value-added improvements include newer windows and updated plumbing (re-piped and newer water heater) offering peace of mind to the next owner. Lakeside Manor is a highly desirable lakefront community offering private access to Lake Killarney a 239-acre spring fed lake. Residents enjoy premium amenities including a private boat ramp, community dock, access to boat slips (subject to availability, a monthly fee applies). The community also features a swimming pool, guest parking, extra parking (subject to availability, additional fee applies), community laundry facilities (nominal usage fee), storage cabinets, outdoor grill and picnic tables. Condo fees conveniently include monthly internet and water service. Ideally located just minutes from Winter Park and Park Avenue’s renowned shopping and dining, with quick access to I-4 and Downtown Orlando, this property offers the perfect combination of comfort, convenience, and lifestyle.
Listing is courtesy of: PINEAPPLE PLACE REALTY, LLC (407-497-8563)
Listing Agent: Andrea Aylett-Hosch (407-497-8563)
2228 HOWARD DR, WINTER PARK, FL 32789
$2,460,00019 Days on yellowkey MLS ID: O6407733
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3294 Built: 2026 Tax: $3,647 (2025)Community: Lake Forest ParkSingle Family
Taxes:$3,647
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Under Construction. Welcome to 2228 Howard, a designer home that complements the irreplaceable natural beauty surrounding it with a one-of-a-kind façade. This curved street-front home winds around century-old oaks while overlooking Lake Howard, creating the kind of property you will love coming home to. Many rooms inside the home are designed to incorporate the outdoor spaces. These artfully designed exterior areas feel like an extension of the interior, making the home feel even larger and more luxurious. The first floor welcomes you and your guests through the 5’ wide steel pivot door near the private office. The extra-large kitchen, open pantry, and breakfast nook are framed by warm natural oak floor-to-ceiling cabinetry and Thermador appliances while overlooking the exterior raised garden bed. This beautiful kitchen flows seamlessly into the living room, which features a modern floating-hearth fireplace. The living room opens to the outdoor living space, summer kitchen, pool, and hot tub. The primary bathroom has a modern natural feel, featuring a glass sauna room that opens to a private outdoor spa with hot and cold plunge tub. The first-floor laundry room is located just off the two-car garage and includes a drop zone for additional organization. Another bonus feature is the inclusion of two laundry rooms—one on each floor. Upstairs, the kids’ lounge is surrounded by three bedrooms and a secret media room. One bedroom is en-suite, while the other two bedrooms share a common bathroom with dual vanity areas. The exterior of the home utilizes every area like a thoughtfully designed park, creating usable space around every corner. The driveway accommodates several vehicles and includes a side drive for additional parking and storage behind the gate and garage. When you do leave your beautiful home, you are surrounded by the best that Winter Park and Orlando have to offer. This neighborhood is zoned for top-rated schools, where kids walk and ride their bikes to school daily, and is surrounded by amazing parks, restaurants, shops, and nature. Your home can feel like a perfect balance of natural and modern architecture, both inside and out. Call us to see how this home delivers that truly unique feeling.
Listing is courtesy of: COLEDEV REAL ESTATE LLC (407-915-0456)
Listing Agent: Ryan Feely (321-663-1433)
639 SAINT JOHNS CT #639, WINTER PARK, FL 32792
$199,90036 Days on yellowkey MLS ID: O6402025
3 Days Off yellowkey (back on 5/30/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1120 Built: 1981 Tax: $3,077 (2025)Community: Winter Park VillasCondo
Taxes:$3,077
Elementary School: Aloma Elem
Middle School: Glenridge Middle
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)
1571 WOODLAND AVE, WINTER PARK, FL 32789
$6,000,0003 Days on yellowkey MLS ID: O6411706
Bed: 5 Bath: 7.0 Gar: 3 Liv Area Sq Ft: 7397 Built: 2007 Tax: $31,040 (2025)Community: Comstock ParkSpa: YesSingle Family
Taxes:$31,040
Elementary School: Lakemont Elem
Middle School: Maitland Middle
Remarks: Experience timeless elegance and deliberate craftsmanship in the heart of prestigious Winter Park. This one-of- a-kind exceptional estate offers more than 7,300 square feet across three beautifully designed levels, blending refined luxury with modern comfort. Rich architectural details include solid red oak flooring with a walnut finish, nearly 10-foot ceilings, stacked crown moldings, custom ironwork, designer lighting, and extensive millwork throughout. The gourmet kitchen is thoughtfully appointed with Viking and GE Monogram appliances, custom Busby cabinetry, an oversized island, and a butler’s pantry. It also includes multiple filtered water and ice zones designed for effortless entertaining. The spacious primary suite offers a true retreat with spa-inspired marble finishes, an oversized walk-in shower, a jetted soaking tub, and exceptional custom closet space. Additional features include a private elevator, Control4 automation, integrated audio/video/security systems, five HVAC systems, a central vacuum system, and a Generac whole-home generator. A fully finished and expansive basement level serves as a unique and exceptional extension of the home’s living and entertaining space. Designed for both relaxation and recreation, it features a game and arcade room, a full beverage center with a dishwasher, microwave, and Scotsman ice machine, a fitness area with a sauna and steam room, an additional laundry room, a creative storage center, and a private 4K theater with seating for multiple guests. Outdoors, resort-style living awaits with a saltwater pool and spa, a summer kitchen with a custom copper hood, an electric gated entry, landscape lighting, lush cascading bougainvillea, and ten mature magnolia trees creating exceptional beauty and privacy. The property also features a dog run with artificial turf. Three ventless gas fireplaces, including one on the private covered porch, add warmth and ambiance throughout the home. This home also features a whole-house water softener system. Top-rated A+ public schools are within a short walk or bike ride. Nearby highly regarded private schools include Park Maitland School, The Christ School, The First Academy, Trinity Preparatory School, Lake Highland Preparatory School, and Bishop Moore Catholic High School. Perfectly positioned within walking distance of the boutiques and dining of Park Avenue, and just minutes from the Winter Park Golf Course, Rollins College, and Advent Health Winter Park, this is a rare opportunity to own an exceptional custom estate in one of Central Florida’s most sought-after communities.
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: Vonda Fields (321-438-6906)
200 SAINT ANDREWS BLVD #704, WINTER PARK, FL 32792
$164,9993 Days on yellowkey MLS ID: O6411608
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 793 Built: 1970 Tax: $2,396 (2025)Community: Four Seasons CondoCondo
Taxes:$2,396
Remarks: Excellent opportunity in the heart of Central Florida! Welcome to this charming 1-bedroom, 1-full-bath condominium located in the desirable Four Seasons Condominiums of Winter Park. Step inside to a spacious living area that flows seamlessly into the dining and kitchen spaces, creating a comfortable and functional layout perfect for everyday living or entertaining. The primary bedroom features a large walk-in closet, offering comfort and convenience. Relax and enjoy the view from the oversized private balcony just off the living room. Ideally situated just steps from the Cady Way Trail, Showalter Field, Ward Park, the YMCA, medical centers, shopping, and dining, this location truly offers convenience at every turn. Enjoy being only minutes from the renowned Park Avenue, local museums, and everything Winter Park has to offer. Four Seasons Condominiums is a beautifully maintained 20-acre community within the Winter Park city limits and located in a highly sought-after school district. Residents enjoy an array of amenities including three swimming pools, tennis courts, shuffleboard courts, laundry facilities, and a clubhouse with a library. Whether you're looking for a primary residence, seasonal retreat, or investment opportunity, this condo is a must-see!
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Veronica Figueroa (407-519-3980)
2614 PARKLAND DR, WINTER PARK, FL 32789
$1,924,450407 Days on yellowkey MLS ID: O6301489
REDUCED by $24,550 (1.3%) on 05/29/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3307 Built: 2007 Tax: $12,712 (2024)Community: Parklando 03Spa: YesSingle Family
Taxes:$12,712
Remarks: Fully remodeled! One of the most competitively priced homes featuring over 3,300 SF, in the 32789 zip code, and in the K-8 Audubon Park School District. The K-8 Audubon Park School District is a small pocket, and ranked one of the best district's in the state. Fully remodeled luxury pool homes in the highly sought-after Audubon K-8 and Winter Park school district with over 3,300 square feet of exceptional living space, capped with a brand-new, architecturally stunning tile barrel roof that blends timeless Mediterranean elegance with lasting durability. 2614 Parkland Drive, a fully reimagined luxury residence in the heart of Winter Park. This is your chance to own a showpiece property with over 3,300 SF zoned for the coveted Audubon Park K-8 and Winter Park High School districts. Completely remodeled in late 2022, this home radiates warmth and sophistication. Solid light oak floors, custom railings, and an open-concept flow make entertaining effortless. The chef’s kitchen is a centerpiece; quartz counters, full-height designer tile, and abundant storage bring form and function together. Out back, discover your private resort. A heatable custom pool & spa finished in ultra-rare Caribbean blue tile sets the tone; elevated with two natural-gas fire pits, dramatic waterfalls, porcelain privacy walls, and a built-in grill. Every evening feels like a five-star escape.The first-floor master suite offers direct access to the outdoor oasis, while upstairs features three oversized bedrooms, a loft, and a private patio for sunset views. Brand-new tile roof, dual tankless water heaters, central vacuum, and all-natural gas appliances ensure low-maintenance, worry-free living. This is more than a home it’s a statement. A chance to live where luxury, location, and lifestyle converge.
Listing is courtesy of: JW GASTON LLC (321-239-5540)
Listing Agent: Ryan Gaston (321-239-5540)
151 OAKWOOD WAY, WINTER PARK, FL 32789
$2,850,000116 Days on yellowkey MLS ID: O6380037
0 Days Off yellowkey (back on 5/29/2026)
REDUCED by $100,000 (3.4%) on 05/26/2026
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 4129 Built: 2023 Tax: $34,218 (2025)Community: CharmontSpa: NoSingle Family
Taxes:$34,218
Remarks: Repositioned at $2,850,000, 151 Oakwood Way is one of the strongest newer luxury opportunities under $3M in Winter Park. Built by LunDev Custom Homes in 2023, this 4,129-square-foot residence sits on a quiet brick street in Charmont and offers a private pool, spa, covered lanai, summer kitchen, automatic screens, and a rare under-$700/sf position for newer luxury construction in 32789. Inside, the home features wide-plank wood flooring, high ceilings, quartz surfaces, Thermador appliances, custom built-ins, a wet bar, walk-in closets, and an open kitchen, dining, and living layout filled with natural light. The main living areas connect directly to the outdoor entertaining space, creating the indoor-outdoor flow buyers want in Winter Park. The floor plan includes 4 bedrooms, 4.5 baths, a main-level primary suite, generous secondary spaces, and a large flex room that can function as an office, family room, media room, game room, or future guest suite, with plumbing already in place. Set on a landscaped 0.26-acre lot with no HOA shown publicly, 151 Oakwood offers a compelling combination in 32789: newer LunDev construction, private pool, outdoor kitchen, brick-street setting, and a sub-$3M position close to Winter Park, Baldwin Park, Audubon Park, and Park Avenue.
Listing is courtesy of: CORCORAN PREMIER REALTY (407-965-1155)
Listing Agent: Matthew Burks (407-257-5347)
3220 NETHERWOOD DR, WINTER PARK, FL 32792
$269,000136 Days on yellowkey MLS ID: O6374172
5 Days Off yellowkey (back on 5/29/2026)
REDUCED by $10,990 (3.9%) on 04/20/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1036 Built: 1982 Tax: $1,222 (2025)Community: Coronation AddHalf Duplex
Taxes:$1,222
Remarks: Under contract-accepting backup offers. Welcome home to this fully renovated 2-bedroom, 1.5-bath residence! This home features a brand-new kitchen, new flooring throughout, and beautifully updated bathrooms. Nestled in a quiet neighborhood, it offers a large backyard—perfect for outdoor entertaining or future expansion. Ideal for a first-time homebuyer or anyone seeking stress-free living. Best of all, NO HOA! Conveniently located near major highways, great schools, shopping, and dining in the highly desirable Winter Park area. Don’t wait—make this home yours today!
Listing is courtesy of: THE FIRM RE (407-227-3345)
Listing Agent: Nimrah Ashraf (786-356-6611)
1750 CAROLLEE LANE, WINTER PARK, FL 32789
$1,820,00073 Days on yellowkey MLS ID: O6391179
REDUCED by $70,000 (3.7%) on 05/26/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3249 Built: 2012 Tax: $24,658 (2025)Community: Green Terrace V/140 Lot 3 Blk BSingle Family
Taxes:$24,658
Elementary School: Brookshire Elem
Remarks: Welcome to 1750 Carollee Lane, where timeless charm meets modern luxury. Set on a homesite with desirable southern exposure in the heart of Winter Park, this four-bedroom, 3.5-bath, custom pool and spa residence offers more than 3,200 square feet of thoughtfully updated living space near Park Avenue, the Chain of Lakes and top-rated schools. The fully renovated 2025 kitchen serves as the centerpiece of the home, featuring quartzite countertops, a custom wood hood, Zellige-style backsplash, induction cooktop, oversized workstation sink and an expansive island designed for gathering and entertaining. The first-floor primary suite offers a private retreat with a completely reimagined spa-inspired bath showcasing marble flooring, quartzite surfaces, custom solid wood cabinetry, a freestanding soaking tub and upgraded walk-in shower. Designed for comfort and entertaining, the home also features a dedicated office and an upstairs loft with a custom dry bar and beverage refrigerator. Outdoors, the backyard lives like a private resort-style oasis, complete with a saltwater pool and spa, sun shelf, travertine decking, electronic roll-down screens and a fully equipped outdoor kitchen designed for year-round enjoyment. Lush new backyard landscaping completed in May 2026, including enhanced privacy elements, creates an intimate outdoor setting rarely found this close to the heart of Winter Park. Additional highlights include updated irrigation supported by a private well, a new downstairs HVAC system and a home warranty provided for the buyer at closing. Move-in ready and impeccably maintained, this residence offers refined living in one of Winter Park’s desirable settings.
Listing Agent: Michelle Hochfelder (407-221-5073)
1161 VALENCIA AVE, WINTER PARK, FL 32789
$3,995,000284 Days on yellowkey MLS ID: O6330736
REDUCED by $80,000 (2.0%) on 05/29/2026
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 4181 Built: 2021 Tax: $30,421 (2024)Community: Valencia TerraceSpa: YesSingle Family
Taxes:$30,421
Remarks: Conveniently situated near the Winter Park Country Club, this contemporary masterpiece, built by premier builder Z Properties, offers the ideal mix of style, comfort, and modern living. Meticulously maintained with great inspection. Completed in 2021, the residence has 4,181 square feet of thoughtfully designed living space, including four bedrooms each with a private ensuite bath and an additional powder room. A 412-square-foot casita with a wet bar and private entrance completes its functionality by providing extra flexibility, perfect for guests, extended family, workspace or workout area. The interiors showcase timeless design with high ceilings, glass walls, and carefully curated finishes. The chef’s kitchen and butler’s pantry pair handcrafted cabinetry and stone surfaces with professional-grade appliances, flowing seamlessly into open living and dining spaces designed for both everyday living and entertaining. Outdoors, a 65-foot lap pool anchors the private backyard retreat, complemented by a covered lanai, marine-grade summer kitchen, fireplace lounge, tree garden and lush landscaping. Solid block construction, advanced state-of-the-art home systems, and a climate-controlled two-car garage with an extended hidden driveway highlight the home’s privacy, quality, and convenience. With a distinct European vibe under canopy trees and cobblestone streets in the desirable Valencia Terrace neighborhood, this home is just moments from Park Avenue’s boutiques, fine dining, Rollins College, the Farmers’ Market, and the Morse Museum. Zoned for top-rated Winter Park schools, it offers both luxury and practicality in one of Central Florida’s most sought-after communities.
Listing is courtesy of: THE REAL ESTATE COLLECTION LLC (407-656-7814)
Listing Agent: Lisa Mahjoub (321-217-9965)
2779 SANBINA ST, WINTER PARK, FL 32789
$429,00080 Days on yellowkey MLS ID: O6388746
REDUCED by $10,000 (2.3%) on 05/29/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1405 Built: 1960 Tax: $5,629 (2024)Community: Howell HeightsSingle Family
Taxes:$5,629
Elementary School: Dommerich Elem
Remarks: Rare opportunity in the heart of 32789 — priced under $500K, this 3-bedroom, 2-bathroom Winter Park home delivers the location, lot, and bones that buyers in this zip code rarely find at this price point. Zoned for Dommerich Elementary and Winter Park High School and situated on a generous 0.23-acre lot, this is the one worth moving quickly on. Upon entry, a sun-drenched living room leads to a formal dining room, which connects to a secondary living area perfect for entertaining. The open kitchen features granite countertops, stainless steel appliances, and a casual eat-in area, while refinished terrazzo floors run throughout the home adding character and easy-care durability that's quintessentially Florida. 2021 roof and HVAC mean the big-ticket items are already done. Step outside to a large screened-in patio overlooking a spacious backyard with plenty of room to add a pool or expand. One or more photo(s) was virtually staged. Minutes from Park Avenue and Downtown Winter Park's incredible restaurants and fantastic shopping, Rollins College, UCF, AdventHealth Winter Park, Downtown Orlando, and more.
Listing is courtesy of: MAINFRAME REAL ESTATE (407-513-4257)
Listing Agent: Caroline Fiore (407-538-2381)
1433 ASTER CT, WINTER PARK, FL 32792
$389,00018 Days on yellowkey MLS ID: O6407873
REDUCED by $10,000 (2.5%) on 05/21/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1363 Built: 1984 Tax: $1,057 (2025)Community: Garden Lake Estates Unit 3Single Family
Taxes:$1,057
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Welcome to this charming 3-bedroom, 2-bath home with a 2-car garage, perfectly situated on a quaint, low-traffic street. This thoughtfully designed split floor plan offers both privacy and functionality, while soaring vaulted ceilings create an open, spacious feel throughout. The updated kitchen serves as the heart of the home, offering modern touches and great flow for everyday living or entertaining. Enjoy peace of mind with a newer A/C, adding comfort and value for years to come. Step outside to a fully fenced backyard overlooking a tranquil pond—perfect for relaxing, entertaining, or enjoying Florida’s beautiful weather. Whether you’re a first-time buyer, downsizing, or looking for a smart investment property, this home offers the ideal combination of comfort, charm, and opportunity in Florida.
Listing is courtesy of: RE/MAX TOWN & COUNTRY REALTY (407-695-2066)
Listing Agent: Dominick Florio (321-377-4045)
234 DETMAR DR, WINTER PARK, FL 32789
$1,599,000111 Days on yellowkey MLS ID: O6379927
2 Days Off yellowkey (back on 5/29/2026)
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
Remarks: Under contract-accepting backup offers. 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 is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)
Listing Agent: Nicole Seybold (407-808-9374)
7120 BROOKSIDE TRL, WINTER PARK, FL 32792
$510,00039 Days on yellowkey MLS ID: O6398534
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1753 Built: 1976 Tax: $3,098 (2025)Community: Replat Of Lts 1 2 & 3 Brookside SubSingle Family
Taxes:$3,098
Elementary School: Eastbrook Elementary
Remarks: Under contract-accepting backup offers. SWIM WHENEVER YOU LIKE! Discover a new dimension of living - Sparkling pool awaits you, so come and dip your toes here! Pool party ideas come naturally in this proud-to-show huge fenced-in backyard with lots of entertaining space. Oversized pool deck and large rock patio, plus huge screened in porch, make a great space for Florida living. This rock-solid ranch offers 4 bedrooms and 2 baths set in over 1700+ sf. Great curb appeal with cool rock trimming and freshly landscaped beds. Roomy formal living room greets you as you enter. The primary bedroom is split from the other 3 bedrooms and lies off the living room. This primary suite offers closet space galore. Plus, pretty double vanity, separated from the shower area. Terrific, updated kitchen with neat rustic tile, quartz counters, tile backsplash, stainless appliances, cool single bowl sink and faucet, shiplap wall and closet pantry round out this kitchen space. The family room is a great size, and the kitchen quartz counter/bar also serves as a gathering place flowing into the family room, which features a shiplap TV wall and blind-inside sliders to the screened in porch. The other 3 bedrooms and 2nd bath are off the family room. All are nice sized and the bath with nifty vintage tile, has an access door to outside/pool area. Pretty luxury vinyl plank flooring through living areas. All set in Winter Park on a .23 acre lot and Cul-De-Sac street. Conveniently close to schools, hospital, shopping, Costco and restaurants. Plus, easy access to highway 436 and straight shot to the Orlando International Airport. Don’t wait on this rock-solid ranch in desirable Winter Park...it’s ready for its new owners!
Listing is courtesy of: KELLY PRICE & COMPANY LLC (407-645-4321)
Listing Agent: Teresa Jones (407-376-2130)
630 KILLARNEY BAY CT #3, WINTER PARK, FL 32789
$495,000123 Days on yellowkey MLS ID: O6375307
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 1428 Built: 1986 Tax: $6,595 (2025)Community: Killarney Bay CondoCondo
Taxes:$6,595
Remarks: Lakefront townhome in desirable Killarney Bay directly on Lake Killarney, offering 2 bedrooms, 2.5 baths, and a one-car carport. This spacious residence features an open living and dining area that flows to a screened porch, perfect for relaxing and enjoying tranquil lake views in a well-maintained complex. Both bedrooms are upstairs for privacy, each with its own bath, with a convenient half bath on the main level for guests. Enjoy community amenities including a swimming pool and a waterfront deck just 30 feet away, ideal for soaking in sunsets and lakeside breezes. All of this in an unbeatable location, just minutes from Winter Park Village, Trader Joe’s, dining, and shopping, with easy access to major roads for commuting.
Listing is courtesy of: FLORIDA ONE REAL ESTATE LLC (407-599-7070)
Listing Agent: Anthony Consalvo (407-599-7070)
4190 BEAR GULLY RD, WINTER PARK, FL 32792
$499,900146 Days on yellowkey MLS ID: O6371014
REDUCED by $25,000 (4.8%) on 05/29/2026
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2058 Built: 2003Monthly Fee: $52 Tax: $5,630 (2024)Community: Bear Gully ForestSingle Family
Taxes:$5,630
Remarks: Price reduced!! Spacious Winter Park home on over a half acre with no rear neighbors!. In Bear Gully Forest community and has over 2,000 s/f- with a Living Room, Dining Room, Eat-in Kitchen and more. The home's fully-equipped kitchen has excellent cabinet space and appliances that include a stove, microwave, and dishwasher. An inside laundry room has a washer/dryer combination for your convenience. Bedroom with 1/2 bath upstairs. Roof new in 2018 with a 10 year full warranty.
Listing is courtesy of: ADVANCE REALTY & MANAGEMENT LLC (407-901-3636)
Listing Agent: Craig Swetnam (407-802-0405)
1340 PLACE PICARDY, WINTER PARK, FL 32789
$1,599,000109 Days on yellowkey MLS ID: O6382113
3 Days Off yellowkey (back on 3/30/2026)
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3459 Built: 1997 Tax: $7,515 (2025)Community: FontainebleauSingle Family
Taxes:$7,515
Remarks: Under contract-accepting backup offers. Set on an oversized 1/3-acre lot in the heart of Winter Park, this one-owner home was custom built in 1997 and has been meticulously maintained ever since. Solid block construction, timeless stone accents, and mature landscaping give it great curb appeal from the moment you arrive. Step inside to a spacious foyer with hardwood floors that carry through most of the main living areas. To the right, the living room features built-in shelving and a bay window that fills the space with natural light. It flows into the formal dining room, also with hardwood floors, plantation shutters, and plenty of room to host. A conveniently located powder bath serves this side of the home. To the left is the heart of the house - a generously sized kitchen with abundant white cabinetry, stone countertops, a center island, double ovens, a built-in pantry with pull-out storage, and a breakfast bar. The separate eat-in area overlooks the backyard and opens to the screened porch through French doors. The kitchen connects to a large family room with coffered ceilings, a gas fireplace, built-ins, and additional French doors leading outside. The home offers a three-way split floor plan for privacy. The primary suite sits on its own wing and is very spacious, featuring crown molding, a bay window, and French doors to the patio. The en-suite bath includes double vanities, large "His & Hers" walk-in closets with custom closet systems, a soaking tub, separate shower, and private water closet. On the opposite side of the home, you’ll find a generously sized secondary bedroom with its own en-suite bathroom and walk-in closet. Toward the back of the house is a third bedroom with a built-in desk, French doors to the exterior, and an en-suite Jack-and-Jill bath that also serves the family room. The first floor also includes an indoor laundry room with ample cabinetry and a utility sink. Upstairs, a huge bonus room offers incredible flexibility - game room, media room, office, or potential fourth bedroom. There is also space to add a bathroom if desired. Out back, a large screened porch with high ceilings overlooks a peaceful, lushly landscaped yard with plenty of room to enjoy Florida living. Additional features include plantation shutters throughout, a spacious two-car garage, and an unbeatable location just minutes from Park Avenue’s shopping and dining. Zoned for highly rated Dommerich Elementary, Maitland Middle, and Winter Park High. Call today to schedule your private showing!
Listing Agent: Maria Van Warner (407-256-8066)
1052 MANCHESTER CIR, WINTER PARK, FL 32792
$460,000128 Days on yellowkey MLS ID: O6376260
REDUCED by $10,000 (2.1%) on 05/28/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1703 Built: 1983 Tax: $5,216 (2025)Community: Howell Estates 1St AddSingle Family
Taxes:$5,216
Remarks: PRICE REDUCED!! Welcome to your dream home! This beautifully renovated single-story residence features 3 spacious bedrooms and 2 baths, all set on an expansive .42-acre lot in the desirable Howell Estates community. Brand New Roof (2024) Replumbed (2024) New HVAC System, Gourmet Kitchen: Brand new upgraded white cabinets, stunning quartz countertops, and new stainless steel appliances. Luxurious Bathrooms: Both completely renovated, featuring modern finishes Oversized Bedrooms: Including a primary suite with his-and-hers closets and an ensuite bath with a gorgeous walk-in shower. In the Family Room: Spacious layout with a cozy wood-burning fireplace, Oversized Garage: Perfect for larger vehicles, including SUVs. The backyard has a: New Fence, New Pergola and New Extended Porch. This home is move-in ready and waiting for your family to create lasting memories. Don’t miss out on this exceptional opportunity in Winter Park!
Listing is courtesy of: FLORIDA INVESTMENT REALTY GRP (407-937-8450)
Listing Agent: Yuleisy Marquez (407-937-8450)
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