Displaying: For Sale
Location: Winter Park
Property Type(s): Townhomes
Beds: 3 to 3
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Winter Park - 24 properties found
2521 GALLIANO CIR, WINTER PARK, FL 32792
$360,000Listed 06/24/2026 2:53PM MLS ID: O6419329
Bed: 3 Bath: 3.5 Gar: 1 Liv Area Sq Ft: 1682 Built: 2003Monthly Fee: $175 Tax: $4,532 (2025)Community: Vistas At Lake HowellTownhouse
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$4,532
Elementary School: Sterling Park Elementary
High School: Lake Howell High
Tax Year: 2025
Middle School: Tuskawilla Middle
Remarks: Welcome to this beautifully maintained townhome located in the heart of Winter Park, Florida. From the moment you arrive, the charming exterior draws you in with its classic stucco finish, attached one-car garage, manicured landscaping, and a welcoming shaded entry framing the front door. Step inside to an inviting foyer featuring high ceilings, modern lighting, and a striking staircase that sets a stylish tone for the rest of the home. The main level transitions into an expansive, light-filled open concept floor plan seamlessly connecting the living room, dining area, and kitchen. Rich wood-look LVP flooring runs throughout the entire lower level, perfectly complementing the crisp neutral walls and providing a cohesive, contemporary aesthetic. The spacious living and dining areas offer an exceptional layout for both daily living and effortless entertaining. Large sliding glass doors at the rear of the home flood the living space with natural light and open directly to a private, screened-in back patio, making it easy to enjoy the Florida breeze. Overlooking the dining area is a spacious kitchen, which features a half-wall cutout that keeps the chef connected to the conversation. Equipped with plenty of warm wood cabinetry, neutral countertops, a deep double sink, and a suite of white appliances, this kitchen is as ample as it is welcoming. A convenient guest half-bathroom with a pedestal sink completes the well-designed ground floor layout. Head upstairs to discover the private living quarters, where the beautiful wood-look flooring continues through the hallway and into each spacious bedroom. The expansive primary suite serves as a true retreat, boasting high vaulted ceilings, an elegant modern ceiling fan, a massive walk-in closet with built-in wire shelving, and a trio of large windows that fill the space with cheerful morning light. This main bedroom easily accommodates king-sized furniture and offers the luxury of an attached en-suite bathroom with dual sinks. The additional bedrooms are equally impressive, each featuring soaring vaulted ceilings, updated stylish ceiling fans, and generous closet space near the dedicated upper-level laundry closet, which comes equipped with a washer and dryer. The outdoor and utility spaces add tremendous value and convenience to this efficient property. The attached garage features an open, clean layout perfect for secure parking, extra storage, or a small home workshop area. At the back of the home, the deep screened-in patio is an ideal spot for outdoor dining, grilling, or relaxing in the shade. The patio steps out onto a beautiful community green belt with pristine lawns and mature shade trees, offering a peaceful residential backdrop. Nestled in a premium, tree-lined enclave, the community boasts pristine, winding roads, manicured privacy hedges, and a scenic retention pond complete with a flowing water fountain feature. This idyllic neighborhood setting perfectly balances the tranquility of nature with outstanding proximity to nearby lakes, parks, major roadways, and local shopping centers. Don't miss the opportunity to own this pristine, move-in ready retreat in one of Central Florida's most highly sought-after locations.
Listing is courtesy of: LPT REALTY LLC (386-388-7877)
Listing Agent: Daniel Lennon (954-483-9760)
1411 MILLER AVE, WINTER PARK, FL 32789
$899,0008 Days on yellowkey MLS ID: O6416926
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 1824 Built: 2023Monthly Fee: $200 Tax: $8,005 (2025)Community: H Vanwies SubTownhouse
Taxes:$8,005
Elementary School: Killarney Elem
High School: Edgewater High
Middle School: College Park Middle
Remarks: Built in 2023 by SGC Homes, this exceptionally livable modern Mediterranean townhome blends comfort and convenience in a classic architectural package, offering 3 bedrooms, 3-1/2 baths, and no shared internal walls, for perfect privacy. There is so much to love here. Situated on a tree-lined brick street in the walkable, convenient area of Minnesota Row, this beauty has been lightly occupied as a second home, and it has never been rented. It is truly a blank slate to make your own. Features that make it special include an open yet cozy floor plan, with a roomy ground floor primary suite which includes a walk-in closet, designer bath with 2 sinks, soaking tub and separate shower, as well as Electrolux washer and dryer, for main-floor convenience. The chef's kitchen with high-end appliances looks into the combined living and dining space. Direct access from the 2-car garage into the kitchen and a very private garden complete the ground floor. Upstairs you'll find two bedrooms, both en suite, separated by an open sitting area for a little extra living space, and a second floor larger laundry with a sink and cabinets for additional storage. Large windows make the rooms light and bright, and the house is ideally situated for maximum privacy. You're going to love the finishes in this unit, including the engineered wood floors, fans in all bedrooms and high end light fixtures, as well tankless hot water, and pavers on the outdoor areas. Easy access to all the options in charming Winter Park including Park Avenue, Winter Park Village, Rollins College and the many parks and green spaces, as well as more shops and dining in College Park. I-4 is minutes away, to get to any place in and around Orlando.
Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)
Listing Agent: Sue Gilman (407-405-0108)
413 W MORSE BLVD, WINTER PARK, FL 32789
$2,695,00018 Days on yellowkey MLS ID: O6412134
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3048 Built: 2018Monthly Fee: $386 Tax: $19,919 (2026)Community: Town Of Winter ParkTownhouse
Taxes:$19,919
Elementary School: Brookshire Elem
High School: Winter Park High
Tax Year: 2026
Middle School: Maitland Middle
Remarks: LUXURIOUS LIVING WITH FANTASTIC LOCATION This Winter Park three story townhouse is within walking distance to all the fun amenities of the city- the many restaurants, boutique shops, banks, post office, farmers market, Central Park and Rollins College. Designed by architect Phil Kean and built in 2017 the owners have embellished this townhome with custom millwork and finishes, wood floors, sound system, full house generator and a private elevator to all floors. The first floor has a two car garage with storage lift above, large laundry room/home office and a downstairs guest suite. The second floor features a stylish and comfortable living room with lovely custom ceiling detail and moldings, gas fireplace, a sophisticated powder bath, and a beautiful dining room that opens to an eat-in chef's kitchen with Subzero, Wolfe and Bosch appliances and light Taj Mahal quartzite countertops. The third floor offers the spacious master bedroom and bath and also has the additional guest bedroom suite. Take the elevator to the roof top for great views of the city and here find even more potential space for fun entertaining. If your dream is to own a townhome in the heart of Winter Park, here is a stunning one for you!
Listing is courtesy of: COLDWELL BANKER REALTY (407-647-1211)
Listing Agent: Av Blalock (407-579-9056)
3443 ALLSTON LN, WINTER PARK, FL 32792
$299,99912 Days on yellowkey MLS ID: O6409708
0 Days Off yellowkey (back on 6/14/2026)
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1133 Built: 1993Monthly Fee: $65 Tax: $1,123 (2025)Community: Villas Of Casselberry Ph 4Townhouse
Taxes:$1,123
Elementary School: Eastbrook Elementary
Remarks: Under contract-accepting backup offers. 3-bedroom, 2-bath SINGLE-story block townhome with garage located in an excellent school district! Recent improvements include a BRAND-NEW ROOF (2025), BRAND-NEW HVAC SYSTEM (June 2026), and BRAND-NEW WATER HEATER (June 2026), all still under warranty! Plus fresh interior paint throughout (June 2026) and new flooring in the rear bedroom (no carpet in the home). With the big-ticket items already completed, this home offers exceptional peace of mind and truly worry-free ownership. The spacious floor plan features soaring living room ceilings, generously sized bedrooms, and a screened rear patio with ceiling fan and lighting, perfect for relaxing or entertaining—all on one level with no interior stairs. Two of the bedrooms feature sliding glass doors providing direct access to the backyard and abundant natural light. In addition to the screened patio, you’ll enjoy a large open patio area ready to become your own private outdoor retreat for grilling, gardening, or entertaining. Enjoy a super low HOA of just $65 per month, which includes access to a community pool just a short walk away, as well as a serene lake with a covered dock and gazebo perfect for relaxing, fishing, or socializing with neighbors. Ideally located near Downtown Winter Park, Park Avenue, Rollins College, Full Sail University, UCF, and Valencia College, with easy access to SR-436 and endless shopping, dining, and entertainment options just minutes away. This home is a true gem offering excellent schools, recent upgrades, a prime location, low HOA fees, and a warm, welcoming atmosphere. Whether you’re a first-time homebuyer, downsizing, or seeking a fantastic investment opportunity, this property checks all the boxes. Don’t miss your opportunity to make it yours!
Listing is courtesy of: FLORIDA REALTY INVESTMENTS (407-207-2220)
Listing Agent: Nikita Ager, Llc (310-800-3100)
1781 INDIANA AVE #A, WINTER PARK, FL 32789
$545,000133 Days on yellowkey MLS ID: O6381195
0 Days Off yellowkey (back on 5/1/2026)
REDUCED by $20,000 (3.5%) on 04/14/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1616 Built: 2008Monthly Fee: $464 Tax: $6,026 (2024)Community: Las Casas De IndianaTownhouse
Taxes:$6,026
Tax Year: 2024
Remarks: Welcome to 1781 Indiana Avenue, Unit A, a beautifully appointed three-bedroom, two and a half bathroom townhouse nestled in the heart of Winter Park. This inviting residence offers the perfect blend of comfort and convenience, featuring a spacious two-car garage and a private courtyard ideal for morning coffee, outdoor dining, or relaxing in the Florida sunshine. Inside, the thoughtfully designed floor plan provides generous living spaces, well-proportioned bedrooms, and an effortless flow for everyday living and entertaining. Located just minutes from Winter Park’s renowned shopping, dining, parks, and top-rated schools, this home presents an exceptional opportunity to enjoy low-maintenance living in one of Central Florida’s most desirable neighborhoods.
Listing is courtesy of: CARLISLE REALTY, LLC (407-557-4024)
Listing Agent: James Rouadi (407-557-4024)
512 W SWOOPE AVE, WINTER PARK, FL 32789
$1,399,0006 Days on yellowkey MLS ID: O6417375
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2585 Built: 2023Monthly Fee: $659 Tax: $15,833 (2025)Community: Vilasa TwnhmsTownhouse
Taxes:$15,833
Elementary School: Lakemont Elem
Remarks: Vilasa Homes — Winter Park’s Expression of Modern Luxury. Perfectly positioned just steps from Park Avenue, this architecturally stunning residence blends refined design with the effortless elegance of Winter Park living. Crafted by Nasrallah Architectural Group, Ted Maines Interiors, and Jordan Builders, this home showcases an Alys Beach–inspired aesthetic with warm wood accents, wrought iron detailing, and two-story block construction for enduring quality. Interiors exude sophistication: soaring 13' ceilings on the main level, 10' upstairs, level-four wall finishes, all-wood flooring, Pella double pain windows and curated designer lighting. The chef’s kitchen is a showpiece— high-end flat panel cabinetry, quartz surfaces, Thermador appliances, and an expansive quartz waterfall island overlooking lush greenery. A private in-unit elevator provides effortless access to the second-floor, enhancing both convenience and sophistication. The second-floor primary retreat offers a serene escape with a loft for office or wellness space, a spa-caliber bath with soaking tub and oversized shower, and generous closet options. Two additional bedrooms provide versatile accommodation for guests, a private office, or fitness space, complemented by a thoughtfully designed shared bath. Outdoor living is exceptional with an expansive 40' x 20' private fenced-in backyard, including a covered patio which extends from the sliding glass doors. A 2-car garage with insulated doors completes the residence. Moments from Winter Park’s finest dining, boutiques, museums, lakes, Hannibal Square and Rollins College. Vilasa Homes offers a rare opportunity to live at the center of it all—wrapped in luxury, design, and timeless style.
Listing Agent: Carmen Quintana (407-340-3932)
2676 BARBADOS DR, WINTER PARK, FL 32792
$340,00026 Days on yellowkey MLS ID: O6411958
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1743 Built: 1978Monthly Fee: $98 Tax: $4,131 (2025)Community: Windward Square Sec 2Townhouse
Taxes:$4,131
Remarks: Welcome to this beautifully maintained 3-bedroom, 2-bathroom corner-unit townhome located in the heart of Winter Park. Offering 1,743 square feet of thoughtfully designed living space, this home combines comfort, style, and an unbeatable location just minutes from shopping, dining, parks, and top-rated schools. The desirable corner-unit placement provides added privacy, extra natural light, and a spacious feel throughout. Inside, you’ll find luxury vinyl plank flooring flowing seamlessly throughout the home and a stunning vaulted ceiling that creates an airy, open atmosphere in the living room. The beautifully updated kitchen is truly the centerpiece of the home, featuring gorgeous wood countertops, ample cabinet space, and an open-concept layout perfect for entertaining family and friends. Step outside to the rear screened-in patio and enjoy peaceful pond views in your own private outdoor retreat. Whether you’re sipping your morning coffee or unwinding after a long day, this tranquil space offers the perfect setting to relax and enjoy Florida living year-round. This exceptional Winter Park townhome is a rare opportunity you won’t want to miss.
Listing Agent: Joseph Sipp (407-820-7016)
2339 INAGUA WAY, WINTER PARK, FL 32792
$299,9994 Days on yellowkey MLS ID: O6415345
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1284 Built: 1979Monthly Fee: $98 Tax: $2,187 (2025)Community: Windward Square Sec 3Spa: NoTownhouse
Taxes:$2,187
Elementary School: None
High School: None
Middle School: None
Remarks: Enjoy abundant natural light throughout this beautifully maintained one-story, 3-bedroom, 2-bath home, enhanced by soaring vaulted ceilings and an inviting open layout. The kitchen features natural wood cabinetry, stainless steel appliances, and a charming breakfast nook with access to the front patio. The spacious primary suite offers a walk-in closet and private access to the patio. A desirable split-bedroom floor plan provides added privacy, with two guest bedrooms and a full guest bath situated at the front of the home. The bright and versatile patio can be accessed from both the living room and primary suite, creating the perfect space to relax, entertain, or enjoy year-round Florida living. Roof 2023, A/C 2020, Water Heater 2020, pex piping upgrades include pavered driveway, bathrooms updated, patio doors updated, and vinyl fencing in backyard.
Listing is courtesy of: BAIRD REALTY, LLC (407-300-4759)
Listing Agent: Eric Swinarski (407-383-0030)
1265 ARLINGTON PL, WINTER PARK, FL 32789
$879,00013 Days on yellowkey MLS ID: O6415981
Bed: 3 Bath: 3.5 Gar: 1 Liv Area Sq Ft: 2030 Built: 2014 Tax: $8,450 (2025)Community: Virginia Hgts RepSpa: NoTownhouse
Taxes:$8,450
Elementary School: Audubon Park K8
Middle School: Audubon Park K-8
Remarks: Virtually Staged. Welcome to 1265 Arlington Place, a beautifully appointed townhome nestled in the heart of Winter Park's coveted College Quarter - just steps from Rollins College, Park Avenue, and all the dining, shopping, and culture that downtown Winter Park provides. The main level features an open living area flowing into a well-equipped kitchen with granite countertops and solid wood cabinetry, a wet bar for effortless entertaining, a dining room, and a convenient half bath - all finished with rich hardwood floors. French doors lead to a private, fenced yard with two deck spaces, one covered with an awning, perfect for outdoor entertaining or quiet mornings outside. Also on the main level, the spacious primary suite offers an oversized walk-in closet and direct yard access. The luxurious primary bath features double vanities, a soaking tub, and a separate standing shower. Upstairs, a generous bonus living space is flanked by two additional bedrooms, one of which includes an en-suite bath and two walk-in closets - ideal for guests or a home office setup. A full hall bath completes the upper level. Throughout the home, storage has been thoughtfully considered, with generous closet space at every turn. Smart home features including remote-controlled outdoor lighting, garage door, irrigation, and alarm system make this the ultimate lock-and-leave lifestyle home. Residents also enjoy exclusive access to Virginia Heights Park, a private lakefront park reserved for neighborhood use only - a rare amenity in the heart of Winter Park. Come see what makes this property so special!
Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)
Listing Agent: Erika Beerbower (407-758-2727)
905 ENCLAVE PL, WINTER PARK, FL 32792
$1,495,00096 Days on yellowkey MLS ID: O6383679
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2756 Built: 2026Monthly Fee: $247 Tax: $9,900 (2026)Community: The Enclave Winter ParkTownhouse
Taxes:$9,900
Remarks: Pre-Construction. To be built. The Enclave is a premier, boutique community in the heart of Winter Park, featuring just 23 thoughtfully designed residences nestled beneath mature oak canopies, being built by FG Schaub Custom Homes. Ideally located within walking distance to Park Avenue and historic Old Winter Park, this exclusive neighborhood blends timeless character with modern luxury. The courtyard homes at The Enclave offer a distinctive design centered around light, openness, and indoor-outdoor living. These four-bedroom residences feature thoughtfully designed floor plans with a first-floor primary suite and expansive living spaces that flow seamlessly to private outdoor areas. Large windows and two unique entry design options allow for abundant natural light, enhancing the open-concept layouts. Each home is finished with high-end selections, including Wolf and Sub-Zero appliances, high-performance double-pane windows, and elevated interior finishes throughout. Blending modern design with comfort and functionality, these homes provide a unique opportunity to enjoy a private courtyard lifestyle in one of Winter Park’s most desirable locations. Design book is available upon request. Please inquire for details and customization options.
Listing is courtesy of: CORCORAN PREMIER REALTY (407-965-1155)
Listing Agent: Matthew Burks (407-257-5347)
1261 INDIANA AVE, WINTER PARK, FL 32789
$534,90065 Days on yellowkey MLS ID: O6400698
REDUCED by $4,100 (0.8%) on 06/09/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1660 Built: 2005Monthly Fee: $360 Tax: $2,892 (2025)Community: Townhomes/Harper PlaceTownhouse
Taxes:$2,892
Remarks: Tucked in the heart of Harper Place, this 3-bedroom, 2.5 bath end unit townhome 1,660 sq ft of light-filled, low maintenance living in a thriving Winter Park location. The main level features a spacious living and dining room combo plus a separate family room and kitchen-perfect for entertaining. The kitchen includes a built-in desk and bookcase, pantry, gas cooktop and range hood, granite counters, island, and breakfast nook. French doors open to a private side patio ideal for relaxing, pot gardening or grilling. The interior laundry located off the kitchen leads out to the functional and spacious 2- car garage. Upstairs, the primary bedroom has a walk-in closet. The primary bath has a walk-in shower. Two secondary bedrooms offer flex space and share a bath with a tub shower. Wood floors downstairs and carpet upstairs. Recent updates include roof and gutters in 2022, exterior paint in 2023 and water heater and AC in 2024. Community improvements continue with road resealing completed in the Spring of 2026, enhancing a well-kept neighborhood. 1261 Indiana is a great fit for a buyer seeking comfort, urban convenience, and a simplified lifestyle. Close to 1-4, shops, restaurants, hospital, and museums. Short drive to downtown Orlando. Great investment opportunity as the community allows rentals.
Listing Agent: Megan Cross (407-353-9997)
2401 ANTILLES DR, WINTER PARK, FL 32792
$320,000231 Days on yellowkey MLS ID: O6357934
0 Days Off yellowkey (back on 5/14/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1719 Built: 1977Monthly Fee: $95Community: Windward Square Sec 1Townhouse
Taxes:$0
Remarks: Under contract-accepting backup offers. Fantastic end unit with enclosed Florida Room in the sought after Windward Square! This 3/2 features several updates including a, updated kitchen with 42" wood cabinets, granite counters and a center island! Most rooms have upgraded ceiling fans from Dan”s Fans with a lifetime guarantee. The home has newer A/C, high impact windows and the home has been re-piped for your peace of mind. This is a wonderful space and great to prep for a dinner party! Open floor concept with dining room and family room. Enclosed Florida room with high impact windows is great extra living space marking this home just over 1700sf. Master bedroom is a good size with walk in closet. Secondary rooms are spacious and full 2nd bath. You have a wonderful front fenced courtyard and a nice sized fenced back yard. End unit and 2 assigned car parking spaces. Community features low HOA and community pool, gated back entrance for easy access to Semoran, tennis courts and club house. Zoned for great Seminole County schools and minutes to shopping/dining, Altamonte Springs Mall, Downtown Winter Park, Full Sail University and to UCF. This is a great one level townhome with very reasonable HOA.
Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)
Listing Agent: George Freelove (407-408-5167)
1250 FORMOSA AVE, WINTER PARK, FL 32789
$560,00021 Days on yellowkey MLS ID: O6412954
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 1937 Built: 2022Monthly Fee: $252 Tax: $8,328 (2025)Community: Urban Green 12Townhouse
Taxes:$8,328
Remarks: Modern living meets unbeatable location in this stunning 3 bedroom, 3.5 bathroom home nestled in the highly sought-after Urban Green Community. Built in 2022, this move-in ready residence showcases sleek, contemporary finishes throughout all three levels. Step up to a welcoming covered and pavered front porch, fenced-in front yard, and into a thoughtfully designed layout. The first floor offers a private bedroom with its own walk in closet and ensuite—perfect for guests or a home office. On the second floor, enjoy open-concept living with a bright and airy great room featuring high ceilings, recessed lighting, and seamless access to an oversized balcony through sliding glass doors. The modern kitchen is a showstopper, complete with quartz countertops, stainless steel appliances, a walk-in pantry, white shaker cabinets and a large center island with breakfast bar seating. Upstairs, you'll find two additional bedrooms, including the spacious primary suite with a walk-in closet, double vanity, glass-enclosed shower, and built-in shelving. The third bedroom also includes its own ensuite for added privacy and comfort. Additional highlights include an oversized rear-entry 2-car garage, laundry room, ample storage, and low-maintenance living. Enjoy unbeatable proximity to I-4, Downtown Orlando, Dubsdread Golf Course, Rollins College, Park Avenue, and Winter Park Village—offering endless dining, shopping, and entertainment options. This modern gem offers the best of both worlds: a turnkey home in a central, vibrant location. Don’t miss your chance to own in one of Orlando’s most desirable areas!
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Jeanine Louis, Llc (407-595-8634)
1768 MONDRIAN CIR, WINTER PARK, FL 32789
$1,099,000110 Days on yellowkey MLS ID: O6375723
0 Days Off yellowkey (back on 6/15/2026)
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2193 Built: 2023Monthly Fee: $395 Tax: $10,379 (2024)Community: Mondrian/Winder Park TwnhmsTownhouse
Taxes:$10,379
Remarks: Virtually Staged. Step into refined lakeside living at the exclusive Lake Killarney Townhomes, where contemporary elegance meets everyday convenience. This ultra-private corner unit boasts one of the community’s most desirable floor plans—perfectly positioned in a peaceful enclave just steps from the vibrant heart of Winter Park Village and mere minutes from I4, offering seamless access to downtown Orlando and beyond. Designed for the modern lifestyle, this stunning residence features an open-concept layout with soaring ceilings, oversized windows, and luxury finishes throughout. The sleek chef’s kitchen anchors the space, showcasing dramatic gray cabinetry, a bold black center island, and a high-end Samsung appliance package, complete with a natural gas cooktop and built-in wall oven. Quartz countertops and a full-height backsplash give a seamless, refined look, while a spacious walk-in pantry adds everyday convenience. Upstairs, three generously sized bedrooms each pair with a spa inspired bathroom deliver elevated comfort. Each bath is thoughtfully designed with floating vanities, designer porcelain tile, and custom closet systems—bringing a boutique hotel aesthetic to your personal retreat. Enjoy quiet mornings or golden-hour gatherings on the expansive private terrace, framed by glass railings and pre-plumbed for a future summer or cocktail kitchen—perfect for effortless indoor-outdoor entertaining. Residents enjoy exclusive access to lakefront pavilion, and an array of watersport amenities including kayak, paddleboard, and canoe storage. With everything Winter Park has to offer just moments away, this location offers the perfect blend of serenity and connectivity.
Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)
Listing Agent: Brandon Geers (941-928-5152)
1995 CANNY CV, WINTER PARK, FL 32792
$425,00038 Days on yellowkey MLS ID: G5112476
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1907 Built: 2023Monthly Fee: $375 Tax: $5,957 (2025)Community: Grayson SquareTownhouse
Taxes:$5,957
Remarks: Welcome to Grayson Square at Winter Park by Pulte Homes. This interior Springdale II two-story townhome has no direct rear neighbors, features 3 bedrooms, 2 full bathrooms, a powder room, single-car garage, a covered rear lanai, washer, dryer, refrigerator, and window blinds. The spacious first floor with over 9' ceilings is ideal for entertaining, featuring an open concept gathering room, cafe and kitchen equipped with a pantry, bright white cabinetry, white subway ceramic tile backsplash, Lyra quartz countertops, and durable ceramic tile flooring, and a powder room. After a long day, retreat upstairs to your private oasis. The Owner's Suite features a spacious walk-in closet and ensuite bathroom with double sink, quartz-topped vanity, linen closet, a private water closet and walk-in glass framed shower. Offering privacy and space for everyone, two additional bedrooms, the secondary bathroom and laundry are also on the second floor. Professionally curated design selections for this popular Springdale II townhome include designer cabinets with crown molding, quartz countertops, oversized ceramic tile flooring covering the first floor living areas and bathrooms, a washer, dryer, refrigerator, and blinds, soft, stain-resistant Shaw carpet in the bedrooms and second floor living areas and so much more! Grayson Square is an intimate gated luxury townhome community located minutes away from downtown Winter Park, right off of Howell Branch Road! Grayson Square is a low-maintenance neighborhood with gated access, a pond, no rear neighbors, a resort-style community pool with cabana,1GM high-speed fiber optic internet, along with 75 streaming cable and music channels, ground maintenance - all with no CDD. Boasting an unbeatable location in coveted Winter Park, just one mile from 436, 434, and less than 3 miles from 417, your like-new home at Grayson Square offers all of your daily conveniences, such as Starbucks and Publix, just minutes away! Plus, you'll have access to quality Seminole County schools. When it's time for a change of pace, you'll love your proximity to the famous shopping and dining of Park Avenue. Make Grayson Square at Winter Park your new address today!
Listing is courtesy of: KELLER WILLIAMS ELITE PARTNERS III REALTY (321-527-5111)
Listing Agent: Rosemary Siegler (845-248-8708)
649 N PARK AVE, WINTER PARK, FL 32789
$3,500,00022 Days on yellowkey MLS ID: O6411141
Bed: 3 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3180 Built: 2019Monthly Fee: $948 Tax: $22,599 (2025)Community: Park HillTownhouse
Taxes:$22,599
Remarks: Park Hill is one of Winter Park's most coveted addresses, a distinguished collection of luxury brownstones situated at the northern end of Park Avenue, moments from the city's finest boutiques, restaurants, cultural landmarks and the historic Winter Park Golf Course. Within this exclusive enclave, residence 649 occupies one of the community's most private settings. Beyond the stately brick courtyard and gas lantern-adorned entrance, this three-story home with a private elevator is thoughtfully scaled for refined living. Not oversized, but extraordinarily well-appointed. Ten-foot ceilings, intricate millwork and moldings and generous windows establish an ambiance of quiet elegance, while hardwood floors and designer fixtures carry that standard throughout. The open-concept main living area is built for effortless entertaining. The chef's kitchen features Wolf and Sub-Zero appliances, custom wood cabinetry, marble accents, a center island with bar seating and a wet bar with a beverage refrigerator and ice maker. The space opens directly to a private courtyard with a summer kitchen and dedicated alfresco dining area, creating a genuinely tranquil retreat that feels removed from the energy of the avenue. Upstairs, two guest suites each offer walk-in closets and en-suite baths. A dedicated laundry room and a covered terrace with a fireplace, wet bar and half bath complete the level. The third-floor primary suite provides a true sense of retreat, with two custom walk-in closets, a private balcony and a spa bath filled with natural light from windows and skylights. Dual vanities, a glass-enclosed steam shower and a soaking tub are finished throughout in premium materials. Constructed of Old Carolina brick with three-story block construction, precast exterior trim and a slate mansard roof, the residence features a two-car air-conditioned garage, ample storage and soundproof hollow core floors. With exterior maintenance managed by the association, the lifestyle here is genuinely lock-and-leave. This is a rare opportunity to own in one of Central Florida's most prestigious communities, in a location that simply cannot be replicated.
Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)
Listing Agent: Drew Henner (407-406-0662)
2808 BRIGHT BIRD LN, WINTER PARK, FL 32792
$399,00025 Days on yellowkey MLS ID: O6410294
0 Days Off yellowkey (back on 6/7/2026)
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1907 Built: 2024Monthly Fee: $375 Tax: $6,126 (2025)Community: Grayson SquareTownhouse
Taxes:$6,126
Remarks: Under contract-accepting backup offers. Impeccable 2-story townhome, newly built in 2024 and located in Grayson Square, a Gated Luxury Townhouse Community in enchanting Winter Park, with modern, sophisticated architecture and landscaping. The interior features the high-end Lux Fresh package, complemented by owner upgrades including light dimmers, ceiling fans, and a custom kitchen island. The chef’s kitchen is equipped with new stainless-steel appliances and expansive white stone countertops. Alabaster cabinetry with ceramic tile plus smooth stone counters adds a touch of elegance throughout. Shaw LVP floors on the main level and 2nd level bathrooms. Owner's suite with an oversized walk-in closet and a dual-sink ensuite. Spacious second and third bedrooms. 9' ceilings throughout. The first floor features a stunning open-concept living area with vinyl wood-plank flooring. Laundry closet on 2nd level. Kohler raised commodes on the 2nd level. Private patio area surrounded by lush greenery. Attached garage with 2 extra off-street parking spaces. The home includes a Ring doorbell and a rear security camera. Eeros internet modem and Extender for boosted device connectivity. includes a resort-style pool oasis with a cabana, with a view of the community lake. Competitive HOA fees cover roof replacement, Spectrum internet and TV, and general property upkeep. Situated in a manicured community with a sparkling pool, this home is close to fine dining, shopping, and entertainment, with easy access to downtown Orlando and local theme parks. It is highly rated for its proximity to quality Seminole County public schools and its convenience to daily necessities like Publix and Starbucks, as well as the shopping and dining of Park Avenue.
Listing Agent: Sean Flatley (609-208-8204)
7470 CANFORD CT #23, WINTER PARK, FL 32792
$245,900222 Days on yellowkey MLS ID: O6360198
REDUCED by $3,000 (1.2%) on 06/05/2026
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 1580 Built: 1974Monthly Fee: $575 Tax: $3,119 (2024)Community: Whisperwood CondoTownhouse
Taxes:$3,119
Remarks: New updates, a new fence, and extra outdoor space on a desirable corner lot. Beautifully updated 3 bedroom, 2.5 bath corner unit townhome located in the heart of Winter Park, offering 1,580 square feet of bright and open living space. This home features a deluxe vinyl-fenced backyard with plenty of privacy and no rear neighbors. The property is currently tenant occupied,making it a great investment opportunity and the tenants are ready to move out after the sale. The spacious living area features sliding doors that open to the private fenced courtyard, perfect for relaxing or entertaining. The kitchen includes modern appliances and plenty of cabinet space and overlooks the dining and living rooms, creating an easy and open flow. The AC system was replaced in 2022, and the new roof was recently replaced by the HOA in 2024 Upstairs, you will find generously sized bedrooms with great natural light, updated bathrooms, and excellent storage space. The home also offers an assigned covered parking space, inside laundry hookups, and a low-maintenance lifestyle. The HOA includes water, sewer, trash, exterior maintenance, and access to the community pool. Conveniently located just minutes from Full Sail, UCF, Sam’s Club, Costco, Winter Park shopping and dining, and major highways including the 417 and 408. Public transportation is also available right in front of the community, making it easy to travel throughout the area.
Listing Agent: Sam Nguyen (321-301-9709)
7522 ALOMA PINES CT, WINTER PARK, FL 32792
$375,00030 Days on yellowkey MLS ID: S5150544
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1872 Built: 2017Monthly Fee: $407 Tax: $4,304 (2025)Community: Aloma TrailsTownhouse
Taxes:$4,304
Remarks: Beautifully maintained 3-bedroom, 2.5-bath two-story townhome featuring a bright and functional open-concept floor plan. The first floor offers tile flooring throughout the spacious living and dining areas, kitchen, and half bath. The modern kitchen is designed for both style and convenience, featuring granite countertops, abundant cabinetry, a large center island, and a walk-in pantry, along with a full appliance package. Sliding glass doors provide abundant natural light and a peaceful backyard view. Upstairs, you’ll find all bedrooms, including a spacious primary suite with plush carpeting, a large walk-in closet, and an en-suite bathroom featuring dual vanities and a glass-enclosed shower. The second floor also includes a full guest bathroom, a convenient laundry closet with washer and dryer, multiple linen closets. Additional highlights include a one-car garage, extended driveway parking, and access to community amenities. Conveniently located near Park Avenue, University of Central Florida, Full Sail University, and Rollins College, with easy access to shopping, dining, and entertainment.
Listing is courtesy of: RIVA REALTY GROUP LLC (407-845-1003)
Listing Agent: Vildan Nigro (352-988-3824)
1540 FLORENTINO LN, WINTER PARK, FL 32792
$335,00032 Days on yellowkey MLS ID: O6408841
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1682 Built: 2004Monthly Fee: $175 Tax: $5,340 (2025)Community: Vistas At Lake HowellTownhouse
Taxes:$5,340
Remarks: Come and see your new home in the sought after Vistas at Howell Branch community. This two story townhouse has 3 bedrooms, 2.5 baths, and open first floor, floor plan. Relax in the evening on your screened in porch. The master bedroom has a walk in closet and large master bath. Your washer and dryer are on the second floor centrally located to all the bedrooms. You will find yourself within walking distance of restaurants, grocery stores, and other retail outlets. It's central location puts within minutes of 436 and 417. Schedule your showing today!
Listing Agent: Ashley Fisak (407-848-7975)
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