Location: Winter Park
Do Not Show Listings
1138 S PENNSYLVANIA AVE, WINTER PARK, FL 32789
$1,025,00033 Days on yellowkey MLS ID: O6420090
REDUCED by $25,000 (2.4%) on 07/22/2026
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2434 Built: 2005Monthly Fee: $500 Tax: $10,213 (2025)Community: Virginia Heights RepTownhouse
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$10,213
Elementary School: Audubon Park K8
High School: Winter Park High
Tax Year: 2025
Middle School: Audubon Park K-8
Remarks: Georgetown-style 'Brownstown' in the Heart of Winter Park, walking distance to Downtown, PLUS deeded Lake Access to Lake Virginia! This spacious property has 3 bedrooms, 3 full baths, 2434 sq ft, 10' ceilings custom details throughout and natural lighting. Foyer with slate flooring, enjoy the double-sided gas fireplace in the Living & Dining areas, beautiful wood floors, crown molding, plantation shutters, a butler bar with custom cabinetry & wine refrigerator. Cooking inspired Kitchen with a lengthy granite island and sitting bar overlooks the Family room. Upgraded stainless appliances, including gas cooktop with griddle, microwave/convection oven, hanging pot rack with lighting, and soft close cabinets with pullouts. French doors to the covered 'English Garden' courtyard with pavers & stainless grill for entertaining. Guest suite or home office with a custom closet and full bath overlooks brick street, Pennsylvania Ave. Large laundry room near the garage with granite countertops, cabinets & utility sink, plus washer & dryer. Upstairs is a spacious Primary bedroom with French doors to a private covered balcony; also, 2 large walk-in closets with closet systems, Jacuzzi tub, huge walk-in shower, dual vanities with granite countertops & more. An additional ensuite bedroom, more wood floors, plus a built-in dehumidifier. Attached 2-car, rear alley access garage, plus an additional side parking pad. Walk to Park Ave. for dining, shopping, WP Tennis Center, outdoor park & Rollins College. Neighborhood Lake Virginia access for paddleboard & kayak launching to the Winter Park Chain of Lakes. Top schools, Audubon K-8 seconds away, and WPHS. NEW TPO membrane roof w/ metal coping March 2026. HOA maintains: landscaping, irrigation, building maintenance & outdoor lighting. Won't last!
Listing is courtesy of: COLDWELL BANKER REALTY (407-647-1211)
Listing Agent: George Stringer (407-222-7047)
1250 FORMOSA AVE, WINTER PARK, FL 32789
$560,00056 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
Elementary School: None
High School: None
Middle School: None
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)
2676 BARBADOS DR, WINTER PARK, FL 32792
$340,00061 Days on yellowkey MLS ID: O6411958
2 Days Off yellowkey (back on 6/26/2026)
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
Elementary School: Eastbrook Elementary
High School: Lake Howell High
Middle School: Tuskawilla Middle
Remarks: Under contract-accepting backup offers. 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 is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)
Listing Agent: Joseph Sipp (407-820-7016)
786 MCINTYRE AVE, WINTER PARK, FL 32789
$625,00017 Days on yellowkey MLS ID: O6424399
0 Days Off yellowkey (back on 7/27/2026)
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1934 Built: 1988 Tax: $4,061 (2025)Community: Trotters RepTownhouse
Taxes:$4,061
Remarks: Under contract-accepting backup offers. Virtually Staged. Welcome to 786 McIntyre Avenue, Winter Park, FL 32789—a serene retreat perched on a picturesque tree-lined brick street in one of Winter Park's most desirable neighborhoods. Just a short stroll from Rollins College and the renowned shops, restaurants, and charm of Park Avenue, this exceptional single-family townhome offers the perfect blend of comfort, style, and location—SINGLE FAMILY TOWNHOME with NO HOA! A charming driveway leads to the attached two-car garage and private front entrance. Inside, you'll be welcomed by a bright, airy interior featuring soaring ceilings, dramatic high windows, abundant natural light, and a cozy wood-burning fireplace. The spacious living room is surrounded by two private patios, creating a seamless connection between indoor and outdoor living. The updated kitchen boasts modern cabinetry, an open breakfast bar, and a cheerful eat-in dining area with direct access to one of the patios. The formal dining room, currently used as a home office, opens to the second patio, making it the perfect setting for al fresco dining or entertaining. Upstairs, the impressive 23' x 12' primary suite offers a peaceful retreat, complete with a spacious 20' x 8' ensuite bathroom. Two additional guest bedrooms share a convenient Jack-and-Jill bathroom, providing comfort and privacy for family or visitors. Meticulously maintained, this home features numerous recent updates, including a new HVAC system (2025) and beautiful wood shutters throughout. Located in the highly sought-after Audubon K-8 and Winter Park High School districts, this exceptional home combines timeless character, modern updates, and an unbeatable location. WELCOME HOME!
Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)
Listing Agent: Catherine D'Amico (407-252-3210)
2487 HARBOUR WAY, WINTER PARK, FL 32792
$290,00014 Days on yellowkey MLS ID: O6422155
REDUCED by $10,000 (3.3%) on 07/27/2026
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 1803 Built: 1978Monthly Fee: $95 Tax: $5,059 (2025)Community: Windward Square Sec 1Townhouse
Taxes:$5,059
High School: Hagerty High
Middle School: Chiles Middle
Remarks: Welcome to 2487 Harbour Way, a spacious single-story townhome offering 3 bedrooms, 3 full bathrooms, and 1,803 square feet of comfortable living space. The practical layout features inviting living and dining areas, a well-equipped kitchen, central air, and a walk-in closet. Outside, garden space, lighting, and sidewalks add to the home's appeal. Enjoy a low-maintenance lifestyle in Windward Square, where residents have access to a community pool and playground, with the pool included in the low monthly HOA fee. Conveniently located near schools, parks, shopping, dining, and everyday essentials, this Winter Park property offers space, convenience, and community amenities in one appealing package. Schedule your private showing today!
Listing is courtesy of: LOKATION (954-545-5583)
Listing Agent: Joel Garay (203-522-2231)
1540 FLORENTINO LN, WINTER PARK, FL 32792
$315,00067 Days on yellowkey MLS ID: O6408841
REDUCED by $20,000 (6.0%) on 07/12/2026
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
Elementary School: Sterling Park Elementary
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)
1995 CANNY CV, WINTER PARK, FL 32792
$425,00073 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)
2339 INAGUA WAY, WINTER PARK, FL 32792
$299,99939 Days on yellowkey MLS ID: O6415345
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1324 Built: 1979Monthly Fee: $98 Tax: $2,187 (2025)Community: Windward Square Sec 3Spa: NoTownhouse
Taxes:$2,187
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)
2521 GALLIANO CIR, WINTER PARK, FL 32792
$350,00035 Days on yellowkey MLS ID: O6419329
REDUCED by $10,000 (2.8%) on 07/22/2026
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1682 Built: 2003Monthly Fee: $175 Tax: $4,532 (2025)Community: Vistas At Lake HowellTownhouse
Taxes:$4,532
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)
2033 CANNY CV, WINTER PARK, FL 32792
$399,0008 Days on yellowkey MLS ID: O6426457
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1907 Built: 2023Monthly Fee: $375 Tax: $6,887 (2025)Community: Grayson SquareTownhouse
Taxes:$6,887
Remarks: Step into this beautifully designed townhome featuring an open-concept kitchen, dining, and living area—perfect for everyday living and entertaining. The modern kitchen boasts stainless steel appliances, gray cabinetry, and quartz countertops. Upstairs, the spacious primary suite offers a walk-in closet and a private in-suite bath with dual quartz vanities, while two additional bedrooms, a full bath, and a convenient laundry closet complete the second floor. Relax on the covered lanai and enjoy the privacy of this home's cul-de-sac location. The HOA includes landscaping, exterior maintenance and repairs, high-speed internet, and access to the gated community, providing low-maintenance living. With no CDD, this home is an excellent option for both homeowners and investors. Ideally located in highly desirable Winter Park, Grayson Square is just minutes from SR-436, SR-434, and SR-417, with Publix, Starbucks, shopping, dining, and top-rated Seminole County schools nearby. Park Avenue is only a short drive away, making this home the perfect combination of convenience, comfort, and value.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Monica Puche (407-545-0692)
1778 MONDRIAN CIR, WINTER PARK, FL 32789
$1,339,00016 Days on yellowkey MLS ID: O6422941
3 Days Off yellowkey (back on 7/20/2026)
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2377 Built: 2023Monthly Fee: $395 Tax: $12,451 (2025)Community: Mondrian/Winter Park TwnhmsSpa: NoTownhouse
Taxes:$12,451
Elementary School: Killarney Elem
High School: Edgewater High
Middle School: College Park Middle
Remarks: Under contract-accepting backup offers. Luxury waterfront living in Winter Park. Perfectly positioned on a premium corner homesite overlooking beautiful Lake Killarney, this exceptional contemporary townhome offers 3 bedrooms, 3.5 bathrooms, and nearly 2,400 square feet of thoughtfully designed living space with spectacular water views, abundant natural light, and the low-maintenance lifestyle today’s buyers desire.A dramatic 17-foot foyer welcomes you into an expansive open-concept living area where soaring 11-foot ceilings and walls of floor-to-ceiling glass showcase breathtaking lake vistas and create an effortless connection between the indoor and outdoor living spaces. The spacious great room flows seamlessly into the dining area and kitchen, creating an ideal setting for both everyday living and entertaining. The chef’s kitchen is beautifully appointed with premium Wolf and Sub-Zero appliances, double-stacked soft-close cabinetry, stone countertops, a large center island with seating, a generous walk-in pantry, new designer RH lighting throughout, and motorized window shades. Just beyond, the covered rear lanai provides the perfect place to enjoy morning coffee, evening cocktails, or simply relax while overlooking the peaceful shoreline. Upstairs, the luxurious primary suite serves as a private retreat featuring expansive waterfront windows, dual walk-in closets, and a spa-inspired bath with an oversized frameless glass shower, a long single vanity with dual sinks, ample storage, and a private water closet. A spacious loft provides the perfect flex space for a home office, media room, or reading lounge. Step outside to the second-floor balcony complete with an outdoor kitchen, where elevated views of Lake Killarney create an unforgettable backdrop for entertaining. Two additional bedrooms, including one with an en-suite bath, provide comfort and privacy for family and guests, while the upstairs laundry room is thoughtfully positioned between the primary and secondary bedrooms. Additional features include engineered hardwood flooring, porcelain tile, high-end contemporary finishes throughout, abundant storage, a two-car attached garage with an epoxy floor, EV charging station, garage door opener, and a tankless gas water heater. Residents of Mondrian at Winter Park enjoy beautifully maintained grounds, private roads, reclaimed irrigation, a community dock, and lake access to one of Central Florida’s most desirable ski lakes. The HOA also includes cable television, high-speed internet, exterior grounds maintenance, and pest control, making for truly effortless ownership. Combining exceptional waterfront views, sophisticated contemporary design, premium finishes, an ideal floor plan, and one of Winter Park’s most convenient locations, this is a rare opportunity to own one of the community’s most desirable lakefront residences. Just minutes from Park Avenue, Winter Park Village, AdventHealth, Rollins College, Interstate 4, and Downtown Orlando, this home offers the perfect balance of luxury, convenience, and low-maintenance living. Schedule your private showing today and discover everything this exceptional Lake Killarney residence has to offer.
Listing is courtesy of: KELLY PRICE & COMPANY LLC (407-645-4321)
Listing Agent: Padgett Mccormick (407-645-4321)
2651 CAYMAN WAY, WINTER PARK, FL 32792
$255,000190 Days on yellowkey MLS ID: O6375086
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1020 Built: 1978Monthly Fee: $99 Tax: $3,553 (2024)Community: Windward Square Sec 2Townhouse
Taxes:$3,553
Tax Year: 2024
Remarks: Virtually Staged. ALL PLAY and NO WORK! Imagine coming home to a space where weekends are made for relaxing, entertaining, and enjoying the best of Florida living. This single-story, two-bedroom, two-bath townhome offers an effortless lifestyle in a location that puts everything within reach. Vaulted ceilings create an open, airy feel in the spacious living and dining area, while sliding glass doors lead to a private, fenced backyard with a large concrete patio?perfect for morning coffee, weekend barbecues, or unwinding after a long day. With no rear neighbors and views of the community green space, you?ll enjoy added privacy and tranquility. The kitchen is designed for everyday ease, featuring ample cabinetry, a breakfast bar, and all appliances included, making move-in simple. Retreat to the oversized primary suite with a walk-in closet and direct patio access, creating a true indoor-outdoor flow. The second bedroom offers flexibility for guests, a home office, or creative space. Step outside your front door and enjoy resort-style amenities, including three swimming pools, tennis courts, a clubhouse, and a playground—all with low HOA fees. With parking for three vehicles, convenience is built right in. Located close to shopping, dining, major roadways, and just minutes from Winter Park’s Park Avenue, this home delivers both comfort and connection. Owner-occupant only community—ideal for those looking to put down roots and enjoy a true neighborhood feel. Live more. Maintain less. Welcome home.
Listing is courtesy of: RE/MAX TOWN & COUNTRY REALTY (407-695-2066)
Listing Agent: Kyle Clark (407-921-3287)
1411 MILLER AVE, WINTER PARK, FL 32789
$899,00043 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
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 Agent: Sue Gilman (407-405-0108)
436 W SWOOPE AVE, WINTER PARK, FL 32789
$719,90017 Days on yellowkey MLS ID: O6423105
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2602 Built: 2014Monthly Fee: $463 Tax: $9,640 (2025)Community: Swoope ParkTownhouse
Taxes:$9,640
Elementary School: Lakemont Elem
Middle School: Maitland Middle
Remarks: Virtually Staged. Welcome to this virtually staged contemporary townhome in the desirable 400 West community, home to just nine residences and steps away from lively Park Avenue. Enter through the private garage or the charming front path, and you'll find a bright and open main floor that perfectly balances comfort and modern style. The main floor features a stylish mix of finishes, including large-format porcelain tiles, level 4 drywall, tall baseboards, and designer lighting. The centerpiece is a sleek kitchen equipped with glossy white cabinetry, chic chrome pulls, quartz countertops, and top-quality stainless-steel appliances. The garage, with alley access, includes a storage closet and built-in shelving for added convenience. On the second level, discover two spacious primary suites with modern LVP flooring and large windows that let in plenty of natural light. The en-suite bathrooms are designed with porcelain tiles, frameless glass showers, wall-to-wall mirrors, and matte white vanities. The primary bath offers a double-sink vanity, a private water closet, and a spacious walk-in closet. A conveniently situated laundry room features a Samsung washer and dryer with overhead storage. The third level has two more bedrooms, each with walk-in closets, connected by a shared Jack-and-Jill bath, making it ideal for guests, a home office, or a workout space. Don’t miss the chance to check out this fantastic home in a prime location where luxury meets practicality!
Listing is courtesy of: RE/MAX EXCLUSIVE COLLECTION (407-447-2829)
Listing Agent: Kim Griffin (407-314-5033)
1122 WASHINGTON AVE #7B, WINTER PARK, FL 32789
$575,00028 Days on yellowkey MLS ID: O6421299
2 Days Off yellowkey (back on 7/16/2026)
Bed: 2 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1556 Built: 1978Monthly Fee: $504 Tax: $5,786 (2025)Community: Quarters At Winter Park CondoTownhouse
Taxes:$5,786
Remarks: Under contract-accepting backup offers. Completely reimagined in 2025, this stunning 2-bedroom, 2.5-bath townhome offers the perfect blend of modern luxury and an unbeatable Winter Park location. Just minutes from Rollins College, Park Avenue, boutique shopping, award-winning dining, and everything that makes Winter Park so desirable, this move-in-ready home has been thoughtfully renovated from top to bottom with timeless, designer-selected finishes. The heart of the home is the beautifully redesigned kitchen featuring Sarah Sherman Samuel cabinetry and hardware, gorgeous marble countertops, a custom marble ledge, and all-new appliances. Throughout the home, you'll find new flooring, smooth-finished walls, fresh interior paint, recessed lighting with dimmers, updated electrical, new interior doors and hardware, and new baseboards, creating a clean, sophisticated aesthetic. Upstairs, both spacious bedrooms feature beautifully updated en-suite bathrooms, while the primary suite includes a custom marble-top vanity and a thoughtfully designed built-in closet system. Every bathroom has been fully renovated with high-end finishes that elevate the home's overall design. Step outside to your own private outdoor retreat featuring a large covered patio with low-maintenance turf—perfect for entertaining, relaxing, or enjoying your morning coffee year-round. Major mechanical updates provide added peace of mind, including a 2023 air handler, 2024 water heater, all-new A/C ductwork, and added attic insulation for improved energy efficiency. With nearly every surface and major system thoughtfully updated, this exceptional Winter Park townhome offers luxurious, turnkey living in one of Central Florida's most sought-after neighborhoods.
Listing is courtesy of: ALL REAL ESTATE & INVESTMENTS (407-917-8206)
Listing Agent: Cara Edwards (407-616-3204)
1265 ARLINGTON PL, WINTER PARK, FL 32789
$849,90048 Days on yellowkey MLS ID: O6415981
REDUCED by $29,100 (3.3%) on 07/11/2026
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
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 Agent: Erika Beerbower (407-758-2727)
512 W SWOOPE AVE, WINTER PARK, FL 32789
$1,399,00041 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
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)
901 ENCLAVE PL, WINTER PARK, FL 32792
$1,495,000131 Days on yellowkey MLS ID: O6383602
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2738 Built: 2026Monthly Fee: $247 Tax: $9,900 (2026)Community: The Enclave Winter ParkTownhouse
Taxes:$9,900
Tax Year: 2026
Remarks: Pre-Construction. To be built. Welcome to The Enclave at Winter Park—an exclusive collection of architecturally distinctive residences crafted by FG Schaub Custom Homes, blending timeless character with modern luxury. 901 Enclave Place (Lot1) is a thoughtfully designed courtyard home offering an elegant yet functional layout centered around private outdoor living. A charming covered front porch and welcoming foyer lead into an expansive open-concept gathering and dining space, seamlessly connected to a designer kitchen featuring a large center island, walk-in pantry, and effortless flow for entertaining. At the heart of the home, a covered lanai and courtyard create a true indoor-outdoor lifestyle—perfect for year-round enjoyment and intimate gatherings. The first-floor primary suite is a private retreat with a spacious walk-in closet and spa-inspired bath, complemented by a convenient powder bath and laundry/pantry area. Upstairs, you’ll find a well-appointed layout including an second primary suite with a luxurious bath and oversized closet, a additional bedroom, full bath, and a versatile gathering loft—ideal as a media room, office, or flex space. Designed with both comfort and sophistication in mind, this residence showcases clean architectural lines, abundant natural light, and carefully curated indoor and outdoor living spaces. Located within a boutique enclave of just a limited number of homes, residents will enjoy a serene setting surrounded by mature trees and thoughtfully designed community green space. Experience the best of Winter Park living with close proximity to renowned dining, shopping, and top-rated schools—all within one of the area’s most sought-after new communities. 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: Laura Earl (443-994-9441)
905 ENCLAVE PL, WINTER PARK, FL 32792
$1,495,000131 Days on yellowkey MLS ID: O6383679
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2756 Built: 2026Monthly Fee: $247 Tax: $9,900 (2026)Community: The Enclave Winter ParkTownhouse
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 Agent: Matthew Burks (407-257-5347)
660 W MORSE BLVD, WINTER PARK, FL 32789
$2,800,00034 Days on yellowkey MLS ID: O6419377
Bed: 3 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3286 Built: 2021Monthly Fee: $625 Tax: $24,472 (2025)Community: Morse & Pennsylvania TwnhmsTownhouse
Taxes:$24,472
Remarks: Hidden Gem! Designed and built by the acclaimed Phil Kean Design Group, this exceptional luxury townhome offers modern living in one of Downtown Winter Park’s most desirable locations. Situated in the heart of Hannibal Square and just three blocks from Park Avenue, this residence places premier dining, shopping, galleries, museums, Central Park and year-round community events within easy walking distance. Thoughtfully designed with both style and functionality in mind, the home showcases high-end finishes throughout including rich Brazilian walnut flooring, oversized 24 x 48 ceramic tile, coffered ceilings, quartz countertops, custom cabinetry and premium stainless-steel appliances. The chef’s kitchen is anchored by an eight-burner Wolf gas range and a Sub-Zero refrigerator, paired with a hidden pantry discreetly concealed behind custom cabinetry. A striking metal staircase serves as a central architectural feature, adding a contemporary design element that complements the home’s clean lines and sophisticated aesthetic. The open-concept floor plan is filled with natural light, enhanced by expansive windows throughout that frame peaceful green views and mature tree-lined surroundings. The main living areas extend seamlessly to the outdoors, where a first-floor entertaining wet bar with a wine refrigerator opens directly to the private courtyard, creating an effortless indoor-outdoor flow ideal for hosting. The courtyard features a fire pit surrounded by greenery, while the balcony off the main living area includes a summer kitchen. A fenced yard offers privacy and space for pets to enjoy. Designed for today’s lifestyle, the home includes a PRIVATE ELEVATOR servicing all three floors, dual HVAC systems, two tankless water heaters hardwired security cameras and a spacious three-car garage with an electric vehicle charging station and generous storage space. RARELY AVAILABLE in Downtown Winter Park, the oversized THREE CAR GARAGE offers exceptional functionality and flexibility. The private driveway provides additional parking while abundant guest parking nearby makes entertaining easy, an uncommon convenience in a downtown setting. The primary suite occupies the third floor, offering a private retreat with separation from the main living areas. It features a very large owner’s closet filled with natural light and a dedicated vanity area, creating a functional yet refined dressing space. Two additional bedrooms and a dedicated office or den provide flexibility for working from home, accommodating guests or creating additional living space. Each bathroom has been thoughtfully appointed with quality finishes and timeless design. Tucked within a quiet enclave , this residence offers a unique balance of privacy and walkability. The property is adjacent to the recently completed $6.1 million residence of internationally respected architect Kamal Rizk further underscoring the caliber of the surrounding neighborhood. Homes of this quality and location rarely come to market, presenting a truly limited opportunity to own in one of Winter Park’s most sought-after addresses. Combining the architectural vision and craftsmanship of Phil Kean Design Group with luxury finishes, modern conveniences and an exceptional location, this residence offers sophisticated low-maintenance living in the heart of Winter Park’s most vibrant neighborhood. Furniture may convey and pricing upon request. New 10 yr. termite bond will convey with the sale.
Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)
Listing Agent: Jennifer Sloan (407-810-8333)
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