Displaying: For Sale
Location: Winter Park
Property Type(s): Townhomes
Living Area Square Feet: 1500 to 1999
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Winter Park - 11 properties found
1871 CASSELWOOD ST, WINTER PARK, FL 32792
$424,9001 Day on yellowkey MLS ID: O6404306
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1616 Built: 1988Monthly Fee: $39 Tax: $1,223 (2024)Community: Villas Of Casselberry Ph 2Townhouse
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$1,223
Elementary School: Eastbrook Elementary
High School: Lake Howell High
Tax Year: 2024
Middle School: Tuskawilla Middle
Remarks: Beautifully updated, move-in ready home in Winter Park with space, comfort, and a clean, modern feel throughout. This 4-bedroom, 2.5-bath home with a 2-car garage features waterproof luxury vinyl flooring, fresh interior finishes, new recessed lighting, and updated ceiling fans, all combined with a bright and functional layout. As you enter, you are welcomed by a custom wood decorative accent wall that adds warmth and character. Just behind the wall, a renovated half bathroom is conveniently located on the first floor. The kitchen is one of the main features of the home, fully renovated with custom green cabinetry, quartz countertops, a farmhouse sink with a modern faucet, gold hardware, and a clean contemporary backsplash. The space includes abundant cabinetry plus a pantry for additional storage and comes equipped with new stainless steel appliances including refrigerator, range, and range hood. Pendant lighting and chandelier details add a designer touch. The living area includes a modern electric fireplace and sliding doors that open to a screened patio, creating a comfortable indoor-outdoor flow. The outdoor space provides a private setting with a low-maintenance yard and room to relax or personalize. Upstairs, you will find all bedrooms along with a conveniently located laundry area. The primary suite is oversized and designed as a true retreat, featuring dual pendant lighting and great natural light. The primary bathroom is fully renovated with a freestanding soaking tub, double vanity, glass-enclosed walk-in shower with rainfall shower head, and modern finishes. The suite also includes dual closets for added functionality. Secondary bedrooms are well-sized and provide flexibility for family, guests, office, or additional living space. Additional improvements include a new front door, updated lighting throughout, and thoughtful design details that make this home feel clean, cohesive, and move-in ready. Located in the Villas of Casselberry community, this property has a low HOA (buyer to verify) with access to a community pool and sidewalks. Conveniently situated near major roads, shopping, dining, Full Sail University, Rollins College, UCF, and just minutes from Downtown Orlando. Move-in ready with extensive updates and a functional layout, this is a strong opportunity in the Winter Park market.
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE 2 REALTY (407-393-5901)
Listing Agent: Alexa Monasterio Flores (786-915-9294)
1781 INDIANA AVE #A, WINTER PARK, FL 32789
$545,00082 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
Elementary School: Killarney Elem
High School: Edgewater High
Middle School: College Park Middle
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)
7474 ALOMA PINES CT, WINTER PARK, FL 32792
$359,500102 Days on yellowkey MLS ID: O6376008
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1872 Built: 2017Monthly Fee: $396 Tax: $4,477 (2024)Community: Aloma TrailsTownhouse
Taxes:$4,477
Elementary School: None
High School: None
Middle School: None
Remarks: ***PRICE REDUCTION*** **Seller offering closing credit** Nestled on a quiet cul-de-sac in desirable Winter Park, this well-maintained home offers a thoughtful layout with bright, open living spaces designed for both comfort and everyday living. The kitchen flows seamlessly into the main living and dining areas, making it ideal for gathering and entertaining. Generously sized bedrooms provide flexibility for guests, a home office, or a growing household. Enjoy a private backyard perfect for relaxing or hosting, all while being conveniently located near shopping, dining, parks, and major roadways. A wonderful opportunity to enjoy the lifestyle Winter Park is known for.
Listing is courtesy of: OAK HOLLOW PROPERTIES (407-949-8809)
Listing Agent: Jakki Kim (407-949-8809)
1261 INDIANA AVE, WINTER PARK, FL 32789
$539,00014 Days on yellowkey MLS ID: O6400698
0 Days Off yellowkey (back on 4/29/2026)
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
Tax Year: 2025
Remarks: Under contract-accepting backup offers. 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 gas cooktop and range, granite counters, island, breakfast nook, and built-in cabinetry and desk. French doors open to a private side patio ideal for relaxing, pot gardening or grilling. The interior laundry off the kitchen leads out to the functional 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 in 2024. Community improvements continue with road resealing 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.
Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)
Listing Agent: Megan Cross (407-353-9997)
2834 BRIGHT BIRD LN, WINTER PARK, FL 32792
$399,000115 Days on yellowkey MLS ID: O6372452
2 Days Off yellowkey (back on 4/29/2026)
REDUCED by $25,000 (5.9%) on 04/18/2026
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1907 Built: 2024Monthly Fee: $375 Tax: $1,200 (2024)Community: Grayson SquareTownhouse
Taxes:$1,200
Remarks: Under contract-accepting backup offers. Priced BELOW appraised value for a quick sale! Welcome to this stunning newer-construction townhome offering modern design, spacious living, and unbeatable value in one of Orlando’s most convenient locations. Featuring 3 bedrooms, 3 bathrooms, and nearly 2,000 sq ft of living space, this home boasts an open-concept layout, contemporary finishes, and abundant natural light throughout. The kitchen flows seamlessly into the main living area—perfect for entertaining—while the generously sized bedrooms provide comfort and flexibility for any lifestyle. Built in 2024, this home offers the peace of mind of newer construction with stylish, move-in-ready appeal.
Listing is courtesy of: LIFESTYLE INTERNATIONAL REALTY (305-809-8085)
Listing Agent: Irene Navarro (786-224-8499)
1515 WINTER GREEN BLVD, WINTER PARK, FL 32792
$300,00060 Days on yellowkey MLS ID: O6384755
REDUCED by $15,000 (4.8%) on 04/28/2026
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 1652 Built: 1984Monthly Fee: $188 Tax: $3,993 (2024)Community: Winter GreenTownhouse
Taxes:$3,993
Elementary School: English Estates Elementary
Remarks: Offering the comfort and feel of a single-family home with the convenience of townhome living, this beautifully maintained two-story residence features 3 bedrooms, 2.5 baths, and a private courtyard conveniently located in Winter Park. Sliding glass doors throughout the home fill the interior with natural light and create a seamless connection to your private outdoor courtyard. Inside, the spacious layout is complemented by low-maintenance tile flooring throughout and a cozy wood-burning fireplace, adding warmth and character to the main living area. The kitchen is well-appointed with granite countertops, stainless steel appliances, and a newer refrigerator, while the generously sized bedrooms provide comfortable retreats. The primary suite features two closets and an ensuite bath with dual sinks. Major system updates provide exceptional peace of mind, including a brand-new roof and HVAC system installed in January 2026, along with fresh exterior paint, newer gutters (approximately three years old), and a newer fence. The washer and dryer convey, making this home truly move-in ready. The community offers an exceptionally low HOA fee of under $200 per month, adding to the home’s overall value. Ideally located with easy access to Winter Park, Maitland, Full Sail University, UCF, Rollins College, and Valencia College, as well as nearby shopping, dining, and major roadways. With its spacious design, private outdoor space, and proven rental history, this property presents an outstanding opportunity as either a primary residence or investment. Reach out to schedule your private showing now!
Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)
Listing Agent: Jill Healey (407-797-1420)
2401 ANTILLES DR, WINTER PARK, FL 32792
$320,000180 Days on yellowkey MLS ID: O6357934
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1719 Built: 1977Monthly Fee: $95Community: Windward Square Sec 1Townhouse
Taxes:$0
Remarks: 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)
7485 ALOMA PINES CT, WINTER PARK, FL 32792
$390,00024 Days on yellowkey MLS ID: O6398259
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1787 Built: 2017Monthly Fee: $407 Tax: $4,585 (2025)Community: Aloma TrailsSpa: NoTownhouse
Taxes:$4,585
Remarks: Experience the perfect blend of luxury and convenience in the highly sought-after GATED community of Aloma Trails. This meticulously maintained 3-bedroom, 2.5-bathroom townhome, built in 2017, offers 1,787 sq. ft. of living space designed for comfort and modern style. Step inside to find an inviting open-concept first floor featuring beautiful ceramic tile flooring and high ceilings. The gourmet chef’s kitchen is a true standout, boasting upgraded granite countertops, a stylish tiled backsplash, 42” solid wood cabinetry, and a large island with plenty of breakfast bar seating. The full suite of stainless steel appliances makes this kitchen as functional as it is beautiful. The second level features plush carpeting throughout the bedrooms for ultimate comfort. The oversized Master Suite is a private sanctuary, complete with a massive walk-in closet and a spa-like en suite bathroom featuring a glass-enclosed shower, dual-sink vanity, and expansive cabinetry. Two additional well-appointed bedrooms share a second full bath, while the dedicated interior laundry closet adds a layer of daily convenience. (One or more photos have been virtually staged to show the potential of the space) Uniquely positioned with a spacious 2-car garage and a private paved driveway, this home easily accommodates multiple vehicles. The community of Aloma Trails provides a true "lock-and-leave" lifestyle with hassle-free lawn care and pristine common areas included in the HOA. Active lifestyles will thrive with the Cady Way Trail and Cross Seminole Trail just steps from your front door. For fitness buffs, Crunch Fitness is located directly across from the community entrance. Retail: 3 minutes to Walmart, Costco, and Publix. Education: Zoned for top-rated Seminole County Schools and minutes from UCF and Full Sail University. Entertainment: Short drive to the world-class dining and shopping of Park Avenue in Winter Park. Commute: Easy access to SR 417 puts you at the airport in 20 minutes or the beach in just 40! Don't miss your chance to own a piece of Winter Park luxury in a premier gated enclave.
Listing is courtesy of: OLYMPUS EXECUTIVE REALTY INC (407-469-0090)
Listing Agent: Gunel Aydamirli (407-907-7704)
1951 CANNY CV, WINTER PARK, FL 32792
$444,900142 Days on yellowkey MLS ID: O6367023
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1782 Built: 2023Monthly Fee: $375 Tax: $6,889 (2025)Community: Grayson SquareTownhouse
Taxes:$6,889
Remarks: Welcome to easy, light-filled living in this beautifully maintained 3-bedroom, 2.5-bath corner townhome in the gated Grayson Square community. Freshly painted and designed for comfort, the open living and dining spaces feel bright and inviting, flowing effortlessly to a covered lanai—perfect for relaxing evenings or casual gatherings. The kitchen offers a clean, modern look with stainless steel appliances, quartz countertops, and plenty of cabinet space for storage and organization. Upstairs, the owner’s suite provides a private retreat with a walk-in closet and a spacious ensuite bath featuring dual vanities and a glass-enclosed shower. A two-car garage with epoxy flooring and an in-unit washer and dryer add everyday convenience. Residents also enjoy access to a resort-style pool with cabana, along with high-speed fiber-optic internet and streaming services included. Located just minutes from downtown Winter Park, with easy access to major roadways, shopping, dining, and everyday essentials, this home offers a great balance of comfort, convenience, and low-maintenance living.HABLO ESPANOL
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Denise Del Castillo (321-960-3110)
1405 MILLER AVE, WINTER PARK, FL 32789
$899,00063 Days on yellowkey MLS ID: O6386405
0 Days Off yellowkey (back on 4/22/2026)
REDUCED by $51,000 (5.4%) on 04/22/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1884 Built: 2023Monthly Fee: $400 Tax: $8,200 (2025)Community: H Vanwies SubTownhouse
Taxes:$8,200
Remarks: Under contract-accepting backup offers. *Under Contract - Accepting Backup Offers* Experience high-end luxury and effortless convenience in one of the most central locations in Winter Park. Built by Makeur Homes and thoughtfully updated by SMRS Design, this stunning Modern Mediterranean detached townhome showcases light-filled interiors and carefully curated custom finishes. Offering 3 bedrooms and 2.5 bathrooms across 1,884 square feet, the home features a desirable first-floor primary suite and elevated design details, including Level 4 drywall, engineered oak floors, Bosch appliances, LED mirrors, and a Lutron Caséta lighting and Triathlon shade system. A Calacatta Gold porcelain slab electric fireplace serves as a striking focal point in the living room. The open-concept floor plan is both functional and inviting, filled with natural light and offering views of a private paved patio and fenced backyard—ideal for relaxing or entertaining. Enjoy a low-maintenance, lock-and-leave lifestyle within an intimate four-unit community tucked along a picturesque, tree-lined brick street. Additional highlights include a private two-car garage with EV charging port, guest parking, and close proximity to premier dining, shopping, and daily conveniences, including Publix and AdventHealth. A rare opportunity to own a design-forward residence in an exceptional location.
Listing Agent: Rikhil Amin (407-792-8069)
1289 HARMON AVE, WINTER PARK, FL 32789
$500,000 MLS ID: O6346480
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1683 Built: 1990Community: Henkel AddTownhouse
Taxes:
Tax Year:
Remarks: Under contract-accepting backup offers. Multiple Offers! Highest and Best due by 12:00pm on Tuesday 3/10! This impeccable townhome is located in sought after Winter Park. A lovely walkway brings you the front door, where you enter into the foyer of the home. The living room boasts loads of natural light from newer large picture windows, vaulted ceilings, newer porcelain floors and a French door which leads to the deck and backyard. The dining room is just beyond the living room where the peaceful views continue. The renovated kitchen features stainless-steel appliances, soft-close drawers and cabinets with pull-out shelving, Quartz counters and a quaint eat-in area. The staircase, with a large landing area, leads you into a generous size loft with a skylight that provides ample space for an office, workout space, or library. Just beyond the loft is the large primary suite complete with dual walk-in closets with closet systems and plenty of storage space, a private balcony overlooking the front of the home and an ensuite bathroom with a dual sink vanity, jetted garden tub and separate shower. A secondary bedroom space is located on the 1st floor along with a guest bathroom that offers a granite counter vanity and separate shower. The backyard is very Zen and includes 2 decks along with green space. Other amenities and updates include: newer roof, newer water heater, newer windows and sliding door and new porcelain floors. Welcome home!
Listing Agent: Beth Logullo (772-633-0670)
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