Winter Springs Townhomes For Sale - 49 townhouses

Remarks: Under contract-accepting backup offers. Welcome to 476 Club Drive, a beautifully cared-for townhome nestled in the highly sought-after Cypress Club section of The Highlands in Winter Springs—a community known for its incredible amenities and natural surroundings. This spacious 3-bedroom, 2-bath residence blends comfort, functionality, and peace of mind with key updates already completed. Enjoy the benefits of a new roof 2026, new water heater 2026, 2020 A/C system, a full repipe completed in 2016, and a 2016 whole home water softener. Inside, you’ll find an inviting layout with knockdown ceilings throughout the main level and an open living and dining area tucked toward the rear of the home for added privacy. Updated recessed lighting enhances the space, creating a warm and welcoming atmosphere. Just beyond, a step-down enclosed patio offers a serene retreat overlooking wooded views—perfect for relaxing or entertaining. The flexible floor plan includes a downstairs bedroom with an adjacent full bath, ideal for guests, a home office, or multi-generational living. Upstairs, two generously sized bedrooms feature soaring ceilings and abundant natural light. The primary suite offers ample closet space and tranquil views of the surrounding greenery, along with a spacious en-suite bath complete with a Jacuzzi tub and separate shower—perfect for unwinding after a long day. Cypress Club stands out as the only neighborhood within The Highlands with its own private pool, in addition to access to the community’s extensive amenities. Residents enjoy multiple pools, tennis courts, scenic walking trails, parks, pavilions, BBQ areas, a clubhouse, as well as volleyball and basketball courts—delivering a true Florida lifestyle right outside your door. Don’t miss this opportunity to own a move-in-ready home in one of Winter Springs’ most desirable communities!

Listing is courtesy of: KELLER WILLIAMS HERITAGE REALTY (407-862-9700)

Listing Agent: Jeff Singletary (407-383-1933)

Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Short Sale. Unlock the potential in the desirable Vineyards of Mount Greenwood! This 3-bedroom, 1.5-bath townhome in Winter Springs is now offered as a short sale and presents an exceptional opportunity for investors, renovators, or buyers ready to create their own vision. Featuring a spacious living and dining area, functional kitchen, convenient half bath downstairs, and additional storage beneath the staircase, the layout offers a strong foundation with endless possibilities. Sliding glass doors lead to a screened rear porch with an exterior storage closet—perfect for enjoying Florida living year-round. Upstairs, the primary suite offers direct access to the full bath, while two additional bedrooms provide flexibility for guests, a home office, or hobby space. This property is ready for cosmetic updates and is priced accordingly, making it an ideal chance to build equity and customize to your taste. The HOA maintains the roof, exterior, and grounds for added convenience, and residents enjoy access to a community pool. Roof replaced in 2019. Ideally located near top-rated Seminole County schools, parks, shopping, dining, and the Seminole Trail, this home offers outstanding value, location, and long-term potential. Schedule your private showing today and bring your vision to life!

Listing is courtesy of: WATSON REALTY CORP (407-332-6000)

Listing Agent: Sarita Cabrera (321-438-4479)

Remarks: Step inside and this townhome in Casa Park Villas that feels nothing like its neighbors. Completely renovated with designer finishes throughout, NEW AC system (2026), NEW hot water heater, luxury vinyl plank flooring throughout, doors, trim, kitchen, and all three bathrooms renovated. The kitchen sets the tone immediately with white shaker cabinets with matte black hardware, quartz countertops and full quartz backsplash, all-new stainless appliances, under mount sink with matte black faucet, and a breakfast bar pass-through that opens to the bright living and dining areas. Large windows flood the main level with natural light, and a slider leads to the screened rear porch overlooking open green space with pond views and no rear neighbors. Upstairs, both bedrooms are true primary suites with private en-suite baths - each one fully custom. The first features floor-to-ceiling dramatic black vertical tile in the tub/shower with a tiled niche and rain shower head, quartz vanity, and black-framed mirror. The second is an equally polished contrast: white vertical tile tub/shower, quartz vanity, glass pendant vanity light, and the same refined matte black hardware. Dark penny tile floors tie both bathrooms together. The powder bath downstairs features bold black-and-white geometric tile - a finishing touch that shows this renovation was done with intention, not budget cuts. Two assigned parking spaces sit directly in front. The community pool is steps away. Directly across the street: Trotwood Park with pickleball and tennis courts, a splash pad, basketball, playgrounds, pavilions, BBQ grills, and a scenic boardwalk over Lake Maria. Zoned for the A+ rated Seminole County School District, with Keeth Elementary and Indian Trails Middle School within walking distance. Minutes to Winter Springs Town Center, Oviedo Mall, SR 417, UCF, and downtown Orlando. Buyers have been waiting for the one that's actually been done right - this is it.

Listing is courtesy of: PROPERTY LOGIC RE (407-909-3436)

Listing Agent: Alex Quezada (407-404-3225)

Remarks: If you are looking for a turnkey property, this home is it! A rare find end unit has been completely updated & meticulously maintained inside this secluded gated community of The Landings at Parkstone. Imagine yourself in this absolutely stunning home featuring a gourmet kitchen with a clean modern look remodeled in 2025 with premuim quartz countertops, backsplash, new custom cabinetry and new appliances that will please the chef in the family. The primary bathroom was updated in 2024 and features a modern soaking tub, a spacious shower, dual vanity with quartz countertops & new plumbing fixtures. All new flooring throughout with plank tile downstairs and luxury vinyl plank upstairs. Some additional updates include: new AC 2024, roof in 2023, exterior paint in 2023, interior paint in 2025, screened in porch & more. This floor plan offers maximum flexibility with one bedroom & full bath downstairs. The Primary bedroom located upstairs has a custom tray ceiling & an incredibly spacious walk in closet with a small window for natural light. The upstairs has a guest bedroom along with a full bathroom. This neighborhood offers a dedicated community pool for The Landings residents only, secured mailboxes & lawncare included in the quarterly dues. Convenient to the Winter Springs Town Center, Cross Seminole Trail, Dog Park, Central Winds Park & easy eaccess to 417 to shorten the commute. Highly rated Seminole Conty Schools. Bring your most discriminating Buyers as this one will not disappoint!

Listing is courtesy of: KELLER WILLIAMS ADVANTAGE REALTY (407-977-7600)

Listing Agent: Ron Verzaro, Ii (407-221-5464)

Remarks: One or more photo(s) has been virtually staged. Location, Location, Location! Welcome to this beautifully designed 3-level townhome in the highly sought-after Jesups Reserve community. Featuring 3 spacious bedrooms—each on its own floor—this home offers exceptional comfort, flexibility, and privacy. The top-floor primary suite is a true retreat, complete with a large private balcony, perfect for relaxing and enjoying the outdoors. The second-floor living area serves as the heart of the home, showcasing a well-appointed kitchen, bright dining space, and an inviting living room ideal for both everyday living and entertaining. Each bedroom features its own en-suite bathroom, providing convenience and thoughtful functionality for any lifestyle. Additional highlights include a 2-car rear-entry garage and a centrally located second-floor laundry room, with washer and dryer included. Major updates provide true peace of mind, including a NEW 15 SEER HVAC system (2026), NEW roof installed by the HOA (2022), a fully rebuilt, permitted and inspected balcony (2023), and a permitted hot water heater (2020). Unbeatable location—walk to Publix, restaurants, bars, and a new gym, with quick access to SR-417 just minutes away. Whether you're looking for a primary residence or a strong investment opportunity, this home checks all the boxes. Opportunities like this in Jesups Reserve are rare—schedule your showing today before it's gone! For Sale only.

Listing is courtesy of: ORLANDO REALTY & PROPERTY MGNT (407-641-5782)

Listing Agent: Brian Goodwin (321-652-4335)

Remarks: Move-in ready 2-bedroom, 2-bathroom single-level townhome in the heart of Winter Springs! Enjoy an updated kitchen with granite countertops, freshly painted interior, and new flooring. Relax on the screened and tiled lanai overlooking serene greenspace. This quiet, secluded community offers two assigned parking spaces and a community pool just steps from your front door. Residents enjoy amenities including community pool, tennis courts, lush parks, and scenic walking trails throughout the neighborhood. Conveniently located near shopping, dining, entertainment, major highways, and all the area’s conveniences.

Listing is courtesy of: CALL IT CLOSED INTL REALTY (407-338-3339)

Listing Agent: Kathleen Harrison (407-435-9565)

Remarks: Under contract-accepting backup offers. Conveniently located in Winter Springs, this property is a Charming end-unit townhome offering extra privacy and a bright, open layout! This well-maintained home features a spacious living area, updated kitchen with modern cabinetry and stainless steel appliances, and a separate dining/flex space perfect for entertaining or working from home. Enjoy durable tile flooring throughout the main living areas, plenty of natural light, and a functional floor plan that feels both comfortable and inviting. The end-unit location provides added yard space and a more private feel. Nearby Attractions: Central Winds Park & Lake Jessup – Large park with trails, sports fields, and lake views Cross Seminole Trail – Popular walking and biking trail nearby Torcaso Cove Park – Playground, splash pad, and family-friendly amenities Overlook Park (Oviedo) – Boardwalks, fishing pier, and scenic lake views Central Florida Zoo & Botanical Gardens (Sanford) – Easy family day trip Winter Springs Town Center – Community events, dining, and festivals Winter Park (20–25 min drive).

Listing is courtesy of: EXP REALTY LLC (888-883-8509)

Listing Agent: Avel Ramirez (321-304-1690)

Remarks: Welcome to this charming townhome in the highly desirable Jesup Reserve community located in beautiful Winter Springs. This 2-bedroom, 2-bath home offers comfort, convenience, and excellent potential for both homeowners and savvy investors. Step inside to find a spacious layout featuring a modern kitchen equipped with stainless steel appliances and a newer Carrier A/C system for year-round comfort. The home includes a 2-car garage plus additional street parking, making it perfect for families or guests. While the property does need new flooring, it presents a fantastic opportunity to add value and customize the space to your style. Residents of Jesup Reserve enjoy access to a beautiful community pool, ideal for relaxing and enjoying the Florida lifestyle. The home is also conveniently located near top schools, shopping, dining, and major retailers including Publix, making every day errands quick and easy. Whether you're a family looking for a welcoming community or an investor seeking a strong rental opportunity, this townhome offers location, amenities, and upside potential. Seller is very motivated to sell!!!!!!

Listing is courtesy of: WEICHERT REALTORS HALLMARK PRO (407-841-0888)

Listing Agent: James Rice (321-247-0583)

Remarks: If you are looking for a Gated Community with the most desirable location in the community you know you have found it! This home boosts an open floorplan that includes a breakfast bar and open to the family and dining area on the main floor, with high ceilings and lots of natural light. Upgraded appliances, kitchen countertops, and flooring. This floor plan offers two spacious master suites upstairs both with walk in closets, divided by a large laundry room complete with storage and large washer and dryer that are staying! No more carrying laundry up the stairs. Beautiful hardwood floors including the stairs with well-appointed finishes throughout. A MUST SEE! Conveniently located near UCF, shopping, roadways, restaurants and the TOP RATED SCHOOLS in the area.

Listing is courtesy of: A+ REALTY PROFESSIONALS, INC (407-702-5243)

Listing Agent: Susan Pinnock (407-435-9125)