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101 S Flamingo Avenue, Winter Springs
$365,500
3 Beds ⋅ 2 Baths ⋅ North Orlando 2nd Add SubDv. ⋅ 32708 Zip Code
BACK on Market after REFRESH/REMODEL for NEW ROOF, NEW BATHROOMS, NEW A/C, NEW EXT PAINT, and MORE! -- Sweet & spacious 3 bed, 2 bath, 1368 sq ft, home on a corner lot in the heart of Winter Springs in a much sought after neighborhood. Fresh Interior Paint, New Kitchen with a floating Island workspace, SS appliances, Tile flooring throughout Dining area, Living and Family Room, inside laundry room. Big, open, wrap-around porch in back is pre-plumbed & trussed for possible expansion of Primary Bedroom. LARGE Fenced backyard, with FRUIT TREES, mature oaks and tidy landscaping. Single car garage can be used as office/storage. Additional Family Room has been added on. Really LOVELY home, TERRIFIC area, GREAT schools! This one is a gem, perfect for first-time buyers! **Note to Investors - offers will need to be at or near full-price**

101 S Flamingo Avenue, Winter Springs

1389 Ponce De Leon Boulevard, Winter Springs
$499,000
4 Beds ⋅ 2 Baths ⋅ Sunrise Unit 2-A SubDv. ⋅ 32708 Zip Code
BACK ON THE MARKET!!PRICE TO SELL. LOCATION, LOCATION, LOCATION! Beautifully remodeled home in the heart of Winter Springs, conveniently located near shopping, dining, banking, fresh market , Publix, Oviedo Mall, YMCA, and major roadways (417 & 408). This spacious residence features 4 bedrooms, 2 full bathrooms, 2 car garage and an open functional floor plan ideal for family living and entertaining, two large separate rooms :a dining room and a living room Recent updates include a water heater (2026)new porch (2026), A/C (2017), and roof (2017). The oversized backyard is shaded by magnificent historic oak trees and includes a utility/workshop, building gym, offering endless possibilities. The community features a playground, basketball court, and park, with an additional neighborhood park conveniently located right next door and the HOA fee is paid anually and is exceptionally affordable.

1389 Ponce De Leon Boulevard, Winter Springs

498 Green Spring Cir, Winter Springs
$244,000
2 Beds ⋅ 2 Baths ⋅ Mount Greenwood Unit 4 Of SubDv. ⋅ 32708 Zip Code
Welcome to 498 Green Spring Circle in the desirable Mount Greenwood community of Winter Springs! This beautifully maintained 2 bedroom, 1.5 bath end-unit townhome offers peaceful pond views, low-maintenance living, and access to top-rated Seminole County schools. Step inside to an open and inviting floor plan featuring ceramic tile flooring throughout the main living areas and fresh interior paint. The spacious living and dining areas flow seamlessly to the oversized screened patio with paver flooring, creating the perfect space to relax, entertain, or enjoy your morning coffee while overlooking the tranquil water and mature trees. The kitchen opens to the main living space, creating a bright and functional layout ideal for everyday living. Upstairs, you'll find two generously sized bedrooms with large closets and ample storage. An additional exterior storage closet off the patio provides even more convenience. Residents of Mount Greenwood enjoy a low HOA and outstanding community amenities, including a sparkling pool, tennis courts, playground, and scenic walking and biking trails. Ideally located just off SR 434 and minutes from Winter Springs Town Center, shopping, dining, parks, and major commuter routes. Whether you're a first-time homebuyer, downsizing, or searching for the perfect Florida retreat, this move-in-ready townhome offers comfort, convenience, and beautiful waterfront views. Don't miss this opportunity to enjoy the Florida lifestyle in one of Winter Springs' most desirable locations. Schedule your private showing today!

498 Green Spring Cir, Winter Springs

717 Adidas Road, Winter Springs
$399,900
2 Beds ⋅ 2 Baths ⋅ Wedgewood Tennis Villas SubDv. ⋅ 32708 Zip Code
Virtually Staged. Welcome home to this absolutely charming and move-in-ready 2-bedroom, 2-bathroom home nestled in one of the most desirable areas of Winter Springs! From the moment you arrive, you'll appreciate the countless updates, beautiful wood beams and inviting curb appeal that make this home truly special. Major improvements provide peace of mind, including a 4-year-old roof, brand-new water heater, new flooring throughout, fresh interior and exterior paint, new appliances, and all-new light fixtures and ceiling fans. The beautifully updated kitchen offers modern style and functionality, while both bathrooms have been thoughtfully remodeled with today's buyer in mind. The spacious and light-filled bonus room overlooks the picturesque backyard and tranquil pond, creating the perfect space for a home office, reading room, playroom, or additional living area. Step outside and enjoy your backyard retreat featuring stunning water views and majestic oak trees that provide natural shade and beauty year-round while enjoying your morning coffee and watching the family of ducks swim by daily to greet you. Located in a great walking neighborhood, you'll love being just minutes from Tuscawilla Country Club and its renowned golf course, with olympic size pool and dining. Near top-rated schools and parks. Conveniently close to everything you need such as shopping, restaurants, medical facilities and your only a short drive to Florida's famous Theme Parks and about a 45 min drive to the best Beaches around. This adorable home offers the perfect blend of comfort, style, and location. Completely move-in ready and waiting for its new owners to fall in love—don't miss this incredible opportunity to own a piece of Winter Springs paradise!

717 Adidas Road, Winter Springs

1357 Mill Stream Lane, Winter Springs
$384,000
3 Beds ⋅ 3 Baths ⋅ Jesups Landing SubDv. ⋅ 32708 Zip Code
Move in Ready, Updated 3-bedroom, 2.5-bath end-unit townhome in the desirable Jesups Landing community of Winter Springs! Recent updates include new flooring,, NO CARPET, new exterior paint and a new roof. The open layout features generous living and dining areas that flow seamlessly into the kitchen. Upstairs, you'll find all three bedrooms, the laundry area, and a gorgeous patio. The spacious primary suite offers ample closet space and a beautiful, spacious en-suite bath. One of the home's most attractive features is its unbeatable location adjacent to Central Winds Park, where residents can enjoy a baseball diamond, basketball court, a fishing pier, nature trail, picnic facilities and pavilion, a soccer field, playground, volleyball courts, NEW PICKLEBALL COURTS AND A GREAT DOG PARK in additiona to year-round community events. Families will also appreciate the proximity to highly rated Seminole County schools, shopping, dining, and major commuter routes. Whether you're a first-time homebuyer, downsizing, or seeking a low-maintenance lifestyle in one of Winter Springs' most desirable locations, this beautifully maintained townhome is a must-see!

1357 Mill Stream Lane, Winter Springs

429 Sheoah Boulevard Unit 9, Winter Springs
$199,000
3 Beds ⋅ 2 Baths ⋅ Baytree Village SubDv. ⋅ 32708 Zip Code
Welcome to this beautifully maintained 3-bedroom, 2-bath condominium nestled in the highly desirable Highlands community of Winter Springs. Offering the perfect blend of comfort, style, and convenience, this move-in-ready home features an updated kitchen with granite countertops, stainless steel appliances, and ample cabinetry. The spacious floor plan is complemented by updated bathrooms, well-maintained interiors, and an inviting atmosphere throughout. Whether you're relaxing at home or hosting guests, you'll appreciate the thoughtful upgrades and pride of ownership evident in every room. Step outside and enjoy the exceptional resort-style amenities the community has to offer, including a sparkling pool, tennis and pickleball courts, scenic walking trails, playgrounds, and picturesque water views. The HOA provides added peace of mind by covering exterior maintenance, roof care, and common area upkeep, allowing for a low-maintenance lifestyle. Conveniently located near parks, shopping, dining, top-rated Seminole County schools, and major roadways, this home offers easy access to everything Central Florida has to offer. Don't miss this opportunity to enjoy resort-style living in one of Winter Springs' most sought-after communities!

429 Sheoah Boulevard Unit 9, Winter Springs

108 Sundance Court, Winter Springs
$349,900
3 Beds ⋅ 2 Baths ⋅ The Seasons SubDv. ⋅ 32708 Zip Code
Welcome home to this beautifully remodeled gem tucked away on a quiet cul-de-sac in desirable Winter Springs! From the moment you walk in, you’ll fall in love with the bright, open-concept layout designed for easy living and effortless entertaining. With 1,161 sq ft under air, every inch of this home has been thoughtfully updated and filled with charm. The stunning fully remodeled kitchen is the heart of the home, featuring modern finishes, updated cabinetry, and a welcoming flow into the spacious living and dining areas. Both bathrooms have also been completely renovated, creating a fresh, stylish feel throughout. Step through the back doors and discover your own private retreat — a peaceful backyard backing directly to a beautiful conservation area with no rear neighbors, offering the perfect blend of privacy and nature. Imagine morning coffee with serene views or relaxing evenings enjoying the Florida breeze. Even better, the major 4 systems have all been replaced within the last 5 years, giving buyers confidence and peace of mind for years to come. Whether you’re a first-time buyer, downsizing, or simply looking for a turnkey home in an amazing location, this one checks all the boxes. Conveniently located near shopping, dining, parks, and great schools, this is the opportunity you’ve been waiting for. Sold as-is and ready for its next owner to fall in love!

108 Sundance Court, Winter Springs

343 San Miguel Street Unit 343, Winter Springs
$145,000
2 Beds ⋅ 2 Baths ⋅ Indian Ridge SubDv. ⋅ 32708 Zip Code
Welcome to this freshly painted 2-bedroom, 2-bathroom condominium located in the desirable Deer Song community in Winter Springs. Offering a low-maintenance lifestyle in a convenient Central Florida location, this residence is a great fit for a first-time buyer, downsizer, seasonal resident, or investor looking for a well-positioned property with everyday comfort and community appeal. Inside, the home features a practical layout with 945 square feet of living space, offering comfortable living areas and a functional design that makes the most of the space. The freshly painted interior provides a clean, refreshed feel and gives the next owner a neutral starting point to make the home their own. With two bedrooms and two full bathrooms, the layout offers flexibility for guests, a home office setup, or shared living arrangements. One of the standout features of this home is the private outdoor space. The fenced patio area creates a comfortable spot for morning coffee, container gardening, pets, outdoor dining, or relaxing at the end of the day. The included storage shed adds valuable functionality, offering extra space for tools, bikes, seasonal items, or outdoor equipment. Deer Song offers a peaceful residential setting known for its established neighborhoods, mature surroundings, and convenient access to parks, trails, shopping, dining, and everyday essentials. The community is located near Winter Springs Town Center, Torcaso Park, the Cross Seminole Trail, Oviedo Mall, Publix, restaurants, and major roadways for easier commuting throughout Central Florida. With its freshly painted interior, efficient 2-bedroom layout, private fenced outdoor space, storage shed, and desirable Winter Springs location, this Deer Song condominium offers comfort, convenience, and low-maintenance living in one of Seminole County’s most appealing areas.

343 San Miguel Street Unit 343, Winter Springs

335 Kirkcaldy Drive, Winter Springs
$324,900
3 Beds ⋅ 2 Baths ⋅ Highland Village 1 SubDv. ⋅ 32708 Zip Code
Seller is offering to contribute towards the buyer's closing cost up to $5,000. Welcome home to this cozy 3-bedroom, 2-bath bungalow-style home located in the resort-like Highlands community, offering 1,178 sq. ft. of living space. This home features vaulted ceilings, ceramic tile throughout, fresh interior paint, and a newly renovated kitchen with granite countertops, solid wood shaker-style cabinets, and black appliances. Major updates include a 2025 water heater and a new electrical panel inside and outside. The generously sized primary bedroom includes a built-in California Closets system, providing stylish and highly functional custom storage. The secondary and third bedrooms are also well-sized—perfect for guests, family, or easily converted into a home office. Washer and dryer are included in the sale. Enjoy the covered and screened lanai overlooking a charming New Orleans-style courtyard with pavers, a firepit, and a lamp post. The oversized, fully fenced, and cleared backyard offers plenty of space to relax, entertain, or garden, providing a strong sense of privacy. The Highlands is a highly sought-after, established community with low HOA fees and beautiful mature trees throughout. Amenities include an Olympic-size community pool, walking trails, playground, tennis court, volleyball court, and a clubhouse. Ideally situated just off State Road 434 Florida and Tuskawilla Road, this home offers quick access to Winter Springs Town Center for shopping and dining, and is just a short stroll from Torcaso Park—a lively neighborhood park featuring basketball courts, soccer and football fields, playgrounds for all ages, a splash pad, sand play areas, and picnic pavilions, perfect for both active days and relaxed family outings.

335 Kirkcaldy Drive, Winter Springs

1304 Ortega Street, Winter Springs
$474,900
4 Beds ⋅ 3 Baths ⋅ Sunrise Estates Unit 1 SubDv. ⋅ 32708 Zip Code
New roof 2023, AC 2020, water heater 2023, whole-home water softener 2024. Non-flood zone. No rental restrictions. HOA only $30/month. The expensive questions are already answered on this Winter Springs home. Major systems have been replaced, the 4-point inspection is straightforward, and insurance-friendly construction (block and stucco, slab foundation, shingle roof 2023) keeps ownership costs predictable. 4 bedrooms, 2.5 baths, 2,152 SqFt of living area on a 10,019 SqFt lot in Sunrise Estates, a short walk to Rainbow Elementary and minutes from Tuskawilla Road, Winter Springs Town Center, Oviedo, and the 417 for an easy commute to Orlando, UCF, and Lake Mary. The three-level split layout gives you the separation most homes in this price range can't have. The main level holds the formal living and dining rooms and a 11x18 eat-in kitchen with pantry, storage closet, solid wood cabinets, and solid surface counters. One level down is a 21x18 family room with a stone wood-burning fireplace and French doors to the lanai. Upstairs, all four bedrooms: a 15x17 primary suite with walk-in closet and ceiling fan, plus three additional bedrooms with built-in closets. Cathedral and vaulted ceilings, ceramic tile throughout, updated bathrooms, freshly painted interior, and an indoor laundry room. Alkaline water filtration at the kitchen sink. Outside is where this home stands apart. A 21x14 covered and screened lanai with ceiling fan and gas fire pit opens to a fully fenced backyard with a second natural fire pit, play area, dog run, garden space, storage shed, and an irrigation system on a private sprinkler well, so the lawn stays green without a water bill. Two-car garage with opener plus open driveway parking. Community amenities include playground and tennis courts. Zoning PUD. Public water and sewer. Schedule your showing today! Seller may consider buyer closing-cost assistance with an acceptable offer.

1304 Ortega Street, Winter Springs

50 Sheoah Boulevard Unit 33, Winter Springs
$167,777
2 Beds ⋅ 2 Baths ⋅ Sheoah Sec 1 SubDv. ⋅ 32708 Zip Code
THIS HOME QUALIFIES FOR $0 DOWN WITH OUR PREFERRED LENDER!!! DON'T MISS YOUR OPPORTUNITY TO OWN THIS BEAUTIFUL HOME!! WELCOME HOME! This elegant, bright, and open first-floor, single-story 2-bedroom, 2-bath condo is located in the highly desirable Winter Springs community. From the moment you step inside, you’ll feel right at home in the spacious living and dining area featuring custom-built shelving and an inviting layout perfect for relaxing or entertaining. The split-bedroom floor plan offers added privacy, with sliding doors from the primary suite leading to a charming brick patio, ideal for enjoying your morning coffee or unwinding in the evening. The kitchen has been beautifully renovated with new appliances, updated countertops, and ample workspace. The primary bathroom features a walk-in shower with safety grab bars, while the guest bathroom includes a tub, with a convenient laundry area located in the guest bath closet. A bright and airy enclosed Florida room with A/C provides flexible space for a home office, reading nook, or additional living area. Step outside to your private patio with room for outdoor furniture, plants, or even your own garden retreat, all overlooking a peaceful wooded conservation area. Additional highlights include approximately 1,196 square feet including the enclosed porch, a newer A/C and water heater, fresh interior paint in a modern light gray, and no carpet throughout. Located in The Highlands, a quiet and friendly community offering a pool, tennis courts, parks, walking trails, scenic water views, reserved parking, and community mailboxes. HOA fees include high-speed internet, cable, pest control, and full grounds maintenance, with weekly lawn care and twice-weekly trash pickup. The home is situated in a top-rated school district with schools nearby and is just minutes from shopping, dining, and everyday conveniences. Schedule your private showing today, this one won’t last long!

50 Sheoah Boulevard Unit 33, Winter Springs

299 Woodgreen Lane, Winter Springs
$275,000
3 Beds ⋅ 3 Baths ⋅ Mount Greenwood Unit 4 Of SubDv. ⋅ 32708 Zip Code
Welcome to this BEAUTIFULLY UPDATED 3-bedroom, 2.5-bath townhome in the PEACEFUL Mount Greenwood community of Winter Springs, where modern upgrades and a thoughtfully designed layout create a truly inviting place to call home. As a CORNER UNIT, this residence enjoys added privacy along with a serene setting, including POND VIEWS just beyond the rear fence, best appreciated from the upstairs bedrooms. Step inside to discover an OPEN and SPACIOUS FLOOR PLAN filled with NATURAL LIGHT, enhanced by LUXURY VINYL PLANK FLOORING (2020) throughout the main level. The Kitchen is both stylish and functional, featuring STAINLESS STEEL APPLIANCES, white cabinetry, a sleek tile backsplash, a closet pantry, and a convenient laundry closet. A PASS-THROUGH WINDOW connects the Kitchen to the Dining Room, creating an easy flow for everyday living and entertaining. The Dining area seamlessly transitions into the generous Living Room, where NEWER DOUBLE DOORS WITH BUILT-IN BLINDS (2022) open to the screened patio, offering a relaxing indoor-outdoor connection. The back and side yards have been thoughtfully designed for LOW MAINTENANCE, with no grass to cut, all enclosed within a NEW WOOD FENCE (2024)—perfect for enjoying quiet evenings or weekend gatherings. A HALF BATH on the main floor adds convenience for guests. Upstairs, the Primary Suite provides a comfortable retreat, complete with an en suite bath featuring a step-in shower and UPDATED VANITY WITH GRANITE COUNTERTOP (2020). TWO ADDITIONA BEDROOMS offer flexibility for family, guests, or a home office. The ROOMS ARE CURRENTLY CONNECTED by an open wall, creating one larger space. The opening can be easily closed off by the Buyer to restore two separate bedrooms, if desired. A second full bath with UPDATED TILE (2023) serves the additional bedrooms. This home has been meticulously maintained and updated with major improvements, including a NEW HVAC SYSTEM (2024), NEW WATER HEATER (2023), and a NEWER ROOF (2019)—providing both style and peace of mind. Residents of Mount Greenwood enjoy LOW HOA fees and access to amenities including a community pool, playground, and included trash service, all within a friendly and WELL-KEPT NEIGHBORHOOD. IDEALLY LOCATED near Central Winds Park and Winter Springs Town Center, you’ll have EASY ACCESS to outdoor recreation, shopping, and dining. The home is also zoned for HIGHLY REGARDED SCHOOLS and offers convenient access to State Road 417, making commuting to Orlando and surrounding areas simple. With its stylish updates, low-maintenance outdoor space, and DESIRABLE LOCATION this Mount Greenwood townhome brings the perfect blend of comfort, convenience, and easy Florida living. Call and schedule your showing today!

299 Woodgreen Lane, Winter Springs

1128 Spotted Sandpiper Loop, Winter Springs
$455,000
4 Beds ⋅ 4 Baths ⋅ Seminole Crossing Twnhms SubDv. ⋅ 32708 Zip Code
Virtually Staged. SELLER MOTIVATED!!! Welcome to an exceptional opportunity in the heart of Winter Springs, where lifestyle, location and luxury converge at 1128 Spotted Sandpiper Loop. Positioned in a thoughtfully planned community, this residence offers the ideal balance of elegance and everyday convenience. From moment you arrive, you are embraced by a neighborhood designed for connection and ease, tree-lined streets, inviting trails and a sense of community that makes this address desirable. Ideally just moments from Winter Springs Town Center, this residence offers an accessible lifestyle. Natural light fills the interiors, creating a warm and welcoming ambiance suited for relaxed living and stylish entertaining. Thoughtfully designed across three levels, the first floor offers a private retreat ideal for guests, complete with its own en suite. The second level unfolds into the heart of the home, featuring an open concept living space with a well-appointed kitchen, dining area and inviting family room. The third floor is dedicated to restful living, showcasing three bedrooms, two full baths and a convenient laundry area. Updates include new carpeting throughout with transferable warranty and fresh interior paint reflecting the home's meticulous maintenance. Beyond your doorstep, accessibility becomes a defining feature of this lifestyle. Enjoy proximity to local shops, dining, parks and top-rated Seminole County schools, all just moments away. With easy access to major roadways, commuting to downtown Orlando, nearby business hubs, or weekend destinations is simple and efficient. Amenities include community pool, trails and accessibility to area favorites.

1128 Spotted Sandpiper Loop, Winter Springs

240 Moree Loop Unit 3, Winter Springs
$170,000
3 Beds ⋅ 2 Baths ⋅ Baytree Village SubDv. ⋅ 32708 Zip Code
One or more photo(s) has been virtually staged. Welcome to Baytree Village in the heart of Winter Springs—where beautifully landscaped grounds and a welcoming atmosphere create the perfect place to call home. This MOVE-IN READY second-floor condo offers 3 bedrooms, 2 full baths, and added privacy, all in a prime location close to top-rated schools, parks, shopping, dining, and major roadways for an easy commute. Step inside to a bright, open-concept living and dining area featuring a wall of windows and two sets of triple sliding glass doors, filling the space with natural light and providing seamless access to a large screened balcony with peaceful garden views—perfect for relaxing or entertaining. The kitchen is well-equipped with stainless steel appliances, ample cabinet and countertop space, and easy-care tile flooring. The spacious primary suite offers a comfortable retreat, while two additional bedrooms provide flexibility for guests, a home office, or additional living space. Additional highlights include in-unit laundry and extra storage off the balcony. Residents of Baytree Village enjoy well-maintained amenities and close proximity to local parks, including Audubon Park just minutes away. Seller is willing to cover up to six (6) months of the buyer’s Homeowners Association (HOA) dues with an acceptable offer. Whether you're a first-time buyer, downsizing, or investing, this is an opportunity you won’t want to miss. Schedule your private showing today!

240 Moree Loop Unit 3, Winter Springs

4113 Hedge Maple Place, Winter Springs
$276,200
2 Beds ⋅ 3 Baths ⋅ Heritage Commons SubDv. ⋅ 32708 Zip Code
PRICE IMPOVEMENT 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.

4113 Hedge Maple Place, Winter Springs

702 Glasgow Court, Winter Springs
$301,000
4 Beds ⋅ 3 Baths ⋅ Highland Patio Homes Amended Plat SubDv. ⋅ 32708 Zip Code
**Fannie Mae approved** Welcome to a beautifully updated patio home tucked away on a quiet, tree-lined cul-de-sac in the desirable Pebble Creek community of The Highlands in Winter Springs. Enjoy Villa-style living with a two-story layout. Offering 4 bedrooms, 2.5 bathrooms, and a thoughtfully designed layout with the primary suite conveniently located on the first floor, this home blends comfort, functionality, and low-maintenance living. From the moment you arrive, you’ll appreciate the private courtyard entry—perfect for morning coffee or relaxing evenings, along with multiple outdoor spaces, including a screened-in porch and two fenced areas ideal for pets or gardening. Inside, the home features warm wood accents, soaring ceilings, and an abundance of natural light throughout. The updated kitchen is equipped with a gas double oven, modern appliances, pantry storage, and flows seamlessly into the main living areas. An interior laundry/utility room adds everyday convenience. Bathrooms have been tastefully renovated with updated vanities, tilework, and glass shower enclosures. Recent upgrades provide peace of mind, including re-piping, updated HVAC system, water heater, garage door, and energy-efficient windows and doors. Additional improvements include updated flooring, custom closet shelving, and enhanced finishes throughout the home. Located within The Highlands, residents enjoy a wide range of amenities, including a community pool, clubhouse, tennis courts, playgrounds, and miles of scenic walking trails and boardwalks. The HOA maintains exterior elements such as the roof, paint, and landscaping, allowing for easy, low-maintenance living

702 Glasgow Court, Winter Springs

476 Club Drive, Winter Springs
$267,500
3 Beds ⋅ 2 Baths ⋅ Cypress Club SubDv. ⋅ 32708 Zip Code
Virtually Staged. Welcome to 476 Club Drive, a beautifully maintained 3-bedroom, 2-bath townhome in the highly sought-after Cypress Club section of The Highlands in Winter Springs. NEW ROOF 2026, NEW WATER HEATER 2026, 2020 A/C, FULL-HOME REPIPE 2016, and WHOLE-HOME WATER SOFTENER 2016! This spacious home offers a flexible floor plan, peaceful wooded views, and an impressive list of updates. The main level features knockdown ceilings, updated recessed lighting, and an inviting living and dining area overlooking the serene, tree-lined surroundings. A step-down enclosed patio provides additional living space and a wonderful private retreat for relaxing or entertaining. A downstairs bedroom with an adjacent full bath offers flexibility for guests, a home office, or multi-generational living. Upstairs, two spacious bedrooms feature soaring ceilings and abundant natural light. The generous primary suite offers ample closet space, tranquil wooded views, and a private bath with a Jacuzzi tub and separate shower. A dedicated tankless water heater serves the Jacuzzi tub and primary suite bathroom, adding an extra level of comfort and convenience. Enjoy the added benefit of a covered carport with TWO dedicated parking spaces, keeping your vehicles protected from the Florida sun and weather. Cypress Club is the only section of The Highlands with its own private pool, while residents also enjoy access to the community’s outstanding amenities, including multiple pools, tennis courts, walking trails, parks, pavilions, BBQ areas, clubhouse, volleyball, and basketball courts. Located in desirable Winter Springs, this move-in-ready townhome combines thoughtful updates, flexible living spaces, natural surroundings, covered parking, and an exceptional amenity-rich community. Don’t miss the opportunity to make 476 Club Drive your new home!

476 Club Drive, Winter Springs

421 Horizon Drive, Winter Springs
$285,000
3 Beds ⋅ 2 Baths ⋅ Seasons The SubDv. ⋅ 32708 Zip Code
MOTIVATED SELLERS!!! Welcome to 421 Horizon Drive in Winter Springs, located in The Seasons community. This move-in ready home checks all the big boxes upfront: a 50-year Rhino shingle roof (2019), a 3.5-ton 14 SEER AC unit with heat pump and updated ductwork, a new electric panel, and a 2019 water heater. Beautifully maintained and thoughtfully updated throughout, this one-story home offers 3 bedrooms, 2 bathrooms, and 1,069 square feet of living space. Inside, you'll find newer Mohawk laminate flooring in the main living areas and bedrooms, tile in the kitchen and baths, updated light fixtures, newer ceiling fans, upgraded baseboards, and modernized doors and hardware throughout. The primary suite features a fully renovated bathroom with a walk-in shower, glass enclosure, rain shower head, and updated vanity. The guest bathroom has also been extensively renovated. High and vaulted ceilings enhance the open great room and dining space, while the sliding glass doors lead to an extended and stamped concrete patio within a private vinyl fenced yard, ideal for relaxing or entertaining. Located on a quiet cul-de-sac with assigned parking and curb parking available, this home is just a short walk to the community pool and directly across from the park, playground, and tennis courts. The HOA covers lawn maintenance, making for easy, low-maintenance living in a prime Seminole County location zoned for Winter Springs schools.

421 Horizon Drive, Winter Springs

600 Northern Way Unit 201, Winter Springs
$274,900
3 Beds ⋅ 2 Baths ⋅ Tuscany Place Ph 1 SubDv. ⋅ 32708 Zip Code
Virtually Staged. Welcome home to this maintained 3-bedroom, 2-bathroom ground-floor condominium offering 1,425 square feet of comfortable, low-maintenance living in a desirable gated community in the heart of Tuscawilla, perfect for investors or those seeking a primary residence. Step inside to a FRESHLY painted inviting open floor plan highlighted by tile flooring throughout the main living areas, creating a seamless space for both everyday living and entertaining. The kitchen is thoughtfully designed with NEW stainless steel appliances, stone countertops, an eat-in dining area, and a convenient laundry closet nearby for added functionality. Privately situated at the rear of the home, the spacious primary suite offers a peaceful retreat complete with a walk-in closet, and a RENOVATED bathroom dual vanity sinks, and a standalone shower. Sliding glass doors provide direct access to your own private patio — the perfect spot to enjoy your morning coffee. Down a separate hallway, you’ll find two additional bedrooms and a guest bathroom featuring an updated vanity and a tub/shower combination, offering comfort and privacy for family or guests. The living area also opens through sliding doors to a covered rear lanai overlooking tranquil green space, creating an ideal setting for relaxing or entertaining outdoors. Residents enjoy access to a beautiful community pool and cabana, enhancing the ease of Florida living. Conveniently located by Trotwood Park, featuring a pavilion, playground, splash pad, tennis courts, and sports fields. The nearby Seminole County Cross Trail offers miles of scenic biking and walking paths. This exceptional condo combines comfort, convenience, and an unbeatable location — a wonderful opportunity to enjoy everything Tuscawilla has to offer.

600 Northern Way Unit 201, Winter Springs

709 Sailfish Road, Winter Springs
$387,500
3 Beds ⋅ 2 Baths ⋅ North Orlando Ranches Sec 10 SubDv. ⋅ 32708 Zip Code
Some neighborhoods offer just a house; this one delivers a true Florida lifestyle, anchored by a beautiful, deep quarter-acre lot and a home built for functional, everyday living. Tucked away in a quiet pocket of Winter Springs—one of Seminole County’s most coveted and safest communities—this 3-bedroom, 2-bathroom gem offers the rare freedom of no HOA combined with unparalleled privacy. The home provides immediate peace of mind with a roof that is only 5 years old. Set beneath a picturesque canopy of mature trees and draping Spanish moss, the curb appeal speaks to the established, friendly vibe that residents of Winter Springs enjoy. Step inside to a flexible layout built for flow, featuring dedicated living and family rooms that give everyone room to spread out. The central kitchen and dining space is positioned perfectly to serve both entertaining areas and acts as the heart of the home. The smart split-bedroom floor plan provides ideal separation, tucking the spacious primary suite on one side of the house for privacy and tranquility. The real magic happens where the indoors meets the outdoors. The home expands dramatically with a large, enclosed Florida Room (22'6" x 11'6") that is fully under A/C with its own dedicated mini-split unit—making this substantial bonus space a year-round extension of the living area, perfect for an office, gym, or sun-soaked den. This room leads directly out to a private, spacious backyard where you will enjoy the unique benefit of no rear neighbors, secured by a perimeter of mature trees and fencing. Even the garage has been elevated: the two-car garage features durable epoxy flooring and includes a dedicated laundry area and a useful closet room, perfect for home projects or tool storage. The location is the final mic drop. You are moments from the convenience of Winter Springs Town Center, Central Winds Park, and the premier amenities of the Tuscawilla area. You are also zoned for the excellent Seminole County School District. You get the quiet, safe suburban environment while maintaining effortless access to major highways (417/I-4) for a convenient commute to Downtown Orlando or Lake Mary. View the 3D Matterport tour now to fully appreciate the space and layout. This is more than a listing—it’s the home where your next chapter begins.

709 Sailfish Road, Winter Springs

506 Club Drive, Winter Springs
$199,000
2 Beds ⋅ 2 Baths ⋅ Cypress Club SubDv. ⋅ 32708 Zip Code
Virtually Staged. 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. The HOA just installed brand new roofs throughout the community. 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.

506 Club Drive, Winter Springs

270 San Gabriel Street, Winter Springs
$242,000
3 Beds ⋅ 2 Baths ⋅ Deersong 2 SubDv. ⋅ 32708 Zip Code
Quick Closing Available. Welcome to 270 San Gabriel Street in Winter Springs—now offered at an updated price and ready for its next owner. This well-maintained, single-story home features vaulted ceilings and a bright, open layout that creates a comfortable and inviting living space. With neutral finishes and ceramic tile flooring throughout, the home is truly move-in ready. All appliances are included for added convenience. Enjoy morning coffee or unwind in the evening on the oversized screened patio, offering a private outdoor retreat. Additional exterior storage provides practical space for bikes, tools, and seasonal items. Located just minutes from the scenic Cross Seminole Trail, the Deersong community also offers access to a pool and cabana for residents to enjoy. Nearby parks, shopping, dining, and top-rated Seminole County schools add to the home’s appeal. Considering making a move to downsize? First-time homebuyer? Buyer needs concessions / closing costs? investor? or seeking a low-maintenance second home in Central Florida? Schedule your private showing today. With a newly reduced price and quick closing available, this is an excellent opportunity to own a well-cared-for home in a desirable location..

270 San Gabriel Street, Winter Springs