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226 Bennett Street, Winter Springs
$310,000
3 Beds ⋅ 2 Baths ⋅ North Orlando Townsite 4th Add Rep SubDv. ⋅ 32708 Zip Code
NO HOA. NO RULES. NO MONTHLY FEES. JUST YOUR HOME, YOUR WAY. Imagine owning a home in Winter Springs where nobody tells you what color to paint your door, where to park your truck, or what you can build in your backyard. That freedom is rare, and it’s right here. This 3-bedroom, 2-bathroom home sits on a quiet, established street and gives you something most new communities can’t: real ownership without the HOA bill every month. A 1-car garage keeps your vehicle protected and gives you extra storage space, while the yard is ready for weekend cookouts, a garden, or your next big idea. And the location? Minutes from SR 434 and SR 417, Winter Springs Town Center, shopping, dining, parks, and Orlando Sanford International Airport. Layer Elementary is just around the corner. Whether you’re a first-time buyer tired of renting or an investor looking for a smart Winter Springs buy, this one checks the boxes. No HOA homes at this price point don’t last. Schedule your showing before someone else does!

226 Bennett Street, Winter Springs

702 Glasgow Court, Winter Springs
$297,490
4 Beds ⋅ 3 Baths ⋅ Highland Patio Homes SubDv. ⋅ 32708 Zip Code
Reduced! Amazing value for this immaculate property! Picture-perfect 4 bedroom townhouse with private outdoor living spaces in the wonderful Highlands community! This beautiful townhouse has had many updates and upgrades in recent years, including tongue and groove ceilings in the living room, updated kitchen and baths and much more! No carpet! Walking in there is a private courtyard and screened-in front porch to relax in and enjoy your morning coffee. You'll appreciate the soaring wood ceilings in the living room lined with windows overlooking the large private fenced patio. The kitchen features wood cabinets and stainless steel appliances, including a gas range with a double oven! The kitchen has an area large enough for an eat-in table and is adjacent to the screened-in front porch. The first-floor primary has a very large seating area/office overlooking the patio, as well as a large custom built-in wood closet. The primary bath has a stylish vanity, newly tiled shower and a seamless glass door. Upstairs, you'll find three other roomy bedrooms, all with beautiful wood flooring. Other recent updates include a full replumb, new energy efficient windows and doors and garage door. Located in the highly desired Highlands Community, which features a clubhouse and community pool, tennis & pickleball courts, a lake for fishing, park and playground and multiple walking trails!

702 Glasgow Court, Winter Springs

466 Tradition Lane, Winter Springs
$289,000
2 Beds ⋅ 3 Baths ⋅ Heritage Park Twnhms SubDv. ⋅ 32708 Zip Code
Virtually Staged. Beautiful townhome in Heritage Park conveniently located in Winter Springs and close to EVERYTHING! Immaculate 2 bedrooms with 2.5 bathrooms with a covered back porch and single car garage. This townhome is very well maintained with faux wood vinyl flooring and berber carpets. Spacious kitchen with stainless steel appliances. Great floor plan. Secluded and covered back patio to relax and chill out and the end of the day. Gated community which provides privacy and security for your family. Heritage Park also has amenities including a fabulous community pool and playground. Heritage Park is near to convenient Winter Springs and Longwood shopping centers, restaurants and retail stores. Great Seminole County school district. Do not miss the opportunity to own this property!!!! Perfect investment property for rental income. Turn key and ready to go! Request your appointment and come see this gem today!

466 Tradition Lane, Winter Springs

135 Cortez Court, Winter Springs
$325,000
3 Beds ⋅ 2 Baths ⋅ North Orlando Terrace Unit 1 Sec 6 SubDv. ⋅ 32708 Zip Code
Virtually Staged. Welcome home to this charming 3-bed/2-bath with an oversized 1-car garage, ideally situated on nearly a 1/4 acre on a quiet cul-de-sac in desirable Seminole County! Featuring durable concrete block construction, this property offers peace of mind with several significant improvements, including BRAND NEW FRENCH DOORS, garage entry DOOR, ROOF (2020), A/C (2018) annually serviced and recently cleaned/new return vents throughout, and ELECTRICAL REWIRE (2024)! Enjoy a spacious fenced backyard with plenty of room for outdoor entertaining, gardening, pets, or creating your own private Florida oasis. The cul-de-sac location provides added privacy and minimal through traffic. Whether you're a first-time homebuyer, investor, or looking for your next primary residence, this property presents an outstanding opportunity to own a solid home with major capital improvements already in place. PRIME SEMINOLE COUNTY LOCATION! Conveniently located near shopping, dining, parks, schools, and major roadways such as US Hwy 17-92 and the 417 Expressway; downtown Winter Springs; near Oviedo on the Park; 7 miles to Sanford Orlando Airport; 15 miles to Downtown Orlando; and 30 miles to Orlando International Airport. Easy access to everything Central Florida offers. Don't miss this opportunity to make this home your own!

135 Cortez Court, Winter Springs

512 Pinebranch Circle, Winter Springs
$325,000
2 Beds ⋅ 3 Baths ⋅ Barclay Reserve Twnhms SubDv. ⋅ 32708 Zip Code
Welcome Home to 512 Pine Branch Circle, a stunning contemporary townhome nestled within a secure gated enclave in the heart of Winter Springs. While originally built in 2006, this residence has been exceptionally well-maintained, offering the peace of mind that comes with a home. Roof replaced in 2021. New vinyl flooring and interior paint on downstairs level. Step inside to discover a bright, open interior elevated by stylish recent upgrades. The layout flows effortlessly from the kitchen into the living spaces, creating an inviting environment for hosting friends or relaxing in comfort. Outside, the community serves as a private retreat. You’ll appreciate the peaceful atmosphere and beautifully maintained grounds centered around a serene community pond—a picturesque spot to unwind and take in the Florida sunshine. This property combines the ease of low-maintenance townhome living with the reliability of a move-in-ready home. Don't miss the opportunity to make this polished, tranquil space your own. Schedule your private viewing today.

512 Pinebranch Circle, Winter Springs

736 Summerland Drive, Winter Springs
$299,900
3 Beds ⋅ 2 Baths ⋅ Wildwood SubDv. ⋅ 32708 Zip Code
WINTER SPRINGS 3-BEDROOM HOME UNDER $300K — PAID-OFF SOLAR, 2022 ROOF AND MOVE-IN READY! If you're comparing homes under $300,000, take a closer look at what 736 Summerland Drive offers: a renovated 3-bedroom, 2-bath single-family home with approximately 1,298 square feet, paid-off solar panels, a newer roof and access to community amenities. Inside, the updating has already been completed. The refreshed kitchen features modern cabinetry, stone countertops, stainless steel appliances and updated finishes, complemented by renovated bathrooms, flooring, lighting and a clean, contemporary feel throughout the home. But the value here goes beyond cosmetic updates. The roof was replaced in 2022, and the solar system is paid off—meaning there is no solar loan for the buyer to assume. These are meaningful improvements already in place rather than projects or expenses waiting for the next owner. The 3-bedroom, 2-bath layout provides flexibility for everyday living, working from home, guests or hobbies, while the home's manageable footprint offers comfortable living without unnecessary upkeep. The community also offers amenities including a swimming pool, tennis courts and playground, providing additional recreational options without the maintenance of a private pool. Conveniently located in Winter Springs with access to shopping, dining, recreation and major Central Florida roadways. If your search is focused on getting the most for your money under $300,000, compare the entire package at Summerland: 3 bedrooms | 2 bathrooms | Approximately 1,298 sq. ft. | Renovated interior | 2022 roof | Paid-off solar | Community amenities | Winter Springs location The renovation gets your attention. The roof, paid-off solar, location and price are what make the value worth a closer look. Schedule your private showing today.

736 Summerland Drive, Winter Springs

617 Pinebranch Circle, Winter Springs
$339,900
3 Beds ⋅ 3 Baths ⋅ Barclay Reserve Twnhms SubDv. ⋅ 32708 Zip Code
Welcome to the beautiful, tree-lined, gated community of Barclay Reserve. This 3 bedroom, 2.5 bathroom, end unit townhome is offered fully furnished and move in ready. Brand new A/C July 2025, new refrigerator April 2025 and new washer & dryer May of 2023. Enjoy a waterfront view with the soothing fountain sound from the living space and two bedrooms. Both the original owner and current owner used the property as a second home which means less wear and tear. The property is less than 10 minutes away from Ovideo on the Park and 15 minutes away from UCF, making the home a perfect purchase for parents needing student housing. It’s only 2 minutes from SR-417 for easy access to the airport, 408 and I-4. 33 guest parking spaces are distributed around the circle so you don’t have to worry about dodging street parking. Peace, security and a prime location seeking its next owner.

617 Pinebranch Circle, Winter Springs

321 Kirkcaldy Drive, Winter Springs
$350,000
2 Beds ⋅ 2 Baths ⋅ Highland Village 1 SubDv. ⋅ 32708 Zip Code
Great Opportunity in Winter Springs! This single family home has 2 bedrooms, 2 bathrooms, and a large upstairs bonus room - great for an office (or used as another bedroom!). Upon entry you'll be impressed with the high vaulted ceilings and wide open view to the living and dining room. The Primary Bedroom is well sized, and the bathroom features a large walk-in closet, dual sinks, and a shower garden tub. The kitchen has newer appliances and solid wood cabinets. Check out the back yard - it's one of the largest lots in the community - with beautiful grass and a new fence! There's also a screened-in back porch and a large shed - great for storage. 2021 ROOF! Amazing Seminole County Schools!

321 Kirkcaldy Drive, Winter Springs

1541 Corkery Court Unit 1541, Winter Springs
$474,900
2 Beds ⋅ 3 Baths ⋅ Greens At Tuscawilla SubDv. ⋅ 32708 Zip Code
Welcome to the exclusive gated enclave know as The Greens of Tuscawilla. This luxury townhome delivers a rare combination of superior construction, premium finishes, prime location, and a maintenance-free lifestyle. Nestled amongst the trees in the heart of Tuscawilla is The Portofino II Model with Golf, Water and Conservation Views. Level One offers Open Concept Living with the ability for a future Elevator. (Elevator closets are located on both floors and are currently used as walk in storage closets). Level Two allows for privacy with all bedrooms located on this floor. Throughout the unit you will find soaring volume ceilings, crown molding, tall doors, recessed lighting, wood or tiled floors, fresh paint, granite countertops, 42 inch cabinets, designer lighting, fans, fire safety sprinkler system and much more. Start and end each day on your private screened porch where the views are unparralleled. The Greens consists of 15 buildings and 60 units. Residents enjoy lush landscaping, manicured lawns and a private dog park. Partake in the Country Club lifestyle with the private Golf Cart path that leads to Tuscawilla Country Club. Membership provides access to championship golf, Har-Tru clay tennis courts, pickleball court, Jr. Olympic-sized pool, fitness center, private restaurant/bar, and social calendar. The Tuscawilla Community has parks, sports courts and fields, playgrounds, hiking trails and splash pads. Walk, run, or ride while taking in the many natural areas throughout the 3500 acre community.

1541 Corkery Court Unit 1541, Winter Springs

162 Constitution Way, Winter Springs
$289,900
3 Beds ⋅ 3 Baths ⋅ Heritage Park Twnhms SubDv. ⋅ 32708 Zip Code
**Back on market due to buyer financing falling through** Welcome to 162 Constitution Way, a well-maintained 3-bedroom, 2.5-bath townhome in the highly desired gated Heritage Park community of Winter Springs. This home features an open-concept floor plan with a kitchen overlooking the living and dining areas, creating a functional layout for everyday living and entertaining. Upstairs, the spacious primary suite offers a walk-in closet and en-suite bath with dual sinks, while two additional bedrooms, a full bath, and an upstairs laundry room complete the second level. Additional highlights include an attached one-car garage and low-maintenance living with access to community amenities, including a pool and playground. Conveniently located near Winter Springs Town Center, Central Winds Park, shopping, dining, major roadways, and highly rated Seminole County schools, this property is an excellent opportunity for first-time buyers, young families, or investors.

162 Constitution Way, Winter Springs

101 S Flamingo Avenue, Winter Springs
$349,900
3 Beds ⋅ 2 Baths ⋅ North Orlando 2nd Add SubDv. ⋅ 32708 Zip Code
PRICE REDUCTION / 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

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

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

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