Casselberrry/Winter Springs / Tuscawilla Homes for Sale

Casselberrry/Winter Springs / Tuscawilla Homes for Sale

Welcome to the enchanting region of Casselberry, Winter Springs, and Tuscawilla, nestled in the heart of Seminole County, Florida. This vibrant area is known for its picturesque landscapes, family-friendly atmosphere, and a strong sense of community. With its lush parks, serene lakes, and scenic trails, outdoor enthusiasts will find plenty of opportunities for recreation and relaxation. The region boasts a rich blend of natural beauty and modern amenities, making it an ideal place for families, young professionals, and retirees alike.

Winter Springs is renowned for its excellent schools, making it a top choice for families. The local community hosts various events throughout the year, fostering a tight-knit environment. Tuscawilla, with its charming golf courses and beautiful homes, offers a tranquil suburban lifestyle while being just a short drive from the bustling city of Orlando.

When it comes to homes for sale in this delightful area, you’ll find a diverse range of properties to suit every taste and budget. From modern single-family homes with spacious backyards to elegant townhomes and luxurious estates, there’s something for everyone. Many homes feature stunning views, updated interiors, and access to community amenities such as pools, playgrounds, and walking trails.

If you’re looking to invest in a home that combines comfort, community, and convenience, the Casselberry, Winter Springs, and Tuscawilla region is the perfect place to call home. Explore the available listings today and discover the lifestyle that awaits you in this beautiful part of Florida!

Newest Casselberrry/Winter Springs / Tuscawilla Homes for Sale

$785,000
5 Beds ⋅ 4 Baths ⋅ Winding Hollow Unit 5 SubDv. ⋅ 32708 Zip Code
WELCOME HOME to 337 Twelve Oaks Drive! This stunning Wisteria II Model offers 5 bedrooms, 3.5 bathrooms, and 3,660 square feet of beautifully maintained living space, perfectly positioned on an oversized .25-acre premium waterfront lot in the sought-after Winding Hollow community of Winter Springs. From the moment you arrive, you'll appreciate the lush landscaping, exceptional curb appeal, and pride of ownership throughout this immaculate home. Inside, an abundance of thoughtful upgrades and elegant finishes create the perfect blend of comfort, style, and functionality. The renovated gourmet kitchen is truly the heart of the home, featuring floor-to-ceiling custom cabinetry, quartz countertops, a large center island, stainless steel appliance package, stylish tile backsplash, and a water filtration system. The spacious kitchen opens beautifully to the expansive family room, creating an ideal space for everyday living and entertaining. Additional upgrades include all-new windows and doors, beautiful wood-plank ceramic tile flooring, plantation shutters, and newer attic insulation, providing both style and improved energy efficiency. The first floor features a spacious primary suite, a versatile den/office, formal living room, formal dining room, and a huge family room with serene views of the private pool, expansive patio, and tranquil pond. The primary suite provides a peaceful retreat with plenty of space and privacy. Upstairs, you'll find three additional generously sized bedrooms, each offering large closets, along with two full bathrooms and an impressive 17' x 24' game room—perfect for a media room, playroom, home gym, or additional entertaining space. The three-car garage provides abundant storage and parking, and features a custom garage floor coating for a polished, durable finish. Step outside and experience your own private oasis. The sparkling pool, spacious patio, lush landscaping, and peaceful waterfront setting create the perfect backdrop for relaxing mornings, afternoon swims, and memorable gatherings with family and friends. Located in desirable Winding Hollow, this home offers an exceptional Winter Springs lifestyle with walking trails, community park areas, close proximity to top-rated Seminole County schools, shopping, Winter Springs Town Center, restaurants, Central Winds Park, the Seminole Trail, and more. With its premium waterfront setting, private pool, spacious floor plan, three-car garage, extensive upgrades, and beautifully appointed living spaces, 337 Twelve Oaks Drive is more than just a home—it’s a lifestyle!

337 Twelve Oaks Drive, Winter Springs
$325,000
3 Beds ⋅ 2 Baths ⋅ Wildwood SubDv. ⋅ 32708 Zip Code
Welcome to 654 Cypress Lane, a move-in-ready 3-bedroom, 2-bathroom home featuring fresh interior paint throughout. The main entry opens into a bright living room that connects seamlessly to the kitchen, complete with quartz countertops and stainless steel appliances. Designed with a practical split floor plan, the primary bedroom sits on one side of the home with its own en-suite bathroom, while two secondary bedrooms share a second full bath on the opposite side. A dedicated laundry room adds extra convenience. Out back, a screened-in back porch offers a quiet spot to relax, leading to a private, fenced yard framed by mature shade trees. Homeowners will also appreciate the benefit of a low HOA fee, with amenities such as a pool, basketball and tennis court, playground, dog park, and much more! Located in Winter Springs, this home puts you near top-rated Seminole County schools, local parks, and the Cross Seminole Trail. Enjoy easy access to shopping and dining at the Winter Springs Town Center, with quick routes to SR 417 for a smooth commute to UCF, Oviedo, and Orlando.

654 Cypress Lane, Winter Springs
$375,000
4 Beds ⋅ 4 Baths ⋅ Tuscawilla Unit 12 SubDv. ⋅ 32708 Zip Code
Looking for a home, you can make your own while living in it? This 4-bedroom, 3.5-bath single-family home provides an excellent opportunity for an owner-occupant to move in, make updates over time, and build equity while turning the property into their own. Also, a great opportunity for investors, landlords, and buyers looking for a fix-and-hold or value-add project. Located in the established Tuscawilla/Winter Springs area of Seminole County, this home sits on a spacious 0.34-acre lot enclosed by PVC fencing on all four sides in a nice neighborhood. The home features a huge living room, fireplace, ceiling fans throughout, covered porch, attached 2-car garage, skylights, and a screened lanai with pool and jacuzzi. The primary suite includes a double/split vanity with both a tub and separate shower. The spacious yard provides plenty of room to enjoy the outdoor space and make the property your own. Conveniently located near parks, shopping, schools, museums, UCF, Rollins College in Winter Park, Orlando Sanford International Airport, and Orlando International Airport. Whether you're searching for a fixer-upper, handyman special, owner-occupant opportunity, investment property, rental property, landlord opportunity, or value-add project, this property provides plenty of potential to update, improve, and build value over time. Being sold AS-IS.

1625 White Dove Drive, Winter Springs
$475,000
3 Beds ⋅ 2 Baths ⋅ Deer Run Unit 23a SubDv. ⋅ 32708 Zip Code
Tucked beneath a canopy of majestic oaks in the established Tuscawilla Forest community, this charming 3-bedroom, 2-bath, 2-car garage home offers approximately 1,700 square feet of living space on a spacious .26-acre lot—along with something you simply can't recreate overnight: character, mature landscaping and the welcoming feel of an established neighborhood. Cherished by the same homeowner since 2004, this has been a much-loved home for more than two decades. The owners have especially treasured their wonderful neighbors and convenient location, and now it's time for a new owner to begin their own chapter here. Step inside and you'll immediately appreciate the desirable split-bedroom floor plan, vaulted ceilings and skylights that bring natural light into the main living areas. At the heart of the home, the inviting living space features a double-sided fireplace, warm wood accents and built-in shelving. The kitchen offers real wood cabinetry, generous counter space, breakfast bar, stainless-steel appliances and stylish tile backsplash, opening naturally to the main living area. The primary suite offers a private retreat with a beautifully remodeled bath featuring dual vanities, soaking tub and separate glass-enclosed walk-in shower with striking tile and pebble-stone accents. The secondary bath has also been beautifully remodeled. MAJOR IMPROVEMENTS HAVE ALREADY BEEN MADE, including a NEW ROOF IN 2021 with new gutters and gutter guards, A/C SYSTEM IN 2020 with parts-and-labor warranty noted through 2030, REMODELED BATHROOMS IN 2024, PEX PLUMBING, TWO-TONE VINYL PRIVACY FENCE IN 2023 and NEW ST. AUGUSTINE GRASS IN 2023. Additional improvements include the updated kitchen, lighting and ceiling fans, flooring and sprinkler system. And then there's the OUTDOOR LIVING! Sliding glass doors lead to an expansive screened and covered lanai, perfect for morning coffee, weekend gatherings or simply enjoying Florida living. Beyond the lanai, the large, private fenced backyard is shaded by beautiful mature trees with plenty of room for gardening, pets, play, entertaining—or perhaps that future pool you've been dreaming about. Whether hosting friends, enjoying a quiet evening under the trees or simply unwinding after a long day, this backyard offers the space and privacy to enjoy being home. LOCATION, LOCATION, LOCATION! Enjoy the charm of an established Winter Springs neighborhood with access to Seminole County Public Schools while staying close to everything. Nearby Trotwood Park, Central Winds Park, Bear Creek Nature Trail and the Cross Seminole Trail provide walking, biking, sports, playgrounds and outdoor recreation. Shopping, dining and everyday conveniences are nearby, with easy access to Oviedo, UCF, Winter Park, SR 417 and the greater Orlando area. With its mature surroundings, nearby parks and trails, convenient location and the kind of neighbors the current owners will truly miss, it's easy to understand why they called this home for more than 20 years. Some homes simply have a story—and this one has been loved for more than two decades. Filled with memories and thoughtfully cared for through the years, 288 Ringwood Drive is ready for its next chapter...and its next owner to call it HOME.

288 Ringwood Drive, Winter Springs
$930,000
4 Beds ⋅ 3 Baths ⋅ Bentley Club At Bentley Green SubDv. ⋅ 32708 Zip Code
Welcome to 864 Bentley Green Circle, a move-in ready luxury sanctuary situated on a quiet cul-de-sac lot in Winter Springs. Offering 4 bedrooms, 3 full bathrooms, and over 2,200 square feet of meticulously updated living space, this home seamlessly blends sophisticated interior accents with private, resort-style outdoor living. Arrive via a grand circular drive centered around a professionally landscaped island, featuring a newly updated limestone walkway that creates an elegant entryway. Inside, the light-filled open floor plan boasts high ceilings, newly painted walls, transoms, interior glass doors, and smart recessed lighting with nightlight mode. The main living area features a custom black marble gas fireplace and expansive sliding glass doors leading out to the lanai. A formal dining room offers luxury vinyl flooring, custom crown molding, and a statement chandelier, while a dedicated lounge/den provides cozy custom built-ins and window seats. The gourmet kitchen comes complete with granite countertops, tile flooring, newly installed stainless-steel appliances (including a new refrigerator), and convenient access to a laundry area with a recently purchased, large-capacity washer and dryer set. The main-level owner's retreat serves as a true sanctuary, featuring hardwood floors, a sitting area, a built-in electric wall fireplace, space for a coffee station, a spacious walk-in closet, and a completely updated spa bath with a deep soaking tub and oversized glass shower. Upstairs, three additional hardwood-floored bedrooms include one configured as an executive home office with scenic views of the nearby pond and golf course. Step outside into your private backyard oasis featuring a saltwater pool and spa with a newly renovated screen enclosure, updated pool equipment, gas heater, and multi-color lighting. Relax under the custom covered lanai showcasing a real wood ceiling, ceiling fan, and custom recessed lights—complete with included patio furniture and exterior TV. The grounds feature manicured landscaping with lush palm trees, privacy hedges, and a tranquil side-yard "Zen garden" designed to attract butterflies and hummingbirds. Rounding out this exceptional property are dual driveways and a 2-car workshop garage equipped with built-in storage shelving and a 240-amp EV charging station.

864 Bentley Green Circle, Winter Springs
$665,000
4 Beds ⋅ 3 Baths ⋅ Tuscawilla Unit 14a SubDv. ⋅ 32708 Zip Code
Welcome to this exceptional 4-bedroom, 3-bath pool home with a dedicated office, situated on an oversized corner lot in the heart of Tuscawilla in Winter Springs. Featuring a unique three-way split floor plan, generous indoor and outdoor living spaces, and thoughtful updates throughout, this home offers the perfect combination of functionality, privacy, and Florida living. Step inside through the grand foyer, where a spacious dedicated office sits just off the entry and features French doors, crown molding, beautiful flooring, and plantation shutters. Continue into the inviting living room, highlighted by a brick accent wall, vaulted ceilings, and sweeping views of the pool and lanai. Natural light fills the space through an impressive three-panel sliding glass door that disappears into the wall, creating a seamless transition between indoor and outdoor living—perfect for entertaining. The open floor plan flows into a charming breakfast nook and spacious kitchen featuring an abundance of cabinetry and counter space, stainless steel appliances, and a breakfast bar for casual dining. For larger gatherings and special occasions, the separate formal dining room offers plenty of space and is finished with a beautiful statement chandelier. Privately positioned on one side of the home, the primary suite is a true retreat with vaulted ceilings and its own enclosed Florida room—an incredible space for morning coffee, a reading nook, or peaceful space. The expansive primary bathroom features dual vanities, a brand-new Kohler walk-in shower (2026), and a massive walk-in closet with direct access to the bedroom. The home's thoughtful three-way split design provides exceptional privacy. A second wing features two additional bedrooms and a spacious shared bathroom, while the third wing offers a separate bedroom with its own full bathroom and newly renovated shower (2025)—an ideal setup for guests, extended family, or in-law accommodations. Step outside and experience the Florida lifestyle with a sparkling saltwater pool, new pool heater (2025), and a generous covered lanai designed for year-round entertaining. Beyond the pool, the expansive, fully fenced backyard features new pavers (2024) and plenty of room to relax, play, garden, or entertain. Private and serene, this oversized corner lot provides outdoor space that is increasingly hard to find. Additional highlights include no HOA, a new roof and skylights (2019), new salt cell and pool heater (2024) and brand new A/C (2024). Located in sought-after Seminole County, this home is zoned for Oviedo High School and offers convenient access to everything the Tuscawilla community is known for, including walking trails, public parks, and Tuscawilla Country Club with golf, clay tennis courts, a lap pool, fitness center, and dining. With its oversized lot, three-way split floor plan, private pool, dedicated office, flexible living spaces, and incredible Tuscawilla location, this Winter Springs home delivers the space and lifestyle you've been searching for. Call for your private showing today!

674 Vistawilla Drive, Winter Springs
$415,000
3 Beds ⋅ 2 Baths ⋅ Oak Forest Unit 2b SubDv. ⋅ 32708 Zip Code
Nestled in the desirable Oak Forest at Tuscawilla community, this 3 bedroom, 2 bathroom home is located near local parks, trails, shops, restaurants, and highly rated Seminole County schools. Inside, a spacious, open floor plan flows effortlessly between the living and dining areas, elevated throughout by custom crown molding and rich wood detailing that add a timeless, tailored feel rarely found at this price point. The lovely kitchen anchors the home with a center island and breakfast bar, perfect for casual meals or entertaining guests. The primary suite offers a peaceful retreat with a generous walk-in closet, while the additional bedrooms are equally impressive, each offering generous space and an abundance of natural light. Outside, a screened patio invites year-round outdoor living, and an attached 2 car garage completes this beautiful Winter Springs residence.

1067 Chokecherry Drive, Winter Springs
$499,900
4 Beds ⋅ 3 Baths ⋅ Parkstone SubDv. ⋅ 32708 Zip Code
Virtually Staged. Live the Florida lifestyle in the beautiful gated community of Parkstone! This 4-bedroom, 3-bath pool home offers the perfect combination of comfort, convenience, and resort-style living. Spend sunny afternoons relaxing by your own private screened pool, enjoy morning walks or bike rides along the nearby Cross Seminole Trail, or take advantage of Parkstone’s community pool, tennis and volleyball courts, playgrounds, and lakefront dock on Lake Jesup. Even better, lawn care is included through the HOA, giving you more time to enjoy everything the community has to offer. Inside, the open and inviting layout is designed for both everyday living and entertaining, with spacious gathering areas and easy access to the covered outdoor living and pool area. A downstairs bedroom and full bath provide flexibility for guests, a home office, or multigenerational living, while the spacious primary suite upstairs creates a comfortable private retreat. The home has also been thoughtfully cared for with approximately $5,000 invested in new gutters and an extensive underground drainage system, including underground downspouts and dual French drains. Approximately two tons of river rock, a side-yard walkway, refreshed landscaping in 2026, and refreshed tile grout in all three bathrooms add to the home’s move-in-ready appeal. Whether it’s coffee by the pool, an evening walk through the neighborhood, a bike ride on the trail, or a day enjoying the community amenities, 909 Devon Creek offers more than a home—it offers an easy, active Florida lifestyle.

909 Devon Creek Road, Winter Springs
$497,000
4 Beds ⋅ 3 Baths ⋅ Fox Glen At Chelsea Parc Tuscawilla SubDv. ⋅ 32708 Zip Code
Welcome to this beautiful 4-bedroom home in the heart of Tuscawilla! This well-appointed home offers a comfortable and versatile floor plan with a primary bedroom conveniently located on the main floor. Upstairs, you'll find three additional bedrooms and a spacious loft-perfect for a reading area, sitting room, home office or additional living space. Relax and enjoy the peaceful private garden views from the enclosed patio, creating a wonderful space for morning coffee, entertaining or simply unwinding at the end of the day. Property amenities include a large community pool, jacuzzi, fitness room and clubhouse. Enjoy an exceptional Tuscawilla location near Tuscawilla Country Club, Bear Creek Nature Trail, Sam Smith Park, Trotwood Park and just minutes from the Oviedo Mall and Oviedo on the Park offering a variety of dining, shopping and entertainment options. The home is located within the highly regarded Seminole County Public Schools, an A-rated school district and minutes from University of Central Florida. Conveniently located in Central Florida, approximately an hour from Walt Disney World, Universal Studios and many of Florida's beautiful beaches making this an ideal location for enjoying everything the area provides. Come see why this Tuscawilla home is the perfect combination of comfort, location and convenience!

1610 Fox Glen Court, Winter Springs
$439,900
3 Beds ⋅ 3 Baths ⋅ North Orlando Ranches Sec 08 SubDv. ⋅ 32708 Zip Code
Welcome home to this beautifully maintained 3 bedroom, 2.5 bathroom pool home tucked away on a quiet, well mainicured Winter Springs Street, where pride of ownership shines. Designed with entertaining in mind, the spacious great room features a wood burning fireplace and overlooks the backyard oasis, complete with a fully paved pool deck, bar area, and entertaining garden, an incredible space for relaxing or hosting family and friends. Inside, you'll find new luxury vinyl flooring (2026), updated bathrooms, and a cersatile third bedroom featuring a murphy bed and built-ins, perfect for guests, a home office or both. Major improvements include a NEW ROOF (2023), insulated impact windows, and new gutters. And there's NO HOA! Enjoy the freedom of home ownership along with a fantastic Winter Springs location convenient to restaurants, shopping, SR 417, and I-4, plus highly regarded Seminole County Schools.

625 Pearl Road, Winter Springs
$525,000
4 Beds ⋅ 2 Baths ⋅ Oak Forest Unit 6 SubDv. ⋅ 32708 Zip Code
Welcome home to this spacious 4-bedroom, 2-bath pool home located in the highly desirable Winter Springs community! Designed with a functional split-bedroom floor plan, this home offers the perfect balance of privacy, space, and comfortable everyday living. Step inside to soaring vaulted ceilings, abundant natural light, and separate formal living and dining rooms that provide plenty of flexibility for entertaining, working from home, or gathering with family. The heart of the home opens to a large screened lanai and sparkling pool, creating the perfect setting for Florida living year-round. Whether you’re enjoying a quiet morning outside, hosting friends for a weekend barbecue, or cooling off on a summer afternoon, the expansive outdoor living space is sure to become a favorite part of the home. The generously sized lot offers plenty of room to enjoy the outdoors and also features a storage shed with electricity—ideal for a workshop, hobby space, or additional storage. Major improvements offer added peace of mind, including a NEW ROOF, NEW PLUMBING, and NEW WATER HEATER. Best of all, the home is ideally situated in sought-after Winter Springs within walking distance of the area’s schools, making everyday routines incredibly convenient. With its spacious floor plan, beautiful natural light, private pool, large lot, and valuable recent updates, this home offers an incredible opportunity to enjoy everything Winter Springs has to offer!

699 N Endeavour Drive, Winter Springs
$425,000
3 Beds ⋅ 2 Baths ⋅ Georgetowne Unit 1 SubDv. ⋅ 32708 Zip Code
Welcome to 744 Barrington Circle, a beautifully maintained home nestled in the heart of the sought-after Tuskawilla community of Winter Springs. Tucked away in the desirable Georgetown neighborhood, this 3-bedroom, 2-bath home offers a thoughtful split-bedroom floor plan, soaring vaulted ceilings, abundant natural light, and an inviting blend of indoor and outdoor living. A private courtyard welcomes you into the home, creating a charming space for gardening and enjoying the outdoors. Inside, the open living and dining areas feature beautiful wood floors and vaulted ceilings, creating an airy and spacious feel. The living room flows seamlessly into the Florida room, where three sets of updated sliding glass doors bring the surrounding greenery indoors and open to the tranquil backyard. With a beautiful greenbelt directly behind the property, there are no rear neighbors, offering exceptional privacy. The spacious eat-in kitchen features white cabinetry and stainless steel appliances, while the generously sized primary suite offers double-door entry, plenty of room for a king-size bed, a walk-in closet, built-in vanity, and an ensuite bath with a separate garden tub and shower. The split-bedroom layout provides privacy for everyone, with two additional bedrooms located separately from the primary suite and sharing a full bathroom. Another unique feature is the air-conditioned bonus room within the garage, providing endless possibilities as a home office, gym, workshop, playroom, hobby space, or additional hangout area. Additional updates include new windows and doors, a new garage door, epoxy garage flooring, and fresh exterior paint. Residents of Georgetown enjoy a community pool, while the HOA includes front-yard lawn maintenance, making it easy to enjoy the neighborhood without the added upkeep. The home is also located in a highly desirable school zone, especially Keeth Elementary, and just minutes from Tuskawilla Country Club (membership separate) and Trotwood Park, one of the area's favorite recreational destinations with a splash pad, playground, tennis and pickleball courts, baseball fields, fishing, open green space, pavilions, and picnic areas. Private, peaceful, and perfectly positioned in the heart of Tuskawilla, 744 Barrington Circle offers the space, flexibility, and lifestyle that make this one of Winter Springs' most desirable places to call home.

744 Barrington Circle, Winter Springs
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