Casselberrry/Winter Springs / Tuscawilla Homes for Sale

Casselberrry/Winter Springs / Tuscawilla Homes for Sale

Casselberry/Winter Springs/Tuscawilla is a vibrant region located in Seminole County, Florida. Nestled in the heart of Winter Springs, this area offers a perfect blend of suburban charm and urban convenience. With a rich history and a strong sense of community, Casselberry/Winter Springs/Tuscawilla is an ideal place to call home.

If you're looking for homes for sale in this region, you're in luck. The real estate market here is thriving, with a wide range of options to suit every taste and budget. From cozy single-family homes to spacious estates, there is something for everyone in Casselberry/Winter Springs/Tuscawilla.

One of the highlights of this area is its natural beauty. With numerous parks, lakes, and trails, outdoor enthusiasts will find plenty of opportunities to explore and enjoy the great outdoors. Whether you prefer hiking, biking, or simply taking a leisurely stroll, you'll be amazed by the picturesque scenery that surrounds you.

In addition to its natural attractions, Casselberry/Winter Springs/Tuscawilla also boasts a bustling commercial district. From local boutiques and restaurants to major shopping centers, you'll find everything you need just a short drive away.

With its excellent schools, friendly neighborhoods, and convenient location, Casselberry/Winter Springs/Tuscawilla is a sought-after destination for homebuyers. Don't miss out on the opportunity to make this wonderful region your new home. Contact a local real estate agent today to explore the homes for sale in Casselberry/Winter Springs/Tuscawilla and start your journey towards finding your dream home.

Newest Casselberrry/Winter Springs / Tuscawilla Homes for Sale

$644,900
4 Beds ⋅ 3 Baths ⋅ O6436630 MLS
There’s something about a home that makes everyday life feel a little more like vacation and this Winter Springs pool home delivers just that. Set on a spacious lot in the established Huntridge community, this 4-bedroom, 3-bath home offers nearly 2,850 square feet with room to gather, work, entertain and unwind. Soaring ceilings and abundant natural light create an open, airy feel, while the family room with wood-burning fireplace gives the home a warm, inviting center. A separate office/bonus space adds flexibility for working from home, hobbies or a quiet retreat. Out back, bring vacation home with your own private pool, covered lanai and summer kitchen, an ideal setup for long Florida afternoons, weekend cookouts and evenings spent lingering outside. The primary suite opens directly to the pool area and features a generous walk-in closet and spacious bath. Beyond the house, Winter Springs offers an easygoing, outdoor-focused lifestyle with nearby Trotwood Park, miles of walking and biking along the Cross Seminole Trail, Tuscawilla Country Club, and shopping and dining around Winter Springs Town Center and Tuskawilla Road.

248 Huntridge Way, Winter Springs
$349,000
3 Beds ⋅ 2 Baths ⋅ O6436607 MLS
ADORABLE and MOVE-IN READY! Whether you're a FIRST-TIME HOMEBUYER or looking to "RIGHT-SIZE" into a more manageable home without sacrificing comfort. This charming 3-Bedroom, 2-Bath WATER-FRONT HOME will meet your needs and more. Paddleboard or canoe on the Water out back! Step inside to discover a bright and inviting open floor plan featuring soaring vaulted ceilings, abundant natural light, and a desirable split-bedroom layout that offers both privacy and functionality. The private OWNER'S SUITE serves as a relaxing retreat with a Vaulted Ceiling, a generous WALK-IN CLOSET and an ENSUITE BATH with a LARGE SHOWER. Nice size Secondary Bedrooms and Hall Bath with Tub/Shower on the opposite side of the home. Double Pane Windows and Sliding Glass Doors to the Back Patio which includes a Pergola with Covering, Fully Fenced Backyard and a variety of Fruit plants and trees; such as Pineapples and Bananas. New WATER HEATER just installed and permitted, ROOF 2021, with a partial reroof 2024, permitted; A/C 2013. New Frigidaire Range and Newer Washer and Dryer. NO HOA! Zoned for Winter Springs top-rated Schools. **Professional Photos Coming Soon!**

203 Cottonwood Drive, Winter Springs
$549,000
4 Beds ⋅ 3 Baths ⋅ O6436090 MLS
Spacious 4 bedroom, 3 bathroom pool home off of Tuskawilla Rd! This home features two story ceiling in the formal living and dining room. The staircase and second story walkway over look the entrance and formal areas. The family room has a fireplace and is joined with the kitchen. On the first floor are also three large bedrooms, two of the bedrooms have attached baths. The primary bedroom is upstairs and has double walk in closets, and an oversized en suite bathroom. The pool has a screen enclosure and the yard is fenced. Roof replaced in 2022, complete Replumb ins 2023.

1142 Oday Drive, Winter Springs
$442,000
3 Beds ⋅ 3 Baths ⋅ O6436014 MLS
?? Welcome Home to Your Winter Springs Garden Oasis! Step into the warmth and charm of this lovingly maintained 3-bedroom, 2-bathroom home, perfectly situated in the heart of Winter Springs, Florida. From the moment you arrive, it’s clear this home has been cared for with pride, offering a welcoming atmosphere both inside and out. One of the true highlights is the beautifully manicured, fully landscaped grounds that surround the entire home. Thoughtfully selected plantings, mature greenery, and carefully maintained gardens create a sense of privacy and tranquility at every turn. Every detail has been thoughtfully considered to create an inviting outdoor retreat. Step out back and discover your own garden oasis! The extended screened porch provides the perfect setting for morning coffee, afternoon relaxation, or gathering with friends and family while enjoying the peaceful beauty of the surrounding landscape. The lush landscaping creates a wonderful backdrop and makes this outdoor space feel like a private retreat. Located in the heart of desirable Winter Springs, this charming home offers the perfect blend of comfort, character, and Florida outdoor living. If you’ve been looking for a home that feels welcoming, cared for, and truly special, this garden retreat is ready to welcome you home.

107 Peregrine Court, Winter Springs
$650,000
4 Beds ⋅ 3 Baths ⋅ O6435785 MLS
UPDATED WINTER SPRINGS POOL HOME IN THE HIGHLY DESIRABLE TUSKAWILLA AREA! Welcome to 4951 Courtland Loop, where timeless character, extensive upgrades and the Florida lifestyle come together. This impressive .38-acre homesite is surrounded by beautiful mature oaks. TUSKABAY is located in the heart of TUSCAWILLA, one of ORLANDO's Best COMMUNITIES. Offering 4 bedrooms, 3 full baths and 2,562 square feet, this is the MOVE-IN READY Winter Springs home you've been waiting for. Top features include a desirable FIRST-FLOOR PRIMARY & Sec.Bedrooms, Gourmet KITCHEN, SIDE-ENTRY GARAGE, spacious living areas and impressive indoor-outdoor layout designed for entertaining. Main entry offers view of large living area with cozy, BRICK WOOD BURNING FIREPLACE with POOL & YARD VIEWS. OPEN CONCEPT DINING- LIVING ROOM COMBO flanking the kitchen, primary and secondary downstairs' bedrooms flows.The PRIMARY BEDROOM boasts CATHEDRAL CEILINGS, DOUBLE CLOSETS, TRANSOM/FULL LENGTH WINDOWS, immersing the room in natural light. Warm, wood style flooring contrasts the lighter finishes exquisitely and leads to the ENSUITE, LUXURY BATHROOM. The remodeled primary bath adds another touch of luxury with QUARTZ COUNTERTOPS, GOLD FINISHES, FARMHOUSE-STYLE SINK and GLASS ENCLOSED SHOWER with SUBWAY TILE. At the heart of the home is a beautifully RENOVATED KITCHEN offering a timeless look,appealing to discriminating buyers. Crisp, LIGHT CABINETRY with clean lines offers abundant storage, complemented by EXPANSIVE QUARTZ COUNTERTOPS and a classic backsplash. The butcher-block island compliments the STAINLESS STEEL APPLIANCES package including the JennAir range, low maintenance KitchenAid appliances with double oven, dishwasher, wine and beverage cooler. This kitchen was created for everyday living and entertaining, blending style and practicality. Upstairs you'll find two large, private bedrooms with a bathroom and loft view of the downstairs. Through the FRENCH DOORS to the outside you'll discover your own backyard retreat. Enjoy the swaying oak trees from your private lanai, in-ground POOL, expansive PAVER PATIO, extended walkways, over .38 ACRE FENCED YARD and mature landscaping provide an incredible setting for weekend gatherings, quiet mornings and year-round outdoor living. Enjoy the parklike feel from the comfort of home. Even more impressive is the investment already made in the home's major systems available to a buyer without having to assume the payment or finance a new roof or solar system. Buy HASSLE FREE, no insurance issues here with a 2021 installed roof, seller-owned 11.745 kW solar system, TESLA POWERWALL BATTERY, DOUBLE PANE WINDOWS, high-efficiency heat-pump water heater, WHOLE-HOME WATER FILTRATION AND SOFTENER, Nest thermostats and EV CHARGING combine modern technology with energy-conscious living. The sellers' transfer offers an incredible opportunity for a savvy buyer to buy an outstanding home at an even better VALUE. Too many improvements like upgraded irrigation, newer gutters and additional improvements to mention that make this home truly stand apart. If you've been searching for a WINTER SPRINGS POOL HOME, Tuskawilla home, updated 4-bedroom home, energy-efficient home or move-in-ready home in Seminole County, 4951 Courtland Loop deserves to be at the top of your list. Space. Pool. Upgrades. Energy efficiency. Exceptional Winter Springs LIFESTYLE. This is the home buyers have been waiting for—schedule your private showing today.

4951 Courtland Loop, Winter Springs
$439,000
3 Beds ⋅ 2 Baths ⋅ O6435377 MLS
Welcome to this beautifully maintained 3-bedroom, 2-bath POOL home nestled on a quiet, tree-lined street in the highly sought-after Country Club Village of Tuscawilla. This inviting home offers a versatile floor plan ideal for both everyday living and entertaining, with volume ceilings, abundant natural light, and attractive, low-maintenance tile and luxury vinyl plank flooring throughout. The spacious living and dining areas provide wonderful flexibility and can easily be arranged to complement your lifestyle. At the heart of the home, the kitchen overlooks the dinette and family room and features stainless steel appliances, ample prep and storage space, pull-out drawers, a built-in pantry and built-in wine rack. Its thoughtful location also offers possibilities to open or expand the kitchen toward the rear of the home, creating an even greater connection to the outdoor living and pool area. A charming greenhouse window in the dinette is perfect for growing fresh herbs or displaying your favorite plants. The spacious owner's suite provides a relaxing retreat with direct access to the back porch, a beautifully updated shower and vanity with granite countertop, an oversized window overlooking the atrium, and generous closet space. Two sizable secondary bedrooms are located toward the front of the home, with one offering direct access to the charming atrium. Step outside and enjoy your morning coffee or unwind at the end of the day on the private back patio overlooking the sparkling pool and hot tub, all tucked behind a privacy wall to create your own peaceful outdoor retreat. The pool screen was replaced in 2022 for added peace of mind. The OVERSIZED two-car garage is another standout feature, offering an extended workshop area with ample room for a golf cart, along with built-in shelving, attic stair access and a convenient rear-exit door. Country Club Village offers the perfect combination of a peaceful neighborhood setting and exceptional convenience. Located adjacent to Tuscawilla Country Club, optional memberships provide access to golf, tennis, fitness facilities, social activities, clubhouse amenities and more. Enjoy nearby parks and nature trails, highly rated Seminole County schools, shopping and dining, along with convenient access to UCF, Seminole State College, Orlando Sanford International Airport, Orlando International Airport and major roadways 417, 408, 528 and I-4. Don't miss the opportunity to make this exceptional Tuscawilla pool home your own—schedule your private showing today!

1162 E Winged Foot Circle, Winter Springs
$300,000
3 Beds ⋅ 3 Baths ⋅ O6435319 MLS
Welcome to 412 Horizon Drive, a beautifully maintained home in the desirable Winter Springs community. The inviting kitchen features granite countertops, stylish cabinetry, and stainless-steel appliances, while ceramic tile and wood-laminate flooring provide a cohesive flow throughout the home. The primary suite is highlighted by a spa-inspired bathroom with a barn-door entry, an expansive tiled shower, and a rainfall-style multifunction shower system with a handheld wand. Additional features include generous living spaces, ceiling fans, updated windows, a 2018 roof, a 2018 A/C system, and new exterior paint completed in 8/2026. The spacious yard is ready for outdoor entertaining. Conveniently located near shopping, dining, parks, and everyday amenities. This is a home you will not want to miss!

412 Horizon Drive, Winter Springs
$449,700
3 Beds ⋅ 2 Baths ⋅ O6432192 MLS
Welcome to 806 Big Buck Circle, a charming 3-bedroom, 2-bath home offering 1,887 square feet of living space in the established Oak Forest community of Winter Springs. This single-story home offers a comfortable, functional layout with plenty of opportunity to make it your own. Step outside to the screened-in back porch, a wonderful spot for morning coffee, outdoor dining, or relaxing while overlooking the spacious, grassy backyard. Enjoy all that Winter Springs has to offer with nearby parks, trails, shopping, dining, and recreation. Trotwood Park is just minutes away, with additional outdoor destinations including Central Winds Park and the Cross Seminole Trail. Winter Springs Town Center, Oviedo Mall, grocery stores, restaurants, and everyday conveniences are also within easy reach. Convenient access to SR-434 and SR-417 makes it easy to reach Oviedo, Winter Park, Lake Mary, UCF, and the greater Orlando area. With three bedrooms, a two-car garage, generous backyard space, and a screened outdoor living area, this well-loved home is ready for its next chapter. Come see the possibilities at 806 Big Buck Circle!

806 Big Buck Circle, Winter Springs
$298,900
3 Beds ⋅ 2 Baths ⋅ O6433718 MLS
SINGLE FAMILY HOME. Stunningly Renovated Gem in Winter Springs. Looking for the perfect blend of modern comfort and community living? Look no further! This spectacular, Renovated home in the desirable Wildwood community is ready for its new owners. Brand New Solar Panel System, Green energy. Paid off. This almost 1,300 sq. ft. residence has been thoughtfully updated with high-end finishes throughout. Offers New roof in 2022. New cabinets and stunning granite countertops. Modern Baths with Porcelain wall tiles, new vanities, and upgraded faucets. Fresh paint inside and out, new baseboards, and elegant tile flooring. Resently replace water heater, A/C unit 2018 . 3 Bedrooms, 2 Bathrooms, spacious living and dining areas, plus a garage and carport. Community & Location Benefits: Enjoy the active Wildwood lifestyle with access to a pool, playground, tennis court, and volleyball court. You will be perfectly positioned in a top-rated school district with easy access to major highways (434, 17-92, I-4, 417, 436) and minutes away from the Altamonte Mall, Lake Mary, premier shopping, dining, and healthcare.

736 Summerland Drive, Winter Springs
$510,000
3 Beds ⋅ 2 Baths ⋅ P4939571 MLS
Property is well maintained, had been owned by a former major league baseball prayer. Adjacent to a nice secluded pond. The pool and lanai area is wonderful for quiet sitting, meditation, reading and then jump into the pool for a refreshing dip. The subdivision is one minute from a convenience store and access to Rt 417 highway to all parts of Central Florida. Spacious master bedroom with very big walk-in closet. This is in move-in condition subject only to your color decorations. Part of the Tuscawilla Master Community !!

133 Redtail Place, Winter Springs
$797,500
3 Beds ⋅ 2 Baths ⋅ O6431657 MLS
ONE OF A KIND! Stunning Renovated Lakefront Home on a Private 2 Acre Peninsula – Welcome to your fully reimagined lakefront retreat at 1450 Bird Road in the heart of Winter Springs. Nestled along the serene shores of Lake Tony, this highly detailed, professionally rehabbed home blends modern luxury with timeless Florida charm. From the moment you arrive, you’ll notice the thoughtful craftsmanship and attention to detail throughout. The home has been completely renovated from top to bottom, featuring a bright, open-concept layout with abundant natural light and stunning lake views from multiple living spaces. The designer kitchen is a true centerpiece, showcasing amazing cabinetry, premium quartz countertops, stainless steel appliances, and a spacious island perfect for entertaining. The living and dining areas flow seamlessly, creating an inviting space for gatherings or quiet evenings overlooking the water. Retreat to the primary suite, where you’ll find a spa-inspired bathroom with high-end finishes, elegant tile work, and a relaxing atmosphere designed for comfort. Most appealing is the OVER-SIZED FAMILY/ FLORIDA ROOM, multiple spaces with FULL LAKE VIEWS! Additional bedrooms offer flexibility for guests, family, or a home office. Step outside to your private backyard oasis, where you can enjoy peaceful mornings or breathtaking sunsets on Lake Tony. Whether you’re kayaking, fishing, or simply unwinding by the water, this property offers the ultimate lakefront lifestyle. Additional upgrades include updated systems, modern fixtures, and quality finishes throughout—providing peace of mind and move-in-ready convenience. Located in a desirable Winter Springs neighborhood with easy access to top-rated schools, parks, shopping, and dining, this home is a rare opportunity to own a turnkey lakefront property offering a Lot-Split Option where you could build another home. Don’t miss your chance to experience luxury living on Lake Tony—schedule your private showing today.

1450 Bird Road, Winter Springs
$275,000
3 Beds ⋅ 2 Baths ⋅ S5155512 MLS
Welcome to this beautifully updated 3-bedroom, 2-bath home in the desirable Deer Song community of Winter Springs! Offering 1,105 square feet of thoughtfully designed living space, this move-in-ready home combines modern updates, smart-home technology, energy efficiency, and comfortable Florida living. Step inside to a bright, welcoming interior featuring fresh paint throughout and an updated kitchen with stainless steel appliances and a Samsung Smart Refrigerator with Family Hub Touchscreen. Both bathrooms have been fully updated with modern finishes and smart mirrors, adding style and technology throughout the home. Major improvements include a complete whole-home re-pipe in 2023, and an HVAC UV light system designed to support indoor air quality. Step outside to the screened-in back porch with newly finished epoxy flooring—the perfect place to relax and enjoy the private backyard. A separate storage shed provides additional space for tools, outdoor equipment, and more. Energy-efficient living is made easier with solar panels that help keep monthly electric costs low Enjoy access to the community pool and a convenient Winter Springs location near shopping, dining, parks, recreation, A-Rated Seminole County Public schools, and more. Come see what makes 272 San Gabriel Street such a sweet place to call home!

272 San Gabriel Street, Winter Springs
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