Casselberrry/Winter Springs / Tuscawilla Homes with Pool Amenities

Casselberrry/Winter Springs / Tuscawilla Homes with Pool Amenities

Welcome to the enchanting neighborhoods of Casselberry, Winter Springs, and Tuscawilla, nestled in the heart of Seminole County, Florida. This vibrant region boasts a harmonious blend of suburban charm and natural beauty, making it an ideal place to call home. With scenic parks, top-rated schools, and a strong sense of community, residents enjoy a lifestyle that balances relaxation and recreation.

Winter Springs is particularly renowned for its family-friendly atmosphere and an abundance of outdoor activities. The area is dotted with picturesque parks and trails, perfect for weekend picnics or evening strolls. Tuscawilla, with its lush landscapes and golf courses, offers a serene escape while still being conveniently located near shopping, dining, and entertainment options. Casselberry adds to the region's allure with its eclectic mix of shops and restaurants, along with its inviting community events that foster connections among neighbors.

For those seeking a home that enhances their lifestyle, the properties in this area often come with sought-after pool amenities. Imagine coming home to your own private oasis, where you can unwind by the poolside after a long day or host summer barbecues with friends and family. Homes featuring pools not only provide a refreshing retreat but also add significant value to your investment.

Whether you're looking for a cozy family home or a luxurious retreat, the Casselberry, Winter Springs, and Tuscawilla area offers a diverse selection of properties that cater to every taste and budget. Dive into the Florida lifestyle and discover your dream home in this captivating region!

Newest Casselberrry/Winter Springs / Tuscawilla Homes with Pool Amenities

$512,000
3 Beds ⋅ 3 Baths ⋅ Hickory Grove Twnhms SubDv. ⋅ 32708 Zip Code
Beautifully Upgraded Sofia Model Townhome on a Premium Conservation Lot! Welcome home to this exceptional Sofia Model townhome, featuring one of the community’s most desirable floorplans—with the primary suite conveniently located on the first floor and two additional bedrooms upstairs. This thoughtfully designed layout is ideal for families, first-time buyers, those looking to downsize, or anyone seeking comfortable living with flexibility for guests, a home office, or additional living space. Situated on a premium lot backing to a peaceful conservation/green area, this home offers a wonderful sense of privacy and a tranquil natural backdrop. Inside, numerous builder upgrades and thoughtful custom enhancements create a beautiful blend of modern style, classic elegance, and everyday functionality. Upgrades include enhanced tile, bathrooms, and kitchen finishes, complemented by a custom-designed stair railing that adds a distinctive touch of sophistication. The spacious primary suite features a custom-built walk-in closet, maximizing storage and organization. An Ecobee Smart Thermostat system with Smart Sensors provides efficient, convenient control of the home's comfort while helping manage energy usage. Premium professionally installed ceiling fans in every room provide excellent air circulation and year-round comfort. The home is also professionally wired for rear surround-sound speakers, making it ready for an enhanced entertainment experience. All the rooms have plenty of natural lights! The garage is equally practical, featuring large custom-built ceiling-hung storage, providing valuable additional space while keeping vehicles and everyday belongings organized. Enjoy an outstanding location within Hickory Grove. The community pool and dog park are just down the street, while the Cross Seminole Trail can be easily accessed just outside the community—perfect for walking, jogging, or biking. The Magnolia Square Fountain and Park and The Winter Springs Town Center are both approximately a five-minute walk away, with roughly a dozen food-and-beverage places within walking distance or a short drive away. Central Winds Park is only about a 10-minute drive away. Access to 417 is about 7-minute drive away. With its highly sought-after first-floor primary suite, premium conservation lot, extensive upgrades, custom touches, and exceptional walkable location, this townhome offers a rare combination of comfort, style, privacy, and convenience.

1378 Tarflower 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
$175,000
2 Beds ⋅ 2 Baths ⋅ Mount Greenwood Unit 4 Of SubDv. ⋅ 32708 Zip Code
INVESTOR SPECIAL! RENOVATION OPPORTUNITY IN WINTER SPRINGS! Bring your vision and transform this 2-bedroom, 1.5-bath townhouse into something special. This property is being sold AS-IS and is in need of a full renovation, offering an excellent opportunity for investors, renovators, or buyers looking to create a home tailored to their own style. The two-story layout features a spacious living room, first-floor kitchen, and two bedrooms upstairs, including a generously sized primary bedroom. A rear porch with storage provides additional outdoor space, while the community offers a pool, playground, and tennis courts for residents to enjoy. The property also includes assigned parking with a spot right out front. Located in Winter Springs with convenient access to major roads, shopping, dining, parks, and area schools, this property has the potential to become a fantastic primary residence, rental, or investment project. Bring your contractor, bring your vision, and unlock the potential! Cash financing only. Buyer to independently verify all information, measurements, restrictions, and renovation requirements.

284 Woodgreen Lane, 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
$369,500
3 Beds ⋅ 4 Baths ⋅ Jesups Reserve Twnhms Rep SubDv. ⋅ 32708 Zip Code
Welcome to 412 Blue Bayou, your beautifully refreshed oasis in Jessups Reserve in Winter Springs! This exceptional home stands out with 3 fully en-suite bedrooms and a carpet-free interior featuring laminate flooring throughout and a brand-new stair railing. The downstairs bedroom can be used as a guest bedroom, office or flex space. Complete peace of mind comes standard thanks to major recent capital upgrades, including a ROOF replacement (2022), a brand-new A/C system (2023), and professional garage door maintenance (2024). The primary suite, situated on the third floor for added privacy, features a large walk-in closet, a soaking tub and separate shower, offering a peaceful retreat away from the home's common areas Enjoy effortless Florida living while cooling off in the community pool and soak away the stress of life in the spa. Unwind at the end of the day in three distinct outdoor spaces: a welcoming front porch, a renovated second-floor patio, and a private third-floor balcony. Convenient location is a bonus: walk across the street to Publix when you run out of sugar, check out the live music at Wine Lounge or hit your fitness goals at Crunch Fitness. The main level boasts a bright, open-concept living and dining area, along with a spacious kitchen equipped with stainless steel appliances in excellent condition and a generous breakfast bar; a convenient laundry area is also located on this floor. A spacious two-car garage comes fully equipped with additional smart storage solutions to keep your life organized and functional. Additional bonuses can be found at the Winter Springs Town Center (Aldi, Hiking/Biking Trails and more). Perfectly priced at $369,500, this turn-key property is ready for its next chapter!

412 Blue Bayou Lane, Winter Springs
$344,900
3 Beds ⋅ 3 Baths ⋅ Tuscawilla Braewick At Ph 1 SubDv. ⋅ 32708 Zip Code
Welcome to 1482 Creekside Circle — a MOVE-IN READY 3-bedroom, 2.5-bath townhome offering thoughtful updates, private outdoor space, and community amenities. This UPDATED Winter Springs townhome features ALL NEW APPLIANCES, UPDATED BATHROOMS, and has been completely replumbed. Major improvements are already taken care of, including a NEW AC IN 2026, WATER HEATER REPLACED IN 2023, and a NEW GARAGE DOOR IN 2026. Upstairs, BRAND-NEW CARPET throughout the bedrooms adds to the fresh, move-in-ready feel. Enjoy Florida living from the PRIVATE SCREENED-IN PATIO overlooking your own small BACKYARD — perfect for morning coffee, pets, or relaxing outdoors. A ONE-CAR GARAGE provides additional parking and storage, while the HOA has recently repainted the exterior for a fresh, well-maintained appearance. The community offers a POOL and FITNESS CENTER, adding to the ease of low-maintenance townhome living. With so many recent updates already completed, 1482 Creekside Circle is a great opportunity for buyers looking to just move in and enjoy!

1482 Creekside Circle, Winter Springs
$284,000
3 Beds ⋅ 2 Baths ⋅ Seasons The SubDv. ⋅ 32708 Zip Code
Welcome to 412 Horizon Drive, a well maintained home in the heart of Winter Springs with the updates already taken care of. Inside, you’ll find a welcoming kitchen with granite countertops, stylish cabinetry, stainless steel appliances, and ceramic tile and wood laminate flooring throughout. The primary bathroom is a standout, featuring a barn door entry, large tiled shower, rainfall shower system, and handheld wand. Recent improvements include a 2018 roof, 2019 HVAC and refrigerator, stove and microwave replaced in 2024, updated windows, and fresh exterior paint completed in August 2026. The backyard offers plenty of room to entertain, relax, or create your own outdoor retreat. Conveniently located near shopping, dining, parks, and everyday conveniences, this Winter Springs home is ready for its next owner.

412 Horizon Drive, Winter Springs
$267,500
3 Beds ⋅ 3 Baths ⋅ Tuscany Place Ph 1 SubDv. ⋅ 32708 Zip Code
Welcome to Tuscany Place in the heart of sought after Tuscawilla! This townhouse styles condo offers a open floor plan with abundant natural light, generous living and dining areas, peaceful green back yard and spacious kitchen perfect for everyday living and entertaining. All bedrooms are upstairs with 2 full bathrooms and laundry. Enjoy the greenery, calmness of the shaded outdoor patio; ideal for relaxing after a long day or lounging. This popular gated community offers many amenities including a community pool, beautifully maintained grounds, located within walking distance to Trotwood Park & little shops AND close to all major roads, amenities, schools, medical facilities, shopping, dining, schools, golf course and parks. A fantastic opportunity to enjoy the Winter Springs lifestyle! Great opportunity to enjoy this community & put your personal touches to this home. Priced to sell Motivated seller, bring your offers!

600 Northern Way Unit 1108, Winter Springs
$295,900
3 Beds ⋅ 2 Baths ⋅ Wildwood SubDv. ⋅ 32708 Zip Code
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
$275,000
3 Beds ⋅ 2 Baths ⋅ Deersong 2 SubDv. ⋅ 32708 Zip Code
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
$234,900
2 Beds ⋅ 3 Baths ⋅ Casa Park Villas Ph 1 SubDv. ⋅ 32708 Zip Code
Welcome to 611 Casa Court, Unit A, a well-located 2-bedroom, 2.5-bath condo offering 1,156 square feet of living space and a great opportunity for an investor or future owner-occupant. The two-story layout provides comfortable separation between the main living areas and bedrooms, with a convenient half bath downstairs and private baths upstairs. Enjoy outdoor space just outside your door along with the benefits of a community setting and shared amenities. Conveniently located near shopping, dining, major roadways, and everything the surrounding Orlando area has to offer, this property provides easy access for everyday living. Whether you're looking to add to your rental portfolio or purchase a property with long-term potential, Unit A offers an affordable opportunity in a convenient Central Florida location.

611 Casa Park A Court, 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
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