Casselberrry/Winter Springs / Tuscawilla Homes with Playground Community Features

Casselberrry/Winter Springs / Tuscawilla Homes with Playground Community Features

Welcome to the enchanting region of Casselberry, Winter Springs, and Tuscawilla, nestled in the heart of Seminole County, Florida. This vibrant community seamlessly blends suburban charm with the conveniences of modern living, making it an ideal destination for families and individuals alike.

Winter Springs, known for its picturesque landscapes and lush greenery, offers a serene environment with an abundance of parks and recreational facilities. The area boasts a strong sense of community, where neighbors become friends, and local events foster a welcoming atmosphere. Residents enjoy the easy access to top-rated schools, shopping centers, and dining options, ensuring that everything you need is just a stone's throw away.

Tuscawilla, a gem within Winter Springs, is particularly renowned for its family-friendly amenities. Many homes in this area are part of vibrant communities that feature playgrounds, perfect for children to explore and make lifelong memories. These playgrounds are not just about fun; they serve as gathering spots for families, encouraging outdoor activities and fostering connections among neighbors.

Whether you’re strolling through the scenic parks, enjoying a weekend at the local farmers' market, or engaging in community events, Casselberry, Winter Springs, and Tuscawilla offer a lifestyle that truly embraces the essence of Florida living. With a variety of homes available, many equipped with playground community features, you’re sure to find the perfect place to call home in this delightful region. Come experience the charm and warmth of this wonderful community – your dream home awaits!

Newest Casselberrry/Winter Springs / Tuscawilla Homes with Playground Community Features

$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
$399,000
3 Beds ⋅ 3 Baths ⋅ Hickory Grove Twnhms SubDv. ⋅ 32708 Zip Code
Built in 2024 and located in the desirable Hickory Grove community of Winter Springs, this move-in-ready home offers modern style, low-maintenance living, and everyday convenience. Featuring 3 bedrooms, 2.5 bathrooms, and a 2-car garage, the home welcomes you with an open-concept layout filled with natural light. The modern kitchen is designed for both entertaining and everyday living with stainless steel appliances, quartz countertops, and a large center island overlooking the main living area. Upstairs, the spacious primary suite provides a private retreat with an en-suite bathroom and generous closet space, while two additional bedrooms offer plenty of flexibility for family, guests, or a home office. Enjoy maintenance-free living with an impressive list of community amenities just steps from your front door, including a resort-style pool and cabana, playground, dog park, serene green spaces, fountains, and walking paths. Monthly HOA dues include landscaping, irrigation, weed control, exterior paint, roof maintenance, 1GB high-speed internet, and a premium cable package. Conveniently located across the street from Winter Springs Town Center, you’ll have shopping, dining, and everyday conveniences just steps away, all while being near top-rated schools and everything Winter Springs has to offer. With its like-new condition, remaining builder warranty, and sought-after location, this home is ready for its next owner!

1406 Blumberg Boulevard, Winter Springs
$629,999
4 Beds ⋅ 2 Baths ⋅ Avery Park SubDv. ⋅ 32708 Zip Code
Welcome to this beautifully upgraded 4-bedroom, 2-bathroom home in Avery Park, where modern finishes, impressive architectural details, and incredible indoor-outdoor living come together. A generous front porch overlooks the community’s large pond, creating a peaceful setting to enjoy your morning coffee or unwind at the end of the day. Inside, the formal entry hall immediately makes an impression with Venetian plaster niches, soaring 10-foot ceilings, crown molding, and artist-painted raised tray ceilings. The thoughtful details continue throughout the home, including a private office with crown molding and recessed lighting, along with formal living and dining rooms featuring beautiful tray ceilings. The kitchen is designed for both everyday living and entertaining, featuring a large island with seating, stainless steel appliances, a walk-in pantry, and a beautiful backsplash. A spacious interior laundry room provides additional storage and convenience. The primary suite offers its own retreat with beautiful tray ceilings, his-and-hers closets, and an updated ensuite bath featuring a spacious walk-in shower with frameless glass, floor-to-ceiling tile, and built-in niches. French doors open directly to the wood-ceilinged rear porch and private garden beyond. Another bedroom also features its own ensuite bathroom, offering added privacy and convenience for guests or family. Upstairs, a large private bonus room offers endless possibilities as an additional bedroom, art studio, hobby space, media room, home gym, or whatever best fits your lifestyle. Step outside to a lush backyard oasis surrounded by mature vegetation, complete with your own private pond and spa/hot tub. Whether entertaining, relaxing on the porch, or simply enjoying the peaceful surroundings, this outdoor space feels tucked away from it all. A rear-entry three-car garage adds even more functionality while maintaining the home’s inviting curb appeal. Located within Avery Park, a premier gated community offering resort-style amenities including a neighborhood pool, playground, basketball court, and stocked fishing pond. The home is also zoned for highly rated Seminole County schools and conveniently located near Winter Springs Town Center, the Cross Seminole Trail, Central Winds Park, SR 417, shopping, dining, and more. With upgraded interiors, flexible living spaces, a three-car garage, and a private backyard retreat, this home offers something special both inside and out.

116 Avery Lake Drive, Winter Springs
$280,000
3 Beds ⋅ 3 Baths ⋅ Heritage Park Twnhms SubDv. ⋅ 32708 Zip Code
Welcome to this beautifully maintained 3-bedroom, 2.5-bath townhome located in the desirable gated community of Heritage Park in Winter Springs. Designed for comfortable, low-maintenance living, this home features an open-concept floor plan with wood flooring throughout—no carpet! The kitchen overlooks the living and dining areas and features stainless steel appliances, a tile backsplash, 42-inch crown-topped cabinetry, a closet pantry, and breakfast bar, 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. Two additional bedrooms, a remodeled full bath, and a conveniently located second-floor laundry room with washer and dryer included complete the upper level. Additional highlights include a 2023 roof, attached one-car garage, and screen-enclosed porch perfect for enjoying the Florida lifestyle. Heritage Park residents enjoy access to a community pool and playground, all within a gated setting. Conveniently located near Winter Springs Town Center, shopping, dining, and major roadways, and zoned for A-rated Seminole County schools.

476 Tradition Lane, 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
$374,900
3 Beds ⋅ 3 Baths ⋅ Greenspointe SubDv. ⋅ 32708 Zip Code
Welcome to this beautifully updated 3 bedroom, 3 bath home nestled in an established Winter Springs community! Conveniently located near shopping, dining, parks, and major roadways, including SR 417 and I-4, this home combines comfort, style, and an incredibly versatile floor plan. Freshly painted inside and out, the home features new carpet, updated bathrooms, and spacious living areas filled with natural light. The beautifully updated kitchen showcases soft close cabinetry, quartz countertops, stainless steel appliances, and a modern tile backsplash. A unique kitchen opening overlooks the adjacent nook and provides views of the outdoors, creating an open and connected feel. The spacious living room is designed for both relaxing and entertaining, featuring a wood burning fireplace, ceiling fan, and large windows overlooking the lush backyard. The versatile bedroom layout is truly a standout feature. One bedroom and a full bathroom are located downstairs, while the two upstairs bedrooms each feature their own private en-suite bathroom, providing excellent privacy and flexibility for family, guests, or a dedicated home office or guest space. Sliding glass doors lead to an impressive elevated balcony, while the lower level provides additional patio space for enjoying the peaceful outdoor setting. Step outside and enjoy a private backyard surrounded by mature tropical landscaping and no rear neighbors, creating a peaceful Florida retreat. A two car garage and durable tile roof add even more appeal. With its stylish updates, unique floor plan, private outdoor spaces, and exceptional bedroom configuration, this Winter Springs home is a rare find that combines space, comfort, privacy, and functionality. Schedule your private showing today!

662 Nighthawk Circle, Winter Springs
$439,900
3 Beds ⋅ 2 Baths ⋅ Greenbriar SubDv. ⋅ 32708 Zip Code
Welcome home to this beautiful, move-in ready single-story residence situated in the highly desirable Greenbriar community in Winter Springs! Nestled along the manicured grounds near Tuscawilla Golf and Country Club, this updated 3-bedroom, 2-bathroom home features 1,587 sq. ft. of comfortable, functional living space with a 2-car attached garage. Major big-ticket improvements offer complete peace of mind, including a brand-new roof, new energy-efficient windows, a new water heater, and a 5-year-young HVAC system. Step inside to an inviting open layout filled with natural light and stylish upgrades throughout. The kitchen and bathrooms feature stunning quartz countertops, creating a fresh, modern aesthetic that makes daily living and entertaining a joy. The primary bedroom serves as a peaceful retreat complete with an updated private en-suite bathroom, while two additional spacious bedrooms offer perfect flexibility for guest quarters, a nursery, or a dedicated home office. Outside, enjoy a low-maintenance lot with mature landscaping and beautiful community surroundings. The Greenbriar neighborhood features tree-lined streets, a community park, and a sparkling pool—all zoned for top-rated Seminole County schools (Rainbow Elementary, Indian Trails Middle, and Winter Springs High). Conveniently located near shopping, dining, parks, and major roadways, this turn-key property is completely ready for its new owners—schedule your private showing today!

998 White Springs Lane, Winter Springs
$179,900
2 Beds ⋅ 2 Baths ⋅ Bay Tree Sec 09 SubDv. ⋅ 32708 Zip Code
Virtually Staged. If you’ve been dreaming of a MOVE-IN READY home where you can enjoy scenic parks, peaceful walking trails, and beautiful green spaces, welcome to Baytree 9, one of the charming communities within the Highlands of Winter Springs. This WELL-MAINTAINED two-story, 2-bedroom, 1½-bath condo offers the perfect blend of comfort, convenience, and carefree Florida living. Ideally located near highly rated schools, top medical facilities, shopping, dining, and major roadways, you’ll enjoy easy access to everything you need while coming home to a peaceful, nature-filled setting. Inside, the thoughtfully designed open floor plan creates an inviting space for everyday living. The kitchen flows into the dining and living areas, while oversized sliding glass doors fill the home with natural light and lead to your private patio – an ideal spot to sip your morning coffee, unwind after a long day, or simply enjoy the tranquil surroundings. The updated kitchen features granite countertops, a breakfast bar, pantry, neutral tile flooring, and all appliances convey. Upstairs, you’ll find a spacious primary suite, a comfortable second bedroom, a shared bath with direct access from the primary suite, and a conveniently located laundry closet designed for everyday ease. Enjoy peace of mind with numerous recent updates, including a NEW A/C in 2023 and, in 2024, a NEW ROOF, WATER HEATER, stainless steel kitchen APPLIANCES, full-size WASHER and DRYER, carpet, blinds, and chair-height toilets. One of the greatest benefits of this home is its low-maintenance lifestyle. The HOA covers exterior and grounds maintenance, giving you more time to enjoy the community’s OUTSTANDING AMENITIES. Spend sunny afternoons at the clubhouse and pool, gather with friends at the picnic areas with grills, explore the scenic nature trails, or enjoy the playgrounds, volleyball, basketball, and tennis courts. Conveniently located just off SR 434 with easy access to SR 436, Highway 17-92, SR 417, and I-4, you can enjoy Cranes Roost Park, Altamonte Mall, Winter Park Village, and the boutiques and restaurants along charming Park Avenue. Whether you’re looking for your first home, an investment, downsizing, or searching for a low-maintenance lifestyle surrounded by nature, this exceptional condo is ready to welcome you home. Schedule your private showing today and discover why so many love calling the Highlands of Winter Springs home! This home may be under audio or video surveillance.

70 Moree Loop Unit 61, Winter Springs
$287,500
3 Beds ⋅ 3 Baths ⋅ Heritage Commons SubDv. ⋅ 32708 Zip Code
Seller willing to provide a credit to Buyers at Closing. Built by Beazer Homes in 2010, this beautifully maintained townhome sits in a gated neighborhood and offers an unbeatable location. It is situated just 8 miles from the University of Central Florida & Siemens, 15 miles from downtown, with easy access to the 417 and just a stroll away from shopping, dining, and everyday conveniences. And let's not forget the highly desirable Seminole County schools nearby, making this an exceptional place to call home. Boasting the ideal floor plan, which features an open-concept living, dining, and kitchen area on the first floor, creating the perfect space for entertaining or everyday living. Upstairs, you'll find all three bedrooms thoughtfully tucked away for added privacy, along with a convenient upstairs laundry room. And an attached garage adds even more convenience with an updated smart opener - an app to open it from anywhere. Recent upgrades include a new roof (2020) and A/C (2023) and new oven/stove. Residents of Heritage Commons enjoy access to a community pool as well as a playground. Start enjoying the low maintenance living that townhome living offers, as the HOA handles all exterior maintenance & lawn care, providing the perfect lock-and-leave lifestyle. Don't delay, schedule your showing today!

1329 Heritage Commons Drive, Winter Springs
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