Casselberrry/Winter Springs / Tuscawilla Homes with Park Community Features

Casselberrry/Winter Springs / Tuscawilla Homes with Park Community Features

Welcome to the enchanting region of Casselberry, Winter Springs, and Tuscawilla, nestled in the heart of Seminole County, Florida. This vibrant area is renowned for its picturesque landscapes, family-friendly atmosphere, and a strong sense of community. With its lush parks, scenic lakes, and winding trails, it offers a perfect blend of nature and suburban living.

Winter Springs, often celebrated for its charming neighborhoods, boasts an array of homes that cater to diverse lifestyles. Many properties in this region feature beautiful park community amenities that enhance the living experience. Imagine stepping outside your door to find meticulously maintained parks, playgrounds, and walking trails just a stone's throw away. These community features not only encourage outdoor activities but also foster connections among neighbors, making it an ideal place for families and individuals alike.

Tuscawilla, a gem within Winter Springs, is particularly known for its golf courses and serene surroundings. Residents can enjoy leisurely afternoons at the local parks, picnicking under the shade of towering oaks or simply taking a stroll along the scenic pathways. The community spirit thrives here, with numerous events and gatherings that bring residents together, creating lasting friendships.

In addition to its natural beauty, this region is conveniently located near top-rated schools, shopping centers, and dining options, ensuring that everything you need is within reach. Whether you’re looking for a cozy family home or a spacious retreat, the Casselberry, Winter Springs, and Tuscawilla area offers an inviting community where you can truly feel at home. Come explore the possibilities and discover your dream home in this remarkable region!

Newest Casselberrry/Winter Springs / Tuscawilla Homes with Park 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
$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
$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
$489,900
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
$605,000
5 Beds ⋅ 2 Baths ⋅ Parkstone SubDv. ⋅ 32708 Zip Code
Enjoy waterfront views and your own private pool in this spacious 5-bedroom, 2-bath home located in the highly sought-after gated community of Parkstone in Winter Springs. Perfectly positioned with tranquil pond views, this home offers a desirable three-way split floor plan, open living spaces, and an ideal blend of comfort, functionality, and outdoor living. Inside, you’ll find luxury vinyl plank flooring throughout the main living areas, a beautifully updated kitchen featuring granite countertops, refinished cabinetry, and a stylish backsplash, along with tastefully remodeled bathrooms showcasing shaker-style vanities, updated fixtures, and wood-look tile flooring. Energy-efficient upgrades include Low-E double-hung windows, an updated roof (2021), Carrier HVAC system, LED lighting, a whole-house water filtration system, two mini-split air conditioning systems (2025), and an energy-efficient year-round. The backyard is also been fully fenced, creating a private space for pets, play, and outdoor enjoyment. Step outside to your own backyard retreat featuring a sparkling pool, relaxing spa, and picturesque water views. Whether you’re entertaining guests or enjoying a quiet evening watching the sunset over the pond, this outdoor space is sure to impress. Additional features include pool deck speaker pre-wiring and a 220-volt outlet ready for an electric vehicle charger. Parkstone residents enjoy an exceptional lifestyle with lawn maintenance included in the HOA, a community pool, fishing pier, tennis courts, playgrounds, walking trails, scenic ponds, and gated security. The community borders the Cross Seminole Trail and is just a short walk to Central Winds Park and the dog park. Located in Seminole County with highly rated A-rated schools and convenient access to shopping, dining, and major roadways, this home truly offers the best of Florida living. Don’t miss your opportunity to own this exceptional waterfront home in one of Winter Springs’ most desirable communities!

216 Tavestock Loop, Winter Springs
$3,199,000
7 Beds ⋅ 7 Baths ⋅ Dunmar Estates SubDv. ⋅ 32708 Zip Code
Rare opportunity to own a private estate in the heart of Central Florida. Situated on nearly 6 acres in Dunmar Estates community of Winter Springs, this exceptional property is fully fenced BY METAL FENCE AND SOLID WALL FENCE FROM 6ft to 10 ft and gated, offering outstanding privacy, security, and a true retreat-like setting. The main residence features over 12,000 square feet of living space, including 7 bedrooms, multiple living and entertaining areas, and a unique indoor heated pool that can be enjoyed year-round regardless of weather. Expansive grounds and mature landscaping create a peaceful and secluded environment rarely found in today’s market. A standout feature of the property is its two separate Mother-in-Law Suites, ideal for multigenerational living, extended family, long-term guests, caregivers, private offices, or flexible living arrangements. Additional amenities include a tennis court, circular driveway, 6-car garage, and abundant outdoor space, offering endless opportunities for customization, renovation, and creating a truly one-of-a-kind family compound. Conveniently located just minutes from top-rated schools, shopping, dining, and major highways, this estate combines the tranquility of private country-style living with the convenience of city access. A rare offering with exceptional space, privacy, and unlimited potential.

593 Dunmar Circle, Winter Springs
$499,000
4 Beds ⋅ 2 Baths ⋅ Sunrise Unit 2-A SubDv. ⋅ 32708 Zip Code
BACK ON THE MARKET!!PRICE TO SELL. LOCATION, LOCATION, LOCATION! Beautifully remodeled home in the heart of Winter Springs, conveniently located near shopping, dining, banking, fresh market , Publix, Oviedo Mall, YMCA, and major roadways (417 & 408). This spacious residence features 4 bedrooms, 2 full bathrooms, 2 car garage and an open functional floor plan ideal for family living and entertaining, two large separate rooms :a dining room and a living room Recent updates include a water heater (2026)new porch (2026), A/C (2017), and roof (2017). The oversized backyard is shaded by magnificent historic oak trees and includes a utility/workshop, building gym, offering endless possibilities. The community features a playground, basketball court, and park, with an additional neighborhood park conveniently located right next door and the HOA fee is paid anually and is exceptionally affordable.

1389 Ponce De Leon Boulevard, Winter Springs
$199,000
3 Beds ⋅ 2 Baths ⋅ Baytree Village SubDv. ⋅ 32708 Zip Code
Welcome to this beautifully maintained 3-bedroom, 2-bath condominium nestled in the highly desirable Highlands community of Winter Springs. Offering the perfect blend of comfort, style, and convenience, this move-in-ready home features an updated kitchen with granite countertops, stainless steel appliances, and ample cabinetry. The spacious floor plan is complemented by updated bathrooms, well-maintained interiors, and an inviting atmosphere throughout. Whether you're relaxing at home or hosting guests, you'll appreciate the thoughtful upgrades and pride of ownership evident in every room. Step outside and enjoy the exceptional resort-style amenities the community has to offer, including a sparkling pool, tennis and pickleball courts, scenic walking trails, playgrounds, and picturesque water views. The HOA provides added peace of mind by covering exterior maintenance, roof care, and common area upkeep, allowing for a low-maintenance lifestyle. Conveniently located near parks, shopping, dining, top-rated Seminole County schools, and major roadways, this home offers easy access to everything Central Florida has to offer. Don't miss this opportunity to enjoy resort-style living in one of Winter Springs' most sought-after communities!

429 Sheoah Boulevard Unit 9, Winter Springs
$557,900
4 Beds ⋅ 3 Baths ⋅ Parkstone SubDv. ⋅ 32708 Zip Code
New Price **268 Tavestock Loop, Winter Springs, FL 32708** Perfectly situated in the heart of Winter Springs, this stunning 4-bedroom, 2.5-bathroom home offers the ideal location with easy access to shopping, dining, theme parks, major roads, and the airport. Nestled within a desirable gated community, you'll enjoy peace of mind along with fantastic amenities including a community Lake Jess Up, pool, park, and 2 playground walking path, community benches. Step inside this beautiful two-story home and immediately notice the high ceilings that create a bright, open atmosphere throughout. Hard flooring runs seamlessly from room to room, giving the entire 2,883 square feet a clean, modern feel that is both stylish and easy to maintain. The kitchen is equipped with sleek stainless steel appliances, making it the perfect space to prepare meals and gather with family and friends. With four spacious bedrooms, there is plenty of room for everyone. The primary bedroom offers a comfortable retreat after a long day, while the additional bedrooms provide flexible space for family, guests, or a home office. Two full and half bathroom ensure convenience for the entire household. This move-in ready home means no waiting and no hassle. Simply unpack and start enjoying everything this wonderful property and community have for you. Whether you are relaxing by the community pool, taking the family to the playground, walking trails, Lake Jess Up or exploring all that Central Florida has in store, this home puts it all within reach. Don't miss your chance to make 268 Tavestock Loop your new home. Schedule your private showing today!

268 Tavestock Loop, Winter Springs
$167,777
2 Beds ⋅ 2 Baths ⋅ Sheoah Sec 1 SubDv. ⋅ 32708 Zip Code
WELCOME HOME! This elegant, bright, and open first-floor, single-story 2-bedroom, 2-bath condo is located in the highly desirable Winter Springs community. From the moment you step inside, you’ll feel right at home in the spacious living and dining area featuring custom-built shelving and an inviting layout perfect for relaxing or entertaining. The split-bedroom floor plan offers added privacy, with sliding doors from the primary suite leading to a charming brick patio, ideal for enjoying your morning coffee or unwinding in the evening. The kitchen has been beautifully renovated with new appliances, updated countertops, and ample workspace. The primary bathroom features a walk-in shower with safety grab bars, while the guest bathroom includes a tub, with a convenient laundry area located in the guest bath closet. A bright and airy enclosed Florida room with A/C provides flexible space for a home office, reading nook, or additional living area. Step outside to your private patio with room for outdoor furniture, plants, or even your own garden retreat, all overlooking a peaceful wooded conservation area. Additional highlights include approximately 1,196 square feet including the enclosed porch, a newer A/C and water heater, fresh interior paint in a modern light gray, and no carpet throughout. Located in The Highlands, a quiet and friendly community offering a pool, tennis courts, parks, walking trails, scenic water views, reserved parking, and community mailboxes. HOA fees include high-speed internet, cable, pest control, and full grounds maintenance, with weekly lawn care and twice-weekly trash pickup. The home is situated in a top-rated school district with schools nearby and is just minutes from shopping, dining, and everyday conveniences. Schedule your private showing today, this one won’t last long!

50 Sheoah Boulevard Unit 33, Winter Springs
$170,000
3 Beds ⋅ 2 Baths ⋅ Baytree Village SubDv. ⋅ 32708 Zip Code
One or more photo(s) has been virtually staged. Welcome to Baytree Village in the heart of Winter Springs—where beautifully landscaped grounds and a welcoming atmosphere create the perfect place to call home. This MOVE-IN READY second-floor condo offers 3 bedrooms, 2 full baths, and added privacy, all in a prime location close to top-rated schools, parks, shopping, dining, and major roadways for an easy commute. Step inside to a bright, open-concept living and dining area featuring a wall of windows and two sets of triple sliding glass doors, filling the space with natural light and providing seamless access to a large screened balcony with peaceful garden views—perfect for relaxing or entertaining. The kitchen is well-equipped with stainless steel appliances, ample cabinet and countertop space, and easy-care tile flooring. The spacious primary suite offers a comfortable retreat, while two additional bedrooms provide flexibility for guests, a home office, or additional living space. Additional highlights include in-unit laundry and extra storage off the balcony. Residents of Baytree Village enjoy well-maintained amenities and close proximity to local parks, including Audubon Park just minutes away. Seller is willing to cover up to six (6) months of the buyer’s Homeowners Association (HOA) dues with an acceptable offer. Whether you're a first-time buyer, downsizing, or investing, this is an opportunity you won’t want to miss. Schedule your private showing today!

240 Moree Loop Unit 3, Winter Springs
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