Casselberrry/Winter Springs / Tuscawilla Homes with Clubhouse Amenities

Casselberrry/Winter Springs / Tuscawilla Homes with Clubhouse Amenities

Welcome to the enchanting region of Casselberry, Winter Springs, and Tuscawilla—three vibrant communities nestled in the heart of Seminole County, Florida. Known for their lush landscapes and friendly atmosphere, these areas offer a perfect blend of suburban tranquility and urban convenience. With easy access to major highways, residents enjoy a seamless commute to nearby Orlando while still being able to relish the charm of small-town living.

Winter Springs is particularly renowned for its commitment to community and recreation. The area boasts a variety of parks, walking trails, and outdoor spaces, making it a haven for nature lovers and families alike. The picturesque Tuscawilla neighborhood is famous for its golf courses and scenic views, providing a serene backdrop for those seeking an active lifestyle.

For homebuyers looking for a community that prioritizes social interaction and leisure, the homes in this region often come with exceptional clubhouse amenities. These well-appointed clubhouses serve as a hub for neighborhood gatherings, offering residents access to fitness centers, swimming pools, and event spaces. Imagine hosting a barbecue with friends or enjoying a quiet afternoon by the pool—all just steps from your front door.

Whether you’re looking for a cozy family home or a luxurious retreat, the properties in Casselberry, Winter Springs, and Tuscawilla cater to diverse tastes and lifestyles. Experience the warmth of community living combined with the allure of resort-style amenities. Discover your dream home in this captivating region today!

Newest Casselberrry/Winter Springs / Tuscawilla Homes with Clubhouse Amenities

$375,000
3 Beds ⋅ 3 Baths ⋅ Jesups Landing SubDv. ⋅ 32708 Zip Code
Welcome to this beautifully maintained townhome located in the highly desirable Winter Springs, where comfort, convenience, and lifestyle come together seamlessly. This exceptional residence offers access to community amenities including a fitness center and a community pool overlooking a serene neighborhood pond—perfect for relaxation and unwinding. Another outstanding feature is its unbeatable location adjacent to Central Winds Park. Residents can enjoy an incredible array of amenities just steps away, including pickleball courts, a baseball diamond, basketball courts, a fishing pier, scenic nature trails, picnic areas with pavilion, soccer fields, a playground, volleyball courts, and a fantastic dog park. The park also hosts year-round community events, making it a vibrant hub for recreation and connection. Inside, the home features a thoughtfully updated interior with a modern kitchen, luxury vinyl plank flooring, fresh interior paint, and stylish new lighting fixtures. Recent improvements also include a NEW ROOF, new A/C system 12/23, and fresh exterior paint, offering peace of mind for years to come. A private balcony provides additional outdoor living space, while the attached two-car garage ensures ample parking and storage. Outdoor enthusiasts will appreciate direct access to the Cross Seminole Trail, ideal for biking, jogging, or simply enjoying Florida’s natural beauty. The location also offers convenient access to dining, shopping, and local wine bars, all within the vibrant Town Center area. Families will benefit from proximity to highly rated Seminole County schools, including being just steps from Winter Springs High School, while still enjoying a setting that feels tucked away from the hustle and bustle. Whether you are a first-time homebuyer, looking to downsize, or seeking a low-maintenance lifestyle in one of Winter Springs’ most sought-after communities, this move-in-ready townhome is a must-see. A one-year home warranty with American Home Shield is included for added peace of mind. Don’t miss your opportunity to own this exceptional home in an unbeatable location!

453 Gee Hammock Lane, Winter Springs
$620,000
4 Beds ⋅ 4 Baths ⋅ Tuskawilla Crossings Ph 1 SubDv. ⋅ 32708 Zip Code
Built in 2019, this thoughtfully designed floor plan is ideal for multigenerational living, extended stays for guests, remote professionals, or anyone seeking additional privacy and versatility. The main residence encompasses 3 bedrooms, 2.5 bathrooms, and an additional dedicated office/flex room, while a separate 1 bedroom, 1 bath suite above the garage creates a private retreat complete with its own entrance. The main level showcases an open concept design where the family room flows seamlessly into the spacious eat in kitchen. The kitchen is beautifully appointed with 42" cabinetry, quartz countertops, upgraded stainless steel appliances, and a generous walk in pantry. A versatile office/flex room offers endless possibilities as a home office, playroom, fitness area, study space, or hobby room. Upstairs, the primary bedroom serves as a comfortable escape, featuring a walk-in closet, French doors that lead to a private balcony and a spacious en suite bath with dual vanities, a garden tub, and separate walk-in shower. Two additional bedrooms and a full bath with dual sinks complete the second floor of the main residence. One of the home's most desirable and unique features is the private in-law suite above the garage. Measuring approximately 19' x 16', this separate living space includes its own full bathroom, dedicated HVAC system, built-in cabinetry and private entrance, making it ideal for in-laws, guests, college aged children, a home business, or additional flex space. The remainder of the home highlights a front porch, a covered rear porch, a brick paved driveway, oversized parking area, two car garage, whole home Gigabit Wi Fi, fiber internet, smart locks, smart lighting and a 60 amp outlet ready for electric vehicle charging. Residents of Tuskawilla Crossings enjoy resort style amenities including a community pool with cabanas, playground, walking trails, multiple dog parks, and direct access to the Seminole County Trail. Ideally located just minutes from Winter Springs Town Center, shopping, dining, top rated Seminole County schools, and SR 417.

170 Wooded Vine Drive, Winter Springs
$210,000
2 Beds ⋅ 2 Baths ⋅ Cypress Club SubDv. ⋅ 32708 Zip Code
Move in Ready!...Beautiful 2/2 townhome in highly desirable Cypress Club community in The Highlands of Winter Springs, located in close proximity to SR 434! **Freshly Painted with light and neutral colors throughout! Vaulted ceiling in the very spacious/huge... family/great room with a wood burning fireplace! Split bedroom floorplan, with one bedroom downstairs. Brand new ceiling fan in upstairs bedroom. Tub and shower combination and linen closets in both bathrooms. Tile flooring in the living areas and laminate in the bedrooms. **Brand New Lennox A/C system and a washer and dryer included! Screened and Covered porch and an outside storage closet for additional storage. Two pools: the Cypress Club Community pool, and The Highlands master community pool! Brand new roofs in the community, HOA covers building insurance and grounds maintenance. Two assigned parking spaces. The community offers a fabulous club house, nature walking trails, parks, playground and tennis courts. Located close to shops and restaurants and very close to SR 434, SR 17/92 and SR 417 for easy commuting.

497 Club Drive, Winter Springs
$424,997
3 Beds ⋅ 2 Baths ⋅ Highlands Sec 1 SubDv. ⋅ 32708 Zip Code
PRICE IMPROVED + SELLER CONTRIBUTES TO CLOSING COSTS!, BACK ON THE MARKET DUE TO BUYERS FINANCING FALL TROUGH!! Updated Pool Home in Winter Springs | Seminole County | Move-In Ready Welcome to this beautifully maintained 3-bedroom, 2-bath home featuring a private screened pool in an established Winter Springs neighborhood. The updated kitchen and updated bathroom deliver a fresh, modern feel, complemented by a bright, open layout that flows seamlessly for both everyday living and entertaining. Step outside to your screened pool and fully fenced backyard — a private retreat for year-round Florida living and weekend gatherings. A 2-car garage and a tree-lined, established community complete the package. Zoned for the Seminole County school district (buyer to verify assigned schools with the district). Surrounded by scenic walking and biking trails and just minutes from shopping, dining, and major roadways for an easy commute. A versatile opportunity whether you're buying a home to live in or adding a pool home to your rental portfolio — updated, low-maintenance, and in a high-demand location. Seller will contribute toward buyer's closing costs with an acceptable FHA | VA | Conventional | Cash all financing welcome. Schedule your showing today!

872 Falkirk Drive, Winter Springs
$489,000
4 Beds ⋅ 3 Baths ⋅ The Oaks Sub SubDv. ⋅ 32708 Zip Code
Check out this spacious 4-bedroom, 2.5 bath home in Winter Springs, located in the highly sought-after Seminole County school district! Discover comfort and space in this corner lot home in The Oaks at the Highlands Subdivision. This well-designed home offers more than 2,300 square feet of living space with a functional layout that features the primary suite on the first floor along with a flex space used as an office or guest room plus 2 additional bedrooms upstairs. Inside, you’ll find a bright, open floor plan that seamlessly connects the main living areas. The kitchen is equipped with stainless steel appliances (new double door fridge) and a convenient breakfast bar overlooking the great room, making it perfect for both casual mornings and entertaining guests. Step outside through French doors to a screened patio and cozy fire pit area, creating an inviting space to unwind year-round. The spacious primary suite includes a walk-in closet and an en-suite bath with dual vanities, a soaking tub, and separate shower. Updates include a 2018 roof, energy-efficient windows, water softener, rain gutters, and irrigation system. Residents enjoy access to community amenities including a pool, clubhouse, park, and scenic walking trails, all just minutes from major roadways, shopping, and dining. Schedule your private tour today!

131 Lisa Loop, Winter Springs
$569,000
4 Beds ⋅ 3 Baths ⋅ Winter Spgs Unit 4 SubDv. ⋅ 32708 Zip Code
REDUCED! Beautiful Executive 4 bedroom POOL home in Tuscawilla Country Club Golf Community! NO HOA! Mediterranean feel with wrought iron accents and courtyard. Huge Kitchen with island in the middle. All appliances. Hot water heater 2017. Lots of cabinet space. Spacious eat-in area beside kitchen. Formal Dining and Living rooms. Large bedrooms. Big Owners bedroom with walk-in closet and updated bath. Inside laundry room. Large Pool (updated to salt system) 8 feet deep. Big fenced yard. Screened in porch. Oversized 2 car side entrance garage (currently part of garage is an office but could easily be converted back). Community allows golf carts. Plenty of room to park jet skis, boats, and RV. Great location near shopping, restaurants, hospital, and major roads. Good schools. Country Club has golf, tennis, swimming, and dining membership. Trotwood park has basketball and tennis courts, soccer field, and covered picnic area. Many parks in neighborhood. Close to Seminole Trail for walking and bike riding. Move right in! Must Seee!

30 Sable Court, Winter Springs
$269,000
3 Beds ⋅ 2 Baths ⋅ Cypress Club SubDv. ⋅ 32708 Zip Code
Discover effortless living in this immaculate 3-bedroom, 2-bath townhome nestled in the desirable Cypress Club at The Highlands. Thoughtfully maintained and beautifully updated, this residence offers the perfect blend of comfort, style, and convenience with a desirable split-bedroom floor plan—featuring one bedroom and a full bathroom on the main level, and the primary suite along with a third bedroom upstairs. Sliding glass doors open to a private screened porch, ideal for morning coffee, evening relaxation, or entertaining guests. This inviting space offers seamless indoor-outdoor living along with additional storage. The upgraded kitchen is a true highlight, showcasing solid wood cabinetry, modern countertops, and a breakfast bar perfect for casual dining or hosting friends and family. Two reserved parking spaces are conveniently located directly at your front door. Enjoy the resort-style lifestyle The Highlands is known for, offering a community pool, recreational building, tennis courts, and scenic hiking trails. Ideally located near I-4 and SR-417, commuting and weekend adventures are effortless. HOA fees provide exceptional value, covering exterior building and grounds maintenance, community amenities, —delivering peace of mind and truly low-maintenance living. IMPORTANT MESSAGE- While this townhouse HOA fees may seem higher, it covers roof replacement and maintenance (brand new 2026), exterior maintenance, landscaping, and more. A single-family home may have lower HOA fees, but usually comes with higher maintenance costs, more upkeep, and added stress - making the overall expense very similar in the end, with far less hassle in a townhouse community. Schedule your private showing today and make this exceptional townhome yours.

446 Club Drive, Winter Springs
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