Casselberrry/Winter Springs / Tuscawilla Homes with Clubhouse Community Features

Casselberrry/Winter Springs / Tuscawilla Homes with Clubhouse 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 known for its lush landscapes, picturesque parks, and a welcoming community that embodies the spirit of Florida living. With easy access to major highways and proximity to the bustling city of Orlando, residents enjoy the perfect blend of suburban tranquility and urban convenience.

Winter Springs, in particular, boasts an array of family-friendly amenities, including top-rated schools, diverse shopping options, and delightful restaurants. The area is renowned for its beautiful parks, including the scenic Central Winds Park, which offers trails, sports facilities, and picnic areas, making it a favorite spot for outdoor enthusiasts. Tuscawilla, known for its stunning golf courses and serene lakes, provides a picturesque backdrop for those seeking an active lifestyle.

One of the standout features of this region is the abundance of homes within clubhouse communities. These neighborhoods offer residents exclusive access to luxurious amenities, including sparkling swimming pools, state-of-the-art fitness centers, and social gathering spaces perfect for hosting events. The clubhouse serves as the heart of the community, where neighbors become friends, and memories are created. Whether you’re enjoying a game of tennis, participating in community events, or relaxing by the pool, these features foster a strong sense of belonging.

If you’re searching for a place that combines natural beauty, community spirit, and modern conveniences, look no further than Casselberry, Winter Springs, and Tuscawilla. Your dream home awaits in this idyllic Florida paradise!

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

$270,000
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
$178,900
2 Beds ⋅ 2 Baths ⋅ Indian Ridge SubDv. ⋅ 32708 Zip Code
Virtually Staged. Enjoy life in this beautiful, recently renovated 2 bedroom, 2 bathroom patio home located in the beautiful Indian River community in Winter Springs. Welcome to a low maintenance lifestyle with the Condo Assn maintaining the lawn, sparkling community pool and clubhouse, tennis courts. This Central Florida location, near roads 434, 419 and 17/92, provides convenient access to the Winter Park restaurant and shopping district, other restaurants, shopping such as Publix, plus the Oviedo Mall and Advent Hospital. It is also only a 25 minute drive to the University of Central Florida and, so, is perfect for Faculty or Students! There are multiple parks in the area, such as Mount Greenwood Park and Big Tree Park, which host many activities throughout the year. The newly installed kitchen and freshly painted interior looks beautiful. One of the standout features of this home is the private outdoor space. The fenced patio area creates a comfortable spot for morning coffee....... ......container gardening, pets, outdoor dining, or relaxing at the end of the day. The included storage shed at 6 ft by 4 ft adds valuable functionality, offering extra space for tools, bikes, surfboards, or outdoor equipment. Indian River offers a peaceful residential setting known for its convenient access to parks, trails, shopping and dining. With its newly renovated interior, efficient 2-bedroom layout, private fenced outdoor space, storage shed, and desirable Winter Springs location, this condominium patio home offers comfort, convenience, and low-maintenance living in one of Seminole County's most appealing areas.

311 San Miguel Street Unit 311, Winter Springs
$263,000
3 Beds ⋅ 3 Baths ⋅ Heritage Commons SubDv. ⋅ 32708 Zip Code
Welcome to Heritage Commons, a gated community in the heart of Winter Springs, where comfort, convenience, and low-maintenance living come together. This 3-bedroom, 2.5-bathroom townhome with a one-car garage offers an excellent opportunity to make it your own and add your personal touches. Step inside to a bright, open floor plan filled with natural light. The spacious living and dining areas flow seamlessly into the well-appointed kitchen, featuring ample cabinetry, generous counter space, a breakfast bar, and a closet pantry — ideal for everyday living and entertaining. Upstairs, you’ll find all three generously sized bedrooms, including a spacious primary suite with a private en-suite bathroom. Two additional bedrooms share a well-appointed full bathroom, providing flexibility for guests, a home office, or additional living space. Enjoy the convenience of an interior laundry area, plenty of storage, and a private outdoor space perfect for relaxing after a long day. Heritage Commons offers a community pool and a convenient location close to shopping, dining, parks, top-rated Seminole County schools, and major roadways. Experience the best of Winter Springs living with easy access to Central Winds Park, the Cross Seminole Trail, and everything the area has to offer. Don’t miss the opportunity to make this wonderful townhome your own!

3880 White Birch Run, Winter Springs
$370,000
3 Beds ⋅ 3 Baths ⋅ Jesups Landing SubDv. ⋅ 32708 Zip Code
Virtually Staged. Welcome home to this beautifully upgraded townhome in the highly sought-after Jesup's Landing community! Designed for both comfortable everyday living and effortless entertaining, this home features an open-concept floor plan, a two-car attached garage, and three bedrooms, all located on the second floor. Adding to its value and peace of mind, the home features a brand-new roof and has been freshly painted on the exterior, enhancing both its curb appeal and long-term durability. The first floor offers a bright and inviting living space that flows seamlessly into the gourmet kitchen, complete with an oversized walk-in pantry that is already set up for your own kegerator, making it easy to enjoy your favorite craft beer on tap at home. A convenient half bath completes the main level. Upstairs, the luxurious primary suite is thoughtfully designed with a custom walk-in closet featuring a stylish barn door, a private balcony for morning coffee or evening cocktails, and a spa-inspired ensuite bath with dual vanities. Every detail has been carefully considered, from crown molding and custom window treatments to designer lighting controlled by wireless smart switches. Smart home features include a Brilliant Home Control System with touch panels in the living room and primary bedroom, a Nest Smart Thermostat, Aquanta Smart Water Heater Controller, Philips Hue smart lighting throughout the home, August Smart Locks on both exterior doors, a Ring Video Doorbell, myQ Smart Garage Door Opener with Amazon Key compatibility, Amazon Alexa integration throughout the home, pre-wired surround sound for Dolby 5.1 in the living room with additional in-ceiling speakers upstairs and in the primary bedroom, and a pre-wired security system. Residents of Jesup's Landing enjoy exceptional community amenities, including a resort-style pool, fitness center, clubhouse with a full kitchen, and game room—perfect for entertaining, gatherings, and special occasions. Conveniently located just minutes from SR 417, this home offers easy access to shopping, dining, parks, and scenic bike and walking trails, combining modern living with an exceptional location.

457 Gee Hammock Lane, Winter Springs
$140,000
1 Beds ⋅ 1 Baths ⋅ Baytree Village SubDv. ⋅ 32708 Zip Code
Virtually Staged. Price improvement for the perfect starter home, investment opportunity or downsizing. Excellent condition! Not every condo feels like HOME the moment you walk in—but this one does. EXCELLENT CONDITION! Tucked beneath the canopy of mature oaks in The Highlands of Winter Springs, this beautifully UPDATED FIRST FLOOR ONE BEDROOM/ONE BATH condominium offers the perfect blend of comfort, convenience, and carefree Florida living. Forget carrying groceries upstairs or tackling weekend projects. This move-in ready home has ceramic tile flooring throughout the main living areas, new luxury vinyl in the bedroom, new appliances, updated lighting, modern ceiling fans, a new water heater - A/C system replaced in 2019. The bedroom features custom-built closet organizers that maximize storage, while two additional exterior storage closets provide room for bicycles, holiday décor, tools, and outdoor gear. In 2010 all interior elements of the building were replaced with new electric, plumbing, doors, windows and all drywall and studs. One of the home's best features is the oversized screened porch—a private outdoor living space where you can sip your morning coffee, read a book, or unwind at the end of the day while enjoying the peaceful, tree-lined setting that has made The Highlands one of Winter Springs' most beloved communities. Life here extends well beyond your front door. Residents enjoy miles of scenic walking and nature trails, a community pool, tennis courts, pickleball courts, clubhouse, playground, and beautifully landscaped common areas that encourage an active outdoor lifestyle. Whether you're taking an evening stroll beneath the oak trees, meeting neighbors for a game of pickleball, or spending the afternoon poolside, you'll quickly see why so many people love calling The Highlands home. Located in the heart of Winter Springs, you'll be just minutes from top-rated Seminole County schools, shopping, dining, medical facilities, parks, and major roadways including SR 434, SR 417, and US 17-92, making commuting to Orlando, Winter Park, Lake Mary, and the surrounding area simple and convenient. Whether you're searching for your first home, a winter retreat, an investment property, or an easy, low-maintenance lifestyle, this updated Winter Springs condo delivers exceptional value in a location that continues to be one of Central Florida's most desirable places to live.

220 Moree Loop Unit 2, Winter Springs
$424,900
2 Beds ⋅ 2 Baths ⋅ Wedgewood Tennis Villas SubDv. ⋅ 32708 Zip Code
Virtually Staged. Welcome home to this absolutely charming and move-in-ready 2-bedroom, 2-bathroom home nestled in one of the most desirable areas of Winter Springs! From the moment you arrive, you'll appreciate the countless updates, beautiful wood beams and inviting curb appeal that make this home truly special. Major improvements provide peace of mind, including a 4-year-old roof, brand-new water heater, new flooring throughout, fresh interior and exterior paint, new appliances, and all-new light fixtures and ceiling fans. The beautifully updated kitchen offers modern style and functionality, while both bathrooms have been thoughtfully remodeled with today's buyer in mind. The spacious and light-filled bonus room overlooks the picturesque backyard and tranquil pond, creating the perfect space for a home office, reading room, playroom, or additional living area. Step outside and enjoy your backyard retreat featuring stunning water views and majestic oak trees that provide natural shade and beauty year-round while enjoying your morning coffee and watching the family of ducks swim by daily to greet you. Located in a great walking neighborhood, you'll love being just minutes from Tuscawilla Country Club and its renowned golf course, with olympic size pool and dining. Near top-rated schools and parks. Conveniently close to everything you need such as shopping, restaurants, medical facilities and your only a short drive to Florida's famous Theme Parks and about a 45 min drive to the best Beaches around. This adorable home offers the perfect blend of comfort, style, and location. Completely move-in ready and waiting for its new owners to fall in love—don't miss this incredible opportunity to own a piece of Winter Springs paradise!

717 Adidas Road, Winter Springs
$699,900
4 Beds ⋅ 3 Baths ⋅ Tuscawilla Unit 14b SubDv. ⋅ 32708 Zip Code
Rare opportunity to own a spacious pool home on a private 2.1-acre conservation homesite in the highly desirable Chelsea Woods section of Tuscawilla. Offering 4 bedrooms, 3 bathrooms and over 3,100 square feet of living space, this home features a dedicated office with custom built-ins, formal living and dining areas, a wood-burning fireplace, and a large upstairs loft that provides flexible space for a media room, game room, home gym, or additional living area. The kitchen overlooks the main living spaces and pool area, while French doors open to an expansive covered lanai and screened pool enclosure designed for year-round Florida living. Step outside and enjoy your own backyard retreat featuring a large pool and spa with waterfall features, outdoor grilling area, generous deck space, mature landscaping, and peaceful conservation views with no rear neighbors. Major improvements include a roof replaced approximately 3 years ago and HVAC systems replaced approximately 3 years ago, providing peace of mind for years to come. Conveniently located near top-rated Seminole County schools, parks, golf, shopping, dining, and major commuter routes. Optional HOA membership available. Homes offering this combination of acreage, privacy, pool, location, and living space rarely become available.

1838 Seneca Blvd, Winter Springs
$475,000
3 Beds ⋅ 2 Baths ⋅ The Highlands Sections Seven & Eight SubDv. ⋅ 32708 Zip Code
Beautifully maintained 3-bedroom, 2-bathroom home located in the highly sought-after Highlands community in Winter Springs, FL. Real hardwood floors flow through the main living areas, adding warmth and timeless appeal. The spacious kitchen features elegant stone countertops, ample cabinetry, and plenty of room for cooking and entertaining. The primary suite serves as a relaxing retreat with an en suite bathroom that includes a dual sink vanity, a large soaking tub, and a walk-in closet. The split-bedroom layout offers added privacy, while the two additional bedrooms provide flexibility for guests, family, or a home office. Step outside to enjoy the oversized lot, offering plenty of space for outdoor living and activities. The screened-in lanai is perfect for enjoying Florida’s weather year-round, whether you're relaxing or hosting guests. A 2-car garage adds convenience and extra storage. Residents also enjoy access to a community pool, as well as tennis courts, pickleball courts, and scenic nature trails, perfect for an active and social lifestyle. Ideally located in Winter Springs, this home is close to top-rated Seminole County schools, beautiful parks and trails, shopping and dining options, and provides easy access to major roadways for commuting to Orlando and surrounding areas. Enjoy a balance of peaceful suburban living with everyday conveniences just minutes away.

629 Ryan Court, Winter Springs
$329,900
3 Beds ⋅ 2 Baths ⋅ Highland Village 1 SubDv. ⋅ 32708 Zip Code
Welcome home to this cozy 3-bedroom, 2-bath bungalow-style home located in the resort-like Highlands community, offering 1,178 sq. ft. of living space. This home features vaulted ceilings, ceramic tile throughout, fresh interior paint, and a newly renovated kitchen with granite countertops, solid wood shaker-style cabinets, and black appliances. Major updates include a 2025 water heater and a new electrical panel inside and outside. The generously sized primary bedroom includes a built-in California Closets system, providing stylish and highly functional custom storage. The secondary and third bedrooms are also well-sized—perfect for guests, family, or easily converted into a home office. Washer and dryer are included in the sale. Enjoy the covered and screened lanai overlooking a charming New Orleans-style courtyard with pavers, a firepit, and a lamp post. The oversized, fully fenced, and cleared backyard offers plenty of space to relax, entertain, or garden, providing a strong sense of privacy. The Highlands is a highly sought-after, established community with low HOA fees and beautiful mature trees throughout. Amenities include an Olympic-size community pool, walking trails, playground, tennis court, volleyball court, and a clubhouse. Ideally situated just off State Road 434 Florida and Tuskawilla Road, this home offers quick access to Winter Springs Town Center for shopping and dining, and is just a short stroll from Torcaso Park—a lively neighborhood park featuring basketball courts, soccer and football fields, playgrounds for all ages, a splash pad, sand play areas, and picnic pavilions, perfect for both active days and relaxed family outings.

335 Kirkcaldy Drive, Winter Springs
$301,000
4 Beds ⋅ 3 Baths ⋅ Highland Patio Homes Amended Plat SubDv. ⋅ 32708 Zip Code
Welcome to a beautifully updated patio home tucked away on a quiet, tree-lined cul-de-sac in the desirable Pebble Creek community of The Highlands in Winter Springs. Enjoy Villa-style living with a two-story layout. Offering 4 bedrooms, 2.5 bathrooms, and a thoughtfully designed layout with the primary suite conveniently located on the first floor, this home blends comfort, functionality, and low-maintenance living. From the moment you arrive, you’ll appreciate the private courtyard entry—perfect for morning coffee or relaxing evenings, along with multiple outdoor spaces, including a screened-in porch and two fenced areas ideal for pets or gardening. Inside, the home features warm wood accents, soaring ceilings, and an abundance of natural light throughout. The updated kitchen is equipped with a gas double oven, modern appliances, pantry storage, and flows seamlessly into the main living areas. An interior laundry/utility room adds everyday convenience. Bathrooms have been tastefully renovated with updated vanities, tilework, and glass shower enclosures. Recent upgrades provide peace of mind, including re-piping, updated HVAC system, water heater, garage door, and energy-efficient windows and doors. Additional improvements include updated flooring, custom closet shelving, and enhanced finishes throughout the home. Located within The Highlands, residents enjoy a wide range of amenities, including a community pool, clubhouse, tennis courts, playgrounds, and miles of scenic walking trails and boardwalks. The HOA maintains exterior elements such as the roof, paint, and landscaping, allowing for easy, low-maintenance living

702 Glasgow Court, Winter Springs
$272,000
3 Beds ⋅ 2 Baths ⋅ Tuscany Place Ph 1 SubDv. ⋅ 32708 Zip Code
Very motivated sellers! Condo in Tuskawilla’s Tuscany Place •Discover comfort and convenience in Winter Springs’ Tuskawilla neighborhood. Tuscany Place is a gated community with a private pool, near Trotwood Park, Cross Seminole Trail, and top-rated schools. •Double Balcony (length of condo) •Corner unit with pool view •Updated kitchen w/stainless steel appliances •New water heater (2023) •New roof (2023) •New AC (2016) •Washer/dryer (2026) •Primary bedroom with walk-in closet, en-suite, and balcony access •Split floor plan for privacy. Seize this opportunity to own a beautifully updated condo in a prime location! FHA Approved Condo complex.

600 Northern Way Unit 1608, 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). New electric panel. House PASSED 4 POINT INSPECTION and copy of report will be given to new Buyer. 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 tennis and pickleball courts, soccer field, and covered picnic area. Many parks in neighborhood. Close to Seminole Trail for walking and bike riding. Move right in! Must See!

30 Sable Court, Winter Springs
Start Your Search