Casselberrry/Winter Springs / Tuscawilla Homes with Deed Restrictions Community Features

Casselberrry/Winter Springs / Tuscawilla Homes with Deed Restrictions Community Features

Welcome to the enchanting communities of Casselberry, Winter Springs, and Tuscawilla, nestled in the heart of Seminole County, Florida. This vibrant region is known for its picturesque landscapes, family-friendly atmosphere, and a strong sense of community. With easy access to major highways, residents enjoy a perfect blend of suburban tranquility and urban convenience, making it an ideal location for families, retirees, and professionals alike.

Winter Springs, in particular, boasts a rich tapestry of parks, recreational facilities, and top-rated schools, ensuring that families have everything they need at their fingertips. The area is dotted with beautiful homes, many of which are located within deed-restricted communities. These neighborhoods offer a heightened level of care and maintenance, ensuring that properties are well-kept and the community remains visually appealing. This commitment to aesthetics and quality of life makes these communities highly desirable.

In Tuscawilla, you’ll find stunning golf courses, serene lakes, and a wealth of outdoor activities that cater to nature lovers and sports enthusiasts. The community is also home to numerous shopping and dining options, providing residents with delightful local experiences.

Whether you’re searching 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 various lifestyles. With its charming neighborhoods, beautiful landscapes, and a strong sense of community, this region truly embodies the essence of Florida living. Come and discover your dream home in this delightful corner of Seminole County!

Newest Casselberrry/Winter Springs / Tuscawilla Homes with Deed Restrictions Community Features

$350,000
3 Beds ⋅ 3 Baths ⋅ Barclay Reserve Twnhms SubDv. ⋅ 32708 Zip Code
Welcome to the beautiful, tree-lined, gated community of Barclay Reserve. This 3 bedroom, 2.5 bathroom, end unit townhome is offered fully furnished and move in ready. Brand new A/C July 2025, new refrigerator April 2025 and new washer & dryer May of 2023. Enjoy a waterfront view with the soothing fountain sound from the living space and two bedrooms. Both the original owner and current owner used the property as a second home which means less wear and tear. The property is less than 10 minutes away from Ovideo on the Park and 15 minutes away from UCF, making the home a perfect purchase for parents needing student housing. It’s only 2 minutes from SR-417 for easy access to the airport, 408 and I-4. 33 guest parking spaces are distributed around the circle so you don’t have to worry about dodging street parking. Peace, security and a prime location seeking its next owner.

617 Pinebranch Circle, Winter Springs
$2,795,000
5 Beds ⋅ 7 Baths ⋅ Sturbridge Oaks SubDv. ⋅ 32708 Zip Code
Beyond the gates of an intimate seven-home enclave, a winding drive beneath a canopy of sculpted oaks introduces one of Winter Springs' most compelling lakefront estates. Set on more than two private acres with 150 feet of frontage on Little Lake Howell, the property pairs an exceptionally functional floor plan with a setting that has become increasingly difficult to find. Designed for both everyday living and effortless entertaining, the residence offers five bedrooms, five-and-one-half baths, a private study, dedicated home theater with professional-grade audio and projection, and nearly 5,800 square feet of thoughtfully designed living space. The primary suite occupies its own private retreat on the first floor, complete with a sitting room overlooking the lake, an expansive walk-in closet with direct access to the laundry room, and a spacious bath. A second en suite bedroom on the main level provides ideal accommodations for guests or multigenerational living. At the heart of the home, the open kitchen and family room flow naturally to the outdoor living spaces, while a soaring two-story gathering room and open second-floor gallery fill the home with natural light and create a remarkable sense of openness. Upstairs, three additional bedrooms and a screened terrace spanning the rear of the home provide exceptional flexibility while capturing sweeping views across the water. Outdoor living is equally inviting. A recently installed screened enclosure surrounds the pool, spa, and summer kitchen, while the covered dock with boat lift invites boating, skiing, paddleboarding, or quiet mornings on one of Central Florida's most beautifully maintained lakes. The usable grounds have been thoughtfully cleared and enhanced to create generous lawn, garden, and recreation space, complemented by mature fruit trees and preserve land bordering the southern property line for an extraordinary sense of privacy. The eastern shoreline offers unforgettable sunrises, rocket launches rising over the horizon, seasonal fireworks reflected across the lake, and frequent visits from native wildlife—creating a setting that feels remarkably peaceful despite being just minutes from everyday conveniences. Completing the estate are two separate two-car garages, three HVAC systems, and an expansive solar array that significantly reduces energy costs. It is a combination of land, privacy, and livability that is becoming increasingly difficult to find in Central Florida.

2117 Sturbridge Court, Winter Springs
$395,000
3 Beds ⋅ 4 Baths ⋅ Jesups Reserve Twnhms Rep SubDv. ⋅ 32708 Zip Code
Experience maintenance-free living in the heart of Winter Springs at Jesup's Reserve, where charming streetscapes, walkability, and everyday convenience come together. Perfectly positioned with peaceful pond views from the front porch and both upper-level balconies, this three-story townhome offers over three levels of thoughtfully designed living space just steps from Winter Springs Town Center. The versatile floor plan begins with a private first-floor bedroom and full bath—ideal for guests, multigenerational living, or a home office. Upstairs, the expansive main living level is designed for entertaining, featuring an open-concept living and dining area that flows seamlessly into the spacious kitchen. Complete with stone countertops, abundant 42” cabinetry, stainless steel appliances, a large center island, and generous prep space, it's a layout equally suited for everyday living and hosting friends and family. The third floor is home to two spacious bedroom suites, including a generous primary retreat with its own private balcony overlooking the water. The en-suite bath features dual vanities, a soaking tub, separate walk-in shower, and large walk-in closet, creating a true owner's sanctuary. Additional highlights include: Roof (2023), AC (2026) with transferrable warranty, fresh interior paint (2026), a convenient second-floor laundry room, powder bath, and attached two-car garage. Beyond your front door, enjoy resort-style amenities including a community pool, spa, and beautifully maintained grounds. Located directly across from Winter Springs Town Center, you'll have Publix, Aldi, restaurants, coffee shops, fitness centers, boutiques, and everyday conveniences just a short walk away. Outdoor enthusiasts will appreciate being minutes from Central Winds Park and the Cross Seminole Trail, while commuters enjoy quick access to SR-417, US-17/92, and top-rated Seminole County schools. Whether you're searching for a low-maintenance primary residence or a lock-and-leave lifestyle without sacrificing space or location, this Jesup's Reserve home delivers the perfect combination of comfort, convenience, and scenic surroundings. Easy to see. Call/Text for your private showing today!

227 Mcleods Way, 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
$689,900
4 Beds ⋅ 3 Baths ⋅ Howell Creek Reserve Ph 3 SubDv. ⋅ 32708 Zip Code
THERE ARE HOMES YOU SEE...and HOMES YOU FEEL! Privacy, space, and a peaceful conservation setting come together in this 4-bedroom, 3-bath pool home in the gated community of Howell Creek Reserve. Backing to conservation with no rear neighbors, the backyard feels like your own private retreat—perfect for relaxing by the pool or entertaining family and friends. Inside, the thoughtfully designed triple-split floor plan offers exceptional privacy, while soaring ceilings, crown molding, and updated lighting create an inviting, open atmosphere. The spacious primary suite features a tray ceiling, sitting area, walk-in closet, and an additional closet for extra storage. The kitchen offers granite countertops, a newer refrigerator and dishwasher, and opens seamlessly to the living spaces. Two bathrooms were renovated in 2020, and major updates include newer roof (2019), new HVAC (2026), newer water heater (2024), and a newer pool pump. Located just minutes from the Cross Seminole Trail, parks, shopping, dining, and top-rated Seminole County schools, this home offers the perfect balance of comfort, convenience, and Florida outdoor living. CALL TODAY to schedule your private Showing.

197 Nandina Terrace, Winter Springs
$450,000
3 Beds ⋅ 2 Baths ⋅ Wedgewood Tennis Villas SubDv. ⋅ 32708 Zip Code
Welcome to 1454 King Court - this is an ideal POOL home or rental property for those seeking an updated living space. This renovated home has 3 bedrooms with 2 bathrooms. The renovations include new kitchen cabinets, kitchen appliances and Quartz countertops, fully renovated luxurious bathrooms, new flooring, new lighting, new ceiling fans and more. NEW Roof in 2026 and Newer Water Heater! This home also has a newly painted interior/exterior. Quiet Neighborhood, Close to all Major Highways, and Shopping Centers. Also an excellent rental investment opportunity.

1454 King Court, Winter Springs
$424,990
3 Beds ⋅ 3 Baths ⋅ Seminole Crossing Townhomes SubDv. ⋅ 32708 Zip Code
BETTER THAN NEW... Experience the perfect blend of luxury, convenience, and lifestyle in this stunning 3-bedroom, 2.5-bath designer townhome, ideally situated in the heart of Winter Springs, one of Central Florida's most sought-after communities. Beautifully appointed with designer finishes throughout, this exceptional residence offers an elevated living experience just moments from everything you love. Step inside to discover a bright, open-concept floor plan where sophistication meets functionality. Premium Wood Laminate flooring, upscale finishes like 42 inch kitchen cabinets with under-cabinet lighting, elegant fixtures, and thoughtfully curated décor create a warm yet contemporary atmosphere that feels straight out of a design magazine. The spacious living and dining areas flow seamlessly into the gourmet kitchen, making this home equally suited for entertaining guests or enjoying a quiet evening at home. EVERY window in this home has electric shades that can be customized with timers, or easily opened-and-closed with a remote as smart-home has other included features such as LED lights, smart thermostat, bluetooth garage door, and more. Upstairs, the spacious owner's retreat provides a private sanctuary complete with a luxurious en-suite bath, a walk-in custom closet, while two additional bedrooms have generous accommodations for family, guests, or a home office. You absolutely cannot overlook the loft and it's feature as an office, extra TV room, or a play area for the little ones - the possibilities of this bonus space upstairs is ready for your imagination! What truly sets this property apart are the rare features that are nearly impossible to find. Enjoy the convenience of being one of only three homes with an oversized driveway, providing additional parking and enhanced curb appeal, including an epoxy floor in the garage. Even more unique, this residence is one of only six homes that feels like a private green space directly outside the front door, offering a refreshing sense of openness, and privacy as you sit on your front porch. Location is everything, and this home delivers. Walk just steps to the renowned Seminole Wekiva Trail, where miles of scenic walking, jogging, and biking paths await. Spend your weekends exploring nearby parks, enjoying local events, or dining at the countless restaurants and cafés just minutes from your doorstep. Shopping, grocery stores, fitness centers, and everyday conveniences are so close that many daily errands can be accomplished within minutes. With easy access to major roadways, top-rated Seminole County schools, and the charming atmosphere that has made Winter Springs one of Central Florida's most desirable places to call home, this property offers an unmatched combination of luxury and location. This is more than just a townhome, it's a lifestyle. Opportunities to own one of the community's most desirable homes, complete with premium upgrades, rare outdoor space, and an unbeatable location, are exceptionally rare. Schedule your private showing today and discover why this remarkable residence stands above the rest.

1153 Spotted Sandpiper Loop, 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
$245,000
2 Beds ⋅ 3 Baths ⋅ Casa Park Villas Ph 2 SubDv. ⋅ 32708 Zip Code
Virtually Staged. Discover carefree living in this BEAUTIFULLY MAINTAINED 2-bedroom, 2.5-bath townhome in Casa Park Villas, ideally located in the heart of Winter Springs. Combining a spacious layout, LOW-MAINTENANCE LIVING, and an unbeatable location within a TOP-RATED SCHOOL DISTRICT, this home is perfect for first-time buyers, downsizers, or anyone seeking a convenient lifestyle. Step inside to find LUXURY VINYL PLANK FLOORING throughout and a bright, welcoming Living Room where a large picture window fills the space with NATURAL LIGHT and a stylish ceiling fan keeps the room comfortable all year long. The OPEN LAYOUT flows seamlessly into the Dining area and Kitchen, creating an inviting setting for both everyday living and entertaining.The Kitchen offers plenty of cabinetry and counter space, a CONVENIENT CLOSET PANTRY, and a breakfast bar perfect for casual meals or morning coffee. A cozy Dining area provides room for a small table and chairs and features sliding glass doors that open to the PRIVATE PATIO, making indoor-outdoor living effortless. A convenient half bath completes the main level. Upstairs, you'll find TWO GENEROUSLY SIZED BEDROOMS, each with the luxury of its own private en suite bathroom. The spacious Primary Suite features DUAL CLOSETS, while the second bedroom includes a walk-in closet, making it ideal for guests, family members, or a home office. Step outside to the rear patio, complete with PRIVACY FENCING on both sides and peaceful views of the garden and GREEN SPACE—an inviting spot to enjoy your morning coffee or unwind at the end of the day. The HOA provides exceptional value by covering exterior maintenance, grounds maintenance, and access to the SPARKLING COMMUNITY POOL, allowing you to spend more time enjoying everything the neighborhood has to offer. One of this home's standout features is its location directly across from TROTWOOD PARK, where you'll enjoy pickleball and tennis courts, basketball courts, a splash pad, playground, picnic pavilions with BBQ grills, and a scenic boardwalk overlooking Lake Maria. The home is also within a SHORT DISTANCE of highly rated elementary and middle schools, making everyday routines even more convenient. You'll love being JUST MINUTES from Winter Springs Town Center, Oviedo Mall, and nearby popular shops and restaurants. OUTDOOR ENTHUSIASTS will enjoy Cross Seminole Trail, offering miles of scenic trails for walking, biking, and jogging. With QUICK ACCESS to SR 417, commuting to University of Central Florida, downtown Orlando, Orlando International Airport, and Central Florida's WORLD-FAMOUS ATTRACTIONS is a breeze. Offering an outstanding location, LOW-MAINTENANCE LIVING, and a thoughtfully designed floor plan, this Casa Park Villas townhome is ready to welcome you home. Call and schedule your tour today!

605 Casa Park Court Unit H, Winter Springs
$630,000
5 Beds ⋅ 2 Baths ⋅ Parkstone SubDv. ⋅ 32708 Zip Code
Welcome to this beautifully maintained 5-bedroom, 2-bath pool home in the highly sought-after gated community of Parkstone in Winter Springs. Perfectly positioned with tranquil pond views, this spacious 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, and a whole-house water filtration system, two mini-split air conditioning systems (2025) —providing enhanced comfort and energy efficiency year-round. The backyard has 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
$3,499,000
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
$1,120,000
5 Beds ⋅ 5 Baths ⋅ Reserve At Tuscawilla Ph 1 The SubDv. ⋅ 32708 Zip Code
Privately set within the exclusive gated community of Tuscawilla Reserve, this stunning custom estate delivers over 4,000 square feet of light-filled, designer-inspired living centered around a spectacular kitchen and family room that truly defines the home. With 5 bedrooms, 5 full baths, plus a private office/bonus room, this residence offers exceptional versatility for today’s lifestyle. Sleek wood flooring flows seamlessly throughout the main living areas, complementing the home’s open, modern design. The impressive kitchen and family room feature soaring two-story ceilings and expansive windows, framing views of the outdoors and pool area while filling the space with natural light—creating an inviting setting for both everyday living and elevated entertaining.The chef’s kitchen is a true centerpiece, anchored by JennAir appliances, including double ovens, convection oven, and microwave combo, along with a massive granite-topped island—all coming together to create a stunning focal point that anchors the kitchen and family room. Custom details further enhance the design, including a built-in buffet with integrated wine refrigerator and an oversized walk-in pantry. The thoughtfully designed floor plan offers incredible flexibility, including an upstairs retreat featuring an additional bedroom, full bath, and expansive flex space that can easily function as a media room, playroom, or second private office.Step outside to your private backyard oasis featuring a sparkling pool and spa with a new heater, surrounded by mature landscaping and a fully fenced yard, offering both openness and privacy. Additional highlights include a 3-car side-entry garage, whole house water softener and expansive living areas that support a variety of lifestyle needs. Ideally located near the Seminole Trail and just minutes from Tuscawilla Country Club, residents enjoy golf, tennis, swimming, and vibrant social amenities. Zoned for highly regarded Seminole County schools, this home offers both lifestyle and long-term value. Golf carts are a popular mode of transportation within the community, adding to the charm and convenience. A seamless blend of modern design, natural light, and elevated living—this is Tuscawilla Reserve at its finest. Schedule your private showing today and experience this exceptional home in person.

149 Cherry Creek Circle, Winter Springs
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