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

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

Welcome to the enchanting region of Casselberry, Winter Springs, and Tuscawilla, nestled in beautiful Seminole County, Florida. This vibrant area is known for its lush landscapes, friendly neighborhoods, and a strong sense of community. Whether you’re seeking a family-friendly environment or a tranquil retreat, this region offers a delightful blend of both.

Winter Springs stands out with its picturesque parks, top-rated schools, and a plethora of recreational activities. The nearby Tuscawilla community is particularly renowned for its stunning golf courses, serene lakes, and meticulously landscaped gardens, making it a haven for nature lovers and outdoor enthusiasts alike. The area is also conveniently located, providing easy access to major highways, shopping centers, and dining options, ensuring that everything you need is just a stone's throw away.

One of the defining features of this region is its homes with deed restrictions. These communities are designed to maintain a high standard of living, ensuring that properties are well-kept and that the overall aesthetic remains appealing. Residents can enjoy a sense of pride in their neighborhoods, knowing that their investment is protected by these guidelines. From charming single-family homes to modern townhouses, the real estate options here cater to a variety of lifestyles and budgets.

Embrace the warmth and charm of Casselberry, Winter Springs, and Tuscawilla, where you’ll find not just a house, but a place to call home. Explore the opportunities that await you in this thriving community, and discover why so many are choosing to make this region their own!

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

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

3 Beds ⋅ 2 Baths ⋅ Deersong 2 SubDv. ⋅ 32708 Zip Code

Welcome to this beautifully updated 3-bedroom, 2-bath home in the desirable Deer Song community of Winter Springs! Offering 1,105 square feet of thoughtfully designed living space, this move-in-ready home combines modern updates, smart-home technology, energy efficiency, and comfortable Florida living. Step inside to a bright, welcoming interior featuring fresh paint throughout and an updated kitchen with stainless steel appliances and a Samsung Smart Refrigerator with Family Hub Touchscreen. Both bathrooms have been fully updated with modern finishes and smart mirrors, adding style and technology throughout the home. Major improvements include a complete whole-home re-pipe in 2023, and an HVAC UV light system designed to support indoor air quality. Step outside to the screened-in back porch with newly finished epoxy flooring—the perfect place to relax and enjoy the private backyard. A separate storage shed provides additional space for tools, outdoor equipment, and more. Enjoy the benefits of energy-efficient living with solar panels that help keep monthly electric costs low and best of all, the solar panels will be paid in full by the seller at closing Enjoy access to the community pool and a convenient Winter Springs location near shopping, dining, parks, recreation, A-Rated Seminole County Public schools, and more. Come see what makes 272 San Gabriel Street such a sweet place to call home!

272 San Gabriel Street, Winter Springs

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

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

3 Beds ⋅ 3 Baths ⋅ Heritage Commons SubDv. ⋅ 32708 Zip Code

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

4 Beds ⋅ 2 Baths ⋅ Oak Forest SubDv. ⋅ 32708 Zip Code

Beautiful pool home in Oak Forest. NEW ROOF, NEW SOD Coming soon.. NEW INTERIOR PAINT and VINYL FLOORS. Gorgeous 42" kitchen cabinets with granite counters and large Island with seating and tiled backsplash. Both bathrooms have beautiful vanities and glass tiles and granite counters. Fourth bedroom has been turned into an office but could be converted back into a bedroom by adding a closet. Tall ceilings, tile and Vinyl floors throughout, open floorplan and neutral colors complete the interior package but there's more! Brick paver front entry and large screened pool area make this a home you won't want to miss. New SOD and landscaping will be done soon.

1114 Seafarer Lane, Winter Springs

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

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

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

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

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

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

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