Casselberrry/Winter Springs / Tuscawilla Homes with Private Yard Exterior Features

Casselberrry/Winter Springs / Tuscawilla Homes with Private Yard Exterior Features

Welcome to the enchanting region of Casselberry, Winter Springs, and Tuscawilla—an idyllic corner of Seminole County, Florida, where suburban charm meets natural beauty. Nestled just north of Orlando, this vibrant area is renowned for its family-friendly atmosphere, excellent schools, and abundant outdoor recreational opportunities, making it a perfect place to call home.

As you explore the neighborhoods, you’ll discover a delightful blend of modern conveniences and serene landscapes. The area is dotted with lush parks, scenic lakes, and winding trails, inviting residents to embrace an active lifestyle. Whether you’re biking along the picturesque paths of the Cross Seminole Trail or enjoying a leisurely afternoon at the nearby Central Winds Park, the natural beauty here is truly captivating.

One of the standout features of homes in Casselberry, Winter Springs, and Tuscawilla is the availability of properties with private yard exterior features. Imagine stepping into your own personal oasis, where you can unwind after a long day or host gatherings with friends and family. These spacious yards provide the perfect backdrop for outdoor living, whether you’re envisioning a vibrant garden, a cozy patio for evening barbecues, or a safe play area for children and pets.

With a strong sense of community, top-notch amenities, and a variety of housing options, this region offers an inviting environment for families, professionals, and retirees alike. Discover your dream home in Casselberry, Winter Springs, or Tuscawilla, and experience the best of Florida living today!

Newest Casselberrry/Winter Springs / Tuscawilla Homes with Private Yard Exterior Features

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 ⋅ Sunrise Village Unit 4 SubDv. ⋅ 32708 Zip Code

Exceptional location in the heart of Winter Springs! Tucked away on a quiet cul-de-sac in the desirable Tuscawilla area of Winter Springs, this home offers an incredible opportunity to enjoy one of Seminole County's most sought-after communities. Known for its top-rated public schools, beautiful parks, and miles of walking and biking trails, Winter Springs consistently ranks among Central Florida's most desirable places to call home. Beyond the interior, the backyard is designed for enjoying the Florida lifestyle, featuring a screen-enclosed pool with plenty of space to relax, entertain, or spend quality time with family and friends year-round. Whether you're hosting summer gatherings, enjoying a quiet evening poolside, or simply taking advantage of Central Florida's sunshine, this outdoor retreat is sure to become a favorite destination. Enjoy being just minutes from Trotwood Park, Central Winds Park, the Cross Seminole Trail, Tuscawilla Country Club, shopping, restaurants, and everyday conveniences. Commuters will appreciate easy access to SR 417, SR 434, while still enjoying the charm of an established residential neighborhood. For added peace of mind, the home's major systems have already been updated, including a 2019 roof, 2020 A/C, and 2020 water heater, allowing the next owner to focus on enjoying everything this outstanding home & location has to provide! It's not just about finding your next home, it's about finding the right community, the right schools, and the right lifestyle. This rare opportunity places you in the center of it all. Schedule your private tour and discover why this address should be at the top of your list.

1350 Palo Alto Court, Winter Springs

4 Beds ⋅ 2 Baths ⋅ Deer Run Unit 21a SubDv. ⋅ 32708 Zip Code

Don’t miss your chance to own this luxury 4-bedroom, 2-bath pool home retreat in the highly sought-after Tuscawilla Forest, featuring a BRAND NEW ROOF upon signed contract. Beautifully designed for everyday living and comfortable formality, this home offers an open layout with multiple living spaces. Walk in to a formal conversation area followed by a chef's kitchen with all granite countertops, and backsplashes. A spacious primary bedroom with an en suite spa like bathroom featuring large his and hers walk-in closets, a custom carrara quartz double vanity, and tied together with modern organic finishes. Have peace of mind with updated plumbing throughout. Step outside to your private fully fenced backyard oasis, featuring a sparkling pool and expansive outdoor area perfect for relaxing evenings, weekend gatherings, and enjoying the Florida nature. Ideally located near shopping, dining, parks, top-rated schools, and major roadways, this home provides the perfect combination of convenience, comfort, and modern luxury.

324 Ringwood Circle, Winter Springs

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

5 Beds ⋅ 3 Baths ⋅ Winter Spgs Unit 4 SubDv. ⋅ 32708 Zip Code

Beautiful 5 bedroom, 3 full bath home, in highly sought after Tuscawilla golf community, on a large lot with desirable side entry 2-car garage. The home boast neutral paint and flooring décor, abundant natural light with views of the lake. The primary bedroom sits on one side of the house and has an adjoining room that can be used as an office or gym area. The remodeled kitchen is a chef’s dream, which includes granite countertops, an oversized pantry, a pot filler and two ovens, plus a large island with a prep sink along with an eating area to entertain. You can sit by your pool overlooking a large backyard with a lake view. The home was recently updated with a new roof, gutters, exterior paint and new fencing in 2026. There are 2 central heat and air systems and a whole house water filtration system. Volunteer HOA with no HOA restrictions. Zoned for Seminole county A-rated school system.

1209 Deer Run Drive, Winter Springs

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

3 Beds ⋅ 2 Baths ⋅ North Orlando Terrace Unit 2 Sec 8 SubDv. ⋅ 32708 Zip Code

This meticulously maintained home offers an impressive combination of recent upgrades, thoughtful features, and exceptional outdoor living. The curb appeal is enhanced by professional landscape lighting, while 10-foot access gates on both sides of the property provide convenience and flexibility. A three-zone irrigation system helps maintain the beautifully landscaped grounds year-round. The backyard is designed for relaxation and enjoyment, featuring a sparkling pool with a removable safety fence, a LED pool light replaced in 2025, and a new pool pump and filter installed in 2026. For additional storage, workshop space, or hobby use, the property also includes a substantial 12’ x 20’ steel accessory building. No HOA, so bring your toys, Rv, camper etc! Inside, the garage has been refreshed with newly painted floors and walls and is illuminated by six custom LED light fixtures, creating a bright and functional space. Major system updates provide peace of mind, including a new roof installed in March 2026, a new central air conditioning system installed in March 2025, and a new hot water heater installed in May 2026. Additional recent improvements include a refrigerator replaced in 2024, a dishwasher installed in 2024, a garbage disposal added in 2025, a Google Nest smart thermostat installed in 2026, and an updated master bathroom toilet. With extensive recent improvements, modern conveniences, and pride of ownership evident throughout, this move-in-ready home offers outstanding value and is ready for its next owner to enjoy.

203 Sweetgum, Winter Springs

3 Beds ⋅ 2 Baths ⋅ Sunrise Estates Unit 2 SubDv. ⋅ 32708 Zip Code

Beautiful 3-bedroom, 2-bath pool/spa home located in the highly desirable Sunrise Estates in Winter Springs, featuring a split floor plan on nearly ¼ acre with no front neighbors for added privacy. This home boasts a newer roof and newer pool/spa heater, making it perfect for entertaining family and friends, while the oversized backyard and large covered screened-in patio provide an ideal outdoor living space. Inside, enjoy a wood-burning fireplace for warmth and ambiance on cooler evenings, along with no carpet throughout for easy maintenance. Sunrise Estates offers open parks, tennis courts, basketball courts, and softball fields, and is zoned for A-rated Seminole County schools, making it perfect for a growing family. Conveniently located near major highways, dining, shopping, and just minutes from Oviedo and Winter Park—schedule your private tour today!

1024 Dinero Drive, Winter Springs

4 Beds ⋅ 3 Baths ⋅ Deer Run Unit 20 SubDv. ⋅ 32708 Zip Code

PAID-OFF SOLAR + 2018 ROOF + WHOLE-HOME 10Gb ETHERNET all on a corner lot in the heart of Winter Springs! Welcome to 440 Buckskin Court, a 4-bedroom, 2.5-bath home in the established Deer Run community with the kind of character and charm you do not find in your average Florida home. Set on a spacious corner lot with fresh landscaping and a brand-new fence, this home blends classic curb appeal, thoughtful updates, and a location that makes everyday life easy. Inside, you’ll find an open floor plan with engineered hardwood flooring, a wood-burning fireplace, and a warm, inviting feel that makes the home instantly memorable. Whether you are hosting friends, working from home, cozying up by the fireplace, or settling into your daily routine, this home offers the space and flexibility to fit the way you actually live. One of the biggest perks? The paid-off 15kW solar system, giving you energy efficiency without the extra payment, so you can run your AC all summer long and enjoy Florida living a little more comfortably. The home also features a 2018 roof, whole-home fiber terminal, and 10Gb wired Ethernet in every room, making it a great fit for remote work, streaming, gaming, and connected living. The owner’s suite has been thoughtfully updated with a new shower and a custom closet with abundant storage. Additional upgrades like the smart thermostat with remote sensors, updated irrigation system, hardwired smoke detectors, GFIs in wet areas, and shower vent fans add convenience and peace of mind without taking away from the home’s personality. Located minutes from the 417, Red Bug Lake Road, Tuskawilla Road, parks, shopping, dining, and highly regarded Seminole County schools, this home puts you right in the middle of what makes Winter Springs so loved. Updated, charming, energy-efficient, and full of personality — 440 Buckskin Court is ready to welcome you home.

440 Buckskin Court, Winter Springs

3 Beds ⋅ 3 Baths ⋅ Fairway Oaks Unit 1 SubDv. ⋅ 32708 Zip Code

Welcome to the highly sought after Fairway Oaks at Tuscawilla community, where homes like this rarely come available! This spacious home features 3 bedrooms and 3 full bathrooms, 2,378 square feet of thoughtfully designed living space, and a private pool in the generously sized, fenced-in backyard oasis. As you enter through the private courtyard, discover the details that make this home so special. The luxury vinyl floors throughout the first floor are not only beautiful but designed for durability. The great room features a floor to ceiling wood burning stone fireplace, soaring cathedral ceilings, and stunning oversized windows which fill the home with natural light throughout. Granite countertops, a breakfast bar, ample storage, and ALL NEW black stainless-steel appliances are just some of the reasons you’ll love this kitchen, which flows naturally into the formal dining room. The first bedroom is situated downstairs, and includes its own ensuite full bathroom, perfect for those needing an in-law suite or multigenerational living. Upstairs you’ll find another full bathroom with a shower/tub combo, the second bedroom, and the primary suite. The primary bathroom includes a walk-in shower and separate bathtub, and the bedroom showcases a private balcony with recently updated flooring; the perfect place to relax and unwind while overlooking the 15th hole of the Tuscawilla golf course! At the back of the house an enclosed Florida room adds additional flex space to fit any lifestyle. Enjoy Florida living in the private pool and large fenced-in backyard, with peace of mind knowing that lawncare (front and back) is covered by the very reasonable, low-cost HOA! Additional features include updated electric panel (2024), new vent fans in all 3 bathrooms, and UV lights installed in both AC intakes to improve the air quality throughout the house and increase energy efficiency. Zoned for some of the best schools Central Florida has to offer, just minutes away from the Oviedo Mall, and right around the corner from the Tuscawilla country club which offers a fitness center, tennis courts, a junior Olympic sized swimming pool, and an 18-hole golf course, you really can’t beat this location! Schedule a showing today!

1200 Royal Oak Drive, Winter Springs

4 Beds ⋅ 3 Baths ⋅ Seville Chase SubDv. ⋅ 32708 Zip Code

SELLER MOTIVATED!! Make OFFER! Freshly Painted Exterior and Interior! Walk in and feel instantly at home! This beautifully renovated 4-bedroom, 3-bathroom triple-split pool home sits on nearly half an acre in the gated community of Seville Chase and is completely move-in ready. Step inside to soaring ceilings and a thoughtfully designed open layout that still offers comfortable separation of space. You’ll immediately notice the stunning porcelain tile floors and a high-end, fully updated kitchen featuring custom cabinetry, pull-out shelving, soft-close drawers and doors, and sleek quartz countertops—perfect for both everyday living and entertaining. Recent upgrades provide peace of mind, including: New tile roof (2025) with a 50-year warranty AC replaced in 2022 Water softener (2022) New pool pump Out back, enjoy your own private retreat with a screened pool overlooking a serene conservation area with a lake—ideal for relaxing or even bass fishing. The expansive yard also features mature fruit trees, including avocado, mango, lemon, and a cherry bush. All of this is conveniently located near Winter Springs, major highways (417 & 434), UCF, Seminole State College, and major employers like Lockheed Martin and Siemens. This home truly has it all—style, space, and location. Schedule your private showing today before it’s gone!

510 Sonata Court, Winter Springs

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

Price Improvements. This 3-bedroom, 2-bathroom home in Deersong-2 is a fantastic opportunity for anyone looking for a move-in-ready property in Winter Springs. With its newly updated kitchen, Modern faucet, granite countertops, and indoor laundry. High ceilings at living room, the home feels both modern and spacious. The community offers excellent amenities, including a gated pool and tennis courts, all for a low HOA fee. It is zoned A+ Seminole county public schools, . Its prime location near top-rated Seminole County schools and the popular Torcaso Cove park makes it ideal for daily living. will not last long, Schedule your private showing today!!

276 San Gabriel Street, Winter Springs

Start Your Search