Casselberrry/Winter Springs / Tuscawilla Real Estate

Casselberrry/Winter Springs / Tuscawilla Real Estate

Welcome to the enchanting region of Casselberry, Winter Springs, and Tuscawilla, nestled in the heart of Seminole County, Florida. This vibrant area is a delightful blend of natural beauty, community spirit, and modern conveniences, making it an ideal destination for families, professionals, and retirees alike.

Winter Springs is known for its picturesque parks and serene lakes, providing residents with ample opportunities for outdoor recreation. The lush landscapes and well-maintained trails invite you to explore, whether you’re hiking, biking, or enjoying a leisurely stroll. The nearby Tuscawilla community boasts a stunning golf course, perfect for golf enthusiasts looking to perfect their swing while soaking in the Florida sunshine.

Education is a cornerstone of this region, with top-rated schools and a strong emphasis on community involvement. Families will appreciate the safe neighborhoods and friendly atmosphere, where children can thrive in a nurturing environment.

Shopping and dining options abound, with local boutiques and restaurants offering a taste of the area’s diverse culinary scene. From cozy cafés to upscale dining, there’s something to satisfy every palate.

Centrally located, Winter Springs provides easy access to major highways, allowing for a quick commute to nearby Orlando and its world-renowned attractions. Whether you’re exploring the magic of theme parks or indulging in the vibrant nightlife, everything is just a short drive away.

In Casselberry, Winter Springs, and Tuscawilla, you’ll find a warm community that embraces both the tranquility of suburban life and the excitement of urban amenities. Come discover your perfect home in this charming Florida haven!

Newest Listings in Casselberrry/Winter Springs / Tuscawilla

250 Moree Loop Unit 2, Winter Springs
$169,900
2 Beds ⋅ 2 Baths ⋅ Baytree Village SubDv. ⋅ 32708 Zip Code
Virtually Staged. Updated and Move-In Ready Condo in Baytree Village – Winter SpringsBeautiful 2-bedroom, 1.5-bathroom condominium with approximately 1,080 square feet, recently updated and presented in excellent condition. The property features fresh paint throughout the interior, a repaired ceiling on the first floor, and newly renovated stairs with LVP flooring (replacing the previous carpet). The kitchen stands out with quartz countertops that perfectly match the two bathrooms, creating a cohesive and modern look.The layout includes an open living/dining area, a private patio ideal for enjoying Florida’s climate, and bedrooms on the second floor. Located in the Baytree Village community (part of Highlands), residents enjoy excellent shared amenities: community pool, tennis and pickleball courts, clubhouse, playground, basketball court, picnic areas, and walking trails.Ideal for first-time buyers, investors, or anyone seeking a low-maintenance lifestyle. Close to Seminole County schools, shopping centers, restaurants, and with easy access to SR 434 and SR 417. Don’t miss this opportunity to own an updated condo in a convenient Winter Springs location!

250 Moree Loop Unit 2, Winter Springs
206 Cottonwood Drive, Winter Springs
$450,000
3 Beds ⋅ 2 Baths ⋅ Foxmoor Unit 1 SubDv. ⋅ 32708 Zip Code
Welcome home to this charming 3-bedroom, 2-bathroom POOL HOME in Winter Springs. It has a 2020 ROOF, a 2024 AC unit, and mature trees on a SPACIOUS lot! Great curb appeal welcomes you inside, where high ceilings, recessed lighting, and laminate flooring create a bright, open feel. The living area is centered on a cozy wood-burning fireplace. The functional floor plan offers comfortable spaces for everyday living and entertaining, and French doors open to a screened-in porch overlooking the private pool. Additional features include a water softener for added everyday convenience. Outside, your backyard retreat has a spacious pool area plus an added back deck with plenty of room for outdoor dining and entertaining, along with a storage shed and a bonfire area with cozy swinging chairs, just in time for the holidays and Florida's cold weather to roll in! Winter Springs is known for its parks, trails, and Seminole County Public School system. You’re minutes from Central Winds Park, the Cross Seminole Trail, and the shops and restaurants at Winter Springs Town Center. Oviedo, UCF, and Lake Jesup are nearby, and SR 417 and SR 434 give easy access to downtown Orlando, Orlando International Airport, and the area’s beaches. This home combines location, lifestyle, and value. Schedule your private showing today!

206 Cottonwood Drive, Winter Springs
111 Mcleods Way, Winter Springs
$395,000
3 Beds ⋅ 4 Baths ⋅ Jesups Reserve Twnhms Rep SubDv. ⋅ 32708 Zip Code
Gorgeous 3 bedroom 3 and 1/2 bath townhouse in Winter Springs FL. Town home is located near the front of this very desirable area across from the Winter Springs Town Center, offering a huge number of shops and amenities. The home was a builders model so you will find high end finishes and fixtures through out. Upgrades include: crown moulding, trim work, granite counter tops, custom windows treatments throughout, intercom with music, high end plumbing and light fixtures, kitchen island and breakfast bar- everything you could want! The kitchen has cherry cabinets with an exotic black granite finish as well as ample cabinets and a pantry for extra storage. A Large open floor plan on the second floor awaits with access to the first of 2 balconies, great for enjoying our beautiful Florida weather. The third story contains a large master suite with a private balcony, walk-in closet and large master bath with shower, garden tub and dual sink. Including another well appointed guest bedroom with a full bath. Roof new in 2022 & paint new in 2023. Furnished and decorated.

111 Mcleods Way, Winter Springs
740 Andover Circle, Winter Springs
$497,000
4 Beds ⋅ 3 Baths ⋅ Georgetowne Unit 3 SubDv. ⋅ 32708 Zip Code
TUSCAWILLA LIVING WITH A DOWNSTAIRS PRIMARY SUITE! Located in the Georgetowne community of Tuscawilla & offers OVER 2,100 SQUARE FEET OF LIVING SPACE, 4 BEDROOMS AND 2.5 BATHROOMS, with a primary bedroom suite conveniently located downstairs. This Winter Springs, Florida 32708 home includes a two-car garage and welcomes you with a paver driveway and side walkway, while its outdoor spaces invite you to enjoy more of Florida living. Start your morning on the screened porch, enjoy dinner outdoors on the rear paver patio, or invite friends over for a little friendly competition on the PROFESSIONALLY INSTALLED CORNHOLE COURT. Complete with a dedicated paver area and boards, the court gives the backyard a distinctive gathering spot. The driveway, side walkway and rear patio were installed in 2025. The Georgetowne community pool adds another way to enjoy time close to home, with Trotwood Park and Tuscawilla Country Club nearby. This Seminole County location offers access to shopping and dining via Winter Springs Boulevard and Tuskawilla Road, with connections to SR 417 for travel to Oviedo, the University of Central Florida (UCF), greater Orlando and Orlando International Airport (MCO). Plan a beach day in New Smyrna Beach, approximately 55 minutes away depending on traffic, or enjoy Central Florida’s major theme parks, including Walt Disney World Resort and Universal Orlando Resort. Inside, the staircase features STUNNING IRON BALUSTERS, adding a distinctive architectural focal point. Renovations completed in 2021–2022 include upstairs flooring, staircase improvements and bathroom remodels, and the interior has been freshly painted. The kitchen features a Bosch refrigerator and dishwasher; the home also has a Maytag washer and dryer. Additional property details include air conditioning replaced in 2021, a plumbing repipe in 2021, a water heater replaced in 2023 and a garage door, opener and tracks replaced in 2023. The roof was replaced in November 2013. Ring Security hardware conveys with the house.

740 Andover Circle, Winter Springs
120 E Bahama Road, Winter Springs
$935,000
4 Beds ⋅ 3 Baths ⋅ Bahama Ranches SubDv. ⋅ 32708 Zip Code
Mid-Century Modern Paradise!! A Beautiful, well-designed home with spectacular architecture offering privacy, space, and long-term versatility on a rare 2.22-acre lot with RV/Toy parking—delivering exceptional value in this area. A separate in-law or guest suite features its own exterior entrance and full bathroom, ideal for multigenerational living, a private office, studio, or extended stays. The main living areas are sprawling, thoughtfully arranged with strong natural light and a functional flow for everyday living and a large Loft for entertaining, office or hobbies. The large primary suite includes a spacious en-suite bath and walk-in closet. Bedrooms two and three are oversized, each with walk-in closets; one includes a hidden play loft/ adventure nook accessible through the Narnia style closet access. The expansive property also includes a detached casita in the backyard, currently used as a workshop, with clear potential to be converted into a guest home, rental unit, or art studio. Located on a quiet street in an established Winter Springs neighborhood, with convenient access to top-rated schools, shopping, dining, and major commuter routes. Concessions considered with the right scenario. Buyer and buyer’s agent to verify all information. Both owners are licensed real estate agents.

120 E Bahama Road, Winter Springs
1324 Via Villa Nova, Winter Springs
$420,000
4 Beds ⋅ 2 Baths ⋅ Sunrise Unit 2-A SubDv. ⋅ 32708 Zip Code
Welcome to 1324 Via Villa Nova, an inviting Winter Springs home situated on a desirable corner lot in an established, peaceful residential community. The open floor plan offers comfortable everyday living along with flexible bonus spaces ideal for a home office, guest room, playroom, nursery or additional living area. Step outside and enjoy your own large private pool, perfect for relaxing, entertaining and enjoying the Florida lifestyle year-round. The surrounding community offers three parks, two tennis courts, recreational areas and seasonal neighborhood events, creating a welcoming atmosphere with plenty to enjoy close to home. Conveniently located near shopping, dining, movie theaters, Oviedo Mall and major roadways, this home also provides easy access to Orlando’s world-famous theme parks, Orlando International Airport, Sanford International Airport and some of Central Florida’s beautiful Atlantic beaches. Enjoy the best of both worlds—close to major attractions and city conveniences, yet tucked away in a quiet residential setting. Located within the highly regarded Seminole County Public Schools district, this home combines location, flexibility and lifestyle in one attractive package. With its spacious layout, private pool, flexible living areas and convenient Central Florida location, 1324 Via Villa Nova offers an exceptional opportunity to enjoy comfortable Florida living.

1324 Via Villa Nova, Winter Springs
1394 San Luis Court, Winter Springs
$294,900
2 Beds ⋅ 2 Baths ⋅ Sunrise Village Unit 1 SubDv. ⋅ 32708 Zip Code
Single-story concrete block home in Winter Springs, and the expensive work is already done. Roof replaced in 2021 under Seminole County permit 13970. A/C replaced in 2020, inside and out. Repiped overhead through the attic. Newer windows. Tile throughout. What’s left is a kitchen remodel and cosmetic updates, so you get solid bones and pick your own finishes. 1394 San Luis Ct has 3 bedrooms, 2 baths and 1,153 heated sq ft on a fenced lot in Sunrise Village. Out front, stucco and lap siding sit under a gable roof with a stone veneer accent, a covered entry and a 2-car garage with a wide driveway. Inside, a floor-to-ceiling stone fireplace with a wood mantel anchors the living room. It opens to a dining area under a vaulted ceiling, which flows straight into the kitchen. The kitchen has wood cabinetry, a double stainless sink with a pull-down faucet, an electric range with hood, a microwave and a dishwasher. It works today and it’s ready for a full redo. Large neutral tile runs through the bedrooms and baths. The main bath has a tub/shower combo with a tile surround, and the toilets are new. Out back, a screened porch overlooks a level yard behind a wood privacy fence. The garage holds the laundry with washer and dryer, plus overhead storage shelving and interior access to the house. City water, public sewer, no CDD, and the HOA is just $29/month. Zoned for Rainbow Elementary, Indian Trails Middle and Oviedo High (buyer to verify). The water heater is the one system that hasn’t been replaced. It pencils as a long-term rental or a flip, and it’s a strong fit for a buyer who’d rather choose their own kitchen than pay for someone else’s. Book your showing.

1394 San Luis Court, Winter Springs
1732 Fox Glen Court, Winter Springs
$469,000
4 Beds ⋅ 3 Baths ⋅ Fox Glen At Chelsea Parc Tuscawilla Ph 2 SubDv. ⋅ 32708 Zip Code
A Fantastic Opportunity in the Heart of Tuscawilla - Four Bedrooms, Three Full Baths and a Desirable Split-Bedroom Floor Plan! Welcome to 1732 Fox Glen Court, located in the desirable Fox Glen at Chelsea Parc Community! This inviting single-story home offers a versatile floor plan designed to accommodate a variety of lifestyles. One of the home's most appealing features is its three-way split-bedroom layout, providing excellent privacy and flexibility. With two spacious bedroom suites positioned to accommodate a variety of living arrangements, this home is ideal for multi-generational living, guests, or those looking for additional space and versatility. The interior features soaring ceilings, a spacious kitchen with NEW stainless steel appliances, and a comfortable family space with generous built-in shelves that create an inviting atmosphere for everyday living and entertaining. Step outside and enjoy the Florida lifestyle from the screened-in, covered porch, providing a wonderful area to relax, enjoy your morning coffee, or unwind at the end of the day. Residents of Chelsea Parc enjoy access to amazing community amenities including a swimming pool, spa, and clubhouse with gym! The Tuscawilla neighborhood offers an abundance of recreational opportunities, including parks, playgrounds, golf, tennis, basketball, and access to the Cross Seminole Trail. It is conveniently located near Winter Springs Town Center, Oviedo, UCF Research Park, shopping, fine dining, and major roadways. This home offers an appealing combination of location, functionality, and lifestyle. Schedule your private showing today!

1732 Fox Glen Court, Winter Springs
624 Huntly Lane, Winter Springs
$245,000
2 Beds ⋅ 2 Baths ⋅ Highlands Sec 6 1st Rep SubDv. ⋅ 32708 Zip Code
Auction Property. Auction Property being sold, occupied. No Interior Access. Welcome to The Highlands, an established community in the heart of Winter Springs! Discover the possibilities of this 2-bedroom, 2-bath residence offering 1,156 square feet of living space with a convenient single-story layout. Whether you're looking to add your personal touch or create a space that suits your lifestyle, this home offers an opportunity to bring your ideas to life. Situated on a 0.12-acre lot, the property features an attached two-car garage and a spacious driveway for additional parking. Enjoy the convenience of being near SR-434 and US-17, providing access to shopping, dining, parks, indoor and outdoor recreation activities, and everyday essentials. With its established neighborhood setting and appealing nearby amenities, this property is ready for its next chapter.

624 Huntly Lane, Winter Springs
585 Green Spring Circle, Winter Springs
$230,000
2 Beds ⋅ 2 Baths ⋅ Mount Greenwood Unit 2 Of SubDv. ⋅ 32708 Zip Code
Move-in ready 2-bedroom, 1.5-bath townhome in the established Mount Greenwood community of Winter Springs. This two-story home offers 1,136 square feet with a combined living and dining area, an eat-in kitchen, tile flooring downstairs, and two bedrooms upstairs. A screened rear porch provides additional space to relax, and two assigned parking spaces add convenience. Residents enjoy a community pool, with community grounds maintenance included in the HOA fees. Convenient to shopping, restaurants, and everyday services along SR 434, with access to US 17-92 and SR 417. Central Winds Park and the Cross Seminole Trail offer recreation options in the surrounding area. Zoned for Winter Springs Elementary, Indian Trails Middle, and Winter Springs High School. A practical home with room to add your own personal touches.

585 Green Spring Circle, Winter Springs
732 Woodhaven Drive, Winter Springs
$300,000
3 Beds ⋅ 2 Baths ⋅ Wildwood SubDv. ⋅ 32708 Zip Code
732 Woodhaven Dr is a single-story Winter Springs home with three bedrooms, two bathrooms and over 1,300 square feet of living space. Sliding doors connect an additional living room to the rear patio, while the main living and dining areas share an open layout. The galley kitchen has counters and cabinets on both sides, a window above the sink and a separate laundry room at one end. The primary bedroom includes a wide closet and an attached bathroom with a tub-shower combination. Two secondary bedrooms sit near the hall bathroom, and an attached one-car garage provides covered parking. Included 100-Day Home Warranty

732 Woodhaven Drive, Winter Springs
138 Peregrine Court, Winter Springs
$535,000
3 Beds ⋅ 2 Baths ⋅ Eagles Watch Ph 2 SubDv. ⋅ 32708 Zip Code
Welcome to this stunning, completely transformed 3-bedroom, 2-bathroom home located in the sought-after gated community of Eagles Watch in Winter Springs. Every inch of this residence has been thoughtfully modernized, offering the ultimate blend of style, peace of mind, and carefree living. The path to easy living begins along the charming garden-like walkway to the front door, inviting you inside to an abundant, light-filled family room featuring vaulted ceilings and a large sliding glass door that opens to your spacious, screened-in lanai. Enjoy the sounds of nature as you sip your morning coffee, or step out onto the brand-new porcelain tile floors that flow seamlessly throughout both the interior and the patio. Comfort and efficiency are top-tier with a brand-new HVAC system and a new water heater, paired with a desirable split floor plan and plantation shutters. The refreshed kitchen is a chef’s dream, showcasing gleaming quartz countertops, a brand-new high-end appliance package, solid wood cabinetry, a built-in buffet for extra storage, kitchen counter bar seating, and an expansive casual dining or secondary living space. The primary suite is a true private oasis, accessible through elegant double doors and customized with a new modular master closet system. Bring your king-size bed and full furniture suite—there is room for everything. The fully remodeled primary en-suite bathroom exudes luxury with its striking quartz countertops and high-end finishes. On the opposite side of the home, two additional bedrooms provide comfort and privacy for guests or family, accompanied by a second bathroom that has also been fully remodeled to match the home's contemporary aesthetic. Every detail has been addressed, including fresh paint throughout and all-new light fixtures that illuminate the home's crisp, modern look. Outside, enjoy true low-maintenance living with HOA-covered front and side lawn care—meaning you can officially throw away the lawnmower—alongside a beautifully landscaped backyard ready for relaxing or entertaining. Kick back and utilize community amenities including a sparkling pool and a playground, ideal for that laid-back lifestyle you deserve. Located close to top-rated schools, shopping, and dining, this home offers the ultimate location. Enjoying golf? You're in luck! Tuscawilla Golf Course is just a golf cart drive away, ready for you to show off your swing. Convenient to the 417 and with direct access to Cross Seminole Trail—what more could you ask for? Don't miss this exceptional, move-in-ready opportunity in one of Winter Springs’ premier communities!

138 Peregrine Court, Winter Springs
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