Casselberrry/Winter Springs / Tuscawilla Homes with Florida Architectural style

Casselberrry/Winter Springs / Tuscawilla Homes with Florida Architectural style

Welcome to the enchanting region of Casselberry, Winter Springs, and Tuscawilla, nestled in the heart of Seminole County, Florida. This vibrant area is renowned for its lush landscapes, friendly communities, and an array of outdoor activities that make it a perfect place to call home. With its proximity to the bustling city of Orlando, residents enjoy the best of both worlds: serene suburban living and easy access to urban amenities.

The charm of this region is further accentuated by its stunning homes that embody the quintessential Florida architectural style. Picture yourself in a beautifully designed residence featuring open floor plans, expansive windows that invite natural light, and inviting outdoor spaces perfect for entertaining. Many homes in this area boast charming details such as terracotta tiles, tropical landscaping, and spacious patios, ideal for soaking up the Florida sun.

Casselberry, Winter Springs, and Tuscawilla are not just about beautiful homes; they are also about community. With top-rated schools, family-friendly parks, and recreational facilities, the area fosters a strong sense of belonging. Residents can enjoy hiking or biking along scenic trails, relaxing by the lake, or indulging in local dining and shopping experiences.

Whether you’re searching for a cozy single-family home or a luxurious estate, this region offers a diverse selection of properties that cater to every lifestyle. Embrace the allure of Florida living in Casselberry, Winter Springs, and Tuscawilla, where your dream home awaits!

Newest Casselberrry/Winter Springs / Tuscawilla Homes with Florida Architectural style

$375,000
3 Beds ⋅ 2 Baths ⋅ Oak Forest Unit 3 SubDv. ⋅ 32708 Zip Code
Welcome to 867 Benchwood Drive, a spacious and inviting 3-bedroom, 2-bathroom home nestled in the desirable Oak Forest at Tuscawilla community of Winter Springs! Situated on an oversized approximately 0.29-acre lot, this property offers a rare combination of comfortable living space, functionality, privacy, and an excellent location. Step inside to an inviting open-concept layout featuring the kitchen, dining area, and living space with easy flow for everyday living and entertaining. The spacious living room boasts a vaulted ceiling and two sliding glass doors that fill the space with natural light while providing beautiful views and direct access to the backyard. Tile flooring enhances the main living areas, while the generously sized bedrooms offer comfortable accommodations. The kitchen is thoughtfully positioned overlooking the living area and backyard, creating a connected and functional space. A versatile flex space provides additional options for a dining room, home office, playroom, or second living area. The spacious primary bedroom suite offers added privacy and features a very large walk-in closet, a mini-split AC/heater, and a freshly painted interior completed approximately one year ago. The primary bathroom was remodeled in 2025 and features a beautiful walk-in shower. One of the home's standout features is the expansive, fenced, organic backyard. Enjoy a private outdoor retreat with mature landscaping, fruit trees, garden areas, wooded views, a fire pit, and no rear neighbors—providing plenty of space for outdoor activities, gardening, entertaining, or simply relaxing in a peaceful setting. Additional features include a 2-car garage, ample driveway parking, and a storage shed. The location puts you minutes from highly rated Seminole County schools (K–12), Trotwood Park, Winter Springs Town Center, shopping, dining, and recreation, with easy access to SR 417. Offering a wonderful combination of neighborhood charm, generous outdoor space, privacy, and convenience, 867 Benchwood Drive is ready to welcome you home. Schedule your private showing today.

867 Benchwood Drive, Winter Springs
$349,000
3 Beds ⋅ 2 Baths ⋅ Foxmoor Unit 1 SubDv. ⋅ 32708 Zip Code
ADORABLE and MOVE-IN READY! Whether you're a FIRST-TIME HOMEBUYER or looking to "RIGHT-SIZE" into a more manageable home without sacrificing comfort. This charming 3-Bedroom, 2-Bath WATER-FRONT HOME will meet your needs and more. Paddleboard or canoe on the Water out back! Step inside to discover a bright and inviting open floor plan featuring soaring vaulted ceilings, abundant natural light, and a desirable split-bedroom layout that offers both privacy and functionality. The private OWNER'S SUITE serves as a relaxing retreat with a Vaulted Ceiling, a generous WALK-IN CLOSET and an ENSUITE BATH with a LARGE SHOWER. Nice size Secondary Bedrooms and Hall Bath with Tub/Shower on the opposite side of the home. Double Pane Windows and Sliding Glass Doors to the Back Patio which includes a Pergola with Covering, Fully Fenced Backyard and a variety of Fruit plants and trees; such as Pineapples and Bananas. New WATER HEATER just installed and permitted, ROOF 2021, with a partial reroof 2024, permitted; A/C 2013. New Frigidaire Range and Newer Washer and Dryer. NO HOA! Zoned for Winter Springs top-rated Schools. **Professional Photos Coming Soon!**

203 Cottonwood Drive, Winter Springs
$442,000
3 Beds ⋅ 2 Baths ⋅ Eagles Watch Ph 2 SubDv. ⋅ 32708 Zip Code
Welcome Home to Your Winter Springs Garden Oasis! Step into the warmth and charm of this lovingly maintained 3-bedroom, 2-bathroom home, perfectly situated in the heart of Winter Springs, Florida. From the moment you arrive, it’s clear this home has been cared for with pride, offering a welcoming atmosphere both inside and out. One of the true highlights is the beautifully manicured, fully landscaped grounds that surround the entire home. Thoughtfully selected plantings, mature greenery, and carefully maintained gardens create a sense of privacy and tranquility at every turn. Every detail has been thoughtfully considered to create an inviting outdoor retreat. Step out back and discover your own garden oasis! The extended screened porch provides the perfect setting for morning coffee, afternoon relaxation, or gathering with friends and family while enjoying the peaceful beauty of the surrounding landscape. The lush landscaping creates a wonderful backdrop and makes this outdoor space feel like a private retreat. Located in the heart of desirable Winter Springs, this charming home offers the perfect blend of comfort, character, and Florida outdoor living. If you’ve been looking for a home that feels welcoming, cared for, and truly special, this garden retreat is ready to welcome you home.

107 Peregrine Court, Winter Springs
$170,000
3 Beds ⋅ 2 Baths ⋅ Baytree Village SubDv. ⋅ 32708 Zip Code
One or more photo(s) has been virtually staged. Welcome to Baytree Village in the heart of Winter Springs—where beautifully landscaped grounds and a welcoming atmosphere create the perfect place to call home. This MOVE-IN READY second-floor condo offers 3 bedrooms, 2 full baths, and added privacy, all in a prime location close to top-rated schools, parks, shopping, dining, and major roadways for an easy commute. Step inside to a bright, open-concept living and dining area featuring a wall of windows and two sets of triple sliding glass doors, filling the space with natural light and providing seamless access to a large screened balcony with peaceful garden views—perfect for relaxing or entertaining. The kitchen is well-equipped with stainless steel appliances, ample cabinet and countertop space, and easy-care tile flooring. The spacious primary suite offers a comfortable retreat, while two additional bedrooms provide flexibility for guests, a home office, or additional living space. Additional highlights include in-unit laundry and extra storage off the balcony. Residents of Baytree Village enjoy well-maintained amenities and close proximity to local parks, including Audubon Park just minutes away. Seller is willing to cover up to six (6) months of the buyer’s Homeowners Association (HOA) dues with an acceptable offer. Whether you're a first-time buyer, downsizing, or investing, this is an opportunity you won’t want to miss. Schedule your private showing today!

240 Moree Loop Unit 3, Winter Springs
$267,500
3 Beds ⋅ 2 Baths ⋅ Cypress Club SubDv. ⋅ 32708 Zip Code
Virtually Staged. Welcome to 476 Club Drive, a beautifully maintained 3-bedroom, 2-bath townhome in the highly sought-after Cypress Club section of The Highlands in Winter Springs. NEW ROOF 2026, NEW WATER HEATER 2026, 2020 A/C, FULL-HOME REPIPE 2016, and WHOLE-HOME WATER SOFTENER 2016! This spacious home offers a flexible floor plan, peaceful wooded views, and an impressive list of updates. The main level features knockdown ceilings, updated recessed lighting, and an inviting living and dining area overlooking the serene, tree-lined surroundings. A step-down enclosed patio provides additional living space and a wonderful private retreat for relaxing or entertaining. A downstairs bedroom with an adjacent full bath offers flexibility for guests, a home office, or multi-generational living. Upstairs, two spacious bedrooms feature soaring ceilings and abundant natural light. The generous primary suite offers ample closet space, tranquil wooded views, and a private bath with a Jacuzzi tub and separate shower. A dedicated tankless water heater serves the Jacuzzi tub and primary suite bathroom, adding an extra level of comfort and convenience. Enjoy the added benefit of a covered carport with TWO dedicated parking spaces, keeping your vehicles protected from the Florida sun and weather. Cypress Club is the only section of The Highlands with its own private pool, while residents also enjoy access to the community’s outstanding amenities, including multiple pools, tennis courts, walking trails, parks, pavilions, BBQ areas, clubhouse, volleyball, and basketball courts. Located in desirable Winter Springs, this move-in-ready townhome combines thoughtful updates, flexible living spaces, natural surroundings, covered parking, and an exceptional amenity-rich community. Don’t miss the opportunity to make 476 Club Drive your new home!

476 Club Drive, Winter Springs
$410,900
3 Beds ⋅ 2 Baths ⋅ Oak Forest Unit 2a SubDv. ⋅ 32708 Zip Code
Virtually Staged. Location, comfort, and functionality come together in this well-designed 3-bedroom, 2-bath home in desirable Winter Springs! Featuring a sought-after split-bedroom floor plan, this home offers privacy and a layout that's perfect for everyday living. The open kitchen includes a casual eat-in dining area and flows effortlessly into both the formal dining room and spacious living room, creating an inviting space for entertaining family and friends. Step outside to an oversized covered porch overlooking a large backyard with endless possibilities for outdoor living, gardening, play, or future enhancements. An added convenience is the garage's direct access to the backyard, making it easy to move equipment, work on projects, or enjoy the outdoor space. Ideally located in the heart of Winter Springs, you'll appreciate the convenience of being close to top-rated Seminole County schools, parks, shopping, dining, and major roadways, all while enjoying the charm and sense of community that make this area one of Central Florida's most desirable places to call home. This home offers the space, layout, and location buyers have been searching for. Schedule your private showing today!

1012 Forest Circle, Winter Springs
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