Casselberrry/Winter Springs / Tuscawilla Homes with Contemporary Architectural style

Casselberrry/Winter Springs / Tuscawilla Homes with Contemporary Architectural style

Welcome to the serene and vibrant community of Casselberry, Winter Springs, and Tuscawilla, nestled in the heart of Seminole County, Florida. This charming region offers a perfect blend of suburban tranquility and urban convenience, making it an ideal place for families, professionals, and retirees alike.

Known for its lush landscapes and picturesque parks, Winter Springs boasts an array of outdoor recreational opportunities. With the scenic Central Winds Park and the picturesque Tuscawilla Golf Club nearby, residents can enjoy leisurely strolls, picnics, or a round of golf while soaking in the beautiful Florida sunshine. The area is also well-connected, with easy access to major highways, ensuring that the vibrant cities of Orlando and Sanford are just a short drive away.

When it comes to real estate, the contemporary architectural style homes in this area stand out for their sleek lines, open floor plans, and modern finishes. These homes are designed to maximize natural light and create a seamless flow between indoor and outdoor spaces, perfect for entertaining or simply enjoying daily life. With a variety of options available, from chic townhomes to spacious single-family residences, there is something to suit every taste and lifestyle.

In addition to their stunning aesthetics, these contemporary homes often feature energy-efficient appliances and smart home technologies, making them not only stylish but also practical. Living in Casselberry, Winter Springs, and Tuscawilla means embracing a lifestyle that values both comfort and modernity. Come explore this inviting community and discover your dream home today!

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

$512,000
3 Beds ⋅ 3 Baths ⋅ Hickory Grove Twnhms SubDv. ⋅ 32708 Zip Code
Beautifully Upgraded Sofia Model Townhome on a Premium Conservation Lot! Welcome home to this exceptional Sofia Model townhome, featuring one of the community’s most desirable floorplans—with the primary suite conveniently located on the first floor and two additional bedrooms upstairs. This thoughtfully designed layout is ideal for families, first-time buyers, those looking to downsize, or anyone seeking comfortable living with flexibility for guests, a home office, or additional living space. Situated on a premium lot backing to a peaceful conservation/green area, this home offers a wonderful sense of privacy and a tranquil natural backdrop. Inside, numerous builder upgrades and thoughtful custom enhancements create a beautiful blend of modern style, classic elegance, and everyday functionality. Upgrades include enhanced tile, bathrooms, and kitchen finishes, complemented by a custom-designed stair railing that adds a distinctive touch of sophistication. The spacious primary suite features a custom-built walk-in closet, maximizing storage and organization. An Ecobee Smart Thermostat system with Smart Sensors provides efficient, convenient control of the home's comfort while helping manage energy usage. Premium professionally installed ceiling fans in every room provide excellent air circulation and year-round comfort. The home is also professionally wired for rear surround-sound speakers, making it ready for an enhanced entertainment experience. All the rooms have plenty of natural lights! The garage is equally practical, featuring large custom-built ceiling-hung storage, providing valuable additional space while keeping vehicles and everyday belongings organized. Enjoy an outstanding location within Hickory Grove. The community pool and dog park are just down the street, while the Cross Seminole Trail can be easily accessed just outside the community—perfect for walking, jogging, or biking. The Magnolia Square Fountain and Park and The Winter Springs Town Center are both approximately a five-minute walk away, with roughly a dozen food-and-beverage places within walking distance or a short drive away. Central Winds Park is only about a 10-minute drive away. Access to 417 is about 7-minute drive away. With its highly sought-after first-floor primary suite, premium conservation lot, extensive upgrades, custom touches, and exceptional walkable location, this townhome offers a rare combination of comfort, style, privacy, and convenience.

1378 Tarflower Drive, Winter Springs
$499,900
4 Beds ⋅ 3 Baths ⋅ Parkstone SubDv. ⋅ 32708 Zip Code
Virtually Staged. Live the Florida lifestyle in the beautiful gated community of Parkstone! This 4-bedroom, 3-bath pool home offers the perfect combination of comfort, convenience, and resort-style living. Spend sunny afternoons relaxing by your own private screened pool, enjoy morning walks or bike rides along the nearby Cross Seminole Trail, or take advantage of Parkstone’s community pool, tennis and volleyball courts, playgrounds, and lakefront dock on Lake Jesup. Even better, lawn care is included through the HOA, giving you more time to enjoy everything the community has to offer. Inside, the open and inviting layout is designed for both everyday living and entertaining, with spacious gathering areas and easy access to the covered outdoor living and pool area. A downstairs bedroom and full bath provide flexibility for guests, a home office, or multigenerational living, while the spacious primary suite upstairs creates a comfortable private retreat. The home has also been thoughtfully cared for with approximately $5,000 invested in new gutters and an extensive underground drainage system, including underground downspouts and dual French drains. Approximately two tons of river rock, a side-yard walkway, refreshed landscaping in 2026, and refreshed tile grout in all three bathrooms add to the home’s move-in-ready appeal. Whether it’s coffee by the pool, an evening walk through the neighborhood, a bike ride on the trail, or a day enjoying the community amenities, 909 Devon Creek offers more than a home—it offers an easy, active Florida lifestyle.

909 Devon Creek Road, Winter Springs
$549,000
4 Beds ⋅ 3 Baths ⋅ Oak Forest Unit 8 SubDv. ⋅ 32708 Zip Code
Spacious 4 bedroom, 3 bathroom pool home off of Tuskawilla Rd! This home features two story ceiling in the formal living and dining room. The staircase and second story walkway over look the entrance and formal areas. The family room has a fireplace and is joined with the kitchen. On the first floor are also three large bedrooms, two of the bedrooms have attached baths. The primary bedroom is upstairs and has double walk in closets, and an oversized en suite bathroom. The pool has a screen enclosure and the yard is fenced. Roof replaced in 2022, complete Replumb ins 2023.

1142 Oday Drive, Winter Springs
$295,900
3 Beds ⋅ 2 Baths ⋅ Wildwood SubDv. ⋅ 32708 Zip Code
SINGLE FAMILY HOME. Stunningly Renovated Gem in Winter Springs. Looking for the perfect blend of modern comfort and community living? Look no further! This spectacular, Renovated home in the desirable Wildwood community is ready for its new owners. Brand New Solar Panel System, Green energy. Paid off. This almost 1,300 sq. ft. residence has been thoughtfully updated with high-end finishes throughout. Offers New roof in 2022. New cabinets and stunning granite countertops. Modern Baths with Porcelain wall tiles, new vanities, and upgraded faucets. Fresh paint inside and out, new baseboards, and elegant tile flooring. Resently replace water heater, A/C unit 2018 . 3 Bedrooms, 2 Bathrooms, spacious living and dining areas, plus a garage and carport. Community & Location Benefits: Enjoy the active Wildwood lifestyle with access to a pool, playground, tennis court, and volleyball court. You will be perfectly positioned in a top-rated school district with easy access to major highways (434, 17-92, I-4, 417, 436) and minutes away from the Altamonte Mall, Lake Mary, premier shopping, dining, and healthcare.

736 Summerland Drive, Winter Springs
$439,900
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
$665,000
4 Beds ⋅ 3 Baths ⋅ Chestnut Estates Ph 2 SubDv. ⋅ 32708 Zip Code
MOTIVATED SELLER! Elegant conservation retreat in prestigious Chestnut Estates-Tuscawilla. On a quiet cul-de-sac, this impeccably maintained four-bedroom, three-bath residence offers a rare combination of privacy, timeless comfort and everyday luxury. Backing to a serene conservation area with no rear neighbors, the home is surrounded by mature landscaping and picturesque natural views, creating a peaceful retreat, and rear patio has new pavers. Thoughtfully designed with a desirable split-bedroom floor plan, the spacious interior offers functionality and elegance. Generous closet space, large pantry and built-in workspace provide everyday convenience, while the open concept kitchen flows seamlessly into the family room and casual dining area, creating a warm and welcoming atmosphere that's ideal for gathering with family and friends. An oversized bonus room/enclosed Florida room with rich wood flooring expands the living space and offers endless possibilities, including a game room, music room and fitness studio. Enhanced with a mini-split system installed in 2025, this versatile space provides year-round comfort and is the ideal setting for entertaining or enjoying quiet evenings while overlooking the tranquil conservation backdrop. Roof (2023) with secondary barrier, HVAC (2025) with AC purification system included, plumbing updates and newer water heater. Schedule your private showing today!

223 Blue Creek Drive, Winter Springs
$199,900
2 Beds ⋅ 2 Baths ⋅ Cypress Club SubDv. ⋅ 32708 Zip Code
Great investment property!...Beautiful 2/2 townhome in highly desirable Cypress Club community in The Highlands of Winter Springs, located in close proximity to SR 434! **Freshly Painted with light and neutral colors throughout! Vaulted ceiling in the very spacious/huge... family/great room with a wood burning fireplace! Split bedroom floorplan, with one bedroom downstairs. Brand new ceiling fan in upstairs bedroom. Tub and shower combination and linen closets in both bathrooms. Tile flooring in the living areas and laminate in the bedrooms. **Brand New Lennox A/C system and a washer and dryer included! Screened and Covered porch and an outside storage closet for additional storage. Two pools: the Cypress Club Community pool, and The Highlands master community pool! Brand new roofs in the community, HOA covers building insurance and grounds maintenance. Two assigned parking spaces. The community offers a fabulous club house, nature walking trails, parks, playground and tennis courts. Located close to shops and restaurants and very close to SR 434, SR 17/92 and SR 417 for easy commuting.

497 Club Drive, Winter Springs
$329,900
3 Beds ⋅ 2 Baths ⋅ Highland Village 1 SubDv. ⋅ 32708 Zip Code
Welcome home to this cozy 3-bedroom, 2-bath bungalow-style home located in the resort-like Highlands community, offering 1,178 sq. ft. of living space. This home features vaulted ceilings, ceramic tile throughout, fresh interior paint, and a newly renovated kitchen with granite countertops, solid wood shaker-style cabinets, and black appliances. Major updates include a 2025 water heater and a new electrical panel inside and outside. The generously sized primary bedroom includes a built-in California Closets system, providing stylish and highly functional custom storage. The secondary and third bedrooms are also well-sized—perfect for guests, family, or easily converted into a home office. Washer and dryer are included in the sale. Enjoy the covered and screened lanai overlooking a charming New Orleans-style courtyard with pavers, a firepit, and a lamp post. The oversized, fully fenced, and cleared backyard offers plenty of space to relax, entertain, or garden, providing a strong sense of privacy. The Highlands is a highly sought-after, established community with low HOA fees and beautiful mature trees throughout. Amenities include an Olympic-size community pool, walking trails, playground, tennis court, volleyball court, and a clubhouse. Ideally situated just off State Road 434 Florida and Tuskawilla Road, this home offers quick access to Winter Springs Town Center for shopping and dining, and is just a short stroll from Torcaso Park—a lively neighborhood park featuring basketball courts, soccer and football fields, playgrounds for all ages, a splash pad, sand play areas, and picnic pavilions, perfect for both active days and relaxed family outings.

335 Kirkcaldy Drive, Winter Springs
$1,200,000
5 Beds ⋅ 4 Baths ⋅ Tuscawilla SubDv. ⋅ 32708 Zip Code
Experience the beauty of city living on 2.3 acres in the highly desirable city of Winter Springs with no HOA—where open space, natural surroundings, and an equestrian friendly lifestyle come together. This unique property offers the freedom of rural living while remaining conveniently located near the Tuscawilla area. The fully usable acreage is ideal for horses, cattle, or other livestock. If livestock isn’t your preference, the expansive space is perfect for recreational vehicles, racing cars, or other outdoor hobbies. The 5 bedroom, 3 bath home is solid and ready for your personal updates. A standout feature is the 1,500 sq. ft. garage, offering ample room for a boat, race cars, or additional storage. This 2.3 acre parcel is one of the few remaining equestrian friendly properties in the city of Winter Springs, providing a rare combination of comfort, privacy, and natural surroundings. The home is zoned for highly rated Seminole County schools, offering the perfect blend of private country living and excellent educational opportunities. Seller motivated!

1281 Natures Way, 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
$210,000
2 Beds ⋅ 2 Baths ⋅ Cypress Club SubDv. ⋅ 32708 Zip Code
Beautiful 2 bedroom 2 bathroom townhome (Not a condo which means more financing choices for you as a buyer) located in the desirable Cypress Club within the Highlands Community. Brand New Roof on this townhome. The 20ft high ceiling in the Great Room gives this home a very open design with lots of natural light. Sliding doors lead out to a screened porch with separate locked storage space. Guest/2nd bedroom on the first floor with direct access to the 2nd bathroom. All appliances purchased New in 2022 and are included with sale. New A/C 2023. Upstairs flexible loft space makes for a nice home office. Large primary bedroom has beautiful laminate floors and plenty of closet space and updated bathroom. Two assigned parking spaces directly in front of your townhome makes coming home convenient. Cypress Club residents enjoy their Own Private Community Pool in addition to All Highlands amenities. They include Audibon Park with BBQ/Picnic Area, Playgrounds, Olympic Size Pool, Kiddie Pool, Nature Walking Trails & Tennis & Pickleball Courts and a Clubhouse. Zoned for highly rated Seminole County Schools with The Highlands elementary school located within the community. Nearby Cross Seminole Trail and Central Winds Park. Located close to 17-92, SR417, grocery stores, fitness clubs.

499 Club Drive, Winter Springs
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