Casselberrry/Winter Springs / Tuscawilla Homes with Contemporary Architectural style

Casselberrry/Winter Springs / Tuscawilla Homes with Contemporary Architectural style

Welcome to the enchanting region of Casselberry, Winter Springs, and Tuscawilla—an idyllic corner of Seminole County, Florida, where modern living meets natural beauty. Nestled just north of Orlando, this vibrant area is renowned for its lush landscapes, picturesque parks, and strong sense of community, making it an ideal place to call home.

Winter Springs boasts a variety of contemporary architectural styles that harmoniously blend with the serene surroundings. These homes are characterized by clean lines, open spaces, and abundant natural light, creating a perfect sanctuary for those who appreciate modern design. With features such as sleek finishes, innovative layouts, and energy-efficient solutions, contemporary homes in this region cater to a lifestyle of comfort and sophistication.

Living in Winter Springs means you’re never far from nature’s embrace. Explore the scenic trails of the nearby Central Winds Park or enjoy a leisurely afternoon at the serene Lake Jesup. The area is also home to a rich array of dining, shopping, and entertainment options, ensuring that residents have access to everything they need right at their fingertips.

Families will appreciate the highly regarded schools in the Seminole County School District, while outdoor enthusiasts can take advantage of the numerous recreational activities available, from hiking and biking to golfing and fishing.

Whether you’re seeking a modern masterpiece in Tuscawilla or a charming contemporary abode in Casselberry, this region offers a unique blend of style, comfort, and community that is sure to captivate your heart. Come discover your dream home in this beautiful part of Florida!

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

$725,000
4 Beds ⋅ 3 Baths ⋅ Northern Oaks SubDv. ⋅ 32708 Zip Code
Welcome to Northern Oaks a newer Winter Springs gated community that features an enclave of just 35 homes. You will love the privacy that surrounds this premium lot with no rear neighbors, water views in the rear and side of the home. Built in 2021 by Dream Finders Homes, you will absolutely fall in love with the open floor plan that connects the Great room, Dining Room and Kitchen all together. This turnkey 4 bedroom/3 bath property features ceramic wood plank tile flooring throughout, plantation shutters, a large covered lanai with a motorized screen overlooking the water, aluminum fencing that defines the backyard and a spacious 3 car garage. The gourmet kitchen will please the chef in the family with the oversized island, granite countertops, custom backsplash, stainless appliances, a pot filler to compliment the cooktop and a walk-in pantry with custom shelving. The alternate bedrooms are all a generous size with the front bedroom having a dedicated bathroom making it perfect for guests. The Primary suite includes dual custom closets for maximum space, enjoy the luxurious bathroom which has a huge walk-in shower & includes dual shower heads, a spacious dual vanity & separate water closet. The 3 car garage was set up with a workshop in the single bay with additional electrical outlets including a dedicated 220 volt. There are motorized ceiling shelving in the dual bay garage for maximum storage without the hassle of using a ladder. This prime location puts you close to highly rated Seminole County Schools, University of Central Florida, Central Winds Park, Oviedo on the Park, the Cross Seminole Trail and the 417 Expressway for a commute to the Beaches, Downtown or to the Airports. This home will appeal to your most discriminating buyer!

940 Talon Place, Winter Springs
$695,000
4 Beds ⋅ 3 Baths ⋅ Chestnut Estates Ph 2 SubDv. ⋅ 32708 Zip Code
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), plumbing updates and newer water heater. Schedule your private showing today!

223 Blue Creek Drive, Winter Springs
$525,000
4 Beds ⋅ 3 Baths ⋅ Greenbriar Sub Ph 2 SubDv. ⋅ 32708 Zip Code
Virtually Staged. Welcome to 947 Glen Abbey Circle in the sought-after Greenbriar Country Club and Golf Course community of Winter Springs. This impeccably maintained 4-bedroom, 3-bathroom home with a spacious loft offers thoughtfully designed living space with beautiful conservation views and a flexible floor plan perfect for everyday living and entertaining. The bright and open layout features soaring ceilings in the formal living and dining areas, creating an impressive first impression. The spacious kitchen is equipped with wood cabinetry, ceramic tile flooring, and overlooks the family room, where sliding glass doors lead to a screened porch overlooking the peaceful conservation area. The first-floor primary suite provides a private retreat with a large walk-in closet, garden tub, separate shower, and dual vanity. An interior laundry room and convenient half bath complete the main level. Upstairs, you'll find three additional bedrooms, a full bathroom, and a versatile loft that overlooks the living and dining areas below, enhancing the home's open and airy feel. Whether used as a game room, home office, media space, or play area, the loft adds flexibility to meet a variety of lifestyle needs. Recent updates and meticulous care throughout make this property truly move-in ready. Enjoy the lifestyle that Greenbriar offers, with access to golf, country club amenities, top-rated Seminole County schools, shopping, dining, and major roadways just minutes away. This is a rare opportunity to own a beautifully maintained home in one of Winter Springs' most desirable communities. Schedule your private showing today.

947 Glen Abbey Circle, Winter Springs
$685,000
4 Beds ⋅ 3 Baths ⋅ Winding Hollow Unit 2 SubDv. ⋅ 32708 Zip Code
Pride of ownership is evident throughout this beautifully updated, MOVE-IN PERFECT, one-owner home located in the highly sought-after WINDING HOLLOW community of Winter Springs. This ideal two-story floor plan offers 4 BEDROOMS, 3 FULL BATHS, BONUS ROOM, 3-CAR GARAGE, and a LARGE SCREENED LANAI, showcasing timeless style, thoughtful updates, and versatility with TILE FLOORING throughout the first floor and LAMINATE WOOD FLOORING upstairs. The bright, OPEN-CONCEPT floor plan offers exceptional flow and is perfect for entertaining, featuring spacious formal living and dining rooms with soaring ceilings that create an inviting sense of space. The heart of the home is the beautifully designed ISLAND KITCHEN, perfectly positioned between the breakfast nook and impressive family room with 18-FOOT CEILINGS and dramatic upper windows that flood the home with natural light. The kitchen features GRANITE COUNTERTOPS, ABUNDANT WOOD CABINETRY with PULL-OUT DRAWERS, STAINLESS STEEL APPLIANCES, PANTRY, and convenient access to the garage and laundry room with additional storage. The spacious FIRST-FLOOR PRIMARY SUITE offers a sitting area, TWO WALK-IN CLOSETS, and an updated spa-inspired bath featuring a SOAKING TUB, GLASS SHOWER, and DUAL QUARTZ VANITIES, creating the perfect private retreat. A SPLIT FIRST-FLOOR GUEST SUITE with a full bath provides ideal accommodations for visitors or MULTI-GENERATIONAL LIVING. Upstairs you’ll find BEDROOMS 3 & 4, a full hallway bath, and a versatile BONUS ROOM/FLEX SPACE with a walk-in closet overlooking the family room below. Easily used as a 5TH BEDROOM, MEDIA ROOM, PLAYROOM, HOME OFFICE, or HOME GYM, this flexible space adapts to your family’s needs. Enjoy Florida living year-round from the expansive TILED SCREENED LANAI, accessible from the formal living room, family room, and primary suite while overlooking the PRIVATE, LUSHLY TREED BACKYARD. Additional highlights include PLANTATION SHUTTERS THROUGHOUT, a spacious 3-CAR GARAGE with overhead storage, an EXPANDED BRICK-PAVER DRIVEWAY, 2018 ROOF, TWO ZONED A/C SYSTEMS (2022 & 2019), 2019 WATER HEATER, and COMPLETE PLUMBING REPIPE (2025). Ideally located WITHIN WALKING DISTANCE TO THE CROSS SEMINOLE TRAIL & CENTRAL WINDS PARK, and just minutes from TOP-RATED WINTER SPRINGS SCHOOLS, shopping, dining, SR 417, and US 17-92, this exceptional home truly offers the perfect combination of LOCATION, LIFESTYLE, AND VALUE. WELCOME HOME!

525 Saddlewood Lane, Winter Springs
$210,000
2 Beds ⋅ 2 Baths ⋅ Cypress Club SubDv. ⋅ 32708 Zip Code
Move in Ready!...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
$275,000
3 Beds ⋅ 2 Baths ⋅ Cypress Club SubDv. ⋅ 32708 Zip Code
Welcome to 476 Club Drive, a beautifully cared-for townhome nestled in the highly sought-after Cypress Club section of The Highlands in Winter Springs—a community known for its incredible amenities and natural surroundings. This spacious 3-bedroom, 2-bath residence blends comfort, functionality, and peace of mind with key updates already completed. Enjoy the benefits of a new roof 2026, new water heater 2026, 2020 A/C system, a full repipe completed in 2016, and a 2016 whole home water softener. Inside, you’ll find an inviting layout with knockdown ceilings throughout the main level and an open living and dining area tucked toward the rear of the home for added privacy. Updated recessed lighting enhances the space, creating a warm and welcoming atmosphere. Just beyond, a step-down enclosed patio offers a serene retreat overlooking wooded views—perfect for relaxing or entertaining. The flexible floor plan includes a downstairs bedroom with an adjacent full bath, ideal for guests, a home office, or multi-generational living. Upstairs, two generously sized bedrooms feature soaring ceilings and abundant natural light. The primary suite offers ample closet space and tranquil views of the surrounding greenery, along with a spacious en-suite bath complete with a Jacuzzi tub and separate shower—perfect for unwinding after a long day. Cypress Club stands out as the only neighborhood within The Highlands with its own private pool, in addition to access to the community’s extensive amenities. Residents enjoy multiple pools, tennis courts, scenic walking trails, parks, pavilions, BBQ areas, a clubhouse, as well as volleyball and basketball courts—delivering a true Florida lifestyle right outside your door. Don’t miss this opportunity to own a move-in-ready home in one of Winter Springs’ most desirable communities!

476 Club Drive, Winter Springs
$219,500
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) 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
$425,000
3 Beds ⋅ 2 Baths ⋅ Wedgewood Tennis Villas SubDv. ⋅ 32708 Zip Code
PRICE REDUCTION!!!Ready to move into! Well maintained and updated 3-bedroom Tuskawilla villa, HOA maintains the lawn. This home boasts an open floor plan featuring beamed vaulted ceilings, a wood burning stone fireplace, an eat in kitchen and a spacious screened porch ROOF INSTALLED IN 2023, AC INSTALLED IN 2021, Resurfaced bath tub, shower and vanity countertops. Professional tennis courts and a clubhouse facility right across the street. Opportunity to join the Tuskawilla Country Club for golf, swimming, dining and more! NEW KITCHEN INSTALLED IN 2023! WITH UPDATED CABINETRY, QUARTZ COUNTERTOPS, STAINLESS STEEL APPLIANCES! CLOSET PANTRY & QUARTZ BREAKFAST BAR! Eat-in kitchen, vaulted ceilings with elegant wooden beams. Enjoy the living space outdoors in a large screened-in patio, enjoy your backyard, with 12 inch concrete tiles, vinyl fence for privacy, creating a relaxed setting for entertaining . Relax and enjoy the enclosed front porch with sliding door access to both bedrooms. Sliding door in the master bedroom with access to the ceramic tiled back screened porch. This home is near Trotwood Park, Cross Seminole Trail and Bear Creek Nature Trail. A short drive to Oviedo Mall, Winter Springs Town Center and the many parks in the area. The location is one of the best with quick access to the 417. The schools include some of the top-rated schools in all of Central Florida. Schedule your showing today, before it’s too late!

1422 Spalding Road, Winter Springs
$249,900
3 Beds ⋅ 2 Baths ⋅ Tuscany Place Ph 1 SubDv. ⋅ 32708 Zip Code
MOTIVATED SELLER!!! Seller offering concession toward buyer closing cost. Location! Location! Location! This pristine condo nestled in the heart of Tuscawilla offers an incredible opportunity for low maintenance living in a serene and gated community. Enjoy summer days by the beautiful community pool and relax in the cabana. Across the way you will find access to Trotwood Park, with its picturesque settings ideal for picnics and recreational activities. Featuring a pavilion, playground, splash pad, tennis courts, and sports fields, it's a hub for family fun. For outdoor enthusiasts, the nearby Seminole County Cross Trail is perfect for biking and walking. As you tour the well maintained 3-bedroom, 2-bathroom condo, it encompasses 1425 sqft of second level living with private screened balconies overlooking the courtyard. Well-appointed kitchen equipped with brand-new stainless-steel appliances: Counter-depth Smart French Door Refrigerator, Smart SLIM Microwave, Bespoke Induction Range with self and steam cleaning Air Fry Convection Oven. A generous living and dining area that are inviting and ideal for entertaining. The split floor plan offers privacy for the owner suite, complete with its own screened balcony. The secluded and spacious secondary bedrooms are delightful for guests, office space or a growing family. New AC installed 7/2025 (16 seer AC unit with 1 year maintenance and 10yr-parts/2yr-labor). Families are drawn to the area thanks to its top-rated schools, making this condo not just a home, but a gateway to a vibrant community. Recently refreshed and ready for its new owners to display their personal touches.

600 Northern Way Unit 502, Winter Springs
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