Casselberrry/Winter Springs / Tuscawilla Homes with Trail(s) Amenities

Casselberrry/Winter Springs / Tuscawilla Homes with Trail(s) Amenities

Welcome to the enchanting region of Casselberry, Winter Springs, and Tuscawilla, where Florida's natural beauty meets suburban charm. Nestled in Seminole County, this vibrant area is renowned for its lush landscapes, picturesque lakes, and a strong sense of community. With its strategic location just north of Orlando, residents enjoy easy access to the bustling city while savoring the tranquility of suburban living.

Winter Springs is celebrated for its family-friendly atmosphere, excellent schools, and a plethora of recreational activities. The community is dotted with beautiful parks, walking trails, and playgrounds, making it an ideal place for families and outdoor enthusiasts alike. Tuscawilla, in particular, stands out with its stunning golf courses and serene residential neighborhoods, offering a peaceful retreat from the hustle and bustle of city life.

One of the standout features of this region is its homes with trail amenities. Imagine stepping out of your backyard and onto a scenic trail that winds through lush greenery and serene lakes. Many residences in Winter Springs and Tuscawilla boast direct access to these trails, providing endless opportunities for walking, jogging, or biking amidst nature's beauty. This unique feature not only enhances the quality of life but also fosters a strong sense of community as neighbors come together to enjoy the outdoors.

Whether you’re seeking a cozy family home, a luxurious estate, or a charming townhouse, the Casselberry/Winter Springs/Tuscawilla area offers a diverse range of real estate options to suit every lifestyle. Experience the perfect blend of nature, community, and convenience in this remarkable Florida region!

Newest Casselberrry/Winter Springs / Tuscawilla Homes with Trail(s) Amenities

$489,900
2 Beds ⋅ 3 Baths ⋅ Greens At Tuscawilla SubDv. ⋅ 32708 Zip Code
Welcome to the exclusive gated enclave know as The Greens of Tuscawilla. This luxury townhome delivers a rare combination of superior construction, premium finishes, prime location, and a maintenance-free lifestyle. Nestled amongst the trees in the heart of Tuscawilla is The Portofino II Model with Golf, Water and Conservation Views. Level One offers Open Concept Living with the ability for a future Elevator. (Elevator closets are located on both floors and are currently used as walk in storage closets). Level Two allows for privacy with all bedrooms located on this floor. Throughout the unit you will find soaring volume ceilings, crown molding, tall doors, recessed lighting, wood or tiled floors, fresh paint, granite countertops, 42 inch cabinets, designer lighting, fans, fire safety sprinkler system and much more. Start and end each day on your private screened porch where the views are unparralleled. The Greens consists of 15 buildings and 60 units. Residents enjoy lush landscaping, manicured lawns and a private dog park. Partake in the Country Club lifestyle with the private Golf Cart path that leads to Tuscawilla Country Club. Membership provides access to championship golf, Har-Tru clay tennis courts, pickleball court, Jr. Olympic-sized pool, fitness center, private restaurant/bar, and social calendar. The Tuscawilla Community has parks, sports courts and fields, playgrounds, hiking trails and splash pads. Walk, run, or ride while taking in the many natural areas throughout the 3500 acre community.

1541 Corkery Court Unit 1541, Winter Springs
$424,990
3 Beds ⋅ 3 Baths ⋅ Seminole Crossing Townhomes SubDv. ⋅ 32708 Zip Code
BETTER THAN NEW . . . Light and Bright and only 3 yrs old . . . Experience a blend of luxury, convenience and lifestyle in this stunning 3 bedroom, 2.5 bath designer townhome ideally situated in the heart of Winter Springs, one of Central Florida's most sought-after communities. This home has it all; crown molding, upgraded kitchen cabinetry with under cabinet LED lighting, Custom Closet, Premium Wood Laminate Flooring, Epoxy Garage Floor and so much more. This smart home features Electric Shades on EVERY window which can be set by timers or easily opened-and-closed with a remote, LED Security Lights on Front Porch and Driveway, WiFi enabled Garage Door opener and Smart Thermostat. Appliances included with this home are a built-in refrigerator, top of the line washer & dryer, oven, microwave and dishwasher. The spacious living and dining rooms flow seamlessly into the gourmet kitchen, making this home equally suited for entertaining guests or enjoying a quiet evening at home. Custom Pantry and Powder Room complete the First Floor. Upstairs you will find a spacious Loft, which can be used as an additional TV room, Playroom, or as an office; a separate 2nd floor Laundry Room, Spacious Owner’s Retreat with luxurious ensuite bath and walk-in custom closet; two additional generous bedrooms and a Full Bath. Enjoy your morning coffee on the large Front Porch overlooking a Park-like setting. Your guests will appreciate the connivence of parking on your oversized driveway. Location is everything and this home delivers. Walk just steps to the renowned Seminole Trail, where miles of scenic walking, jogging, and biking paths await. Spend your weekends exploring nearby parks, enjoying local events, or dining at the countless restaurants and cafés just minutes from your doorstep. Shopping, grocery stores, fitness centers, and everyday conveniences are so close that many daily errands can be accomplished within minutes. With easy access to major roadways, top-rated Seminole County schools, and the charming atmosphere that has made Winter Springs one of Central Florida's most desirable places to call home. Schedule your private showing today and discover why this remarkable residence stands above the rest.

1153 Spotted Sandpiper Loop, Winter Springs
$199,900
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
$475,000
3 Beds ⋅ 2 Baths ⋅ The Highlands Sections Seven & Eight SubDv. ⋅ 32708 Zip Code
Beautifully maintained 3-bedroom, 2-bathroom home located in the highly sought-after Highlands community in Winter Springs, FL. Real hardwood floors flow through the main living areas, adding warmth and timeless appeal. The spacious kitchen features elegant stone countertops, ample cabinetry, and plenty of room for cooking and entertaining. The primary suite serves as a relaxing retreat with an en suite bathroom that includes a dual sink vanity, a large soaking tub, and a walk-in closet. The split-bedroom layout offers added privacy, while the two additional bedrooms provide flexibility for guests, family, or a home office. Step outside to enjoy the oversized lot, offering plenty of space for outdoor living and activities. The screened-in lanai is perfect for enjoying Florida’s weather year-round, whether you're relaxing or hosting guests. A 2-car garage adds convenience and extra storage. Residents also enjoy access to a community pool, as well as tennis courts, pickleball courts, and scenic nature trails, perfect for an active and social lifestyle. Ideally located in Winter Springs, this home is close to top-rated Seminole County schools, beautiful parks and trails, shopping and dining options, and provides easy access to major roadways for commuting to Orlando and surrounding areas. Enjoy a balance of peaceful suburban living with everyday conveniences just minutes away.

629 Ryan Court, Winter Springs
$799,900
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
$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
$539,900
4 Beds ⋅ 3 Baths ⋅ Winter Spgs Unit 4 SubDv. ⋅ 32708 Zip Code
REDUCED! Beautiful Executive 4 bedroom POOL home in Tuscawilla Country Club Golf Community! NO HOA! Mediterranean feel with wrought iron accents and courtyard. Huge Kitchen with island in the middle. All appliances. Hot water heater 2017. Lots of cabinet space. Spacious eat-in area beside kitchen. Formal Dining, Living room, and family room. Big Owners bedroom with walk-in closet and updated bath on right side of house. On the left side of the house 3 large bedrooms and Inside laundry room. Large Pool (updated to salt system) 8 feet deep. Big fenced yard. Screened in porch. Oversized 2 car side entrance garage (currently part of garage is an office but could easily be converted back). New electric panel. House PASSED 4 POINT INSPECTION and copy of report will be given to new Buyer. Community allows golf carts. Plenty of room to park jet skis, boats, and RV. Great location near shopping, restaurants, hospital, and major roads. Good schools. Country Club has golf, tennis, swimming, and dining membership. Trotwood park has basketball tennis and pickleball courts, soccer field, and covered picnic area. Many parks in neighborhood. Close to Seminole Trail for walking and bike riding. Move right in! Must See!

30 Sable Court, Winter Springs
$215,000
2 Beds ⋅ 2 Baths ⋅ Cypress Club SubDv. ⋅ 32708 Zip Code
Move-in ready 2-bedroom, 2-bathroom single-level townhome in the heart of Winter Springs! Enjoy an updated kitchen with granite countertops, freshly painted interior, and new flooring. Relax on the screened and tiled lanai overlooking serene greenspace. This quiet, secluded community offers two assigned parking spaces and a community pool just steps from your front door. The HOA just installed brand new roofs throughout the community. Residents enjoy amenities including community pool, tennis courts, lush parks, and scenic walking trails throughout the neighborhood. Conveniently located near shopping, dining, entertainment, major highways, and all the area’s conveniences.

506 Club Drive, Winter Springs
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