Winter Springs Homes with Trail(s) Amenities

Winter Springs Homes with Trail(s) Amenities

Welcome to Winter Springs, Florida, a picturesque gem nestled in Seminole County, where the charm of suburban living meets the beauty of the great outdoors. Known for its friendly community atmosphere and rich natural landscapes, Winter Springs is a haven for families and outdoor enthusiasts alike. With its lush parks, scenic trails, and vibrant local culture, this city offers an ideal backdrop for both relaxation and recreation.

One of the standout features of Winter Springs is its extensive network of trails and parks, perfect for those who appreciate an active lifestyle. Imagine stepping outside your door to find a winding trail that invites you to explore the beauty of nature, whether you’re jogging, biking, or simply taking a leisurely stroll. Homes in Winter Springs with trail amenities provide residents with direct access to these scenic paths, promoting a healthy and active way of life.

In addition to the trails, Winter Springs boasts a variety of recreational facilities, including playgrounds, sports fields, and picnic areas that foster community engagement and family fun. The city hosts numerous events throughout the year, from farmers’ markets to seasonal festivals, ensuring there’s always something happening just around the corner.

Whether you’re looking for a cozy single-family home or a spacious property with room to grow, Winter Springs offers a diverse range of real estate options. Discover the perfect home that not only provides comfort and style but also embraces the outdoor lifestyle that Winter Springs is celebrated for. Experience the charm of this vibrant city—your future home awaits!

Newest Winter Springs 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
$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
$423,997
3 Beds ⋅ 2 Baths ⋅ Highlands Sec 1 SubDv. ⋅ 32708 Zip Code
PRICE IMPROVED + SELLER CONTRIBUTES TO CLOSING COSTS! Back on Market Financing Fell Through, Not the Home. Heated Pool | Winter Springs | Move-In Ready. Welcome to this well-maintained 3-bedroom, 2-bath home in an established Winter Springs neighborhood, featuring a private, heated pool with screen enclosure ready to enjoy year-round. The updated kitchen with gas range flows into a bright, open living area anchored by a cozy wood-burning fireplace, a rare find in Central Florida. Step outside to your screened pool and fully fenced backyard, ideal for entertaining or quiet weekends at home. A 2-car garage and tree-lined streets complete the setting. HOA dues are just $35.35/month notably low for a community with this level of amenity access. Zoned for Seminole County schools (buyer to verify assigned schools with the district). Minutes from walking and biking trails, shopping, and major roadways. Seller will contribute toward buyer's closing costs. FHA | VA | Conventional | Cash all financing welcome. Schedule your showing today.

872 Falkirk Drive, Winter Springs
$569,000
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 and Living rooms. Large bedrooms. Big Owners bedroom with walk-in closet and updated bath. 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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