Homes for Sale Near Winter Springs High in Winter Springs - 104 homes

Remarks: Welcome to Cypress Club, a townhome community located in The Highlands within Winter Springs. Two bedrooms/two bath home is two stories offering split bedrooms. The living room/dining room combo provides high lofty ceilings with celestial windows providing natural sunlight to the home. Sliding glass doors open to a screen enclosed patio to the rear of the property that overlooks Winter Springs peaceful conservation area. Open stairwell that leads to the loft where you will find a spacious laundry arrangement set up. The master bedroom and bath are on the second floor. The home has been freshly painted. The Highlands offers many amenities to include tennis/pickle ball courts, basketball and volleyball, park with BBQ areas and a covered pavilion and boasts it's Junior Olympic size swimming pool. Playgrounds throughout the community. Cypress Club also provides a community pool. The roof is new 2026.

Listing is courtesy of: PAINE-ANDERSON PROPERTIES, INC (407-695-7898)

Listing Agent: Joyce Gary (407-782-3276)

Remarks: Live luxuriously in almost New Townhouse! Immaculate 3-story townhouse (built 2023) boasts $20,000 in builder upgrades and offers a modern living experience! Unwind while sipping your morning coffee or taking a break on the front porch overlooking serene conservation. Inside, a flexible space on the first floor can be your home office, den, or 4th bedroom with a full en-suite bathroom (including a tub!). Park with ease in the epoxy-floored garage featuring overhead storage racks and extra space for storage. The open-concept second floor features high ceilings and a perfectly sized dining area convenient for family and friends meal time. Unleash your inner chef in the gourmet kitchen with built-in oven, HUGE expansive pantry, granite countertops, soft-close drawers, upgraded cabinets (42" with crown molding), designer fixtures, and updated lighting fixtures. A convenient half bath completes this level. Relax in the spacious living room with room for a desk or play area. The third floor features a well-sized primary bedroom with a HUGE walk-in closet. Upgrades galore: Level 5 textured carpeting provides durability with a touch of luxury. Home is prewired for whole house security including camera hook up. The upgraded laundry room boasts additional storage cabinets and designer tile flooring. Two more bedrooms and a full bath with tub round out the top floor. Enjoy the Florida lifestyle! Take a dip in the community pool just 20 steps away, explore the nearby town center, or hop on the scenic 23-mile Cross Seminole bike trail directly accessible from your doorstep. Conveniently accessible to the 417 highway, local restaurants, shopping, playgrounds and parks, a splash pad, and more just minutes away!

Listing is courtesy of: CREEGAN GROUP (407-622-1111)

Listing Agent: Sylvana Minnetto (321-946-9876)

Remarks: HUGE PRICE DROP! SELLERS NEED TO SELL! WALK ON IN AND CALL IT HOME! Welcome to this stunning 4-bedroom, 3-bathroom home nestled in the highly sought-after Tuskawilla Crossings community of Winter Springs. From the moment you step inside, you’ll be greeted by a tastefully decorated foyer that opens up into a spacious living room and a beautifully designed open kitchen, perfect for entertaining and everyday living. On the first floor, you’ll find a guest bedroom and a full bathroom, offering flexibility for visitors or a home office. One of the standout features of this home? Outdoor living spaces galore! Enjoy not one, not two, but three screened-in patios — a cozy side porch off the living room, a private patio between the kitchen and garage, and an upper-level patio accessible from the loft — ideal for relaxing after a long day. Upstairs, you’ll find a generously sized loft, a large laundry room, and three more bedrooms, including the spacious primary suite. Located in the desirable Seminole County School District, this home is just minutes from the 417, making commutes a breeze. Don’t miss your chance to own this incredible home in Tuskawilla Crossings — schedule your private tour today before it’s gone!

Listing is courtesy of: VOSS REALTY INC (407-456-0777)

Listing Agent: Lindsay Kaye Voss (407-456-0777)

Remarks: Under contract-accepting backup offers. Welcome to a home where smart technology, everyday comfort, and an unbeatable location come together in one exceptional package. Nestled on a beautifully landscaped corner lot in the highly sought-after Winter Springs/Tuskawilla area, this 4-bedroom, 3-bath residence with a 2-car garage offers the perfect blend of function, style, and convenience — with room to grow thanks to a pool-planned backyard ready for your personal vision. Inside, you’ll find a home designed for modern living. The kitchen is outfitted with sleek LG appliances (2023), paired with a matching LG washer and dryer (2023) for a fresh, move-in-ready feel. A Kinetico® whole-house water filtration and soft water system ensures high-quality water throughout, while the energy-efficient GE hybrid heat pump water heater not only saves on utility costs but also helps keep the garage cooler — a practical bonus for Florida living. Tech-savvy buyers will appreciate the CAT 5e high-speed ethernet wiring and smart home features that make daily life effortless. Control your garage from anywhere with the brand-new Chamberlain Bluetooth-enabled opener (2025), and manage irrigation with ease using the Orbit wireless sprinkler system (2021), complete with internet-based weather forecasting. This home is also built for enjoyment and entertaining. Whether you’re hosting friends or relaxing after a long day, you’ll love the in-ceiling speaker system in both the garage and back lanai, plus a living room pre-wired for a premium Bose® surround sound experience. Additional highlights include refreshed attic insulation (2022) for enhanced energy efficiency and an insulated, hurricane-reinforced garage door, backed by a lifetime maintenance and repair agreement with Precision Door Service — offering both durability and peace of mind. Location truly seals the deal. Just minutes from SR 434, 417, Publix, and a wide array of shopping and dining options, this home places everything you need right at your fingertips while still offering the charm and appeal of one of Central Florida’s most desirable communities. Meticulously maintained and thoughtfully upgraded, this home delivers the lifestyle today’s buyers are looking for — smart, stylish, and ready to enjoy from day one.

Listing is courtesy of: RE/MAX 200 REALTY (407-629-6330)

Listing Agent: John Muccigrosso, Pa (407-234-6330)