Winter Springs Homes under $500,000

One or more photo(s) has been virtually staged. Stylish two-story home offering spacious living and great design flow. The main level features a formal dining room ideal for gatherings, along with a kitchen highlighted by accent lighting, ample cabinetry, and a clear view into the living room for easy conversation and entertaining. Upstairs, all four bedrooms provide generous space, while both

Cheryl Fabian MAINSTAY BROKERAGE LLC

This lovely and desirable home is located in one of Winter Springs most desirable neighborhoods. The serene community is outstanding with Oak tree canopies and spacious lots with nice curb appeal and lush landscaping. Welcome to this inviting 4 bedroom, 2 bath home which has over 2,000 square feet living area. As you enter into a nice foyer, there is a comfortable great room to your left and a

Nancy Langley PREMIUM PROPERTIES R.E SERVICE

Beautiful home in the heart of Tuscawilla Country Club — a well-established, walkable, and extremely safe neighborhood. Zoned for top-rated A+ schools: Rainbow Elementary, Indian Trails Jr. High, and Winter Springs High School. This 3-bed, 2-bath home offers 1,889 sq ft, a 2-car garage, and a long list of upgrades throughout: • Architectural-shingle roof (2017)• Carrier HVAC (10/6/2021)•

Bob Knowles RED CARPET REALTY FLORIDA

Welcome home! This charming Winter Springs property features high ceilings, an updated kitchen, and a new roof installed May 2025. The spacious yard is perfect for entertaining, relaxing, or giving your pets room to play. Located in an excellent Central Florida location, you’ll enjoy convenient access to shops, restaurants, parks, and major highways. A comfortable home with great upgrades in a

Kim Pollaro REAL BROKER, LLC

Lovely 3 bed, 2 bath ONE STORY home in the quiet, sought after Tuscawilla community! NEW A/C installed 2025. Enter this home and you're welcomed by beautiful, bamboo flooring, accented by impressive, vaulted ceilings! This comfortable home has plenty of space. Kitchen features gorgeous granite countertops, Stainless Steel appliances, NEW DISHWASHER, plenty of solid wood cabinets, a snack bar, and

Harry Kazarian STRONG FOUNDATION REALTY LLC

Located in the highly desirable Tuscawilla community, this home offers an open floor plan with a blend of tile and wood flooring throughout. The spacious kitchen features striking black galaxy granite countertops and ample cabinet space. Enjoy the outdoors in your fully fenced backyard retreat, complete with mature landscaping, a cozy fire pit area, and plenty of room to relax or entertain. The

Rick Cole KELLER WILLIAMS WINTER PARK

Welcome to this spacious and inviting single-family home nestled in the heart of Winter Springs. This residence at 1294 Madelena Ave. offers a wonderful blend of comfort, value and potential. Key features include: 3 bedrooms, 2 full bathrooms. Approximate 1,722 sq ft of living space. Lot size approximately 0.26 acre. Built in 1980. Beautiful and spacious in-ground swimming pool and area. Open and

Raymond Rauber MAGNA PROPERTY GROUP, LLC

There’s still time to get in before the end of year. You can now make this beautifully renovated 3 bed 2 bath Single Family Home in the popular Winter Springs Ranchlands your very own. No HOA and 1 Full Acre. This terrific home has vaulted ceilings and a skylight, a super spacious layout with large windows, new flooring, all new cabinets and new granite countertops throughout the home including

John Vincent JR REALTY GROUP LLC

Spectacular Corner Townhome Awaits!!!Experience the lifestyle you’ve always dreamed of in this stunning three-story townhome showcasing modern finishes and serene conservation views. Sip your favorite beverage or unwind on the spacious private front porch. The first floor offers a versatile flex space, ideal for a home office, den, or even a fourth bedroom. On the second floor, enjoy an

Monica Puche LPT REALTY, LLC

Experience elevated living in this beautifully appointed 4-bedroom, 2.5-bath end-unit townhome, designed for both comfort and style. Start your day with a serene walk or bike ride on the Cross Seminole Trail, just steps from your door. Enjoy exclusive access to the resort-style pool, fully equipped fitness center, and clubhouse ideal for private gatherings. Nearby, explore Central Winds Park and

Ileana Irizarry Melendez EXCLUSIVE HOMES REALTY, INC.

One or more photo(s) has been virtually staged. Welcome to Greenbriar at Tuscawilla, where this beautiful 3-bedroom, 2.5-bath home enjoys direct golf course frontage on the prestigious Tuscawilla Country Club—a private club offering championship golf, tennis, pickleball, swimming, fitness facilities, and upscale dining. Inside, soaring vaulted ceilings and abundant natural light create an

James Clark CENTURY 21 ALTON CLARK

One or more photo(s) has been virtually staged. NEW ROOF, JUST COMPLETED 10/2025. Check out this beautifully maintained 3-Bedroom 2-Bath Home on a Corner Lot with Screened Porch & Community Amenities. As you drive up, you are immediately welcomed by the well-manicured yard, majestic oak trees, and a brick paver driveway that enhances the home’s charming curb appeal. Step inside to find elegant

Renee Killiri RED BIRD REALTY OF FLORIDA INC

ELEGANT CONTEMPORARY HOUSE WELCOMES YOU THROUGH A FOYER INTO THE LIVING/DINING AREA. THE HOUSE HAS 3 BEDROOMS AND THE POTENTIAL TO EASILY BUILD A 4TH ONE, AS IT IS ALREADY IN PUBLIC RECORDS. ADD EQUITY TO YOUR HOME! FRESH COAT OF PAINT ON ALL THE HOUSE AND NEW ENGINEERED WOOD FLOORS. ALL WINDOWS HAVE WOOD SHUTTERS. KITCHEN IS SPACIOUS, WITH STONE COUNTERS, STONE BACKSPLASH AND STAINLESS STEEL

Connie Shepherd HOME WISE REALTY GROUP, INC.

One or more photo(s) has been virtually staged. Welcome to your beautiful new home in the heart of Winter Springs! This spacious and low-maintenance townhome in the highly desirable Jesup’s Landing community is 100% move-in ready and filled with modern updates and smart features. This three-story home offers 3 bedrooms, 3.5 bathrooms, and plenty of space to spread out. On the ground level, you’ve

Debbie Bergeron PREMIUM PROPERTIES R.E SERVICE

Welcome to this beautifully updated, move-in ready, fully furnished 3-bedroom, 2-bath single-family home — with FURNITURE, DECOR, and APPLIANCES INCLUDED! Located in the desirable Sunrise community of Winter Springs. The house has an enclosed rear patio an additional 4th air conditioned space/room, offering flexible space for a gym, sun room or home office. Set on an oversized 0.27-acre lot, this

Renan Serretiello FLORIDA CONNEXION PROPERTIES

"We're Opening the Door Wider (price flex) so YOU can come in on the BIGGEST is BEST! END UNIT! with the Brightest and Best Views, Longest Driveway, Largest Yard, and First Time on the Market! Are you looking for a "good enough" copy or looking for "THE RIGHT ONE" who won't settle? Well, we have the right one when it comes to low-maintenance luxury. You will find this fairway-facing townhome in a

Rafael Kawala WHITE WHALE REAL ESTATE

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

Ramon Ortiz Cruz DIAMOND 2000 REALTY, INC

Very well maintained home in Tuskawilla! Updated kitchen with Granite countertops, Elegant mirrored wall, Ceramic Tile throughout. Double sinks in beautiful master bathroom with garden shower tub! Owners have access to the neighborhood clubhouse and Community pool, HOA takes care of front yard lawn maintenance. Two parks and a nature trail are walking distance from the home. Walk to Trotwood Park

Ramon Ortiz Cruz DIAMOND 2000 REALTY, INC

Set at the quiet end of the community, this 2023 three-story townhome backs to preserved land and connects directly to the 23-mile Cross Seminole Trail—perfect for morning runs, dog walks, and weekend rides. Enjoy peaceful, green views from your private cozy front porch while drinking your morning coffee!. 4 bedrooms, 3.5 baths, and a 2-car garage in Winter Springs!!!!First floor offers a

Cindy Sosa-Castro COLDWELL BANKER RESIDENTIAL RE

With a spacious open concept ground floor, the Catalina II has plenty of room for entertaining. This floorplan features 4 bedrooms, 2.5 bathrooms and a rear-loading 2-car garage. The owner’s suite features an ensuite owner's bath and a walk-in closet. This chef-worthy kitchen features stainless steel appliances, a walk-in pantry, and a breakfast bar.

Amanda Warren MATTAMY REAL ESTATE SERVICES