Winter Springs Homes For Sale & Real Estate - 157 homes

Remarks: Welcome to this charming townhome in the highly desirable Jesup Reserve community located in beautiful Winter Springs. This 2-bedroom, 2-bath home offers comfort, convenience, and excellent potential for both homeowners and savvy investors. Step inside to find a spacious layout featuring a modern kitchen equipped with stainless steel appliances and a newer Carrier A/C system for year-round comfort. The home includes a 2-car garage plus additional street parking, making it perfect for families or guests. While the property does need new flooring, it presents a fantastic opportunity to add value and customize the space to your style. Residents of Jesup Reserve enjoy access to a beautiful community pool, ideal for relaxing and enjoying the Florida lifestyle. The home is also conveniently located near top schools, shopping, dining, and major retailers including Publix, making every day errands quick and easy. Whether you're a family looking for a welcoming community or an investor seeking a strong rental opportunity, this townhome offers location, amenities, and upside potential. Seller is very motivated to sell!!!!!!

Listing is courtesy of: WEICHERT REALTORS HALLMARK PRO (407-841-0888)

Listing Agent: James Rice (321-247-0583)

Remarks: Beautiful 2 bedroom, 2 bathroom townhome in Winter Springs, located in the sought-after Cypress Club at The Highlands community, known for its lush landscaping, fantastic amenities, and serene walking trails. Step inside to a spacious open floor plan with soaring vaulted ceilings and tile flooring throughout the main living areas. The living room features a cozy wood-burning fireplace, creating a warm and inviting focal point. The galley kitchen is fully equipped with all appliances, a glass tile backsplash, and a closet pantry for added storage. This home offers double suites, thoughtfully split between the two levels, each with its own private bathroom. The upstairs loft provides the perfect flex space for a home office, reading nook, or creative studio. Step out back to a lovely screened patio overlooking a private, park-like setting with no rear neighbors, creating a peaceful outdoor retreat. An exterior storage closet offers convenient space for bikes, tools, or gardening supplies. Recent updates include a full professional re-pipe (2026), new water heater (2025), new refrigerator (2024), new interior paint in modern greige tones (2023), and new carpet in bedrooms and stairs (2023). This townhome includes two reserved parking spaces, side-by-side, including one covered carport space. Cypress Club residents enjoy their own private community pool along with full access to The Highlands’ amenities, including a lap pool, tennis courts, playground, BBQ/picnic areas, and more. Ideally located with easy access to SR-434, 17-92, SR-417, and I-4, and zoned for top-rated Seminole County schools. Outdoor recreation and weekend adventure are just minutes away with convenient access to the Cross Seminole Trail and Central Winds Park, offering miles of scenic biking and walking paths, sports fields, and community events. Everyday conveniences are equally close by, with Winter Springs Town Center and other major shopping plazas just a short drive away, providing easy access to grocery stores, fitness centers, banks, restaurants, and all your daily essentials.

Listing is courtesy of: INFINITY REAL ESTATE GROUP (407-760-0835)

Listing Agent: Tamara Martin (407-760-0835)

Remarks: Under contract-accepting backup offers. Welcome to 130 Lombardy Road in Winter Springs! This 4-bedroom, 2 bath pool home is ready for new owners. With a newer roof (2024), vinyl flooring through most of the home, and an updated kitchen -- it's a great investment and priced to sell. A fenced yard, in ground pool and large screened patio make living the Florida lifestyle easy. The house has been replumbed and the interior recently painted. All appliances and washer and dryer included. This home is minutes to shopping, dining and a short ride to all Central Florida has to offer. Schedule your showing today!

Listing is courtesy of: COLDWELL BANKER REALTY (407-333-8088)

Listing Agent: Shannon Riva (813-789-7532)

Remarks: Under contract-accepting backup offers. Welcome to 1340 Delaney Drive, a move-in-ready home nestled in the heart of Winter Springs, FL. This beautifully maintained 3-bedroom, 2-bath residence offers 1,420 square feet of smartly designed living space, featuring a desirable split-bedroom floor plan that perfectly balances privacy and function. Step inside to discover a bright and neutral interior complemented by stunning laminate floors that flow seamlessly throughout the main living areas. The spacious kitchen is a modern delight with sleek stainless steel appliances, providing both style and practicality for your culinary adventures. The primary suite is tucked away for privacy and includes a private ensuite bathroom, offering a perfect retreat at the end of the day. Bedrooms two and three are generously sized and share a well-appointed full bathroom complete with a double vanity—ideal for guests or family members. You'll love the convenience of the in-home laundry closet, adding to the overall functionality of this thoughtfully designed home. Located just minutes from top-rated schools, shopping, dining, and local entertainment, this home offers both comfort and convenience in one of Central Florida’s most desirable communities. Whether you're a first-time homebuyer, downsizing, or looking for an ideal investment, 1340 Delaney Drive checks all the boxes. Don't miss your opportunity to call this lovely Winter Springs home your own!

Listing is courtesy of: EXP REALTY LLC (407-641-2808)

Listing Agent: Todd Schroth, Pa (407-641-2808)

Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Winter Springs POOL HOME Immediately Available! Voluntary HOA!! Bonus RV Accessible Pad w/ New 50-amp Outlet!!! This 4 bedroom, 3 bathroom property offers a split plan bedroom arrangement with 3 bedrooms & 2 bathrooms on one side of the home and the primary bedroom & bathroom far away on the other side. In between are multiple areas for gathering and entertaining: formal living room, formal dining room w/ pocket door access to the kitchen, dinette area w/ built-in desk, and family room with wood-burning fireplace & passthrough window for the wet bar. The family room, dinette and two bathrooms all have exits that lead out to the lanai for pool access. The L-shaped lanai highlights the pool and features an outdoor kitchen area & breezy ceiling fans, allowing the whole space to become a welcomed extension of the home. Situated on over half an acre, this home offers generous space both indoors and out, with added storage provided by a 10' x 12' shed. Add your very own vision to this well-loved home.

Listing is courtesy of: REDFIN CORPORATION (407-708-9747)

Listing Agent: Sheri Malin (407-603-5221)

Remarks: A home with its very own private oasis. This home boasts a 2019 AC UNIT and a 2021 ROOF REPLACEMENT. Enjoy the simple living that Seminole County offers. An updated kitchen centers the floorplan of 1307 Ortega St with an adjoining living room, dining room, and fully enclosed Florida room with attractive cedar plank built in storage. The true showstopper of the home sits in the backyard. A majestic and well loved Oak Tree towers over the backyard. Enjoy a quiet morning coffee as you contemplate life over your reflection pond. A small seating area resides in the far corner of the backyard. Sunrise in Winter Springs is a well established neighborhood with a community park within a short walk of this home! Rainbow Elementary, the zoned school, is an A-Rated school! 1307 Ortega St has been owned by the same family since construction and is now available on the market for the first time ever! Come see this well maintained home today!

Listing is courtesy of: CENTURY 21 ALTON CLARK (407-636-4637)

Listing Agent: James Evans (407-462-1348)

Remarks: Very motivated sellers! Condo in Tuskawilla’s Tuscany Place •Discover comfort and convenience in Winter Springs’ Tuskawilla neighborhood. Tuscany Place is a gated community with a private pool, near Trotwood Park, Cross Seminole Trail, and top-rated schools. •Double Balcony (length of condo) •Corner unit with pool view •Updated kitchen w/stainless steel appliances •New water heater (2023) •New roof (2023) •New AC (2016) •Washer/dryer (2026) •Primary bedroom with walk-in closet, en-suite, and balcony access •Split floor plan for privacy. Seize this opportunity to own a beautifully updated condo in a prime location! FHA Approved Condo complex.

Listing is courtesy of: WORTH CLARK REALTY (352-988-7777)

Listing Agent: Kelly Boulton (407-906-8348)

Remarks: Under contract-accepting backup offers. 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 oversized driveway provides additional parking for guests or recreational vehicles. Rest assured, knowing that the roof was replaced in 2017. This home combines comfort, style, and function in a prime Winter Springs location close to parks, trails, golf, and top-rated schools.

Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)

Listing Agent: Derek Cole (407-733-1061)

Remarks: One or more photo(s) has been virtually staged. Top-Rated Schools! Beautiful and well-maintained 4-bedroom, 2-bath home located in desirable Winter Springs. This home features ceramic tile flooring throughout for easy maintenance and a spacious layout perfect for comfortable living. Enjoy a huge patio—ideal for family gatherings and entertaining guests. Brand new roof (2025) provides peace of mind for years to come. Prime location close to shopping, restaurants, and supermarkets, offering both convenience and lifestyle.

Listing is courtesy of: JOY ESTATE ENTERPRISE INC (321-754-9131)

Listing Agent: Joyce Tang (407-666-9388)

Remarks: Welcome to this charming 4-bedroom, 2-bath home tucked away in a quiet, tree-lined neighborhood in desirable Winter Springs. Surrounded by mature trees, this property offers a peaceful atmosphere and a spacious backyard, ideal for entertaining, relaxing, or enjoying Florida outdoor living. Inside, you’ll find a warm and inviting layout highlighted by an original masonry fireplace, adding timeless character and charm. Skylights in the living room and hallway flood the home with natural light, creating a bright and airy feel throughout the main living spaces. Conveniently located near schools, parks, shopping, dining, and major roadways, this home offers the perfect blend of tranquility and accessibility in an established community.

Listing is courtesy of: LPT REALTY, LLC (877-366-2213)

Listing Agent: Nairobi Rondon (786-935-0365)

Remarks: BEAUTIFUL HOME! TOTALLY UPGRADED 3 BEDROOMS 2 BATHS!! & IN-LAW SUITE 1 BEDROOM 1 BATHROOM AND LAUNDRY. Priced to Sell! This home is not like no other home in this area, Nice Kitchen Cabinets and Granite counter tops, modern tile floors, Stain Steel appliances, Refrigerator, Range & microwave. This home is clean, immaculate and a pleasure to show.

Listing is courtesy of: ESG INVESTMENT ENTERPRISE INC (407-376-3896)

Listing Agent: Everardo Santos (407-376-3896)

Remarks: Under contract-accepting backup offers. Welcome to Chelsea Woods in Winter Springs! This beautifully maintained 4-bedroom, 3-full-bath single-family residence sits on a large lot with a fully vinyl-fenced backyard, perfect for privacy and outdoor living. Enjoy Florida living at its best with a saltwater pool that is fully screened, plus added patio space ideal for a fire pit and grilling area. The home also features a welcoming front patio, a long driveway with ample parking, and is located in a desirable golf cart–friendly community. Inside and out, this home offers peace of mind with major upgrades, including all new A/C ducts and insulation in 2023, a newer roof, and a whole-home backup generator powered by an in-ground 100-gallon propane tank. Zoned for top-rated schools, this property combines comfort, functionality, and lifestyle in one of Winter Springs’ most sought-after neighborhoods. Don’t miss this exceptional opportunity in Chelsea Woods!

Listing is courtesy of: EXIT REALTY PREMIER LEGACY (407-801-8219)

Listing Agent: Chandler Williams (407-702-3815)

Remarks: Welcome to this charming 3-bedroom, 2-bath home nestled on a spacious cul-de-sac lot in the heart of Winter Springs. Offering added privacy and room to spread out, the oversized homesite provides a peaceful setting while still being close to everything you need. Inside, you’ll find a warm and inviting interior with tile and wood flooring throughout, complemented by neutral tones that make it easy to personalize. The kitchen features solid wood cabinetry and updated appliances, blending functionality with classic style. Conveniently located near local shopping, dining, and everyday amenities in Winter Springs, this home offers the perfect balance of comfort, privacy, and accessibility. Don’t miss the opportunity to make it your own!

Listing is courtesy of: THE AGENCY FL (407-335-4119)

Listing Agent: Amanda Brown (386-248-5754)

Remarks: The Catalina I is a harmonious blend of style, functionality, and comfort, offering a lifestyle that caters to your every need. As you step inside you are greeted by an open-concept design that seamlessly integrates the gathering room, dining room, and kitchen, creating an inviting space for both everyday living and entertaining. This townhome features 3 bedrooms, providing flexible living options for families, professionals, or those in need of a dedicated home office space. The loft adds an additional dimension, allowing you to customize this versatile area to suit your lifestyle.

Listing is courtesy of: MATTAMY REAL ESTATE SERVICES (407-440-1760)

Listing Agent: Amanda Warren (321-662-0779)

Remarks: Welcome to this charming 2-bedroom, 2 1/2-bath home located in the heart of Winter Springs! This beautifully maintained residence offers an open and functional layout, perfect for both everyday living and entertaining. The bright kitchen features ample cabinet space and a breakfast bar that overlooks the spacious living and dining areas. Step outside to a large wood deck and fenced backyard—ideal for relaxing evenings, weekend gatherings, or letting pets roam freely. The primary suite boasts generous closet space and a private en-suite bath, while the additional bedroom provides flexibility for family, guests, or a home office. Nestled in a quiet community with mature landscaping, this home is just minutes from top-rated Seminole County schools, parks, shopping, dining, and major highways, making commuting a breeze. Highlights include: •2 bedrooms, 2 full bathrooms •Open-concept living and dining space •Large deck and fenced yard •Convenient Winter Springs location • Community features I would add the following 2 playgrounds. Nature trails throughout the community. Basketball and volleyball courts Don’t miss your chance to make this lovely home yours—schedule a private showing today!

Listing is courtesy of: LPT REALTY LLC (877-366-2213)

Listing Agent: Matt Magee (407-383-0852)

Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Welcome to your dream home, a stunning estate style home on 1.2 acres of beautifully landscaped grounds located in the highly desirable Tuscawilla area of Winter Springs, FL. Nestled on a tree-lined street, this four bedroom, two and one half bathroom home is designed for comfort and entertaining, offering the perfect blend of elegance and tranquility, backing up to Howell Creek. Stepping inside, the foyer and expansive living and dining rooms flow seamlessly into the Florida room with 40 feet of expansive hurricane impact windows overlooking the pool and patio. The kitchen with granite countertops opens into the eat in area and family room which includes a gas fireplace. The luxurious primary suite features an elegant spa bath, dual sinks with onyx countertops, exquisite shower and two customized walk-in closets. There are three additional bedrooms as well as a home office overlooking the patio. The layout connects the living spaces, ensuring a harmonious flow throughout. Stepping into the screened-in patio, you will find a beautiful pebble tec pool surrounded by the extended patio area. This inviting outdoor retreat is perfect for hosting gatherings or enjoying quiet mornings with a cup of coffee while soaking in view of Howell Creek. Additional features include a generous sized laundry/mud room with washer and dryer, a spacious extended garage, extended side driveway, whole house generator capable of powering up to two weeks and a beautifully manicured lawn. Winter Springs is known for its quiet atmosphere, A rated public schools including close proximity to several private schools and mature trees that line the streets. It has been voted several times one of the best places to live in Florida. Ride your bike or golf cart to the beautiful parks or golf course, take advantage of the Seminole Trail or just take a stroll around the beautiful tree lined sidewalks. Conveniently located to restaurants, shopping, hospitals and major highways. Clearly this home is perfect for entertaining guests or relaxing with family. Come take a look.

Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)

Listing Agent: Lou Diberardino (315-569-6900)

Remarks: Under contract-accepting backup offers. Looking for a move in ready & affordable home in Winter Springs? This home features new paint and updated LPV flooring, with block construction, 2 Car Garage and an updated roof. You will enjoy a large backyard with no rear neighbors, a pond view, and Boat / RV Parking. With No HOA restrictions, you have the freedom to customize and personalize your space. Perfect for the family looking for the local Winter Springs / Seminole County Schools. *All information is intended to be accurate but is not guaranteed.

Listing is courtesy of: COLDWELL BANKER REALTY (407-647-1211)

Listing Agent: Ryan Minadie (407-765-9990)