Winter Springs Homes For Sale & Real Estate - 165 homes

Remarks: Under contract-accepting backup offers. Greenbriar of Tuscawilla offers a spacious, Light & Bright, open-concept 3-bedroom, 2-bath layout with peaceful views and an easy, connected flow for everyday living and entertaining. The kitchen opens directly to the living area, so you’re always part of the conversation—whether it’s morning coffee or game day. Gas fireplace in the living room for those cozy winter nights. Bedroom 3 is currently used as a home office and includes a Murphy bed, making it perfect for guests without giving up your work space. You’ll love the low-maintenance lifestyle here—the HOA handles the lawn care—and you’re also close to the Cross Seminole Trail, ideal for biking, walking, and getting outside whenever you feel like it. And here’s the big bonus: an enclosed Florida room (approx. 693 sq ft) that is NOT included in the recorded/MLS square footage—a huge flex space for entertaining, a playroom, hobby zone, home gym, or just spreading out and enjoying life. Tuscawilla is a Golfcart community, so bring your golfcart and meet at the park. ~Located conveniently 55 minutes from the beach and amusement parks.

Listing is courtesy of: RE/MAX TOWN & COUNTRY REALTY (407-695-2066)

Listing Agent: Laura Leigh Wood (407-310-4908)

Remarks: Welcome to 1096 Dyson Drive, a truly one-of-a-kind pool home in the heart of Winter Springs, FL! This spacious and well-maintained property is packed with unique features and thoughtful upgrades, offering the ideal Florida lifestyle—both inside and out. Step inside and you’ll immediately notice the charm and craftsmanship, including solid wood interior doors in a timeless Craftsman style. The home features 3 bedrooms and 2 bathrooms, a flowing layout, and plenty of natural light throughout. The screened porch offers a relaxing space to unwind while overlooking the huge in-ground pool—perfect for entertaining or cooling off on warm Florida days. And that’s just the beginning! Your A/C-equipped pool house adds comfort and convenience for guests, a home office, or creative space. Outside, you’ll also find three storage sheds, giving you ample room for tools, hobbies, or even a workshop. Plus, the property includes an RV 50-amp hook-up, making it ideal for RV owners or travelers looking for flexibility at home. Located in a peaceful, well-established neighborhood with no HOA, this home is just minutes from top-rated schools, local parks, shopping, dining, and major roadways—making it as convenient as it is charming. Don't miss your chance to own a property with space, character, and endless possibilities in beautiful Winter Springs! Situated in a well-established neighborhood with no HOA, this property is conveniently located near top-rated schools, parks, shopping, and dining, with easy access to major highways for commuting or exploring all that Central Florida has to offer. Don’t miss this rare opportunity to own a home with character, space, and all the extras in one of Winter Springs’ most desirable areas!

Listing is courtesy of: EXP REALTY LLC (888-883-8509)

Listing Agent: Lorena Cabal Ospina (321-348-7315)

Remarks: Now offered at an ADJUSTED price of $764,900 for this stunning six-bedroom, four-bath home in a gated community, perfectly positioned with a view of a conservation lot without rear neighbors. Winter Springs address, with top-rated Oviedo Schools! Soak up the Florida lifestyle in this stunning backyard retreat with a sparkling pool and spa. Brand new pool heater plus a spacious outdoor kitchen, complete with a dedicated gas grill area, seating space, and brand new refrigerator. It is the ideal place to enjoy warm Florida days and breezy nights. Inside, the home offers a highly desirable layout, with both the primary suite and an additional bedroom on the first floor, perfect for a mother-in-law suite, guests, or a home office. The open living areas feature tile flooring throughout the main level, while the kitchen is finished with granite countertops and ample workspace for everyday living and hosting. Upstairs, you’ll find generously sized secondary bedrooms and baths, providing flexibility for large families, multigenerational living, or vacation use. The peaceful conservation views create a private, serene backdrop both indoors and out. Located in a gated community, this home combines space, privacy, and resort-style amenities in one exceptional property.

Listing is courtesy of: PALMANO GROUP RE BROKERAGE LLC (321-214-1211)

Listing Agent: Denise Pohlmann (407-701-3346)

Remarks: Welcome home to this charming 3-bedroom, 2-bathroom home, which offers 1,032 square feet of beautifully updated living space. This property features a newly painted interior and a fully remodeled eat-in kitchen equipped with brand-new stainless steel appliances, shaker cabinets with modern hardware, a trendy backsplash, and granite countertops. The home is designed with a functional split-floor plan for added privacy. The master suite includes a private bathroom with a new vanity, lighted mirror, and updated lighting. On the opposite side of the home, you will find two additional bedrooms and a second bathroom, which also features a new vanity and modern lighting fixtures. The layout includes separate living and dining rooms, with brand-new ceiling fans installed in the living area and all bedrooms. Major high-ticket maintenance items have been recently addressed, including a new roof installed in 2025, a new hot water heater in 2023, and an HVAC system from 2018 with air ducts replaced in 2020. Exterior features include a private patio with a storage shed, and residents can enjoy a low monthly HOA fee that provides access to a community pool and tennis courts. Located conveniently near schools, major highways, medical centers, and prime shopping and dining, this home is an ideal choice for a growing family or a strategic investment opportunity.

Listing is courtesy of: REALTY TECH INC (407-332-9757)

Listing Agent: Carmen Vazquez (407-617-9045)

Remarks: NEW ROOF!!! NEW ROOF!!! NEW ROOF!!! The roof is currently being replaced — what you have been waiting for is finally here. Take advantage of this opportunity to own a home with a BRAND NEW roof, offering peace of mind, easier insurance, and long-term value. This 3-bedroom, 2.5-bathroom home offers over 1,700 sq ft of living space and is located in a top-rated Seminole County school zone. The layout is highly desirable with the primary bedroom downstairs, featuring a spacious walk-in closet and a large private bathroom with dual vanities, separate shower, soaking tub, and private toilet space. The home offers a bright and open layout with high ceilings and tile flooring throughout the main living areas. The kitchen features granite countertops, stainless steel appliances, light cabinetry, and a breakfast bar, with sliding glass doors leading to a cute backyard with shade, perfect to relax or entertain. Upstairs you’ll find a spacious loft along with two additional bedrooms and a full bathroom, offering flexibility for guests, family, or working from home. Major systems include HVAC 2017–2018 and water heater 2022, with electrical and plumbing in good condition. A 4-Point Inspection is available in the MLS for buyer review. Additional features include a 2-car garage, interior laundry room, neutral finishes throughout, and the home is vacant and easy to show. Ideally located near UCF, Valencia College, SR-417, SR-434, and I-4, with easy access to shopping, dining, Downtown Orlando, and Central Florida beaches.

Listing is courtesy of: KELLER WILLIAMS ADVANTAGE 2 REALTY (407-393-5901)

Listing Agent: Alexa Monasterio Flores (786-915-9294)

Remarks: Assumable VA Loan : 2.75%...in the heart of Winter Springs—where comfort, convenience, and lifestyle come together. This spacious 4-bedroom, 3.5-bath home offers a highly desirable layout with a private bedroom and full bath on the first floor, perfect for guests, multi-generational living, or a home office. Your second floor is for entertaining with a big open kitchen, dining space and livingroom close by.Upstairs, you’ll find generously sized secondary bedrooms and a primary suite designed for relaxation. Located just minutes from the vibrant dining and nightlife scene along State Road 434 and the popular Central Winds Park, you’ll enjoy easy access to community events, sports fields, and scenic walking trails. Outdoor enthusiasts will love being near the Cross Seminole Trail—ideal for biking, jogging, or evening strolls. Whether you're entertaining at home or exploring the best of Winter Springs, this property offers the perfect balance of space, flexibility, and location.

Listing is courtesy of: WATSON REALTY CORP (407-323-3200)

Listing Agent: Carla Robles (407-462-2347)

Remarks: Check out this spacious 4-bedroom, 2.5 bath home in Winter Springs, located in the highly sought-after Seminole County school district! Discover comfort and space in this corner lot home in The Oaks at the Highlands Subdivision. This well-designed home offers more than 2,300 square feet of living space with a functional layout that features the primary suite on the first floor along with a flex space used as an office or guest room plus 2 additional bedrooms upstairs. Inside, you’ll find a bright, open floor plan that seamlessly connects the main living areas. The kitchen is equipped with stainless steel appliances (new double door fridge) and a convenient breakfast bar overlooking the great room, making it perfect for both casual mornings and entertaining guests. Step outside through French doors to a screened patio and cozy fire pit area, creating an inviting space to unwind year-round. The spacious primary suite includes a walk-in closet and an en-suite bath with dual vanities, a soaking tub, and separate shower. Updates include a 2018 roof, energy-efficient windows, water softener, rain gutters, and irrigation system. Residents enjoy access to community amenities including a pool, clubhouse, park, and scenic walking trails, all just minutes from major roadways, shopping, and dining. Schedule your private tour today!

Listing is courtesy of: BAILEY CAMPBELL PROPERTIES (321-228-7985)

Listing Agent: Nate Bailey (321-331-8658)

Remarks: Under contract-accepting backup offers. Facade Grass is photoshopped green, due to Winter. This beautifully designed 3 bedroom, 2.5-bath townhome offers the perfect balance of space, comfort, and style. With over 1,800 square feet of living space, the open and airy floor plan features distinct living and dining areas, along with a versatile flex space upstairs—ideal for today’s modern lifestyle. The 42" Kitchen Cabinets are lovely and in very good condition. Two flex spaces on the first floor, too. Stunning PLANTATION SHUTTERS THROUGHOUT. One of the home’s most impressive features is the private rear patio, a rare find for a townhome. This serene outdoor retreat provides the perfect setting for relaxing, entertaining, or enjoying everyday moments in privacy. Upstairs, the thoughtfully planned second level is dedicated to rest and relaxation, featuring a spacious primary suite, two additional bedrooms, and two full bathrooms. A generous loft area adds even more flexibility and can easily serve as a home office, playroom, or additional living space. Newly painted interior, carpet and tile freshly cleaned and beautifully staged, too. Residents enjoy access to a community pool and the added peace of mind of gated access. Conveniently located near SR-434, Winter Springs Town Center, top-rated schools, shopping, and dining, this home presents an exceptional opportunity to enjoy modern living with privacy, space, and convenience. Roof replaced 2022, AC 2021, Appliances 2018, Washer 2022, Dryer 2023, Interior Paint 2026.

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

Listing Agent: Gale Milgrim (407-443-9832)

Remarks: One or more photo(s) has been virtually staged. Welcome home to Bentley Green! Set within the desirable Bentley Green neighborhood of Tuscawilla, this beautifully maintained three-bedroom, two-bath home offers a blend of space, comfort, and thoughtful updates. A gracious main living area welcomes you with a formal dining space that flows seamlessly into the living room, anchored by a wood-burning fireplace—ideal for both everyday living and entertaining. The kitchen is both functional and inviting, featuring a center island, eat-in area, and a full suite of appliances, including the washer and dryer. The home’s split-bedroom floor plan places the two secondary bedrooms and a full bath at the front of the home, while the private primary suite is tucked away at the rear, offering a spacious retreat with a soaking tub, separate shower, dual vanities, walk-in closet, and generous bedroom space. A substantial addition expands the home’s versatility, providing a bonus family room with sink and refrigerator—perfect for entertaining along with a light-filled Florida room that easily adapts to your lifestyle, whether as a home gym, craft room, or quiet escape. The Florida room has been updated to make it a blank canvas for whatever suits your lifestyle best! Peace of mind comes from the major updates already completed, including a new roof (2018), replumbing (December 2025), and HVAC (2022). Paid-for solar, including a solar hot water heater and a system producing approximately 17,000 watts, along with a whole-house water softener, adds both efficiency and long-term value. Bentley Green offers a truly low-maintenance lifestyle, with lawn care included in the HOA, allowing you more time to enjoy nearby amenities such as Tuscawilla Country Club, the Cross Seminole Trail, and local parks. This is a home where comfort meets convenience in a highly sought-after location. Schedule your private showing today and experience firsthand what makes this Bentley Green home so special.

Listing is courtesy of: KELLER WILLIAMS ADVANTAGE REALTY (407-977-7600)

Listing Agent: Barrett Spray (407-927-3650)

Remarks: Under contract-accepting backup offers. Build your dream home on this rare 0.47 acre corner lot located at 1219 Swan Street in the highly desirable Tuscawilla area of Winter Springs. This spacious homesite offers plenty of room to design a custom residence while enjoying the charm and established beauty of one of Seminole County’s most loved communities. The property is zoned for single family residential use, allowing for the construction of a custom single family home that fits your vision and lifestyle. Located in an optional HOA section of Tuscawilla, homeowners enjoy flexibility while still benefiting from the surrounding community amenities and pride of ownership. Just a short walk away is the Tuscawilla Country Club, a private club offering a full golf course with Diamond Zoysia greens surrounded by majestic Live Oak trees draped in Spanish moss. Members enjoy a well stocked Golf Pro Shop, fitness center, and The Oaks Restaurant which serves lunch, dinner, and brunch in a welcoming setting. The club also features six Har Tru clay tennis courts with LED lighting and a Jr Olympic sized swimming pool at the Aquatics Center along with numerous social activities throughout the year for both adults and children. Beyond the club, the Tuscawilla community is known for its beautiful parks, playgrounds, and scenic walking and biking trails that wind through the neighborhood, creating a peaceful and active outdoor lifestyle. With its large size, corner location, and unbeatable proximity to golf, tennis, dining, and recreation, this lot presents an exceptional opportunity to build a custom home in one of Winter Springs’ most sought after communities. Close to 417 highway which connects easily to I-4 to take you anywhere from Downtown Orlando, to Tampa or Daytona beach! Zoned for Keeth Elementary, Indian Trails Middle School, and Winter Springs High School in highly rated Seminole County Public Schools. Cash or hard-money only please.

Listing is courtesy of: RE/MAX TOWN & COUNTRY REALTY (407-695-2066)

Listing Agent: Kristine Mckinley (407-415-2412)

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: 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. 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)