Winter Springs Single Family Homes For Sale - 122 homes

Remarks: Under contract-accepting backup offers. This 4 bedroom, 3 bath home with a side entry two car garage, is located in the golf course community of Tuscawilla, and is sited on a large lot (almost .4 of an acre). There is a formal foyer and a formal living, dining and family room. The kitchen has a pass-through window above the double bowl stainless sink gives the cook access to easily serving meals on the brick covered porch. There is a closet pantry in the kitchen. There is a plumbing stub out below the window for a future summer kitchen. All appliances are included. The family room has a brick, wood burning fireplace. There are built-in shelves on either side of the fireplace. The ceiling has been finished in cedar. The primary bedroom is large and the primary bath area has a large shower with a newer shower enclosure.. There is also a mirrored walk-in closet. The interior of the home has recently been painted. New plumbing and light fixtures have been added and a new HVAC system installed. The hot water heater is new. The roof was replaced in 2019. There is a large covered back porch. The backyard is quite large and has several fruit trees and there is a storage shed on a concrete slab that is a great place for storing seasonal items. Mature landscaping. There are 5 ceiling fans throughout the house. The ceilings are vaulted in the family room, primary bedroom, and two of the auxiliary bedrooms. There is convenient shopping, a large array of restaurants, and major employers are located nearby. The beautiful and dramatic entrance to this Tuscawilla community creates a wonderful sense of arrival. This home has a versatile floorplan and is a great value. Outstanding family-oriented neighbors.

Listing is courtesy of: THE WILLIAMS REAL ESTATE CO (407-310-6980)

Listing Agent: Morris Williams, Jr (407-310-6980)

Remarks: Under contract-accepting backup offers. Discover a rare opportunity in the heart of Tuscawilla. Perched high on a hill and surrounded by beautiful custom homes, this one-of-a-kind property sits on over 0.6 acres with no HOA—a true find in this sought-after area. From the moment you arrive, the home impresses with exceptional curb appeal and a thoughtfully designed interior filled with upgrades. Inside, you’ll find soaring ceilings, elegant crown molding, under cabinet lighting, multiple sliding glass doors bringing the outside into the home, custom blinds and window treatments, split bedroom plan, spacious bedrooms, and a striking glass-enclosed office that creates a unique and inviting workspace or flex space. The oversized deep side-entry garage provides ample room for vehicles, storage, or hobbies. Located on Howell Creek Drive, one of Tuscawilla’s most beloved streets, the neighborhood is known for its rolling hills, stunning custom homes, and the charming presence of local families of peacocks that make the area truly special. Major updates offer peace of mind, including a 2016 roof, 2023 HVAC system, and updated PEX plumbing. This distinctive home combines character, space, and location—making it a true Tuscawilla treasure.

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

Listing Agent: Tanya Mcdonnell (407-625-2719)

Remarks: Move in Ready home in Greenspointe section of The Highlands. This Light & Bright Home has No Rear Neighbors and a Nice View of the open space out back. New Tile Roof 2017, New A/C. Primary Bathroom has a Large Step-In Shower/Tub. The community offers a variety of amenities including a Olympic Size Community Pool, Tennis & Pickleball Courts, Audibon Park, Nature Trails and a Clubhouse. Highly rated Seminole County Schools.

Listing is courtesy of: FLORIDA HOME TEAM REALTY LLC (407-774-8100)

Listing Agent: Paul Buscemi (407-716-2874)

Remarks: 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) • Exterior paint (11/18/2019) • Granite & quartz surfaces, maple wood cabinetry, travertine stone & tile details • Laminate bedroom flooring with upgraded padding • NEST thermostat with full app control • Schlage digital front-door lock with app control • Four installed Wyze interior cameras (app-controlled) • Lighted attic space with flooring for storage, accessible from garage The HOA is only $115/mo and includes: • Weekly yard maintenance (including hedges) • Lap pool, large hot tub, and workout room • Rentable clubhouse (small fee + refundable deposit) This is one of the most walkable and peaceful areas in Tuscawilla. Sam Smith Park is a 5-minute walk, Bear Creek Nature Trail is close by, and the Cross Seminole Trail is just 2.3 miles away. Convenient to everything: • Publix – 1 mile • Oviedo Mall, major highways (417), and restaurants – 2–5 miles • 7 miles to UCF • Orlando International Airport is a straight shot down 417 — 20–30 minutes depending on traffic. The seller will provide a home warranty.

Listing is courtesy of: RED CARPET REALTY FLORIDA (407-808-3663)

Listing Agent: Robert Knowles (407-808-3663)

Remarks: Under contract-accepting backup offers. Step through grand double doors into this beautifully updated 4 bedroom, 3 bath pool home filled with natural light and thoughtful design. The bright, open living space features a cozy wood burning fireplace and panoramic views of the screened pool and deck, creating the perfect setting for everyday living and entertaining. The fully renovated kitchen shines with brand new quartz California style countertops, new 42 inch white shaker cabinets, double sinks, and a convenient indoor laundry room just steps away. Fresh interior paint gives the entire home a crisp, modern feel. Designed with a split floor plan for privacy, the spacious primary suite offers dual walk in closets, a relaxing garden tub, and a glass walk in shower. Bedrooms two and three share a full bath, while the fourth bedroom and third bath at the rear of the home serve perfectly as a private in law suite or guest retreat with easy pool access. Multiple sliding glass doors open to a covered, screened pool area with space for outdoor dining and grilling, ideal for enjoying Florida living year round. Roof 2014, AC 2012, and a new 40 gallon electric water heater in 2025. Located in desirable Winding Hollow, you are just minutes from the Cross Seminole Trail, Central Winds Park with new pickleball courts, dog park, sports fields, playgrounds, and year round community events. Easy access to UCF, Seminole State College, 417, 419, east coast beaches, and Orlando attractions makes this home both convenient and connected. Move in ready and designed for comfort, this one checks all the boxes.

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

Listing Agent: Sanjeev Malik (321-297-3009)

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: 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: 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: 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: 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)