Winter Springs Schools and Nearby Homes for Sale and Rent

Please click on one of the below schools to see properties that are marked as being nearby those schools in the MLS.

Elementary Schools


Middle Schools

High Schools





Newest Winter Springs Homes by School

  • 240 N DEVON AVE, WINTER SPRINGS, FL - MLS# O6416300

    Winter Springs High - O6416300 - 240 N DEVON AVE, WINTER SPRINGS, FL 32708
    Just Added on 06/12/2026 7:20AM

    $384,900 | Single Family Home | 3 beds | 2.0 baths | 1 gar

    Welcome to 240 N Devon Avenue, a fully updated three-bedroom, two-bath home in the heart of Winter Springs, where the renovation has been done for you and the only thing left to do is move in. Inside, the open-concept main living area is anchored by a stunning stone fireplace with built-in shelving and crown molding throughout. The kitchen has been beautifully upgraded with custom wood cabinetry, quartz countertops, tile backsplash, and stainless steel appliances. Both bathrooms are finished with custom tile showers and the same level of detail you'll find throughout the home. Light, bright, and timeless. Beyond the finishes, the major systems have all been addressed: metal roof installed 2024, full HVAC replacement in 2022 (inside and outside units), whole-home repipe in 2022, updated electrical, and a gas tankless water heater. Nothing left to update or worry about! A 16x16 sunroom with AC extends the living space year-round, opening to a backyard built for play and entertaining. A putting green, paver patio, and pergola sit behind an eight-foot privacy fence, surrounded by low-maintenance xeriscaping that means weekends free from mowing. A detached 20x20 garage and workshop offers serious storage, project space, or whatever your hobby calls for. Ample off-street parking handles guests, trailers, RVs, or boats. Step out the front door and you are one block from the community park with its ocean-inspired playground, splash pad, pond, and walking trails. The Cross Seminole Trail is also nearby, putting miles of paved trail at your fingertips. Quick access to both I-4 and the 417 makes commuting a breeze, and you are surrounded by top-rated Seminole County schools. 240 N Devon is a rare combination of move-in-ready renovation, generous outdoor living, freedom from HOA restrictions, and a central Winter Springs location with parks and trails just steps from your door. Call today for your private showing!

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    Listing is courtesy of: REAL BROKER, LLC

  • 70 MOREE LOOP #63, WINTER SPRINGS, FL - MLS# O6416039

    Winter Springs High - O6416039 - 70 MOREE LOOP #63, WINTER SPRINGS, FL 32708
    1 Day on yellowkey

    $170,000 | Condo | 2 beds | 1.5 baths

    Two story condominium in Winter Springs. The two bedroom, 1 and 1/2 bath unit is located in the Highlands Community. Tile and laminate flooring, fresh paint, spacious layout, kitchen has a pass thru window to the dining area. Combo living/dining with sliding glass doors which offers natural sunlight and opens to an exterior patio. Two bedrooms, master full bath and laundry utility on the second floor. The Highlands Master HOA offers endless amenities to include jr. Olympic pool, picnic areas with a covered pavilion, basketball, volleyball, tennis, pickleball, playgrounds and community events.

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    Listing is courtesy of: PAINE-ANDERSON PROPERTIES, INC

  • 577 WALDEN CT, WINTER SPRINGS, FL - MLS# V4949540

    Winter Springs High - V4949540 - 577 WALDEN CT, WINTER SPRINGS, FL 32708
    5 Days on yellowkey

    $405,000 | Single Family Home | 4 beds | 2.0 baths | 2 gar

    NO HOA Corner Lot Single Family Home features 4 beds, 2 baths. Open layout design home with tons of upgrades: Windows replaced back in 2020, ROOF replaced in 2022, Water Heater replaced 2025, Luxury Vinyl floors installed 2026. BRAND NEW INTERIOR PAINT gives a clean look. The kitchen is the focal point of the house. It features subway tiles EXHAUST FAN, STAINLESS STEEL APPLIANCES and cabinets. GRANITE COUNTER TOP installed in 2019 and a brand new fridge 2026. Bathroom with brand new glass doors and brand new bath tub. AC unit installed 2017. A fully fenced yard provides privacy with expansive open space ready for outdoor entertaining and dining space, gardening, play area, fire pit area and also has a chicken coop and chicken run area. All outdoor furniture plus the BBQ grill are included with the sale. 2 car garage and metal husky shelves for storage. Zoned for Seminole County top A rated schools. The property is located in a minimal flood risk area (Zone X). Schedule your viewing today.

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    Listing is courtesy of: RISE REALTY OF FLORIDA LLC

  • 10 N FAIRFAX AVE #10, WINTER SPRINGS, FL - MLS# O6414606

    Winter Springs High - O6414606 - 10 N FAIRFAX AVE #10, WINTER SPRINGS, FL 32708
    7 Days on yellowkey

    $1,595 | Apartment | 2 beds | 1.5 baths

    LOCATION, LOCATION, LOCATION FULLY RENOVATED Condos in desirable Winter Springs. NO HOA!! BLOCK BUILDING! Unit offers 2 bedrooms, 1 full bath, 1 half bath, COMPLETELY FENCED BACKYARD!! Which provides you with Privacy and Security, a screened PRIVATE PORCH with storage, and NEWER SAMSUNG WASHER/DRYER IN EACH UNIT! Upgraded with STAINLESS STEEL appliances, GRANITE countertops, and engineered WOOD FLOORING. NO CARPET! Ample FRONT PARKING. Located near Winter Springs Town Center, Central Winds Park, TOP Seminole County SCHOOLS, shopping, and dining. Easy access to SunRail via Longwood SunRail Station. Call today! MAKE THIS YOUR NEW HOME TODAY ONLY 4 UNITS AT THIS PRICE, HURRY BEFORE THEY ARE GONE!!

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    Listing is courtesy of: ALL SEASONS REALTY

  • 224 BITTERWOOD ST, WINTER SPRINGS, FL - MLS# O6414223

    Winter Springs High - O6414223 - 224 BITTERWOOD ST, WINTER SPRINGS, FL 32708
    8 Days on yellowkey

    $2,399 | Single Family Home | 3 beds | 2.0 baths | 2 gar

    Welcome home! This charming 3-bedroom, 2-bath home is available for immediate move-in. Located in Winter Springs, the property offers a functional layout, spacious living areas, generously sized bedrooms, and a well-equipped kitchen with plenty of cabinet and counter space. The first bedroom is scheduled to be painted next week, providing a fresh update for the new resident. All applicants are required to complete a credit and background screening. Renters insurance is required. All residents are automatically enrolled in a master renters insurance policy for $11.95 per month. Residents can opt out of the master policy by providing proof of their own policy that meets minimum requirements.

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    Listing is courtesy of: 407 PROPERTIES

  • 472 DEWARS CT, WINTER SPRINGS, FL - MLS# O6413206

    Winter Springs High - O6413206 - 472 DEWARS CT, WINTER SPRINGS, FL 32708
    9 Days on yellowkey

    $499,900 | Single Family Home | 4 beds | 2.5 baths | 2 gar

    Welcome to 472 Dewars Court, a beautifully maintained 4-bedroom, 2.5-bath pool home offering over 2,200 square feet of living space in one of Winter Springs' most desirable communities. Tucked away at the end of a quiet cul-de-sac, this exceptional property provides the perfect combination of privacy, comfort, and convenience with a serene wooded backdrop and no rear neighbors. Inside, you'll find a spacious and functional floor plan designed for both everyday living and entertaining. The kitchen features a gas stove for the home chef, while the home's whole-house Generac gas generator provides peace of mind and uninterrupted comfort year-round. Multiple living and dining spaces offer flexibility for growing families, remote work, or hosting guests. Step outside to your private backyard oasis featuring a sparkling pool, expansive patio space, and tranquil wooded views—perfect for relaxing, entertaining, or enjoying Florida's beautiful weather. Located within The Highlands, one of Winter Springs' most sought-after communities, residents enjoy access to incredible amenities including a large Olympic-sized community pool, scenic nature trails, multiple parks, playgrounds, and recreation areas surrounded by mature oak trees that create a picturesque neighborhood setting. The Highlands is known for its strong sense of community, low traffic streets, and family-friendly atmosphere. Winter Springs consistently ranks among the most desirable places to live in Seminole County thanks to its highly rated schools, beautiful parks, excellent shopping and dining options, and convenient access to Lake Mary, Oviedo, Winter Park, Downtown Orlando, and major highways. This is a rare opportunity to own a private pool home on a cul-de-sac lot with wooded views in one of Central Florida's most established and sought-after communities. Schedule your private showing today.

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    Listing is courtesy of: KELLER WILLIAMS WINTER PARK

  • 1055 CHESTERFIELD CIR, WINTER SPRINGS, FL - MLS# O6413841

    Winter Springs High - O6413841 - 1055 CHESTERFIELD CIR, WINTER SPRINGS, FL 32708
    9 Days on yellowkey

    $515,000 | Single Family Home | 3 beds | 2.0 baths | 2 gar

    Beautiful pool home located in the highly desirable Amherst community of Winter Springs! Situated on an oversized .34-acre lot, this well-maintained 3-bedroom, 2-bath home offers a spacious split-bedroom floor plan with vaulted ceilings, abundant natural light, and a cozy wood-burning fireplace in the oversized family room. Updated bathrooms and ceramic wood looking flooring in main living areas. The screened with an large pool and covered lanai create the perfect setting for year-round outdoor living and entertaining, and no rear neighbors for privacy. The primary suite features a walk-in closet and spacious bath with dual sinks newly remodeled. Additional highlights include a 2-car garage, irrigation system, rain gutters, public utilities, and low annual HOA dues. New Roof (2025), New Water Heater & A/C (2024). Conveniently located near top-rated Seminole County schools, parks, shopping, dining, major roadways, and the 417.

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    Listing is courtesy of: LPT REALTY, LLC

  • 358 BRUSHWOOD LN, WINTER SPRINGS, FL - MLS# O6412915

    Lake Howell High - O6412915 - 358 BRUSHWOOD LN, WINTER SPRINGS, FL 32708
    9 Days on yellowkey

    $468,000 | Single Family Home | 4 beds | 2.0 baths | 2 gar

    Welcome to 358 Brushwood Lane, a beautifully maintained 4-bedroom, 2-bathroom home located in the highly sought-after Tuscawilla Forest community of Deer Run in Winter Springs. Offering nearly 2,000 square feet of living space, this spacious single-story home combines timeless character with thoughtful updates throughout. From the moment you step inside, you'll appreciate the soaring vaulted ceilings, abundant natural light, and open-concept layout designed for comfortable everyday living and entertaining. The inviting living room features a cozy wood-burning fireplace, skylights, and French doors to connect the indoor and outdoor living spaces. The kitchen serves as the heart of the home with granite countertops, stainless steel appliances, ample cabinetry, and a functional layout that flows effortlessly into the living and dining areas. Plantation shutters throughout the home add both style and privacy. The spacious primary suite offers a large walk-in closet and an ensuite bathroom with dual sinks. The guest bedrooms are all generous in size and share the guest bathroom, which has been tastefully updated, while additional features include a large laundry room with utility sink, generous storage throughout, and a two-car garage. Additional improvements include an updated hot water heater and updated flooring. Step outside to enjoy the oversized screened porch, paver patio, fenced backyard, and mature landscaping, creating the perfect setting for relaxing evenings or weekend gatherings. Located in one of Winter Springs' most desirable neighborhoods, residents enjoy low HOA fees, top-rated Seminole County schools, nearby parks, golf, shopping, dining, and convenient access to major roadways. This move-in ready home offers the perfect combination of comfort, functionality, and location.

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    Listing is courtesy of: RE/MAX TOWN & COUNTRY REALTY

  • 1110 SHADOWBROOK TRL, WINTER SPRINGS, FL - MLS# O6413323

    Winter Springs High - O6413323 - 1110 SHADOWBROOK TRL, WINTER SPRINGS, FL 32708
    9 Days on yellowkey

    $575,000 | Single Family Home | 4 beds | 3.0 baths | 3 gar

    Nestled within the DESIRABLE Winding Hollow community, this residence presents a CHARMING front exterior, highlighted by a meticulously maintained lawn and lush landscaping. An inviting entryway, featuring distinctive double doors, sets a welcoming tone upon arrival. The interior unfolds into an OPEN CONCEPT living, dining, and kitchen area, designed for both comfort and connectivity. The spacious living room offers ample space for various arrangements, and overlooks the lanai & pool. Perfectly positioned adjacent to the living room, the DINING area is bathed in NATURAL LIGHT from the large window enhancing the home's OPEN and airy feel. Culinary endeavors are elevated in the well appointed GORGEOUS kitchen, boasting GRANITE countertops, SS appliances, and abundant wooden cabinet space for storage. The KITCHEN is the heart of the home with a LARGE ISLAND offering a vantage point into the family and dining areas, fostering a sense of togetherness. An additional eat-in kitchen area provides flexibility for casual dining. This home encompasses 4 well-proportioned bedrooms and 3 FULL bathrooms, spanning 2,214 square feet. The PRIMARY suite offers a private retreat, featuring a double vanity, a LUXURIOUS soaking tub, and a separate walk-in shower, creating a spa-like experience. The additional bathrooms are thoughtfully designed with contemporary fixtures and tiled showers, ensuring comfort and style. Practical amenities include a dedicated laundry room, equipped with a stacked washer and dryer and ample storage cabinets, enhancing daily convenience. A 3-car garage provides extensive parking and storage solutions, catering to diverse needs. OUTDOOR LIVING is seamlessly integrated with a screened-in patio, offering a comfortable space to relax and enjoy the surroundings. Beyond the patio, a sparkling POOL invites recreation and leisure, and is the perfect oasis for unwinding. The property's location offers exceptional convenience to a wealth of local amenities. Proximate to the vibrant Winter Springs Town Center, an array of shopping and dining options are readily available. Award-winning CENTRAL WINDS PARK provides expansive green spaces with a DOG PARK and 14 PICKLEBALL COURTS, and the CROSS SEMINOLE TRAIL is right outside the neighborhood. Top Rated Seminole County Schools and easy access to the 417. This home has it ALL. Make YOUR showing appointment today.

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    Listing is courtesy of: KELLER WILLIAMS WINTER PARK

  • 504 GREEN SPRING CIR, WINTER SPRINGS, FL - MLS# O6413016

    Winter Springs High - O6413016 - 504 GREEN SPRING CIR, WINTER SPRINGS, FL 32708
    9 Days on yellowkey

    $250,000 | Townhouse | 2 beds | 2.5 baths

    Welcome to 504 Green Spring Circle, a beautifully maintained 2 bedroom 2.5 bath townhome nestled in the heart of Winter Springs, where comfort, charm, and everyday functionality come together effortlessly. Inside, the UPDATED KITCHEN features modern finishes, GRANITE countertops, ample prep space, and room for a dine-in table. The home has been thoughtfully maintained, offering peace of mind and move-in-ready convenience. Step outside to one of this home’s standout features a SERENE BACKYARD retreat complete with a screened in porch perfect for morning coffee, evening unwinding, or hosting friends and family. Surrounded by mature landscaping and a peaceful setting, this outdoor space offers the privacy and tranquility you've been searching for. Located in an established community with a LOW HOA FEE, residents enjoy affordability without sacrificing location or lifestyle. A community playground, tennis courts and pool to use as you wish. Conveniently situated near shopping, dining, parks, and top-rated Seminole County amenities, this Winter Springs gem is one you won’t want to miss.

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    Listing is courtesy of: EXP REALTY LLC

  • 819 DUNDEE DR, WINTER SPRINGS, FL - MLS# O6412585

    Winter Springs High - O6412585 - 819 DUNDEE DR, WINTER SPRINGS, FL 32708
    10 Days on yellowkey

    $429,000 Increased | Single Family Home | 4 beds | 2.0 baths | 2 gar

    Welcome home to this charming 4-bedroom, 2-bath residence nestled on a spacious corner lot in the highly desirable Highlands community of Winter Springs. From the moment you arrive, you'll appreciate the inviting curb appeal, mature surroundings, and move-in ready condition that make this home truly special. Inside, vaulted ceilings and abundant natural light create an open and airy atmosphere, while updated flooring adds a fresh, modern touch throughout. The heart of the home features a cozy wood-burning fireplace, perfect for gathering with family and friends. The kitchen is both stylish and functional, offering beautiful wood cabinetry, granite countertops, and stainless steel appliances. The thoughtfully updated bathrooms provide comfort and convenience, while sliding glass doors from the living room lead to an expansive covered and screened patio—an ideal space for morning coffee, weekend barbecues, or simply relaxing and enjoying Florida's beautiful weather. The partially fenced backyard offers plenty of outdoor space, complete with a storage shed for tools, hobbies, or seasonal items. Located within The Highlands, residents enjoy access to exceptional community amenities including a swimming pool, playground, and tennis courts. Conveniently situated near shopping, dining, parks, and major highways, this home offers the perfect blend of comfort, convenience, and community. Don't miss your opportunity to make this wonderful Winter Springs home your own!

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    Listing is courtesy of: KGV REALTY GROUP

  • 724 LAKESIDE DR, WINTER SPRINGS, FL - MLS# O6412679

    Winter Springs High - O6412679 - 724 LAKESIDE DR, WINTER SPRINGS, FL 32708
    10 Days on yellowkey

    $264,900 | Single Family Home | 2 beds | 2.0 baths | 1 gar

    Virtually Staged. Welcome to 724 Lakeside Dr, nestled in the highly sought-after Wildwood community. This beautifully maintained 2-bedroom, 2-bathroom home offers 1,168 square feet of comfortable living space and presents an excellent opportunity for first-time homebuyers, downsizers, or anyone seeking a move-in-ready home in one of Winter Springs' most established neighborhoods. As you step inside, you'll immediately notice the fresh updates throughout, including brand-new carpet that adds warmth and comfort to every room. The functional floor plan offers a spacious living and dining area filled with natural light, creating an inviting atmosphere for both everyday living and entertaining guests. The kitchen provides ample cabinet and countertop space with easy access to the main living areas, making meal preparation and gatherings effortless. The primary suite offers a private retreat complete with an en-suite bathroom and generous closet space. A well-sized secondary bedroom and full guest bathroom provide flexibility for family members, guests, or a home office setup. The guest bathroom has been enhanced with a newly installed backsplash, adding a stylish and modern touch. Step outside and enjoy all that the Wildwood community has to offer. Residents have access to a community swimming pool, tennis courts, playground, and a community clubhouse, providing plenty of opportunities for recreation and social gatherings. The neighborhood's mature landscaping, tree-lined streets, and established character create a welcoming environment that homeowners have enjoyed for years. Conveniently located in the heart of Winter Springs, this home is just minutes from the Cross Seminole Trail, Central Winds Park, Winter Springs Town Center, shopping, dining, and top-rated Seminole County schools. Easy access to major roadways makes commuting throughout Central Florida a breeze while still allowing you to enjoy the charm and tranquility of this sought-after community. Whether you're searching for your first home, looking to downsize, or seeking a low-maintenance lifestyle in a prime location, this property offers the perfect combination of comfort, convenience, and community. Schedule your private showing today and discover everything 724 Lakeside Dr has to offer.

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    Listing is courtesy of: LPT REALTY, LLC

  • 207 BIRCH TERRACE, WINTER SPRINGS, FL - MLS# O6411799

    Winter Springs High - O6411799 - 207 BIRCH TERRACE, WINTER SPRINGS, FL 32708
    12 Days on yellowkey

    $297,000 | Single Family Home | 3 beds | 2.0 baths | 2 gar

    Under contract-accepting backup offers. 3 BEDROOM 2 BATH HOME LOCATED ON CUL DE SAC STREET. WOOD CABINETS, SOLID SURFACE COUNTERS IN KITCHEN. SPLIT BEDROOM PLAN. FENCED REAR YARD. NEW ROOF IN 2025. A LITTLE TLC MAKES THIS A GREAT HOME. GREAT HOME FOR OWNER OCCUPANT OR INVESTOR.

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    Listing is courtesy of: REILLY REALTY & MGMT.

  • 4901 PETRA CT, WINTER SPRINGS, FL - MLS# O6412001

    Winter Springs High - O6412001 - 4901 PETRA CT, WINTER SPRINGS, FL 32708
    15 Days on yellowkey

    $674,900 | Single Family Home | 4 beds | 2.0 baths | 2 gar

    Make yourself at home in this spacious, beautifully undated residence located in one of the most desirable and sophisticated neighborhoods in Winter Springs, in the heart of Central Florida. This spacious four bedroom, two bath split-plan home offers comfort and versatility throughout . Features include a formal dining room; inviting Florida room, private den, and a generously sized master suite designed for relaxation. With a thoughtful layout and plenty of space, this home is perfect for both everyday living and entertaining. All kitchen appliances are included featuring 42" custom, cabinetry, carpet in the living room and all bedrooms. Bamboo flooring in the sunroom and office with ceramic tile in the kitchen, bathrooms and laundry room (with pull-down ironing board). The living room features an electric fireplace, built in bookshelves, vaulted ceiling, that creates a warm and inviting atmosphere in the heart of the home. Move in ready. Roof; 2016, AC/heat pump; 12/24, microwave; 2026, electric box; 1/2025, replumbed entire house; 2023.

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    Listing is courtesy of: FLORIDA HOME TEAM REALTY LLC

  • 1618 WRENTHAM CT, WINTER SPRINGS, FL - MLS# O6411489

    Oviedo High - O6411489 - 1618 WRENTHAM CT, WINTER SPRINGS, FL 32708
    16 Days on yellowkey

    $799,900 | Single Family Home | 5 beds | 3.5 baths | 3 gar

    Florida living at its finest! Nestled within the quaint gated community of Barrington Estates in Winter Springs, this stunning two-story home is ideally situated on a private cul-de-sac with no front or rear neighbors. Enjoy serene pond and conservation views from the front of the home, while the expansive fenced backyard overlooks mature trees, creating exceptional privacy and tranquility. Inside, the grand entry opens to elegant living and dining spaces highlighted by soaring ceilings and an impressive staircase. Luxury vinyl flooring flows throughout the first floor, adding both style and durability. The first-floor primary suite offers a private retreat featuring dual walk-in closets, separate vanities, a water closet, and a walk-in shower. The main level also includes a half bath, laundry room with access to the 3-car garage, and a spacious open-concept kitchen overlooking the family room perfect for entertaining. The chef’s kitchen is beautifully appointed with a large island and sink, granite countertops and backsplash, stainless steel appliances, double ovens, beverage fridge, oversized pantry, and an eat-in dining area. French doors seamlessly connect the indoor living spaces to the lanai and pool area. A dramatic double staircase leads to the second floor where you’ll find a spacious bonus room surrounded by four additional bedrooms. Two bedrooms feature walk-in closets, while the fourth bedroom serves as a private ensuite complete with two closets and a tub/shower combination bath. An additional full bath with a linen closet is also located upstairs. Wood flooring throughout the staircase, bonus room, and upstairs bedrooms adds warmth and elegance, while abundant windows fill the home with natural light. Designed for both entertaining and everyday living, the outdoor space offers the perfect backyard retreat featuring a sparkling saltwater pool with sun shelf, pavered pool deck, covered lanai, and cozy fire pit. Additional highlights include a paver driveway and an exceptional location with convenient access to Toll Road 417 and SR-434. Zoned for A-rated Oviedo schools and just minutes from shopping, restaurants, Oviedo on the Park, Winter Springs Town Center, UCF, Research Park, and Oviedo Medical Center. Community amenities include a playground, and the home is just a short distance from the Seminole Trail, ideal for biking, walking, and enjoying the outdoors. Welcome Home!

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    Listing is courtesy of: URBANISTA BROKERS

  • 1838 SENECA BLVD, WINTER SPRINGS, FL - MLS# O6411007

    Oviedo High - O6411007 - 1838 SENECA BLVD, WINTER SPRINGS, FL 32708
    16 Days on yellowkey

    $724,900 Reduced | Single Family Home | 4 beds | 3.0 baths | 2 gar

    Rare opportunity to own a spacious pool home on a private 2.1-acre conservation homesite in the highly desirable Chelsea Woods section of Tuscawilla. Offering 4 bedrooms, 3 bathrooms and over 3,100 square feet of living space, this home features a dedicated office with custom built-ins, formal living and dining areas, a wood-burning fireplace, and a large upstairs loft that provides flexible space for a media room, game room, home gym, or additional living area. The kitchen overlooks the main living spaces and pool area, while French doors open to an expansive covered lanai and screened pool enclosure designed for year-round Florida living. Step outside and enjoy your own backyard retreat featuring a large pool and spa with waterfall features, outdoor grilling area, generous deck space, mature landscaping, and peaceful conservation views with no rear neighbors. Major improvements include a roof replaced approximately 3 years ago and HVAC systems replaced approximately 3 years ago, providing peace of mind for years to come. Conveniently located near top-rated Seminole County schools, parks, golf, shopping, dining, and major commuter routes. Optional HOA membership available. Homes offering this combination of acreage, privacy, pool, location, and living space rarely become available.

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    Listing is courtesy of: HOPKEY REALTY

  • 877 BENCHWOOD DR, WINTER SPRINGS, FL - MLS# O6410431

    Winter Springs High - O6410431 - 877 BENCHWOOD DR, WINTER SPRINGS, FL 32708
    16 Days on yellowkey

    $460,000 | Single Family Home | 3 beds | 2.0 baths | 2 gar

    Inviting curb appeal welcomes you into this beautifully maintained Winter Springs pool home tucked within the peaceful established subdivision of Oak Forest. Step inside to an open floor plan with immediate views of the backyard oasis, creating a light and airy feel perfect for everyday living and entertaining. The spacious kitchen opens seamlessly to the living and dining areas and features granite countertops, stainless steel appliances and a breakfast bar ideal for gathering with family and friends. The floor plan offers comfortable living spaces, while sliding doors lead out to the screened porch overlooking the private backyard retreat. Enjoy Florida living year-round with the screened patio, resurfaced pool featuring a PebbleTec finish completed in 2020, a fully fenced yard and plenty of room to relax or entertain outdoors. Major updates provide peace of mind, including the roof, AC, and water heater all replaced in 2015. Additional improvements include gutters added in 2020, pool pump replaced in 2016, new garage door opener in 2025, and updated microwave, dishwasher, and garbage disposal in 2026. This home sits on a spacious lot in a quiet, established neighborhood. Conveniently located near SR-417, shopping, dining, and top-rated Seminole County schools - walking distance to both the elementary and middle school. This home is also just minutes from Trotwood Park and Central Winds Park which features pickleball courts, sports fields, playgrounds, walking trails, and community events.

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    Listing is courtesy of: COMPASS FLORIDA LLC

  • 984 TURKEY HOLLOW CIR, WINTER SPRINGS, FL - MLS# O6410083

    Winter Springs High - O6410083 - 984 TURKEY HOLLOW CIR, WINTER SPRINGS, FL 32708
    17 Days on yellowkey

    $410,000 | Single Family Home | 3 beds | 2.0 baths

    One or more photo(s) has been virtually staged. A spacious 3-bedroom, 2-bathroom home located in the highly sought-after community of Oak Forest in Winter Springs. Known for its beautiful tree-lined streets, mature oak trees, and quiet suburban charm, this family-friendly neighborhood also offers access to top-rated schools and is conveniently located near popular restaurants, shopping, and everyday conveniences. Inside, this home features a versatile and functional floor plan with a spacious family room, separate living room, dining room, large kitchen, dedicated office space, and an indoor laundry room. The detached shed provides the perfect opportunity for extra storage, a workshop, or hobby space. Step outside to enjoy the private backyard complete with a fire pit — ideal for relaxing or entertaining guests. The garage has been split into an office and storage space but can be converted back into a two car garage. Major upgrades and improvements include an updated roof (2018), gutters(2018), HVAC system(2022), windows(2020), garage door(2020), hot water heater(2021), electrical panels(2023), and added insulation(2019). Additional features include an indoor electric fireplace (2022), and numerous updates throughout, offering peace of mind and move-in-ready convenience. Call today to schedule your private tour!

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    Listing is courtesy of: ALL REAL ESTATE & INVESTMENTS

  • 451 HARBOR WINDS CT, WINTER SPRINGS, FL - MLS# O6406257

    Winter Springs High - O6406257 - 451 HARBOR WINDS CT, WINTER SPRINGS, FL 32708
    18 Days on yellowkey

    $357,500 | Townhouse | 3 beds | 2.5 baths | 2 gar

    Under contract-accepting backup offers. Virtually Staged. Welcome to 451 Harbor Winds Court, located in the desirable Winter Springs’ gated community of Harbor Winds! This beautifully maintained and truly move-in ready two-story townhome offers 3 bedrooms, 2.5 bathrooms, and an attached 2-car garage with updates throughout. Major improvements have already been completed for peace of mind, including a new roof, gutters, A/C system, water heater, and stainless steel kitchen appliances—all installed in 2023. Step inside to discover an inviting floor plan featuring an upgraded kitchen with granite countertops, 42" wood cabinetry, stainless steel appliances, a walk-in pantry, breakfast bar, and a charming breakfast nook perfect for casual dining. The kitchen opens seamlessly to the spacious living area, where sliding glass doors lead to the rear lanai—ideal for relaxing or entertaining. Upstairs, the spacious primary suite easily accommodates a king-sized bedroom set and features a large walk-in closet along with a private ensuite bath complete with dual vanities, a soaking tub, and a separate glass-enclosed shower. The additional bedrooms provide plenty of space and flexibility for guests or a home office. Residents of Harbor Winds enjoy access to a resort-style community pool and well maintained neighborhood, all while being conveniently located near shopping, dining, and everyday conveniences. Centrally located with easy access to Orlando’s world-famous attractions, including Walt Disney World and Universal Studios, and less than an hour from the beautiful beaches of New Smyrna and Daytona. Schedule your private showing today, don't miss out!

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    Listing is courtesy of: KELLER WILLIAMS HERITAGE REALTY

  • 294 SAN GABRIEL ST, WINTER SPRINGS, FL - MLS# O6409921

    Winter Springs High - O6409921 - 294 SAN GABRIEL ST, WINTER SPRINGS, FL 32708
    20 Days on yellowkey

    $249,990 | Single Family Home | 2 beds | 2.0 baths

    Under contract-accepting backup offers. Beautifully maintained 2-bedroom, 2-bath single-family home located in the desirable Deersong community of Winter Springs! Built in 1994 and offering 1,105 heated square feet, this move-in-ready home features numerous major updates for peace of mind. Recent improvements include interior paint (2025), waterproof laminate flooring in the living room and both bedrooms (2025), a full-home repipe (2026), and a water heater (2026). Additional big-ticket upgrades include the roof replacement in 2018 and the AC installed in 2015. The functional floor plan offers comfortable living spaces filled with natural light, vaulted ceilings, and the updated laminate flooring adds a modern touch throughout. Conveniently located near shopping, dining, parks, Winter Springs Town Center, and top-rated Seminole County schools, this home is perfect for first-time buyers, downsizers, or anyone looking for low-maintenance living in a great location.

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    Listing is courtesy of: KELLER WILLIAMS ADVANTAGE REALTY

  • 721 S ENDEAVOUR DR, WINTER SPRINGS, FL - MLS# O6409924

    Winter Springs High - O6409924 - 721 S ENDEAVOUR DR, WINTER SPRINGS, FL 32708
    22 Days on yellowkey

    $2,599 | Single Family Home | 3 beds | 2.0 baths | 2 gar

    Welcome home to this charming property 3 beds 2 baths located in the heart of Winter Springs! Nestled in a well-established community, this home offers comfortable living spaces, a functional layout, and a welcoming atmosphere perfect for everyday living and entertaining. Enjoy features such as spacious bedrooms, an inviting living area, and a private backyard ideal for relaxing or gatherings. Conveniently located near shopping, dining, parks, and major roadways with access to highly rated Seminole County schools. Don’t miss the opportunity to make this beautiful home yours! All applicants are required to complete a credit and background screening. Renters insurance is required. All residents are automatically enrolled in a master renters insurance policy for $11.95 per month. Residents can opt out of the master policy by providing proof of their own policy that meets minimum requirements.

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    Listing is courtesy of: 407 PROPERTIES

  • 1322 CASA PARK CIR, WINTER SPRINGS, FL - MLS# O6409227

    Winter Springs High - O6409227 - 1322 CASA PARK CIR, WINTER SPRINGS, FL 32708
    22 Days on yellowkey

    $1,700 | Townhouse | 2 beds | 2.5 baths

    Very nice 2 story townhouse in Winter Springs, Fl. Located within the Tuscawilla community, this home is within walking distance of a huge park, playground and athletic fields. very convenient to shopping and major roadways.

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    Listing is courtesy of: CLASSIC 1 REALTY INC

  • 280 MOREE LOOP #2, WINTER SPRINGS, FL - MLS# O6409577

    Winter Springs High - O6409577 - 280 MOREE LOOP #2, WINTER SPRINGS, FL 32708
    22 Days on yellowkey

    $150,000 | Condo | 2 beds | 2.0 baths

    One or more photo(s) has been virtually staged. Welcome home to this first-floor condo in the desirable Bay Village community of Winter Springs! Nestled among beautiful tree-lined streets, this spacious unit offers a fantastic opportunity to make it your own. The upgraded kitchen features stainless steel appliances, ample cabinetry, and plenty of workspace for cooking and entertaining. The open-concept living and dining area is filled with natural light thanks to the wall of sliders and windows along the living room. Laminate flooring runs throughout the home with no carpet anywhere for easy maintenance and a cohesive look. Residents of Bay Village enjoy access to the community pool and a prime location close to parks, shopping, dining, and top-rated schools. This home is move-in ready and waiting for its new owner to bring their vision, add some fresh updates, and give it the love and facelift to truly make it shine!

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    Listing is courtesy of: KELLER WILLIAMS HERITAGE REALTY

  • 412 BLUE BAYOU LN, WINTER SPRINGS, FL - MLS# O6407027

    Winter Springs High - O6407027 - 412 BLUE BAYOU LN, WINTER SPRINGS, FL 32708
    23 Days on yellowkey

    $380,000 Reduced | Townhouse | 3 beds | 3.5 baths | 2 gar

    PRICED TO SELL - Quick move in available. Welcome to 412 Blue Bayou Lane in the highly desirable Jesups Reserve community, where elevated style, smart design, and an unbeatable Winter Springs location come together without the luxury price tag. This beautifully maintained 3-bedroom, 3-bathroom, three-story townhome offers low-maintenance living just steps from Winter Springs Town Center. The flexible first-floor bedroom with full bath is ideal for guests, a home office, or multi-generational living. The main level features a bright open-concept living and dining area, an oversized kitchen with like-new stainless steel appliances, a generous breakfast bar, and convenient second-floor laundry. The private third-floor owner’s suite offers a large walk-in closet, en-suite bath with soaking tub and separate shower, and peaceful separation from the main living spaces. Enjoy three outdoor living areas, including a welcoming front porch, updated second-floor patio, and private third-floor balcony perfect for relaxing evenings. Major updates include a new roof in 2022, new A/C in 2023, garage door maintenance in 2024, brand-new stair railing, and laminate flooring throughout with no carpet. The oversized 2-car garage with added storage solutions keeps everything organized and functional. Jesups Reserve residents enjoy a resort-style community pool and spa, scenic pond views, and a well-kept neighborhood setting. The location is hard to beat – you’re minutes from Central Winds Park, Trotwood Park, with convenient access to shopping, dining and major likes like SR-417. This move-in-ready home delivers style, location, and value in one exceptional package. Move-in ready, meticulously maintained, and priced to sell—this is the opportunity buyers have been waiting for.

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    Listing is courtesy of: COLDWELL BANKER REALTY

  • 4991 COURTLAND LOOP, WINTER SPRINGS, FL - MLS# O6409511

    Winter Springs High - O6409511 - 4991 COURTLAND LOOP, WINTER SPRINGS, FL 32708
    23 Days on yellowkey

    $750,000 | Single Family Home | 4 beds | 2.5 baths | 2 gar

    Under contract-accepting backup offers. MULTIPLE OFFERS : HIGHEST AND BEST DUE BY SATURDAY, MAY 23 at 5PM. Welcome to this beautifully updated 4-bedroom, 2.5-bath pool home in the highly sought-after Winter Springs community of Tuskabay, offering the perfect blend of style, comfort, and convenience. Ideally located near shopping, dining, and major commuter routes, this home boasts lush landscaping, exceptional curb appeal, and a desirable side-entry 2-car garage. Inside, you’ll find neutral paint and flooring, abundant natural light, and an open floorplan designed for both everyday living and entertaining. The inviting foyer showcases stunning custom woodwork that flows seamlessly into the spacious dining area, while custom wood ceilings in both the foyer and loft up above add warmth and character. Elegant wrought iron railings accent the staircase and dining space for a sophisticated touch. The thoughtfully designed kitchen is situated at the front of the home and features an oversized opening to the living areas for great lines of sight, 42” cabinetry, granite countertops, tile backsplash, stainless steel appliances including built-in microwave, oven, and cooktop, plus a dinette area and walk-in pantry with convenient laundry access. The oversized family room is truly the heart of the home, highlighted by vaulted ceilings, a cozy wood-burning fireplace, two skylights, and French doors that open to the covered patio for seamless indoor/outdoor living. The spacious upstairs primary suite is a private retreat complete with its own wood-burning fireplace, custom accent wall, French doors leading to a private balcony, and a large walk-in closet with custom organization system. The luxurious en-suite bath offers a wrap-around, double-sink vanity, jacuzzi tub, and oversized shower. Adjacent to the primary suite are a versatile loft and an office/nursery space perfect for working from home or additional flexibility. Downstairs, three generously sized bedrooms feature large closets and ceiling fans. One bedroom includes a private half bath with direct access to the pool deck, making it an ideal cabana bath. An additional full hall bath features an oversized vanity, linen closet, and shower/tub combination. Step outside to your own backyard oasis featuring a large, screened and covered paver patio with custom wood ceiling overlooking the spacious, heated, chlorine pool. Beyond the screened enclosure, there’s still plenty of yard space to enjoy, all enclosed by a vinyl fence for added privacy. Additional upgrades include newer AC, crown molding, plantation shutters, engineered wood flooring, and added lighting and electrical outlets throughout. This exceptional home offers the perfect combination of timeless character, modern updates, and resort-style outdoor living.

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    Listing is courtesy of: KELLER WILLIAMS ADVANTAGE REALTY