Winter Springs, FL Homes for Sale under $500,000

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  /46

  $315,000

  $10K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,468 Sq Ft

  171 Constitution Way, Winter Springs, FL 32708

  Welcome to this beautifully maintained townhome located in the desirable gated community of Heritage Park in Winter Springs. Perfectly positioned directly across from the community pool with ample guest parking nearby, this move-in ready home offers both comfort and convenience. Step inside to find attractive laminate flooring flowing throughout the first floor, complemented by neutral paint and

  Jean Scott KELLER WILLIAMS ADVANTAGE REALTY

  171 Constitution Way, Winter Springs, FL 32708
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  /68

  $329,900

  $10K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 1,504 Sq Ft

  439 Old Farm Ln, Winter Springs, FL 32708

  One or more photo(s) has been virtually staged. Location, Location, Location! Welcome to this beautifully designed 3-level townhome in the highly sought-after Jesups Reserve community. Featuring 3 spacious bedrooms—each on its own floor—this home offers exceptional comfort, flexibility, and privacy.The top-floor primary suite is a true retreat, complete with a large private balcony, perfect

  Brian Goodwin ORLANDO REALTY & PROPERTY MGNT

  439 Old Farm Ln, Winter Springs, FL 32708
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  /26

  $430,000

  $15K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,881 Sq Ft

  1307 Ortega St, Winter Springs, FL 32708

  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 though.

  James Evans CENTURY 21 ALTON CLARK

  1307 Ortega St, Winter Springs, FL 32708
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  /42

  $325,000

  $10K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,188 Sq Ft

  140 N Fairfax Ave, Winter Springs, FL 32708

  Fully Renovated Winter Springs Home with No HOA – Move-In Ready in Seminole County Welcome to 140 N. Fairfax Avenue in Winter Springs, Florida, a beautifully renovated home that blends classic Florida charm with modern upgrades in one of Seminole County’s most desirable and convenient locations. This extensively updated 3-bedroom, 1-bath home sits on a generous 8,900-square-foot lot and offers a

  Shawn McCormick ERA GRIZZARD REAL ESTATE

  140 N Fairfax Ave, Winter Springs, FL 32708
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  /20

  $373,000

  $12K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,582 Sq Ft

  1328 Andes Dr, Winter Springs, FL 32708

  Welcome to 1328 Andes Dr! Tile floors run throughout this well-maintained 4-bed, 2-bath in Sunrise Village, giving the home a clean, consistent look from room to room. The living room flows naturally into the dining area and kitchen, an open feel that works well for everyday living and entertaining.The kitchen includes stone countertops, well-maintained cabinetry, and easy access to the back

  Chad Jarvis AVENIR REAL ESTATE BROKERS LLC

  1328 Andes Dr, Winter Springs, FL 32708
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  /62

  $379,900

  Open Sat 11AM - 1PM Coming Soon

  • 3 Beds
  • 2.5 Baths
  • 1,519 Sq Ft

  453 Gee Hammock Ln, Winter Springs, FL 32708

  Welcome to this beautifully maintained townhome located in the highly desirable Winter Springs, where comfort, convenience, and lifestyle come together seamlessly. This exceptional residence offers access to community amenities including a fitness center and a community pool overlooking a serene neighborhood pond—perfect for relaxation and unwinding. Another outstanding feature is its unbeatable

  Margo Rochelle WEICHERT REALTORS HALLMARK PROPERTIES

  453 Gee Hammock Ln, Winter Springs, FL 32708
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  /29

  $330,000

  $5K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,680 Sq Ft

  471 Harbor Winds Ct, Winter Springs, FL 32708

  Welcome to your own slice of Winter Springs paradise at 417 Harbor Winds Court! Tucked away inside a secure gated community, this beautiful home offers the perfect blend of privacy and suburban tranquility. Step inside to a bright, open-concept floor plan designed for seamless everyday living and effortless entertaining. This home is thoughtfully designed with the primary bedroom suite privately

  Terrica Francois KELLER WILLIAMS ADVANTAGE III

  471 Harbor Winds Ct, Winter Springs, FL 32708
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  /36

  $460,000

  $25K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 2,066 Sq Ft

  1126 Trotwood Blvd, Winter Springs, FL 32708

  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

  Joyce Tang JOY ESTATE ENTERPRISE INC

  1126 Trotwood Blvd, Winter Springs, FL 32708
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  /30

  $430,000

  $5K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 1,678 Sq Ft

  1326 Tarflower Dr, Winter Springs, FL 32708

  Welcome to 1326 Tarflower Drive, a stunning 2025-built townhome located in the highly sought-after Hickory Grove community in Winter Springs. Perfectly positioned on one of the most desirable lots in the neighborhood, this rare corner-unit offers exceptional privacy, abundant natural light, and beautiful green space views. With no neighboring building on one side, two mature magnolia trees, and

  Yuly Rodriguez DOUGLAS EDMUND REAL ESTATE LLC

  1326 Tarflower Dr, Winter Springs, FL 32708
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  /33

  $438,997

  $11K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,554 Sq Ft

  872 Falkirk Dr, Winter Springs, FL 32708

  BACK ON THE MARKET DUE TO BUYERS FINANCING FALL TROUGH!! Beautifully maintained home located in one of the most desirable areas of Winter Springs, offering the perfect blend of comfort, convenience, and outdoor living. Surrounded by scenic walking and biking trails throughout the neighborhood, this home delivers a peaceful setting while staying close to everything you need. This property features

  Elizabeth Rodriguez CAISSA REALTY INVESTMENT INC

  872 Falkirk Dr, Winter Springs, FL 32708
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  /25

  $285,000

  $5K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,326 Sq Ft

  299 Woodgreen Ln, Winter Springs, FL 32708

  Welcome to this BEAUTIFULLY UPDATED 3-bedroom, 2.5-bath townhome in the PEACEFUL Mount Greenwood community of Winter Springs, where modern upgrades and a thoughtfully designed layout create a truly inviting place to call home. As a CORNER UNIT, this residence enjoys added privacy along with a serene setting, including POND VIEWS just beyond the rear fence, best appreciated from the upstairs

  Jennifer Wemert WEMERT GROUP REALTY LLC

  299 Woodgreen Ln, Winter Springs, FL 32708
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  /36

  $230,000

  $15K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,359 Sq Ft

  4490 Brook Hollow Cir, Winter Springs, FL 32708

  Welcome to 4490 Brook Hollow, a beautifully maintained property nestled in a quiet and desirable Florida community. This home offers the perfect blend of comfort, functionality, and Florida lifestyle living.Step inside to find a light-filled interior with an open and inviting floor plan, ideal for both everyday living and entertaining. The spacious living areas flow seamlessly into a

  Nicolas Merino EXP REALTY LLC

  4490 Brook Hollow Cir, Winter Springs, FL 32708
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  /28

  $399,900

  Open Sat 11AM - 1PM

  • 3 Beds
  • 2.5 Baths
  • 1,606 Sq Ft

  1357 Mill Stream Ln, Winter Springs, FL 32708

  Welcome to this beautifully updated 3-bedroom, 2.5-bath end-unit townhome in the desirable Jesups Landing community of Winter Springs! Recent updates include new flooring, new exterior paint and a new roof creating a fresh, modern feel. The thoughtfully designed layout features generous living and dining areas that flow seamlessly into the kitchen, making entertaining easy. Upstairs, you'll find

  Michelle Richardson KELLER WILLIAMS CLASSIC

  1357 Mill Stream Ln, Winter Springs, FL 32708
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  /25

  $221,000

  $19K PRICE DROP

  • 2 Beds
  • 2.5 Baths
  • 1,180 Sq Ft

  510 Green Spring Cir, Winter Springs, FL 32708

  Explore 510 Green Spring Cir, a residence recently enhanced with fresh interior paint and partial flooring replacement throughout. The kitchen includes an accent backsplash, complementing the recent updates for a refreshed interior feel. This property blends modern updates and practical style, ready for you to enjoy. Included 100-Day Home Warranty with buyer activation

  Karen Albright OPENDOOR BROKERAGE LLC

  510 Green Spring Cir, Winter Springs, FL 32708
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  /25

  $375,000

  • 3 Beds
  • 2 Baths
  • 1,574 Sq Ft

  807 Buckie Dr, Winter Springs, FL 32708

  Move Right In this Updated Highlands Home! Desirable Gas Stove in Kitchen along with newer Appliances & Granite Countertops, New Bathroom Vanities New Roof 2024. Large Fenced Yard, Fireplace & Inside Laundry Room. The Highlands has a Large Community Pool, Playgrounds, Clubhouse with BBQ Area, Audibon Park, Tennis & Pickleball Courts & Nature Walking Trails. Highly rated Seminole County Schools.

  Paul Buscemi FLORIDA HOME TEAM REALTY LLC

  807 Buckie Dr, Winter Springs, FL 32708
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  /29

  $294,900

  $30K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,069 Sq Ft

  421 Horizon Dr, Winter Springs, FL 32708

  Welcome to 421 Horizon Drive in Winter Springs, located in The Seasons community. This move-in ready home checks all the big boxes upfront: a 50-year Rhino shingle roof (2019), a 3.5-ton 14 SEER AC unit with heat pump and updated ductwork, a new electric panel, and a 2019 water heater. Beautifully maintained and thoughtfully updated throughout, this one-story home offers 3 bedrooms, 2 bathrooms,

  Peter Luu REAL BROKER, LLC

  421 Horizon Dr, Winter Springs, FL 32708
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  /26

  $315,000

  • 3 Beds
  • 2 Baths
  • 1,500 Sq Ft

  781 Bayou Dr, Casselberry, FL 32707

  Brand New 2026! This home sits in a desirable location in Casselberry Florida. Living near Lake Kathryn Park in Casselberry, Florida, offers a balanced lifestyle that combines quiet residential charm with modern recreational amenities. Commuter Friendly to Downtown Orlando, 5 minutes to I-4, convenient shopping, Altamonte Mall and ''the Greater Marketplace providing easy access to retailers. In

  Aimee Anselmi LLC Keller Williams Heritage

  781 Bayou Dr, Casselberry, FL 32707
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  /62

  $400,000

  • 3 Beds
  • 2.5 Baths
  • 1,807 Sq Ft

  942 Legacy Winds Way, Casselberry, FL 32707

  Welcome to Legacy Place—where style, function, and low-maintenance living come together in this beautifully maintained townhome. Built in 2022 and offering 3 bedrooms, 2.5 bathrooms, 1,806 square feet, and an attached 2-car garage, this move-in ready home delivers the benefits of newer construction without the wait. Step inside to a bright open-concept floor plan where abundant natural light

  Marci Blanchard KELLER WILLIAMS ADVANTAGE REALTY

  942 Legacy Winds Way, Casselberry, FL 32707
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  /28

  $344,900

  $10K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,498 Sq Ft

  1562 Grand Rue Dr, Casselberry, FL 32707

  Welcome to this like-new 2022 Craftsman-style END-UNIT townhome in the heart of highly desirable Seminole County! This beautifully maintained 3-bedroom, 2.5-bath home offers the perfect blend of modern design, energy efficiency, and low-maintenance living. As an end unit, the home is filled with abundant natural light and offers additional privacy along with extra green space to enjoy—without the

  Simon Colak USCO CAPITAL GROUP

  1562 Grand Rue Dr, Casselberry, FL 32707
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  /26

  $299,000

  New Construction $16K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,500 Sq Ft

  781 Bayou Dr, Casselberry, FL 32707

  One or more photo(s) has been virtually staged. Brand New 2026! This home sits in a desirable location in Casselberry Florida. Living near Lake Kathryn Park in Casselberry, Florida, offers a balanced lifestyle that combines quiet residential charm with modern recreational amenities. Commuter Friendly to Downtown Orlando, 5 minutes to I-4, convenient shopping, Altamonte Mall and "the Greater

  Aimee Anselmi LLC KELLER WILLIAMS HERITAGE REALTY

  781 Bayou Dr, Casselberry, FL 32707

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