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Modern Homes for Sale in Winter Springs, FL

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  • /36

    $549,900

    $30K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,153 Sq Ft

    50 Oak Bend Ct, Oviedo, FL 32765

    Nestled in the highly desirable Tuskawilla community of Oviedo, this beautifully maintained home offers the perfect blend of comfort, privacy, and timeless charm. Featuring 3 bedrooms, 2.5 bathrooms, and a versatile BONUS LOFT area ideal for a home office, playroom, or potential 4th bedroom, this home is thoughtfully designed for both everyday living and entertaining. Enjoy peace of mind with

    Agent Photo

    Evelyn Hartnett

    SOUTHERN REALTY ENTERPRISES

    50 Oak Bend Ct, Oviedo, FL 32765
  • /40

    $595,000

    • 4 Beds
    • 2 Baths
    • 2,398 Sq Ft

    696 Wyckliffe Place, Winter Springs, FL 32708

    Welcome to this beautifully updated 4-bedroom, 2-bath home in the highly desirable Tuskawilla area of Winter Springs, offering picturesque views of Lake Skittles. Nestled along a charming oak tree-lined street, this home makes a lasting first impression with beautiful, mature landscaping that greets you as you arrive. Thoughtfully maintained and upgraded, the home features new laminate flooring

    Marion Thacker RED BIRD REALTY OF FLORIDA INC

    696 Wyckliffe Place, Winter Springs, FL 32708
  • /31

    $685,000

    Open Sat 1PM - 3PM
    • 4 Beds
    • 3 Baths
    • 3,246 Sq Ft

    525 Saddlewood Ln, Winter Springs, FL 32708

    Pride of ownership is evident throughout this beautifully updated, MOVE-IN PERFECT, one-owner home located in the highly sought-after WINDING HOLLOW community of Winter Springs. This ideal two-story floor plan offers 4 BEDROOMS, 3 FULL BATHS, BONUS ROOM, 3-CAR GARAGE, and a LARGE SCREENED LANAI, showcasing timeless style, thoughtful updates, and versatility with TILE FLOORING throughout the first

    Rob Breese, III RE/MAX TOWN & COUNTRY REALTY

    525 Saddlewood Ln, Winter Springs, FL 32708
  • /50

    $329,900

    $10K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,178 Sq Ft

    335 Kirkcaldy Dr, Winter Springs, FL 32708

    Welcome home to this cozy 3-bedroom, 2-bath bungalow-style home located in the resort-like Highlands community, offering 1,178 sq. ft. of living space. This home features vaulted ceilings, ceramic tile throughout, fresh interior paint, and a newly renovated kitchen with granite countertops, solid wood shaker-style cabinets, and black appliances. Major updates include a 2025 water heater and a new

    Irina Carp MILLENIUM REALTY GROUP

    335 Kirkcaldy Dr, Winter Springs, FL 32708
  • /44

    $425,000

    $15K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,456 Sq Ft

    1422 Spalding Rd, Winter Springs, FL 32708

    PRICE REDUCTION!!!Ready to move into! Well maintained and updated 3-bedroom Tuskawilla villa, HOA maintains the lawn. This home boasts an open floor plan featuring beamed vaulted ceilings, a wood burning stone fireplace, an eat in kitchen and a spacious screened porch ROOF INSTALLED IN 2023, AC INSTALLED IN 2021, Resurfaced bath tub, shower and vanity countertops. Professional tennis courts and a

    Ramon Ortiz Cruz DIAMOND 2000 REALTY, INC

    1422 Spalding Rd, Winter Springs, FL 32708
  • /47

    $249,900

    $40K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,425 Sq Ft

    600 Northern Way Unit 502, Winter Springs, FL 32708

    MOTIVATED SELLER!!! Seller offering concession toward buyer closing cost. Location! Location! Location! This pristine condo nestled in the heart of Tuscawilla offers an incredible opportunity for low maintenance living in a serene and gated community. Enjoy summer days by the beautiful community pool and relax in the cabana. Across the way you will find access to Trotwood Park, with its

    Robert Bretz, PA EXP REALTY LLC

    600 Northern Way Unit 502, Winter Springs, FL 32708
  • /43

    $1,200,000

    • 5 Beds
    • 3.5 Baths
    • 3,212 Sq Ft

    1281 Natures Way, Winter Springs, FL 32708

    Experience the beauty of city living on 2.3 acres in the highly desirable city of Winter Springs with no HOA—where open space, natural surroundings, and an equestrian friendly lifestyle come together. This unique property offers the freedom of rural living while remaining conveniently located near the Tuscawilla area.The fully usable acreage is ideal for horses, cattle, or other livestock. If

    Javid Owji EQUITY REAL ESTATE BROKERS

    1281 Natures Way, Winter Springs, FL 32708
  • /50

    $695,000

    • 4 Beds
    • 3 Baths
    • 2,724 Sq Ft

    223 Blue Creek Dr, Winter Springs, FL 32708

    Elegant conservation retreat in prestigious Chestnut Estates-Tuscawilla. On a quiet cul-de-sac, this impeccably maintained four-bedroom, three-bath residence offers a rare combination of privacy, timeless comfort and everyday luxury. Backing to a serene conservation area with no rear neighbors, the home is surrounded by mature landscaping and picturesque natural views, creating a peaceful

    Gwyn Picerne PREMIER SOTHEBYS INT'L REALTY

    223 Blue Creek Dr, Winter Springs, FL 32708
  • /35

    $210,000

    $23K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,224 Sq Ft

    497 Club Dr, Winter Springs, FL 32708

    Move in Ready!...Beautiful 2/2 townhome in highly desirable Cypress Club community in The Highlands of Winter Springs, located in close proximity to SR 434! **Freshly Painted with light and neutral colors throughout! Vaulted ceiling in the very spacious/huge... family/great room with a wood burning fireplace! Split bedroom floorplan, with one bedroom downstairs. Brand new ceiling fan in upstairs

    Edyta Olejnik WATSON REALTY CORP

    497 Club Dr, Winter Springs, FL 32708
  • /37

    $275,000

    $10K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,460 Sq Ft

    476 Club Dr, Winter Springs, FL 32708

    Welcome to 476 Club Drive, a beautifully cared-for townhome nestled in the highly sought-after Cypress Club section of The Highlands in Winter Springs—a community known for its incredible amenities and natural surroundings. This spacious 3-bedroom, 2-bath residence blends comfort, functionality, and peace of mind with key updates already completed. Enjoy the benefits of a new roof 2026, new water

    Jeff Singletary KELLER WILLIAMS HERITAGE REALTY

    476 Club Dr, Winter Springs, FL 32708
  • /25

    $219,500

    $36K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,224 Sq Ft

    499 Club Dr, Winter Springs, FL 32708

    Beautiful 2 bedroom 2 bathroom townhome (Not a condo which means more financing choices for you as a buyer) within The Highlands Community. Brand New Roof on this townhome. The 20ft high ceiling in the Great Room gives this home a very open design with lots of natural light. Sliding doors lead out to a screened porch with separate locked storage space. Guest/2nd bedroom on the first floor with

    Paul Buscemi FLORIDA HOME TEAM REALTY LLC

    499 Club Dr, Winter Springs, FL 32708
  • /41

    $525,000

    • 4 Beds
    • 2.5 Baths
    • 2,416 Sq Ft

    947 Glen Abbey Cir, Winter Springs, FL 32708

    Virtually Staged. Welcome to 947 Glen Abbey Circle in the sought-after Greenbriar Country Club and Golf Course community of Winter Springs. This impeccably maintained 4-bedroom, 3-bathroom home with a spacious loft offers thoughtfully designed living space with beautiful conservation views and a flexible floor plan perfect for everyday living and entertaining.The bright and open layout

    Denise McKinley RE/MAX TOWN & COUNTRY REALTY

    947 Glen Abbey Cir, Winter Springs, FL 32708
  • /43

    $989,000

    $110K PRICE DROP
    • 5 Beds
    • 5 Baths
    • 3,885 Sq Ft

    1815 Seneca Blvd, Winter Springs, FL 32708

    Welcome to this beautifully reimagined 5-bedroom, 3 full bath, 2 half bath pool home located in the highly sought-after Chelsea Woods community of Tuscawilla. Blending timeless architectural character with extensive modern updates, this move-in ready home offers exceptional space, style, and functionality throughout. Step inside to discover expansive living areas designed for both everyday living

    Belinda Gonzales RE/MAX TOWN & COUNTRY REALTY

    1815 Seneca Blvd, Winter Springs, FL 32708
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