37,947

Winter Garden, FL Homes

Section Image Section Image Section Image
  • /49

    $419,000

    Open Sun 11AM - 2PM
    • 2 Beds
    • 2 Baths
    • 1,574 Sq Ft

    13640 Splashing Isla Dr, Winter Garden, FL 34787

    Short Sale. ***SHORT SALE***Built in 2024, this like new 2 bedroom plus den, 2 bathroom home offers modern finishes, thoughtful upgrades, and a private setting tucked toward the back of the community with no rear neighbors. The flexible den features French doors, making it ideal for a home office, hobby room, or additional living space. The open concept layout is filled with natural light and

    Agent Photo

    Vanessa Scotland, PA

    SERHANT

    13640 Splashing Isla Dr, Winter Garden, FL 34787
  • /23

    Starting at $1,805

    Total Monthly Price

    • 1 - 3 Beds

    15000 Stratus Loop, Winter Garden, FL 34787

    Take the next step in life at Corban Horizon West. A place that draws inspiration from the warmth of the neighborhood and the endless possibilities that surround it, our homes offer a refreshing experience guaranteed to exceed your expectations for modern living. Timeless yet contemporary. Comfortable yet connected. Our residences are a wonderful blend of tasteful design, thoughtful amenities and

    Corban Horizon West

    15000 Stratus Loop, Winter Garden, FL 34787
  • /2

    $645,000

    Sold Sep 19, 2025

    1208 Castleport Rd, Winter Garden, FL 34787

    • 5 Beds
    • 3.5 Baths
    • 3,074 Sq Ft
    • Built 2001

    Last Sold Summary

    • 8% Below List Price
    • $210/SF
    • 85 Days On Market

    Current Estimated Value $643,825

    Last Listing Agent Barbara Waltman KELLER WILLIAMS CLASSIC

    1208 Castleport Rd, Winter Garden, FL 34787
    • /2

      Est $592,384

      Not Listed For Sale

      13940 Magnolia Ridge Loop, Winter Garden, FL 34787

      • 3 Beds
      • 3 Baths
      • 2,559 Sq Ft
      • Built 2017
      13940 Magnolia Ridge Loop, Winter Garden, FL 34787

      Last Sold Summary

      • 15 Days On Market

  • /56

    $723,000

    Pending
    • 5 Beds
    • 4 Baths
    • 3,602 Sq Ft

    7187 Wild Strawberry Run, Winter Garden, FL 34787

    Under contract-accepting backup offers. There are homes that simply check the boxes... And then there are homes that instantly make you feel something the moment you walk through the door. This former model home tucked inside one of Winter Garden’s most loved communities, Independence. From the soaring ceilings to the warm engineered wood floors flowing throughout the home, every space feels

    Agent Photo

    Carmelo Nuccio

    RE/MAX EXCLUSIVE COLLECTION

    7187 Wild Strawberry Run, Winter Garden, FL 34787
  • /50

    Starting at $1,830 Per Month

    • 1 - 3 Beds

    14012 Shoreside Way, Winter Garden, FL 34787

    Warm lake breezes and sunshine define the luxe lakeside lifestyle of the Lakewalk apartment residences that will wrap the shoreline of Lake Hancock next to the Town Center’s shopping, dining and entertainment. We offer 1 bedroom, 2 bedroom, and 3 bedroom apartment homes with the most up-to-date luxurious furnishings. If you are looking for relaxing, luxury living, look no further than Lakewalk at

    Lakewalk at Hamlin

    14012 Shoreside Way, Winter Garden, FL 34787
  • /2

    $510,000

    Sold Nov 14, 2025

    16394 Silver Brook Way, Winter Garden, FL 34787

    • 4 Beds
    • 2.5 Baths
    • 2,114 Sq Ft
    • Built 2025

    Last Sold Summary

    • $241/SF

    Current Estimated Value $518,466

    Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

    16394 Silver Brook Way, Winter Garden, FL 34787
    • /2

      Est $695,982

      Not Listed For Sale

      8120 Soldierwood St, Winter Garden, FL 34787

      • 4 Beds
      • 2.5 Baths
      • 3,048 Sq Ft
      • Built 2016
      8120 Soldierwood St, Winter Garden, FL 34787

      Last Sold Summary

      • 11 Days On Market

  • /74

    $1,399,999

    • 4 Beds
    • 3.5 Baths
    • 4,000 Sq Ft

    15264 Shonan Gold Dr, Winter Garden, FL 34787

    Welcome to this spacious 4-bedroom, 3.5-bath pool home offering 4,000 square feet in the highly sought-after Overlook at Hamlin community in Horizon West. Showcasing Lake Hancock views throughout the home and Disney fireworks in the distance, this property combines generous living space, impressive architecture, and an unbeatable location in one of Winter Garden's most desirable communities. From

    Agent Photo

    Tiffany Pantozzi

    ALIGN REAL ESTATE LLC

    15264 Shonan Gold Dr, Winter Garden, FL 34787
  • /28

    Starting at $2,048

    Total Monthly Price

    • 1 - 2 Beds

    5795 Citrus Village Blvd, Winter Garden, FL 34787

    Schedule your in-person or virtual tour today! Walk-ins are also welcome!

    Overture Hamlin 55+ Active Adult Apartment...

    5795 Citrus Village Blvd, Winter Garden, FL 34787
  • /2

    $695,000

    Sold Oct 20, 2025

    9863 Summerlake Groves St, Winter Garden, FL 34787

    • 3 Beds
    • 2.5 Baths
    • 2,072 Sq Ft
    • Built 2020

    Last Sold Summary

    • 7% Below List Price
    • $335/SF
    • 103 Days On Market

    Current Estimated Value $691,511

    Last Listing Agent Viviane Rocha WRA BUSINESS & REAL ESTATE

    9863 Summerlake Groves St, Winter Garden, FL 34787
    • /2

      Est $886,996

      Not Listed For Sale

      1078 Vinsetta Cir, Winter Garden, FL 34787

      • 6 Beds
      • 4.5 Baths
      • 4,733 Sq Ft
      • Built 2014
      1078 Vinsetta Cir, Winter Garden, FL 34787

      Last Sold Summary

      • 75 Days On Market

  • /37

    $525,000

    $10K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,170 Sq Ft

    1343 Castleport Rd, Winter Garden, FL 34787

    Virtually Staged. Welcome to this beautifully landscaped 3-bedroom, 2-bathroom home in the 24-hour guard-gated Stoneybrook West community. Featuring a split-bedroom floor plan, the layout includes a versatile flex room ideal for a home office or den. The kitchen is equipped with white appliances and granite countertops and flows easily into the main living spaces, with ceiling fans installed

    Agent Photo

    Kristi Matthew

    CENTURY 21 CARIOTI

    1343 Castleport Rd, Winter Garden, FL 34787
  • /21

    Starting at $1,499

    Total Monthly Price

    • 1 - 3 Beds

    15122 W Colonial Dr, Winter Garden, FL 34787

    Learn more about our current specials! Experience stylish living at a price that's right at Country Gardens Apartment Homes. Ideally situated in beautiful Winter Garden, Florida, our welcoming community blends quiet charm with excellent access to the greater Orlando area. Located right on the corner of SR-50 (West Colonial Drive)

    Country Gardens

    15122 W Colonial Dr, Winter Garden, FL 34787
  • /43

    $439,990

    Sold Oct 28, 2025

    15034 Grove Lake Dr, Winter Garden, FL 34787

    • 3 Beds
    • 2.5 Baths
    • 1,881 Sq Ft
    • Built 2025

    Move in Ready Sold Summary

    • $234/SF
    • 23 Days On Market

    Current Estimated Value $457,728

    DRB Homes Parkview at Hamlin

    15034 Grove Lake Dr, Winter Garden, FL 34787
    • /2

      Not Listed For Sale

      14501 Grove Resort Ave Unit 2133, Winter Garden, FL 34787

      • 3 Beds
      • 2 Baths
      • 1,396 Sq Ft
      • Built 2018
      14501 Grove Resort Ave Unit 2133, Winter Garden, FL 34787

      Last Sold Summary

      • 510 Days On Market

  • /30

    $497,000

    $25K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,042 Sq Ft

    16105 Water Spring Blvd, Winter Garden, FL 34787

    PRICE IMPROVEMENT!!! Now offered at a substantially reduced price. The seller will pay off the existing solar panel loan (approximately $29,000) in full at closing, allowing the buyer to enjoy the benefits of solar energy without assuming this debt.Perfect for buyers seeking convenience, accessibility, and a family-friendly setting—just steps from the elementary school!!Discover this

    Agent Photo

    Yesenia Barrios

    URBAN-O REAL ESTATE SOLUTIONS

    16105 Water Spring Blvd, Winter Garden, FL 34787
  • /24

    Starting at $1,591 Per Month

    • Studio - 3 Beds

    14680 Westerly Dr, Winter Garden, FL 34787

    Luxury apartment living has never been easier than in your dream apartment home at The Westerly Apartments in Horizon West. Offering pet-friendly homes with modern interiors, abundant amenity spaces and an unparalleled location near Orlando's theme parks.With exceptional craftsmanship and attention to detail, our rentals offer a variety of studio, one, two, and three-bedroom layout to meet your

    The Westerly

    14680 Westerly Dr, Winter Garden, FL 34787
  • /2

    $600,000

    Sold Dec 17, 2025

    3390 Current Ave, Winter Garden, FL 34787

    • 5 Beds
    • 3 Baths
    • 2,916 Sq Ft
    • Built 2020

    Last Sold Summary

    • 6% Below List Price
    • $206/SF
    • 74 Days On Market

    Current Estimated Value $616,221

    Last Listing Agent Jessica Macias KELLER WILLIAMS ADVANTAGE III

    3390 Current Ave, Winter Garden, FL 34787
    • /2

      Not Listed For Sale

      13048 Serene Glade Rd, Winter Garden, FL 34787

      • 3 Beds
      • 3 Baths
      • 2,083 Sq Ft
      • Built 2024
      13048 Serene Glade Rd, Winter Garden, FL 34787

      Last Sold Summary

      • 531 Days On Market

  • /23

    $574,999

    $45K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,420 Sq Ft

    12566 Westhaven Oak Dr, Winter Garden, FL 34787

    PRICE IMPROVEMENT! PRICED TO SELL!Welcome to 12566 Westhaven Oak Drive in the desireable Osprey Ranch community of Winter Garden.This beautifully designed 4-bedroom, 3-bath home offers the perfect blend of modern comfort andluxury finishes, featuring an open-concept layout ideal for everyday living and entertaining. Thegourmet kitchen shines with quartz countertops, a spacious

    Agent Photo

    Kendra Wallace

    UNITED REAL ESTATE PREFERRED

    12566 Westhaven Oak Dr, Winter Garden, FL 34787
  • /23

    Starting at $1,460 Per Month

    • 1 - 3 Beds

    1301 Inland Seas Blvd, Winter Garden, FL 34787

    Inland Seas Apartments

    1301 Inland Seas Blvd, Winter Garden, FL 34787
  • /2

    $739,000

    Sold Jan 05, 2026

    214 S Main St, Winter Garden, FL 34787

    • 4 Beds
    • 4 Baths
    • 2,268 Sq Ft
    • Built 1993

    Last Sold Summary

    • 1% Below List Price
    • $326/SF
    • 0 Days On Market

    Current Estimated Value $735,682

    Last Listing Agent Joe Wynkoop CHARLES RUTENBERG REALTY ORLANDO

    214 S Main St, Winter Garden, FL 34787
    • /2

      Est $809,431

      Not Listed For Sale

      17996 Adrift Rd, Winter Garden, FL 34787

      • 4 Beds
      • 3 Baths
      • 3,323 Sq Ft
      • Built 2024
      17996 Adrift Rd, Winter Garden, FL 34787

      Last Sold Summary

      • 16 Days On Market

  • /43

    $339,500

    $15K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,544 Sq Ft

    1532 Scarlet Oak Loop Unit 70B, Winter Garden, FL 34787

    ***SELLER MOTIVATED*** Wonderful primary residence or rental investment opportunity! This beautifully maintained 3-bedroom, 2.5-bath condo in the central and peaceful Tucker Oaks community offers the perfect blend of comfort and convenience with a spacious and practical layout.The main level offers a well-appointed kitchen with granite countertops, 42” cabinetry, and a newer refrigerator,

    Agent Photo

    David Hartigan

    JASON MITCHELL REAL ESTATE FLO

    1532 Scarlet Oak Loop Unit 70B, Winter Garden, FL 34787
  • /17

    $2,870

    Total Monthly Price

    • 4 Beds
    • 2 Baths
    • 1,770 Sq Ft
    • House for Rent

    153 Timbercreek Pines Cir, Winter Garden, FL 34787

    Now offering 19-month leases. Sign today and lock in today’s low rate for the next 19 months! Offer valid for new applicants who sign a 19-month lease and move-in by August 31, 2026. Base rent will remain at the 12-month lease rate for the duration of the 19-month term. Offer is contingent on application approval and execution of a lease agreement. Other terms and conditions may apply. This

    153 Timbercreek Pines Cir, Winter Garden, FL 34787
  • /2

    $650,000

    Sold Apr 03, 2026

    14008 Jomatt Loop, Winter Garden, FL 34787

    • 4 Beds
    • 3 Baths
    • 2,952 Sq Ft
    • Built 2019

    Last Sold Summary

    • $220/SF
    • 35 Days On Market

    Current Estimated Value $653,603

    Last Listing Agent David Fontana CHARLES RUTENBERG REALTY ORLANDO

    14008 Jomatt Loop, Winter Garden, FL 34787
    • /20

      Est $398,841

      Not Listed For Sale

      12035 Holystone St, Winter Garden, FL 34787

      • 3 Beds
      • 2.5 Baths
      • 1,567 Sq Ft
      • Built 2023
      12035 Holystone St, Winter Garden, FL 34787

      Last Sold Summary

      • 51 Days On Market

  • /31

    $500,000

    • 3 Beds
    • 2 Baths
    • 1,705 Sq Ft

    16802 Oakboro St, Winter Garden, FL 34787

    Welcome to this beautifully maintained Laurel floor plan, featuring fresh professional exterior paint (2026), 3 bedrooms, 2 bathrooms, and an open-concept layout thoughtfully designed for comfortable everyday living and effortless entertaining. The spacious kitchen serves as the heart of the home, featuring stainless steel appliances, a breakfast bar, a walk-in pantry, and an adjoining dining

    Agent Photo

    Rick Brown

    KELLER WILLIAMS ADVANTAGE 2 REALTY

    16802 Oakboro St, Winter Garden, FL 34787
  • /20

    $2,700 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,868 Sq Ft
    • Condo for Rent

    11193 Hanlon Ter Aly, Winter Garden, FL 34787

    Welcome to your new home in the charming district of Winter Garden, FL. This property offers a fantastic location, just a short drive from several delightful restaurants and a variety of department stores. Enjoy peace of mind knowing that Orlando Health Horizon West Hospital is only 10 minutes away, making it ideal for those seeking convenience and accessibility.This spacious home

    11193 Hanlon Ter Aly, Winter Garden, FL 34787
  • /2

    $150,000

    Sold Feb 13, 2026

    0 Avalon Rd Unit MFRJ997704, Winter Garden, FL 34787

    • Land
    • 23,522 Sq Ft
    • $277,778 per Acre

    Last Sold Summary

    Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

    0 Avalon Rd Unit MFRJ997704, Winter Garden, FL 34787
    • /2

      Est $832,255

      Not Listed For Sale

      15343 Lebeau Loop, Winter Garden, FL 34787

      • 4 Beds
      • 3.5 Baths
      • 3,041 Sq Ft
      • Built 2022
      15343 Lebeau Loop, Winter Garden, FL 34787

      Last Sold Summary

      • 13 Days On Market

  • /89

    $2,295,000

    $150K PRICE DROP Under Contract
    • 6 Beds
    • 5.5 Baths
    • 4,817 Sq Ft

    7460 John Hancock Dr, Winter Garden, FL 34787

    Under contract-accepting backup offers. Experience lakefront luxury at its finest. Situated on the pristine shores of Lake Hancock in Overlook at Hamlin, this 2020-built Mediterranean masterpiece offers the perfect blend of elegance and recreation. Boasting 6 spacious bedrooms and 5.5 baths, this home features an open-concept layout with soaring cathedral ceilings and high-end finishes

    Agent Photo

    Mauro Costa

    VISTA CAY REALTY COMPANY

    7460 John Hancock Dr, Winter Garden, FL 34787
  • /15

    $2,735 Per Month

    • 4 Beds
    • 2.5 Baths
    • 1,606 Sq Ft
    • House for Rent

    1961 Portcastle Cir, Winter Garden, FL 34787

    Apply now or schedule your self-tour today and take the first step toward getting more than just a place to live. Rent with FirstKey Homes for a home that's right for you, plus professional service and maintenance, innovative resident programs, and more; that's the power of purple! This 4-bedroom, 2.5-bathroom rental home in Winter Garden, FL, may be the right place for you. See the pictures

    1961 Portcastle Cir, Winter Garden, FL 34787
  • /2

    $515,000

    Sold Jun 22, 2026

    3276 Sailing Pier Ave, Winter Garden, FL 34787

    • 3 Beds
    • 2 Baths
    • 1,990 Sq Ft
    • Built 2020

    Last Sold Summary

    • 2% Below List Price
    • $259/SF
    • 21 Days On Market

    Current Estimated Value $524,875

    Last Listing Agent Erica Diaz HOMEVEST REALTY

    3276 Sailing Pier Ave, Winter Garden, FL 34787
    • /2

      Est $83,979

      Not Listed For Sale

      821 Pine St, Winter Garden, FL 34787

      821 Pine St, Winter Garden, FL 34787

      Last Sold Summary

      • 58 Days On Market

  • /26

    $1,250,000

    $1M PRICE DROP
    • Land
    • 5.11 Acres
    • $244,618 per Acre

    10133 Colt Ln, Winter Garden, FL 34787

    Discover 5.1 beautiful acres in Avalon Hills, an exclusive community featuring just 16 premium luxury home 5 acre lots. No need to move almost an hour away just to find some land and more privacy when this gem is minutes to Windermere and everywhere you want to be. This vacant land represents the essence of premium real estate, nestled at the end of a one-way street ending in a serene cul-de-sac

    Agent Photo

    Jessica McKinney

    FLORIDA REALTY EXCHANGE LLC

    10133 Colt Ln, Winter Garden, FL 34787
  • /19

    $1,850 Per Month

    • 2 Beds
    • 2 Baths
    • 1,144 Sq Ft
    • Condo for Rent

    1257 Winter Green Way, Winter Garden, FL 34787

    Welcome to this extremely spacious 2-bedroom, 1 full-bathroom and 1 half-bath townhome, offering modern updates and a peaceful retreat in a quiet community. Step inside to find a bright and open floor plan with stylish finishes throughout. The fully updated kitchen features new cabinetry, sleek countertops, and stainless-steel appliances, making it a dream for cooking and entertaining. Enjoy the

    1257 Winter Green Way, Winter Garden, FL 34787
  • /28

    $640,000

    Sold Apr 17, 2026

    16055 Silver Brook Way, Winter Garden, FL 34787

    • 3 Beds
    • 2.5 Baths
    • 2,072 Sq Ft
    • Built 2023

    Last Sold Summary

    • 7% Below List Price
    • $309/SF
    • 9 Days On Market

    Current Estimated Value $644,784

    Last Listing Agent Viviane Rocha WRA BUSINESS & REAL ESTATE

    16055 Silver Brook Way, Winter Garden, FL 34787
    • /2

      Est $1,826,941

      Not Listed For Sale

      960 Civitas Way, Winter Garden, FL 34787

      • 5 Beds
      • 4.5 Baths
      • 4,508 Sq Ft
      • Built 2020
      960 Civitas Way, Winter Garden, FL 34787

      Last Sold Summary

      • 50 Days On Market

Showing Results 81 - 120, Page 3 of 18

How to Buy a Home How to Finance a Home How to Sell a Home