37,759

Winter Garden, FL Homes

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  • /43

    $669,000

    $70K PRICE DROP Pending
    • 4 Beds
    • 3 Baths
    • 2,117 Sq Ft

    9723 Lost Creek Dr, Winter Garden, FL 34787

    Beautiful 4-bedroom, 3 bath water view home in Waterleigh, Horizon West’s Premier Community! Welcome to your next chapter in Waterleigh, where resort-style amenities and thoughtful design come together in one of Horizon West’s most desirable neighborhoods. This impeccably maintained 4-bedroom, 3-bath home offers 2,117 sq. ft. of single-story comfort, ideal for families, first-time buyers, or

    Ping Ma

    CHARLES RUTENBERG REALTY ORLANDO

    (321) 478-2658

    9723 Lost Creek 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...

    (689) 600-3037

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

    $212,500

    Sold Jul 11, 2025

    385 Eron Way Unit 45, Winter Garden, FL 34787

    • 2 Beds
    • 2 Baths
    • 930 Sq Ft
    • Built 1988

    Last Sold Summary

    • 10% Below List Price
    • $228/SF
    • 99 Days On Market

    Current Estimated Value $209,230

    Last Listing Agent Matt Erickson RE/MAX PRIME PROPERTIES

    385 Eron Way Unit 45, Winter Garden, FL 34787
    • /2

      Est $1,779,725

      Not Listed For Sale

      16182 Johns Lake Overlook Dr, Winter Garden, FL 34787

      • 5 Beds
      • 5.5 Baths
      • 4,084 Sq Ft
      • Built 2019
      16182 Johns Lake Overlook Dr, Winter Garden, FL 34787

      Last Sold Summary

      • 36 Days On Market

  • /89

    $2,445,000

    • 6 Beds
    • 5.5 Baths
    • 4,817 Sq Ft

    7460 John Hancock Dr, Winter Garden, FL 34787

    Experience lakefront luxury at its finest. Situated on the pristine shores of Lake Hancock in the gated 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 throughout. The gourmet kitchen,

    Agent Photo

    Mauro Costa

    VISTA CAY REALTY COMPANY

    (321) 449-2572

    7460 John Hancock Dr, Winter Garden, FL 34787
  • /21

    Starting at $1,449

    Total Monthly Price

    • 1 - 3 Beds

    15122 W Colonial Dr, Winter Garden, FL 34787

    Stylish design at a price that's right! Country Gardens Apartment Homes is located in Winter Garden, Florida, with easy access to Florida's Turnpike and SR-50/Colonial Drive. You'll experience a top selection of amenities and features at this community, like a resort-style pool with sundeck, lake/pond views, and a heart-healthy cardio & fitness center. The leasing team is ready for you to come by

    Country Gardens

    (352) 717-2792

    15122 W Colonial Dr, 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 $500,885

      Not Listed For Sale

      7823 Summerlake Groves St, Winter Garden, FL 34787

      • 4 Beds
      • 2.5 Baths
      • 2,101 Sq Ft
      • Built 2017
      7823 Summerlake Groves St, Winter Garden, FL 34787

      Last Sold Summary

      • 39 Days On Market

  • /70

    $1,046,000

    $46K PRICE INCREASE
    • 5 Beds
    • 4 Baths
    • 3,863 Sq Ft

    1711 Amsel Falls Park Terrace, Winter Garden, FL 34787

    Back on the Market- Buyer’s Financing Fell through! No fault of the Seller. The home successfully completed the contract process, Inspections, i.e. Four Point, Wind Mitigation, and WDO along with the Appraisal. Now Welcome to this stunning architectural masterpiece nestled in the heart of Twinwaters, one of Winter Garden’s most sought-after communities. This elegant two-story home seamlessly

    Agent Photo

    Jamil C. Winston (Jay)

    COLDWELL BANKER REALTY

    (321) 273-8188

    1711 Amsel Falls Park Terrace, Winter Garden, FL 34787
  • /16

    $2,715 Per Month

    • 3 Beds
    • 2 Baths
    • 2,057 Sq Ft
    • House for Rent

    1052 Sadie Ln, Winter Garden, FL 34787

    Please note, our homes are available on a first-come, first-serve basis and are not reserved until the holding fee agreement is signed and the holding fee is paid by the primary applicant.Coming soon! This home is currently being enjoyed by another resident but will be available soon. Please respect their privacy and do not disturb. You can complete the application process and reserve

    (689) 225-3657

    1052 Sadie Ln, Winter Garden, FL 34787
  • /36

    $567,990

    Sold Apr 14, 2026

    13169 Calming Breeze Way, Winter Garden, FL 34787

    • 3 Beds
    • 2.5 Baths
    • 2,078 Sq Ft
    • Built 2026

    Move in Ready Sold Summary

    • 4% Above List Price
    • $273/SF
    • 19 Days On Market

    Current Estimated Value $546,513

    Dream Finders Homes Serenade at Ovation - Bungalows

    13169 Calming Breeze Way, Winter Garden, FL 34787
    • /2

      Est $1,255,337

      Not Listed For Sale

      240 Stanton Estates Cir, Winter Garden, FL 34787

      • 4 Beds
      • 4 Baths
      • 3,170 Sq Ft
      • Built 2019
      240 Stanton Estates Cir, Winter Garden, FL 34787

      Last Sold Summary

      • 4 Days On Market

  • /43

    $525,000

    $10K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,197 Sq Ft

    14075 Lochend Way, Winter Garden, FL 34787

    Gorgeous, pristine and clean, four-bedroom, three-bath, like-new townhome, is approximately 20 minutes to the Disney area and approximately 35 minutes to Universal and on a prime corner lot in the desirable West Haven Ovation community of Winter Garden. Built by Toll Brothers, this nearly new townhome offers an opportunity to move in now so why wait to build! This two-story townhome features an

    Agent Photo

    Wendy Fischer

    PREMIER SOTHEBYS INT'L REALTY

    (321) 425-7974

    14075 Lochend Way, Winter Garden, FL 34787
  • /5

    $1,295 Per Month

    • Studio
    • 1 Bath
    • 305 Sq Ft
    • House for Rent

    203 N Dillard St, Winter Garden, FL 34787

    Property Id: 1041843Cute STUDIO apartment with full size kitchen /private bath and all within one block of Downtown Winter Garden. (1) Dedicated on-site parking space. Close to Crooked Can Brewery, WG Farmers market, annual Parade route, houses of worship, grocery shopping, laundrette, and 429 expressway. Hardwood floors and tile in wet areas. Shower-no tub. Like new refrigerator,

    (689) 407-6543

    203 N Dillard St, Winter Garden, FL 34787
  • /40

    $780,000

    Sold Dec 26, 2025

    12886 Harvest Rain Ave, Winter Garden, FL 34787

    • 5 Beds
    • 4.5 Baths
    • 3,101 Sq Ft
    • Built 2025

    Move in Ready Sold Summary

    • $252/SF
    • 62 Days On Market

    Current Estimated Value $778,000

    Taylor Morrison Harvest at Ovation

    12886 Harvest Rain Ave, Winter Garden, FL 34787
    • /2

      Est $843,283

      Not Listed For Sale

      13032 Sunrise Harvest Dr, Winter Garden, FL 34787

      • 5 Beds
      • 4 Baths
      • 3,432 Sq Ft
      • Built 2024
      13032 Sunrise Harvest Dr, Winter Garden, FL 34787

      Last Sold Summary

      • 286 Days On Market

  • /65

    $829,000

    Pending
    • 7 Beds
    • 4 Baths
    • 4,612 Sq Ft

    15232 Firelight Dr, Winter Garden, FL 34787

    Virtually Staged. FIRST TIME ON THE MARKET SINCE NEW! Located within the beautiful gated community of Belle Meade in Winter Garden, this exceptional 7-bedroom, 4-bathroom home offers the perfect combination of space, comfort, and lifestyle in one of Central Florida’s most sought-after locations. Freshly painted throughout and featuring a brand-new roof, this move-in ready residence provides peace

    Agent Photo

    Rodney Melendez

    CORCORAN PREMIER REALTY

    (689) 329-3494

    15232 Firelight Dr, Winter Garden, FL 34787
  • /14

    $2,715 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,857 Sq Ft
    • House for Rent

    1725 Portcastle Cir, Winter Garden, FL 34787

    Please note, our homes are available on a first-come, first-serve basis and are not reserved until the holding fee agreement is signed and the holding fee is paid by the primary applicant.This home is priced to rent and won't be around for long. Apply now, while we make this home ready for you, or call to arrange a meeting with your local Progress Residential leasing specialist

    (689) 225-3162

    1725 Portcastle Cir, Winter Garden, FL 34787
  • /2

    $510,000

    Sold Oct 31, 2025

    706 Grandhaven Way, Winter Garden, FL 34787

    • 4 Beds
    • 3 Baths
    • 1,904 Sq Ft
    • Built 2010

    Last Sold Summary

    • 5% Below List Price
    • $268/SF
    • 37 Days On Market

    Current Estimated Value $513,467

    Last Listing Agent Amy Moline EXP REALTY LLC

    706 Grandhaven Way, Winter Garden, FL 34787
    • /2

      Est $436,131

      Not Listed For Sale

      13406 Princess St, Winter Garden, FL 34787

      • 2 Beds
      • 2 Baths
      • 1,579 Sq Ft
      • Built 2024
      13406 Princess St, Winter Garden, FL 34787

      Last Sold Summary

      • 348 Days On Market

  • /3

    $2,997,000

    $3M PRICE DROP
    • Land
    • 9.64 Acres
    • $310,892 per Acre

    17902 Seidner Rd, Winter Garden, FL 34787

    Probably the finest site for a huge estate home in Orange County! No need to move almost an hour away to Montverde just to find enough land to build your private estate or Equestrian estate when this gem is minutes to Windermere and everywhere you want to be. This highly sought after 10 acre property in the Lake Avalon rural settlement, is a declining citrus grove and sits on the highest

    Agent Photo

    Jessica McKinney

    FLORIDA REALTY EXCHANGE LLC

    (321) 490-3947

    17902 Seidner Rd, Winter Garden, FL 34787
  • /9

    $2,795 Per Month

    • 3 Beds
    • 2 Baths
    • House for Rent

    238 N Main St, Winter Garden, FL 34787

    Property Id: 2479973HEART OF DOWTOWN WINTER GARDEN **** A LITTLE GEM MERELY A BLOCK TO HISTORIC DOWNTOWN WINTER GARDEN----SERIOUSLY! WALK HOME FROM DINNER OR A NIGHT OF DANCING OR SOCIALIZING!!!--- FRESH OWNER REDO WITH DISCERNING DESIGN CHOICES ON THIS SOLID & ADORABLE CONCRETE BLOCK 3 BEDROOM/2 BATH CHARMER WITH FENCED YARD AND BARBECUE DECK. WITHIN STEPS TO DOWNTOWN PLANT STREET,

    (689) 407-5524

    238 N Main St, Winter Garden, FL 34787
  • /2

    $526,000

    Sold Oct 15, 2025

    13029 Tranquil Water Aly, Winter Garden, FL 34787

    • 3 Beds
    • 2.5 Baths
    • 1,836 Sq Ft
    • Built 2024

    Last Sold Summary

    • 2% Below List Price
    • $286/SF
    • 0 Days On Market

    Current Estimated Value $533,025

    Last Listing Agent Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

    13029 Tranquil Water Aly, Winter Garden, FL 34787
    • /2

      Est $968,739

      Not Listed For Sale

      10091 Austrina Oak Loop, Winter Garden, FL 34787

      • 6 Beds
      • 4.5 Baths
      • 4,475 Sq Ft
      • Built 2019
      10091 Austrina Oak Loop, Winter Garden, FL 34787

      Last Sold Summary

      • 134 Days On Market

  • /30

    $320,000

    • 2 Beds
    • 2 Baths
    • 1,434 Sq Ft

    Unlisted Address

    Welcome to the 4-Star rated Grove Resort & Spa Orlando! This high floor, Cypress model corner unit offers a spacious, split bedroom, open layout with over 1,400+ SF of living area. This model features an oversized Primary Suite with separate corner sitting area and guest bedroom features 2 queen size beds. This condo sleeps 8! Other features include a modern interior with solid wood cabinets and

    Agent Photo

    Consuelo Vilar

    WELCOME HOME REALTY GROUP LLC

    (321) 463-3420

    Unlisted Address
  • /20

    $5,454

    Total Monthly Price

    • 2 Beds
    • 2 Baths
    • 11,840 Sq Ft
    • Condo for Rent

    1231 E Plant St Unit SI ID1511056P, Winter Garden, FL 34787

    The advertised rate of $5,454/month is the lowest available price, based on a 30 day(s) stay with a move-in date of July 17, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

    (321) 510-4328

    1231 E Plant St Unit SI ID1511056P, Winter Garden, FL 34787
  • /2

    $555,000

    Sold Jun 12, 2026

    723 Sunburst Cove Ln, Winter Garden, FL 34787

    • 4 Beds
    • 2.5 Baths
    • 2,189 Sq Ft
    • Built 2000

    Last Sold Summary

    • $254/SF
    • 22 Days On Market

    Current Estimated Value $550,782

    Last Listing Agent Lois Cox WATSON REALTY CORP

    723 Sunburst Cove Ln, Winter Garden, FL 34787
    • /2

      Not Listed For Sale

      13012 Serene Glade Rd, Winter Garden, FL 34787

      • 3 Beds
      • 3 Baths
      • 2,083 Sq Ft
      • Built 2024
      13012 Serene Glade Rd, Winter Garden, FL 34787

      Last Sold Summary

      • 0 Days On Market

  • /50

    $875,000

    • Land
    • 4.94 Acres
    • $177,126 per Acre

    16838 Old Highway 50, Winter Garden, FL 34787

    Rare opportunity to own 5 acres of highly versatile land near Orlando, Clermont, and Winter Garden, located at 16838 Old Highway 50 in one of Lake County’s rapidly growing corridors. With 300 feet of frontage and already divided into three parcels, this property features agricultural, commercial, and residential zoning, creating endless possibilities for developers, builders, investors, or anyone

    Agent Photo

    Thomas Nickley

    KELLER WILLIAMS REALTY AT THE PARKS

    (321) 353-6756

    16838 Old Highway 50, Winter Garden, FL 34787
  • /15

    $2,650 Per Month

    • 3 Beds
    • 2 Baths
    • 1,971 Sq Ft
    • House for Rent

    1958 Pantheon Dr, 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 3-bedroom, 2-bathroom rental home in Winter Garden, FL, has a lot to offer; does it check all your

    (321) 587-0894

    1958 Pantheon Dr, Winter Garden, FL 34787
  • /2

    $1,218,750

    Sold Jan 06, 2026

    7833 Freestyle Ln, Winter Garden, FL 34787

    • 4 Beds
    • 3 Baths
    • 3,364 Sq Ft
    • Built 2018

    Last Sold Summary

    • 13% Below List Price
    • $362/SF
    • 71 Days On Market

    Current Estimated Value $1,214,565

    Last Listing Agent Dennesha Leachman GLOBAL SAPPHIRE REALTY LLC

    7833 Freestyle Ln, Winter Garden, FL 34787
    • /2

      Est $529,180

      Not Listed For Sale

      16992 Hamlin Oasis Loop, Winter Garden, FL 34787

      • 3 Beds
      • 2.5 Baths
      • 1,836 Sq Ft
      • Built 2025
      16992 Hamlin Oasis Loop, Winter Garden, FL 34787

      Last Sold Summary

      • 0 Days On Market

  • /60

    $799,000

    Pending
    • 4 Beds
    • 3.5 Baths
    • 3,149 Sq Ft

    10693 Petrillo Way, Winter Garden, FL 34787

    Under contract-accepting backup offers. Located in Winding Bay in Winter Garden, this move-in ready home for sale near Walt Disney World offers a rare combination of privacy, functionality, and luxury. Positioned on one of the best CONSERVATION LOTS in the community with NO REAR NEIGHBORS, this home delivers peaceful green space views and a truly private setting that’s increasingly hard to find.

    Agent Photo

    Alexis Bress

    EXP REALTY LLC

    (689) 334-2634

    10693 Petrillo Way, Winter Garden, FL 34787
  • /14

    $2,545 Per Month

    • 3 Beds
    • 2 Baths
    • 1,477 Sq Ft
    • House for Rent

    397 Regal Downs Cir, Winter Garden, FL 34787

    Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare® professional maintenance. Your estimated total monthly payment is $2689.90. That covers your base rent, $2545.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

    (689) 407-2405

    397 Regal Downs Cir, Winter Garden, FL 34787
  • /27

    $639,990

    Sold Mar 25, 2026

    12445 Clear Sapphire Dr, Winter Garden, FL 34787

    • 4 Beds
    • 3.5 Baths
    • 2,693 Sq Ft
    • Built 2026

    Move in Ready Sold Summary

    • 1% Below List Price
    • $238/SF
    • 6 Days On Market

    K. Hovnanian Homes Osprey Ranch

    12445 Clear Sapphire Dr, Winter Garden, FL 34787
    • /2

      Est $671,489

      Not Listed For Sale

      16436 Parable Way, Winter Garden, FL 34787

      • 4 Beds
      • 4 Baths
      • 2,722 Sq Ft
      • Built 2023
      16436 Parable Way, Winter Garden, FL 34787

      Last Sold Summary

      • 7 Days On Market

  • /48

    $529,999

    Pending
    • 4 Beds
    • 3.5 Baths
    • 2,474 Sq Ft

    16230 Carraway Bay Aly, Winter Garden, FL 34787

    Welcome to 16230 Carraway Bay Alley, a beautifully maintained home located in one of Winter Garden's most desirable communities. This move-in ready residence features a functional open-concept layout with spacious living areas, abundant natural light, and modern finishes throughout. The kitchen overlooks the main living and dining areas, creating an ideal space for both everyday living and

    Agent Photo

    Tiffany Matics-Machusak

    Watson Realty Corporation

    (321) 471-0124

    16230 Carraway Bay Aly, Winter Garden, FL 34787
  • /15

    $3,120 Per Month

    • 4 Beds
    • 3 Baths
    • 2,022 Sq Ft
    • House for Rent

    988 Glenview 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, 3-bathroom rental home in Winter Garden, FL, has a lot to offer; does it check all your

    (321) 346-5112

    988 Glenview Cir, Winter Garden, FL 34787
  • /2

    $275,000

    Sold Sep 15, 2025

    1300 Eastern Pecan Place Unit 104, Winter Garden, FL 34787

    • 3 Beds
    • 2 Baths
    • 1,340 Sq Ft
    • Built 2005

    Last Sold Summary

    • 8% Below List Price
    • $205/SF
    • 90 Days On Market

    Current Estimated Value $276,244

    Last Listing Agent Todd Schroth EXP REALTY LLC

    1300 Eastern Pecan Place Unit 104, Winter Garden, FL 34787
    • /2

      Est $601,025

      Not Listed For Sale

      2224 Romanum Dr, Winter Garden, FL 34787

      • 4 Beds
      • 4 Baths
      • 2,562 Sq Ft
      • Built 2014
      2224 Romanum Dr, Winter Garden, FL 34787

      Last Sold Summary

      • 63 Days On Market

Showing Results 81 - 120, Page 3 of 18

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