37,933

Winter Garden, FL Homes

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  • /54

    $295,000

    • 2 Beds
    • 2 Baths
    • 1,265 Sq Ft

    14501 Grove Resort Ave Unit 2703, Winter Garden, FL 34787

    NEWEST TOWER | TOP FLOOR | FOUNTAIN VIEW This is resort-style living at its absolute finest. This Fountain View Palm Unit in Tower 2 — the newest and most beautifully appointed tower in the community — offers the perfect blend of luxury, lifestyle, and income-generating opportunity. Step into a world-class destination that rivals the finest resorts anywhere in the world. With stunning superior

    Agent Photo

    Bill Traback

    MBI REALTY LLC

    14501 Grove Resort Ave Unit 2703, Winter Garden, FL 34787
  • /32

    $2,995 Per Month

    • 4 Beds
    • 2 Baths
    • 2,459 Sq Ft
    • House for Rent

    273 Avalon Rd, Winter Garden, FL 34787

    Welcome home to 273 Avalon Road, a stunningly beautiful 4 Bedroom, 2 Bath home with 2,459 sqft of living space on almost a 1/2 acre lot !!! Just minutes from Down Town Winter Garden, this is a one of a kind property that was remodeled giving a modern flair to a farmhouse style property. The kitchen has a large center Island, with granite counter tops, stainless steel appliances, custom cabinets,

    Sarah Gholami THE FLORIDA PROPERTY SHOP SALE

    273 Avalon Rd, Winter Garden, FL 34787
  • /2

    $540,000

    Sold Dec 02, 2025

    14342 White Moss Way, Winter Garden, FL 34787

    • 3 Beds
    • 2.5 Baths
    • 2,368 Sq Ft
    • Built 2015

    Last Sold Summary

    • 9% Below List Price
    • $228/SF
    • 81 Days On Market

    Current Estimated Value $536,311

    Last Listing Agent Silvia Kinkela SERHANT

    14342 White Moss Way, Winter Garden, FL 34787
    • /2

      Est $586,540

      Not Listed For Sale

      16013 Tollington Aly, Winter Garden, FL 34787

      • 4 Beds
      • 3.5 Baths
      • 2,807 Sq Ft
      • Built 2020
      16013 Tollington Aly, Winter Garden, FL 34787

      Last Sold Summary

      • 30 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

    16838 Old Highway 50, Winter Garden, FL 34787
  • /27

    $3,045

    Total Monthly Price

    • 3 Beds
    • 2 Baths
    • 1,280 Sq Ft
    • Condo for Rent

    14200 Avalon Rd Unit SI ID1244724P, Winter Garden, FL 34787

    The advertised rate of $3,045/month is the lowest available price, based on a 30 day(s) stay with a move-in date of October 21, 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

    14200 Avalon Rd Unit SI ID1244724P, Winter Garden, FL 34787
  • /2

    $584,000

    Sold Oct 06, 2025

    15249 Purple Martin St, Winter Garden, FL 34787

    • 3 Beds
    • 2.5 Baths
    • 2,186 Sq Ft
    • Built 2017

    Last Sold Summary

    • 3% Below List Price
    • $267/SF
    • 29 Days On Market

    Current Estimated Value $565,722

    Last Listing Agent Diana Basch Connery MS LAND & BUILDING LLC

    15249 Purple Martin St, Winter Garden, FL 34787
    • /2

      Est $773,756

      Not Listed For Sale

      4789 Terrace Bluff St, Winter Garden, FL 34787

      • 4 Beds
      • 4.5 Baths
      • 3,002 Sq Ft
      • Built 2020
      4789 Terrace Bluff St, Winter Garden, FL 34787

      Last Sold Summary

      • 112 Days On Market

  • /23

    $594,000

    $6K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 2,695 Sq Ft

    15043 Pigeon Plum Ln, Winter Garden, FL 34787

    Welcome to this beautifully maintained 4-bedroom, 3.5-bath home located in the desirable Winter Garden area. This spacious residence offers a well-designed floor plan with generous living areas, ideal for both everyday living and entertaining. The home features a bright and open layout with abundant natural light, a large kitchen with ample cabinetry and counter space, and a seamless flow into

    Agent Photo

    Ceila Morales

    EXP REALTY LLC

    15043 Pigeon Plum Ln, Winter Garden, FL 34787
  • /32

    $2,650 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,568 Sq Ft
    • Townhouse for Rent

    12007 Holystone St, Winter Garden, FL 34787

    BEAUTIFUL TOWMHOUSE, available to rent in WATERLEIGH, Located in the Winter Garden area's 3-bedroom, 2.5-bath townhouse in Waterleigh, Winter Garden! This home features a modern kitchen with 42-inch cabinets, granite countertops, stainless-steel appliances, and a convenient second-floor laundry room. Enjoy access to resort-style community amenities, including a pool with pond views, dog park, and

    Erwin Vargas MR VARGAS PROPERTY MANAGEMENT LLC

    12007 Holystone St, Winter Garden, FL 34787
  • /2

    $1,700,000

    Sold Jan 21, 2026

    9072 Bradleigh Dr, Winter Garden, FL 34787

    • 5 Beds
    • 4.5 Baths
    • 3,750 Sq Ft
    • Built 2019

    Last Sold Summary

    • 10% Below List Price
    • $453/SF
    • 74 Days On Market

    Current Estimated Value $1,688,259

    Last Listing Agent Ronald Ziolkowski RE/MAX PRIME PROPERTIES

    9072 Bradleigh Dr, Winter Garden, FL 34787
    • /2

      Est $309,836

      Not Listed For Sale

      1552 Broken Oak Dr Unit B, Winter Garden, FL 34787

      • 3 Beds
      • 2.5 Baths
      • 1,544 Sq Ft
      • Built 2007
      1552 Broken Oak Dr Unit B, Winter Garden, FL 34787

      Last Sold Summary

      • 115 Days On Market

  • /56

    $314,900

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

    14501 Grove Resort Ave Unit 2536, Winter Garden, FL 34787

    Owner Motivated – Largest 2-Bedroom Floor Plan at The Grove Resort OrlandoThis exceptional 5th-floor condo offers rare convenience with high ceilings, spacious bedrooms, and immediate access to parking. The primary suite includes a generous sitting area, while the second bedroom features two full beds — an ideal layout for families, groups, or high-occupancy rentals.Positioned on the

    Agent Photo

    Bill Traback

    MBI REALTY LLC

    14501 Grove Resort Ave Unit 2536, Winter Garden, FL 34787
  • /18

    $3,600 Per Month

    • 4 Beds
    • 3.5 Baths
    • 2,474 Sq Ft
    • House for Rent

    11170 Hollow Bay Dr, Winter Garden, FL 34787

    Property Id: 2748630 Beautiful 4-bedroom, 3-bath home located in the highly desirable Waterleigh community in Winter Garden. This spacious home features an open-concept floor plan with a modern kitchen, stainless steel appliances, quartz countertops, and a large island perfect for entertaining. The primary suite offers a generous walk-in closet and a luxurious en-suite bathroom. Enjoy a

    11170 Hollow Bay Dr, Winter Garden, FL 34787
  • /2

    $390,000

    Sold Aug 18, 2025

    15574 Murcott Blossom Blvd, Winter Garden, FL 34787

    • 3 Beds
    • 2.5 Baths
    • 1,868 Sq Ft
    • Built 2017

    Last Sold Summary

    • 13% Below List Price
    • $209/SF
    • 155 Days On Market

    Current Estimated Value $394,315

    Last Listing Agent Erica Diaz HOMEVEST REALTY

    15574 Murcott Blossom Blvd, Winter Garden, FL 34787
    • /2

      Est $416,917

      Not Listed For Sale

      15580 Blackbead St, Winter Garden, FL 34787

      • 3 Beds
      • 2.5 Baths
      • 1,710 Sq Ft
      • Built 2015
      15580 Blackbead St, Winter Garden, FL 34787

      Last Sold Summary

      • 103 Days On Market

  • /69

    $1,200,000

    Under Contract
    • 6 Beds
    • 4 Baths
    • 4,247 Sq Ft

    1812 Lake Roberts Landing Dr, Winter Garden, FL 34787

    Under contract-accepting backup offers. Experience elevated living perfectly situated on a private conservation homesite with no rear neighbors in the gated community of Lake Roberts Landing in Winter Garden. This fully renovated luxury pool home offers an exceptional blend of privacy, elegance, and convenience in the heart of Winter Garden. Spanning over 4,200 square feet, this move-in-ready

    Agent Photo

    Alexis Jacobsen

    EXP REALTY LLC

    1812 Lake Roberts Landing Dr, Winter Garden, FL 34787
  • /12

    $3,500 Per Month

    • 4 Beds
    • 4.5 Baths
    • 2,667 Sq Ft
    • House for Rent

    15026 Summer Harvest St, Winter Garden, FL 34787

    Exceptional opportunity in Winter Garden for rent. This stunning 2024 home offers 4 bedrooms, 3.5 bathrooms, With over $60,000 in completed upgrades, with a comeplete 1 bedroom and 1 bathroom, kitchenente studio, completely independent. This property delivers exceptional value and a truly move-in-ready experience. Ideally located just minutes from Disney, Flamingo Crossings, Hamlin Town Center,

    Chanel Munoz MOSAIC PARTNERS GROUP

    15026 Summer Harvest St, Winter Garden, FL 34787
  • /2

    $1,700,000

    Sold Sep 11, 2025

    557 Lake Cove Pointe Cir, Winter Garden, FL 34787

    • 5 Beds
    • 4.5 Baths
    • 4,176 Sq Ft
    • Built 2015

    Last Sold Summary

    • 6% Below List Price
    • $407/SF
    • 90 Days On Market

    Current Estimated Value $1,642,864

    Last Listing Agent Erica Diaz HOMEVEST REALTY

    557 Lake Cove Pointe Cir, Winter Garden, FL 34787
    • /2

      Est $403,601

      Not Listed For Sale

      15030 Book Club Rd, Winter Garden, FL 34787

      • 3 Beds
      • 2.5 Baths
      • 1,727 Sq Ft
      • Built 2020
      15030 Book Club Rd, Winter Garden, FL 34787

      Last Sold Summary

      • 22 Days On Market

  • /62

    $434,900

    Open Sun 2PM - 5PM $30K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,725 Sq Ft

    8113 Red Stopper Ln, Winter Garden, FL 34787

    Perfectly positioned in the heartbeat of Horizons West, just 3 miles from Disney’s Magic Kingdom. This impeccably maintained 3-bedroom, 2.5-bath townhome in the highly sought-after Summerlake community offers the rare blend of style, efficiency, and everyday magic - including a spacious two-car garage attached to the largest oversized patio in Summerlake! Enjoy the nightly Disney fireworks and

    Agent Photo

    Kassandra Lopez

    EXP REALTY LLC

    8113 Red Stopper Ln, Winter Garden, FL 34787
  • /24

    $2,644

    Total Monthly Price

    • 3 Beds
    • 2 Baths
    • 1,722 Sq Ft
    • Condo for Rent

    14200 Avalon Rd Unit SI ID1244728P, Winter Garden, FL 34787

    The advertised rate of $2,644/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 24, 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

    14200 Avalon Rd Unit SI ID1244728P, Winter Garden, FL 34787
  • /5

    $432,590

    Sold Dec 24, 2025

    16264 Merry Aly, Winter Garden, FL 34787

    • 3 Beds
    • 2.5 Baths
    • 1,683 Sq Ft
    • Built 2025

    Move in Ready Sold Summary

    • $257/SF
    • 11 Days On Market

    Current Estimated Value $420,997

    Pulte Homes Silverleaf Oaks - Townhome

    16264 Merry Aly, Winter Garden, FL 34787
    • /2

      Est $565,484

      Not Listed For Sale

      9971 Beach Port Dr, Winter Garden, FL 34787

      • 4 Beds
      • 3.5 Baths
      • 2,477 Sq Ft
      • Built 2019
      9971 Beach Port Dr, Winter Garden, FL 34787

      Last Sold Summary

      • 30 Days On Market

  • /52

    $1,495,000

    New Construction Open Sun 1PM - 4PM
    • 4 Beds
    • 4.5 Baths
    • 3,015 Sq Ft

    412 N Boyd St, Winter Garden, FL 34787

    Discover elevated living and the Winter Garden lifestyle in downtown's newest custom residence! Ideally positioned off the shores of Lake Apopka and within the beloved golf cart district, this exceptional home offers effortless access to Plant Street’s charming shops, restaurants, Farmers Market, Brewery and West Orange Trail. Thoughtfully designed by locals with a deep appreciation for the

    Agent Photo

    Karla Ryan

    WATSON REALTY CORP

    412 N Boyd St, Winter Garden, FL 34787
  • /57

    $5,895 Per Month

    • 5 Beds
    • 4.5 Baths
    • 4,199 Sq Ft
    • House for Rent

    8222 Topsail Place, Winter Garden, FL 34787

    STUNNING, well-maintained Executive estate home with everything you've been looking for! This gorgeous GARDENIA model by TOLL BROTHERS features 4200 square feet of living space with AMAZING VIEWS of a tranquil pond in the front, retention space in back in the desirable LAKESHORE community in HORIZON WEST, providing the perfect ONE OF A KIND idyllic space you've been looking for! You will enjoy

    Jonathan Jankowski CHASTAIN REAL ESTATE COMPANY LLC

    8222 Topsail Place, Winter Garden, FL 34787
  • /2

    $620,000

    Sold Jul 15, 2026

    8955 Lakeshore Pointe Dr, Winter Garden, FL 34787

    • 4 Beds
    • 3.5 Baths
    • 2,539 Sq Ft
    • Built 2018

    Last Sold Summary

    • 5% Below List Price
    • $244/SF
    • 304 Days On Market

    Current Estimated Value $639,073

    Last Listing Agent Ana Paula Teixeira ANA TEIXEIRA REALTY

    8955 Lakeshore Pointe Dr, Winter Garden, FL 34787
    • /2

      Est $584,189

      Not Listed For Sale

      15500 Fountain Cove Ct, Winter Garden, FL 34787

      • 4 Beds
      • 3 Baths
      • 2,117 Sq Ft
      • Built 2017
      15500 Fountain Cove Ct, Winter Garden, FL 34787

      Last Sold Summary

      • 37 Days On Market

  • /10

    $454,990

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 1,817 Sq Ft

    Sandhill Plan at Waterleigh - Townhomes, Winter Garden, FL 34787

    Welcome to your charming townhome located at Waterleigh, in Winter Garden, Florida. The Sandhill townhome is where comfort, style, and modern convenience come together to create the perfect haven for you and your family. This delightful residence features 1,817 square feet, three spacious bedrooms, 2 1/2 baths, a convenient one-car garage, ample loft space, and cutting-edge smart home technology.

    D.R. Horton Builder
    10482 Atwater Bay Dr Unit 36202693, Winter Garden, FL 34787
  • /15

    $1,500 Per Month

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

    396 Regal Downs Cir, Winter Garden, FL 34787

    Property Id: 2771176 Welcome to your dream home in Winter Garden, FL! This charming 3 bed, 2 bath single-family property offers modern amenities including a dishwasher, washer/dryer in unit, and security cameras. Enjoy the fenced yard and garage. Pets allowed. Rent includes utilities. Don't miss out on this gem! Reach out to: 813-38five-1652

    396 Regal Downs Cir, Winter Garden, FL 34787
  • /2

    $650,000

    Sold Feb 27, 2026

    14525 Sabal Crest Way, Winter Garden, FL 34787

    • 4 Beds
    • 3 Baths
    • 2,527 Sq Ft
    • Built 2017

    Last Sold Summary

    • $257/SF
    • 5 Days On Market

    Current Estimated Value $645,327

    Last Listing Agent Fran Zvaigzne COLDWELL BANKER REALTY

    14525 Sabal Crest Way, Winter Garden, FL 34787
    • /31

      Est $455,534

      Not Listed For Sale

      15416 Blackbead St, Winter Garden, FL 34787

      • 3 Beds
      • 2.5 Baths
      • 1,853 Sq Ft
      • Built 2018
      15416 Blackbead St, Winter Garden, FL 34787

      Last Sold Summary

      • 191 Days On Market

  • /3

    $704,990

    New Construction
    • 4 Beds
    • 2.5 Baths
    • 2,752 Sq Ft

    Tidewater Plan at Hamlin Meadows - 60' Homesites, Winter Garden, FL

    The Tidewater floorplan offers a versatile and spacious one-story layout, featuring 4 bedrooms and 2.5 bathrooms. Spanning 2,752 sq. ft., this home includes a large two-car garage for ample storage and convenience. The first floor boasts an inviting great room connected to an open kitchen and dining area, perfect for entertaining. The owner’s suite provides a private retreat with a generous

    Dream Finders Homes Builder
    0 Hamlin Meadows St Unit 39127938, Winter Garden, FL
  • /38

    $3,965 Per Month

    • 3 Beds
    • 2 Baths
    • 2,210 Sq Ft
    • House for Rent

    720 Parkmont Place, Winter Garden, FL 34787

    Welcome to 720 Parkmont Place, a charming 3-bedroom, 2-bathroom, single-story home located in the desirable Covington Chase community, nestled along the West Orange Trail in the heart of Winter Garden. Fully furnished and move-in ready, this home offers generous living space and well-sized rooms throughout.Upon entering, you'll find French doors leading to a flexible bonus room currently set

    Anthony O'Reilly Brookes WINTER GARDEN REAL ESTATE

    720 Parkmont Place, Winter Garden, FL 34787
  • /2

    $875,000

    Sold May 06, 2026

    16554 Raven Rock Place, Winter Garden, FL 34787

    • 4 Beds
    • 3 Baths
    • 3,032 Sq Ft
    • Built 2015

    Last Sold Summary

    • $289/SF
    • 16 Days On Market

    Current Estimated Value $880,516

    Last Listing Agent Andrew Philippone INDEPENDENCE REALTY GROUP LLC

    16554 Raven Rock Place, Winter Garden, FL 34787
    • /17

      Est $520,470

      Not Listed For Sale

      9014 Pinch Shot Dr, Winter Garden, FL 34787

      • 3 Beds
      • 2 Baths
      • 2,089 Sq Ft
      • Built 2018
      9014 Pinch Shot Dr, Winter Garden, FL 34787

      Last Sold Summary

      • 2 Days On Market

  • /61

    $760,900

    New Construction
    • 5 Beds
    • 4.5 Baths
    • 3,296+ Sq Ft

    Frost Plan at Northlake at Ovation, Winter Garden, FL 34787

    New Home by RockWell Homes, Now Selling! Discover the elegance and comfort of the Frost plan, a luxurious new home designed to meet all your needs. This stunning home features 5 bedrooms, 4.5 bathrooms, and a spacious layout that includes both a primary suite and a guest bedroom on the first floor, making it ideal for multi-generational living or hosting visitors. The Frost plan also boasts an

    RockWell Homes Builder
    17551 Lake Star Rd Unit 36901645, Winter Garden, FL 34787
  • /23

    $2,900 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,850 Sq Ft
    • House for Rent

    9137 Grand Is Way, Winter Garden, FL 34787

    Welcome home to this beautifully maintained 3-bedroom, 2.5-bath residence in the highly desirable Winter Garden area. Designed with both comfort and functionality in mind, this home features a bright, open-concept layout that seamlessly connects the living, dining, and kitchen spaces—perfect for everyday living and entertaining.Upstairs, you'll find a versatile loft/den that can easily

    9137 Grand Is Way, Winter Garden, FL 34787
  • /2

    $1,000,000

    Sold Aug 21, 2025

    15900 Citrus Knoll Dr, Winter Garden, FL 34787

    • 5 Beds
    • 3 Baths
    • 3,844 Sq Ft
    • Built 2015

    Last Sold Summary

    • 13% Below List Price
    • $260/SF
    • 48 Days On Market

    Current Estimated Value $1,002,644

    Last Listing Agent Ronald Ziolkowski RE/MAX PRIME PROPERTIES

    15900 Citrus Knoll Dr, Winter Garden, FL 34787
    • /2

      Est $566,305

      Not Listed For Sale

      9250 Cut Shot Dr, Winter Garden, FL 34787

      • 5 Beds
      • 3 Baths
      • 2,461 Sq Ft
      • Built 2018
      9250 Cut Shot Dr, Winter Garden, FL 34787

      Last Sold Summary

      • 144 Days On Market

Showing Results 241 - 280, Page 7 of 18

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