37,945

Winter Garden, FL Homes

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  • /45

    $550,000

    $124K PRICE DROP Under Contract
    • 3 Beds
    • 3.5 Baths
    • 2,571 Sq Ft

    15456 Gilligan Ct, Winter Garden, FL 34787

    Under contract-accepting backup offers. Disney fireworks views, single-story living, low HOA — just 3.9 miles from Disney. Welcome to Winding Bay in Winter Garden, where location, lifestyle, and long-term value come together in one beautifully maintained home. This pristine 3-bedroom, 3.5-bath residence with a flexible bonus room offers the perfect setup for everyday living, visiting guests,

    Agent Photo

    Loren Rosenthal

    NEXTHOME CASA BELLA ELITE

    15456 Gilligan Ct, Winter Garden, FL 34787
  • /18

    $2,550

    Total Monthly Price

    • 3 Beds
    • 2 Baths
    • 1,390 Sq Ft
    • House for Rent

    15333 Harrowgate Way, 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

    15333 Harrowgate Way, Winter Garden, FL 34787
  • /2

    $742,475

    Sold Jul 20, 2026

    Unlisted Address

    • 4 Beds
    • 3.5 Baths
    • 2,271 Sq Ft
    • Built 2026

    Last Sold Summary

    • $327/SF

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

    Unlisted Address
    • /2

      Est $549,866

      Not Listed For Sale

      1569 Victoria Way, Winter Garden, FL 34787

      • 4 Beds
      • 2 Baths
      • 2,258 Sq Ft
      • Built 1997
      1569 Victoria Way, Winter Garden, FL 34787

      Last Sold Summary

      • 167 Days On Market

  • /51

    $190,000

    • 2 Beds
    • 2 Baths
    • 1,375 Sq Ft

    14501 Grove Resort Ave Unit 3231, Winter Garden, FL 34787

    TOWER 3 LOCATION CLOSEST TO THE WATERPARK! Exceptional opportunity to own at The Grove Resort & Water Park, one of Central Florida’s premier vacation ownership destinations just minutes from Walt Disney World. This condo is a beautifully furnished Birch Plan residence offering a comfortable, turnkey layout designed for personal enjoyment and income-producing vacation rental use. The open living

    Agent Photo

    Bill Traback

    MBI REALTY LLC

    14501 Grove Resort Ave Unit 3231, Winter Garden, FL 34787
  • /16

    $2,700 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 lease is signed by all applicants and security deposits are collected.Interested in this home? You clearly have exceptional taste. This charming 3-bedroom, 2.0-bathroom home is not only pet-friendly, but also equipped with smart home features to make everyday life more convenient and

    1052 Sadie Ln, Winter Garden, FL 34787
  • /2

    $555,960

    Sold Sep 19, 2025

    13520 Autumn Harvest Ave, Winter Garden, FL 34787

    • 3 Beds
    • 3 Baths
    • 2,198 Sq Ft
    • Built 2025

    Last Sold Summary

    • $253/SF

    Current Estimated Value $546,338

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

    13520 Autumn Harvest Ave, Winter Garden, FL 34787
    • /2

      Est $687,016

      Not Listed For Sale

      40 W Smith St, Winter Garden, FL 34787

      • 3 Beds
      • 2 Baths
      • 2,225 Sq Ft
      • Built 1923
      40 W Smith St, Winter Garden, FL 34787

      Last Sold Summary

      • 8 Days On Market

  • /25

    $325,000

    $44K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,265 Sq Ft

    14501 Grove Resort Ave Unit 3205, Winter Garden, FL 34787

    Luxury vacation rental within The Grove Resort and Spa. Beautifully furnished with modern furniture and fixtures that make for a one-of-a-kind vacation property, this fully furnished 2-bedroom, 2-bath unit can sleep up to 8 people (room with1 king bed, room with 2 full beds and queen sleeper sofa) and has a gourmet kitchen with stainless steel appliances and quartz counters. The Grove Resort and

    Agent Photo

    Jamie Ampel

    ALL SELLERS & BUYERS REALTY INC

    14501 Grove Resort Ave Unit 3205, Winter Garden, FL 34787
  • /20

    $2,931

    Total Monthly Price

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

    14200 Avalon Rd Unit SI ID1244709P, Winter Garden, FL 34787

    The advertised rate of $2,931/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 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 ID1244709P, Winter Garden, FL 34787
  • /2

    $750,000

    Sold May 21, 2026

    13001 Harvest Rain Ave, Winter Garden, FL 34787

    • 4 Beds
    • 3.5 Baths
    • 2,858 Sq Ft
    • Built 2026

    Last Sold Summary

    • $262/SF
    • 14 Days On Market

    Last Listing Agent Michelle Campbell TAYLOR MORRISON REALTY OF FLORIDA INC

    13001 Harvest Rain Ave, Winter Garden, FL 34787
    • /2

      Est $485,409

      Not Listed For Sale

      206 N Highland Ave, Winter Garden, FL 34787

      • 4 Beds
      • 1 Bath
      • 1,738 Sq Ft
      • Built 1925
      206 N Highland Ave, Winter Garden, FL 34787

      Last Sold Summary

      • 32 Days On Market

  • /48

    $304,000

    $35K PRICE INCREASE
    • 2 Beds
    • 2 Baths
    • 1,265 Sq Ft

    14501 Grove Resort Ave Unit 1105, Winter Garden, FL 34787

    Skip the Elevator. Start the Vacation.First-floor units in Tower 1 at The Grove Resort don't come up often — and when they do, they don't last. Guests love them. No elevator wait, instant access to the pools and waterpark, and the kind of easy resort flow that earns five-star reviews and repeat bookings.This fully furnished 2-bedroom split-plan features soaring ceilings and generous room

    Agent Photo

    Bill Traback

    MBI REALTY LLC

    14501 Grove Resort Ave Unit 1105, Winter Garden, FL 34787
  • /20

    $3,000 Per Month

    • 3 Beds
    • 2.5 Baths
    • House for Rent

    15120 Sunrise Grove Ct, Winter Garden, FL 34787

    Property Id: 950390 Unfinished home- looking for a long term rental The home is located in the Winter Garden area, about 10 minutes from the Winter Garden Village; which has Target, Panera Bread, Starbucks, Best Buy, Lowes etc. It is also near many elementary schools since it is in a newer neighborhood. And the house itself is on the end with a larger area of space. The

    15120 Sunrise Grove Ct, Winter Garden, FL 34787
  • /2

    $594,948

    Sold Nov 18, 2025

    12749 Harvest Rain Ave, Winter Garden, FL 34787

    • 4 Beds
    • 3.5 Baths
    • 2,441 Sq Ft
    • Built 2025

    Last Sold Summary

    • $244/SF

    Current Estimated Value $637,000

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

    12749 Harvest Rain Ave, Winter Garden, FL 34787
    • /2

      Est $576,840

      Not Listed For Sale

      16324 Brisk Breeze Aly, Winter Garden, FL 34787

      • 4 Beds
      • 3.5 Baths
      • 2,477 Sq Ft
      • Built 2018
      16324 Brisk Breeze Aly, Winter Garden, FL 34787

      Last Sold Summary

      • 4 Days On Market

  • /48

    $325,890

    • 2 Beds
    • 2 Baths
    • 1,375 Sq Ft

    14501 Grove Resort Ave Unit 1220, Winter Garden, FL 34787

    The Birch — 2 Bed / 2 Bath Condo-HotelThe only floorplan at The Grove with two true primary suites.Most two-bedroom resort units give you a primary suite and a noticeably smaller second room. Not the Birch. Both bedrooms are generously sized, both feature private en suite baths, and both feel like the primary suite — making this the ideal choice for two couples traveling together,

    Agent Photo

    Bill Traback

    MBI REALTY LLC

    14501 Grove Resort Ave Unit 1220, Winter Garden, FL 34787
  • /28

    $2,750

    Total Monthly Price

    • 3 Beds
    • 2 Baths
    • 1,682 Sq Ft
    • House for Rent

    16279 Taliesin St, Winter Garden, FL 34787

    Hawksmoor is nestled within Winter Garden’s beautiful Horizon West area. The unique architectural details and mix of modern, craftsman and prairie-inspired designs add to the unique streetscapes of this community. Just minutes away from historic downtown Winter Garden, the magic of Disney and other world-class theme parks, a wide-variety of shopping, dining, and entertainment, plus, convenient

    16279 Taliesin St, Winter Garden, FL 34787
  • /2

    $645,000

    Sold Sep 11, 2025

    14664 Spotted Sandpiper Blvd, Winter Garden, FL 34787

    • 4 Beds
    • 2.5 Baths
    • 2,701 Sq Ft
    • Built 2014

    Last Sold Summary

    • 3% Below List Price
    • $239/SF
    • 0 Days On Market

    Current Estimated Value $629,816

    Last Listing Agent Andreia Beraldo TALENT REALTY SOLUTIONS

    14664 Spotted Sandpiper Blvd, Winter Garden, FL 34787
    • /2

      Est $364,952

      Not Listed For Sale

      1356 Scarlet Oak Loop, Winter Garden, FL 34787

      • 3 Beds
      • 2.5 Baths
      • 1,701 Sq Ft
      • Built 2013
      1356 Scarlet Oak Loop, Winter Garden, FL 34787

      Last Sold Summary

      • 12 Days On Market

  • /42

    $530,000

    Under Contract
    • 3 Beds
    • 2.5 Baths
    • 2,195 Sq Ft

    7725 Purple Finch St, Winter Garden, FL 34787

    Under contract-accepting backup offers. **This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.** Welcome to 7725 Purple Finch Street in Winter Garden, a 2-story home offering 3 bedrooms, 2.5 bathrooms, an open floorplan, and a comfortable layout designed for everyday living, with

    Agent Photo

    Thomas Nickley

    KELLER WILLIAMS REALTY AT THE PARKS

    7725 Purple Finch St, Winter Garden, FL 34787
  • /11

    $1,800

    Total Monthly Price

    • 2 Beds
    • 1.5 Baths
    • 1,100 Sq Ft
    • Townhouse for Rent

    1345 Winter Green Way, Winter Garden, FL 34787

    1345 Winter Green Way, Winter Garden, FL 34787
  • /27

    $659,420

    Sold Oct 31, 2025

    12595 Grape Chardonnay Aly, Winter Garden, FL 34787

    • 4 Beds
    • 3.5 Baths
    • 2,693 Sq Ft
    • Built 2025

    Move in Ready Sold Summary

    • $245/SF
    • 9 Days On Market

    K. Hovnanian Homes Osprey Ranch

    12595 Grape Chardonnay Aly, Winter Garden, FL 34787
    • /2

      Est $621,629

      Not Listed For Sale

      6275 Hamlin Reserve Blvd, Winter Garden, FL 34787

      • 4 Beds
      • 3 Baths
      • 2,410 Sq Ft
      • Built 2017
      6275 Hamlin Reserve Blvd, Winter Garden, FL 34787

      Last Sold Summary

      • 220 Days On Market

  • /67

    $695,990

    • 5 Beds
    • 3.5 Baths
    • 3,366 Sq Ft

    5320 Lake Virginia St, Winter Garden, FL 34787

    Welcome to Hamlin Reserve in the heart of Horizon West! Built in 2024, this beautifully designed two-story home offers 5 bedrooms, 3 full bathrooms, 1 half bathroom, and over 3,300 square feet of thoughtfully designed living space. Step inside to a bright and inviting open-concept floor plan filled with natural light. The spacious kitchen seamlessly connects to the dining and living areas,

    Agent Photo

    Juliana Garcia Moraes

    PRISTINE INTERNATIONAL REALTY LLC

    5320 Lake Virginia St, Winter Garden, FL 34787
  • /10

    $1,500

    Total Monthly Price

    • 1 Bed
    • 1 Bath
    • 653 Sq Ft
    • House for Rent

    230 E Story Rd, Winter Garden, FL 34787

    This property is a one bedroom, one bath with a private driveway and backyard. Inside is all new appliances and fixtures. Shower is brand new and remodeled. The backyard has artificial turf and outdoor lighting.

    230 E Story Rd, Winter Garden, FL 34787
  • /2

    $575,000

    Sold Dec 12, 2025

    14700 Spotted Sandpiper Blvd, Winter Garden, FL 34787

    • 3 Beds
    • 2 Baths
    • 2,340 Sq Ft
    • Built 2014

    Last Sold Summary

    • $246/SF
    • 5 Days On Market

    Current Estimated Value $572,053

    Last Listing Agent Eve Metlis WATSON REALTY CORP

    14700 Spotted Sandpiper Blvd, 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

  • /29

    $250,000

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

    14501 Grove Resort Ave Unit 2423, Winter Garden, FL 34787

    Welcome to resort-style living at its absolute finest. This Superior 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 views, the most updated and

    Agent Photo

    Bill Traback

    MBI REALTY LLC

    14501 Grove Resort Ave Unit 2423, Winter Garden, FL 34787
  • /13

    $2,000

    Total Monthly Price

    • 2 Beds
    • 1 Bath
    • 1,000 Sq Ft
    • Condo for Rent

    1547 Spring Ridge Cir Unit 1, Winter Garden, FL 34787

    Welcome to your new home in the heart of Winter Garden! This charming apartment offers all the amenities you need for comfortable living and is perfectly situated in a wonderful neighborhood. You’ll also enjoy a shared, fully-fenced yard where you can pick fresh fruit or let your dog out to roam free!Located in a beautiful and friendly neighborhood, this apartment is in the golf cart

    1547 Spring Ridge Cir Unit 1, Winter Garden, FL 34787
  • /2

    $1,650,000

    Sold Mar 12, 2026

    9 E Newell St, Winter Garden, FL 34787

    • 4 Beds
    • 4.5 Baths
    • 3,686 Sq Ft
    • Built 2025

    Last Sold Summary

    • $448/SF
    • 11 Days On Market

    Current Estimated Value $1,524,788

    Last Listing Agent Alexis Anderson REGENCY REAL ESTATE LLC

    9 E Newell 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

  • /59

    $299,900

    $15K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,434 Sq Ft

    14501 Grove Resort Ave Unit 3109, Winter Garden, FL 34787

    PREMIUM BUILDING 3 | RARE 14-FOOT CEILINGS | ELEVATOR-FREE ACCESS | ONSITE RENTAL PROGRAMStep into the largest and most unique 2-bedroom footprint available at The Grove Resort & Water Park. Located on the highly coveted 1st floor of Building 3, Unit 3109 boasts massive 14-foot architectural ceilings exclusive to the ground level, delivering an incredible sense of volume, grandeur, and

    Agent Photo

    Bill Traback

    MBI REALTY LLC

    14501 Grove Resort Ave Unit 3109, Winter Garden, FL 34787
  • /28

    $2,185

    Total Monthly Price

    • 3 Beds
    • 2 Baths
    • 1,352 Sq Ft
    • Townhouse for Rent

    1007 Butterfly Blvd, Winter Garden, FL 34787

    -Conveniently located by major highways, stores, restaurants, shopping centers, Winter Garden Village, medical centers, and great schools-4 parking spaces located right in front of the townhome providing easy access-Large master bedroom with ensuite bathroom-New dishwasher-Community pool-First month, last month, and security deposit required

    1007 Butterfly Blvd, Winter Garden, FL 34787
  • /25

    $459,990

    Sold Sep 03, 2025

    9404 Bolshoi Aly, Winter Garden, FL 34787

    • 3 Beds
    • 2.5 Baths
    • 1,833 Sq Ft
    • Built 2025

    Move in Ready Sold Summary

    • $251/SF
    • 12 Days On Market

    Current Estimated Value $453,829

    9404 Bolshoi Aly, 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

  • /64

    $795,000

    • 5 Beds
    • 4 Baths
    • 3,174 Sq Ft

    8866 Bismarck Palm Dr, Winter Garden, FL 34787

    Luxury living in the ENZO Model townhome located in Lakeshore Preserve, a Toll Brothers community surrounded by million-dollar homes in Winter Garden. This spacious executive style townhome offers 5 bedrooms, 4 bathrooms, and over 3,100 square feet of living space, including a private 1-bedroom apartment with kitchenette above the garage and its own private entrance perfect for guests,

    Agent Photo

    Phil and Yuliya Mariani

    EXP REALTY LLC

    8866 Bismarck Palm Dr, Winter Garden, FL 34787
  • /13

    $3,350

    Total Monthly Price

    • 4 Beds
    • 3.5 Baths
    • 2,500 Sq Ft
    • House for Rent

    15308 Honeybell Dr, Winter Garden, FL 34787

    Located in the heart of Horizon West. Beautiful highly sought out Hamlin Reserve Community. Built in 2018 this 4 bed/ 3.5 bath home features an open concept space floor plan with a formal dining room and a modern kitchen with granite countertops and stainless steel appliances. There is an extra family room and a convenient second-floor laundry room. 2 car attached garage. The Community

    15308 Honeybell Dr, Winter Garden, FL 34787
  • /2

    $415,000

    Sold Jan 12, 2026

    8105 Red Stopper Ln, Winter Garden, FL 34787

    • 3 Beds
    • 2.5 Baths
    • 1,725 Sq Ft
    • Built 2017

    Last Sold Summary

    • 2% Below List Price
    • $241/SF
    • 7 Days On Market

    Current Estimated Value $418,476

    Last Listing Agent Heather Carr, PA BERKSHIRE HATHAWAY HOMESERVICES RESULTS REALTY

    8105 Red Stopper Ln, 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

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