37,947

Winter Garden, FL Homes

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  • /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
  • /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

    $900,000

    Sold May 19, 2026

    15324 Gilligan Ct, Winter Garden, FL 34787

    • 4 Beds
    • 3.5 Baths
    • 2,794 Sq Ft
    • Built 2020

    Last Sold Summary

    • 5% Below List Price
    • $322/SF
    • 18 Days On Market

    Current Estimated Value $902,861

    Last Listing Agent Gretchen Carlson REAL ESTATE HOUSE FL INC

    15324 Gilligan Ct, Winter Garden, FL 34787
    • /2

      Est $471,492

      Not Listed For Sale

      719 Stevelynn Cir, Winter Garden, FL 34787

      • 3 Beds
      • 2 Baths
      • 1,222 Sq Ft
      • Built 1998
      719 Stevelynn Cir, Winter Garden, FL 34787

      Last Sold Summary

      • 20 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
  • /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
  • /11

    $1,050,560

    Sold Jan 16, 2026

    226 Woodfall Ln, Winter Garden, FL 34787

    • 5 Beds
    • 5 Baths
    • 4,442 Sq Ft
    • Built 2026

    Move in Ready Sold Summary

    • $237/SF
    • 229 Days On Market

    Current Estimated Value $1,023,000

    Pulte Homes Winter Grove - Estate

    226 Woodfall Ln, Winter Garden, FL 34787
    • /2

      Est $206,084

      Not Listed For Sale

      996 Dolphin Dr, Winter Garden, FL 34787

      • 3 Beds
      • 2 Baths
      • 984 Sq Ft
      • Built 1989
      996 Dolphin Dr, Winter Garden, FL 34787

      Last Sold Summary

      • 70 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
  • /20

    $2,732

    Total Monthly Price

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

    14200 Avalon Rd Unit SI ID1244719P, Winter Garden, FL 34787

    The advertised rate of $2,732/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 16, 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 ID1244719P, Winter Garden, FL 34787
  • /2

    $1,100,000

    Sold Jul 31, 2026

    9976 Beach Port Dr, Winter Garden, FL 34787

    • 5 Beds
    • 3.5 Baths
    • 3,910 Sq Ft
    • Built 2020

    Last Sold Summary

    • 14% Below List Price
    • $281/SF
    • 0 Days On Market

    Current Estimated Value $1,001,840

    Last Listing Agent JoAnn Best CHARLES RUTENBERG REALTY ORLANDO

    9976 Beach Port Dr, Winter Garden, FL 34787
    • /2

      Est $877,422

      Not Listed For Sale

      12649 Dallington Terrace, Winter Garden, FL 34787

      • 5 Beds
      • 4 Baths
      • 3,563 Sq Ft
      • Built 2007
      12649 Dallington Terrace, Winter Garden, FL 34787

      Last Sold Summary

      • 27 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
  • /20

    $3,399 Per Month

    • 5 Beds
    • 3 Baths
    • 2,231 Sq Ft
    • House for Rent

    6503 Tabebuia Pkwy, 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 $3496.90. That covers your base rent, $3399.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Community

    6503 Tabebuia Pkwy, Winter Garden, FL 34787
  • /2

    $929,500

    Sold Dec 03, 2025

    17234 Cork St, Winter Garden, FL 34787

    • 3 Beds
    • 2 Baths
    • 2,325 Sq Ft
    • Built 1979

    Last Sold Summary

    • 2% Below List Price
    • $400/SF
    • 20 Days On Market

    Current Estimated Value $910,719

    Last Listing Agent Jaime Galeoto FLORIDA REALTY RESULTS LLC

    17234 Cork St, Winter Garden, FL 34787
    • /2

      Est $465,978

      Not Listed For Sale

      2407 Oakington St, Winter Garden, FL 34787

      • 4 Beds
      • 2 Baths
      • 1,755 Sq Ft
      • Built 2003
      2407 Oakington St, Winter Garden, FL 34787

      Last Sold Summary

      • 35 Days On Market

  • /52

    $714,999

    $80K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,027 Sq Ft

    14050 Fairway Willow Ln, Winter Garden, FL 34787

    Welcome to this beautifully maintained home in the highly sought-after Woodbridge on the Green community, overlooking West Orange Country Club and perfectly situated in the hub of Winter Garden. This waterfront home offers a blend of comfort, style, and convenience—ideal for anyone looking to enjoy the best of Central Florida living. Step inside to an inviting, light-filled layout featuring

    Agent Photo

    Drew Ross

    LAKEFIELD REALTY GROUP LLC

    14050 Fairway Willow Ln, Winter Garden, FL 34787
  • /20

    $2,610

    Total Monthly Price

    • 3 Beds
    • 2 Baths
    • 1,536 Sq Ft
    • House for Rent

    109 Zachary Wade St, 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

    109 Zachary Wade St, Winter Garden, FL 34787
  • /2

    $902,500

    Sold Apr 08, 2026

    149 S Park Ave, Winter Garden, FL 34787

    • 3 Beds
    • 3.5 Baths
    • 2,938 Sq Ft
    • Built 2019

    Last Sold Summary

    • 18% Below List Price
    • $307/SF
    • 222 Days On Market

    Current Estimated Value $914,571

    Last Listing Agent Brigitte Knott CHARLES RUTENBERG REALTY ORLANDO

    149 S Park Ave, Winter Garden, FL 34787
    • /2

      Est $583,906

      Not Listed For Sale

      15144 Spinnaker Cove Ln, Winter Garden, FL 34787

      • 4 Beds
      • 2 Baths
      • 2,153 Sq Ft
      • Built 2005
      15144 Spinnaker Cove Ln, Winter Garden, FL 34787

      Last Sold Summary

      • 101 Days On Market

  • /72

    $1,046,000

    • 5 Beds
    • 4 Baths
    • 3,863 Sq Ft

    1711 Amsel Falls Park Terrace, Winter Garden, FL 34787

    Back on the market through no fault of the seller! This home successfully passed the buyer’s 4-Point Inspection, Wood-Destroying Organism (WDO) Inspection, and appraisal, demonstrating its excellent condition. The appraisal has already been completed, and the seller has the appraisal and inspections in hand for you peace of mind. Unfortunately, the previous buyer was unable to secure financing,

    Agent Photo

    Jamil C. Winston (Jay)

    LPT REALTY, LLC

    1711 Amsel Falls Park Terrace, Winter Garden, FL 34787
  • /17

    $2,395 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 lease is signed by all applicants and security deposits are collected.Interested in this home? You clearly have exceptional taste. This charming 3-bedroom, 2.5-bathroom home is not only pet-friendly, but also equipped with smart home features to make everyday life more convenient and

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

    $824,500

    Sold Jun 29, 2026

    1432 Marble Crest Way, Winter Garden, FL 34787

    • 5 Beds
    • 4 Baths
    • 3,734 Sq Ft
    • Built 2005

    Last Sold Summary

    • $221/SF
    • 1 Day On Market

    Current Estimated Value $837,797

    Last Listing Agent Ken Pozek REAL BROKER, LLC

    1432 Marble Crest Way, Winter Garden, FL 34787
    • /2

      Est $473,361

      Not Listed For Sale

      470 Regal Downs Cir, Winter Garden, FL 34787

      • 4 Beds
      • 2.5 Baths
      • 2,316 Sq Ft
      • Built 2001
      470 Regal Downs Cir, Winter Garden, FL 34787

      Last Sold Summary

      • 33 Days On Market

  • /15

    $515,000

    $20K 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

    14075 Lochend Way, Winter Garden, FL 34787
  • /20

    $3,115

    Total Monthly Price

    • 4 Beds
    • 3 Baths
    • 2,381 Sq Ft
    • House for Rent

    1238 Rain Lily Rd, 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

    1238 Rain Lily Rd, Winter Garden, FL 34787
  • /2

    $485,000

    Sold Apr 17, 2026

    12272 Bracco St, Winter Garden, FL 34787

    • 3 Beds
    • 2.5 Baths
    • 1,788 Sq Ft
    • Built 2024

    Last Sold Summary

    • 9% Below List Price
    • $271/SF
    • 315 Days On Market

    Current Estimated Value $483,406

    Last Listing Agent Dana Gold RE/MAX ASSURED

    12272 Bracco St, Winter Garden, FL 34787
    • /2

      Est $758,328

      Not Listed For Sale

      13108 Lakeshore Grove Dr, Winter Garden, FL 34787

      • 4 Beds
      • 3 Baths
      • 2,674 Sq Ft
      • Built 2000
      13108 Lakeshore Grove Dr, Winter Garden, FL 34787

      Last Sold Summary

      • 32 Days On Market

  • /24

    $195,000

    • Land
    • 23,522 Sq Ft
    • $361,111 per Acre

    0 Avalon Rd Unit 53, Winter Garden, FL 34787

    Discover the potential of this exceptional 0.54-acre vacant lot in the heart of established Winter Garden. Measuring approximately 120 feet wide by 200 feet deep, this residentially zoned (R-2) property offers an outstanding opportunity to build your dream home or make a smart investment in one of Central Florida's most desirable and rapidly growing communities. Enjoy the freedom of no HOA and

    Agent Photo

    Rick Brown

    KELLER WILLIAMS ADVANTAGE 2 REALTY

    0 Avalon Rd Unit 53, Winter Garden, FL 34787
  • /20

    $3,000 Per Month

    • 4 Beds
    • 3 Baths
    • 1,853 Sq Ft
    • Townhouse for Rent

    6536 Calamondin Dr, Winter Garden, FL 34787

    Welcome to your dream townhome in the heart of Winter Garden! This stunning 4-bedroom, 3-bathroom gem offers a perfect blend of comfort and modern living, making it an ideal choice for anyone looking to settle down in style. With 1,853 square feet of spacious living, you'll have plenty of room to create lasting memories.Step inside and be greeted by a bright and airy layout that flows

    6536 Calamondin Dr, Winter Garden, FL 34787
  • /2

    $820,000

    Sold Jul 29, 2026

    8124 Red Crossbill St, Winter Garden, FL 34787

    • 6 Beds
    • 4 Baths
    • 3,708 Sq Ft
    • Built 2013

    Last Sold Summary

    • 9% Below List Price
    • $221/SF
    • 288 Days On Market

    Current Estimated Value $816,158

    Last Listing Agent Juan Castro REDFIN CORPORATION

    8124 Red Crossbill St, Winter Garden, FL 34787
    • /2

      Est $542,939

      Not Listed For Sale

      570 Cascading Creek Ln, Winter Garden, FL 34787

      • 3 Beds
      • 2 Baths
      • 2,365 Sq Ft
      • Built 2006
      570 Cascading Creek Ln, Winter Garden, FL 34787

      Last Sold Summary

      • 56 Days On Market

  • /3

    $2,700,000

    $3M PRICE DROP
    • Land
    • 9.64 Acres
    • $280,083 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

    17902 Seidner Rd, Winter Garden, FL 34787
  • /20

    $6,116

    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 $6,116/month is the lowest available price, based on a 1 month(s) stay with a move-in date of September 13, 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

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

    $772,500

    Sold Feb 02, 2026

    15485 Sandfield Loop, Winter Garden, FL 34787

    • 4 Beds
    • 3.5 Baths
    • 4,010 Sq Ft
    • Built 2015

    Last Sold Summary

    • 3% Below List Price
    • $193/SF
    • 53 Days On Market

    Current Estimated Value $773,302

    Last Listing Agent Angel Iglesia LUXE PROPERTIES

    15485 Sandfield Loop, Winter Garden, FL 34787
    • /2

      Est $774,402

      Not Listed For Sale

      13524 Lake Luntz Dr, Winter Garden, FL 34787

      • 5 Beds
      • 2.5 Baths
      • 2,755 Sq Ft
      • Built 1991
      13524 Lake Luntz Dr, Winter Garden, FL 34787

      Last Sold Summary

      • 0 Days On Market

  • /51

    $560,000

    • 4 Beds
    • 3.5 Baths
    • 2,487 Sq Ft

    16031 Pebble Bluff Loop, Winter Garden, FL 34787

    Move in ready home in Waterleigh one of Winter Garden’s most desirable places to live! Ideally positioned within the community for quick and convenient access, this home also sits directly across from a playground and green space perfect for families and outdoor fun. Freshly updated with new interior paint and brand new carpet throughout the bedrooms and upstairs, this home is truly turnkey.

    Agent Photo

    Phil and Yuliya Mariani

    EXP REALTY LLC

    16031 Pebble Bluff Loop, Winter Garden, FL 34787
  • /15

    $2,999 Per Month

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

    703 Bainbridge Loop, Winter Garden, FL 34787

    Coming soon - this home is currently being enjoyed by another resident but will be available soon. Pre-lease this home now with Tricon Pre-Lease Guarantee. This home is professionally managed by Tricon, dedicated to creating exceptional rental experiences. Featuring 3 bedrooms, 2.0 bathrooms, and approximately 2,022 square feet, this well-maintained home offers a high standard of rental living,

    703 Bainbridge Loop, Winter Garden, FL 34787
  • /2

    $1,070,000

    Sold Dec 05, 2025

    14400 Shocklach Dr, Winter Garden, FL 34787

    • 5 Beds
    • 4.5 Baths
    • 3,616 Sq Ft
    • Built 2015

    Last Sold Summary

    • 5% Below List Price
    • $296/SF
    • 67 Days On Market

    Current Estimated Value $1,038,407

    Last Listing Agent Mauricio Penha VOLKE REAL ESTATE LLC

    14400 Shocklach Dr, Winter Garden, FL 34787
    • /2

      Est $272,719

      Not Listed For Sale

      321 Beard Rd, Winter Garden, FL 34787

      • 2 Beds
      • 2 Baths
      • 919 Sq Ft
      • Built 1960
      321 Beard Rd, Winter Garden, FL 34787

      Last Sold Summary

      • 3 Days On Market

Showing Results 161 - 200, Page 5 of 18

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