37,933

Winter Garden, FL Homes

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  • /49

    $695,000

    $24K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 2,839 Sq Ft

    5966 Cypress Hill Rd, Winter Garden, FL 34787

    Price Improvement – Welcome to 5966 Cypress Hill Rd, located in the highly sought-after Independence community of Winter Garden. This well-maintained home offers a rare blend of privacy, space, and lifestyle amenities. Situated on a larger-than-average lot with no rear neighbors, the home backs up to an open area, creating a peaceful and private setting—perfect for relaxing or entertaining.

    Mahmoud Mango DALTON WADE INC

    5966 Cypress Hill Rd, Winter Garden, FL 34787
  • /55

    $4,300 Per Month

    • 4 Beds
    • 3 Baths
    • 3,000 Sq Ft
    • House for Rent

    2413 Prairie View Dr, Winter Garden, FL 34787

    MOVE IN in AUGUST and GET 50% OFF towards August rent. Beautiful FULLY FURNISHED house in a gated community offers 4 bedrooms, 3 full bathrooms, separate office area and a bonus space! Recent upgrades are new flooring throughout and carpet in the bedrooms. Comes with furniture, rugs, TV's, full appliance package, outdoor furniture and table tennis. Ready to move in and live the Florida life!

    Sevara Botirova Patel CHARLES RUTENBERG REALTY ORLANDO

    2413 Prairie View Dr, Winter Garden, FL 34787
  • /2

    $2,050,000

    Sold May 29, 2026

    5340 Bowman Dr, Winter Garden, FL 34787

    • 5 Beds
    • 6.5 Baths
    • 5,749 Sq Ft
    • Built 2017

    Last Sold Summary

    • 7% Below List Price
    • $357/SF
    • 17 Days On Market

    Current Estimated Value $2,094,066

    Last Listing Agent Steve Healy CORCORAN PREMIER REALTY

    5340 Bowman Dr, Winter Garden, FL 34787
    • /2

      Est $422,166

      Not Listed For Sale

      11084 Suspense Dr, Winter Garden, FL 34787

      • 3 Beds
      • 2.5 Baths
      • 1,636 Sq Ft
      • Built 2018
      11084 Suspense Dr, Winter Garden, FL 34787

      Last Sold Summary

      • 26 Days On Market

  • /8

    $438,990

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 1,635 Sq Ft

    Regina II Plan at Northlake at Ovation - Townhomes, Winter Garden, FL 34787

    The Regina II is a two-story townhome offering three bedrooms, two full bathrooms, one half bathroom, and a two-car garage. The open-concept main floor connects the kitchen, dining, and family rooms, creating a bright and inviting space for everyday living. Upstairs, the private primary suite features a walk-in closet, accompanied by two additional bedrooms and a conveniently located laundry

    Ashton Woods Builder
    17551 Lake Star Rd Unit 36453066, Winter Garden, FL 34787
  • /17

    $2,700 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,624 Sq Ft
    • Townhouse for Rent

    17332 Sweet Moro Dr, Winter Garden, FL 34787

    Brand New Townhouse, MOVE IN READY, Be the first one to live in this beautiful Townhome with a detached 2-car garage, and a very convenient private rear courtyard with privacy. With a great and functional open floor plan. All Apoliances included Washer, Dryer and Fridge included. Close to retail and zoned for top-rated schools.Experience Luxury Living in This BRAND NEW 3 Bedroom, 2.5 Bathroom

    17332 Sweet Moro Dr, Winter Garden, FL 34787
  • /16

    $453,351

    Sold Apr 15, 2026

    13343 Peaceful Melody Dr, Winter Garden, FL 34787

    • 3 Beds
    • 2.5 Baths
    • 1,644 Sq Ft
    • Built 2026

    Move in Ready Sold Summary

    • $276/SF
    • 7 Days On Market

    Dream Finders Homes Serenade at Ovation - Townhomes

    13343 Peaceful Melody Dr, Winter Garden, FL 34787
    • /84

      Est $846,863

      Not Listed For Sale

      5060 Palmetto Park Dr, Winter Garden, FL 34787

      • 4 Beds
      • 3.5 Baths
      • 3,866 Sq Ft
      • Built 2017
      5060 Palmetto Park Dr, Winter Garden, FL 34787

      Last Sold Summary

      • 32 Days On Market

  • /37

    $782,990

    New Construction
    • 4 Beds
    • 3.5 Baths
    • 3,291 Sq Ft

    Tidewater With Bonus Plan at Avalon Woods - 60' Homesites, Winter Garden, FL

    The Tidewater with Bonus floorplan offers a versatile and spacious two-story layout, featuring 4 bedrooms and 3.5 bathrooms. Spanning 3,289 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

    Dream Finders Homes Builder
    0 Avalon Woods St Unit 37162284, Winter Garden, FL
  • /44

    $3,400 Per Month

    • 4 Beds
    • 3 Baths
    • 2,048 Sq Ft
    • House for Rent

    17820 Sharp Pummelo Aly, Winter Garden, FL 34787

    Beautiful 4-bedroom, 3-bath single-family home built in 2024 in the highly sought-after Northlake at Ovation community in the heart of Winter Garden. This thoughtfully designed home features an open-concept floor plan filled with natural light, a spacious kitchen with quartz countertops, a large center island, modern cabinetry, and stainless steel appliances, plus a washer and dryer for added

    Viviane Almeida WRA BUSINESS & REAL ESTATE

    17820 Sharp Pummelo Aly, Winter Garden, FL 34787
  • /2

    $900,000

    Sold Aug 26, 2025

    14415 Lake Huckleberry Ln, Winter Garden, FL 34787

    • 3 Beds
    • 2 Baths
    • 1,269 Sq Ft
    • Built 1979

    Last Sold Summary

    • 18% Below List Price
    • $709/SF
    • 151 Days On Market

    Current Estimated Value $885,652

    Last Listing Agent Rob Rahter STOCKWORTH REALTY GROUP

    14415 Lake Huckleberry Ln, Winter Garden, FL 34787
    • /24

      Est $328,854

      Not Listed For Sale

      14038 Avenue of the Groves, Winter Garden, FL 34787

      • 2 Beds
      • 2.5 Baths
      • 1,263 Sq Ft
      • Built 2011
      14038 Avenue of the Groves, Winter Garden, FL 34787

      Last Sold Summary

      • 31 Days On Market

  • /79

    $735,900

    New Construction
    • 4 Beds
    • 2.5 - 3.5 Baths
    • 2,889+ Sq Ft

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

    Luxurious New Home by RockWell Homes, Now Selling! Welcome to the Eliot design, a thoughtfully crafted home offering a balance of comfort, style, and flexibility. This popular floorplan includes 4 bedrooms, 2.5 to 3.5 bathrooms, and a spacious loft, with multiple structural options available to personalize the layout. The exterior design enhances curb appeal and functionality, featuring a covered

    RockWell Homes Builder
    17551 Lake Star Rd Unit 36901640, Winter Garden, FL 34787
  • /23

    $2,545 Per Month

    • 3 Beds
    • 3 Baths
    • 1,300 Sq Ft
    • Condo for Rent

    1120 Lincoln Terrace Unit B, Winter Garden, FL 34787

    Welcome to this stunning brand-new 3-bedroom, 3-bathroom home, thoughtfully designed with modern finishes and abundant natural light throughout. Featuring tile flooring throughout the entire home, this property offers both style and easy maintenance.The contemporary kitchen is equipped with elegant quartz countertops, white cabinetry, stainless steel appliances, and a gas stove, creating

    1120 Lincoln Terrace Unit B, Winter Garden, FL 34787
  • /2

    $641,000

    Sold Apr 30, 2026

    2425 Prairie View Dr, Winter Garden, FL 34787

    • 5 Beds
    • 3 Baths
    • 3,524 Sq Ft
    • Built 2003

    Last Sold Summary

    • 8% Below List Price
    • $182/SF
    • 65 Days On Market

    Current Estimated Value $647,099

    Last Listing Agent Amaal Barakat KELLER WILLIAMS ADVANTAGE III

    2425 Prairie View Dr, Winter Garden, FL 34787
    • /2

      Est $755,608

      Not Listed For Sale

      13870 Jomatt Loop, Winter Garden, FL 34787

      • 4 Beds
      • 3.5 Baths
      • 3,462 Sq Ft
      • Built 2018
      13870 Jomatt Loop, Winter Garden, FL 34787

      Last Sold Summary

      • 26 Days On Market

  • /3

    $651,990

    New Construction
    • 4 Beds
    • 2.5 Baths
    • 2,235 Sq Ft

    Anna Maria Plan at Avalon Woods - 50' Homesites, Winter Garden, FL

    The Anna Maria floorplan is a thoughtfully designed one-story home featuring four bedrooms and two and a half bathrooms, perfect for comfortable family living. The open-concept layout highlights a spacious great room that flows seamlessly into the kitchen and dining area, making it ideal for gatherings and relaxation. The primary bedroom offers privacy with a well-appointed ensuite and a large

    Dream Finders Homes Builder
    0 Avalon Woods St Unit 37123076, Winter Garden, FL
  • /28

    $3,150 Per Month

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

    15236 Tribute Ovation Way, Winter Garden, FL 34787

    Beautiful Townhome in Prime Horizon West Location Available Now! Welcome to Tribute at Ovation, ideally situated just across the street from the new Publix Shopping Center and the upcoming Promenade at Horizon West . This New Windham townhome is around 1850 Sq Ft and offers 3 bedrooms, a flex, 2.5 bathrooms, and an open concept floor plan. Detached 2 car garage with paver courtyard area and

    ChandraMohan Narayana Swamy DALTON WADE INC

    15236 Tribute Ovation Way, Winter Garden, FL 34787
  • /2

    $530,000

    Sold Jul 01, 2026

    8906 Doddington Way, Winter Garden, FL 34787

    • 4 Beds
    • 3 Baths
    • 2,352 Sq Ft
    • Built 2016

    Last Sold Summary

    • 7% Below List Price
    • $225/SF
    • 95 Days On Market

    Current Estimated Value $541,376

    Last Listing Agent Tyler Somers KELLER WILLIAMS REALTY AT THE PARKS

    8906 Doddington Way, Winter Garden, FL 34787
    • /2

      Est $894,092

      Not Listed For Sale

      9192 Bradleigh Dr, Winter Garden, FL 34787

      • 5 Beds
      • 4.5 Baths
      • 3,543 Sq Ft
      • Built 2018
      9192 Bradleigh Dr, Winter Garden, FL 34787

      Last Sold Summary

      • 11 Days On Market

  • /3

    $617,990

    New Construction
    • 4 Beds
    • 2.5 Baths
    • 2,235 Sq Ft

    Anna Maria Plan at Hamlin Meadows - 50' Homesites, Winter Garden, FL

    The Anna Maria floorplan is a thoughtfully designed one-story home featuring four bedrooms and two and a half bathrooms, perfect for comfortable family living. The open-concept layout highlights a spacious great room that flows seamlessly into the kitchen and dining area, making it ideal for gatherings and relaxation. The primary bedroom offers privacy with a well-appointed ensuite and a large

    Dream Finders Homes Builder
    0 Hamlin Meadows St Unit 39127934, Winter Garden, FL
  • /16

    $1,450 Per Month

    • 2 Beds
    • 2 Baths
    • 918 Sq Ft
    • Great location! 2nd floor condo in Winter Garden

    88 Windtree Ln, Winter Garden, FL 34787

    Great location! 2nd floor condo in Winter Garden offers 918 square feet of living space, split floor plan, screened in patio, and two assigned parking spaces.Lessee(s) are required to provide proof of liability insurance in the amount of $100,000, prior to occupancy. Real Property Management South Orlando can provide the required coverage for an additional charge of $13.00 per month or

    88 Windtree Ln, Winter Garden, FL 34787
  • /2

    $488,430

    Sold Jun 23, 2026

    15044 Groveside Rd, Winter Garden, FL 34787

    • 3 Beds
    • 2.5 Baths
    • 1,846 Sq Ft
    • Built 2025

    Last Sold Summary

    • 2% Above List Price
    • $265/SF
    • 90 Days On Market

    Current Estimated Value $481,361

    Last Listing Agent Adam Schott DRB GROUP REALTY, LLC

    15044 Groveside Rd, Winter Garden, FL 34787
    • /49

      Est $519,648

      Not Listed For Sale

      16025 Pebble Bluff Loop, Winter Garden, FL 34787

      • 3 Beds
      • 2.5 Baths
      • 2,220 Sq Ft
      • Built 2018
      16025 Pebble Bluff Loop, Winter Garden, FL 34787

      Last Sold Summary

      • 79 Days On Market

  • /13

    $625,990

    New Construction
    • 3 Beds
    • 2 Baths
    • 1,857+ Sq Ft

    Ashford Plan at Lake Star at Ovation - Cottage Collection, Winter Garden, FL 34787

    It's love at first sight when you first see the Ashford! With the inviting front porch, carriage-style garage doors, brick paver driveway and lead walk, this home is reminiscent of a simpler time! This single-story, 3 bedroom, 2 bathroom, 2-car garage home ranges from 1,857 - 1,912 square feet. Schedule your tour today!

    M/I Homes Builder
    12025 Encore at Ovation Way Unit 36487483, Winter Garden, FL 34787
  • /18

    $2,750 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,661 Sq Ft
    • Townhouse for Rent

    6406 Tabebuia Pkwy, Winter Garden, FL 34787

    Welcome to this beautiful and home located in a desirable community with excellent amenities. This spacious residence offers a modern layout, comfortable living areas, and plenty of natural light, making it perfect for everyday living and entertaining. Conveniently located near shopping, dining, schools, major highways, and local attractions. Community amenities are available for residents to

    Beatrice Do Amaral RE/MAX REX

    6406 Tabebuia Pkwy, Winter Garden, FL 34787
  • /2

    $570,000

    Sold Jan 27, 2026

    15107 Kirsty Aly, Winter Garden, FL 34787

    • 4 Beds
    • 2.5 Baths
    • 2,292 Sq Ft
    • Built 2017

    Last Sold Summary

    • 3% Below List Price
    • $249/SF
    • 17 Days On Market

    Current Estimated Value $564,497

    Last Listing Agent Raphael Sena Oliveira de Sena KAZA REAL ESTATE LLC

    15107 Kirsty Aly, Winter Garden, FL 34787
    • /33

      Est $829,261

      Not Listed For Sale

      10277 Spring Shores Dr, Winter Garden, FL 34787

      • 4 Beds
      • 3.5 Baths
      • 3,316 Sq Ft
      • Built 2018
      10277 Spring Shores Dr, Winter Garden, FL 34787

      Last Sold Summary

      • 14 Days On Market

  • /3

    $646,990

    New Construction
    • 3 - 4 Beds
    • 2 - 3 Baths
    • 2,066 Sq Ft

    Douglas II Plan at Northlake at Ovation - Traditional, Winter Garden, FL 34787

    The Douglas II is a one-story home offering three bedrooms, two full bathrooms, and a two-car garage. The open-concept layout connects the kitchen to the great room, creating a spacious and bright central living space. A private primary suite offers comfort and seclusion, while an oversized laundry room and a large, covered lanai enhance everyday functionality and outdoor living. Thoughtful

    Ashton Woods Builder
    17551 Lake Star Rd Unit 36470845, Winter Garden, FL 34787
  • /34

    $1,695 Per Month

    • 1 Bed
    • 1 Bath
    • 942 Sq Ft
    • Condo for Rent

    430 Southern Pecan Cir Unit 207, Winter Garden, FL 34787

    Amazing opportunity in resort style Southern Pines Condos, Winter Garden! The primary bedroom has ample space, a walk-in closet, and a bathroom that doubles as a guest bath with double entry doors. Gourmet kitchen with separate dining area and bonus/flex room. Additional features include a laundry room, extra closets, and no carpet throughout. This gated community boasts a multi-million-dollar

    Seyed Azimi AFT PROPERTY LLC

    430 Southern Pecan Cir Unit 207, Winter Garden, FL 34787
  • /2

    $153,000

    Sold Jan 13, 2026

    117 Windtree Ln Unit 102, Winter Garden, FL 34787

    • 2 Beds
    • 2 Baths
    • 918 Sq Ft
    • Built 1984

    Last Sold Summary

    • 22% Below List Price
    • $167/SF
    • 46 Days On Market

    Current Estimated Value $163,145

    Last Listing Agent Tony Vicari VICARI REALTY CORP

    117 Windtree Ln Unit 102, Winter Garden, FL 34787
    • /2

      Est $637,213

      Not Listed For Sale

      10344 Atwater Bay Dr, Winter Garden, FL 34787

      • 4 Beds
      • 3 Baths
      • 2,909 Sq Ft
      • Built 2018
      10344 Atwater Bay Dr, Winter Garden, FL 34787

      Last Sold Summary

      • 165 Days On Market

  • /67

    $620,000

    $10K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,692 Sq Ft

    17059 Harbor Oak Pkwy, Winter Garden, FL 34787

    Motivated Seller! Don't miss your opportunity with this Winter Garden home - offering elegance, convenience and affordability. Situated inside the desirable Waterside community, you will find this beautifully designed residence, blending timeless sophistication with modern comfort, offering an open floor plan, designer finishes, and exceptional indoor-outdoor living.From the moment you

    Wendy Moore ERA GRIZZARD REAL ESTATE

    17059 Harbor Oak Pkwy, Winter Garden, FL 34787
  • /28

    $3,000 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,829 Sq Ft
    • House for Rent

    9350 Woodcrane Dr, Winter Garden, FL 34787

    Amazing corner lot property located in the heart of Central, FL. Disney World and several major attractions are within a 6 mile drive. Hwy 429 is within a mile. Winter Garden Village, Hamlin Town Center and top rated schools are also only a few minutes away. Get to the happiest place on Earth and much more in minutes! The community has resort-like amenities that include a pool with splash pad,

    Vinny Apolinario WRA BUSINESS & REAL ESTATE

    9350 Woodcrane Dr, Winter Garden, FL 34787
  • /2

    $570,000

    Sold Oct 29, 2025

    16484 Angel Fish Rd, Winter Garden, FL 34787

    • 4 Beds
    • 3.5 Baths
    • 2,472 Sq Ft
    • Built 2021

    Last Sold Summary

    • 10% Below List Price
    • $231/SF
    • 116 Days On Market

    Current Estimated Value $572,200

    Last Listing Agent Fanny Stollmeyer LIFESTYLE INTERNATIONAL REALTY

    16484 Angel Fish Rd, Winter Garden, FL 34787
    • /2

      Est $1,392,046

      Not Listed For Sale

      10151 Savannah Ridge Ln, Winter Garden, FL 34787

      10151 Savannah Ridge Ln, Winter Garden, FL 34787

      Last Sold Summary

      • 205 Days On Market

  • /31

    $179,950

    $20K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,265 Sq Ft

    14501 Grove Resort Ave Unit 1732, Winter Garden, FL 34787

    Experience the ultimate Orlando resort lifestyle and investment opportunity at The Grove Resort & Water Park, one of Central Florida’s premier vacation destinations located just minutes from Disney World and close to Universal Studios, SeaWorld, Margaritaville Resort, shopping, dining, and Orlando International Airport. This fully furnished, turnkey condominium offers a spacious open-concept

    Shaunda Hall GENSTONE REALTY

    14501 Grove Resort Ave Unit 1732, Winter Garden, FL 34787
  • /39

    $5,400 Per Month

    • 6 Beds
    • 4 Baths
    • 4,704 Sq Ft
    • House for Rent

    17987 Gourd Neck Loop, Winter Garden, FL 34787

    Prepare to be amazed by this expansive, newly renovated rental in a charming sub-division of Winter Garden, Florida! Offering a rare SIX bedrooms and FOUR bathrooms, this is the perfect solution for a large family or corporate housing. Best of all, the home is fully furnished and ready for immediate move-in, with a preferred lease start of August 1st. The entire home has been spectacularly

    Joel Parrott EXPERT REALTY SOLUTIONS INC.

    17987 Gourd Neck Loop, Winter Garden, FL 34787
  • /2

    $530,000

    Sold Jan 20, 2026

    2332 Black Lake Blvd, Winter Garden, FL 34787

    • 4 Beds
    • 3 Baths
    • 1,986 Sq Ft
    • Built 2006

    Last Sold Summary

    • 4% Below List Price
    • $267/SF
    • 56 Days On Market

    Current Estimated Value $527,107

    Last Listing Agent David Johnston CREEGAN GROUP

    2332 Black Lake Blvd, Winter Garden, FL 34787
    • /23

      Est $840,748

      Not Listed For Sale

      1021 Huntspoint St, Winter Garden, FL 34787

      • 3 Beds
      • 3.5 Baths
      • 2,373 Sq Ft
      • Built 2018
      1021 Huntspoint St, Winter Garden, FL 34787

      Last Sold Summary

      • 52 Days On Market

Showing Results 521 - 560, Page 14 of 18

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