37,760

Winter Garden, FL Homes

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  • /55

    $650,000

    $140K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,931 Sq Ft

    18339 Oliver Twist Way, Winter Garden, FL 34787

    Short Sale. *Motivated Seller* This 2023 built home has only had One-owner, highly upgraded luxury 4-bedroom, 3-bathroom home with 2-car garage, fenced-in oversized yard, and overhead storage in the highly desirable Waterleigh community—just minutes from Walt Disney World in the Top-Rated School zone. No lawn mower needed - the HOA maintains all lawn care in this beautiful community! This home is

    Edward Guerrette HAMLIN REALTY

    18339 Oliver Twist Way, Winter Garden, FL 34787
  • /33

    $3,000 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,974 Sq Ft
    • House for Rent

    5917 Grassy Point Rd, Winter Garden, FL 34787

    New Independence Neighborhood, Horizon West, Orange County, Florida. Welcome to the amenity-rich Independence community! This spacious 3-bedroom single-family home offers a cozy living experience within the well-planned Independence neighborhood. Enjoy the comfort of modern amenities and the convenience of an active lifestyle in this master-planned community. The property features a spacious

    Christian Mendez EXP REALTY LLC

    5917 Grassy Point Rd, Winter Garden, FL 34787
  • /2

    $1,039,060

    Sold Jun 05, 2026

    318 Crystal Wood Dr, Winter Garden, FL 34787

    • 5 Beds
    • 4.5 Baths
    • 3,643 Sq Ft
    • Built 2026

    Last Sold Summary

    • $285/SF

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

    318 Crystal Wood Dr, Winter Garden, FL 34787
    • /12

      Est $520,352

      Not Listed For Sale

      10187 Shallow Water Dr, Winter Garden, FL 34787

      • 3 Beds
      • 3 Baths
      • 2,040 Sq Ft
      • Built 2018
      10187 Shallow Water Dr, Winter Garden, FL 34787

      Last Sold Summary

      • 43 Days On Market

  • /85

    $535,000

    $23K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 2,477 Sq Ft

    16754 Oakboro St, Winter Garden, FL 34787

    Welcome to the highly sought-in the desirable Waterleigh community of Horizon West — where resort-style living meets everyday convenience! From the moment you enter, you’re greeted by a grand, palm tree-lined entrance that sets the tone for a private tropical retreat. Waterleigh is thoughtfully designed around picturesque ponds and lakes, with beautifully maintained landscaping throughout the

    Chun Cai SPRING REALTY ONE LLC

    16754 Oakboro St, Winter Garden, FL 34787
  • /28

    $2,100 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,544 Sq Ft
    • House for Rent

    1516 Scarlet Oak Loop, Winter Garden, FL 34787

    This well-maintained 3-bedroom, 2.5-bathroom two-story condo is located in the gated Tucker Oaks community of Winter Garden with no rear neighbors. The open-concept main living area features a spacious great room that combines the kitchen, dining, and living spaces, ideal for both everyday living and entertaining. The kitchen offers ample cabinet storage with honey-colored cabinetry, granite

    1516 Scarlet Oak Loop, Winter Garden, FL 34787
  • /13

    $577,745

    Sold Sep 27, 2025

    16418 Silver Brook Way, Winter Garden, FL 34787

    • 4 Beds
    • 2.5 Baths
    • 2,114 Sq Ft
    • Built 2025

    Move in Ready Sold Summary

    • $273/SF
    • 149 Days On Market

    Current Estimated Value $561,085

    16418 Silver Brook Way, Winter Garden, FL 34787
    • /2

      Est $671,533

      Not Listed For Sale

      10145 Beach Port Dr, Winter Garden, FL 34787

      • 5 Beds
      • 4 Baths
      • 2,840 Sq Ft
      • Built 2018
      10145 Beach Port Dr, Winter Garden, FL 34787

      Last Sold Summary

      • 89 Days On Market

  • /19

    $533,990

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 1,983 Sq Ft

    Jensen Plan at Lake Star at Ovation - Avenue Collection, Winter Garden, FL 34787

    The Jensen, with 3 bedrooms, 2 1⁄2 baths, and 1,932 square feet, is the only plan from our Bungalow Series that features a detached alley-loaded 2-car garage. To learn more about this home schedule your personal tour today!

    M/I Homes Builder
    12025 Encore at Ovation Way Unit 36491344, Winter Garden, FL 34787
  • /31

    $3,299 Per Month

    • 3 Beds
    • 2 Baths
    • 2,300 Sq Ft
    • House for Rent

    7564 Bishop Square Dr, Winter Garden, FL 34787

    This spacious and beautifully maintained one-story home offers 3 bedrooms, 2 baths, and a 2-car garage with approximately 2,300 sq. ft. of living space. The thoughtfully designed floor plan features an open-concept layout perfect for both everyday living and entertaining. The large kitchen is a true centerpiece, complete with a generous granite island, stainless steel appliances, 42” cherry

    Courtney James LA ROSA REALTY ORLANDO LLC

    7564 Bishop Square Dr, Winter Garden, FL 34787
  • /2

    $625,000

    Sold Jul 23, 2025

    6275 Hamlin Reserve Blvd, Winter Garden, FL 34787

    • 4 Beds
    • 3 Baths
    • 2,410 Sq Ft
    • Built 2017

    Last Sold Summary

    • 7% Below List Price
    • $259/SF
    • 220 Days On Market

    Current Estimated Value $622,730

    Last Listing Agent Elle Probst EXP REALTY LLC

    6275 Hamlin Reserve Blvd, Winter Garden, FL 34787
    • /40

      Est $806,112

      Not Listed For Sale

      8001 Key West Dove St, Winter Garden, FL 34787

      • 5 Beds
      • 5 Baths
      • 3,842 Sq Ft
      • Built 2013
      8001 Key West Dove St, Winter Garden, FL 34787

      Last Sold Summary

      • 12 Days On Market

  • /15

    $558,990

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 2,341 Sq Ft

    Sebring Plan at Lake Star at Ovation - Avenue Collection, Winter Garden, FL 34787

    This home is built with features that meet the Energy Star 3.1 home building requirements and is third party verified for energy efficiency. It’s also backed by M/I Homes' 10-Year Transferrable Warranty. Learn how these two features will benefit you and save you money starting the day you close.

    M/I Homes Builder
    12025 Encore at Ovation Way Unit 36450820, Winter Garden, FL 34787
  • /23

    $995 Per Month

    • 1 Bed
    • 1 Bath
    • 500 Sq Ft
    • 314 1/2 S Boyd St

    314 1/2 S Boyd St, Winter Garden, FL 34787

    Discover this charming 1-bedroom, 1-bathroom residence nestled in the vibrant community of Winter Garden. The inviting kitchen is equipped with modern appliances, including a refrigerator and stove, perfect for preparing delicious meals. The home features a comfortable blend of linoleum and carpet flooring, offering both practicality and coziness. Don't miss the opportunity to make this

    314 1/2 S Boyd St, Winter Garden, FL 34787
  • /2

    $500,000

    Sold Aug 29, 2025

    519 Hearthglen Blvd, Winter Garden, FL 34787

    • 4 Beds
    • 3 Baths
    • 3,009 Sq Ft
    • Built 2007

    Last Sold Summary

    • 20% Below List Price
    • $166/SF
    • 137 Days On Market

    Current Estimated Value $552,759

    Last Listing Agent Lauren Graham COLDWELL BANKER HUBBARD HANSEN

    519 Hearthglen Blvd, Winter Garden, FL 34787
    • /9

      Est $265,728

      Not Listed For Sale

      417 Southern Pecan Cir Unit 208, Winter Garden, FL 34787

      • 2 Beds
      • 2 Baths
      • 1,264 Sq Ft
      • Built 2005
      417 Southern Pecan Cir Unit 208, Winter Garden, FL 34787

      Last Sold Summary

      • 2 Days On Market

  • /3

    $749,990

    New Construction $7K PRICE INCREASE
    • 4 Beds
    • 3.5 Baths
    • 3,291 Sq Ft

    Tidewater With Bonus Plan at Hamlin Meadows - 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 Hamlin Meadows St Unit 39127942, Winter Garden, FL
  • /29

    $2,750 Per Month

    • 4 Beds
    • 3 Baths
    • 2,042 Sq Ft
    • House for Rent

    13071 Inkwell Aly, Winter Garden, FL 34787

    This spacious two-story home offers 4 bedrooms, 3 bathrooms, and approximately 2,042 sq ft of well-designed living space. The open-concept kitchen, complete with a large island, overlooks a bright and expansive family and dining area—perfect for everyday living and entertaining. The primary suite features an oversized bathroom with dual sinks and a generous walk-in closet. Additional highlights

    Amanda Yuan MULTI CHOICE REALTY LLC

    13071 Inkwell Aly, Winter Garden, FL 34787
  • /14

    $534,000

    Sold Sep 23, 2025

    5003 Railroad Vine Aly, Winter Garden, FL 34787

    • 3 Beds
    • 2.5 Baths
    • 1,788 Sq Ft
    • Built 2025

    Move in Ready Sold Summary

    • $299/SF
    • 265 Days On Market

    Current Estimated Value $500,400

    5003 Railroad Vine Aly, Winter Garden, FL 34787
    • /2

      Est $807,124

      Not Listed For Sale

      5657 Mangrove Cove Ave, Winter Garden, FL 34787

      • 5 Beds
      • 3.5 Baths
      • 3,881 Sq Ft
      • Built 2016
      5657 Mangrove Cove Ave, Winter Garden, FL 34787

      Last Sold Summary

      • 190 Days On Market

  • /3

    $742,990

    New Construction
    • 4 - 5 Beds
    • 3 - 4 Baths
    • 2,380+ Sq Ft

    Abbington Plan at Lake Star at Ovation - Manor Series, Winter Garden, FL 34787

    The Abbington is a beautiful single-story 4-bed, 3-bath, open-concept plan with a 2-car garage and covered lanai with sliding glass 8 ft. doors. To find out more about this home contact us today.

    M/I Homes Builder
    12025 Encore at Ovation Way Unit 36475471, Winter Garden, FL 34787
  • /18

    $1,700 Per Month

    • 2 Beds
    • 2 Baths
    • 918 Sq Ft
    • Townhouse for Rent

    165 Windtree Ln, Winter Garden, FL 34787

    Wonderful Windtree Gardens! Renovated 2 brm 2 bath 1st floor unit with screen enclosed balcony. No carpet in unit. Unit has 2 assigned parking spots, washer /dryer. Close to bus lines, shopping & restaurants. Requirements are 600+ credit score and income 2.5 times rent with no evictions on record. Application fee $75 per adult and security deposit = to 1 months rent. Applications can be made

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

    $420,000

    Sold Apr 24, 2026

    15590 Murcott Blossom Blvd, Winter Garden, FL 34787

    • 4 Beds
    • 3 Baths
    • 2,196 Sq Ft
    • Built 2017

    Last Sold Summary

    • 10% Below List Price
    • $191/SF
    • 97 Days On Market

    Current Estimated Value $430,112

    Last Listing Agent Paul Torola AMERICAN IDEAL HOMES, LLC

    15590 Murcott Blossom Blvd, Winter Garden, FL 34787
    • /2

      Est $2,024,542

      Not Listed For Sale

      15162 Shonan Gold Dr, Winter Garden, FL 34787

      • 6 Beds
      • 5.5 Baths
      • 4,817 Sq Ft
      • Built 2019
      15162 Shonan Gold Dr, Winter Garden, FL 34787

      Last Sold Summary

      • 79 Days On Market

  • /37

    $552,999

    New Construction
    • 3 - 4 Beds
    • 2.5 - 4.5 Baths
    • 2,441 Sq Ft

    Baldwin Plan at Harvest at Ovation, Winter Garden, FL 34787

    Enter the charming oasis that lies within the Baldwin bungalow floor plan. The 2,441 sq. ft. two-story home with 3 bedrooms, 2.5 bathrooms, and a 2-car detached garage presents an inviting living space perfect for entertaining and relaxation needs. Just passed the foyer and formal dining room, you'll find a capacious great room. The beautiful designer kitchen overlooks this first-floor,

    Taylor Morrison Builder
    15069 Summer Harvest St Unit 36664491, Winter Garden, FL 34787
  • /31

    $3,400 Per Month

    • 4 Beds
    • 3 Baths
    • 2,598 Sq Ft
    • House for Rent

    7148 Desert Mandarin St, Winter Garden, FL 34787

    Welcome to this beautifully maintained home in the highly desirable Summerlake community of Winter Garden! Perfectly situated directly across from a playground, offers comfort, style, and convenience for families and professionals alike.he home features an open-concept layout with a spacious kitchen, ample counter space, and seamless flow into the main living area, creating an ideal setting

    Any Alves WRA BUSINESS & REAL ESTATE

    7148 Desert Mandarin St, Winter Garden, FL 34787
  • /2

    $580,000

    Sold Jun 05, 2026

    117 Steinbeck St, Winter Garden, FL 34787

    • 4 Beds
    • 2 Baths
    • 1,928 Sq Ft
    • Built 2001

    Last Sold Summary

    • 7% Below List Price
    • $301/SF
    • 17 Days On Market

    Current Estimated Value $599,452

    Last Listing Agent Brian Masih Das SHAHRAM SONDI + CO.

    117 Steinbeck St, Winter Garden, FL 34787
    • /2

      Est $654,452

      Not Listed For Sale

      10272 Atwater Bay Dr, Winter Garden, FL 34787

      • 5 Beds
      • 4 Baths
      • 2,840 Sq Ft
      • Built 2018
      10272 Atwater Bay Dr, Winter Garden, FL 34787

      Last Sold Summary

      • 93 Days On Market

  • /16

    $960,990

    New Construction
    • 5 Beds
    • 4.5 - 5.5 Baths
    • 4,172 Sq Ft

    Serenity Plan at Lake Star at Ovation - Lakefront Series, Winter Garden, FL 34787

    Enter the home and be welcomed with views through to the back included lanai. To one side of the 2-story entry, you’ll find a full bedroom with en-suite bath, perfect for guests and to the other side the stairs. The main living area of this home is begging for entertaining with its open concept design; the dining room, with optional tray ceiling for extra pizazz, family room, and kitchen are all

    M/I Homes Builder
    12025 Encore at Ovation Way Unit 36465309, Winter Garden, FL 34787
  • /27

    $3,250 Per Month

    • 5 Beds
    • 3 Baths
    • 3,237 Sq Ft
    • House for Rent

    1065 Vinsetta Cir, Winter Garden, FL 34787

    Beautiful 5-Bedroom Home in Avalon ReserveWelcome to this spacious and beautifully designed 2-story single-family home located in the highly desirable Avalon Reserve community of Winter Garden, FL. Offering over 3,200 square feet of bright, open living space, this 5-bedroom, 3-bathroom home is perfect for comfortable living and entertaining.Home Highlights:Main Level: Features a

    1065 Vinsetta Cir, Winter Garden, FL 34787
  • /21

    $534,990

    Sold Apr 03, 2026

    12432 Clear Sapphire Dr, Winter Garden, FL 34787

    • 3 Beds
    • 2 Baths
    • 1,533 Sq Ft
    • Built 2026

    Move in Ready Sold Summary

    • $349/SF
    • 15 Days On Market

    K. Hovnanian Homes Osprey Ranch

    12432 Clear Sapphire Dr, Winter Garden, FL 34787
    • /2

      Est $334,609

      Not Listed For Sale

      1468 Scarlet Oak Loop, Winter Garden, FL 34787

      • 3 Beds
      • 2.5 Baths
      • 1,592 Sq Ft
      • Built 2013
      1468 Scarlet Oak Loop, Winter Garden, FL 34787

      Last Sold Summary

      • 81 Days On Market

  • /17

    $613,990

    New Construction
    • 4 Beds
    • 3.5 Baths
    • 2,780+ Sq Ft

    Wekiva Plan at Lake Star at Ovation - Avenue Collection, Winter Garden, FL 34787

    Fall in love with this 4 bedroom, 3 1⁄2 bath, with 2-car ally-load garage home. The Wekiva offers 3 elevations, each with various sized front porches and accents of stone, shutters, siding, or shaker shingles.

    M/I Homes Builder
    12025 Encore at Ovation Way Unit 36456346, Winter Garden, FL 34787
  • /47

    $3,200 Per Month

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

    15179 Blue Peacock Ln, Winter Garden, FL 34787

    Welcome to this stunning and spacious 4-bedroom, 3-bathroom residence located in the highly sought-after Osprey Ranch community in Winter Garden. Offering approximately 2,500 square feet of thoughtfully designed living space, this home combines modern elegance with everyday comfort. The open-concept floor plan features a bright and inviting living area that seamlessly connects to a beautifully

    Ayrys Torres TALENT REALTY SOLUTIONS

    15179 Blue Peacock Ln, Winter Garden, FL 34787
  • /2

    $750,000

    Sold Dec 19, 2025

    15242 Heron Hideaway Cir, Winter Garden, FL 34787

    • 5 Beds
    • 4 Baths
    • 4,247 Sq Ft
    • Built 2012

    Last Sold Summary

    • 12% Below List Price
    • $177/SF
    • 155 Days On Market

    Current Estimated Value $767,754

    Last Listing Agent Pat Hancock THOMAS LYNNE REALTY GROUP LLC

    15242 Heron Hideaway Cir, Winter Garden, FL 34787
    • /67

      Est $1,303,334

      Not Listed For Sale

      10345 Atwater Bay Dr, Winter Garden, FL 34787

      • 5 Beds
      • 3.5 Baths
      • 3,911 Sq Ft
      • Built 2018
      10345 Atwater Bay Dr, Winter Garden, FL 34787

      Last Sold Summary

      • 3 Days On Market

  • /97

    $1,290,000

    • 5 Beds
    • 5 Baths
    • 3,458 Sq Ft

    16689 Toccoa Row, Winter Garden, FL 34787

    Luxurious 5-bedroom 5-bathroom home with TWO MASTER SUITES. The primary suite is on the second floor. The second suite is located on the first floor. 8 x 48 Ceramic tile with warm wood-look throughout the entire home. Massive Kitchen Island. Quartz Waterfall for Kitchen Island. Farmhouse Undermount Cast Iron Kitchen Sink. Butler’s Pantry area and Large Walk-in pantry between the Kitchen and

    Charisma Marin CHARISMA REALTY CORP

    16689 Toccoa Row, Winter Garden, FL 34787
  • /35

    $3,500 Per Month

    • 4 Beds
    • 3.5 Baths
    • 2,781 Sq Ft
    • House for Rent

    12513 Encore at Ovation Way, Winter Garden, FL 34787

    Gas Community, Master bedroom on the second floor. Located in the heart of Orlando's attractions, our new construction homes in Winter Garden provide a unique opportunity to live where you vacation. Encore at Ovation offers quick access to 429 via the 1.6-mile extension of Western Way, making it the most connected location in Village I. Our community's stellar location to nearby 192, World Drive,

    12513 Encore at Ovation Way, Winter Garden, FL 34787
  • /2

    $524,900

    Sold Jan 12, 2026

    14649 Old Thicket Trace, Winter Garden, FL 34787

    • 5 Beds
    • 4.5 Baths
    • 3,436 Sq Ft
    • Built 2006

    Last Sold Summary

    • $153/SF
    • 14 Days On Market

    Current Estimated Value $534,017

    Last Listing Agent Joseph Doher BERKSHIRE HATHAWAY HOMESERVICES RESULTS REALTY

    14649 Old Thicket Trace, Winter Garden, FL 34787
    • /2

      Est $599,608

      Not Listed For Sale

      14401 Black Lake Preserve St, Winter Garden, FL 34787

      • 5 Beds
      • 2.5 Baths
      • 2,511 Sq Ft
      • Built 2018
      14401 Black Lake Preserve St, Winter Garden, FL 34787

      Last Sold Summary

      • 159 Days On Market

Showing Results 361 - 400, Page 10 of 18

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