37,760

Winter Garden, FL Homes

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  • /30

    $335,000

    Pending
    • 2 Beds
    • 2 Baths
    • 1,100 Sq Ft

    243 Florida Ave, Winter Garden, FL 34787

    Fully Renovated Turnkey Home in the Heart of Winter Garden, Better Than New! This beautifully reimagined 2-bedroom, 2-bath home has been transformed from the ground up. Every major system and finish is brand new, including the foundation, structural reinforcement, roof, windows, flooring, A/C system, and fully remodeled bathrooms, plus an ADDED second bathroom. The modern kitchen features a

    Laury Cruz Penalo De Gomez MY REALTY GROUP, LLC.

    243 Florida Ave, Winter Garden, FL 34787
  • /52

    $11,500 Per Month

    • 5 Beds
    • 5.5 Baths
    • 5,005 Sq Ft
    • House for Rent

    15704 Marina Bay Dr, Winter Garden, FL 34787

    Location, Location, Location!?This spectacular lakefront estate truly has it all. Thoughtfully upgraded throughout, the home features a gourmet kitchen with 42" cabinetry, an oversized island, and an expansive walk-in pantry—ideal for both everyday living and entertaining. A modern wine room adds a distinctive touch, while breathtaking lake views welcome you the moment you enter the home.The

    Marcelo Moura DOUBLE M GROUP COMPANY

    15704 Marina Bay Dr, Winter Garden, FL 34787
  • /31

    $459,990

    Sold Nov 26, 2025

    15505 Bay Bridge St, Winter Garden, FL 34787

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

    Move in Ready Sold Summary

    • $251/SF
    • 6 Days On Market

    Current Estimated Value $459,365

    15505 Bay Bridge St, Winter Garden, FL 34787
    • /2

      Not Listed For Sale

      14200 Avalon Rd Unit 225, Winter Garden, FL 34787

      • 2 Beds
      • 2 Baths
      • 1,203 Sq Ft
      • Built 2008
      14200 Avalon Rd Unit 225, Winter Garden, FL 34787

      Last Sold Summary

      • 55 Days On Market

  • /24

    $899,999

    New Construction
    • 5 Beds
    • 5.5 Baths
    • 4,591 Sq Ft

    Ravenna Plan at Esplanade at McKinnon Groves 50' Lot, Winter Garden, FL 34787

    This 2-story home with a courtyard features 5 bedrooms, 5.5 bathrooms, a 3-car garage and 4,591 square feet. This sprawling home has so much to offer, with a formal dining room, an oversized great room, and a stunning kitchen. The Ravenna has a variety of structural options to make this home uniquely yours, with a multi-gen suite, media room, study, outdoor kitchen, and so much more.

    Taylor Morrison Builder
    0 Marsh Rd Unit 40619864, Winter Garden, FL 34787
  • /31

    $2,800 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,844 Sq Ft
    • Townhouse for Rent

    15221 Sunrise Grove Ct, Winter Garden, FL 34787

    Elegant Townhome in Gated Winter Garden Community – Resort-Style Living Awaits. Welcome to your next home in the charming and sought-after community of Hickory Hammock at Johns Lake, nestled in the heart of Winter Garden. This beautifully maintained townhome offers theperfect blend of comfort, convenience, and natural beauty — all within a secure, gated neighborhood just minutes from

    Mary Heitz REALTY ONE SPECIALISTS LLC

    15221 Sunrise Grove Ct, Winter Garden, FL 34787
  • /2

    $479,000

    Sold May 08, 2026

    1419 Hunterman Ln, Winter Garden, FL 34787

    • 5 Beds
    • 4.5 Baths
    • 2,840 Sq Ft
    • Built 2005

    Last Sold Summary

    • $169/SF
    • 7 Days On Market

    Current Estimated Value $490,092

    Last Listing Agent Robert Salmons ENTERA REALTY LLC

    1419 Hunterman Ln, Winter Garden, FL 34787
    • /24

      Est $427,835

      Not Listed For Sale

      6431 Sweet Clementine Aly, Winter Garden, FL 34787

      • 3 Beds
      • 3 Baths
      • 1,903 Sq Ft
      • Built 2018
      6431 Sweet Clementine Aly, Winter Garden, FL 34787

      Last Sold Summary

      • 0 Days On Market

  • /78

    $1,525,000

    Pending
    • 5 Beds
    • 6 Baths
    • 4,964 Sq Ft

    15047 Gaulberry Run, Winter Garden, FL 34787

    Under contract-accepting backup offers. This is the one you’ve been waiting for! Tucked away on a peaceful cul-de-sac and situated on an expansive half-acre corner lot, this stunning Horizon West home, in the highly sought-after community of Independence, offers exceptional curb appeal, privacy and luxury living at every turn. Inside, experience soaring, double-height ceilings and an abundance of

    Lynda Miller PREMIER SOTHEBYS INT'L REALTY

    15047 Gaulberry Run, Winter Garden, FL 34787
  • /22

    $3,999 Per Month

    • 4 Beds
    • 3 Baths
    • 2,541 Sq Ft
    • House for Rent

    10194 Atwater Bay Dr, Winter Garden, FL 34787

    Beautiful 4-bedroom, 3-bath home available for rent in the highly desirable Waterleigh community of Winter Garden. This spacious residence features an open-concept floor plan, a modern kitchen with stainless steel appliances, generous living areas, and abundant natural light throughout. Enjoy access to resort-style community amenities including pools, fitness centers, playgrounds, walking trails,

    Frederico Hexsel KARDOSH REALTY

    10194 Atwater Bay Dr, Winter Garden, FL 34787
  • /2

    $1,600,000

    Sold Dec 02, 2025

    16629 Broadwater Ave, Winter Garden, FL 34787

    • 5 Beds
    • 5 Baths
    • 4,048 Sq Ft
    • Built 2016

    Last Sold Summary

    • 20% Below List Price
    • $395/SF
    • 220 Days On Market

    Current Estimated Value $1,638,477

    Last Listing Agent Sean Spencer PREMIER SOTHEBYS INT'L REALTY

    16629 Broadwater Ave, Winter Garden, FL 34787
    • /71

      Est $1,228,416

      Not Listed For Sale

      132 Stanton Estates Cir, Winter Garden, FL 34787

      • 4 Beds
      • 4 Baths
      • 3,571 Sq Ft
      • Built 2018
      132 Stanton Estates Cir, Winter Garden, FL 34787

      Last Sold Summary

      • 33 Days On Market

  • /2

    $712,634

    New Construction Pending
    • 3 Beds
    • 3.5 Baths
    • 2,515 Sq Ft

    6050 Flowering Cherry Bend, Winter Garden, FL 34787

    One or more photo(s) has been virtually staged. Pre-Construction. To be built. Opportunity in Avalon Woods! Discover the newest community by Dream Finders Homes in highly sought-after Hamlin, Winter Garden. Welcome to the Carter, a thoughtfully designed bungalow that combines style, comfort, and modern functionality. This brand-new home offers 4 bedrooms, 3.5 bathrooms, and 2,520 sq. ft. of

    Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

    6050 Flowering Cherry Bend, Winter Garden, FL 34787
  • /23

    $2,850 Per Month

    • 3 Beds
    • 2 Baths
    • 1,992 Sq Ft
    • Property for Rent

    8112 Red Crossbill St, Winter Garden, FL 34787

    ... Available on July 1, 2026... This rare find beautiful one story house offers 3 bedroom/2 bath/2 car garage... No carpet in the entire house... It features stainless steel appliances, tile flooring, and luxury vinyl plank in all bedrooms. It is located in Summerlake community which offers resort style pool, gym, tennis courts, basketball courts, zip liner, dog park, and many more. Lawn

    Jennie Ho MAY HO REALTY

    8112 Red Crossbill St, Winter Garden, FL 34787
  • /2

    $860,000

    Sold Jun 23, 2025

    Unlisted Address

    • 4 Beds
    • 3 Baths
    • 3,555 Sq Ft
    • Built 2023

    Last Sold Summary

    • $242/SF

    Current Estimated Value $811,791

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

    Unlisted Address
    • /49

      Est $687,473

      Not Listed For Sale

      14224 Sunridge Blvd, Winter Garden, FL 34787

      • 4 Beds
      • 3 Baths
      • 2,810 Sq Ft
      • Built 2017
      14224 Sunridge Blvd, Winter Garden, FL 34787

      Last Sold Summary

      • 18 Days On Market

  • /40

    $1,020,000

    • 3 Beds
    • 2 Baths
    • 1,364 Sq Ft

    16104 Sandhill Rd, Winter Garden, FL 34787

    Rare opportunity to own nearly 5 acres in the coveted Lake Avalon Rural Settlement—where horses, heritage oaks, and peaceful country living meet the convenience of Winter Garden.Escape the hustle and discover one of Winter Garden's last remaining rural neighborhoods. Set on 4.85 fully fenced acres, this picturesque property offers expansive green pastures, majestic oak and heritage trees, and

    Cheryl Gritzer CLOCK TOWER REALTY

    16104 Sandhill Rd, Winter Garden, FL 34787
  • /18

    $2,100 Per Month

    • 3 Beds
    • 2 Baths
    • 984 Sq Ft
    • Townhouse for Rent

    1000 Dolphin Dr, Winter Garden, FL 34787

    Enjoy living in this beautiful 3-bedroom, 2-bath home featuring a spacious fenced backyard and situated on a desirable corner lot. The modern kitchen offers elegant quartz countertops, perfect for cooking and entertaining. Conveniently located just 5 minutes from Downtown Winter Garden, you’ll love being close to great schools, restaurants, shopping, farmers markets, and plenty of activities

    Gian Balsamo LA ROSA REALTY KISSIMMEE

    1000 Dolphin Dr, Winter Garden, FL 34787
  • /2

    $443,000

    Sold Jul 21, 2025

    6418 Tabebuia Pkwy, Winter Garden, FL 34787

    • 3 Beds
    • 2.5 Baths
    • 1,683 Sq Ft
    • Built 2024

    Last Sold Summary

    • 4% Below List Price
    • $263/SF
    • 78 Days On Market

    Last Listing Agent Adrienne Escott PULTE REALTY OF NORTH FLORIDA LLC

    6418 Tabebuia Pkwy, Winter Garden, FL 34787
    • /2

      Est $1,488,837

      Not Listed For Sale

      14968 Porter Rd, Winter Garden, FL 34787

      • 6 Beds
      • 6.5 Baths
      • 5,084 Sq Ft
      • Built 2017
      14968 Porter Rd, Winter Garden, FL 34787

      Last Sold Summary

      • 427 Days On Market

  • /58

    $600,000

    Pending
    • 3 Beds
    • 2 Baths
    • 2,075 Sq Ft

    13958 Magnolia Ridge Loop, Winter Garden, FL 34787

    Under contract-accepting backup offers. MUST SEE IN PERSON! Incredible Upgrades! Welcome to this meticulously maintained home located in the desired ORCHARD HILLS community within the Winter Garden zip-code. This 3 bedroom home with the potential to become 4 bedrooms (currently an office), 2 full custom bathrooms and a screened-in patio blends thoughtful design with modern convenience. The

    Raymond Glenn LAKESIDE REALTY WINDERMERE INC

    13958 Magnolia Ridge Loop, Winter Garden, FL 34787
  • /22

    $3,000 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,881 Sq Ft
    • House for Rent

    14624 Watowan Aly, Winter Garden, FL 34787

    Welcome to this beautiful 3-bedroom, 2.5-bath home with a spacious loft, located in the desirable Watermark community! The open-concept floor plan offers an inviting family room that seamlessly flows into a stylish kitchen featuring 42" cabinets, granite countertops, and stainless steel appliances—perfect for entertaining and everyday living. The primary suite boasts a generous walk-in closet and

    Andre Kressler KRESSLER REAL ESTATE

    14624 Watowan Aly, Winter Garden, FL 34787
  • /2

    $540,000

    Sold Jul 07, 2025

    1013 Glensprings Ave, Winter Garden, FL 34787

    • 3 Beds
    • 2 Baths
    • 1,680 Sq Ft
    • Built 1986

    Last Sold Summary

    • 2% Below List Price
    • $321/SF
    • 47 Days On Market

    Current Estimated Value $526,399

    Last Listing Agent Jenny Ramirez COLDWELL BANKER REALTY

    1013 Glensprings Ave, Winter Garden, FL 34787
    • /49

      Est $601,926

      Not Listed For Sale

      15307 Southern Martin St, Winter Garden, FL 34787

      • 4 Beds
      • 3 Baths
      • 2,428 Sq Ft
      • Built 2017
      15307 Southern Martin St, Winter Garden, FL 34787

      Last Sold Summary

      • 29 Days On Market

  • /46

    $199,000

    $30K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,375 Sq Ft

    14501 Grove Resort Ave Unit 3724, Winter Garden, FL 34787

    This stunning 7th-floor condo at The Grove Resort & Spa offers breathtaking water views, overlooking the pond, water park and conservation serene area. This fully furnished, all-inclusive condo-hotel provides a truly hands-off investment opportunity with onsite property management and a full-service rental program. Located in Building 3, this luxury 2-bedroom, 2-bath unit is perfectly situated

    Alexis McKenzie REAL BROKER, LLC

    14501 Grove Resort Ave Unit 3724, Winter Garden, FL 34787
  • /42

    $2,950 Per Month

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

    15883 Tollington Aly, Winter Garden, FL 34787

    LIKE-NEW CORNER LOT MODEL TOWNHOME available for lease in the HIGHLY DESIRABLE HORIZON WEST COMMUNITY! This FULLY UPGRADED 2-story residence offers the perfect blend of style, comfort, and functionality, featuring 3 spacious bedrooms, 2 bathrooms, and a 2-car garage. The thoughtfully designed open-concept floor plan creates a seamless flow between the living room, dining area, and gourmet

    Fanny Stollmeyer LIFESTYLE INTERNATIONAL REALTY

    15883 Tollington Aly, Winter Garden, FL 34787
  • /2

    $625,000

    Sold Nov 14, 2025

    617 Glenview Dr, Winter Garden, FL 34787

    • 4 Beds
    • 2 Baths
    • 3,050 Sq Ft
    • Built 1984

    Last Sold Summary

    • 4% Below List Price
    • $205/SF
    • 25 Days On Market

    Current Estimated Value $613,650

    Last Listing Agent Julia Meffen FLORIDA HOMES & LOANS INC.

    617 Glenview Dr, Winter Garden, FL 34787
    • /2

      Est $488,894

      Not Listed For Sale

      11072 Folklore St, Winter Garden, FL 34787

      • 4 Beds
      • 3 Baths
      • 2,042 Sq Ft
      • Built 2017
      11072 Folklore St, Winter Garden, FL 34787

      Last Sold Summary

      • 195 Days On Market

  • /35

    $474,990

    $10K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,070 Sq Ft

    16396 Prairie School Dr, Winter Garden, FL 34787

    Step into this exceptionally maintained corner townhome, built in 2021, filled with natural light and thoughtful upgrades throughout. With 3 bedrooms, 2.5 bathrooms, a flexible first-floor space perfect for a home office, and a cozy second-floor loft, this home adapts seamlessly to your lifestyle.The chef-ready kitchen features a butler’s pantry with an extra sink, ideal for entertaining or

    Carly Ruecker DENIZ REALTY PARTNERS LLC

    16396 Prairie School Dr, Winter Garden, FL 34787
  • /15

    $2,800 Per Month

    • 3 Beds
    • 2.5 Baths
    • 2,000 Sq Ft
    • House for Rent

    14384 Braemar St, Winter Garden, FL 34787

    SPECIAL $300 OFF THE 1ST MO RENT - terms apply This Beautiful home is located in the Highland Ridge community in Winter Garden. The house features a family and dining room with a mix of laminate and carpet flooring, as well as stunning fixtures throughout. The open kitchen is equipped with stainless steel appliances, a breakfast bar, and a large pantry. The spacious master bedroom includes both a

    Nancy Guadagnino SPECIALIZED PROPERTY MANAGEMENT

    14384 Braemar St, Winter Garden, FL 34787
  • /2

    $550,000

    Sold Oct 14, 2025

    18 Cooledge St, Winter Garden, FL 34787

    • 4 Beds
    • 2 Baths
    • 2,128 Sq Ft
    • Built 2006

    Last Sold Summary

    • 11% Below List Price
    • $258/SF
    • 154 Days On Market

    Current Estimated Value $560,906

    Last Listing Agent Ty McTague KELLER WILLIAMS REALTY AT THE PARKS

    18 Cooledge St, Winter Garden, FL 34787
    • /34

      Est $438,252

      Not Listed For Sale

      17107 Harbor Oak Pkwy, Winter Garden, FL 34787

      • 3 Beds
      • 2 Baths
      • 1,692 Sq Ft
      • Built 2017
      17107 Harbor Oak Pkwy, Winter Garden, FL 34787

      Last Sold Summary

      • 31 Days On Market

  • /50

    $230,000

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

    14501 Grove Resort Ave Unit 1310, Winter Garden, FL 34787

    Fully Furnished & Turn-Key Ready! Welcome to your dream vacation retreat at the highly sought-after Grove Resort & Spa—a full-service luxury resort just 10 minutes from Disney World! This spacious 2-bedroom, 2-bathroom Jasmine Model is located on the 3rd floor and offers 1,265 sqft of comfortable living space, including a screened-in balcony with serene views. Enjoy the ultimate resort lifestyle

    Vinny Apolinario WRA BUSINESS & REAL ESTATE

    14501 Grove Resort Ave Unit 1310, Winter Garden, FL 34787
  • /45

    $3,600 Per Month

    • 4 Beds
    • 3 Baths
    • 2,424 Sq Ft
    • House for Rent

    11965 Bracco St, Winter Garden, FL 34787

    Step into this stunning and move-in ready home, completed in April 2025 and loaded with modern upgrades and designer touches throughout! Featuring a bright open-concept layout, the chef-inspired kitchen showcases elegant gold fixtures and flows seamlessly into the spacious dining and living areas, perfect for entertaining or enjoying everyday family life. Need extra flexibility? The private study

    Denise Batista ALLUX REAL ESTATE LLC

    11965 Bracco St, Winter Garden, FL 34787
  • /26

    $739,990

    Sold Sep 04, 2025

    13122 Faro Ct, Winter Garden, FL 34787

    • 5 Beds
    • 4.5 Baths
    • 3,719 Sq Ft
    • Built 2025

    Move in Ready Sold Summary

    • $199/SF
    • 9,378 Days On Market

    13122 Faro Ct, Winter Garden, FL 34787
    • /83

      Est $474,536

      Not Listed For Sale

      15136 Sunrise Grove Ct, Winter Garden, FL 34787

      • 3 Beds
      • 2.5 Baths
      • 2,360 Sq Ft
      • Built 2017
      15136 Sunrise Grove Ct, Winter Garden, FL 34787

      Last Sold Summary

      • 50 Days On Market

  • /46

    $745,000

    Pending
    • 3 Beds
    • 2 Baths
    • 1,916 Sq Ft

    708 Orange Belt Loop, Winter Garden, FL 34787

    LOCATED IN THE HIGHLY SOUGHT AFTER GOLF CART DISTRICT OF DOWNTOWN WINTER GARDEN!!! This beautifully maintained and move-in ready, this immaculate 3-bedroom, 2-bath home offers comfort, style, and convenience in one exceptional package. Featuring all tile flooring throughout with no carpet, stunning plantation shutters, the open and spacious floor plan seamlessly connects the kitchen, dining, and

    Kristi Lowery OLYMPUS EXECUTIVE REALTY INC

    708 Orange Belt Loop, Winter Garden, FL 34787
  • /46

    $2,750 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,996 Sq Ft
    • Townhouse for Rent

    13881 Easdale Aly, Winter Garden, FL 34787

    GORGEOUS modern end-unit Toll Brothers townhome located in the desired Horizon West Area is available for rent! Built in 2024, this 3-bedroom, 2.5-bath residence delivers a nearly-new feel and is immaculate throughout! This two-story home features a beautiful kitchen with ample cabinetry, built-in oven, island and so much more! High-ceilings throughout on the main level. Living and dining areas

    Cleve Loveland LOVELAND PROPERTIES

    13881 Easdale Aly, Winter Garden, FL 34787
  • /2

    $579,900

    Sold Apr 24, 2026

    14568 Spotted Sandpiper Blvd, Winter Garden, FL 34787

    • 3 Beds
    • 2 Baths
    • 1,997 Sq Ft
    • Built 2013

    Last Sold Summary

    • 3% Below List Price
    • $290/SF
    • 17 Days On Market

    Current Estimated Value $582,768

    Last Listing Agent Jared Lippelgoos COLDWELL BANKER REALTY

    14568 Spotted Sandpiper Blvd, Winter Garden, FL 34787
    • /70

      Est $1,831,827

      Not Listed For Sale

      6723 Point Hancock Dr, Winter Garden, FL 34787

      • 6 Beds
      • 6 Baths
      • 5,022 Sq Ft
      • Built 2012
      6723 Point Hancock Dr, Winter Garden, FL 34787

      Last Sold Summary

      • 544 Days On Market

Showing Results 601 - 640, Page 16 of 18

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