37,945

Winter Garden, FL Homes

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  • /48

    $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
  • /25

    $4,995 Per Month

    • 3 Beds
    • 3.5 Baths
    • 2,030 Sq Ft
    • Townhouse for Rent

    129 S Park Ave, Winter Garden, FL 34787

    Fully furnished rental, turnkey Urban retreat in Downtown Winter Garden — perfect for snowbirds, recent life-changes, divorcees, or anyone craving an active, walkable Florida lifestyle. This immaculate three-story townhome at Park Place offers 2,030 sq ft of stylish is ready for quality living with 3 beds, 3.5 baths and a custom elevator for easy access to every level. Why you’ll love it? Move-in

    Marc Holland BOARDWALK REALTY, LLC

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

    $540,000

    Sold Apr 22, 2026

    1500 N Fullers Cross Rd, Winter Garden, FL 34787

    • 3 Beds
    • 2 Baths
    • 2,416 Sq Ft
    • Built 2006

    Last Sold Summary

    • $224/SF
    • 5 Days On Market

    Current Estimated Value $539,465

    Last Listing Agent Jorge Coello DENIZ REALTY PARTNERS LLC

    1500 N Fullers Cross Rd, Winter Garden, FL 34787
    • /71

      Est $1,186,441

      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

  • /35

    $469,990

    $15K 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
  • /17

    $1,850 Per Month

    • 2 Beds
    • 1 Bath
    • 966 Sq Ft
    • Condo for Rent

    Unlisted Address

    2 bedrooms, 1 Bath condo with an attached garage. No carpets, all vinyl flooring, including the stairs. Excellent location, end unit. Excellent second bedroom for someone who works from home or for a growing family. Stainless steel appliances in the kitchen.

    Maria Lloret HOMESMART

    Unlisted Address
  • /2

    $1,008,840

    Sold May 20, 2026

    Unlisted Address

    • 5 Beds
    • 3.5 Baths
    • 3,575 Sq Ft
    • Built 2026

    Last Sold Summary

    • $282/SF

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

    Unlisted Address
    • /49

      Est $658,898

      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

  • /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
  • /16

    $3,249 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,908 Sq Ft
    • House for Rent

    12899 Westhaven Oak Dr, Winter Garden, FL 34787

    MODERN 3BR HOME | FENCED YARD | 4-CAR PARKING | PETS WELCOME. Built in 2025 and immaculately maintained, this single-family home in Westhaven at Ovation is the total package and it's move-in ready. The open-concept main floor is light-filled and spacious, with a modern kitchen, generous counter space, and a layout built for real living. Upstairs, the primary suite delivers a walk-in closet and

    Marisol Goncalvez De Ayala AGENT TRUST REALTY CORPORATION

    12899 Westhaven Oak Dr, Winter Garden, FL 34787
  • /2

    $472,000

    Sold Nov 25, 2025

    16341 Lakelet Aly, Winter Garden, FL 34787

    • 3 Beds
    • 2.5 Baths
    • 1,817 Sq Ft
    • Built 2025

    Last Sold Summary

    • 2% Below List Price
    • $260/SF
    • 159 Days On Market

    Current Estimated Value $509,000

    Last Listing Agent Stephen Cline DR HORTON REALTY OF CENTRAL FLORIDA LLC

    16341 Lakelet Aly, Winter Garden, FL 34787
    • /2

      Est $1,439,339

      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

  • /3

    $469,000

    • 4 Beds
    • 3.5 Baths
    • 1,920 Sq Ft

    7030 Twilight Bay Dr, Winter Garden, FL 34787

    Short Sale. Great home, great shape, let's talk

    Richard Cazeau EXP REALTY LLC

    7030 Twilight Bay Dr, Winter Garden, FL 34787
  • /13

    $1,900 Per Month

    • 2 Beds
    • 2 Baths
    • 1,264 Sq Ft
    • Condo for Rent

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

    For rent: Spacious 2-bedroom, 2-bath, fully renovated corner unit 1264 sq.ft. Featuring fresh paint, modern vinyl flooring, and a peaceful wooded view. Located in a resort-style subdivision with top-notch amenities: indoor basketball and racquet ball courts, a full gym, and a barbecue pavilion. Available now for a quick move-in.

    Maria Lloret HOMESMART

    304 Southern Pecan Cir Unit 208, Winter Garden, FL 34787
  • /2

    $408,000

    Sold Nov 26, 2025

    6572 Calamondin Dr, Winter Garden, FL 34787

    • 3 Beds
    • 3 Baths
    • 1,908 Sq Ft
    • Built 2018

    Last Sold Summary

    • 9% Below List Price
    • $214/SF
    • 82 Days On Market

    Current Estimated Value $415,538

    Last Listing Agent Matt Mobley CENTURY 21 HANCOCK

    6572 Calamondin Dr, Winter Garden, FL 34787
    • /49

      Est $590,442

      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

  • /34

    $489,000

    Pending
    • 3 Beds
    • 2 Baths
    • 1,685 Sq Ft

    9318 Mclaren Aly, Winter Garden, FL 34787

    Beautiful corner-lot home in a highly desirable location and excellent condition featuring 3 spacious bedrooms, 2 full bathrooms, a 2-car garage, and a long driveway with space for 2 additional vehicles. This well-maintained, move-in ready property also includes solar panels and a water purification system, offering both comfort and energy efficiency. With great natural lighting and located in a

    Jorge Sanchez Nunez MD3 HOMES LLC

    9318 Mclaren Aly, Winter Garden, FL 34787
  • /23

    $1,895 Per Month

    • 2 Beds
    • 2 Baths
    • 1,152 Sq Ft
    • Condo for Rent

    Unlisted Address

    Prime Location & Resort-Style Living! Welcome home to this beautifully appointed first-floor, 2-bedroom, 2-bath condo in the highly sought-after GATED community of Southern Pines, offering amenities not found in many places: Enjoy resort-style amenities right outside your door, including a community pool, fitness center, indoor basketball court, tennis court, sand volleyball, playground, business

    Marti Purdy MARTI PURDY PROPERTIES INC

    Unlisted Address
  • /2

    $662,000

    Sold Jul 14, 2026

    4231 Oak Lodge Way, Winter Garden, FL 34787

    • 4 Beds
    • 3.5 Baths
    • 2,821 Sq Ft
    • Built 2015

    Last Sold Summary

    • 1% Above List Price
    • $235/SF
    • 10 Days On Market

    Current Estimated Value $621,453

    Last Listing Agent Avi Maganda EMPIRE NETWORK REALTY

    4231 Oak Lodge Way, Winter Garden, FL 34787
    • /2

      Est $493,071

      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

  • /22

    $215,000

    Under Contract
    • 2 Beds
    • 2 Baths
    • 814 Sq Ft

    1008 Stucki Terrace, Winter Garden, FL 34787

    Under contract-accepting backup offers. FULLY RENOVATED 2 BED / 2 BATH UNIT! This beautifully updated home features a modern kitchen and completely renovated bathrooms, offering a clean, move-in-ready feel. The split floor plan provides privacy with both bedrooms designed as en-suite retreats, positioned on *opposite ends of the unit. Enjoy low-maintenance living with tile flooring throughout the

    Gabriella Philippone INDEPENDENCE REALTY GROUP LLC

    1008 Stucki Terrace, Winter Garden, FL 34787
  • /17

    $1,950 Per Month

    • 2 Beds
    • 2 Baths
    • 1,152 Sq Ft
    • Condo for Rent

    316 Southern Pecan Cir Unit 102, Winter Garden, FL 34787

    Beautiful and move-in ready 2-bedroom, 2-bathroom condo located in the highly desirable Winter Garden area. This well-maintained condo offers an open-concept layout, spacious bedrooms, and a modern kitchen with ample cabinet space. Enjoy a comfortable primary suite with a private bathroom and generous closet space. Rent includes water, high-speed internet and TV cable providing added value and

    Vanessa Naim NAIM REAL ESTATE LLC

    316 Southern Pecan Cir Unit 102, Winter Garden, FL 34787
  • /2

    $595,000

    Sold Jan 06, 2026

    14012 Peach Orchard Way, Winter Garden, FL 34787

    • 4 Beds
    • 2 Baths
    • 2,516 Sq Ft
    • Built 2016

    Last Sold Summary

    • $236/SF
    • 5 Days On Market

    Current Estimated Value $598,122

    Last Listing Agent Abby Greenberg COMPASS FLORIDA LLC

    14012 Peach Orchard Way, Winter Garden, FL 34787
    • /34

      Est $447,559

      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

  • /13

    $99,000

    $11K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,248 Sq Ft

    14816 Sugura Dr Unit 2111, Winter Garden, FL 34787

    This nicely maintained two-bedroom, two-bathroom home offers the perfect blend of comfort and convenience. Step inside to discover a spacious layout with a separate Florida room and plenty of natural light. The French doors open up to the main living space with built in cabinet and dining area. The spacious bedrooms are very comfortable for anyone. The screened in porch offers a lovely outdoor

    Kim Unger CFL PROPERTY GROUP

    14816 Sugura Dr Unit 2111, Winter Garden, FL 34787
  • /32

    $2,665 Per Month

    • 3 Beds
    • 2 Baths
    • 1,591 Sq Ft
    • House for Rent

    224 Faulkner St, Winter Garden, FL 34787

    Welcome to 224 Faulkner St, a well-maintained 3-bedroom, 2-bathroom single-story home located within the golf cart district of desirable Winter Garden.As you enter the home, you're welcomed into a spacious living and dining area featuring vaulted ceilings, abundant natural light, and direct access to the backyard. The kitchen includes a breakfast bar, refrigerator, oven, and dishwasher, and

    Anthony O'Reilly Brookes WINTER GARDEN REAL ESTATE

    224 Faulkner St, Winter Garden, FL 34787
  • /2

    $595,000

    Sold Mar 31, 2026

    14430 Orchard Hills Blvd, Winter Garden, FL 34787

    • 3 Beds
    • 2.5 Baths
    • 2,471 Sq Ft
    • Built 2016

    Last Sold Summary

    • $241/SF
    • 5 Days On Market

    Current Estimated Value $591,147

    Last Listing Agent Cari Fitzgerald PREMIER SOTHEBYS INT'L REALTY

    14430 Orchard Hills Blvd, Winter Garden, FL 34787
    • /2

      Est $274,269

      Not Listed For Sale

      130 Southern Pecan Cir Unit 204, Winter Garden, FL 34787

      • 3 Beds
      • 2 Baths
      • 1,453 Sq Ft
      • Built 2005
      130 Southern Pecan Cir Unit 204, Winter Garden, FL 34787

      Last Sold Summary

      • 33 Days On Market

  • /53

    $549,990

    $9K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,042 Sq Ft

    16153 Water Spring Blvd, Winter Garden, FL 34787

    Single Family bungalow, 4 bedrooms and 3 full bathrooms, with backyard is rare. Designed for comfort and modern living, this property offers no carpet throughout, creating a clean and elegant look with luxury vinyl plank flooring. All pictures are real, no virtual staging or AI. The home includes a dedicated office space, thoughtfully designed and decorated, perfect for working from home. Enjoy

    Rodrigo Khoury Francisco WRA BUSINESS & REAL ESTATE

    16153 Water Spring Blvd, Winter Garden, FL 34787
  • /11

    $1,600 Per Month

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

    430 Southern Pecan Cir Unit 203, Winter Garden, FL 34787

    Beautiful 1 bedroom 1 bath condo on second floor in gated community of Southern Pines. Features additional office/solarium room. Open floor plan concept with carpeted living areas and tiled wet areas. Kitchen and bathroom both have granite counter tops. Master bedroom with walk in closet. Community features pool, tennis, basketball, fitness room, playground and more. Great location close to

    Nicholas Horton BANNER INT'L REAL ESTATE

    430 Southern Pecan Cir Unit 203, Winter Garden, FL 34787
  • /2

    $666,502

    Sold Mar 10, 2026

    17091 Haggerty Hollow Dr, Winter Garden, FL 34787

    • 4 Beds
    • 3.5 Baths
    • 2,515 Sq Ft
    • Built 2026

    Move in Ready Sold Summary

    • $265/SF
    • 10 Days On Market

    Current Estimated Value $669,000

    Dream Finders Homes Hamlin Meadows - 40' Homesites

    17091 Haggerty Hollow Dr, Winter Garden, FL 34787
    • /83

      Est $472,464

      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

  • /49

    $310,000

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

    14501 Grove Resort Ave Unit 1518, Winter Garden, FL 34787

    BEST VIEW IN THE ENTIRE RESORT! A rare opportunity to own a beautifully appointed 5th-floor, 2-bedroom, 2-bath luxury residence in the MAIN BUILDING at The Grove Resort & Water Park—offering breathtaking, UNOBSTRUCTED PANORAMIC VIEWS of LAKE AUSTIN and the SPRING POOLS. This exceptional condo features an open, light-filled floor plan and a private screened balcony, creating the perfect setting to

    Edit Gabor FLORIDA CAPITAL REALTY

    14501 Grove Resort Ave Unit 1518, Winter Garden, FL 34787
  • /29

    $2,995 Per Month

    • 4 Beds
    • 2 Baths
    • 1,867 Sq Ft
    • House for Rent

    2227 Oakington St, Winter Garden, FL 34787

    Must see!! Welcome Home, beautiful property with a lots of upgrades, freshly painted. Four ample bedrooms, separated Living and Dining,kitchen with granite counter tops. All appliances are included. Master suite with a large walking closet, and separate upgraded master bathroom with skylights. Big patio fenced. Conveniently Gated Community with Security Guard 24 hrs, closed Shopping centers,

    Milena Nunez REALTY ONE GROUP EVOLUTION

    2227 Oakington St, Winter Garden, FL 34787
  • /35

    $67,000

    Sold Oct 27, 2025

    16526 Menorca Dr, Winter Garden, FL 34787

    • 2 Beds
    • 2 Baths
    • Built 1988

    Last Sold Summary

    • 26% Below List Price
    • 52 Days On Market

    Last Listing Agent Chrissy Walter Sunset Home Sales

    16526 Menorca Dr, Winter Garden, FL 34787
    • /70

      Est $1,753,359

      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

  • /26

    $599,000

    $31K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 2,484 Sq Ft

    17865 Adrift Rd, Winter Garden, FL 34787

    A home full of charm, comfort, and practicality. It features four bedrooms, including a spacious master suite, three full bathrooms, and a powder room, distributed in a clever layout that enhances each room. Right at the entrance, the balcony invites you to slow down and enjoy the home's cozy atmosphere. The kitchen is modern and functional, equipped with all essential appliances and a central

    Joao De Souza Freitas, Jr WRA BUSINESS & REAL ESTATE

    17865 Adrift Rd, Winter Garden, FL 34787
  • /30

    $1,795 Per Month

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

    53 Windtree Ln Unit 102, Winter Garden, FL 34787

    Virtually Staged. This 2 bedroom and 2 bath condo is located on the FIRST FLOOR and it comes with tiled flooring throughout, all appliances, and fresh paint. Two assigned parking spaces for your convenience and beautiful amenities like pool, and basketball courts. Located at closed proximity to Downtown Winter Garden, shopping, public transportation, and restaurants. Clean and ready for you!

    Francisco Nieves-Taranto CT HOMES REALTY CORPORATION

    53 Windtree Ln Unit 102, Winter Garden, FL 34787
  • /25

    $469,990

    Sold Mar 18, 2026

    17311 Beachgrass Aly, Winter Garden, FL 34787

    • 3 Beds
    • 2 Baths
    • 1,510 Sq Ft
    • Built 2026

    Move in Ready Sold Summary

    • $311/SF
    • 6 Days On Market

    Current Estimated Value $470,000

    M/I Homes Lake Star at Ovation - Avenue Collection

    17311 Beachgrass Aly, Winter Garden, FL 34787
    • /9

      Est $207,621

      Not Listed For Sale

      225 Southern Pecan Cir Unit 106, Winter Garden, FL 34787

      • 1 Bed
      • 1 Bath
      • 838 Sq Ft
      • Built 2005
      225 Southern Pecan Cir Unit 106, Winter Garden, FL 34787

      Last Sold Summary

      • 144 Days On Market

Showing Results 641 - 680, Page 17 of 18

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