Winter Garden, FL Homes

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  /59

  $695,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 2,763 Sq Ft

  15508 Pebble Ridge St, Winter Garden, FL 34787

  This is the one you’ve been waiting for. A beautifully maintained four bedroom pool home in Stoneybrook West, offering the space, layout, and updates that are so hard to find all in one place. Inside, the home opens with a traditional yet functional flow formal living to the left, dining to the right, leading you into a spacious family room with views of the pool and backyard. The outdoor space

  

  Barrett Spray

  KELLER WILLIAMS ADVANTAGE REALTY

  (321) 529-3911

  15508 Pebble Ridge St, Winter Garden, FL 34787
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  /34

  $3,950 per month

  • 4 Beds
  • 3 Baths
  • 2,470 Sq Ft
  • House for Rent

  16822 Wingspread Loop, Winter Garden, FL 34787

  Beautifully fully fenced, 4-bed, 3-bathroom home plus a flex room that can serve as a home office, entertainment room, or kids' play area. Modern model by "Mattamy homes" located in the community of Hawksmoor. Featuring an open floor plan tiled from wall to wall, gourmet kitchen with 42" upper kitchen cabinets, quartz countertops, mosaic glass backsplash, huge pantry, and smart technology

  Evelsi Conqueth ASSURANCE FLORIDA REALTY

  16822 Wingspread Loop, Winter Garden, FL 34787
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  /2

  $807,000 Sold Jun 03, 2025

  16694 Olive Hill Dr, Winter Garden, FL 34787

  • 4 Beds
  • 2.5 Baths
  • 2,862 Sq Ft
  • Built 2019

  Last Sold Summary

  • 8% Below List Price
  • $282/SF
  • 43 Days On Market

  Current Estimated Value $803,960

  Last Listing Agent Vanessa Franz Barnes KELLER WILLIAMS REALTY AT THE LAKES

  16694 Olive Hill Dr, Winter Garden, FL 34787
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  /17

  Est $536,758 Not Listed For Sale

  9014 Pinch Shot Dr, Winter Garden, FL 34787

  • 3 Beds
  • 2 Baths
  • 2,089 Sq Ft
  • Built 2018

  9014 Pinch Shot Dr, Winter Garden, FL 34787

  Last Sold Summary

  • 1% Below List Price
  • $258/SF
  • 2 Days On Market

  • Last Sold Price $540,000
  • Aug 21, 2023

  Last Listing Agent Junior Pipo WRA BUSINESS & REAL ESTATE
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  /40

  $359,900

  • 3 Beds
  • 2.5 Baths
  • 1,590 Sq Ft

  13705 Golden Russet Dr, Winter Garden, FL 34787

  Welcome to The Orchard, a tidy gated community of townhomes in sought-after Winter Garden. This residence blends modern comfort with low-maintenance living, offering a bright, open layout that feels inviting from the moment you step inside. Thoughtful upgrades elevate every space—stylish flooring, fresh finishes, and a contemporary color palette create a clean, move-in-ready atmosphere.The

  

  Drew Ross

  LAKEFIELD REALTY GROUP LLC

  (321) 399-2408

  13705 Golden Russet Dr, Winter Garden, FL 34787
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  /23

  $1,772 - $3,128 total monthly price

  Corban Horizon West

  1 - 3 Beds

  15000 Stratus Loop, Winter Garden, FL 34787

  Take the next step in life at Corban Horizon West. A place that draws inspiration from the warmth of the neighborhood and the endless possibilities that surround it, our homes offer a refreshing experience guaranteed to exceed your expectations for modern living. Timeless yet contemporary. Comfortable yet connected. Our residences are a wonderful blend of tasteful design, thoughtful amenities and

  15000 Stratus Loop, Winter Garden, FL 34787
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  /2

  $275,000 Sold Sep 15, 2025

  1300 Eastern Pecan Place Unit 104, Winter Garden, FL 34787

  • 3 Beds
  • 2 Baths
  • 1,340 Sq Ft
  • Built 2005

  Last Sold Summary

  • 8% Below List Price
  • $205/SF
  • 90 Days On Market

  Last Listing Agent Todd Schroth EXP REALTY LLC

  1300 Eastern Pecan Place Unit 104, Winter Garden, FL 34787
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  /51

  Est $506,125 Not Listed For Sale

  Unlisted Address

  • 4 Beds
  • 3.5 Baths
  • 2,321 Sq Ft
  • Built 2019

  Unlisted Address

  Last Sold Summary

  • 1% Below List Price
  • $220/SF
  • 7 Days On Market

  • Last Sold Price $510,000
  • Apr 28, 2023

  Last Listing Agent Richard Lokhnauth RL LUXURY REAL ESTATE
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  /36

  $270,000

  • 3 Beds
  • 3 Baths
  • 1,544 Sq Ft

  14501 Grove Resort Ave Unit 2527, Winter Garden, FL 34787

  Short Sale. Short Sale Opportunity – Fully Furnished 3BR/3BA Condo at The Grove Resort – Vacation Rental Only / No Full-Time ResidencyInvestor Alert! Rare opportunity to own a FULLY FURNISHED and equipped 3-bedroom, 3-bath condo in the sought-after The Grove Resort, one of Orlando’s top vacation-only condo-hotel communities, just minutes from Disney. Turnkey for immediate rental. Large

  

  Nayane Seabra

  WRA BUSINESS & REAL ESTATE

  (321) 341-5486

  14501 Grove Resort Ave Unit 2527, Winter Garden, FL 34787
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  /45

  $3,150 per month

  • 5 Beds
  • 3 Baths
  • 2,638 Sq Ft
  • House for Rent

  9131 Cut Shot Dr, Winter Garden, FL 34787

  Freshly Painted!!! Now available for lease is this gorgeous 5-bedroom, 3-bathroom residence situated in one of Central Florida's most coveted neighborhoods! This exceptional home boasts an attached rear load 2-car garage and a charming front porch. Inside, you'll find an inviting open-concept layout with tile flooring adorning the living spaces. The airy kitchen features 42" cabinets, stone

  Zane Place BLUE CHIP INTERNATIONAL REALTY LLC

  9131 Cut Shot Dr, Winter Garden, FL 34787
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  /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 $923,057

  Last Listing Agent Jaime Galeoto FLORIDA REALTY RESULTS LLC

  17234 Cork St, Winter Garden, FL 34787
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  /2

  Est $575,703 Not Listed For Sale

  9250 Cut Shot Dr, Winter Garden, FL 34787

  • 5 Beds
  • 3 Baths
  • 2,461 Sq Ft
  • Built 2018

  9250 Cut Shot Dr, Winter Garden, FL 34787

  Last Sold Summary

  • $234/SF
  • 144 Days On Market

  • Last Sold Price $575,000
  • Sep 04, 2024

  Last Listing Agent peipei Qiao BAY STREET GROUP FLORIDA LLC
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  /33

  $559,900 Open Sat 11AM - 2PM

  • 3 Beds
  • 2.5 Baths
  • 1,964 Sq Ft

  14280 Braemar St, Winter Garden, FL 34787

  Welcome to this beautifully maintained 3-bedroom, 2.5-bath single-family home built in 2023, offering 2,048 sq ft of modern living in the highly desirable city of Winter Garden. This thoughtfully designed home features a stylish kitchen with stainless steel appliances and granite countertops, seamlessly connecting to the main living and dining areas—perfect for everyday living and entertaining.

  

  Keegan Siegfried

  LPT REALTY, LLC

  (321) 497-0945

  14280 Braemar St, Winter Garden, FL 34787
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  /38

  $1,500 - $1,750 per month

  Garden City Apartments

  2 Beds

  521 S Park Ave, Winter Garden, FL 34787

  Garden City Apartments is nestled in the heart of Downtown Winter Garden, Florida. Within walking distance or a quick golf cart ride to Historic Plant Street, life is full of excitement with local arts and entertainment, trails and restaurants galore you will surely feel at home and safe living in our newly renovated industrial designed family-friendly apartments. We have a mix between

  521 S Park Ave, Winter Garden, FL 34787
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  /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 $484,139

  Last Listing Agent Dana Gold RE/MAX ASSURED

  12272 Bracco St, Winter Garden, FL 34787
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  /2

  Est $685,200 Not Listed For Sale

  14891 Winter Stay Dr, Winter Garden, FL 34787

  • 4 Beds
  • 3 Baths
  • 2,662 Sq Ft
  • Built 2018

  14891 Winter Stay Dr, Winter Garden, FL 34787

  Last Sold Summary

  • $257/SF
  • 128 Days On Market

  • Last Sold Price $685,000
  • Sep 06, 2024

  Last Listing Agent Natsue Siqueira FLORIDA REALTY INVESTMENTS
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  /31

  $735,000

  • 5 Beds
  • 4 Baths
  • 2,878 Sq Ft

  14345 Wabasso Loop, Winter Garden, FL 34787

  Located within the gated community of Tilden Place, this thoughtfully designed home offers exceptional flexibility and everyday comfort in one of Winter Garden’s most convenient locations. The main level features a private primary suite along with three additional bedrooms, including an en suite option ideal for guests, multigenerational living, or a home office. Upstairs, a spacious loft,

  

  Hilary Hall

  COMPASS FLORIDA LLC

  (321) 461-2856

  14345 Wabasso Loop, Winter Garden, FL 34787
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  /23

  $2,400 per month

  • 3 Beds
  • 2 Baths
  • 1,453 Sq Ft
  • Condo for Rent

  143 Southern Pecan Cir Unit 201, Winter Garden, FL 34787

  Awesome opportunity to live in a recently renovated, bottom floor unit in Southern Pines. Granite counter tops, brand new carpeting, new ceiling fans in bedrooms, brand new appliances in the kitchen. Close to the Winter Garden Village and major highways. Condominium has a community pool, tennis court, racquetball court, fitness center, hot tub, computer room, clubhouse, basketball court,

  Francisco Orchilles LAKESIDE REALTY WINDERMERE INC

  143 Southern Pecan Cir Unit 201, Winter Garden, FL 34787
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  /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 $777,478

  Last Listing Agent Angel Iglesia LUXE PROPERTIES

  15485 Sandfield Loop, Winter Garden, FL 34787
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  /31

  Est $818,277 Not Listed For Sale

  876 Landrum Dr, Winter Garden, FL 34787

  • 3 Beds
  • 3.5 Baths
  • 2,485 Sq Ft
  • Built 2014

  876 Landrum Dr, Winter Garden, FL 34787

  Last Sold Summary

  • 5% Above List Price
  • $315/SF
  • 26 Days On Market

  • Last Sold Price $783,000
  • Oct 03, 2023

  Last Listing Agent MARIO DENIZ DENIZ REALTY PARTNERS LLC
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  /36

  $455,000 Open Sat 1PM - 4PM

  • 3 Beds
  • 2.5 Baths
  • 1,626 Sq Ft

  16413 Prairie School Dr, Winter Garden, FL 34787

  Built in 2021 and located in the desirable Hawksmoor community in Horizon West, this three bedroom, two and a half bath townhome offers a modern layout with thoughtful upgrades throughout. The open concept main living area flows seamlessly into a stylish kitchen featuring quartz countertops and contemporary finishes, while upgraded interior details and custom wallpaper add character and warmth.

  

  Rob Aponte

  REAL BROKER, LLC

  (321) 284-2245

  16413 Prairie School Dr, Winter Garden, FL 34787
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  /50

  $1,790 - $3,525 per month

  Lakewalk at Hamlin

  1 - 3 Beds

  14012 Shoreside Way, Winter Garden, FL 34787

  Warm lake breezes and sunshine define the luxe lakeside lifestyle of the Lakewalk apartment residences that will wrap the shoreline of Lake Hancock next to the Town Center’s shopping, dining and entertainment. We offer 1 bedroom, 2 bedroom, and 3 bedroom apartment homes with the most up-to-date luxurious furnishings. If you are looking for relaxing, luxury living, look no further than Lakewalk at

  14012 Shoreside Way, Winter Garden, FL 34787
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  /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 $1,043,651

  Last Listing Agent Mauricio Penha VOLKE REAL ESTATE LLC

  14400 Shocklach Dr, Winter Garden, FL 34787
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  /2

  Est $548,437 Not Listed For Sale

  15162 Book Club Rd, Winter Garden, FL 34787

  • 3 Beds
  • 2 Baths
  • 2,089 Sq Ft
  • Built 2019

  15162 Book Club Rd, Winter Garden, FL 34787

  Last Sold Summary

  • 1% Below List Price
  • $266/SF
  • 202 Days On Market

  • Last Sold Price $555,000
  • Apr 07, 2025

  Last Listing Agent Nayara Martins Goncalves ENGEL & VOLKERS CLERMONT
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  /37

  $224,000

  • 3 Beds
  • 2 Baths
  • 1,396 Sq Ft

  14501 Grove Resort Ave Unit 2438, Winter Garden, FL 34787

  AGENTS - PLEASE VIEW REALTOR REMARKS IN THE MLS. Perfect as a family getaway or a high-performing investment property, this beautifully designed fully furnished 3-bedroom, 2-bath condo is located in the luxurious Grove Resort & Water Park in Winter Garden, FL. Thoughtfully outfitted with every comfort, this turn-key home welcomes you with style and convenience. Enjoy resort-style living with

  

  Rick Brown

  KELLER WILLIAMS ADVANTAGE 2 REALTY

  (321) 382-2706

  14501 Grove Resort Ave Unit 2438, Winter Garden, FL 34787
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  /19

  $2,300 per month

  • 3 Beds
  • 2.5 Baths
  • 1,365 Sq Ft
  • Townhouse for Rent

  13527 Daniels Landing Cir, Winter Garden, FL 34787

  Opportunity Awaits in Highly Sought-After Daniels Landing! Welcome to this charming 3-bedroom, 2.5-bath townhome offering comfort, convenience, and an unbeatable location. Perfect for homeowners or investors, this property is nestled in a well-maintained, gated community designed for easy living. Residents of Daniels Landing enjoy resort-style amenities, including a sparkling community pool,

  Mary Clevenger WEICHERT REALTORS HALLMARK PRO

  13527 Daniels Landing Cir, Winter Garden, FL 34787
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  /2

  $555,960 Sold Sep 19, 2025

  13520 Autumn Harvest Ave, Winter Garden, FL 34787

  • 3 Beds
  • 3 Baths
  • 2,198 Sq Ft
  • Built 2025

  Last Sold Summary

  • $253/SF

  Current Estimated Value $544,832

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

  13520 Autumn Harvest Ave, Winter Garden, FL 34787
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  /76

  Est $746,391 Not Listed For Sale

  1620 Highbanks Cir, Winter Garden, FL 34787

  • 5 Beds
  • 4.5 Baths
  • 3,775 Sq Ft
  • Built 2018

  1620 Highbanks Cir, Winter Garden, FL 34787

  Last Sold Summary

  • 7% Above List Price
  • $185/SF
  • 298 Days On Market

  • Last Sold Price $700,000
  • Jun 23, 2023

  Last Listing Agent Shaunda Hall GENSTONE REALTY
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  /59

  $939,000 Pending

  • 4 Beds
  • 4 Baths
  • 2,881 Sq Ft

  14354 Wabasso Loop, Winter Garden, FL 34787

  Welcome to this beautifully maintained Scandinavian-inspired home built in 2022, located in an intimate gated boutique community of just 55 homes in Winter Garden. Perfectly positioned on the premier lot in the neighborhood with a direct fountain water view, this home offers breathtaking sunsets from the living room, kitchen, lanai, pool, and balcony—while enjoying sun-filled interiors throughout

  

  Daniel Robinson

  HOUWZER INC

  (321) 373-7260

  14354 Wabasso Loop, Winter Garden, FL 34787
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  /50

  $1,699 - $3,423 total monthly price

  The Lodge at Hamlin

  1 - 3 Beds

  6151 Lake Lodge Dr, Winter Garden, FL 34787

  It’s human nature to want everything at your fingertips. It’s rare to find it. Tucked between the water, sunshine, and cypress trees, discover The Lodge at Hamlin. With nature surrounding you at home and a lakefront village at your doorstep, your hunt for the perfect lifestyle begins and ends here.

  6151 Lake Lodge Dr, Winter Garden, FL 34787
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  /2

  $594,948 Sold Nov 18, 2025

  12749 Harvest Rain Ave, Winter Garden, FL 34787

  • 4 Beds
  • 3.5 Baths
  • 2,441 Sq Ft
  • Built 2025

  Last Sold Summary

  • $244/SF

  Current Estimated Value $599,000

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

  12749 Harvest Rain Ave, Winter Garden, FL 34787
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  /2

  Est $763,429 Not Listed For Sale

  15870 Citrus Grove Loop, Winter Garden, FL 34787

  • 4 Beds
  • 4 Baths
  • 3,074 Sq Ft
  • Built 2015

  15870 Citrus Grove Loop, Winter Garden, FL 34787

  Last Sold Summary

  • 6% Above List Price
  • $234/SF
  • 92 Days On Market

  • Last Sold Price $720,000
  • Apr 17, 2025

  Last Listing Agent Sharon O'malley MBA REALTY GROUP, INC
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  /26

  $1,299,000

  • Land
  • 5.11 Acres
  • $254,207 per Acre

  10133 Colt Ln, Winter Garden, FL 34787

  Discover 5.1 beautiful acres in Avalon Hills, an exclusive community featuring just 16 premium luxury home 5 acre lots. No need to move almost an hour away just to find some land and more privacy when this gem is minutes to Windermere and everywhere you want to be. This vacant land represents the essence of premium real estate, nestled at the end of a one-way street ending in a serene cul-de-sac

  

  Jessica McKinney

  FLORIDA REALTY EXCHANGE LLC

  (321) 386-1622

  10133 Colt Ln, Winter Garden, FL 34787
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  /30

  $4,299 per month

  • 3 Beds
  • 2 Baths
  • 2,501 Sq Ft
  • House for Rent

  17877 Phil C Peters Rd, Winter Garden, FL 34787

  Location, Location, Location! Exceptional opportunity in Winter Garden, just 4 minutes from Hamlin Town Center, in one of the fastest-growing areas in Central Florida. This unique property features approximately 2.5 acres of land, delivering something increasingly rare in today’s market: space, privacy, and flexibility of use. The home includes 3 bedrooms, 2 bathrooms, and a bonus room, with a

  Mara Brasil REIS E SILVA REALTY GROUP LLC

  17877 Phil C Peters Rd, Winter Garden, FL 34787
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  /2

  $645,000 Sold Sep 11, 2025

  14664 Spotted Sandpiper Blvd, Winter Garden, FL 34787

  • 4 Beds
  • 2.5 Baths
  • 2,701 Sq Ft
  • Built 2014

  Last Sold Summary

  • 3% Below List Price
  • $239/SF
  • 0 Days On Market

  Current Estimated Value $632,280

  Last Listing Agent Andreia Beraldo TALENT REALTY SOLUTIONS

  14664 Spotted Sandpiper Blvd, Winter Garden, FL 34787
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  /47

  Est $922,213 Not Listed For Sale

  14843 Winter Stay Dr, Winter Garden, FL 34787

  • 4 Beds
  • 3.5 Baths
  • 3,505 Sq Ft
  • Built 2018

  14843 Winter Stay Dr, Winter Garden, FL 34787

  Last Sold Summary

  • 2% Below List Price
  • $268/SF
  • 22 Days On Market

  • Last Sold Price $940,000
  • Aug 21, 2023

  Last Listing Agent Daniel Betancourt EXP REALTY LLC
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  /38

  $555,000 Pending

  • 4 Beds
  • 3.5 Baths
  • 2,489 Sq Ft

  8685 Bayview Crossing Dr, Winter Garden, FL 34787

  Must see and make your new home today!! Situated in front of a most beautiful, sweeping lakefront view, it's the perfect place to wind down or just relax. It has A+ rated school district. Waterleigh provides a perfect blend of activities, amenities, trails, nature, parks, Tennis, clubhouse pools, fitness, parks, lush landscaping, parks & playgrounds allwing activities for everyone. Beautiful

  

  Karan Wienker

  COLDWELL BANKER REALTY

  (321) 461-5441

  8685 Bayview Crossing Dr, Winter Garden, FL 34787
• 

  

  /24

  $1,501 - $6,225 per month

  The Westerly

  Studio - 3 Beds

  14680 Westerly Dr, Winter Garden, FL 34787

  Luxury apartment living has never been easier than in your dream apartment home at The Westerly Apartments in Horizon West. Offering pet-friendly homes with modern interiors, abundant amenity spaces and an unparalleled location near Orlando's theme parks.With exceptional craftsmanship and attention to detail, our rentals offer a variety of studio, one, two, and three-bedroom layout to meet your

  14680 Westerly Dr, Winter Garden, FL 34787
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  /27

  $659,420 Sold Oct 31, 2025

  12595 Grape Chardonnay Aly, Winter Garden, FL 34787

  • 4 Beds
  • 3.5 Baths
  • 2,693 Sq Ft
  • Built 2025

  Move in Ready Sold Summary

  • $245/SF
  • 9 Days On Market

  K. Hovnanian Homes Osprey Ranch - 32'/40' Single Family

  12595 Grape Chardonnay Aly, Winter Garden, FL 34787
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  /54

  Est $566,439 Not Listed For Sale

  14043 Snowy Owl Ln, Winter Garden, FL 34787

  • 4 Beds
  • 3 Baths
  • 2,136 Sq Ft
  • Built 2016

  14043 Snowy Owl Ln, Winter Garden, FL 34787

  Last Sold Summary

  • 5% Below List Price
  • $279/SF
  • 73 Days On Market

  • Last Sold Price $595,000
  • Apr 12, 2024

  Last Listing Agent Maurince Pierre EXP REALTY LLC

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