Winter Garden, FL Homes

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  $799,900

  • 4 Beds
  • 4.5 Baths
  • 3,871 Sq Ft

  2015 Sandy Garden Ln, Winter Garden, FL 34787

  One or more photo(s) has been virtually staged. Welcome home to a lifestyle of space, comfort, and effortless entertaining in this beautifully designed two-story residence with charming exterior stone accents, set on an almost 1⁄4-acre lot in a gated community. From the moment you step inside, you’ll appreciate the open, airy layout, high ceilings, and bamboo flooring throughout — no carpet

  

  Kristi Matthew

  CENTURY 21 CARIOTI

  (321) 599-3873

  2015 Sandy Garden Ln, Winter Garden, FL 34787
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  $1,519 - $1,999 per month

  Country Gardens

  1 - 3 Beds

  15122 W Colonial Dr, Winter Garden, FL 34787

  Learn more about our current specials! Stylish design at a price thats right! Country Gardens Apartment Homes is located in Winter Garden, Florida, with easy access to Florida's Turnpike and SR-50/Colonial Drive. You'll experience a top selection of amenities and features at this community, like a resort-style pool with sundeck,

  15122 W Colonial Dr, Winter Garden, FL 34787
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  $510,000 Sold Oct 31, 2025

  706 Grandhaven Way, Winter Garden, FL 34787

  • 4 Beds
  • 3 Baths
  • 1,904 Sq Ft
  • Built 2010

  Last Sold Summary

  • 5% Below List Price
  • $268/SF
  • 37 Days On Market

  Current Estimated Value $514,501

  Last Listing Agent Amy Moline EXP REALTY LLC

  706 Grandhaven Way, Winter Garden, FL 34787
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  Est $988,343 Not Listed For Sale

  16983 Wingspread Loop, Winter Garden, FL 34787

  • 4 Beds
  • 3 Baths
  • 2,691 Sq Ft
  • Built 2021

  16983 Wingspread Loop, Winter Garden, FL 34787

  Last Sold Summary

  • 14% Below List Price
  • $427/SF
  • 1 Day On Market

  Last Sold Price $1,150,000

  Last Listing Agent Gail Moynihan LUXURY PROPERTIES FLORIDA REAL
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  $415,000

  • 3 Beds
  • 1.5 Baths
  • 1,086 Sq Ft

  750 S Park Ave, Winter Garden, FL 34787

  MOVE-IN-READY!! PRICE REDUCTION!! SELLER OFFERING $6,000.00 TOWARDS CLOSING COST!! Welcome to 750 S Park Avenue, a beautifully maintained and FULLY RENOVATED home offering comfort, charm, and modern convenience to downtown Winter Garden.This 3-bedroom, 1.5-bath residence spans approximately 1,186 square feet and sits on a HUGE FENCED IN well-kept lot- perfect for both relaxing and

  

  Keegan Siegfried

  LPT REALTY, LLC

  (321) 462-6888

  750 S Park Ave, Winter Garden, FL 34787
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  /27

  $2,400 per month

  • 3 Beds
  • 2 Baths
  • 985 Sq Ft
  • House for Rent

  1323 Daniels Cove Dr, Winter Garden, FL 34787

  Turn-key, FULLY FURNISHED executive style rental, including housewares, linens and TV's. This charming 3 bedroom 2 bathroom home is light and bright and has been luxuriously upgrade to feature updated flooring, kitchen and bathrooms with a spacious living room and 1 car garage with laundry. The backyard is fully fenced and beautifully landscaped. It is perfectly situated close to downtown Winter

  Erin Wanner STOCKWORTH REALTY GROUP LLC

  1323 Daniels Cove Dr, Winter Garden, FL 34787
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  $1,350,000 Sold May 28, 2025

  13638 Sunset Lakes Cir, Winter Garden, FL 34787

  • 4 Beds
  • 3 Baths
  • 2,985 Sq Ft
  • Built 2000

  Last Sold Summary

  • 4% Below List Price
  • $452/SF
  • 35 Days On Market

  Current Estimated Value $1,307,468

  Last Listing Agent Tom Rumph SAND DOLLAR REALTY GROUP INC

  13638 Sunset Lakes Cir, Winter Garden, FL 34787
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  Est $808,190 Not Listed For Sale

  8025 Gray Kingbird Dr, Winter Garden, FL 34787

  • 5 Beds
  • 4 Baths
  • 3,729 Sq Ft
  • Built 2019

  8025 Gray Kingbird Dr, Winter Garden, FL 34787

  Last Sold Summary

  • 3% Above List Price
  • $211/SF
  • 47 Days On Market

  Last Sold Price $785,000

  Last Listing Agent Hojin Chang RE/MAX
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  /25

  $332,500

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

  14501 Grove Resort Ave Unit 3205, Winter Garden, FL 34787

  Luxury vacation rental within The Grove Resort and Spa. Beautifully furnished with modern furniture and fixtures that make for a one-of-a-kind vacation property, this fully furnished 2-bedroom, 2-bath unit can sleep up to 8 people (room with1 king bed, room with 2 full beds and queen sleeper sofa) and has a gourmet kitchen with stainless steel appliances and quartz counters. The Grove Resort and

  

  Jamie Ampel

  ALL SELLERS & BUYERS REALTY INC

  (321) 710-1042

  14501 Grove Resort Ave Unit 3205, Winter Garden, FL 34787
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  $1,099 - $1,800 per month

  Winterwoods

  Studio - 2 Beds

  15300 W Colonial Dr, Winter Garden, FL 34787

  Welcome to Winterwoods, apartments in Winter Garden, FL. Rest easy knowing you will be in a great neighborhood with convenient access to all that Winter Garden has to offer. Our single-story, garden-style West Winter Garden apartments feature private entrances and patios for your enjoyment. We offer Studio, 1 & 2 bedroom apartments in Winter Garden near Fowler Groves Winter Garden

  15300 W Colonial Dr, Winter Garden, FL 34787
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  $526,000 Sold Oct 15, 2025

  13029 Tranquil Water Aly, Winter Garden, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,836 Sq Ft
  • Built 2024

  Last Sold Summary

  • 2% Below List Price
  • $286/SF
  • 0 Days On Market

  Current Estimated Value $524,970

  Last Listing Agent Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

  13029 Tranquil Water Aly, Winter Garden, FL 34787
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  Est $579,719 Not Listed For Sale

  3288 Sailing Pier Ave, Winter Garden, FL 34787

  • 3 Beds
  • 2 Baths
  • 2,070 Sq Ft
  • Built 2020

  3288 Sailing Pier Ave, Winter Garden, FL 34787

  Last Sold Summary

  • 1% Below List Price
  • $283/SF
  • 2 Days On Market

  Last Sold Price $585,000

  Last Listing Agent Nesterine Blair BLAIR REALTY GROUP INC
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  $519,000

  • 4 Beds
  • 3 Baths
  • 2,042 Sq Ft

  16105 Water Spring Blvd, Winter Garden, FL 34787

  Discover this immaculate 4-bedroom, 3-bath home in the beautiful Storey Grove community. Designed for family living, it offers bright and spacious interiors that flow seamlessly from the open-concept kitchen to the main living area. The master suite features a private bathroom and generous storage space, while the additional bedrooms are perfect for guests, or a home office. Outside, enjoy a

  

  Yesenia Barrios

  URBAN-O REAL ESTATE SOLUTIONS

  (321) 346-5456

  16105 Water Spring Blvd, Winter Garden, FL 34787
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  $2,990 per month

  • 4 Beds
  • 2.5 Baths
  • 1,948 Sq Ft
  • Townhouse for Rent

  9743 Amber Chestnut Way, Winter Garden, FL 34787

  Beautiful and well-maintained 4-bedroom, 2.5-bath townhome located in the highly desirable Watermark community in Winter Garden. This thoughtfully designed floor plan features a spacious open-concept living and dining area, a well-appointed kitchen, and comfortable bedrooms with neutral finishes throughout, creating a bright and move-in-ready atmosphere.Enjoy a private covered brick-paver

  Renato Melo SIGNATURE INTERNATIONAL REAL E

  9743 Amber Chestnut Way, Winter Garden, FL 34787
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  $495,000 Sold Apr 25, 2025

  849 Bending Oak Trail, Winter Garden, FL 34787

  • 5 Beds
  • 2.5 Baths
  • 2,212 Sq Ft
  • Built 2012

  Last Sold Summary

  • 10% Below List Price
  • $224/SF
  • 318 Days On Market

  Current Estimated Value $506,736

  Last Listing Agent GREGORY BLACKALL VERANDA REALTY GROUP

  849 Bending Oak Trail, Winter Garden, FL 34787
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  Est $724,861 Not Listed For Sale

  12829 Charmed Dr, Winter Garden, FL 34787

  • 4 Beds
  • 3 Baths
  • 2,924 Sq Ft
  • Built 2024

  12829 Charmed Dr, Winter Garden, FL 34787

  Last Sold Summary

  • 1% Above List Price
  • $245/SF
  • 158 Days On Market

  Last Sold Price $717,000

  Last Listing Agent Jay Love DR HORTON REALTY OF CENTRAL FLORIDA LLC
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  /97

  $1,150,000

  • 3 Beds
  • 3 Baths
  • 2,400 Sq Ft

  17661 Davenport Rd, Winter Garden, FL 34787

  Located in the Rare Lake Avalon Rural Settlement where oversized lots and protected rural zoning create one of Winter Garden’s last truly rare, low-density communities. Welcome to this fully remodeled, modern lakefront retreat on the shores of Lake Avalon, offering the perfect balance of sophistication, privacy, and convenience. Situated on almost 1.5 acres of fenced, irrigated land, this

  

  Denise Gregorie

  CLOCK TOWER REALTY

  (321) 467-7885

  17661 Davenport Rd, Winter Garden, FL 34787
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  /23

  $1,460 - $1,950 per month

  Inland Seas Apartments

  1 - 3 Beds

  1301 Inland Seas Blvd, Winter Garden, FL 34787

  1301 Inland Seas Blvd, Winter Garden, FL 34787
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  $1,218,750 Sold Jan 06, 2026

  7833 Freestyle Ln, Winter Garden, FL 34787

  • 4 Beds
  • 3 Baths
  • 3,364 Sq Ft
  • Built 2018

  Last Sold Summary

  • 13% Below List Price
  • $362/SF
  • 71 Days On Market

  Current Estimated Value $1,264,599

  Last Listing Agent Dennesha Leachman GLOBAL SAPPHIRE REALTY LLC

  7833 Freestyle Ln, Winter Garden, FL 34787
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  Est $687,997 Not Listed For Sale

  15515 Sandfield Loop, Winter Garden, FL 34787

  • 4 Beds
  • 3 Baths
  • 2,788 Sq Ft
  • Built 2014

  15515 Sandfield Loop, Winter Garden, FL 34787

  Last Sold Summary

  • 3% Above List Price
  • $240/SF
  • 194 Days On Market

  Last Sold Price $670,000

  Last Listing Agent Kelly Thompson CHARLES RUTENBERG REALTY ORLANDO
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  $299,000

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

  Unlisted Address

  Come One, Come All! This is perfect for a family or anyone looking to use as an investment home. This beautiful home comes with really thought-out details to make you feel right at home. The Community also offers TONS of recreational items to choose from: You can choose from relaxing at the spa, working out in one or both of the two fitness centers provided. 3 swimming pools with food and drink

  

  Consuelo Vilar

  WELCOME HOME REALTY GROUP LLC

  (321) 386-1360

  Unlisted Address
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  $2,900 per month

  • 4 Beds
  • 3.5 Baths
  • 2,486 Sq Ft
  • House for Rent

  15187 Chapter Way, Winter Garden, FL 34787

  Well-maintained single-family home located in a highly desirable Winter Garden community within a top-rated school zone. This thoughtfully designed residence offers a functional and comfortable layout ideal for modern living. The first floor is completely carpet-free, providing a clean, contemporary feel and easy maintenance, and features a spacious primary bedroom suite on the main level for

  Jing Yue INTEREALTY SERVICE

  15187 Chapter Way, Winter Garden, FL 34787
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  $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 $808,268

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

  16694 Olive Hill Dr, Winter Garden, FL 34787
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  Est $615,498 Not Listed For Sale

  5615 Cypress Hill Rd, Winter Garden, FL 34787

  • 4 Beds
  • 2.5 Baths
  • 2,635 Sq Ft
  • Built 2017

  5615 Cypress Hill Rd, Winter Garden, FL 34787

  Last Sold Summary

  • 1% Below List Price
  • $235/SF
  • 22 Days On Market

  Last Sold Price $620,000

  Last Listing Agent Silvia Kinkela SERHANT
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  $625,000

  • 3 Beds
  • 2.5 Baths
  • 2,684 Sq Ft

  393 Lake Amberleigh Dr, Winter Garden, FL 34787

  Located in a quiet, gated community within a highly rated school zone, this well-maintained home offers comfort, privacy, and thoughtful upgrades. The home features two AC systems, including a main unit with an electronic air cleaner, a high-efficiency water heater, and a whole-house reverse osmosis and water softening system, along with updated double-pane windows on the back of the home. A NEW

  

  Yusuf Gencay

  RE/MAX Town & Country Realty

  (321) 252-5917

  393 Lake Amberleigh Dr, Winter Garden, FL 34787
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  $1,932 - $2,647 per month

  Overture Hamlin 55+ Active Adult Apartment...

  1 - 2 Beds

  5795 Citrus Village Blvd, Winter Garden, FL 34787

  Schedule your in-person or virtual tour today! Walk-ins are also welcome!

  5795 Citrus Village Blvd, Winter Garden, FL 34787
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  $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

  Current Estimated Value $276,530

  Last Listing Agent Todd Schroth EXP REALTY LLC

  1300 Eastern Pecan Place Unit 104, Winter Garden, FL 34787
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  Est $545,340 Not Listed For Sale

  13157 Calming Breeze Way, Winter Garden, FL 34787

  • 4 Beds
  • 3 Baths
  • 2,083 Sq Ft
  • Built 2024

  13157 Calming Breeze Way, Winter Garden, FL 34787

  Last Sold Summary

  • 2% Above List Price
  • $257/SF
  • 125 Days On Market

  Last Sold Price $535,542

  Last Listing Agent Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC
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  $786,000

  • 4 Beds
  • 3.5 Baths
  • 3,272 Sq Ft

  8901 Lakeshore Pointe Dr, Winter Garden, FL 34787

  Stunning ENZO model townhome by Toll Brothers designed living space in the highly sought after Lakeshore Preserve community, where elegance meets convenience. Located among luxury homes and premium surroundings, this executive style residence delivers an exceptional combination of location, floor plan, and upgrades. Built in 2017, this spacious townhome features 4 bedrooms and four full

  

  Carmelo Nuccio

  RE/MAX EXCLUSIVE COLLECTION

  (321) 382-3371

  8901 Lakeshore Pointe Dr, Winter Garden, FL 34787
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  $2,650 per month

  • 3 Beds
  • 2.5 Baths
  • 1,683 Sq Ft
  • Townhouse for Rent

  16258 Merry Aly, Winter Garden, FL 34787

  Brand new beautiful 3-bedroom, 2.5-bath townhome with 1,683 sqft located in a newer Winter Garden community. This home features an open floor plan, brand-new appliances, and a rare extended driveway. All bedrooms are upstairs, along with a conveniently located second-floor laundry room.Property offers pond views, no front neighbors, and is within walking distance to the community pool. Zoned

  Andrea Pointon POINTON REALTY INC

  16258 Merry Aly, Winter Garden, FL 34787
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  $458,000 Sold Apr 07, 2025

  703 Grand Royal Cir, Winter Garden, FL 34787

  • 4 Beds
  • 2 Baths
  • 1,779 Sq Ft
  • Built 2001

  Last Sold Summary

  • $257/SF
  • 4 Days On Market

  Current Estimated Value $447,921

  Last Listing Agent Kwaku Mitchell KELLER WILLIAMS CLASSIC

  703 Grand Royal Cir, Winter Garden, FL 34787
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  Est $1,379,274 Not Listed For Sale

  16882 Sanctuary Dr, Winter Garden, FL 34787

  • 5 Beds
  • 4.5 Baths
  • 4,038 Sq Ft
  • Built 2022

  16882 Sanctuary Dr, Winter Garden, FL 34787

  Last Sold Summary

  • $342/SF
  • 148 Days On Market

  Last Sold Price $1,380,000

  Last Listing Agent Mary Ann Foley CHARLES RUTENBERG REALTY ORLANDO
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  $589,000

  • 4 Beds
  • 3.5 Baths
  • 2,477 Sq Ft

  10625 Atwater Bay Dr, Winter Garden, FL 34787

  Welcome to this beautifully designed, move-in ready 4-bedroom, 3.5-bath home with a 2-car garage, perfectly situated on an elevated lot in the highly sought-after Waterleigh community of Horizon West, Winter Garden. The main level boasts an open-concept layout featuring a stunning kitchen with granite countertops, stainless steel appliances, a walk-in pantry, and an inviting eat-in nook that

  

  Daniel Robinson

  HOUWZER INC

  (321) 252-6030

  10625 Atwater Bay Dr, Winter Garden, FL 34787
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  $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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  $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 $911,071

  Last Listing Agent Jaime Galeoto FLORIDA REALTY RESULTS LLC

  17234 Cork St, Winter Garden, FL 34787
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  Est $544,098 Not Listed For Sale

  16504 Water Whisper Aly, Winter Garden, FL 34787

  • 4 Beds
  • 2.5 Baths
  • 1,836 Sq Ft
  • Built 2024

  16504 Water Whisper Aly, Winter Garden, FL 34787

  Last Sold Summary

  • 3% Below List Price
  • $306/SF
  • 0 Days On Market

  Last Sold Price $561,915

  Last Listing Agent Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC
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  $594,989 New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,078 Sq Ft

  13011 Tranquil Water Aly, Winter Garden, FL 34787

  The Cooper – 2,078 Sq. Ft. | 3 Bedrooms + Loft | 2.5 Baths | 2-Car Garage Beautiful open-concept home featuring 2,078 sq. ft. with three bedrooms, a loft, and 2.5 bathrooms with the front of the home facing conservation! The gourmet kitchen offers quartz countertops and linen cabinets, overlooking the dining and living areas for seamless entertaining. Elegant level-three natural wood-look plank

  

  Cindy Sapp

  OLYMPUS EXECUTIVE REALTY INC

  13011 Tranquil Water Aly, Winter Garden, FL 34787
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  $3,995 per month

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

  17049 Seville Orange Rd, Winter Garden, FL 34787

  Beautiful 4 Bed, 3 Bath home with high end custom finishes Available Immediately! Small to medium pets are allowed. This neighborhood also include a community pool, clubhouse, playground, and dog park! This home features an open floorplan with tons of natural light. There are 4 large bedrooms and a gorgeous master suite with a huge walk in closet. There is a front porch for sitting and relaxing

  Ben Becton KELLER WILLIAMS REALTY SMART

  17049 Seville Orange Rd, Winter Garden, FL 34787
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  $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 $792,403

  Last Listing Agent Angel Iglesia LUXE PROPERTIES

  15485 Sandfield Loop, Winter Garden, FL 34787
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  Not Listed For Sale

  9499 Emerald Berry Dr, Winter Garden, FL 34787

  • 4 Beds
  • 2.5 Baths
  • 2,060 Sq Ft
  • Built 2025

  9499 Emerald Berry Dr, Winter Garden, FL 34787

  Last Sold Summary

  • $301/SF
  • 137 Days On Market

  Last Sold Price $619,500

  Last Listing Agent William Maltbie MALTBIE REALTY GROUP

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