Winter Garden, FL Homes

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  /28

  $535,000

  • 3 Beds
  • 2 Baths
  • 2,170 Sq Ft

  1343 Castleport Rd, Winter Garden, FL 34787

  Welcome to this beautifully landscaped 3-bedroom, 2-bathroom home in the 24-hour guard-gated Stoneybrook West community. Featuring a split-bedroom floor plan, the layout includes a versatile flex room ideal for a home office or den. The kitchen is equipped with white appliances and granite countertops and flows easily into the main living spaces, with ceiling fans installed throughout the home

  

  Kristi Matthew

  CENTURY 21 CARIOTI

  (321) 329-0584

  1343 Castleport Rd, Winter Garden, FL 34787
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  /50

  Starting at $1,699 Per Month

  • 1 - 3 Beds

  14520 Avalon Rd, Winter Garden, FL 34787

  Welcome home to Registry on Grass Lake, our brand-new apartment community that prioritizes a connection to comfort & convenience through designer touches and thorough consideration of your needs. Enjoy your own space with our studio, one-, two-, and three-bedroom floor plans all thoughtfully curated to bring you the best of apartment living. Within Registry on Grass Lake, you'll find amenities

  Registry on Grass Lake

  (321) 382-3310

  

  14520 Avalon Rd, Winter Garden, FL 34787
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  /31

  $469,990

  Sold Oct 17, 2025

  15405 Hamlin Park Dr, Winter Garden, FL 34787

  • 3 Beds
  • 3.5 Baths
  • 2,072 Sq Ft
  • Built 2025

  Move in Ready Sold Summary

  • $227/SF
  • 16 Days On Market

  Current Estimated Value $482,861

  15405 Hamlin Park Dr, Winter Garden, FL 34787
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  /2

  Est $639,925

  Not Listed For Sale

  12506 Westhaven Oak Dr Unit 115, Winter Garden, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 2,500 Sq Ft
  • Built 2025

  12506 Westhaven Oak Dr Unit 115, Winter Garden, FL 34787

  Last Sold Summary

  • 10 Days On Market
• 

  

  

  /23

  $592,000

  $28K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,420 Sq Ft

  12566 Westhaven Oak Dr, Winter Garden, FL 34787

  PRICE IMPROVEMENT! PRICED TO SELL, SELLER WILLING TO CONTRIBUTE UP TO $7,500.00 TOWARDS CLOSING COSTS OR BUYER RATE BUY-DOWN!Welcome to 12566 Westhaven Oak Drive in the desireable Osprey Ranch community of Winter Garden.This beautifully designed 4-bedroom, 3-bath home offers the perfect blend of modern comfort andluxury finishes, featuring an open-concept layout ideal for everyday

  

  Kendra Wallace

  UNITED REAL ESTATE PREFERRED

  (689) 336-1539

  12566 Westhaven Oak Dr, Winter Garden, FL 34787
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  /25

  Starting at $1,675

  Total Monthly Price

  • 1 - 3 Beds

  14619 Casita Ridge, Winter Garden, FL 34787

  IMT Sonoma Hills’ stunning one, two and three-bedroom apartments will take your breath away with a new level of luxury for West Orlando. Inside each home are five-star features and amenities, including spacious walk-in closets, gourmet kitchens with granite countertops, soaring ten-foot ceilings and sophisticated designer finishes. Start a tour of IMT Sonoma Hills and it won’t take long to

  IMT Sonoma Hills

  (689) 407-5242

  

  14619 Casita Ridge, Winter Garden, FL 34787
• 

  /2

  $1,160,000

  Sold Jun 15, 2026

  441 Courtlea Oaks Blvd, Winter Garden, FL 34787

  • 5 Beds
  • 4.5 Baths
  • 4,001 Sq Ft
  • Built 2000

  Last Sold Summary

  • 16% Below List Price
  • $290/SF
  • 64 Days On Market

  Current Estimated Value $1,181,839

  Last Listing Agent Jennifer Coon LAKESIDE REALTY WINDERMERE INC

  441 Courtlea Oaks Blvd, Winter Garden, FL 34787
• 

  /2

  Est $714,964

  Not Listed For Sale

  15491 Lebeau Loop, Winter Garden, FL 34787

  • 4 Beds
  • 3 Baths
  • 2,117 Sq Ft
  • Built 2025

  15491 Lebeau Loop, Winter Garden, FL 34787

  Last Sold Summary

  • 52 Days On Market
• 

  

  /43

  $345,000

  $9K PRICE DROP

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

  1532 Scarlet Oak Loop Unit 70B, Winter Garden, FL 34787

  Wonderful primary residence or rental investment opportunity! This beautifully maintained 3-bedroom, 2.5-bath condo in the central and peaceful Tucker Oaks community offers the perfect blend of comfort and convenience with a spacious and practical layout.The main level offers a well-appointed kitchen with granite countertops, 42” cabinetry, and a newer refrigerator, seamlessly connected to

  

  David Hartigan

  JASON MITCHELL REAL ESTATE FLO

  (321) 381-4644

  1532 Scarlet Oak Loop Unit 70B, Winter Garden, FL 34787
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  /30

  Starting at $1,446 Per Month

  • 1 - 3 Beds

  9405 Ascend Falls Dr, Winter Garden, FL 34787

  Welcome to Birchstone Waterleigh, where luxury meets tranquility in the heart of Winter Garden, FL. Designed for those who seek the extraordinary, our community offers an elevated living experience with refined interiors, resort-inspired amenities, and thoughtfully curated experiences. From impeccably crafted apartments to exclusive social spaces, every detail embodies sophistication and

  Birchstone Waterleigh

  (689) 600-2639

  

  9405 Ascend Falls Dr, Winter Garden, FL 34787
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  /43

  $330,000

  Sold Apr 17, 2026

  823 Magnolia Ave, Winter Garden, FL 34787

  • 3 Beds
  • 2 Baths
  • 1,210 Sq Ft
  • Built 2025

  Last Sold Summary

  • 4% Below List Price
  • $273/SF
  • 192 Days On Market

  Current Estimated Value $328,322

  Last Listing Agent Bosco Meira BELLA FLORIDA REALTY LLC

  823 Magnolia Ave, Winter Garden, FL 34787
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  /2

  Not Listed For Sale

  13043 Serene Glade Rd, Winter Garden, FL 34787

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

  13043 Serene Glade Rd, Winter Garden, FL 34787

  Last Sold Summary

  • 0 Days On Market
• 

  

  /42

  $449,000

  $10K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,853 Sq Ft

  8156 Wood Sage Dr, Winter Garden, FL 34787

  Winter Garden – Rare, immaculate end-unit townhome in highly sought-after Summerlake, fully updated and truly MOVE-IN READY. Step onto the charming front porch—perfect for morning coffee as the neighborhood comes to life—and then into a bright, open interior with soaring ceilings, a freshly painted interior, and an inviting floor plan.The chef’s kitchen features abundant real wood cabinetry,

  

  Kathy Aparo-Griffin

  APARO-GRIFFIN PROPERTIES INC

  (321) 384-8375

  8156 Wood Sage Dr, Winter Garden, FL 34787
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  /96

  Starting at $1,605 Per Month

  • 1 - 3 Beds

  16200 Ascend Village Ln, Winter Garden, FL 34787

  Retreat to a life of ultimate luxury at Ascend Waterleigh Village, a brand-new community offering one, two, and three bedroom apartments in a beautiful lakeside neighborhood. Our open floor plans offer the perfect mix of form and function, with features ranging from modern kitchens with stainless steel appliances and prep islands to spacious bedrooms with oversized walk-in closets. As a resident,

  Ascend Waterleigh Village

  (689) 407-6455

  

  16200 Ascend Village Ln, Winter Garden, FL 34787
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  /2

  $645,000

  Sold Sep 19, 2025

  1208 Castleport Rd, Winter Garden, FL 34787

  • 5 Beds
  • 3.5 Baths
  • 3,074 Sq Ft
  • Built 2001

  Last Sold Summary

  • 8% Below List Price
  • $210/SF
  • 85 Days On Market

  Current Estimated Value $652,646

  Last Listing Agent Barbara Waltman KELLER WILLIAMS CLASSIC

  1208 Castleport Rd, Winter Garden, FL 34787
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  /2

  Est $742,800

  Not Listed For Sale

  13106 Dendy Way Unit 19, Winter Garden, FL 34787

  • 4 Beds
  • 4 Baths
  • 3,243 Sq Ft
  • Built 2025

  13106 Dendy Way Unit 19, Winter Garden, FL 34787

  Last Sold Summary

  • 63 Days On Market
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  /69

  $799,000

  • 4 Beds
  • 3.5 Baths
  • 3,572 Sq Ft

  14252 Creekbed Cir, Winter Garden, FL 34787

  Welcome to 14252 Creekbed Circle, a spacious and beautifully designed home located in the heart of Winter Garden, in Bradford Creek, one of Central Florida's most sought-after communities. Perfectly situated near Downtown Winter Garden, you'll enjoy convenient access to popular restaurants, boutique shopping, farmers markets, community events, walking trails, and entertainment year-round.This

  

  Carla Robles

  WATSON REALTY CORP

  (321) 478-2739

  14252 Creekbed Cir, Winter Garden, FL 34787
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  /23

  Starting at $1,826

  Total Monthly Price

  • 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

  Corban Horizon West

  (689) 407-6619

  

  15000 Stratus Loop, Winter Garden, FL 34787
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  /2

  $510,000

  Sold Nov 14, 2025

  16394 Silver Brook Way, Winter Garden, FL 34787

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

  Last Sold Summary

  • $241/SF

  Current Estimated Value $517,487

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

  16394 Silver Brook Way, Winter Garden, FL 34787
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  /2

  Est $809,467

  Not Listed For Sale

  9438 Emerald Berry Dr, Winter Garden, FL 34787

  • 4 Beds
  • 3.5 Baths
  • 3,211 Sq Ft
  • Built 2025

  9438 Emerald Berry Dr, Winter Garden, FL 34787

  Last Sold Summary

  • 105 Days On Market
• 

  

  /48

  $1,025,000

  $75K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 2,758 Sq Ft

  10174 Merrymeeting Bay Dr, Winter Garden, FL 34787

  Welcome to 10174 Merrymeeting Bay Dr — a gorgeous 4-bedroom, 3.5-bath home in the heart of Winter Garden that checks all the boxes and then some. Step inside and you'll notice the open floor plan right away. Tile floors run through the main living areas with cozy carpet in the bedrooms. The kitchen is a dream with quartz counters, stainless appliances, wood cabinets, and a walk-in pantry. The

  

  Deanna Meredith

  LUXE PROPERTIES LLC

  (321) 382-5840

  10174 Merrymeeting Bay Dr, Winter Garden, FL 34787
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  /35

  Starting at $1,499

  Total Monthly Price

  • 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

  Garden City Apartments

  (689) 407-2270

  521 S Park Ave, Winter Garden, FL 34787
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  /2

  $695,000

  Sold Oct 20, 2025

  9863 Summerlake Groves St, Winter Garden, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 2,072 Sq Ft
  • Built 2020

  Last Sold Summary

  • 7% Below List Price
  • $335/SF
  • 103 Days On Market

  Current Estimated Value $706,398

  Last Listing Agent Viviane Rocha WRA BUSINESS & REAL ESTATE

  9863 Summerlake Groves St, Winter Garden, FL 34787
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  /2

  Est $579,157

  Not Listed For Sale

  4591 Gliding Wave St, Winter Garden, FL 34787

  • 3 Beds
  • 2 Baths
  • 2,144 Sq Ft
  • Built 2022

  4591 Gliding Wave St, Winter Garden, FL 34787

  Last Sold Summary

  • 9 Days On Market
• 

  

  /69

  $899,000

  • 4 Beds
  • 3.5 Baths
  • 2,671 Sq Ft

  8801 Fountain Palm Aly, Winter Garden, FL 34787

  Prepare to see the most decked out and finely finished townhome in Central Florida! This Toll Brothers end unit has been completely customized with over $140,000 in structural upgrades and $270,000 in design upgrades--that's right, more than $400k in upgrades, and the original sale was more than DOUBLE the price of many of the other townhomes in the community. Facing the lush landscape of the

  

  Drew Ross

  LAKEFIELD REALTY GROUP LLC

  (321) 252-7848

  8801 Fountain Palm Aly, Winter Garden, FL 34787
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  /50

  Starting at $1,815 Per Month

  • 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

  Lakewalk at Hamlin

  (689) 600-3888

  

  14012 Shoreside Way, Winter Garden, FL 34787
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  /43

  $439,990

  Sold Oct 28, 2025

  15034 Grove Lake Dr, Winter Garden, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,881 Sq Ft
  • Built 2025

  Move in Ready Sold Summary

  • $234/SF
  • 23 Days On Market

  Current Estimated Value $453,097

  DRB Homes Parkview at Hamlin

  15034 Grove Lake Dr, Winter Garden, FL 34787
• 

  /2

  Est $2,132,824

  Not Listed For Sale

  15633 Panther Lake Dr, Winter Garden, FL 34787

  • 4 Beds
  • 4.5 Baths
  • 4,556 Sq Ft
  • Built 2019

  15633 Panther Lake Dr, Winter Garden, FL 34787

  Last Sold Summary

  • 65 Days On Market
• 

  

  /42

  $834,000

  $61K PRICE DROP

  • 3 Beds
  • 3.5 Baths
  • 1,906 Sq Ft

  131 Oak Laurel Dr, Winter Garden, FL 34787

  131 Oak Laurel Drive is a stunning, modern townhome built in 2019 in the highly desirable Park Place community in the heart of historic Winter Garden, Florida. This beautifully designed three-story home offers 3 bedrooms, 3.5 bathrooms, and 1,906 square feet of heated living space. Each bedroom features its own en-suite bathroom, providing privacy and comfort for all. This home includes an

  

  Thomas Nickley

  KELLER WILLIAMS REALTY AT THE PARKS

  (321) 405-1381

  131 Oak Laurel Dr, Winter Garden, FL 34787
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  /50

  Starting at $1,700

  Total Monthly Price

  • 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.

  The Lodge at Hamlin

  (689) 400-7193

  

  6151 Lake Lodge Dr, Winter Garden, FL 34787
• 

  /2

  $600,000

  Sold Dec 17, 2025

  3390 Current Ave, Winter Garden, FL 34787

  • 5 Beds
  • 3 Baths
  • 2,916 Sq Ft
  • Built 2020

  Last Sold Summary

  • 6% Below List Price
  • $206/SF
  • 74 Days On Market

  Current Estimated Value $632,348

  Last Listing Agent Jessica Macias KELLER WILLIAMS ADVANTAGE III

  3390 Current Ave, Winter Garden, FL 34787
• 

  /2

  Est $648,974

  Not Listed For Sale

  3136 Winesap Way, Winter Garden, FL 34787

  • 4 Beds
  • 3 Baths
  • 2,540 Sq Ft
  • Built 2016

  3136 Winesap Way, Winter Garden, FL 34787

  Last Sold Summary

  • 66 Days On Market
• 

  

  /44

  $650,000

  $19K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,334 Sq Ft

  14005 Aldford Dr, Winter Garden, FL 34787

  Welcome to 14005 Aldford Drive in Winter Garden, a beautifully designed two-story home built by Ashton Woods, known for its modern architecture, creative floor plans, and thoughtful design. This inviting residence offers 3 bedrooms, 2 full baths, and 1 half bath, with a layout that blends everyday comfort with welcoming indoor and outdoor living spaces. Inside, the home features a bright and

  

  Thomas Nickley

  KELLER WILLIAMS REALTY AT THE PARKS

  (689) 272-3634

  14005 Aldford Dr, Winter Garden, FL 34787
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  /24

  Starting at $1,563 Per Month

  • 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

  The Westerly

  (321) 395-5822

  

  14680 Westerly Dr, Winter Garden, FL 34787
• 

  /2

  $739,000

  Sold Jan 05, 2026

  214 S Main St, Winter Garden, FL 34787

  • 4 Beds
  • 4 Baths
  • 2,268 Sq Ft
  • Built 1993

  Last Sold Summary

  • 1% Below List Price
  • $326/SF
  • 0 Days On Market

  Current Estimated Value $737,528

  Last Listing Agent Joe Wynkoop CHARLES RUTENBERG REALTY ORLANDO

  214 S Main St, Winter Garden, FL 34787
• 

  /2

  Est $529,245

  Not Listed For Sale

  4233 Mistwood St, Winter Garden, FL 34787

  • 4 Beds
  • 3.5 Baths
  • 2,342 Sq Ft
  • Built 2021

  4233 Mistwood St, Winter Garden, FL 34787

  Last Sold Summary

  • 32 Days On Market
• 

  

  /35

  $595,000

  • 3 Beds
  • 2.5 Baths
  • 2,401 Sq Ft

  1019 Portmoor Way, Winter Garden, FL 34787

  **This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.** Welcome to 1019 Portmoor Way in Winter Garden, a 2-story home offering 3 bedrooms, 3 bathrooms, a balcony, and a layout designed for comfortable everyday living. All bedrooms are located on the upper floor, creating

  

  Thomas Nickley

  KELLER WILLIAMS REALTY AT THE PARKS

  (321) 467-7860

  1019 Portmoor Way, Winter Garden, FL 34787
• 

  

  /23

  Starting at $1,460 Per Month

  • 1 - 3 Beds

  1301 Inland Seas Blvd, Winter Garden, FL 34787

  Inland Seas Apartments

  (689) 407-2434

  

  1301 Inland Seas Blvd, Winter Garden, FL 34787
• 

  /2

  $650,000

  Sold Apr 03, 2026

  14008 Jomatt Loop, Winter Garden, FL 34787

  • 4 Beds
  • 3 Baths
  • 2,952 Sq Ft
  • Built 2019

  Last Sold Summary

  • $220/SF
  • 35 Days On Market

  Current Estimated Value $655,394

  Last Listing Agent David Fontana CHARLES RUTENBERG REALTY ORLANDO

  14008 Jomatt Loop, Winter Garden, FL 34787
• 

  /2

  Est $1,376,664

  Not Listed For Sale

  15008 Sunstar Way, Winter Garden, FL 34787

  • 5 Beds
  • 4 Baths
  • 3,084 Sq Ft
  • Built 2021

  15008 Sunstar Way, Winter Garden, FL 34787

  Last Sold Summary

  • 7 Days On Market

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