Windermere, FL Homes

• 

  

  /2

  Est $1,889,142

  Not Listed For Sale

  12408 Corso Ct, Windermere, FL 34786

  • 6 Beds
  • 5.5 Baths
  • 5,497 Sq Ft
  • Built 2017

  12408 Corso Ct, Windermere, FL 34786

  Last Sold Summary

  • 2 Days On Market
• 

  

  

  /35

  $1,175,000

  $75K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,816 Sq Ft

  5128 Butler Ridge Dr, Windermere, FL 34786

  Calling all car enthusiasts or artisans needing a large, detached workshop on your property! This house has it all; including a gorgeous interior, huge pool and lanai equipped with an outdoor kitchen, and a large 30 x 30 detached 5 car garage/workshop in addition to a 2 car attached garage. This house is perfect for work and play! Situated on a rare, 1 acre lot in the coveted town of Windermere,

  Taylar Colangelo, LLC LOKATION

  5128 Butler Ridge Dr, Windermere, FL 34786
• 

  

  /2

  $1,050,000

  Sold May 21, 2026

  316 E 5th Ave, Windermere, FL 34786

  • 4 Beds
  • 3 Baths
  • 2,412 Sq Ft
  • Built 1962

  Last Sold Summary

  • 5% Below List Price
  • $435/SF
  • 22 Days On Market

  Current Estimated Value $1,074,637

  Last Listing Agent Darrell Nunnelley VINTAGE REALTY GROUP LLC

  316 E 5th Ave, Windermere, FL 34786
• 

  

  /2

  Est $519,732

  Not Listed For Sale

  13832 Summerport Trail Loop, Windermere, FL 34786

  • 4 Beds
  • 3.5 Baths
  • 2,245 Sq Ft
  • Built 2016

  13832 Summerport Trail Loop, Windermere, FL 34786

  Last Sold Summary

  • 91 Days On Market
• 

  

  

  /31

  $800,000

  $75K PRICE DROP Pending

  • 4 Beds
  • 3.5 Baths
  • 3,124 Sq Ft

  5413 Walsh Pond Ct, Windermere, FL 34786

  Under contract-accepting backup offers. Discover the charm of this water front, 4 bedroom 3.5 bath home located in the desirable Summerport community. This unique property is nestled in the cul de sac for complete privacy. Enjoy scenic water views while relaxing poolside on the spacious screen enclosed lanai, which is also great for entertaining. The interior features granite countertops,

  Brenda Jebailey HAVEN PROPERTY GROUP LLC

  5413 Walsh Pond Ct, Windermere, FL 34786
• 

  /2

  $1,400,000

  Sold Apr 08, 2026

  6023 Blakeford Dr, Windermere, FL 34786

  • 5 Beds
  • 3 Baths
  • 3,013 Sq Ft
  • Built 1999

  Last Sold Summary

  • 8% Below List Price
  • $465/SF
  • 9 Days On Market

  Current Estimated Value $1,403,806

  Last Listing Agent Angela Durruthy KEENE'S POINTE REALTY

  6023 Blakeford Dr, Windermere, FL 34786
• 

  

  /46

  Est $823,086

  Not Listed For Sale

  8738 Iron Mountain Trail, Windermere, FL 34786

  • 4 Beds
  • 3.5 Baths
  • 3,127 Sq Ft
  • Built 2013

  8738 Iron Mountain Trail, Windermere, FL 34786

  Last Sold Summary

  • 313 Days On Market
• 

  /2

  $3,750,000

  New Construction

  • 5 Beds
  • 5.5 Baths
  • 6,182 Sq Ft

  9960 6th St, Windermere, FL 34786

  Under Construction. Experience unparalleled luxury in this custom-built Davila Homes estate, ideally located in the heart of Windermere. Showcasing the highly sought-after Stanford floor plan, this magnificent residence offers approximately 6,182 square feet of living space with 5 bedrooms, 5 full baths, 1 half bath, and a spacious 3-car garage. Designed for both elegant entertaining and

  Fernanda Negromonte NOVA REAL ESTATE SERVICES INC

  9960 6th St, Windermere, FL 34786
• 

  /2

  $600,000

  Sold Jul 09, 2025

  5063 Carillon Ln, Windermere, FL 34786

  • 4 Beds
  • 3 Baths
  • 2,406 Sq Ft
  • Built 2004

  Last Sold Summary

  • $249/SF
  • 7 Days On Market

  Current Estimated Value $598,718

  Last Listing Agent Jared Dunn LIVE MVRK LLC

  5063 Carillon Ln, Windermere, FL 34786
• 

  

  /3

  Est $1,258,626

  Not Listed For Sale

  7861 Ficquette Rd, Windermere, FL 34786

  7861 Ficquette Rd, Windermere, FL 34786

  Last Sold Summary

  • 27 Days On Market
• 

  

  /30

  $675,000

  • 3 Beds
  • 2 Baths
  • 1,819 Sq Ft

  9110 Palm Tree Dr, Windermere, FL 34786

  Welcome home. This wonderfully kept move-in ready 3 bedroom, 2 bathroom pool home is located in one of SouthWest Orlando's sought after communities, Silver Woods. It features travertine tile flooring throughout most of the home with engineered hardwood flooring in all the bedrooms, an open kitchen with stainless steel appliances and granite countertops overlooking the family room and an inside

  Tony Vicari VICARI REALTY CORP

  9110 Palm Tree Dr, Windermere, FL 34786
• 

  /2

  $820,000

  Sold Mar 06, 2026

  416 Magnolia St, Windermere, FL 34786

  • 2 Beds
  • 1.5 Baths
  • 2,115 Sq Ft
  • Built 1915

  Last Sold Summary

  • 7% Below List Price
  • $388/SF
  • 74 Days On Market

  Current Estimated Value $829,735

  Last Listing Agent Judy Black UPSIDE REAL ESTATE INC

  416 Magnolia St, Windermere, FL 34786
• 

  /2

  Est $1,276,667

  Not Listed For Sale

  14416 Crest Palm Ave, Windermere, FL 34786

  • 6 Beds
  • 4.5 Baths
  • 4,443 Sq Ft
  • Built 2024

  14416 Crest Palm Ave, Windermere, FL 34786

  Last Sold Summary

  • 0 Days On Market
• 

  /2

  $650,000

  Pending

  • 5 Beds
  • 4 Baths
  • 3,015 Sq Ft

  6956 Trellis Vine Loop, Windermere, FL 34786

  This is a gorgeous two-story home with five bedrooms, four baths, and a two-car garage. This home offers an open floor plan with an expansive great room featuring an elegant display of windows to create a naturally luminous home, casual dining area, and kitchen. The casual dining area allows outdoor access to a lanai and the kitchen provides plenty of counter space as well as an oversized island

  Dan Li EAST PEARL REALTY

  6956 Trellis Vine Loop, Windermere, FL 34786
• 

  /2

  $685,000

  Sold May 20, 2026

  13243 Charfield St, Windermere, FL 34786

  • 4 Beds
  • 3.5 Baths
  • 2,794 Sq Ft
  • Built 2010

  Last Sold Summary

  • 2% Below List Price
  • $245/SF
  • 6 Days On Market

  Current Estimated Value $695,668

  Last Listing Agent Ken Pozek REAL BROKER, LLC

  13243 Charfield St, Windermere, FL 34786
• 

  

  /55

  Est $584,266

  Not Listed For Sale

  6820 Merrick Landing Blvd, Windermere, FL 34786

  • 3 Beds
  • 2 Baths
  • 2,126 Sq Ft
  • Built 2014

  6820 Merrick Landing Blvd, Windermere, FL 34786

  Last Sold Summary

  • 1 Day On Market
• 

  

  /16

  $895,000

  Open Sat 11AM - 2PM $55K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,224 Sq Ft

  13542 Gorgona Isle Dr, Windermere, FL 34786

  Virtually Staged. Lake View Home with Private Pool & Fireworks Views – Minutes from Walt Disney World Imagine living in a home that perfectly combines comfort, elegance, and practicality in one of the most desirable areas of Windermere. This beautiful residence offers stunning lake views and magical nightly fireworks views from Walt Disney World, creating a truly unique living experience. From

  Jennifer Paiano Olmeda WRA BUSINESS & REAL ESTATE

  13542 Gorgona Isle Dr, Windermere, FL 34786
• 

  /2

  $1,650,000

  Sold Sep 29, 2025

  4108 Downeast Ln, Windermere, FL 34786

  • 4 Beds
  • 3 Baths
  • 3,150 Sq Ft
  • Built 1979

  Last Sold Summary

  • 50% Below List Price
  • $524/SF
  • 208 Days On Market

  Current Estimated Value $1,636,348

  Last Listing Agent Padgett McCormick KELLY PRICE & COMPANY LLC

  4108 Downeast Ln, Windermere, FL 34786
• 

  /2

  Est $423,624

  Not Listed For Sale

  11866 Water Run Aly, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 1,722 Sq Ft
  • Built 2016

  11866 Water Run Aly, Windermere, FL 34786

  Last Sold Summary

  • 85 Days On Market
• 

  

  /47

  $1,999,999

  Pending

  • 4 Beds
  • 4.5 Baths
  • 4,013 Sq Ft

  6036 Greatwater Dr, Windermere, FL 34786

  Under contract-accepting backup offers. Classic elegance defined in this stately Keene’s Pointe residence, set along the 17th Fairway of the renowned Jack Nicklaus Signature Golf Course. An impressive grand foyer with warm hardwood flooring greets guests to a traditional-style home with office and formal plus family living spaces on the first floor, along with a guest suite. The primary bedroom

  Rob Rahter STOCKWORTH REALTY GROUP

  6036 Greatwater Dr, Windermere, FL 34786
• 

  

  /29

  $655,000

  Sold Apr 16, 2026

  9426 Palm Tree Dr, Windermere, FL 34786

  • 4 Beds
  • 2 Baths
  • 2,063 Sq Ft
  • Built 1986

  Last Sold Summary

  • 1% Above List Price
  • $317/SF
  • 54 Days On Market

  Current Estimated Value $648,542

  Last Listing Agent Richard Alpizar IVRE ORLANDO

  9426 Palm Tree Dr, Windermere, FL 34786
• 

  /2

  Est $1,154,667

  Not Listed For Sale

  14316 Crest Palm Ave, Windermere, FL 34786

  • 4 Beds
  • 3.5 Baths
  • 3,724 Sq Ft
  • Built 2024

  14316 Crest Palm Ave, Windermere, FL 34786

  Last Sold Summary

  • 0 Days On Market
• 

  

  /54

  $370,000

  $5K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,647 Sq Ft

  14005 Sparkling Cove Ln, Windermere, FL 34786

  Welcome to resort-style living in the gated community of Oasis Cove in the heart of Windermere! This beautifully maintained three-bedroom, 2.5-bath townhome with a two-car garage also features a spacious loft and a versatile bonus room/home office, offering flexible living space beyond the traditional bedroom layout. Tucked away on a quiet dead-end street with minimal traffic, the home enjoys

  Carrie Bantel PREMIER SOTHEBY'S INTL. REALTY

  14005 Sparkling Cove Ln, Windermere, FL 34786
• 

  /2

  $1,030,000

  Sold Apr 27, 2026

  6569 Crestmont Glen Ln, Windermere, FL 34786

  • 4 Beds
  • 3.5 Baths
  • 3,080 Sq Ft
  • Built 2002

  Last Sold Summary

  • 5% Above List Price
  • $334/SF
  • 2 Days On Market

  Current Estimated Value $987,270

  Last Listing Agent Kim Gilbert THE AGENCY FL

  6569 Crestmont Glen Ln, Windermere, FL 34786
• 

  

  /28

  Est $410,129

  Not Listed For Sale

  13303 Gorgona Isle Dr, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 1,441 Sq Ft
  • Built 2020

  13303 Gorgona Isle Dr, Windermere, FL 34786

  Last Sold Summary

  • 24 Days On Market
• 

  

  /77

  $2,590,000

  $299K PRICE DROP

  • 5 Beds
  • 4.5 Baths
  • 3,888 Sq Ft

  5061 Sawyer Cove Way, Windermere, FL 34786

  A truly exceptional CUSTOM residence in the gated enclave of SAWYER SOUND, a private neighborhood of 20 luxury homes. Across the street from Windermere Prep and Windermere High School! This MODERN TRANSITIONAL FARMHOUSE is a rare blend of architectural presence, intentional design, and elevated livability - set on nearly half an acre. Built in 2020 by Cam Bradford Homes, this home showcases solid

  Tammy Carns REVEL REALTY LLC

  5061 Sawyer Cove Way, Windermere, FL 34786
• 

  /2

  $1,350,000

  Sold Oct 30, 2025

  11425 Claymont Cir, Windermere, FL 34786

  • 5 Beds
  • 4 Baths
  • 3,684 Sq Ft
  • Built 1999

  Last Sold Summary

  • 10% Below List Price
  • $366/SF
  • 99 Days On Market

  Current Estimated Value $1,390,064

  Last Listing Agent Ken Pozek REAL BROKER, LLC

  11425 Claymont Cir, Windermere, FL 34786
• 

  /2

  Est $431,582

  Not Listed For Sale

  11405 Brownstone St, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 1,881 Sq Ft
  • Built 2015

  11405 Brownstone St, Windermere, FL 34786

  Last Sold Summary

  • 76 Days On Market
• 

  

  /100

  $2,599,000

  Open House 7/09 $100K PRICE DROP

  • 5 Beds
  • 6 Baths
  • 5,323 Sq Ft

  9222 Tibet Pointe Cir, Windermere, FL 34786

  LOCATION, LOCATION, LOCATION!!! This beautifully custom 5 Bedroom/ 6 full bathroom located a few walks to lake Tibet at KEENE'S POINTE man guard gated Windermere community. Situated on almost half-acre lot, as soon as you walk in toward this custom double-door facade door, you feel the true flawless finish of this stunning Home. The property is richly appointed with travertine floors, granite

  Khadija Webber EPIQUE REALTY INC.

  9222 Tibet Pointe Cir, Windermere, FL 34786
• 

  /2

  $800,000

  Sold Jan 09, 2026

  6905 Nobleton Dr, Windermere, FL 34786

  • 5 Beds
  • 5 Baths
  • 3,345 Sq Ft
  • Built 2005

  Last Sold Summary

  • 2% Below List Price
  • $239/SF
  • 46 Days On Market

  Current Estimated Value $793,593

  Last Listing Agent Tony Tate LPT REALTY, LLC

  6905 Nobleton Dr, Windermere, FL 34786
• 

  /2

  Est $471,092

  Not Listed For Sale

  7653 Ripplepointe Way, Windermere, FL 34786

  • 4 Beds
  • 3 Baths
  • 2,212 Sq Ft
  • Built 2015

  7653 Ripplepointe Way, Windermere, FL 34786

  Last Sold Summary

  • 86 Days On Market
• 

  

  /57

  $1,490,000

  • 5 Beds
  • 4 Baths
  • 3,487 Sq Ft

  12718 Windermere Isles Place, Windermere, FL 34786

  Welcome to 12718 Windermere Isles Place, a spectacular residence tucked away on a quiet cul-de-sac in the heart of Windermere. Situated on a sprawling nearly one-acre lot, this beautifully remodeled home offers an exceptional blend of privacy, space, and elegance. Enjoy serene views of the expansive backyard and picturesque koi pond from the spacious shaded patio or the screened rear porch. The

  Patricia Mascarenhas Bonina Zimath CHARLES RUTENBERG REALTY ORLANDO

  12718 Windermere Isles Place, Windermere, FL 34786
• 

  /2

  $535,000

  Sold Sep 04, 2025

  6830 Mapperton Dr, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 2,230 Sq Ft
  • Built 2005

  Last Sold Summary

  • 1% Below List Price
  • $240/SF
  • 25 Days On Market

  Current Estimated Value $537,606

  Last Listing Agent Kristin Haughwout-Osorio PARKSIDE PROPERTIES, LLC

  6830 Mapperton Dr, Windermere, FL 34786
• 

  

  /61

  Est $1,071,376

  Not Listed For Sale

  8361 Torcello Isle Dr, Windermere, FL 34786

  • 5 Beds
  • 3.5 Baths
  • 4,176 Sq Ft
  • Built 2018

  8361 Torcello Isle Dr, Windermere, FL 34786

  Last Sold Summary

  • 22 Days On Market
• 

  

  /27

  $915,000

  • 4 Beds
  • 3 Baths
  • 2,988 Sq Ft

  9150 Outlook Rock Trail, Windermere, FL 34786

  Welcome to this exquisite and impeccably maintained home filled with natural light and elegant open spaces. As you step inside, you are greeted by a soaring ceiling in the grand foyer that immediately sets the tone for the home’s impressive design.The first floor features a versatile bedroom with a full bath, perfect for guests or multi-generational living, along with a formal dining room

  Chanel Munoz AGENT TRUST REALTY CORPORATION

  9150 Outlook Rock Trail, Windermere, FL 34786
• 

  /2

  $815,000

  Sold Jul 21, 2025

  9601 Ambleside Dr, Windermere, FL 34786

  • 4 Beds
  • 2.5 Baths
  • 3,018 Sq Ft
  • Built 1975

  Last Sold Summary

  • 2% Above List Price
  • $270/SF
  • 5 Days On Market

  Current Estimated Value $854,848

  Last Listing Agent Matt Davies COLDWELL BANKER REALTY

  9601 Ambleside Dr, Windermere, FL 34786
• 

  

  /43

  Est $781,780

  Not Listed For Sale

  8711 Lookout Pointe Dr, Windermere, FL 34786

  • 4 Beds
  • 3.5 Baths
  • 3,419 Sq Ft
  • Built 2015

  8711 Lookout Pointe Dr, Windermere, FL 34786

  Last Sold Summary

  • 10 Days On Market
• 

  

  /61

  $1,425,000

  Pending

  • 4 Beds
  • 3.5 Baths
  • 3,660 Sq Ft

  1125 Kelso Blvd, Windermere, FL 34786

  This is a must see!!! Offering four bedrooms and three and one half baths, this home sits on a beautifully landscaped, estate-sized 1 acre lot! The floor plan is flexible and allows for multiple entertaining options. The kitchen is a cook's dream with an abundance of wood cabinetry, expansive granite counters, a huge center island and built in appliances. It is light and bright and open to the

  Ken Teixeira WEICHERT REALTORS HALLMARK PROPERTIES

  1125 Kelso Blvd, Windermere, FL 34786
• 

  /2

  $1,025,000

  Sold Feb 19, 2026

  1804 Maple Leaf Dr, Windermere, FL 34786

  • 4 Beds
  • 3.5 Baths
  • 2,971 Sq Ft
  • Built 1989

  Last Sold Summary

  • $345/SF
  • 3 Days On Market

  Current Estimated Value $1,010,539

  Last Listing Agent Anna McIntyre LAKESIDE REALTY WINDERMERE INC

  1804 Maple Leaf Dr, Windermere, FL 34786
• 

  

  /37

  Est $438,164

  Not Listed For Sale

  13477 Gorgona Isle Dr, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 1,756 Sq Ft
  • Built 2020

  13477 Gorgona Isle Dr, Windermere, FL 34786

  Last Sold Summary

  • 54 Days On Market

Showing Results 521 - 560, Page 14 of 18