Windermere, FL Homes

• 

  

  

  /36

  $1,349,000

  Pending

  • 4 Beds
  • 3 Baths
  • 2,937 Sq Ft

  5837 Caymus Loop, Windermere, FL 34786

  Under contract-accepting backup offers. Completely renovated and thoughtfully reconfigured in 2023, this stunning 4-bedroom, 3-bath home is located in the highly sought-after, 24-hour gated and guarded community of Keene’s Pointe. Designed for modern living, the home features an open and refreshed layout with new flooring throughout and elegant paneling details that elevate the interior design.

  Jay Stewart SOUTHERN REALTY GROUP LLC

  5837 Caymus Loop, Windermere, FL 34786
• 

  

  /2

  $302,500

  Sold Dec 23, 2025

  12748 Langstaff Dr, Windermere, FL 34786

  • 2 Beds
  • 2.5 Baths
  • 1,380 Sq Ft
  • Built 2004

  Last Sold Summary

  • 11% Below List Price
  • $219/SF
  • 31 Days On Market

  Current Estimated Value $310,072

  Last Listing Agent Steven Koleno BEYCOME OF FLORIDA LLC

  12748 Langstaff Dr, Windermere, FL 34786
• 

  

  /2

  Est $547,991

  Not Listed For Sale

  7742 Brofield Ave, Windermere, FL 34786

  • 3 Beds
  • 2 Baths
  • 2,211 Sq Ft
  • Built 2011

  7742 Brofield Ave, Windermere, FL 34786
• 

  

  

  /81

  $2,550,000

  • 4 Beds
  • 3.5 Baths
  • 3,736 Sq Ft

  5624 W Lake Butler Rd, Windermere, FL 34786

  Opportunities like this in Windermere rarely reach the open market and are often treasured for generations.Welcome to an extraordinary lakefront estate in the highly coveted community of Kelso on Lake Butler, where timeless architecture, unmatched privacy and the ultimate Florida lifestyle come together on over 2 pristine acres along the shores of private Lake Davis.This sprawling custom

  Ronald Ziolkowski RE/MAX PRIME PROPERTIES

  5624 W Lake Butler Rd, Windermere, FL 34786
• 

  

  /2

  $750,000

  Sold May 22, 2026

  5018 River Gem Ave, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 2,379 Sq Ft
  • Built 2005

  Last Sold Summary

  • 4% Below List Price
  • $315/SF
  • 86 Days On Market

  Current Estimated Value $761,235

  Last Listing Agent Anastasia Fischer KELLER WILLIAMS SOUTH TAMPA

  5018 River Gem Ave, Windermere, FL 34786
• 

  

  /20

  Est $451,216

  Not Listed For Sale

  13731 Beringer St, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 1,912 Sq Ft
  • Built 2015

  13731 Beringer St, Windermere, FL 34786

  Last Sold Summary

  • 11 Days On Market
• 

  

  /48

  $710,000

  $29K PRICE DROP

  • 5 Beds
  • 3 Baths
  • 3,050 Sq Ft

  6965 Tettenhall Ln, Windermere, FL 34786

  Beautiful updated windermere home featuring 5 bedrooms 3 full bathrooms , with major upgrades already completed for a peace of mind . Enjoy a brand new roof 05/26 , a brand new Ac 2 Units 05/26 and a brand new water heater 05/26 . Marble floor through downstairs and laminate upstairs , along with remodeled Bathrooms . The house is looking over a stunning view of a pond with a water fountain and

  Nabil Chakrouni VISION HOME REAL ESTATE, LLC

  6965 Tettenhall Ln, Windermere, FL 34786
• 

  /2

  $445,000

  Sold Mar 27, 2026

  13752 Bressler Aly, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 1,976 Sq Ft
  • Built 2018

  Last Sold Summary

  • 4% Below List Price
  • $225/SF
  • 70 Days On Market

  Current Estimated Value $444,501

  Last Listing Agent Jennifer Wemert WEMERT GROUP REALTY LLC

  13752 Bressler Aly, Windermere, FL 34786
• 

  /2

  Est $590,384

  Not Listed For Sale

  8329 Lookout Pointe Dr, Windermere, FL 34786

  • 5 Beds
  • 3.5 Baths
  • 2,633 Sq Ft
  • Built 2016

  8329 Lookout Pointe Dr, Windermere, FL 34786

  Last Sold Summary

  • 56 Days On Market
• 

  

  /36

  $499,900

  Pending

  • 3 Beds
  • 2 Baths
  • 1,700 Sq Ft

  5225 Lemon Twist Ln, Windermere, FL 34786

  Under contract-accepting backup offers. Welcome to Summerport, one of Windermere's most sought-after communities! This charming 3 bedroom, 2 bath single-story home offers nearly 1,700 heated square feet of well-designed living space with a split bedroom floor plan, 2-car garage, and some of the most beautiful curb appeal on the street — complete with a brick paver walkway and low maintenance

  Jonathan Ruiz KELLER WILLIAMS WINTER PARK

  5225 Lemon Twist Ln, Windermere, FL 34786
• 

  /2

  $1,165,000

  Sold Oct 27, 2025

  14404 Crest Palm Ave, Windermere, FL 34786

  • 6 Beds
  • 4.5 Baths
  • 4,565 Sq Ft
  • Built 2024

  Last Sold Summary

  • 3% Below List Price
  • $255/SF
  • 0 Days On Market

  Last Listing Agent Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

  14404 Crest Palm Ave, Windermere, FL 34786
• 

  

  /77

  Est $694,074

  Not Listed For Sale

  8355 Vivaro Isle Way, Windermere, FL 34786

  • 3 Beds
  • 3 Baths
  • 2,224 Sq Ft
  • Built 2019

  8355 Vivaro Isle Way, Windermere, FL 34786

  Last Sold Summary

  • 49 Days On Market
• 

  

  /3

  $1,069,989

  New Construction

  • 6 - 7 Beds
  • 4.5 Baths
  • 4,443 Sq Ft

  Sweetwater Plan at Palms at Windermere, Windermere, FL 34786

  The Sweetwater floorplan offers expansive living with its thoughtfully designed two-story layout. This home features six spacious bedrooms and four and a half bathrooms, perfectly accommodating larger households or guests. With over 4,400 square feet of living space, the Sweetwater includes both a flex room and multiple bonus spaces, offering flexibility for hobbies, workspaces, or entertainment

  Dream Finders Homes Builder

  14207 Crest Palm Ave Unit 36469004, Windermere, FL 34786
• 

  

  /77

  $1,450,000

  Sold Dec 15, 2025

  8117 Whitford Ct, Windermere, FL 34786

  • 4 Beds
  • 3 Baths
  • 3,264 Sq Ft
  • Built 2004

  Last Sold Summary

  • 9% Below List Price
  • $444/SF
  • 11 Days On Market

  Current Estimated Value $1,455,602

  Last Listing Agent Mary Tisdale Keller Williams Realty Emerald

  8117 Whitford Ct, Windermere, FL 34786
• 

  

  /34

  Not Listed For Sale

  6043 Savannah Oak Aly, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 2,117 Sq Ft
  • Built 2019

  6043 Savannah Oak Aly, Windermere, FL 34786

  Last Sold Summary

  • 3 Days On Market
• 

  

  /40

  $565,000

  $5K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,411 Sq Ft

  4627 Blue Major Dr, Windermere, FL 34786

  Welcome to your new forever home in Summerport! This beautifully designed 4-bedroom, 3-bath home offers 2,411 square feet of spacious living with stunning golf course views and no rear neighbors, creating a sense of privacy that’s hard to find. A manicured front lawn welcomes you in, while inside, long hallways with tray ceilings and arched doorways set an elegant tone from the moment you enter.

  Daniel DeLuca DENIZ REALTY PARTNERS LLC

  4627 Blue Major Dr, Windermere, FL 34786
• 

  /2

  $735,000

  Sold Jul 14, 2025

  12880 Westside Village Loop, Windermere, FL 34786

  • 5 Beds
  • 4.5 Baths
  • 3,769 Sq Ft
  • Built 2018

  Last Sold Summary

  • 8% Below List Price
  • $195/SF
  • 118 Days On Market

  Current Estimated Value $785,262

  Last Listing Agent Eric Jia NUMBER 1 BROKER, LLC

  12880 Westside Village Loop, Windermere, FL 34786
• 

  /2

  Not Listed For Sale

  12514 Summer Port Beach Way, Windermere, FL 34786

  • 3 Beds
  • 2 Baths
  • 2,168 Sq Ft
  • Built 1940

  12514 Summer Port Beach Way, Windermere, FL 34786

  Last Sold Summary

  • 198 Days On Market
• 

  

  /44

  $999,000

  • 4 Beds
  • 3 Baths
  • 2,357 Sq Ft

  8525 Bowden Way, Windermere, FL 34786

  Keene's Pointe - 24-hour gated/attended community in Windermere, Florida. 4 bedroom/3 bath home with formal living and dining rooms, kitchen and great room. This quaint home features a functional floor plan. Kitchen with newer stainless appliances, open concept floor plan joining the kitchen, nook and great room and private primary with walk-in closet and bath with dual vanities, shower and

  Teresa Stewart SOUTHERN REALTY GROUP LLC

  8525 Bowden Way, Windermere, FL 34786
• 

  /2

  $615,000

  Sold Jul 30, 2025

  12524 Aldershot Ln, Windermere, FL 34786

  • 4 Beds
  • 2.5 Baths
  • 2,460 Sq Ft
  • Built 2003

  Last Sold Summary

  • 1% Below List Price
  • $250/SF
  • 7 Days On Market

  Current Estimated Value $615,391

  Last Listing Agent Tara Moore TARA MOORE REAL ESTATE

  12524 Aldershot Ln, Windermere, FL 34786
• 

  /2

  Est $1,121,333

  Not Listed For Sale

  14372 Crest Palm Ave, Windermere, FL 34786

  • 6 Beds
  • 4.5 Baths
  • 4,443 Sq Ft
  • Built 2025

  14372 Crest Palm Ave, Windermere, FL 34786

  Last Sold Summary

  • 376 Days On Market
• 

  

  /26

  $1,396,000

  $56K PRICE DROP

  • 6 Beds
  • 4.5 Baths
  • 3,794 Sq Ft

  13596 Gorgona Isle Dr, Windermere, FL 34786

  Stunning Two-Story Pool Home in Prime Windermere LocationWelcome to this exceptional two-story residence located in the highly desirable Windermere area, offering the perfect blend of luxury, space, and comfort. With 6 generously sized bedrooms and an open, airy design, this home is ideal for families seeking both elegance and functionality.The primary suite is a true retreat, featuring a

  Jennifer Paiano Olmeda WRA BUSINESS & REAL ESTATE

  13596 Gorgona Isle Dr, Windermere, FL 34786
• 

  /2

  $305,000

  Sold May 12, 2026

  11434 Jasper Kay Terrace Unit 1120, Windermere, FL 34786

  • 3 Beds
  • 2 Baths
  • 1,332 Sq Ft
  • Built 2007

  Last Sold Summary

  • 6% Below List Price
  • $229/SF
  • 63 Days On Market

  Current Estimated Value $307,000

  Last Listing Agent alonso delgado REALTY ONE GROUP MVP

  11434 Jasper Kay Terrace Unit 1120, Windermere, FL 34786
• 

  

  /37

  Est $2,587,528

  Not Listed For Sale

  6127 Orta Ct, Windermere, FL 34786

  • 4 Beds
  • 4.5 Baths
  • 4,685 Sq Ft
  • Built 2015

  6127 Orta Ct, Windermere, FL 34786

  Last Sold Summary

  • 67 Days On Market
• 

  

  /34

  $650,000

  $60K PRICE DROP

  • 5 Beds
  • 3 Baths
  • 2,511 Sq Ft

  13232 Longacre Dr, Windermere, FL 34786

  Wonderful home in desired Windermere. This two-story home features five large bedrooms and 3 bathrooms and a spacious 2 car garage. Designed with an open floor plan has a large living and dining area and a kitchen with lots of cabinets and pantry.The main floor offers 2 first-floor bedrooms for added convenience and flexibility, for guests or multipurpose room/office plus pantry and storage

  Maria Kronenberg CHARLES RUTENBERG REALTY ORLANDO

  13232 Longacre Dr, Windermere, FL 34786
• 

  /2

  $3,120,000

  Sold Jun 10, 2026

  4029 Isabella Cir, Windermere, FL 34786

  • 6 Beds
  • 8 Baths
  • 7,217 Sq Ft
  • Built 2018

  Last Sold Summary

  • 5% Below List Price
  • $432/SF
  • 18 Days On Market

  Current Estimated Value $3,252,054

  Last Listing Agent Mauro Costa VISTA CAY REALTY COMPANY

  4029 Isabella Cir, Windermere, FL 34786
• 

  

  /37

  Est $439,443

  Not Listed For Sale

  8368 Iron Mountain Trail, Windermere, FL 34786

  • 4 Beds
  • 3 Baths
  • 1,760 Sq Ft
  • Built 2016

  8368 Iron Mountain Trail, Windermere, FL 34786

  Last Sold Summary

  • 31 Days On Market
• 

  

  /11

  $690,000

  Pending

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

  8360 Vivaro Isle Way, Windermere, FL 34786

  Beautiful home located in a quiet and well-maintained community. This property features a functional layout with spacious, light-filled interiors. It offers 4 bedrooms and 2.5 bathrooms. The kitchen is equipped with appliances, and ample storage space—perfect for everyday living and entertaining. Additionally, it includes a private patio, perfect for relaxing or enjoying outdoor time. The

  Monica Duran MD3 HOMES LLC

  8360 Vivaro Isle Way, Windermere, FL 34786
• 

  /2

  $375,000

  Sold Oct 14, 2025

  7819 Hardenton St, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 1,500 Sq Ft
  • Built 2012

  Last Sold Summary

  • 11% Below List Price
  • $250/SF
  • 144 Days On Market

  Current Estimated Value $376,150

  Last Listing Agent Cory Prado COLDWELL BANKER REALTY

  7819 Hardenton St, Windermere, FL 34786
• 

  

  /50

  Est $555,226

  Not Listed For Sale

  7861 Berkshire Oak Aly, Windermere, FL 34786

  • 4 Beds
  • 2.5 Baths
  • 2,214 Sq Ft
  • Built 2018

  7861 Berkshire Oak Aly, Windermere, FL 34786

  Last Sold Summary

  • 8 Days On Market
• 

  

  /91

  $560,000

  • 4 Beds
  • 2.5 Baths
  • 1,840 Sq Ft

  8225 Bryce Canyon Ave, Windermere, FL 34786

  Beautiful 4-Bedroom Home in Windermere, FL – Prime Location and Comfort for the Whole Family! Discover this amazing homelocated in one of Florida’s most desirable neighborhoods – Windermere! Featuring 4 spacious bedrooms, 2 full bathrooms and a half bath, this property offers the ideal space and layout for families seeking comfort and quality of life. The home is vacant and move-in ready,

  Fernando Zucato CHARLES RUTENBERG REALTY ORLANDO

  8225 Bryce Canyon Ave, Windermere, FL 34786
• 

  /2

  $362,500

  Sold Jan 15, 2026

  12307 Langstaff Dr, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 1,520 Sq Ft
  • Built 2013

  Last Sold Summary

  • 2% Below List Price
  • $238/SF
  • 0 Days On Market

  Current Estimated Value $361,759

  Last Listing Agent Kim Hogan HOGAN REALTY GROUP INC

  12307 Langstaff Dr, Windermere, FL 34786
• 

  

  /25

  Est $378,043

  Not Listed For Sale

  12852 Calderdale Ave, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 1,505 Sq Ft
  • Built 2010

  12852 Calderdale Ave, Windermere, FL 34786

  Last Sold Summary

  • 57 Days On Market
• 

  

  /61

  $3,800,000

  Pending

  • 3 Beds
  • 3.5 Baths
  • 4,751 Sq Ft

  9648 Mccormick Place, Windermere, FL 34786

  Stunning golf and lake views and beautifully updated grounds are hallmarks of this elegant Isleworth estate. Nestled along the front nine overlooking Isleworth’s 2nd fairway and beautiful Lake Chase, this two-story home spans more than 4,800 square feet and features modern finishes throughout. Beautiful porcelain tile travels throughout the main level from the spacious living room with an

  Michelle Corbin ISLEWORTH REALTY LLC

  9648 Mccormick Place, Windermere, FL 34786
• 

  /2

  $760,000

  Sold Oct 17, 2025

  13218 Orange Isle Dr, Windermere, FL 34786

  • 4 Beds
  • 3.5 Baths
  • 3,109 Sq Ft
  • Built 2021

  Last Sold Summary

  • 3% Below List Price
  • $244/SF
  • 57 Days On Market

  Current Estimated Value $767,950

  Last Listing Agent Gonzalo Senior IRM INVEST., REAL EST.& MGMT.

  13218 Orange Isle Dr, Windermere, FL 34786
• 

  /2

  Est $778,014

  Not Listed For Sale

  9156 Outlook Rock Trail, Windermere, FL 34786

  • 5 Beds
  • 4 Baths
  • 3,319 Sq Ft
  • Built 2016

  9156 Outlook Rock Trail, Windermere, FL 34786

  Last Sold Summary

  • 12 Days On Market
• 

  

  /8

  $549,999

  • 4 Beds
  • 3 Baths
  • 2,190 Sq Ft

  13424 Hopkinton Ct, Windermere, FL 34786

  Virtually Staged. Nestled on a quiet cul-de-sac in the highly sought-after Lakes of Windermere – Peachtree community, this spacious 4-bedroom, 3-bath residence offers the perfect blend of comfort, functionality, and location. With over 2,100 square feet of living space, the thoughtfully designed floor plan provides ample room for both everyday living and entertaining. Residents of Lakes of

  Erik Lynch LJL REAL ESTATE, INC.

  13424 Hopkinton Ct, Windermere, FL 34786
• 

  /2

  $700,000

  Sold Jun 17, 2026

  13609 Ancilla Blvd, Windermere, FL 34786

  • 4 Beds
  • 3.5 Baths
  • 3,360 Sq Ft
  • Built 2005

  Last Sold Summary

  • 12% Below List Price
  • $208/SF
  • 88 Days On Market

  Current Estimated Value $742,074

  Last Listing Agent Fernanda Soares Santos de Oliveira WRA BUSINESS & REAL ESTATE

  13609 Ancilla Blvd, Windermere, FL 34786
• 

  /2

  Est $1,098,288

  Not Listed For Sale

  13981 Reams Rd, Windermere, FL 34786

  13981 Reams Rd, Windermere, FL 34786

  Last Sold Summary

  • 111 Days On Market
• 

  

  /34

  $389,000

  $6K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 1,632 Sq Ft

  6390 Southbridge St, Windermere, FL 34786

  One or more photo(s) has been virtually staged. Seller may consider buyer concessions if made in an offer ~ Immaculately maintained from top to bottom, including a NEWER A/C (2023) and newer roof (2021), this 4-bedroom, 2.5-bath townhome in the desirable Southbridge Village community delivers the ideal blend of style and location in the heart of Windermere! Framed by mature landscaping and a

  Jennifer Wemert WEMERT GROUP REALTY LLC

  6390 Southbridge St, Windermere, FL 34786

Showing Results 601 - 640, Page 16 of 18