Windermere, FL Homes

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  /39

  $1,098,000

  Open Sat 12PM - 3PM $22K PRICE DROP

  • 6 Beds
  • 4.5 Baths
  • 4,625 Sq Ft

  13525 Gorgona Isle Dr, Windermere, FL 34786

  Set within the highly sought-after Windermere Isle community, this exceptional estate offers elevated living defined by space, craftsmanship, and an unbeatable location just minutes from Walt Disney World. Featuring 6 bedrooms, 4.5 bathrooms, and over 4,600 square feet, the home is thoughtfully designed for both everyday living and effortless entertaining.A dramatic two-story foyer creates a

  

  Roo Klaers

  COLDWELL BANKER REALTY

  13525 Gorgona Isle Dr, Windermere, FL 34786
• Explore Windermere

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  /24

  $1,995 Per Month

  • 2 Beds
  • 2 Baths
  • 1,161 Sq Ft
  • Condo for Rent

  11564 Mizzon Dr Unit 902, Windermere, FL 34786

  Beautiful ground floor unit in the Lakes of Windermere! This unit features 2 bedrooms, 2 bathrooms, ceramic tile flooring throughout and elegant crown molding in the living areas. The kitchen is complete with granite countertops, a breakfast bar and pantry. There is a separate dining area and living room that leads to the large screened in porch. The split floor plan allows privacy, and each

  

  Nicholas Wild

  GATE PROPERTIES & MANAGEMENT INC

  11564 Mizzon Dr Unit 902, Windermere, FL 34786
• 

  

  /2

  $2,335,000

  Sold Jun 10, 2026

  105 Pine St, Windermere, FL 34786

  • 5 Beds
  • 5.5 Baths
  • 5,696 Sq Ft
  • Built 2015

  Last Sold Summary

  • 7% Below List Price
  • $410/SF
  • 9 Days On Market

  Current Estimated Value $2,291,802

  Last Listing Agent Tiffany Pantozzi ALIGN REAL ESTATE LLC

  105 Pine St, Windermere, FL 34786
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  /2

  Est $492,241

  Not Listed For Sale

  12691 Calderdale Ave, Windermere, FL 34786

  • 3 Beds
  • 2 Baths
  • 1,742 Sq Ft
  • Built 2012

  12691 Calderdale Ave, Windermere, FL 34786

  Last Sold Summary

  • 4 Days On Market
• 

  

  

  /81

  $2,125,000

  Pending

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

  12699 Hawkstone Dr, Windermere, FL 34786

  Under contract-accepting backup offers. Welcome to Chalet du Lac, set on the exclusive and private Lake Sawyer chain of lakes in Windermere—where mornings are welcomed by sunrise over glistening waters dancing through a veil of Cypress trees and Spanish moss. Nestled along the western shoreline of Lake Sawyer within an enclave of custom-built lakefront homes, Chalet du Lac features 4 bedrooms and

  

  Drew Ross

  LAKEFIELD REALTY GROUP LLC

  12699 Hawkstone Dr, Windermere, FL 34786
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  Starting at $1,718

  Total Monthly Price

  • 1 - 3 Beds

  6506 San Francesco Way, Windermere, FL 34786

  A beautiful community with luxury one, two and three-bedroom apartment homes with a Mediterranean flair.We invite you to transport yourself to an upgraded level of luxury right at your front door. Every finish is hand-selected with the finest touch to make every day surpass the next. Our elegant, resort-inspired amenities have a level of sophistication you'll find awe-inspiring day and night.

  Venetian Isle

  

  6506 San Francesco Way, Windermere, FL 34786
• 

  /2

  $1,150,000

  Sold Jun 23, 2026

  8409 Vivaro Isle Way, Windermere, FL 34786

  • 6 Beds
  • 4.5 Baths
  • 4,176 Sq Ft
  • Built 2019

  Last Sold Summary

  • 7% Below List Price
  • $275/SF
  • 30 Days On Market

  Current Estimated Value $1,008,036

  Last Listing Agent Katherine Figueroa Santiago WATSON REALTY CORP., REALTORS

  8409 Vivaro Isle Way, Windermere, FL 34786
• 

  /2

  Est $322,489

  Not Listed For Sale

  8168 Boat Hook Loop Unit 201/718, Windermere, FL 34786

  • 3 Beds
  • 2 Baths
  • 1,442 Sq Ft
  • Built 2006

  8168 Boat Hook Loop Unit 201/718, Windermere, FL 34786

  Last Sold Summary

  • 4 Days On Market
• 

  

  /66

  $425,000

  Open Sun 1PM - 4PM

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

  7435 Ripplepointe Way, Windermere, FL 34786

  Welcome home to Lake Burden, one of Windermere's most peaceful and welcoming neighborhoods. This beautifully maintained 3-bedroom, 2.5-bath townhouse — built in 2013 — is move-in ready, waiting for you with the BEST PRICE in the area! Start your mornings on the charming front porch, where you can sip your coffee and watch the neighborhood come to life. Inside, the main floor covered with

  

  HERNY MENDEZ

  LPT REALTY, LLC

  7435 Ripplepointe Way, Windermere, FL 34786
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  /23

  $3,100 Per Month

  • 4 Beds
  • 2.5 Baths
  • 2,830 Sq Ft
  • House for Rent

  6746 Duncaster St, Windermere, FL 34786

  Welcome to 6746 Duncaster Street, a spacious and beautifully maintained two-story home nestled within the highly sought-after Lakes of Windermere community. Offering 4 bedrooms, 2.5 bathrooms, and approximately 2,830 square feet of living space, this residence combines comfort, functionality, and an exceptional location. Tons of storage space. The thoughtfully designed floor plan features formal

  

  Cheryl Rozanski

  JC FLORIDA REALTY LLC

  6746 Duncaster St, Windermere, FL 34786
• 

  /2

  $350,000

  Sold Jun 12, 2026

  6528 Helmsley Cir, Windermere, FL 34786

  • 2 Beds
  • 2.5 Baths
  • 1,411 Sq Ft
  • Built 2008

  Last Sold Summary

  • 8% Above List Price
  • $248/SF
  • 8 Days On Market

  Current Estimated Value $466,355

  Last Listing Agent Daniel Rodriguez NEW HEIGHTS REALTY GROUP

  6528 Helmsley Cir, Windermere, FL 34786
• 

  /2

  Est $321,510

  Not Listed For Sale

  8256 Maritime Flag St Unit 103, Windermere, FL 34786

  • 3 Beds
  • 2 Baths
  • 1,442 Sq Ft
  • Built 2009

  8256 Maritime Flag St Unit 103, Windermere, FL 34786

  Last Sold Summary

  • 33 Days On Market
• 

  

  /100

  $5,250,000

  Pending

  • 6 Beds
  • 8 Baths
  • 7,818 Sq Ft

  9713 Endicott Ct, Windermere, FL 34786

  Experience elevated lakefront living in this beautifully updated estate, within the prestigious guard gated golf community of Keene’s Pointe, offering direct access to the Butler Chain of Lakes. With over $850,000 in upgrades, this home is perfectly positioned to capture breathtaking sunset views and nightly Disney fireworks from the primary suite. This home delivers a rare combination of

  

  Amy Moline

  EXP REALTY LLC

  9713 Endicott Ct, Windermere, FL 34786
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  Starting at $1,689 Per Month

  • 1 - 3 Beds

  13644 Tortona Ln, Windermere, FL 34786

  Addison At Windermere is located at 13644 Tortona Lane Windermere, FL and is managed by GrayCo Properties, LLC, a reputable property management company. Addison At Windermere offers 1 to 3 bedroom apartments ranging in size from 592 to 1508 sq.ft. Amenities include Microwave and more. This rental community is pet friendly, welcoming both cats and dogs. Property is located in the 34786 ZIP code.

  Addison At Windermere

  13644 Tortona Ln, Windermere, FL 34786
• 

  /2

  $767,000

  Sold May 28, 2026

  9164 Patrimonio Loop, Windermere, FL 34786

  • 4 Beds
  • 3 Baths
  • 2,449 Sq Ft
  • Built 2020

  Last Sold Summary

  • 1% Below List Price
  • $313/SF
  • 6 Days On Market

  Current Estimated Value $763,913

  Last Listing Agent Lisa Grinceri KELLER WILLIAMS REALTY AT THE LAKES

  9164 Patrimonio Loop, Windermere, FL 34786
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  /2

  Est $460,856

  Not Listed For Sale

  13727 Bressler Aly, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 2,001 Sq Ft
  • Built 2019

  13727 Bressler Aly, Windermere, FL 34786

  Last Sold Summary

  • 86 Days On Market
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  /47

  $725,000

  Pending

  • 5 Beds
  • 3 Baths
  • 2,464 Sq Ft

  7174 Beek St, Windermere, FL 34786

  Welcome to this solid built 1-story 5 bedroom split plan, 3 full baths home with 2464 square feet of well designed living space, plus a 3 car garage and no rear neighbor as it backs to the brick wall of Windermere Terrace. Inside you'll find soaring 10' ceilings & 6-incht baseboards throughout, crown moldings in the family/kitchen area, ceramic tile in the kitchen & bathrooms and engineered wood

  

  Ron Hernquist

  RE/MAX CENTRAL REALTY

  7174 Beek St, Windermere, FL 34786
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  $9,950 Per Month

  • 5 Beds
  • 4.5 Baths
  • 4,291 Sq Ft
  • House for Rent

  11050 Coniston Way, Windermere, FL 34786

  Welcome to this stunning FULLY FURNISHED luxury estate in the GUARD-GATED community of Lake Butler Sound in Windermere. Designed in timeless French Country style, this remarkable residence offers an effortless blend of elegance, comfort, and refined living. Beautifully appointed and professionally furnished throughout, this turnkey home is ready for immediate enjoyment. From the moment you

  

  Alexis Jacobsen

  EXP REALTY LLC

  11050 Coniston Way, Windermere, FL 34786
• 

  /2

  $750,000

  Sold Sep 18, 2025

  14654 Yellow Butterfly Rd, Windermere, FL 34786

  • 5 Beds
  • 3.5 Baths
  • 3,094 Sq Ft
  • Built 2015

  Last Sold Summary

  • 6% Below List Price
  • $242/SF
  • 44 Days On Market

  Current Estimated Value $744,891

  Last Listing Agent Elijah Lewis FLORIDA IN MOTION REALTY INC

  14654 Yellow Butterfly Rd, Windermere, FL 34786
• 

  /2

  Est $742,695

  Not Listed For Sale

  9227 Outlook Rock Trail, Windermere, FL 34786

  • 4 Beds
  • 4 Baths
  • 3,239 Sq Ft
  • Built 2016

  9227 Outlook Rock Trail, Windermere, FL 34786

  Last Sold Summary

  • 69 Days On Market
• 

  

  /70

  $322,000

  $14K PRICE DROP Pending

  • 3 Beds
  • 2 Baths
  • 1,442 Sq Ft

  8180 Boat Hook Loop Unit 108/301, Windermere, FL 34786

  Under contract-accepting backup offers. Discover the best of Windermere living in this meticulously maintained 3-bedroom, 2-bath CORNER UNIT condo in Lakeside at Lakes of Windermere. An expansive wrap-around screened porch embraces tranquil views and Florida breezes while providing an ideal space for morning coffee or evening relaxation. Inside, the open-concept layout features silestone

  

  Erin Aaron

  EXP REALTY LLC

  8180 Boat Hook Loop Unit 108/301, Windermere, FL 34786
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  Starting at $1,945 Per Month

  • 1 - 2 Beds

  1231 Arya Way, Ocoee, FL 34761

  Discover refined active adult living at Arya at Windermere, a premier 55+ community offering luxury and vibrancy of Windermere. Our spacious one- and two-bedroom residences feature impressive finishes and thoughtful designs that elevate everyday living. Residents enjoy resort-style amenities including a massage room, steam room, and a host of social and wellness opportunities in a pet-friendly

  Arya at Windermere

  

  1231 Arya Way, Ocoee, FL 34761
• 

  /2

  $2,350,000

  Sold Oct 14, 2025

  1003 Oakdale St, Windermere, FL 34786

  • 6 Beds
  • 5.5 Baths
  • 4,599 Sq Ft
  • Built 2003

  Last Sold Summary

  • 22% Below List Price
  • $511/SF
  • 280 Days On Market

  Current Estimated Value $2,356,824

  Last Listing Agent Darrell Nunnelley VINTAGE REALTY GROUP LLC

  1003 Oakdale St, Windermere, FL 34786
• 

  /2

  Est $871,136

  Not Listed For Sale

  9248 Legado Dr, Windermere, FL 34786

  • 4 Beds
  • 3 Baths
  • 2,823 Sq Ft
  • Built 2021

  9248 Legado Dr, Windermere, FL 34786

  Last Sold Summary

  • 33 Days On Market
• 

  

  /45

  $1,299,000

  $50K PRICE DROP Pending

  • 6 Beds
  • 3.5 Baths
  • 3,364 Sq Ft

  2219 Ridgewind Way, Windermere, FL 34786

  Under contract-accepting backup offers. Set behind the gates of The Estates at Windermere—an intimate enclave of just 67 homes—2219 Ridgewind Way is the kind of property that stops you mid-scroll. A true Victorian-inspired residence, its architectural presence is unforgettable: a statement turret, wraparound porch, and intricate trim work that feels both rare and timeless in today’s market. It’s

  

  Hilary Hall

  COMPASS FLORIDA LLC

  2219 Ridgewind Way, Windermere, FL 34786
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  Starting at $1,525 Per Month

  • 1 - 3 Beds

  11353 Citra Cir, Windermere, FL 34786

  Experience the finest apartments in Windermere, Florida at The Citra at Windermere. Our apartment community offers a variety of distinctive one, two, and three bedroom apartment homes. Conveniently located, Citra at Windermere is walking distance to shopping, restaurants and entertainment. In addition, we are located within some of the top rated schools in Orange county, including Bay

  Citra at Windermere

  

  11353 Citra Cir, Windermere, FL 34786
• 

  /2

  $1,000,000

  Sold Jun 26, 2025

  11415 N Camden Commons Dr, Windermere, FL 34786

  • 4 Beds
  • 3 Baths
  • 3,034 Sq Ft
  • Built 2005

  Last Sold Summary

  • 9% Below List Price
  • $330/SF
  • 15 Days On Market

  Current Estimated Value $1,000,799

  Last Listing Agent Christina Fata REAL BROKER, LLC

  11415 N Camden Commons Dr, Windermere, FL 34786
• 

  /2

  Est $1,741,072

  Not Listed For Sale

  10988 Down Park Ln, Windermere, FL 34786

  10988 Down Park Ln, Windermere, FL 34786

  Last Sold Summary

  • 214 Days On Market
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  $455,000

  $15K PRICE DROP Pending

  • 3 Beds
  • 2.5 Baths
  • 2,002 Sq Ft

  13733 Bressler Aly, Windermere, FL 34786

  Under contract-accepting backup offers. Location location location!! This beautiful 3 bedrooms, 2 1/2 baths, includes a spacious open floor plan with a breakfast bar in the kitchen area and Living Room/Dining Room Combo. Master Bedroom is located on the second floor, as well as two more bedrooms. This two car garage townhouse has a charming front porch which overlooks the pond and offers, not

  

  Robert Welker, III

  CORCORAN PREMIER REALTY

  13733 Bressler Aly, Windermere, FL 34786
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  Starting at $1,595 Per Month

  • 1 - 3 Beds

  7826 Crosswater Trail, Windermere, FL 34786

  TOUR YOUR WAY! We have a tour to fit your needs- virtual, self-guided, or agent-guided. Discover resort-style living at MAA Crosswater in Windermere, FL. Garden tubs, double vanity sinks, and washer/dryer units are featured in these one-, two-, and three-bedroom apartment homes. Admire the lake view from our sparkling swimming pool and cabana, or dig your toes in the sand \"beach\" lounging area.

  MAA Crosswater

  

  7826 Crosswater Trail, Windermere, FL 34786
• 

  /2

  $753,000

  Sold Jan 21, 2026

  11660 Delwick Dr, Windermere, FL 34786

  • 4 Beds
  • 4.5 Baths
  • 3,051 Sq Ft
  • Built 2004

  Last Sold Summary

  • 16% Below List Price
  • $247/SF
  • 146 Days On Market

  Current Estimated Value $775,717

  Last Listing Agent Natalie Rosario FATHOM REALTY FL LLC

  11660 Delwick Dr, Windermere, FL 34786
• 

  /2

  Est $1,426,811

  Not Listed For Sale

  5950 Blakeford Dr, Windermere, FL 34786

  • 4 Beds
  • 3 Baths
  • 2,996 Sq Ft
  • Built 1999

  5950 Blakeford Dr, Windermere, FL 34786

  Last Sold Summary

  • 11 Days On Market
• 

  

  /64

  $1,375,000

  $75K PRICE DROP

  • 6 Beds
  • 4.5 Baths
  • 3,463 Sq Ft

  11617 Camden Park Dr, Windermere, FL 34786

  Welcome to one of Central Florida’s premier guard-gated golf communities. This impeccably maintained, move-in ready residence showcases refined finishes throughout, including tile and laminate flooring (no carpet), crown molding in every room, and upgraded designer lighting. An abundance of space with 6 bedrooms and 4 1/2 baths. The living room is enhanced by striking wood-look tiled accent

  

  Carla Robles

  WATSON REALTY CORP

  11617 Camden Park Dr, Windermere, FL 34786
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  Starting at $1,608 Per Month

  • 1 - 3 Beds

  11598 Lachlan Ln, Windermere, FL 34786

  TOUR YOUR WAY! We have a tour to fit your needs- virtual, self-guided, or agent-guided. Call MAA Windermere home in Windermere, FL. Our one-, two-, and three-bedroom apartment homes have all of the modern conveniences you're looking for. Select apartments feature spacious showers, double vanities, and soaking tubs. All units come with a washer/dryer and lots of natural light. Enjoy an expansive

  MAA Windermere

  

  11598 Lachlan Ln, Windermere, FL 34786
• 

  /2

  $849,000

  Sold Dec 09, 2025

  11108 Ledgement Ln Unit 2, Windermere, FL 34786

  • 4 Beds
  • 3.5 Baths
  • 3,024 Sq Ft
  • Built 2003

  Last Sold Summary

  • $281/SF
  • 3 Days On Market

  Current Estimated Value $846,438

  Last Listing Agent Terrie Giles KELLER WILLIAMS CLASSIC

  11108 Ledgement Ln Unit 2, Windermere, FL 34786
• 

  /2

  Est $2,123,461

  Not Listed For Sale

  11227 Macaw Ct, Windermere, FL 34786

  • 6 Beds
  • 5 Baths
  • 5,030 Sq Ft
  • Built 2004

  11227 Macaw Ct, Windermere, FL 34786

  Last Sold Summary

  • 231 Days On Market
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  $480,000

  $10K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,996 Sq Ft

  13755 Bravante Aly, Windermere, FL 34786

  **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 13755 Bravante Aly, Windermere, FL 34786, a charming two story home featuring 3 bedrooms and 2 bathrooms located in a desirable Windermere community. This home offers a bright open floor plan with comfortable

  

  Thomas Nickley

  KELLER WILLIAMS REALTY AT THE PARKS

  13755 Bravante Aly, Windermere, FL 34786
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  /25

  Starting at $1,760

  Total Monthly Price

  • 1 - 3 Beds

  101 Casa Mirella Way, Windermere, FL 34786

  Welcome to Casa Mirella Apartments, where lakeside living meets luxury in the heart of Windermere, FL. Enjoy sunny Florida days by the resort-style swimming pool, stay active in the fully equipped fitness center, or relax with friends at the picnic area with outdoor grills. Your furry friend will love the dog park at our luxury apartments in Windermere, FL, and you’ll appreciate the peace of mind

  Casa Mirella

  

  101 Casa Mirella Way, Windermere, FL 34786
• 

  /2

  $840,646

  Sold Mar 30, 2026

  4926 Indian Deer Rd, Windermere, FL 34786

  • 5 Beds
  • 4.5 Baths
  • 3,849 Sq Ft
  • Built 2006

  Last Sold Summary

  • 12% Below List Price
  • $218/SF
  • 135 Days On Market

  Current Estimated Value $859,263

  Last Listing Agent Shelley Dawson COMPASS FLORIDA LLC

  4926 Indian Deer Rd, Windermere, FL 34786
• 

  /2

  Est $2,397,926

  Not Listed For Sale

  8148 Tibet Butler Dr, Windermere, FL 34786

  • 4 Beds
  • 4.5 Baths
  • 5,118 Sq Ft
  • Built 2001

  8148 Tibet Butler Dr, Windermere, FL 34786

  Last Sold Summary

  • 119 Days On Market

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