Windermere, FL Homes

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  /17

  $1,052,990

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,791 Sq Ft

  Moseley Plan at Lake Cawood Cove - Traditional, Windermere, FL 34786

  The Moseley is a thoughtfully designed two-story home with three bedrooms, two full bathrooms, one half bathroom, and a two-car garage. This plan features a dramatic two-story family room that creates a bright and open living space. The second-floor primary suite offers privacy and comfort, while additional flexible living areas provide room to relax or entertain. Modern finishes, abundant

  Ashton Woods Builder

  5432 Winter Garden Vineland Rd Unit 37932785, Windermere, FL 34786
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  /11

  $7,500 Per Month

  • 6 Beds
  • 4 Baths
  • 3,916 Sq Ft
  • House for Rent

  3302 Butler Bay Dr N, Windermere, FL 34786

  Welcome home to this stunning two-story custom estate located in one of Orlando’s most sought-after communities, The Windermere Club. Set on over an acre and surrounded by natural landscape, this home offers exceptional privacy and space. An expansive driveway and impressive elevation lead to a grand foyer with a spiral staircase, formal dining room, and pass-through fireplace. The fully

  3302 Butler Bay Dr N, Windermere, FL 34786
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  /2

  $760,000

  Sold Apr 10, 2026

  12676 Salomon Cove Dr, Windermere, FL 34786

  • 6 Beds
  • 4 Baths
  • 3,667 Sq Ft
  • Built 2018

  Last Sold Summary

  • 15% Below List Price
  • $207/SF
  • 120 Days On Market

  Current Estimated Value $767,384

  Last Listing Agent Anna Shi LPT REALTY, LLC

  12676 Salomon Cove Dr, Windermere, FL 34786
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  /69

  Est $317,517

  Not Listed For Sale

  8110 Enchantment Dr Unit 1704, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 1,371 Sq Ft
  • Built 2011

  8110 Enchantment Dr Unit 1704, Windermere, FL 34786

  Last Sold Summary

  • 19 Days On Market
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  /71

  $1,295,000

  • 3 Beds
  • 2.5 Baths
  • 3,021 Sq Ft

  516 Jennifer Ln, Windermere, FL 34786

  OUTDOOR LIVING, ONE-STORY COMFORT & IN-TOWN WINDERMERE LIFESTYLE COME TOGETHER AT THIS RARE 1.27-ACRE WINDERMERE OAKS PROPERTY. Set within the TOWN OF WINDERMERE, this beautifully maintained one-story pool home offers privacy, space & the lifestyle buyers hope to find, with NATURAL GAS, mature landscaping, a PARTIAL BUTLER CHAIN LAKE VIEW, and exceptional outdoor living that feels like a true

  Cindy Rosenbloom THE ROSENBLOOM TEAM

  516 Jennifer Ln, Windermere, FL 34786
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  /32

  $6,990 Per Month

  • 4 Beds
  • 3 Baths
  • 2,817 Sq Ft
  • House for Rent

  11820 Waterstone Loop Dr, Windermere, FL 34786

  Welcome to this beautifully maintained single-story home located in the highly sought-after Waterstone community in Windermere. Offering 4 bedrooms and 3 full bathrooms, this residence combines comfort, functionality, and elegant living in a prime Central Florida location.The spacious floor plan features a large living room with a cozy fireplace, a centrally located dining area, and an

  Charles Kohlinger BHHS FLORIDA REALTY

  11820 Waterstone Loop Dr, Windermere, FL 34786
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  /2

  $2,700,000

  Sold Feb 09, 2026

  9151 Tibet Pointe Cir, Windermere, FL 34786

  • Land
  • 2.21 Acres
  • $1,221,719 per Acre

  Last Sold Summary

  • 16% Below List Price
  • 341 Days On Market

  Current Estimated Value $2,707,834

  Last Listing Agent Janet Allen PREMIER SOTHEBYS INT'L REALTY

  9151 Tibet Pointe Cir, Windermere, FL 34786
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  /31

  Est $356,913

  Not Listed For Sale

  8167 Enchantment Dr Unit 1501, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 1,786 Sq Ft
  • Built 2010

  8167 Enchantment Dr Unit 1501, Windermere, FL 34786

  Last Sold Summary

  • 1 Day On Market
• 

  

  /33

  $440,000

  • 3 Beds
  • 2.5 Baths
  • 1,742 Sq Ft

  7612 Fairgrove Ave, Windermere, FL 34786

  Beautiful two-story townhome in the desirable Windermere Sound community! This stunning residence offers 3 bedrooms, 2.5 bathrooms, and a spacious 2-car garage, spanning 1,742 sq. ft. of elegant living space. The home features stainless steel appliances, granite countertops, and modern finishes throughout. Windermere Sound provides residents with resort-style amenities, including a swimming pool,

  Maribel Minarro FLORIDA FANTASY REAL ESTATE INC

  7612 Fairgrove Ave, Windermere, FL 34786
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  /8

  $1,349 Per Month

  • 1 Bed
  • 1 Bath
  • 500 Sq Ft
  • Townhouse for Rent

  12645 Salomon Cove Dr, Windermere, FL 34786

  1/1 guest house above the garage for rent, included HOA, lawn care, shared internet, garage is not included, one parking spot. Close to shopping center and Disney parks. requirement, income 3X of rent, good credit. NO PETS.

  12645 Salomon Cove Dr, Windermere, FL 34786
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  /2

  $2,171,470

  Sold Apr 29, 2026

  1020 Oakdale St, Windermere, FL 34786

  • 5 Beds
  • 4.5 Baths
  • 3,994 Sq Ft
  • Built 2025

  Last Sold Summary

  • 1% Below List Price
  • $544/SF
  • 107 Days On Market

  Current Estimated Value $1,981,648

  Last Listing Agent Christopher Christensen ONE LUXURY INTERNATIONAL LLC

  1020 Oakdale St, Windermere, FL 34786
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  /43

  Est $2,837,595

  Not Listed For Sale

  5054 Sawyer Cove Way, Windermere, FL 34786

  • 5 Beds
  • 6.5 Baths
  • 5,353 Sq Ft
  • Built 2020

  5054 Sawyer Cove Way, Windermere, FL 34786

  Last Sold Summary

  • 7 Days On Market
• 

  

  /18

  $408,000

  $42K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,584 Sq Ft

  11636 Water Run Aly, Windermere, FL 34786

  This property is a beautifully maintained 3-bedroom, 2.5-bath townhouse located in the desirable Ashlin Park community of Windermere. Built in 2017, this home features an open-concept layout filled with natural light, a modern kitchen with quartz countertops, stainless steel appliances, and espresso cabinetry. The spacious primary suite offers a walk-in closet and an elegant ensuite bath. Enjoy a

  Jose Jimenez EXP REALTY LLC

  11636 Water Run Aly, Windermere, FL 34786
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  /30

  $2,850 Per Month

  • 4 Beds
  • 2.5 Baths
  • 2,068 Sq Ft
  • House for Rent

  12030 Silverlake Park Dr, Windermere, FL 34786

  LOCATION, LOCATION, LOCATION. Beautiful 4/bed 2.5/bath home in desirable Windermere Trails. Watch Disney fireworks nightly fromspacious front porch! The home has tile and luxury vinyl throughout (NO CARPET) with plenty of room for families or individuals. Family room and dining room are downstairs along with a kitchen that features stainless steel appliances and granite counters. Master

  Carolyn Hunt TOPSKY REALTY INC

  12030 Silverlake Park Dr, Windermere, FL 34786
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  /2

  $860,000

  Sold May 21, 2026

  8415 Vivaro Isle Way, Windermere, FL 34786

  • 4 Beds
  • 3 Baths
  • 3,038 Sq Ft
  • Built 2019

  Last Sold Summary

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

  Current Estimated Value $832,601

  Last Listing Agent Amy Kidwell PA PREFERRED REAL ESTATE BROKERS

  8415 Vivaro Isle Way, Windermere, FL 34786
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  /41

  Est $1,573,090

  Not Listed For Sale

  1121 Estancia Woods Loop, Windermere, FL 34786

  • 4 Beds
  • 4 Baths
  • 3,493 Sq Ft
  • Built 2017

  1121 Estancia Woods Loop, Windermere, FL 34786

  Last Sold Summary

  • 41 Days On Market
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  /40

  $3,299,999

  $200K PRICE DROP

  • 5 Beds
  • 4.5 Baths
  • 4,417 Sq Ft

  5001 Latrobe Dr, Windermere, FL 34786

  One or more photo(s) has been virtually staged. Traditional five-bedroom four and a half bath pool home with an open layout in Isleworth Golf & Country Club. Perfectly positioned on a quiet cul-de-sac along the 6th fairway with serene views of Lake Bessie. Offering 4,417 square feet of refined living space, this elegant two-story residence features two primary suites downstairs with private

  Laura Diss Q BOUTIQUE SPECIALTY REALTY INC

  5001 Latrobe Dr, Windermere, FL 34786
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  /28

  $7,995 Per Month

  • 4 Beds
  • 3 Baths
  • 3,062 Sq Ft
  • House for Rent

  8122 Whitford Ct, Windermere, FL 34786

  Keenes Pointe Golf front beauty!!. The home backs up to the driving This lovely 4 bed 3 bath home available is for rent in the popular and exclusive Keenes Pointe Golf Community. This is a gated community with manned security . Keenes Pointe is popular because of the strong community atmosphere. It has a restaurant on site, fitness and tennis courts . All the facilities are close to this

  8122 Whitford Ct, Windermere, FL 34786
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  /2

  $380,000

  Sold Nov 13, 2025

  5219 Keenes Pheasant Dr, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 1,461 Sq Ft
  • Built 2004

  Last Sold Summary

  • 1% Below List Price
  • $260/SF
  • 6 Days On Market

  Current Estimated Value $383,538

  Last Listing Agent Roland Cotardo THE SIMON SIMAAN GROUP

  5219 Keenes Pheasant Dr, Windermere, FL 34786
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  /8

  Est $2,191,790

  Not Listed For Sale

  7085 Horizon Cir, Windermere, FL 34786

  • 5 Beds

  7085 Horizon Cir, Windermere, FL 34786

  Last Sold Summary

  • 113 Days On Market
• 

  

  /26

  $900,000

  $100K PRICE DROP

  • Land
  • 21,780 Sq Ft
  • $1,800,000 per Acre

  2504 Windermere Reserve Ct, Windermere, FL 34786

  Final Opportunity – Last Lot Available in The Reserve at Windermere! Build your dream home in the exclusive community of The Reserve at Windermere with acclaimed custom builder Element Home Builders. This final remaining homesite of 8 offers a rare opportunity to craft a one-of-a-kind luxury residence in one of Central Florida’s most prestigious neighborhoods. Surrounded by the natural beauty of

  Carolina Dumit CORCORAN PREMIER REALTY

  2504 Windermere Reserve Ct, Windermere, FL 34786
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  /58

  $13,000 Per Month

  • 5 Beds
  • 5.5 Baths
  • 5,498 Sq Ft
  • House for Rent

  11051 Coniston Way, Windermere, FL 34786

  A rare opportunity to lease a furnished executive estate in the prestigious guard-gated community of Lake Butler Sound. Perfect for corporate relocations, executive families, or those building, renovating, or transitioning between homes, this turnkey residence offers flexible lease terms in one of Windermere's most sought-after communities. Thoughtfully designed for comfortable everyday living

  Julian Correa THE SIMON SIMAAN GROUP

  11051 Coniston Way, Windermere, FL 34786
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  /2

  $475,000

  Sold Sep 23, 2025

  5130 Sun Palm Dr, Windermere, FL 34786

  • 3 Beds
  • 2 Baths
  • 1,723 Sq Ft
  • Built 1987

  Last Sold Summary

  • 16% Below List Price
  • $276/SF
  • 23 Days On Market

  Current Estimated Value $521,145

  Last Listing Agent Elle Walters JASON MITCHELL REAL ESTATE FLO

  5130 Sun Palm Dr, Windermere, FL 34786
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  /59

  Est $1,872,320

  Not Listed For Sale

  13407 Bellaria Cir, Windermere, FL 34786

  • 4 Beds
  • 6 Baths
  • 3,640 Sq Ft
  • Built 2014

  13407 Bellaria Cir, Windermere, FL 34786

  Last Sold Summary

  • 10 Days On Market
• 

  

  /49

  $1,200,000

  • 4 Beds
  • 4 Baths
  • 2,787 Sq Ft

  1361 Whitney Isles Dr, Windermere, FL 34786

  Stunning residence with a private fenced backyard, located in the highly sought-after gated community of Belmere in Windermere, just minutes from the town center. Featuring 4 bedrooms, 4 bathrooms, and approximately 2,800 sq. ft. of air-conditioned living space, this home immediately captivates with its elegant Mediterranean architecture and lush tropical landscaping. Fully renovated this year,

  Gabriel Mantovani ALVES AND HOWELL REALTY

  1361 Whitney Isles Dr, Windermere, FL 34786
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  /6

  $1,950 Per Month

  • 2 Beds
  • 2 Baths
  • 2 bed 2 bath condo at LAKESIDE WINDERMERE

  11562 Amidship Ln, Windermere, FL 34786

  great 2-bedroom condo with laminate floors located at Lakeside at Windermere; all appliances included access to community pool, club house and gym. 2 parking spaces.

  11562 Amidship Ln, Windermere, FL 34786
• 

  /2

  $675,000

  Sold Apr 15, 2026

  6990 Smithshire Ln, Windermere, FL 34786

  • 4 Beds
  • 3.5 Baths
  • 2,986 Sq Ft
  • Built 2007

  Last Sold Summary

  • $226/SF
  • 10 Days On Market

  Current Estimated Value $672,900

  Last Listing Agent Beverly Brown RE/MAX PRIME PROPERTIES

  6990 Smithshire Ln, Windermere, FL 34786
• 

  

  /58

  Est $1,751,687

  Not Listed For Sale

  11603 Vinci Dr, Windermere, FL 34786

  • 5 Beds
  • 4.5 Baths
  • 3,672 Sq Ft
  • Built 2013

  11603 Vinci Dr, Windermere, FL 34786

  Last Sold Summary

  • 60 Days On Market
• 

  

  /44

  $750,000

  Pending

  • 4 Beds
  • 3.5 Baths
  • 3,413 Sq Ft

  11903 Cave Run Ave, Windermere, FL 34786

  Under contract-accepting backup offers. Stunning move-in ready home in the highly sought-after Windermere Trails community, located in a top-rated school district and just 2 miles from Walt Disney World! This beautifully upgraded 4-bedroom, 3.5-bath home features a gourmet kitchen with an oversized center island, custom solid wood cabinetry, granite countertops, built-in ovens, and a spacious

  Yan Zheng LOKATION

  11903 Cave Run Ave, Windermere, FL 34786
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  /42

  $3,995 Per Month

  • 4 Beds
  • 2 Baths
  • 2,373 Sq Ft
  • House for Rent

  17514 Black Rail St, Windermere, FL 34786

  Luxury one-level Mediterranean Style home located in the highly desirable Enclave community at WINDERMERE. This elegant home is Energy Star Certified and also come with Solar Panels, monthly electric bill is only around $33! Step into the grand entryway with extensive natural light throughout, this 4 bedrooms, 2 baths with an office home deliver a bright open atmosphere.Open floor open, well

  Eleanor Wong SUNSHINE REALTY & PROP. MGNT

  17514 Black Rail St, Windermere, FL 34786
• 

  /2

  $1,220,000

  Sold Jan 23, 2026

  2828 Ingeborg Ct, Windermere, FL 34786

  • 5 Beds
  • 4.5 Baths
  • 3,190 Sq Ft
  • Built 1990

  Last Sold Summary

  • 8% Below List Price
  • $382/SF
  • 40 Days On Market

  Current Estimated Value $1,200,767

  Last Listing Agent Tiffany Pantozzi ALIGN REAL ESTATE LLC

  2828 Ingeborg Ct, Windermere, FL 34786
• 

  /2

  Est $3,107,934

  Not Listed For Sale

  4261 Isabella Cir, Windermere, FL 34786

  • 6 Beds
  • 9 Baths
  • 7,129 Sq Ft
  • Built 2016

  4261 Isabella Cir, Windermere, FL 34786

  Last Sold Summary

  • 37 Days On Market
• 

  /2

  $575,000

  $25K PRICE INCREASE

  • Land
  • 20,473 Sq Ft
  • $1,223,404 per Acre

  9802 6th St, Windermere, FL 34786

  Vacant lot on the corner of 6th and Hempel. Prime investment property.

  Judy Plett UPSIDE REAL ESTATE INC

  9802 6th St, Windermere, FL 34786
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  /6

  $2,450 Per Month

  • 3 Beds
  • 2.5 Baths
  • 3 bedroom townhome in Legado

  13381 Gorgona Isle Dr, Windermere, FL 34786

  Gorgeous townhome in the charming Legado community of Windermere; Look no further and schedule a tour today with one of our rental specialist agents in order to discover your future dream home!We offer you a modern and spacious, 1578 sq ft, 3-bedroom, 2,5-bathroom townhome which was newly built in 2019! The ground floor includes an open-concept, spacious kitchen and living room area. While the

  13381 Gorgona Isle Dr, Windermere, FL 34786
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  /2

  $1,310,000

  Sold May 01, 2026

  8447 Woburn Ct, Windermere, FL 34786

  • 4 Beds
  • 3 Baths
  • 2,945 Sq Ft
  • Built 1999

  Last Sold Summary

  • 1% Below List Price
  • $445/SF
  • 4 Days On Market

  Current Estimated Value $1,159,409

  Last Listing Agent Amy Seelman FLORIDA REALTY INVESTMENTS

  8447 Woburn Ct, Windermere, FL 34786
• 

  

  /58

  Est $614,583

  Not Listed For Sale

  7610 Brofield Ave, Windermere, FL 34786

  • 4 Beds
  • 3.5 Baths
  • 2,610 Sq Ft
  • Built 2010

  7610 Brofield Ave, Windermere, FL 34786

  Last Sold Summary

  • 95 Days On Market
• 

  

  /31

  $390,000

  • 3 Beds
  • 2.5 Baths
  • 1,680 Sq Ft

  7723 Fairgrove Ave, Windermere, FL 34786

  Well maintained, move-in ready 3 bedrooms, 2.5 bathrooms townhouse in the Lake Sawyer South community in Windermere. The kitchen features a breakfast bar, granite countertops, stainless steel appliances and a walk-in pantry. The dining room has French doors that lead to an enclosed brick paver courtyard that connects to a detached 2 car garage. The first floor also includes a large family room, a

  Larry Bautista CHARLES RUTENBERG REALTY ORLANDO

  7723 Fairgrove Ave, Windermere, FL 34786
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  /69

  $6,000 Per Month

  • 3 Beds
  • 2 Baths
  • 1,713 Sq Ft
  • House for Rent

  820 East Blvd, Windermere, FL 34786

  Fully Furnished Executive Rental in downtown Windermere! Welcome to Sunrise on the Lake, a beautifully renovated, fully furnished executive home on Lake Bessie in Windermere. Tucked along winding lakeside roads, this peaceful retreat is perfectly positioned for stunning sunrises, refreshing lake breezes, and panoramic water views. From the moment you arrive, you will appreciate the exceptional

  Simon Simaan THE SIMON SIMAAN GROUP

  820 East Blvd, Windermere, FL 34786
• 

  /2

  $384,900

  Sold Apr 09, 2026

  7711 Fairgrove Ave, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 1,680 Sq Ft
  • Built 2009

  Last Sold Summary

  • 3% Below List Price
  • $229/SF
  • 127 Days On Market

  Current Estimated Value $385,028

  Last Listing Agent Lindsay Kaye Voss VOSS REALTY INC

  7711 Fairgrove Ave, Windermere, FL 34786
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  /51

  Est $842,069

  Not Listed For Sale

  4240 Blue Major Dr, Windermere, FL 34786

  • 4 Beds
  • 3.5 Baths
  • 3,345 Sq Ft
  • Built 2015

  4240 Blue Major Dr, Windermere, FL 34786

  Last Sold Summary

  • 55 Days On Market

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