Windermere, FL Homes

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  $359,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 1,480 Sq Ft

  7462 Bentonshire Ave, Windermere, FL 34786

  BIG price reduction for this move in ready 3/2.5 Townhome in Windermere! New roof 2024. AC compressor new June 2025. Rear entry 2 car garage. All stainless-steel fridge, stove, microwave and dishwasher with solid surface counter tops. Versatile all ceramic tiled 1st floor plan with formal dining room or use as front office. Open kitchen to rear great room that opens to covered screened private

  Ivan Petkov FLORIDA REALTY INVESTMENTS

  7462 Bentonshire Ave, Windermere, FL 34786
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  /31

  $6,000 per month

  • 3 Beds
  • 2.5 Baths
  • 2,309 Sq Ft
  • House for Rent

  8418 Bowden Way, Windermere, FL 34786

  Welcome to this beautifully updated 3-bedroom, 2.5-bathroom home located in the highly sought-after, guard-gated community of Keene’s Pointe in Windermere. Situated on a desirable corner lot, this stunning residence offers both privacy and charm in one of Central Florida’s most exclusive neighborhoods.The home has undergone a full renovation, featuring modern finishes throughout, including

  Jessica Dessire Cueva PA CHARLES RUTENBERG REALTY ORLANDO

  8418 Bowden Way, Windermere, FL 34786
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  $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

  Last Listing Agent Elle Walters JASON MITCHELL REAL ESTATE FLO

  5130 Sun Palm Dr, Windermere, FL 34786
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  Est $3,263,685 Not Listed For Sale

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

  4261 Isabella Cir, Windermere, FL 34786

  4261 Isabella Cir, Windermere, FL 34786
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  $1,149,000

  • 4 Beds
  • 3.5 Baths
  • 3,050 Sq Ft

  8746 Crescendo Ave, Windermere, FL 34786

  HUGE PRICE REDUCTION — PRICE TO SELL!Discover refined Florida living in this beautifully appointed premium CORNER-LOT residence located in one of Windermere’s most desirable communities. Built in 2015 and offering 3,050 SqFt of thoughtfully designed interior living, this FULLY FURNISHED, move-in-ready home delivers outstanding value, convenience, and lifestyle appeal—now at an exceptional new

  Mariana Micheti M2M REALTY

  8746 Crescendo Ave, Windermere, FL 34786
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  $7,000 per month

  • 5 Beds
  • 4.5 Baths
  • 3,835 Sq Ft
  • House for Rent

  7231 Sangalla Dr, Windermere, FL 34786

  Perfect for Executive Rentals * 7 month lease available * Exclusive Gated Community • Updated Interior • Low Maintenance Resort-Style Backyard with Artificial Turf • 5 Bedrooms + Office + Huge Loft • Live in one of Windermere’s most prestigious gated communities, surrounded by breathtaking lakefront estates and just minutes from everything Central Florida has to offer. This luxury 5-bedroom,

  Darrell Nunnelley VINTAGE REALTY GROUP LLC

  7231 Sangalla Dr, Windermere, FL 34786
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  /2

  $484,000 Sold Jun 16, 2025

  12285 Joshua Tree Trail, Windermere, FL 34786

  • 4 Beds
  • 2.5 Baths
  • 2,149 Sq Ft
  • Built 2015

  Last Sold Summary

  • 15% Below List Price
  • $225/SF
  • 161 Days On Market

  Current Estimated Value $495,555

  Last Listing Agent Erin Legler CHARLES RUTENBERG REALTY ORLANDO

  12285 Joshua Tree Trail, Windermere, FL 34786
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  Est $538,296 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,709 Sq Ft

  7688 Brofield Ave, Windermere, FL 34786

  7688 Brofield Ave, Windermere, FL 34786
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  $1,044,989 New Construction

  • 5 Beds
  • 4.5 Baths
  • 4,571 Sq Ft

  14427 Crest Palm Ave, 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 4,500 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

  14427 Crest Palm Ave, Windermere, FL 34786
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  $4,200 per month

  • 4 Beds
  • 2.5 Baths
  • 2,648 Sq Ft
  • House for Rent

  5426 Gemgold Ct, Windermere, FL 34786

  Discover the best current value for a lakefront property in Windermere with this stunning WATERFRONT HOUSE featuring a private DOCK in the highly sought-after Summerport community! Recently remodeled on the first floor, this home now features a captivating open layout complemented by newer luxury vinyl floors throughout. With 4 bedrooms, 21⁄2 baths, and a 2-car garage, this lovely property is an

  Hector Leon LPT REALTY, LLC

  5426 Gemgold Ct, Windermere, FL 34786
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  /2

  $1,080,813 Sold Feb 28, 2025

  14291 Crest Palm Ave, Windermere, FL 34786

  • 6 Beds
  • 4 Baths
  • 4,222 Sq Ft
  • Built 2024

  Last Sold Summary

  • 1% Below List Price
  • $256/SF
  • 0 Days On Market

  Current Estimated Value $1,080,307

  Last Listing Agent Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

  14291 Crest Palm Ave, Windermere, FL 34786
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  Est $630,189 Not Listed For Sale

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

  7610 Brofield Ave, Windermere, FL 34786

  7610 Brofield Ave, Windermere, FL 34786
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  $4,650,000

  • 5 Beds
  • 5.5 Baths
  • 7,183 Sq Ft

  12540 Park Ave, Windermere, FL 34786

  Offering a prime lakefront location along the shores of Lake Butler in the esteemed gated community of Chaine du Lac, this distinguished estate features timeless architecture paired with transitional interiors and gorgeous views to showcase Windermere lakefront living at its finest. The estate has been elevated with significant recent improvements, including a brand-new roof, an all-new primary

  Carey Sheffield ISLEWORTH REALTY LLC

  12540 Park Ave, Windermere, FL 34786
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  /35

  $2,600 per month

  • 3 Beds
  • 2.5 Baths
  • 1,881 Sq Ft
  • Property for Rent

  7448 Leighside Dr, Windermere, FL 34786

  Live in one of Windermere’s most desirable communities! This beautifully maintained 3-bedroom, 2.5-bath townhome offers a spacious open-concept layout perfect for comfortable living. The kitchen features granite countertops, stainless steel appliances, 42” solid wood cabinets, and a generous amount of storage. The first floor offers ceramic tile throughout, while all bedrooms are located upstairs

  Vicente Virgilio ALTIS REALTY

  7448 Leighside Dr, Windermere, FL 34786
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  /2

  $539,900 Sold Nov 20, 2025

  11091 Bagley Aly, Windermere, FL 34786

  • 4 Beds
  • 2.5 Baths
  • 2,222 Sq Ft
  • Built 2018

  Last Sold Summary

  • 2% Below List Price
  • $243/SF
  • 123 Days On Market

  Last Listing Agent Mariana Cezar Ovalle WRA BUSINESS & REAL ESTATE

  11091 Bagley Aly, Windermere, FL 34786
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  Est $856,011 Not Listed For Sale

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

  4240 Blue Major Dr, Windermere, FL 34786

  4240 Blue Major Dr, Windermere, FL 34786
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  $1,650,000

  • 4 Beds
  • 4.5 Baths
  • 3,288 Sq Ft

  1703 Roberts Landing Rd, Windermere, FL 34786

  This elegant and fully renovated lakefront home on Lake Olivia in Windermere offers the ultimate blend of luxury, comfort, and Florida lifestyle. Featuring three master suites plus a guest bedroom and bathroom, the spacious layout is designed for both entertaining and everyday living. Large windows fill the home with natural light and frame breathtaking views of the water, while recent

  Wui Keong Goh INTERNATIONAL NETWORK REALTY

  1703 Roberts Landing Rd, Windermere, FL 34786
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  $18,500 per month

  • 6 Beds
  • 7.5 Baths
  • 6,853 Sq Ft
  • House for Rent

  6115 Orta Ct, Windermere, FL 34786

  Extravagant and Luxurious Lakefront Estate located within the exclusive gated Waterstone Community in Windermere. Expansive open floorplan with stunning wood and porcelain/ceramic throughout. The Primary Bedroom is located on the ground floor and features a private patio with scenic views of the lake as well as a custom Walk-In closet and an amazing primary bathroom. An additional suite is

  Billy Cannon, Jr BHHS FLORIDA REALTY

  6115 Orta Ct, Windermere, FL 34786
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  $560,000 Sold Aug 13, 2025

  6539 Chagford Ln, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 2,265 Sq Ft
  • Built 2007

  Last Sold Summary

  • 2% Below List Price
  • $247/SF
  • 19 Days On Market

  Current Estimated Value $560,146

  Last Listing Agent Lori Lucente-Nelson RE/MAX PRIME PROPERTIES

  6539 Chagford Ln, Windermere, FL 34786
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  /16

  Est $327,491 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,455 Sq Ft

  11564 Mizzon Dr Unit 904, Windermere, FL 34786

  11564 Mizzon Dr Unit 904, Windermere, FL 34786
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  $1,100,000

  • 4 Beds
  • 5 Baths
  • 3,425 Sq Ft

  7545 Lake Albert Dr, Windermere, FL 34786

  Welcome to 7545 Lake Albert Drive. Where timeless architecture meets modern luxury. Nestled on an expansive lot in one of Windermere's most sought after communities, this stunning estate offers the perfect balance of privacy, comfort, and resort-style living just minutes from Walt Disney World and the best of Central Florida. Arrive via a long, elegant driveway, framed by lush landscaping,

  Nicole Mickle OLYMPUS EXECUTIVE REALTY INC

  7545 Lake Albert Dr, Windermere, FL 34786
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  $14,800 per month

  • 6 Beds
  • 9 Baths
  • 7,337 Sq Ft
  • House for Rent

  4012 Isabella Cir, Windermere, FL 34786

  Step into elegance! This beautifully designed luxury home in Casabella, Windermere, offers the perfect blend of comfort and sophistication. Casabella features 79 exclusive luxury homes and private gated entry. This Toll Brothers community features half acre home sites, two beautifully designed ponds with fountains and a playground area, 4012 Isabella Circle is the Villa Lago Floor plan with

  Alejandra Silva METROPOLITAN R.E SOLUTIONS INC

  4012 Isabella Cir, Windermere, FL 34786
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  $590,000 Sold Aug 06, 2025

  5263 Beach River Rd, Windermere, FL 34786

  • 4 Beds
  • 3 Baths
  • 2,432 Sq Ft
  • Built 2004

  Last Sold Summary

  • 1% Below List Price
  • $243/SF
  • 26 Days On Market

  Current Estimated Value $589,050

  Last Listing Agent Ariel Vargas EXP REALTY LLC

  5263 Beach River Rd, Windermere, FL 34786
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  Est $1,239,171 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 3,818 Sq Ft

  7219 Sangalla Dr, Windermere, FL 34786

  7219 Sangalla Dr, Windermere, FL 34786
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  /18

  $1,299,000

  • 5 Beds
  • 4 Baths
  • 3,557 Sq Ft

  11021 Hawkshead Ct Unit 2, Windermere, FL 34786

  Welcome to this exquisite 5-bedroom, 4-bathroom residence nestled on a premium corner lot in one of Windermere’s most beautiful, gated communities. Boasting 3,557 square feet of thoughtfully designed living space, this Spanish Colonial-style home blends timeless elegance with modern comfort.Step inside to discover spacious living areas, rich architectural details, and a seamless flow

  Kara Manuchia ALL REAL ESTATE & INVESTMENTS

  11021 Hawkshead Ct Unit 2, Windermere, FL 34786
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  /20

  $2,750 per month

  • 3 Beds
  • 2.5 Baths
  • 1,912 Sq Ft
  • Townhouse for Rent

  13718 Beckman Dr, Windermere, FL 34786

  Beautiful TOWHOME AT WINDERMERE AREA. kitchen with upgraded 42`` cabinets, stainless steel appliances. Upstairs vinyl floor, Master suite with walk in closet ,bathroom with dual sinks. Club house with pool.

  Monica Duran MD3 HOMES LLC

  13718 Beckman Dr, Windermere, FL 34786
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  $975,000 Sold Oct 20, 2025

  635 Butler St, Windermere, FL 34786

  • 3 Beds
  • 3 Baths
  • 2,353 Sq Ft
  • Built 1924

  Last Sold Summary

  • 2% Below List Price
  • $414/SF
  • 0 Days On Market

  Last Listing Agent Scott Arthur KELLER WILLIAMS REALTY AT THE LAKES

  635 Butler St, Windermere, FL 34786
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  Est $2,863,570 Not Listed For Sale

  • 6 Beds
  • 6.5 Baths
  • 6,011 Sq Ft

  13100 Bellaria Cir, Windermere, FL 34786

  13100 Bellaria Cir, Windermere, FL 34786
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  /40

  $637,500

  • 5 Beds
  • 3 Baths
  • 2,555 Sq Ft

  6846 Helmsley Cir, Windermere, FL 34786

  NEW ROOF! Welcome to 6846 Helmsley Circle in beautiful Windermere, FL! This stunning 5-bedroom, 3-bathroom home is situated on the largest lot in the neighborhood, offering over a quarter-acre of space with two expansive backyards. Imagine the possibilities—perhaps a pool or even a pickleball court! The home boasts two primary suites, one conveniently located on the main floor and another

  Nickolas Amburgey COMPASS FLORIDA LLC

  6846 Helmsley Cir, Windermere, FL 34786
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  $17,900 per month

  • 7 Beds
  • 6 Baths
  • 4,609 Sq Ft
  • House for Rent

  4303 Isabella Cir, Windermere, FL 34786

  Luxury Windermere House for Lease Discover an exceptional opportunity to lease a stunning, fully furnished luxury house in the highly sought-after community of Windermere. Recently renovated and meticulously maintained, this rental property offers the perfect blend of elegance, comfort, and modern convenience. This two-story residence features five spacious bedrooms, including a grand primary

  Jennifer Olmeda WRA BUSINESS & REAL ESTATE

  4303 Isabella Cir, Windermere, FL 34786
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  $635,000 Sold Sep 05, 2025

  13978 Darchance Rd, Windermere, FL 34786

  • 4 Beds
  • 3.5 Baths
  • 2,884 Sq Ft
  • Built 2007

  Last Sold Summary

  • 4% Below List Price
  • $220/SF
  • 43 Days On Market

  Current Estimated Value $637,658

  Last Listing Agent Sean Popat BUYER REBATES REALTY

  13978 Darchance Rd, Windermere, FL 34786
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  Est $357,389 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,601 Sq Ft

  8259 Maritime Flag St Unit 1, Windermere, FL 34786

  8259 Maritime Flag St Unit 1, Windermere, FL 34786
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  /73

  $1,224,000

  • 4 Beds
  • 3.5 Baths
  • 2,791 Sq Ft

  109 E 12th Ave, Windermere, FL 34786

  Modern sophistication and timeless Windermere charm come together in this fully reimagined residence located just steps from Lake Bessie and the heart of Windermere Town. Set on a beautifully landscaped corner lot with no HOA, this home offers a rare blend of luxury comfort and walkable small town living in one of Central Florida’s most desirable communities. Every detail has been thoughtfully

  Brian Hyser THE AGENCY ORLANDO

  109 E 12th Ave, Windermere, FL 34786
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  /59

  $15,000 per month

  • 5 Beds
  • 5.5 Baths
  • 5,339 Sq Ft
  • House for Rent

  6844 Valhalla Way, Windermere, FL 34786

  Beautiful and fully furnished home in Keene's Pointe golf community. Guard gated community. A Tuscan style luxury home with a large covered back patio with fireplace and large pool overlooking the 14th green Bear Club. Master and extra suite on first floor and three more suites upstairs. This house has a very big loft, perfect for entertaining.

  Marilene Auge CHARLES RUTENBERG REALTY ORLANDO

  6844 Valhalla Way, Windermere, FL 34786
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  $1,370,000 Sold Apr 15, 2025

  5518 Oxford Moor Blvd, Windermere, FL 34786

  • 4 Beds
  • 4.5 Baths
  • 5,260 Sq Ft
  • Built 2003

  Last Sold Summary

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

  Current Estimated Value $1,427,505

  Last Listing Agent Sean Flatley KELLER WILLIAMS REALTY AT THE PARKS

  5518 Oxford Moor Blvd, Windermere, FL 34786
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  Est $1,203,885 Not Listed For Sale

  • 8 Beds
  • 5 Baths
  • 4,751 Sq Ft

  6228 Roseate Spoonbill Dr, Windermere, FL 34786

  6228 Roseate Spoonbill Dr, Windermere, FL 34786
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  $799,900

  • 5 Beds
  • 3.5 Baths
  • 3,390 Sq Ft

  6615 Helmsley Cir, Windermere, FL 34786

  Beautifully remodeled and impeccably maintained, this spacious 3,390 sq. ft. two-story home offers 5 bedrooms, 3.5 bathrooms, an office, and an attached 2-car garage in the highly desirable community of Preston Square in Windermere. Perfectly situated on a premium lot with no rear neighbors, the home features a charming front porch and covered balcony overlooking the serene, tree-lined

  Angela Gann KELLER WILLIAMS ELITE PARTNERS III REALTY

  6615 Helmsley Cir, Windermere, FL 34786
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  $5,000 per month

  • 4 Beds
  • 4.5 Baths
  • 3,483 Sq Ft
  • House for Rent

  11905 Camden Park Dr, Windermere, FL 34786

  This rare opportunity for a lovely two-story rental home in Keene's Pointe is now available and move in ready for immediate occupancy. Located in the highly sought after guard gated community of Keene's Pointe, this terrific floor plan boasts 4BR/4.5 Baths + office + bonus room and a 3 Car Garage. Primary Suite is located on the man floor with all other bedrooms on the second floor along with a

  Angela Durruthy KEENE'S POINTE REALTY

  11905 Camden Park Dr, Windermere, FL 34786
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  $365,000 Sold Mar 03, 2025

  12662 Langstaff Dr, Windermere, FL 34786

  • 2 Beds
  • 2.5 Baths
  • 1,200 Sq Ft
  • Built 2003

  Last Sold Summary

  • 3% Below List Price
  • $304/SF
  • 89 Days On Market

  Current Estimated Value $352,919

  Last Listing Agent Jane Sims SIMS REALTY LLC

  12662 Langstaff Dr, Windermere, FL 34786
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  Est $1,075,550 Not Listed For Sale

  • 5 Beds
  • 4 Baths
  • 3,393 Sq Ft

  9127 Tintori Ln, Windermere, FL 34786

  9127 Tintori Ln, Windermere, FL 34786

Showing Results 241 - 280, Page 7 of 18