Windermere, FL Homes

• 

  

  

  /22

  $641,681

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,714 Sq Ft

  13325 Lush Lime Aly, Windermere, FL 34786

  Enjoy convenient, low-maintenance living in this two-story townhome featuring a private paver courtyard and two-car garage, perfectly located in the heart of Windermere. Designed for both comfort and functionality, this home offers a smart layout ideal for everyday living and entertaining. Interior finishes reflect the AW Collection Serene with upgrades including 42 kitchen cabinets, quartz

  Ashton Woods Builder

  13325 Lush Lime Aly, Windermere, FL 34786
• 

  

  

  /26

  $2,750 Per Month

  • 3 Beds
  • 2.5 Baths
  • 1,644 Sq Ft
  • Townhouse for Rent

  8470 Iron Mountain Trail, Windermere, FL 34786

  AVAILABLE NOW! Welcome to this spacious and beautifully maintained 3-bedroom, 2.5-bath townhome in the highly desirable Windermere Trails community. Offering 1,644 sq. ft. of living space, this two-story home features NO CARPET THROUGHOUT, a modern kitchen with 42" cabinets, granite countertops, stainless steel appliances, and a large island overlooking the open-concept living and dining areas.

  Francis Acosta LPT REALTY, LLC

  8470 Iron Mountain Trail, Windermere, FL 34786
• 

  

  /2

  $830,000

  Sold Feb 27, 2026

  9495 Westover Club Cir, Windermere, FL 34786

  • 4 Beds
  • 3 Baths
  • 2,773 Sq Ft
  • Built 2001

  Last Sold Summary

  • 2% Below List Price
  • $299/SF
  • 3 Days On Market

  Current Estimated Value $823,957

  Last Listing Agent Jeff Powell ALL FLORIDA PREMIER REALTY GROUP LLC

  9495 Westover Club Cir, Windermere, FL 34786
• 

  

  /2

  Est $443,248

  Not Listed For Sale

  11420 Center Lake Dr, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 1,881 Sq Ft
  • Built 2014

  11420 Center Lake Dr, Windermere, FL 34786

  Last Sold Summary

  • 9 Days On Market

  Last Listing Agent Millie Brockmeyer RE/MAX INNOVATION
• 

  

  

  /33

  $2,299,000

  $96K PRICE DROP

  • 5 Beds
  • 5.5 Baths
  • 4,094 Sq Ft

  11113 Lake Butler Blvd, Windermere, FL 34786

  Welcome to this beautiful, unique, and modern luxury home, built in 2023 and nestled on a generously sized, secluded lot in the highly sought-after and exclusive City of Windermere.Known for its lush natural landscapes, scenic trails, recreation parks, charming local shops, restaurants, beautiful lakes, top-rated schools, and exceptional quality of life, Windermere offers a truly

  Stella Freeman QUATTRO R E SOLUTIONS LLC

  11113 Lake Butler Blvd, Windermere, FL 34786
• 

  

  /37

  $2,000 Per Month

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

  8156 Boat Hook Loop Unit 602, Windermere, FL 34786

  Welcome to this spacious 2-bedroom, 2-bathroom first-floor condo in the highly desirable Lakeside at Lakes of Windermere community! Designed with comfort and privacy in mind, this split floor plan offers two oversized primary suites, each with its own full bathroom—perfect for roommates, guests, or a home office setup.Inside, you'll find a well-appointed kitchen featuring stainless steel

  Hector Leon LPT REALTY, LLC

  8156 Boat Hook Loop Unit 602, Windermere, FL 34786
• 

  /2

  $1,435,000

  Sold Nov 12, 2025

  1450 Belfiore Way, Windermere, FL 34786

  • 5 Beds
  • 4.5 Baths
  • 4,477 Sq Ft
  • Built 2007

  Last Sold Summary

  • 4% Below List Price
  • $321/SF
  • 109 Days On Market

  Current Estimated Value $1,423,596

  Last Listing Agent Laura Teixeira NOBSKA REAL ESTATE LLC

  1450 Belfiore Way, Windermere, FL 34786
• 

  /2

  Est $429,303

  Not Listed For Sale

  11213 Grander Dr, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 1,884 Sq Ft
  • Built 2013

  11213 Grander Dr, Windermere, FL 34786

  Last Sold Summary

  • 55 Days On Market

  Last Listing Agent Farzana Zalil CHARLES RUTENBERG REALTY ORLANDO
• 

  

  /81

  $4,778,000

  $711K PRICE DROP

  • 6 Beds
  • 9 Baths
  • 8,305 Sq Ft

  9721 Carillon Park Dr, Windermere, FL 34786

  Welcome to 9721 Carillon Park Dr, Windermere, FL 34786, a stunning estate inside the guard-gated community of Keene’s Pointe.This extraordinary residence offers 8,305 square feet of luxury living space with refined architectural details, elegant wood beams, and designer finishes throughout.MAIN FEATURES:• Five bedrooms plus DETACHED GUEST HOUSE and OFFICE— providing exceptional

  Dianna Desboyaux DOUGLAS ELLIMAN

  9721 Carillon Park Dr, Windermere, FL 34786
• 

  

  /27

  $3,000 Per Month

  • 1 Bed
  • 2 Baths
  • 1,000 Sq Ft
  • House for Rent

  5028 Autumn Ridge Ln, Windermere, FL 34786

  Fully Furnished Windermere Casita | 1BR/2BA + Den | 3–6 Month RentalBeautifully furnished and private casita nestled in a peaceful, secluded neighborhood surrounded by a forest of 33 mature pine trees and serene nature views. Maximum occupancy is 2 people. The light-filled interior features 3 skylights, leather couches with electric recliners, electric fireplace, 2 new smart TVs, a peaceful

  Joyce Teixeira THE OUTLIER GROUP

  5028 Autumn Ridge Ln, Windermere, FL 34786
• 

  /2

  $960,000

  Sold Aug 13, 2026

  2125 Kane Park Way, Windermere, FL 34786

  • 4 Beds
  • 3 Baths
  • 2,743 Sq Ft
  • Built 1992

  Last Sold Summary

  • 11% Below List Price
  • $350/SF
  • 213 Days On Market

  Current Estimated Value $968,647

  Last Listing Agent Deb Schroeder INFINITY REALTY GROUP LLC

  2125 Kane Park Way, Windermere, FL 34786
• 

  /2

  Est $1,145,667

  Not Listed For Sale

  14378 Crest Palm Ave, Windermere, FL 34786

  • 6 Beds
  • 4 Baths
  • 4,222 Sq Ft
  • Built 2025

  14378 Crest Palm Ave, Windermere, FL 34786

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC
• 

  

  /76

  $1,130,000

  • 8 Beds
  • 5 Baths
  • 4,830 Sq Ft

  6152 Golden Dewdrop Trail, Windermere, FL 34786

  Spacious corner-lot residence offering 4,830 sq ft of living space with 8 bedrooms and 5 bathrooms across two levels. Two-story foyer with open staircase and abundant natural light. The kitchen features a large center island with granite countertops, breakfast bar seating, stainless steel appliances and pendant lighting, opening directly to the main living area. Fenced backyard. Corner lot

  Vitor Silva VESTI LLC

  6152 Golden Dewdrop Trail, Windermere, FL 34786
• 

  

  /91

  $9,990 Per Month

  • 4 Beds
  • 3 Baths
  • 2,737 Sq Ft
  • House for Rent

  10355 Trout Rd, Orlando, FL 32836

  Exceptional single-story lakefront residence on 1.57 acres of beautifully landscaped, mature grounds offering privacy, exclusivity, and breathtaking water views. This home features custom finishes throughout, including wood beam ceilings, personalized flooring, and seamless indoor-outdoor living with expansive glass doors connecting the living, dining, and kitchen areas. The chef’s kitchen

  Any Alves WRA BUSINESS & REAL ESTATE

  10355 Trout Rd, Orlando, FL 32836
• 

  /2

  $405,000

  Sold Dec 22, 2025

  12838 Strode Ln, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 1,748 Sq Ft
  • Built 2015

  Last Sold Summary

  • 6% Below List Price
  • $232/SF
  • 58 Days On Market

  Current Estimated Value $412,194

  Last Listing Agent Luis Leon Medina LA ROSA REALTY LLC

  12838 Strode Ln, Windermere, FL 34786
• 

  /2

  Not Listed For Sale

  0 Westover Roberts Rd Unit MFRO6286777, Windermere, FL 34786

  0 Westover Roberts Rd Unit MFRO6286777, Windermere, FL 34786

  Last Sold Summary

  • 6 Days On Market

  Last Listing Agent Christopher Lyons AGILE GROUP REALTY
• 

  

  /19

  $4,276,160

  New Construction $2M PRICE INCREASE Pending

  • 5 Beds
  • 6.5 Baths
  • 6,401 Sq Ft

  1821 Windermere Rd, Windermere, FL 34786

  Pre-Construction. To be built. Discover an unparalleled opportunity to acquire a sovereign 1.16-acre estate homesite in the heart of Windermere. This meticulously positioned property, oriented east-west for optimal light, is ensconced within a private setting and borders a permanent conservation area, ensuring absolute privacy and serene, unimpeded vistas. The absence of an HOA affords complete

  Matt Matthews ORLANDO TBI REALTY LLC

  1821 Windermere Rd, Windermere, FL 34786
• 

  

  /100

  $5,500 Per Month

  • 4 Beds
  • 2.5 Baths
  • 2,549 Sq Ft
  • House for Rent

  9247 Legado Dr, Windermere, FL 34786

  FULLY FURNISHED HOME FOR RENT IN WINDERMERE!Experience comfort, convenience, and the best of the Florida lifestyle in this beautiful 4-bedroom home, offered for rent 100% fully furnished and move-in ready.Ideally located in one of Windermere’s most desirable areas, just minutes from Walt Disney World, this home combines an exceptional location with privacy, space, and beautiful

  Silvia Cervi ONLI REALTY GROUP LLC

  9247 Legado Dr, Windermere, FL 34786
• 

  /2

  $13,200,000

  Sold Jun 05, 2026

  9121 Tibet Pointe Cir, Windermere, FL 34786

  • 6 Beds
  • 11 Baths
  • 11,071 Sq Ft
  • Built 2006

  Last Sold Summary

  • 9% Below List Price
  • $1,192/SF
  • 5 Days On Market

  Current Estimated Value $8,119,531

  Last Listing Agent Jay Martin CORCORAN PREMIER REALTY

  9121 Tibet Pointe Cir, Windermere, FL 34786
• 

  /2

  Est $455,742

  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

  Last Listing Agent Nicholas Vaseloff PRIMEFIT PROPERTIES LLC
• 

  

  /34

  $1,159,000

  $28K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 2,665 Sq Ft

  12989 Westside Village Loop, Windermere, FL 34786

  Beautifully upgraded 4-bedroom residence featuring a thoughtfully designed floor plan, custom finishes, and exceptional indoor-outdoor living.The main level offers a private en-suite bedroom, ideal for guests or multigenerational living, along with a dedicated home office, spacious living areas, and a beautifully designed custom kitchen featuring tailored cabinetry, a large center island,

  Ramon Brandão WEBB FLORIDA REALTY LLC

  12989 Westside Village Loop, Windermere, FL 34786
• 

  

  /30

  $7,500 Per Month

  • 4 Beds
  • 3 Baths
  • 2,562 Sq Ft
  • House for Rent

  8411 Woburn Ct, Windermere, FL 34786

  Welcome to this 4-bedroom, 3-bathroom home located on a quiet cul-de-sac in the guard-gated community of Keene's Pointe. Backing to the Tibet-Butler Preserve, this property offers peaceful conservation views and added privacy.Inside, you'll find a bright, open floor plan with plenty of natural light and tasteful updates throughout. The remodeled kitchen features modern cabinetry, granite

  Jessica Dessire Cueva PA CHARLES RUTENBERG REALTY ORLANDO

  8411 Woburn Ct, Windermere, FL 34786
• 

  /2

  $2,100,000

  Sold Jun 10, 2026

  505 Jennifer Ln, Windermere, FL 34786

  • 4 Beds
  • 3.5 Baths
  • 3,525 Sq Ft
  • Built 1989

  Last Sold Summary

  • 7% Below List Price
  • $596/SF
  • 72 Days On Market

  Current Estimated Value $2,054,698

  Last Listing Agent Ahmad Hassan COMPASS FLORIDA LLC

  505 Jennifer Ln, Windermere, FL 34786
• 

  /2

  Est $1,744,400

  Not Listed For Sale

  11856 Vinci Dr, Windermere, FL 34786

  • 5 Beds
  • 4.5 Baths
  • 3,680 Sq Ft
  • Built 2011

  11856 Vinci Dr, Windermere, FL 34786

  Last Sold Summary

  • 108 Days On Market

  Last Listing Agent Oscar Rodriguez B LIVE COMMERCIAL AND RESIDENT
• 

  

  /70

  $3,200,000

  $50K PRICE DROP

  • 6 Beds
  • 6.5 Baths
  • 6,308 Sq Ft

  13448 Bellaria Cir, Windermere, FL 34786

  Virtually Staged. Buyer walked days before closing due to personal reasons! All inspections and milestones clean/clear!! - This exceptional Florida residence is perfectly sited on an acre within the exclusive guard-gated community of Bellaria. Thoughtfully designed to balance sophistication with comfort, the home welcomes you with an abundance of natural light streaming through broad front

  Shawn Kennedy KENNEDY REALTY GROUP LLC

  13448 Bellaria Cir, Windermere, FL 34786
• 

  

  /32

  $2,750 Per Month

  • 3 Beds
  • 2.5 Baths
  • 1,588 Sq Ft
  • Townhouse for Rent

  7243 Shadeview Aly, Windermere, FL 34786

  Beautiful Windermere Townhome Near Top-Rated Schools. Discover the perfect blend of comfort, convenience, and location in this charming Windermere townhome. Just a short walk from local groceries, shops and Horizon West Middle School, this home is also zoned for highly regarded Sunset Park Elementary and Windermere High School. The thoughtfully designed floor plan keeps all three bedrooms, two

  Claudia Panella COLDWELL BANKER REALTY

  7243 Shadeview Aly, Windermere, FL 34786
• 

  /2

  $2,600,000

  Sold Aug 07, 2026

  13304 Bellaria Cir, Windermere, FL 34786

  • 6 Beds
  • 6 Baths
  • 4,920 Sq Ft
  • Built 2013

  Last Sold Summary

  • 9% Below List Price
  • $528/SF
  • 116 Days On Market

  Current Estimated Value $2,753,208

  Last Listing Agent Caroline De Castro Marcellini COMPASS FLORIDA, LLC

  13304 Bellaria Cir, Windermere, FL 34786
• 

  /2

  Est $1,106,001

  Not Listed For Sale

  3302 Just-A-mere Ct, Windermere, FL 34786

  • 4 Beds
  • 3 Baths
  • 2,450 Sq Ft
  • Built 1986

  3302 Just-A-mere Ct, Windermere, FL 34786

  Last Sold Summary

  • 18 Days On Market

  Last Listing Agent Sue Webb WATSON REALTY CORP.
• 

  

  /98

  $475,000

  • 3 Beds
  • 2.5 Baths
  • 1,600 Sq Ft

  11861 Vermillion Ave, Windermere, FL 34786

  TOP RATED SCHOOLS. NO CARPET throughout the home!! Welcome to this beautifully maintained 3-bedroom, 2.5-bath townhome located in the highly sought-after Windermere Trails community! This spacious two-story home features an open-concept layout with a modern kitchen offering stainless steel appliances, ample cabinet space, and a large island overlooking the living and dining areas — perfect for

  Frederico Hexsel KARDOSH REALTY

  11861 Vermillion Ave, Windermere, FL 34786
• 

  

  /31

  $6,799 Per Month

  • 4 Beds
  • 3 Baths
  • 2,398 Sq Ft
  • House for Rent

  8507 Bowden Way, Windermere, FL 34786

  Virtually Staged. Beautiful single-story home in the highly desirable gated community of Keene’s Pointe! This 4-bedroom, 3-bath residence 2,398 square feet with a split floor plan, tile flooring throughout, full-home solar power, updated appliances, and a wine refrigerator.Enjoy your private pool with pool enclosure and fenced backyard overlooking the 440-acre Tibet-Butler Nature Preserve,

  Jessica Dessire Cueva PA CHARLES RUTENBERG REALTY ORLANDO

  8507 Bowden Way, Windermere, FL 34786
• 

  /2

  $1,900,000

  Sold Apr 23, 2026

  6330 Lake Burden View Dr, Windermere, FL 34786

  • 4 Beds
  • 4.5 Baths
  • 4,460 Sq Ft
  • Built 2006

  Last Sold Summary

  • 3% Below List Price
  • $426/SF
  • 30 Days On Market

  Current Estimated Value $1,890,117

  Last Listing Agent Karla Ryan WATSON REALTY CORP

  6330 Lake Burden View Dr, Windermere, FL 34786
• 

  /2

  Est $470,470

  Not Listed For Sale

  13805 Bressler Aly, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 2,093 Sq Ft
  • Built 2019

  13805 Bressler Aly, Windermere, FL 34786

  Last Sold Summary

  • 34 Days On Market

  Last Listing Agent Kenneth Wilder CREEGAN GROUP
• 

  

  /40

  $750,000

  Under Contract

  • 5 Beds
  • 4 Baths
  • 3,373 Sq Ft

  6208 Talaria Dr, Windermere, FL 34786

  Under contract-accepting backup offers. Welcome to this move-in ready 5-bedroom, 4-bath home in the desirable Providence community of Windermere. This spacious home features an open-concept layout with soaring 8-foot doors, arched entryways, crown molding, recessed lighting, tile flooring, and fresh interior paint. The gourmet kitchen offers granite countertops, stainless steel appliances, a

  Olga Kaza OLYMPUS EXECUTIVE REALTY INC

  6208 Talaria Dr, Windermere, FL 34786
• 

  

  /29

  $7,000 Per Month

  • 4 Beds
  • 3 Baths
  • 2,578 Sq Ft
  • House for Rent

  8351 Bowden Way, Windermere, FL 34786

  Virtually Staged. Nestled within the highly acclaimed guard-gated community of Keene’s Pointe, this completely remodeled 4-bedroom, 3-bathroom Windermere residence offers an exceptional blend of timeless architecture, sophisticated finishes, and effortless Florida living. From the moment you enter, the light-filled interior welcomes you with soaring coffered ceilings, custom-laid wood-look tile

  John Goggin STOCKWORTH REALTY GROUP

  8351 Bowden Way, Windermere, FL 34786
• 

  /2

  $360,000

  Sold Jun 22, 2026

  14368 Desert Haven St Unit 4106, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 1,840 Sq Ft
  • Built 2013

  Last Sold Summary

  • $196/SF
  • 38 Days On Market

  Current Estimated Value $358,303

  Last Listing Agent Karen Albright OPENDOOR BROKERAGE LLC

  14368 Desert Haven St Unit 4106, Windermere, FL 34786
• 

  

  /15

  Est $1,060,000

  Not Listed For Sale

  14428 Crest Palm Ave, Windermere, FL 34786

  • 4 Beds
  • 3.5 Baths
  • 3,199 Sq Ft
  • Built 2025

  14428 Crest Palm Ave, Windermere, FL 34786

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC
• 

  /2

  $700,000

  • 1 Bed
  • 1 Bath
  • 750 Sq Ft

  628 Forest St, Windermere, FL 34786

  Pro pics coming soon * Charming 1 Bedroom 1 Bath Craftsman Cottage on a spacious lot in Downtown Windermere * Mature Oak Trees * The covered porches on the front and rear offer additional spaces to entertain, watch nature or read your favorite book while you slow down and truly experience the "Old Windermere" lifestyle * Home has been lovingly maintained and will impress even the most finicky

  Darrell Nunnelley VINTAGE REALTY GROUP LLC

  628 Forest St, Windermere, FL 34786
• 

  

  /28

  $3,150 Per Month

  • 4 Beds
  • 3.5 Baths
  • 2,469 Sq Ft
  • House for Rent

  13314 Roxboro Rd, Windermere, FL 34786

  Roomy and Updated 4 bedrooms and 3 Bath in Berkshire Park Subdivision. Located across the street from the amazing community playground, pool and clubhouse amenities, providing a million-dollar view. Enjoy the pool without the responsibility of maintenance. Very spacious downstairs with beautiful Granite Kitchen and Nice Appliance package inc. Washer & Dryer. Kitchen is equipped with an Island and

  Charles Woolley BHHS FLORIDA REALTY

  13314 Roxboro Rd, Windermere, FL 34786
• 

  /2

  $692,000

  Sold May 22, 2026

  17514 Black Rail St, Windermere, FL 34786

  • 4 Beds
  • 2 Baths
  • 2,373 Sq Ft
  • Built 2014

  Last Sold Summary

  • 13% Below List Price
  • $292/SF
  • 86 Days On Market

  Current Estimated Value $701,057

  Last Listing Agent He Gao U S GLORY REALTY

  17514 Black Rail St, Windermere, FL 34786
• 

  

  /3

  Est $1,092,667

  Not Listed For Sale

  14410 Crest Palm Ave, Windermere, FL 34786

  • 4 Beds
  • 3 Baths
  • 3,100 Sq Ft
  • Built 2025

  14410 Crest Palm Ave, Windermere, FL 34786

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

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