Windermere, FL Homes

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  /39

  Est $744,281 Not Listed For Sale

  13207 Orange Isle Dr, Windermere, FL 34786

  • 4 Beds
  • 3.5 Baths
  • 3,136 Sq Ft
  • Built 2021

  13207 Orange Isle Dr, Windermere, FL 34786

  Last Sold Summary

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

  Last Sold Price $765,000

  Last Listing Agent Shelley Dawson COMPASS FLORIDA LLC
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  /31

  $2,425,000

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

  11113 Lake Butler Blvd, Windermere, FL 34786

  Welcome to this beautiful, unique and modern home. Recently built in 2023. Secluded in a great sized lot and within the sought-after and exclusive City of Windermere, known for its lush nature landscape trails, recreation parks, restaurants, cozy stores, beautiful lakes, great schools and much more!!! This luxury property also has a HOA 1/24th private deeded land with lake access, dock and ramp

  Stella Freeman QUATTRO R E SOLUTIONS LLC

  11113 Lake Butler Blvd, Windermere, FL 34786
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  /2

  $1,800,000 Sold Jan 15, 2026

  5412 Water Creek Dr, Windermere, FL 34786

  • 4 Beds
  • 4.5 Baths
  • 4,247 Sq Ft
  • Built 2005

  Last Sold Summary

  • 10% Below List Price
  • $424/SF
  • 39 Days On Market

  Current Estimated Value $1,811,163

  Last Listing Agent Kari Fleck THE REAL ESTATE COLLECTION LLC

  5412 Water Creek Dr, Windermere, FL 34786
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  /48

  Est $723,879 Not Listed For Sale

  13608 Gorgona Isle Dr, Windermere, FL 34786

  • 4 Beds
  • 3 Baths
  • 2,834 Sq Ft
  • Built 2020

  13608 Gorgona Isle Dr, Windermere, FL 34786

  Last Sold Summary

  • $256/SF
  • 28 Days On Market

  Last Sold Price $725,000

  Last Listing Agent Amy Kidwell PA PREFERRED REAL ESTATE BROKERS
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  /47

  $3,500,000

  • 4 Beds
  • 4.5 Baths
  • 4,676 Sq Ft

  6130 Grosvenor Shore Dr, Windermere, FL 34786

  Remarkable Waterview Estate in Keene’s Pointe! Heated Saltwater Pool, Main-Floor Living, and Expansive Outdoor Living Space. Discover an exceptional custom Goehring & Morgan home offering the perfect blend of functionality and breathtaking outdoor living, located in a cul-de-sac of the exclusive Grosvenor Village within Keene’s Pointe, known for its privacy, guard-gated security, and Golden Bear

  Dianna Desboyaux DOUGLAS ELLIMAN

  6130 Grosvenor Shore Dr, Windermere, FL 34786
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  /2

  $8,000,000 Sold Apr 21, 2025

  12238 Park Ave, Windermere, FL 34786

  • 3 Beds
  • 3.5 Baths
  • 4,110 Sq Ft
  • Built 1962

  Last Sold Summary

  • $1,946/SF

  Current Estimated Value $3,845,491

  Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

  12238 Park Ave, Windermere, FL 34786
• 

  

  /23

  Est $708,925 Not Listed For Sale

  9216 Outlook Rock Trail, Windermere, FL 34786

  • 4 Beds
  • 3 Baths
  • 2,985 Sq Ft
  • Built 2016

  9216 Outlook Rock Trail, Windermere, FL 34786

  Last Sold Summary

  • 5% Above List Price
  • $226/SF
  • 113 Days On Market

  Last Sold Price $675,000

  Last Listing Agent Olga Petrova CHOICE ONE REALTY LLC
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  /41

  $30,000,000

  • 7 Beds
  • 14 Baths
  • 51,000 Sq Ft

  9508 Windy Ridge Rd, Windermere, FL 34786

  Presenting Windy Ridge Estate on 18 gated acres with 614 feet of pristine frontage on Lake Down, Butler Chain of Lakes. Manicured grounds, panoramic water views, and over 50,000 SF across multiple structures create an unrivaled lakefront compound.The walled entry opens to a grand foyer with a floating mahogany staircase, marble floors, paneled walls, and Murano chandeliers. An art gallery

  Christine Gelman DOUGLAS ELLIMAN

  9508 Windy Ridge Rd, Windermere, FL 34786
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  /2

  $1,755,000 Sold Aug 15, 2025

  11856 Vinci Dr, Windermere, FL 34786

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

  Last Sold Summary

  • 5% Below List Price
  • $477/SF
  • 108 Days On Market

  Current Estimated Value $1,731,739

  Last Listing Agent Oscar Rodriguez B LIVE COMMERCIAL AND RESIDENT

  11856 Vinci Dr, Windermere, FL 34786
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  /60

  Est $662,662 Not Listed For Sale

  7949 Jailene Dr, Windermere, FL 34786

  • 4 Beds
  • 3.5 Baths
  • 3,015 Sq Ft
  • Built 2012

  7949 Jailene Dr, Windermere, FL 34786

  Last Sold Summary

  • 1% Below List Price
  • $222/SF
  • 122 Days On Market

  Last Sold Price $670,000

  Last Listing Agent Chris Bunnell EXP REALTY LLC
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  /49

  $835,000

  • 4 Beds
  • 2 Baths
  • 2,713 Sq Ft

  9225 Mcdavid Ct, Windermere, FL 34786

  Welcome to this beautifully maintained custom 4-bedroom, 2-bath pool home set on a full 1-acre lot in a quiet, established neighborhood. Built and lovingly cared for by the original owner, this home offers a bright, airy interior with timeless wood trim details that add warmth and character throughout. The spacious family room features a wood-burning fireplace, creating a comfortable gathering

  David Vannoy CENTURY 21 CARIOTI

  9225 Mcdavid Ct, Windermere, FL 34786
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  /2

  $1,045,000 Sold Jan 20, 2026

  8764 Lookout Pointe Dr, Windermere, FL 34786

  • 4 Beds
  • 3.5 Baths
  • 3,423 Sq Ft
  • Built 2015

  Last Sold Summary

  • 4% Below List Price
  • $305/SF
  • 71 Days On Market

  Current Estimated Value $1,038,429

  Last Listing Agent Ken Pozek REAL BROKER, LLC

  8764 Lookout Pointe Dr, Windermere, FL 34786
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  /28

  Est $3,457,527 Not Listed For Sale

  9950 6th St, Windermere, FL 34786

  • 4 Beds
  • 7 Baths
  • 5,561 Sq Ft
  • Built 2024

  9950 6th St, Windermere, FL 34786

  Last Sold Summary

  • 1% Below List Price
  • $629/SF
  • 55 Days On Market

  Last Sold Price $3,500,000

  Last Listing Agent David Dorman CENTURY 21 CARIOTI
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  /43

  $3,999,000

  • Land
  • 2.79 Acres
  • $1,433,333 per Acre

  11010 Schooner Way, Windermere, FL 34786

  Featuring 713 feet of pristine waterfront along the shores of beautiful Lake Down in Windermere, this exceptional peninsula property encompasses 2.79 acres with water wrapping around multiple sides, offering extraordinary privacy and panoramic views. With direct access to the Butler Chain of Lakes, it’s perfect for boating, paddleboarding, skiing, and embracing the ultimate lake life lifestyle. A

  Michelle Corbin ISLEWORTH REALTY LLC

  11010 Schooner Way, Windermere, FL 34786
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  /2

  $670,000 Sold Sep 09, 2025

  9473 Palm Tree Dr, Windermere, FL 34786

  • 3 Beds
  • 2 Baths
  • 2,084 Sq Ft
  • Built 1986

  Last Sold Summary

  • 3% Below List Price
  • $321/SF
  • 7 Days On Market

  Current Estimated Value $648,453

  Last Listing Agent Mike Long COLDWELL BANKER REALTY

  9473 Palm Tree Dr, Windermere, FL 34786
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  /41

  Est $438,300 Not Listed For Sale

  13760 Calera Aly, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 1,912 Sq Ft
  • Built 2017

  13760 Calera Aly, Windermere, FL 34786

  Last Sold Summary

  • 2% Below List Price
  • $233/SF
  • 15 Days On Market

  Last Sold Price $446,000

  Last Listing Agent Saida Ali COLDWELL BANKER REALTY
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  /32

  $560,000

  • 4 Beds
  • 2 Baths
  • 2,044 Sq Ft

  11355 Arborside Bend Way Unit 1, Windermere, FL 34786

  Oversized .47 Acre Lot | Single-Story Home | Gated Community | Priced to sell | Open and bright single-story home is located in the gated community of Glenmuir. Vaulted ceilings in the formal living and dining rooms, and a kitchen with stainless steel appliances, that opens to the family room. Situated on one of the largest lots in the neighborhood, the backyard offers space to create your own

  Jeffrey Funk EXP REALTY LLC

  11355 Arborside Bend Way Unit 1, Windermere, FL 34786
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  /2

  $939,000 Sold Apr 16, 2025

  315 E 6th Ave, Windermere, FL 34786

  • 4 Beds
  • 3 Baths
  • 2,869 Sq Ft
  • Built 1964

  Last Sold Summary

  • $327/SF
  • 13 Days On Market

  Current Estimated Value $941,630

  Last Listing Agent Thomas Nickley KELLER WILLIAMS REALTY AT THE PARKS

  315 E 6th Ave, Windermere, FL 34786
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  /33

  Est $1,291,159 Not Listed For Sale

  1109 Estancia Woods Loop, Windermere, FL 34786

  • 4 Beds
  • 4 Baths
  • 3,493 Sq Ft
  • Built 2020

  1109 Estancia Woods Loop, Windermere, FL 34786

  Last Sold Summary

  • 5% Above List Price
  • $351/SF
  • 39 Days On Market

  Last Sold Price $1,225,000

  Last Listing Agent Ginny Bissonnette IRON VALLEY REAL ESTATE CENTRAL FLORIDA
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  /28

  $349,000 Pending

  • 2 Beds
  • 2.5 Baths
  • 1,360 Sq Ft

  7422 Bentonshire Ave, Windermere, FL 34786

  Under contract-accepting backup offers. **WELCOME HOME** NEW ROOF (2024), NEW A/C (2024), new window screens (2026), new window framing (2024), new kitchen sink (2024), accent walls (2022), and new hypoallergenic carpeting upstairs (2022) – the big-ticket updates are done, so you can simply move in and enjoy! Perfectly positioned across the street from Bentonshire Park, this well-maintained

  Jennifer Wemert WEMERT GROUP REALTY LLC

  7422 Bentonshire Ave, Windermere, FL 34786
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  /2

  $475,000 Sold Oct 23, 2025

  9375 Woodbreeze Blvd, Windermere, FL 34786

  • 3 Beds
  • 2 Baths
  • 1,492 Sq Ft
  • Built 1986

  Last Sold Summary

  • 23% Below List Price
  • $318/SF
  • 136 Days On Market

  Current Estimated Value $474,577

  Last Listing Agent Jackie Victoria Patellis COLDWELL BANKER REALTY

  9375 Woodbreeze Blvd, Windermere, FL 34786
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  /71

  Est $593,857 Not Listed For Sale

  6769 Merrick Landing Blvd, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 2,374 Sq Ft
  • Built 2014

  6769 Merrick Landing Blvd, Windermere, FL 34786

  Last Sold Summary

  • 5% Below List Price
  • $263/SF
  • 4 Days On Market

  Last Sold Price $625,000

  Last Listing Agent John Silva JOHN SILVA REALTY & ASSOCIATES
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  /50

  $670,000

  • 4 Beds
  • 3.5 Baths
  • 2,297 Sq Ft

  8582 Powder Ridge Trail, Windermere, FL 34786

  AN IRRESISTIBLE INVESTMENT OPPORTUNITY — OR YOUR FIRST HOME!Welcome to this stunning Kipling model offering serene lake views and a host of exceptional upgrades. This home features fully paid-off solar panels, electric vehicle charging outlets, and a whole-house water filtration system for maximum efficiency and comfort. Step inside and enjoy the spacious loft above the garage, new carpeting,

  Mariana Rondon LPT REALTY, LLC

  8582 Powder Ridge Trail, Windermere, FL 34786
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  $1,172,945 Sold Nov 19, 2025

  14342 Crest Palm Ave, Windermere, FL 34786

  • 5 Beds
  • 3.5 Baths
  • 4,084 Sq Ft
  • Built 2025

  Move in Ready Sold Summary

  • $287/SF
  • 20 Days On Market

  Current Estimated Value $1,058,543

  Dream Finders Homes Palms at Windermere

  14342 Crest Palm Ave, Windermere, FL 34786
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  /55

  Est $1,120,246 Not Listed For Sale

  8388 Lookout Pointe Dr, Windermere, FL 34786

  • 6 Beds
  • 4.5 Baths
  • 4,511 Sq Ft
  • Built 2016

  8388 Lookout Pointe Dr, Windermere, FL 34786

  Last Sold Summary

  • 2% Below List Price
  • $254/SF
  • 4 Days On Market

  Last Sold Price $1,145,000

  Last Listing Agent Emilia Rivero FOLIO REALTY LLC
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  $1,039,091 New Construction

  • 4 Beds
  • 3 Baths
  • 2,687 Sq Ft

  14353 Crest Palm Ave, Windermere, FL 34786

  Welcome to the Arlington! This single-story floor plan features 3-4 bedrooms, 3 bathrooms, and a 2-car garage, offering 2,687 square feet of spacious living. Enjoy an open-concept design that seamlessly connects the dining, kitchen, and living areas. The garage also includes an extra hobby/work space. Relax on the large covered patio or create culinary masterpieces in the chef's kitchen. The

  Dream Finders Homes Builder

  14353 Crest Palm Ave, Windermere, FL 34786
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  /2

  $925,000 Sold Jun 12, 2025

  9502 Hempel Cove Blvd, Windermere, FL 34786

  • 5 Beds
  • 4.5 Baths
  • 4,524 Sq Ft
  • Built 1998

  Last Sold Summary

  • 26% Below List Price
  • $204/SF
  • 319 Days On Market

  Current Estimated Value $1,001,898

  Last Listing Agent Jason Braddock EXP REALTY LLC

  9502 Hempel Cove Blvd, Windermere, FL 34786
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  /43

  Est $513,326 Not Listed For Sale

  11560 Charnock Dr, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 2,089 Sq Ft
  • Built 2018

  11560 Charnock Dr, Windermere, FL 34786

  Last Sold Summary

  • 2% Below List Price
  • $251/SF
  • 56 Days On Market

  Last Sold Price $525,000

  Last Listing Agent Whitney Bell CENTURY 21 CARIOTI
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  /53

  $798,900

  • 4 Beds
  • 3.5 Baths
  • 2,559 Sq Ft

  13263 Strode Ln, Windermere, FL 34786

  This beautifully maintained residence showcases rich engineered oak wood flooring throughout, a designer kitchen featuring quartz countertops with a full-height quartz backsplash, and newer stainless steel appliances.Step into your private backyard retreat with a solar-heated screened pool, propane-heated spa, elegant pavers, and wireless app-controlled access to all pool features. Additional

  Pedro Garcia Ponce HOME WISE REALTY GROUP, INC.

  13263 Strode Ln, Windermere, FL 34786
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  /2

  $365,000 Sold Aug 29, 2025

  8031 Enchantment Dr Unit GE, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 1,826 Sq Ft
  • Built 2007

  Last Sold Summary

  • 9% Below List Price
  • $200/SF
  • 84 Days On Market

  Current Estimated Value $361,348

  Last Listing Agent Sean Flatley KELLER WILLIAMS REALTY AT THE PARKS

  8031 Enchantment Dr Unit GE, Windermere, FL 34786
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  /52

  Est $726,078 Not Listed For Sale

  12961 Holdenbury Ln, Windermere, FL 34786

  • 4 Beds
  • 3 Baths
  • 2,943 Sq Ft
  • Built 2014

  12961 Holdenbury Ln, Windermere, FL 34786

  Last Sold Summary

  • 5% Below List Price
  • $260/SF
  • 16 Days On Market

  Last Sold Price $765,000

  Last Listing Agent Robert Foutz ASSIST 2 SELL FOUTZ REALTY
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  /64

  $444,900

  • 3 Beds
  • 2.5 Baths
  • 1,997 Sq Ft

  13712 Summerport Village Pkwy, Windermere, FL 34786

  Location!!! Great price!!! Top-rated school district!!! and a Renovated!!! Property ready for you to move in or invest. High rental demand and low inventory, ideal for investors or families.Fresh paint inside and out, new carpets, new indoor A/C with warranty, rear entry 2-car garage with epoxy flooring, and a spacious driveway. Kitchen island, granite counters, breakfast bar, stainless

  Carines Hernandez Bustillo AGENT TRUST REALTY CORPORATION

  13712 Summerport Village Pkwy, Windermere, FL 34786
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  /2

  $900,000 Sold Jan 12, 2026

  11025 Ledgement Ln, Windermere, FL 34786

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

  Last Sold Summary

  • 9% Below List Price
  • $298/SF
  • 222 Days On Market

  Current Estimated Value $897,656

  Last Listing Agent Christina Fata REAL BROKER, LLC

  11025 Ledgement Ln, Windermere, FL 34786
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  /21

  Est $520,400 Not Listed For Sale

  11019 Bagley Aly, Windermere, FL 34786

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

  11019 Bagley Aly, Windermere, FL 34786

  Last Sold Summary

  • 7% Above List Price
  • $218/SF
  • 113 Days On Market

  Last Sold Price $485,000

  Last Listing Agent Yuhong Wang BRIGHT REALTY GROUP LLC
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  /36

  $2,248,000 Pending

  • 4 Beds
  • 3.5 Baths
  • 4,440 Sq Ft

  6134 Keenes Pointe Dr, Windermere, FL 34786

  Under contract-accepting backup offers. A turnkey, fully furnished golf-front home in Keene’s Pointe — ready for immediate enjoyment, not renovation. With over 4,400 square feet of living space, has been reimagined to deliver not just a home, but an extraordinary lifestyle where every detail speaks of elegance, comfort, and sophistication. Renovated, move in ready and fully furnished!!! From the

  Babi Hennemann WRA BUSINESS & REAL ESTATE

  6134 Keenes Pointe Dr, Windermere, FL 34786
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  /2

  $680,000 Sold Aug 28, 2025

  4445 Blue Major Dr, Windermere, FL 34786

  • 4 Beds
  • 2.5 Baths
  • 2,620 Sq Ft
  • Built 2006

  Last Sold Summary

  • 3% Below List Price
  • $260/SF
  • 8 Days On Market

  Current Estimated Value $679,405

  Last Listing Agent Candace Tulensru LPT REALTY, LLC

  4445 Blue Major Dr, Windermere, FL 34786
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  /20

  Est $770,224 Not Listed For Sale

  11722 Gray Rock Trail, Windermere, FL 34786

  • 4 Beds
  • 3 Baths
  • 3,677 Sq Ft
  • Built 2017

  11722 Gray Rock Trail, Windermere, FL 34786

  Last Sold Summary

  • 1% Above List Price
  • $207/SF
  • 24 Days On Market

  Last Sold Price $760,000

  Last Listing Agent Jozsef Muriel-Pagan DEAL MAKERS REALTY TEAM CORP
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  /33

  $675,000

  • 3 Beds
  • 2.5 Baths
  • 2,280 Sq Ft

  7271 Sunny Meadow Aly, Windermere, FL 34786

  This meticulously maintained contemporary home is ideally situated on a premium FENCED corner lot just steps from the resort style community pool and clubhouse in sought after Ashlin Park in Windermere. Your family will enjoy the private and large fenced yard! This home is like new and features a long list of amazing upgrades - including recently installed luxury vinyl plank flooring and designer

  Denise Crabbe REVEL REALTY LLC

  7271 Sunny Meadow Aly, Windermere, FL 34786
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  /2

  $1,665,000 Sold Apr 28, 2025

  11931 Provincial Way, Windermere, FL 34786

  • 5 Beds
  • 5 Baths
  • 4,316 Sq Ft
  • Built 2004

  Last Sold Summary

  • 2% Below List Price
  • $386/SF
  • 20 Days On Market

  Current Estimated Value $1,658,345

  Last Listing Agent Brigitte Elzarki COLDWELL BANKER REALTY

  11931 Provincial Way, Windermere, FL 34786
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  /45

  Est $825,743 Not Listed For Sale

  7016 Kiwano Way, Windermere, FL 34786

  • 5 Beds
  • 4.5 Baths
  • 3,680 Sq Ft
  • Built 2021

  7016 Kiwano Way, Windermere, FL 34786

  Last Sold Summary

  • 1% Above List Price
  • $221/SF
  • 2 Days On Market

  Last Sold Price $815,000

  Last Listing Agent Shelley Dawson COMPASS FLORIDA LLC

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