Windermere, FL Homes

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  $355,000 Sold Jun 13, 2025

  8933 Newmarket Dr, Windermere, FL 34786

  • 2 Beds
  • 2.5 Baths
  • 1,336 Sq Ft
  • Built 2006

  Last Sold Summary

  • 10% Below List Price
  • $266/SF
  • 74 Days On Market

  Current Estimated Value $344,372

  Last Listing Agent Jenna Palmero COLDWELL BANKER REALTY

  8933 Newmarket Dr, Windermere, FL 34786
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  Est $430,208 Not Listed For Sale

  8972 Matriarca Aly, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 1,692 Sq Ft
  • Built 2020

  8972 Matriarca Aly, Windermere, FL 34786

  Last Sold Summary

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

  Last Sold Price $465,000

  Last Listing Agent Jacob Hara RE/MAX
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  $2,970,000

  • 5 Beds
  • 4 Baths
  • 3,737 Sq Ft

  10203 Trout Rd, Orlando, FL 32836

  Discover this exquisite lakefront property nestled on over 1.9 acres with more than 100 feet of water frontage on LAKE TIBET and part of the Butler Chain of Lakes. This home offers breathtaking views and absolutely stunning sunsets. As you drive onto the winding paver circular driveway with lovely fountain and beautiful landscaping, you will notice the terracotta tile roof and the undeniable

  Darlene O'Hara HOMEVEST REALTY

  10203 Trout Rd, Orlando, FL 32836
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  $710,000 Sold Nov 25, 2025

  9631 Hollyglen Place, Windermere, FL 34786

  • 4 Beds
  • 2.5 Baths
  • 2,854 Sq Ft
  • Built 1979

  Last Sold Summary

  • 5% Below List Price
  • $249/SF
  • 14 Days On Market

  Current Estimated Value $721,917

  Last Listing Agent Hilary Hall COMPASS FLORIDA LLC

  9631 Hollyglen Place, Windermere, FL 34786
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  Est $317,481 Not Listed For Sale

  8256 Maritime Flag St Unit 305, Windermere, FL 34786

  • 3 Beds
  • 2 Baths
  • 1,332 Sq Ft
  • Built 2009

  8256 Maritime Flag St Unit 305, Windermere, FL 34786

  Last Sold Summary

  • 7% Below List Price
  • $255/SF
  • 50 Days On Market

  Last Sold Price $340,000

  Last Listing Agent Claire Jesso SERHANT
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  $14,250,000

  • 5 Beds
  • 5.5 Baths
  • 9,511 Sq Ft

  5525 Isleworth Country Club Dr, Windermere, FL 34786

  One or more photo(s) has been virtually staged. Exceptional in both style and scale, this extraordinary Isleworth estate represents the pinnacle of luxury living in one of the finest golf club communities in the world. Designed by architect Terry Irwin and built by Ballard Construction, with interior designs by Faith Fournet, the property has been fully transformed and thoughtfully curated over

  Monica Lochmandy ISLEWORTH REALTY LLC

  5525 Isleworth Country Club Dr, Windermere, FL 34786
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  $435,000 Sold Jan 01, 2026

  13775 Bressler Aly, Windermere, FL 34786

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

  Last Sold Summary

  • 7% Below List Price
  • $217/SF
  • 84 Days On Market

  Current Estimated Value $436,290

  Last Listing Agent Sonia Frederick BAHIA INTERNATIONAL REALTY

  13775 Bressler Aly, Windermere, FL 34786
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  Est $473,267 Not Listed For Sale

  10706 Reams Rd, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 1,837 Sq Ft
  • Built 2013

  10706 Reams Rd, Windermere, FL 34786

  Last Sold Summary

  • 3% Below List Price
  • $267/SF
  • 62 Days On Market

  Last Sold Price $490,000

  Last Listing Agent Hector Leon LPT REALTY, LLC
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  $1,599,000 Pending

  • 5 Beds
  • 5 Baths
  • 3,520 Sq Ft

  6001 Caymus Loop, Windermere, FL 34786

  Under contract-accepting backup offers. Stunning Remodeled Golf Home in Keene’s Pointe – Windermere’s Premier Golf Community. Discover this unique, fully remodeled home in the highly sought-after Keene’s Pointe neighborhood, nestled in the picturesque lake community of Windermere. Offering privacy, breathtaking golf course views, and upgrades at every turn, this move-in-ready gem is the perfect

  Stella Freeman QUATTRO R E SOLUTIONS LLC

  6001 Caymus Loop, Windermere, FL 34786
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  $819,500 Sold Jun 13, 2025

  2151 Tillman Ave, Winter Garden, FL 34787

  • 5 Beds
  • 4 Baths
  • 3,506 Sq Ft
  • Built 2007

  Last Sold Summary

  • 4% Below List Price
  • $234/SF
  • 41 Days On Market

  Current Estimated Value $800,551

  Last Listing Agent Andy Neal THE AGENCY FL

  2151 Tillman Ave, Winter Garden, FL 34787
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  /18

  Est $397,203 Not Listed For Sale

  13179 Kegan St, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 1,617 Sq Ft
  • Built 2015

  13179 Kegan St, Windermere, FL 34786

  Last Sold Summary

  • 7% Below List Price
  • $265/SF
  • 6 Days On Market

  Last Sold Price $429,000

  Last Listing Agent Miguel Lopez AGENT TRUST REALTY CORPORATION
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  $1,650,000

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

  8438 Tibet Butler Dr, Windermere, FL 34786

  Located within the prestigious golf community of Keene’s Pointe, this elegant residence by renowned builder David Weekley Homes offers a refined blend of sophistication, comfort, and privacy in one of Windermere’s most sought-after addresses. Featuring 5 bedrooms and 4 full bathrooms, this two-story home presents a thoughtfully designed and versatile layout, ideal for both everyday living and

  Daniel Pavel WRA BUSINESS & REAL ESTATE

  8438 Tibet Butler Dr, Windermere, FL 34786
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  $835,000 Sold Jul 03, 2025

  2538 Carter Grove Cir, Windermere, FL 34786

  • 4 Beds
  • 3 Baths
  • 2,523 Sq Ft
  • Built 1996

  Last Sold Summary

  • 3% Below List Price
  • $331/SF
  • 8 Days On Market

  Current Estimated Value $826,367

  Last Listing Agent Tara Moore TARA MOORE REAL ESTATE

  2538 Carter Grove Cir, Windermere, FL 34786
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  Est $526,592 Not Listed For Sale

  12166 Canyon Sun Trail, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 2,156 Sq Ft
  • Built 2016

  12166 Canyon Sun Trail, Windermere, FL 34786

  Last Sold Summary

  • 4% Below List Price
  • $255/SF
  • 17 Days On Market

  Last Sold Price $550,000

  Last Listing Agent Jin Cheng ARION REALTY
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  $375,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 1,428 Sq Ft

  12683 Langstaff Dr, Windermere, FL 34786

  Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Fantastic opportunity to own this exceptional END UNIT townhouse with a beautiful POND VIEW in Lake Reams Townhomes community near Disney World! This sought-after townhouse features an impressive 3 bedrooms, 2.5 bathrooms, a 2-car garage, and a spacious paved patio where the best outdoor gatherings are

  Vlad Kizlo KELLER WILLIAMS REALTY AT THE LAKES

  12683 Langstaff Dr, Windermere, FL 34786
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  $1,349,000 Sold May 02, 2025

  11748 Waterstone Loop Dr, Windermere, FL 34786

  • 5 Beds
  • 4 Baths
  • 3,235 Sq Ft
  • Built 2012

  Last Sold Summary

  • 10% Below List Price
  • $417/SF
  • 59 Days On Market

  Current Estimated Value $1,371,053

  Last Listing Agent Immu Korvenmaa ALIGN REAL ESTATE LLC

  11748 Waterstone Loop Dr, Windermere, FL 34786
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  Est $910,449 Not Listed For Sale

  8349 Torcello Isle Dr, Windermere, FL 34786

  • 4 Beds
  • 3 Baths
  • 2,968 Sq Ft
  • Built 2018

  8349 Torcello Isle Dr, Windermere, FL 34786

  Last Sold Summary

  • 7% Below List Price
  • $330/SF
  • 60 Days On Market

  Last Sold Price $979,000

  Last Listing Agent Chris Creegan CREEGAN GROUP
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  $2,175,000 New Construction

  • 4 Beds
  • 5 Baths
  • 3,136 Sq Ft

  436 E 7th Ave, Windermere, FL 34786

  Seller is Motivated and open to negotiate! Luxury new construction lakefront home in Windermere, newly completed. Situated on Lake Bessie, this modern custom residence delivers architectural elegance, premium finishes, and a prime location just steps from the Town Center. The home offers 3,136 sq ft of air-conditioned space, featuring 4 en-suite bedrooms, a dedicated office at the entry, 5 full

  DENILEY VALDES TALENT REALTY SOLUTIONS

  436 E 7th Ave, Windermere, FL 34786
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  $590,000 Sold Feb 24, 2026

  4533 River Gem Ave, Windermere, FL 34786

  • 4 Beds
  • 3 Baths
  • 2,406 Sq Ft
  • Built 2006

  Last Sold Summary

  • 6% Below List Price
  • $245/SF
  • 49 Days On Market

  Current Estimated Value $614,812

  Last Listing Agent George Stringer COLDWELL BANKER REALTY

  4533 River Gem Ave, Windermere, FL 34786
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  Est $486,456 Not Listed For Sale

  8320 Bryce Canyon Ave, Windermere, FL 34786

  • 4 Beds
  • 2.5 Baths
  • 2,047 Sq Ft
  • Built 2016

  8320 Bryce Canyon Ave, Windermere, FL 34786

  Last Sold Summary

  • 1% Above List Price
  • $234/SF
  • 9 Days On Market

  Last Sold Price $480,000

  Last Listing Agent Alfredo Romero LPT REALTY, LLC
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  $1,100,000 Pending

  • 4 Beds
  • 3 Baths
  • 2,412 Sq Ft

  316 E 5th Ave, Windermere, FL 34786

  Under contract-accepting backup offers. Don’t let the 1962 build date keep you from considering this 4 Bedroom 3 Bath home that received a major renovation to the Electrical, Water Heater & Bath Updates in 2016 * New HVAC 2017 and a New Roof in 2018 made obtaining low cost Tower Hill property insurance easy * in 2025 the luxurious Kitchen was updated with a Thermador Natural Gas Range & top of

  Darrell Nunnelley VINTAGE REALTY GROUP LLC

  316 E 5th Ave, Windermere, FL 34786
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  $292,000 Sold Oct 03, 2025

  11434 Jasper Kay Terrace Unit 306, Windermere, FL 34786

  • 3 Beds
  • 2 Baths
  • 1,455 Sq Ft
  • Built 2007

  Last Sold Summary

  • 20% Below List Price
  • $201/SF
  • 348 Days On Market

  Current Estimated Value $297,461

  Last Listing Agent Jay Stewart SOUTHERN REALTY GROUP LLC

  11434 Jasper Kay Terrace Unit 306, Windermere, FL 34786
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  Est $1,514,807 Not Listed For Sale

  1295 Estancia Woods Loop, Windermere, FL 34786

  • 4 Beds
  • 5 Baths
  • 4,098 Sq Ft
  • Built 2018

  1295 Estancia Woods Loop, Windermere, FL 34786

  Last Sold Summary

  • 3% Above List Price
  • $360/SF
  • 22 Days On Market

  Last Sold Price $1,475,000

  Last Listing Agent Desiree LaRoche KEENE'S POINTE REALTY
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  $1,525,000 Pending

  • 5 Beds
  • 3 Baths
  • 3,013 Sq Ft

  6023 Blakeford Dr, Windermere, FL 34786

  Under contract-accepting backup offers. Keene's Pointe is a "Lifestyle!" Start living it now in this 5BR/3FULL Bath + office + all in a single story home located on the 13th fairway of the renown Jack Nicklaus Signature Golf Course in Keene's Pointe. Sited on a golf course frontage lot nearly half acre in size, this home has remodeled interiors, beautiful plank flooring and a fabulous covered

  Angela Durruthy KEENE'S POINTE REALTY

  6023 Blakeford Dr, Windermere, FL 34786
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  $665,000 Sold Mar 27, 2025

  12706 Bideford Ave, Windermere, FL 34786

  • 5 Beds
  • 3 Baths
  • 2,967 Sq Ft
  • Built 2006

  Last Sold Summary

  • 3% Below List Price
  • $224/SF
  • 47 Days On Market

  Current Estimated Value $671,194

  Last Listing Agent Sangita Khatri BRIC REALTY LLC

  12706 Bideford Ave, Windermere, FL 34786
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  Est $1,823,179 Not Listed For Sale

  12408 Corso Ct, Windermere, FL 34786

  • 6 Beds
  • 5.5 Baths
  • 5,497 Sq Ft
  • Built 2017

  12408 Corso Ct, Windermere, FL 34786

  Last Sold Summary

  • 4% Below List Price
  • $346/SF
  • 2 Days On Market

  Last Sold Price $1,900,000

  Last Listing Agent Simon Simaan THE SIMON SIMAAN GROUP
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  $4,395,000

  • Land
  • 1 Acre
  • $4,395,000 per Acre

  12418 Park Ave, Windermere, FL 34786

  WELCOME TO PARK AVENUE. An extraordinary opportunity awaits on 1 acre of prime lakefront with coveted southeastern exposure and sweeping panoramic views. Perfectly positioned along the pristine shoreline of Lake Butler on the renowned Butler Chain of Lakes, this exclusive homesite is located within one of Windermere’s most desirable gated enclaves—Chaine Du Lac. Offering the rare distinction of

  Michael Julian JULIAN PROPERTIES, INC.

  12418 Park Ave, Windermere, FL 34786
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  $585,000 Sold Apr 09, 2025

  8468 Powder Ridge Trail, Windermere, FL 34786

  • 4 Beds
  • 3.5 Baths
  • 2,633 Sq Ft
  • Built 2016

  Last Sold Summary

  • 5% Below List Price
  • $222/SF
  • 30 Days On Market

  Current Estimated Value $595,097

  Last Listing Agent Thomas Weclew THE REALTY MEDICS

  8468 Powder Ridge Trail, Windermere, FL 34786
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  Est $605,583 Not Listed For Sale

  13786 Summer Harbor Ct, Windermere, FL 34786

  • 4 Beds
  • 2.5 Baths
  • 2,236 Sq Ft
  • Built 2015

  13786 Summer Harbor Ct, Windermere, FL 34786

  Last Sold Summary

  • 10% Above List Price
  • $246/SF
  • 12 Days On Market

  Last Sold Price $550,000

  Last Listing Agent Lisa Camphire PREMIER SOTHEBYS INT'L REALTY
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  $899,000

  • 4 Beds
  • 3.5 Baths
  • 3,315 Sq Ft

  8724 Peachtree Park Ct, Windermere, FL 34786

  Recent pricing adjustment creates an exceptional opportunity to own a thoughtfully designed home in one of Windermere’s most sought-after hidden gems. With bonus spaces including a loft, mudroom, screened outdoor patio that goes around the house and a well-appointed this residence offers both refined living and everyday practicality. Experience the magic of Windermere living at Peachtree Park, a

  Marcelo Machado LA ROSA REALTY LLC

  8724 Peachtree Park Ct, Windermere, FL 34786
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  $1,290,000 Sold Oct 24, 2025

  13527 Lake Cawood Dr, Windermere, FL 34786

  • 5 Beds
  • 4.5 Baths
  • 3,379 Sq Ft
  • Built 2003

  Last Sold Summary

  • 1% Above List Price
  • $382/SF
  • 6 Days On Market

  Current Estimated Value $1,245,333

  Last Listing Agent Simon Simaan THE SIMON SIMAAN GROUP

  13527 Lake Cawood Dr, Windermere, FL 34786
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  Est $871,022 Not Listed For Sale

  7242 Rambling Water Way, Windermere, FL 34786

  • 5 Beds
  • 4 Baths
  • 3,051 Sq Ft
  • Built 2015

  7242 Rambling Water Way, Windermere, FL 34786

  Last Sold Summary

  • 5% Below List Price
  • $302/SF
  • 71 Days On Market

  Last Sold Price $920,000

  Last Listing Agent Carolina Mariano Da Silva PREMIER SOTHEBYS INT'L REALTY
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  $985,000 Pending

  • 4 Beds
  • 3.5 Baths
  • 3,080 Sq Ft

  6569 Crestmont Glen Ln, Windermere, FL 34786

  Under contract-accepting backup offers. Located in the gated community of Glenmuir, this beautifully renovated 3,080 SF pool residence offers 4 bedrooms + office and 3.5 bathrooms on an over 1/3-acre lot. Thoughtfully designed with both elegance and everyday functionality in mind, the home features a highly desirable split floorplan and seamless indoor-outdoor living.Upon entering, a

  Kim Gilbert THE AGENCY FL

  6569 Crestmont Glen Ln, Windermere, FL 34786
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  $1,460,000 Sold Jul 07, 2025

  11521 Camden Park Dr, Windermere, FL 34786

  • 5 Beds
  • 4.5 Baths
  • 3,483 Sq Ft
  • Built 2005

  Last Sold Summary

  • 2% Below List Price
  • $419/SF
  • 54 Days On Market

  Current Estimated Value $1,400,989

  Last Listing Agent Kathryn Stelljes KELLER WILLIAMS REALTY AT THE PARKS

  11521 Camden Park Dr, Windermere, FL 34786
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  Est $563,782 Not Listed For Sale

  6820 Merrick Landing Blvd, Windermere, FL 34786

  • 3 Beds
  • 2 Baths
  • 2,126 Sq Ft
  • Built 2014

  6820 Merrick Landing Blvd, Windermere, FL 34786

  Last Sold Summary

  • 3% Below List Price
  • $273/SF
  • 1 Day On Market

  Last Sold Price $580,000

  Last Listing Agent Chris Bunnell EXP REALTY LLC
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  $2,200,000

  • 8 Beds
  • 8.5 Baths
  • 4,735 Sq Ft

  11545 Brickyard Pond Ln, Windermere, FL 34786

  Luxury Lakefront Estate – Windermere, FL Discover a truly extraordinary lakefront residence located at one of Windermere's most prestigious addresses. Situated on a sprawling 0.75-acre lot, this property impresses with its grandeur, elegance, and impeccable attention to detail. With 8 spacious bedrooms, 9 full bathrooms, and 1 powder room, the home was designed to offer absolute comfort and a

  Jennifer Olmeda WRA BUSINESS & REAL ESTATE

  11545 Brickyard Pond Ln, Windermere, FL 34786
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  $430,000 Sold Feb 06, 2026

  7411 Ripplepointe Way, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 1,948 Sq Ft
  • Built 2010

  Last Sold Summary

  • 2% Below List Price
  • $221/SF
  • 55 Days On Market

  Current Estimated Value $432,181

  Last Listing Agent John Cunningham KELLER WILLIAMS CLASSIC

  7411 Ripplepointe Way, Windermere, FL 34786
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  /2

  Est $427,912 Not Listed For Sale

  11866 Water Run Aly, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 1,722 Sq Ft
  • Built 2016

  11866 Water Run Aly, Windermere, FL 34786

  Last Sold Summary

  • 6% Below List Price
  • $264/SF
  • 85 Days On Market

  Last Sold Price $454,900

  Last Listing Agent Steve Glose PREFERRED REAL ESTATE BROKERS
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  $585,000

  • 3 Beds
  • 2.5 Baths
  • 2,139 Sq Ft

  6442 Golden Dewdrop Trail, Windermere, FL 34786

  Come see this beautiful place. This immaculate home features include over 2,100 square feet of living space, a desirable Kitchen with 42" Cabinets and Granite, Stainless Steel Appliances, Beautiful Backsplash, engineered hardwood flooring on the first floor, vinyl on the second floor, ceramic tile in bathrooms and laundry, screened-in patio porch with a ceiling fan, an elegant courtyard, and much

  Yindy Reyes EMPIRE NETWORK REALTY

  6442 Golden Dewdrop Trail, Windermere, FL 34786
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  $1,450,000 Sold Aug 18, 2025

  11402 Camden Loop Way, Windermere, FL 34786

  • 5 Beds
  • 4.5 Baths
  • 3,880 Sq Ft
  • Built 2005

  Last Sold Summary

  • 9% Below List Price
  • $374/SF
  • 60 Days On Market

  Current Estimated Value $1,422,553

  Last Listing Agent Brian Hyser THE AGENCY FL

  11402 Camden Loop Way, Windermere, FL 34786

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