Windermere, FL Homes

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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 $296,633

  Last Listing Agent Jay Stewart SOUTHERN REALTY GROUP LLC

  11434 Jasper Kay Terrace Unit 306, Windermere, FL 34786
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  /2

  Est $431,788 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

  • 5% Below List Price
  • $264/SF
  • 85 Days On Market

  • Last Sold Price $454,900
  • Sep 25, 2024

  Last Listing Agent Steve Glose PREFERRED REAL ESTATE BROKERS
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  /30

  $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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  /2

  $812,000 Sold Apr 20, 2026

  2641 Hempel Ave, Windermere, FL 34786

  • 4 Beds
  • 2 Baths
  • 2,404 Sq Ft
  • Built 1985

  Last Sold Summary

  • 2% Below List Price
  • $338/SF
  • 11 Days On Market

  Current Estimated Value $815,913

  Last Listing Agent Frank Mediavilla KNIGHTS REALTY

  2641 Hempel Ave, Windermere, FL 34786
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  /2

  Est $1,126,500 Not Listed For Sale

  14316 Crest Palm Ave, Windermere, FL 34786

  • 4 Beds
  • 3.5 Baths
  • 3,724 Sq Ft
  • Built 2024

  14316 Crest Palm Ave, Windermere, FL 34786

  Last Sold Summary

  • 6% Below List Price
  • $322/SF
  • 0 Days On Market

  • Last Sold Price $1,197,935
  • Mar 19, 2025

  Last Listing Agent Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC
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  /51

  $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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  /2

  $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 $1,251,762

  Last Listing Agent Simon Simaan THE SIMON SIMAAN GROUP

  13527 Lake Cawood Dr, Windermere, FL 34786
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  /28

  Est $419,281 Not Listed For Sale

  13303 Gorgona Isle Dr, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 1,441 Sq Ft
  • Built 2020

  13303 Gorgona Isle Dr, Windermere, FL 34786

  Last Sold Summary

  • 5% Below List Price
  • $306/SF
  • 24 Days On Market

  • Last Sold Price $441,500
  • Jun 24, 2024

  Last Listing Agent Charles Kohlinger BHHS FLORIDA REALTY
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  /70

  $369,990

  • 3 Beds
  • 2.5 Baths
  • 1,512 Sq Ft

  14236 Oasis Cove Blvd, Windermere, FL 34786

  If watching Magic Kingdom fireworks from your own home sounds like a dream, this is where it becomes your reality. Welcome to Oasis Cove, a gated, resort-style community located just a few miles from Walt Disney World. This beautifully updated 3-bedroom, 2.5-bath residence stands out as one of the most upgraded and move-in ready homes in the community. As you walk in, you are welcomed by a

  Raquel Saunders WRA BUSINESS & REAL ESTATE

  14236 Oasis Cove Blvd, Windermere, FL 34786
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  /2

  $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 $1,408,224

  Last Listing Agent Kathryn Stelljes KELLER WILLIAMS REALTY AT THE PARKS

  11521 Camden Park Dr, Windermere, FL 34786
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  /2

  Est $438,215 Not Listed For Sale

  11405 Brownstone St, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 1,881 Sq Ft
  • Built 2015

  11405 Brownstone St, Windermere, FL 34786

  Last Sold Summary

  • 4% Below List Price
  • $243/SF
  • 76 Days On Market

  • Last Sold Price $457,500
  • Sep 03, 2024

  Last Listing Agent Philip Foo FUTURE HOME REALTY INC
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  /60

  $975,000 Pending

  • 4 Beds
  • 3 Baths
  • 3,516 Sq Ft

  1002 Oakdale St, Windermere, FL 34786

  Under contract-accepting backup offers. Set on a prominent corner lot in one of Windermere’s most sought-after enclaves, this thoughtfully updated residence blends timeless character with modern upgrades, enormous walk out bottom level, massive multiple garages and a lifestyle that is uniquely local to this area. Relax on the expansive front porch and take in the surroundings as neighbors and

  Frank Smith KELLER WILLIAMS SUBURBAN TAMPA

  1002 Oakdale St, 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 $428,946

  Last Listing Agent John Cunningham KELLER WILLIAMS CLASSIC

  7411 Ripplepointe Way, Windermere, FL 34786
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  /2

  Est $477,865 Not Listed For Sale

  7653 Ripplepointe Way, Windermere, FL 34786

  • 4 Beds
  • 3 Baths
  • 2,212 Sq Ft
  • Built 2015

  7653 Ripplepointe Way, Windermere, FL 34786

  Last Sold Summary

  • 3% Below List Price
  • $223/SF
  • 86 Days On Market

  • Last Sold Price $492,500
  • Aug 16, 2024

  Last Listing Agent Nina Oh JUPITER PROPERTIES, INC
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  /26

  $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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  $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 $1,409,442

  Last Listing Agent Brian Hyser THE AGENCY FL

  11402 Camden Loop Way, Windermere, FL 34786
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  Est $1,091,315 Not Listed For Sale

  8361 Torcello Isle Dr, Windermere, FL 34786

  • 5 Beds
  • 3.5 Baths
  • 4,176 Sq Ft
  • Built 2018

  8361 Torcello Isle Dr, Windermere, FL 34786

  Last Sold Summary

  • 5% Below List Price
  • $275/SF
  • 22 Days On Market

  • Last Sold Price $1,150,000
  • Jun 10, 2024

  Last Listing Agent Sherri Palmer EXP REALTY LLC
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  /39

  $699,000 Pending

  • 4 Beds
  • 3.5 Baths
  • 2,794 Sq Ft

  13243 Charfield St, Windermere, FL 34786

  Under contract-accepting backup offers. A Windermere pool home under $700K like this is hard to come by, especially on one of the best tree-lined streets in the community.As soon as you walk in, you’re greeted by a two-story entrance and open living area that brings in great natural light and gives the home a larger, more elevated feel. The layout includes a formal dining room and hardwood

  Ken Pozek REAL BROKER, LLC

  13243 Charfield St, Windermere, FL 34786
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  /2

  $285,000 Sold Sep 19, 2025

  8277 Maritime Flag St Unit 205, Windermere, FL 34786

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

  Last Sold Summary

  • 10% Below List Price
  • $196/SF
  • 39 Days On Market

  Current Estimated Value $292,018

  Last Listing Agent Raymond Glenn LAKESIDE REALTY WINDERMERE INC

  8277 Maritime Flag St Unit 205, Windermere, FL 34786
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  /40

  Est $492,741 Not Listed For Sale

  13856 Summerport Trail Loop, Windermere, FL 34786

  • 4 Beds
  • 2.5 Baths
  • 2,107 Sq Ft
  • Built 2016

  13856 Summerport Trail Loop, Windermere, FL 34786

  Last Sold Summary

  • $235/SF
  • 3 Days On Market

  • Last Sold Price $495,000
  • May 30, 2023

  Last Listing Agent Skyler Warden COLDWELL BANKER REALTY
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  /27

  $1,100,000

  • 6 Beds
  • 4 Baths
  • 4,176 Sq Ft

  8236 Procida Isle Ln, Windermere, FL 34786

  This house is the perfect blend of luxury, comfort and modern convenience. From the moment you arrive, you're welcomed by a charming brick paver front porch that leads into a light-filled foyer with a private office at the front of the home. Beautiful wood-look tile flooring flows seamlessly throughout the main level. The stunning gourmet kitchen features 42” cabinets, gas appliances, light

  Babi Hennemann WRA BUSINESS & REAL ESTATE

  8236 Procida Isle Ln, Windermere, FL 34786
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  /2

  $530,000 Sold Aug 15, 2025

  12868 Holdenbury Ln, Windermere, FL 34786

  • 4 Beds
  • 2.5 Baths
  • 2,460 Sq Ft
  • Built 2006

  Last Sold Summary

  • 11% Below List Price
  • $215/SF
  • 39 Days On Market

  Current Estimated Value $537,755

  Last Listing Agent Victor Nawrocki VISION HOME REAL ESTATE, LLC

  12868 Holdenbury Ln, Windermere, FL 34786
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  /43

  Est $760,710 Not Listed For Sale

  8711 Lookout Pointe Dr, Windermere, FL 34786

  • 4 Beds
  • 3.5 Baths
  • 3,419 Sq Ft
  • Built 2015

  8711 Lookout Pointe Dr, Windermere, FL 34786

  Last Sold Summary

  • 1% Above List Price
  • $219/SF
  • 10 Days On Market

  • Last Sold Price $750,000
  • May 24, 2024

  Last Listing Agent Pilar Fernandez SIX STAR REALTY GROUP LLC
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  /45

  $850,000

  • 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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  /2

  $375,000 Sold Apr 27, 2026

  12683 Langstaff Dr, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 1,428 Sq Ft
  • Built 2003

  Last Sold Summary

  • $263/SF
  • 3 Days On Market

  Current Estimated Value $370,524

  Last Listing Agent Vlad Kizlo KELLER WILLIAMS REALTY AT THE LAKES

  12683 Langstaff Dr, Windermere, FL 34786
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  /37

  Est $450,384 Not Listed For Sale

  13477 Gorgona Isle Dr, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 1,756 Sq Ft
  • Built 2020

  13477 Gorgona Isle Dr, Windermere, FL 34786

  Last Sold Summary

  • 5% Below List Price
  • $271/SF
  • 54 Days On Market

  • Last Sold Price $475,000
  • Jun 28, 2024

  Last Listing Agent Jen Dantas THE FLORIDA LOUNGE REALTY LLC
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  /35

  $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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  /2

  $580,000 Sold Sep 22, 2025

  12867 Penshurst Ln, Windermere, FL 34786

  • 3 Beds
  • 2 Baths
  • 2,300 Sq Ft
  • Built 2004

  Last Sold Summary

  • 3% Below List Price
  • $252/SF
  • 3 Days On Market

  Current Estimated Value $576,335

  Last Listing Agent Stefany Marcelino RE/MAX INNOVATION

  12867 Penshurst Ln, Windermere, FL 34786
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  /95

  Est $870,209 Not Listed For Sale

  11947 Otterbrooke Trail, Windermere, FL 34786

  • 5 Beds
  • 3.5 Baths
  • 3,407 Sq Ft
  • Built 2013

  11947 Otterbrooke Trail, Windermere, FL 34786

  Last Sold Summary

  • 3% Below List Price
  • $264/SF
  • 58 Days On Market

  • Last Sold Price $900,000
  • Jun 06, 2023

  Last Listing Agent Caroline De Castro Marcellini COMPASS FLORIDA, LLC
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  /46

  $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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  /2

  $695,000 Sold Jun 13, 2025

  116 Main St, Windermere, FL 34786

  • 3 Beds
  • 2 Baths
  • 1,269 Sq Ft
  • Built 1958

  Last Sold Summary

  • $548/SF
  • 91 Days On Market

  Current Estimated Value $711,444

  Last Listing Agent Adam Judd METROPOLIS R.E. SOLUTIONS, LLC

  116 Main St, Windermere, FL 34786
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  Est $712,849 Not Listed For Sale

  11813 Cave Run Ave, Windermere, FL 34786

  • 4 Beds
  • 3.5 Baths
  • 2,935 Sq Ft
  • Built 2014

  11813 Cave Run Ave, Windermere, FL 34786

  Last Sold Summary

  • 1% Below List Price
  • $245/SF
  • 16 Days On Market

  • Last Sold Price $719,000
  • May 13, 2024

  Last Listing Agent Jaime Leizan EXP REALTY LLC
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  /65

  $2,500,000

  • 6 Beds
  • 4 Baths
  • 4,482 Sq Ft

  9648 Weatherstone Ct, Windermere, FL 34786

  Set within the private gates of Weatherstone on Lake Olivia, this stunning lakefront residence offers a rare opportunity to enjoy refined living along the peaceful shoreline of Lake Olivia in Windermere. Situated on an expansive lakefront homesite, an increasingly rare find in this area, the property provides exceptional space, privacy, and unobstructed water views. Boasting 6 bedrooms and 4 full

  Andy Neal THE AGENCY FL

  9648 Weatherstone Ct, Windermere, FL 34786
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  /2

  $305,000 Sold Jun 06, 2025

  8276 Maritime Flag St Unit 110, Windermere, FL 34786

  • 3 Beds
  • 2 Baths
  • 1,442 Sq Ft
  • Built 2007

  Last Sold Summary

  • 7% Below List Price
  • $212/SF
  • 62 Days On Market

  Current Estimated Value $302,777

  Last Listing Agent Evan Caulfield STOCKWORTH REALTY GROUP

  8276 Maritime Flag St Unit 110, Windermere, FL 34786
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  Est $2,186,526 Not Listed For Sale

  11817 Vinci Dr, Windermere, FL 34786

  • 4 Beds
  • 4.5 Baths
  • 5,023 Sq Ft
  • Built 2012

  11817 Vinci Dr, Windermere, FL 34786

  Last Sold Summary

  • 1% Below List Price
  • $438/SF
  • 36 Days On Market

  • Last Sold Price $2,200,000
  • Jun 13, 2024

  Last Listing Agent Hojin Chang RE/MAX
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  /66

  $3,699,000

  • 3 Beds
  • 5 Baths
  • 4,262 Sq Ft

  4812 Alexandra Garden Ct, Windermere, FL 34786

  Luxury villa living within the exclusive Gardens of Isleworth, part of the Isleworth Golf & Country Club. This exceptional Southpoint built residence boasts a captivating courtyard floor plan that provides breathtaking views from every corner of the home. The rear of the residence presents serene views of a picturesque pond and the tranquil Isleworth Gardens, while interior windows reveal a

  Rob Rahter STOCKWORTH REALTY GROUP

  4812 Alexandra Garden Ct, Windermere, FL 34786
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  /46

  $825,000 Sold May 15, 2025

  8738 Iron Mountain Trail, Windermere, FL 34786

  • 4 Beds
  • 3.5 Baths
  • 3,127 Sq Ft
  • Built 2013

  Last Sold Summary

  • 13% Below List Price
  • $264/SF
  • 313 Days On Market

  Current Estimated Value $823,644

  Last Listing Agent Crystal Washington Booth CENTURY 21 BE3

  8738 Iron Mountain Trail, Windermere, FL 34786
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  /29

  Not Listed For Sale

  14264 Desert Haven St Unit GE, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 1,840 Sq Ft
  • Built 2012

  14264 Desert Haven St Unit GE, Windermere, FL 34786

  Last Sold Summary

  • $215/SF
  • 106 Days On Market

  • Last Sold Price $395,000
  • Jul 19, 2024

  Last Listing Agent Jennifer McCarty ORCHARD BROKERAGE, LLC
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  /9

  $5,995,000 New Construction

  • 5 Beds
  • 6 Baths
  • 6,000 Sq Ft

  13377 Lake Butler Blvd, Winter Garden, FL 34787

  Pre-Construction. To be built. To be Built, Rendering provided by master custom home builder, David Konkol of Konkol Custom Homes. However, buyer can work with builder to build any design buyer prefers (pricing to adjust accordingly). The property is spectacular waterfront acreage with boat dock on boatable, skiable Lake Roper. Acreage is 12.4 +/- with some conservation. Zoned A-1 (agricultural

  Dawn Briggs BLUE MAGNOLIA REALTY LLC

  13377 Lake Butler Blvd, Winter Garden, FL 34787
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  /2

  $1,400,000 Sold Apr 08, 2026

  6023 Blakeford Dr, Windermere, FL 34786

  • 5 Beds
  • 3 Baths
  • 3,013 Sq Ft
  • Built 1999

  Last Sold Summary

  • 8% Below List Price
  • $465/SF
  • 9 Days On Market

  Current Estimated Value $1,505,095

  Last Listing Agent Angela Durruthy KEENE'S POINTE REALTY

  6023 Blakeford Dr, Windermere, FL 34786

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