Windermere, FL Homes for Sale with Acreage

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  /90

  $6,995,000

  $405K PRICE DROP

  • 5 Beds
  • 8 Baths
  • 7,529 Sq Ft

  9349 Tibet Pointe Cir, Windermere, FL 34786

  Set along the pristine shores of Lake Tibet Butler, this exceptional estate within Keene's Pointe is a masterclass in timeless design, refined craftsmanship, and elevated lakefront living. Spanning over 7,500 square feet, every detail has been thoughtfully curated to balance grandeur with comfort. This home is meticulously cared for with improvements which recent improvements such as a new tile

  Jay Martin CORCORAN PREMIER REALTY

  9349 Tibet Pointe Cir, Windermere, FL 34786
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  /38

  $1,775,000

  • 3 Beds
  • 3 Baths
  • 3,135 Sq Ft

  12001 Lake Butler Blvd, Windermere, FL 34786

  Exceptional Contemporary Estate in the Heart of Windermere!Discover the perfect blend of modern design, timeless comfort, and unmatched location with this beautifully updated estate home, ideally situated on a 1-acre lot in the desirable Town of Windermere. Surrounded by multi-million-dollar residences, and just moments from the famed Butler Chain of Lakes, this property offers a rare

  Michael Julian JULIAN PROPERTIES, INC.

  12001 Lake Butler Blvd, Windermere, FL 34786
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  /4

  $4,950,000

  • Land
  • 2.9 Acres
  • $1,706,897 per Acre

  0 Windy Ridge Rd Unit MFRO6439500, Windermere, FL 34786

  Exceptional lakefront opportunity to build on one of the most coveted sites along The Butler Chain of Lakes. This prime and elevated lot is 215 feet wide and one of three being carved out of a larger compound to create an extraordinary and private home site being offered for the first time. No time frame to build, no HOA approval, and a convenient location in East Windermere, bypassing downtown

  Rob Rahter STOCKWORTH REALTY GROUP

  0 Windy Ridge Rd Unit MFRO6439500, Windermere, FL 34786
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  /81

  $3,300,000

  $500K PRICE DROP

  • 5 Beds
  • 5 Baths
  • 5,018 Sq Ft

  11539 Lake Butler Blvd, Windermere, FL 34786

  Incredible 1st Floor Inlaw Apartment with Full Bath, Sitting Room with Fireplace & Bedroom with Large Walk in Closet * Purchase before October 31, 2026 and receive a full size Pickleball & Sport Court * Welcome to this spectacular 5-bedroom, 5-bathroom custom home offering over 8,000 square feet of thoughtfully designed luxury living—spared no expense and crafted to perfection. * Nestled on a

  Darrell Nunnelley VINTAGE REALTY GROUP LLC

  11539 Lake Butler Blvd, Windermere, FL 34786
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  /90

  $2,150,000

  $200K PRICE DROP

  • 5 Beds
  • 4 Baths
  • 4,876 Sq Ft

  2068 Roberts Point Dr, Windermere, FL 34786

  One or more photo(s) has been virtually staged. Private Windermere Estate in Guard-Gated Waterford Pointe with Detached Guest Casita, and Lake Access.A rare opportunity in one of Windermere’s most established guard-gated communities, this private estate offers the space, flexibility, and lifestyle today’s luxury buyers are actively seeking. Set on over an acre within Waterford Pointe, the

  David Dorman CENTURY 21 CARIOTI

  2068 Roberts Point Dr, Windermere, FL 34786
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  /73

  $1,995,000

  Open Sat 12PM - 3PM

  • 6 Beds
  • 6 Baths
  • 5,869 Sq Ft

  4282 Mckinnon Rd, Windermere, FL 34786

  Welcome to 4282 McKinnon Rd, a beautifully updated Windermere estate offering exceptional space, privacy, and flexibility on approximately 1.15 acres—with NO HOA. Featuring 6 bedrooms, 6 baths, nearly 5,900 square feet of living space, a private pool, and 3-car garage, this custom home combines an impressive floor plan with extensive recent improvements.Move-in ready and refreshed inside and

  Shelley Dawson COMPASS FLORIDA LLC

  4282 Mckinnon Rd, Windermere, FL 34786
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  /74

  $3,100,000

  • 4 Beds
  • 4.5 Baths
  • 4,296 Sq Ft

  12102 Montalcino Cir, Windermere, FL 34786

  Virtually Staged. Welcome to 12102 Montalcino Circle, an exceptional custom built waterfront estate located in one of Windermere's most sought after gated communities, Casa Del Lago. Perfectly positioned at the end of a quiet cul-de-sac on 1.41 acres along the shores of Lake Burden, this extraordinary residence is offered fully furnished and showcases breathtaking water views, nightly Disney

  Kristy Cook EXP REALTY LLC

  12102 Montalcino Cir, Windermere, FL 34786
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  /53

  $8,695,000

  • Land
  • 2.19 Acres
  • $3,970,320 per Acre

  12422 Park Ave, Windermere, FL 34786

  WELCOME TO PARK AVENUE. This tremendous opportunity offers 2.19 acres of sprawling possibilities over 2 parcels with Southeastern exposure and sweeping lake views. Nestled on the gorgeous shoreline of Lake Butler among the famed Butler Chain of Lakes, within one of Windermere’s most desirable communities - Chaine Du Lac – this exclusive homesite truly has it all. The gates within the gates that

  Michael Julian JULIAN PROPERTIES, INC.

  12422 Park Ave, Windermere, FL 34786
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  /39

  $1,830,000

  $270K PRICE DROP

  • 5 Beds
  • 4.5 Baths
  • 4,716 Sq Ft

  2958 Marquesas Ct, Windermere, FL 34786

  PRICE IMPROVEMENT! Rarely available property featuring a separate GUEST HOUSE! Recently appraised - Pricing adjusted to reflect current appraised value. This beautiful and elegant courtyard-style estate, complete with a PRIVATE GUEST HOUSE/IN-LAW SUITE, offers the ideal retreat for multi-generational living within one of the most exclusive gated communities in the Town of Windermere. Designed for

  Dianna Desboyaux DOUGLAS ELLIMAN

  2958 Marquesas Ct, Windermere, FL 34786
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  /43

  $2,275,000

  $125K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 3,004 Sq Ft

  9620 Maywood Dr, Windermere, FL 34786

  Lakefront living on the Butler Chain of Lakes in the heart of Windermere. This rare offering on Lake Down presents 100 feet of direct frontage, expansive water views and a private setting on a quiet cul-de-sac with no HOA. Set across 1.35 acres, this two-story pool home captures the essence of Windermere’s enduring lakefront lifestyle, where space, privacy, and natural beauty come together in a

  Linda O'Grady PREMIER SOTHEBYS INT'L REALTY

  9620 Maywood Dr, Windermere, FL 34786
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  /57

  $4,995,000

  • 6 Beds
  • 6.5 Baths
  • 7,349 Sq Ft

  5070 Down Point Ln, Windermere, FL 34786

  Nestled behind the gates in the heart of Windermere, this exceptional lakefront estate commands sweeping views across the renowned Butler Chain of Lakes. Designed for refined living and effortless entertaining, the residence offers six bedrooms, six full baths, and a powder bath — including a fully equipped private guest apartment ideal for extended family or long-term visitors.From the

  Isis Sarcos EXP REALTY LLC

  5070 Down Point Ln, Windermere, FL 34786

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