Homes for Sale near Windermere Elementary School

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  /57

  $6,150,000

  • 7 Beds
  • 7 Baths
  • 8,000 Sq Ft

  9725 Chestnut Ridge Dr, Windermere, FL 34786

  Newly renovated, this private Isleworth residence offers a rare balance of architectural authority, thoughtful design, and quiet indulgence.Spanning approximately 8,000 square feet, the home unfolds with intention. Rich walnut cabinetry and wood detailing create warmth and continuity throughout, while the fireplace and wine cellar anchor the living spaces with understated elegance. Every room

  Dianna Desboyaux DOUGLAS ELLIMAN

  9725 Chestnut Ridge Dr, Windermere, FL 34786
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  /44

  $3,995,000 Open Sat 1PM - 3PM

  • 5 Beds
  • 6.5 Baths
  • 5,639 Sq Ft

  801 W 2nd Ave, Windermere, FL 34786

  Priced below appraised value, this extraordinary Windermere estate presents a rare opportunity to enjoy refined lakefront living on the Butler Chain of Lakes. Set along one of the area’s most desirable streets, the residence has undergone more than $350,000 in recent luxurious upgrades, including a reimagined kitchen and fireplace, new windows and doors, upgraded landscape lighting, refreshed

  Harif Hazera LLC PREMIER SOTHEBY'S INTL. REALTY

  801 W 2nd Ave, Windermere, FL 34786
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  /19

  $834,000

  • 4 Beds
  • 3.5 Baths
  • 3,068 Sq Ft

  6631 Crestmont Glen Ln Unit 1, Windermere, FL 34786

  Welcome to 6631 Crestmont Glen Lane, a beautifully maintained executive home in the gated community of Glenmuir. Set on a large and spacious, landscaped lot, this 4-bedroom, 3.5-bath residence offers an ideal blend of space, comfort, and everyday functionality.Step inside to soaring ceilings, abundant natural light, and an open-concept layout designed for both entertaining and relaxed living.

  Gonzalo Senior IRM INVEST., REAL EST.& MGMT.

  6631 Crestmont Glen Ln Unit 1, Windermere, FL 34786
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  $1,250,000

  • 4 Beds
  • 3 Baths
  • 2,882 Sq Ft

  11536 Claymont Cir, Windermere, FL 34786

  One or more photo(s) has been virtually staged. Welcome to luxury living inside the guard-gated community of Keene’s Pointe, home to the renowned Golden Bear Club and its Jack Nicklaus Signature golf course. Perfectly positioned within one of Windermere’s most sought-after neighborhoods, this exceptional single-story residence offers a refined blend of elegance, comfort, and

  Matt Allen MATT ALLEN REAL ESTATE LLC

  11536 Claymont Cir, Windermere, FL 34786
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  $5,500,000

  • 4 Beds
  • 5 Baths
  • 4,330 Sq Ft

  5138 Fairway Oaks Dr, Windermere, FL 34786

  Set along Isleworth’s signature 12th fairway, this fully reimagined estate captures the essence of refined golf course living within the renowned Isleworth Golf & Country Club—recognized among the finest private club communities in the world. Encompassing more than 4,300 square feet, the single-story residence has been completely transformed inside and out. Thoughtfully redesigned interiors

  Monica Lochmandy ISLEWORTH REALTY LLC

  5138 Fairway Oaks Dr, Windermere, FL 34786
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  /65

  $5,100,000

  • 4 Beds
  • 5.5 Baths
  • 6,424 Sq Ft

  5243 Isleworth Country Club Dr, Windermere, FL 34786

  Presenting a magnificent Isleworth golf front estate with sweeping lake views, perched above holes #2 and #9 and Lake Chase, combining a completely reimagined interior with designer elegance and modern grand style. With no neighbors on three sides, this stunning home offers a unique combination of privacy mixed with rare golf and water vistas. Home recently underwent a major “spare no expense”

  Rob Rahter STOCKWORTH REALTY GROUP

  5243 Isleworth Country Club Dr, Windermere, FL 34786
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  $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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  /58

  $4,599,000

  • 5 Beds
  • 5.5 Baths
  • 7,740 Sq Ft

  12540 Park Ave, Windermere, FL 34786

  Extraordinary Lake Butler views abound from this classically elegant yet recently updated Chaine du Lac estate residence. Cradled in a private cove on Windermere’s signature lake on The Butler Chain, this showplace address stands supreme for its majestic presence, distinguished features and updates, and unsurpassed outdoor resort-style entertainment and living areas. Boasting a new roof, new

  Rob Rahter STOCKWORTH REALTY GROUP

  12540 Park Ave, Windermere, FL 34786
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  $2,895,000

  • 6 Beds
  • 6.5 Baths
  • 5,882 Sq Ft

  12720 Jacob Grace Ct, Windermere, FL 34786

  Nestled within one of **Windermere**’s most exclusive communities, this extraordinary custom-built lakefront estate with an almost 2 acres lot offers an elegant lifestyle defined by privacy, prestige, and breathtaking nightly views of the **Walt Disney World** fireworks. With nearly 6,000 square feet, six bedrooms, and six and a half baths, this residence is the pinnacle of refined Central

  Adrian Jacob REDFIN CORPORATION

  12720 Jacob Grace Ct, Windermere, FL 34786
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  /41

  $1,250,000

  • 4 Beds
  • 3 Baths
  • 2,582 Sq Ft

  8411 Woburn Ct, Windermere, FL 34786

  Welcome to this beautifully reimagined luxury residence in the highly sought-after Keene’s Pointe, ideally positioned on a quiet cul-de-sac and backing onto the serene natural beauty of the Tibet Butler Preserve. This exceptional 4 bedroom, 3 bathroom home with a dedicated office has been extensively renovated to an outstanding standard, offering a perfect blend of modern design, comfort, and

  Andy Neal THE AGENCY FL

  8411 Woburn Ct, Windermere, FL 34786
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  /2

  $3,500,000 New Construction

  • 4 Beds
  • 4 Baths
  • 2,500 Sq Ft

  43 Main St, Windermere, FL 34786

  Under Construction. Modern New Construction on the Butler Chain Canal – Downtown WindermereExperience bright, modern waterfront living in the heart of the Town of Windermere. This brand-new construction single-story home is currently under construction with an anticipated completion date of late Summer 2026. The residence will offer approximately 2,500 square feet of living space and 4,280

  Milena Fernandes GOLDEN GROUP REALTY LLC

  43 Main St, Windermere, FL 34786
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  $3,725,000

  • 5 Beds
  • 4 Baths
  • 4,875 Sq Ft

  58 Main St, Windermere, FL 34786

  Nestled in the heart of Old Town Windermere, this exceptional lakefront residence offers direct access to the Butler Chain of Lakes from the tranquil waters of Wauseon Bay, prized for its reduced boat traffic and peaceful setting. Set on an oversized waterfront lot with western exposure, the home captures breathtaking lake views from nearly every room—delivering spectacular sunsets and a seamless

  Michelle Ingrassia LPT REALTY, LLC

  58 Main St, Windermere, FL 34786
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  /25

  $618,000

  • 3 Beds
  • 2 Baths
  • 2,077 Sq Ft

  6315 Clearmeadow Ct, Windermere, FL 34786

  One or more photo(s) has been virtually staged. Welcome to this beautifully maintained home in the gated community of Glenmuir in Windermere. Perfectly located just minutes from Walt Disney World, Universal Orlando Resort, SeaWorld Orlando, and the charming downtown areas of Winter Garden and Downtown Windermere, this location offers both luxury and convenience. Tucked away on a quiet cul-de-sac,

  Jessica Otero KELLER WILLIAMS REALTY AT THE PARKS

  6315 Clearmeadow Ct, Windermere, FL 34786
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  /44

  $789,995

  • 3 Beds
  • 2 Baths
  • 2,469 Sq Ft

  9237 Sabal Palm Cir, Windermere, FL 34786

  Nestled in the charming and highly desirable Silverwoods subdivision of Windermere, this beautifully maintained home offers the perfect blend of comfort, convenience, and community living. Ideally situated between Bay Hill and Isleworth, Silverwoods is a sought-after neighborhood of just over 250 homes, known for its tree-lined streets, sidewalks, street lighting, and welcoming atmosphere.

  Chelsea Murphy OLYMPUS EXECUTIVE REALTY INC

  9237 Sabal Palm Cir, Windermere, FL 34786
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  /57

  $1,700,000

  • 6 Beds
  • 4.5 Baths
  • 4,572 Sq Ft

  5106 Tildens Grove Blvd, Windermere, FL 34786

  PARADISE...FOUND. Welcome to this incredible custom-built executive home in Windermere’s esteemed & highly desired Tildens Grove community which welcomes you with 24-hour guard gated security and beautiful quiet tree-lined streets. Get ready for LUXURY around every corner of this home spanning nearly 6,000 square feet of indoor & outdoor living space. Starting with one-of-a-kind curb appeal, this

  Tara Moore TARA MOORE REAL ESTATE

  5106 Tildens Grove Blvd, Windermere, FL 34786
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  /50

  $749,901

  • 4 Beds
  • 3 Baths
  • 2,622 Sq Ft

  11450 Arborside Bend Way, Windermere, FL 34786

  Beautifully maintained 4BR/3BA pool home in gated Glenmuir, Windermere. Open floor plan with high ceilings, formal dining, and spacious family room. Kitchen with breakfast nook overlooks screened pool/lanai. Primary suite features dual closets, spa bath, and pool access. Home includes water softener system, water heater from 2022 and air handler from 2020. Enjoy a private 0.25-acre lot in a

  David Sanchez LOKATION

  11450 Arborside Bend Way, Windermere, FL 34786
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  /32

  $1,885,000

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

  2958 Marquesas Ct, Windermere, FL 34786

  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 comfort, refinement, and privacy, this home embodies Florida luxury living at

  Dianna Desboyaux DOUGLAS ELLIMAN

  2958 Marquesas Ct, Windermere, FL 34786
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  /57

  $4,100,000

  • 4 Beds
  • 4.5 Baths
  • 5,301 Sq Ft

  5151 Latrobe Dr, Windermere, FL 34786

  Positioned along the stunning 4th fairway of the renowned Isleworth Golf & Country Club, this exceptional single-story estate offers four bedrooms and more than 5,300 square feet of meticulously crafted living space. Every detail of this residence reflects the owner’s exceptional craftsmanship, with bespoke woodwork woven throughout the home, culminating in the crown jewel: the primary suite’s

  Monica Lochmandy ISLEWORTH REALTY LLC

  5151 Latrobe Dr, Windermere, FL 34786
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  $2,950,000

  • 5 Beds
  • 4 Baths
  • 7,153 Sq Ft

  4301 Down Point Ln, Windermere, FL 34786

  Lakefront estate on Lake Down in the Butler Chain of Lakes with over 150 feet of frontage and no HOA in Sunset Bay. Built in 1983, this 5 bedroom, 4 bath pool home offers nearly 7,000 square feet across three levels and presents a rare opportunity to renovate a true chain-of-lakes property to your own style and standards. Home retains much of its original character and is priced accordingly,

  Phillip Mariani EXP REALTY LLC

  4301 Down Point Ln, Windermere, FL 34786
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  /50

  $792,500

  • 3 Beds
  • 2 Baths
  • 1,664 Sq Ft

  825 Oakdale St, Windermere, FL 34786

  Back on the market no fault of the home! ONLY HOME ON WINDERMERE’S ICONIC SANDY STREETS UNDER $800,000 — DON’T MISS YOUR CHANCE.Back on the market and better than ever, this charming traditional cottage now features thoughtful exterior enhancements that further showcase its incredible homesite and future potential. Nestled along one of Windermere’s signature sandy streets, this property

  Mildred Hershiser EXP REALTY LLC

  825 Oakdale St, 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 moment

  Isis Sarcos EXP REALTY LLC

  5070 Down Point Ln, Windermere, FL 34786
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  $925,000 Open Sat 3:30PM - 5:30PM

  • 4 Beds
  • 4 Baths
  • 2,636 Sq Ft

  3328 Wax Berry Ct, Windermere, FL 34786

  One or more photo(s) has been virtually staged. Located within Lake Butler Estates, one of Windermere’s most private and established communities, this 4-bedroom, 4-bath pool home is situated on a one-acre cul-de-sac lot surrounded by mature oak trees and only 11 neighboring homes. Originally constructed in 1959 and renovated in 2022, this single-story home offers an open, split floor plan that

  Ferris Kassar PREFERRED REAL ESTATE BROKERS

  3328 Wax Berry Ct, Windermere, FL 34786
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  /27

  $4,690,000

  • 3 Beds
  • 4.5 Baths
  • 6,236 Sq Ft

  4906 Aviva Garden Ct, Windermere, FL 34786

  Welcome to an exceptional opportunity within the gates of Isleworth, one of Central Florida’s most Acclaimed private golf communities. Perfectly positioned along a tranquil pond and scenic walking trail, this move-in ready residence offers a rare blend of privacy, natural beauty, and refined living in the heart of Windermere.Thoughtfully designed for both everyday comfort and elevated

  William Campbell CAMPBELL CUSTOM HOMES INC

  4906 Aviva Garden Ct, Windermere, FL 34786
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  $3,495,000

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

  5538 W Lake Butler Rd, Windermere, FL 34786

  Welcome to 5538 W Lake Butler Road—an expansive, newly renovated estate set on 1.9 acres of lush, lakefront land in arguably one of Central Florida’s most coveted locations, Kelso on Lake Butler. What distinguishes this property is its remarkable dual lake access. Your own private boat dock provides direct skiable waterfront on Lake Davis, while exclusive community privileges grant you gated

  Julie Bettosini STOCKWORTH REALTY GROUP

  5538 W Lake Butler Rd, Windermere, FL 34786

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