Windermere, FL Homes for Sale

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  $575,000

  • Land
  • 19,166 Sq Ft
  • $1,306,818 per Acre

  2 Chase Rd, Windermere, FL 34786

  Almost half an acre located on Main Street in the Town of Windermere

  Matthew Hughes REAL BROKER, LLC

  2 Chase Rd, Windermere, FL 34786
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  $459,000

  • 3 Beds
  • 2.5 Baths
  • 1,531 Sq Ft

  7327 Millstone St, Windermere, FL 34786

  A rare find in townhome living in the exclusive Lake Burden community of Windermere — this pristine corner unit sits tucked at the edge of the community, offering exceptional privacy and natural light, with views of beautiful and well-kept gardens. Enjoy morning coffee on the beautiful front porch before stepping inside to soaring ceilings and hardwood floors. The well-appointed kitchen features

  Storm Miller COMPASS FLORIDA LLC

  7327 Millstone St, Windermere, FL 34786
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  $415,000

  • 3 Beds
  • 2.5 Baths
  • 1,644 Sq Ft

  12804 Salomon Cove Dr, Windermere, FL 34786

  Experience elevated living in this beautifully updated Windermere townhouse, where timeless design meets modern convenience. Fresh interior paint, plush new carpeting, new water heater, and a full array of new appliances- including refrigerator, dishwasher, stove, washer and dryer - offers effortless, move-in-ready comfort. An elegant and generous workspace ideal for daily living and

  Beverly Bray BLUEWATER REALTY SERVICES LLC

  12804 Salomon Cove Dr, Windermere, FL 34786
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  $1,630,000

  • 3 Beds
  • 2 Baths
  • 2,238 Sq Ft

  11923 Lake Butler Blvd, Windermere, FL 34786

  Nestled on one of Windermere’s most desirable streets, this charming home offers a rare opportunity to enjoy small-town living on a beautifully wooded one-acre lot. The property features a welcoming covered entry with double doors that open into a light-filled foyer and spacious family room with soaring vaulted ceilings and a cozy wood-burning fireplace. The open-concept kitchen includes a large

  Michael Julian JULIAN PROPERTIES, INC.

  11923 Lake Butler Blvd, Windermere, FL 34786
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  $330,000

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

  8179 Maritime Flag St Unit 101, Windermere, FL 34786

  Located just 10 minutes from Disney's Magic Kingdom and Transportation and Ticket Center, welcome to this beautifully maintained FIRST FLOOR END UNIT in the highly sought after Lakeside at Lakes of Windermere. Move in ready and thoughtfully updated, this home offers a bright, open split floor plan with high ceilings and a light, neutral palette throughout. The home has been wired with high speed

  Chris Sartwell CENTURY 21 CARIOTI

  8179 Maritime Flag St Unit 101, Windermere, FL 34786
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  $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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  $849,900

  • 4 Beds
  • 2.5 Baths
  • 2,698 Sq Ft

  14255 Sonco Ave, Windermere, FL 34786

  Super Rare Opportunity! Tucked away in one of Windermere’s most desirable areas is the beautiful home on over 1 half acre homesite on a corner lot with no rear neighbors and a gorgeous lake view. Don't sleep 'on' this home if you want to sleep 'in' this home! New roof 2023. Interior features include a fully remodeled kitchen with white 42" cabinets with crown moulding and gold hardware, custom

  Carmen Aridas RE/MAX PRIME PROPERTIES

  14255 Sonco Ave, Windermere, FL 34786
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  $3,995,000

  • 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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  $512,990 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,649 Sq Ft

  Cypress Plan at Lake Cawood Cove - Townhomes, Windermere, FL 34786

  Ashton Woods Builder

  5432 Winter Garden Vineland Rd Unit 37932786, Windermere, FL 34786
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  /19

  $2,500,000

  • Land
  • 5 Acres
  • $500,000 per Acre

  13377 Lake Butler Blvd, Winter Garden, FL 34787

  Fantastic opportunity to purchase 12+ acres of private, quiet lake front property in Winter Garden/Windermere area on West Lake Butler Blvd. with 4+ acres high and dry and no HOA. Property currently boasts dock with electricity and boat lift on a skiable lake. There is an existing house that could be remodeled or torn down and start fresh. Home is 4961 square feet and built in 1990 with

  Dawn Briggs BLUE MAGNOLIA REALTY LLC

  13377 Lake Butler Blvd, Winter Garden, FL 34787
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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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  $1,295,000

  • 5 Beds
  • 3.5 Baths
  • 3,694 Sq Ft

  12640 Salomon Cove Dr, Windermere, FL 34786

  Luxurious contemporary residence featuring 5 bedrooms, including the primary suite on the main floor. The main level with porcelain tile and marble staircase add sophistication, while the upper level with luxury vinyl flooring provides comfort and durability. Gourmet kitchen with custom cabinetry, waterfall island, premium stone countertops, and Samsung appliances. Walk-in closets in every

  Ramon Brandão WEBB FLORIDA REALTY LLC

  12640 Salomon Cove Dr, Windermere, FL 34786
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  $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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  $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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  $815,000

  • 5 Beds
  • 4.5 Baths
  • 3,312 Sq Ft

  13106 Orange Isle Dr, Windermere, FL 34786

  Explore the WINTERSET model from Ryan Homes of the Sanctuary at Lakes of Windermere, a corner unit, this 5- bedroom, 4.5 bathroom in Windermere combines the modern elegance, and a touch of magic with its a DISNEY Fireworks view, offering a lifestyle of unparalleled comfort. Upon entering, you are greeted by those who appreciate a dedicated workspace, the home includes a spacious office and a

  Victor De Oliveira FLORIDA CONNEXION PROPERTIES

  13106 Orange Isle Dr, Windermere, FL 34786
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  $575,000

  • Land
  • 21,344 Sq Ft
  • $1,173,469 per Acre

  1516 Hempel Ave, Windermere, FL 34786

  Vacant Land – 1⁄2 Acre in WindermereBuild your dream home or secure a smart investment in one of Central Florida’s most highly desired communities—Windermere!Spacious 1⁄2 acre lot with endless possibilitiesPrime location in the heart of WindermereSurrounded by A+ rated schoolsEasy access to shopping, dining, and major highwaysRare opportunity in a highly desirable

  Matthew Hughes REAL BROKER, LLC

  1516 Hempel Ave, Windermere, FL 34786
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  $2,300,000

  • 4 Beds
  • 4.5 Baths
  • 4,257 Sq Ft

  6550 Cartmel Ln, Windermere, FL 34786

  This is a rare, one of a kind stunning Luxury Contemporary Home in Windermere – Over Half Acre with Private Pound View Welcome to 6550 Cartmel Ln, located in the exclusive community of Reserve at Lake Butler Sound — one of the most desirable gated neighborhoods in Windermere. This beautifully renovated, modern-contemporary residence sits on an oversized lot with over half an acre and features its

  Jennifer Olmeda WRA BUSINESS & REAL ESTATE

  6550 Cartmel Ln, Windermere, FL 34786
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  $2,350,000

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

  2068 Roberts Point Dr, Windermere, FL 34786

  One or more photo(s) has been virtually staged. 1+ Acre Estate in Guard-Gated Windermere with Private Courtyard Pool, Detached Casita & Whole-Home Generator. Rare opportunity in Waterford Pointe offering space, privacy, and Lake Roberts access. Situated in one of Windermere’s premier guard-gated communities, this 5-bedroom, 4-bath estate features a private pool, a new Generac Guardian 24kW

  David Dorman CENTURY 21 CARIOTI

  2068 Roberts Point Dr, Windermere, FL 34786
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  $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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  $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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  $1,039,091 New Construction

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

  Arlington Plan at Palms at Windermere, 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

  14207 Crest Palm Ave Unit 36498773, 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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  $970,000

  • 5 Beds
  • 3.5 Baths
  • 3,820 Sq Ft

  6752 Trellis Vine Loop, Windermere, FL 34786

  ONLY APPROXIMATELY 7 YEARS NEW, THIS HOME OFFERS MODERN DESIGN AND PEACE OF MIND. MAJOR PRICE DROP - $80,000 OFF! Designed for those who crave space, privacy, and elevated living, this exceptional newer home offers 5 BEDROOMS PLUS TWO BONUS ROOMS, including ALL 4 MAIN BEDROOMS with WALK-IN CLOSETS and a private guest suite featuring an EN-SUITE and WALK-IN CLOSET—all complemented by NO REAR

  Candice Collins COLDWELL BANKER REALTY

  6752 Trellis Vine Loop, Windermere, FL 34786
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  $669,994

  • 4 Beds
  • 2.5 Baths
  • 2,053 Sq Ft

  13013 Overstreet Rd, Windermere, FL 34786

  Welcome to 13013 Overstreet Rd — a beautifully upgraded 4-bedroom, 2.5-bath home located in one of Windermere’s most desirable and sought-after communities. This property combines modern living, elegant design, and the true Florida lifestyle you’ve been searching for.Step inside to an open, bright floor plan featuring gorgeous wood floors, a spacious living area, and a modern kitchen with

  Omar Andreasen EXP REALTY LLC

  13013 Overstreet Rd, Windermere, FL 34786
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  $13,550,000 New Construction

  • 9 Beds
  • 16 Baths
  • 20,445 Sq Ft

  9621 Windy Ridge Rd, Windermere, FL 34786

  Under Construction. Under Construction. Experience unmatched privacy, prestige, and personalization with this brand-new mansion on 2.5 pristine acres in the heart of Windermere. Tucked against protected government land that can never be developed, this estate offers the serenity of untouched nature with the ultimate in luxury living.Two Pools one outdoor with a swim up bar and grill area and the

  Natalie Citarelli CITARELLI REALTY GROUP LLC

  9621 Windy Ridge Rd, Windermere, FL 34786
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  $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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  $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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  $2,475,000

  • 4 Beds
  • 3 Baths
  • 3,975 Sq Ft

  325 Magnolia St, Windermere, FL 34786

  Location Location Location. Set along the shores of Lake Down, part of the Butler Chain of Lakes, this Windermere home offers a rare mix of laid-back lake living and walkability to town. The Town of Windermere has much to offer. Walk to the local park and tennis courts just a few blocks from your home. It’s an easy stroll or bike ride to Main Street—home to local spots like Dixie Cream, Paloma

  Rebekkah Boskovich REVEL REALTY LLC

  325 Magnolia St, Windermere, FL 34786
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  $1,108,989 New Construction

  • 4 Beds
  • 4 Baths
  • 3,100 Sq Ft

  Arlington w/ Bonus Plan at Palms at Windermere, Windermere, FL 34786

  Welcome to the Arlington with Bonus! This stunning 3,099 square foot, two-story floor plan boasts 4 bedrooms, 4 bathrooms, and a spacious 2-car garage. Experience the ultimate in open-concept living on the main level, perfect for entertaining family and friends. The garage includes an extra hobby/work space for all your creative projects. Step outside and unwind under the inviting covered patio,

  Dream Finders Homes Builder

  14207 Crest Palm Ave Unit 36493225, Windermere, FL 34786
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  $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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  $880,000

  • 5 Beds
  • 3 Baths
  • 3,063 Sq Ft

  1925 Breezy Hill Dr, Windermere, FL 34786

  Modern luxury meets resort-style living in this stunning 5-bedroom estate located in the highly desirable Westover Club community. From the moment you step inside, you’re greeted by soaring ceilings and dramatic second-story windows that flood the home with natural light, creating a bright and inviting atmosphere.Just off the entry, a custom-designed office features hardwood flooring,

  Michelle Melo FLORIDA REALTY INVESTMENTS

  1925 Breezy Hill Dr, Windermere, FL 34786
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  $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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  $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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  $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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  $5,900,000

  • 5 Beds
  • 8.5 Baths
  • 11,861 Sq Ft

  9639 Westover Roberts Rd, Windermere, FL 34786

  Welcome to a residence that transcends even the highest expectations of luxury living! This is a once-in-a-lifetime estate where architecture, scale, and location combine to create an experience that is as rare as it is breathtaking.From the moment you arrive, the home commands attention with a grand, Mediterranean-inspired façade that opens to interiors of soaring scale and meticulous marble

  Julie Bettosini STOCKWORTH REALTY GROUP

  9639 Westover Roberts Rd, Windermere, FL 34786
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  $1,475,000

  • 5 Beds
  • 4.5 Baths
  • 3,835 Sq Ft

  7231 Sangalla Dr, Windermere, FL 34786

  Located in the gated community of Casa Del Lago in Windermere, featuring just 88 luxury homes surrounding Lake Burden, this neighborhood offers an exceptional setting near top-rated schools and only minutes from Orlando’s most popular destinations, including major highways, airports, shopping, dining, and world-renowned attractions. Built by one of the nation’s top private homebuilders, David

  Matt Kester THE REAL ESTATE COLLECTION LLC

  7231 Sangalla Dr, Windermere, FL 34786

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