Windermere, FL Homes for Sale

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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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  $785,000

  • Land
  • 1.44 Acres
  • $545,139 per Acre

  0 Quail Cove Ct, Windermere, FL 34786

  Welcome to Quail Cove Court—an exceptional opportunity to own 1.44 acres in the highly sought-after Windermere area. Nestled within the desirable Windermere Downs community yet not subject to an HOA, this homesite offers privacy, flexibility, and the freedom to design and build your dream residence with the builder of your choice.The property is well-positioned at the end of a quiet

  Alexis Anderson REGENCY REAL ESTATE LLC

  0 Quail Cove Ct, Windermere, FL 34786
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  $1,399,000

  • 4 Beds
  • 3.5 Baths
  • 3,359 Sq Ft

  7135 Horizon Cir, Windermere, FL 34786

  NEW PRICE, NEW YEAR! Nestled in the TRUE TOWN of WINDERMERE is this Absolutely stunning, meticulously maintained pool home with TALL CEILINGS and lots of land surrounding on both sides! This HIDDEN GEM has majestic mature oaks on a private .74 ACRE CONSERVATION LOT in QUIET, highly desirable Windermere Reserve with access to the BUTLER CHAIN OF LAKES. This solid BLOCK one-story home features a

  Sarah Bosch THE BOSCH GROUP

  7135 Horizon Cir, Windermere, FL 34786
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  $2,145,000

  • 4 Beds
  • 4.5 Baths
  • 4,013 Sq Ft

  6036 Greatwater Dr, Windermere, FL 34786

  Welcome to Keene’s Pointe! Discover the charm of this custom-built home located on the 17th Fairway of the renown Jack Nicklaus Signature Golf Course and across from the lakefront mansions that line this quiet cul-de- sac on Greatwater Drive. This 4BR/4Full Bath/1 Half Bath golf course estate home exudes warmth from the gorgeous hardwood floors and abundant natural light. You will find your main

  Angela Durruthy KEENE'S POINTE REALTY

  6036 Greatwater Dr, Windermere, FL 34786
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  $657,000

  • 4 Beds
  • 3 Baths
  • 2,400 Sq Ft

  1369 Glenwick Dr, Windermere, FL 34786

  Welcome to this glamorous, fully renovated home featuring high-end upgrades throughout. As you enter, you’ll be greeted by a stunning custom-designed kitchen with abundant storage, top-of-the-line appliances, and a beautiful quartz island that seamlessly connects to the spacious living area—perfect for entertaining guests. A large dining area comfortably accommodates family gatherings, while the

  Mae Wang FL SUNSHINE STATE REALTY

  1369 Glenwick Dr, Windermere, FL 34786
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  /22

  $615,000 Open Sun 12PM - 4PM

  • 4 Beds
  • 3.5 Baths
  • 2,551 Sq Ft

  8533 Greenbank Blvd, Windermere, FL 34786

  A beautiful Home in a wonderful Gated Community in Windermere. Home is very spacious with Master downstairs, one owner, the upper floor was not even being used by seller. Come see this beauty, priced to sell.

  Faneeza Mohamed CENTURY 21 CARIOTI

  8533 Greenbank Blvd, Windermere, FL 34786
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  $870,000

  • 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

  Gladys Bezerra FLORIDA CONNEXION PROPERTIES

  13106 Orange Isle Dr, Windermere, FL 34786
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  /30

  $629,000

  • Land
  • 0.49 Acre
  • $1,283,673 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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  $320,000

  • 3 Beds
  • 2.5 Baths
  • 1,460 Sq Ft

  8259 Maritime Flag St Unit 4, Windermere, FL 34786

  One or more photo(s) has been virtually staged. Experience the best of Windermere living! This freshly updated two-story townhome offers resort-style amenities and unbeatable convenience, all just 10 minutes from Disney! Step inside to discover fresh paint throughout, brand new carpet, and an open-concept first floor with a kitchen/living room combo and a half bath. Upstairs, you’ll find three

  Lindsey Hudson REAL BROKER, LLC

  8259 Maritime Flag St Unit 4, Windermere, FL 34786
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  $1,088,989 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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  $418,000 Open Sun 12PM - 3PM

  • 3 Beds
  • 2.5 Baths
  • 1,547 Sq Ft

  13285 Gorgona Isle Dr, Windermere, FL 34786

  One or more photo(s) has been virtually staged. Welcome to this meticulously maintained 2 story townhome offering 3 bedrooms and 2.5 bathrooms, located in the highly desirable Windermere area. Built in 2020, this home offers approximately 1,547 square feet of well-designed living space, combining modern finishes with everyday functionality. The main level features an open-concept layout that

  Rodrigo Andrade REALTY HUB

  13285 Gorgona Isle Dr, Windermere, FL 34786
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  /15

  $11,800,000

  • 5 Beds
  • 3 Baths
  • 5,316 Sq Ft

  4226 Downeast Ln, Windermere, FL 34786

  Exceptional DEVELOPMENT OPPORTUNITY, currently R-CE zoning should allow for 3 Lakefront Luxury Home Sites Discover over 5+acres of waterfront land with 300 feet of pristine shoreline on LAKE DOWN, part of the coveted BUTLER CHAIN of Lakes. This is a rare chance to create a premier LAKEFRONT ESTATE or subdivide to create three ideally sized lots with water frontage. At present, the property

  Thad Czapka COLDWELL BANKER RESIDENTIAL RE

  4226 Downeast Ln, Windermere, FL 34786
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  /65

  $849,000

  • 4 Beds
  • 3.5 Baths
  • 3,235 Sq Ft

  8778 Peachtree Park Ct, Windermere, FL 34786

  Live the Orlando Dream, Disney at Your Doorstep! This 8-year-old stunner is just outside the back entrance to Disney, putting magic literally in your backyard! Minutes from epic dining, shopping, highways, and all Orlando attractions, this home is perfect for thrill-seekers, foodie friends, and anyone who loves city perks with suburban chill. Backing up to a peaceful conservation area, you get

  Erica Diaz HOMEVEST REALTY

  8778 Peachtree Park Ct, Windermere, FL 34786
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  $2,600,000

  • 5 Beds
  • 7 Baths
  • 5,366 Sq Ft

  6288 Blakeford Dr, Windermere, FL 34786

  Golfers, entertainers, and chefs- this is the home that checks every box. Perfectly positioned on the 18th tee box of the Golden Bear Golf & Country Club, this move-in ready, three-story five-bedroom, four full and three half bath custom residence is one of the most unique properties in all of Keene’s Pointe.Located within the highly coveted 24-hour guard-gated community, residents have the

  Ken Pozek REAL BROKER, LLC

  6288 Blakeford Dr, Windermere, FL 34786
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  $1,275,000

  • 4 Beds
  • 3 Baths
  • 3,021 Sq Ft

  11334 Camden Loop Way, Windermere, FL 34786

  Nestled within the guard-gated community of Keene’s Pointe, this beautifully updated single-story home offers a well-designed, functional layout with tasteful upgrades throughout. Recent improvements include luxury vinyl flooring, updated lighting, fresh interior and exterior paint, and a new roof installed in 2024, making the home truly move-in ready. The open-concept kitchen and family room are

  Rob Rahter STOCKWORTH REALTY GROUP

  11334 Camden Loop Way, Windermere, FL 34786
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  $1,060,000

  • 4 Beds
  • 4 Baths
  • 4,676 Sq Ft

  2107 Westover Reserve Blvd, Windermere, FL 34786

  Discover this beautifully updated 4-bedroom, 4-bathroom home tucked inside the exclusive gated community of Westover Reserve in Windermere, renowned for its tree-lined streets and serene setting. This home seamlessly blends spacious living with exceptional craftsmanship and thoughtful design throughout.Upon entering, you’re welcomed by a bright, open floor plan that showcases a recently

  Ken Pozek REAL BROKER, LLC

  2107 Westover Reserve Blvd, Windermere, FL 34786
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  $999,000

  • 5 Beds
  • 5.5 Baths
  • 3,680 Sq Ft

  6947 Cucamelon Ct, Windermere, FL 34786

  Welcome Home to Your Personal Oasis — tucked within the prestigious Sanctuary at Lakes of Windermere, this move-in-ready sanctuary is designed for inspired living and effortless entertaining. From the moment you step inside, you’ll feel how open, airy rooms and thoughtful finishes create a haven you can’t wait to come home to. With five full suites (including a main-floor guest suite), a

  Mahmoud Mango DALTON WADE INC

  6947 Cucamelon Ct, Windermere, FL 34786
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  $749,900

  • 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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  $1,999,000

  • 4 Beds
  • 4.5 Baths
  • 4,550 Sq Ft

  12235 Montalcino Cir, Windermere, FL 34786

  Casa del Lago gated community in Windermere, Florida. Exquisite 4 bedroom/4.5 bath luxury residence showcasing exceptional craftsmanship and high-end finishes throughout. As you arrive you are welcomed by a circular driveway and quaint courtyard entrance. The first floor boasts a formal dining room,and a spacious gathering room anchored by a stunning stone two-sided fireplace. A dedicated

  Teresa Stewart SOUTHERN REALTY GROUP LLC

  12235 Montalcino Cir, Windermere, FL 34786
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  $650,000

  • 3 Beds
  • 2 Baths
  • 2,146 Sq Ft

  13290 Orange Isle Dr, Windermere, FL 34786

  Welcome to this beautifully crafted Windermere residence, where timeless elegance meets modern comfort. Perfectly positioned on a quiet street, this home offers the ideal blend of privacy, sophistication, and convenience—just minutes from top-rated schools, upscale dining restaurants premier golf courses, and the world-renowned attractions of Orlando. Step inside to discover an inviting concept

  Christian Posegger EMPIRE NETWORK REALTY

  13290 Orange Isle Dr, 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

  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 its finest, where indoor grace meets outdoor serenity. The split floor

  Dianna Desboyaux DOUGLAS ELLIMAN

  2958 Marquesas Ct, Windermere, FL 34786
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  $1,545,000

  • 4 Beds
  • 3.5 Baths
  • 3,844 Sq Ft

  2509 Ridgewind Way, Windermere, FL 34786

  If you’ve dreamed of a home that feels both timeless and tailor-made for modern living, welcome to 2509 Ridgewind Way in the gated Estates at Windermere. Set on .75 acre this updated Southern estate combines architectural charm and every day comfort. A wrap-around front porch framed by copper lanterns and stately oaks sets the tone for the relaxed elegance inside. Flooded with natural light, the

  Hilary Hall COMPASS FLORIDA LLC

  2509 Ridgewind Way, Windermere, FL 34786
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  /65

  $6,395,000

  • 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 facade 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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  $695,000

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

  7616 Colbury Ave, Windermere, FL 34786

  Location, location, location! Welcome to this beautiful Windermere pool home, perfectly positioned with serene lake views and just a short distance from the tennis courts. This 4-bedroom, 3-bathroom residence offers over 2,700 square feet of living space and is truly a must-see. As you arrive, you’ll immediately appreciate the oversized driveway, 3-car garage, and charming front porch—the perfect

  Jenny Miller PROVIDENCE REALTY AND PROPERTY MANAGEMENT LLC

  7616 Colbury Ave, Windermere, FL 34786
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  $675,000

  • 4 Beds
  • 3 Baths
  • 2,830 Sq Ft

  13413 Zori Ln, Windermere, FL 34786

  Welcome to this Charming and stunning home located in a quiet Windermere neighborhood where the Lake Front homes with valuesexceeding millions of dollars. This single story home contain 4-bedroom, 3 full bathroom, 3 car garage, screened lanai and fenced back yard. Formal dining room & living room/office combined, 12' high ceiling, open breakfast nook, kitchen, spacious large family room,

  Annie Kwan ORLANDO SUNSHINE REALTY

  13413 Zori Ln, Windermere, FL 34786
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  /98

  $1,989,999

  • 3 Beds
  • 3.5 Baths
  • 3,240 Sq Ft

  13137 Lake Butler Blvd, Windermere, FL 34786

  Welcome to your very own slice of Windermere paradise—where luxury meets laid-back country living and yes, HORSES are welcome! Nestled on over an ACRE with NO HOA or DEED RESTRICTIONS, this stunning 3-bedroom, 3.5-bath home is perfect for anyone craving space, style, and a little bit of saddle time. Step through the oversized double wood doors and you feel the openness with gable ceiling

  Tricia Davis KELLER WILLIAMS REALTY SMART

  13137 Lake Butler Blvd, Windermere, FL 34786
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  $559,000

  • Land
  • 2.62 Acres
  • $213,359 per Acre

  1661 Roberts Landing Rd, Windermere, FL 34786

  Windermere Lot 2.62 acres and 1 acre buildable for an incredible luxury designer estate with partial water views of Lake Olivia and a stream. NO HOA REQUIRED! Bring your builder and no time restrictions to build on the lot. When you see this land and the particular lot, you will admire the beauty and nature. Gorgeous conservation views and spacious areas between the homes in the community.

  Lana Watts CHARLES RUTENBERG REALTY ORLANDO

  1661 Roberts Landing Rd, Windermere, FL 34786
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  $2,499,000

  • 4 Beds
  • 5.5 Baths
  • 4,810 Sq Ft

  6102 S Hampshire Ct, Windermere, FL 34786

  PRICE REDUCED $150K This elegant single-story Rick Watson home, located at 6102 S Hampshire Court, Windermere, FL 34786, sits on a private Jack Nicklaus–designed golf course lot in the exclusive, 24-hour manned and gated community of Keene’s Pointe. Enjoy uninterrupted views of the 6th hole by day and Disney Fireworks at night from key living areas and the outdoor lanai. The home features 4

  Jessica Dessire Cueva PA CHARLES RUTENBERG REALTY ORLANDO

  6102 S Hampshire Ct, Windermere, FL 34786
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  $634,900 Open Sun 1PM - 4PM

  • 5 Beds
  • 3.5 Baths
  • 2,396 Sq Ft

  11578 Ashlin Park Blvd, Windermere, FL 34786

  Welcome to this stunning 5-bedroom, 3.5 bath single-family home located in the highly desirable Ashlin Park community of Windermere. Designed with both style and functionality in mind, this open-concept home features a spacious kitchen with quartz countertops, ample cabinetry, and a walk-in pantry, perfect for entertaining and everyday living. The fenced backyard offers low-maintenance synthetic

  Erika Garcia CENTURY 21 CARIOTI

  11578 Ashlin Park Blvd, Windermere, FL 34786
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  $837,500

  • 4 Beds
  • 2.5 Baths
  • 2,269 Sq Ft

  9237 Mcdavid Ct, Windermere, FL 34786

  Come see a truly exceptional single-family residence nestled in the highly regarded Roberts Landing enclave of Windermere. With 4 bedrooms and 21⁄2 bathrooms, this home offers all the space needed to comfortably fit a family looking to stretch out. Located on over an acre of land, this home sits on an elevated lot providing beautiful views of the neighborhood, and a glimpse of Lake Olivia from

  David Ruizcalderon GENESYS REALTY LLC

  9237 Mcdavid Ct, Windermere, FL 34786
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  $1,599,000

  • 5 Beds
  • 4.5 Baths
  • 3,868 Sq Ft

  11015 Hawkshead Ct, Windermere, FL 34786

  REDUCED - Dream home in Windermere! Nestled inside the gates of the luxurious community of Reserve at Lake Sound. Move-in ready home! Tile roof replaced in 2021. Heated area of 3868 sqft built with high quality material and finishing, tall ceilings and travertine floors in the common areas. The refurbishment, done 4 years ago, resulted in adding modern sophistication to the home. The double door

  Ahmed Elkomy CENTURY 21 CARIOTI

  11015 Hawkshead Ct, Windermere, FL 34786
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  $950,000

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

  3328 Wax Berry Ct, Windermere, FL 34786

  One or more photo(s) has been virtually staged. ** Price improvement of $25,000! ** A rare find in the heart of Downtown Windermere! This 4 bedroom, 4 full bath home with an in ground pool sits not only on 1 acre but also in a semi-private cul-de-sac with only 8 other homes. You are welcomed by the circular driveway plus rear side entry garage and additional parking pad perfect for an RV or boat.

  Ferris Kassar PREFERRED REAL ESTATE BROKERS

  3328 Wax Berry Ct, Windermere, FL 34786
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  $975,000 Open Sun 11AM - 2PM

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

  12530 Climbing Vine Ct, Windermere, FL 34786

  Tucked at the end of a quiet cul-de-sac in the sought after community of Windstone, this beautifully appointed Windermere residence offers a lifestyle centered on comfort, connection, and effortless everyday luxury. Designed with both relaxation and entertaining in mind, the home welcomes you with an open layout filled with natural light and refined finishes that elevate each space. The main

  Andy Neal THE AGENCY ORLANDO

  12530 Climbing Vine Ct, Windermere, FL 34786
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  $680,000

  • 4 Beds
  • 2.5 Baths
  • 2,947 Sq Ft

  13339 Roskin Ln, Windermere, FL 34786

  Welcome to an exceptional opportunity in one of Central Florida’s most sought-after areas. This ginormous 4 bedroom, 2.5 bath, two story home offers 2,947 square feet of versatile living space designed for comfort, entertaining, and everyday luxury. The layout is ideal, featuring a private den/office, a massive upstairs loft, and generously sized bedrooms throughout. The primary suite is a true

  Karla Price COLDWELL BANKER REALTY

  13339 Roskin Ln, Windermere, FL 34786
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  $950,000

  • Land
  • 1.55 Acres
  • $612,903 per Acre

  6331 Little Lake Sawyer Dr, Windermere, FL 34786

  LAST & ONLY remaining homesite in the neighborhood — a rare Windermere waterfront opportunity! Build your custom residence on this 1.55-acre cul-de-sac lot featuring waterfront living on Little Lake Sawyer, plus water access for the ultimate lake lifestyle. Tucked at the end of the street for maximum privacy, this property offers a true estate setting with room for an exceptional home design and

  Daniel Pavel WRA BUSINESS & REAL ESTATE

  6331 Little Lake Sawyer Dr, Windermere, FL 34786

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