Windermere, FL Homes for Sale with Pool

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  $4,950,000

  • 5 Beds
  • 7 Baths
  • 6,188 Sq Ft

  11618 Vinci Dr, Windermere, FL 34786

  Behind the gates of Keene's Pointe, on the pristine shores of Lake Burden, an extraordinary lakefront estate awaits where modern design, curated luxury, and a truly magical setting come together in perfect harmony! Vinci Drive is a custom-built, fully furnished, turnkey masterpiece offering over 6,000 square feet of refined living on a desirable 1.16 acre lakefront lot. From the moment you

  Jennifer Wemert WEMERT GROUP REALTY LLC

  11618 Vinci Dr, Windermere, FL 34786
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  $4,999,999 New Construction

  • 6 Beds
  • 8 Baths
  • 6,816 Sq Ft

  1003 Down Reserve Ct, Windermere, FL 34786

  Welcome to a rare modern estate in an intimate gated enclave. Imagine 6,816 square feet of fully furnished luxury with six bedrooms, six full baths and two half baths. Every detail of this custom-built masterpiece was designed for those who value privacy, prestige and perfection. Go inside to discover European white oak flooring, soaring ceilings and designer-curated finishes that define

  Peyton Lewis PREMIER SOTHEBYS INT'L REALTY

  1003 Down Reserve Ct, Windermere, FL 34786
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  $6,950,000

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

  9725 Chestnut Ridge Dr, Windermere, FL 34786

  Private showings are easily accommodated, including same-day requests. Newly renovated and fully turnkey, 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

  Dianna Desboyaux DOUGLAS ELLIMAN

  9725 Chestnut Ridge Dr, Windermere, FL 34786
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  $2,390,000

  • 5 Beds
  • 4 Baths
  • 4,287 Sq Ft

  6252 Blakeford Dr, Windermere, FL 34786

  Now it’s your turn to live on the 18th hole of the Golden Bear Club golf course in a fully updated custom home, located on one of the most desirable streets in Keene’s Pointe. This house with a timeless design inside and out, has five bedrooms (two down and three up), four full bathrooms, three car garage, and incredible outdoor living with renovated pool and brand new pool enclosure. Upstairs

  Shane Croft COLDWELL BANKER RESIDENTIAL RE

  6252 Blakeford Dr, Windermere, FL 34786
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  $4,150,000

  • 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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  $830,000

  • 6 Beds
  • 5.5 Baths
  • 3,698 Sq Ft

  4345 Saltmarsh Sparrow Dr, Windermere, FL 34786

  Welcome HOME to Summerport! This stunning fully indoor and outdoor repainted 6-bedroom, 5.5-bathroom residence is now listed for sale in the highly desirable Summerport neighborhood—zoned for top-rated A+ schools! Step inside and enjoy a thoughtfully designed split two-story floor plan with plenty of room for family and entertaining. The first floor features a versatile office/den with French

  Silvia Odebrecht ICON REALTY ASSOCIATES INC

  4345 Saltmarsh Sparrow Dr, Windermere, FL 34786
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  $565,000

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

  6718 Romney Ln, Windermere, FL 34786

  One or more photo(s) has been virtually staged. Well-maintained 4-bedroom, 2.5-bath home in the heart of Windermere featuring inviting curb appeal with a covered front porch and classic columns. The bright, open layout offers high ceilings, crown molding, and tile and wood-look flooring throughout the main living areas. The kitchen includes dark wood cabinetry, granite countertops, stainless

  Tyler Gibson LPT REALTY, LLC

  6718 Romney Ln, Windermere, FL 34786
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  $4,495,000

  • 5 Beds
  • 7 Baths
  • 5,895 Sq Ft

  6109 Orta Ct, Windermere, FL 34786

  Within the gates of the Waterstone community, this exceptional lakefront estate offers approximately 5,895 square feet of refined living space, seamlessly blending modern elegance with timeless sophistication. The thoughtfully designed floor plan features five bedrooms, five full bathrooms, and two half bathrooms, with the primary suite conveniently located on the main level.At the heart of

  Monica Lochmandy ISLEWORTH REALTY LLC

  6109 Orta Ct, Windermere, FL 34786
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  $2,750,000

  • 5 Beds
  • 4.5 Baths
  • 5,005 Sq Ft

  12923 Water Point Blvd, Windermere, FL 34786

  Welcome to 12923 Water Point Blvd., a stunning lakefront estate nestled in the exclusive, man-guard gated community of Waterford Pointe in Windermere. This impressive residence offers over 5,000 square feet of luxurious living space with 4 bedrooms in the main home, including a spacious primary suite conveniently located on the first floor. Designed for both relaxation and entertaining, the home

  Kevin Sullivan LAKESIDE REALTY WINDERMERE INC

  12923 Water Point Blvd, Windermere, FL 34786
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  $3,600,000

  • 5 Beds
  • 6.5 Baths
  • 5,501 Sq Ft

  5024 Sawyer Cove Way, Windermere, FL 34786

  Welcome to “The Sounding:” a captivating lakefront estate residence with inviting water views and a serene and peaceful setting offering the best of Florida living. Tucked inside this privately gated and intimate enclave of estate homes across the street from Windermere Prep, Sawyer Sound offers an escape from the ordinary and this showplace residence sets the standard for lakefront living. A

  Rob Rahter STOCKWORTH REALTY GROUP

  5024 Sawyer Cove Way, Windermere, FL 34786
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  $1,200,000

  • 5 Beds
  • 3 Baths
  • 2,918 Sq Ft

  3443 Wild Myrtle Ct, Windermere, FL 34786

  Welcome to 3443 Wild Myrtle Court, a beautifully renovated executive home nestled on a serene 1.2-acre cul-de-sac lot in the esteemed Lake Butler Estates of Windermere, Florida. This expansive 5-bedroom, 3-bathroom residence offers 2,918 square feet of thoughtfully designed living space, combining modern updates with timeless charm.The home boasts a formal living room featuring a

  Michael Julian JULIAN PROPERTIES, INC.

  3443 Wild Myrtle Ct, Windermere, FL 34786
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  $5,325,000

  • 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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  $1,600,000 Pre-Foreclosure

  • 5 Beds
  • 6 Baths
  • 6,375 Sq Ft

  11056 Clipper Ct, Windermere, FL 34786

  Professional Pictures Coming Soon * Huge 5 Bedroom 6 Bath Multi-Generational Pool Home Has 1 Full Suite on 1st Floor & 2 Spacious Suites on the 2nd Floor * Open Floorplan * The Marina Bay Community Includes a Waterfront Marina for your boat that is directly connected to Lake Down and the Butler Chain of Lakes * Oversized 4 Car Garage with Drive Through Doors on Front & Rear of the 3rd Bay * Over

  Darrell Nunnelley VINTAGE REALTY GROUP LLC

  11056 Clipper Ct, 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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  $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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  $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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  $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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  $415,000 Open Sat 1PM - 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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  $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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  $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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  $970,000

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

  6947 Cucamelon Ct, Windermere, FL 34786

  PRICE IMPROVEMENT — exceptional value in Windermere! Welcome home to your personal oasis — tucked within the prestigious Sanctuary at Lakes of Windermere, this move-in-ready retreat is designed for inspired living and effortless entertaining. From the moment you step inside, you’ll feel how the open, airy layout and thoughtful finishes create a haven you can’t wait to come home to. With five full

  Mahmoud Mango DALTON WADE INC

  6947 Cucamelon Ct, Windermere, FL 34786
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  $419,000

  • 3 Beds
  • 2.5 Baths
  • 1,583 Sq Ft

  12944 Garridan Ave, Windermere, FL 34786

  Welcome to this well-maintained 3-bedroom, 2.5-bath home offering 1,583 square feet of comfortable living space in the well established Wickham Park community. The home is in excellent condition and has been thoughtfully cared for, making it truly move-in ready. Enjoy low-maintenance living with an HOA that covers exterior maintenance for normal wear and tear, including roof, exterior painting,

  Fred Jackson 407 PROPERTIES

  12944 Garridan Ave, 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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  $1,975,000

  • 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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  $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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  $595,000

  • 4 Beds
  • 3.5 Baths
  • 2,628 Sq Ft

  8650 Abbotsbury Dr, Windermere, FL 34786

  Welcome to this beautifully maintained 4-bedroom, 3.5-bath residence located in the sought-after, gated Lakes of Windermere community. This two-story home offers peace of mind with a brand-new roof installed in 2025 and features a light-filled, open-concept layout designed for both everyday living and entertaining. The main level includes formal living and dining spaces, a generous family room, a

  Andy Neal THE AGENCY FL

  8650 Abbotsbury Dr, Windermere, FL 34786
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  $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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  $1,939,999

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

  13137 Lake Butler Blvd, Windermere, FL 34786

  Kitchen refresh...Quartz countertops, seamless oversized sink. A kitchen designed to gather, host, and impress. Welcome to a private Windermere estate where thoughtful design meets relaxed luxury—set on over an acre with no restrictions. This beautifully updated 3-bedroom, 3.5-bath home offers space, privacy, and versatility, all surrounded by natural beauty. Enter through oversized double wood

  Tricia Davis KELLER WILLIAMS REALTY SMART

  13137 Lake Butler Blvd, 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

  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 bedrooms, 5 bathrooms, a

  Jessica Dessire Cueva PA CHARLES RUTENBERG REALTY ORLANDO

  6102 S Hampshire Ct, Windermere, FL 34786
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  $634,900

  • 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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  $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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  $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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