Windermere, FL Homes for Sale with Pool

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  $644,900

  • 4 Beds
  • 2.5 Baths
  • 2,683 Sq Ft

  12830 Cragside Ln, Windermere, FL 34786

  Virtually Staged. Welcome to this beautifully maintained 2,683-square-foot home located in the highly desirable Lakes of Windermere community! Offering the perfect blend of comfort, functionality, and Florida living, this spacious residence features an open-concept floor plan designed for both everyday living and entertaining. Thoughtfully updated for peace of mind, the home features a roof

  Mora Perez NONA LEGACY POWERED BY LA ROSA

  12830 Cragside Ln, 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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  /48

  $409,975

  $10K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,840 Sq Ft

  8218 Mystic View Way Unit 2801, Windermere, FL 34786

  NEW PRICE ADJUSTMENT! Welcome home to GATED OASIS COVE COMMUNITY offering resort style living! END UNIT Condo, impeccable condition, features 3 BR, 2.5 Baths and NEW A/C, minutes from Disney, you'll enjoy FIREWORKS every night! This home is MOVE-IN READY with NEW A/C, high end upgrades including Luxury Vinyl Floors, Plantation Shutters, Upgraded Lighting, elevated ceilings, and lots of natural

  Deb Obert WEICHERT REALTORS HALLMARK PRO

  8218 Mystic View Way Unit 2801, Windermere, FL 34786
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  /10

  $899,999

  • 3 Beds
  • 2 Baths
  • 2,258 Sq Ft

  2630 Stanton Hall Ct, Windermere, FL 34786

  Incredible Opportunity to own a pool home with a huge lot in a fantastic neighborhood * Good Floorplan * Close to Everything * Home has 7 Rooms * Separate Office * Formal Living Room * 3 Bedrooms * Breakfast Nook with Open Kitchen * Formal Dining Room * Family or Great Room * Pool Bath * Vaulted Ceilings * Inside Laundry * Screened & Covered Pool with Large Deck * Formal Dining Room * Large

  Darrell Nunnelley VINTAGE REALTY GROUP LLC

  2630 Stanton Hall Ct, Windermere, FL 34786
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  $695,000

  • 5 Beds
  • 4.5 Baths
  • 2,963 Sq Ft

  7236 Penkridge Ln, Windermere, FL 34786

  Gorgeous former model home situated on an oversized corner lot with a beautiful private swimming pool! Designed for comfortable living and entertaining, this spacious home offers an exceptional layout and a highly desirable location near Walt Disney World, shopping, dining, and everyday conveniences. Fresh interior and exterior paint gives the home a clean, refreshed feel.The first floor

  Amine Berrada ATLAS BLUE REALTY INC

  7236 Penkridge Ln, Windermere, FL 34786
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  $745,000

  • 5 Beds
  • 4 Baths
  • 2,989 Sq Ft

  8931 Lookout Pointe Dr, Windermere, FL 34786

  Investor opportunity in the sought after Windermere Trails community! This tenant-occupied home offers immediate rentalincome in a high-demand location just minutes from Disney World (Magic Kingdom, Hollywood Studios, Animal Kingdom,Epcot Center and Disney Springs), Winter Garden Historic District, Doctor Philips Restaurant hub, Hamlin Town Center,Horizon West, top-rated schools,

  Lilly Vazquez SPECIALIZED PROPERTY MANAGEMENT

  8931 Lookout Pointe Dr, Windermere, FL 34786
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  $3,300,000

  $500K PRICE DROP

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

  11539 Lake Butler Blvd, Windermere, FL 34786

  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 sprawling acre-plus level lot, this residence redefines your Florida lifestyle with elegance and comfort.Step inside to discover more than 5,000 heated square feet filled with spacious rooms adorned with

  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, Lake Access & an Exceptional Seller Incentive: Up to $36,000 Toward a Rate Buy-Down or Buyer Closing Costs.A rare opportunity in one of Windermere’s most established guard-gated communities, this private estate offers the space, flexibility, and lifestyle

  David Dorman CENTURY 21 CARIOTI

  2068 Roberts Point Dr, Windermere, FL 34786
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  $1,995,000

  • 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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  /47

  $624,994

  $55K PRICE DROP

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

  13013 Overstreet Rd, Windermere, FL 34786

  Welcome to one of the best opportunities in Windermere's highly sought-after Lakes of Windermere community! This beautifully maintained 4-bedroom, 2.5-bath home offers the perfect combination of comfort, convenience, and the Florida lifestyle buyers are searching for.Step inside to discover a thoughtfully designed floor plan featuring spacious living areas, abundant natural light, and stylish

  Omar Andreasen EXP REALTY LLC

  13013 Overstreet Rd, Windermere, FL 34786
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  /29

  $9,750,000

  $5M PRICE DROP

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

  4226 Downeast Ln, Windermere, FL 34786

  DRAMATIC PRICE IMPROVEMENT on this exceptional 5+ acre LAKE DOWN development opportunity, offering 300 feet of pristine shoreline on the coveted BUTLER CHAIN of Lakes and positioned on the best side of Windermere with unmatched convenience to SR-408 and downtown Orlando. This rare parcel, zoned R-CE, allows for the creation of up to three luxury lakefront homes or a single premier estate

  Thad Czapka COLDWELL BANKER REALTY

  4226 Downeast Ln, Windermere, FL 34786
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  $1,100,000

  $130K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 3,478 Sq Ft

  2512 Tryon Place, Windermere, FL 34786

  Welcome to a rare opportunity in the highly sought-after The Manors at Butler Bay, in the heart of Windermere. This custom-built home is situated on nearly three-quarters of an acre and a corner lot. This impressive single-story residence offers 3,478 square feet of thoughtfully designed living space with 4 bedrooms, 3 full bathrooms, a side-entry 2-car garage, an extended driveway, and a

  Jamie Stolinas Crame CENTURY 21 CARIOTI

  2512 Tryon Place, Windermere, FL 34786
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  /28

  $12,999,999

  New Construction $550K PRICE DROP

  • 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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  $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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  $1,825,000

  $100K PRICE DROP

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

  6560 Lake Burden View Dr, Windermere, FL 34786

  Experience refined, single-level living in this exceptional custom home located within Keene’s Pointe, Windermere’s premier guard-gated golf and lakefront community. Designed with both privacy and comfort in mind, this beautifully appointed residence offers 4 bedrooms, 4 full baths, a private office, and a resort-style pool and spa. At the front of the home, the dedicated office enjoys tranquil

  Rob Rahter STOCKWORTH REALTY GROUP

  6560 Lake Burden View Dr, Windermere, FL 34786
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  /19

  $299,500

  • 2 Beds
  • 2 Baths
  • 1,161 Sq Ft

  8180 Boat Hook Loop Unit 109, Windermere, FL 34786

  Discover comfort and convenience in this well-appointed first-floor condo located in the heart of Windermere. Unit 109 offers a functional split-bedroom layout with inviting living spaces, generous natural light, and easy ground-level access. The kitchen opens seamlessly to the main living area, creating a welcoming flow that works equally well for everyday living or entertaining guests.The

  Reinaldo Roman ROMAN'S PRO REALTY LLC

  8180 Boat Hook Loop Unit 109, Windermere, FL 34786
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  /39

  $649,500

  • 5 Beds
  • 3.5 Baths
  • 2,626 Sq Ft

  11773 Bella Milano Ct, Windermere, FL 34786

  Virtually Staged. Welcome home to 11773 Bella Milano Ct — a 5-bedroom, 3.5-bath residence on a quiet cul-de-sac in the sought-after gated community of Belmere Village. Enjoy rare privacy with a wooded conservation view at the rear, bordering a park with no through-access, and a lot size just under a quarter acre. Inside, engineered hardwood and tile flooring flow through the main living areas

  BILL STARKEY KELLER WILLIAMS ADVANTAGE 2 REALTY

  11773 Bella Milano Ct, Windermere, FL 34786
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  $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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  /57

  $3,900,000

  $200K PRICE DROP

  • 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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  /58

  $30,000,000

  • 7 Beds
  • 14 Baths
  • 51,000 Sq Ft

  9508 Windy Ridge Rd, Windermere, FL 34786

  Showcasing Central Florida’s most iconic lakefront estate: an 18-acre compound with 614 feet of pristine frontage on Lake Down on The Butler Chain of Lakes. The Windy Ridge Estate is comprised of multiple buildings spanning 51,000 square feet of space including an expansive 20,333 square-foot Georgian-style Plantation mansion that is a showplace residence with generous luxurious spaces, classic

  Rob Rahter STOCKWORTH REALTY GROUP

  9508 Windy Ridge Rd, Windermere, FL 34786
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  $2,349,000

  $51K 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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  /58

  $930,000

  $20K PRICE DROP

  • 5 Beds
  • 4.5 Baths
  • 4,043 Sq Ft

  12929 Westside Village Loop, Windermere, FL 34786

  Virtually Staged. Enjoy the best of Central Florida living in a highly sought-after neighborhood, just minutes from local schools, shopping, great restaurants, and magic of Disney. This 5-bedroom, 4.5-bathroom pool home is clean, well-maintained, and ready for move-in, featuring a freshly painted interior along with a newly painted exterior stucco, patio, and doors.THE FIRST FLOOR Walking in

  Steven Koleno BEYCOME OF FLORIDA LLC

  12929 Westside Village Loop, Windermere, FL 34786
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  /74

  $1,075,000

  • 5 Beds
  • 4 Baths
  • 4,332 Sq Ft

  8316 Lookout Pointe Dr, Windermere, FL 34786

  Fully Furnished- Located in the highly desirable Windermere Trails community, this impressive residence offers 5 bedrooms, 4 full bathrooms, a media room, loft, gym, and game room, providing plenty of space for both everyday living and entertaining. The home features elegant iron stair railings, formal living and dining areas, and an open-concept layout designed for comfort and functionality. The

  Gian Balsamo LA ROSA REALTY KISSIMMEE

  8316 Lookout Pointe 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 moment

  Isis Sarcos EXP REALTY LLC

  5070 Down Point Ln, Windermere, FL 34786
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  $900,000

  $75K PRICE DROP

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

  3328 Wax Berry Ct, Windermere, FL 34786

  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 1984 and renovated in 2022, this single-story home offers an open, split floor plan that seamlessly integrates luxury

  Ferris Kassar PREFERRED REAL ESTATE BROKERS

  3328 Wax Berry Ct, Windermere, FL 34786
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  /95

  $1,090,000

  • 4 Beds
  • 3 Baths
  • 2,842 Sq Ft

  1407 Hempel Ave, Windermere, FL 34786

  Welcome to this incredible investment opportunity located in one of the most desirable areas in Central Florida. This beautiful property offers the perfect combination of space, privacy, freedom, and location. Featuring 4 spacious bedrooms and 3 full bathrooms, this home sits on more than half an acre of land, giving you and your family the opportunity to truly enjoy comfort and outdoor

  Lina Abi Hanna De El Bonne MY REALTY GROUP, LLC.

  1407 Hempel Ave, Windermere, FL 34786
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  /27

  $4,190,000

  $279K PRICE DROP

  • 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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  /95

  $1,500,000

  • 5 Beds
  • 4 Baths
  • 3,656 Sq Ft

  17526 Black Rail St, Windermere, FL 34786

  An exceptional residence where refined design and effortless living converge. Meticulously remodeled throughout, the home welcomes you with bespoke modern woodwork gracing the foyer, living room, bedrooms, and loft — a testament to artisan-level craftsmanship rarely found at any price point. The loft has been reimagined as a private cinema, complete with a high-resolution projector, integrated

  Fernando Zucato CHARLES RUTENBERG REALTY ORLANDO

  17526 Black Rail St, Windermere, FL 34786
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  /65

  $1,399,000

  $100K PRICE DROP

  • 4 Beds
  • 4 Baths
  • 4,052 Sq Ft

  9119 Balmoral Mews Square, Windermere, FL 34786

  Virtually Staged. Welcome to an exceptional opportunity in the exclusive gated enclave of Balmoral, home to just 32 distinctive custom residences, where privacy, timeless elegance, and the coveted Windermere lifestyle come together seamlessly. Situated on over half an acre, this beautifully landscaped property offers a serene and private retreat surrounded by mature greenery, lush tropical

  Seana Abdelmajid LA ROSA REALTY BEACHES LLC

  9119 Balmoral Mews Square, Windermere, FL 34786

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