Windermere, FL Homes for Sale with Parking

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  $6,000,000

  • 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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  /100

  $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

  $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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  $779,900

  • 4 Beds
  • 3 Baths
  • 2,606 Sq Ft

  1430 Glenwick Dr, Windermere, FL 34786

  Beautifully updated 4-bed, 3-bath home in the Reserve at Belmere, a 24-hour guard-gated community in Windermere. Major upgrades include a new tile roof (2024), new energy-efficient windows (2025), and a new storm front door, and new plantation shutters with a lifetime warranty offering exceptional durability, style and long-term value, curb appeal, and long-term insurance benefits. The bright,

  Chloe Joseph PREMIUM REAL ESTATE SERVICES

  1430 Glenwick Dr, 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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  /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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  /68

  $7,400,000

  • 5 Beds
  • 8 Baths
  • 7,529 Sq Ft

  9349 Tibet Pointe Cir, Windermere, FL 34786

  Set along the pristine shores of Lake Tibet Butler, this exceptional estate within Keene's Pointe is a masterclass in timeless design, refined craftsmanship, and elevated lakefront living. Spanning over 7,500 square feet, every detail has been thoughtfully curated to balance grandeur with comfort. A dramatic foyer makes a lasting first impression, overlooking formal living and dining spaces

  Jay Martin CORCORAN PREMIER REALTY

  9349 Tibet Pointe Cir, 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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  /80

  $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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  /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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  $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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  /6

  $562,095 New Construction

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

  13411 Lemon Orchard Bend, Windermere, FL 34786

  This stylish two-story townhome features three spacious suites, including a second-floor primary suite and two additional bedrooms. The open-concept first floor offers a bright living area and a gourmet kitchen with 42” cabinets, quartz countertops, stainless steel appliances, and luxury vinyl plank flooring. Enjoy a private courtyard and detached two-car garage. Located in the heart of

  Ashton Woods Builder

  13411 Lemon Orchard Bend, Windermere, FL 34786
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  /30

  $930,000

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

  6752 Trellis Vine Loop, Windermere, FL 34786

  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 NEIGHBORS and NO FRONT NEIGHBORS, creating extraordinary flexibility for refined living, entertaining, and everyday

  Candice Collins COLDWELL BANKER REALTY

  6752 Trellis Vine Loop, Windermere, FL 34786
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  $664,994

  • 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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  /29

  $10,500,000

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

  4226 Downeast Ln, Windermere, FL 34786

  DRAMATIC PRICE IMPROVEMENT. Exceptional DEVELOPMENT OPPORTUNITY, currently R-CE zoning should allow for 3 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,

  Thad Czapka COLDWELL BANKER REALTY

  4226 Downeast Ln, Windermere, FL 34786
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  $13,540,000 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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  $769,995

  • 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 with walkability to town, and a bike ride to Windermere Elementary. 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

  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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  $1,890,000

  • 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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  $1,650,000

  • 5 Beds
  • 5 Baths
  • 4,329 Sq Ft

  7503 Lake Albert Dr, Windermere, FL 34786

  7503 Lake Albert Drive presents a beautifully renovated residence in the Lake Burden South community of Windermere. Completely renovated in 2023, the home showcases modern finishes, soaring ceilings, abundant natural light, and an open-concept layout designed for both everyday living and entertaining. Interior features include porcelain tile flooring, designer lighting, updated bathrooms, a

  Mariana Haddad LA ROSA REALTY LLC

  7503 Lake Albert Dr, 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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  $445,000

  • 4 Beds
  • 3.5 Baths
  • 1,905 Sq Ft

  7560 Bentonshire Ave, Windermere, FL 34786

  Welcome Home! Do not miss out on this Turnkey Corner Lot Townhome with 2 PRIMARY BEDROOMS. This desirable unit features 4 bedrooms, 3.5 bathrooms a rear-entry 2-car garage. The oversized kitchen is equipped with stainless steel appliances that are 5 years of age, Silestone countertops, 42-inch soft-close cabinets with under cabinet lighting and a double size pantry providing plenty of storage.

  Sharon Six SOLD BY SIX REALTY, LLC

  7560 Bentonshire Ave, 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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  $3,900,000

  • 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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  $625,000

  • 4 Beds
  • 3.5 Baths
  • 2,720 Sq Ft

  8632 Abbotsbury Dr, Windermere, FL 34786

  One or more photo(s) has been virtually staged. Welcome to this beautifully updated 4-bedroom, 3.5-bath home located in the highly desirable gated community of Lakes of Windermere. Featuring fresh interior paint and luxury vinyl flooring, this spacious residence offers a modern, clean, and move-in-ready feel with an ideal layout for both everyday living and entertaining.The remodeled first

  Priscila Policarpo Attuy de Albuqu WRA BUSINESS & REAL ESTATE

  8632 Abbotsbury 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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  $2,400,000

  • 4 Beds
  • 3 Baths
  • 2,865 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 offers approximately 2,865 square feet of living space and captures the essence of Windermere’s enduring lakefront lifestyle,

  Linda O'Grady PREMIER SOTHEBYS INT'L REALTY

  9620 Maywood Dr, Windermere, FL 34786
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  $1,450,000

  • 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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  $600,000

  • 4 Beds
  • 3 Baths
  • 2,419 Sq Ft

  14217 Bridgewater Crossings Blvd, Windermere, FL 34786

  Don't miss out on this 4 bedroom 3 bathrooms in the tranquil Summerport community in Windermere. The first floor consists of the Kitchen, dining, family room, living room, the Master bedroom and the 3 other bedrooms and the guest bathroom. The second floor consists of the large loft, closets and a full bathroom. Don’t miss your chance to experience exceptional living very close to Keenes Crossing

  Azim Manji WEICHERT REALTORS HALLMARK PRO

  14217 Bridgewater Crossings Blvd, Windermere, FL 34786
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  /53

  $1,189,000

  • 6 Beds
  • 4 Baths
  • 3,577 Sq Ft

  13932 Florigold Dr, Windermere, FL 34786

  One or more photo(s) has been virtually staged. Tucked within the gated enclave of Eden Isle in Windermere’s Summerport, this beautiful canal-front, three-car garage and pool home has an ideal layout for multigenerational living. It offers an abundance of amenities with the canal leading directly to skiable Lake Speer and a rare combination of privacy, flexibility and outdoor living, and features

  Courtney Bass PREMIER SOTHEBY'S INTL. REALTY

  13932 Florigold Dr, 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 custom-built residence by Rick Watson is located in the sought-after community of Keene’s Pointe, positioned on a private lot overlooking the Jack Nicklaus Golden Bear Club golf course. The home offers consistent views of the 6th hole, along with the added bonus of nightly Disney fireworks visible from multiple areas, including the living room, primary bedroom, kitchen, and outdoor living

  Jessica Dessire Cueva PA CHARLES RUTENBERG REALTY ORLANDO

  6102 S Hampshire Ct, 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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