Homes for Sale in Windermere, FL with 5-Bedrooms

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  $2,500,000 New Construction

  • 5 Beds
  • 4 Baths
  • 5,516 Sq Ft

  6606 Sawyer Shores Ln, Horizon West, FL 34786

  One or more photo(s) has been virtually staged. Pre-Construction. To be built. One or more photo(s) has been virtually staged. UNIQUE CANAL-FRONT PROPERTY ON LAKE SAWYER | BUILD-READY | NO HOA | WINDERMERE An extraordinary opportunity awaits on the shores of Lake Sawyer, tucked along a picturesque canal, this beautiful parcel delivers the perfect blend of privacy and possibility. With no HOA fees

  Nick Khela PREMIUM PROPERTIES R.E. SERVICE

  6606 Sawyer Shores Ln, Horizon West, FL 34786
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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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  $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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  $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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  $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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  $850,000

  • 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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  $1,375,000

  • 5 Beds
  • 4.5 Baths
  • 3,686 Sq Ft

  11419 Camden Park Dr, Windermere, FL 34786

  Beautifully positioned on a private pond-front corner lot within the guard-gated community of Keene’s Pointe, this residence offers the perfect blend of space, comfort, and timeless design. Designed for both everyday living and effortless entertaining, the home features 5 bedrooms, 4.5 bathrooms, and a thoughtfully designed floor plan with formal living and dining rooms, a dedicated office, and

  Jay Martin CORCORAN PREMIER REALTY

  11419 Camden Park Dr, 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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  $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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  $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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  $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 Open Sat 11AM - 1PM

  • 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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  $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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  $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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  $2,950,000

  • 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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  $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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  $1,119,000

  • 5 Beds
  • 4 Baths
  • 3,804 Sq Ft

  6379 Swanson St, Windermere, FL 34786

  From the moment you arrive, this Mediterranean home in the highly sought after Enclave makes an impression. It offers a balance of grand design and everyday livability.Inside, the entryway features rich paneling and an open railed staircase that sets the tone. The open floor plan flows into a bright family room and gourmet kitchen designed for both daily living and entertaining. The oversized

  John Cunningham KELLER WILLIAMS CLASSIC

  6379 Swanson St, 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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