Windermere, FL 2-Story Homes for Sale

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  $1,075,989 New Construction

  • 5 Beds
  • 3.5 Baths
  • 3,628 Sq Ft

  Ellington II Plan at Palms at Windermere, Windermere, FL 34786

  The Ellington II floor plan offers a modern, spacious two-story layout ideal for families and entertaining. It includes 4-5 bedrooms, 3 bathrooms, and expansive living areas. The main level features an open concept kitchen, dining, and great room, perfect for socializing. A private owner’s suite and an optional guest suite offer versatility. Upstairs, additional bedrooms, a loft, and a

  Dream Finders Homes Builder

  14207 Crest Palm Ave Unit 36503508, Windermere, FL 34786
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  $1,200,000

  • 7 Beds
  • 4 Baths
  • 3,928 Sq Ft

  12023 Gold Creek Trail, Windermere, FL 34786

  Welcome to this beautiful single-family residence, located on a premium corner lot spanning over 9,000 square feet in the prestigious and highly sought-after community in Windermere. This exceptional home combines comfort, and functionality, offering an unmatched lifestyle in one of Central Florida’s most desirable neighborhoods, the Windermere Trails.As you arrive, you’ll be captivated by

  Sabrina Guedes Williams KAZA REAL ESTATE LLC

  12023 Gold Creek Trail, Windermere, FL 34786
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  $2,300,000

  • 4 Beds
  • 4.5 Baths
  • 5,084 Sq Ft

  3413 Lilas Ct, Windermere, FL 34786

  Welcome to 3413 Lilas Court, a stunning residence located in the well renowned community of Chaine Du Lac. This exceptional home blends modern luxury with timeless elegance, offering a perfect combination of comfort and style. Upon arrival, you’re greeted by a beautifully landscaped front yard and an inviting exterior that sets the tone for the sophistication within. The grand entrance, complete

  Christopher Christensen ONE LUXURY INTERNATIONAL LLC

  3413 Lilas Ct, Windermere, FL 34786
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  $815,000

  • 5 Beds
  • 3 Baths
  • 3,211 Sq Ft

  4415 Blue Major Dr, Windermere, FL 34786

  This beautiful MOVE-IN-READY two-story home is located in the highly desired community of Summerport in Windermere! The Wow factor begins the moment the front door opens to a towering cathedral ceiling making for a dramatic and elegant entry into the main living area. The open floor plan creates a seamless flow throughout the home, whereby the family room opens to the kitchen and dinette space,

  Renata Vieira M2M REALTY

  4415 Blue Major Dr, Windermere, FL 34786
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  $18,500,000

  • 7 Beds
  • 8.5 Baths
  • 10,649 Sq Ft

  11900 Lake Butler Blvd, Windermere, FL 34786

  Presenting Sunset Isle: an iconic waterfront estate compound capturing timeless elegance on Windermere’s largest and most prestigious Lake Butler, offering captivating unobstructed views from its 700 feet of lake frontage, a private island with moat and drawbridge, sandy beaches, two story double residence guest house, and a majestic and stunning grand mansion with additional guest retreat, all

  Julie Bettosini STOCKWORTH REALTY GROUP

  11900 Lake Butler Blvd, Windermere, FL 34786
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  $599,000

  • 4 Beds
  • 2 Baths
  • 2,505 Sq Ft

  11520 Via Lucerna Cir, Windermere, FL 34786

  Beautifully Freshly painted Home in Windermere’s Belmere Village Welcome to this light and bright 4-bedroom, 2-bathroom home with a spacious second-floor loft, offering 2,505 square feet of meticulously maintained living space. Located in the gated community of Belmere Village, this home features fresh interior and exterior paint, creating a crisp, clean feel throughout. Step inside to an open

  Gretchen Carlson REAL BROKER, LLC

  11520 Via Lucerna Cir, Windermere, FL 34786
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  $6,800,000

  • 5 Beds
  • 5.5 Baths
  • 6,257 Sq Ft

  9259 Tibet Pointe Cir, Windermere, FL 34786

  Welcome to 9259 Tibet Pointe Circle, an extraordinary lakefront residence nestled within the highly sought after guard-gated community of Keene’s Pointe. Completely renovated in 2025, this exquisite home combines timeless elegance with modern luxury, offering breathtaking views and direct frontage on the pristine waters of Lake Tibet. This meticulously updated estate showcases high-end finishes

  Teresa Stewart SOUTHERN REALTY GROUP LLC

  9259 Tibet Pointe Cir, Windermere, FL 34786
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  $1,762,000

  • 7 Beds
  • 5 Baths
  • 4,914 Sq Ft

  11312 Shandon Park Way, Windermere, FL 34786

  Welcome to this stunning seven-bedroom, five-bath residence in the exclusive guard-gated community of Reserve at Belmere. This beautifully remodeled home offers 4,902 square feet of living space and a functional two-story layout featuring a spacious family room, formal living and dining areas, and a large kitchen with granite countertops, modern cabinetry and stainless steel appliances. The

  Daniel De Souza PREMIER SOTHEBYS INT'L REALTY

  11312 Shandon Park Way, Windermere, FL 34786
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  $4,925,000

  • 7 Beds
  • 8 Baths
  • 8,931 Sq Ft

  9575 Westover Roberts Rd, Windermere, FL 34786

  Discover “Bella Olivia”: a grand mediterranean estate perched high above Lake Olivia showcasing sweeping lake views, private gates, and an expansive luxury residence spanning over 8,900 square feet of living space across 7 bedrooms, including two primary suites, two guest apartments, garage space for 6 cars, an enormous screened enclosure with resort-style pool and spa, over 5.4 acres and no HOA.

  Rob Rahter STOCKWORTH REALTY GROUP

  9575 Westover Roberts Rd, Windermere, FL 34786
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  $2,700,000

  • 8 Beds
  • 5.5 Baths
  • 5,607 Sq Ft

  3103 Seigneury Dr, Windermere, FL 34786

  Stunning 8BR/5BA Renovated Estate in Exclusive Windermere CommunityBeautifully updated 7-bedroom, 5-bathroom home located in one of Windermere’s most exclusive neighborhoods, known for its quiet setting and top-rated schools. This spacious residence offers extensive renovations completed by the current owner, including four new A/C units, all new interior and exterior lighting, and updated

  Arletis Delram NEW SOLUTIONS REALTY INC

  3103 Seigneury Dr, Windermere, FL 34786
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  $539,990 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,699 Sq Ft

  Cawood Plan at Lake Cawood Cove - Townhomes, Windermere, FL 34786

  Ashton Woods Builder

  5432 Winter Garden Vineland Rd Unit 37932780, Windermere, FL 34786
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  /55

  $637,000

  • 4 Beds
  • 3.5 Baths
  • 3,078 Sq Ft

  13826 Eden Isle Blvd, Windermere, FL 34786

  Step into the pinnacle of comfort and ease in this gated community of Eden Isle, nestled in the picturesque town of Windermere. This stunning 4-bedroom single-family home exemplifies refined living and thoughtful design at every turn. Upon entry, be greeted by the dedicated home office, seamlessly merging work and lifestyle needs for modern living. With its high ceilings, the family room exudes

  XieChan Xiao BLUE CHIP INTERNATIONAL REALTY LLC

  13826 Eden Isle Blvd, Windermere, FL 34786
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  /55

  $1,045,000

  • 4 Beds
  • 3.5 Baths
  • 3,248 Sq Ft

  11162 Ledgement Ln, Windermere, FL 34786

  NEW TILE ROOF INSTALLED BEFORE CLOSING! Welcome to Glenmuir—one of Windermere’s most sought-after gated communities. This 4 bedroom, 3 full bath, plus 2 half bath home includes a dedicated office and an upstairs bonus room within a primarily single-story layout—a thoughtful blend of functionality and comfort.Double doors open to a bright foyer with immediate views of the custom 2021

  Deb Schroeder INFINITY REALTY GROUP LLC

  11162 Ledgement Ln, Windermere, FL 34786
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  $4,900,000

  • 5 Beds
  • 4.5 Baths
  • 5,548 Sq Ft

  5036 Latrobe Dr, Windermere, FL 34786

  Within the gates of the renowned Isleworth Golf & Country Club, this beautiful lakefront estate captures the essence of timeless luxury and gracious living. Poised on the shores of Lake Bessie, the 5,548 square-foot residence unfolds across two levels, designed to frame sweeping water views and create effortless spaces for both grand entertaining and quiet retreat. The upper level greets guests

  Monica Lochmandy ISLEWORTH REALTY LLC

  5036 Latrobe Dr, Windermere, FL 34786
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  $2,825,000

  • 5 Beds
  • 6.5 Baths
  • 6,105 Sq Ft

  11209 Macaw Ct, Windermere, FL 34786

  A Masterpiece on the 4th Hole – Keene’s Pointe Luxury Living Perfectly poised on a premium golf-front lot in the gorgeous, guard-gated community of Keene’s Pointe, this custom-built residence by Unnerstall blends refined craftsmanship with thoughtful design and breathtaking views of the Golden Bear Club’s 4th hole and tranquil water features. Boasting over 6,100 square feet of impeccably designed

  Jay Martin CORCORAN PREMIER REALTY

  11209 Macaw Ct, Windermere, FL 34786
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  $375,000

  • 3 Beds
  • 2.5 Baths
  • 1,786 Sq Ft

  14025 Oasis Springs Ln Unit 901, Windermere, FL 34786

  ***3D Tour on Virtual Tour Link 1*** This immaculately kept, gated end unit townhome boasts 3 bedrooms and 2.5 bathrooms. Step inside to discover a spacious layout seamlessly connecting the kitchen to the family room. The kitchen shines with stainless steel appliances, elegant wood cabinetry, and a convenient breakfast bar. Upstairs, the master suite awaits with a walk-in closet, double vanity,

  Jorge Martinez, Jr KELLER WILLIAMS CLASSIC

  14025 Oasis Springs Ln Unit 901, Windermere, FL 34786
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  $410,000 Open Sat 11AM - 2PM

  • 3 Beds
  • 2.5 Baths
  • 1,588 Sq Ft

  11818 Water Run Aly, Windermere, FL 34786

  SELLER OFFERS up to $3,000 toward buyer's closing costs. NEW exterior paint completed by HOA. NEW INTERIOR PAINT and NEW REFRIGERATOR, DISHWASHER AND MICROWAVE - all ready to go. Beautiful and fully decorated 3-bedroom, 3-bathroom home with elegant finishes and many upgrades throughout. This property offers a private patio and a two-car garage, providing comfort and style in the desirable Ashley

  Nelia Perez Urdaneta LA ROSA REALTY LLC

  11818 Water Run Aly, Windermere, FL 34786
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  $875,000

  • 4 Beds
  • 3 Baths
  • 3,040 Sq Ft

  1803 Glenbay Ct, Windermere, FL 34786

  Welcome to The Reserve at Belmere. Experience refined living in this exclusive guard-gated enclave, where sophistication meets comfort. Perfectly positioned on a premium corner lot, this elegant 4-bedroom, 3-bath home showcases a seamless blend of timeless design and modern luxury. The newly remodeled chef’s kitchen features top-of-the-line finishes and craftsmanship, opening to spacious living

  Melissa Tyrcha LAKESIDE REALTY WINDERMERE INC

  1803 Glenbay Ct, Windermere, FL 34786
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  $5,499,999 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, complete with your own social membership to Isleworth Golf & Country Club. 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

  Peyton Lewis PREMIER SOTHEBYS INT'L REALTY

  1003 Down Reserve Ct, Windermere, FL 34786
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  $1,979,000

  • 4 Beds
  • 4 Baths
  • 4,156 Sq Ft

  6047 Blakeford Dr, Windermere, FL 34786

  Stunning Golf-Front Luxury in Keene’s Pointe! Welcome to 6047 Blakeford Drive—an impeccably remodeled 4-bedroom, 4-bath residence offering 4,156 sq. ft. of A/C living space and 6,230 sq. ft. under roof. Perfectly situated along the renowned Jack Nicklaus Signature Golf Course, this home blends timeless elegance with modern comfort in one of Windermere’s most sought-after communities. Step inside

  Jay Martin CORCORAN PREMIER REALTY

  6047 Blakeford Dr, Windermere, FL 34786
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  $649,000

  • 3 Beds
  • 2.5 Baths
  • 2,463 Sq Ft

  12815 Westside Village Loop, Windermere, FL 34786

  come take look this newly build energy efficient home by Meritage , spacious 3 bedroom 2.5 bath house with office and the den 3 car garage beautiful tile roof with charming front porch for you to have morning coffee , once step in , the private office on your right , and walk in you will see the beautiful kitchen with beautiful counter top and dark wood cabinet ,and the dining room , you won't

  Eric Jia NUMBER 1 BROKER, LLC

  12815 Westside Village Loop, Windermere, FL 34786
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  $4,299,999

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

  5500 W Lake Butler Rd, Windermere, FL 34786

  Nestled on a 5-acre lot with 320 feet of lakefront and a private beach on the skiable Lake Davis. This Contemporary 8-bedroom, 6 full bath home wrapped with open porches spans nearly 7000 sq ft. Grand foyer with spiral staircase which features a magnificent glass wine cellar below. Modern, open concept with water views from nearly every room. Master bedroom is located on 1st level along with a

  Jack Keller JACK KELLER INC

  5500 W Lake Butler Rd, Windermere, FL 34786
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  $1,345,000

  • 5 Beds
  • 4 Baths
  • 3,358 Sq Ft

  11524 Claymont Cir, Windermere, FL 34786

  Completely updated in recent years, this 5-bedroom, 4-bathroom home offers 3,358 SqFt of luxury living in Keene’s Pointe, Windermere’s premier 24-hour guard-gated community and home of the Golden Bear Club. From the start, the oversized driveway, accommodating up to nine vehicles, and three-car garage set this home apart. Inside, the first floor features commercial-grade porcelain tile flooring

  Immu Korvenmaa ALIGN REAL ESTATE LLC

  11524 Claymont Cir, Windermere, FL 34786
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  $509,990 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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  $1,114,990 New Construction

  • 5 Beds
  • 3.5 Baths
  • 3,550 Sq Ft

  14261 Crest Palm Ave, Windermere, FL 34786

  The Ellington II floor plan offers a modern, spacious two-story layout ideal for families and entertaining. It includes 4-5 bedrooms, 3 bathrooms, and expansive living areas. The main level features an open concept kitchen, dining, and great room, perfect for socializing. A private owner’s suite and an optional guest suite offer versatility. Upstairs, additional bedrooms, a loft, and a

  Dream Finders Homes Builder

  14261 Crest Palm Ave, Windermere, FL 34786
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  $399,000

  • 3 Beds
  • 2.5 Baths
  • 1,670 Sq Ft

  7777 Moser Ave, Windermere, FL 34786

  This upscale, meticulously maintained end-unit townhome, formerly a model home, offers exceptional curb appeal, abundant green space, and a welcoming front porch. Featuring three bedrooms, 2.5 bathrooms, and a two-car garage, this move-in-ready residence combines thoughtful design with modern upgrades throughout. Inside, the spacious eat-in kitchen is a chef’s delight with granite countertops,

  Rebekah Beumel CREEGAN GROUP

  7777 Moser Ave, Windermere, FL 34786
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  $2,999,999

  • 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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  $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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  /22

  $640,000

  • 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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  $899,000

  • 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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  $330,000

  • 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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  $14,800,000

  • 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

  $900,000

  • 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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  /90

  $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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  $1,080,000

  • 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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  /51

  $985,000

  • 4 Beds
  • 3.5 Baths
  • 3,766 Sq Ft

  11507 Center Lake Dr, Windermere, FL 34786

  2025 PARADE OF HOMES GRAND AWARD WINNING BUILDER | 2017 PARADE OF HOMES WINNER |CUSTOM CRAFTSMAN BUILT HOME | HIGH QUALITY | PRIME LOCATION | PUTTING GREEN | FENCED IN YARD | SCREENED IN LANAI | POND VIEW Discover luxury and craftsmanship in this remarkable 2017 Parade of Homes Winner, built by the renowned Westmont Custom Homes. this 4-bedroom, 3.5-bathroom masterpiece spans 3,766 sqft.

  Kristy Cook EXP REALTY LLC

  11507 Center Lake Dr, Windermere, FL 34786

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