Windermere, FL Homes for Sale with Parking

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  $360,000

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

  14368 Desert Haven St Unit 4106, Windermere, FL 34786

  Don't miss 14368 Desert Haven St, recently enhanced with a partial flooring replacement, providing an updated surface throughout. The kitchen is equipped with stainless steel appliances for functional meal preparation. This residence includes a primary bedroom with a spacious walk-in closet, and its connecting bathroom provides double sinks and a separate tub and shower, contributing to its

  Karen Albright OPENDOOR BROKERAGE LLC

  14368 Desert Haven St Unit 4106, Windermere, FL 34786
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  $1,999,900

  • 5 Beds
  • 4.5 Baths
  • 5,922 Sq Ft

  5421 Tildens Grove Blvd, Windermere, FL 34786

  Welcome to one of Windermere’s finest offerings — an impressive 5-bedroom, 4.5-bath estate spanning almost 6,000 sq ft on a premium 0.62-acre direct water-view lot in the exclusive 24-hour guard-gated community of Tildens Grove. This is a luxury build that combines sophistication with fun and accommodates an active lifestyle for family and entertaining: a custom private movie theater,

  Mike Derenthal DERENTHAL REALTY

  5421 Tildens Grove Blvd, Windermere, FL 34786
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  $587,990 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,714 Sq Ft

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

  Ashton Woods Builder

  5432 Winter Garden Vineland Rd Unit 37932782, Windermere, FL 34786
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  $629,000

  • 5 Beds
  • 3.5 Baths
  • 2,960 Sq Ft

  12936 Droxford Rd, Windermere, FL 34786

  Lakes of Windermere STUNNER! This Ashton Woods Kensington model comes with an amazing bonus room and much more! The well-established neighborhood is out of a Norman Rockwell painting, lined with trees, 15 minutes from Disney, and loaded with charm. All you will need are a couple of Adirondack chairs for the front patio and a glass of sweet tea to become part of this amazing neighborhood. The

  Leo Rico UNITED REAL ESTATE PREFERRED

  12936 Droxford Rd, Windermere, FL 34786
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  $5,000,000

  • 6 Beds
  • 9 Baths
  • 8,305 Sq Ft

  9721 Carillon Park Dr, Windermere, FL 34786

  Welcome to 9721 Carillon Park Dr, Windermere, FL 34786, a stunning estate inside the guard-gated community of Keene’s Pointe.This extraordinary residence offers 8,305 square feet of luxury living space with refined architectural details, elegant wood beams, and designer finishes throughout. MAIN FEATURES: • Five bedrooms plus DETACHED GUEST HOUSE and OFFICE— providing exceptional space and

  Dianna Desboyaux DOUGLAS ELLIMAN

  9721 Carillon Park Dr, Windermere, FL 34786
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  $1,130,000

  • 8 Beds
  • 5 Baths
  • 4,830 Sq Ft

  6152 Golden Dewdrop Trail, Windermere, FL 34786

  More pictures coming soon. Beautiful and spacious 8-bedroom, 5-bathroom corner home offering 4,830 sqft of living space. This well-designed property features a generous layout with plenty of room for comfortable living and entertaining. The fenced backyard provides a great outdoor space, perfect for relaxing or enjoying time outside. Located on a desirable corner lot, offering added space and

  Vitor Silva VESTI LLC

  6152 Golden Dewdrop Trail, Windermere, FL 34786
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  $3,400,000

  • 4 Beds
  • 4 Baths
  • 4,877 Sq Ft

  9731 Chestnut Ridge Dr, Windermere, FL 34786

  Nestled within the gates of the renowned Isleworth Golf & Country Club, this beautiful four-bedroom estate offers nearly 5,000 square feet and showcases an elegant transitional style. The main level welcomes you with gracious formal living and dining rooms, each crowned with sparkling chandeliers and framed by oversized windows that capture elevated views of the resort-style pool and spa below.

  Monica Lochmandy ISLEWORTH REALTY LLC

  9731 Chestnut Ridge Dr, Windermere, FL 34786
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  $3,200,000

  • 6 Beds
  • 6.5 Baths
  • 6,308 Sq Ft

  13448 Bellaria Cir, Windermere, FL 34786

  Buyer walked days before closing due to personal reasons! All inspections and milestones clean/clear!! - This exceptional Florida residence is perfectly sited on an acre within the exclusive guard-gated community of Bellaria. Thoughtfully designed to balance sophistication with comfort, the home welcomes you with an abundance of natural light streaming through broad front windows, highlighting

  Shawn Kennedy KENNEDY REALTY GROUP LLC

  13448 Bellaria Cir, Windermere, FL 34786
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  $3,699,888

  • 4 Beds
  • 5.5 Baths
  • 6,054 Sq Ft

  12812 Jacob Grace Ct, Windermere, FL 34786

  Experience Unmatched Lakeside Luxury in a Custom-Built MasterpieceDiscover the pinnacle of elegance and tranquility in this exquisite custom-built estate, ideally positioned on an expansive lot within an exclusive guard-gated community. With direct access to a crystal-clear spring-fed lake that permits private boat docks, this home offers a rare blend of relaxation, recreation, and refined

  Alireza Partovi EXP REALTY LLC

  12812 Jacob Grace Ct, Windermere, FL 34786
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  $1,250,000 Open Sat 1PM - 3PM

  • 4 Beds
  • 3 Baths
  • 3,349 Sq Ft

  2127 Lilypad Ln, Windermere, FL 34786

  Welcome to a rare opportunity in the highly sought-after Willows at Lake Rhea, where incredible design, extensive upgrades, and an elevated Windermere lifestyle come together on a private 1⁄2-acre cul-de-sac lot in one of Central Florida’s most desirable luxury communities. This exceptional 4-bedroom, 3-bath residence features a thoughtfully designed split floor plan with two dedicated home

  Angela Jaspon UNITED REAL ESTATE PREFERRED

  2127 Lilypad Ln, Windermere, FL 34786
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  $5,760,000

  • 4 Beds
  • 7 Baths
  • 7,872 Sq Ft

  12264 Montalcino Cir, Windermere, FL 34786

  Lakefront, Luxurious, home with Private Pool in Windermere. A True Paradise! Discover this rare gem in the heart of Windermere,located in the gated community of Casa Del Lago — a spectacular residence that combines sophistication, comfort, and stunning lake views. with over eight expertly designed rooms, this home was carefully customized by the builder down to the smallest detail — from

  Jennifer Olmeda WRA BUSINESS & REAL ESTATE

  12264 Montalcino Cir, Windermere, FL 34786
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  $1,900,000

  • 4 Beds
  • 4 Baths
  • 3,196 Sq Ft

  6110 Keenes Pointe Dr, Windermere, FL 34786

  Welcome to a truly exceptional custom home in Keene's Pointe, one of Windermere’s most sought-after guard-gated communities. Built by W. J. Sauerwine and set on a beautifully landscaped .43-acre homesite with mature oak trees, this residence offers a rare combination of privacy, thoughtful design, and extensive modern upgrades.This 4-bedroom plus office, 4-bath home features a highly

  Donna Calhoun KELLER WILLIAMS CLASSIC

  6110 Keenes Pointe Dr, Windermere, FL 34786
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  $1,895,000

  • 5 Beds
  • 6 Baths
  • 3,728 Sq Ft

  11051 Hawkshead Ct, Windermere, FL 34786

  Discover an exceptional expression of modern luxury in the heart of Windermere. Welcome to 11051 Hawkshead Court, gracefully positioned within the prestigious Reserve at Lake Butler Sound—an exclusive guard-gated enclave renowned for its elegance, privacy, and lakefront lifestyle. Set on an expansive half-acre homesite at the end of a cul-de-sac, this fully reimagined contemporary estate offers a

  Ken Pozek REAL BROKER, LLC

  11051 Hawkshead Ct, Windermere, FL 34786
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  $3,950,000

  • 6 Beds
  • 7 Baths
  • 5,709 Sq Ft

  12132 Montalcino Cir, Windermere, FL 34786

  Experience the essence of luxury lakefront living in this stunning contemporary Mediterranean estate, ideally positioned on Lake Burden within the exclusive gated community of Casa Del Lago in Windermere. This elegant two-story residence combines refined design, functionality, and breathtaking panoramic lake views throughout.The gourmet kitchen features custom dark cabinetry, quartz

  Caroline Perotti BELLA VIEW REALTY LLC

  12132 Montalcino Cir, Windermere, FL 34786
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  $749,888

  • 5 Beds
  • 3 Baths
  • 2,620 Sq Ft

  13842 Orange Crest Dr, Windermere, FL 34786

  PRICED UNDER APPRAISED VALUE! Nestled behind the gated enclave of Eden Isle in Summerport, this stunning five-bedroom, three-bath residence blends modern updates with generous living space. Newly renovated in 2024, the home showcases luxury vinyl plank flooring throughout, a reimagined kitchen, and fully upgraded downstairs bathrooms. Step inside to soaring ceilings and an abundance of natural

  Erica Sadelfeld THE REAL ESTATE COLLECTION LLC

  13842 Orange Crest Dr, Windermere, FL 34786
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  $7,595,000

  • 5 Beds
  • 6.5 Baths
  • 6,937 Sq Ft

  5074 Isleworth Country Club Dr, Windermere, FL 34786

  A masterfully reimagined golf-front estate, this residence offers an unparalleled standard of luxury within the acclaimed guard-gated community of Isleworth. Completely reimagined and expanded, the residence offers over 6,900 square feet of refined living space, including a 2,400+ square-foot second-story addition designed by acclaimed architect Mark Nasrallah. Situated on over half an acre, the

  Armaan Memarpouri MEMARPOURI REALTY LLC

  5074 Isleworth Country Club Dr, Windermere, FL 34786
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  $465,000

  • 3 Beds
  • 2.5 Baths
  • 1,974 Sq Ft

  12353 Via Derna Place, Windermere, FL 34786

  The house does not include furniture.Welcome to this beautifully maintained 3-bedroom, 3-bathroom townhouse, with furniture available for negotiation, located in the desirable Carrington at Windermere community. This residence provides a well-designed open-concept floor plan that seamlessly blends comfort and functionality, ideal for both everyday living and entertaining. The home features

  Tiago Ferreira AUTHENTIC REAL ESTATE TEAM

  12353 Via Derna Place, Windermere, FL 34786
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  $680,000

  • 5 Beds
  • 3.5 Baths
  • 2,976 Sq Ft

  6712 Thornhill Cir, Windermere, FL 34786

  With timeless curb appeal and a front porch built for slow mornings, this Windermere home blends classic charm with the upgrades that make everyday life easier. Step inside and the ceilings rise, sunlight floods through, and hardwood floors (2021) lead you through open living and dining spaces that flow seamlessly into a remodeled kitchen with quartz countertops, updated cabinetry, and dual

  Brad Young HOMEVEST REALTY

  6712 Thornhill Cir, Windermere, FL 34786
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  $2,899,000

  • 5 Beds
  • 4 Baths
  • 3,737 Sq Ft

  10203 Trout Rd, Orlando, FL 32836

  Discover this exquisite lakefront property nestled on over 1.9 acres with more than 100 feet of water frontage on LAKE TIBET and part of the Butler Chain of Lakes. This home offers breathtaking views and absolutely stunning sunsets. As you drive onto the winding paver circular driveway with lovely fountain and beautiful landscaping, you will notice the terracotta tile roof and the undeniable

  Darlene O'Hara HOMEVEST REALTY

  10203 Trout Rd, Orlando, FL 32836
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  $3,700,000

  • 5 Beds
  • 7 Baths
  • 7,153 Sq Ft

  6857 Valhalla Way, Windermere, FL 34786

  Perfection has an address along with comfortable Florida living. Located on the 17th fairway of Jack Nicklaus-designed Golden Bear Club's golf course, this stunning home offers 5 bedrooms with the master on the 1st floor, 5 full baths, 2 half baths, home theatre, game room, office, and 2nd floor gathering room overlooking a stunning balcony. Invest in quality in this Rick Watson built masterpiece

  Mely Carrero EMPIRE NETWORK REALTY

  6857 Valhalla Way, Windermere, FL 34786
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  $385,000

  • 3 Beds
  • 2.5 Baths
  • 1,480 Sq Ft

  12210 Langstaff Dr, Windermere, FL 34786

  WELL MAINTAINED TOWNHOME IN WINDERMERE! 3 BEDROOM 2.5 BATHROOMS! Located in the sought after Lake Reams Community only a minute drive to the backside of Disney! As you open the front door you are drawn to Upscale Interior, filled with Upgrades & a Warm Family Décor. The eating area overlooks an Enclosed Courtyard leading to a Detached 2 Car Garage with Rear Entry Alleyway that backs up to a

  Ernesto Cisneros ELITE REALTY ENTERPRISES LLC

  12210 Langstaff Dr, Windermere, FL 34786
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  $410,000

  • 3 Beds
  • 2.5 Baths
  • 1,569 Sq Ft

  7249 Shadeview Aly, Windermere, FL 34786

  This enchanting home located near all of Florida’s theme parks, necessities, and more can be yours today! What a stunning home located in a great neighborhood, feel safe in this community that also has a community pool and a playground! Minutes away from Disney, several shopping centers, spectacular schools, and more feel wonderful living close to everything one would need! Stepping into the

  Blanca Armada REMAX PREMIER PROPERTIES

  7249 Shadeview Aly, Windermere, FL 34786
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  $572,500

  • 3 Beds
  • 2 Baths
  • 1,721 Sq Ft

  9072 Woodbreeze Blvd, Windermere, FL 34786

  Welcome to 9072 Woodbreeze Blvd, a beautifully maintained and thoughtfully updated home nestled in the highly desirable Silver Woods community of Windermere. This charming single-story residence offers 3 bedrooms, 2 bathrooms, and 1,728 square feet of comfortable living space, perfectly blending classic character with modern improvements.Set on a spacious quarter-acre lot, the property

  Charles Kohlinger BHHS FLORIDA REALTY

  9072 Woodbreeze Blvd, Windermere, FL 34786
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  $2,175,000 New Construction

  • 4 Beds
  • 5 Baths
  • 3,136 Sq Ft

  436 E 7th Ave, Windermere, FL 34786

  Seller is Motivated and open to negotiate! Luxury new construction lakefront home in Windermere, newly completed. Situated on Lake Bessie, this modern custom residence delivers architectural elegance, premium finishes, and a prime location just steps from the Town Center. The home offers 3,136 sq ft of air-conditioned space, featuring 4 en-suite bedrooms, a dedicated office at the entry, 5 full

  DENILEY VALDES TALENT REALTY SOLUTIONS

  436 E 7th Ave, Windermere, FL 34786
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  $369,990

  • 3 Beds
  • 2.5 Baths
  • 1,512 Sq Ft

  14236 Oasis Cove Blvd, Windermere, FL 34786

  If watching Magic Kingdom fireworks from your own home sounds like a dream, this is where it becomes your reality. Welcome to Oasis Cove, a gated, resort-style community located just a few miles from Walt Disney World. This beautifully updated 3-bedroom, 2.5-bath residence stands out as one of the most upgraded and move-in ready homes in the community. As you walk in, you are welcomed by a

  Raquel Saunders WRA BUSINESS & REAL ESTATE

  14236 Oasis Cove Blvd, Windermere, FL 34786
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  $1,100,000

  • 6 Beds
  • 4 Baths
  • 4,176 Sq Ft

  8236 Procida Isle Ln, Windermere, FL 34786

  This house is the perfect blend of luxury, comfort and modern convenience. From the moment you arrive, you're welcomed by a charming brick paver front porch that leads into a light-filled foyer with a private office at the front of the home. Beautiful wood-look tile flooring flows seamlessly throughout the main level. The stunning gourmet kitchen features 42” cabinets, gas appliances, light

  Babi Hennemann WRA BUSINESS & REAL ESTATE

  8236 Procida Isle Ln, Windermere, FL 34786
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  $850,000

  • 4 Beds
  • 3.5 Baths
  • 3,315 Sq Ft

  8724 Peachtree Park Ct, Windermere, FL 34786

  Recent pricing adjustment creates an exceptional opportunity to own a thoughtfully designed home in one of Windermere’s most sought-after hidden gems. With bonus spaces including a loft, mudroom, screened outdoor patio that goes around the house and a well-appointed this residence offers both refined living and everyday practicality. Experience the magic of Windermere living at Peachtree Park, a

  Marcelo Machado LA ROSA REALTY LLC

  8724 Peachtree Park Ct, Windermere, FL 34786
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  $2,200,000

  • 8 Beds
  • 8.5 Baths
  • 4,735 Sq Ft

  11545 Brickyard Pond Ln, Windermere, FL 34786

  Luxury Lakefront Estate – Windermere, FL Discover a truly extraordinary lakefront residence located at one of Windermere's most prestigious addresses. Situated on a sprawling 0.75-acre lot, this property impresses with its grandeur, elegance, and impeccable attention to detail. With 8 spacious bedrooms, 9 full bathrooms, and 1 powder room, the home was designed to offer absolute comfort and a

  Jennifer Olmeda WRA BUSINESS & REAL ESTATE

  11545 Brickyard Pond Ln, Windermere, FL 34786
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  $585,000

  • 3 Beds
  • 2.5 Baths
  • 2,139 Sq Ft

  6442 Golden Dewdrop Trail, Windermere, FL 34786

  Come see this beautiful place. This immaculate home features include over 2,100 square feet of living space, a desirable Kitchen with 42" Cabinets and Granite, Stainless Steel Appliances, Beautiful Backsplash, engineered hardwood flooring on the first floor, vinyl on the second floor, ceramic tile in bathrooms and laundry, screened-in patio porch with a ceiling fan, an elegant courtyard, and much

  Yindy Reyes EMPIRE NETWORK REALTY

  6442 Golden Dewdrop Trail, Windermere, FL 34786
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  $2,500,000

  • 6 Beds
  • 4 Baths
  • 4,482 Sq Ft

  9648 Weatherstone Ct, Windermere, FL 34786

  Set within the private gates of Weatherstone on Lake Olivia, this stunning lakefront residence offers a rare opportunity to enjoy refined living along the peaceful shoreline of Lake Olivia in Windermere. Situated on an expansive lakefront homesite, an increasingly rare find in this area, the property provides exceptional space, privacy, and unobstructed water views. Boasting 6 bedrooms and 4 full

  Andy Neal THE AGENCY FL

  9648 Weatherstone Ct, Windermere, FL 34786
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  $3,699,000

  • 3 Beds
  • 5 Baths
  • 4,262 Sq Ft

  4812 Alexandra Garden Ct, Windermere, FL 34786

  Luxury villa living within the exclusive Gardens of Isleworth, part of the Isleworth Golf & Country Club. This exceptional Southpoint built residence boasts a captivating courtyard floor plan that provides breathtaking views from every corner of the home. The rear of the residence presents serene views of a picturesque pond and the tranquil Isleworth Gardens, while interior windows reveal a

  Rob Rahter STOCKWORTH REALTY GROUP

  4812 Alexandra Garden Ct, Windermere, FL 34786
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  $5,995,000 New Construction

  • 5 Beds
  • 6 Baths
  • 6,000 Sq Ft

  13377 Lake Butler Blvd, Winter Garden, FL 34787

  Pre-Construction. To be built. To be Built, Rendering provided by master custom home builder, David Konkol of Konkol Custom Homes. However, buyer can work with builder to build any design buyer prefers (pricing to adjust accordingly). The property is spectacular waterfront acreage with boat dock on boatable, skiable Lake Roper. Acreage is 12.4 +/- with some conservation. Zoned A-1 (agricultural

  Dawn Briggs BLUE MAGNOLIA REALTY LLC

  13377 Lake Butler Blvd, Winter Garden, FL 34787
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  $499,000

  • 3 Beds
  • 2.5 Baths
  • 1,876 Sq Ft

  8648 Powder Ridge Trail, Windermere, FL 34786

  LOCATION, LOCATION, LOCATION! Welcome to this stunning bungalow-style single-family home located in the highly sought-after Windermere Trails community—where lifestyle, convenience, and charm meet at your front door.Built by Meritage Homes (consistently ranked among the best builders in Florida), this residence features the desirable Angelou floor plan offering 3 bedrooms, 2.5 bathrooms, a

  Renan Serretiello NOVA REAL ESTATE SERVICES INC

  8648 Powder Ridge Trail, Windermere, FL 34786
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  $15,500,000

  • 10 Beds
  • 17 Baths
  • 13,425 Sq Ft

  12488 Park Ave, Windermere, FL 34786

  Commanding a rare 2.75-acre lakefront setting on the coveted Butler Chain of Lakes, this extraordinary Windermere estate is a true work of art. Recently completed after a meticulous, ground-up transformation, the residence showcases a level of craftsmanship, design integrity, and finish quality that is simply unrivaled in Central Florida. From the moment you arrive, the estate announces itself

  Julie Christensen ONE LUXURY INTERNATIONAL LLC

  12488 Park Ave, Windermere, FL 34786
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  $579,900

  • 4 Beds
  • 3 Baths
  • 2,229 Sq Ft

  6897 Northwich Dr, Windermere, FL 34786

  Welcome to the highly desirable Lakes of Windermere! Where comfort, convenience, and thoughtful updates come together in one of Central Florida’s most sought-after communities. This move-in ready 4-bedroom, 3-bathroom home offers a functional, open layout perfect for both everyday living and entertaining. Step inside to find upgraded flooring installed in 2023, creating a warm, modern feel

  Blake Blahut REALTY ONE GROUP INSPIRATION

  6897 Northwich Dr, Windermere, FL 34786
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  $2,299,000

  • 5 Beds
  • 4 Baths
  • 3,461 Sq Ft

  5067 Sawyer Cove Way, Windermere, FL 34786

  This custom estate in the exclusive, 20-home gated enclave of Sawyer Sound is an extraordinary property curated under the meticulous supervision of an accomplished interior designer. Located directly across from Windermere Prep, the residence pairs architectural grandeur— natural MARBLE FLOORS and soaring wood-beamed ceilings with the warmth of an impeccably appointed and maintained home. Every

  Denise Crabbe REVEL REALTY LLC

  5067 Sawyer Cove Way, Windermere, FL 34786
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  $800,000

  • 4 Beds
  • 3.5 Baths
  • 3,124 Sq Ft

  5413 Walsh Pond Ct, Windermere, FL 34786

  Discover the charm of this water front, 4 bedroom 3.5 bath home located in the desirable Summerport community. This unique property is nestled in the cul de sac for complete privacy. Enjoy scenic water views while relaxing poolside on the spacious screen enclosed lanai, which is also great for entertaining. The interior features granite countertops, stainless appliances, 42" cabinets, built in

  Brenda Jebailey HAVEN PROPERTY GROUP LLC

  5413 Walsh Pond Ct, Windermere, FL 34786
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  /2

  $3,000,000 New Construction

  • 5 Beds
  • 5 Baths
  • 2,565 Sq Ft

  19 Main St, Windermere, FL 34786

  Under Construction. New Construction in Downtown Windermere Waterfront on the Butler Chain of Lakes!Experience modern lakefront living in the heart of the golf cart–friendly Town of Windermere. This brand-new construction 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

  Milena Fernandes GOLDEN GROUP REALTY LLC

  19 Main St, Windermere, FL 34786
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  $870,000

  • 5 Beds
  • 3.5 Baths
  • 3,724 Sq Ft

  8767 Iron Mountain Trail, Windermere, FL 34786

  The Melville floor plan features a functional and well-designed layout with formal living and dining areas, a spacious primary suite, an open-concept family room and a versatile flex space that can be used as a game room or adapted to suit a variety of lifestyle needs. Located in the desirable Windermere Trails community, the property offers convenient access to area lakes, daily essentials,

  Gilson Rodrigues KARDOSH REALTY

  8767 Iron Mountain Trail, Windermere, FL 34786
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  $749,999

  • 4 Beds
  • 3.5 Baths
  • 3,360 Sq Ft

  13609 Ancilla Blvd, Windermere, FL 34786

  One or more photo(s) has been virtually staged. Welcome to this stunning and spacious single-family home located in the heart of Windermere, offering breathtaking lake views from both the front and rear of the property. With 3,360 sqft heated living space, this beautifully maintained residence features a thoughtfully designed floor plan ideal for comfort and functionality. The first floor

  Fernanda Soares Santos de Oliveira WRA BUSINESS & REAL ESTATE

  13609 Ancilla Blvd, Windermere, FL 34786

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