Windermere, FL Homes

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  /57

  $679,900

  • 5 Beds
  • 3.5 Baths
  • 3,072 Sq Ft

  12654 Cragside Ln, Windermere, FL 34786

  Welcome to a truly rare opportunity in Windermere with full GARAGE APARTMENT, FULLY PAID solar panels, NEW ROOF 2023, top rated schools, access to the famous Chain of Lakes, a beautifully REMODELED interior. Located in one of the most lushly landscaped communities in Windermere and just minutes from Disney, shopping, and dining, this residence combines location, lifestyle, and value in a way

  Mariana Cezar Ovalle WRA BUSINESS & REAL ESTATE

  12654 Cragside Ln, Windermere, FL 34786
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  /2

  $1,158,517 Sold Aug 08, 2025

  • 4,443 Sq Ft
  • $261/SF
  • 0 Days On Market

  • 6 Beds
  • 4.5 Baths
  • Built 2025

  14360 Crest Palm Ave, Windermere, FL 34786

  One or more photo(s) has been virtually staged. Sample Images The Sweetwater Experience Living in the Sweetwater means embracing alifestyle where luxury meets practicality. Start your day in the spa-like owner's suite, where dual walk-in closets eliminate the morning rush.Enjoy coffee on the covered patio while the kids prepare for school in their own well-appointed spaces. Throughout the

  Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

  14360 Crest Palm Ave, Windermere, FL 34786
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  /60

  Est $670,255 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,015 Sq Ft

  7949 Jailene Dr, Windermere, FL 34786

  7949 Jailene Dr, Windermere, FL 34786
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  /38

  $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

  $1,975,000 Sold Aug 08, 2025

  • 4,190 Sq Ft
  • $471/SF
  • 3 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1999

  6138 Greatwater Dr, Windermere, FL 34786

  Nestled on the coveted Greatwater Drive in the luxurious Keene’s Pointe community, this stunning Stonebridge custom home offers the perfect blend of luxury, privacy, and timeless elegance. Situated on over half an acre, the home boasts breathtaking views of the 17th green of The Golden Bear Club, providing a serene and private retreat, yet it’s just minutes from all of Windermere's amenities .

  Jay Martin CORCORAN PREMIER REALTY

  6138 Greatwater Dr, Windermere, FL 34786
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  /28

  Est $2,072,000 Not Listed For Sale

  • 4 Beds
  • 7 Baths
  • 5,561 Sq Ft

  9950 6th St, Windermere, FL 34786

  9950 6th St, Windermere, FL 34786
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  /66

  $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 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 private courtyard

  Rob Rahter STOCKWORTH REALTY GROUP

  4812 Alexandra Garden Ct, Windermere, FL 34786
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  /2

  $325,000 Sold Aug 08, 2025

  • 1,512 Sq Ft
  • $215/SF
  • 36 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2012

  14231 Desert Haven St Unit GE, Windermere, FL 34786

  Experience the elegance of resort-style living in this beautifully appointed 3-bedroom, 3-bathroom home, ideally located in the prestigious Oasis Cove community—just minutes from the magic of Disney World.Owned by a discerning foreign national and used exclusively as a private vacation retreat, this impeccably maintained residence shows minimal wear and exudes pride of ownership throughout.

  Mercia Sousa ACCORD REAL ESTATE SERVICES

  14231 Desert Haven St Unit GE, Windermere, FL 34786
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  /41

  Est $448,808 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,912 Sq Ft

  13760 Calera Alley, Windermere, FL 34786

  13760 Calera Alley, 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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  /2

  $515,000 Sold Aug 07, 2025

  • 1,696 Sq Ft
  • $304/SF
  • 13 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2012

  12795 Bosworth Ave, Windermere, FL 34786

  UNFURNISHED - WELCOME TO BOSWORTH AVENUE! Located in the beautiful Wickham Park community in Windermere, Florida, this home offers 3 bedrooms, 2 baths, and 1,700 square feet of Florida dream living! This home has been newly renovated in 2021. Upgrades include luxurious vinyl plank flooring throughout the home, fresh paint, Silestone calacatta quartz countertops and backsplash in the kitchen,

  Michelle Dunkley RE/MAX PRIME PROPERTIES

  12795 Bosworth Ave, Windermere, FL 34786
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  /29

  Est $539,251 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,152 Sq Ft

  12273 Joshua Tree Trail, Windermere, FL 34786

  12273 Joshua Tree Trail, Windermere, FL 34786
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  /63

  $765,000

  • 4 Beds
  • 3.5 Baths
  • 3,414 Sq Ft

  11849 Cave Run Ave, Windermere, FL 34786

  Immaculate and light-filled 4-bedroom, 3.5-bath home with a huge bonus room and flex space, located in the desirable Windermere Trails community. Just one block from the elementary school and right across from a playground that feels almost private. This spacious two-story property features an open-concept kitchen with granite waterfall-edge countertops, stainless steel appliances, and views of

  Any Alves WRA BUSINESS & REAL ESTATE

  11849 Cave Run Ave, Windermere, FL 34786
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  /2

  $1,100,000 Sold Aug 07, 2025

  • 2,838 Sq Ft
  • $388/SF
  • 25 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1999

  2106 Ridgewind Way, Windermere, FL 34786

  If you love being close to all the incredible amenities Central Florida has to offer—but crave a peaceful retreat to call home—look no further than the Estates at Windermere, a hidden community just off the beaten path. Tucked behind the community gates, down a canopy of majestic oak-lined streets, you’ll find 2106 Ridgewind Way: a rare single-story gem offering 4 bedrooms and 3 baths.Set

  Hilary Hall COMPASS FLORIDA LLC

  2106 Ridgewind Way, Windermere, FL 34786
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  /33

  Est $1,340,004 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 3,493 Sq Ft

  1109 Estancia Woods Loop, Windermere, FL 34786

  1109 Estancia Woods Loop, Windermere, FL 34786
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  /30

  $3,200,000

  • 5 Beds
  • 5 Baths
  • 4,500 Sq Ft

  13161 Lake Butler Blvd, Windermere, FL 34786

  Extraordinary lake front opportunity in Windermere on 1.75 acres! PRIVATE GATES! NO HOA! SPECTACULAR LAKE VIEWS, PRIVACY, SPORTS COURT, AND GAZEBO ON LAKE ROPER - A WATER SKI FRIENDLY LAKE! A grand entryway leads you to magnificent two story ceilings and welcomes you into a separate living and family room. Beautiful 5-bedroom, 3/2-bathroom Mediterranean-style home with inlaid marble medallion

  Karolina Taylor EPIQUE REALTY, INC.

  13161 Lake Butler Blvd, Windermere, FL 34786
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  /2

  $590,000 Sold Aug 06, 2025

  • 2,432 Sq Ft
  • $243/SF
  • 26 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 2004

  5263 Beach River Rd, Windermere, FL 34786

  Welcome to this beautifully maintained 4-bedroom, 3-bath corner home in the highly sought-after Summerport community of Windermere! Roof 2022, AC 2023, Double Pane Windows 2017, Screened-In Deck 2018, Garage Opener 2023, PAID OFF Solar 2018. Boasting 2,432 sq ft of heated living space, this spacious residence features an open floor plan, a formal dining room, and a generous kitchen with ample

  Ariel Vargas EXP REALTY LLC

  5263 Beach River Rd, Windermere, FL 34786
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  /71

  Est $623,097 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,374 Sq Ft

  6769 Merrick Landing Blvd, Windermere, FL 34786

  6769 Merrick Landing Blvd, Windermere, FL 34786
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  /81

  $5,489,000

  • 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 FULLY FURNISHED (furniture included-with exception of a few items) , professionally designed 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

  Dianna Desboyaux EXP REALTY LLC

  9721 Carillon Park Dr, Windermere, FL 34786
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  /2

  $1,600,000 Sold Aug 06, 2025

  • 4,026 Sq Ft
  • $397/SF
  • 84 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 1986

  2926 Marquesas Ct Unit 1, Windermere, FL 34786

  Great opportunity to own a lakefront home on Lake Crescent in one of Windermere’s most exclusive gated private ski lake communities, Lake Crescent Reserve. Located in the town limits of beautiful Windermere, this property sits on the highest elevated lot on 175-acre spring-fed Lake Crescent designated as an Outstanding Florida Waterway. This well-loved private lake, known for its awesome

  Kari Fleck THE REAL ESTATE COLLECTION LLC

  2926 Marquesas Ct Unit 1, Windermere, FL 34786
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  /25

  Est $453,433 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,976 Sq Ft

  13752 Bressler Alley, Windermere, FL 34786

  13752 Bressler Alley, Windermere, FL 34786
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  /49

  $1,890,000

  • 6 Beds
  • 4 Baths
  • 3,894 Sq Ft

  9922 Brentford Ct, Windermere, FL 34786

  If you want something turn-key in Keene’s Pointe, sitting in one of the most desirable locations in the community, then look no further. This is a home you can move into today, sit down and live, without touching a single thing. This home has not only been renovated from end to end, but also has a three year old new tile roof!! Every square inch of the house feels brand new as you walk thru. It

  Shane Croft COLDWELL BANKER RESIDENTIAL RE

  9922 Brentford Ct, Windermere, FL 34786
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  /2

  $315,999 Sold Aug 04, 2025

  • 1,332 Sq Ft
  • $237/SF
  • 101 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2006

  11564 Mizzon Dr Unit 305/925, Windermere, FL 34786

  **Video Tour Available** Welcome to the Lakeside Condos at Lakes of Windermere. This isn’t just a neighborhood, it’s a lifestyle! Residents have access to the resort-style community pool, fitness center with kid’s room, clubhouse with billiards room, beach volleyball court, outdoor fireplace and BBQ areas, access to the Lake Burden tennis courts, playground and dock for fishing on Lake Burden!

  Tennille Biggers KELLER WILLIAMS ELITE PARTNERS III REALTY

  11564 Mizzon Dr Unit 305/925, Windermere, FL 34786
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  /55

  Est $1,119,034 Not Listed For Sale

  • 6 Beds
  • 4.5 Baths
  • 4,511 Sq Ft

  8388 Lookout Pointe Dr, Windermere, FL 34786

  8388 Lookout Pointe Dr, Windermere, FL 34786
• 

  

  /47

  $739,900

  • 4 Beds
  • 4 Baths
  • 3,129 Sq Ft

  13649 Zori Ln, Windermere, FL 34786

  Welcome to 13649 Zori Lane, a conveniently located home in the highly sought-after Providence Community and within the top-rated Windermere school district! This beautiful move-in-ready, four-bedroom, four-bathroom property radiates luxury and comfort, features light-filled spaces with 10-foot high ceilings, creating an open and airy feeling. Upon entrance, you will be greeted with a charming

  Deon Paul VYLLA HOME

  13649 Zori Ln, Windermere, FL 34786
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  /2

  $685,000 Sold Aug 01, 2025

  • 3,268 Sq Ft
  • $210/SF
  • 0 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2005

  1444 Whitney Isles Dr, Windermere, FL 34786

  FLORIDA living at its finest. Windermere gated community of Whitney Isles?Belmere. This 4 bedroom, 3 full baths and a half bath will give your family a perfect blend of comfort and convenience. The new roof is only 3 years old! Master bedroom is on the first floor with two Walkin closets, a large bathroom with a large walk-in shower and garden tub. Sliding glass door opens to your private

  Kimberly Cook ENGEL & VOLKERS CLERMONT

  1444 Whitney Isles Dr, Windermere, FL 34786
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  /43

  Est $527,596 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,089 Sq Ft

  11560 Charnock Dr, Windermere, FL 34786

  11560 Charnock Dr, Windermere, FL 34786
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  /57

  $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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  /2

  $498,000 Sold Aug 01, 2025

  • 2,085 Sq Ft
  • $239/SF
  • 55 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2006

  4813 River Gem Ave, Windermere, FL 34786

  PRICED TO SELL...Seller is motivated! Fall in Love with this Windermere Charmer! From the shaded front porch swing nestled beneath mature trees to the extended paver patio overlooking tranquil water views, this beautifully maintained 3-bedroom, 2-bath home is the picture of comfort and charm. Located in highly desirable Summerport, this home features a thoughtful split-bedroom

  Suzanne Hosmer RE/MAX SELECT GROUP

  4813 River Gem Ave, Windermere, FL 34786
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  /52

  Est $729,090 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,943 Sq Ft

  12961 Holdenbury Ln, Windermere, FL 34786

  12961 Holdenbury Ln, Windermere, FL 34786
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  /49

  $934,900

  • 4 Beds
  • 3.5 Baths
  • 3,938 Sq Ft

  1451 Whitney Isles Dr, Windermere, FL 34786

  Welcome to your luxury oasis in the exclusive, gated community of Belmere. This beautifully landscaped, Mediterranean-style residence is the perfect blend of elegance and comfort, offering four bedrooms, three and a half baths, and a three-car garage. Step inside through grand double glass doors into a two-story foyer with soaring ceilings. The open-concept layout is perfect for entertaining,

  Odel Ximinies COLDWELL BANKER RESIDENTIAL RE

  1451 Whitney Isles Dr, Windermere, FL 34786
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  /2

  $345,000 Sold Jul 31, 2025

  • 1,520 Sq Ft
  • $227/SF
  • 11 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2013

  12359 Langstaff Dr, Windermere, FL 34786

  Beautiful Townhome with Disney Firework Views in Sought-After WindermereAC FIVE YEAR OLD, OVEN 1 YEAR OLD, NEW MASTER BATHROOM SHOWER DOORThis charming end-unit townhome offers stunning Disney firework views and is ideally located in one of Windermere’s most desirable communities. With no front neighbors, the master bedroom enjoys tranquil views of a dry pond and mature trees,

  Jing Yue INTEREALTY SERVICE

  12359 Langstaff Dr, Windermere, FL 34786
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  /21

  Est $513,978 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,222 Sq Ft

  11019 Bagley Alley, Windermere, FL 34786

  11019 Bagley Alley, Windermere, FL 34786
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  /63

  $3,375,000

  • 5 Beds
  • 5.5 Baths
  • 4,701 Sq Ft

  2012 Bellamere Ct, Windermere, FL 34786

  Exquisitely appointed and elegantly packaged former model home, showcasing the pinnacle of perfection, from luxury home builder Element Homes. This masterpiece stands supreme for its high-quality fit and finish and a highly desirable floorplan – featuring a great room combination of family room, dining room, and kitchen – masterfully crafted to exhibit transitional style and function. A wall of

  Rob Rahter STOCKWORTH REALTY GROUP

  2012 Bellamere Ct, Windermere, FL 34786
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  /2

  $1,468,000 Sold Jul 31, 2025

  • 5,247 Sq Ft
  • $280/SF
  • 42 Days On Market

  • 5 Beds
  • 4.5 Baths
  • Built 2007

  9032 Tavolini Terrace, Windermere, FL 34786

  Luxury Meets Lifestyle at 9032 Tavolini Terrace, Windermere, FL!Welcome to an exceptional blend of refined design and resort-style living nestled in the heart of Windermere. This stunning 5-bedroom, 4.5-bath estate spans just over 5200 square feet of meticulously upgraded interiors and masterfully redesigned outdoor spaces — all curated for the most discerning homeowner.Step

  Jacky Herrera COMPASS FLORIDA LLC

  9032 Tavolini Terrace, Windermere, FL 34786
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  /20

  Est $798,973 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 3,677 Sq Ft

  11722 Gray Rock Trail, Windermere, FL 34786

  11722 Gray Rock Trail, Windermere, FL 34786
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  /38

  $550,000

  • 4 Beds
  • 3.5 Baths
  • 2,604 Sq Ft

  12621 Salomon Cove Dr, Windermere, FL 34786

  Welcome to this move-in ready home in sought-after Westside Village, offering a FLEXIBLE FLOOR PLAN and SEPARATE 1-BEDROOM IN-LAW SUITE above the garage — perfect for guests, rental income, or multi-generational living. The main home up front offers 3 bedrooms plus a versatile loft room—ideal as an office, playroom, or media space—anchored by an open great room and a granite-island kitchen with

  Jun Zhou MAGICMIND REALTY LLC

  12621 Salomon Cove Dr, Windermere, FL 34786
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  /2

  $890,000 Sold Jul 31, 2025

  • 2,562 Sq Ft
  • $347/SF
  • 274 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1971

  235 Oakdale St, Windermere, FL 34786

  Best priced home within the town! Here is your opportunity to own a single-story fully remodeled pool home on a corner lot in the desirable downtown Windermere with NO HOA on county water! At first glance you will immediately appreciate the charming curb appeal your home has to offer. It is constructed with masonry block and Hardie board siding on a concrete slab. The main living areas of your

  Simon Simaan THE SIMON SIMAAN GROUP

  235 Oakdale St, Windermere, FL 34786
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  /45

  Est $822,611 Not Listed For Sale

  • 5 Beds
  • 4.5 Baths
  • 3,680 Sq Ft

  7016 Kiwano Way, Windermere, FL 34786

  7016 Kiwano Way, Windermere, FL 34786
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  /51

  $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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