Windermere, FL Homes

• 

  

  /2

  $850,000 Sold Aug 15, 2025

  • Land
  • 0.26 Acre
  • $3,269,231 per Acre

  • 19 Days On Market

  0 Gladys Garden Ct, Windermere, FL 34786

  Within the gates of Isleworth, this beautiful home site is positioned within the Gardens of Isleworth - an intimate enclave of custom homes surrounded by lush gardens, water features, bridges, and walking paths. The home site will feature a beautiful estate celebrating the best of indoor-outdoor living to be built by leading luxury custom home builder Goehring & Morgan Construction.

  Wayne Sheffield ISLEWORTH REALTY LLC

  0 Gladys Garden Ct, Windermere, FL 34786
• 

  

  

  /38

  Est $399,776 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,584 Sq Ft

  11685 Water Run Alley, Windermere, FL 34786

  11685 Water Run Alley, Windermere, FL 34786
• 

  

  

  /83

  $1,999,000

  • 5 Beds
  • 3.5 Baths
  • 4,130 Sq Ft

  13048 Lake Roper Ct, Windermere, FL 34786

  Priced to sell fast. Unmatched Value! The only Windermere lakefront home with boat access available under $2M. Don't miss this opportunity. Enjoy the e evenings to a breathtaking sunset at your own private lake in this stunning custom-built home.Land: 1.6 acres including lake portion with 135 feet direct lake frontage. Lake Roper is renowned for its water sports, water skiing, jet skiing and

  Fernando Teixeira WOODSTONE INVESTMENTS LLC

  13048 Lake Roper Ct, Windermere, FL 34786
• 

  

  /2

  $635,000 Sold Aug 15, 2025

  • 2,020 Sq Ft
  • $314/SF
  • 44 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1985

  4833 Palm Tree Ct, Windermere, FL 34786

  Welcome to your Oasis at 4833 Palm Tree Ct. a beautifully maintained single-story residence nestled in the heart of Windermere's most desirable community. This charming 4-bedroom 2.5-bathroom home offers the perfect blend of comfort style & convenience creating an idyllic Florida lifestyle for you and your family.Step inside and be greeted by a sense of light and spaciousness. The tile

  Charles Kohlinger BHHS FLORIDA REALTY

  4833 Palm Tree Ct, Windermere, FL 34786
• 

  

  

  /6

  Est $420,219 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,826 Sq Ft

  2216 Bear Peak Rd, Minneola, FL 34715

  2216 Bear Peak Rd, Minneola, FL 34715
• 

  

  /35

  $420,000

  • 3 Beds
  • 2.5 Baths
  • 1,748 Sq Ft

  12838 Strode Ln, Windermere, FL 34786

  Motivated Seller offering $5,000 Flex Cash to help make this home yours! With a recently replaced roof providing added peace of mind, this beautifully maintained residence also features upgraded flooring throughout—no carpet, just a clean, modern look designed for easy living. The spacious primary suite boasts a walk-in closet and private en-suite bath, while the rear-entry 2-car garage enhances

  Luis Leon Medina LA ROSA REALTY LLC

  12838 Strode Ln, Windermere, FL 34786
• 

  /2

  $1,655,000 Sold Aug 15, 2025

  • 3,104 Sq Ft
  • $533/SF
  • 112 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1975

  1424 Kelso Blvd, Windermere, FL 34786

  Welcome to 1424 Kelso Boulevard, a stunning luxury waterfront estate that seamlessly blends elegance and modern comfort. This 4-bedroom, 2.5 bathroom masterpiece offers unparalleled craftsmanship and breathtaking water views, creating the perfect sanctuary for refined living. Upon approaching the home you are greeted by the recently brick paved circular driveway with ample parking for all the

  Carmen Aridas RE/MAX PRIME PROPERTIES

  1424 Kelso Blvd, Windermere, FL 34786
• 

  

  /16

  Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,332 Sq Ft

  8256 Maritime Flag St Unit 1725, Windermere, FL 34786

  8256 Maritime Flag St Unit 1725, Windermere, FL 34786
• 

  

  /57

  $12,995,000

  • 7 Beds
  • 10 Baths
  • 16,257 Sq Ft

  9935 Lake Louise Dr, Windermere, FL 34786

  Experience the pinnacle of luxury living in this extraordinary lakefront estate located in the world-renowned Isleworth Golf & Country Club. Positioned on 2.14 private acres along Lake Louise, part of the Butler Chain of Lakes, this 24,950 sq ft masterpiece (16,259 under air) blends timeless craftsmanship, modern amenities, and a warm, inviting design that makes even the most expansive spaces

  Jill Irwin IRWIN REALTY GROUP LLC

  9935 Lake Louise Dr, Windermere, FL 34786
• 

  /2

  $1,755,000 Sold Aug 15, 2025

  • 3,680 Sq Ft
  • $477/SF
  • 108 Days On Market

  • 5 Beds
  • 4.5 Baths
  • Built 2011

  11856 Vinci Dr, Windermere, FL 34786

  Beautiful Keene's Pointe custom mediterranean home featuring 5 bedrooms, 4-1/2 bathrooms and a 3 car side garage on a large homesite. As soon as you enter through the oversized double wood doors, you will immediately be greeted by the spacious formal living room with an oversized covered lanai with views of the pool. The primary bedroom is bathed in light from the extra tall windows and high

  Oscar Rodriguez B LIVE COMMERCIAL AND RESIDENTIAL REAL ESTATE

  11856 Vinci Dr, Windermere, FL 34786
• 

  

  /24

  Not Listed For Sale

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

  14348 Desert Haven St Unit 14348, Windermere, FL 34786

  14348 Desert Haven St Unit 14348, Windermere, FL 34786
• 

  

  /49

  $950,000

  • 5 Beds
  • 3 Baths
  • 4,089 Sq Ft

  1924 Katie Hill Way, Windermere, FL 34786

  Welcome to your dream home in the exclusive gated community of Westover Club, ideally situated in highly sought-after East Windermere and zoned for top-rated Thornebrooke Elementary, Gotha Middle, and Olympia High School. This expansive 5-bedroom, 3-bathroom executive residence offers over 4,000 square feet of elegantly upgraded living space, perfectly blending comfort, functionality, and

  Andy Neal MAXIM REALTY ORLANDO

  1924 Katie Hill Way, Windermere, FL 34786
• 

  /2

  $1,075,000 Sold Aug 14, 2025

  • 2,976 Sq Ft
  • $361/SF
  • 6 Days On Market

  • 5 Beds
  • 3.5 Baths
  • Built 1999

  6054 Caymus Loop, Windermere, FL 34786

  Welcome to 6054 Caymus Loop in the 24-hr gated/attended community of Keene's Pointe. One of the most desired communities in Orlando. This updated home has 5 bedrooms, 3 1/2 baths, office/den and formal dining/living, and is located on the 13th fairway of The Golden Bear Club. The first floor features the office/den and bedroom with walk-in closet, as well as functional kitchen with updated

  Teresa Stewart SOUTHERN REALTY GROUP LLC

  6054 Caymus Loop, Windermere, FL 34786
• 

  

  /23

  Est $441,684 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,631 Sq Ft

  8650 Wellington Blue Ln, Windermere, FL 34786

  8650 Wellington Blue Ln, Windermere, FL 34786
• 

  

  /30

  $775,000

  • Land
  • 0.49 Acre
  • $1,581,633 per Acre

  1516 Hempel Ave, Windermere, FL 34786

  Vacant Land – 1⁄2 Acre in WindermereBuild your dream home or secure a smart investment in one of Central Florida’s most highly desired communities—Windermere!Spacious 1⁄2 acre lot with endless possibilitiesPrime location in the heart of WindermereSurrounded by A+ rated schoolsEasy access to shopping, dining, and major highwaysRare opportunity in a highly desirable

  Matthew Hughes REAL BROKER, LLC

  1516 Hempel Ave, Windermere, FL 34786
• 

  

  /67

  $1,250,402 Sold Aug 13, 2025

  • 4,443 Sq Ft
  • $281/SF

  • 6 Beds
  • 4.5 Baths
  • Built 2025

  14249 Crest Palm Ave, Windermere, FL 34786

  The Sweetwater floorplan offers expansive living with its thoughtfully designed two-story layout. This home features six spacious bedrooms and four and a half bathrooms, perfectly accommodating larger households or guests. With over 4,400 square feet of living space, the Sweetwater includes both a flex room and multiple bonus spaces, offering flexibility for hobbies, workspaces, or entertainment

  Dream Finders Homes

  14249 Crest Palm Ave, Windermere, FL 34786
• 

  

  /36

  Est $394,127 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,584 Sq Ft

  11618 Water Run Alley, Windermere, FL 34786

  11618 Water Run Alley, Windermere, FL 34786
• 

  

  /65

  $6,395,000

  • 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 facade that opens to interiors of soaring scale and meticulous marble

  Julie Bettosini STOCKWORTH REALTY GROUP

  9639 Westover Roberts Rd, Windermere, FL 34786
• 

  /2

  $560,000 Sold Aug 13, 2025

  • 2,265 Sq Ft
  • $247/SF
  • 19 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2007

  6539 Chagford Ln, Windermere, FL 34786

  Welcome to 6539 Chagford Lane located within the beautiful community of Lakes of Windermere! This charming and well-maintained single-story home features 3 bedrooms and office with spacious closets, fenced-in backyard, new roof (2021) and numerous thoughtful upgrades throughout including custom closet systems by Closets by Design installed in the office, laundry room, and primary bedroom. The

  Lori Lucente-Nelson RE/MAX PRIME PROPERTIES

  6539 Chagford Ln, Windermere, FL 34786
• 

  

  /33

  Est $497,775 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,233 Sq Ft

  13874 Summerport Trail Loop, Windermere, FL 34786

  13874 Summerport Trail Loop, Windermere, FL 34786
• 

  

  /48

  $905,000

  • 5 Beds
  • 4 Baths
  • 3,640 Sq Ft

  9335 Westover Club Cir, Windermere, FL 34786

  Welcome to Westover Club, one of Windermere’s most desirable gated communities where tree-lined streets and a perfect location set the stage for your dream home!This beautifully maintained 5-bedroom, 4-bath home sits on an expansive one-third acre lot and offers the perfect blend of comfort, style, and functionality. Step inside to an inviting foyer that opens to a formal dining room and

  Jason Neves MARK SPAIN REAL ESTATE

  9335 Westover Club Cir, Windermere, FL 34786
• 

  /2

  $4,100,000 Sold Aug 13, 2025

  • 6,196 Sq Ft
  • $662/SF
  • 41 Days On Market

  • 5 Beds
  • 7 Baths
  • Built 2018

  3428 Chaine Du Lac Blvd, Windermere, FL 34786

  From the moment you arrive, this home makes a statement. Meticulous architectural details like rafter tails, handcrafted corbels, and a bell cast roof flare immediately set the tone for the craftsmanship within. Subtle soffit LED lighting and artfully placed landscape lighting create an evening ambiance that feels both welcoming and cinematic.Step through the grand double doors and enter

  Mauro Costa CORCORAN PREMIER REALTY

  3428 Chaine Du Lac Blvd, Windermere, FL 34786
• 

  

  /47

  Est $365,862 Not Listed For Sale

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

  14005 Oasis Springs Ln Unit 906, Windermere, FL 34786

  14005 Oasis Springs Ln Unit 906, Windermere, FL 34786
• 

  

  /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
• 

  /2

  $1,450,000 Sold Aug 13, 2025

  • 3,319 Sq Ft
  • $437/SF
  • 64 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1999

  8430 Woburn Ct, Windermere, FL 34786

  Waterfront Luxury in Keene’s Pointe – Fully Renovated & Priced to MoveWelcome to resort-style living in one of Windermere’s most exclusive 24/7 guard-gated communities. Set on a quiet cul-de-sac with peaceful lake views, this bold, fully renovated masterpiece in Keene’s Pointe blends timeless elegance with modern design—and it’s move-in ready.Inside, you’ll find high-end imported

  Mauricio Penha VOLKE REAL ESTATE LLC

  8430 Woburn Ct, Windermere, FL 34786
• 

  

  /45

  Est $1,675,813 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 3,585 Sq Ft

  9012 Pinnacle Cir, Windermere, FL 34786

  9012 Pinnacle Cir, Windermere, FL 34786
• 

  

  /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
• 

  /2

  $910,000 Sold Aug 12, 2025

  • 2,897 Sq Ft
  • $314/SF
  • 5 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 2004

  13838 Bluebird Park Rd, Windermere, FL 34786

  Waterfront Living in Windermere! Welcome home to this exquisite one-story pool home in Summerport, ideally positioned with sweeping water and sunset views—and nightly Magic Kingdom fireworks from your backyard. With elevated views of Walsh Pond in the rear and sunrise water views in the front, this property offers a rare and serene setting. Walsh Pond is a spring-fed lake known for bass fishing,

  Deb Schroeder INFINITY REALTY GROUP LLC

  13838 Bluebird Park Rd, Windermere, FL 34786
• 

  

  /39

  Est $745,749 Not Listed For Sale

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

  13207 Orange Isle Dr, Windermere, FL 34786

  13207 Orange Isle Dr, Windermere, FL 34786
• 

  

  /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
• 

  /2

  $1,560,000 Sold Aug 11, 2025

  • 3,797 Sq Ft
  • $411/SF
  • 105 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2005

  8437 Lake Burden Cir, Windermere, FL 34786

  "Price Improvement" Beautiful Mediterranean custom home in gated/24-hour guarded Keene's Pointe Golf Community. This home features 4 bedrooms and 3 1/2 baths. The kitchen and family room are definitely the heart of the home with a very open concept perfect to entertain family and friends, recently painted cabinets, island and stainless appliances. The family room is spacious with sliding doors to

  Daniela de Rodriguez B LIVE COMMERCIAL AND RESIDENTIAL REAL ESTATE

  8437 Lake Burden Cir, Windermere, FL 34786
• 

  

  /48

  Est $763,305 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,834 Sq Ft

  13608 Gorgona Isle Dr, Windermere, FL 34786

  13608 Gorgona Isle Dr, Windermere, FL 34786
• 

  

  /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
• 

  /2

  $6,600,000 Sold Aug 11, 2025

  • 10,200 Sq Ft
  • $647/SF
  • 494 Days On Market

  • 5 Beds
  • 11 Baths
  • Built 2008

  5507 Worsham Ct, Windermere, FL 34786

  Presenting one of Isleworth’s most iconic mansions: magnificent and grand, impressively positioned along the 14th fairway of the Isleworth golf course, behind the secured and guarded gates of one of the world’s most prestigious private golf club communities. This palatial estate offers a stunning mix of stately elegance and classic grandeur - and has been just reimagined with new custom touches

  Rob Rahter STOCKWORTH REALTY GROUP

  5507 Worsham Ct, Windermere, FL 34786
• 

  

  /23

  Est $705,527 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,985 Sq Ft

  9216 Outlook Rock Trail, Windermere, FL 34786

  9216 Outlook Rock Trail, Windermere, FL 34786
• 

  

  /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
• 

  /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
• 

  

  /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
• 

  

  /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
• 

  /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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