Windermere, FL Homes for Sale

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  $749,995

  $40K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,469 Sq Ft

  9237 Sabal Palm Cir, Windermere, FL 34786

  Nestled in the charming and highly desirable Silverwoods subdivision of Windermere, this beautifully maintained home offers the perfect blend of comfort, convenience, and community living. Ideally situated between Bay Hill and Isleworth, Silverwoods is a sought-after neighborhood of just over 250 homes, known for its tree-lined streets, sidewalks, street lighting, and welcoming atmosphere.

  Chelsea Murphy OLYMPUS EXECUTIVE REALTY INC

  9237 Sabal Palm Cir, Windermere, FL 34786
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  /4

  $1,572,000

  $3K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 2,130 Sq Ft

  33 Main St, Windermere, FL 34786

  BUTLER CHAIN WATERFRONT Windermere 4/3 HOME WITH BOAT SLIP on a .37 acre Lot. Cypress trees line the beautiful serene canal leading directly to the 12 lakes of the Butler Chain. PRIVATE FINANCING IS AVAILABLE - (ask for terms and conditions). Access the Butler chain of lakes from your back yard to Lake Down or Lake Wauseon. Renovate or Build your own modern upscale dream home. Town of Windermere

  Bruce Higgins SAND DOLLAR REALTY GROUP INC

  33 Main St, Windermere, FL 34786
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  /2

  $3,100,000

  Coming Soon

  • 4 Beds
  • 4.5 Baths
  • 4,296 Sq Ft

  12102 Montalcino Cir, Windermere, FL 34786

  This corner lakefront lot is coming soon!

  Kristy Cook EXP REALTY LLC

  12102 Montalcino Cir, Windermere, FL 34786
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  /36

  $1,825,000

  $100K PRICE DROP

  • 4 Beds
  • 4 Baths
  • 3,687 Sq Ft

  6560 Lake Burden View Dr, Windermere, FL 34786

  Experience refined, single-level living in this exceptional custom home located within Keene’s Pointe, Windermere’s premier guard-gated golf and lakefront community. Designed with both privacy and comfort in mind, this beautifully appointed residence offers 4 bedrooms, 4 full baths, a private office, and a resort-style pool and spa. At the front of the home, the dedicated office enjoys tranquil

  Rob Rahter STOCKWORTH REALTY GROUP

  6560 Lake Burden View Dr, Windermere, FL 34786
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  /19

  $299,500

  • 2 Beds
  • 2 Baths
  • 1,161 Sq Ft

  8180 Boat Hook Loop Unit 109, Windermere, FL 34786

  Discover comfort and convenience in this well-appointed first-floor condo located in the heart of Windermere. Unit 109 offers a functional split-bedroom layout with inviting living spaces, generous natural light, and easy ground-level access. The kitchen opens seamlessly to the main living area, creating a welcoming flow that works equally well for everyday living or entertaining guests.The

  Reinaldo Roman ROMAN'S PRO REALTY LLC

  8180 Boat Hook Loop Unit 109, Windermere, FL 34786
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  /89

  $1,300,000

  • 6 Beds
  • 4 Baths
  • 3,667 Sq Ft

  12676 Salomon Cove Dr, Windermere, FL 34786

  This exceptional, fully renovated residence offers the perfect blend of contemporary design, luxury finishes, smart technology, and resort-style living. Every detail has been thoughtfully curated, featuring large-format porcelain tile throughout the main level and luxury vinyl flooring throughout the second floor, complemented by custom millwork, imported Italian wallpaper, designer lighting, and

  Ramon Brandão WEBB FLORIDA REALTY LLC

  12676 Salomon Cove Dr, Windermere, FL 34786
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  /53

  $8,695,000

  • Land
  • 2.19 Acres
  • $3,970,320 per Acre

  12422 Park Ave, Windermere, FL 34786

  WELCOME TO PARK AVENUE. This tremendous opportunity offers 2.19 acres of sprawling possibilities over 2 parcels with Southeastern exposure and sweeping lake views. Nestled on the gorgeous shoreline of Lake Butler among the famed Butler Chain of Lakes, within one of Windermere’s most desirable communities - Chaine Du Lac – this exclusive homesite truly has it all. The gates within the gates that

  Michael Julian JULIAN PROPERTIES, INC.

  12422 Park Ave, Windermere, FL 34786
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  /39

  $649,500

  • 5 Beds
  • 3.5 Baths
  • 2,626 Sq Ft

  11773 Bella Milano Ct, Windermere, FL 34786

  Virtually Staged. Welcome home to 11773 Bella Milano Ct — a 5-bedroom, 3.5-bath residence on a quiet cul-de-sac in the sought-after gated community of Belmere Village. Enjoy rare privacy with a wooded conservation view at the rear, bordering a park with no through-access, and a lot size just under a quarter acre. Inside, engineered hardwood and tile flooring flow through the main living areas

  BILL STARKEY KELLER WILLIAMS ADVANTAGE 2 REALTY

  11773 Bella Milano Ct, Windermere, FL 34786
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  /34

  $360,000

  • 2 Beds
  • 2 Baths
  • 1,155 Sq Ft

  14250 Sonco Ave, Windermere, FL 34786

  Location, Location, Location! Welcome to this charming one-story end-unit townhome in the highly desirable Summerport community of Windermere! Ideally situated to Keene's Crossing Elementary School and the community's exceptional amenities. The open-concept floor plan creates a bright, spacious atmosphere, seamlessly connecting the living room, dining area, and kitchen—perfect for everyday living

  Vicki Bray-Fagan, PA WATSON REALTY CORP

  14250 Sonco Ave, Windermere, FL 34786
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  /39

  $1,855,000

  $245K PRICE DROP

  • 5 Beds
  • 4.5 Baths
  • 4,716 Sq Ft

  2958 Marquesas Ct, Windermere, FL 34786

  PRICE IMPROVEMENT! Rarely available property featuring a separate GUEST HOUSE! Recently appraised - Pricing adjusted to reflect current appraised value. This beautiful and elegant courtyard-style estate, complete with a PRIVATE GUEST HOUSE/IN-LAW SUITE, offers the ideal retreat for multi-generational living within one of the most exclusive gated communities in the Town of Windermere. Designed for

  Dianna Desboyaux DOUGLAS ELLIMAN

  2958 Marquesas Ct, Windermere, FL 34786
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  /57

  $3,900,000

  $200K PRICE DROP

  • 4 Beds
  • 4.5 Baths
  • 5,301 Sq Ft

  5151 Latrobe Dr, Windermere, FL 34786

  Positioned along the stunning 4th fairway of the renowned Isleworth Golf & Country Club, this exceptional single-story estate offers four bedrooms and more than 5,300 square feet of meticulously crafted living space. Every detail of this residence reflects the owner’s exceptional craftsmanship, with bespoke woodwork woven throughout the home, culminating in the crown jewel: the primary suite’s

  Monica Lochmandy ISLEWORTH REALTY LLC

  5151 Latrobe Dr, Windermere, FL 34786
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  /58

  $30,000,000

  • 7 Beds
  • 14 Baths
  • 51,000 Sq Ft

  9508 Windy Ridge Rd, Windermere, FL 34786

  Showcasing Central Florida’s most iconic lakefront estate: an 18-acre compound with 614 feet of pristine frontage on Lake Down on The Butler Chain of Lakes. The Windy Ridge Estate is comprised of multiple buildings spanning 51,000 square feet of space including an expansive 20,333 square-foot Georgian-style Plantation mansion that is a showplace residence with generous luxurious spaces, classic

  Rob Rahter STOCKWORTH REALTY GROUP

  9508 Windy Ridge Rd, Windermere, FL 34786
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  /19

  $790,900

  $41K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 2,987 Sq Ft

  2128 Lake Crescent Ct, Windermere, FL 34786

  Auction Property. 4 bedroom 2 bathroom 2,987 square foot home sitting on a 34,848 square foot lot in the gates of Windermere Club, this lakefront residence has resort-style amenities surrounding the beautiful Lake Crescent. Jump on this great deal before its gone! All buyers are responsible to confirm City, County, Zoning, Tax, and other records to their satisfaction before bidding. No inspection

  Jamarr Zellner REALHOME SERVICE & SOLUTIONS INC

  2128 Lake Crescent Ct, Windermere, FL 34786
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  /63

  $890,000

  $49K PRICE DROP

  • 5 Beds
  • 3.5 Baths
  • 3,182 Sq Ft

  11326 Ledgement Ln, Windermere, FL 34786

  Virtually Staged. Experience refined living in this beautifully updated 5-bedroom home, nestled in an exclusive gated community zoned for top-rated schools. The open-concept main level boasts soaring high ceilings, abundant natural light, elegant tile flooring, and a convenient primary suite for ultimate privacy. At the heart of the home is a fully remodeled kitchen (2021) featuring upgraded

  Jingjing Guan AAA GLOBAL VENTURES PA

  11326 Ledgement Ln, Windermere, FL 34786
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  /2

  $579,857

  New Construction

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

  5577 Lemon Orchard Bend, Windermere, FL 34786

  Enjoy convenient, low-maintenance living in this two-story townhome featuring a private paver courtyard and two-car garage, perfectly located in the heart of Windermere. Designed for both comfort and functionality, this home offers a smart layout ideal for everyday living and entertaining. Design upgrades include 42 cabinets, quartz countertops, tiled backsplash, pendant lighting and stainless

  Ashton Woods Builder

  5577 Lemon Orchard Bend, Windermere, FL 34786
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  $2,349,000

  $51K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 3,004 Sq Ft

  9620 Maywood Dr, Windermere, FL 34786

  Lakefront living on the Butler Chain of Lakes in the heart of Windermere. This rare offering on Lake Down presents 100 feet of direct frontage, expansive water views and a private setting on a quiet cul-de-sac with no HOA. Set across 1.35 acres, this two-story pool home captures the essence of Windermere’s enduring lakefront lifestyle, where space, privacy, and natural beauty come together in a

  Linda O'Grady PREMIER SOTHEBYS INT'L REALTY

  9620 Maywood Dr, Windermere, FL 34786
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  Price To Be Determined

  New Construction

  • 5 Beds
  • 4.5 Baths
  • 6,119 Sq Ft

  Soudron Plan at Saddlecrest at Windermere, Windermere, FL

  The Soudron's inviting covered porch and double-door entry flow into the impressive two-story foyer and lovely formal dining room, with views to the two-story great room, casual dining area, and desirable large covered lanai beyond. The well-equipped kitchen is enhanced by a large center island with breakfast bar, plenty of counter and cabinet space, thoughtful workspace, and huge walk-in pantry.

  Toll Brothers, Inc. Builder

  1841 Windermere Rd Unit 41281969, Windermere, FL
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  /58

  $930,000

  $20K PRICE DROP

  • 5 Beds
  • 4.5 Baths
  • 4,043 Sq Ft

  12929 Westside Village Loop, Windermere, FL 34786

  Virtually Staged. Enjoy the best of Central Florida living in a highly sought-after neighborhood, just minutes from local schools, shopping, great restaurants, and magic of Disney. This 5-bedroom, 4.5-bathroom pool home is clean, well-maintained, and ready for move-in, featuring a freshly painted interior along with a newly painted exterior stucco, patio, and doors.THE FIRST FLOOR Walking in

  Steven Koleno BEYCOME OF FLORIDA LLC

  12929 Westside Village Loop, Windermere, FL 34786
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  /34

  $2,240,000

  $410K PRICE DROP

  • 4 Beds
  • 5.5 Baths
  • 4,810 Sq Ft

  6102 S Hampshire Ct, Windermere, FL 34786

  Virtually Staged. This custom-built residence by Rick Watson is located in the sought-after community of Keene’s Pointe, positioned on a private lot overlooking the Jack Nicklaus Golden Bear Club golf course. The home offers consistent views of the 6th hole, along with the added bonus of nightly Disney fireworks visible from multiple areas, including the living room, primary bedroom, kitchen, and

  Jessica Dessire Cueva PA CHARLES RUTENBERG REALTY ORLANDO

  6102 S Hampshire Ct, Windermere, FL 34786
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  /74

  $1,075,000

  • 5 Beds
  • 4 Baths
  • 4,332 Sq Ft

  8316 Lookout Pointe Dr, Windermere, FL 34786

  Fully Furnished- Located in the highly desirable Windermere Trails community, this impressive residence offers 5 bedrooms, 4 full bathrooms, a media room, loft, gym, and game room, providing plenty of space for both everyday living and entertaining. The home features elegant iron stair railings, formal living and dining areas, and an open-concept layout designed for comfort and functionality. The

  Gian Balsamo LA ROSA REALTY KISSIMMEE

  8316 Lookout Pointe Dr, Windermere, FL 34786
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  /11

  $900,000

  • 4 Beds
  • 4.5 Baths
  • 3,119 Sq Ft

  11835 Gold Creek Trail, Windermere, FL 34786

  Windermere Trails Award Winning Model - Voted #1 Model by HBA 2013 It's surrounded by The Butler Chain of Lakes, with fabulous shopping and dining just minutes away. These are just a few of the celebrated qualities you'll love about Windermere Trails. Located in Windermere, FL, Windermere Trails is a community of new, incredibly energy-efficient homes, ranging 2,260 - 4,400 sq. ft. just

  Flavio Melo BB GROUP REALTY CORP

  11835 Gold Creek Trail, Windermere, FL 34786
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  /57

  $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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  /56

  $900,000

  $75K PRICE DROP

  • 4 Beds
  • 4 Baths
  • 2,636 Sq Ft

  3328 Wax Berry Ct, Windermere, FL 34786

  Virtually Staged. **Back on the market! 25k price improvement and a new roof being added! Buyers financing fell through.** Located within Lake Butler Estates, one of Windermere’s most private and established communities, this 4-bedroom, 4-bath pool home is situated on a one-acre cul-de-sac lot surrounded by mature oak trees and only 11 neighboring homes. Originally constructed in 1984 and

  Ferris Kassar PREFERRED REAL ESTATE BROKERS

  3328 Wax Berry Ct, Windermere, FL 34786
• 

  Price To Be Determined

  New Construction

  • 5 Beds
  • 5.5 Baths
  • 5,801 Sq Ft

  Varen Plan at Saddlecrest at Windermere, Windermere, FL

  The Varen's welcoming covered porch and double-door entry open onto the stunning two-story foyer and two-story great room, with views to the desirable large covered lanai beyond. The well-designed kitchen overlooks a bright casual dining area, and is highlighted by a large center island with breakfast bar, plenty of counter and cabinet space, and ample walk-in pantry. The marvelous primary

  Toll Brothers, Inc. Builder

  1841 Windermere Rd Unit 41281972, Windermere, FL
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  /95

  $1,090,000

  • 4 Beds
  • 3 Baths
  • 2,842 Sq Ft

  1407 Hempel Ave, Windermere, FL 34786

  Welcome to this incredible investment opportunity located in one of the most desirable areas in Central Florida. This beautiful property offers the perfect combination of space, privacy, freedom, and location. Featuring 4 spacious bedrooms and 3 full bathrooms, this home sits on more than half an acre of land, giving you and your family the opportunity to truly enjoy comfort and outdoor

  Lina Abi Hanna De El Bonne MY REALTY GROUP, LLC.

  1407 Hempel Ave, Windermere, FL 34786
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  /34

  $655,000

  • 4 Beds
  • 2 Baths
  • 2,745 Sq Ft

  13228 Roskin Ln, Windermere, FL 34786

  Virtually Staged. 13228 Roskin Ln is a two-story Windermere home with a two-story foyer and hardwood flooring through the main level. The kitchen features granite countertops, stainless steel appliances, wood cabinetry, and a center island that opens to the great room for connected living. A separate living area provides space for larger gatherings, with sliding doors leading to the screened

  Karen Albright OPENDOOR BROKERAGE LLC

  13228 Roskin Ln, Windermere, FL 34786
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  /27

  $4,190,000

  $279K PRICE DROP

  • 3 Beds
  • 4.5 Baths
  • 6,236 Sq Ft

  4906 Aviva Garden Ct, Windermere, FL 34786

  Welcome to an exceptional opportunity within the gates of Isleworth, one of Central Florida’s most Acclaimed private golf communities. Perfectly positioned along a tranquil pond and scenic walking trail, this move-in ready residence offers a rare blend of privacy, natural beauty, and refined living in the heart of Windermere.Thoughtfully designed for both everyday comfort and elevated

  William Campbell CAMPBELL CUSTOM HOMES INC

  4906 Aviva Garden Ct, Windermere, FL 34786
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  /52

  $650,000

  • 5 Beds
  • 3.5 Baths
  • 2,966 Sq Ft

  12912 Droxford Rd, Windermere, FL 34786

  Welcome to this beautifully maintained two-story home in the highly sought-after Lakes of Windermere, offering 5 bedrooms, 3.5 bathrooms, a private screened pool, and a brand-NEW ROOF currently being installed for added value and peace of mind. Designed with both comfort and functionality in mind, the home features a bright, open floor plan with spacious living and dining areas, tile flooring

  Phat Nguyen LPT REALTY, LLC

  12912 Droxford Rd, Windermere, FL 34786
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  /59

  $679,999

  • 4 Beds
  • 2.5 Baths
  • 2,947 Sq Ft

  13339 Roskin Ln, Windermere, FL 34786

  Your Windermere lifestyle starts here. This beautifully designed 4 Bed 2.5 Bath home with nearly 3,000 square feet combines space, savings, and an unbeatable location.From the moment you walk in, you'll appreciate the flexible layout featuring a private home office, expansive upstairs loft, oversized bedrooms, and a spacious primary suite designed for comfort. Whether you're working from home,

  Karla Price COLDWELL BANKER REALTY

  13339 Roskin Ln, Windermere, FL 34786
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  /65

  $1,399,000

  $100K PRICE DROP

  • 4 Beds
  • 4 Baths
  • 4,052 Sq Ft

  9119 Balmoral Mews Square, Windermere, FL 34786

  Virtually Staged. Welcome to an exceptional opportunity in the exclusive gated enclave of Balmoral, home to just 32 distinctive custom residences, where privacy, timeless elegance, and the coveted Windermere lifestyle come together seamlessly. Situated on over half an acre, this beautifully landscaped property offers a serene and private retreat surrounded by mature greenery, lush tropical

  Seana Abdelmajid LA ROSA REALTY BEACHES LLC

  9119 Balmoral Mews Square, Windermere, FL 34786

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