Windermere Homes for Sale

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  /100

  $3,990,000

  $10K PRICE DROP

  • 6 Beds
  • 7 Baths
  • 6,896 Sq Ft

  4201 Isabella Cir, Windermere, FL 34786

  Welcome to this beautifully furnished luxury residence in the guard-gated community of Casabella in Windermere. Situated on a private half-acre homesite, this impressive Toll Brothers Villa Divina model offers approximately 6,881 square feet of thoughtfully designed living space featuring 6 bedrooms, and 7 full bathrooms. The home showcases elegant architectural details, soaring ceilings,

  Any Alves WRA BUSINESS & REAL ESTATE

  4201 Isabella Cir, Windermere, FL 34786
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  /59

  $1,569,000

  $28K PRICE DROP

  • 5 Beds
  • 3.5 Baths
  • 3,486 Sq Ft

  11027 Hawkshead Ct, Windermere, FL 34786

  Back on market due to buyer non-performance. Exceptional value in Lake Butler Sound! Welcome to 11027 Hawkshead Court, a beautifully updated luxury home in Windermere, FL offering 4 bedrooms, a dedicated office, 4 bathrooms, approximately 3,500 square feet, and a private 0.4-acre corner lot within one of Central Florida's premier guard-gated communities with 24-hour roving

  Justyna Tchorni KENNEDY REALTY GROUP LLC

  11027 Hawkshead Ct, Windermere, FL 34786
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  /19

  $2,500,000

  • Land
  • 5 Acres
  • $500,000 per Acre

  13377 Lake Butler Blvd, Winter Garden, FL 34787

  Fantastic opportunity to purchase 12+ acres of private, quiet lake front property in Winter Garden/Windermere area on West Lake Butler Blvd. with 4+ acres high and dry and no HOA. Property currently boasts dock with electricity and boat lift on a skiable lake. There is an existing house that could be remodeled or torn down and start fresh. Home is 4961 square feet and built in 1990 with

  Dawn Briggs BLUE MAGNOLIA REALTY LLC

  13377 Lake Butler Blvd, Winter Garden, FL 34787
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  /40

  $969,000

  • 5 Beds
  • 4.5 Baths
  • 3,797 Sq Ft

  9609 Westover Club Cir, Windermere, FL 34786

  WELCOME HOME ! WELL MAINTAINED , LARGE, 5 BEDROOM, 4 BATH HOME . ALSO INCLUDES OFFICE, MOVIE ROOM , STORAGE ROOM AND LOFT. OVERSIZE 3 CAR GARAGE,BRICK PAVER DRIVEWAY AND PATIO. FEATURES POOL AND POND WITH WATER FOUNTAIN. CLOSE TO MILLENNIA MALL,DOWNTOWN ORLANDO ,RESTAURANT ROW,DISNEY,UNIVERSAL,PARKS AND RECREATION. NO REAR NEIGHBORS AND QUIET NEIGHBORHOOD. KITCHEN FEAUTERES ISLAND, UPGRADED

  John Petit ALPHA R.E. OF CENTRAL FL LLC

  9609 Westover Club Cir, Windermere, FL 34786
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  /81

  $3,500,000

  • 4 Beds
  • 6 Baths
  • 7,669 Sq Ft

  5524 Worsham Ct, Windermere, FL 34786

  Welcome to the exclusive gates of Isleworth, golf front estate offers over 7,600 square feet of refined luxury living overlooking the fairway of the renowned Isleworth Golf & Country Club, one of the worlds most prestigious golf club communities, this championship course was designed by Arnold Palmer and set along the Butler Chain of Lakes. The neighborhood is defined by beautifully landscaped

  Ayoub Aitelhaj ATLIS REALTY GROUP LLC

  5524 Worsham Ct, Windermere, FL 34786
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  /40

  $448,000

  $12K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 1,910 Sq Ft

  11429 Brownstone St, Windermere, FL 34786

  Virtually Staged. Seller may consider buyer concessions if made in an offer ~ Enjoy the best of Windermere living in this beautifully maintained 4-bedroom, 2.5-bath townhome with a rear facing 2-car garage in the sought-after Lake Burden South community! Offering a spacious, LOW MAINTENANCE LIFESTYLE, this home combines an ideal SPLIT BEDROOM floor plan with timeless finishes and an unbeatable

  Jennifer Wemert WEMERT GROUP REALTY LLC

  11429 Brownstone St, Windermere, FL 34786
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  /92

  $27,000,000

  • 7 Beds
  • 10 Baths
  • 22,108 Sq Ft

  5603 Marleon Dr, Windermere, FL 34786

  A rare legacy estate of extraordinary scale and architectural significance, this magnificent lakefront compound spans over 22,000 square feet across more than 11 private acres with over 440 feet of pristine frontage on Cypress Lake. Masterfully designed to deliver the ultimate blend of grandeur, privacy, and resort-inspired living, the residence is statement of uncompromising luxury. Beyond the

  Llin Lu PREMIER SOTHEBYS INT'L REALTY

  5603 Marleon 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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  /58

  $4,599,000

  • 5 Beds
  • 5.5 Baths
  • 7,740 Sq Ft

  12540 Park Ave, Windermere, FL 34786

  Extraordinary Lake Butler views abound from this classically elegant yet recently updated Chaine du Lac estate residence. Cradled in a private cove on Windermere’s signature lake on The Butler Chain, this showplace address stands supreme for its majestic presence, distinguished features and updates, and unsurpassed outdoor resort-style entertainment and living areas. Boasting a new roof, new

  Rob Rahter STOCKWORTH REALTY GROUP

  12540 Park Ave, Windermere, FL 34786
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  /30

  $595,000

  $203K PRICE DROP

  • Land
  • 21,344 Sq Ft
  • $1,214,286 per Acre

  1516 Hempel Ave, Windermere, FL 34786

  Vacant Land – ½ Acre in Windermere - Property is zoned R-CE with Variance to allow construction of single family!Build your dream home or secure a smart investment in one of Central Florida’s most highly desired communities—Windermere!Spacious ½ acre lot with endless possibilitiesPrime location in the heart of WindermereSurrounded by A+ rated schoolsEasy access to shopping,

  Matthew Hughes REAL BROKER, LLC

  1516 Hempel Ave, Windermere, FL 34786
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  /10

  $899,999

  • 3 Beds
  • 2 Baths
  • 2,258 Sq Ft

  2630 Stanton Hall Ct, Windermere, FL 34786

  Incredible Opportunity to own a pool home with a huge lot in a fantastic neighborhood * Good Floorplan * Close to Everything * Home has 7 Rooms * Separate Office * Formal Living Room * 3 Bedrooms * Breakfast Nook with Open Kitchen * Formal Dining Room * Family or Great Room * Pool Bath * Vaulted Ceilings * Inside Laundry * Screened & Covered Pool with Large Deck * Formal Dining Room * Large

  Darrell Nunnelley VINTAGE REALTY GROUP LLC

  2630 Stanton Hall Ct, Windermere, FL 34786
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  /81

  $3,300,000

  $500K PRICE DROP

  • 5 Beds
  • 5 Baths
  • 5,018 Sq Ft

  11539 Lake Butler Blvd, Windermere, FL 34786

  Incredible 1st Floor Inlaw Apartment with Full Bath, Sitting Room with Fireplace & Bedroom with Large Walk in Closet * Purchase before October 31, 2026 and receive a full size Pickleball & Sport Court * Welcome to this spectacular 5-bedroom, 5-bathroom custom home offering over 8,000 square feet of thoughtfully designed luxury living—spared no expense and crafted to perfection. * Nestled on a

  Darrell Nunnelley VINTAGE REALTY GROUP LLC

  11539 Lake Butler Blvd, Windermere, FL 34786
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  /90

  $2,150,000

  $200K PRICE DROP

  • 5 Beds
  • 4 Baths
  • 4,876 Sq Ft

  2068 Roberts Point Dr, Windermere, FL 34786

  One or more photo(s) has been virtually staged. Private Windermere Estate in Guard-Gated Waterford Pointe with Detached Guest Casita, Lake Access & an Exceptional Seller Incentive: Up to $36,000 Toward a Rate Buy-Down or Buyer Closing Costs.A rare opportunity in one of Windermere’s most established guard-gated communities, this private estate offers the space, flexibility, and lifestyle

  David Dorman CENTURY 21 CARIOTI

  2068 Roberts Point Dr, Windermere, FL 34786
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  /73

  $1,995,000

  • 6 Beds
  • 6 Baths
  • 5,869 Sq Ft

  4282 Mckinnon Rd, Windermere, FL 34786

  Welcome to 4282 McKinnon Rd, a beautifully updated Windermere estate offering exceptional space, privacy, and flexibility on approximately 1.15 acres—with NO HOA. Featuring 6 bedrooms, 6 baths, nearly 5,900 square feet of living space, a private pool, and 3-car garage, this custom home combines an impressive floor plan with extensive recent improvements.Move-in ready and refreshed inside and

  Shelley Dawson COMPASS FLORIDA LLC

  4282 Mckinnon Rd, Windermere, FL 34786
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  /65

  $1,100,000

  $130K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 3,478 Sq Ft

  2512 Tryon Place, Windermere, FL 34786

  Welcome to a rare opportunity in the highly sought-after The Manors at Butler Bay, in the heart of Windermere. This custom-built home is situated on nearly three-quarters of an acre and a corner lot. This impressive single-story residence offers 3,478 square feet of thoughtfully designed living space with 4 bedrooms, 3 full bathrooms, a side-entry 2-car garage, an extended driveway, and a

  Jamie Stolinas Crame CENTURY 21 CARIOTI

  2512 Tryon Place, Windermere, FL 34786
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  /28

  $12,999,999

  New Construction $550K PRICE DROP

  • 9 Beds
  • 16 Baths
  • 20,445 Sq Ft

  9621 Windy Ridge Rd, Windermere, FL 34786

  Under Construction. Under Construction. Experience unmatched privacy, prestige, and personalization with this brand-new mansion on 2.5 pristine acres in the heart of Windermere. Tucked against protected government land that can never be developed, this estate offers the serenity of untouched nature with the ultimate in luxury living.Two Pools one outdoor with a swim up bar and grill area and the

  Natalie Citarelli CITARELLI REALTY GROUP LLC

  9621 Windy Ridge Rd, Windermere, FL 34786
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  /68

  $999,900

  $200K PRICE DROP

  • 5 Beds
  • 4 Baths
  • 3,389 Sq Ft

  13536 Sunset Lakes Cir, Winter Garden, FL 34787

  Experience luxury living in this gorgeous home in the highly sought after Sunset Lakes community in Winter Garden. This FULLY-REMODELED, 5-bedroom, 4-bath POOL/SPA home sits on a SERENE POND and offers 3,389 sq. ft. of beautifully designed living space on OVER HALF AN ACRE, complete with a three-car side entry garage. Four of the 5 bedrooms are conveniently located on the first floor (including

  Diane Sterling KELLER WILLIAMS ADVANTAGE REALTY

  13536 Sunset Lakes Cir, Winter Garden, FL 34787
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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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  /6

  $200,000

  • Land
  • 10,890 Sq Ft
  • $800,000 per Acre

  0 Park Ridge Gotha Rd Unit MFRS5156135, Un-Incorporated, FL 34786

  Great investment opportunity!

  Margarita Morales OLYMPUS EXECUTIVE REALTY INC

  0 Park Ridge Gotha Rd Unit MFRS5156135, Un-Incorporated, FL 34786
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  /74

  $3,100,000

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

  12102 Montalcino Cir, Windermere, FL 34786

  Virtually Staged. Welcome to 12102 Montalcino Circle, an exceptional custom built waterfront estate located in one of Windermere's most sought after gated communities, Casa Del Lago. Perfectly positioned at the end of a quiet cul-de-sac on 1.41 acres along the shores of Lake Burden, this extraordinary residence is offered fully furnished and showcases breathtaking water views, nightly Disney

  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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  /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

  $1,830,000

  $270K 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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  /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

  Jingjing Guan AAA GLOBAL VENTURES PA

  11326 Ledgement Ln, Windermere, FL 34786
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  /43

  $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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  /2

  $1,495,000

  Coming Soon

  • 5 Beds
  • 4.5 Baths
  • 4,238 Sq Ft

  6239 Rydal Ct, Windermere, FL 34786

  Coming Soon! Located in the exclusive Reserve at Lake Butler Sound — one of Windermere’s premier 24-hour guard-gated communities — this custom 5-bedroom, 4.5-bath pool home offers 4,238 square feet of living space, four bedrooms on the first floor, exceptional indoor-outdoor living, and a prime Windermere location near the renowned Butler Chain of Lakes.Situated on an oversized cul-de-sac

  Deb Schroeder INFINITY REALTY GROUP LLC

  6239 Rydal Ct, Windermere, FL 34786
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  /7

  $964,500

  • 5 Beds
  • 3 Baths
  • 2,717 Sq Ft

  11348 Willow Gardens Dr, Windermere, FL 34786

  YOUR SEARCH IS OVER! NOW AVAILABLE! Exceptional custom CAHILL pool home situated on a private sprawling .92 acre oversized lot in the highly desirable Willows at Lake Rhea in the Town Limits of Windermere. Offering 5 bedrooms, 3 bathrooms, the thoughtfully designed split floor plan provides an ideal balance of privacy, comfort and functionality. The home features elegant formal living and dining

  Golden Begley VINTAGE REALTY GROUP LLC

  11348 Willow Gardens Dr, Windermere, FL 34786
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  $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

  Isis Sarcos EXP REALTY LLC

  5070 Down Point Ln, Windermere, FL 34786
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  $850,000

  $125K PRICE DROP

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

  3328 Wax Berry Ct, Windermere, FL 34786

  Virtually Staged. ** Price just reduced by 50k for a quick sale!** 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 renovated in 2022, this single-story home offers an open, split

  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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  /29

  $3,599,000

  • 5 Beds
  • 7 Baths
  • 5,342 Sq Ft

  3986 Isabella Cir, Windermere, FL 34786

  EXCEPTIONAL LAKEFRONT LUXURY ESTATE IN CASABELLA AT WINDERMEREDiscover an extraordinary luxury residence in the prestigious gated community of Casabella at Windermere, where elegant architecture, exceptional outdoor living, and one of the community’s most desirable lots come together.The true highlight of this property is its exceptional waterfront setting. The lake beautifully

  Ricardo Konageski da Fonseca WRA BUSINESS & REAL ESTATE

  3986 Isabella Cir, Windermere, FL 34786
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  /95

  $1,500,000

  • 5 Beds
  • 4 Baths
  • 3,656 Sq Ft

  17526 Black Rail St, Windermere, FL 34786

  An exceptional residence where refined design and effortless living converge. Meticulously remodeled throughout, the home welcomes you with bespoke modern woodwork gracing the foyer, living room, bedrooms, and loft — a testament to artisan-level craftsmanship rarely found at any price point. The loft has been reimagined as a private cinema, complete with a high-resolution projector, integrated

  Fernando Zucato CHARLES RUTENBERG REALTY ORLANDO

  17526 Black Rail St, 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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