Windermere Homes for Sale

• 

  

  

  /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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  /33

  $649,999

  • 2 Beds
  • 1.5 Baths
  • 1,398 Sq Ft

  811 Main St, Windermere, FL 34786

  Exclusive Rare Opportunity to own this expansive 100'x160' double lot in downtown Windermere. Whether you’re looking for a charming home or a prime location to build your dream residence, this property delivers endless potential. The home features arched doorways, luxury vinyl plank (LVP) flooring, and a sunroom filled with natural light. The updated kitchen includes 42” soft-close cabinets,

  Asim Iftikhar CAMERON REALTY GROUP LLC

  811 Main St, Windermere, FL 34786
• 

  

  

  /19

  $834,000

  $86K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 3,068 Sq Ft

  6631 Crestmont Glen Ln Unit 1, Windermere, FL 34786

  Welcome to 6631 Crestmont Glen Lane, a beautifully maintained executive home in the gated community of Glenmuir. Set on a large and spacious, landscaped lot, this 4-bedroom, 3.5-bath residence offers an ideal blend of space, comfort, and everyday functionality.Step inside to soaring ceilings, abundant natural light, and an open-concept layout designed for both entertaining and relaxed living.

  Gonzalo Senior IRM INVEST., REAL EST.& MGMT.

  6631 Crestmont Glen Ln Unit 1, Windermere, FL 34786
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  /73

  $4,650,000

  New Construction $350K PRICE DROP

  • 5 Beds
  • 8 Baths
  • 7,940 Sq Ft

  1009 Down Reserve Ct, Windermere, FL 34786

  One or more photo(s) has been virtually staged. Just completed | Never lived in | A rare opportunity to be the very first to call this architectural showpiece home! Positioned in the highly sought after Lake Down Reserve community of Windermere, this custom-built modern Mediterranean estate delivers nearly 8,000 square feet of elevated design, cutting-edge construction, and curated luxury. This

  Jennifer Wemert WEMERT GROUP REALTY LLC

  1009 Down Reserve Ct, Windermere, FL 34786
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  /68

  $1,175,000

  $75K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,882 Sq Ft

  11536 Claymont Cir, Windermere, FL 34786

  One or more photo(s) has been virtually staged. Price Improvement! Welcome to luxury living inside the guard-gated community of Keene’s Pointe, home to the renowned Golden Bear Club and its Jack Nicklaus Signature golf course. Perfectly positioned within one of Windermere’s most sought-after neighborhoods, this exceptional single-story residence offers a refined blend of elegance, comfort, and

  Matt Allen MATT ALLEN REAL ESTATE LLC

  11536 Claymont Cir, Windermere, FL 34786
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  /25

  $850,000

  • 3 Beds
  • 2 Baths
  • 1,935 Sq Ft

  11155 Lake Butler Blvd, Windermere, FL 34786

  Rare Opporunity to own a property in Windermere that is in Move In Condition anywhere near this price * 3 Bedroom 2 Bath Open Concept with a remodeled Kitchen and Baths * Large Lot * County Water * Natural Gas * Lake Butler Blvd is the Perfect Road for Exercise & Enjoying the Outdoors * This Home Includes A Gated Private Park & Boat Ramp with a Fishing Pier & Wood Dock to tie up your Boat or Jet

  Darrell Nunnelley VINTAGE REALTY GROUP LLC

  11155 Lake Butler Blvd, 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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  /88

  $2,845,000

  $205K PRICE DROP

  • 6 Beds
  • 6.5 Baths
  • 5,882 Sq Ft

  12720 Jacob Grace Ct, Windermere, FL 34786

  Nestled within one of **Windermere**’s most exclusive communities, this extraordinary custom-built lakefront estate with an almost 2 acres lot offers an elegant lifestyle defined by privacy, prestige, and breathtaking nightly views of the **Walt Disney World** fireworks. With nearly 6,000 square feet, six bedrooms, and six and a half baths, this residence is the pinnacle of refined Central

  Adrian Jacob REDFIN CORPORATION

  12720 Jacob Grace Ct, Windermere, FL 34786
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  /30

  $575,000

  $223K PRICE DROP

  • Land
  • 21,344 Sq Ft
  • $1,173,469 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
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  /32

  $2,190,000

  $110K PRICE DROP

  • 4 Beds
  • 4.5 Baths
  • 4,257 Sq Ft

  6550 Cartmel Ln, Windermere, FL 34786

  RARE, ONE-OF-A-KIND FULLY RENOVATED LUXURY CONTEMPORARY ESTATE IN WINDERMERE – OVER HALF AN ACRE WITH PRIVATE POND VIEW Welcome to 6550 Cartmel Ln, located in the exclusive Reserve at Lake Butler Sound — one of Windermere’s most prestigious gated communities. Completely and extensively renovated from top to bottom, this exceptional modern-contemporary residence offers the perfect blend of luxury,

  Jennifer Paiano Olmeda WRA BUSINESS & REAL ESTATE

  6550 Cartmel Ln, Windermere, FL 34786
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  /81

  $2,250,000

  $100K 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 and Lake Access. A rare opportunity in one of Windermere’s most established guard-gated communities, this private estate offers the space, flexibility, and lifestyle today’s luxury buyers are actively seeking. Set on over an acre within Waterford Pointe, the

  David Dorman CENTURY 21 CARIOTI

  2068 Roberts Point Dr, Windermere, FL 34786
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  /2

  $3,500,000

  New Construction

  • 4 Beds
  • 4 Baths
  • 2,500 Sq Ft

  43 Main St, Windermere, FL 34786

  Under Construction. Modern New Construction on the Butler Chain Canal – Downtown WindermereExperience bright, modern waterfront living in the heart of the Town of Windermere. This brand-new construction single-story 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 4,280

  Milena Fernandes GOLDEN GROUP REALTY LLC

  43 Main St, Windermere, FL 34786
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  /52

  $3,725,000

  • 5 Beds
  • 4 Baths
  • 4,875 Sq Ft

  58 Main St, Windermere, FL 34786

  Nestled in the heart of Old Town Windermere, this exceptional lakefront residence offers direct access to the Butler Chain of Lakes from the tranquil waters of Wauseon Bay, prized for its reduced boat traffic and peaceful setting. Set on an oversized waterfront lot with western exposure, the home captures breathtaking lake views from nearly every room—delivering spectacular sunsets and a seamless

  Michelle Ingrassia LPT REALTY, LLC

  58 Main St, Windermere, FL 34786
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  /28

  $13,430,000

  New Construction $120K 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

  $1,100,000

  $100K 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

  $1,575,000

  • 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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  /30

  $1,890,000

  $35K 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
• 

  

  /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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  /2

  $6,500,000

  New Construction

  • 5 Beds
  • 5.5 Baths
  • 6,182 Sq Ft

  12334 Summerport Ln, Windermere, FL 34786

  Under Construction. Welcome to 12334 Summerport Lane, an extraordinary lakefront estate on the prestigious Butler Chain of Lakes in Windermere. Custom built by Davila Homes and featuring the stunning Stanford floor plan, this exceptional residence offers approximately 6,182 square feet of luxurious living space with 5 bedrooms, 5 full baths, 1 half bath, and a spacious 3-car garage. Perfectly

  Fernanda Negromonte NOVA REAL ESTATE SERVICES INC

  12334 Summerport Ln, Windermere, FL 34786
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  /32

  $1,875,000

  $225K PRICE DROP

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

  2958 Marquesas Ct, Windermere, FL 34786

  PRICE IMPROVEMENT! 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 comfort, refinement, and privacy, this home embodies

  Dianna Desboyaux DOUGLAS ELLIMAN

  2958 Marquesas Ct, 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
• 

  

  /19

  $832,000

  • 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

  $939,000

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

  11326 Ledgement Ln, Windermere, FL 34786

  One or more photo(s) has been 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

  Jingjing Guan AAA GLOBAL VENTURES PA

  11326 Ledgement Ln, Windermere, FL 34786
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  /4

  $2,400,000

  • 4 Beds
  • 3.5 Baths
  • 3,101 Sq Ft

  10520 Park Ridge Gotha Rd, Windermere, FL 34786

  This listing presents two distinct 1+ acre residential properties, located at 10532 & 10520 Park Ridge Gotha Rd, offering a unique opportunity: a 2.522-acre residential estate parcel situated in Windermere, Florida. The two adjacent lots, both exceeding one acre, currently feature vacant, yet well-maintained, older single-family homes. Windermere is renowned as one of Central Florida's most

  David Weaver DAVID WEAVER, REALTOR

  10520 Park Ridge Gotha Rd, Windermere, FL 34786
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  /43

  $2,400,000

  • 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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  /53

  $1,398,000

  $100K PRICE DROP

  • 5 Beds
  • 4.5 Baths
  • 3,835 Sq Ft

  7231 Sangalla Dr, Windermere, FL 34786

  Located in the gated community of Casa Del Lago in Windermere, featuring just 88 luxury homes surrounding Lake Burden, this neighborhood offers an exceptional setting near top-rated schools and only minutes from Orlando’s most popular destinations, including major highways, airports, shopping, dining, and world-renowned attractions. Built by one of the nation’s top private homebuilders, David

  Matt Kester THE REAL ESTATE COLLECTION LLC

  7231 Sangalla Dr, Windermere, FL 34786
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  /6

  $2,400,000

  • Land
  • 2.52 Acres
  • $952,381 per Acre

  10532 Park Ridge Gotha Rd, Windermere, FL 34786

  This listing presents two distinct 1+ acre residential properties, located at 10532 & 10520 Park Ridge Gotha Rd, offering a unique opportunity: a 2.522-acre residential estate parcel situated in Windermere, Florida. The two adjacent lots, both exceeding one acre, currently feature vacant, yet well-maintained, older single-family homes. Windermere is renowned as one of Central Florida's most

  David Weaver DAVID WEAVER, REALTOR

  10532 Park Ridge Gotha Rd, Windermere, FL 34786
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  /61

  $2,950,000

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

  4301 Down Point Ln, Windermere, FL 34786

  Lakefront estate on Lake Down in the Butler Chain of Lakes with over 150 feet of frontage and no HOA in Sunset Bay. Built in 1983, this 5 bedroom, 4 bath pool home offers nearly 7,000 square feet across three levels and presents a rare opportunity to renovate a true chain-of-lakes property to your own style and standards. Home retains much of its original character and is priced accordingly,

  Phillip Mariani EXP REALTY LLC

  4301 Down Point Ln, 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

  $925,000

  $50K PRICE DROP

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

  3328 Wax Berry Ct, Windermere, FL 34786

  One or more photo(s) has been virtually staged. 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 floor plan that

  Ferris Kassar PREFERRED REAL ESTATE BROKERS

  3328 Wax Berry Ct, Windermere, FL 34786
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  /28

  $750,000

  $100K PRICE DROP

  • 4 Beds
  • 4 Baths
  • 3,435 Sq Ft

  9669 Westover Club Cir, Windermere, FL 34786

  PRICED TO SELLLL!!! Behind the gates of Westover Club, 9669 Westover Club Circle offers a timeless Windermere setting with privacy, mature landscaping, and seamless indoor-outdoor living on nearly half an acre. Designed for both entertaining and everyday comfort, the home blends classic style with a functional layout in one of the area’s most desirable gated communities. Featuring 4 bedrooms, 4

  Regina Ferdinand FIRST WORLD REALTY GROUP

  9669 Westover Club Cir, Windermere, FL 34786
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  /35

  $1,119,000

  • 5 Beds
  • 4 Baths
  • 3,804 Sq Ft

  6379 Swanson St, Windermere, FL 34786

  From the moment you arrive, this Mediterranean home in the highly sought after Enclave makes an impression. It offers a balance of grand design and everyday livability.Inside, the entryway features rich paneling and an open railed staircase that sets the tone. The open floor plan flows into a bright family room and gourmet kitchen designed for both daily living and entertaining. The oversized

  John Cunningham KELLER WILLIAMS CLASSIC

  6379 Swanson St, Windermere, FL 34786
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  /71

  $3,195,000

  $300K PRICE DROP

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

  5538 W Lake Butler Rd, Windermere, FL 34786

  Welcome to 5538 W Lake Butler Road—an expansive, newly renovated estate set on 1.9 acres of lush, lakefront land in arguably one of Central Florida’s most coveted locations, Kelso on Lake Butler. What distinguishes this property is its remarkable dual lake access. Your own private boat dock provides direct skiable waterfront on Lake Davis, while exclusive community privileges grant you gated

  Julie Bettosini STOCKWORTH REALTY GROUP

  5538 W Lake Butler Rd, Windermere, FL 34786
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  /64

  $1,450,000

  $49K PRICE DROP

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

  9119 Balmoral Mews Square, Windermere, FL 34786

  Welcome to an exceptional opportunity in the exclusive gated enclave of Balmoral home to just 32 custom residences—where privacy, elegance, and the coveted Windermere lifestyle come together seamlessly. Situated on over half an acre, this beautifully landscaped property offers a serene retreat with mature greenery and a fully fenced yard designed for both relaxation and entertaining. Step through

  Seana Abdelmajid LA ROSA REALTY BEACHES LLC

  9119 Balmoral Mews Square, Windermere, FL 34786

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