Windermere Homes for Sale

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  /100

  $1,490,000

  • 5 Beds
  • 4 Baths
  • 3,492 Sq Ft

  11339 Camden Park Dr, Windermere, FL 34786

  Luxury Pond-View Home in Keene’s Pointe – WindermereLocated in the highly sought-after gated golf community of Keenes Pointe, this beautiful 5-bedroom, 4-bathroom residence offers an exceptional combination of space, comfort, and scenic surroundings.The home features a thoughtfully designed floor plan with a private den/office, formal living and dining rooms, and expansive living areas

  Martonio Pinto AMERICAN HORIZONS REALTY

  11339 Camden Park Dr, 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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  /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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  /73

  $3,950,000

  New Construction $1M 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. SELLER MOTIVATED!!! UNMATCHED PRICE AND OPPORTUNITY! 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,

  Jennifer Wemert WEMERT GROUP REALTY LLC

  1009 Down Reserve Ct, 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
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  /35

  $2,200,000

  • 8 Beds
  • 8.5 Baths
  • 4,735 Sq Ft

  11545 Brickyard Pond Ln, Windermere, FL 34786

  Luxury Lakefront Estate – Windermere, FL Discover a truly extraordinary lakefront residence located at one of Windermere's most prestigious addresses. Situated on a sprawling 0.75-acre lot, this property impresses with its grandeur, elegance, and impeccable attention to detail. With 8 spacious bedrooms, 9 full bathrooms, and 1 powder room, the home was designed to offer absolute comfort and a

  Jennifer Paiano Olmeda WRA BUSINESS & REAL ESTATE

  11545 Brickyard Pond Ln, Windermere, FL 34786
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  /62

  $1,750,000

  $140K PRICE DROP

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

  3013 Seigneury Dr, Windermere, FL 34786

  Stylish and elegant with contemporary touches, welcome home to a magnificent and expansive retreat situated on a 1-acre lot, with full-size lighted sport court with double pickleball courts (or tennis or basketball), set inside the gated enclave of Harbor Isle. This spectacular residence is unduplicated for its secluded setting – yet so close to everything – while offering an abundance of

  Rob Rahter STOCKWORTH REALTY GROUP

  3013 Seigneury Dr, 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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  /100

  $3,350,000

  $150K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 5,273 Sq Ft

  10577 Down Lakeview Cir, Windermere, FL 34786

  Experience true lakefront living on the famed Butler Chain of Lakes. This exceptional custom home offers 137 feet of pristine shoreline and sits on nearly one acre of high, dry land with sweeping panoramic water views and nightly Disney fireworks. Arrive via a circular paved drive framed by mature oaks and step onto the covered porch through an impressive 8 inch solid cedar entry door with

  Simon Simaan THE SIMON SIMAAN GROUP

  10577 Down Lakeview Cir, Windermere, FL 34786
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  /46

  $575,000

  $10K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,139 Sq Ft

  6442 Golden Dewdrop Trail, Windermere, FL 34786

  Short Sale. Come see this beautiful place. This immaculate home features include over 2,100 square feet of living space, a desirable Kitchen with 42" Cabinets and Granite, Stainless Steel Appliances, Beautiful Backsplash, engineered hardwood flooring on the first floor, vinyl on the second floor, ceramic tile in bathrooms and laundry, screened-in patio porch with a ceiling fan, an elegant

  Yindy Reyes EMPIRE NETWORK REALTY

  6442 Golden Dewdrop Trail, Windermere, FL 34786
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  /26

  $4,395,000

  • Land
  • 1 Acre
  • $4,395,000 per Acre

  12418 Park Ave, Windermere, FL 34786

  WELCOME TO PARK AVENUE. An extraordinary opportunity awaits on 1 acre of prime lakefront with coveted southeastern exposure and sweeping panoramic views. Perfectly positioned along the pristine shoreline of Lake Butler on the renowned Butler Chain of Lakes, this exclusive homesite is located within one of Windermere’s most desirable gated enclaves—Chaine Du Lac. Offering the rare distinction of

  Michael Julian JULIAN PROPERTIES, INC.

  12418 Park Ave, Windermere, FL 34786
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  /82

  $2,175,000

  $110K PRICE DROP

  • 6 Beds
  • 6 Baths
  • 5,031 Sq Ft

  713 Main St, Windermere, FL 34786

  Architecturally refined and thoughtfully designed, this custom built Transitional Craftsman residence blends timeless craftsmanship with modern luxury in the heart of Historic Olde Windermere with excellent walkability. Rich wood detailing, exposed pecky cypress beams, and dramatic stonework create warmth and depth throughout. The chef’s kitchen is both functional and sculptural, featuring a

  

  Kari Fleck

  THE REAL ESTATE COLLECTION LLC

  713 Main St, Windermere, FL 34786
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  /28

  $10,500,000

  $1M PRICE DROP

  • Land
  • 9.03 Acres
  • $1,162,791 per Acre

  4226 Downeast Ln, Windermere, FL 34786

  Dramatic price improvement on this exceptional 5+ acre Lake Down development opportunity, offering 300 feet of pristine shoreline on the coveted Butler Chain of Lakes and positioned on the best side of Windermere with unmatched convenience to SR-408 and downtown Orlando. This rare parcel, zoned R-CE, allows for the creation of up to three luxury lakefront homes or a single premier estate

  Thad Czapka COLDWELL BANKER REALTY

  4226 Downeast Ln, Windermere, FL 34786
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  /58

  $965,000

  $110K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,743 Sq Ft

  2125 Kane Park Way, Windermere, FL 34786

  Fresh Exterior Updates! This beautifully updated custom home has just been refreshed with new exterior paint and a newly painted pool deck, enhancing its curb appeal and outdoor living spaces. Updated professional photography will be added soon to showcase the refreshed exterior and recent improvements. Rare opportunity to own a custom pool home on .71 acres in the Town of Windermere for under $1

  Deb Schroeder INFINITY REALTY GROUP LLC

  2125 Kane Park Way, Windermere, FL 34786
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  /32

  $1,855,000

  $245K 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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  $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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  /55

  $995,000

  $50K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 3,248 Sq Ft

  11162 Ledgement Ln, Windermere, FL 34786

  NEW TILE ROOF INSTALLED PRIOR TO CLOSING! Located in Glenmuir, one of Windermere's most sought-after gated communities, this beautifully maintained pool home offers 4 bedrooms, 3 full baths, 2 half baths, a private office, bonus room, and a desirable mostly single-story floor plan. Backing to peaceful greenspace with NO REAR NEIGHBORS, this home combines privacy, functionality, and resort-style

  Deb Schroeder INFINITY REALTY GROUP LLC

  11162 Ledgement Ln, Windermere, FL 34786
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  /30

  $2,175,000

  New Construction $250K PRICE DROP

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

  436 E 7th Ave, Windermere, FL 34786

  Seller is Motivated and open to negotiate! Luxury new construction lakefront home in Windermere, newly completed. Situated on Lake Bessie, this modern custom residence delivers architectural elegance, premium finishes, and a prime location just steps from the Town Center. The home offers 3,136 sq ft of air-conditioned space, featuring 4 en-suite bedrooms, a dedicated office at the entry, 5 full

  DENILEY VALDES TALENT REALTY SOLUTIONS

  436 E 7th Ave, Windermere, FL 34786
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  /32

  $1,390,000

  Open Sat 12PM - 3PM $110K PRICE DROP

  • 6 Beds
  • 4.5 Baths
  • 4,999 Sq Ft

  17538 Black Rail St, Windermere, FL 34786

  Spacious 6-bedroom, 4-bath Windermere home with dual master suites, pond views, and a fenced yard. Built in 2014, this residence features an open layout with a gourmet kitchen, granite counters, stainless steel appliances, and 42” cabinets. Upstairs includes a loft/media room and generously sized bedrooms. Enjoy serene water views, a private backyard, and a 3-car garage. Located in a desirable

  

  Elaine Garcia

  GARCIA REALTY GROUP

  17538 Black Rail St, Windermere, FL 34786
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  /2

  $575,000

  $25K PRICE INCREASE

  • Land
  • 20,473 Sq Ft
  • $1,223,404 per Acre

  9802 6th St, Windermere, FL 34786

  Vacant lot on the corner of 6th and Hempel. Prime investment property.

  Judy Plett UPSIDE REAL ESTATE INC

  9802 6th St, Windermere, FL 34786
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  /63

  $1,875,000

  $75K PRICE DROP

  • 5 Beds
  • 4 Baths
  • 4,489 Sq Ft

  13420 Bonica Way, Windermere, FL 34786

  Experience the Florida lifestyle in this stunning FULLY FURNISHED 5-Bed/4-Bath pool home on over 1/2-acre, with a welcoming open floor plan spanning 4,500 square feet, spectacular Theater Room, custom upgrades and designer accents throughout, and new dual-zoned AC system in August 2025 including Nest smart thermostat. Situated across from the community park and tennis on one of the best

  Frank Ferrell FERRELL REALTY, INC.

  13420 Bonica Way, Windermere, FL 34786
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  /65

  $3,200,000

  $50K PRICE DROP

  • 6 Beds
  • 6.5 Baths
  • 6,308 Sq Ft

  13448 Bellaria Cir, Windermere, FL 34786

  Buyer walked days before closing due to personal reasons! All inspections and milestones clean/clear!! - This exceptional Florida residence is perfectly sited on an acre within the exclusive guard-gated community of Bellaria. Thoughtfully designed to balance sophistication with comfort, the home welcomes you with an abundance of natural light streaming through broad front windows, highlighting

  Shawn Kennedy KENNEDY REALTY GROUP LLC

  13448 Bellaria Cir, Windermere, FL 34786
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  /3

  $2,200,000

  New Construction $1M PRICE DROP

  • 4 Beds
  • 4.5 Baths
  • 3,889 Sq Ft

  2 Chase Rd, Windermere, FL 34786

  Pre-Construction. To be built. Pre-Construction. To be built. Pre-Construction | To Be Built | Designed for Unparalleled Luxury Discover an extraordinary opportunity to own a masterfully designed luxury residence in this Windermere community. This exquisite estate, crafted by the renowned Supreme Construction, offers a perfect blend of sophistication, innovation, and timeless elegance. Property

  Matthew Hughes REAL BROKER, LLC

  2 Chase Rd, Windermere, FL 34786
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  $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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  /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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  /46

  $975,000

  $225K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 2,618 Sq Ft

  3629 Lake Buynak Rd, Windermere, FL 34786

  Now offered at an exceptional value, this 1.3-acre property in Lake Buynak Estates presents a rare opportunity to enjoy acreage, privacy and flexibility in one of Central Florida's most desirable locations. Located within the highly sought-after Windermere ZIP code, this 4-bedroom, 3.5-bath residence offers more than 2,600 square feet of living space with a thoughtfully designed split floor plan,

  

  Tania Matthews

  KELLER WILLIAMS ELITE PARTNERS III REALTY

  3629 Lake Buynak Rd, Windermere, FL 34786
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  /9

  $5,995,000

  New Construction

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

  13377 Lake Butler Blvd, Winter Garden, FL 34787

  Pre-Construction. To be built. To be Built, Rendering provided by master custom home builder, David Konkol of Konkol Custom Homes. However, buyer can work with builder to build any design buyer prefers (pricing to adjust accordingly). The property is spectacular waterfront acreage with boat dock on boatable, skiable Lake Roper. Acreage is 12.4 +/- with some conservation. Zoned A-1 (agricultural

  Dawn Briggs BLUE MAGNOLIA REALTY LLC

  13377 Lake Butler Blvd, Winter Garden, FL 34787
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  /19

  $809,000

  $111K 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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  /62

  $1,151,000

  $344K PRICE DROP

  • 5 Beds
  • 4.5 Baths
  • 3,449 Sq Ft

  11333 Camden Park Dr Unit 7, Windermere, FL 34786

  Virtually Staged. "HUGE PRICE REDUCTION" - Nestled within highly sought after guard gated community, this exceptionally maintained two-story residence combines timeless elegance offering the ideal blend of style, comfort, and functionality. The home features 5 spacious bedrooms, 4.5 bathrooms, dinning room, separate living room from family room and a generously sized loft—ideal for a secondary

  Cynthia Noto KARDOSH REALTY

  11333 Camden Park Dr Unit 7, Windermere, FL 34786
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  /63

  $2,375,000

  $120K PRICE DROP

  • 5 Beds
  • 4 Baths
  • 4,793 Sq Ft

  4224 Clarice Estates Dr, Windermere, FL 34786

  Welcome to The Estates at Lake Clarice—one of Windermere's best-kept secrets. If your dream home checklist includes private lake views, breathtaking sunsets, peace and tranquility, and a boutique neighborhood setting, your search may be over. Built in 2018 and recently refreshed with numerous upgrades, this immaculate custom lakefront residence offers an exceptional blend of luxury, comfort, and

  Paul Hickey FLORIDA GOLD REAL ESTATE LLC

  4224 Clarice Estates Dr, Windermere, FL 34786
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  /26

  $900,000

  $100K PRICE DROP

  • Land
  • 21,780 Sq Ft
  • $1,800,000 per Acre

  2504 Windermere Reserve Ct, Windermere, FL 34786

  Final Opportunity – Last Lot Available in The Reserve at Windermere! Build your dream home in the exclusive community of The Reserve at Windermere with acclaimed custom builder Element Home Builders. This final remaining homesite of 8 offers a rare opportunity to craft a one-of-a-kind luxury residence in one of Central Florida’s most prestigious neighborhoods. Surrounded by the natural beauty of

  Carolina Dumit CORCORAN PREMIER REALTY

  2504 Windermere Reserve Ct, Windermere, FL 34786
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  $1,630,000

  • 3 Beds
  • 2 Baths
  • 2,238 Sq Ft

  11923 Lake Butler Blvd, Windermere, FL 34786

  Nestled on one of Windermere’s most desirable streets, this charming home offers a rare opportunity to enjoy small-town living on a beautifully wooded one-acre lot. The property features a welcoming covered entry with double doors that open into a light-filled foyer and spacious family room with soaring vaulted ceilings and a cozy wood-burning fireplace. The open-concept kitchen includes a large

  Michael Julian JULIAN PROPERTIES, INC.

  11923 Lake Butler Blvd, Windermere, FL 34786
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  /28

  $2,500,000

  • 4 Beds
  • 4.5 Baths
  • 4,961 Sq Ft

  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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  /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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  /51

  $1,575,000

  $114K PRICE DROP

  • 5 Beds
  • 3 Baths
  • 3,300 Sq Ft

  13124 Filly Ct, Windermere, FL 34786

  Welcome to a rare opportunity in one of Windermere’s most exquisite communities where luxury living meets farmland feel. The Farms community consists of 12 properties of one or more acres each. The community also has a horse stable that homeowners can keep horses. Nestled at the end of a cul-de-sac, this gorgeous estate offers sophistication, premium finishes and a quaint feeling throughout.As

  Marcelo Brandao HOME N OFFICES INTERNATIONAL

  13124 Filly Ct, Windermere, FL 34786
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  /71

  $3,999,999

  $200K PRICE DROP

  • 5 Beds
  • 8 Baths
  • 6,248 Sq Ft

  11002 Lake Butler Blvd, Windermere, FL 34786

  Price Adjustment! Lakefront Living in the Heart of Windermere – A Rare Opportunity for Multigenerational Luxury Situated along the tranquil, open waters of Wauseon Bay—part of the world-renowned Butler Chain of Lakes—this expansive estate on prestigious Lake Butler Boulevard is more than just a home: it’s a lifestyle destination, purposefully designed to inspire connection, relaxation, and

  Sean Oakley SERENDIPITY REALTY LLC

  11002 Lake Butler Blvd, Windermere, FL 34786
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  /91

  $17,250,000

  $3M PRICE DROP

  • 7 Beds
  • 8.5 Baths
  • 10,649 Sq Ft

  11900 Lake Butler Blvd, Windermere, FL 34786

  Presenting Sunset Isle: an iconic waterfront estate compound capturing timeless elegance on Windermere’s largest and most prestigious Lake Butler, offering captivating unobstructed views from its 700 feet of lake frontage, a private island with moat and drawbridge, sandy beaches, two story double residence guest house, and a majestic and stunning grand mansion with additional guest retreat, all

  Julie Bettosini STOCKWORTH REALTY GROUP

  11900 Lake Butler Blvd, Windermere, FL 34786

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