Windermere, FL Homes for Sale

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  /49

  $1,200,000

  • 4 Beds
  • 4 Baths
  • 2,787 Sq Ft

  1361 Whitney Isles Dr, Windermere, FL 34786

  Stunning residence with a private fenced backyard, located in the highly sought-after gated community of Belmere in Windermere, just minutes from the town center. Featuring 4 bedrooms, 4 bathrooms, and approximately 2,800 sq. ft. of air-conditioned living space, this home immediately captivates with its elegant Mediterranean architecture and lush tropical landscaping. Fully renovated this year,

  Gabriel Mantovani ALVES AND HOWELL REALTY

  1361 Whitney Isles Dr, Windermere, FL 34786
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  /44

  $750,000

  • 4 Beds
  • 3.5 Baths
  • 3,413 Sq Ft

  11903 Cave Run Ave, Windermere, FL 34786

  Stunning move-in ready home in the highly sought-after Windermere Trails community, located in a top-rated school district and just 2 miles from Walt Disney World! This beautifully upgraded 4-bedroom, 3.5-bath home features a gourmet kitchen with an oversized center island, custom solid wood cabinetry, granite countertops, built-in ovens, and a spacious walk-in pantry — perfect for entertaining

  Yan Zheng LOKATION

  11903 Cave Run Ave, Windermere, FL 34786
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  /2

  $575,000

  • Land
  • 0.47 Acre
  • $1,223,404 per Acre

  9802 6th St, Windermere, FL 34786

  Corner residential lot in Gotha. Small town charm near Windermere. No HOA. Shaded with Oaks. Easy access to 408 and Florida Turnpike. Great location, desirable schools and convenient to shopping, hospital, restaurants and more.

  Judy Plett UPSIDE REAL ESTATE INC

  9802 6th St, Windermere, FL 34786
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  /35

  $814,000

  • 4 Beds
  • 3.5 Baths
  • 3,044 Sq Ft

  7123 Calm Cove Ct, Windermere, FL 34786

  Beautifully updated 4-bedroom, 3.5-bath two-story home located on a quiet cul-de-sac in the highly sought-after Ashlin Park community of Windermere. This spacious residence offers a functional layout with generous living and dining areas, perfect for both everyday living and entertaining. The kitchen and main living spaces flow seamlessly toward the backyard, where you’ll enjoy the privacy of no

  Brandon McCarter RE/MAX PRIME PROPERTIES

  7123 Calm Cove Ct, Windermere, FL 34786
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  /63

  $1,590,000

  • 4 Beds
  • 4.5 Baths
  • 3,288 Sq Ft

  1703 Roberts Landing Rd, Windermere, FL 34786

  This elegant and fully renovated lakefront home on Lake Olivia in Windermere offers the ultimate blend of luxury, comfort, and Florida lifestyle. Featuring three master suites plus a guest bedroom and bathroom, the spacious layout is designed for both entertaining and everyday living. Large windows fill the home with natural light and frame breathtaking views of the water, while recent

  Wui Keong Goh INTERNATIONAL NETWORK REALTY

  1703 Roberts Landing Rd, Windermere, FL 34786
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  /42

  $769,900

  • 5 Beds
  • 3.5 Baths
  • 3,390 Sq Ft

  6615 Helmsley Cir, Windermere, FL 34786

  Beautifully remodeled and impeccably maintained, this spacious 3,390 sq. ft. two-story home offers 5 bedrooms, 3.5 bathrooms, an office, and an attached 2-car garage in the highly desirable community of Preston Square in Windermere. Perfectly situated on a premium lot with no rear neighbors, the home features a charming front porch and covered balcony overlooking the serene, tree-lined

  Angela Gann KELLER WILLIAMS ELITE PARTNERS III REALTY

  6615 Helmsley Cir, Windermere, FL 34786
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  /34

  $389,000

  • 3 Beds
  • 2.5 Baths
  • 2,028 Sq Ft

  14215 Desert Haven St, Windermere, FL 34786

  Welcome to this stunning, move-in-ready townhome in the highly sought-after Windermere community of Oasis Cove at Lakeview Village. Boasting over 2,000 heated Sq. Ft. of meticulously maintained living space, this residence offers the perfect blend of modern updates and functional design. The first floor features a bright, open-concept living and dining area that flows seamlessly into a spacious

  Brandi Crain Iron Valley R.E.Osceola

  14215 Desert Haven St, Windermere, FL 34786
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  /62

  $1,875,000

  • 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 AC system in August 2025. Situated across from the community park and tennis on one of the best waterfront lots in sought-after gated Tildens Grove,

  Frank Ferrell FERRELL REALTY, INC.

  13420 Bonica Way, 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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  /71

  $1,199,000

  • 4 Beds
  • 3 Baths
  • 2,599 Sq Ft

  8351 Bowden Way, Windermere, FL 34786

  Nestled within the highly acclaimed guard-gated community of Keene’s Pointe, this completely remodeled Windermere home offers a 4-bedroom, 3-bathroom estate that showcases timeless architectural details, curated modern finishes, and a seamless indoor-outdoor luxury lifestyle. Step inside to discover a light-filled open layout with tall coffered ceilings, custom-laid wood tile flooring, formal

  Sharon Brandt KELLER WILLIAMS REALTY AT THE LAKES

  8351 Bowden Way, Windermere, FL 34786
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  /47

  $929,900

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

  12941 Westside Village Loop, Windermere, FL 34786

  Experience the elegance of Westside Village in Windermere, where timeless design meets modern luxury. This five-bedroom, four-bath residence spans 3,717 square feet of thoughtfully designed living space, built in 2018. The foyer welcomes you with porcelain tile floors, vaulted ceilings, and chandelier lighting that set a tone of quiet sophistication. French doors open to a versatile home office,

  Keren Reyes CENTURY 21 CARIOTI

  12941 Westside Village Loop, Windermere, FL 34786
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  /18

  $539,000

  • 3 Beds
  • 2 Baths
  • 2,148 Sq Ft

  12863 Holdenbury Ln, Windermere, FL 34786

  Experience refined living in this impeccably upgraded residence located in Lakes of Windermere.This elegant 3-bedroom, 2-bathroom home showcases a seamless blend of modern sophistication and everyday comfort, featuring a thoughtfully designed split floor plan and no carpet throughout for a clean, contemporary aesthetic.From the moment you enter, you’re welcomed by light-filled living

  Maria Castro-Aversano LPT REALTY, LLC

  12863 Holdenbury Ln, Windermere, FL 34786
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  /4

  $395,000

  • 3 Beds
  • 2.5 Baths
  • 1,520 Sq Ft

  8638 Brookvale Dr, Windermere, FL 34786

  Great opportunity to own this wonderful townhouse in the beautiful Lake Reams community near Disney World! This townhouse features 3bedrooms, 2.5 bathrooms, a 2-car garage, and a spacious courtyard for outdoor gatherings, a fully equipped kitchen that opens up into a living room. All bedrooms are located upstairs for privacy. The primary bedroom offers high ceilings and a spacious walk-in

  Karina Aumaitre AK GLOBAL REALTY LLC

  8638 Brookvale Dr, Windermere, FL 34786
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  /28

  $1,350,000

  • 4 Beds
  • 4.5 Baths
  • 3,831 Sq Ft

  3138 Seigneury Dr, Windermere, FL 34786

  Timeless style and classic design unfold behind the gates of Harbor Isle, one of Windermere’s most sought-after communities. This custom-built estate residence offers captivating views of Lake Down on the pristine Butler Chain of Lakes. Featuring all living areas on the first floor except for a bonus room upstairs, this thoughtfully crafted home offers separate formal and living spaces and a

  Rob Rahter STOCKWORTH REALTY GROUP

  3138 Seigneury Dr, Windermere, FL 34786
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  /46

  $899,900

  • 4 Beds
  • 3.5 Baths
  • 3,424 Sq Ft

  13302 Roskin Ln, Windermere, FL 34786

  Welcome to this impeccably maintained former model home in Windermere, beautifully positioned on a premium corner lot in a quiet, highly desirable community and zoned for top-rated schools. Offering over 3,400 square feet with 4 bedrooms and 3.5 bathrooms, this home stands out for its smart use of space, generous room sizes, and the refined “model home” presentation that feels clean, polished,

  Xiaoyu Su RATIO REAL ESTATE, LLC

  13302 Roskin Ln, Windermere, FL 34786
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  /3

  $1,172,945 New Construction

  • 5 Beds
  • 3.5 Baths
  • 3,764 Sq Ft

  Deerfield Plan at Palms at Windermere, Windermere, FL 34786

  The Deerfield floorplan is a spacious two-story home designed for growing families, featuring 5 bedrooms and 3.5 bathrooms. This layout offers an ideal combination of private retreats and open gathering spaces. The first floor includes the primary bedroom suite, complete with a luxurious bathroom and walk-in closet, a separate study perfect for working from home, and an expansive great room

  Dream Finders Homes Builder

  14207 Crest Palm Ave Unit 36467792, Windermere, FL 34786
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  /97

  $3,299,000

  • 6 Beds
  • 8 Baths
  • 7,217 Sq Ft

  4029 Isabella Cir, Windermere, FL 34786

  Experience an architectural masterpiece in the gated enclave of Casabella. Situated on a rare, oversized .85-acre lot, this estate has been transformed by the original owner with impeccable attention to detail. The interior features 6 beds, 6 full and 2 half baths, all the high-scratch-resistant flooring throughout the home comes in a beautiful white oak finish with bathrooms featuring porcelain

  Mauro Costa CORCORAN PREMIER REALTY

  4029 Isabella Cir, Windermere, FL 34786
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  /75

  $9,999,000

  • 6 Beds
  • 8 Baths
  • 6,783 Sq Ft

  6149 Grosvenor Shore Dr, Windermere, FL 34786

  Keene's Pointe - Stunning lakefront home on Lake Tibet of the famed Butler Chain of Lakes. No detail was spared in this completely renovated home boasting formal living and dining rooms, family and media room, 2 offices, 6 full/2 half baths and 6 bedrooms - one of which could serve as a in-law suite with separate entrance from the outside. From the moment you enter this impeccably designed home

  Teresa Stewart SOUTHERN REALTY GROUP LLC

  6149 Grosvenor Shore Dr, Windermere, FL 34786
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  /60

  $2,995,000

  • 4 Beds
  • 5 Baths
  • 4,693 Sq Ft

  10870 Bayshore Dr, Windermere, FL 34786

  Set against the shimmering waters of Little Lake Down, this extraordinary lakefronthome offers an elevated expression of luxury living. Thoughtfully designed to maximizesweeping water views, the residence delivers a refined yet inviting atmosphere ideal forboth intimate living and grand entertaining. As you step inside you are greetedby a spacious open floor plan, highlighted by a

  Julie Christensen ONE LUXURY INTERNATIONAL LLC

  10870 Bayshore Dr, Windermere, FL 34786
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  /30

  $6,490,000

  • 6 Beds
  • 5.5 Baths
  • 6,706 Sq Ft

  1002 Down Reserve Ct, Windermere, FL 34786

  Luxury, architectural elegance, and an unparalleled lakefront lifestyle on the Butler Chain of Lakes in Windermere. Set on a sprawling lot of over one acre, this extraordinary waterfront estate offers direct access to the prestigious Butler Chain of Lakes — a rare interconnected system of 12 private lakes, providing one of the most exclusive boating lifestyles in Central Florida. From the moment

  Jennifer Olmeda WRA BUSINESS & REAL ESTATE

  1002 Down Reserve Ct, Windermere, FL 34786
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  /60

  $639,900

  • 4 Beds
  • 3.5 Baths
  • 2,812 Sq Ft

  5224 Lemon Twist Ln, Windermere, FL 34786

  Welcome to the lowest-priced single-family home in the highly desirable Summerport community in Windermere. This well-maintained home features 4 bedrooms, 3.5 baths, a formal dining room, a private office, and a versatile loft/bonus space. Recent updates include a new roof (2021), fresh interior paint, and two new HVAC units (2023). The open-concept layout offers a spacious kitchen with 42” maple

  Carmen Aridas RE/MAX PRIME PROPERTIES

  5224 Lemon Twist Ln, Windermere, FL 34786
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  /41

  $574,995

  • 4 Beds
  • 2 Baths
  • 1,798 Sq Ft

  9319 Woodbreeze Blvd, Windermere, FL 34786

  WONDERFUL WINDERMERE 4 BED/ 2 BATH HOME LOCATED IN THE CHARMING COMMUNITY OF SILVER WOODS. The moment you drive up to this home you are greeted by low maintence landscaping, paver driveway and a unique courtyard entry which makes this home standout. The courtyard is a perfect space to spend the evenings or start your mornings. Sliders from the kitchen lead onto the courtyard. Upon entering you

  Steven Looper CHARLES RUTENBERG REALTY ORLANDO

  9319 Woodbreeze Blvd, Windermere, FL 34786
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  /69

  $2,868,000

  • 6 Beds
  • 6 Baths
  • 4,920 Sq Ft

  13304 Bellaria Cir, Windermere, FL 34786

  Some residences are simply houses. Others are a statement. Welcome to Casa Pietra — an exceptional estate nestled within Bellaria, one of Windermere's most exclusive guard-gated communities, where only 64 homes share the privilege of calling this address home. Set on nearly 3⁄4 of an acre with serene water views, this meticulously curated two-story residence offers just under 5,000 square feet of

  Caroline De Castro Marcellini COMPASS FLORIDA, LLC

  13304 Bellaria Cir, Windermere, FL 34786
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  /29

  $725,000

  • 4 Beds
  • 2 Baths
  • 2,373 Sq Ft

  17514 Black Rail St, Windermere, FL 34786

  New painting interior and doors and baseboards. This elegant single-level detached home features soaring 10-foot ceilings throughout, creating a bright and spacious atmosphere rarely found in one-story living. The home is thoughtfully positioned with a tranquil pond at the rear, offering both beautiful water views and exceptional privacy. A classic tiled roof adds timeless character and

  He Gao U S GLORY REALTY

  17514 Black Rail St, Windermere, FL 34786
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  $587,990 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,714 Sq Ft

  Butler Plan at Lake Cawood Cove - Townhomes, Windermere, FL 34786

  Ashton Woods Builder

  5432 Winter Garden Vineland Rd Unit 37932782, Windermere, FL 34786
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  /29

  $649,000

  • 5 Beds
  • 3.5 Baths
  • 2,960 Sq Ft

  12936 Droxford Rd, Windermere, FL 34786

  Lakes of Windermere STUNNER! This Ashton Woods Kensington model comes with an amazing bonus room and much more! The well-established neighborhood is out of a Norman Rockwell painting, lined with trees, 15 minutes from Disney, and loaded with charm. All you will need are a couple of Adirondack chairs for the front patio and a glass of sweet tea to become part of this amazing neighborhood. The

  Leo Rico UNITED REAL ESTATE PREFERRED

  12936 Droxford Rd, Windermere, FL 34786
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  /81

  $5,000,000

  • 6 Beds
  • 9 Baths
  • 8,305 Sq Ft

  9721 Carillon Park Dr, Windermere, FL 34786

  Welcome to 9721 Carillon Park Dr, Windermere, FL 34786, a stunning estate inside the guard-gated community of Keene’s Pointe.This extraordinary residence offers 8,305 square feet of luxury living space with refined architectural details, elegant wood beams, and designer finishes throughout. MAIN FEATURES: • Five bedrooms plus DETACHED GUEST HOUSE and OFFICE— providing exceptional space and

  Dianna Desboyaux DOUGLAS ELLIMAN

  9721 Carillon Park Dr, Windermere, FL 34786
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  /57

  $3,400,000

  • 4 Beds
  • 4 Baths
  • 4,877 Sq Ft

  9731 Chestnut Ridge Dr, Windermere, FL 34786

  Nestled within the gates of the renowned Isleworth Golf & Country Club, this beautiful four-bedroom estate offers nearly 5,000 square feet and showcases an elegant transitional style. The main level welcomes you with gracious formal living and dining rooms, each crowned with sparkling chandeliers and framed by oversized windows that capture elevated views of the resort-style pool and spa below.

  Monica Lochmandy ISLEWORTH REALTY LLC

  9731 Chestnut Ridge Dr, Windermere, FL 34786
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  /65

  $3,200,000

  • 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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  /52

  $532,000

  • 4 Beds
  • 2.5 Baths
  • 2,048 Sq Ft

  8243 Bryce Canyon Ave, Windermere, FL 34786

  Beautiful and cozy residence located in the desirable WINDERMERE area. This single-family - bungalow style home offers four bedrooms, two-and-a-half baths and a two-car garage. There's a LOFT UPSTAIRS, perfect for a TV or office/study room. With an open floor plan and ENERGY-EFFICIENT built, the kitchen features stainless steel appliances, overlooking the family room. All bedrooms and family

  Cristian Cen Chen SIMPSON REALTY LLC

  8243 Bryce Canyon Ave, Windermere, FL 34786
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  /81

  $1,500,000

  • 4 Beds
  • 3.5 Baths
  • 4,437 Sq Ft

  13734 Lake Cawood Dr, Windermere, FL 34786

  NEW PRICE - SELLER MOTIVATED!Welcome to this stunning single-story luxury estate located in the highly sought-after gated community of Lake Cawood Estates in Windermere, Florida. Situated on nearly a full acre at the end of a cul-de-sac, this beautifully maintained four-bedroom, three-and-a-half-bathroom home offers over 4,400 square feet of spacious, thoughtfully designed living with a

  Angela Schifano CHARLES RUTENBERG REALTY ORLANDO

  13734 Lake Cawood Dr, Windermere, FL 34786
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  /91

  $3,699,888

  • 4 Beds
  • 4.5 Baths
  • 6,054 Sq Ft

  12812 Jacob Grace Ct, Windermere, FL 34786

  Experience Unmatched Lakeside Luxury in a Custom-Built MasterpieceDiscover the pinnacle of elegance and tranquility in this exquisite custom-built estate, ideally positioned on an expansive lot within an exclusive guard-gated community. With direct access to a crystal-clear spring-fed lake that permits private boat docks, this home offers a rare blend of relaxation, recreation, and refined

  Alireza Partovi EXP REALTY LLC

  12812 Jacob Grace Ct, Windermere, FL 34786
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  /47

  $900,000 Open Sat 11AM - 2PM

  • 3 Beds
  • 2 Baths
  • 2,386 Sq Ft

  4 Chase Rd, Windermere, FL 34786

  FULLY RENOVATED DREAM HOME. This home is located right in the heart of the Town of Windermere. Welcome to 4 Chase Rd, Windermere - a refined expression of luxury living where elevated design, privacy, and lifestyle converge.Set within one of Windermere’s most desirable areas, this exceptional residence delivers a seamless blend of sophistication and comfort. From its striking curb appeal to

  Matthew Hughes REAL BROKER, LLC

  4 Chase Rd, Windermere, FL 34786
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  /91

  $3,950,000

  • 6 Beds
  • 7 Baths
  • 5,709 Sq Ft

  12132 Montalcino Cir, Windermere, FL 34786

  Experience the essence of luxury lakefront living in this stunning contemporary Mediterranean estate, ideally positioned on Lake Burden within the exclusive gated community of Casa Del Lago in Windermere. This elegant two-story residence combines refined design, functionality, and breathtaking panoramic lake views throughout.The gourmet kitchen features custom dark cabinetry, quartz

  Caroline Perotti BELLA VIEW REALTY LLC

  12132 Montalcino Cir, Windermere, FL 34786
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  /39

  $449,980

  • 3 Beds
  • 2.5 Baths
  • 1,767 Sq Ft

  13369 Gorgona Isle Dr, Windermere, FL 34786

  Back on the Market! The Buyer was not able to obtain financing; you now have a new opportunity to own this gorgeous Townhome! Wow! Gorgeous, newly updated three-bedroom luxury townhome with a scenic water and fountain view. This spacious, light-filled home is open, bright, clean and move-in ready. This home features a new HVAC system with programmable thermostat, new flooring, trim and fresh

  Wendy Fischer PREMIER SOTHEBYS INT'L REALTY

  13369 Gorgona Isle Dr, Windermere, FL 34786
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  /83

  $7,595,000

  • 5 Beds
  • 6.5 Baths
  • 6,937 Sq Ft

  5074 Isleworth Country Club Dr, Windermere, FL 34786

  Luxury living perfectly positioned along the 6th fairway in the world-renowned guard-gated community of Isleworth. This exceptional estate offers over 6,900 square feet of completely remodeled space which includes over 2,400 square foot addition upstairs thoughtfully reimagined by acclaimed architect Mark Nasrallah. Featuring 5 bedrooms and 6.5 bathrooms, the home sits on over half an acre and

  Armaan Memarpouri MEMARPOURI REALTY LLC

  5074 Isleworth Country Club Dr, Windermere, FL 34786
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  /21

  $465,000

  • 3 Beds
  • 2.5 Baths
  • 1,974 Sq Ft

  12353 Via Derna Place, Windermere, FL 34786

  The house does not include furniture.Welcome to this beautifully maintained 3-bedroom, 3-bathroom townhouse, with furniture available for negotiation, located in the desirable Carrington at Windermere community. This residence provides a well-designed open-concept floor plan that seamlessly blends comfort and functionality, ideal for both everyday living and entertaining. The home features

  Tiago Ferreira AUTHENTIC REAL ESTATE TEAM

  12353 Via Derna Place, Windermere, FL 34786
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  /15

  $490,000

  • 3 Beds
  • 2.5 Baths
  • 1,977 Sq Ft

  6310 Golden Dewdrop Trail, Windermere, FL 34786

  Windermere Landings, Highly desirable community, only five minutes from downtown Windermere, and great school district. Beautiful two story home, Three bedroom Two and half bath with upstairs loft space for a home office. The Kitchen has overlooking the great family room and dining room.wood cabinets, granite countertops, an island, and counter height bar seating. A/C unit was replaced in 2019

  Mengshi Lu JOY ESTATE ENTERPRISE INC

  6310 Golden Dewdrop Trail, Windermere, FL 34786
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  /81

  $2,970,000

  • 5 Beds
  • 4 Baths
  • 3,737 Sq Ft

  10203 Trout Rd, Orlando, FL 32836

  Discover this exquisite lakefront property nestled on over 1.9 acres with more than 100 feet of water frontage on LAKE TIBET and part of the Butler Chain of Lakes. This home offers breathtaking views and absolutely stunning sunsets. As you drive onto the winding paver circular driveway with lovely fountain and beautiful landscaping, you will notice the terracotta tile roof and the undeniable

  Darlene O'Hara HOMEVEST REALTY

  10203 Trout Rd, Orlando, FL 32836
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  /100

  $14,250,000

  • 5 Beds
  • 5.5 Baths
  • 9,511 Sq Ft

  5525 Isleworth Country Club Dr, Windermere, FL 34786

  One or more photo(s) has been virtually staged. Exceptional in both style and scale, this extraordinary Isleworth estate represents the pinnacle of luxury living in one of the finest golf club communities in the world. Designed by architect Terry Irwin and built by Ballard Construction, with interior designs by Faith Fournet, the property has been fully transformed and thoughtfully curated over

  Monica Lochmandy ISLEWORTH REALTY LLC

  5525 Isleworth Country Club Dr, Windermere, FL 34786

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