Windermere, FL Homes

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  /39

  $2,150,000 Open Sat 12:30PM - 3:30PM

  • 3 Beds
  • 3 Baths
  • 2,681 Sq Ft

  647 Ridgewood Dr, Windermere, FL 34786

  One or more photo(s) has been virtually staged. Back on market — buyer’s home sale contingency did not clear. Inspection and appraisal were completed satisfactorily, no fault of the seller or property. Welcome to an extraordinary lakefront retreat on the prestigious Butler Chain of Lakes in Windermere. On a rare 1.43-acre double lot with over 200 feet of prime shoreline on Lake Down, this

  

  Linda O'Grady

  PREMIER SOTHEBYS INT'L REALTY

  (689) 302-3809

  647 Ridgewood Dr, Windermere, FL 34786
• Explore Windermere

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  /34

  $3,000 per month

  • 4 Beds
  • 3 Baths
  • 2,419 Sq Ft
  • House for Rent

  14217 Bridgewater Crossings Blvd, Windermere, FL 34786

  Don't miss out on this 4 bedroom 3 bathrooms in the tranquil Summerport community in Windermere. The first floor consists of the Kitchen, dining, family room, living room, the Master bedroom and the 3 other bedrooms and the guest bathroom. The second floor consists of the large loft, closets and a full bathroom. Don’t miss your chance to experience exceptional living very close to Keenes Crossing

  

  Azim Manji

  WEICHERT REALTORS HALLMARK PRO

  (407) 378-1123

  14217 Bridgewater Crossings Blvd, Windermere, FL 34786
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  /2

  $470,000 Sold Nov 03, 2025

  • 1,609 Sq Ft
  • $292/SF
  • 18 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2009

  6864 Helmsley Cir, Windermere, FL 34786

  One or more photo(s) has been virtually staged. *** Multiple offers received, deadline for highest and best is Monday 10/13/2025 @ 6pm ***Welcome to this beautifully updated 3-bedroom, 2-bathroom home in the highly sought-after Preston Square community of Windermere. This single-story residence offers 1,609 sq. ft. of open living space and fresh updates throughout.The heart of the home is

  Stephanie Pitts KELLER WILLIAMS CLASSIC

  6864 Helmsley Cir, Windermere, FL 34786
• 

  

  /2

  Est $652,382 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,666 Sq Ft

  8563 Greenbank Blvd, Windermere, FL 34786

  8563 Greenbank Blvd, Windermere, FL 34786
• 

  

  

  /80

  $1,499,900 Pending

  • 5 Beds
  • 4.5 Baths
  • 4,477 Sq Ft

  1450 Belfiore Way, Windermere, FL 34786

  Under contract-accepting backup offers. Welcome to Refined Living in Tuscany RidgeStep into luxury with this fully renovated, move-in-ready home, perfectly situated in the exclusive, gated community of Tuscany Ridge. Every detail of this exquisite residence has been thoughtfully updated to offer modern elegance, comfort, and timeless sophistication.The main level features a

  

  Laura Teixeira

  NOBSKA REAL ESTATE LLC

  (689) 308-3110

  1450 Belfiore Way, Windermere, FL 34786
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  /55

  $13,500 per month

  • 5 Beds
  • 6.5 Baths
  • 5,104 Sq Ft
  • House for Rent

  4302 Isabella Cir, Windermere, FL 34786

  Welcome to Casabella at Windermere, a private gated community where Spanish-inspired architecture meets modern luxury. This solar-powered estate offers 5 bedrooms, 6.5 bathrooms, and nearly an acre of beautifully landscaped grounds. Designed for a turnkey lifestyle, the home features hardwood floors, soaring ceilings, and high-quality finishes throughout. The gourmet kitchen includes KitchenAid

  

  Bruce Kalin

  JC FLORIDA REALTY LLC

  (407) 783-8539

  4302 Isabella Cir, Windermere, FL 34786
• 

  /2

  $619,000 Sold Oct 31, 2025

  • 2,076 Sq Ft
  • $298/SF
  • 6 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 2015

  13260 Penshurst Ln, Windermere, FL 34786

  **Accepting BackUp offers** Amazing opportunity to own this Professionally Designed & Renovated Gem – 4BR / 3BA in Windermere.**This property qualifies for a closing cost credit up to $5,000 through the Seller’s preferred lender.** There is truly no home like this in the area! This 4-bedroom, 3-bathroom residence has been thoughtfully renovated with over $100,000 in upgrades since 2023,

  Nadia Eggers FUTURE HOME REALTY INC

  13260 Penshurst Ln, Windermere, FL 34786
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  /2

  Est $521,823 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,151 Sq Ft

  12533 Cragside Ln, Windermere, FL 34786

  12533 Cragside Ln, Windermere, FL 34786
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  /34

  $659,000

  • 5 Beds
  • 4.5 Baths
  • 2,991 Sq Ft

  7401 Ella Ln, Windermere, FL 34786

  Spectacular Windermere Home WITH LUXURIOUS IN-LAW SUITE! Freshly painted, and brand new luxury vinyl floors. Experience the perfect blend of elegance, comfort, and versatility in this stunning 5-bedroom, 4.5-bathroom home in the prestigious Windermere community. Boasting a fully-equipped mother-in-law or older kid suite above the garage, this separate studio apartment offers privacy, abundant

  

  Kriselys Tapia

  SERHANT

  (407) 934-0478

  7401 Ella Ln, Windermere, FL 34786
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  /64

  $1,895 - $3,395 per month

  Arya at Windermere 55+ Active Adult Living

  1 - 2 Beds

  1231 Arya Way, Ocoee, FL 34761

  Enjoy a vibrant lifestyle at Arya at Windermere, a 55+ community in Ocoee, FL offering unparalleled luxury amenities, including a massage room, steam room, outdoor putting green and a micro market. Arya features open concept 1 and 2-bedroom apartments with chef-inspired kitchens, granite countertops, stainless steel appliances, breakfast bar, wood-style plank floors, walk-in shower, washer and

  1231 Arya Way, Ocoee, FL 34761
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  /2

  $1,130,000 Sold Oct 31, 2025

  • 4,213 Sq Ft
  • $268/SF
  • 23 Days On Market

  • 5 Beds
  • 4.5 Baths
  • Built 2006

  1438 Belfiore Way, Windermere, FL 34786

  Discover a home where luxury meets convenience, perfectly crafted for today's way of life. Welcome to 1438 Belfiore Way, a Luxury Single family home located in the distinguished Gated community of Tuscany Ridge in desirable city of Windermere, Florida. This beautiful home is a move-in-ready gem, modern, elegant and comfortable. Situated on a private lot at the end of the road, with no rear

  Danilo Novak NOVAK REALTY CORP

  1438 Belfiore Way, Windermere, FL 34786
• 

  /2

  Est $715,621 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,935 Sq Ft

  12995 Westside Village Loop, Windermere, FL 34786

  12995 Westside Village Loop, Windermere, FL 34786
• 

  

  /100

  $2,650,000

  • 5 Beds
  • 8 Baths
  • 7,621 Sq Ft

  9905 Lanai View Ct, Windermere, FL 34786

  BACK ON THE MARKET - BUYERS' FINANCE FELL THROUGH.Welcome to a home that isn’t just designed—it’s curated.Tucked behind the gates of one of Central Florida’s most exclusive golf communities, 9905 Lanai View Court is the kind of estate that makes you pause. Nearly 7,000 square feet of single-level, custom-crafted living plus more than 800 square feet private media room on the

  

  Bent Danholm

  MAXIM REALTY ORLANDO

  (407) 512-8409

  9905 Lanai View Ct, Windermere, FL 34786
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  /60

  $4,200 per month

  • 4 Beds
  • 2.5 Baths
  • 2,145 Sq Ft
  • House for Rent

  2943 Marquesas Ct, Windermere, FL 34786

  Come tour this incredible New England-style pool home in the Town of Windermere that sits on a meticulously manicured one-acre corner lot on a serene, tree-lined street, in the gated community of Lake Crescent Reserve. Lake Crescent is an exclusive community of 21 custom homes with mostly waterfront homes on Lake Crescent. All residents have full use of a private boat ramp to the Butler Chain of

  Jessica Alicea INTEGRITY REAL ESTATE GROUP, LLC

  2943 Marquesas Ct, Windermere, FL 34786
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  /2

  $1,050,000 Sold Oct 31, 2025

  • 2,191 Sq Ft
  • $479/SF
  • 34 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1959

  65 Oakdale St, Windermere, FL 34786

  BUTLER CHAIN OF LAKES. Tucked away on the charming, tree-lined Oakdale Street, one of the most cherished streets in the Town of Windermere, this unique property offers a rare opportunity to enjoy lake views and quick access to Lake Down, part of the prestigious Butler Chain of Lakes, which consists of 13 interconnected, spring-fed lakes known for their clarity, beauty, and recreational lifestyle.

  Tiffany Pantozzi ALIGN REAL ESTATE LLC

  65 Oakdale St, Windermere, FL 34786
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  /87

  Est $735,777 Not Listed For Sale

  • 5 Beds
  • 4.5 Baths
  • 3,512 Sq Ft

  4313 Blue Major Dr, Windermere, FL 34786

  4313 Blue Major Dr, Windermere, FL 34786
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  /40

  $535,000 Open Wed 11AM - 2PM

  • 3 Beds
  • 2.5 Baths
  • 2,009 Sq Ft

  8160 Iron Mountain Trail, Windermere, FL 34786

  BUYDOWN YOUR INTEREST RATE WITH $5000 SELLER'S CREDIT! ENERGY EFFICIENT HOME nestled in the highly desirable Windermere Trails community, this beautiful home offers an unparalleled blend of modern design, high end finishes and everyday functionality. The 3 bedrooms, 2 1/2 baths home's open-concept design seamlessly integrates the living and dining areas with the spacious kitchen and family room,

  

  Francine Arroyo Santowski

  BHHS FLORIDA REALTY

  (407) 955-9391

  8160 Iron Mountain Trail, Windermere, FL 34786
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  /46

  $1,613 - $2,657 per month

  Talcott at Windermere

  1 - 3 Beds

  5820 Nature View Dr, Windermere, FL 34786

  With thoughtful design and exclusive amenities, Talcott at Windermere, is your premier destination for luxury living in Windermere, Florida! Our luxury one, two, and three-bedroom apartments, ranging up to 1,380 square feet, redefine luxury with a range of modern interior features. Step into a home with soaring 9 foot ceilings, a stylish two-tone paint scheme, wood-style flooring, and AirPlay

  5820 Nature View Dr, Windermere, FL 34786
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  /2

  $3,840,000 Sold Oct 31, 2025

  • 6,265 Sq Ft
  • $613/SF
  • 99 Days On Market

  • 4 Beds
  • 7 Baths
  • Built 2008

  9253 Tibet Pointe Cir, Windermere, FL 34786

  Welcome to 9253 Tibet Pointe Circle in the beautiful 24-hour gated/guarded community of Keene's Pointe in Windermere, Florida. This elegantly timeless JR Watson custom-built mediterranean style home located on over 224 feet of lake frontage on Lake Tibet of the Butler Chain of Lakes, offers a functional and spacious floor plan to accommodate any buyer. Entering the drive up to the courtyard is a

  Teresa Stewart SOUTHERN REALTY GROUP LLC

  9253 Tibet Pointe Cir, Windermere, FL 34786
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  /52

  Est $2,826,222 Not Listed For Sale

  • 5 Beds
  • 6 Baths
  • 6,227 Sq Ft

  1336 Lake Olivia Ln, Windermere, FL 34786

  1336 Lake Olivia Ln, Windermere, FL 34786
• 

  

  /46

  $1,200,000

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

  3629 Lake Buynak Rd, Windermere, FL 34786

  BACK ON THE MARKET DUE TO NO FAULT OF THE PROPERTY OR SELLERS, BUT DUE TO BUYER UNFORSEEN CANCELLATION.Welcome to 3629 Lake Buynak Drive—an exceptional opportunity for investors, a custom home build or buyers seeking multigenerational living with flexibility and future upside. Situated in a desired area and on an oversized 1.3 acre lot in the Lake Buynak Estate community located off Lake

  

  Tania Matthews

  KELLER WILLIAMS ELITE PARTNERS III REALTY

  (407) 519-3922

  3629 Lake Buynak Rd, Windermere, FL 34786
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  /26

  $3,100 per month

  • 4 Beds
  • 2.5 Baths
  • 2,618 Sq Ft
  • House for Rent

  4542 Blue Major Dr, Windermere, FL 34786

  VACANT! Great location! Great Home! Move in this Great home inside the lovely SUMMERPORT/WINDERMERE community. This house is full of upgrades and is an Energy Star certified home. Downstairs has all tiled floor and new laminate. Kitchen has all fully appliances and granite counter top. You can also enjoy Disney firework at night. Upstairs has a large master bedroom, and three bedrooms. Master

  Daniel Zheng CINO INTERNATIONAL INC

  4542 Blue Major Dr, Windermere, FL 34786
• 

  /2

  $2,100,000 Sold Oct 31, 2025

  • 4,345 Sq Ft
  • $483/SF
  • 175 Days On Market

  • 5 Beds
  • 4.5 Baths
  • Built 2015

  4279 Isabella Cir, Windermere, FL 34786

  Welcome to 4279 Isabella Cir, Windermere, FL 34786. This 5-bedroom, 4/2-bathroom home has been completely remodeled and upgraded, perfectly marrying luxury with comfort. As you enter, you are greeted by an impressive formal living room with 30’ ceilings and two stories of windows that offer a stunning view of the sparkling swimming pool. Within the foyer, you will find the office to your left and

  John Silva JOHN SILVA REALTY & ASSOCIATES

  4279 Isabella Cir, Windermere, FL 34786
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  /30

  Est $878,456 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,690 Sq Ft

  8460 Elba Isle Ct, Windermere, FL 34786

  8460 Elba Isle Ct, Windermere, FL 34786
• 

  

  /32

  $1,500,000

  • 6 Beds
  • 4.5 Baths
  • 4,522 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

  (689) 312-9273

  17538 Black Rail St, Windermere, FL 34786
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  /91

  $1,835 - $3,835 per month

  Addison At Windermere

  1 - 3 Beds

  13644 Tortona Ln, Windermere, FL 34786

  Addison At Windermere is located at 13644 Tortona Lane Windermere, FL and is managed by GrayCo Properties, LLC, a reputable property management company. Addison At Windermere offers 1 to 3 bedroom apartments ranging in size from 592 to 1508 sq.ft. Amenities include Microwave and more. This rental community is pet friendly, welcoming both cats and dogs. Property is located in the 34786 ZIP code.

  13644 Tortona Ln, Windermere, FL 34786
• 

  /2

  $2,750,000 Sold Oct 31, 2025

  • 6,219 Sq Ft
  • $442/SF
  • 123 Days On Market

  • 5 Beds
  • 8 Baths
  • Built 1997

  5067 Latrobe Dr, Windermere, FL 34786

  Set along the lush fairways of Isleworth’s exclusive golf course, this Mediterranean-inspired villa blends timeless elegance with an incredible opportunity to create something truly special. Freshly updated with a new roof, newer air conditioning units, most of the windows have been replaced. The home has new paint inside and out, and new wood flooring upstairs. Starting at the grand wooden doors

  Todd Norwood BESPOKE REAL ESTATE

  5067 Latrobe Dr, Windermere, FL 34786
• 

  /2

  Est $1,411,931 Not Listed For Sale

  • 6 Beds
  • 6.5 Baths
  • 4,634 Sq Ft

  7431 Lake Albert Dr, Windermere, FL 34786

  7431 Lake Albert Dr, Windermere, FL 34786
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  /52

  $414,999

  • 3 Beds
  • 2.5 Baths
  • 1,461 Sq Ft

  13808 Ancilla Blvd, Windermere, FL 34786

  One or more photo(s) has been virtually staged. Back on the Market! Buyer’s financing fell through — their loss is your gain! During the transaction, the sellers installed a brand-new A/C unit, so the home is ready for its next owners to move in with comfort and peace of mind. Beautiful 3-bedroom, 2.5-bath townhome located in the desirable SUMMERPORT community of Windermere. Residents enjoy

  

  Carlos German

  EXP REALTY LLC

  (407) 329-6677

  13808 Ancilla Blvd, Windermere, FL 34786
• 

  

  /27

  $2,500 per month

  • 3 Beds
  • 2.5 Baths
  • 1,840 Sq Ft
  • Townhouse for Rent

  14284 Desert Haven St Unit 806, Windermere, FL 34786

  VACANT! Great location! Great Home! Move in this Great home inside the lovely Oasis Cove community in the very desirable town of Windermere. This house is full of upgrades and is an Energy Star certified home. Downstairs has all tiled floor. It oversees the front porch. Kitchen has all fully appliances and granite counter top. You can also enjoy Disney firework at night. Upstairs has a large

  Daniel Zheng CINO INTERNATIONAL INC

  14284 Desert Haven St Unit 806, Windermere, FL 34786
• 

  /2

  $432,500 Sold Oct 30, 2025

  • 1,686 Sq Ft
  • $257/SF
  • 38 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2020

  8942 Matriarca Alley, Windermere, FL 34786

  Welcome to this stunning corner unit townhouse built in 2020, offering 3 spacious bedrooms (located in the 2nd floor), 2 full bathroom in the 2nd floor and half bathroom on the first floor, and a 2 car garage. Perfectly positioned right in front of a serene lake, you’ll love starting your mornings with a coffee and peaceful water views. Right next to the community pool, community mailbox and

  Alexandra Lattuf ANCHOR REAL ESTATE

  8942 Matriarca Alley, Windermere, FL 34786
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  /37

  Est $1,692,903 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 4,396 Sq Ft

  1214 Estancia Woods Loop, Windermere, FL 34786

  1214 Estancia Woods Loop, Windermere, FL 34786
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  /62

  $1,639,985

  • 6 Beds
  • 7 Baths
  • 3,625 Sq Ft

  11342 S Camden Commons Dr, Windermere, FL 34786

  SELLER MOTIVATED. SOLD PARTIALLY FURNISHED. Situated at highly coveted community of Keenes Point in Windermere, this exquisitely home refined luxury living. FULLY REMODELED, Featuring six expansive bedrooms and five impeccably full bathrooms, and two half baths, every detail of this residence has been thoughtfully elevated.At the heart of the home lies a chef-inspired kitchen, appointed

  

  Laura Teixeira

  NOBSKA REAL ESTATE LLC

  (407) 974-4620

  11342 S Camden Commons Dr, Windermere, FL 34786
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  /51

  $1,389 - $2,489 per month

  Citra at Windermere

  1 - 3 Beds

  11353 Citra Cir, Windermere, FL 34786

  Experience the finest apartments in Windermere, Florida at The Citra at Windermere. Our apartment community offers a variety of distinctive one, two, and three bedroom apartment homes. Conveniently located, Citra at Windermere is walking distance to shopping, restaurants and entertainment. In addition, we are located within some of the top rated schools in Orange county, including Bay

  11353 Citra Cir, Windermere, FL 34786
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  /2

  $830,000 Sold Oct 30, 2025

  • 3,151 Sq Ft
  • $263/SF
  • 136 Days On Market

  • 5 Beds
  • 4 Baths
  • Built 2004

  1638 Whitney Isles Dr, Windermere, FL 34786

  Welcome to luxury living in the highly desirable gated community of Belmere, located in Windermere. This beautifully upgraded 5 bedroom, 4 bath pool home offers the perfect blend of elegance, comfort, and functionality. Featuring new luxury vinyl flooring, upgraded appliances, and an open concept split floor plan, the home is flooded with natural light that enhances its spacious and inviting

  Morgan Horsley THE REAL ESTATE COLLECTION LLC

  1638 Whitney Isles Dr, Windermere, FL 34786
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  /62

  Est $2,382,886 Not Listed For Sale

  • 5 Beds
  • 7 Baths
  • 5,734 Sq Ft

  13334 Bellaria Cir, Windermere, FL 34786

  13334 Bellaria Cir, Windermere, FL 34786
• 

  

  /51

  $675,000 Open Sat 12PM - 3PM

  • 3 Beds
  • 2.5 Baths
  • 3,094 Sq Ft

  6734 Bridgewater Village Rd, Windermere, FL 34786

  Welcome to 6734 Bridgewater Village Road, a true gem nestled in the highly sought-after Vineyards of Horizon West in Windermere. This exquisite property offers unparalleled privacy on an oversized CONSERVATION lot, creating a serene oasis where you can truly unwind and enjoy the beauty of nature. As you approach the home, the stunning paver driveway leads you to an inviting entrance. Step inside

  

  Alexis Bress

  EXP REALTY LLC

  (689) 345-8480

  6734 Bridgewater Village Rd, Windermere, FL 34786
• 

  

  /15

  $2,375 per month

  • 3 Beds
  • 2.5 Baths
  • 1,644 Sq Ft
  • Townhouse for Rent

  8265 Maritime Flag St Unit 101, Windermere, FL 34786

  Built in 2012, this spacious 3-bedroom, 2.5-bath townhouse offers the perfect blend of comfort, convenience, and community living. Step inside to find a bright and open floor plan featuring a large kitchen, dining area, and living room, perfect for entertaining or relaxing at home. All bedrooms are conveniently located on the second floor, providing added privacy. The home includes all major

  Carissa Lawhun FLORIDA REALTY INVESTMENTS

  8265 Maritime Flag St Unit 101, Windermere, FL 34786
• 

  /2

  $789,000 Sold Oct 29, 2025

  • 2,642 Sq Ft
  • $299/SF
  • 224 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2005

  13413 Hopkinton Ct, Windermere, FL 34786

  Newly Renovated Home near Disney!Stunning cul-de-sac Windermere residence, just minutes away from the enchanting world of Disney! 4 spacious bedrooms offering comfort and privacy for the whole family with 3.5 well-appointed bathrooms ensuring convenience and luxury. The 3-car garage providing ample space and storage options. with a host of state of the art features! Step into a space where

  Jennifer Olmeda WRA BUSINESS & REAL ESTATE

  13413 Hopkinton Ct, Windermere, FL 34786
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  /80

  Est $2,554,849 Not Listed For Sale

  • 5 Beds
  • 7 Baths
  • 5,161 Sq Ft

  11628 Waterstone Loop Dr, Windermere, FL 34786

  11628 Waterstone Loop Dr, Windermere, FL 34786

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