Windermere, FL Homes

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  /37

  $599,999

  • 4 Beds
  • 2.5 Baths
  • 2,981 Sq Ft

  12925 Holdenbury Ln, Windermere, FL 34786

  This splendid two-story home features four large bedrooms and 2.5 bathrooms. The true highlight of the home is its stunning, oversized kitchen, which has a huge amount of cabinet and counter space. Not one, but two islands provide a setting for casual dining and culinary creativity. The main floor offers a cozy first-floor bedroom for added convenience and flexibility, suitable for guests or as a

  Eric Nelson SIGNATURE HOMES

  12925 Holdenbury Ln, Windermere, FL 34786
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  /15

  $2,500 per month

  • 3 Beds
  • 2 Baths
  • 1,510 Sq Ft
  • Townhouse for Rent

  7351 Millstone St, Windermere, FL 34786

  Beautiful Unfurnished 3/2 townhome in the best location in entire community! This upgraded, sparkling clean unit with stainless steal appliances, Fridge, Washer and Dryer located directly across from the park and the baseball diamond and is practically in Disney World's backyard! You'll love the spectacular nightly fireworks show from your master bedroom or front porch and fall in love with the

  Luciana Lagreca FRONTLINE FLORIDA REALTY, INC.

  7351 Millstone St, Windermere, FL 34786
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  /2

  $840,000 Sold Oct 17, 2025

  • 2,412 Sq Ft
  • $348/SF
  • 10 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 2006

  4509 Indian Deer Rd, Windermere, FL 34786

  Stunningly Upgraded Pool Home with Water Views in Summerport, Windermere!This 4-bedroom, 3-bath single-family home offers the perfect blend of elegance, functionality, and peace of mind with recent major upgrades. From the moment you arrive, you’ll notice the meticulous care and designer touches that make this residence feel like a model home.The heart of the home opens to a

  Clementine Costantini KELLER WILLIAMS REALTY AT THE LAKES

  4509 Indian Deer Rd, Windermere, FL 34786
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  /36

  Est $1,605,352 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 4,374 Sq Ft

  1146 Estancia Woods Loop, Windermere, FL 34786

  1146 Estancia Woods Loop, Windermere, FL 34786
• 

  

  

  /53

  $650,000

  • 4 Beds
  • 2 Baths
  • 2,555 Sq Ft

  6139 Andreozzi Ln, Windermere, FL 34786

  Here is your chance to own this spacious well-maintained one-story 4-bedroom waterfront home on a pond located in the desirable Providence neighborhood of Windermere. As you enter through the front porch and foyer you will immediately notice the high 10’ ceilings and inviting rooms to your well-thought-out floor plan. The living room is spacious with an elegant dining room overlooking the

  Simon Simaan THE SIMON SIMAAN GROUP

  6139 Andreozzi Ln, Windermere, FL 34786
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  /13

  $2,950 per month

  • 5 Beds
  • 3 Baths
  • 2,701 Sq Ft
  • House for Rent

  13353 Overstreet Rd, Windermere, FL 34786

  VACANT !! Downstairs has all tiled floors, and a private study or in-law bedroom. It oversees the front porch. Kitchen has granite counter top and a large island that can be used for breakfast bar. It opens up to the Great Room and provides a best place for family and friends' gathering. Upstairs has a large master bedroom, and three bedrooms. Master bathroom has double sink, granite counter top,

  Jeff Li CINO INTERNATIONAL INC

  13353 Overstreet Rd, Windermere, FL 34786
• 

  /2

  $649,000 Sold Oct 17, 2025

  • 2,628 Sq Ft
  • $247/SF
  • 4 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2008

  13225 Charfield St, Windermere, FL 34786

  Welcome Home to your Spacious ENCLOSED and Private POOL HOME located in the sought-after community of Lake Sawyer in Windermere. This home offers a perfect blend of style, comfort, and convenience. Inside, the gourmet kitchen is appointed with granite countertops, stainless steel appliances, and ample cabinetry, flowing seamlessly into open living spaces ideal for entertaining or family

  Karlene Grimes KELLER WILLIAMS ADVANTAGE III

  13225 Charfield St, Windermere, FL 34786
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  /26

  Est $321,480 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,442 Sq Ft

  11434 Jasper Kay Terrace Unit 208, Windermere, FL 34786

  11434 Jasper Kay Terrace Unit 208, Windermere, FL 34786
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  /43

  $939,500

  • 5 Beds
  • 5 Baths
  • 3,285 Sq Ft

  11096 Ledgement Ln, Windermere, FL 34786

  This Windermere home proliferates in privacy, luxury, and modernconvenience. Tucked away on a third of an acre within the gated Glenmuircommunity and backing onto a protected conservation area, this stunninghome presents tranquil forested views and absolute peace with no rearneighbors, ever. The saltwater pool, complete with solar heating, child-safe fencing, LEDaccent

  James Ellis CHARLES RUTENBERG REALTY ORLANDO

  11096 Ledgement Ln, Windermere, FL 34786
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  /35

  $2,100 per month

  • 3 Beds
  • 2 Baths
  • 1,332 Sq Ft
  • Condo for Rent

  8168 Boat Hook Loop Unit 725, Windermere, FL 34786

  MOVE IN SPECIAL: FIRST TWO WEEKS ARE FREE

  Rick Sein REALSOURCE PROPERTY MANGNT LLC

  8168 Boat Hook Loop Unit 725, Windermere, FL 34786
• 

  /2

  $760,000 Sold Oct 17, 2025

  • 3,109 Sq Ft
  • $244/SF
  • 57 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2021

  13218 Orange Isle Dr, Windermere, FL 34786

  Back on the market, move fast before its gone! Welcome to 13218 Orange Isle Drive, located in the highly desirable Sanctuary at Lakes of Windermere! This beautifully maintained home features 4 bedrooms, 3.5 bathrooms, a private office/flex space, and a spacious 3-car tandem garage.Step inside to a bright, open floor plan with high ceilings, gorgeous wood stairways, modern finishes, and an

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

  13218 Orange Isle Dr, Windermere, FL 34786
• 

  

  /53

  Est $1,001,946 Not Listed For Sale

  • 5 Beds
  • 4 Baths
  • 3,934 Sq Ft

  11708 Hampstead St, Windermere, FL 34786

  11708 Hampstead St, Windermere, FL 34786
• 

  

  /40

  $499,999

  • 3 Beds
  • 2.5 Baths
  • 2,154 Sq Ft

  8575 Lookout Pointe Dr, Windermere, FL 34786

  This beautiful 3 bedroom, 2.5 bath home is nestled in the highly desirable Windermere Trails community. Enjoy the magic of theme parks just minutes away from Disney World with a direct view of the fireworks from your front porch! With over 2,000 SqFt, this home boasts an open floor plan that offers an upgraded kitchen, a large dining space, a spacious family room, and an upstairs loft. The

  Thomas Weclew THE REALTY MEDICS

  8575 Lookout Pointe Dr, Windermere, FL 34786
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  /50

  $3,200 per month

  • 4 Beds
  • 3.5 Baths
  • 2,420 Sq Ft
  • House for Rent

  7224 Halton Ct, Windermere, FL 34786

  Welcome to this beautifully refreshed two-story home offering over 2,400 sq ft of living space in the desirable Enclave community in Windermere. The first floor features a functional layout with living and dining areas, a comfortable family room, and a kitchen equipped with stainless-steel appliances, a breakfast bar, big pantry and plenty of space for everyday living and entertaining. Step

  Tatyana Clark COLDWELL BANKER RESIDENTIAL RE

  7224 Halton Ct, Windermere, FL 34786
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  /2

  $797,000 Sold Oct 17, 2025

  • 2,867 Sq Ft
  • $278/SF
  • 101 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 2002

  1932 Reed Hill Dr, Windermere, FL 34786

  Updated and Modern in the heart of Windermere, this well cared for pool home is now available in the highly desirable and gated Westover Club community. This chic home is a showplace of style with new custom luxury wood flooring, open concept floor plan with plenty of natural light, and a renovated kitchen with new imported stone countertops. The primary suite has beautiful views of the backyard

  Michael blank FL PRO BROKERS LLC

  1932 Reed Hill Dr, Windermere, FL 34786
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  /4

  Est $1,207,799 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,806 Sq Ft

  5819 Caymus Loop Unit 1, Windermere, FL 34786

  5819 Caymus Loop Unit 1, Windermere, FL 34786
• 

  

  /63

  $1,264,000

  • 4 Beds
  • 3.5 Baths
  • 2,791 Sq Ft

  109 E 12th Ave, Windermere, FL 34786

  Modern upgrades meet timeless Windermere charm in this fully reimagined four-bedroom, three-and-a-half-bath home, just steps from Lake Bessie. Set on a beautifully manicured corner lot with no HOA, this thoughtfully updated property blends luxury, comfort, and functionality in one of Central Florida’s most desirable communities.Every detail has been considered—NEW ROOF, NEW A/C, NEW

  Robert Larkan EXECUTIVE PROPERTIES

  109 E 12th Ave, Windermere, FL 34786
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  /20

  $3,100 per month

  • 3 Beds
  • 2 Baths
  • 2,156 Sq Ft
  • House for Rent

  6920 Helmsley Cir, Windermere, FL 34786

  Beautiful One-Story Home in Windermere. The Perfect Place to Call Home!Discover comfort and elegance in this stunning single-story home located in the highly desirable community of Windermere. Featuring 3 spacious bedrooms and 2 full bathrooms, this property combines modern style with everyday functionality.Perfectly positioned on a private corner lot, this home offers extra space,

  Jessica Dessire Cueva PA CHARLES RUTENBERG REALTY ORLANDO

  6920 Helmsley Cir, Windermere, FL 34786
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  /2

  $966,400 Sold Oct 17, 2025

  • 3,206 Sq Ft
  • $301/SF
  • 144 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 2003

  11508 Delwick Dr, Windermere, FL 34786

  Fully Renovated with Modern Upgrades. Nestled in the distinguished, 24-hour guard-gated community of The Reserve at Belmere in Windermere, FL. Experience the best of Florida living in this exceptional home. Featuring a distinctive barrel-tiled roof, this move-in-ready residence exemplifies pride of ownership both inside and out.This newly completely remodeled home spans nearly 3206 sq. ft. on

  Ziad El Aryan FLORIDA REALTY INVESTMENTS

  11508 Delwick Dr, Windermere, FL 34786
• 

  

  /98

  Est $2,613,681 Not Listed For Sale

  • 5 Beds
  • 6.5 Baths
  • 5,390 Sq Ft

  13509 Bellaria Cir, Windermere, FL 34786

  13509 Bellaria Cir, Windermere, FL 34786
• 

  

  /42

  $550,000

  • 4 Beds
  • 2 Baths
  • 2,159 Sq Ft

  11322 Rapallo Ln, Windermere, FL 34786

  One or more photo(s) has been virtually staged. ***Back on Market due to Buyer not depositing Escrow*** “Mortgage savings may be available for buyers of this listing.” Located in the gated Windermere community of Belmere Village, this beautifully maintained 4-bedroom, 2-bathroom home offers both comfort and convenience. Residents enjoy low HOA fees and a wealth of amenities including a clubhouse,

  John Callahan REDFIN CORPORATION

  11322 Rapallo Ln, Windermere, FL 34786
• 

  

  /45

  $12,000 per month

  • 3 Beds
  • 3.5 Baths
  • 2,848 Sq Ft
  • House for Rent

  6132 Payne Stewart Dr, Windermere, FL 34786

  Isleworth Golf and Country Club opportunity. Located inside the gates of the private and renowned Isleworth Golf & Country Club, this beautifully renovated home is now available. Spanning over 2,800 square feet, this updated home offers 3 bedrooms and 3.5 bathrooms. The thoughtfully designed interior features separate living and family rooms, a separate dining room, and a casual breakfast nook.

  Ryan Rapolti LPT REALTY, LLC

  6132 Payne Stewart Dr, Windermere, FL 34786
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  /2

  $560,000 Sold Oct 15, 2025

  • 1,971 Sq Ft
  • $284/SF
  • 6 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2015

  7266 Penkridge Ln, Windermere, FL 34786

  NOW AVAILABLE! This beautiful move-in-ready home in Windermere, FL features 3 bedrooms, 2 bathrooms, and a den in a sought-after school district, just minutes from Walt Disney World and Orlando’s best entertainment. Blending modern finishes with a practical open layout, this one-story property is a perfect fit for families, professionals, and relocation buyers.Enjoy modern luxury details

  Dennis Raffeo REALTY EXECUTIVES IN THE VILLAGES

  7266 Penkridge Ln, Windermere, FL 34786
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  /30

  Est $2,476,383 Not Listed For Sale

  12624 Park Ave, Windermere, FL 34786

  12624 Park Ave, Windermere, FL 34786
• 

  

  /100

  $3,250,000

  • 4 Beds
  • 5.5 Baths
  • 4,849 Sq Ft

  6186 Louise Cove Dr, Windermere, FL 34786

  A Masterpiece of Design in Isleworth – 6186 Louise Cove Drive. Stunning, design magazine-worthy residence nestled behind the exclusive 24-hour guard-gated community of Isleworth, one of Central Florida’s most prestigious neighborhoods. This exquisite estate sits on a spacious 0.75-acre corner lot, surrounded by mature landscaping and a stately circular driveway that sets the tone for the luxury

  Simon Simaan THE SIMON SIMAAN GROUP

  6186 Louise Cove Dr, Windermere, FL 34786
• 

  

  /20

  $2,700 per month

  • 4 Beds
  • 3.5 Baths
  • 2,176 Sq Ft
  • House for Rent

  6242 Golden Dewdrop Trail, Windermere, FL 34786

  Well-deserved Windermere home with fresh paint throughout and brand-new vinyl flooring on the first floor. This spacious residence features 4 bedrooms and 3.5 bathrooms, including two master suites—one downstairs and one upstairs. The first floor offers formal living and dining areas, while the second floor includes a loft and two additional bedrooms, providing plenty of space for family

  Alice Wang FOURSQUARE REAL ESTATE

  6242 Golden Dewdrop Trail, Windermere, FL 34786
• 

  /2

  $318,500 Sold Oct 15, 2025

  • 1,455 Sq Ft
  • $219/SF
  • 17 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2006

  8156 Boat Hook Loop Unit 107, Windermere, FL 34786

  One or more photo(s) has been virtually staged. $1500 CREDIT OFFERED FOR BUYERS PREPAIDS AND CLOSING COSTS.Step into this beautifully maintained first -floor unit in the sought-after Lakeside at Lakes of Windermere community. Ideally located Directly across from the community pool and clubhouse. Offering 1,455 square feet, this 3-bedroom, 2-bathroom home is designed for effortless

  Corey Cannon BHHS FLORIDA REALTY

  8156 Boat Hook Loop Unit 107, Windermere, FL 34786
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  /58

  Est $440,633 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,722 Sq Ft

  8668 Wellington Blue Ln, Windermere, FL 34786

  8668 Wellington Blue Ln, Windermere, FL 34786
• 

  

  /53

  $774,000

  • 4 Beds
  • 3.5 Baths
  • 2,745 Sq Ft

  13519 Bicton Ln, Windermere, FL 34786

  Stunning 4-Bedroom, 3 bathroom Home with NEW ROOF, NEW WINDOWS, 3-car garage, a putting green, and a $35,000 BUYER CREDIT in Gated Windermere Community. This beautifully maintained home offers nearly 3,000 square feet of thoughtfully designed living space in one of Windermere’s most sought-after gated communities combining comfort, quality, and convenience.Enjoy nightly Walt Disney World

  Tiphany Weeks DIAMOND REAL ESTATE GROUP

  13519 Bicton Ln, Windermere, FL 34786
• 

  

  /25

  $2,700 per month

  • 3 Beds
  • 2.5 Baths
  • 1,880 Sq Ft
  • House for Rent

  11049 Bagley Alley, Windermere, FL 34786

  Beautiful Two-Story Home featuring 3 bedrooms, 2.5 baths. Spacious living, dining, and kitchen area. The loft and all bedrooms are located on the 2nd floor. The house offers stainless steel appliances. The laundry room is located on the 2nd floor as well. 1st floor all laminate and tile flooring, and new carpet on stairs, and new laminate flooring on 2nd floor. Home is approximately 2082 sq. Ft.

  Amanda Yuan MULTI CHOICE REALTY LLC

  11049 Bagley Alley, Windermere, FL 34786
• 

  /2

  $1,625,000 Sold Oct 15, 2025

  • 3,810 Sq Ft
  • $427/SF
  • 50 Days On Market

  • 5 Beds
  • 4 Baths
  • Built 2002

  8424 Lake Burden Cir, Windermere, FL 34786

  Keene’s Pointe is more than a neighborhood; it’s a lifestyle. This 24-hour attended, gated community in Windermere is home to The Golden Bear Club, a Jack Nicklaus–designed 18-hole golf course featuring resort-style amenities including tennis, fitness, swimming, and dining.Tucked within this sought-after community, you'll find a fully renovated, move-in-ready home offering 5 bedrooms, 4 full

  Ken Pozek REAL BROKER, LLC

  8424 Lake Burden Cir, Windermere, FL 34786
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  /62

  Est $1,128,267 Not Listed For Sale

  • 5 Beds
  • 4 Baths
  • 3,881 Sq Ft

  5522 Remsen Cay Ln, Windermere, FL 34786

  5522 Remsen Cay Ln, Windermere, FL 34786
• 

  

  /90

  $6,799,000

  • 5 Beds
  • 8 Baths
  • 8,443 Sq Ft

  11103 Bridge House Rd, Windermere, FL 34786

  Step into timeless elegance, luxury, and sophisticated living. Located in the exclusive man-gated community of Lake Butler Sound—one of Central Florida’s most prestigious communities. From the moment you enter, you're greeted by high-end finishes, open-concept living space, and meticulous attention to detail. This stunning residence offers nearly 9,000 sqft of elevated living space featuring 5

  Ayoub Aitelhaj THE SIMON SIMAAN GROUP

  11103 Bridge House Rd, Windermere, FL 34786
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  /37

  $8,800 per month

  • 5 Beds
  • 4.5 Baths
  • 3,835 Sq Ft
  • House for Rent

  7231 Sangalla Dr, Windermere, FL 34786

  WINDERMERE LUXURY LISTING EXCELLENT FLOOR PLAN • GATED COMMUNITY • WINDERMERE LOCATION • RESORT-STYLE BACKYARD • SCREENED POOL • LUXURY FINISHES • TOP-RATED SCHOOLS Live in one of Windermere’s most exclusive gated communities, surrounded by multi-million-dollar lakefront estates.This elegant 5-bedroom, 5-bath home features an excellent floor plan with a beautiful office, large loft, and

  Darrell Nunnelley VINTAGE REALTY GROUP LLC

  7231 Sangalla Dr, Windermere, FL 34786
• 

  /2

  $500,000 Sold Oct 14, 2025

  • 1,696 Sq Ft
  • $295/SF
  • 45 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2012

  12796 Garridan Ave, Windermere, FL 34786

  A Rare Windermere Treasure You Don’t Want to Miss! Welcome to Wickham Park, one of Central Florida’s most coveted communities, where top-rated schools, stunning surroundings, and unbeatable convenience come together. This is your chance to own a home in a neighborhood that’s just minutes from Winter Garden Village with its premier shopping, full-service grocery stores, casual dining, and more.

  Patricia Alvares FLORIDA REALTY INVESTMENTS

  12796 Garridan Ave, Windermere, FL 34786
• 

  

  /73

  Est $2,790,579 Not Listed For Sale

  • 5 Beds
  • 5.5 Baths
  • 6,768 Sq Ft

  13323 Bellaria Cir, Windermere, FL 34786

  13323 Bellaria Cir, Windermere, FL 34786
• 

  

  /100

  $3,500,000

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

  10577 Down Lakeview Cir, Windermere, FL 34786

  This exceptional lakefront home is located on The Butler Chain of Lakes with 137 feet of pristine shoreline and is situated on almost one dry acre. At first glance you will immediately fall in love with this beautiful custom home boasting amazing panoramic views and nightly Disney fireworks. The circular paved drive flanked with mature oak trees welcome you home to a covered porch and an

  Simon Simaan THE SIMON SIMAAN GROUP

  10577 Down Lakeview Cir, Windermere, FL 34786
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  /62

  $4,500 per month

  • 4 Beds
  • 2.5 Baths
  • 2,648 Sq Ft
  • House for Rent

  5426 Gemgold Ct, Windermere, FL 34786

  Welcome to this stunning WATERFRONT HOUSE with a DOCK in the highly sought-after Summerport community! Recently remodeled on the first floor, this home now features a captivating open layout complemented by newer luxury vinyl floors throughout. With 4 bedrooms, 21⁄2 baths, and a 2-car garage, this lovely property is an absolute must-see.As you approach, you’ll notice the FRESHLY PAINTED

  Hector Leon LPT REALTY, LLC

  5426 Gemgold Ct, Windermere, FL 34786
• 

  /2

  $550,000 Sold Oct 14, 2025

  • 1,984 Sq Ft
  • $277/SF
  • 33 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2012

  6266 Golden Dewdrop Trail, Windermere, FL 34786

  Welcome to this exceptional corner-lot home located just steps away from Keenes Pointe and the Chase Road. Featuring a recently replaced air conditioning system for added comfort and efficiency, this residence boasts a spacious, fully fenced backyard that offers maximum privacy. The expansive outdoor space is beautifully landscaped with low-maintenance artificial turf,perfect for entertaining or

  Margot Villacinda Chavez WRA BUSINESS & REAL ESTATE

  6266 Golden Dewdrop Trail, Windermere, FL 34786
• 

  

  /36

  Est $4,023,049 Not Listed For Sale

  • 5 Beds
  • 6.5 Baths
  • 7,649 Sq Ft

  12300 Montalcino Cir, Windermere, FL 34786

  12300 Montalcino Cir, Windermere, FL 34786

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