Windermere, FL Homes

• 

  

  

  /30

  $385,000 Pending

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

  5219 Keenes Pheasant Dr, Windermere, FL 34786

  Under contract-accepting backup offers. Beautifully Maintained 3-Bedroom Townhome in Sought-After Summerport! Don’t miss this spacious and move-in ready townhouse located in the heart of Summerport, one of the area’s most desirable communities. This light-filled home features 3 bedrooms, 2.5 bathrooms, and an open floor plan perfect for modern living. The primary suite is conveniently located on

  Roland Cotardo THE SIMON SIMAAN GROUP

  5219 Keenes Pheasant Dr, Windermere, FL 34786
• 

  

  

  /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

  $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
• 

  

  

  /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
• 

  

  

  /60

  $795,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 2,766 Sq Ft

  12905 Strode Ln, Windermere, FL 34786

  Under contract-accepting backup offers. Completely remodeled in 2021! Welcome home to your stunning 4-bedroom craftsman with contemporary finishes in the highly sought after community of Windermere Sound. This well-maintained waterfront home with no rear neighbors has it all. At first glance you will immediately notice the amazing curb appeal with its charming architecture, manicured landscaping,

  Simon Simaan THE SIMON SIMAAN GROUP

  12905 Strode Ln, Windermere, FL 34786
• 

  

  /36

  $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

  $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
• 

  

  /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
• 

  

  /22

  $399,900 Pending

  • 3 Beds
  • 2.5 Baths
  • 1,468 Sq Ft

  7361 Brightland St, Windermere, FL 34786

  Under contract-accepting backup offers. New Price! Nestled in the heart of Windermere, this two-story townhome is a perfect blend of charm, comfort, and modern living. As you approach, the cute front porch entrance welcomes you, hinting at the warmth that lies within. The exterior is adorned with stone columns and crowned with a stylish barrel-tiled roof, adding character to this inviting abode.

  Peter Luu REAL BROKER, LLC

  7361 Brightland St, Windermere, FL 34786
• 

  

  /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
• 

  /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
• 

  

  /56

  $615,000

  • 3 Beds
  • 3.5 Baths
  • 2,720 Sq Ft

  6626 Bridgewater Village Rd, Windermere, FL 34786

  --Beautiful Corner-Lot Home in The Vineyards of Horizons West-- Welcome to one of Horizon West’s most desirable neighborhoods — where scenic parks, walkable streets, and friendly neighbors create a true sense of community. This corner-lot home sits across from a peaceful green space and offers the perfect blend of comfort, style, and outdoor living.From the moment you arrive, the inviting

  David Dorman CENTURY 21 CARIOTI

  6626 Bridgewater Village Rd, Windermere, FL 34786
• 

  

  /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
• 

  /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
• 

  

  /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
• 

  

  /50

  $2,500,000

  • 6 Beds
  • 7.5 Baths
  • 8,137 Sq Ft

  1724 Windermeredown Place, Windermere, FL 34786

  Nestled in Windermere's exclusive lakefront community, this over-acre estate offers private access to the Butler Chain of Lakes. Recognized by K+BB Magazine as Bathroom of the Year, the spa-inspired primary suite features dual rain showers, a freestanding stone tub, sauna, and outdoor shower. The resort-style pool and grotto—crafted by Disney's Animal Kingdom designer—feature a waterfall, slide,

  Chad Going Serhant

  1724 Windermeredown Place, 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
• 

  /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
• 

  

  /62

  $1,600,000

  • 4 Beds
  • 3.5 Baths
  • 3,809 Sq Ft

  8375 Bowden Way, Windermere, FL 34786

  This charming four-bedroom, three-and-a-half-bath home in the highly sought-after Keene’s Pointe community perfectly combines elegance, comfort, and character. Designed with a timeless French-inspired décor, every space feels warm, inviting, and beautifully curated.The highlight of this home is its backyard oasis — a peaceful retreat overlooking the sparkling pool and tranquil pond views,

  Oscar Rodriguez B LIVE COMMERCIAL AND RESIDENTIAL REAL ESTATE

  8375 Bowden Way, 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

  $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
• 

  

  /30

  Est $2,476,383 Not Listed For Sale

  12624 Park Ave, Windermere, FL 34786

  12624 Park Ave, Windermere, FL 34786
• 

  

  /50

  $695,000

  • 5 Beds
  • 3.5 Baths
  • 2,976 Sq Ft

  6712 Thornhill Cir, Windermere, FL 34786

  With timeless curb appeal and a front porch built for slow mornings, this Windermere home blends classic charm with the upgrades that make everyday life easier. Step inside and the ceilings rise, sunlight floods through, and hardwood floors (2021) lead you through open living and dining spaces that flow seamlessly into a remodeled kitchen with quartz countertops, updated cabinetry, and dual

  Brad Young HOMEVEST REALTY

  6712 Thornhill Cir, 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

  $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
• 

  

  /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
• 

  

  /48

  $3,700,000

  • 3 Beds
  • 5 Baths
  • 4,333 Sq Ft

  9310 Isleworth Gardens Dr, Windermere, FL 34786

  Experience the art of fine living in this exquisite one-story Modern Mediterranean garden villa, offered fully furnished with a curated designer furniture package. Every detail has been thoughtfully crafted, blending timeless architecture with refined finishes and effortless comfort.Inside, travertine floors, wood-beamed ceilings, and solid wood doors set a warm, sophisticated tone. Custom

  Linnae Williams UPSIDE REAL ESTATE INC

  9310 Isleworth Gardens Dr, Windermere, FL 34786
• 

  

  /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

  $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
• 

  

  /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
• 

  

  /54

  $824,900

  • 5 Beds
  • 5.5 Baths
  • 3,598 Sq Ft

  13327 Fernow St, Windermere, FL 34786

  One or more photo(s) has been virtually staged. Immaculate 4-Bedroom + Loft, 5.5-Bath Home Minutes from Disney! Perfectly blending luxury, comfort, and location, this 3,600 SF home offers 4 spacious bedrooms plus a versatile loft that can easily be enclosed as a 5th bedroom. Nestled in a top-rated school zone, the property features a 3-car garage, paver driveway, and a fully fenced backyard with

  Jonathan Ruiz KELLER WILLIAMS WINTER PARK

  13327 Fernow St, Windermere, FL 34786
• 

  

  /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

  $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
• 

  

  /33

  $585,000

  • 3 Beds
  • 2 Baths
  • 1,732 Sq Ft

  13430 Hopkinton Ct, Windermere, FL 34786

  ***Charming Windermere Home in Lakes of Windermere – Peachtree! ***Welcome to this beautifully maintained 3-bedroom, 2-bath single-story home located on a quiet cul-de-sac in the desirable Lakes of Windermere – Peachtree community, behind the famous Walt Disney World Magic Kingdom! This home combines comfort, convenience, and style in one of Central Florida’s most sought-after locations.

  Lynn London EXP REALTY LLC

  13430 Hopkinton Ct, Windermere, FL 34786
• 

  

  /35

  $2,700 per month

  • 3 Beds
  • 2.5 Baths
  • 1,881 Sq Ft
  • Property for Rent

  7448 Leighside Dr, Windermere, FL 34786

  Live in one of Windermere’s most desirable communities! This beautifully maintained 3-bedroom, 2.5-bath townhome offers a spacious open-concept layout perfect for comfortable living. The kitchen features granite countertops, stainless steel appliances, 42” solid wood cabinets, and a generous amount of storage. The first floor offers ceramic tile throughout, while all bedrooms are located upstairs

  Vicente Virgilio ALTIS REALTY

  7448 Leighside Dr, 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

Showing Results 121 - 160, Page 4 of 18