Windermere, FL Homes

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  /2

  $439,900 Sold Jun 30, 2025

  • 1,861 Sq Ft
  • $236/SF
  • 23 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2009

  7508 Bentonshire Ave, Windermere, FL 34786

  Discover this ideal 4-bedroom, 3.5-bath END-UNIT townhome in the heart of Windermere! This home features beautiful knotty wood LVP throughout the downstairs. Lots of storage in the large solid wood cabinets with crown molding and under cabinet lights. NEW APPLIANCES (range, microwave, dishwasher), solid stone counters with tile backsplash. Breakfast bar with a view to the great room gives an open

  Hannah Thompson FLORIDA REALTY INVESTMENTS

  7508 Bentonshire Ave, Windermere, FL 34786
• 

  

  

  /17

  Est $678,550 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,926 Sq Ft

  8712 Crescendo Ave, Windermere, FL 34786

  8712 Crescendo Ave, Windermere, FL 34786
• 

  

  

  /21

  $399,990

  • 3 Beds
  • 2.5 Baths
  • 1,462 Sq Ft

  5235 Keenes Pheasant Dr, Windermere, FL 34786

  Charming 3-Bedroom Townhome in a Prime Location!Welcome home to this beautifully maintained 3-bedroom, 2.5-bath townhome offering 1,462 sq. ft. of comfortable living space. The spacious open-concept floor plan features a roomy kitchen, cozy family room, and a flex space that could be used as a home office—all conveniently located downstairs. Upstairs, you’ll find all three bedrooms, including

  Ronda Shively COMPASS FLORIDA LLC

  5235 Keenes Pheasant Dr, Windermere, FL 34786
• 

  

  /2

  $1,175,000 Sold Jun 30, 2025

  • 4,061 Sq Ft
  • $289/SF
  • 34 Days On Market

  • 5 Beds
  • 4.5 Baths
  • Built 2018

  8530 Vivaro Isle Way, Windermere, FL 34786

  One or more photo(s) has been virtually staged. Elegant Pool Home with Conservation & Fireworks Views Near Disney in the Most Desired Horizon West.Discover refined luxury and upscale comfort at 8530 Vivaro Isle Way, a stunning Spanish/Mediterranean-style residence located in the desired Windermere Isle community—just 2.5 miles from Disney’s Magic Kingdom and close to Central Florida’s

  Katherine Figueroa Santiago WATSON REALTY CORP., REALTORS

  8530 Vivaro Isle Way, Windermere, FL 34786
• 

  

  

  /39

  Est $754,283 Not Listed For Sale

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

  13207 Orange Isle Dr, Windermere, FL 34786

  13207 Orange Isle Dr, Windermere, FL 34786
• 

  

  /28

  $340,000

  • 3 Beds
  • 2.5 Baths
  • 1,534 Sq Ft

  14242 Desert Haven St Unit GE, Windermere, FL 34786

  Located in the gated community of Oasis Cove, this 3-bedroom, 2.5-bathroom condo offers a comfortable, low-maintenance lifestyle just minutes from Disney—with clear views of the nightly fireworks from your own home.The interior features a functional two-story layout with all bedrooms located upstairs, providing separation between living and private spaces. The main floor includes an

  James Goodyear REAL BROKER, LLC

  14242 Desert Haven St Unit GE, Windermere, FL 34786
• 

  /2

  $1,225,000 Sold Jun 30, 2025

  • 3,808 Sq Ft
  • $322/SF
  • 7 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 1998

  9138 Pinnacle Cir, Windermere, FL 34786

  Elegant Estate Living in Gated Windermere Enclave. Set on a beautifully landscaped 1+ acre corner lot, this impressive 4-bedroom, 4-bathroom estate offers a rare blend of elegance, space, and thoughtful design in one of Windermere’s most sought-after gated communities. From the moment you step through the front door, you're greeted with a direct view of the sparkling pool and outdoor oasis—an

  Frank Del Toro REVEL REALTY LLC

  9138 Pinnacle Cir, Windermere, FL 34786
• 

  

  /48

  Est $768,161 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,834 Sq Ft

  13608 Gorgona Isle Dr, Windermere, FL 34786

  13608 Gorgona Isle Dr, Windermere, FL 34786
• 

  

  /16

  $759,500

  • 4 Beds
  • 3.5 Baths
  • 2,820 Sq Ft

  6832 Thornhill Cir, Windermere, FL 34786

  4 bed, 3.5 bath, 2,827 SF home in desirable Windermere Florida, minutes from Disney - see the fireworks from home !!! Oversized corner lot (8,850 sq ft) in cul-de-sac, 22’ ceiling in family room with high tinted windows giving lots of natural light, Kitchen with plenty of counter space as well as a walk in pantry and 41” cabinets, 39x39 center island with cabinets, 100” bar/counter, Butler’s

  Jonathan Minerick HOMECOIN.COM

  6832 Thornhill Cir, Windermere, FL 34786
• 

  /2

  $1,800,000 Sold Jun 30, 2025

  • 3,759 Sq Ft
  • $479/SF
  • 49 Days On Market

  • 5 Beds
  • 4.5 Baths
  • Built 2004

  11139 Camden Park Dr Unit 5, Windermere, FL 34786

  Discover unparalleled luxury in this stunning 5-bedroom, 4.5-bathroom estate nestled within the prestigious Keene's Pointe country club community in Windermere, Florida. Perfectly positioned along the second hole and green of the renowned Golden Bear Club, this turn-key golf course home offers breathtaking views and an exceptional lifestyle for discerning buyers. Step inside to find high-end

  Shane Croft COLDWELL BANKER RESIDENTIAL RE

  11139 Camden Park Dr Unit 5, Windermere, FL 34786
• 

  

  /23

  Est $698,885 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,985 Sq Ft

  9216 Outlook Rock Trail, Windermere, FL 34786

  9216 Outlook Rock Trail, Windermere, FL 34786
• 

  

  /21

  $397,499

  • 2 Beds
  • 2.5 Baths
  • 1,510 Sq Ft

  12335 Cruxbury Dr, Windermere, FL 34786

  Discover this spacious 2-bedroom, 2.5-bath end-unit townhome nestled in a charming Windermere community known for its tree-lined streets, sidewalks, and beautiful canopied trees. Step inside to find brand new carpet throughout and a functional layout featuring a large kitchen and great room, plus an additional flex space at the front of the home—perfect for a home office or playroom. The kitchen

  Amy Kidwell PREFERRED REAL ESTATE BROKERS

  12335 Cruxbury Dr, Windermere, FL 34786
• 

  /2

  $799,000 Sold Jun 30, 2025

  • 2,772 Sq Ft
  • $288/SF
  • 34 Days On Market

  • 5 Beds
  • 2.5 Baths
  • Built 2017

  8803 Peachtree Park Ct, Windermere, FL 34786

  On a private cul-de-sac in a prime Windermere location, this meticulously maintained home offers an abundance of custom upgrades and unparalleled views of Walt Disney World’s Magic Kingdom fireworks as the park entrance is just a two-minute drive. Whether you work at Disney and need a nice short commute or are a Disney aficionado looking for the ideal Florida second home, this home will check all

  Janice Edwards-Diaz, PA PREMIER SOTHEBYS INT'L REALTY

  8803 Peachtree Park Ct, Windermere, FL 34786
• 

  

  /60

  Est $684,195 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,015 Sq Ft

  7949 Jailene Dr, Windermere, FL 34786

  7949 Jailene Dr, Windermere, FL 34786
• 

  

  /70

  $8,325,000

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

  5074 Isleworth Country Club Dr, Windermere, FL 34786

  Experience luxury living at its finest in the high end gated community of Isleworth. Nestled on the 6th fairway of Isleworth’s world-renowned golf course, this beautifully redesigned estate offers over 6,900 square feet of exquisite living space, featuring 5 bedrooms and 6.5 bathrooms. Completely reimagined by renowned architect Mark Nasrallah, the home blends modern elegance with resort-style

  Armaan Memarpouri MEMARPOURI REALTY LLC

  5074 Isleworth Country Club Dr, Windermere, FL 34786
• 

  /2

  $840,000 Sold Jun 30, 2025

  • 2,835 Sq Ft
  • $296/SF
  • 168 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 2017

  9036 Arbors Edge Trail, Windermere, FL 34786

  Located in Windermere and 2 miles from Disney Attractions, this inviting ENERGY STAR Certified home features 4 Bedrooms, 3 Baths, LOFT, Covered Lanai and 2 Car Garage. First floor bedroom perfect for visiting guests or as an office. FORMAL DINING with Tray Ceiling. Kitchen open to Family Room and features 42" Designer Cabinets in Nutmeg w/Crown Molding, Granite counters in Uba Tuba, Stainless

  Eduardo Pavone ON ME REALTY

  9036 Arbors Edge Trail, Windermere, FL 34786
• 

  

  /28

  Est $2,477,667 Not Listed For Sale

  • 4 Beds
  • 7 Baths
  • 5,561 Sq Ft

  9950 6th St, Windermere, FL 34786

  9950 6th St, Windermere, FL 34786
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  /66

  $378,000

  • 3 Beds
  • 2.5 Baths
  • 1,480 Sq Ft

  7462 Bentonshire Ave, Windermere, FL 34786

  Move in ready 3/2.5 Townhome in Windermere! New roof 2024. AC compressor new June 2025. Rear entry 2 car garage. All stainless-steel fridge, stove, microwave and dishwasher and solid surface counter tops. Versatile all ceramic tiled 1st floor plan with formal dining room or use as front office. Open kitchen to rear great room that opens to covered screened private patio and fenced yard. All

  Ivan Petkov FLORIDA REALTY INVESTMENTS

  7462 Bentonshire Ave, Windermere, FL 34786
• 

  /2

  $1,150,000 Sold Jun 27, 2025

  • 3,958 Sq Ft
  • $291/SF
  • 79 Days On Market

  • 5 Beds
  • 4.5 Baths
  • Built 2002

  1613 Glenwick Dr, Windermere, FL 34786

  Envision yourself living in this beautifully updated 5-bedroom, 4.5-bath home in the prestigious, guard-gated Reserve at Belmere. Situated on over half an acre, this elegant residence offers ample space, privacy, and luxurious features for refined living. As you arrive on the cul de sac, a circular driveway leads you into a sophisticated courtyard entryway, setting the tone for the elegance

  Kelly Whitaker PREMIER SOTHEBYS INT'L REALTY

  1613 Glenwick Dr, Windermere, FL 34786
• 

  

  /41

  Est $456,835 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,912 Sq Ft

  13760 Calera Alley, Windermere, FL 34786

  13760 Calera Alley, Windermere, FL 34786
• 

  

  /76

  $3,499,000

  • 4 Beds
  • 4.5 Baths
  • 7,222 Sq Ft

  3426 Cocard Ct, Windermere, FL 34786

  An exceptional estate, masterfully renovated and transformed into a reimagined showplace: complete with a brand-new exquisite chef’s kitchen, family room, and bar with glass enclosed wine rack – plus mammoth private swimming pool and spa with new decking and checkerboard synthetic turf with multiple sitting venues. Featured on CNBC as “most sought-after floor plan,” this masterpiece residence

  Rob Rahter STOCKWORTH REALTY GROUP

  3426 Cocard Ct, Windermere, FL 34786
• 

  /2

  $540,000 Sold Jun 26, 2025

  • 2,073 Sq Ft
  • $260/SF
  • 6 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2014

  8607 Crescendo Ave, Windermere, FL 34786

  ENERGY-EFFICIENT HOME READY FOR MOVE IN APPROX JUNE 13 2025! The Alcott floor plan includes master suite, 2 additional bedrooms and a den that can be used as the 4 bedroom , as well as 2 and1/2 baths, and a 2-car garage. Over-sized family room is open to functional kitchen which features a casual dining area. Master Suite offers corner soaking tub, separate shower, plus separate vanities. And a

  Shirlei Devito CENTURY 21 CARIOTI

  8607 Crescendo Ave, Windermere, FL 34786
• 

  

  /29

  Est $547,546 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,152 Sq Ft

  12273 Joshua Tree Trail, Windermere, FL 34786

  12273 Joshua Tree Trail, Windermere, FL 34786
• 

  

  /26

  $1,770,000

  • 5 Beds
  • 3.5 Baths
  • 4,000 Sq Ft

  12663 Hawkstone Dr, Windermere, FL 34786

  Discover the only single-story lakefront home available under $2 million on the prestigious Lake Sawyer. This rare opportunity offers unmatched privacy, breathtaking views, and true single-level luxury in one of Windermere’s most desirable neighborhoods.With 5 bedrooms, 3.5 bathrooms, an office, and a 3-car garage, this home blends comfort and sophistication. Inside, you'll find

  John Cunningham KELLER WILLIAMS CLASSIC

  12663 Hawkstone Dr, Windermere, FL 34786
• 

  /2

  $1,000,000 Sold Jun 26, 2025

  • 3,034 Sq Ft
  • $330/SF
  • 15 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 2005

  11415 N Camden Commons Dr, Windermere, FL 34786

  Welcome to 11415 N Camden Commons Drive—an exceptional pool home in the prestigious, guard-gated golf community of Keene’s Pointe. This beautifully well maintained 4-bedroom, 3-bathroom residence features a dedicated office/den, formal and casual living spaces, and a host of upgrades for worry-free living.Charming curb appeal greets you with a classic front porch, mature trees, and a

  Christina Fata REAL BROKER, LLC

  11415 N Camden Commons Dr, Windermere, FL 34786
• 

  

  /33

  Est $1,321,032 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 3,493 Sq Ft

  1109 Estancia Woods Loop, Windermere, FL 34786

  1109 Estancia Woods Loop, Windermere, FL 34786
• 

  

  /73

  $849,900

  • 5 Beds
  • 4.5 Baths
  • 2,844 Sq Ft

  11761 Bella Milano Ct, Windermere, FL 34786

  One or more photo(s) has been virtually staged. Welcome to 11761 Bella Milano Ct, a fully renovated 5-bedroom, 4.5-bath sanctuary nestled within the private gates of Belmere, one of Windermere’s most sought-after communities. This is more than a home — it's a lifestyle crafted for those who value refined beauty, thoughtful upgrades, and connection to everything that makes Central Florida truly

  Lizzette Bolivar Rubio PMI ORLANDO PARKS

  11761 Bella Milano Ct, Windermere, FL 34786
• 

  /2

  $850,000 Sold Jun 26, 2025

  • 2,478 Sq Ft
  • $343/SF
  • 21 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1978

  2532 Waterview Place, Windermere, FL 34786

  LOCATION, LOCATION, LOCATION! Here's your opportunity to join the coveted Windermere Downs community, just minutes from downtown Windermere,and with private access to the renowned Butler Chain of Lakes. This tranquil home is set on a .43-acre lot in a peaceful cul-de-sac, offering a serene setting with mature trees and partial lake views that promise breathtaking sunsets.The open and airy

  Tammy Schuster COMPASS FLORIDA LLC

  2532 Waterview Place, Windermere, FL 34786
• 

  

  /71

  Est $619,380 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,374 Sq Ft

  6769 Merrick Landing Blvd, Windermere, FL 34786

  6769 Merrick Landing Blvd, Windermere, FL 34786
• 

  

  /48

  $2,545,000

  • 5 Beds
  • 7 Baths
  • 5,934 Sq Ft

  11106 Coniston Way, Windermere, FL 34786

  A one-of-a-kind French Provincial estate, "The Monet," was crafted by Master Custom Builder Castleworks in 2008 and has been updated a smart home for today’s buyers. This luxurious residence is situated on a rare corner lot within the prestigious gated community of The Reserve at Lake Butler Sound, featuring a 24-hour manned entrance, picturesque English garden parks, a lakeside gazebo, and a

  Toni Marie Cafferty COMPASS FLORIDA LLC

  11106 Coniston Way, Windermere, FL 34786
• 

  /2

  $1,015,000 Sold Jun 26, 2025

  • 4,751 Sq Ft
  • $214/SF
  • 20 Days On Market

  • 8 Beds
  • 5 Baths
  • Built 2012

  6008 Golden Dewdrop Trail, Windermere, FL 34786

  Welcome to your dream home! This stunning 8-bedroom, 5-bathroom residence offers unparalleled luxury and comfort. Nestled in a serene neighborhood, this property boasts a spacious layout perfect for large families or those who love to entertain.

  Paulo Silva GRINDSTONE REALTY & PROPERTY MANAGEMENT LLC

  6008 Golden Dewdrop Trail, Windermere, FL 34786
• 

  

  /25

  Est $465,147 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,976 Sq Ft

  13752 Bressler Alley, Windermere, FL 34786

  13752 Bressler Alley, Windermere, FL 34786
• 

  

  /90

  $1,700,000

  • 5 Beds
  • 4.5 Baths
  • 3,868 Sq Ft

  11015 Hawkshead Ct, Windermere, FL 34786

  Dream home in Windermere! Nestled inside the gates of the luxurious community of Reserve at Lake Sound. Move-in ready home! Tile roof replaced in 2021. Heated area of 3868 sqft built with high quality material and finishing, tall ceilings and travertine floors in the common areas. The refurbishment, done 4 years ago, resulted in adding modern sophistication to the home. The double door entrance

  Ahmed Elkomy CENTURY 21 CARIOTI

  11015 Hawkshead Ct, Windermere, FL 34786
• 

  /2

  $1,100,000 Sold Jun 26, 2025

  • 5,010 Sq Ft
  • $220/SF
  • 513 Days On Market

  • 6 Beds
  • 4.5 Baths
  • Built 2015

  9149 Outlook Rock Trail, Windermere, FL 34786

  Stunning property located in WINDERMERE Florida. The grand entrance opens to an expansive great room, perfect for entertaining or relaxing with family. With 6 bedrooms, 4.5 bathrooms, and a bonus room/theater/game room. The luxurious master bedroom with comfort, privacy, two walking closet and walking shower. The gourmet kitchen boasts fully equipped. The screened pool gives you more privacy and

  Christian Posegger DE PAULA REALTY USA INC.

  9149 Outlook Rock Trail, Windermere, FL 34786
• 

  

  /55

  Est $1,127,430 Not Listed For Sale

  • 6 Beds
  • 4.5 Baths
  • 4,511 Sq Ft

  8388 Lookout Pointe Dr, Windermere, FL 34786

  8388 Lookout Pointe Dr, Windermere, FL 34786
• 

  

  /39

  $650,000

  • 4 Beds
  • 2 Baths
  • 2,211 Sq Ft

  7214 Tattant Blvd, Windermere, FL 34786

  Beautiful 4 Bed / 2 Bath Pool Home in Windermere!?This move-in ready home features a private screened pool & spa with no rear neighbors, low HOA, and a spacious open floor plan perfect for entertaining. Enjoy granite countertops, stainless steel appliances, and a large kitchen island that flows into the family room.The primary suite offers a walk-in closet, double vanities, garden tub, and

  Rebeca Lima ORLANDO BROTHERS REAL ESTATE LLC

  7214 Tattant Blvd, Windermere, FL 34786
• 

  /2

  $330,000 Sold Jun 25, 2025

  • 1,442 Sq Ft
  • $229/SF
  • 33 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2009

  8256 Maritime Flag St Unit 103, Windermere, FL 34786

  **LUXURIOUS LAKESIDE LIVING**Tucked into the heart of Windermere’s desirable Lakeside at Lakes of Windermere community, this first-floor, corner unit condo at **8256 Maritime Flag St #103 (Unit 1710)** delivers an ideal blend of privacy, accessibility, and vibrant resort-style amenities. With no stairs to climb, this ground-floor location offers added convenience for everyday living,

  Brad Rosel EXP REALTY LLC

  8256 Maritime Flag St Unit 103, Windermere, FL 34786
• 

  

  /43

  Est $527,136 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,089 Sq Ft

  11560 Charnock Dr, Windermere, FL 34786

  11560 Charnock Dr, Windermere, FL 34786
• 

  

  /52

  $5,494,000

  • 5 Beds
  • 6.5 Baths
  • 4,665 Sq Ft

  5199 Latrobe Dr, Windermere, FL 34786

  Nestled in the exclusive and coveted gated community of Isleworth, this fully remodeled, turn-key golf estate is positioned along Isleworth’s famed championship golf course. This remarkable golf-front property reveals a stylish and modern retreat you are sure to fall in love with. Spanning more than 6,600 square feet of indoor living and outdoor covered space, the estate blends warmth, elegance

  Shane Croft COLDWELL BANKER RESIDENTIAL RE

  5199 Latrobe Dr, Windermere, FL 34786
• 

  /2

  $455,000 Sold Jun 25, 2025

  • 2,001 Sq Ft
  • $227/SF
  • 86 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2019

  13727 Bressler Alley, Windermere, FL 34786

  Price Improvement! Now Listed at $458,500 – Turnkey Townhome in the Vineyards of Horizon West!Welcome to 13727 Bressler Alley, a beautifully upgraded townhome in the highly desirable Vineyards of Horizon West community in Windermere, FL. This meticulously maintained home combines modern luxury with functionality, offering an ideal living space in one of Central Florida’s most sought-after

  Nicholas Vaseloff REAL BROKER, LLC

  13727 Bressler Alley, Windermere, FL 34786

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