Windermere, FL Homes for Sale

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  $1,950,000

  • 4 Beds
  • 4.5 Baths
  • 4,460 Sq Ft

  6330 Lake Burden View Dr, Windermere, FL 34786

  The coveted Keene's Pointe lifestyle awaits behind the guarded gates of this world renowned golf community. Perfectly positioned near the tranquil shores of Lake Burden, this Mediterranean-inspired estate and it’s stunning architecture captures the eye and invites you to a front-row seat to the nightly water front display of Walt Disney World fireworks. This custom-built residence showcases

  

  Karla Ryan

  WATSON REALTY CORP

  (689) 314-7434

  6330 Lake Burden View Dr, Windermere, FL 34786
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  $469,999

  • 3 Beds
  • 2.5 Baths
  • 2,002 Sq Ft

  13733 Bressler Aly, Windermere, FL 34786

  Location location location!! This beautiful 3 bedrooms, 2 1/2 baths, includes a spacious open floor plan with a breakfast bar in the kitchen area and Living Room/Dining Room Combo. Master Bedroom is located on the second floor, as well as two more bedrooms. This two car garage townhouse has a charming front porch which overlooks the pond and offers, not one, but two community pools and a

  

  Robert Welker, III

  CORCORAN PREMIER REALTY

  (689) 336-7911

  13733 Bressler Aly, Windermere, FL 34786
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  $1,390,000

  • 7 Beds
  • 4.5 Baths
  • 4,563 Sq Ft

  11658 Hampstead St, Windermere, FL 34786

  **This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.** Welcome to 11658 Hampstead Street, a refined Windermere showpiece tucked inside the highly sought-after Enclave community, zoned for Orange County’s top-rated schools. This home defines elevated Florida living, offering

  

  Thomas Nickley

  KELLER WILLIAMS REALTY AT THE PARKS

  (689) 319-8390

  11658 Hampstead St, Windermere, FL 34786
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  $330,000

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

  8180 Boat Hook Loop Unit 108/301, Windermere, FL 34786

  Discover the best of Windermere living in this meticulously maintained 3-bedroom, 2-bath CORNER UNIT condo in Lakeside at Lakes of Windermere. An expansive wrap-around screened porch embraces tranquil views and Florida breezes while providing an ideal space for morning coffee or evening relaxation. Inside, the open-concept layout features silestone countertops, cherry cabinets, and stainless

  

  Erin Aaron

  EXP REALTY LLC

  (689) 300-6265

  8180 Boat Hook Loop Unit 108/301, Windermere, FL 34786
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  $609,999

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

  8632 Abbotsbury Dr, Windermere, FL 34786

  **This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.** Welcome to 8632 Abbotsbury Drive, a beautifully situated 4-bedroom, 3.5-bath residence offering 2,720 square feet of heated living space in the heart of Windermere, one of Central Florida’s most desirable communities. This

  

  Thomas Nickley

  KELLER WILLIAMS REALTY AT THE PARKS

  (689) 232-4855

  8632 Abbotsbury Dr, Windermere, FL 34786
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  $727,500

  • 4 Beds
  • 3.5 Baths
  • 2,594 Sq Ft

  13519 Bicton Ln, Windermere, FL 34786

  **Sellers are offering a 5.5% INTERESTED RATE** Luxury Windermere Home for Sale in Gated Community with New Roof & Windows!Welcome to this stunning 4-bedroom, 3-bathroom home in a sought-after gated Windermere community, offering nearly 3,000 square feet of beautifully designed living space, a 3-car garage, NEW ROOF and NEW WINDOWS. Enjoy nightly Walt Disney World firework views from the

  

  Tiphany Weeks

  DIAMOND REAL ESTATE GROUP

  (407) 974-7651

  13519 Bicton Ln, Windermere, FL 34786
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  $1,200,000

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

  3629 Lake Buynak Rd, Windermere, FL 34786

  Back on market—buyer withdrew for personal reasons, not due to any home-related issues.Set on 1.3 acres in the Lake Buynak Estate community, this 4-bedroom, 3.5-bath home presents an outstanding opportunity for investors, builders, or buyers wanting space and a Windermere-area address with NO HOA. Offering over 2,600 square feet, two ensuite bedrooms, a split layout, multiple screened

  

  Tania Matthews

  KELLER WILLIAMS ELITE PARTNERS III REALTY

  (407) 519-3922

  3629 Lake Buynak Rd, Windermere, FL 34786
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  $3,390,000

  • 4 Beds
  • 4.5 Baths
  • 3,365 Sq Ft

  5050 Isleworth Country Club Dr, Windermere, FL 34786

  Situated on the 6th fairway along the course of Isleworth Golf & Country Club, this updated golf front sparkles with new porcelain tile throughout and modern chandeliers. This single-story residence was renovated in 2020 featuring a new tile roof, fresh paint inside and out, all bathrooms updated and a fully renovated kitchen. Spanning over 3,300 square feet, the 4-bedroom, 4.5-bath is nestled in

  

  Toni Marie Cafferty

  COMPASS FLORIDA LLC

  (407) 807-6191

  5050 Isleworth Country Club Dr, Windermere, FL 34786
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  $824,900

  • 4 Beds
  • 2 Baths
  • 2,404 Sq Ft

  2641 Hempel Ave, Windermere, FL 34786

  Welcome to this beautifully renovated home in highly desirable Windermere, where modern upgrades meet timeless comfort on a rare one-acre lot with NO HOA.Completely remodeled this home has been thoughtfully updated from top to bottom. Renovations include new flooring throughout, fresh interior paint, a fully redesigned kitchen, updated bathrooms, new windows, new interior doors and custom

  

  Frank Mediavilla

  KNIGHTS REALTY

  (689) 263-6722

  2641 Hempel Ave, Windermere, FL 34786
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  $595,000

  • 3 Beds
  • 2.5 Baths
  • 2,139 Sq Ft

  6382 Golden Dewdrop Trail, Windermere, FL 34786

  Ideally situated within WINDERMERE LANDINGS and in close proximity to highly rated schools, convenience stores, restaurants, golf courses & other amenities, this IMMACULATELY presented 3 bedroom and 2.5 bath property with 2 car garage and private driveway is a true GEM with its stunning curb appeal and TURNKEY presentation! On approach the front porch feels inviting with its welcoming entryway

  

  Alice Anne Jackson

  CORCORAN PREMIER REALTY

  (689) 308-0830

  6382 Golden Dewdrop Trail, Windermere, FL 34786
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  $1,029,990 New Construction

  • 4 Beds
  • 4 Baths
  • 3,123 Sq Ft

  14285 Crest Palm Ave, Windermere, FL 34786

  Welcome to the Arlington with Bonus! This stunning 3,123 square foot, two-story floor plan boasts 4 bedrooms, 4 bathrooms, and a spacious 2-car garage. Experience the ultimate in open-concept living on the main level, perfect for entertaining family and friends. The garage includes an extra hobby/work space for all your creative projects. Step outside and unwind under the inviting covered patio,

  

  Cindy Sapp

  OLYMPUS EXECUTIVE REALTY INC

  14285 Crest Palm Ave, Windermere, FL 34786
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  $2,235,000

  • 6 Beds
  • 6 Baths
  • 5,031 Sq Ft

  713 Main St, Windermere, FL 34786

  Architecturally refined and thoughtfully designed, this custom built Transitional Craftsman residence blends timeless craftsmanship with modern luxury in the heart of Historic Olde Windermere. Rich wood detailing, exposed pecky cypress beams, and dramatic stonework create warmth and depth throughout. The chef’s kitchen is both functional and sculptural, featuring a stone-framed cooking alcove,

  

  Kari Fleck

  THE REAL ESTATE COLLECTION LLC

  (407) 494-6941

  713 Main St, Windermere, FL 34786
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  $1,480,000

  • 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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  $679,994

  • 4 Beds
  • 2.5 Baths
  • 2,053 Sq Ft

  13013 Overstreet Rd, Windermere, FL 34786

  Welcome to 13013 Overstreet Rd — a beautifully upgraded 4-bedroom, 2.5-bath home located in one of Windermere’s most desirable and sought-after communities. This property combines modern living, elegant design, and the true Florida lifestyle you’ve been searching for.Step inside to an open, bright floor plan featuring gorgeous wood floors, a spacious living area, and a modern kitchen with

  

  Omar Andreasen

  EXP REALTY LLC

  (689) 263-7353

  13013 Overstreet Rd, Windermere, FL 34786
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  $2,650,000

  • 5 Beds
  • 6.5 Baths
  • 6,248 Sq Ft

  8402 Lake Burden Cir Unit 2, Windermere, FL 34786

  One or more photo(s) has been virtually staged. Newly added virtually staged images to help with your interior design inspiration! Experience luxury waterfront living in the prestigious guard gated community of Keene's Pointe. This custom estate offers over 6,000 sq ft of elegant living space with 5-bedroom ensuites and a full pool bath with shower and powder room off of the Theater. A chef's

  

  Toni Marie Cafferty

  COMPASS FLORIDA LLC

  (689) 312-8950

  8402 Lake Burden Cir Unit 2, Windermere, FL 34786
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  $625,000

  • 5 Beds
  • 3 Baths
  • 2,555 Sq Ft

  6846 Helmsley Cir, Windermere, FL 34786

  Seller to provide $10,000 in concessions to be used for closing costs or rate buydown. NEW ROOF! Welcome to 6846 Helmsley Circle in beautiful Windermere, FL! This stunning 5-bedroom, 3-bathroom home is situated on the largest lot in the neighborhood, offering over a quarter-acre of space with two expansive backyards. Imagine the possibilities—perhaps a pool or even a pickleball court! The home

  

  Nickolas Amburgey

  COMPASS FLORIDA LLC

  (407) 392-9729

  6846 Helmsley Cir, Windermere, FL 34786
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  $1,024,990 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,783 Sq Ft

  Tuttle Plan at Lake Cawood Cove - Traditional, Windermere, FL 34786

  The Tuttle is a two-story home offering four bedrooms, two full bathrooms, one half bathroom, and a two-car garage. The first-floor primary suite provides privacy and comfort. The spacious kitchen opens to a covered lanai, ideal for outdoor living and entertaining. Additional features include an oversized laundry room and an optional butler’s pantry to enhance functionality. Modern finishes,

  Ashton Woods Builder

  5432 Winter Garden Vineland Rd Unit 37932784, Windermere, FL 34786
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  $1,034,990 New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,791 Sq Ft

  Moseley Plan at Lake Cawood Cove - Traditional, Windermere, FL 34786

  The Moseley is a thoughtfully designed two-story home with three bedrooms, two full bathrooms, one half bathroom, and a two-car garage. This plan features a dramatic two-story family room that creates a bright and open living space. The second-floor primary suite offers privacy and comfort, while additional flexible living areas provide room to relax or entertain. Modern finishes, abundant

  Ashton Woods Builder

  5432 Winter Garden Vineland Rd Unit 37932785, Windermere, FL 34786
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  $680,000

  • 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
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  $650,000

  • 4 Beds
  • 2 Baths
  • 2,063 Sq Ft

  9426 Palm Tree Dr, Windermere, FL 34786

  This is it! Welcome home to this updated, showstopper in Windermere with an oversized pool. From the moment you walk in the door, you will be impressed with how open and expansive the home feels- the kitchen, dining, family and living areas are included in one great space. The family and living room share a double-sided wood burning fireplace and both overlook the pool area. The kitchen has been

  Richard Alpizar IRON VALLEY REAL ESTATE CENTRAL FLORIDA

  9426 Palm Tree Dr, Windermere, FL 34786
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  $4,960,000

  • 4 Beds
  • 5 Baths
  • 4,739 Sq Ft

  5186 Vardon Dr, Windermere, FL 34786

  One or more photo(s) has been virtually staged. Presenting a newly remodeled luxury estate ideally positioned along Isleworth’s renowned championship golf course, showcasing stunning views of the signature 3rd hole. This exceptional residence offers approximately 4739 square feet of refined living space with 4 bedrooms and 4 1/2 bathrooms, soaring ceilings, elegant formal living and dining rooms,

  Winnie Tam FLORIDA REALTY INVESTMENTS

  5186 Vardon Dr, Windermere, FL 34786
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  $1,074,990 New Construction

  • 4 Beds
  • 3.5 Baths
  • 3,074 Sq Ft

  Griffin Plan at Lake Cawood Cove - Traditional, Windermere, FL 34786

  The Griffin is a two-story home offering four bedrooms, three full bathrooms, one half bathroom, and a two-car garage. The kitchen opens to a dramatic two-story family room, creating a bright and inviting living space. The second-floor primary suite offers privacy and comfort, while a conveniently located laundry room and optional butler’s pantry enhance everyday functionality. Additional

  Ashton Woods Builder

  5432 Winter Garden Vineland Rd Unit 37932783, Windermere, FL 34786
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  $1,390,000

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

  8375 Bowden Way, Windermere, FL 34786

  "Price Improvement". 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

  Oscar Rodriguez B LIVE COMMERCIAL AND RESIDENT

  8375 Bowden Way, Windermere, FL 34786
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  $3,500,000 Open Sat 11AM - 2PM

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

  10577 Down Lakeview Cir, Windermere, FL 34786

  Experience true lakefront living on the famed Butler Chain of Lakes. This exceptional custom home offers 137 feet of pristine shoreline and sits on nearly one acre of high, dry land with sweeping panoramic water views and nightly Disney fireworks. Arrive via a circular paved drive framed by mature oaks and step onto the covered porch through an impressive 8 inch solid cedar entry door with

  Simon Simaan THE SIMON SIMAAN GROUP

  10577 Down Lakeview Cir, Windermere, FL 34786
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  $1,129,990 New Construction

  • 4 Beds
  • 3.5 Baths
  • 3,692 Sq Ft

  14354 Crest Palm Ave, Windermere, FL 34786

  The Tidewater with Bonus floorplan offers a versatile and spacious two-story layout, featuring 4 bedrooms and 3.5 bathrooms. Spanning 3,692 sq. ft., this home includes a large two-car garage for ample storage and convenience. The first floor boasts an inviting great room connected to an open kitchen and dining area, perfect for entertaining. The owner’s suite provides a private retreat with a

  Dream Finders Homes Builder

  14354 Crest Palm Ave, Windermere, FL 34786
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  /15

  $979,990 New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,226 Sq Ft

  Plant at Lake Cawood Cove - Traditional, Windermere, FL 34786

  The Plant is a one-story home offering three bedrooms, two full bathrooms, one half bathroom, and a two-car garage. The spacious kitchen features a large island and flows seamlessly into the dining and family rooms. A private primary suite includes a walk-in closet, while a generously sized den and covered lanai provide versatile living spaces for work, relaxation, and outdoor enjoyment. Modern

  Ashton Woods Builder

  5432 Winter Garden Vineland Rd Unit 37932781, Windermere, FL 34786
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  /2

  $855,990 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,712 Sq Ft

  Tidewater Plan at Palms at Windermere, Windermere, FL 34786

  The Tidewater floorplan offers a versatile and spacious two-story layout, featuring 4 bedrooms and 2.5 bathrooms. Spanning 2,712 sq. ft., this home includes a large two-car garage for ample storage and convenience. The first floor boasts an inviting great room connected to an open kitchen and dining area, perfect for entertaining. The owner’s suite provides a private retreat with a generous

  Dream Finders Homes Builder

  14207 Crest Palm Ave Unit 36489841, Windermere, FL 34786
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  $499,000

  • 4 Beds
  • 2.5 Baths
  • 2,092 Sq Ft

  10624 Reams Rd, Windermere, FL 34786

  Welcome to this beautiful 4-bedroom, 2.5-bath home in the highly desirable Windermere Trails community. Just minutes from Disney World, you can enjoy nightly fireworks right from your front porch. The kitchen features 42" maple cabinets, granite countertops, and under-cabinet lighting. An open-concept design connects the spacious living and with the kitchen, perfect for entertaining. The primary

  Jeff Taulbee CHARLES RUTENBERG REALTY ORLANDO

  10624 Reams Rd, Windermere, FL 34786
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  $1,050,000

  • 5 Beds
  • 4 Baths
  • 3,070 Sq Ft

  13858 Caywood Pond Dr, Windermere, FL 34786

  JUST REMODELED! Stunning lakefront pool home located in the heart of Windermere, offering 5 bedrooms, 4 full bathrooms, and nearly 3,100 square feet of beautifully updated living space. Perfectly positioned between downtown Windermere and Winter Garden Village, this exceptional property is nestled within the highly desirable Summerport community and features pristine waterfront views. This is

  Chun Cai SPRING REALTY ONE LLC

  13858 Caywood Pond Dr, Windermere, FL 34786
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  $1,029,990 New Construction

  • 4 Beds
  • 4 Baths
  • 3,100 Sq Ft

  Arlington w/ Bonus Plan at Palms at Windermere, Windermere, FL 34786

  Welcome to the Arlington with Bonus! This stunning 3,099 square foot, two-story floor plan boasts 4 bedrooms, 4 bathrooms, and a spacious 2-car garage. Experience the ultimate in open-concept living on the main level, perfect for entertaining family and friends. The garage includes an extra hobby/work space for all your creative projects. Step outside and unwind under the inviting covered patio,

  Dream Finders Homes Builder

  14207 Crest Palm Ave Unit 36493225, Windermere, FL 34786
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  $999,989 New Construction

  • 4 Beds
  • 3.5 Baths
  • 3,239 Sq Ft

  14377 Crest Palm Ave, Windermere, FL 34786

  The Tidewater with Bonus floorplan offers a versatile and spacious two-story layout, featuring 4 bedrooms and 3.5 bathrooms. Spanning 3,239 sq. ft., this home includes a large two-car garage for ample storage and convenience. The first floor boasts an inviting great room connected to an open kitchen and dining area, perfect for entertaining. The owner’s suite provides a private retreat with a

  Dream Finders Homes Builder

  14377 Crest Palm Ave, Windermere, FL 34786
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  /13

  $1,129,990 New Construction

  • 5 Beds
  • 4.5 Baths
  • 3,542 Sq Ft

  Duval Plan at Lake Cawood Cove - Traditional, Windermere, FL 34786

  The Duval is a two‐story home offering five bedrooms, four full bathrooms, one half bathroom, and a two‐car garage. A bright kitchen with breakfast nook anchors the open main floor, while a second‐floor loft overlooks the family room below. The private second‐floor primary suite, optional butler’s pantry, and centrally located laundry room add convenience and luxury to this spacious plan.

  Ashton Woods Builder

  5432 Winter Garden Vineland Rd Unit 37932788, Windermere, FL 34786
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  /2

  $999,989 New Construction

  • 4 - 6 Beds
  • 3.5 Baths
  • 3,199 Sq Ft

  Tidewater w/ Bonus Plan at Palms at Windermere, Windermere, FL 34786

  The Tidewater with Bonus floorplan offers a versatile and spacious two-story layout, featuring 4 bedrooms and 3.5 bathrooms. Spanning 3,199 sq. ft., this home includes a large two-car garage for ample storage and convenience. The first floor boasts an inviting great room connected to an open kitchen and dining area, perfect for entertaining. The owner’s suite provides a private retreat with a

  Dream Finders Homes Builder

  14207 Crest Palm Ave Unit 36498094, Windermere, FL 34786
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  $1,400,000

  • 5 Beds
  • 5.5 Baths
  • 3,383 Sq Ft

  1625 Down Lake Dr, Windermere, FL 34786

  One or more photo(s) has been virtually staged. A rare opportunity in Windermere's established Lakes / Lake Down neighborhood — an exceptional builder's home offering the quality & finishes typically found at much higher price points. Set on a beautifully manicured ONE-ACRE LOT with BOAT ACCESS to the BUTLER CHAIN OF LAKES, this residence blends comfort, sophistication & the true Central Florida

  Cindy Rosenbloom THE ROSENBLOOM TEAM

  1625 Down Lake Dr, Windermere, FL 34786
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  $2,500,000

  • 5 Beds
  • 4.5 Baths
  • 4,284 Sq Ft

  81 Oakdale St, Windermere, FL 34786

  Gorgeous canal-front home with direct access to the Butler Chain of Lakes and just four blocks from the heart of downtown Windermere, this 2024 luxury remodel offers the perfect blend of modern living and small-town charm. Minutes from Food Truck Fridays, local cafés, parks, tennis courts, and year-round community events, this home blends modern elegance with the warmth of small-town living. Step

  David Warzycha COLDWELL BANKER REALTY

  81 Oakdale St, Windermere, FL 34786
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  $600,000

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

  6626 Bridgewater Village Rd, Windermere, FL 34786

  **Corner-Lot Home Across from Park in The Vineyards of Horizon West** Perfectly positioned on a corner lot directly across from a peaceful green space, this bright and beautifully upgraded home is located in one of Horizon West’s most sought-after communities. With park views, walkable streets, and a true neighborhood feel, this home offers the ideal blend of comfort, style, and location. The

  David Dorman CENTURY 21 CARIOTI

  6626 Bridgewater Village Rd, Windermere, FL 34786
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  $999,998

  • 4 Beds
  • 3 Baths
  • 2,743 Sq Ft

  2125 Kane Park Way, Windermere, FL 34786

  Welcome to this beautifully updated single-story pool home on a rare 0.71-acre cul-de-sac lot in Windermere’s Willows at Lake Rhea, zoned for A-rated schools and offering exceptional privacy between homes. Surrounded by mature landscaping, the property provides a peaceful setting rarely found in newer communities while still offering convenient access to major roads, shopping, dining, and area

  Deb Schroeder INFINITY REALTY GROUP LLC

  2125 Kane Park Way, Windermere, FL 34786
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  $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. Step

  Lynn London EXP REALTY LLC

  13430 Hopkinton Ct, Windermere, FL 34786
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  /2

  $3,200,000

  • Land
  • 6.76 Acres
  • $473,373 per Acre

  934 Roberson Rd, Ocoee, FL 34761

  PROPERTY DESCRIPTION - We are pleased to present a premier investment opportunity at 934 Roberson Road in Ocoee, just west of Orlando. This 6.76-acre parcel of vacant land comes with full site plan approval from the City of Ocoee for a 120-bed assisted living facility, making it an exceptional prospect for those looking to capitalize on the burgeoning demand for senior care services in Central

  Chase Collier Eshenbaugh Land Company

  934 Roberson Rd, Ocoee, FL 34761
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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

Showing Results 1 - 40, Page 1 of 7

Why Live in Windermere

Windermere, Florida, is a small town known for its Old Florida charm and scenic setting on the Butler Chain of Lakes. It celebrated its centennial in 2025, and features quiet, walkable streets shaded by loblolly pines and live oaks draped with Spanish moss. The community is family-friendly, with highly rated public and private schools, including Windermere Elementary, Bridgewater Middle, Windermere High and Windermere Preparatory Academy. Windermere is composed of multiple subdivisions, many gated, with homes ranging from Mediterranean and French Provincial estates in Isleworth to Colonial Revivals and Contemporary styles in other developments. Townhomes and condos are also available in communities like Lake Burden and the Lakes of Windermere. The town offers various amenities, including the Windermere Recreation Center, Town Square Park, and private clubs like Isleworth Golf & Country Club. Residents enjoy local events such as the Windermere Wine & Dine and the weekly Windermere Farmer’s Market. Main Street features locally owned shops and dining options, while the nearby Grove shopping center and Dr. Phillips Restaurant Row provide additional choices. Windermere is conveniently located less than 15 miles from Orlando’s major attractions, hospitals, and about 25 miles from Orlando International Airport.

Learn more about living in Windermere

Frequently Asked Questions

What is the average home price in Windermere, FL?

Homes for sale in Windermere, FL have an average home price of $1,532,642.

Are home prices dropping in Windermere?

Yes, home prices in Windermere are down 2% in the last 12 months.

How many homes have sold over the last 12 months in Windermere, FL?

669 homes have sold in Windermere, FL over the last 12 months.

Is Windermere, FL a safe city?

In general, the safest neighborhood in Windermere, FL with lower crime scores is Bay Hill.

What are the most popular zip codes in Windermere, FL?

The most popular zip codes in Windermere, FL include 34786, 34761, 34734, 32835 and 32819.

What are the most popular neighborhoods in Windermere, FL?

The most popular neighborhood in Windermere, FL with the most homes for sale is Bay Hill.

How much do you need to make to afford a house in Windermere?

The median home price in Windermere is $975,000. If you put a 20% down payment of $195,000 and had a 30-year fixed mortgage with an interest rate of 6%, your estimated principal and interest payment would be $4,680 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $201K a year to afford the median home price in Windermere. Learn how much home you can afford with our Home Affordability Calculator.

How are the schools in Windermere, FL?

Windermere, FL has highly rated public and private schools. Some of the best schools in Windermere based on Niche Grades are Windermere Preparatory School, Thornebrooke Elementary School and Windermere Elementary School. The neighborhood in Windermere with the highest rated schools is Bay Hill. Browse all the schools in Windermere, FL to learn more.

Home Trends in Windermere, FL

On average, homes in Windermere, FL sell after 73 days on the market compared to the national average of 54 days. The median sale price for homes in Windermere, FL over the last 12 months is $844,000, up 4% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$844,000

Median Single Family Sale Price

$1,084,557

Median Townhouse Sale Price

$405,000

Median 2 Bedroom Sale Price

$295,000

Average Price Per Sq Ft

$368

Number of Homes for Sale

236

Last 12 months Home Sales

669

Months of Supply

4.20

Median List Price

$975,000

Median Change From 1st List Price

5%

Median Home Sale Price YoY Change

4%