Windermere, FL Houses for Sale

• 

  

  

  /39

  $1,098,000

  Open Sun 1PM - 3PM $22K PRICE DROP

  • 6 Beds
  • 4.5 Baths
  • 4,625 Sq Ft

  13525 Gorgona Isle Dr, Windermere, FL 34786

  Set within the highly sought-after Windermere Isle community, this exceptional estate offers elevated living defined by space, craftsmanship, and an unbeatable location just minutes from Walt Disney World. Featuring 6 bedrooms, 4.5 bathrooms, and over 4,600 square feet, the home is thoughtfully designed for both everyday living and effortless entertaining.A dramatic two-story foyer creates a

  

  Roo Klaers

  COLDWELL BANKER REALTY

  13525 Gorgona Isle Dr, Windermere, FL 34786
• Explore Windermere

• 

  

  

  /64

  $1,375,000

  $75K PRICE DROP

  • 6 Beds
  • 4.5 Baths
  • 3,463 Sq Ft

  11617 Camden Park Dr, Windermere, FL 34786

  Welcome to one of Central Florida’s premier guard-gated golf communities. This impeccably maintained, move-in ready residence showcases refined finishes throughout, including tile and laminate flooring (no carpet), crown molding in every room, and upgraded designer lighting. An abundance of space with 6 bedrooms and 4 1/2 baths. The living room is enhanced by striking wood-look tiled accent

  

  Carla Robles

  WATSON REALTY CORP

  11617 Camden Park Dr, Windermere, FL 34786
• 

  

  

  /87

  $2,225,000

  $70K PRICE DROP

  • 4 Beds
  • 5.5 Baths
  • 5,722 Sq Ft

  1136 Lake Whitney Dr, Windermere, FL 34786

  Experience resort-style living in the exclusive Villa D’Este, a masterpiece of sophistication designed by the renowned Arlington Homes. Positioned on the pristine shores of Lake Whitney, this estate welcomes you with a grand 20-foot entryway featuring a custom rustic wrought-iron chandelier and immediate, unobstructed water views. The main floor is a sanctuary of luxury, featuring an Executive

  

  Mauro Costa

  VISTA CAY REALTY COMPANY

  1136 Lake Whitney Dr, Windermere, FL 34786
• 

  

  

  /54

  $717,000

  $32K PRICE DROP

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

  13519 Bicton Ln, Windermere, FL 34786

  Welcome to one of Windermere's most sought-after gated communities — where luxury living meets unbeatable Central Florida convenience. This impeccably maintained 4-bedroom, 3-bathroom home offers nearly 3,000 square feet of thoughtfully designed living space, a 3-car garage, and a brand-new roof and windows, giving buyers peace of mind and long-term value from day one.DISNEY VIEWS & OUTDOOR

  

  Tiphany Weeks

  DIAMOND REAL ESTATE GROUP

  13519 Bicton Ln, Windermere, FL 34786
• 

  

  

  /43

  $1,198,000

  Open Sun 1PM - 4PM $27K PRICE DROP

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

  109 E 12th Ave, Windermere, FL 34786

  Modern style blends with Windermere charm. This totally renovated home is located just steps from Lake Bessie in the Town of Windermere. Set on a beautifully landscaped corner lot with no HOA, this home combines luxury and comfort in one of Central Florida’s most desirable communities. Every detail has been thoughtfully updated to include roof (2018), a/c (2016), plumbing, flooring, drain field

  

  Judy Black

  UPSIDE REAL ESTATE INC

  109 E 12th Ave, Windermere, FL 34786
• 

  

  /65

  $1,439,000

  $111K PRICE DROP

  • 4 Beds
  • 4.5 Baths
  • 3,399 Sq Ft

  12411 Montalcino Cir, Windermere, FL 34786

  A custom home in the desirable Casa del Lago community. The Spanish-style exterior and elegant, clean transitional interior will surely catch your attention. This home offers 4 beds, 4.5 baths, plus an office, 3,400 sq ft under air, a saltwater pool and spa, an outdoor kitchen, and a gas fireplace near the pool. This home is full of upgrades! Porcelain floors, exotic granite throughout the home a

  

  Mauro Costa

  VISTA CAY REALTY COMPANY

  12411 Montalcino Cir, Windermere, FL 34786
• 

  

  /65

  $627,900

  • 4 Beds
  • 3 Baths
  • 3,001 Sq Ft

  6601 Duncaster St, Windermere, FL 34786

  Welcome to this spacious 4-bedroom, 3-bath Victorian-style home in the highly desirable Lakes of Windermere community. Boasting over 3,000 square feet of living space, this beautifully designed home offers an exceptional layout ideal for both everyday living and entertaining. A charming covered front porch and elegant curved staircase create a warm and inviting first impression. The open-concept

  

  Wenyu Wang

  ANTS REALTY LLC

  6601 Duncaster St, Windermere, FL 34786
• 

  

  /80

  $2,650,000

  • 5 Beds
  • 5.5 Baths
  • 5,433 Sq Ft

  1408 Lake Whitney Dr, Windermere, FL 34786

  Presenting this stunning LAKEFRONT RESIDENCE showcasing spectacular PANORAMIC VIEWS and ideally located within the premier GUARD GATED COMMUNITY of Reserve at Belmere in WINDERMERE. The property is approached by a circular driveway with centerpiece WATER FOUNTAIN set in mature landscaping alongside an adjoining 3 car garage with side entry. Upon arrival, an impressive entryway opens to the foyer

  

  Alice Anne Jackson

  CORCORAN PREMIER REALTY

  1408 Lake Whitney Dr, Windermere, FL 34786
• 

  

  /72

  $625,000

  • 4 Beds
  • 2.5 Baths
  • 2,236 Sq Ft

  13786 Summer Harbor Ct, Windermere, FL 34786

  Virtually Staged. Why wait to build when the value of time to settle your family is now? You won't get this one wrong! Location, Location, Location. PLUS, Experience the magic of Disney from the comfort of your own home in this beautiful four-bedroom, two-and-a-half-bath residence located in the sought-after Summerport Trail community of Windermere. Perfectly positioned, this home offers a rare

  

  Deborah Garson

  DEBORAH E GARSON PA

  13786 Summer Harbor Ct, Windermere, FL 34786
• 

  

  /29

  $569,000

  • 4 Beds
  • 3.5 Baths
  • 2,306 Sq Ft

  5032 Beach River Rd, Windermere, FL 34786

  Imagine living where everything you love is just a short walk away. Welcome to 5032 Beach River in Windermere's beloved Summerport community. This move-in ready 4-bedroom, 2.5-bath home offers a lifestyle that's hard to find and even harder to leave. Start your mornings with a stroll to Foxtail Coffee, cool off with an afternoon treat from Kelly's Homemade Ice Cream, walk to highly sought-after

  

  Nickolas Amburgey

  COMPASS FLORIDA LLC

  5032 Beach River Rd, Windermere, FL 34786
• 

  

  /46

  $975,000

  Open Fri 5PM - 7PM $225K PRICE DROP

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

  3629 Lake Buynak Rd, Windermere, FL 34786

  Now offered at an exceptional value, this 1.3-acre property in Lake Buynak Estates presents a rare opportunity to enjoy acreage, privacy and flexibility in one of Central Florida's most desirable locations. Located within the highly sought-after Windermere ZIP code, this 4-bedroom, 3.5-bath residence offers more than 2,600 square feet of living space with a thoughtfully designed split floor plan,

  

  Tania Matthews

  KELLER WILLIAMS ELITE PARTNERS III REALTY

  3629 Lake Buynak Rd, Windermere, FL 34786
• 

  

  /34

  $600,000

  • 4 Beds
  • 3 Baths
  • 2,419 Sq Ft

  14217 Bridgewater Crossings Blvd, Windermere, FL 34786

  **BUYER INCENTIVE AVAILABLE!! Preferred Lender is offering a COMPLIMENTARY TEMPORARY RATE BUY DOWN for qualified buyers on new loan locks completed on or before 6/30/26!!** 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

  

  Azim Manji

  WEICHERT REALTORS HALLMARK PRO

  14217 Bridgewater Crossings Blvd, Windermere, FL 34786
• 

  

  /40

  $3,390,000

  $585K PRICE DROP

  • 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

  5050 Isleworth Country Club Dr, Windermere, FL 34786
• 

  

  /82

  $2,175,000

  $110K PRICE DROP

  • 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 with excellent walkability. 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

  

  Kari Fleck

  THE REAL ESTATE COLLECTION LLC

  713 Main St, Windermere, FL 34786
• 

  

  /66

  $1,150,000

  • 5 Beds
  • 4 Baths
  • 3,971 Sq Ft

  8394 Lookout Pointe Dr, Windermere, FL 34786

  FREE DISNEY FIREWORKS show nightly with purchase! Perfectly positioned in the highly sought-after community of Windermere Trails, this beautifully updated home overlooks picturesque Lake Reams and offers the kind of lifestyle that makes people fall in love with Central Florida. From the stately elevation featuring stone accents, a tile roof, paver driveway, and elegant color palette, you'll

  

  Autumn Makin

  LAKEFIELD REALTY GROUP LLC

  8394 Lookout Pointe Dr, Windermere, FL 34786
• 

  

  /32

  $1,390,000

  $110K PRICE DROP

  • 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

  17538 Black Rail St, Windermere, FL 34786
• 

  /2

  $1,039,091

  New Construction $10K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,740 Sq Ft

  14353 Crest Palm Ave, Windermere, FL 34786

  Welcome to the Arlington! This single-story floor plan features 4 bedrooms, 3 bathrooms, and a 2-car garage, offering 2,740 square feet of spacious living. Enjoy an open-concept design that seamlessly connects the dining, kitchen, and living areas. The garage also includes an extra hobby/work space. Relax on the large covered patio or create culinary masterpieces in the chef's kitchen. The

  

  Cindy Sapp

  OLYMPUS EXECUTIVE REALTY INC

  14353 Crest Palm Ave, Windermere, FL 34786
• 

  

  /3

  $7,999,000

  New Construction

  • 6 Beds
  • 9 Baths
  • 8,038 Sq Ft

  9317 Gladys Garden Ct, Windermere, FL 34786

  Under Construction. Currently under construction in the renowned golf course community of Isleworth, this exceptional residence by Goehring & Morgan, thoughtfully designed by Ashley Martin, offers 8,038 square feet of refined luxury living. Featuring 6 bedrooms, 6 full bathrooms, 3 half bathrooms, and a 4-car garage, this custom home showcases timeless architecture paired with elevated finishes

  

  Robert Welker, III

  CORCORAN PREMIER REALTY

  9317 Gladys Garden Ct, Windermere, FL 34786
• 

  

  /42

  $1,049,990

  New Construction Open Sat 1PM - 5PM $65K PRICE DROP

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

  14371 Crest Palm Ave, Windermere, FL 34786

  Virtually Staged. Arlington Floorplan – 3,140 Sq. Ft. | 4 Beds | 4Baths | 2.5-Car Garage | Move-In ReadyWelcome to the Arlington with Bonus – a thoughtfully designed, 2-story home that perfectly blends luxury, functionality, and comfort. This brand new 3,140 square foot residence sits on an wooded lot, offering expansive indoor and outdoor living space, ready for immediate move-in.Key Features:4

  

  Cindy Sapp

  OLYMPUS EXECUTIVE REALTY INC

  14371 Crest Palm Ave, Windermere, FL 34786
• 

  

  /15

  $989,990

  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
• 

  /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
• 

  

  /30

  $629,900

  $19K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,147 Sq Ft

  13622 Darchance Rd, Windermere, FL 34786

  Welcome home to Berkshire Park. This 3bedroom, 2bath residence offers a balance of comfort and convenience in a quiet residential setting. Ideally located just minutes from world-class attractions including Walt Disney World, as well as shopping, dining, and major highways, this property places you at the center of Central Florida living. The community is surrounded by nearby schools, adding

  Javin Lopez AVANTI WAY REALTY LLC

  13622 Darchance Rd, Windermere, FL 34786
• 

  

  /98

  $1,799,000

  • 4 Beds
  • 3 Baths
  • 3,297 Sq Ft

  2503 Butler Bay Dr N, Windermere, FL 34786

  Set behind the gates of Windermere Club, this lakefront residence delivers everyday comfort with a resort-style backdrop on beautiful Lake Crescent. Offering 4 bedrooms and 3 baths, the home is designed for easy living and effortless entertaining, with bright, open gathering spaces that keep the water views front and center. At the heart of the home, the kitchen pairs generous prep space with a

  Simon Simaan THE SIMON SIMAAN GROUP

  2503 Butler Bay Dr N, Windermere, FL 34786
• 

  

  /13

  $1,146,990

  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
• 

  

  /17

  $1,052,990

  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
• 

  

  /14

  $1,085,990

  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
• 

  

  /38

  $749,900

  • 4 Beds
  • 3 Baths
  • 2,665 Sq Ft

  6363 Sedona Leaf Ct, Windermere, FL 34786

  Virtually Staged. Welcome to this beautifully maintained 4-bedroom, 3-bathroom home tucked away on a quiet cul-de-sac in the highly desirable Eden Isle community of Windermere. Offering 2,665 square feet of thoughtfully designed living space on an oversized .32-acre lot, this home combines comfort, functionality, and an unbeatable location. Step inside to discover a light and inviting floor plan

  Abby Nelson RE/MAX 200 REALTY

  6363 Sedona Leaf Ct, Windermere, FL 34786
• 

  

  /100

  $3,350,000

  Open Sat 11AM - 1PM $150K PRICE DROP

  • 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
• 

  

  /51

  $1,575,000

  Open Sat 12PM - 3PM $114K PRICE DROP

  • 5 Beds
  • 3 Baths
  • 3,300 Sq Ft

  13124 Filly Ct, Windermere, FL 34786

  Welcome to a rare opportunity in one of Windermere’s most exquisite communities where luxury living meets farmland feel. The Farms community consists of 12 properties of one or more acres each. The community also has a horse stable that homeowners can keep horses. Nestled at the end of a cul-de-sac, this gorgeous estate offers sophistication, premium finishes and a quaint feeling throughout.As

  Marcelo Brandao HOME N OFFICES INTERNATIONAL

  13124 Filly Ct, Windermere, FL 34786
• 

  

  /40

  $3,299,999

  $200K PRICE DROP

  • 5 Beds
  • 4.5 Baths
  • 4,417 Sq Ft

  5001 Latrobe Dr, Windermere, FL 34786

  One or more photo(s) has been virtually staged. Traditional five-bedroom four and a half bath pool home with an open layout in Isleworth Golf & Country Club. Perfectly positioned on a quiet cul-de-sac along the 6th fairway with serene views of Lake Bessie. Offering 4,417 square feet of refined living space, this elegant two-story residence features two primary suites downstairs with private

  Laura Diss Q BOUTIQUE SPECIALTY REALTY INC

  5001 Latrobe Dr, Windermere, FL 34786
• 

  

  /49

  $1,200,000

  • 4 Beds
  • 4 Baths
  • 2,787 Sq Ft

  1361 Whitney Isles Dr, Windermere, FL 34786

  Stunning residence with a private fenced backyard, located in the highly sought-after gated community of Belmere in Windermere, just minutes from the town center. Featuring 4 bedrooms, 4 bathrooms, and approximately 2,800 sq. ft. of air-conditioned living space, this home immediately captivates with its elegant Mediterranean architecture and lush tropical landscaping. Fully renovated this year,

  Gabriel Mantovani ALVES AND HOWELL REALTY

  1361 Whitney Isles Dr, Windermere, FL 34786
• 

  

  /63

  $1,520,000

  $160K PRICE DROP

  • 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
• 

  

  /34

  $2,999,000

  • 4 Beds
  • 6 Baths
  • 4,706 Sq Ft

  5073 Latrobe Dr, Windermere, FL 34786

  Set on an elevated corner homesite within Isleworth, this four-bedroom residence presents a unique opportunity to secure a coveted address in one of Central Florida's most distinguished private golf communities. Encompassing more than 4,700 square feet, the property offers exceptional potential for renovation, customization, or the creation of a new vision tailored to today's luxury

  Michelle Corbin ISLEWORTH REALTY LLC

  5073 Latrobe Dr, Windermere, FL 34786
• 

  

  /59

  $749,900

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

  7242 Londale Blvd, Windermere, FL 34786

  Welcome to this stunning former model home located in highly desirable Windermere! From the moment you step inside you will be greeted by it's open space layout for living and dining rooms with meticulous attention to detail featuring crown molding, wrought iron staircase and custom built-in entertainment center in family room. The gourmet kitchen has plenty of counter space for the pickiest of

  Lisa McNeilly TAYLOR REAL ESTATE SVC OF C FL

  7242 Londale Blvd, Windermere, FL 34786
• 

  

  /41

  $1,450,000

  • 4 Beds
  • 4 Baths
  • 3,997 Sq Ft

  9548 Crown Prince Ln, Windermere, FL 34786

  Nestled on a rare half-acre lot in one of Windermere’s most sought-after communities, Windsor Hills, this FULLY RENOVATED luxury home delivers the ultimate move-in-ready, like-new lifestyle buyers are searching for. Featuring 4 spacious bedrooms, 4 beautifully updated bathrooms, and a highly desirable open-concept layout, every inch of this residence has been meticulously redesigned with today’s

  Dianna Desboyaux DOUGLAS ELLIMAN

  9548 Crown Prince Ln, Windermere, FL 34786
• 

  

  /63

  $1,875,000

  $75K PRICE DROP

  • 5 Beds
  • 4 Baths
  • 4,489 Sq Ft

  13420 Bonica Way, Windermere, FL 34786

  Experience the Florida lifestyle in this stunning FULLY FURNISHED 5-Bed/4-Bath pool home on over 1/2-acre, with a welcoming open floor plan spanning 4,500 square feet, spectacular Theater Room, custom upgrades and designer accents throughout, and new dual-zoned AC system in August 2025 including Nest smart thermostat. Situated across from the community park and tennis on one of the best

  Frank Ferrell FERRELL REALTY, INC.

  13420 Bonica Way, Windermere, FL 34786
• 

  

  /28

  $2,500,000

  • 4 Beds
  • 4.5 Baths
  • 4,961 Sq Ft

  13377 Lake Butler Blvd, Winter Garden, FL 34787

  Fantastic opportunity to purchase 12+ acres of private, quiet lake front property in Winter Garden/Windermere area on West Lake Butler Blvd. with 4+ acres high and dry and no HOA. Property currently boasts dock with electricity and boat lift on a skiable lake. There is an existing house that could be remodeled or torn down and start fresh. Home is 4961 square feet and built in 1990 with

  Dawn Briggs BLUE MAGNOLIA REALTY LLC

  13377 Lake Butler Blvd, Winter Garden, FL 34787
• 

  

  /52

  $765,000

  • 4 Beds
  • 3.5 Baths
  • 3,161 Sq Ft

  7211 Still Pond Ln, Windermere, FL 34786

  Welcome to this stunning FORMER MODEL HOME in the sought-after ASLIN PARK, a community in the heart of WINDERMERE. This former CUSTOM CARLISLE model was designed and built by renowned ASHTON HOMES. Perfectly positioned on a premium corner lot with not rear neighbor and pond view, located in one of Windermere desired subdivision. This exceptional former model home blends timeless architecture,

  Arturo Castillo PREFERRED REAL ESTATE BROKERS

  7211 Still Pond Ln, Windermere, FL 34786
• 

  

  /92

  $4,399,000

  • 5 Beds
  • 6 Baths
  • 5,580 Sq Ft

  6120 Greatwater Dr, Windermere, FL 34786

  Keene’s Pointe – 24-hour gated/attended community in Windermere, Florida. Experience refined luxury in this exceptional golf-front estate perfectly positioned along the 17th fairway of The Golden Bear Club. Fully renovated, architecturally refined and intentionally designed by Ashley Martin Home. From the moment you enter, an inviting foyer opens to a spacious living room framed by 12-foot

  Teresa Stewart SOUTHERN REALTY GROUP LLC

  6120 Greatwater Dr, Windermere, FL 34786
• 

  

  /42

  $1,049,989

  New Construction $64K PRICE INCREASE

  • 4 Beds
  • 4 Baths
  • 3,138 Sq Ft

  14371 Crest Palm Ave, Windermere, FL 34786

  Welcome to the Arlington with Bonus – a thoughtfully designed, 2-story home that perfectly blends luxury, functionality, and comfort. This brand new 3,140 square foot residence sits on an wooded lot, offering expansive indoor and outdoor living space, ready for immediate move-in. Key Features:4 Spacious Bedrooms: Designed for privacy and flexibility, including a luxurious owner’s suite with

  Dream Finders Homes Builder

  14371 Crest Palm Ave, Windermere, FL 34786

Showing Results 1 - 40, Page 1 of 6

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

Single Family Home Prices in Windermere, FL

The median price for single family homes in Windermere is $1,089,503, and there are 225 single family home listings available for sale.

Single Family Home Price Trends

Median Home Price $1,089,503	Median 3-Bedroom Home Price $563,750
Median 4-Bedroom Home Price $966,400	Median 5-Bedroom Home Price $1,410,000