Windermere, FL Houses for Sale

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  /39

  $2,150,000

  • 3 Beds
  • 3 Baths
  • 2,681 Sq Ft

  647 Ridgewood Dr, Windermere, FL 34786

  One or more photo(s) has been virtually staged. Back on market — buyer’s home sale contingency did not clear. Inspection and appraisal were completed satisfactorily, no fault of the seller or property. Welcome to an extraordinary lakefront retreat on the prestigious Butler Chain of Lakes in Windermere. On a rare 1.43-acre double lot with over 200 feet of prime shoreline on Lake Down, this

  

  Linda O'Grady

  PREMIER SOTHEBYS INT'L REALTY

  (689) 302-3809

  647 Ridgewood Dr, Windermere, FL 34786
• Explore Windermere

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  /69

  $759,900

  • 4 Beds
  • 3 Baths
  • 2,425 Sq Ft

  7167 Beek St, Windermere, FL 34786

  One or more photo(s) has been virtually staged. WELCOME TO YOUR DREAM WATERFRONT RETREAT! THIS STUNNING ONE-STORY HOME OFFERS 4 BEDROOMS, 3 BATHS, AND A 3-CAR GARAGE, ALL PERFECTLY DESIGNED FOR COMFORT AND STYLE. ENJOY A LARGE SOLAR HEATED SCREENED POOL (30x14) WITH PAVER DECKING AND RELAX WITH PEACEFUL WATER VIEWS—NO REAR NEIGHBORS! THE COMMUNITY WALKWAY AROUND THE WATER INVITES YOU TO UNWIND

  

  Ron Hernquist

  RE/MAX CENTRAL REALTY

  (689) 399-2143

  7167 Beek St, Windermere, FL 34786
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  $515,000

  • 3 Beds
  • 2.5 Baths
  • 2,149 Sq Ft

  12136 Canyon Sun Trail, Windermere, FL 34786

  ***The Veranda on Canyon Sun***A day in the life — where sunlight, serenity, and thoughtful design meet.***Morning begins on the wide, covered Craftsman-style front porch, where you can sip coffee and take in the park view across the green. A gentle breeze moves through the trees as joggers and dog walkers pass along the trail — a scene that captures the peaceful charm of Windermere

  

  Karan Wienker

  COLDWELL BANKER REALTY

  (689) 336-3849

  12136 Canyon Sun Trail, Windermere, FL 34786
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  /34

  $629,000

  • 5 Beds
  • 4.5 Baths
  • 2,991 Sq Ft

  7401 Ella Ln, Windermere, FL 34786

  Spectacular Windermere Home WITH LUXURIOUS IN-LAW SUITE! Freshly painted, and brand new luxury vinyl floors. Experience the perfect blend of elegance, comfort, and versatility in this stunning 5-bedroom, 4.5-bathroom home in the prestigious Windermere community. Boasting a fully-equipped mother-in-law or older kid suite above the garage, this separate studio apartment offers privacy, abundant

  

  Kriselys Tapia

  SERHANT

  (407) 934-0478

  7401 Ella Ln, Windermere, FL 34786
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  /46

  $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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  /50

  $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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  /30

  $1,200,000

  • 4 Beds
  • 3.5 Baths
  • 2,658 Sq Ft

  11325 Fenimore Ct, Windermere, FL 34786

  One or more photo(s) has been virtually staged. Newly added virtually staged images to help with your interior design inspiration! Come home to a golf enthusiast’s dream set along the 6th Hole of the renowned Jack Nicklaus Signature 18-Hole golf course, The Golden Bear Club (est. 1999). The community of Keene's Pointe features 24-hr guards at both entrances (Main Entrance off Chase Rd

  

  Toni Marie Cafferty

  COMPASS FLORIDA LLC

  (407) 986-2096

  11325 Fenimore Ct, Windermere, FL 34786
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  /32

  $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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  /58

  $5,000,000

  • 6 Beds
  • 8 Baths
  • 6,855 Sq Ft

  4089 Isabella Cir, Windermere, FL 34786

  Welcome to 4089 Isabella Cir. A Home Like No Other, Exquisite Custom Luxury in Casabella, Windermere, FLStep into unparalleled luxury with this completely reimagined six-bedroom, six-bathroom estate in the prestigious Casabella community of Windermere. Every inch of this home has been custom-curated with the finest materials and designer touches, creating an ambiance of modern

  

  Fernanda Negromonte

  NOVA REAL ESTATE SERVICES INC

  (689) 312-9381

  4089 Isabella Cir, Windermere, FL 34786
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  /47

  $1,075,990 New Construction

  • 6 Beds
  • 4.5 Baths
  • 3,550 Sq Ft

  7007 Windy Palm Way, Windermere, FL 34786

  One or more photo(s) has been virtually staged. The Ellington II offers the perfect balance of space, comfort, and style. This modern two-story home features 5 bedrooms, 3 baths, and over 3,500 square feet of living space designed for today’s lifestyle. The open-concept main level includes a spacious kitchen, dining area, and great room ideal for entertaining. The private owner’s suite provides a

  

  Cindy Sapp

  OLYMPUS EXECUTIVE REALTY INC

  (689) 407-6441

  7007 Windy Palm Way, Windermere, FL 34786
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  /55

  $1,134,990 New Construction

  • 6 Beds
  • 4.5 Baths
  • 4,443 Sq Ft

  14225 Crest Palm Ave, Windermere, FL 34786

  One or more photo(s) has been virtually staged. Step into your next home at the Sweetwater in Palms at Windermere.With over 4,400 square feet, this expansive two-story floorplan offers six bedrooms and four and a half baths, blending luxury and function for today’s modern living.On the first floor, the owner’s suite is a private retreat with dual walk-in closets and a spa-inspired bath. A

  

  Cindy Sapp

  OLYMPUS EXECUTIVE REALTY INC

  (407) 602-6772

  14225 Crest Palm Ave, Windermere, FL 34786
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  $1,084,990 New Construction

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

  14371 Crest Palm Ave, Windermere, FL 34786

  One or more photo(s) has been virtually staged. Under Construction. Sample Image Experience the perfect blend of elegance, comfort, andpracticality with this beautifully crafted Arlington Bonus new home in Windermere. Every element of this residence has been thoughtfully designed to create aspace that feels both luxurious and inviting. With soaring ceilings—up to 10 feet on the first

  

  Cindy Sapp

  OLYMPUS EXECUTIVE REALTY INC

  (689) 314-5712

  14371 Crest Palm Ave, Windermere, FL 34786
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  $2,000,000 New Construction

  • 5 Beds
  • 4.5 Baths
  • 3,685 Sq Ft

  6564 Lagoon St, Windermere, FL 34786

  Listed BELOW appraised value & PRICED TO SELL! With this brand new construction home, your dream lakefront lifestyle starts here!! Set along the tranquil waters of Lake Sawyer, this brand-new Davila Homes masterpiece blends refined luxury with the magic of everyday lake life. With 5 bedrooms, 4.5 baths, and 3,685 sq. ft. of beautifully designed living space, every element is crafted to

  

  Fernanda Negromonte

  NOVA REAL ESTATE SERVICES INC

  (407) 901-5358

  6564 Lagoon St, Windermere, FL 34786
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  /2

  $1,098,990 New Construction

  • 4 Beds
  • 3.5 Baths
  • 3,404 Sq Ft

  7019 Windy Palm Way, Windermere, FL 34786

  One or more photo(s) has been virtually staged. Sample Image The Baldwin is a beautifully designed two-story home offering 4 bedrooms, 3.5 baths, and over 3,400 square feet of living space. The open-concept main level features a spacious great room and dining area that flow seamlessly into the kitchen—perfect for family gatherings or entertaining. The first-floor owner’s suite includes a private

  

  Cindy Sapp

  OLYMPUS EXECUTIVE REALTY INC

  (689) 600-1926

  7019 Windy Palm Way, Windermere, FL 34786
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  $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
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  /63

  $1,075,000

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

  2125 Kane Park Way, Windermere, FL 34786

  Welcome to this beautifully updated residence on one of the largest lots in the highly sought-after Willows at Lake Rhea in Windermere. Set on a 0.71-acre cul-de-sac lot surrounded by lush landscaping, the home offers exceptional privacy and a tranquil setting. Custom built by renowned local builder Richard Watson, known for his craftsmanship, thoughtful design, and quality construction, this

  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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  /55

  $2,375,000

  • 5 Beds
  • 4.5 Baths
  • 4,688 Sq Ft

  409 W 2nd Ave, Windermere, FL 34786

  Step inside this beautifully updated home where clean lines, soaring ceilings, and two-story windows fill every corner with natural light. A floating staircase makes a stunning first impression, while the spacious family room with its cozy fireplace is the perfect spot to gather with friends and family.The open living and dining room features built-ins with floating shelves, and the gourmet

  Amanda Black PA UPSIDE REAL ESTATE INC

  409 W 2nd Ave, Windermere, FL 34786
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  /9

  $944,990 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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  /16

  $954,990 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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  $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
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  /53

  $650,000

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

  6139 Andreozzi Ln, Windermere, FL 34786

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

  Simon Simaan THE SIMON SIMAAN GROUP

  6139 Andreozzi Ln, Windermere, FL 34786
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  /10

  $994,990 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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  $1,490,000

  • 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
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  /72

  $2,750,000

  • 7 Beds
  • 5.5 Baths
  • 5,221 Sq Ft

  6219 Tiroco Way, Windermere, FL 34786

  Welcome to luxury living in the guarded gated community of Waterstone in Windermere, Florida. This exquisite residence at 6219 Tiroco Way offers unparalleled elegance and modern comfort featuring Solar power. The home offers 7 bedrooms, 5 1⁄2 baths, a media room, a loft, a storage room, separate formal rooms, and a dedicated office. Live in a world of sophistication and comfort with granite

  María Gabriela Lara CENTURY 21 CARIOTI

  6219 Tiroco Way, Windermere, FL 34786
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  /39

  $550,000

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

  11322 Rapallo Ln, Windermere, FL 34786

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

  John Callahan REDFIN CORPORATION

  11322 Rapallo Ln, Windermere, FL 34786
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  /90

  $6,799,000

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

  11103 Bridge House Rd, Windermere, FL 34786

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

  Ayoub Aitelhaj THE SIMON SIMAAN GROUP

  11103 Bridge House Rd, Windermere, FL 34786
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  /50

  $1,077,990 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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  /11

  $899,990 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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  $939,500

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

  11096 Ledgement Ln, Windermere, FL 34786

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

  James Ellis CHARLES RUTENBERG REALTY ORLANDO

  11096 Ledgement Ln, Windermere, FL 34786
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  /31

  $974,990 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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  $939,989 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

  Cindy Sapp OLYMPUS EXECUTIVE REALTY INC

  14377 Crest Palm Ave, Windermere, FL 34786
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  /10

  $1,049,990 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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  /72

  $2,450,000

  • 5 Beds
  • 6 Baths
  • 5,291 Sq Ft

  9204 Tibet Pointe Cir, Windermere, FL 34786

  Your stunning Keene’s Pointe custom home by Stonebridge was built for luxurious everyday living and effortless entertaining. The grand first floor features travertine and hardwood floors throughout, a formal living room with gas fireplace and stone mantle, elegant dining room with adjoining dry bar, and a private office with French doors. The secluded primary suite includes a glamorous dressing

  Simon Simaan THE SIMON SIMAAN GROUP

  9204 Tibet Pointe Cir, Windermere, FL 34786
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  /2

  $939,989 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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  /51

  $911,400

  • 5 Beds
  • 4.5 Baths
  • 3,849 Sq Ft

  4926 Indian Deer Rd, Windermere, FL 34786

  WOW! Check out this stunningly renovated Summerport multi-generational home! This expansive residence features 4 spacious bedrooms and 3 baths, PLUS a private multigenerational suite on the first floor complete with its own bedroom, full bath, and sitting area overlooking the serene pond.Designed with both comfort and versatility in mind, the home boasts a modern chef’s kitchen with quartz

  Shelley Dawson COMPASS FLORIDA LLC

  4926 Indian Deer Rd, Windermere, FL 34786
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  /35

  $1,398,888

  • 4 Beds
  • 3.5 Baths
  • 3,751 Sq Ft

  6533 Cartmel Ln, Windermere, FL 34786

  Tucked away in the prestigious guard-gated community of The Reserve at Lake Butler Sound, this exceptional 4-bedroom, 3.5-bath single-story pool home blends timeless Mediterranean style with modern sophistication. Set on over half an acre in a quiet cul-de-sac, the home welcomes you with a paver driveway, lush mature landscaping, and an elegant entry framed by architectural columns.As you

  Andy Neal THE AGENCY ORLANDO

  6533 Cartmel Ln, Windermere, FL 34786
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  /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
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  /49

  $19,995,000

  • 6 Beds
  • 14 Baths
  • 20,865 Sq Ft

  9508 Windy Ridge Rd, Windermere, FL 34786

  Discover this Perfectly positioned Georgian Estate situated on 12 acres (additional 6 acres available) of lakefront property with meticulously manicured grounds. This walled and gated compound includes approx 614 feet of pristine lake frontage and panoramic views on Lake Down of the Butler Chain of Lakes. The magnificent sprawling primary residence pairs classic Georgian architecture with modern

  Johnny DelPrete Douglas Elliman (Jupiter)

  9508 Windy Ridge Rd, Windermere, FL 34786
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  /51

  $1,149,000

  • 4 Beds
  • 3.5 Baths
  • 3,050 Sq Ft

  8746 Crescendo Ave, Windermere, FL 34786

  HUGE PRICE REDUCTION — PRICE TO SELL!Discover refined Florida living in this beautifully appointed premium CORNER-LOT residence located in one of Windermere’s most desirable communities. Built in 2015 and offering 3,050 SqFt of thoughtfully designed interior living, this FULLY FURNISHED, move-in-ready home delivers outstanding value, convenience, and lifestyle appeal—now at an exceptional new

  Mariana Micheti M2M REALTY

  8746 Crescendo Ave, Windermere, FL 34786

Showing Results 1 - 40, Page 1 of 5

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

Home Trends in Windermere, FL

On average, homes in Windermere, FL sell after 74 days on the market compared to the national average of 53 days. The median sale price for homes in Windermere, FL over the last 12 months is $850,000, up 9% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$850,000

Median Single Family Sale Price

$1,080,406

Median Townhouse Sale Price

$410,000

Median 2 Bedroom Sale Price

$297,500

Average Price Per Sq Ft

$364

Number of Homes for Sale

224

Last 12 months Home Sales

643

Months of Supply

4.20

Median List Price

$974,900

Median Change From 1st List Price

5%

Median Home Sale Price YoY Change

9%