Windermere, FL Homes for Sale

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  /61

  $580,000

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

  9056 Woodbreeze Blvd, Windermere, FL 34786

  Welcome to 9056 Woodbreeze Blvd, a remarkable 4-bedroom, 2-bathroom home with a 2-car garage, nestled in the serene Silver Woods neighborhood of Windermere, FL. This exceptional residence offers a unique blend of privacy and community amenities. With only one adjacent neighbor and community tennis courts on the other side, the property provides a tranquil retreat. The backyard overlooks a

  

  Tom Langmann

  RE/MAX 200 REALTY

  (689) 305-3637

  9056 Woodbreeze Blvd, Windermere, FL 34786
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  Explore Windermere

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  /15

  $315,000

  • 3 Beds
  • 2 Baths
  • 1,455 Sq Ft

  11434 Jasper Kay Terrace Unit 306, Windermere, FL 34786

  Beautiful Lakeside at Lakes of Windermere condominium - Third floor corner unit with screened balcony. This unit features an open floor plan that combines kitchen, living room, and dining room. The kitchen feature 42 inch wood cabinets and a breakfast bar. Spacious primary bedroom. The A/C was replaced in October 2020. Tons of storage throughout the unit! The community features Clubhouse, Pool,

  

  Jay Stewart

  SOUTHERN REALTY GROUP LLC

  (689) 314-5683

  11434 Jasper Kay Terrace Unit 306, Windermere, FL 34786
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  /27

  $325,500

  • 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

  (407) 410-3997

  8180 Boat Hook Loop Unit 108/301, Windermere, FL 34786
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  /80

  $1,499,900

  • 5 Beds
  • 4.5 Baths
  • 4,477 Sq Ft

  1450 Belfiore Way, Windermere, FL 34786

  Welcome to Refined Living in Tuscany RidgeStep into luxury with this fully renovated, move-in-ready home, perfectly situated in the exclusive, gated community of Tuscany Ridge. Every detail of this exquisite residence has been thoughtfully updated to offer modern elegance, comfort, and timeless sophistication.The main level features a spacious primary suite designed to evoke a

  

  Laura Teixeira

  NOBSKA REAL ESTATE LLC

  (689) 308-3110

  1450 Belfiore Way, Windermere, FL 34786
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  /39

  $546,000

  • 3 Beds
  • 2.5 Baths
  • 2,009 Sq Ft

  8160 Iron Mountain Trail, Windermere, FL 34786

  Nestled in the highly desirable Windermere Trails community, this beautiful home offers an unparalleled blend of modern design, high end finishes and everyday functionality. The 3 bedrooms, 2 1/2 baths home's open-concept design seamlessly integrates the living and dining areas with the spacious kitchen and family room, creating an inviting space for everyday living and entertaining.

  

  Francine Arroyo Santowski

  BHHS FLORIDA REALTY

  (407) 955-9391

  8160 Iron Mountain Trail, Windermere, FL 34786
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  /44

  $1,200,000

  • 6 Beds
  • 4.5 Baths
  • 4,457 Sq Ft

  12002 Angle Pond Ave, Windermere, FL 34786

  Discover the elegance of this spacious residence situated on a premium corner lot within the highly sought-after Windermere Trails community. This exquisite home features a formal living room and dining room, complemented by a generous family room that seamlessly connects to a gourmet kitchen. You will appreciate the impressive oversized kitchen island, stylish granite countertops, and

  

  Yadira Kitterman

  ORLANDO ADVANTAGE REALTY INC

  (407) 863-8455

  12002 Angle Pond Ave, Windermere, FL 34786
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  /100

  $2,650,000

  • 5 Beds
  • 8 Baths
  • 7,621 Sq Ft

  9905 Lanai View Ct, Windermere, FL 34786

  Welcome to a home that isn’t just designed—it’s curated.Tucked behind the gates of one of Central Florida’s most exclusive golf communities, 9905 Lanai View Court is the kind of estate that makes you pause. Nearly 7,000 square feet of single-level, custom-crafted living plus more than 800 square feet private media room on the second floor. Every detail intentional. Every space

  

  Bent Danholm

  MAXIM REALTY ORLANDO

  (407) 512-8409

  9905 Lanai View Ct, Windermere, FL 34786
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  /75

  $3,490,000

  • 6 Beds
  • 8 Baths
  • 6,930 Sq Ft

  13305 Bellaria Cir, Windermere, FL 34786

  In the gated Bellaria community, featuring six expansive bedrooms, including two primary suites and four en suites, this residence is an ideal blend of privacy and convenience with a beautiful lake view. Enjoy your private cinema, this Toll Brothers estate blends luxury and comfort with dramatic ceilings, an open floor plan, and travertine marble flooring on main areas. The chef's kitchen

  

  Alessandro Minato

  PREMIER SOTHEBYS INT'L REALTY

  (407) 565-9509

  13305 Bellaria Cir, Windermere, FL 34786
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  /39

  $2,150,000 Open Sat 12PM - 2PM

  • 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
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  /30

  $1,575,000

  • Land
  • 2.12 Acres
  • $742,925 per Acre

  10948 Down Park Ln, Windermere, FL 34786

  BUILD YOUR DREAM HOME in this incredibly rare vacant lot located in the highly sought after Town of Windermere! Zoned for single family residential and offering over 2.12 acres of land, this property is located on a lovely pond with 2 fountains and is in close proximity to the Butler Chain of Lakes offering the possibility for views of Lake Down which is situated incredibly close by! The private

  

  Andrew Kincaid

  BHHS FLORIDA REALTY

  (689) 314-5758

  10948 Down Park Ln, Windermere, FL 34786
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  /35

  $675,000

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

  7401 Ella Ln, Windermere, FL 34786

  Spectacular Windermere Home WITH LUXURIOUS IN-LAW SUITE! 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 space, and its own entrance—ideal for guests, extended

  

  Kriselys Tapia

  SERHANT

  (407) 934-0478

  7401 Ella Ln, Windermere, FL 34786
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  /52

  $699,000

  • 3 Beds
  • 2.5 Baths
  • 3,094 Sq Ft

  6734 Bridgewater Village Rd, Windermere, FL 34786

  Welcome to 6734 Bridgewater Village Road, a true gem nestled in the highly sought-after Vineyards of Horizon West in Windermere. This exquisite property offers unparalleled privacy on an oversized CONSERVATION lot, creating a serene oasis where you can truly unwind and enjoy the beauty of nature. As you approach the home, the stunning paver driveway leads you to an inviting entrance. Step inside

  

  Alexis Bress

  EXP REALTY LLC

  (407) 753-6824

  6734 Bridgewater Village Rd, Windermere, FL 34786
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  /93

  $7,500,000

  • 5 Beds
  • 8 Baths
  • 9,403 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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  /100

  $4,777,000

  • 6 Beds
  • 8.5 Baths
  • 5,721 Sq Ft

  5157 Latrobe Dr, Windermere, FL 34786

  Newly remodeled in 2019 — a rare find in the community! Sunlit single-storey layout, bright in every corner ! Panoramic views of Hole 4 from the living room!Live the legendary lifestyle in this fully rebuilt and expanded single-story, golf-front Isleworth estate, masterfully designed by renowned architect Terry Irwin. In 2019, the home underwent a comprehensive reconstruction and significant

  peipei Qiao BAY STREET GROUP FLORIDA LLC

  5157 Latrobe Dr, Windermere, FL 34786
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  /44

  $1,099,000

  • 5 Beds
  • 3.5 Baths
  • 3,407 Sq Ft

  12530 Climbing Vine Ct, Windermere, FL 34786

  Welcome to this beautifully upgraded 5-bedroom, 3.5-bath home, just 11 minutes from Disney, where you can enjoy magical firework views from your second floor. Step inside to find a thoughtfully designed layout, featuring a front bedroom with an ensuite bath—perfect for guests or multigenerational living. The spacious kitchen is a chef’s dream, complete with a large island, double ovens, induction

  Abby Nelson RE/MAX 200 REALTY

  12530 Climbing Vine Ct, Windermere, FL 34786
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  /49

  $679,900

  • 5 Beds
  • 3.5 Baths
  • 2,396 Sq Ft

  11578 Ashlin Park Blvd, Windermere, FL 34786

  Beautiful 5 bedrooms and 3.5 bathroom home conveniently located right across the street from the clubhouse and pool.Great location near schools, West side shoppes, banks restaurants, supermarkets, etc.the house offers open floor concept, large kitchen with breakfast bar, quartz countertop, stainless steal appliances and large eating area.New floors and new artificial grass at the

  Juan Barbosa INVIRTIENDO EN USA, LLC

  11578 Ashlin Park Blvd, Windermere, FL 34786
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  /100

  $3,650,000

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

  10577 Down Lakeview Cir, Windermere, FL 34786

  This exceptional lakefront home is located on The Butler Chain of Lakes with 137 feet of pristine shoreline and is situated on almost one dry acre. At first glance you will immediately fall in love with this beautiful custom home boasting amazing panoramic views and nightly Disney fireworks. The circular paved drive flanked with mature oak trees welcome you home to a covered porch and an

  Simon Simaan THE SIMON SIMAAN GROUP

  10577 Down Lakeview Cir, Windermere, FL 34786
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  /40

  $729,000

  • 4 Beds
  • 3.5 Baths
  • 2,876 Sq Ft

  6799 Helmsley Cir, Windermere, FL 34786

  MOTIVATED SELLER! One or more photos have been virtually staged. Imagine starting your mornings with a warm coffee on the front porch, surrounded by beautifully landscaped views and a rare sense of privacy — no rear neighbors, just the quiet calm of nature behind you. This isn’t just a house; it’s a home designed for meaningful living, where every space invites connection, comfort, and a deeper

  Emilia Faria KARDOSH REALTY

  6799 Helmsley Cir, Windermere, FL 34786
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  /30

  $480,000

  • 3 Beds
  • 2.5 Baths
  • 1,904 Sq Ft

  13829 Ingelnook Dr, Windermere, FL 34786

  Welcome to this charming 3-bedroom, 2.5-bathroom townhome nestled in the highly sought-after Vineyards of Horizon West community in Windermere, Florida. Designed for both comfort and functionality, this home offers a versatile layout to complement your lifestyle. This home has no carpet and the driveway backs into a private cul-de-sac!Upon entering, you'll be greeted by a spacious

  Kayla Korvenmaa ALIGN REAL ESTATE LLC

  13829 Ingelnook Dr, Windermere, FL 34786
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  /50

  $974,000

  • 6 Beds
  • 4 Baths
  • 4,319 Sq Ft

  8298 Lookout Pointe Dr, Windermere, FL 34786

  This stunning Wallace II Floorplan by Meritage Homes, located in the beautiful Windermere Trails Community. This home sits on a special conservation view lot and is just a 500ft walk from the Clubhouse.This magnificent 6-bedroom, 4-full-bathroom home boasts an open floor concept and over $100,000 in original builder's structural and design upgrades. The many aftermarket upgrades truly make

  Lee Goldberg COLDWELL BANKER RESIDENTIAL RE

  8298 Lookout Pointe Dr, Windermere, FL 34786
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  /84

  $1,093,144 New Construction

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

  14285 Crest Palm Ave, 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

  14285 Crest Palm Ave, Windermere, FL 34786
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  /31

  $1,093,144 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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  /37

  $625,000

  • 4 Beds
  • 2.5 Baths
  • 2,981 Sq Ft

  12925 Holdenbury Ln, Windermere, FL 34786

  This splendid two-story home features four large bedrooms and 2.5 bathrooms. The true highlight of the home is its stunning, oversized kitchen, which has a huge amount of cabinet and counter space. Not one, but two islands provide a setting for casual dining and culinary creativity. The main floor offers a cozy first-floor bedroom for added convenience and flexibility, suitable for guests or as a

  Eric Nelson SIGNATURE HOMES

  12925 Holdenbury Ln, Windermere, FL 34786
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  /36

  $790,000

  • 4 Beds
  • 3 Baths
  • 2,622 Sq Ft

  11450 Arborside Bend Way, Windermere, FL 34786

  One or more photo(s) has been virtually staged. Welcome to this well-maintained 4-bedroom, 3-bathroom home located in the gated community of Glenmuir. This traditional-layout residence offers a blend of classic elegance and modern comfort. Step inside to discover beautiful hardwood and tile flooring that flows seamlessly throughout the home.The heart of this home is its inviting living

  John Callahan REDFIN CORPORATION

  11450 Arborside Bend Way, Windermere, FL 34786
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  /75

  $1,450,000

  • 6 Beds
  • 4.5 Baths
  • 3,793 Sq Ft

  10430 Birch Tree Ln, Windermere, FL 34786

  Elegant & spacious 6BR/4.5BA estate on 1+ acre in Windermere Downs, a highly desirable community favored by buyers for its prime location and refined lifestyle. The long, circular driveway welcomes you to soaring ceilings, beautiful luxury vinyl plank flooring, and a tastefully designed kitchen featuring solid surface Sablestone countertops, tile backsplash, and maple cabinetry with 36" & 42"

  Nankumar Seelall HOMESMART

  10430 Birch Tree Ln, Windermere, FL 34786
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  /53

  $675,000

  • 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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  /43

  $974,900

  • 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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  /40

  $550,000

  • 3 Beds
  • 2.5 Baths
  • 2,154 Sq Ft

  8575 Lookout Pointe Dr, Windermere, FL 34786

  This beautiful 3 bedroom, 2.5 bath home is nestled in the highly desirable Windermere Trails community. Enjoy the magic of theme parks just minutes away from Disney World with a direct view of the fireworks from your front porch! With over 2,000 SqFt, this home boasts an open floor plan that offers an upgraded kitchen, a large dining space, a spacious family room, and an upstairs loft. The

  Thomas Weclew THE REALTY MEDICS

  8575 Lookout Pointe Dr, Windermere, FL 34786
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  /64

  $1,300,000

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

  109 E 12th Ave, Windermere, FL 34786

  Modern upgrades meet timeless Windermere charm in this fully reimagined four-bedroom, three-and-a-half-bath home, just steps from Lake Bessie. Set on a beautifully manicured corner lot with no HOA, this thoughtfully updated property blends luxury, comfort, and functionality in one of Central Florida’s most desirable communities.Every detail has been considered—NEW ROOF, NEW A/C, NEW

  Robert Larkan EXECUTIVE PROPERTIES

  109 E 12th Ave, Windermere, FL 34786
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  /42

  $585,000

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

  11322 Rapallo Ln, Windermere, FL 34786

  One or more photo(s) has been virtually staged. “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, fitness center, resort-style pool, playground,

  John Callahan REDFIN CORPORATION

  11322 Rapallo Ln, Windermere, FL 34786
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  /100

  $3,250,000

  • 4 Beds
  • 5.5 Baths
  • 4,849 Sq Ft

  6186 Louise Cove Dr, Windermere, FL 34786

  A Masterpiece of Design in Isleworth – 6186 Louise Cove Drive. Stunning, design magazine-worthy residence nestled behind the exclusive 24-hour guard-gated community of Isleworth, one of Central Florida’s most prestigious neighborhoods. This exquisite estate sits on a spacious 0.75-acre corner lot, surrounded by mature landscaping and a stately circular driveway that sets the tone for the luxury

  Simon Simaan THE SIMON SIMAAN GROUP

  6186 Louise Cove Dr, Windermere, FL 34786
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  /33

  $549,900

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

  12255 Joshua Tree Trail, Windermere, FL 34786

  Welcome home to this impeccably maintained and move-in ready residence in Windermere Trails! Situated on a corner lot, one block from the community pool and amenities with a fenced yard, this home offers both convenience and privacy. Step inside to find updated plank flooring on the main level and fresh paint, creating a bright and inviting atmosphere. The spacious, modern floorplan seamlessly

  Nancy Grabowski REDFIN CORPORATION

  12255 Joshua Tree Trail, Windermere, FL 34786
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  /51

  $745,000

  • 4 Beds
  • 3.5 Baths
  • 2,745 Sq Ft

  13519 Bicton Ln, Windermere, FL 34786

  Live Just Minutes from the Magic – Stunning 4-Bedroom Home in Gated Windermere Community. Welcome to 13519 Bicton Dr, a beautifully maintained 4-bedroom, 3.5-bathroom home offering nearly 3,000 square feet of thoughtfully designed living space with countless upgrades in one of Windermere's most sought-after gated communities. With a 3-car garage, a new roof, and new windows, this home combines

  Tiphany Weeks DIAMOND REAL ESTATE GROUP

  13519 Bicton Ln, Windermere, FL 34786
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  /40

  $589,900

  • 4 Beds
  • 2 Baths
  • 1,798 Sq Ft

  9319 Woodbreeze Blvd, Windermere, FL 34786

  WONDERFUL WINDERMERE 4 BED/ 2 BATH HOME LOCATED IN THE CHARMING COMMUNITY OF SILVER WOODS. The moment you drive up to this home you are greeted by low maintence landscaping, paver driveway and a unique courtyard entry which makes this home standout. The courtyard is a perfect space to spend the evenings or start your mornings. Sliders from the kitchen lead onto the courtyard. Upon entering you

  Steven Looper CHARLES RUTENBERG REALTY ORLANDO

  9319 Woodbreeze Blvd, Windermere, FL 34786
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  /27

  $1,449,000

  • 5 Beds
  • 4 Baths
  • 3,358 Sq Ft

  11524 Claymont Cir, Windermere, FL 34786

  *** INTERIOR PICTURES coming soon! *** Completely updated in recent years, this 5-bedroom, 4-bathroom home offers 3,358 SqFt of luxury living in Keene’s Pointe, Windermere’s premier 24-hour guard-gated community and home of the Golden Bear Club. From the start, the oversized driveway, accommodating up to nine vehicles, and three-car garage set this home apart. Inside, the first floor features

  Immu Korvenmaa ALIGN REAL ESTATE LLC

  11524 Claymont Cir, Windermere, FL 34786
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  /54

  $1,325,000

  • 4 Beds
  • 3 Baths
  • 3,021 Sq Ft

  11334 Camden Loop Way, Windermere, FL 34786

  Welcome to this beautifully refreshed single-story ranch in the desirable guard-gated community of Keene’s Pointe! Move-in ready and thoughtfully updated, this home features new luxury vinyl flooring, modern light fixtures, fresh interior and exterior paint, and a brand-new roof (2024).The oversized 3-car garage, complete with newly painted floors, provides abundant storage. Inside, the

  Angela Durruthy KEENE'S POINTE REALTY

  11334 Camden Loop Way, Windermere, FL 34786
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  /86

  $1,590,000

  • 5 Beds
  • 4.5 Baths
  • 4,226 Sq Ft

  9649 Weatherstone Ct, Windermere, FL 34786

  Welcome to Weatherstone on Lake Olivia, one of Windermere’s most sought-after gated communities. With only 13 custom executive homes, each set on expansive one-acre homesites, this neighborhood offers a rare blend of exclusivity, privacy, and charm.From the moment you arrive, you’ll be greeted by beautiful curb appeal and a sweeping semi-circle driveway. Step inside this thoughtfully designed

  Newton Hieda SUMMERHILL REALTY GROUP LLC

  9649 Weatherstone Ct, Windermere, FL 34786
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  /61

  $1,175,000 Open Sat 12PM - 4PM

  • 5 Beds
  • 4.5 Baths
  • 4,061 Sq Ft

  8420 Vivaro Isle Way, Windermere, FL 34786

  MAJESTIC Mediterranean-Style Estate in Windermere Isle — 2 Stories, 5 Bedrooms, Resort-Caliber Backyard!! Prepare to be awestruck by this expansive 2 story home nestled in this luxurious community of lush conservation landscapes, impeccably manicured common areas, a sparkling resort-style heated self-cleaning pool and spa with a custom outdoor kitchen that’s convenient proximity to Disney,

  Tyler Labod COLDWELL BANKER REALTY

  8420 Vivaro Isle Way, Windermere, FL 34786
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  /49

  $1,890,000

  • 6 Beds
  • 4 Baths
  • 3,894 Sq Ft

  9922 Brentford Ct, Windermere, FL 34786

  If you want something turn-key in Keene’s Pointe, sitting in one of the most desirable locations in the community, then look no further. This is a home you can move into today, sit down and live, without touching a single thing. This home has not only been renovated from end to end, but also has a three year old new tile roof!! Every square inch of the house feels brand new as you walk thru. It

  Shane Croft COLDWELL BANKER RESIDENTIAL RE

  9922 Brentford Ct, Windermere, FL 34786
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  /74

  $2,600,000

  • 6 Beds
  • 5.5 Baths
  • 4,599 Sq Ft

  1003 Oakdale St, Windermere, FL 34786

  Be the 1st to Live In This Completely Remodeled and Expanded Luxurious Lakefront Home - Total of 6 Bedrooms - 5 Full Baths - 1 Pool or Guest Bath - Primary Suite & Guest Suite on 1st Floor - 4 More Bedrooms & 3 Bathrooms on 2nd Floor - Huge Bonus Room / Theatre / Game Room with Full Bathroom Over Garage - Separate Office on 1st Floor - 12 Foot Wide Folding Glass Doors Overlooking The Screened

  Darrell Nunnelley VINTAGE REALTY GROUP LLC

  1003 Oakdale St, Windermere, FL 34786

Showing Results 1 - 40, Page 1 of 7

Why Live in Windermere

Windermere, Florida, is a lakeside community known for its Old Florida charm and elegant homes along the Butler Chain of Lakes. With a population of about 3,000, Windermere attracts both affluent retirees and younger families, drawn by its beauty, privacy, and proximity to Orlando, approximately 20 miles away. The area features multiple gated neighborhoods, including the luxury community of Isleworth, known for its Mediterranean and French Provincial-style estates. Other notable neighborhoods include Reserve at Lake Butler Sound and Keene’s Point, offering large New Traditional and Mediterranean-style homes. Townhouses and condos, mainly on the west side, provide amenities like lake views and playgrounds.

Windermere's children attend highly rated Orange County Public Schools, and Windermere Preparatory School is a standout private institution serving prekindergarten through 12th grade. Residents enjoy various outdoor activities, including boating and fishing in the lakes, and memberships at Isleworth Golf & Country Club or The Golden Bear Club at Keene’s Point for golf, tennis, pickleball, and swimming. The town boasts over 10 parks, such as Central Park and Lake Bessie Lakefront Park, which offer playgrounds and scenic trails.

Main Street features locally owned shops and restaurants, and the weekly Windermere Farmers Market at Town Square Park is a local highlight. Nearby, The Grove shopping center and Restaurant Row in Dr. Phillips provide additional dining and shopping options. Windermere hosts popular events like the Windermere Wine and Dine in February and Food Truck Night from September to May. The community is conveniently located near Florida's Turnpike, Interstate 4, and Orlando International Airport, about 15 miles away.

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 $1,242,342.

Are home prices dropping in Windermere?

Yes, home prices in Windermere are down 11% in the last 12 months.

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

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

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

The most popular zip codes in Windermere, FL include 34786, 34761, 34734, 34787 and 32835.

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 $745,000. If you put a 20% down payment of $149,000 and had a 30-year fixed mortgage with an interest rate of 6.58%, your estimated principal and interest payment would be $3,800 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $163K a year to afford the median home price in Windermere.

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, Lake Whitney 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 67 days on the market compared to the national average of 52 days. The median sale price for homes in Windermere, FL over the last 12 months is $675,000, up 4% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$675,000

Median Single Family Sale Price

$927,000

Median Townhouse Sale Price

$414,000

Average Price Per Sq Ft

$340

Number of Homes for Sale

148

Last 12 months Home Sales

408

Months of Supply

4.40

Median List Price

$745,000

Median Change From 1st List Price

4%

Median Home Sale Price YoY Change

4%