Windermere, FL Homes for Sale

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  $1,166,989 New Construction

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

  14383 Crest Palm Ave, Windermere, FL 34786

  ELLINGTON II - Our beautiful huge 2 story home, with 6 Bedrooms and 4 Baths. This great floor plan boasts an open concept family/dining/kitchen area along with a formal dining room, gourmet kitchen, extended 42 cabinets and an extended island. Primary Suite on 1st floor along with an additional bedroom & bath. The primary bath also contains a spa package with upgraded 3/8 glass enclosure, an

  

  Cindy Sapp

  OLYMPUS EXECUTIVE REALTY INC

  14383 Crest Palm Ave, Windermere, FL 34786
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  $325,000

  • 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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  $1,349,000

  • 6 Beds
  • 3.5 Baths
  • 3,364 Sq Ft

  2219 Ridgewind Way, Windermere, FL 34786

  Set behind the gates of The Estates at Windermere—an intimate enclave of just 67 homes—2219 Ridgewind Way is the kind of property that stops you mid-scroll. A true Victorian-inspired residence, its architectural presence is unforgettable: a statement turret, wraparound porch, and intricate trim work that feels both rare and timeless in today’s market. It’s not just different—it’s irreplaceable.

  

  Hilary Hall

  COMPASS FLORIDA LLC

  (407) 233-3382

  2219 Ridgewind Way, 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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  $455,000

  • 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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  $1,120,000 Open Fri 4PM - 6PM

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

  13525 Gorgona Isle Dr, Windermere, FL 34786

  One or more photo(s) has been virtually staged. 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

  

  Roo Klaers

  COLDWELL BANKER REALTY

  (407) 842-8447

  13525 Gorgona Isle Dr, Windermere, FL 34786
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  $1,114,989 New Construction

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

  14371 Crest Palm Ave, Windermere, FL 34786

  Welcome to the Arlington with Bonus! This stunning 3,138 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

  14371 Crest Palm Ave, 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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  $1,225,000 Open Thu 12PM - 2PM

  • 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

  (689) 262-5600

  109 E 12th Ave, Windermere, FL 34786
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  $1,550,000

  • 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

  (689) 334-2915

  12411 Montalcino Cir, Windermere, FL 34786
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  $2,125,000

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

  12699 Hawkstone Dr, Windermere, FL 34786

  Welcome to Chalet du Lac, set on the exclusive and private Lake Sawyer chain of lakes in Windermere—where mornings are welcomed by sunrise over glistening waters dancing through a veil of Cypress trees and Spanish moss. Nestled along the western shoreline of Lake Sawyer within an enclave of custom-built lakefront homes, Chalet du Lac features 4 bedrooms and 5 baths, lives large at 3751 sq ft

  

  Drew Ross

  LAKEFIELD REALTY GROUP LLC

  (407) 676-7612

  12699 Hawkstone Dr, 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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  $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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  $3,299,000

  • 6 Beds
  • 8 Baths
  • 7,217 Sq Ft

  4029 Isabella Cir, Windermere, FL 34786

  Experience an architectural masterpiece in the gated enclave of Casabella. Situated on a rare, oversized .85-acre lot, this estate has been transformed by the original owner with impeccable attention to detail. The interior features 6 beds, 6 full and 2 half baths, all the high-scratch-resistant flooring throughout the home comes in a beautiful white oak finish with bathrooms featuring porcelain

  

  Mauro Costa

  VISTA CAY REALTY COMPANY

  (407) 584-1756

  4029 Isabella Cir, 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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  $1,390,000

  • 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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  $1,099,989 New Construction

  • 4 Beds
  • 3.5 Baths
  • 3,728 Sq Ft

  14348 Crest Palm Ave, Windermere, FL 34786

  The Baldwin floor plan is a thoughtfully designed two-story home featuring 4 spacious bedrooms and 3.5 bathrooms, offering over 3,400 square feet of living space. The first floor boasts an inviting open-concept design, with a large great room adjacent to a dining room, perfect for gatherings and entertaining. The owner’s suite, complete with a walk-in closet and private bath, offers a comfortable

  

  Cindy Sapp

  OLYMPUS EXECUTIVE REALTY INC

  14348 Crest Palm Ave, Windermere, FL 34786
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  $1,595,000

  • Land
  • 2.12 Acres
  • $752,358 per Acre

  10948 Down Park Ln, Windermere, FL 34786

  LAST REMAINING LOT OF THE FOUR IN THIS EXCLUSIVE PRIVATE ESTATE LAKEFRONT COMMUNITY! Rare opportunity to build your dream home in the highly sought after Town of Windermere. This exceptional vacant homesite offers over 2.12 acres and is the largest buildable lot within this private gated enclave of only four estate properties, providing exceptional privacy and generous spacing between homes. The

  

  Andrew Kincaid

  BHHS FLORIDA REALTY

  (689) 588-0828

  10948 Down Park Ln, Windermere, FL 34786
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  $750,000 Open Sat 1PM - 4PM

  • 5 Beds
  • 4 Baths
  • 3,597 Sq Ft

  13145 Zori Ln, Windermere, FL 34786

  One or more photo(s) has been virtually staged. Priced right and move-in ready! Situated in the Windermere community of Providence, this home offers spacious living across two floors. Upon entering, you are greeted by the formal living and dining rooms. The family room is open to the kitchen for easy entertaining. The primary suite along with three other bedrooms are on the first floor. On the

  

  Toni Marie Cafferty

  COMPASS FLORIDA LLC

  (689) 265-3814

  13145 Zori Ln, Windermere, FL 34786
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  $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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  $847,500

  • 5 Beds
  • 3 Baths
  • 3,248 Sq Ft

  9639 Westover Club Cir, Windermere, FL 34786

  There's room for everyone here. Nearly 3,300 square feet with five beds, three baths, a three-car garage, a pool, and no rear neighbors tucked behind the gates of Westover Club in Windermere. TStep inside and the house opens up. Soaring ceilings, a two-story family room with a fireplace stretching up the wall, a catwalk overhead, and sightlines that carry all the way through to the pool. Gorgeous

  Brad Young HOMEVEST REALTY

  9639 Westover Club Cir, Windermere, FL 34786
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  $1,119,990 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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  $2,300,000

  • 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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  $975,000

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

  2125 Kane Park Way, Windermere, FL 34786

  A rare opportunity to own a .71-acre pool home in the Town of Windermere for under $1 million—beautifully updated and truly move-in ready. Welcome to this beautifully updated single-story pool home on an oversized 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

  Deb Schroeder INFINITY REALTY GROUP LLC

  2125 Kane Park Way, Windermere, FL 34786
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  /17

  $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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  $6,980,000

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

  5186 Vardon Dr, Windermere, FL 34786

  One or more photo(s) has been virtually staged. Fully reimagined golf-front estate in the prestigious Isleworth community with sweeping views of the iconic 3rd hole. Situated on approximately 1 acre, this 4,739 sq ft residence offers 4 bedrooms and 4.5 baths, soaring ceilings, and an upper level Terrace captures stunning golf course views. Fully upgraded front and rear grounds offer a

  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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  $979,999

  • 4 Beds
  • 3.5 Baths
  • 3,299 Sq Ft

  8796 Peachtree Park Ct, Windermere, FL 34786

  Come live in paradise!! Minutes from the Magic Kingdom with amazing fireworks view from front porch and private pool. This exceptional builder model offers an unmatched combination of luxury upgrades, thoughtful design, and a premier location in the coveted Peachtree Park community. Perfectly positioned with conservation views and no rear neighbors, this home delivers privacy, style, and a true

  Lee Goldberg COLDWELL BANKER REALTY

  8796 Peachtree Park Ct, Windermere, FL 34786
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  $3,475,000

  • 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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  $1,575,000 Open Sat 1PM - 4PM

  • 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
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  $1,119,990 New Construction

  • 6 Beds
  • 4.5 Baths
  • 3,692 Sq Ft

  14354 Crest Palm Ave, Windermere, FL 34786

  TIDEWATER W/BONUS - Our beautiful huge 2 story home, located on a beautiful conservation lot, with 6 Bedrooms and 4.5Baths. This great floor plan boasts an open concept family/dining/kitchen area with a gourmet kitchen, extended 42 wrap around cabinets, and an extended island. The owner's bath also contains a spa package with upgraded 3/8 glass enclosure, an additional rainfall shower head, and

  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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  /67

  $1,949,000

  • 6 Beds
  • 5.5 Baths
  • 5,430 Sq Ft

  9057 Balmoral Mews Square, Windermere, FL 34786

  Located within the prestigious gated community of Balmoral Estates, this spectacular 6-bedroom, 5.5-bath 4 car garage luxury estate sits on an expansive 3⁄4-acre homesite and has been completely renovated with exceptional custom upgrades throughout. From the moment you arrive, the property makes a striking impression with a brand-new circular paver driveway centered around a dramatic custom water

  Ryan Rogers REAL BROKER, LLC

  9057 Balmoral Mews Square, Windermere, FL 34786
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  /61

  $487,000

  • 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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  /30

  $629,900

  • 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
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  /18

  $425,000

  • 3 Beds
  • 2.5 Baths
  • 1,584 Sq Ft

  11636 Water Run Aly, Windermere, FL 34786

  This property is a beautifully maintained 3-bedroom, 2.5-bath townhouse located in the desirable Ashlin Park community of Windermere. Built in 2017, this home features an open-concept layout filled with natural light, a modern kitchen with quartz countertops, stainless steel appliances, and espresso cabinetry. The spacious primary suite offers a walk-in closet and an elegant ensuite bath. Enjoy a

  Jose Jimenez EXP REALTY LLC

  11636 Water Run Aly, Windermere, FL 34786
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  /78

  $3,499,999

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

  5001 Latrobe Dr, Windermere, FL 34786

  One or more photo(s) has been virtually staged. Don’t miss this rare opportunity to own a stunning estate home in the prestigious 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 five spacious bedrooms, four-and-a-half

  Laura Diss Q BOUTIQUE SPECIALTY REALTY INC

  5001 Latrobe Dr, Windermere, FL 34786
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  /63

  $1,520,000

  • 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 $1,528,972.

Are home prices dropping in Windermere?

Yes, home prices in Windermere are down 3% in the last 12 months.

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

657 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 $950,000. If you put a 20% down payment of $190,000 and had a 30-year fixed mortgage with an interest rate of 6.23%, your estimated principal and interest payment would be $4,670 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $200K 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 74 days on the market compared to the national average of 56 days. The median sale price for homes in Windermere, FL over the last 12 months is $830,000, down 2% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$830,000

Median Single Family Sale Price

$1,082,946

Median Townhouse Sale Price

$393,500

Median 2 Bedroom Sale Price

$295,000

Average Price Per Sq Ft

$360

Number of Homes for Sale

234

Last 12 months Home Sales

657

Months of Supply

4.30

Median List Price

$950,000

Median Change From 1st List Price

5%

Median Home Sale Price YoY Change

-2%