Windermere, FL Real Estate & Homes For Sale

256 homes

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NEW
COMING SOON
3D VIEW
0.4 ACRES
$3,250,000
5 Beds
5 Baths
6,370 sqft
6024 GREATWATER DRIVE,
Windermere, FL 34786
CORCORAN PREMIER REALTY
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NEW
COMING SOON
3D VIEW
$799,900
4 Beds
3 Baths
3,038 sqft
8325 VIVARO ISLE WAY,
Windermere, FL 34786
COLDWELL BANKER REALTY
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NEW - 6 HRS AGO
3D VIEW
$369,990
3 Beds
2.5 Baths
1,398 sqft
7663 BRAMWELL STREET,
Windermere, FL 34786
LOKATION
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NEW - 7 HRS AGO
3D VIEW
$465,000
3 Beds
2.5 Baths
2,113 sqft
13731 CALERA ALLEY,
Windermere, FL 34786
STOCKWORTH REALTY GROUP
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NEW
COMING SOON
0.41 ACRES
$1,250,000
4 Beds
3.5 Baths
4,175 sqft
1521 LAKE WHITNEY DRIVE,
Windermere, FL 34786
EXP REALTY LLC
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NEW - 1 DAY AGO
3D VIEW
$625,000
4 Beds
3 Baths
2,427 sqft
5021 CARILLON LANE,
Windermere, FL 34786
REALTY OF AMERICA
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NEW - 1 DAY AGO
1.35 ACRES
$6,995,000
5 Beds
7 Baths
7,529 sqft
9349 TIBET POINTE CIRCLE,
Windermere, FL 34786
CORCORAN PREMIER REALTY
NEW - 2 DAYS AGO
3D VIEW
$559,900
4 Beds
3.5 Baths
2,311 sqft
5231 LEMON TWIST LANE,
Windermere, FL 34786
AGENT TRUST REALTY CORPORATION
3D VIEW
$630,000
4 Beds
3.5 Baths
2,454 sqft
8582 POWDER RIDGE TRAIL,
Windermere, FL 34786
LPT REALTY, LLC
COMING SOON
3D VIEW
1.08 ACRES
$1,100,000
4 Beds
4 Baths
3,348 sqft
14038 BLUEBIRD PARK ROAD,
Windermere, FL 34786
RE/MAX TOWN & COUNTRY REALTY
3D VIEW
$669,000
4 Beds
3.5 Baths
2,686 sqft
8631 GREENBANK BOULEVARD,
Windermere, FL 34786
CLASSIC 1 REALTY INC
3D VIEW
1.44 ACRES
$995,000
QUAIL COVE COURT LOT 14,
Windermere, FL 34786
REGENCY REAL ESTATE LLC
3D VIEW
$1,100,000
4 Beds
4 Baths
2,787 sqft
1361 WHITNEY ISLES DRIVE,
Windermere, FL 34786
ALVES AND HOWELL REALTY
$350,000
2 Beds
2.5 Baths
1,280 sqft
8516 DANFORTH DRIVE,
Windermere, FL 34786
HOGAN REALTY GROUP INC
AUCTION
3D VIEW
$5,000
2 Beds
2.5 Baths
1,181 sqft
12712 Langstaff Dr,
Windermere, FL 34786
3D VIEW
$400,000
4 Beds
2.5 Baths
1,706 sqft
14500 BRIDGEWATER CROSSINGS BOULEVARD,
Windermere, FL 34786
NOVA REAL ESTATE SERVICES INC
NEW CONSTRUCTION
3D VIEW
2.5 ACRES
$8,999,999
9 Beds
13 Baths
20,445 sqft
9621 WINDY RIDGE ROAD,
Windermere, FL 34786
CITARELLI REALTY GROUP LLC
OPEN SAT, 12-3PM
3D VIEW
1 ACRE
$1,160,000
4 Beds
2.5 Baths
3,018 sqft
9601 AMBLESIDE DRIVE,
Windermere, FL 34786
CENTURY 21 CARIOTI
NEW CONSTRUCTION
3D VIEW
1.7 ACRES
$1,475,000
5 Beds
4.5 Baths
3,612 sqft
5650 NECTARINE DRIVE,
Windermere, FL 34786
LA ROSA REALTY LLC
3D VIEW
1.13 ACRES
$3,250,000
4 Beds
5.5 Baths
4,200 sqft
12620 S LAKE SAWYER LANE,
Windermere, FL 34786
SERHANT
3D VIEW
0.6 ACRES
$11,750,000
6 Beds
8.5 Baths
11,100 sqft
9832 LAUREL VALLEY DRIVE,
Windermere, FL 34786
REAL BROKER, LLC
COMING SOON
3D VIEW
0.45 ACRES
$2,790,000
5 Beds
6 Baths
5,225 sqft
6850 VALHALLA WAY,
Windermere, FL 34786
COLDWELL BANKER REALTY
3D VIEW
$435,000
3 Beds
2.5 Baths
1,743 sqft
11267 GRANDER DRIVE,
Windermere, FL 34786
AUTHENTIC REAL ESTATE TEAM
COMING SOON
$349,000
3 Beds
2.5 Baths
1,644 sqft
12930 VENNETTA WAY,
Windermere, FL 34786
RE/MAX TOWN & COUNTRY REALTY
3D VIEW
$620,000
4 Beds
3.5 Baths
2,461 sqft
13019 GARRIDAN AVENUE,
Windermere, FL 34786
LA ROSA REALTY LLC
3D VIEW
0.81 ACRES
$2,899,000
7 Beds
8.5 Baths
7,042 sqft
4205 CLARICE COURT,
Windermere, FL 34786
LAKESIDE REALTY WINDERMERE INC
3D VIEW
$689,900
5 Beds
3 Baths
3,006 sqft
6614 BRIDGEWATER VILLAGE RD,
Windermere, FL 34786
MY REALTY GROUP, LLC.
3D VIEW
$1,189,000
5 Beds
4.5 Baths
4,999 sqft
17538 BLACK RAIL STREET,
Windermere, FL 34786
KARDOSH REALTY
NEW CONSTRUCTION
3D VIEW
0.39 ACRES
$2,190,000
5 Beds
5.5 Baths
3,582 sqft
6518 SAWYER SHORES LANE,
Windermere, FL 34786
WRA BUSINESS & REAL ESTATE
3D VIEW
$599,000
3 Beds
2 Baths
1,948 sqft
13125 PENSHURST LANE,
Windermere, FL 34786
CASTLE REALTY PROFESSIONAL GROUP LLC
NEW CONSTRUCTION
BUILDABLE PLAN
$545,990+
3 Beds
2.5 Baths
1,699 sqft
Cawood Plan in Lake Cawood Cove,
Windermere, FL 34786
3D VIEW
$299,500
2 Beds
2 Baths
1,161 sqft
8180 BOAT HOOK LOOP #109,
Windermere, FL 34786
ROMAN'S PRO REALTY LLC
NEW CONSTRUCTION
BUILDABLE PLAN
$516,740+
3 Beds
2.5 Baths
1,649 sqft
Cypress Plan in Lake Cawood Cove,
Windermere, FL 34786
3D VIEW
$405,000
3 Beds
2.5 Baths
1,382 sqft
8867 HERENCIA ALLEY,
Windermere, FL 34786
AAA GLOBAL VENTURES PA
3D VIEW
$1,450,000
7 Beds
4.5 Baths
4,443 sqft
14274 CREST PALM AVENUE,
Windermere, FL 34786
DOUGLAS ELLIMAN
3D VIEW
$324,900
3 Beds
2 Baths
1,455 sqft
8276 MARITIME FLAG ST #1204,
Windermere, FL 34786
HOMEVEST REALTY
3D VIEW
0.26 ACRES
$1,050,000
4 Beds
3 Baths
2,984 sqft
5944 CAYMUS LOOP,
Windermere, FL 34786
SOUTHERN REALTY GROUP LLC
3D VIEW
$1,348,000
5 Beds
4.5 Baths
3,835 sqft
7231 SANGALLA DRIVE,
Windermere, FL 34786
ONE LUXURY INTERNATIONAL LLC
0.27 ACRES
$554,555
4 Beds
2 Baths
1,798 sqft
9319 WOODBREEZE BOULEVARD,
Windermere, FL 34786
CHARLES RUTENBERG REALTY ORLANDO
3D VIEW
$769,000
4 Beds
3.5 Baths
2,996 sqft
12785 WESTSIDE VILLAGE LOOP,
Windermere, FL 34786
KELLER WILLIAMS WINTER PARK
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Windermere, FL Real Estate Trends

Learn about the Windermere, FL housing market through trends and averages.

Affordability
Home Value
What Locals Say

Affordability of Living in Windermere, FL

The median home value is $709,948

Month	Median home value
October 2025	$703k
November 2025	$703k
December 2025	$704k
January 2026	$705k
February 2026	$706k
March 2026	$706k
April 2026	$706k
May 2026	$706k
June 2026	$706k
July 2026	$707k
August 2026	$708k
September 2026	$710k

View as a graph

Trends and affordability stats are provided by third party data sources.

Average Home Value in Windermere, FL, by Home Size

Currently, there are 19 new listings in Windermere, FL and 256 homes for sale.

Home Size	Home Value*
2 bedrooms (12 homes)	$333,034
3 bedrooms (49 homes)	$441,190
4 bedrooms (91 homes)	$768,018

*Home value over the past month

What Locals Say about Windermere

Review Highlights

Windermere offers enduring family appeal: top schools, low crime, cared-for streets, steady value ROI. Residents love safety, top-rated schools, clean well-kept streets, parks, and a tight-knit community. Concerns include rush-hour traffic, no public transit, rapid growth, crowded schools, and nightly fireworks.

AI-generated summary of moderated reviews.

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Anjalique Creative Concepts
Resident
1y ago
"We’ve lived in this area for 5 years and absolutely love it! The people in the community are always friendly, welcoming and supportive of one another. All the surrounding neighborhoods are well maintained and there are always organized activities in the community that makes it fun to meet new residents moving in."
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Snkdrwbwms
Resident
1y ago
"Very safe area. Police is very present and effective. Amazing place to live. I will definitely be here forever."
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Valentina
Resident
2y ago
"Trick or treating is big but it’s more about small groups of neighbors doing things together rather than large activities in the entire neighborhood."
0
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Juliana Daurio
Resident
2y ago
"I moved to Windermere in 2004. When my kids were 3 and 4. This feels like home since then. Now that my kids are gone I see no need to move. I have many nice neighbors and enjoy everything that this area has to offer. "
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Snkdrwbwms
Resident
2y ago
"Great neighborhood! I live here for 12 years and intend to stay. Very safe with great administrative support from the HOA. "
0
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Snkdrwbwms
Resident
2y ago
"Easy to go everywhere. Sometimes traffic delays due to school drop off and pick up. I love to live here."
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Juliana Daurio
Resident
2y ago
"Festivals , school events,Hallowed, Christmas and food truck events on Fridays in downtown Windermere "
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Datylberman
Resident
2y ago
"I work at home so I’m not versed in the commute anywhere.many people in Windermere work at hone also.friends who work downtown are happy with their commute."
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John Malloy
Resident
2y ago
"Work from home Commute to stores, health care, friendly community. Safe and secure in my neighborhood. "
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Garrett Hendrickson
Resident
2y ago
"Some home owners don’t want neighbors dogs to relieve themselves in their yard. This is even if you clean up after your pet. "
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Ngandhi62
Resident
6y ago
"Great areas to walk dogs and great puppy parks. Very close convenient veterinarians and pet supply stores. There are also many pet owners in area, therefore a nice social community is created."
5
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Sean H.
Resident
6y ago
"It is a very pet friendly neighborhood. And has many fenced in dog areas and 90% of people are respectful enough to clean up after their dogs."
3
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Limegreenlilo
Resident
6y ago
"Quiet & neighbors look out for one another. We have a FB page for residents to help each other out. I have been a resident ten years and love living here. HOA is good and they keep everything nice."
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Carylpalmerini17
Resident
6y ago
"Great place to raise children and just enjoy life. Schools are amazing and the 4th is no joke. Get a move on ....."
3
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Carylpalmerini17
Resident
6y ago
"Great place to live in. Everyone has been kind, neighborhood is well kept, activities are always taking place. "
3
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Shariel A.
Resident
6y ago
"tons of baggies available. tons of space and good clean environment for your pets. worth living for safety and pet compliance. "
1
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Msldancer
Resident
6y ago
"See lots of dogs in the area, most are very social. But I do not like that some owners do not put their dogs on leashes, they also then get mad when you come by even though you’re dog is leashes as it should be."
2
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Mckenziejl
Resident
6y ago
"They would like the many trails and dog parks. Most of the neighborhoods are not gated or man guarded, so you can easily move in and out of them. Each neighborhood is unique and wherher you're going for walk with or without you pet, the time would be enjoyable."
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Jessica
Resident
6y ago
"30min or less to get to any of the central Florida locations. Some locations can even see fireworks. Traffic can be a little heavy during the am/pm rush but nothing super crazy."
2
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Stephanie F.
Resident
6y ago
"Easy to get to Disney. I work on Disney property. High traffic during rush hour times. Very quick during non peak rush hour times. "
1
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Afanador713
Resident
6y ago
"Great parks for families to bike, walk and enjoy a picnic. The area is beautiful, homes are very well cared for."
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Saige L.
Resident
6y ago
"Lot of area to walk the dogs on leashes. Not so many dog parks are available where they can run free. "
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David M.
Resident
6y ago
"I’ve lived in Windermere for 3+ years and absolutely love it! Great schools, homes and atmosphere! Wouldnt live in any other neighborhood! "
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Jessica
Resident
6y ago
"lots of families and super safe and pet friendly. also super active community and lots of greenspace to excercise in. "
2
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Fabiana B.
Resident
6y ago
"Great family neighborhood. Great Lakes for water activities. Good for walking with your family, pet or go for a bike ride. "
1
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Dasom.jang
Resident
6y ago
"It’s a nice and safe area to live in. There isn’t much going on, but there are food truck nights once a month, and farmer’s market on every Saturday in Winter Garden. "
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John F.
Resident
6y ago
"I have lived in Windermere for 20 years. Very safe and good clean people. The cops are very responsive and people are rich and have class "
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Anthony G.
Resident
6y ago
"People are very family oriented. Neighbors came about the appearance and condition of their property."
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Jessica
Resident
6y ago
"There are so many open spaces and intermittent dog poop stations which are always stocked. There is even a small dog park."
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Evelyn T.
Resident
6y ago
"It’s a small oasis away from the hustle and bustle of such a vacation heavy town. I love getting to feel like I’m actually away from work and in a calm space but still be a 20 minute commute."
1
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Alex P.
Resident
6y ago
"Great neighborhood. Family oriented. Great schools. Affluent, but not overly pretentious. Not much to in town. "
0
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Jessica M.
Visitor
6y ago
"Great neighborhood, great people, great atmosphere. I always love visiting this area. Communities are kept clean and look inviting. "
1
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Jamesgkoshy
Resident
6y ago
"Quiet neighborhood, that is short distance to major attractions. Safe with great schools. Beautiful, clean and uncrowded. "
0
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Loypippin
Resident
7y ago
"It’s a safe area but growing too quickly. Too many new houses and schools getting crowded. The schools are great, but need to be built faster to keep up. "
1
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Beverly B.
Resident
7y ago
"It is very safe well lighted small community with many families with and without children. Everyone is friendly and keep their properties in great shape"
0
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Joanna T.
Resident
7y ago
"Accessibility, close to highways, malls, restaurants. the community is safe and they have frequent events for the family"
1
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Princess J.
Resident
7y ago
"Great place to live, and I feel safe in this area. I moved to this area when I moved to Florida and it was the best decision. "
1
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Windy
Resident
7y ago
"Nice , clean , safe area . Okay with my kids playing out side with other kids. Nice pool area friendly people . "
0
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Browse Windermere, FL homes by type

IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. Some IDX listings have been excluded from this website.
Listing Information presented by local MLS brokerage: Zillow, Inc - (407) 904-3511

Windermere, FL Real Estate & Homes For Sale