501 Haley Dr, Windermere, FL 34786
OFF MARKET

501 Haley Dr
Windermere, FL 34786

  • 4 Beds
  • 2.5 Baths
  • 4,000 sqft (on 1.09 acres)

$1,098,900

Trulia Estimate
as of Aug 13, 2026
Est. Refi. Payment $7,612/mo*
Refinance Your Home

$1,098,900

Trulia Estimate
as of Aug 13, 2026
Est. Refi. Payment $7,612/mo*
Refinance Your Home
4 Beds
2.5 Baths
4,000 sqft
(on 1.09 acres)

Home Value

Trulia Estimate
$1.1M
Since last month
Decreased$10K (-0.9%)
Since last year
Increased$25K (+2.3%)
Since last sale
Increased$588K (+115.4%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +93% in the last 10 years
MonthEstimated value
2026
August 2026$1.1M
July 2026$1.11M
June 2026$1.11M
May 2026$1.12M
April 2026$1.1M
March 2026$1.09M
February 2026$1.07M
January 2026$1.07M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
2702 CARTER GROVE CIRCLE, Windermere, FL
0.27
Single-Family Home
$945,000
05/21/26
4
2.5
2,292
2931 SUNBITTERN COURT, Windermere, FL
0.57
Single-Family Home
$1,050,000
06/12/26
4
3
4,018
2128 LAKE CRESCENT COURT, Windermere, FL
0.60
Single-Family Home
$585,700
02/25/26
4
2
2,987
11401 WILLOW STOWE LANE, Windermere, FL
0.34
Single-Family Home
$1,025,000
09/18/25
4
3
2,951
11472 PARK AVENUE NE, Windermere, FL
0.48
Single-Family Home
$880,000
06/17/26
5
3.5
3,166
2804 MARQUESAS COURT, Windermere, FL
0.35
Single-Family Home
$1,999,000
06/23/26
5
4
3,649
2127 LILYPAD LANE, Windermere, FL
0.41
Single-Family Home
$1,200,000
07/01/26
4
3
3,349
11407 WILLOW GARDENS DRIVE, Windermere, FL
0.36
Single-Family Home
$1,200,000
07/20/26
5
3
3,501
3417 BAY MEADOW COURT, Windermere, FL
0.48
Single-Family Home
$1,100,000
02/06/26
4
4
2,681
2635 TRYON PLACE, Windermere, FL
0.44
Single-Family Home
$1,375,000
06/12/26
6
4.5
4,027

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
520 HALEY DRIVE, Windermere, FL 34786
0.08
$1,619,200
4
3.5
4,283
Off Market
2625 CRESCENT LAKE COURT, Windermere, FL 34786
0.16
$1,025,000
4
3
2,911
Off Market
2608 CARTER GROVE CIRCLE, Windermere, FL 34786
0.18
$958,500
4
3.5
2,854
Off Market
2516 WINDERMERE RESERVE COURT, Windermere, FL 34786
0.15
$2,692,400
5
5.5
4,953
Off Market
2632 CARTER GROVE CIRCLE, Windermere, FL 34786
0.20
$969,500
4
3
2,835
Off Market
2146 KANE PARK WAY, Windermere, FL 34786
0.17
$1,205,700
5
4
2,948
Off Market
2504 WINDERMERE RESERVE COURT LOT 040, Windermere, FL 34786
0.17
$900,000
-
-
-
For Sale
2138 KANE PARK WAY, Windermere, FL 34786
0.19
$1,072,700
5
3.5
3,210
Off Market
2511 WINDERMERE RESERVE Court, Windermere, FL 34786
0.17
$2,805,500
5
5.5
5,175
Off Market
2563 CARTER GROVE CIRCLE, Windermere, FL 34786
0.23
$1,042,100
5
4.5
3,027
Off Market
2505 WINDERMERE RESERVE COURT, Windermere, FL 34786
0.20
$3,169,600
5
6
5,218
Off Market
2702 CARTER GROVE CIRCLE, Windermere, FL 34786
0.27
$945,000
4
2.5
2,292
Recently Sold

Local Information

  • Map ViewExplore the area around 501 Haley Dr.
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Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1984
Lot Size
1.09 acres
Living Area
4,000 sqft
Price/Sqft
$275
Parking
Garage

About this House

Country Manor Estate on 1 acre in established, quiet, Windermere neighborhood. Comes with TENNIS COURT. HOA $25 per year!! Designed and built for Maintenance Free living. Nearby community ramp provides access to Lake Crescent. The two story brick home sits well off the road in a natural shaded setting. A long drive leads to a detached 1,000 sf building with two car garage and large multi purpose room. Air conditioned and finished with fir paneling, this room is plumbed and easily converted to guest apartment, game room, office, work shop. 1/2 of garage is also air conditioned. There is an adjacent garden building and beyond colorful gardens a private tennis court. This well built, energy efficient home has fine finishes throughout. Wood floors, built-in book shelves, Anderson thermal wood windows and solid wood doors to name a few. The large island country kitchen is the center of the home. The family room provides a separate activity retreat. All bedrooms are on the 2nd floor. This home was built, meticulously maintained and is being sold by the original owner. A true gem for someone who appreciates space with a bonus of being conveniently located near shopping, golf, fine dining and area attractions. The main home consists of 3200 s.f. and there is an additional 800s.f. under air in the detached building.
501 Haley Dr, Windermere, FL 34786 is a 4 bedroom, 3 bathroom, 4,000 sqft single-family home built in 1984. It last sold for $510,000 on Dec 17, 2014. It is currently off market. The Trulia Estimate is $1,098,900, with a rent estimate of $6,183/month.

Home Details for 501 Haley Dr

Interior Features

Heating & Cooling
Heating: Heat Pump, Other, ElectricAir ConditioningCooling System: Central, OtherHeating Fuel: Heat Pump
Levels, Entrance, & Accessibility
Stories: 2Floors: Tile, Carpet, Laminate
Interior Details
Additional StorageAtticNumber of Rooms: 11Types of Rooms: Walk In Closet, Breakfast Nook, Family Room, Laundry Room, Master Bath, Mud Room, Pantry, Recreation Room, WorkshopStorageCeiling Fan
Appliances & Utilities
Cable ReadyDishwasherDisposalDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Hot Tub or Spa

Exterior Features

Exterior Home Features
Roof: Metal, Shake ShingleExterior: BrickGardenLawnPorchSprinkler System
Parking & Garage
GarageParking Spaces: 6Parking: Garage Detached

Property Information

Year Built
Year Built: 1984Year Updated: 1984
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 1.09 acres

Building

Fitness & Sports
Tennis Court

Price and Tax history

DateEventPrice
Dec 17, 2014
Source: Stellar MLS #O5304076
Sold
$510,000
Nov 5, 2014
Source: Agent Provided
PriceChange
$516,000
Price decreased by 9%
Jul 2, 2014
Source: Agent Provided
Listed For Sale
$568,000

Market trends in Windermere

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$814K
$92.5KMoM
Sale-to-List Price
97.2%
0.1%MoM
Price per sq ft
$292
$18MoM
Available listings
296
11MoM
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Around this home

View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Windermere

At least 271 Trulia users voted on each feature.

  • 93 % Say it's dog friendly

  • 92 % Say there are sidewalks

  • 87 % Say car is needed

  • 87 % Say parking is easy

  • 81 % Say people would walk alone at night

  • 80 % Say it's quiet

  • 80 % Say there's holiday spirit

  • 78 % Say kids play outside

  • 75 % Say streets are well-lit

  • 64 % Say yards are well-kept

  • 60 % Say they plan to stay for at least 5 years

  • 59 % Say it's walkable to grocery stores

  • 56 % Say there's wildlife

  • 55 % Say it's walkable to restaurants

  • 54 % Say neighbors are friendly

  • 40 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Anjalique Creative Concepts
    "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."
    0
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  • Snkdrwbwms
    "Very safe area. Police is very present and effective. Amazing place to live. I will definitely be here forever."
    0
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  • Valentina
    "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
    "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. "
    0
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  • Snkdrwbwms
    "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
    "Easy to go everywhere. Sometimes traffic delays due to school drop off and pick up. I love to live here."
    0
    Flag
  • Juliana Daurio
    "Festivals , school events,Hallowed, Christmas and food truck events on Fridays in downtown Windermere "
    0
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  • Datylberman
    "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."
    0
    Flag
  • John Malloy
    "Work from home Commute to stores, health care, friendly community. Safe and secure in my neighborhood. "
    0
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  • Garrett Hendrickson
    "Some home owners don’t want neighbors dogs to relieve themselves in their yard. This is even if you clean up after your pet. "
    0
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  • Ngandhi62
    "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
    Flag
  • Sean H.
    "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
    Flag
  • Limegreenlilo
    "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."
    0
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  • Carylpalmerini17
    "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
    "Great place to live in. Everyone has been kind, neighborhood is well kept, activities are always taking place. "
    3
    Flag
  • Shariel A.
    "tons of baggies available. tons of space and good clean environment for your pets. worth living for safety and pet compliance. "
    1
    Flag
  • Msldancer
    "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
    Flag
  • Mckenziejl
    "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."
    0
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  • Jessica
    "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
    Flag
  • Stephanie F.
    "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
    Flag
  • Afanador713
    "Great parks for families to bike, walk and enjoy a picnic. The area is beautiful, homes are very well cared for."
    0
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  • Saige L.
    "Lot of area to walk the dogs on leashes. Not so many dog parks are available where they can run free. "
    0
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  • David M.
    "I’ve lived in Windermere for 3+ years and absolutely love it! Great schools, homes and atmosphere! Wouldnt live in any other neighborhood! "
    0
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  • Jessica
    "lots of families and super safe and pet friendly. also super active community and lots of greenspace to excercise in. "
    2
    Flag
  • Fabiana B.
    "Great family neighborhood. Great Lakes for water activities. Good for walking with your family, pet or go for a bike ride. "
    1
    Flag
  • Dasom.jang
    "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. "
    0
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  • John F.
    "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 "
    0
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  • Anthony G.
    "People are very family oriented. Neighbors came about the appearance and condition of their property."
    0
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  • Jessica
    "There are so many open spaces and intermittent dog poop stations which are always stocked. There is even a small dog park."
    0
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  • Evelyn T.
    "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
    Flag
  • Alex P.
    "Great neighborhood. Family oriented. Great schools. Affluent, but not overly pretentious. Not much to in town. "
    0
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  • Jessica M.
    "Great neighborhood, great people, great atmosphere. I always love visiting this area. Communities are kept clean and look inviting. "
    1
    Flag
  • Jamesgkoshy
    "Quiet neighborhood, that is short distance to major attractions. Safe with great schools. Beautiful, clean and uncrowded. "
    0
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  • Loypippin
    "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
    Flag
  • Beverly B.
    "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
    Flag
  • Joanna T.
    "Accessibility, close to highways, malls, restaurants. the community is safe and they have frequent events for the family"
    1
    Flag
  • Princess J.
    "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
    Flag
  • Windy
    "Nice , clean , safe area . Okay with my kids playing out side with other kids. Nice pool area friendly people . "
    0
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Apartments for Rent

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Explore by feature - Pet Friendly

51 pet-friendly rentals in Windermere, FL

Explore by feature - Garage

73 rentals with a garage in Windermere, FL

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88 rentals with air conditioning in Windermere, FL

Explore by feature - Pool

89 rentals with a pool in Windermere, FL

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Homes for sale near 501 Haley Dr

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Off Market Homes Near 501 Haley Dr

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Frequently asked questions about 501 Haley Dr

  • What is 501 Haley Dr estimated to be worth?
    Trulia's estimated value for 501 Haley Dr in Windermere, FL is $1,098,900.
  • What is the price history for 501 Haley Dr?
    501 Haley Dr in Windermere, FL last sold for $510,000 in December 2014.
  • Is Windermere a buyer's or seller's market?
    Windermere is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Windermere?
    The median sale price in Windermere is $814K. That is up $92.5K from the prior month.
  • Does 501 Haley Dr have air conditioning?
    Yes, 501 Haley Dr in Windermere, FL has air conditioning.
  • Does 501 Haley Dr have laundry facilities?
    Yes, 501 Haley Dr in Windermere, FL has in-unit laundry.