500 Haley Dr
Windermere, FL 34786
- 3 Beds
- 3 Baths
- 2,996 sqft (on 1.11 acres)
3 Beds
3 Baths
2,996 sqft
(on 1.11 acres)
Local Information
-- mins to
Home Highlights
Property Type
Single-Family Home
Year Built
1980
Lot Size
1.11 acres
Living Area
2,996 sqft
Price/Sqft
$322
Parking
Garage
About this House
Rare find ! For the buyer seeking a HUGE lot, no hoa, space for all their toys, "A" rated schools and still located minutes from the finest restaurants and shopping in Central Flroida. If you like to boat and ski, well this home has that covered too..boat launch at end of the the cul de sac with access to crystal clear Lake Crescent, the largest navigatable non chain of lakes, lake in Windermere. Set on MASSIVE OVER 1 ACRE CORNER LOT with 4 car oversized side entry garage (one bay has door to accommodate large truck clearance even) , DETACHED ADDITIONAL GARAGE/ ideal workshop. Recently poured concrete RV parking pad is also a welcome and unique improvement. Current owner has replaced the windows with double pane efficient windows, new a/c system and duct work. Home boasts 2 wood burning fireplaces , one is the focal point of the great room, the other is a romantic accent in the owners retreat. NO CARPET ANYWHERE IN THIS HOME, all tiled floors.PLANTATION SHUTTERS ON ALL THE NEW WINDOWS TOO. Large BONUS ROOM and huge kitchen with lots of counter space and real wood cabinets. TWO WASHER AND DRYER sets another unique and welcome feature of this home. Zoned for Windermere Elementary and WINDERMERE HIGH SCHOOL and minutes from expressways, eating and shopping. THis home offers you space and freedom of the OVER ACRE lot and NO HOA but the convenience of being centrally located. You will not come across a home like this again and there is obviously plenty of room to build a pool of your dreams if desired.
500 Haley Dr, Windermere, FL 34786 is a 3 bedroom, 3 bathroom, 2,996 sqft single-family home built in 1980. It last sold for $490,000 on Apr 13, 2018. It is currently off market. The Trulia Estimate is $964,800, with a rent estimate of $5,402/month.
Home Details for 500 Haley Dr
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Heating & Cooling Heating: Forced Air, ElectricAir ConditioningCooling System: CentralHeating Fuel: Forced Air |
Levels, Entrance, & Accessibility Stories: 1Floors: Tile |
Interior Details Types of Rooms: Walk In Closet |
Appliances & Utilities DryerMicrowaveRefrigerator |
Fireplace & Spa Fireplace |
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Exterior Home Features Roof: CompositionExterior: Stone, Stucco |
Parking & Garage GarageParking: Garage Attached, Garage Detached |
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Year Built Year Built: 1980Year Updated: 1980 |
Property Type / Style Property Type: Single Family Home |
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Units in Building: 1 |
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Lot Area: 1.11 acres |
Price History for 500 Haley Dr
| Date | Price | Event | Source |
|---|---|---|---|
| 04/13/2018 | $490,000 | Sold | N/A |
| 02/13/2018 | $496,000 | Pending | Agent Provided |
| 01/05/2018 | $496,000 | PriceChange | Agent Provided |
| 11/04/2017 | $538,800 | Listed For Sale | Agent Provided |
| 09/30/2015 | $465,000 | Sold | Stellar MLS #O5384887 |
| 08/17/2015 | $489,000 | Listed For Sale | Agent Provided |
| 10/14/1994 | $150,000 | Sold | N/A |
Market trends in Windermere
Last updated June 2026
Avg. sale price
$722K
$50KMoM
Sale-to-List Price
97.3%
0.2%MoM
Price per sq ft
$273
$11MoM
Available listings
285
6MoM
Property Tax and Assessment
| Year | 2024 |
|---|---|
| Tax | $7,605 |
| Assessment | $607,230 |
Home facts updated by county records
Comparable Sales for 500 Haley Dr
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.32 | Single-Family Home | $945,000 | 05/21/26 | 4 | 2.5 | 2,292 | |
0.54 | Single-Family Home | $585,700 | 02/25/26 | 4 | 2 | 2,987 | |
0.38 | Single-Family Home | $1,025,000 | 09/18/25 | 4 | 3 | 2,951 | |
0.57 | Single-Family Home | $1,050,000 | 06/12/26 | 4 | 3 | 4,018 | |
0.52 | Single-Family Home | $1,100,000 | 02/06/26 | 4 | 4 | 2,681 | |
0.53 | Single-Family Home | $880,000 | 06/17/26 | 5 | 3.5 | 3,166 | |
0.46 | Single-Family Home | $1,200,000 | 07/01/26 | 4 | 3 | 3,349 | |
0.39 | Single-Family Home | $1,999,000 | 06/23/26 | 5 | 4 | 3,649 | |
0.39 | Single-Family Home | $1,200,000 | 07/20/26 | 5 | 3 | 3,501 | |
0.62 | Single-Family Home | $1,120,000 | 11/20/25 | 4 | 3.5 | 3,053 |
Nearby homes
Get a sense of prices in the area by checking nearby homes.Assigned Schools
These are the assigned schools for 500 Haley Dr.
What Locals Say about Windermere
At least 270 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
79 % 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.
LGBTQ Local Legal Protections
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Apartments for Rent
Homes for sale near 500 Haley Dr
Off Market Homes Near 500 Haley Dr
Frequently asked questions about 500 Haley Dr
- What is 500 Haley Dr estimated to be worth?Trulia's estimated value for 500 Haley Dr in Windermere, FL is $964,800.
- What is the price history for 500 Haley Dr?500 Haley Dr in Windermere, FL last sold for $490,000 in April 2018.
- 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 $722K. That is up $50K from the prior month.
- Does 500 Haley Dr have air conditioning?Yes, 500 Haley Dr in Windermere, FL has air conditioning.
- How big is the lot at 500 Haley Dr?The lot at 500 Haley Dr in Windermere, FL is about 1.1 acres.

