27 Diane Dr, Windham, NY 12496
Primary Bedroom w/closet
Lower Level Bedroom
SOLD
JUL 22, 2026

$620,000

Last sold price
  • 4 Beds
  • 2.5 Baths
  • 2,800 sqft (on 3 acres)

27 Diane Dr, Windham, NY 12496

Est. Refi. Payment $4,081/mo*
Refinance Your Home
Currently Off Market - Sold Jul 22, 2026 for $620,000

Home Value

Learn more about this home's value by checking out the value of nearby homes and how much similar homes have sold for.

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
46 Cardinal Dr, Windham, NY
0.11
Single-Family Home
$1,100,000
12/11/25
5
3
1,700
19 Brook Hollow Lane, Windham, NY
0.55
Single-Family Home
$639,000
01/30/26
4
2
2,240
91 Beaver Hill Road, Windham, NY
0.55
Single-Family Home
$755,000
05/01/26
4
3
1,839
73 Beaver Hill Road, Windham, NY
0.66
Single-Family Home
$702,000
12/22/25
4
2.5
2,500
91 Beaver Hl, Windham, NY
0.55
Single-Family Home
$755,000
05/08/26
3
3
1,839
233 Begley Road, Windham, NY
0.40
Single-Family Home
$795,000
10/27/25
3
2
2,542
73 Beaver Hl, Windham, NY
0.66
Single-Family Home
$717,000
04/01/26
4
3
1,554
205 Nauvoo Road Road, Windham, NY
0.76
Single-Family Home
$850,000
10/03/25
4
2
2,200
31 Koonan Road Ext, Windham, NY
0.54
Single-Family Home
$560,000
06/01/26
4
2
1,800

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
0 Cardinal Drive, Windham, NY 12496
0.12
-
-
-
-
Off Market
12 Lauren Lane, Windham, NY 12496
0.30
$1,709,999
6
4.5
4,855
Recently Sold
39 Trail View Lane, Windham, NY 12496
0.25
$1,055,600
3
3
3,914
Off Market
0 High Point Rd, Windham, NY 12496
0.29
$755,000
3
2.5
1,897
Off Market
0 Mountain View Drive, Windham, NY 12496
0.34
$872,400
3
2.5
2,130
Off Market
0 Mountain View Road, Windham, NY 12496
0.34
$75,000
-
-
-
For Sale
233 Begley Road, Windham, NY 12496
0.40
$819,400
3
2
2,542
Off Market
36 - 2 Holiday Court #2, Windham, NY 12496
0.41
$485,700
3
3
1,600
Off Market
5 Chalet Drive, Windham, NY 12496
0.45
$1,053,100
4
4.5
4,208
Off Market
0 Chalet Drive, Windham, NY 12496
0.45
$995,000
4
3.5
3,700
Off Market
0 Trail View Lane, Windham, NY 12496
0.40
$75,000
-
-
-
For Sale
191 Mitchell Hollow Road, Windham, NY 12496
0.42
$916,200
3
2.5
2,000
Off Market

Local Information

  • Map ViewExplore the area around 27 Diane Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1970
3 acre lot
2,800 sqft
$221/sqft
Garage

About this House

On a very quiet cul de sac minutes from Windham Mountain sits this lovely home on 3.3 secluded acres. It features four bedrooms including an ensuite primary bedroom, 2.5 baths, sauna, 2 large family rooms with large wood burning fireplaces, an oversized garage, eat in kitchen, mudroom, utility room, ample closets, large deck, with newer windows and sliders. There is plenty of parking for your entire crew and the current configuration sleeps 10 in beds.
27 Diane Dr, Windham, NY 12496 is a 4 bedroom, 3 bathroom, 2,800 sqft single-family home built in 1970. It last sold for $620,000 on Jul 22, 2026. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate rent is $7,586/month.

Home Details for 27 Diane Dr

Interior Features

Interior Details
BasementNumber of Rooms: 8Types of Rooms: Breakfast Nook, Dining Room, Family Room, Laundry Room, Master Bath, Mud Room, Recreation RoomCeiling Fan
Heating & Cooling
Heating: Baseboard, OilHeating Fuel: Baseboard
Levels, Entrance, & Accessibility
Stories: 1Floors: Carpet, Laminate, Slate
Appliances & Utilities
Cable ReadyDishwasherDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace
Windows, Doors, Floors & Walls
Double Paned Windows
Security
Security System

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: Stucco, Wood
Parking & Garage
GarageParking Spaces: 6Parking: Garage Attached

Property Information

Year Built
Year Built: 1970
Property Type / Style
Property Type: Single Family HomeArchitecture: Ranch / Rambler

Price & Status

Price
Price Per Sqft: $221/sqft

Community

Units in Building: 1

Lot Information

Lot Area: 3.00 acres

Price and Tax history

DateEventPrice
Jul 22, 2026
Source: N/A
Sold
$620,000
May 1, 2026
Source: N/A
Listed For Sale
$649,000
Oct 30, 2006
Source: N/A
Sold
$390,000

Market trends in Windham

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
67
5MoM

Around this home

What Locals Say about Windham

At least 14 Trulia users voted on each feature.

  • 95 % Say there's holiday spirit

  • 90 % Say there's wildlife

  • 88 % Say parking is easy

  • 80 % Say yards are well-kept

  • 80 % Say it's quiet

  • 79 % Say car is needed

  • 71 % Say they plan to stay for at least 5 years

  • 68 % Say people would walk alone at night

  • 65 % Say it's dog friendly

  • 62 % Say neighbors are friendly

  • 53 % Say kids play outside

  • 47 % Say it's walkable to grocery stores

  • 47 % Say streets are well-lit

  • 40 % Say there are community events

  • 37 % Say it's walkable to restaurants

  • 37 % Say there are sidewalks

Sourced by Trulia users. Learn more about our methodology.
  • Claudia H.
    "School parades the primary grade students mid day. The police are out keeping an eye on the children and the fire department gives away hot chocolate and hot dogs!"
    2
    Flag
  • Dan H.
    "Whether you've lived here all your life or if you're just visiting, the people will welcome you and make you feel at home. I encourage people to visit and maybe stay a while. "
    6
    Flag
  • Julissa K.
    "4th of July I can see the parade passing by my house and even fireworks. Winter we have a lot of visitors here because the ski resort. And the summer is always a lot to do including walking in the Windham Path and all the trails around here are just amazing "
    0
    Flag
  • Steven N.
    "You will see dog owners walking their dogs often. The one thing missing for dogs would be a dog run "
    3
    Flag
  • Steven N.
    "It’s a lovely town to walk in with your dog and rumor has it there is a dog run in the town next door. Great trails for walking with your dog as well."
    1
    Flag
  • howardc1
    "I have a vacation condo here. The location is excellent about 3 miles from Ski Windham, and this is one of the very few properties in the area with a swimming pool and two tennis courts. Property management is excellent. Excellent cultural attractions, chamber music performances right in town, jazz and classical performances during the summer in nearby Hunter and Tannersville. "
    1
    Flag
  • Patti
    "Best Place to live, lots of clean air, beautiful scenery, nice people and lots of places to go"
    5
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 27 Diane Dr

  • What is the price history for 27 Diane Dr?
    27 Diane Dr in Windham, NY last sold for $620,000 in July 2026.
  • Is Windham a buyer's or seller's market?
    Windham is currently a buyer's market, based on recent for-sale activity.
  • What do residents say about Windham?
    Residents describe Windham, NY as easy to park in, well-kept, and quiet. Most residents say you need a car. See recently sold homes in Windham, NY.
  • What are the closest schools to 27 Diane Dr?
    The closest schools to 27 Diane Dr in Windham, NY are Windham Ashland Central School (K-12, rated 6/10).
  • Does 27 Diane Dr have laundry facilities?
    Yes, 27 Diane Dr in Windham, NY has in-unit laundry.
  • How big is the lot at 27 Diane Dr?
    The lot at 27 Diane Dr in Windham, NY is about 3 acres.

Explore by feature - Air Conditioning

Explore by feature - Pool

Explore by feature - Washer/dryer

7 rentals with a washer/dryer in Windham, NY

Apartments for Rent

Skip to last item
Skip to first item

Off Market Homes Near 27 Diane Dr

Skip to last item
Skip to first item

Homes for sale near 27 Diane Dr

Skip to last item
Skip to first item
Skip to last item
  • Results are loading
Skip to first item