20 Windy Rdg, Cold Spring, NY 10516
Property image
Property image
OFF MARKET

20 Windy Rdg
Cold Spring, NY 10516

  • 4 Beds
  • 2.5 Baths
  • 5,707 sqft (on 4 acres)

$5,432,500

Trulia Estimate
as of Aug 24, 2026
Est. Refi. Payment $37,668/mo*
Refinance Your Home

$5,432,500

Trulia Estimate
as of Aug 24, 2026
Est. Refi. Payment $37,668/mo*
Refinance Your Home
4 Beds
2.5 Baths
5,707 sqft
(on 4 acres)

Home Value

Trulia Estimate
$5.43M
Since last month
Increased$113K (+2.1%)
Since last year
Increased$284K (+5.5%)
Since last sale
Decreased$225K (-3.9%)
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 +258% in the last 10 years
MonthEstimated value
2026
August 2026$5.49M
July 2026$5.38M
June 2026$5.45M
May 2026$5.24M
April 2026$5.23M
March 2026$5.06M
February 2026$5.02M
January 2026$4.87M
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
120 Lane Gate Road, Cold Spring, NY
0.66
Single-Family Home
$1,145,000
12/23/25
3
2.5
2,512
17 Half Moon Ridge, Nelsonville, NY
1.14
Single-Family Home
$3,411,000
10/31/25
5
5.5
4,935
64 Paulding Avenue, Cold Spring, NY
0.70
Single-Family Home
$1,125,000
10/31/25
5
4.5
3,630
107 Lane Gate Road, Cold Spring, NY
0.76
Single-Family Home
$950,000
02/20/26
3
2
1,836
1710 Route 9D, Cold Spring, NY
0.53
Single-Family Home
$750,000
05/04/26
3
2
1,680
1 Jaycox Rd, Cold Spring, NY
1.09
Single-Family Home
$950,000
05/11/26
4
3
3,022
Brave Scout Rd, Philipstown, NY
0.78
Single-Family Home
$885,000
06/09/26
3
3.5
2,635
20 Division Street, Nelsonville, NY
0.68
Single-Family Home
$550,000
11/26/25
4
2.5
2,002
25 Chestnut Street, Cold Spring, NY
0.98
Single-Family Home
$1,310,000
07/01/26
4
3.5
2,620
1051 Old Albany Post Road, Garrison, NY
1.52
Single-Family Home
$1,400,000
06/19/26
3
3
2,464

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
10 Windy Ridge, Cold Spring, NY 10516
0.09
$3,125,700
5
6.5
5,700
Off Market
172 Moffat Road, Cold Spring, NY 10516
0.17
$1,338,600
3
2
1,836
Off Market
135 Moffat Road, Nelsonville, NY 10516
0.36
$1,003,900
4
3.5
2,946
Off Market
55 Moffat Road, Cold Spring, NY 10516
0.37
$1,649,400
3
3
5,018
Off Market
474 Lane Gate Road, Cold Spring, NY 10516
0.49
$1,350,000
-
-
-
For Sale
1710 Route 9D, Cold Spring, NY 10516
0.53
$750,000
3
2
1,680
Recently Sold
72 Billys Way, Nelsonville, NY 10516
0.56
$1,201,300
3
4
3,758
Off Market
55 Healy Road, Nelsonville, NY 10516
0.57
$671,700
3
1.5
1,398
Off Market
47 Healy Road, Nelsonville, NY 10516
0.60
$575,000
3
1
1,042
Recently Sold
11 Healy Road, Nelsonville, NY 10516
0.61
$472,300
1
2
1,080
Off Market
3-5 Healy Road, Cold Spring, NY 10516
0.61
-
4
5
2,576
Off Market
1 Healy Road, Cold Spring, NY 10516
0.62
$560,000
2
1
1,200
Off Market

Local Information

  • Map ViewExplore the area around 20 Windy Rdg.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1980
Lot Size
4 acres
Living Area
5,707 sqft
Price/Sqft
$952
Parking
Garage

About this House

This single-family home is located at 20 Windy Rdg, Cold Spring, NY. 20 Windy Rdg is in Cold Spring, NY and in ZIP code 10516. This property has 4 bedrooms, 3 bathrooms and approximately 5,707 sqft of floor space. This property has a lot size of 4.00 acres and was built in 1980.
20 Windy Rdg, Cold Spring, NY 10516 is a 4 bedroom, 3 bathroom, 5,707 sqft single-family home built in 1980. It last sold for $5,720,000 on May 5, 2022. It is currently off market. The Trulia Estimate is $5,432,500, with a rent estimate of $7,456/month.

Home Details for 20 Windy Rdg

Interior Features

Heating & Cooling
Heating: Heat Pump, Radiant, GasAir ConditioningCooling System: CentralHeating Fuel: Heat Pump
Levels, Entrance, & Accessibility
Stories: 3Floors: Hardwood
Interior Details
Number of Rooms: 10Types of Rooms: Master Bath
Appliances & Utilities
DishwasherWasher
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: OtherDeckExterior: Wood
Pool
Pool
Parking & Garage
GarageParking Spaces: 2Parking: Garage Attached

Property Information

Year Built
Year Built: 1980Year Updated: 2020
Property Type / Style
Property Type: Single Family HomeArchitecture: Contemporary

Community

Units in Building: 1

Lot Information

Lot Area: 4.00 acres

Price and Tax history

DateEventPrice
May 5, 2022
Source: OneKey® MLS as distributed by MLS GRID #H6142893
Sold
$5,720,000
Feb 22, 2022
Source: OneKey® MLS as distributed by MLS GRID #H6142893
Pending
$6,250,000
Sep 24, 2021
Source: OneKey® MLS as distributed by MLS GRID #H6142893
Listed For Sale
$6,250,000
Dec 18, 2017
Source: OneKey® MLS as distributed by MLS GRID #H4714842
Sold
$2,050,000
Nov 9, 2017
Source: Agent Provided
PriceChange
$1,995,000
Price decreased by 23%

Market trends in Cold Spring

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
20
2MoM

Around this home

What Locals Say about Cold Spring

At least 49 Trulia users voted on each feature.

  • 93 % Say there's holiday spirit

  • 86 % Say people would walk alone at night

  • 85 % Say yards are well-kept

  • 84 % Say it's dog friendly

  • 83 % Say there's wildlife

  • 80 % Say there are sidewalks

  • 78 % Say they plan to stay for at least 5 years

  • 75 % Say car is needed

  • 72 % Say neighbors are friendly

  • 71 % Say it's walkable to grocery stores

  • 70 % Say kids play outside

  • 69 % Say parking is easy

  • 68 % Say it's walkable to restaurants

  • 67 % Say it's quiet

  • 67 % Say streets are well-lit

  • 62 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Trulia User
    "I live in the deep woods. Wild and free and quiet!"
    0
    Flag
  • Ldesbrisay
    "Lots of tourists but lovely place. Beautiful. I don’t have kids but supposedly good schools. A special pocket of the world. "
    0
    Flag
  • Ldesbrisay
    "Dog town through and through. So many and they all know each other. Meet your neighbors at the park. "
    0
    Flag
  • George.schuler
    "Wfh is how it works for me and my family and the community is really good for kids. Our commutes are zero now but easy in any condition "
    1
    Flag
  • Sam R.
    "I’ve lived here for 12 years and my only regret is I didn’t get the chance to grow up here. A perfect little town, with a breathtaking waterfront - only 50 miles north of NYC. "
    0
    Flag
  • Cjnaughti
    "I have lived here for 12 years and have loved it. People are friendly and family oriented. Many people are creative and artistic."
    1
    Flag
  • Cjnaughti
    "We are a small town of family oriented people, lots of artist and independent business owners. Great school district as well."
    0
    Flag
  • ColdSpringGuy
    "Great places for active families, and people looking for a better quality of life but still commute to the city."
    1
    Flag
  • Trulia User
    "1 hour 20 min train ride to Grand Central. No real jobs on town. Need to drive north or south or catch train."
    1
    Flag
  • Vandermerwede
    "Not a single traffic light and great hikes. Right next to Cold Spring. Can commute to NYC. Just South of Beacon"
    0
    Flag
  • Mollyadmana
    "I’ve been living here for 4 years now. It’s a great neighborhood for NYC expats with kids. Amazing schools. "
    0
    Flag
  • Dstracci
    "I wouldn’t call it a neighborhood, I’d call it an area. I like that it’s quiet but still close to everything and just Minutes away from the village of cold spring which always has something to do."
    0
    Flag
  • Stephanie
    "I have lived here for 6 years and know everyone of our neighbors. We all came together to help one another in the last couple of storms. Neighbors look out for each other’s kids. It’s a special community within the larger communities of garrison and cold spring."
    0
    Flag
  • Stephanie
    "Gorgeous neighborhood. Not in town, not too far from town. Nice community of neighbors and access to good schools."
    0
    Flag
  • Alexanderverron
    "You couldn’t ask for a better neighborhood to commute to Nyc from if you have a family and enjoy being active outdoors."
    2
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 20 Windy Rdg

  • What is 20 Windy Rdg estimated to be worth?
    Trulia's estimated value for 20 Windy Rdg in Cold Spring, NY is $5,432,500.
  • What is the price history for 20 Windy Rdg?
    20 Windy Rdg in Cold Spring, NY last sold for $5,720,000 in May 2022.
  • Is Cold Spring a buyer's or seller's market?
    Cold Spring is currently a seller's market, based on recent for-sale activity.
  • What do residents say about Cold Spring?
    Residents describe Cold Spring, NY as well-kept, dog-friendly, and pedestrian-friendly. See recently sold homes in Cold Spring, NY.
  • Does 20 Windy Rdg have air conditioning?
    Yes, 20 Windy Rdg in Cold Spring, NY has air conditioning.
  • Does 20 Windy Rdg have a pool?
    Yes, 20 Windy Rdg in Cold Spring, NY has a pool.

Explore by feature - Air Conditioning

Explore by feature - Washer/dryer

7 rentals with a washer/dryer in Cold Spring, NY

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