23 Cunningham Loop, Chestertown, NY 12817
OFF MARKET

23 Cunningham Loop
Chestertown, NY 12817

  • 3 Beds
  • 2 Baths
  • 1,696 sqft (on 1.30 acres)

$294,100

Trulia Estimate
as of Aug 11, 2026
Est. Refi. Payment $1,882/mo*
Refinance Your Home

$294,100

Trulia Estimate
as of Aug 11, 2026
Est. Refi. Payment $1,882/mo*
Refinance Your Home
3 Beds
2 Baths
1,696 sqft
(on 1.30 acres)

Local Information

  • Map ViewExplore the area around 23 Cunningham Loop.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1867
Lot Size
1.3 acres
Living Area
1,696 sqft
Price/Sqft
$173
Parking
Garage

About this House

This single-family home is located at 23 Cunningham Loop, Chestertown, NY. 23 Cunningham Loop is in Chestertown, NY and in ZIP code 12817. This property has 3 bedrooms, 2 bathrooms and approximately 1,696 sqft of floor space. This property has a lot size of 1.30 acres and was built in 1867.
23 Cunningham Loop, Chestertown, NY 12817 is a 3 bedroom, 2 bathroom, 1,696 sqft single-family home built in 1867. It last sold for $40,000 on May 20, 2002. It is currently off market. The Trulia Estimate is $294,100, with a rent estimate of $2,446/month.

Home Details for 23 Cunningham Loop

Interior Features

Interior Details
Basement
Heating & Cooling
Heating: Other, OtherHeating Fuel: Other
Levels, Entrance, & Accessibility
Stories: 2

Property Information

Year Built
Year Built: 1867Year Updated: 2005
Property Type / Style
Property Type: Single Family HomeArchitecture: Old Style

Exterior Features

Exterior Home Features
Exterior: Wood
Parking & Garage
GarageParking: Garage Detached

Community

Units in Building: 1

Lot Information

Lot Area: 1.30 acres

Price History for 23 Cunningham Loop

DatePriceEventSource
05/20/2002$40,000Sold
N/A

Market trends in Chestertown

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
20
4MoM
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Property Tax and Assessment

Year2025
Tax
Assessment$282,500
Home facts updated by county records

Comparable Sales for 23 Cunningham Loop

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
11 Mill St, Chestertown, NY
1.09
Single-Family Home
$339,500
11/17/25
4
2
1,651
11 Mill Street, Chestertown, NY
1.09
Single-Family Home
$339,500
10/24/25
3
1
1,651
280 Knapp Hill Rd, Chestertown, NY
0.99
Single-Family Home
$20,000
11/18/25
2
1
782
23 Theriot Avenue, Chestertown, NY
1.00
Single-Family Home
$220,000
10/28/25
2
1
1,200
484 Rock Ave, Chestertown, NY
1.66
Single-Family Home
$370,000
12/18/25
3
1.5
1,344
1382 Friends Lake Road, Chestertown, NY
2.03
Single-Family Home
$325,000
09/26/25
2
1.5
1,456
123 Stock Farm Road, Chestertown, NY
1.82
Single-Family Home
$605,000
12/08/25
3
2.5
2,528
972 Friends Lake Road, Chestertown, NY
2.38
Single-Family Home
$1,213,000
10/20/25
3
2
2,316
5387-5391 State Route 8, Chestertown, NY
2.51
Single-Family Home
$725,000
01/22/26
4
2
1,768
90 Dixon Road, Chestertown, NY
2.65
Single-Family Home
$184,370
12/23/25
3
2
1,312

Nearby homes

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Assigned Schools

These are the assigned schools for 23 Cunningham Loop.

What Locals Say about Chestertown

At least 6 Trulia users voted on each feature.

  • 100 % Say there's wildlife

  • 92 % Say parking is easy

  • 90 % Say yards are well-kept

  • 83 % Say car is needed

  • 74 % Say neighbors are friendly

  • 73 % Say it's dog friendly

  • 73 % Say people would walk alone at night

  • 70 % Say there's holiday spirit

  • 69 % Say they plan to stay for at least 5 years

  • 64 % Say it's quiet

  • 60 % Say there are community events

  • 54 % Say it's walkable to restaurants

  • 50 % Say streets are well-lit

  • 46 % Say kids play outside

  • 36 % Say it's walkable to grocery stores

  • 31 % Say there are sidewalks

Sourced by Trulia users. Learn more about our methodology.
  • Prbyerin
    "This island setting couldn't be more peaceful. The lake views are outstanding. Being an island it is safe, (no unwanted traffic), long-term residents who are about 90% seasonal. Loon Lake has the cleanest water of any lake you could ever want to live on. Lots of quiet roads and woods for walks alone or with a pet. Location is about 20 minutes west to Gore Mountain for skiing and the same distance south to Lake George and Great Escape for family fun. All sorts of water sports right at your front door. Only 2 1/2 hours north to Montreal for an international adventure."
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    Flag

LGBTQ Local Legal Protections

Apartments for Rent

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Homes for sale near 23 Cunningham Loop

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Off Market Homes Near 23 Cunningham Loop

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Frequently asked questions about 23 Cunningham Loop

  • What is 23 Cunningham Loop estimated to be worth?
    Trulia's estimated value for 23 Cunningham Loop in Chestertown, NY is $294,100.
  • What is the price history for 23 Cunningham Loop?
    23 Cunningham Loop in Chestertown, NY last sold for $40,000 in May 2002.
  • Is Chestertown a buyer's or seller's market?
    Chestertown is currently a seller's market, based on recent for-sale activity.
  • What do residents say about Chestertown?
    Residents describe Chestertown, NY as easy to park in, well-kept, and neighborly. Most residents say you need a car. See recently sold homes in Chestertown, NY.
  • How big is the lot at 23 Cunningham Loop?
    The lot at 23 Cunningham Loop in Chestertown, NY is about 1.3 acres.
  • Does 23 Cunningham Loop have a garage?
    Yes, 23 Cunningham Loop in Chestertown, NY has a garage.