53 E Main St, Pawling, NY 12564
Property image
Property image
OFF MARKET

$442,500

Trulia Estimate
  • 3 Beds
  • 3 Baths
  • 1,500 sqft

53 E Main St, Pawling, NY 12564

Est. Refi. Payment $3,000/mo*
Refinance Your Home

Home Value

Trulia Estimate
$443K
Since last month
Increased$4K (+1%)
Since last year
Decreased$16K (-3.4%)
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 +97% in the last 10 years
MonthEstimated value
2026
August 2026$444K
July 2026$439K
June 2026$449K
May 2026$456K
April 2026$435K
March 2026$434K
February 2026$393K
January 2026$436K
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
23 Union Street, Pawling, NY
0.34
Single-Family Home
$405,000
02/11/26
3
2
1,480
30 Smith St, Pawling, NY
0.17
Single-Family Home
$180,000
01/27/26
3
2
1,679
24 Fairway Dr, Pawling, NY
0.11
Single-Family Home
$343,500
10/27/25
3
1
1,300
66 Fairway Drive, Pawling, NY
0.22
Single-Family Home
$535,000
03/10/26
3
2
1,490
36 Elm Street, Pawling, NY
0.40
Single-Family Home
$436,000
12/18/25
3
1.5
1,680
16 Townsend Boulevard, Pawling, NY
0.19
Single-Family Home
$375,000
03/04/26
2
1
1,080
37 Baxter Road, Pawling, NY
0.73
Single-Family Home
$560,000
10/06/25
3
3.5
2,616
33 Spruce Street, Pawling, NY
0.58
Single-Family Home
$350,000
12/18/25
2
2.5
1,413
36 Spruce Street #36, Pawling, NY
0.59
Single-Family Home
$330,000
10/02/25
2
2.5
1,414
16 Juniper Lane, Pawling, NY
0.55
Single-Family Home
$385,000
07/13/26
2
2
1,639

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
77 E Main Street, Pawling, NY 12564
0.11
$484,900
3
2
1,940
Off Market
18 Coulter Avenue, Pawling, NY 12564
0.14
$762,700
5
2.5
2,722
Off Market
92 E Main Street, Pawling, NY 12564
0.17
$661,300
4
3
1,824
Off Market
15 Fairway Drive, Pawling, NY 12564
0.14
$472,200
4
2
1,680
Off Market
16 Townsend Boulevard, Pawling, NY 12564
0.19
$375,000
2
1
1,080
Recently Sold
15 Memorial Avenue, Pawling, NY 12564
0.16
$785,100
4
3
3,778
Off Market
12 Henry Street, Pawling, NY 12564
0.19
$451,100
3
1
1,512
Off Market
99 E Main Street, Pawling, NY 12564
0.22
$773,000
4
2.5
4,013
Off Market
66 Fairway Drive, Pawling, NY 12564
0.22
$535,000
3
2
1,490
Recently Sold
19 Dutcher Avenue, Pawling, NY 12564
0.24
$532,900
3
2
1,792
Off Market
33 Coulter Avenue, Pawling, NY 12564
0.28
$641,600
4
1.5
3,731
Off Market
85 Fairway Drive, Pawling, NY 12564
0.32
$471,700
3
1.5
1,079
Off Market

Local Information

  • Map ViewExplore the area around 53 E Main St.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1927
Living Area
1,500 sqft
Price/Sqft
$295

About this House

Charm & Character! Totally Re-Built & Finished In 2004. Full Of Beadboard, Chair-Rail, And Interesting Angles This Village Of Pawling Home Has It All. Beautiful Oak And Maple Hardwood Floors, Central Ac, 2 Fireplaces, Cherry Cabinets W/Antique Glaze, Granite Countertops, Ge Profile Stainless Appliances, Mahogany Covered Porch, Large, Unique Bluestone Patio, Stone Walls, Fully Networked Cat5e, Radiant Heat, Marvin Integrity Windows, Custom Blinds And More. Walk To Train & Shops. Amazing Value!!
53 E Main St, Pawling, NY 12564 is a 3 bedroom, 3 bathroom, 1,500 sqft single-family home built in 1927. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $442,500, with a rent estimate of $3,155/month.

Home Details for 53 E Main St

Interior Features

Heating & Cooling
Heating: Forced AirHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2
Interior Details
Number of Rooms: 10

Property Information

Year Built
Year Built: 1927Year Updated: 1996
Property Type / Style
Property Type: Single Family HomeArchitecture: Old Style

Exterior Features

Exterior Home Features
Exterior: Wood

Community

Units in Building: 2

Lot Information

Lot Area: 4356 sqft

Price and Tax history

YearProperty taxTax assessment
2025Unavailable
$338,100
Home facts updated by county records

Market trends in Pawling

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
25
2MoM

Around this home

What Locals Say about Pawling

At least 43 Trulia users voted on each feature.

  • 84 % Say parking is easy

  • 82 % Say car is needed

  • 81 % Say yards are well-kept

  • 80 % Say it's dog friendly

  • 78 % Say there's wildlife

  • 76 % Say there's holiday spirit

  • 71 % Say people would walk alone at night

  • 66 % Say neighbors are friendly

  • 65 % Say it's quiet

  • 64 % Say kids play outside

  • 56 % Say they plan to stay for at least 5 years

  • 50 % Say streets are well-lit

  • 47 % Say it's walkable to restaurants

  • 46 % Say there are sidewalks

  • 35 % Say there are community events

  • 21 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • Jriina78
    "Pawling is very family friendly. Fun hiking trails and easy to get around if you need public transportation. "
    0
    Flag
  • Suzie F.
    "My work is 3 mins away so my commute is super easy. My husband drives to Poughkeepsie and it’s not bad either. "
    5
    Flag
  • Dawn Z.
    "picking up after there animal, and making sure where they went is cleaned up. It's a nice place for animals and people to walk."
    1
    Flag
  • Trulia User
    "I lived in Pawling my whole life. It's a small and friendly community. My biggest criticism is the sudden increase on the rentals and the housing market, making it near!y impossible for long time locals to maintain cost of living"
    10
    Flag
  • Trulia User
    "People walk their dogs out on the road due to lack of sidewalks. Not very safe. We do have a local park with access to trails and a lake where dogs can go for a swim."
    0
    Flag
  • Francesca T. B.
    "It’s a 35 minute drive to Poughkeepsie. It’s an easy drive straight down Rt. 55. I leave daily by 7:30 and get home by 5. "
    0
    Flag
  • Francesca T. B.
    "I’ve lived here for 20 years. You can walk unafraid. Restaurants, small store, library all close by. "
    0
    Flag
  • Sarah
    "Quiet country life with lots of space For dogs to run around or take a long walk. Plenty of beauty and fresh air for all with reasonable proximity to conveniences. "
    0
    Flag
  • Christine O. l.
    "Good trails, lots of great veterinarians, good doggy day cares. It’s a very country/animal focused and welcoming community. "
    0
    Flag
  • Carolyn C.
    "Have lived in the area for 15 years. Pawling is a very small town surrounded by mountains, hiking trails, art and culture. Very safe and a decidedly suburban vibe. Since I am a city girl born and raised in NYC, I thought I would become very bored very quickly but it has grown on me. I live within 2 hrs drive of the Berkshire Mountains, Long Island Sound and New York City (depending on traffic) but I can come home and revel in the silence. "
    0
    Flag
  • Annmarie P.
    "Good area for commuting to work - Metro North to most major areas. Lots of things to do in the area, friendly, helpful people. Affordable. Municiple water and sewers. "
    0
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 53 E Main St

  • What is 53 E Main St estimated to be worth?
    Trulia's estimated value for 53 E Main St in Pawling, NY is $442,500.
  • Is Pawling a buyer's or seller's market?
    Pawling is currently a seller's market, based on recent for-sale activity.
  • What do residents say about Pawling?
    Residents describe Pawling, NY as easy to park in, well-kept, and dog-friendly. Most residents say you need a car. See recently sold homes in Pawling, NY.
  • What are the closest schools to 53 E Main St?
    The closest schools to 53 E Main St in Pawling, NY are Pawling Elementary School (Pre-K, rated 5/10), Pawling High School (rated 7/10), Pawling Middle School (Elementary, rated 7/10).
  • How big is the lot at 53 E Main St?
    The lot at 53 E Main St in Pawling, NY is about 0.10 acres (4,356 sq ft).

Apartments for Rent

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Off Market Homes Near 53 E Main St

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