2 Circle Dr, Pawling, NY 12564
Property image
Property image
OFF MARKET

$496,800

Trulia Estimate
  • 3 Beds
  • 2.5 Baths
  • 1,524 sqft (on 0.45 acres)

2 Circle Dr, Pawling, NY 12564

Est. Refi. Payment $3,442/mo*
Refinance Your Home
Currently Off Market - Sold May 22, 2012 for $200,000

Home Value

Trulia Estimate
$497K
Since last month
Decreased$2K (-0.4%)
Since last year
Increased$39K (+8.5%)
Since last sale
Increased$298K (+149.1%)
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 +167% in the last 10 years
MonthEstimated value
2026
August 2026$498K
August 2026$497K
July 2026$500K
June 2026$510K
May 2026$510K
April 2026$495K
March 2026$464K
February 2026$450K
January 2026$449K
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
66 Fairway Drive, Pawling, NY
0.07
Single-Family Home
$535,000
03/10/26
3
2
1,490
30 Smith St, Pawling, NY
0.46
Single-Family Home
$180,000
01/27/26
3
2
1,679
24 Fairway Dr, Pawling, NY
0.25
Single-Family Home
$343,500
10/27/25
3
1
1,300
17 Townsend Boulevard, Pawling, NY
0.41
Single-Family Home
$410,000
08/31/26
2
2
1,088
36 Elm Street, Pawling, NY
0.62
Single-Family Home
$436,000
12/18/25
3
1.5
1,680
16 Townsend Boulevard, Pawling, NY
0.46
Single-Family Home
$375,000
03/04/26
2
1
1,080
79 W Main Street, Pawling, NY
0.59
Single-Family Home
$615,000
04/02/26
3
2
2,254
23 Union Street, Pawling, NY
0.54
Single-Family Home
$405,000
02/11/26
3
2
1,480
40 Walnut Street, Pawling, NY
0.69
Single-Family Home
$439,370
05/20/26
4
1.5
1,776
12 Anderson Way, Pawling, NY
0.56
Single-Family Home
$392,000
01/08/26
2
1
1,160

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
8 Circle Drive, Pawling, NY 12564
0.06
$464,900
3
1
1,110
Off Market
85 Fairway Drive, Pawling, NY 12564
0.04
$471,700
3
1.5
1,079
Off Market
66 Fairway Drive, Pawling, NY 12564
0.07
$535,000
3
2
1,490
Recently Sold
77 E Main Street, Pawling, NY 12564
0.22
$481,400
3
2
1,940
Off Market
12 Henry Street, Pawling, NY 12564
0.25
$448,400
3
1
1,512
Off Market
19 Dutcher Avenue, Pawling, NY 12564
0.26
$528,900
3
2
1,792
Off Market
99 E Main Street, Pawling, NY 12564
0.23
$766,700
4
2.5
4,013
Off Market
15 Fairway Drive, Pawling, NY 12564
0.28
$469,200
4
2
1,680
Off Market
5 Henry Street, Pawling, NY 12564
0.30
$399,000
4
3
2,424
For Sale
92 E Main Street, Pawling, NY 12564
0.29
$663,900
4
3
1,824
Off Market
7 Evergreen Way, Pawling, NY 12564
0.32
$356,800
2
2.5
1,413
Off Market
4 Juniper Lane, Pawling, NY 12564
0.34
$401,600
2
2.5
2,100
Off Market

Local Information

  • Map ViewExplore the area around 2 Circle Dr.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1958
0.45 acre lot
1,524 sqft
$326/sqft
Garage

About this House

Classic split with level park like property. Entry level features Living room which opens to the dining room and eat in kitchen. Upper level boasts Master with half bath, 2 add'l bedrooms and hall bath. Door over these stairs for attic entry. Family room, laundry, half bath and garage comprise the lower level with access to the outdoors. Other features include wood floors,easy access to train, commuter routes and picturesque village center. Well maintained home in neighborhood setting.
2 Circle Dr, Pawling, NY 12564 is a 3 bedroom, 3 bathroom, 1,524 sqft single-family home built in 1958. It last sold for $200,000 on May 22, 2012. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $496,800, with a rent estimate of $3,749/month.

Home Details for 2 Circle Dr

Interior Features

Interior Details
BasementAdditional StorageAtticNumber of Rooms: 7Types of Rooms: Dining Room, Family Room, Master Bath, Recreation RoomStorage
Levels, Entrance, & Accessibility
Stories: 3Floors: Hardwood, Linoleum Vinyl
Appliances & Utilities
DryerRefrigeratorWasher
Fireplace & Spa
Fireplace

Property Information

Year Built
Year Built: 1958
Property Type / Style
Property Type: Single Family HomeArchitecture: Split-level

Building

Levels, Entrance, & Accessibility
Disabled Access

Exterior Features

Exterior Home Features
DeckExterior: WoodLawn
Pool
Pool
Parking & Garage
GarageParking: Garage Attached

Community

Units in Building: 1

Lot Information

Lot Area: 0.45 acres

Price and Tax history

DateEventPrice
May 22, 2012
Source: OneKey® MLS as distributed by MLS GRID #H3204383
Sold
$200,000
Feb 11, 2012
Source: Agent Provided
Listed For Sale
$200,000
Jan 2, 2012
Source: Agent Provided
ListingRemoved
$225,000
Nov 9, 2011
Source: Agent Provided
PriceChange
$225,000
Price decreased by 6%
Sep 15, 2011
Source: Agent Provided
PriceChange
$240,000
Price decreased by 4%

Market trends in Pawling

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
23
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 2 Circle Dr

  • What is 2 Circle Dr estimated to be worth?
    Trulia's estimated value for 2 Circle Dr in Pawling, NY is $496,800.
  • What is the price history for 2 Circle Dr?
    2 Circle Dr in Pawling, NY last sold for $200,000 in May 2012.
  • 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.
  • Does 2 Circle Dr have a pool?
    Yes, 2 Circle Dr in Pawling, NY has a pool.
  • Does 2 Circle Dr have laundry facilities?
    Yes, 2 Circle Dr in Pawling, NY has in-unit laundry.

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