4 Overlook Dr, Pawling, NY 12564
Property image
Property image
OFF MARKET

$495,200

Trulia Estimate
  • 3 Beds
  • 2 Baths
  • 1,748 sqft (on 1.24 acres)

4 Overlook Dr, Pawling, NY 12564

Est. Refi. Payment $3,553/mo*
Refinance Your Home
Currently Off Market - Sold May 31, 2022 for $338,000

Home Value

Trulia Estimate
$495K
Since last month
$100 (0%)
Since last year
Increased$21K (+4.4%)
Since last sale
Increased$155K (+45.9%)
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 +102% in the last 10 years
MonthEstimated value
2026
October 2026$493K
September 2026$499K
August 2026$493K
July 2026$499K
June 2026$502K
May 2026$498K
April 2026$488K
March 2026$490K
February 2026$471K
January 2026$475K
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
85 Harmony Hill Road, Pawling, NY
0.17
Single-Family Home
$610,500
06/25/26
3
3
1,640
2 Bridle Way, Pawling, NY
0.35
Single-Family Home
$485,000
02/11/26
3
3.5
3,467
24 Overlook Drive, Pawling, NY
0.31
Single-Family Home
$735,000
07/21/26
3
3.5
3,175
103 S Harmony Hill Road, Pawling, NY
0.11
Single-Family Home
$762,000
09/29/26
3
3
3,729
40 Harmony Road, Pawling, NY
0.47
Single-Family Home
$550,000
09/30/26
4
2.5
1,968
5 Perri Lane, Pawling, NY
0.92
Single-Family Home
$697,500
01/24/26
3
2.5
2,796
36 Horseshoe Path, Pawling, NY
0.78
Single-Family Home
$775,000
05/01/26
3
2.5
4,627
6 Martingale Way, Pawling, NY
0.49
Single-Family Home
$705,000
08/28/26
4
3.5
4,687
4 Mane Way, Pawling, NY
0.71
Single-Family Home
$775,000
04/24/26
4
2.5
3,611
29 Cunningham Lane, Pawling, NY
0.72
Single-Family Home
$660,000
01/16/26
4
4
4,199

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 Overlook Dr, Pawling, NY 12564
0.03
$505,100
3
1.5
2,112
Off Market
6 Overlook Dr, Pawling, NY 12564
0.04
$689,999
3
3
2,659
For Sale
8 Overlook Rd, Pawling, NY 12564
0.04
-
-
-
-
Off Market
2 Overlook Dr, Pawling, NY 12564
0.05
$521,400
3
2
2,268
Off Market
Overlook Dr, Pawling, NY 12564
0.05
-
-
-
-
Off Market
3 Overlook Dr, Pawling, NY 12564
0.06
$468,500
3
2
1,563
Off Market
5 Overlook Dr, Pawling, NY 12564
0.07
$523,600
3
2
1,689
Off Market
8 Overlook Dr, Pawling, NY 12564
0.07
-
3
2
1,056
Off Market
8 Overlook Dr, Pawling, NY 12564
0.07
-
3
2
1,056
Off Market
91 Harmony Hill Rd, Pawling, NY 12564
0.08
$571,200
3
2
2,700
Off Market
S Harmony Hill Rd, Pawling, NY 12564
0.09
-
-
-
-
Off Market
S Harmony Hill Rd #1, Pawling, NY 12564
0.09
-
Studio
-
-
Off Market
S Harmony Hill Rd #2, Pawling, NY 12564
0.09
-
-
-
-
Off Market
102 S Harmony Hill Rd, Pawling, NY 12564
0.09
$536,000
3
2
1,696
Off Market
10 Overlook Dr, Pawling, NY 12564
0.10
$488,700
3
2
2,112
Off Market
12 Overlook Rd, Pawling, NY 12564
0.10
-
-
-
-
Off Market
103 S Harmony Hill Road, Pawling, NY 12564
0.11
$762,000
3
3
3,729
Recently Sold
3820 Route 55, Pawling, NY 12564
0.12
-
3
2
2,152
Off Market
3820 Route 55, Pawling, NY 12564
0.12
-
-
-
-
Off Market
96 Harmony Hill Rd, Pawling, NY 12564
0.14
-
3
2
1,352
Off Market

Local Information

  • Map ViewExplore the area around 4 Overlook Dr.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1966
1.24 acre lot
1,748 sqft
$283/sqft
Garage

About this House

What's unique:Huge family roomHalf bathFull hall bathWalk-in closetHuge deckLarge deck
Beautiful Property, Great Location, Private Setting! 5 minutes or less to the picturesque Village of Pawling, which offers Metro-North (Harlem Line), Lakeside Park w/beach, Dutcher Golf Course, quaint shops, library, cafe's, bakeries, pubs, great restaurants & deli's. This spacious home offers solid Hardwood Floors, Living Rm with picture window, open Dining Rm with slider to large deck. Walk-Out lower level features a Family Rm with Fireplace plus a home office/den. The upper level consists of a Main Bedroom with a walk-in closet and half bath. There are two additional Bedrooms and a full Hall Bath. The house needs some work, which is reflected in the price. (Just imagine the difference a new kitchen and gleaming refinished hardwood floors would make!) *Additional activities include Daryl's House (Daryl Hall) Restaurant & Music Club, Thunder Ridge Ski Center, World Gym, Pickleball courts at Lakeside Park, more! Hike the Appalachian Trail and the Oblong Reserve. Something for everyone!
4 Overlook Dr, Pawling, NY 12564 is a 3 bedroom, 3 bathroom, 1,748 sqft single-family home built in 1966. It last sold for $338,000 on May 31, 2022. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $495,200, with a rent estimate of $3,919/month.

Home Details for 4 Overlook Dr

Interior Features

Interior Details
BasementNumber of Rooms: 7
Heating & Cooling
Heating: Baseboard, ElectricHeating Fuel: Baseboard
Levels, Entrance, & Accessibility
Stories: 1Floors: Hardwood
Appliances & Utilities
DishwasherMicrowaveRefrigerator
Fireplace & Spa
Fireplace

Property Information

Year Built
Year Built: 1966Year Updated: 1966
Property Type / Style
Property Type: Single Family HomeArchitecture: split level

Exterior Features

Exterior Home Features
DeckExterior: Brick
Parking & Garage
GarageParking: Garage Attached

Community

Units in Building: 1

Lot Information

Lot Area: 1.24 acres

Price and Tax history

DateEventPrice
May 31, 2022
Source: OneKey® MLS as distributed by MLS GRID #H6141543
Sold
$338,000
Mar 8, 2022
Source: MHMLS #404459
Pending
$339,000
Feb 24, 2022
Source: OneKey® MLS as distributed by MLS GRID #H6141543
PendingToActive
$339,000
Nov 29, 2021
Source: OneKey® MLS as distributed by MLS GRID #H6141543
Pending
$339,000
Oct 29, 2021
Source: OneKey® MLS as distributed by MLS GRID #H6141543
PriceChange
$339,000
Price decreased by 3%

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 4 Overlook Dr

  • What is 4 Overlook Dr estimated to be worth?
    Trulia's estimated value for 4 Overlook Dr in Pawling, NY is $495,200.
  • What is the price history for 4 Overlook Dr?
    4 Overlook Dr in Pawling, NY last sold for $338,000 in May 2022.
  • 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.
  • How big is the lot at 4 Overlook Dr?
    The lot at 4 Overlook Dr in Pawling, NY is about 1.2 acres.
  • Does 4 Overlook Dr have a garage?
    Yes, 4 Overlook Dr in Pawling, NY has a garage.

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