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

8 Overlook Dr
Pawling, NY 12564

  • 3 Beds
  • 1.5 Baths
  • 2,112 sqft (on 1.16 acres)

$506,800

Trulia Estimate
as of Aug 13, 2026
Est. Refi. Payment $3,429/mo*
Refinance Your Home

$506,800

Trulia Estimate
as of Aug 13, 2026
Est. Refi. Payment $3,429/mo*
Refinance Your Home
3 Beds
1.5 Baths
2,112 sqft
(on 1.16 acres)

Home Value

Trulia Estimate
$507K
Since last month
Decreased$8K (-1.6%)
Since last year
Increased$21K (+4.2%)
Since last sale
Increased$251K (+98.3%)
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 +55% in the last 10 years
MonthEstimated value
2026
August 2026$506K
July 2026$511K
June 2026$514K
May 2026$509K
April 2026$499K
March 2026$487K
February 2026$477K
January 2026$475K
2025
2024
2023
2022
2021
2020
2019

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
0.16
Single-Family Home
$610,500
06/25/26
3
3
1,640
2 Bridle Way, Pawling, NY
0.32
Single-Family Home
$485,000
02/11/26
3
3.5
3,467
24 Overlook Drive, Pawling, NY
0.34
Single-Family Home
$735,000
07/21/26
3
3.5
3,175
42 Harmony Road, Pawling, NY
0.56
Single-Family Home
$415,000
08/19/25
2
1
1,152
36 Horseshoe Path, Pawling, NY
0.75
Single-Family Home
$775,000
05/01/26
3
2.5
4,627
5 Perri Lane, Pawling, NY
0.90
Single-Family Home
$697,500
01/24/26
3
2.5
2,796
4 Mane Way, Pawling, NY
0.69
Single-Family Home
$775,000
04/24/26
4
2.5
3,611
14 Old Route 55, Pawling, NY
1.15
Single-Family Home
$269,950
04/15/26
3
1
1,653
29 Cunningham Lane, Pawling, NY
0.71
Single-Family Home
$660,000
01/16/26
4
4
4,199
79 W Main Street, Pawling, NY
1.14
Single-Family Home
$615,000
04/02/26
3
2
2,254

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
6 Overlook Dr, Pawling, NY 12564
0.07
$729,999
3
3
2,659
For Sale
85 Harmony Hill Road, Pawling, NY 12564
0.16
$610,500
3
3
1,640
Recently Sold
15 Stirrup Trail, Pawling, NY 12564
0.28
$762,000
4
3.5
3,246
Off Market
3846 Route 55, Pawling, NY 12564
0.25
$639,000
4
2.5
1,696
For Sale
2 Bridle Way, Pawling, NY 12564
0.32
$485,000
3
3.5
3,467
Recently Sold
74 Harmony Hill Road, Pawling, NY 12564
0.34
$546,600
4
2
1,736
Off Market
21 Overlook Drive, Pawling, NY 12564
0.33
$699,000
3
2.5
1,460
For Sale
24 Overlook Drive, Pawling, NY 12564
0.34
$735,000
3
3.5
3,175
Recently Sold
10 Canter Circle, Pawling, NY 12564
0.43
$632,000
3
2.5
2,004
Off Market
22 Martingale Way, Pawling, NY 12564
0.56
$683,200
4
2.5
2,359
Off Market
197 Highlands Drive, Pawling, NY 12564
0.56
$825,400
5
3
2,719
Off Market
7 Anderson Way, Pawling, NY 12564
0.57
$570,400
4
1.5
1,919
Off Market

Local Information

  • Map ViewExplore the area around 8 Overlook Dr.
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1971
Lot Size
1.16 acres
Living Area
2,112 sqft
Price/Sqft
$240
Parking
Garage

About this House

Expanded Raised Ranch that can fit the Whole Family! Sunny Family Room off the Eat-in-Kitchen plus a formal Dining Room and an Over-sized Living Room. There are hardwoods floors throughout most of the home. Besides the 2 car garage there is a 12 x 26 Storage Area with an Over Head Door. The home sits on a great lot on a quiet street which is convenient to the Metro North Railroad and Major Highways. Convenient to Lakeside Park with a 36 Acre Lake and Dutchess Golf Course!
8 Overlook Dr, Pawling, NY 12564 is a 3 bedroom, 2 bathroom, 2,112 sqft single-family home built in 1971. It last sold for $255,000 on Jun 8, 2016. It is currently off market. The Trulia Estimate is $506,800, with a rent estimate of $3,791/month.

Home Details for 8 Overlook Dr

Interior Features

Interior Details
BasementNumber of Rooms: 10Types of Rooms: Dining Room, Office
Heating & Cooling
Heating: Baseboard, ElectricAir ConditioningCooling System: WallHeating Fuel: Baseboard
Levels, Entrance, & Accessibility
Stories: 2Floors: Hardwood
Appliances & Utilities
DishwasherDryerMicrowaveRefrigeratorWasher

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Vinyl
Pool
Pool
Parking & Garage
GarageParking Space: 1Parking: Garage Attached

Property Information

Year Built
Year Built: 1971Year Updated: 1985
Property Type / Style
Property Type: Single Family HomeArchitecture: Ranch / Rambler

Lot Information

Lot Area: 1.16 acres

Price and Tax history

DateEventPrice
Jun 8, 2016
Source: OneKey® MLS as distributed by MLS GRID #H4605870
Sold
$255,000
Mar 29, 2016
Source: Agent Provided
Pending
$269,900
Feb 17, 2016
Source: Agent Provided
Listed For Sale
$269,900
Jan 1, 2016
Source: Agent Provided
ListingRemoved
$269,000
Nov 19, 2015
Source: Agent Provided
PriceChange
$269,000
Price decreased by 4%

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
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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
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  • 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
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Apartments for Rent

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Homes for sale near 8 Overlook Dr

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Off Market Homes Near 8 Overlook Dr

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Frequently asked questions about 8 Overlook Dr

  • What is 8 Overlook Dr estimated to be worth?
    Trulia's estimated value for 8 Overlook Dr in Pawling, NY is $506,800.
  • What is the price history for 8 Overlook Dr?
    8 Overlook Dr in Pawling, NY last sold for $255,000 in June 2016.
  • 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 8 Overlook Dr have air conditioning?
    Yes, 8 Overlook Dr in Pawling, NY has air conditioning.
  • Does 8 Overlook Dr have a pool?
    Yes, 8 Overlook Dr in Pawling, NY has a pool.