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

20 Overlook Dr
Pawling, NY 12564

  • 3 Beds
  • 2.5 Baths
  • 1,728 sqft (on 1 acre)

$560,700

Trulia Estimate
as of Aug 14, 2026
Est. Refi. Payment $3,783/mo*
Refinance Your Home

$560,700

Trulia Estimate
as of Aug 14, 2026
Est. Refi. Payment $3,783/mo*
Refinance Your Home
3 Beds
2.5 Baths
1,728 sqft
(on 1 acre)

Home Value

Trulia Estimate
$561K
Since last month
Decreased$8K (-1.3%)
Since last year
Increased$11K (+2%)
Since last sale
Increased$143K (+34.1%)
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 +128% in the last 10 years
MonthEstimated value
2026
August 2026$561K
July 2026$564K
June 2026$569K
May 2026$565K
April 2026$556K
March 2026$550K
February 2026$539K
January 2026$540K
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
24 Overlook Drive, Pawling, NY
0.07
Single-Family Home
$735,000
07/21/26
3
3.5
3,175
85 Harmony Hill Road, Pawling, NY
0.31
Single-Family Home
$610,500
06/25/26
3
3
1,640
2 Bridle Way, Pawling, NY
0.56
Single-Family Home
$485,000
02/11/26
3
3.5
3,467
42 Harmony Road, Pawling, NY
0.42
Single-Family Home
$415,000
08/19/25
2
1
1,152
79 W Main Street, Pawling, NY
0.91
Single-Family Home
$615,000
04/02/26
3
2
2,254
5 Perri Lane, Pawling, NY
0.96
Single-Family Home
$697,500
01/24/26
3
2.5
2,796
36 Horseshoe Path, Pawling, NY
0.94
Single-Family Home
$775,000
05/01/26
3
2.5
4,627
4 Mane Way, Pawling, NY
0.83
Single-Family Home
$775,000
04/24/26
4
2.5
3,611
29 Cunningham Lane, Pawling, NY
0.69
Single-Family Home
$660,000
01/16/26
4
4
4,199
27 Millstream Court, Pawling, NY
0.95
Single-Family Home
$725,000
12/17/25
4
2.5
3,283

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
24 Overlook Drive, Pawling, NY 12564
0.07
$735,000
3
3.5
3,175
Recently Sold
21 Overlook Drive, Pawling, NY 12564
0.10
$699,000
3
2.5
1,460
For Sale
3846 Route 55, Pawling, NY 12564
0.13
$639,000
4
2.5
1,696
For Sale
6 Overlook Dr, Pawling, NY 12564
0.21
$729,999
3
3
2,659
For Sale
39 Overlook Drive, Pawling, NY 12564
0.35
$1,186,000
3
2.5
2,441
Off Market
85 Harmony Hill Road, Pawling, NY 12564
0.31
$610,500
3
3
1,640
Recently Sold
42 Harmony Road, Pawling, NY 12564
0.42
$442,900
2
1
1,152
Off Market
33 FAWN RIDGE Drive, Pawling, NY 12564
0.48
$1,546,600
5
4.5
4,200
Off Market
74 Harmony Hill Road, Pawling, NY 12564
0.46
$546,600
4
2
1,736
Off Market
15 Stirrup Trail, Pawling, NY 12564
0.48
$762,000
4
3.5
3,246
Off Market
27 Fawn Ridge Drive, Pawling, NY 12564
0.56
$773,100
4
3
3,012
Off Market
7 Anderson Way, Pawling, NY 12564
0.55
$557,200
4
1.5
1,919
Off Market

Local Information

  • Map ViewExplore the area around 20 Overlook Dr.
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1965
Lot Size
1 acre
Living Area
1,728 sqft
Price/Sqft
$324
Parking
Garage

About this House

What a Beautiful home with spectacular views!! Move in condition! Walk into the main floor with a great kitchen w/breakfast nook, stainless steel appliances, Dining area and Living Rm w/ Sliding Glass doors out to a deck that over looks back yard.. A great place to relax and enjoy the views. 3rd story has 3 Bedrooms - Master Bedroom has 1/2 Bath and Main Bathroom in hallway. Bottom level has a nice size family room to enjoy your family with a full bath - laundry room and another level to the basement with lots of storage and exterior excess. Generator hook up. Water Tank is 1 year old, A/C is 6 years old, Rood is 7 years old, Refrigerator is 1 1/2 years old.
20 Overlook Dr, Pawling, NY 12564 is a 3 bedroom, 3 bathroom, 1,728 sqft single-family home built in 1965. It last sold for $418,500 on Jan 29, 2021. It is currently off market. The Trulia Estimate is $560,700, with a rent estimate of $3,929/month.

Home Details for 20 Overlook Dr

Interior Features

Interior Details
BasementAttic
Heating & Cooling
Heating: Baseboard, OtherAir ConditioningCooling System: CentralHeating Fuel: Baseboard
Levels, Entrance, & Accessibility
Stories: 3Floors: Hardwood
Appliances & Utilities
DishwasherDryerRefrigeratorWasher

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Wood
Parking & Garage
GarageParking Spaces: 3Parking: Garage Detached

Property Information

Year Built
Year Built: 1965
Property Type / Style
Property Type: Single Family HomeArchitecture: split level

Community

Units in Building: 1

Lot Information

Lot Area: 1 acre

Additional Information

On Site Laundry Available

Price and Tax history

DateEventPrice
Jan 29, 2021
Source: OneKey® MLS as distributed by MLS GRID #H6077408
Sold
$418,500
Dec 6, 2020
Source: Agent Provided
Pending
$429,995
Nov 4, 2020
Source: Agent Provided
PriceChange
$429,995
Price decreased by 4%
Oct 15, 2020
Source: Agent Provided
Listed For Sale
$449,000

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
    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
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Apartments for Rent

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Homes for sale near 20 Overlook Dr

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Off Market Homes Near 20 Overlook Dr

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Frequently asked questions about 20 Overlook Dr

  • What is 20 Overlook Dr estimated to be worth?
    Trulia's estimated value for 20 Overlook Dr in Pawling, NY is $560,700.
  • What is the price history for 20 Overlook Dr?
    20 Overlook Dr in Pawling, NY last sold for $418,500 in January 2021.
  • 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 20 Overlook Dr have air conditioning?
    Yes, 20 Overlook Dr in Pawling, NY has air conditioning.
  • Does 20 Overlook Dr have laundry facilities?
    Yes, 20 Overlook Dr in Pawling, NY has in-unit laundry.