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

18 Overlook Dr
Pawling, NY 12564

  • 4 Beds
  • 1.5 Baths
  • 2,072 sqft (on 1 acre)

$557,100

Trulia Estimate
as of Aug 14, 2026
Est. Refi. Payment $3,759/mo*
Refinance Your Home

$557,100

Trulia Estimate
as of Aug 14, 2026
Est. Refi. Payment $3,759/mo*
Refinance Your Home
4 Beds
1.5 Baths
2,072 sqft
(on 1 acre)

Home Value

Trulia Estimate
$557K
Since last month
Decreased$1K (-0.3%)
Since last year
Increased$15K (+2.7%)
Since last sale
Increased$90K (+19.4%)
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 +139% in the last 10 years
MonthEstimated value
2026
August 2026$557K
July 2026$556K
June 2026$558K
May 2026$557K
April 2026$547K
March 2026$543K
February 2026$535K
January 2026$537K
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
0.10
Single-Family Home
$735,000
07/21/26
3
3.5
3,175
85 Harmony Hill Road, Pawling, NY
0.29
Single-Family Home
$610,500
06/25/26
3
3
1,640
2 Bridle Way, Pawling, NY
0.53
Single-Family Home
$485,000
02/11/26
3
3.5
3,467
42 Harmony Road, Pawling, NY
0.43
Single-Family Home
$415,000
08/19/25
2
1
1,152
79 W Main Street, Pawling, NY
0.94
Single-Family Home
$615,000
04/02/26
3
2
2,254
29 Cunningham Lane, Pawling, NY
0.69
Single-Family Home
$660,000
01/16/26
4
4
4,199
4 Mane Way, Pawling, NY
0.81
Single-Family Home
$775,000
04/24/26
4
2.5
3,611
27 Millstream Court, Pawling, NY
0.95
Single-Family Home
$725,000
12/17/25
4
2.5
3,283
5 Perri Lane, Pawling, NY
0.95
Single-Family Home
$697,500
01/24/26
3
2.5
2,796
40 Walnut Street, Pawling, NY
1.34
Single-Family Home
$439,370
05/20/26
4
1.5
1,776

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
0.10
$735,000
3
3.5
3,175
Recently Sold
3846 Route 55, Pawling, NY 12564
0.12
$639,000
4
2.5
1,696
For Sale
21 Overlook Drive, Pawling, NY 12564
0.12
$699,000
3
2.5
1,460
For Sale
6 Overlook Dr, Pawling, NY 12564
0.18
$729,999
3
3
2,659
For Sale
85 Harmony Hill Road, Pawling, NY 12564
0.29
$610,500
3
3
1,640
Recently Sold
39 Overlook Drive, Pawling, NY 12564
0.38
$1,186,000
3
2.5
2,441
Off Market
42 Harmony Road, Pawling, NY 12564
0.43
$442,900
2
1
1,152
Off Market
74 Harmony Hill Road, Pawling, NY 12564
0.44
$546,600
4
2
1,736
Off Market
15 Stirrup Trail, Pawling, NY 12564
0.46
$762,000
4
3.5
3,246
Off Market
33 FAWN RIDGE Drive, Pawling, NY 12564
0.48
$1,546,600
5
4.5
4,200
Off Market
2 Bridle Way, Pawling, NY 12564
0.53
$485,000
3
3.5
3,467
Recently Sold
27 Fawn Ridge Drive, Pawling, NY 12564
0.56
$773,100
4
3
3,012
Off Market

Local Information

  • Map ViewExplore the area around 18 Overlook Dr.
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1969
Lot Size
1 acre
Living Area
2,072 sqft
Price/Sqft
$269
Parking
Garage

About this House

Beautiful well maintained home with Panoramic forever views. What a great home with 4 bedrooms, 1.5 baths, HWF's on main level with updated Bathroom. Granite counters in Kitchen with Breakfast nook, Dining Room with Sliding Glass Doors that lead out to your deck that overlooks the back yard and the above ground pool. Great for entertaining. Full finished basement with new flooring, 1/2 Bath & 2 Bedrooms, spacious laundry room - excess out to 2 car garage.
18 Overlook Dr, Pawling, NY 12564 is a 4 bedroom, 2 bathroom, 2,072 sqft single-family home built in 1969. It last sold for $466,240 on Aug 22, 2022. It is currently off market. The Trulia Estimate is $557,100, with a rent estimate of $4,166/month.

Home Details for 18 Overlook Dr

Interior Features

Interior Details
BasementNumber of Rooms: 8
Heating & Cooling
Heating: Baseboard, ElectricHeating Fuel: Baseboard
Appliances & Utilities
DishwasherDryerMicrowaveRefrigeratorWasher

Exterior Features

Exterior Home Features
Roof: Asphalt, Shake ShingleExterior: Vinyl
Pool
Pool
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 1969Year Updated: 1969
Property Type / Style
Property Type: Single Family HomeArchitecture: ranch

Community

Units in Building: 1

Lot Information

Lot Area: 1 acre

Price and Tax history

DateEventPrice
Aug 22, 2022
Source: OneKey® MLS as distributed by MLS GRID #H6183337
Sold
$466,240
Aug 22, 2022
Source: BHHS broker feed #H6183337
Pending
$465,000
Jul 28, 2022
Source: Berkshire Hathaway HomeServices New England Properties #6183337
Contingent
$465,000
May 23, 2022
Source: MHMLS #407852
Pending
$465,000
May 5, 2022
Source: MHMLS #407852
Listed For Sale
$465,000

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 18 Overlook Dr

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Off Market Homes Near 18 Overlook Dr

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Frequently asked questions about 18 Overlook Dr

  • What is 18 Overlook Dr estimated to be worth?
    Trulia's estimated value for 18 Overlook Dr in Pawling, NY is $557,100.
  • What is the price history for 18 Overlook Dr?
    18 Overlook Dr in Pawling, NY last sold for $466,240 in August 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.
  • Does 18 Overlook Dr have a pool?
    Yes, 18 Overlook Dr in Pawling, NY has a pool.
  • Does 18 Overlook Dr have laundry facilities?
    Yes, 18 Overlook Dr in Pawling, NY has in-unit laundry.