14 Overlook Dr, Pawling, NY 12564
OFF MARKET

14 Overlook Dr
Pawling, NY 12564

  • 3 Beds
  • 3 Baths
  • 2,670 sqft (on 2.60 acres)

$602,300

Trulia Estimate
as of Aug 15, 2026
Est. Refi. Payment $4,062/mo*
Refinance Your Home

$602,300

Trulia Estimate
as of Aug 15, 2026
Est. Refi. Payment $4,062/mo*
Refinance Your Home
3 Beds
3 Baths
2,670 sqft
(on 2.60 acres)

Home Value

Trulia Estimate
$602K
Since last month
Decreased$600 (-0.1%)
Since last year
Increased$54K (+9.8%)
Since last sale
Increased$434K (+255.4%)
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 +140% in the last 10 years
MonthEstimated value
2026
August 2026$604K
July 2026$601K
June 2026$605K
May 2026$586K
April 2026$574K
March 2026$576K
February 2026$566K
January 2026$578K
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
96 Charles Colman Blvd, Pawling, NY
1.43
Multi-Family Home
$350,000
02/20/26
5
2
1,991
322 Old Route 22, Pawling, NY
2.33
Multi-Family Home
$580,000
05/28/26
4
2
1,950
9 Elm St, Pawling, NY
1.37
Multi-Family Home
$375,000
06/08/26
-
1,776
16 Route 292 #14, Patterson, NY
2.87
Multi-Family Home
$685,000
12/31/25
6
3
4,108
18 Equestrian Way, Poughquag, NY
5.52
Multi-Family Home
$580,000
02/13/26
3
3
2,016
15 Meadow Ridge Road, Brewster, NY
6.64
Multi-Family Home
$641,000
11/14/25
6
4
3,000
545-547 Fair Street, Carmel, NY
7.00
Multi-Family Home
$890,000
10/09/25
5
5
4,236
233-235 Haviland Drive, Patterson, NY
7.22
Multi-Family Home
$765,000
07/15/26
5
3
2,976

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
3846 Route 55, Pawling, NY 12564
0.11
$639,000
4
2.5
1,696
For Sale
6 Overlook Dr, Pawling, NY 12564
0.11
$729,999
3
3
2,659
For Sale
24 Overlook Drive, Pawling, NY 12564
0.17
$735,000
3
3.5
3,175
Recently Sold
21 Overlook Drive, Pawling, NY 12564
0.18
$699,000
3
2.5
1,460
For Sale
85 Harmony Hill Road, Pawling, NY 12564
0.24
$610,500
3
3
1,640
Recently Sold
74 Harmony Hill Road, Pawling, NY 12564
0.41
$546,600
4
2
1,736
Off Market
15 Stirrup Trail, Pawling, NY 12564
0.41
$762,000
4
3.5
3,246
Off Market
39 Overlook Drive, Pawling, NY 12564
0.45
$1,186,000
3
2.5
2,441
Off Market
42 Harmony Road, Pawling, NY 12564
0.44
$442,900
2
1
1,152
Off Market
2 Bridle Way, Pawling, NY 12564
0.47
$485,000
3
3.5
3,467
Recently Sold
33 FAWN RIDGE Drive, Pawling, NY 12564
0.49
$1,546,600
5
4.5
4,200
Off Market
7 Anderson Way, Pawling, NY 12564
0.56
$557,200
4
1.5
1,919
Off Market

Local Information

  • Map ViewExplore the area around 14 Overlook Dr.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Multi-Family
Year Built
1966
Lot Size
2.6 acres
Living Area
2,670 sqft
Price/Sqft
$226
Parking
Garage

About this House

This multi-family home is located at 14 Overlook Dr, Pawling, NY. 14 Overlook Dr is in Pawling, NY and in ZIP code 12564. This property has 3 bedrooms, 3 bathrooms and approximately 2,670 sqft of floor space. This property has a lot size of 2.60 acres and was built in 1966.
14 Overlook Dr, Pawling, NY 12564 is a 3 bedroom, 3 bathroom, 2,670 sqft multi-family built in 1966. It last sold for $170,000 on Jan 6, 1997. It is currently off market. The Trulia Estimate is $602,300, with a rent estimate of $2,900/month.

Home Details for 14 Overlook Dr

Interior Features

Interior Details
Basement
Heating & Cooling
Heating: Other, OtherAir ConditioningCooling System: CentralHeating Fuel: Other
Levels, Entrance, & Accessibility
Stories: 1
Fireplace & Spa
Fireplace

Property Information

Year Built
Year Built: 1966
Property Type / Style
Property Type: Multi FamilyArchitecture: ranch

Exterior Features

Exterior Home Features
Exterior: Wood
Parking & Garage
GarageParking Spaces: 2Parking: Garage Attached, Garage Detached

Community

Units in Building: 1

Lot Information

Lot Area: 2.60 acres

Price and Tax history

DateEventPrice
Jan 6, 1997
Source: N/A
Sold
$170,000

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
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  • Francesca T. B.
    "I’ve lived here for 20 years. You can walk unafraid. Restaurants, small store, library all close by. "
    0
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  • 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. "
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  • 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
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  • 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. "
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Apartments for Rent

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Homes for sale near 14 Overlook Dr

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Off Market Homes Near 14 Overlook Dr

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Frequently asked questions about 14 Overlook Dr

  • What is 14 Overlook Dr estimated to be worth?
    Trulia's estimated value for 14 Overlook Dr in Pawling, NY is $602,300.
  • What is the price history for 14 Overlook Dr?
    14 Overlook Dr in Pawling, NY last sold for $170,000 in January 1997.
  • 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 14 Overlook Dr have air conditioning?
    Yes, 14 Overlook Dr in Pawling, NY has air conditioning.