15 Overlook Dr, Pawling, NY 12564
OFF MARKET

15 Overlook Dr
Pawling, NY 12564

  • 3 Beds
  • 2 Baths
  • 3,000 sqft (on 1.49 acres)

$483,300

Trulia Estimate
as of Aug 22, 2026
Est. Refi. Payment $3,289/mo*
Refinance Your Home

$483,300

Trulia Estimate
as of Aug 22, 2026
Est. Refi. Payment $3,289/mo*
Refinance Your Home
3 Beds
2 Baths
3,000 sqft
(on 1.49 acres)

Home Value

Trulia Estimate
$483K
Since last month
Decreased$500 (-0.1%)
Since last year
Increased$10K (+2%)
Since last sale
Increased$278K (+135.6%)
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 +87% in the last 10 years
MonthEstimated value
2026
August 2026$483K
July 2026$483K
June 2026$487K
May 2026$481K
April 2026$464K
March 2026$453K
February 2026$446K
January 2026$455K
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
0.15
Single-Family Home
$735,000
07/21/26
3
3.5
3,175
85 Harmony Hill Road, Pawling, NY
0.21
Single-Family Home
$610,500
06/25/26
3
3
1,640
2 Bridle Way, Pawling, NY
0.47
Single-Family Home
$485,000
02/11/26
3
3.5
3,467
5 Perri Lane, Pawling, NY
0.87
Single-Family Home
$697,500
01/24/26
3
2.5
2,796
29 Cunningham Lane, Pawling, NY
0.62
Single-Family Home
$660,000
01/16/26
4
4
4,199
27 Millstream Court, Pawling, NY
0.87
Single-Family Home
$725,000
12/17/25
4
2.5
3,283
36 Horseshoe Path, Pawling, NY
0.84
Single-Family Home
$775,000
05/01/26
3
2.5
4,627
4 Mane Way, Pawling, NY
0.73
Single-Family Home
$775,000
04/24/26
4
2.5
3,611
79 W Main Street, Pawling, NY
0.94
Single-Family Home
$615,000
04/02/26
3
2
2,254
14 Old Route 55, Pawling, NY
0.99
Single-Family Home
$269,950
04/15/26
3
1
1,653

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
21 Overlook Drive, Pawling, NY 12564
0.13
$699,000
3
2.5
1,460
For Sale
24 Overlook Drive, Pawling, NY 12564
0.15
$735,000
3
3.5
3,175
Recently Sold
6 Overlook Dr, Pawling, NY 12564
0.16
$729,999
3
3
2,659
For Sale
3846 Route 55, Pawling, NY 12564
0.19
$639,000
4
3.5
1,696
For Sale
85 Harmony Hill Road, Pawling, NY 12564
0.21
$610,500
3
3
1,640
Recently Sold
74 Harmony Hill Road, Pawling, NY 12564
0.35
$548,600
4
2
1,736
Off Market
15 Stirrup Trail, Pawling, NY 12564
0.38
$763,200
4
3.5
3,246
Off Market
39 Overlook Drive, Pawling, NY 12564
0.42
$1,186,000
3
2.5
2,441
Off Market
2 Bridle Way, Pawling, NY 12564
0.47
$485,000
3
3.5
3,467
Recently Sold
7 Anderson Way, Pawling, NY 12564
0.48
$563,800
4
1.5
1,919
Off Market
42 Harmony Road, Pawling, NY 12564
0.51
$444,400
2
1
1,152
Off Market
10 Canter Circle, Pawling, NY 12564
0.53
$632,000
3
2.5
2,004
Off Market

Local Information

  • Map ViewExplore the area around 15 Overlook Dr.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1967
Lot Size
1.49 acres
Living Area
3,000 sqft
Price/Sqft
$161

About this House

Put all your own touches on this wonderful, bright floor plan. Private backyard, view of the valley below from the sun room, living room, and kitchen. Minutes to the lovely village of Pawling, Metro North Railroad, schools, parks and shopping.
15 Overlook Dr, Pawling, NY 12564 is a 3 bedroom, 2 bathroom, 3,000 sqft single-family home built in 1967. It last sold for $205,000 on Jan 27, 2012. It is currently off market. The Trulia Estimate is $483,300, with a rent estimate of $4,266/month.

Home Details for 15 Overlook Dr

Interior Features

Interior Details
BasementAdditional StorageAtticNumber of Rooms: 6Types of Rooms: Walk In Closet, Dining Room, Laundry Room, Master Bath, Office, Recreation Room, Sun RoomStorage
Heating & Cooling
Heating: Baseboard, Stove, Oil, SolarAir ConditioningCooling System: SolarHeating Fuel: Baseboard
Levels, Entrance, & Accessibility
Stories: 2Floors: Tile, Hardwood
Appliances & Utilities
DishwasherMicrowaveRefrigeratorWasher
Security
Security System

Exterior Features

Exterior Home Features
Roof: Shake ShingleDeckExterior: Stucco, MetalGardenLawnPatioPorch
Pool
Pool
Parking & Garage
Parking: Carport

Property Information

Year Built
Year Built: 1967
Property Type / Style
Property Type: Single Family HomeArchitecture: Ranch / Rambler

Community

Units in Building: 1

Lot Information

Lot Area: 1.49 acres

Price and Tax history

DateEventPrice
Jan 27, 2012
Source: N/A
Sold
$205,000
Oct 27, 2011
Source: N/A
Sold
$202,000
Jun 15, 2011
Source: Agent Provided
PriceChange
$225,000
Price decreased by 10%
Apr 20, 2011
Source: Agent Provided
PriceChange
$250,000
Price decreased by 12%
Sep 21, 2010
Source: Agent Provided
PriceChange
$285,000
Price decreased by 12%

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

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 15 Overlook Dr

  • What is 15 Overlook Dr estimated to be worth?
    Trulia's estimated value for 15 Overlook Dr in Pawling, NY is $483,300.
  • What is the price history for 15 Overlook Dr?
    15 Overlook Dr in Pawling, NY last sold for $205,000 in January 2012.
  • 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 15 Overlook Dr have air conditioning?
    Yes, 15 Overlook Dr in Pawling, NY has air conditioning.
  • Does 15 Overlook Dr have a pool?
    Yes, 15 Overlook Dr in Pawling, NY has a pool.

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