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

4 Overlook Dr
Pawling, NY 12564

  • 3 Beds
  • 2 Baths
  • 1,748 sqft (on 1.24 acres)

$497,600

Trulia Estimate
as of Aug 11, 2026
Est. Refi. Payment $3,340/mo*
Refinance Your Home

$497,600

Trulia Estimate
as of Aug 11, 2026
Est. Refi. Payment $3,340/mo*
Refinance Your Home
3 Beds
2 Baths
1,748 sqft
(on 1.24 acres)

Local Information

  • Map ViewExplore the area around 4 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
1966
Lot Size
1.24 acres
Living Area
1,748 sqft
Price/Sqft
$285
Parking
Garage

About this House

Beautiful Property, Great Location, Private Setting! 5 minutes or less to the picturesque Village of Pawling, which offers Metro-North (Harlem Line), Lakeside Park w/beach, Dutcher Golf Course, quaint shops, library, cafe's, bakeries, pubs, great restaurants & deli's. This spacious home offers solid Hardwood Floors, Living Rm with picture window, open Dining Rm with slider to large deck. Walk-Out lower level features a Family Rm with Fireplace plus a home office/den. The upper level consists of a Main Bedroom with a walk-in closet and half bath. There are two additional Bedrooms and a full Hall Bath. The house needs some work, which is reflected in the price. (Just imagine the difference a new kitchen and gleaming refinished hardwood floors would make!) *Additional activities include Daryl's House (Daryl Hall) Restaurant & Music Club, Thunder Ridge Ski Center, World Gym, Pickleball courts at Lakeside Park, more! Hike the Appalachian Trail and the Oblong Reserve. Something for everyone!
4 Overlook Dr, Pawling, NY 12564 is a 3 bedroom, 3 bathroom, 1,748 sqft single-family home built in 1966. It last sold for $338,000 on May 31, 2022. It is currently off market. The Trulia Estimate is $497,600, with a rent estimate of $3,943/month.

Home Details for 4 Overlook Dr

Interior Features

Interior Details
BasementNumber of Rooms: 7
Heating & Cooling
Heating: Baseboard, ElectricHeating Fuel: Baseboard
Levels, Entrance, & Accessibility
Stories: 1Floors: Hardwood
Appliances & Utilities
DishwasherMicrowaveRefrigerator
Fireplace & Spa
Fireplace

Property Information

Year Built
Year Built: 1966Year Updated: 1966
Property Type / Style
Property Type: Single Family HomeArchitecture: split level

Exterior Features

Exterior Home Features
DeckExterior: Brick
Parking & Garage
GarageParking: Garage Attached

Community

Units in Building: 1

Lot Information

Lot Area: 1.24 acres

Price History for 4 Overlook Dr

DatePriceEventSource
05/31/2022$338,000Sold
OneKey® MLS as distributed by MLS GRID #H6141543
03/08/2022$339,000PendingMHMLS #404459
02/24/2022$339,000PendingToActiveOneKey® MLS as distributed by MLS GRID #H6141543
11/29/2021$339,000PendingOneKey® MLS as distributed by MLS GRID #H6141543
10/29/2021$339,000PriceChange
OneKey® MLS as distributed by MLS GRID #H6141543
10/21/2021$349,000Listed For SaleOneKey® MLS as distributed by MLS GRID #H6141543
07/21/2006$890,000Sold
N/A
05/02/2000$160,000Sold
N/A

Market trends in Pawling

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
27
3MoM
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Property Tax and Assessment

Year2025
Tax
Assessment$365,800
Home facts updated by county records

Comparable Sales for 4 Overlook Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
85 Harmony Hill Road, Pawling, NY
0.17
Single-Family Home
$610,500
06/25/26
3
3
1,640
2 Bridle Way, Pawling, NY
0.35
Single-Family Home
$485,000
02/11/26
3
3.5
3,467
24 Overlook Drive, Pawling, NY
0.31
Single-Family Home
$735,000
07/21/26
3
3.5
3,175
42 Harmony Road, Pawling, NY
0.53
Single-Family Home
$415,000
08/19/25
2
1
1,152
5 Perri Lane, Pawling, NY
0.92
Single-Family Home
$697,500
01/24/26
3
2.5
2,796
36 Horseshoe Path, Pawling, NY
0.78
Single-Family Home
$775,000
05/01/26
3
2.5
4,627
4 Mane Way, Pawling, NY
0.71
Single-Family Home
$775,000
04/24/26
4
2.5
3,611
29 Cunningham Lane, Pawling, NY
0.72
Single-Family Home
$660,000
01/16/26
4
4
4,199
79 W Main Street, Pawling, NY
1.13
Single-Family Home
$615,000
04/02/26
3
2
2,254
27 Millstream Court, Pawling, NY
0.96
Single-Family Home
$725,000
12/17/25
4
2.5
3,283

Nearby homes

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Assigned Schools

These are the assigned schools for 4 Overlook Dr.
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The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

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

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Apartments for Rent

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Homes for sale near 4 Overlook Dr

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Off Market Homes Near 4 Overlook Dr

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Frequently asked questions about 4 Overlook Dr

  • What is 4 Overlook Dr estimated to be worth?
    Trulia's estimated value for 4 Overlook Dr in Pawling, NY is $497,600.
  • What is the price history for 4 Overlook Dr?
    4 Overlook Dr in Pawling, NY last sold for $338,000 in May 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.
  • How big is the lot at 4 Overlook Dr?
    The lot at 4 Overlook Dr in Pawling, NY is about 1.2 acres.
  • Does 4 Overlook Dr have a garage?
    Yes, 4 Overlook Dr in Pawling, NY has a garage.