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

9 Overlook Dr
Pawling, NY 12564

  • 3 Beds
  • 1 Bath
  • 1,632 sqft (on 2.70 acres)

$464,900

Trulia Estimate
as of Jul 4, 2026
Est. Refi. Payment $3,133/mo*
Refinance Your Home

$464,900

Trulia Estimate
as of Jul 4, 2026
Est. Refi. Payment $3,133/mo*
Refinance Your Home
3 Beds
1 Bath
1,632 sqft
(on 2.70 acres)

Local Information

  • Map ViewExplore the area around 9 Overlook Dr.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

Think Unique! Wonderful starter home that needs a little TLC, property is on private 2.7 acres. A house you can make your own. Being sold as is. 3 Bedrooms, one bath, unfinished basement that can be made into family room. Generator hook up. Nice neighborhood, close to Metro North Train, main roads and the Village of Pawling.
9 Overlook Dr, Pawling, NY 12564 is a 3 bedroom, 1 bathroom, 1,632 sqft single-family home built in 1967. It last sold for $185,000 on Sep 4, 2015. It is currently off market. The Trulia Estimate is $464,900, with a rent estimate of $3,438/month.

Home Highlights

Parking
Garage
Outdoor
Pool
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 9 Overlook Dr

Interior Features

Heating & Cooling
Heating: Other, OilAir ConditioningCooling System: CentralHeating Fuel: Other
Levels, Entrance, & Accessibility
Stories: 1
Interior Details
Number of Rooms: 6Ceiling Fan
Appliances & Utilities
DryerRefrigeratorWasher

Property Information

Year Built
Year Built: 1967
Property Type / Style
Property Type: Single Family HomeArchitecture: ranch

Exterior Features

Exterior Home Features
Exterior: Wood
Pool
Pool
Parking & Garage
GarageParking: Garage Attached

Community

Units in Building: 1

Lot Information

Lot Area: 2.70 acres

Price History for 9 Overlook Dr

DatePriceEventSource
09/04/2015$185,000Sold
OneKey® MLS as distributed by MLS GRID #H4515877
05/14/2015$210,000ListingRemovedAgent Provided
05/14/2015$210,000PendingAgent Provided
04/17/2015$210,000Listed For SaleAgent Provided

Market trends in Pawling

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
24
3MoM
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Property Tax and Assessment

Year2025
Tax
Assessment$424,200
Home facts updated by county records

Comparable Sales for 9 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
74 Harmony Hill Road, Pawling, NY
0.32
Single-Family Home
$510,000
07/24/25
4
2
1,736
42 Harmony Road, Pawling, NY
0.53
Single-Family Home
$415,000
08/19/25
2
1
1,152
14 Old Route 55, Pawling, NY
1.02
Single-Family Home
$269,950
04/15/26
3
1
1,653
2 Bridle Way, Pawling, NY
0.41
Single-Family Home
$485,000
02/11/26
3
3.5
3,467
5 Perri Lane, Pawling, NY
0.86
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
79 W Main Street, Pawling, NY
0.99
Single-Family Home
$615,000
04/02/26
3
2
2,254
27 Millstream Court, Pawling, NY
0.88
Single-Family Home
$725,000
12/17/25
4
2.5
3,283
36 Horseshoe Path, Pawling, NY
0.80
Single-Family Home
$775,000
05/01/26
3
2.5
4,627

Nearby homes

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Assigned Schools

These are the assigned schools for 9 Overlook Dr.
View nearby schools on GreatSchools
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
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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
    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 9 Overlook Dr

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Off Market Homes Near 9 Overlook Dr

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