18 Overlook Dr, Pawling, NY 12564
OFF MARKET

18 Overlook Dr
Pawling, NY 12564

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

$559,200

Trulia Estimate
as of Jun 25, 2026
Est. Refi. Payment $3,691/mo*
Refinance Your Home

$559,200

Trulia Estimate
as of Jun 25, 2026
Est. Refi. Payment $3,691/mo*
Refinance Your Home
4 Beds
1.5 Baths
2,072 sqft
(on 1 acre)

Local Information

  • Map ViewExplore the area around 18 Overlook Dr.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

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.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

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

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 History for 18 Overlook Dr

DatePriceEventSource
08/22/2022$466,240Sold
OneKey® MLS as distributed by MLS GRID #H6183337
08/22/2022$465,000PendingBHHS broker feed #H6183337
07/28/2022$465,000ContingentBerkshire Hathaway HomeServices New England Properties #6183337
05/23/2022$465,000PendingMHMLS #407852
05/05/2022$465,000Listed For SaleMHMLS #407852

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$397,800
Home facts updated by county records

Comparable Sales for 18 Overlook Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
74 Harmony Hill Road, Pawling, NY
0.44
Single-Family Home
$510,000
07/24/25
4
2
1,736
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
36 Horseshoe Path, Pawling, NY
0.92
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 18 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
    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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Homes for sale near 18 Overlook Dr

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Off Market Homes Near 18 Overlook Dr

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18 Overlook Dr, Pawling, NY 12564 is a 4 bedroom, 2 bathroom, 2,072 sqft single-family home built in 1969. This property is not currently available for sale. 18 Overlook Dr was last sold on Aug 22, 2022 for $466,240. The current Trulia Estimate for 18 Overlook Dr is $559,200.