20 Overlook Dr, Pawling, NY 12564
OFF MARKET

20 Overlook Dr
Pawling, NY 12564

  • 3 Beds
  • 2.5 Baths
  • 1,728 sqft (on 1 acre)

$559,500

Trulia Estimate
as of May 16, 2026
Est. Refi. Payment $3,636/mo*
Refinance Your Home

$559,500

Trulia Estimate
as of May 16, 2026
Est. Refi. Payment $3,636/mo*
Refinance Your Home
3 Beds
2.5 Baths
1,728 sqft
(on 1 acre)

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

What a Beautiful home with spectacular views!! Move in condition! Walk into the main floor with a great kitchen w/breakfast nook, stainless steel appliances, Dining area and Living Rm w/ Sliding Glass doors out to a deck that over looks back yard.. A great place to relax and enjoy the views. 3rd story has 3 Bedrooms - Master Bedroom has 1/2 Bath and Main Bathroom in hallway. Bottom level has a nice size family room to enjoy your family with a full bath - laundry room and another level to the basement with lots of storage and exterior excess. Generator hook up. Water Tank is 1 year old, A/C is 6 years old, Rood is 7 years old, Refrigerator is 1 1/2 years old.
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
No Info
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
No Info

Home Details for 20 Overlook Dr

Interior Features

Interior Details
BasementAttic
Heating & Cooling
Heating: Baseboard, OtherAir ConditioningCooling System: CentralHeating Fuel: Baseboard
Levels, Entrance, & Accessibility
Stories: 3Floors: Hardwood
Appliances & Utilities
DishwasherDryerRefrigeratorWasher

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Wood
Parking & Garage
GarageParking Spaces: 3Parking: Garage Detached

Property Information

Year Built
Year Built: 1965
Property Type / Style
Property Type: Single Family HomeArchitecture: split level

Community

Units in Building: 1

Lot Information

Lot Area: 1 acre

Additional Information

On Site Laundry Available

Price History for 20 Overlook Dr

DatePriceEventSource
01/29/2021$418,500Sold
OneKey® MLS as distributed by MLS GRID #H6077408
12/06/2020$429,995PendingAgent Provided
11/04/2020$429,995PriceChange
Agent Provided
10/15/2020$449,000Listed For SaleAgent Provided
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Property Tax and Assessment

Year2024
Tax
Assessment$381,700
Home facts updated by county records

Comparable Sales for 20 Overlook Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
74 Harmony Hill Road, Pawling, NY
0.46
Single-Family Home
$510,000
07/24/25
4
2
1,736
2 Bridle Way, Pawling, NY
0.56
Single-Family Home
$485,000
02/11/26
3
3.5
3,467
42 Harmony Road, Pawling, NY
0.42
Single-Family Home
$415,000
08/19/25
2
1
1,152
79 W Main Street, Pawling, NY
0.91
Single-Family Home
$615,000
04/02/26
3
2
2,254
5 Perri Lane, Pawling, NY
0.96
Single-Family Home
$697,500
01/24/26
3
2.5
2,796
36 Horseshoe Path, Pawling, NY
0.94
Single-Family Home
$775,000
05/01/26
3
2.5
4,627
4 Mane Way, Pawling, NY
0.83
Single-Family Home
$775,000
04/24/26
4
2.5
3,611
29 Cunningham Lane, Pawling, NY
0.69
Single-Family Home
$660,000
01/16/26
4
4
4,199
27 Millstream Court, Pawling, NY
0.95
Single-Family Home
$725,000
12/17/25
4
2.5
3,283
66 Fairway Drive, Pawling, NY
1.20
Single-Family Home
$535,000
03/10/26
3
2
1,490

Assigned Schools

These are the assigned schools for 20 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

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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Off Market Homes Near 20 Overlook Dr

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20 Overlook Dr, Pawling, NY 12564 is a 3 bedroom, 3 bathroom, 1,728 sqft single-family home built in 1965. This property is not currently available for sale. 20 Overlook Dr was last sold on Jan 29, 2021 for $418,500. The current Trulia Estimate for 20 Overlook Dr is $559,500.