8 Overlook Dr, Pawling, NY 12564
OFF MARKET

8 Overlook Dr
Pawling, NY 12564

  • 3 Beds
  • 1.5 Baths
  • 2,112 sqft (on 1.16 acres)

$502,900

Trulia Estimate
as of May 16, 2026
Est. Refi. Payment $3,278/mo*
Refinance Your Home

$502,900

Trulia Estimate
as of May 16, 2026
Est. Refi. Payment $3,278/mo*
Refinance Your Home
3 Beds
1.5 Baths
2,112 sqft
(on 1.16 acres)

Local Information

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

Description

Expanded Raised Ranch that can fit the Whole Family! Sunny Family Room off the Eat-in-Kitchen plus a formal Dining Room and an Over-sized Living Room. There are hardwoods floors throughout most of the home. Besides the 2 car garage there is a 12 x 26 Storage Area with an Over Head Door. The home sits on a great lot on a quiet street which is convenient to the Metro North Railroad and Major Highways. Convenient to Lakeside Park with a 36 Acre Lake and Dutchess Golf Course!
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 & Cooling
HOA
None
Price/Sqft
No Info
Listed
No Info

Home Details for 8 Overlook Dr

Interior Features

Interior Details
BasementNumber of Rooms: 10Types of Rooms: Dining Room, Office
Heating & Cooling
Heating: Baseboard, ElectricAir ConditioningCooling System: WallHeating Fuel: Baseboard
Levels, Entrance, & Accessibility
Stories: 2Floors: Hardwood
Appliances & Utilities
DishwasherDryerMicrowaveRefrigeratorWasher

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Vinyl
Pool
Pool
Parking & Garage
GarageParking Space: 1Parking: Garage Attached

Property Information

Year Built
Year Built: 1971Year Updated: 1985
Property Type / Style
Property Type: Single Family HomeArchitecture: Ranch / Rambler

Lot Information

Lot Area: 1.16 acres

Price History for 8 Overlook Dr

DatePriceEventSource
06/08/2016$255,000Sold
OneKey® MLS as distributed by MLS GRID #H4605870
03/29/2016$269,900PendingAgent Provided
02/17/2016$269,900Listed For SaleAgent Provided
01/01/2016$269,000ListingRemovedAgent Provided
11/19/2015$269,000PriceChange
Agent Provided
08/14/2015$279,000PriceChange
Agent Provided
07/08/2015$290,000PriceChange
Agent Provided
05/21/2015$299,000Listed For SaleAgent Provided
03/20/2014$299,000ListingRemovedAgent Provided
07/23/2013$299,000PriceChange
Agent Provided
05/11/2013$310,000Listed For SaleAgent Provided
04/21/2012$339,000ListingRemovedAgent Provided
10/17/2011$339,000PriceChange
Agent Provided
12/20/2010$354,900Listed For SaleAgent Provided
11/01/2010$354,900ListingRemovedAgent Provided
10/22/2010$354,900Listed For SaleAgent Provided
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Property Tax and Assessment

Year2024
Tax
Assessment$417,700
Home facts updated by county records

Comparable Sales for 8 Overlook Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
74 Harmony Hill Road, Pawling, NY
0.34
Single-Family Home
$510,000
07/24/25
4
2
1,736
2 Bridle Way, Pawling, NY
0.32
Single-Family Home
$485,000
02/11/26
3
3.5
3,467
42 Harmony Road, Pawling, NY
0.56
Single-Family Home
$415,000
08/19/25
2
1
1,152
36 Horseshoe Path, Pawling, NY
0.75
Single-Family Home
$775,000
05/01/26
3
2.5
4,627
5 Perri Lane, Pawling, NY
0.90
Single-Family Home
$697,500
01/24/26
3
2.5
2,796
4 Mane Way, Pawling, NY
0.69
Single-Family Home
$775,000
04/24/26
4
2.5
3,611
14 Old Route 55, Pawling, NY
1.15
Single-Family Home
$269,950
04/15/26
3
1
1,653
29 Cunningham Lane, Pawling, NY
0.71
Single-Family Home
$660,000
01/16/26
4
4
4,199
79 W Main Street, Pawling, NY
1.14
Single-Family Home
$615,000
04/02/26
3
2
2,254
27 Millstream Court, Pawling, NY
0.95
Single-Family Home
$725,000
12/17/25
4
2.5
3,283

Assigned Schools

These are the assigned schools for 8 Overlook Dr.
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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 8 Overlook Dr

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8 Overlook Dr, Pawling, NY 12564 is a 3 bedroom, 2 bathroom, 2,112 sqft single-family home built in 1971. This property is not currently available for sale. 8 Overlook Dr was last sold on Jun 8, 2016 for $255,000. The current Trulia Estimate for 8 Overlook Dr is $502,900.