Sold
Last Sold Price
3 beds2,441 sqft$461/sqft
39 Overlook Rd, Pawling, NY 12564
Single FamilyProperty Type
5.77 acresLot Size
1998Year Built
$461/sq ftPrice per sq ft
2 carsParking Spaces

Description

Get ready to feel the All-American dream come to life as you make your way up to this impeccably maintained 5.77-acre property just minutes from the bucolic Village of Pawling. As you pass the 4-stall horse barn (crafted by Old Town Barns) and riding ring to your right, you’ll find the inviting, contemporary home accompanied by the gleaming, freshly epoxy coated 2-bay garage with workshop, two overhangs, 2nd floor studio space situated around the circular drive topped off with a charming garden shed....Get ready to feel the All-American dream come to life as you make your way up to this impeccably maintained 5.77-acre property just minutes from the bucolic Village of Pawling. As you pass the 4-stall horse barn (crafted by Old Town Barns) and riding ring to your right, you’ll find the inviting, contemporary home accompanied by the gleaming, freshly epoxy coated 2-bay garage with workshop, two overhangs, 2nd floor studio space situated around the circular drive topped off with a charming garden shed. Step onto the newly re-finished hardwood wraparound porch, offering views galore, plenty of space for rocking chairs, BBQing, sunbathing & more - 'tis the season! Step inside the front door to be greeted with the living room’s cathedral, abundant windows letting in natural light, a stone fireplace with a custom wooden mantle and a dining area. The kitchen boasts custom wood cabinetry, quartz countertops, a double oven, and a propane cooktop island, creating an inviting space that inspires culinary creativity. The dining nook offers daily enjoyment, where you can relax and watch birds. The 1st floor master suite offers a spacious walk-in closet, a cozy bay window nook (perfect for reading) and a sensationally updated wet-room with a sliding barn door, double yet separate sinks, a freestanding soaking tub and a walk-in shower. Up the stairs you will find bedroom #2 & #3, each with ample closet space and stunning views (one with a balcony facing East). Between them is the second updated full bathroom with dual sinks and a step-in shower. The 2nd floor also includes a multi-use room currently being used as an office. In the basement, you will find plenty of storage space, a utility room and roughed-in plumbing for the potential of a bathroom. Here, you can enjoy the best of both worlds—peaceful, scenic surroundings and easy access to Pawling restaurants and shopping, as well as major highways and Metro-North for a convenient commute. Additional Information: HeatingFuel:Oil Above Ground,ParkingFeatures:2 Car Detached,
  • Listed by: Colleen McGrath 845.855.5550 cmcgrath@mcgrathny.com • McGrath Realty Inc
  • Listed by: Brian McGrath 845.855.5550 bmcgrath@mcgrathrealtyinc.com • McGrath Realty Inc
Listing closed: 10/01/2024 12:00 AM • Source: ONEKEY as distributed by MLS GRID, MLS#: H6303832

Recent comparable sales

Median sold price

$662,500

Avg days on market

73

Sale-to-list ratio

97.9%

Pawling, NY

9 comparable properties found

$680,000 | Undisclosed Address, Pawling, NY 12564
1

$680,000

Sold 11/15/24

3
Bedrooms
2,599
Square Feet
1.11
Acres
a kitchen with stainless steel appliances granite countertop a refrigerator a stove a sink dishwasher and white cabinets with wooden floor
2

$575,000

Sold 12/22/25

3
Bedrooms
2,318
Square Feet
0.97
Acres
a front view of house with yard and green space
3

$615,000

Sold 04/02/26

3
Bedrooms
2,254
Square Feet
0.57
Acres
a front view of a house with garden and trees
4

$662,500

Sold 12/10/24

3
Bedrooms
2,344
Square Feet
19
Acres
a front view of a house with a yard covered in snow
5

$775,000

Sold 05/01/26

3
Bedrooms
4,627
Square Feet
1.06
Acres
$645,000 | 32 Elm Street, Pawling, NY 12564
6

$645,000

Sold 06/13/25

3
Bedrooms
1,900
Square Feet
0.27
Acres
front view of house with a yard
7

$674,900

Sold 05/21/25

3
Bedrooms
2,876
Square Feet
6.9
Acres
a front view of a house with a yard
8

$550,000

Sold 07/10/26

3
Bedrooms
2,104
Square Feet
0.24
Acres
a front view of a house with garden and swimming pool
9

$697,500

Sold 01/24/26

3
Bedrooms
3,564
Square Feet
1.4
Acres

Location

Listing Courtesy of McGrath Realty Inc

Sold By Houlihan Lawrence Inc.

Add your commute

Payment Calculator

$7,424 per month

30 year fixed, 6.55% Interest

Principal and Interest

$5,718

Property Taxes

$1,705

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

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Property Information for 39 Overlook Road

Property Details
  • Taxes: $20,465 / year
  • MLS Type: Single Family
  • City/Township: Pawling
  • Architectural Style: Colonial, Farm House
  • Waterfront: No
Building Information
  • Stories: 2
  • Year Built: 1998
  • Lot Size: 5.77 AC / 251,341 SF
Summary
Location and General Information
  • Village: Pawling
  • Senior Community YN: No
  • Directions: From Route 22 - Take Route 55 W, turn right onto Overlook Drive, second right into driveway and follow up to the left for #39.
  • Property Attached: No
  • Structure Type: Detached
  • Levels: Two
  • State Or Province: NY
School Information
  • School District: Pawling
  • Elementary School: Pawling Elementary School
  • Middle Or Junior School: Pawling Middle School
  • High School District: Pawling
  • High School: Pawling High School
Rental
Rental
  • Lease Considered: No
  • Seasonal Rental: No
  • RentSpree Y/N: false
Unit Information
Unit Information
  • Building Units Total: 1
Taxes and HOA Information
Taxes and HOA Information
  • Parcel Number: 134089-6956-00-618750-0000
  • Tax Assessed Value: $285,300.00
  • Additional Fees: No
  • Association Amenities: Park
  • Tax Source: Municipality
  • Tax Year: 2023
  • Association: No
Interior and Exterior Features
Interior Features
  • Amenities: 1st Floor Bedrm, Balcony, Barn(s), Casement, Cathedral/Vaulted/High Ceiling, Ceiling Fan(s), Central Vacuum, Colonial, Deck, Double Vanity, Drilled Well, Eat in Kitchen, Farm House, First Floor Full Bath, Oven/Range, Park, Screens
  • Interior Features: Ceiling Fan(s), Central Vacuum, 1st Fl Master Bedroom, First Floor Full Bath, Cathedral Ceiling(s), Double Vanity, Eat-in Kitchen
  • Appliances: Electric Water Heater, Cooktop, Dishwasher, Dryer, Microwave, Refrigerator, Oven, Washer
  • Total Rooms: 7
  • Primary on Main: Yes
  • Basement: Full, See Remarks
  • Attic Description: Scuttle
  • Location Amenities: Balcony, 1st Fl Master Bedroom, Cathedral/Vaulted/High Ceiling, Dual Sinks, Eat in Kitchen, Scenic View, Barn(s), Deck, Casement Windows
  • Window Features: Screens, Casement
  • Inclusions: Oven/Range
  • Living Area: 2441
  • Basement: Yes
Exterior Features
  • Exterior Features: Balcony
  • Exterior Property Features: Balcony, Deck, Detached, Covered, Driveway, Screens, Casement, Near Public Transit, Near School, Near Shops, Views, Sloped
  • Elevation Certificate: No
  • Patio And Porch Features: Deck
  • Construction Materials: Block, Vinyl Siding
  • Road Responsibility: Private Maintained Road
  • Other Structures: Barn(s)
  • Horse: Yes
Lot Information
  • Lot Features: Near Public Transit, Near School, Near Shops, Views, Sloped
  • Site Features: Near Public Transit, Near School, Near Shops, Views, Sloped
Parking
  • Parking Features: Detached, Covered, Driveway
  • Parking Total: 2.00
Utilities
  • Cooling: Central Air
  • Heating: Oil, Propane, Hot Water, Steam
  • Heat Fuel Type: Oil, Propane, Hot Water, Steam
  • Sewer: Septic Tank
  • Water Source: Drilled Well
  • Utilities: Trash Collection Private
Green Features
  • Green Features: Screens, Casement, Electric Water Heater, Cooktop, Dishwasher, Dryer, Microwave, Refrigerator, Oven, Washer, Oil, Propane, Hot Water, Steam, Balcony
Virtual Tour
Agent
Payment and Rate
  • Down Payment Resource: No

Property History for 39 Overlook Road

DateEvent & SourcePriceAppreciation
Oct 1, 2024

Sold (Public Record)

Public Record #1542922542

$1,125,000
Oct 1, 2024

Sold

ONEKEY #H6303832

$1,125,000
Aug 29, 2024

Pending

ONEKEY #H6303832

DateEvent & SourcePrice
10/01/2024

Sold (Public Record)

Public Record #1542922542

$1,125,000
10/01/2024

Sold

ONEKEY #H6303832

$1,125,000
08/29/2024

Pending

ONEKEY #H6303832

For completeness, we often displays two records for one sale: the MLS record and the public record.

Public Records for 39 Overlook Road

Taxable ValueLand$36,400Additions$248,900Total$285,300
Tax Record2025$21,195 ($1,766 / month)
Home Facts
Beds3Baths2.5Total Finished SqFt3,291 SqFtAbove Grade Finished SqFt2,441 SqFtFinished Basement SqFt850 SqFtStories2Lot Size251,341 SqFtStyleSingle Family ResidenceYear Built1998Year Renovated2024ZoningR-3CountyDUTCHESSAPN134089 6956-00-618750-0000Fireplace TypeHas Fireplace

Schools near 39 Overlook Road

This home is within Pawling Central School District.
Rating
School
Type
Grades
Distance
Public - PK to 4
Public - 5 to 8
Public - 9 to 12
Private - PK to 8
Rating
School
Distance
Pawling Elementary School
PublicPK to 4

Pawling Middle School
Public5 to 8

Pawling High School
Public9 to 12

Mizzentop Day School
PrivatePK to 8

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

Similar Homes

Nearby home values

AddressSold priceBedsBathsSqftLot (Sqft)
This home: 39 Overlook Road, Pawling, NY 12564
$1,125,000
3
2,441
251,341
2,520
3
1
1,888
121,968
3
2
1,080
125,017
3
1
1,840
52,272
3
1,778
192,971

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the seller's discretion. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of McGrath Realty Inc

Based on information submitted to the MLS GRID as of 12/07/2024 03:52 PM. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Properties displayed may be listed or sold by various participants in the MLS. IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed by MLS GRID. Use of the MLS GRID data may be subject to an end user license agreement prescribed by the applicable MLS of the Member Participant, if any, and as amended from time to time.