161 Whalesback Rd

Red Hook, NY 12571

$1,700,000
Last Sold Price
5
Beds
5,490 Sq. Ft.
$310 / Sq. Ft.
5,490
Sq. Ft.
$310
per Sq. Ft.
Closed 9/8/25
Closed 9/8/25
Very private on 15+ acres

Description

Don’t miss this rare opportunity to own a breathtaking, fully renovated 5,500 sq ft converted barn in the heart of the Hudson Valley. Nestled on 15 private, picturesque acres in the safety and tranquility of Red Hook, NY, this extraordinary 5-bedroom, 4.5-bathroom home seamlessly blends historic charm with modern luxury. Originally built in 1900, the barn has been thoughtfully transformed to preserve its character—soaring ceilings, exposed beams, and expansive open spaces—while offering every contemporary...Don’t miss this rare opportunity to own a breathtaking, fully renovated 5,500 sq ft converted barn in the heart of the Hudson Valley. Nestled on 15 private, picturesque acres in the safety and tranquility of Red Hook, NY, this extraordinary 5-bedroom, 4.5-bathroom home seamlessly blends historic charm with modern luxury. Originally built in 1900, the barn has been thoughtfully transformed to preserve its character—soaring ceilings, exposed beams, and expansive open spaces—while offering every contemporary convenience. The home features a gracious open floor plan, oversized rooms, and a stunning in-ground pool with a flagstone patio, perfect for entertaining or peaceful country living. Designed for both relaxation and productivity, the home also includes plenty of room for an office, a spacious game/family room, gym, studio, or guest space. Whether you're working remotely, hosting family and friends, or simply unwinding, this home offers space for every lifestyle. Set in the center of equestrian country, this location offers unrivaled access to world-class destinations including Mashomack Preserve Club, Tamarack Preserve, and several notable new clubs emerging in the area. Families will appreciate proximity to top-tier public and private schools, a variety of excellent children’s camps, and some of the best skiing in the region. The vibrant local culture is further enriched by nearby Bard and Vassar Colleges, bringing world-class arts and events to your doorstep. Conveniently located just minutes from the charming villages of Red Hook and Rhinebeck, 20 minutes to Hudson and Pine Plains, 30 minutes to Millbrook, and less than an hour to the Berkshires. You're also just 10 minutes from the Amtrak station with direct service to NYC, and under two hours away by car. This is more than a home—it’s a lifestyle.
  1. Listed by Ann C. Stettner • Neil Charles Real Estate, LLC
    P: (845)-266-8374 C: (917)-660-3266 ann@neilcharlesrealestate.com

Property Details for 161 Whalesback Road

City/Township
Red Hook
View
Open, Park/Greenbelt
Architectural Style
Other, Traditional
Garage Spaces
4.00
Waterfront
No
LISTING UPDATED: 09/08/2025 05:20 PM

Property Details for 161 Whalesback Road

StatusClosed
MLS #885582
Days on Market23
Taxes$20,586 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeSingle Family
Year Built1900
Lot Size15.10 AC / 657,756 SF
CountyDutchess County

Location

Listing Courtesy of Neil Charles Real Estate, LLC

Sold By The Kinderhook Group, Inc.

Add your commute

Building Information for 161 Whalesback Road

Stories-Year Built1900Building Size-Lot Size15.10 AC / 657,756 SF

Payment Calculator

$10,001 per month

30 year fixed, 6.15% Interest

Principal and Interest

$8,286

Property Taxes

$1,716

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 161 Whalesback Road

Summary
Location and General Information
  • Senior Community YN: No
  • Directions: From Stoplight in Red Hook take West Market St (Route 199) and take right on Linden Avenue (CR-78). Follow Linden 1.8 miles to left on Whalesback. Go 0.7 miles to 161 on the right
  • Property Attached: No
  • Structure Type: false
  • Levels: Two
  • Property Condition: Updated/Remodeled
  • State Or Province: NY
School Information
  • School District: Red Hook
  • Elementary School District: Red Hook
  • Elementary School: Mill Road-Primary Grades
  • Middle Or Junior School District: Red Hook
  • Middle Or Junior School: Linden Avenue Middle School
  • High School District: Red Hook
  • High School: Red Hook Senior High School
Rental
Rental
  • Lease Considered: No
Unit Information
Unit Information
  • Building Units Total: 1
Room Information
Room 1 Information
  • Room Level: First
  • Room Type: Dining Room
  • RoomDescription 1: Wood floors, light-filled, high ceiling, open floor plan to kitchen
Room 2 Information
  • Room Level: First
  • Room Type: Kitchen
  • Room Description: Light-filled, counter seating, center Island, new flooring with radiant heat, open floor plan
Room 3 Information
  • Room Level: First
  • Room Type: Living Room
  • Room Description: Large, light-filled living room with fireplace, high ceiling, wood floors and open floor plan
Room 4 Information
  • Room Level: First
  • Room Type: Family Room
  • Room Description: Wood floors, high ceiling, currently set up as game room with ping pong table
Room 5 Information
  • Room Level: First
  • Room Type: Laundry
  • Room Description: Large laundry room
Room 6 Information
  • Room Level: First
  • Room Type: Office
Room 7 Information
  • Room Level: First
  • Room Type: Bedroom 1
  • Room Description: Currently set up as large bedroom suite with bathroom en suite and radiant heat throughout, but could be gym, family room, media room etc
Room 8 Information
  • Room Level: First
  • Room Type: Bathroom 1
  • Room Description: Modern full bathroom on main floor in bonus suite
Room 9 Information
  • Room Level: Second
  • Room Type: Primary Bedroom
  • Room Description: Stunning, light-filled large bedroom with radiant heat, large dressing room/closet and primary bath
Room 10 Information
  • Room Level: Second
  • Room Type: Primary Bathroom
  • Room Description: Double sinks, large soaking tub, large stall shower, custom make up vanity, radiant heat
Room 11 Information
  • Room Level: Second
  • Room Type: Bedroom 3
  • Room Description: Large bedroom with wood floors, and bathroom en suite
Room 12 Information
  • Room Level: Second
  • Room Type: Bedroom 4
  • Room Description: Light-filled corner bedroom with new large bath en suite
Room 13 Information
  • Room Level: Second
  • Room Type: Bedroom 5
  • Room Description: Nice bedroom with bathroom en suite
Room 14 Information
  • Room Level: Second
  • Room Type: Office
Room 15 Information
  • Room Level: First
  • Room Type: Bathroom 2
Room 16 Information
  • Room Level: Second
  • Room Type: Bathroom 3
Room 17 Information
  • Room Level: Second
  • Room Type: Bathroom 4
Room 18 Information
  • Room Level: Second
  • Room Type: Bathroom 5
Taxes and HOA Information
Taxes and HOA Information
  • Parcel Number: 134889-6273-00-085713-0000
  • Tax Assessed Value: $1,005,500.00
  • Additional Fees: No
  • Association: No
Interior and Exterior Features
Interior Features
  • Amenities: 1st Floor Bedrm, Beamed Ceilings, Carpet, Cathedral/Vaulted/High Ceiling, Ceiling Fan(s), Chefs Kitchen, Double Vanity, Eat in Kitchen, Entrance Foyer, First Floor Full Bath, Formal Dining, Garage(s), Garden, Hardwood Floors As Seen, High Ceilings, High Speed Internet, His and Hers Closets, In Ground, Kitchen Island, Laundry Room, Living Room, Open, Open Floorplan, Original Details, Other, Pantry, Park/Greenbelt, Patio, Porch, Primary Bathroom, Screened, Security System, Shed(s), Smoke Detector(s), Soaking Tub, Stone Counters, Tile, Traditional, Walk In Closet, Well, Wood Burning
  • Interior Features: First Floor Bedroom, First Floor Full Bath, Beamed Ceilings, Cathedral Ceiling(s), Ceiling Fan(s), Chefs Kitchen, Double Vanity, Eat-in Kitchen, Entrance Foyer, Formal Dining, High Ceilings, High Speed Internet, His and Hers Closets, Kitchen Island, Open Floorplan, Original Details, Pantry, Primary Bathroom, 1st Fl Master Bedroom, Soaking Tub, Stone Counters, Walk-In Closet(s)
  • Appliances: Cooktop, Dishwasher, Dryer, Oven, Refrigerator, Stainless Steel Appliance(s), Washer
  • Total Rooms: 13
  • Primary on Main: Yes
  • Basement: Partial, Storage Space, Unfinished, Walk-Out Access
  • Attic Description: Partial,Pull Stairs,Unfinished
  • Fireplace: Yes
  • Fireplaces Total: 1
  • Fireplace Features: Living Room, Wood Burning
  • Location Amenities: Other/See Remarks, Stainless Steel Appliances, Walk Out Basement, Hardwood Floors As Seen, 1st Fl Master Bedroom, Cathedral/Vaulted/High Ceiling, Chef's Kitchen, Dual Sinks, Eat in Kitchen, Entry Foyer, Foyer, Formal Dining Room, High Ceilings, High Speed Internet, Island Kitchen, Original Details, Pantry, Soacking Tub, Walk In Closet, Garden, Privacy, Scenic View, Patio, Porch, In Ground Pool, Security System, Park View
  • Laundry Features: Laundry Room
  • Security Features: Security System,Smoke Detector(s)
  • Spa: No
  • Flooring: Carpet, Hardwood, Tile
  • Living Area: 5,490.00
  • Foundation Details: Pillar/Post/Pier, Slab, Stone
  • Basement: Yes
Exterior Features
  • Exterior Features: Garden
  • Exterior Property Features: Garden, In Ground, Patio, Porch, Screened, Driveway, Garage, Off Street, Private, Back Yard, Cleared, Front Yard, Landscaped, Level, Near School, Near Shops, Part Wooded, Views
  • Elevation Certificate: No
  • Patio And Porch Features: Patio,Porch,Screened
  • Construction Materials: Blown-In Insulation, HardiPlank Type
  • Other Structures: Garage(s),Shed(s)
  • Pool Private: Yes
  • Pool Features: In Ground
  • Pool Details: In Ground
Lot Information
  • Lot Features: Back Yard, Cleared, Front Yard, Garden, Landscaped, Level, Near School, Near Shops, Part Wooded, Private, Views
  • Additional Parcel: No
  • Site Features: Back Yard, Cleared, Front Yard, Garden, Landscaped, Level, Near School, Near Shops, Part Wooded, Private, Views
  • Building Area Units: Square Feet
Parking
  • Parking Features: Driveway, Garage, Off Street, Private
  • Parking Total: 8.00
  • Garage: Yes
  • Carport: No
Utilities
  • Cooling: Central Air
  • Heating: Baseboard, Hot Water, Propane, Radiant, Radiant Floor
  • Heat Fuel Type: Baseboard, Hot Water, Propane, Radiant, Radiant Floor
  • Number Of Heating Zones: 6
  • Sewer: Septic Tank
  • Water Source: Well
  • Utilities: Cable Available, Electricity Available, Phone Available, Propane, Sewer Connected, Trash Collection Private, Water Connected
Green Features
  • Green Features: Cooktop, Dishwasher, Dryer, Oven, Refrigerator, Stainless Steel Appliance(s), Washer, Baseboard, Hot Water, Propane, Radiant, Radiant Floor, Garden, In Ground
Agent
Payment and Rate
  • Down Payment Resource: No

Property History for 161 Whalesback Road

DateEvent & SourcePriceAppreciation
Sep 8, 2025

Sold

ONEKEY #885582

$1,700,000—
Jul 30, 2025

Pending

ONEKEY #885582

—
Jul 8, 2025

Listed (Active)

ONEKEY #885582

$1,799,000—
Mar 15, 2006

Sold (Public Record)

Public Record #277490369

$630,000—
Mar 15, 2006

Sold (Public Record)

Public Record #277490369

$630,000—
Mar 15, 2006

Sold

MHMLS #235772

$630,000—
Mar 15, 2006

Sold

HVCR MLS #61024

$630,000—
Mar 14, 2006

Pending

MHMLS #235772

—
Feb 26, 2006

Pending

HVCR MLS #61024

—
Sep 18, 2005

Listed (Active)

HVCR MLS #61024

$689,000—
Sep 18, 2005

Listed (Active)

MHMLS #235772

$659,000—
Oct 29, 2001

Sold

MHMLS #202687

$411,500—
Oct 8, 2001

Pending

MHMLS #202687

—
Mar 20, 2001

Listed (Active)

MHMLS #202687

$435,000—
DateEvent & SourcePrice
09/08/2025

Sold

ONEKEY #885582

$1,700,000
07/30/2025

Pending

ONEKEY #885582

—
07/08/2025

Listed (Active)

ONEKEY #885582

$1,799,000
03/15/2006

Sold (Public Record)

Public Record #277490369

$630,000
03/15/2006

Sold (Public Record)

Public Record #277490369

$630,000
03/15/2006

Sold

MHMLS #235772

$630,000
03/15/2006

Sold

HVCR MLS #61024

$630,000
03/14/2006

Pending

MHMLS #235772

—
02/26/2006

Pending

HVCR MLS #61024

—
09/18/2005

Listed (Active)

HVCR MLS #61024

$689,000
09/18/2005

Listed (Active)

MHMLS #235772

$659,000
10/29/2001

Sold

MHMLS #202687

$411,500
10/08/2001

Pending

MHMLS #202687

—
03/20/2001

Listed (Active)

MHMLS #202687

$435,000

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

Public Records for 161 Whalesback Road

Taxable ValueLand$266,500Additions$739,000Total$1,005,500
Tax Record2024$20,586 ($1,716 / month)
Home Facts
Beds4Baths2.5Total Finished SqFt5,490 SqFtAbove Grade Finished SqFt5,490 SqFtStories2Lot Size657,756 SqFtStyleSingle Family ResidenceYear Built1900ZoningRD3CountyDUTCHESSAPN134889 6273-00-085713-0000Fireplace TypeHas Fireplace

Schools near 161 Whalesback Road

This home is within Red Hook Central School District.
Rating
School
Type
Grades
Distance
Mill Road Primary Grades
Public - PK to 2
Mill Road Intermediate Grades
Public - 3 to 5
Linden Avenue Middle School
Public - 6 to 8
Red Hook Senior High School
Public - 9 to 12
Rating
School
Distance
Mill Road Primary Grades
PublicPK to 2

Mill Road Intermediate Grades
Public3 to 5

Linden Avenue Middle School
Public6 to 8

Red Hook Senior High School
Public9 to 12

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

Similar Sold Homes

Explore Nearby Homes

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims 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 discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of Neil Charles Real Estate, LLC

Based on information submitted to the MLS GRID as of 09/08/2025 05:20 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.