161 Whalesback Road
Red Hook, NY 12571
5 Beds
4.5 Baths
5,490 sqft (on 15.10 acres)
5 Beds
4.5 Baths
5,490 sqft
(on 15.10 acres)
Local Information
- Map ViewExplore the area around 161 Whalesback Road.
- Schools1 Preschool School1 Elementary School1 Middle School1 High School
- Shop & Eat
-- mins to
Home Highlights
Property Type
Single-Family Home
Year Built
1900
Lot Size
15.1 acres
Living Area
5,490 sqft
Price/Sqft
$331
Parking
Garage
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 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.
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.
161 Whalesback Road, Red Hook, NY 12571 is a 5 bedroom, 5 bathroom, 5,490 sqft single-family home built in 1900. It last sold for $1,700,000 on Sep 8, 2025 (6% below the $1,799,000 asking price). It is currently off market. The Trulia Estimate is $1,815,900, with a rent estimate of $6,747/month.
Home Details for 161 Whalesback Road
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Interior Details Basement: Partial,Storage Space,Unfinished,Walk-Out AccessNumber of Rooms: 13Types of Rooms: Master Bedroom, Bedroom 1, Bedroom 3, Bedroom 4, Bedroom 5, Master Bathroom, Bathroom 1, Bathroom 2, Bathroom 3, Bathroom 4, Bathroom 5, Dining Room, Family Room, Kitchen, Laundry, Living Room, Office |
Beds & Baths Number of Bedrooms: 5Number of Bathrooms: 5Number of Bathrooms (full): 4Number of Bathrooms (half): 1 |
Dimensions and Layout Living Area: 5490 Square Feet |
Appliances & Utilities Utilities: Cable Available, Phone Available, Propane, Sewer Connected, Trash Collection Private, Water ConnectedAppliances: Cooktop, Dishwasher, Dryer, Oven, Refrigerator, Stainless Steel Appliance(s), WasherDishwasherDryerLaundry: Laundry RoomRefrigeratorWasher |
Heating & Cooling Heating: Baseboard,Hot Water,Propane,RadiantHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Baseboard |
Fireplace & Spa Number of Fireplaces: 1Fireplace: Living Room, Wood BurningHas a FireplaceNo Spa |
Gas & Electric Has Electric on Property |
Windows, Doors, Floors & Walls Flooring: Carpet, Hardwood, Tile |
Levels, Entrance, & Accessibility Levels: TwoFloors: Carpet, Hardwood, Tile |
View Has a ViewView: Open, Park/Greenbelt |
Security Security: Security System, Smoke Detector(s) |
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Exterior Home Features Patio / Porch: Patio, Porch, ScreenedVegetation: Partially WoodedOther Structures: Garage(s)Exterior: GardenFoundation: Slab, StoneGardenHas a Private Pool |
Parking & Garage Number of Garage Spaces: 4Number of Covered Spaces: 4No CarportHas a GarageHas Open ParkingParking Spaces: 8Parking: Driveway,Garage,Off Street,Private |
Pool Pool: In GroundPool |
Water & Sewer Sewer: Septic Tank |
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Cumulative Days on Market: 23 |
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Year Built Year Built: 1900 |
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family Residence, ResidentialArchitecture: Other,Traditional |
Building Construction Materials: Blown-In Insulation, HardiPlank TypeNot Attached Property |
Property Information Condition: Updated/RemodeledParcel Number: 1348896273000857130000 |
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Price List Price: $1,799,000 |
Status Change & Dates Off Market Date: Thu Jul 31 2025 |
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MLS Status: Sold |
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Direction & Address City: Red Hook |
School Information Elementary School: Mill Road-Primary GradesJr High / Middle School: Linden Avenue Middle SchoolHigh School: Red Hook Senior High SchoolHigh School District: Red Hook |
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Building Area Building Area: 5490 Square Feet |
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Not Senior Community |
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No HOA |
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Lot Area: 15.1 Acres |
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Special Conditions: None |
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Listing Agreement Type: Exclusive Right To Sell |
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BasementMls Number: 885582Attic: Partial, Pull Stairs, UnfinishedShowing Advance Notice: 24Showing Requirements: 24 Hour Notice, Appointment Only, Call Listing Agent, See Remarks |
Last check for updates: about 8 hours ago
Listed by Ann C. Stettner, (917) 660-3266
Neil Charles Real Estate, LLC, (845) 266-8374
Bought with: Sarah Finch, (845) 514-3628, The Kinderhook Group, Inc., (845) 802-5005
Source: OneKey® MLS as distributed by MLS GRID, MLS#885582
Price History for 161 Whalesback Road
| Date | Price | Event | Source |
|---|---|---|---|
| 09/08/2025 | $1,700,000 | Sold | OneKey® MLS as distributed by MLS GRID #885582 |
| 07/31/2025 | $1,799,000 | Pending | OneKey® MLS as distributed by MLS GRID #885582 |
| 07/08/2025 | $1,799,000 | Listed For Sale | OneKey® MLS as distributed by MLS GRID #885582 |
| 11/03/2008 | $100,000 | Sold | N/A |
| 03/15/2006 | $630,000 | Sold | HVCRMLS #61024 |
| 10/29/2001 | $411,500 | Sold | MHMLS #202687 |
Market trends in Red Hook
Last updated June 2026
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
31
1MoM
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Property Tax and Assessment
| Year | 2025 |
|---|---|
| Tax | |
| Assessment | $1,096,000 |
Home facts updated by county records
Comparable Sales for 161 Whalesback Road
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.10 | Single-Family Home | $1,200,000 | 11/17/25 | 4 | 4.5 | 4,500 | |
0.46 | Single-Family Home | $999,999 | 07/13/26 | 5 | 4 | 3,628 | |
0.27 | Single-Family Home | $695,000 | 10/01/25 | 3 | 2.5 | 3,020 | |
0.69 | Single-Family Home | $900,000 | 07/24/25 | 3 | 1.5 | 2,556 | |
0.63 | Single-Family Home | $525,000 | 12/11/25 | 3 | 3 | 2,126 | |
1.11 | Single-Family Home | $850,000 | 03/09/26 | 4 | 3.5 | 3,152 | |
0.53 | Single-Family Home | $535,000 | 07/06/26 | 3 | 2 | 1,986 | |
0.59 | Single-Family Home | $500,000 | 08/28/25 | 3 | 2 | 1,689 |
Nearby homes
Get a sense of prices in the area by checking nearby homes.
SOLDNOV 17, 2025Coldwell Banker American Homes
OFF MARKETHoulihan Lawrence Inc.
OFF MARKETBHHS Hudson Valley Properties
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SOLDOCT 1, 2025Rouse + Co Real Estate, LLC, Closed
FOR SALEListing by: Mondello Upstate Properties
OFF MARKETPaul Hallenbeck Real Estate
SOLDAPR 21, 2026Mondello Upstate Properties
Assigned Schools
These are the assigned schools for 161 Whalesback Road.
- Mill Road Intermediate Grades
- PK-5
- Public
- 636 Students
5/10GreatSchools RatingParent Rating AverageThe school makes you feel like a family and the teachers are caring and loving. There are no racism in this school.Student Review10y ago - Linden Avenue Middle School
- 6-9
- Public
- 391 Students
5/10GreatSchools RatingParent Rating AverageToo much bullying and administration/staff don’t handle it wellOther Review5mo ago - Red Hook Senior High School
- 9-12
- Public
- 549 Students
7/10GreatSchools RatingParent Rating AverageMy daughter has been a student in the Red Hook schools since Kindergarten, and she's had an excellent experience all the way through. We could have sent her to a private school, but because she has thrived at Red Hook, we chose not to. The HS prepares students well, offering a first-rate, high-caliber curriculum that students are encouraged to take advantage of. The majority of her classmates are academically gifted and ambitious, and my daughter has benefitted from the challenging atmosphere. She'll be graduating with an International Baccalaureate diploma, and applying to top-tier colleges. Yes, an auditorium needs to be built, but in the meantime, the Red Hook band has been holding some performances at the world-class Fisher Center at Bard College. Not too shabby! If your child is talented, bright, motivated, and comes from a supportive home, she/he will do well!Parent Review11y ago 
Check out schools near 161 Whalesback Road.
What Locals Say about Red Hook
At least 63 Trulia users voted on each feature.
91 % Say car is needed
88 % Say parking is easy
83 % Say yards are well-kept
81 % Say it's dog friendly
81 % Say people would walk alone at night
79 % Say there's wildlife
76 % Say it's quiet
69 % Say there's holiday spirit
68 % Say kids play outside
65 % Say neighbors are friendly
59 % Say they plan to stay for at least 5 years
57 % Say it's walkable to restaurants
45 % Say there are community events
38 % Say streets are well-lit
37 % Say it's walkable to grocery stores
31 % Say there are sidewalks
Sourced by Trulia users. Learn more about our methodology.
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5.18 ACRESListing by: Legacy Land & Homes LLC
3.4 ACRESListing by: Corcoran Country Living
1.42 ACRESListing by: eXp Realty, Active
34.84 ACRESListing by: Compass Greater New York, LLC, Active
18.6 ACRESListing by: Rouse + Co Real Estate, LLC, Active
0.84 ACRESListing by: Upstate Down, Active
0.34 ACRESListing by: Rouse + Co Real Estate, LLC, Active
1 ACREListing by: Chapman Realty of the Hudson V, Active
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Off Market Homes Near 161 Whalesback Road
SOLDJUL 10, 2026BHHS HUDSON VALLEY PROP-WDST, Closed
SOLDJUN 18, 2026Houlihan Lawrence, Inc., Closed
SOLDAPR 22, 2026Four Seasons Sotheby's Int., Closed
SOLDAPR 6, 2026Four Seasons Sotheby's Int., Closed
SOLDAPR 6, 2026Compass Greater NY, LLC, Closed
SOLDMAR 27, 2026Brown Harris Stevens HV LLC
SOLDMAR 13, 2026HV Catskill Region MLS, Closed
SOLDFEB 25, 2026Four Seasons Sotheby's Int., Closed
SOLDFEB 11, 2026Corcoran Country Living- See more homes for sale inRed Hook
Based on information submitted to the MLS GRID as of 2026-07-22 07:53:11 PDT 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. Some IDX listings have been excluded from this website. Click here for more information