161 Whalesback Road, Red Hook, NY 12571
OFF MARKET

$1,831,800

Trulia Estimate
  • 5 Beds
  • 4.5 Baths
  • 5,490 sqft (on 15.10 acres)

161 Whalesback Road, Red Hook, NY 12571

Est. Refi. Payment $12,646/mo*
Refinance Your Home
Currently Off Market - Sold Sep 8, 2025 for $1,700,000

Home Value

Trulia Estimate
$1.83M
Since last month
Increased$16K (+0.9%)
Since last year
Increased$129K (+7.5%)
Since last sale
Increased$132K (+7.8%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +144% in the last 10 years
MonthEstimated value
2026
September 2026$1.83M
August 2026$1.82M
July 2026$1.81M
June 2026$1.83M
May 2026$1.76M
April 2026$1.77M
March 2026$1.75M
February 2026$1.76M
January 2026$1.75M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
145 Whalesback Road, Red Hook, NY
0.10
Single-Family Home
$1,200,000
11/17/25
4
4.5
4,500
17 Elm Street, Red Hook, NY
0.46
Single-Family Home
$999,999
07/13/26
5
4
3,628
115 Whalesback Road, Red Hook, NY
0.27
Single-Family Home
$695,000
10/01/25
3
2.5
3,020
6 Dogwood Street, Red Hook, NY
0.63
Single-Family Home
$525,000
12/11/25
3
3
2,126
84 Rockefeller Lane, Red hook, NY
1.11
Single-Family Home
$850,000
03/09/26
4
3.5
3,152
41 Cornell Avenue, Red Hook, NY
0.53
Single-Family Home
$535,000
07/06/26
3
2
1,986
14 Princeton Street, Red Hook, NY
0.34
Single-Family Home
$390,000
04/21/26
3
1
1,228
2 Princeton Street, Red Hook, NY
0.41
Single-Family Home
$449,000
07/23/26
3
1
1,325
5 Harvard Street, Red Hook, NY
0.37
Single-Family Home
$400,000
11/24/25
3
1
1,108

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
145 Whalesback Road, Red Hook, NY 12571
0.10
$4,455,600
4
4.5
4,500
Off Market
10 COLUMBIA Avenue, Red Hook, NY 12571
0.25
$378,300
3
1
1,075
Off Market
223 WHALESBACK Road, Red Hook, NY 12571
0.24
$342,300
2
2
924
Off Market
21 HARVARD Street, Red Hook, NY 12571
0.26
$376,600
3
1
1,008
Off Market
224 Whalesback Road, Red Hook, NY 12571
0.29
$445,600
3
1
1,435
Off Market
42 Pond View Drive, Red Hook, NY 12571
0.23
$1,718,400
5
3
5,324
Off Market
0 Whalesback Road, Red Hook, NY 12571
0.30
-
-
-
-
Off Market
115 Whalesback Road, Red Hook, NY 12571
0.27
$745,600
3
2.5
3,020
Off Market
11 Princeton, Red Hook, NY 12571
0.32
$399,000
3
1
1,075
For Sale
20 AMHERST Street, Red Hook, NY 12571
0.34
$409,100
3
2
1,152
Off Market
14 Princeton Street, Red Hook, NY 12571
0.34
$390,000
3
1
1,228
Recently Sold

Local Information

  • Map ViewExplore the area around 161 Whalesback Road.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1900
15.1 acre lot
5,490 sqft
$334/sqft
Garage

About this House

What's unique:Modern luxuryGuest spaceFlagstone patioOpen floor planConverted barnStunning in-ground pool
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.
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). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,831,800, with a rent estimate of $5,329/month.
Last check for updates: about 4 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

Home Details for 161 Whalesback Road

Interior Features

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)

Exterior Features

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

Days on Market

Cumulative Days on Market: 23

Property Information

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

Price & Status

Price
List Price: $1,799,000
Status Change & Dates
Off Market Date: Thu Jul 31 2025

Active Status

MLS Status: Sold

Location

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

Building

Building Area
Building Area: 5490 Square Feet

Community

Not Senior Community

HOA

No HOA

Lot Information

Lot Area: 15.1 Acres

Listing Info

Special Conditions: None

Offer

Listing Agreement Type: Exclusive Right To Sell

Miscellaneous

BasementMls Number: 885582Attic: Partial, Pull Stairs, UnfinishedShowing Advance Notice: 24Showing Requirements: 24 Hour Notice, Appointment Only, Call Listing Agent, See Remarks

Price and Tax history

DateEventPrice
Sep 8, 2025
Source: OneKey® MLS as distributed by MLS GRID #885582
Sold
$1,700,000
Jul 31, 2025
Source: OneKey® MLS as distributed by MLS GRID #885582
Pending
$1,799,000
Jul 8, 2025
Source: OneKey® MLS as distributed by MLS GRID #885582
Listed For Sale
$1,799,000
Nov 3, 2008
Source: N/A
Sold
$100,000
Mar 15, 2006
Source: HVCRMLS #61024
Sold
$630,000

Market trends in Red Hook

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
39
3MoM

Around this home

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.
  • Pat
    "We have street festivals and music often. Great little shopping area and dining options. Clean. Very friendly people."
    0
    Flag
  • Pat
    "Fabulous schools! Nice parks and outstanding family atmosphere. Great neighbors, great restaurants. Easy to get around."
    0
    Flag
  • Pat
    "The sidewalks are plentiful. Our neighbors clean up after themselves and people are very friendly throughout the community."
    1
    Flag
  • Pat
    "We have a dog park in Red hook, but most people do walk their dogs along the sidewalk and do thankfully pick up after them"
    0
    Flag
  • Kns Carter
    "Beautiful trees, respectful neighbors, well cared for homes and intergenerational community. Small town feeling."
    0
    Flag
  • Pat
    "It’s a very family oriented village filled with great little shops and many many wonderful people. It is easy access to go to New York State, New Jersey and Connecticut and Massachusetts."
    0
    Flag
  • Alyssa Dicarlo
    "I’ve lived in this town my whole life and now am raising a family here as well. We always feel safe. Everything is easily accessible and most people are very neighborly and helpful. We love that we can walk to certain hot spots in the summertime, makes for great memories "
    0
    Flag
  • Trulia User
    "The school district is amazing, friendly people and I live in college park which if you cross through the woods in Linden Acres your there. Safe and beautiful area. "
    2
    Flag
  • Adrienne L.
    "I work from home. I don’t commute. If I want to go to town it’s about a 15 minute drive. There is a gas station 5 minutes away. I like the location and enjoy the great outdoor feel. I am not sure what else to say. "
    2
    Flag
  • Elaine D.
    "Lived here 16 years and can’t imagine living anywhere else. Friendly, warm. Safe. Great shopping. AAA"
    2
    Flag
  • Kelly F.
    "Country lanes with lots of walkers. Tics are an issue here so you must check often. Great veterinarians in town. "
    1
    Flag
  • Jessica C.
    "Hardscrabble, Apple Blossom & Red Hook & the Chocolate Festivals. Parades are common and well-attended. "
    1
    Flag
  • Rav0311
    "you will love it here. it's the perfect place to raise a family. the school is the best . the taxes suck but that about it"
    1
    Flag
  • Kellyakozlowski
    "My neighborhood has quick access to the taconic parkway making it quick and easy to access many neighboring areas. "
    0
    Flag
  • Elaine D.
    "Excellent environment! Slow speed, 2 traffic lights, many restaurants, easy highway access! Kind people, family community."
    4
    Flag
  • Olivia T.
    "milan is great for private living and beautiful nature it is a luxury but far from town. love it out here "
    0
    Flag
  • Rav0311
    "it's perfect to start a family and feel at home. everybody is nice and the schools are great. plenty of restaurants and places to get together"
    0
    Flag
  • Sashaaha37qt
    "We live at one of the highest points in Milan/Red Hook (same zip code ). This is a family area with an excellent school system! There is also a beautiful, nearby Rec Park"
    3
    Flag
  • Nicole G.
    "Definitely need a car in this area. Unless you are a college student. Then there is a shuttle that will get you where you need to go. There is a bus but it is doesn’t run often, and is not optimal. "
    0
    Flag
  • Shannonfasce
    "Many dogs in the neighborhood very dog-friendly. Dogs are always leashed never running loose. Dog owners a very respectful of neighbors property "
    0
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  • Jkdive8
    "I have lived hear for 20+ years it’s quite and well preserved they try to keep it country living and they do very well at it !"
    1
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  • Tamara
    "Very family friendly. I love living here and found it easy to meet people and find a community. Love that I’m near many stores, restaurants, and theaters, but in the middle of the woods as well. "
    0
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  • Kristen M.
    "I’ve lived here all my life. It’s a comfortable small town where you become a regular at the dunkin or the restaurants. "
    0
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  • Plass r.
    "I've lived in red hook for 8 yrs and alot of people seem to put there head up like there better than anyone else"
    0
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  • Jeannette W.
    "I’ve lived in this neighborhood for 5 1/2 months and really enjoy it. Everyone is super friendly and stores and restaurants are easy to get to."
    0
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LGBTQ Local Legal Protections

Based on information submitted to the MLS GRID as of 2026-09-22 13:58:22 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

Frequently asked questions about 161 Whalesback Road

  • What is 161 Whalesback Road estimated to be worth?
    Trulia's estimated value for 161 Whalesback Road in Red Hook, NY is $1,831,800.
  • What is the price history for 161 Whalesback Road?
    161 Whalesback Road in Red Hook, NY last sold for $1,700,000 in September 2025.
  • Is Red Hook a buyer's or seller's market?
    Red Hook is currently a balanced market, based on recent for-sale activity.
  • What do residents say about Red Hook?
    Residents describe Red Hook, NY as easy to park in, well-kept, and dog-friendly. Most residents say you need a car. See recently sold homes in Red Hook, NY.
  • Does 161 Whalesback Road have air conditioning?
    Yes, 161 Whalesback Road in Red Hook, NY has air conditioning.
  • Does 161 Whalesback Road have a pool?
    Yes, 161 Whalesback Road in Red Hook, NY has a pool.

Explore by feature - Pet Friendly

6 pet-friendly rentals in Red Hook, NY

Explore by feature - Air Conditioning

14 rentals with air conditioning in Red Hook, NY

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14 rentals with a washer/dryer in Red Hook, NY

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Off Market Homes Near 161 Whalesback Road

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