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MLS ID KEY998694Last updated Sep 18, 2026

Single Family

303 Hicks Hill Road

Active · Pine Plains · Dutchess County, NY 12582

Bedrooms
5 Beds
Bathrooms
3 Baths
Year built
1860
Est. monthly taxes
$1,812.5
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About this home

Nestled on a country road in West Pine Plains, the Historic Hanlon Hill Farmstead offers a rare opportunity to own a piece of history. This 87-acre property, spanning five parcels, has been in the Hanlon family for six generations. The centerpiece is an 1840s eyebrow colonial home, set back from the road for ultimate privacy. As you enter the farm, you'll pass a serene pond and a charming one-bedroom guest cottage featuring wood floors and a beautiful brick fireplace. Currently rented for $1,000 per month, the tenant covers all utilities. The main house is a lovely blend of historic charm and modern comfort, with 4 bedrooms, 2 bathrooms, and gorgeous wide-board wood floors throughout. Nature lovers will appreciate the meadows, abundant woodlands, and diverse wildlife that surround the property. Farm roads wind through the land, leading to the highest points, where you can take in breathtaking sunset views. This land offers incredible development potential, with standing hardwoods ready for harvest, and the barn—24’ x 36’ with a metal roof—could easily be transformed into horse stalls or used for other farming needs. Whether you're an investor or an outdoor enthusiast, this property has endless possibilities. It’s ideal for hiking, hunting, or any outdoor activity you can imagine. The historic colonial features a large, covered front porch with its original door, opening into a grand staircase. To the right, a spacious living room boasts a large stone fireplace, and a small galley kitchen sits adjacent. To the left, you'll find a formal dining room and a bedroom with an antique bath, plus the main kitchen, complete with a wood stove. Upstairs, there are 3 bedrooms and a modern, fully-tiled bathroom with both a tub and shower. A cozy office or nursery is located off the largest bedroom. A three-season porch overlooks the meadows and orchard, offering a peaceful spot to relax. The property also includes a creamery, a smokehouse, and stunning stone retaining walls that add to its rustic charm. Conveniently located just off the Taconic Parkway, this farm is an easy drive to Rhinebeck, Red Hook, and Pine Plains. Whether you're looking for a serene retreat, a development opportunity, or a place to pursue farming, this historic property offers something for everyone.

Listing snapshot

Days on site
59 days
Listed on MLS
May 12, 2026
Full baths
3
Half baths
0
Annual property tax (MLS)
$21,750
Tax year
2025
Area source (MLS)
Public Records
Listing brokerage
Staley Real Estate, LLC
MLS ID
KEY998694
Last updated
Sep 18, 2026

General features

Property type
Single Family
Property subtype
Single Family Residence
Year built
1860
Garage
No
Total parking
6
Parking
Off Street
Water source
Spring
Sewer
Cesspool, Septic Tank
Utilities
Cable Available, Cable Connected, Electricity Available, Electricity Connected

Interior features

Basement
Unfinished
Heating
Baseboard, Hot Water, Oil
Cooling
None
Interior
First Floor Bedroom, Beamed Ceilings
Appliances
Convection Oven, Dishwasher, Electric Cooktop, Electric Oven
Fireplaces
2

Exterior features

Architectural style
Colonial
Construction materials
Frame
Private pool
No

Schools (MLS)

Elementary school
Cold Spring Early Learning Ctr
Elementary school district
Pine Plains
Middle school
Stissing Mountain Junior/Senior High School
Middle school district
Pine Plains
High school
Stissing Mountain Jr/Sr High School
High school district
Pine Plains

School information is provided by the MLS. Confirm attendance eligibility with the school district.

Recent activity

  1. Listing updated from MLS
  2. First seen on this site
  3. MLS status changed

Location

Pine Plains · Dutchess County, NY 12582Show interactive map
303 Hicks Hill Road

Pine Plains · Dutchess County, NY 12582

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Estimate monthly payment

Loan detailsFixed-rate, fully amortizing loan. Edit the assumptions below; no market rate is supplied.
Property expenses (USD)
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Estimated monthly principal & interest—

Monthly property taxNot provided

Monthly association / maintenance feesNot provided

Estimated monthly total of entered costs—

Excludes insurance, mortgage insurance, special assessments and lender fees. MLS taxes may reflect abatements or exemptions and can change.

Listing data is supplied by the MLS and may change without notice.