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#WOODWARD HILL STISSNG MOUNT HICKS HILL, Pine Plains, NY 12567

$36,000,000

A once-in-a-lifetime opportunity to own 1,945 acres of pristine land, with expansive road frontage and multiple contiguous parcels. This estate includes 4 single-family homes, a two-family residence, a large commercial building, and a secluded storage or workshop. The diverse landscape features woodlands, rolling meadows, ponds, streams, and striking homesites surrounded by hedgerows, offering a perfect canvas for development or personal retreat. Located across both the Town of Milan and Town of Pine Plains, this property truly captures the essence of rural luxury. From its sweeping western views of the Catskills, where the sunsets are nothing short of spectacular, to the tranquil northern vistas and the stunning Taconic range to the northeast, the scenery here is simply unparalleled. Stissing Mountain graces the horizon at every turn, creating a sense of belonging. With a subdivision already in place, the groundwork for future development has been laid, while hundreds of untouched acres await your imagination. Nestled in the tranquil countryside of Dutchess County, this magnificent property offers easy access to charming towns like Red Hook, Rhinebeck, Millbrook, Pine Plains, Millerton, and Amenia.

Highlights

  • Land
  • 1946.0 Acre Lot
  • 762 days on Market


  • Acres
    1946.0
  • Lot Features
    Wooded, Rolling Slope, Sloped, Cleared, Views
  • Water Front Features
    Waterfront Access
  • View
    Water
  • Water
    Public, Private, Well

  • County
    Dutchess
  • City
    Pine Plains
  • Zip Code
    12567
  • High School
    Stissing Mountain Jr/Sr High School
  • Middle School
    Stissing Mountain Junior/Senior High School
  • Elementary School
    Seymour Smith Intermediate Lrn Ctr

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Frequently Asked Questions

How do I schedule a tour of #WOODWARD HILL STISSNG MOUNT HICKS HILL?

We can make that happen quickly. Click Tour This Home and we'll connect you directly with our vetted local partner to schedule your visit to #WOODWARD HILL STISSNG MOUNT HICKS HILL.

They know lands in the area well and can give you the guidance you need to buy with confidence.

How do I get more information about #WOODWARD HILL STISSNG MOUNT HICKS HILL?

Click Ask a Question to talk with our team. You already know it is a N/A bed, N/A bath, listed for $36,000,000. We can talk through recent upgrades, potential seller motivation, how this land compares to others in Pine Plains, and can even get you in to see the property quickly.

How much is the monthly mortgage payment for #WOODWARD HILL STISSNG MOUNT HICKS HILL?

With a 20% down payment and a 30-year fixed loan at an illustrative 7.25% rate, the ez Mortgage Calculator estimates the monthly payment for #WOODWARD HILL STISSNG MOUNT HICKS HILL at around $228,884. This includes estimated property taxes and insurance.

Want to see how this changes with different down payments or interest rates? Jump to the calculator to run the numbers and fine-tune your plan.

How do I get pre-approved to buy #WOODWARD HILL STISSNG MOUNT HICKS HILL?

Stand out in a competitive market by getting pre-approved today. Our quick and private pre-approval process helps you understand your true buying power—no credit pull required to explore all of your options.

Or, let us connect you with our preferred local lender in Dutchess County. They will give you all of your available financing options, based on your specific situation and what is available to you.

Can I negotiate the asking price for #WOODWARD HILL STISSNG MOUNT HICKS HILL?

In most cases, yes. Whether #WOODWARD HILL STISSNG MOUNT HICKS HILL is priced competitively or not, your best offer depends on your personal situation, the seller's timeline, and recent activity in Pine Plains's market. Our preferred local partner will help you craft a strategy—factoring in comparable properties that have sold, timing, and deal structure—to make a smart, strong offer. Click here to ask about negotiation opportunities.

How do I make an offer on #WOODWARD HILL STISSNG MOUNT HICKS HILL?

We can handle that for you. Our preferred local agent specializes in lands in Pine Plains and can guide you through every step of the offer process.

You need an expert who is looking out for your best interests. From market valuation to contingencies and timing, they'll help you present a compelling offer that fits your goals. Click Ask a Question to get started today.

How long has this property been on the market?

#WOODWARD HILL STISSNG MOUNT HICKS HILL was listed on October 13, 2024, which means it's been on the market for 762 days.

Want to keep tabs on it? Click the ♥ to favorite this home and get notified of price drops or changes.

What is the lot size of this property?

#WOODWARD HILL STISSNG MOUNT HICKS HILL sits on a 1946.0-acre lot, which is 84,767,760 square feet.

What schools are assigned to this property?

Based on MLS info, this home is zoned for:

  • Elementary: Seymour Smith Intermediate Lrn Ctr
  • Middle: Stissing Mountain Junior/Senior High School
  • High: Stissing Mountain Jr/Sr High School

Want to see how these schools compare? Check out our Dutchess County School Guide to see ratings, reviews, and more for the schools in the area.

What are the property taxes for #WOODWARD HILL STISSNG MOUNT HICKS HILL?

The most recent public record shows annual property taxes for #WOODWARD HILL STISSNG MOUNT HICKS HILL were approximately $288,201. This may change with reassessment or exemptions. Our local partner can verify current tax amounts and help you estimate future costs based on your situation.

Is #WOODWARD HILL STISSNG MOUNT HICKS HILL still available for sale?

Yes, this home is still available! Click the ♥ to favorite it so you don't miss any changes—or ask our local expert to schedule a time to see it in person.

Source: ez Home Search, MLS Data

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Listing information 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. Information deemed reliable but not guaranteed by the MLS. The listing broker’s offer of compensation is made only to participants of the MLS where the listing is filed. Copyright 2026, OneKey MLS. All rights reserved.

Last Updated: November 14, 2026 at 12:23AM | Source: OneKey MLS | MLS#: H6332462