Skip main navigation
Active
  • $2,955,000

    31 Chestnut Street, Rhinebeck, NY 12572

    4beds
    3,380sqft
    Loading
    Single Family Residence
    Built in 1870
    0.77 Acres Lot
    $-- Zestimate®
    $874/sqft
    $-- HOA

    What's special

    Marble fireplacesNatural lightPlaster wallsSoaring ceilingsExceptional acousticsGrand arched openingsIntact soft-coal heating stove
    This is a rare opportunity to thoughtfully steward and restore one of Rhinebeck Village's most architecturally compelling historic residences -- a property defined by provenance, scale, and enduring beauty. Set on coveted Chestnut Street, this distinguished circa-1870 Italianate villa offers 4 bedrooms and 2.5 baths and is among the few remaining historic homes in the village to retain such remarkable original detail and integrity. Soaring ceilings, grand arched openings, oversized bay windows, marble fireplaces, original plaster medallions, plaster walls, crown moldings, decorative chandeliers, and beautifully preserved original windows speak to a level of craftsmanship rarely found today. The home's exceptional acoustics -- enhanced by the original plaster walls -- create a quiet richness and warmth throughout the interiors that is immediately felt upon entering. Built for local attorney and town supervisor George Esselstyn, the residence unfolds across graciously proportioned rooms filled with natural light, including a richly atmospheric library anchored by an intact soft-coal heating stove and original glass-front bookcases. Outside, the property becomes even more extraordinary. An original two-bay carriage barn with a walk-up loft offers exceptional potential for studio, guest, or creative use. The residence sits on an oversized village parcel with 100 feet of road frontage, accompanied by an additional separately deeded adjoining lot with another 50 feet of frontage -- a rarity within Rhinebeck Village and an offering that creates an estate-like setting of unusual scale, privacy, and presence. A truly exceptional offering for those who value architectural authenticity, history, and the rare privilege of bringing a significant home into its next chapter.
    43 days
    |
    1,743
    |
    112
    |

    Zillow last checked:

    Listing updated:

    Listed by:

    Four Seasons Sotheby's Int. 845-876-5100,

    Sheri Sceroler,

    Gary DiMauro 518-755-3973,

    Four Seasons Sotheby's Int.

    Source: HVCRMLS,MLS#: 20262855MLS Logo

    Loading...

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 4
      • Bathrooms: 3
      • Full bathrooms: 2
      • 1/2 bathrooms: 1
      Heating
      • Forced Air, Oil
      Cooling
      • None
      Appliances
      • Included: Refrigerator, Range
      Features
      • Crown Molding, Entrance Foyer, High Ceilings, Other
      • Flooring: Parquet, Wood
      • Doors: Storm Door(s)
      • Windows: Storm Window(s), Wood Frames
      • Has basement: No
      • Number of fireplaces: 4
      • Fireplace features: Other
      Interior area
      • Total structure area: 3,380
      • Total interior livable area: 3,380 sqft
      • Finished area above ground: 3,380
      • Finished area below ground: 1,690

      Property

      Parking
      • Total spaces: 2
      • Parking features: Garage Faces Front, Off Street, Driveway
      • Garage spaces: 2
      • Has uncovered spaces: Yes
      Lot
      • Size: 0.77 Acres
      Details
      • Parcel number: 1350016170155473350000
      • Zoning: R35 zoning

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Victorian
      • Property subtype: Single Family Residence
      Materials
      • Frame, Plaster, Wood Siding
      • Foundation: Stone
      Condition
      • New construction: No
      • Year built: 1870

      Utilities & green energy

      • Electric: 200+ Amp Service
      • Sewer: Septic Tank
      • Utilities for property: Electricity Connected, Propane

      Community & HOA

      Community
      • Features: Golf, Playground, Restaurant, Tennis Court(s)
      Location
      • Region: Rhinebeck

      Financial & listing details

      • Price per square foot: $874/sqft
      • Tax assessed value: $949,200
      • Annual tax amount: $23,943
      • Date on market: 5/30/2026
      • Listing terms: Conventional,FHA
      • Electric utility on property: Yes

        Estimated market value

        Not available

        Estimated sales range

        Not available

        $5,460/mo

        Price history

        DateEventPrice
        5/30/2026Listed for sale$2,955,000+25.7%$874/sqft
        Source: OneKey® MLS as distributed by MLS GRID #1006579 Report a problem
        12/1/2022Listing removed--
        Source: Columbia Greene Northern Dutchess MLS #144045 Report a problem
        9/29/2022Listed for sale$2,350,000+11.9%$695/sqft
        Source: Columbia Greene Northern Dutchess MLS #144045 Report a problem
        12/1/2021Listing removed$2,100,000$621/sqft
        Source: MHMLS #403625 Report a problem
        9/18/2021Listed for sale$2,100,000+125.8%$621/sqft
        Source: MHMLS #403625 Report a problem
        9/28/2013Listing removed$929,900$275/sqft
        Source: Prudential Serls Prime Properties #314871 Report a problem
        3/28/2013Price change$929,900+5.7%$275/sqft
        Source: Prudential Serls Prime Properties #314871 Report a problem
        12/9/2012Price change$880,000-1.7%$260/sqft
        Source: Owner Report a problem
        7/30/2012Price change$895,000-6.7%$265/sqft
        Source: H.H. HILL REALTY SERVICE #305187 Report a problem
        3/9/2012Listed for sale$959,000$284/sqft
        Source: H.H. HILL REALTY SERVICE #305187 Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025-- $949,200 -2.8%
        2024-- $976,200 +18.1%
        2023-- $826,900 +10.3%
        2022-- $750,000 -2.3%
        2021-- $767,300 +5%
        2020-- $730,800 +43.4%
        2019-- $509,600
        2018-- $509,600
        2017$9,677 $509,600
        2016-- $509,600
        2015-- $509,600
        2014-- $509,600
        2012-- $509,600
        2011-- $509,600
        2010-- $509,600 -8%
        2009-- $553,900 -5%
        2008-- $583,000 +2.5%
        2007-- $569,000
        2006-- $569,000 +14%
        2005-- $499,000 +141.1%
        2004-- $207,000
        2003-- $207,000
        2002-- $207,000
        2001-- $207,000
        2000-- $207,000
        Find assessor info on the county website

        Monthly payment

        Estimated monthly payment$1,822
        All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
        HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
        Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
        See how much you could borrow to make a competitive offer.

        Climate risks

        Neighborhood: 12572

        Getting around

        63 / 100
        Somewhat Walkable
        52 / 100
        Bikeable

        Nearby schools

        GreatSchools rating

        A local agent can set up tours, give advice and negotiate with sellers.

        Browse local experts

        Similar homes