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31 Chestnut Street

Rhinebeck, NY 12572
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Bed 4

Bed

Bath 3

Bath

SqFt3,380

Sqft

Acres0.77

Acre(Lot)

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 a nd 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.

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Detail Ic Property Details

Property Type : Residential

Price : $2,955,000

AD Id : 79660586

MLS Id : 1006579

Beds : 4

Lot Size : 0.77 Acre

Living Area Size : 3,380

Year Built : 1870

Garage : 2

County : Dutchess

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Feature Features

  • Bedroom Information

    Total beds: 4

    Bathroom Information

    Total Baths: 3 Full Baths: 2 Half Baths: 1

    Room Information

    Rooms Total: 12 Basement: Unfinished
  • Flooring Information

    Wood
  • Interior Features

    Crown Molding, Entrance Foyer, High Ceilings Appliances: Range, Refrigerator Window Features: Storm Window(s), Wood Frames
  • Heating & Cooling

    Has Heating: Yes Heating: Forced Air, Oil Cooling: None

  • Building Information

    Year Built: 1870 Construction Materials: Cedar, Clapboard, Wood Siding Private Pool: No

  • Lot Information

    Lot Size Acres: 0.77 Lot Size Square Feet: 33541

  • Listing Price Information

    Listing Price: $2955000

  • Tax Information

    Parcel Number: 135001-6170-15-547335-0000 Annual Tax: $23943

  • Parking Information

    Driveway, Garage, Off Street

    Garage Information

    Has Garage: Yes Garage Space: 2

  • School Information

    Elementary School: Chancellor Livingston Elementary Sch
    Junior High School: Rhinebeck Senior High School
    Senior High School: Rhinebeck Senior High School
  • Utility Information

    Electricity Connected, Propane
  • Location Information

    Direction: 31 Chestnut Street in Rhinebeck Village. WaterSource: Public
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Nearby Home Value

Address Estimate Bed Bath Sq. Ft Lot Size
Mill Road, Rhinebeck, NY, 12572 $960,000 -- -- --
Beckrick Drive, Rhinebeck, NY, 12572 $544,900 1 1 1,200 1,200 SqFt
440 Milan Hollow Road, Rhinebeck, NY, 12572 $1,400,000 4 3 3,224 3,224 SqFt
70 Camp Drive, Rhinebeck, NY, 12572 $699,000 2 2 1,900 1,900 SqFt
457 Round Lake Road, Rhinebeck, NY, 12572 $2,850,000 3 4 3,952 3,952 SqFt
334 Lake Drive, Rhinebeck, NY, 12572 $1,195,000 3 3 2,900 2,900 SqFt
40 Lakeside Drive, Rhinebeck, NY, 12572 $2,495,000 3 2 2,770 2,770 SqFt
6 Woods Road, Rhinebeck, NY, 12572 $349,000 2 1 968 968 SqFt
292 Mountain View Road, Rhinebeck, NY, 12572 $1,250,000 2 2 1,750 1,750 SqFt
1231 Route 308, Rhinebeck, NY, 12572 $525,000 2 2 976 976 SqFt

The data relating to real estate for sale on this website comes in part from the Internet Data exchange of OneKey MLS. IDX information is 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. Copyright © 2026 OneKey MLS. All Rights Reserved

ByOwner last updated this listing 06/18/2026 @ 01:50

MLS: 1006579 LISTED BY: SHERI SCEROLER, Four Seasons Sothebys Intl 845-876-5100 SOURCE: OneKey MLS

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