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31 Chestnut Street

Rhinebeck, NY 12572

$2,955,000 PRICE
4 Beds
2/1 Baths
3,380 Sqft
0.77 Acres
1870 Built

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.

Additional Information

ADDITIONAL INFORMATION

BASEMENT DESCRIPTION: Unfinished
DAYS ON MARKET: 23
ELEMENTARY SCHOOL: Chancellor Livingston Elementary Sch
ELEMENTARY SCHOOL DISTRICT: Rhinebeck
HIGH SCHOOL: Rhinebeck Senior High School
LIVING AREA SQFT: 3380
MIDDLE SCHOOL: Rhinebeck Senior High School
ON MARKET DATE: 2026-05-30
PARKING: Driveway, Garage, Off Street
SEWER: Septic Tank
STYLE: Victorian
TAX AMOUNT: $23,943
TYPE: Residential
UTILITIES: Electricity Connected, Propane
YEAR BUILT: 1870

INTERIOR/EXTERIOR FEATURES

APPLIANCES INCLUDED: Range, Refrigerator
BEDS: 4
CONSTRUCTION MATERIALS: Cedar, Clapboard, Wood Siding
FLOORING: Wood
FULL BATHS: 2
HEAT: Forced Air, Oil
INTERIOR FEATURES: Crown Molding, Entrance Foyer, High Ceilings
ROOMS: 12

Listing Courtesy of SHERI SCEROLER of Four Seasons Sothebys Intl (845.876.5100).

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Location for 31 Chestnut Street, Rhinebeck, NY

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Schools for 31 Chestnut Street, Rhinebeck, NY

Our community offers residents access to a number of fine private and public schools for all grade levels. Please read below for information on each of the schools in our area.

Elementary School
Chancelor/Livingston
Middle School
Rhinebeck Senior High School
High School
Rhinebeck Senior High School
45 North Park Road
Rhinebeck, NY 12572

Grades: 9 - UG
(845) 871-5500

Private Schools

SCHOOL	LOCATION	GRADE
Astor Learning Center	Po Box 5005 Rhinebeck, NY 12572	UG
Astor Home for Children	6339 Mill St P.O. Box 5005 Rhinebeck, NY 12572	UG
Primrose Hill School	23 Spring Brook Park Rhinebeck, NY 12572	PK - 5
Primrose Hill School	23 Spring Brook Park Rhinebeck, NY 12572	PK - 6
Kingston Catholic School	159 Broadway Kingston, NY 12401	PK - 8
Good Shepherd School	83 East Chester Street Kingston, NY 12401	PK - 8
Abundant Life Academy	PO BOX 1565 Kingston, NY 12402	1 - 9

*UG = ungraded.
Detailed school information provided by GreatSchools.org © . All rights reserved.

Public and private school information is provided by sources including GreatSchools.org and various MLS services including the One Key, SMARTMLS, NCMLS, DARMLS and Greenwich MLS, and is subject to the terms of use on those sites. William Pitt and Julia B. Fee Sotheby’s International Realty believes the information provided by these sources to be accurate but will not be held responsible if any data as well as information such as school districts for listings is inaccurate.

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Community

Rhinebeck

Hudson Valley, New York

Rhinebeck, New York, is a popular historic town in Dutchess County in the Northern Hudson Valley. From dramatic views of the Catskill Mountains and the Hudson River to the sights and sounds of a thriving...

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