Leah Long
Licensed Real Estate Salesperson
REALTOR®
Oneonta, NY
Office: (607) 435-3280 (607) 437-2771 Cell

31 Chestnut Street, Rhinebeck, NY 12572

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Property Description

This is a rare opportunity to thoughtfully steward and restore one of Rhinebeck Villages 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 homes 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.

31 Chestnut Street | MLS# 20262855

This single family home located at 31 Chestnut Street, Rhinebeck, NY 12572 is currently listed for sale with an asking price of $2,955,000. This property was built in 1870 and has 4 bedrooms and 2 full and 1 partial baths with 3380 sq. ft. Chestnut Street is located within the Rhinebeck Central School District school district. Search Rhinebeck real estate on leah-long.timberlandproperties.com today.

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Property Features

Property Type: Residential - Single Family
Cooling: None
Fireplaces: 4
Fuel Type: Oil
Garage: 2
Heating: Forced Air, Oil
Home Style: Victorian
Lot Size: 0.77 Acres
Taxes: $23,943
Year Built: 1870

Amenities

Crown Molding
Entrance Foyer
High Ceilings
Other

Feature Descriptions

Appliances: Refrigerator, Range
Community Features: Golf, Playground, Restaurant, Tennis Court(s)
Days on Site: 2
Exterior: Frame, Plaster, Wood Siding
Fireplace: Other
Flooring: Parquet, Wood
Parcel #: 135001-6170-15-547335-0000
Parking: Garage Faces Front, Off Street, Driveway
Sewer: Septic Tank
SQFT Total: 3380
Swimming Pool: Yes
Utilities: Electricity Connected, Propane

Local Schools

School District: Rhinebeck Central School District

Estimate Your Payment

Estimated Payment

$ 9,433.67 per month $6,576.55 Principal & Interest $1,995.25 Property Tax $861.88 Homeowner's Insurance

Change Payment Information

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years/fixed
yearly
yearly (est.)
(Payments are an estimate and may vary by lender)

Demographics

Listed By / Shown By

Listing By

Agency Name: Four Seasons Sotheby's Int.

Shown By

Agent Name: Leah Long
Agent Phone: (607) 437-2771 Cell
Agency Title: Timberland Properties

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All information is deemed reliable but not guaranteed. All properties are subject to prior sale, change, or withdrawal. Neither broker(s), nor agent(s) shall be responsible for any typographical errors, misinformation, or misprints, and shall be held totally harmless. Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided 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 on this site was last updated 06/02/2026. The listing information on this page last changed on 06/02/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Tue 06/02/2026 12:00:18 AM EST) or Global MLS (last updated Mon 06/01/2026 11:52:15 PM EST) or New York State Alliance MLS (last updated Mon 06/01/2026 11:58:59 PM EST) or Hudson Valley Catskill Region MLS (last updated Mon 06/01/2026 11:51:14 PM EST) or OneKey MLS (last updated Mon 06/01/2026 11:53:21 PM EST). Real estate listings held by brokerage firms other than Timberland Properties may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.

All information is deemed reliable but not guaranteed. All properties are subject to prior sale, change, or withdrawal. Neither broker(s), nor agent(s) shall be responsible for any typographical errors, misinformation, or misprints, and shall be held totally harmless.

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