New Listing - 05/30/2026
31 Chestnut Street, Rhinebeck, NY, 12572
12 rooms
4 beds
2 Full / 1 Half baths
1870
Victorian
3,380 sqft
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.
Status:
Active
Type:
Single-family residential
Garage:
2-car
Heating:
Forced Air, Oil
Cooling:
None
Basement:
Bilco Door(s), Unfinished
Parking:
Driveway, Garage, Off Street
Acreage:
0.77
Est. Taxes:
$23,943
Assessment
$949,200
Construction
Cedar, Clapboard, Wood Siding
Utilities
Electricity Connected, Propane
Elementary School:
Chancellor Livingston Elementary Sch
Middle School:
Rhinebeck Senior High School
High School:
Rhinebeck Senior High School
School District:
Rhinebeck
Appliances:
Range, Refrigerator
MLS #:
1006579
Community Info
School Info
Walk Score
Mass Transit
Yelp
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Listing courtesy of Four Seasons Sothebys Intl 845-876-5100