Property Description

Welcome to Brook Farm – Village of Chester, New York – Circa 1851 – 6.8 Acres.
There’s a moment, just after you turn onto Main Street and the house comes into view above the lawn, when you understand that this is not an ordinary property. The covered porch stretches wide across the front, the slate roof catches the afternoon light, and the whole thing sits there with the quiet confidence of something that has absolutely nothing to prove. Brook Farm has been here since 1851. It will be here long after you.
This is the kind of home that changes the way you think about time.
Originally the crown jewel of financier Richard Delafield’s 128-acre Brook Farm estate — named after his Tuxedo Park retreat — the manor was designed from the very beginning for a life lived generously. For gathering people. For long dinners that drift into evening. For the kind of entertaining that doesn’t need a theme, because the house is the occasion.
Step through the front door and the ceilings rise to greet you — twelve feet of plaster and molding, the proportions of a home that was never meant to feel small. The formal rooms flow one into the next: parlor, drawing room, dining room, each anchored by original fireplaces, each telling you without a word that whoever built this place understood how a house should feel. The hardwood oak floors, the walnut trim, the two grand staircases with their original woodwork — these aren’t period details. They’re the bones of the place, still standing, still beautiful, still doing exactly what they were put here to do.
Upstairs, four bedrooms carry the same unhurried character — rooms with depth and soul, served by two full baths. A walk-up third floor adds two finished bonus rooms: a studio, a library, a playroom, a quiet office above the treetops. The house keeps offering more.
And then there’s the basement. Name it what you want — a tavern, a speakeasy, a rumpus room — but nothing quite prepares you for it. A massive brick fireplace. A built-in bar. Full-size windows flooding the space with light. And a door that opens directly onto a sunken pebbled courtyard, walled and private, where summer evenings could easily become a habit.
Beyond the main house, the estate unfolds across 6.8 acres of lawn, mature trees, and open land. A charming 882-square-foot guest cottage — two bedrooms, one bath, fully independent utilities — sits privately apart from the manor. It’s the kind of setup that solves problems you haven’t had to solve yet: visiting loved ones, aging parents, a long-term guest, a rental income stream, a caretaker’s quarters. The dairy barn and outbuildings hint at the property’s agricultural past and offer a footprint ready for whatever comes next — a workshop, a studio, a small farm, a vision that hasn’t quite taken shape yet but will the moment you walk the land. There’s even a tennis court.
Fifty-five minutes from Midtown Manhattan, minutes from the village, close to the Rail Trail, the Goshen Historic Track, Legoland, the Shawangunk Wine Trail, and some of the best farm-to-table dining in the Hudson Valley — Brook Farm is private without being remote, historic without being frozen in time.
Properties like this — with this much land, this much character, this much history — don’t come back on the market. This one hasn’t been available in over seventy years. The people who have lived here understood what they had. Now it’s your turn.
A special property steeped in character, with a story already written… and a bold new one waiting to begin. Full of soul and raw possibility, it’s ready for reinvention, for reimagination, for a whole new energy. Awaken its potential, elevate its spirit, and make it entirely your own. The next chapter is yours to craft. Your vision. Your legacy.

Features
Heating System:
Baseboard, Steam, Propane
Cooling System:
No
Basement:
Full, Walk-out Access
View:
Mountain(s), Neighborhood
Patio:
Patio, Porch, Covered
Appliances:
Dishwasher, Oven, Refrigerator, Range, Gas Water Heater
Flooring:
Hardwood
Interior Features:
Eat-in Kitchen, Entrance Foyer, High Ceilings, Original Details, Formal Dining, Built-in Features, Crown Molding
Laundry Features:
Washer Hookup, Electric Dryer Hookup
Lot Features:
Near Public Transit, Views, Part Wooded, Near Shops, Near School, Front Yard
Parking Features:
Driveway
Sewer:
Public Sewer
Utilities:
Trash Collection Public, Propane, Water Connected, Electricity Connected, Sewer Connected
Address Map
City:
Chester Town
State:
NY
Street:
Oakland
Street Number:
1
Street Suffix:
Avenue
Postal Code:
10918
Floor Number:
0
Longitude:
W75° 43' 22.3''
Latitude:
N41° 21' 34.3''
Directions:
Main Street to Oakland Avenue. First driveway on the left.
PostalCity:
Chester
Additional Information
Architectural Style:
Colonial, Mini Estate, Farmhouse
Construction Materials:
Brick, Stone
Elementary School:
Chester Elementary School
High School:
Chester Academy-Middle/High School
Levels:
Three Or More
Agent MlsId:
38186
MiddleOrJunior School:
Chester Academy-Middle/High School
PhotosCount:
50
Special Listing Conditions:
No
Tax Annual Amount:
$27,805
Water Source:
Public
Office MlsId:
RAND18

Residential - MLS# 1006113

1 Oakland Avenue, Chester Town, NY

4 Bedrooms
2 Bathrooms
3,955 Sqft
$1,000,000
Listing ID #1006113
Basic Details
Property Type :
Residential
Property SubType :
Single Family Residence
Listing Type :
For Rent
Listing ID :
1006113
Price :
$1,000,000
Rooms :
11
Bedrooms :
4
Bathrooms :
2
Half Bathrooms :
1
Bathrooms Total :
3
Square Footage :
3,955 Sqft
Lot Area :
6.80 Acre
Year Built :
1851
Status :
Active
Listing Agent :
Christina Rowan
Listing Office :
Howard Hanna Rand Realty
Agent info
Coldwell Banker American Homes
284 West Park Ave
Contact Agent
Walkscore