1 Oakland Avenue, Chester, NY 10918
Local realty services provided by:ERA Insite Realty Services
1 Oakland Avenue,Chester, NY 10918
$1,000,000
- 4 Beds
- 3 Baths
- 3,955 sq. ft.
- Single family
- Active
Upcoming open houses
- Sat, Jun 1312:00 pm - 02:00 pm
Listed by: christina rowan
Office: howard hanna rand realty
MLS#:1006113
Source:OneKey MLS
Price summary
- Price:$1,000,000
- Price per sq. ft.:$252.84
About this home
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 and a dressing room. 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, charming village setting, close to the Rail Trail, highways, 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....
Contact an agent
Home facts
- Year built:1851
- Listing ID #:1006113
- Added:2 day(s) ago
- Updated:June 10, 2026 at 10:44 PM
Rooms and interior
- Bedrooms:4
- Total bathrooms:3
- Full bathrooms:2
- Half bathrooms:1
- Rooms Total:11
- Flooring:Hardwood
- Dining Description:Eat-In Kitchen, Formal Dining
- Kitchen Description:Dishwasher, Eat-in Kitchen, Oven, Range, Refrigerator
- Basement:Yes
- Basement Description:Full, Walk-Out Access
- Living area:3,955 sq. ft.
Heating and cooling
- Heating:Baseboard, Propane, Steam
Structure and exterior
- Year built:1851
- Building area:3,955 sq. ft.
- Lot area:6.8 Acres
- Lot Features:Near Public Transit, Part Wooded, Views
- Architectural Style:Colonial, Farmhouse, Mini Estate
- Construction Materials:Brick, Stone
- Levels:3 Story
Schools
- High school:Chester Academy-Middle/High School
- Middle school:Chester Academy-Middle/High School
- Elementary school:Chester Elementary School
Utilities
- Water:Public
- Sewer:Public Sewer
Finances and disclosures
- Price:$1,000,000
- Price per sq. ft.:$252.84
- Tax amount:$27,805 (2026)
Features and amenities
- Appliances:Dishwasher, Oven, Refrigerator
- Amenities:Entrance Foyer, High Ceilings
Parking
- Parking description:Driveway
New listings near 1 Oakland Avenue
- Coming Soon
$1,195,000Coming Soon4 beds 4 baths22 Goshen Road, Chester, NY 10918
MLS# 1010585Listed by: HOWARD HANNA RAND REALTY - New
$675,000Active4 beds 3 baths3,100 sq. ft.9 Derose Lane, Chester, NY 10918
MLS# 1010959Listed by: HOWARD HANNA RAND REALTY - New
$875,000Active4 beds 3 baths3,656 sq. ft.49 Stone Mountain Trail, Chester, NY 10918
MLS# 1011165Listed by: EREALTY ADVISORS, INC - New
$720,000Active4 beds 3 baths1,718 sq. ft.26 Bridle Lane, Chester, NY 10918
MLS# 1011224Listed by: OWNER ENTRY.COM - New
$1,200,000Active4 beds 3 baths2,711 sq. ft.63 Whitetail Run, Chester, NY 10918
MLS# 1010784Listed by: SPIRAL NY REAL ESTATE LLC - Open Sat, 12 to 2pmNew
$1,000,000Active4 beds 3 baths3,955 sq. ft.1 Oakland Avenue, Chester, NY 10918
MLS# 1006113Listed by: HOWARD HANNA RAND REALTY - New
$949,000Active4 beds 3 baths3,332 sq. ft.19 Bull Mine Road, Chester, NY 10918
MLS# 1007687Listed by: BHG REAL ESTATE GREEN TEAM - New
$549,900Active3 beds 2 baths2,138 sq. ft.3318 State Route 94, Chester, NY 10918
MLS# 1008703Listed by: HOWARD HANNA RAND REALTY - Open Sun, 11am to 1pmNew
$715,000Active4 beds 3 baths2,784 sq. ft.335 Laroe Road, Chester, NY 10918
MLS# 1009848Listed by: COLDWELL BANKER CHOICE PROP. - New
$1,200,000Active-- beds -- baths4,032 sq. ft.206 Greycourt Road, Chester, NY 10918
MLS# 1003998Listed by: CRONIN & COMPANY REAL ESTATE