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MLS 24199280 For Sale Updated September 19, 2026
28 Deep Hollow Road

Chester, Connecticut 06412

$559,000
On market 4 days
28 Deep Hollow Road
1 / 37

About This Property

This beautifully maintained 1890 Farm House in coveted Deep Hollow Road is a rare opportunity and has been a labor of love over the time that the sellers have lived here. This 1.04 acre property on "The Hollow" consists of a house, an oversized 24' x 24' garage/shop, antique "pony" barn with authentic outhouse and custom built service barn suited for a man cave, cigar lounge or whatever else you can envision. Walking into the front door, expect an open floor plan with beautiful knotty alder doors, custom moldings, newly refinished arctic maple flooring, 2 tongue & groove cedar ceilings (1 w/rattan ceiling fans). New Kitchen Aid appliances in a kitchen just waiting for your vision & a spacious walk-in pantry w/ample storage. Gorgeous powder room tucked away features pedestal sink and a 100+ yr old antique cabinet. 2nd floor features 3 bedrooms, 2 which have cathedral ceilings w/remotely operated skylights w/rain sensors to automatically close at first sign of precipitation. Master bedroom has been plugged & wired for stackable washer/dryer. A stand up attic includes a whole house attic fan which creates an impressive amount of air flow. Second floor is on 4 zones of radiant heat; first floor is 1 zone. Basement is walk out and 400 sq ft of newly refreshed space. New carpet, great lighting and wonderful space for a playroom for children, man cave or home office/small business as utilized by the previous owners. Half bath in basement as well.

Property Details

Interior

Heat
Radiant — Oil
Cooling
Window Unit
Basement
Full,Partially Finished,Full With Walk-Out
In-Law Apartment
No

Exterior & Lot

Roof
Shingle
Construction
Construction
Exterior Features
Barn Deck French Doors
Lot Description
Fence - Wood Fence - Partial Fence - Privacy Borders Open Space
Garage & Parking
Detached Garage

Utilities & Systems

Water Source
Private Well
Sewer
Septic

Community & Schools

Elementary
Chester
High
Valley
Nearby Amenities
Shopping/Mall

Appliances

Included
Oven/Range Refrigerator Dishwasher

28 Deep Hollow Road

Chester , Connecticut 06412

$559,000

On market 4 days

Beds
3
Baths
3
SqFt
1,740
Type
Single Family
County Middlesex
Garage 2
Rooms -
Lot Size 1.03 Acres
Property Tax $4,951
Assessed Value $182,840
Year Built 1890
Style Colonial
Zoning R-2

Payment Estimate

30-year fixed. Includes taxes; estimates only.

Estimated Monthly Payment
Open the full mortgage calculator →

Property Map

Map location is based on the property address.

Listing information is deemed reliable but not guaranteed and is sourced from the local MLS feed. Brokerage shown: PTYS20.

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