28 Deep Hollow Road, Chester, Connecticut

$559,000

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3

Beds

3

Baths

1,740

Square feet

1.03

Acres

About 28 Deep Hollow Road

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.

Features of 28 Deep Hollow Road

MLS® # 24199280
Price $559,000
Bedrooms 3
Bathrooms 3.00
Full Baths 1
Half Baths 2
Square Footage 1,740
Acres 1.03
Type Single Family For Sale
Style Colonial
Status Under Contract - Continue to Show

Community Information

Address 28 Deep Hollow Road
Area N/A
City Chester
County Middlesex
State Connecticut
Zip Code 06412

Amenities

Parking Detached Garage
# of Garages 2
Is Waterfront No
Waterfront Not Applicable
Has Pool No

Interior

Appliances Oven/Range, Refrigerator, Dishwasher
Heating Radiant, Oil
Cooling Window Unit
Fireplace No
Has Basement Yes
Basement Full, Partially Finished, Full With Walk-Out

Exterior

Exterior Cedar
Exterior Features Barn, Deck, French Doors
Lot Description Fence - Wood, Fence - Partial, Fence - Privacy, Borders Open Space
Roof Shingle
Foundation Stone

School Information

Elementary Chester
High Valley

Additional Information

Date Listed September 17th, 2026
Days on Market 21
Zoning R-2
RE / Bank Owned No

Listing Details

OfficeProperty Shoppe, LLC

Listing Map

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Listing information last updated on October 6th, 2026 at 10:14pm EDT.