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28 Deep Hollow Road, 
Chester, CT 06412

$559,000


3

Beds


3

Baths


1,740

Sq Ft


Single Family

Pending

Listed by

Tom Pentalow, (860) 883-9001

Property Shoppe, LLC., (203) 829-0418

(203) 829-0418

Last updated:

October 22, 2026, 12:02 PM

MLS#

24199280

Source:

CT

About This Home

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.

Home Facts

Single Family

3 Baths

3 Bedrooms

Built in 1890

Price Summary

559,000

$321 per Sq. Ft.

MLS #:

24199280

Last Updated:

October 22, 2026, 12:02 PM

Added:

a month ago


Rooms & Interior

Bedrooms

Total Bedrooms:

3

Bathrooms

Total Bathrooms:

3

Full Bathrooms:

1

Interior

Living Area:

1,740 Sq. Ft.


Structure

Structure

Architectural Style:

Colonial

Building Area:

1,740 Sq. Ft.

Year Built:

1890


Lot

Lot Size (Sq. Ft):

44,866


Finances & Disclosures

Finances

Price:

$559,000

Price per Sq. Ft:

$321 per Sq. Ft.

Source:CT
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Contact an Agent

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Contact, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If a Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby's International Realty®). I acknowledge that I have read and agree to the terms of use and privacy notice.