28 Deep Hollow Road, Chester, CT 06412 | RYZE Realty Group
Home Homes for Sale Chester, CT 28 Deep Hollow Road

28 Deep Hollow Road, Chester, CT 06412

Single Family For Sale

28 Deep Hollow Road, Chester, CT
Active
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$559,000
Est. Payment: $3,479/mo  Get Pre-Approved
3
Beds
3
Baths
1,740
Sq Ft
1.03
Acres
1890
Yr Built

About This Home

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.

Listed by Tom Pentalow (860) 883-9001 with Property Shoppe, LLC (203) 829-0418

Listing Snapshot

Price $559,000 Days on Our Site 0 days
Property Tax $4,951/yr Style Colonial
Year Built 1890 Total Sq Ft 1,740
Lot Size 1.03 acres HOA Fees N/A
Bedrooms 3 Full Bathrooms 1
Total Rooms 6 Half Baths 2

Key Features

Appliances
  • Oven/Range
  • Refrigerator
  • Dishwasher
Outdoor
  • Barn
  • Deck
  • French Doors
Nearby
  • Shopping/Mall

Structure & Parking

Construction Frame
Roof Shingle
Garage Spaces 2
Garage Type Detached Garage

Systems & Utilities

Heat Radiant
Fuel Oil
Cooling Window Unit
Hot Water Oil, Domestic
Water Private Well
Sewer Septic

Schools

Elem Chester
High Valley

Mortgage Calculator

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Est. Monthly Payment
Principal & Interest
Est. Property Tax $413/mo
Est. Home Insurance

Estimate only. Contact a lender for accurate figures.

Listing History

Date Event Price
Sep 14, 2026 Listed $559,000

Frequently Asked Questions

How much does 28 Deep Hollow Road in Chester, CT cost?
This property is listed at $559,000, which works out to $321 per square foot.
How many bedrooms does 28 Deep Hollow Road have?
This home has 3 bedrooms and 3 bathrooms.
What is the square footage of 28 Deep Hollow Road?
The home is 1,740 square feet, situated on 1.03 acres.
When was 28 Deep Hollow Road in Chester built?
This property was built in 1890.
Is 28 Deep Hollow Road, Chester, CT still available?
The current MLS status of this property is "Active". Contact RYZE Realty Group for the latest availability.
What school district is 28 Deep Hollow Road, Chester in?
This home is served by the Chester public school system, with Chester as the elementary school and Valley as the high school.
How do I schedule a tour of 28 Deep Hollow Road, Chester, CT?
Contact RYZE Realty Group to schedule a private showing. You can submit a tour request directly on this page or call our office.

Listing Agent

Tom Pentalow · (860) 883-9001

Property Shoppe, LLC · (203) 829-0418

MLS# 24199280 · Data provided by SmartMLS. Information deemed reliable but not guaranteed.
Listing updated Sep 17, 2026 7:49 PM UTC

Est. $3,479/mo
$559,000
3 bd · 3 ba · 1,740 sqft
28 Deep Hollow Road, Chester, CT 06412