28 Deep Hollow Road Chester, CT $ 559,000
28 Deep Hollow Road
$ 559,000
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28 Deep Hollow Road

Chester, CT, 06412
$ 559,000
Bedrooms3 Baths1.2 Sq 1,740

Monthly Estimate*

$ 3,530

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Single Family Home for sale in Chester, CT

for $559,000 with 3 bedrooms and 1 full bath, 2 half baths. This 1,740 square foot home was built in 1890 on a lot size of 1.03.

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. Last, but not least, living on "The Hollow" is all about living on a most beautiful dead end road that affords you access to hiking, fishing, the ability to walk into town and enjoy its old town charm or short bike ride to the Chester Hadlyme Ferry to enjoy a day of wandering the grounds of Gilette Castle. Whether you are looking for a forever home to raise your family, retiring to peaceful surrounds this home is worth a visit!

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Single Family Contingent

Price

$ 559,000

Bedrooms

3

Full Bath

1

Half Bath

2

Property Type

Single Family

Taxes

$ 5,079

Style

Lot Size

1.03

Year Built

1890

Town/City

Chester

MLS | Web ID

24199280

Features
General
Zoning R-2
Neighborhood N/A
County Middlesex
Tax Year July 2026-June 2027
Property Type Single Family For Sale
Status Under Contract - Continue to Show
Acres 1.03
Directions Use GPS
High School Valley
City Chester
Elementary School Chester
Sq Ft Total 1740
DOM 10
Year Built 1890
Style Colonial
Year Built Source Public Records
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Interior
Cooling System Window Unit
Total Rooms 6
Basement Description Full Partially Finished Full With Walk-Out
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Exterior
Water Source Private Well
Lot Description Fence - Wood Fence - Partial Fence - Privacy Borders Open Space
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* Excluded Features
List By
Tom Pentalow

Listing Agent

Property Shoppe, Llc

Broker

thomas.pentalow@gmail.com

Email

Affordability Calculator

$3,953
Per Month
89%
11%
0%
Monthly Principal & Interest
$3,530
Monthly Property Taxes
$423
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
3042126 Elementary School
4789714 Middle School
Valley High School High School
Pricing History
DatePricePrice ChangeDescription
9/17/2026$559,000 Listed Price

Map


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28 Deep Hollow Road, Chester, CT, 06412 is a Single Family Home for sale at $559,000 with 1,740 sqft and a lot size of 1.03. 28 Deep Hollow Road has 3 bedrooms, 1.2 baths, and was built in 1890. The property's zip code is 06412 which is in Chester, CT