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28 Deep Hollow Road

Chester, Connecticut 06412

ACTIVE - NEW$559,000
Beds
3
Baths
1 | 2
SqFt
1,740
Acres
1.03
Year Built
1890
Matt Caiola

Matt Caiola

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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.

Key Facts

City/Town
Chester
Neighborhood
N/A
Property / Style
Single Family · Colonial
Year Built
1890
Days on Market
0 days
Beds
3
Baths
1 full · 2 half
Living Area
1,740 sq ft
Lot Size
1.03 acres
Garage / Parking
2 garage
Property Taxes
$4,951 / Annually

Market Snapshot

The Chester Market

Single Family · trailing 12 months

Median Days on Market

9

12 active listings

Median $ / Sq Ft

$285

12 active listings

Sale-to-List Ratio

100.0%

38 sales

How this home compares

List Price

$559,000

vs $499,450 median

11.9% above median

Price / Sq Ft

$321

vs $285 median

12.6% above median

Days on Market

0 days

vs 9 days median

9 days fresher than median

Based on 12 active and 38 closed sales (trailing 12 mo) of single family in Chester. Source: SmartMLS · As of September 18, 2026.

Location

28 Deep Hollow Road, Chester, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$3,559

per month

  • Principal & Interest$2,960
  • Property Taxes$413
  • Insurance$186
  • HOA$0

Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.

Location

City/Town
Chester
Neighborhood
N/A
County
Middlesex

Residence

Property Type
Single Family
Style
Colonial
Year Built
1890
New Construction
No/Resale
Living Area
1,740 sq ft

Schools

Elementary
Chester
High
Valley

Interior

Heating
Radiant
Heat Fuel
Oil
Cooling
Window Unit
Laundry
Lower Level
Laundry Location
basement
Appliances
Oven/RangeRefrigeratorDishwasher
Basement
FullPartially FinishedFull With Walk-Out
In-Law Apartment
No

Exterior & Lot

Lot Size
1.03 acres
Zoning
R-2
Garage / Parking
2 garage spacesDetached Garage
Waterfront Details
Not Applicable
Water Source
Private Well
Sewer
Septic
Flood Zone
No
Construction
Cedar
Color
tan
Roof
Shingle
Foundation
Stone
Exterior Features
BarnDeckFrench Doors
Lot Description
Fence - WoodFence - PartialFence - PrivacyBorders Open Space

Listing & Financials

Property Taxes
$4,951 / Annually
Days on Market
0
MLS #
24199280
MLS Status
Active

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Listed By

Tom Pentalow

(860) 883-9001

Property Shoppe, LLC

(203) 829-0418

This information is believed to be accurate, but without warranty.

The IDX display contains information sourced from SmartMLS, Inc. as of 9/18/2026. This information is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing or leasing. Data is deemed reliable but is not guaranteed accurate by the MLS, the listing broker, the listing agent, or Matt Caiola. Buyers and tenants should independently verify all information that matters to their decision.

Map locations may be approximate. Any offer of compensation, if applicable, is made only to participants of the MLS where the listing is filed. ©2026 Smart MLS, Inc. All rights reserved.

Data last updated on 9/18/2026 at 12:00 AM UTC.