28 Deep Hollow Road
Chester, Connecticut 06412
- Beds
- 3
- Baths
- 1 | 2
- SqFt
- 1,740
- Acres
- 1.03
- Year Built
- 1890
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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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
Active Listings
12
2 under contract
Median List Price
$499,450
12 active listings
Median Closed Price
$549,500
38 sales
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
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Sep 17, 2026per 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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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.