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$559,000

  • For Sale
  • Active
  • Single Family
  • 3 Beds
  • 1 Full Bath
  • 2 Partial Baths
  • 1,740 Sq. Ft.
  • 2 Car Garage
  • Updated 3 days ago
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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.

Full Property Details for 28 Deep Holw Rd

General

  • Price: $559,000
  • Taxes: (July 2026-June 2027)
  • Status: Active
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24199280
  • Updated: 9/20/2026
  • Added to Site: 10 day(s) ago

Interior

  • Number of Rooms: 6
  • Appliances: Oven/Range, Refrigerator, Dishwasher

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Full Bathrooms: 1
  • Half Bathrooms: 2

Bedrooms

  • Total Bedrooms: 3
  • Primary Bedroom: Primary Bedroom - Remodeled, Built-Ins, Upper
  • Bedroom 1: Bedroom - Skylight, Wall/Wall Carpet, Main
  • Bedroom 2: Bedroom - Skylight, Wall/Wall Carpet, Upper

Other Rooms

  • Living Room: Living Room - Remodeled, Ceiling Fan, Hardwood Floor, Wide Board Floor, Main
  • Kitchen: Kitchen - Hardwood Floor, Wide Board Floor, Main
  • Dining Room: Dining Room - Remodeled, French Doors, Hardwood Floor, Wide Board Floor, Main
  • Laundry: Lower Level

Exterior

  • Exterior Features: Barn, Deck, French Doors
  • Color: tan

Parking

  • Garage: Yes
  • Garage Spaces: 2
  • Parking: Detached Garage

Location

  • County: Middlesex
  • Driving Directions: Use GPS

School Information

  • Elementary School: Chester
  • High School: Valley

Heating & Cooling

  • Cooling Type: Window Unit
  • Heating Type: Radiant, Oil
  • Heating Fuel: Oil
  • Water Heater: Oil, Domestic

Utilities

  • Sewer: Septic
  • Water: Private Well

Structural Information

  • Architectural Style: Colonial
  • Construction Status: No/Resale
  • Exterior Const.: Cedar
  • Basement Desc.: Full, Partially Finished, Full With Walk-Out
  • Roof: Shingle
  • Attic: Yes
  • Square Feet: 1,740
  • Above Ground: 1,740 Sq. Ft.
  • Year Built: 1890

Lot Features

  • Lot Size (Acres): 1.03
  • Zoning: R-2
  • Lot Description: Fence - Wood, Fence - Partial, Fence - Privacy, Borders Open Space

Financial Considerations

  • Assessment Amount: $182,840
  • Tax Year: July 2026-June 2027

Disclosures and Reports

  • Property ID: 941507

Listed by Property Shoppe, LLC, Tom Pentalow

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Listing agent

— 28 Deep Holw Rd —

  • Tom Pentalow

    Property Shoppe, LLC

Agent Contact: (860) 883-9001 Office Contact: (203) 829-0418

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 28 Deep Holw Rd

School Districts:Chester School District, Regional High School District 04
NameGradesDistance
Chester Elementary School, Chester, CT
23 Ridge Road, Chester, CT 06412
K-61.4 mi
John Winthrop Middle School
1 Winthrop Road, Deep River, CT 06417
7-83.1 mi
Valley Regional High School
256 Kelsey Hill Road, Deep River, CT 06417
9-123 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 28 Deep Holw Rd Get Price Alerts and Save Property

Date
Details
Price
Change
Source
9/14/2026
Listed
$559,000
166.19%
MLS
9/07/2001
Sold
$210,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 28 Deep Holw Rd

Year
Property Taxes
Change
Tax Assessment
Change
2025
$4,951
11%
$182,840
—
2023
$4,470
10%
$182,840
34%
2023
$4,046
1%
$136,240
—
2022
$4,019
—
$136,240
—
2021
$4,019
3%
$136,240
—
2020
$3,899
-1%
$136,240
—
2019
$3,922
5%
$136,240
-1%
2018
$3,734
3%
$137,750
—
2017
$3,631
3%
$137,750
—
2016
$3,522
1%
$137,750
—
2015
$3,488
2%
$137,750
—
2014
$3,419
-33%
$137,750
-41%
2011
$5,085
—
$231,680
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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*These costs are estimates, and the interest rates assume exceptional credit standing.

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with our affiliated lender
NMLS#: 1598647

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Listed by Property Shoppe, LLC, Tom Pentalow

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28 Deep Hollow Road, Chester, CT 06412 (MLS# 24199280) is a Single Family property with 3 bedrooms, 1 full bathroom and 2 partial bathrooms. 28 Deep Hollow Road is currently listed for $559,000 and was received on September 14, 2026. Want to learn more about 28 Deep Hollow Road? Do you have questions about finding other Single Family real estate for sale in Chester? You can browse all Chester real estate or contact a Coldwell Banker agent to request more information.

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