Active Under Contract
Single family home for sale at 28 Deep Holw Rd, Chester, CT 06412 | MLS# 24199280 | Listing updated on 2026-09-24
Photo 1 of Single family home for sale at 28 Deep Holw Rd, Chester, CT 06412 | MLS# 24199280 | Listing updated on 2026-09-24
Photo 2 of Single family home for sale at 28 Deep Holw Rd, Chester, CT 06412 | MLS# 24199280 | Listing updated on 2026-09-24
Photo 3 of Single family home for sale at 28 Deep Holw Rd, Chester, CT 06412 | MLS# 24199280 | Listing updated on 2026-09-24
Photo 4 of Single family home for sale at 28 Deep Holw Rd, Chester, CT 06412 | MLS# 24199280 | Listing updated on 2026-09-24
33+
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Street View

$559,000

Monthly Est:$2,782

  • Beds Icon3 Beds
  • Beds Icon
    3 Baths
  • Beds Icon1,740sqft

28 Deep Holw Rd, Chester, CT 06412

$2,782/moEst:

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  • Single Family Residence

  • Built in 1890

  • $-- HOA

  • 1.03 acres lot

  • $321/sq.ft

Description

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.

  • Houzeo last checked: 7 hours ago
  • Listing updated: September 24, 2026 at 1:13 pm
  • Listing Provided by: Tom Pentalow | Property Shoppe, LLC
  • Source: SMART MLS-CT | MLS#: 24199280 SMART MLS-CT

Property Details

  • Status

    Active Under Contract

  • Type

    Single Family Residence

  • No. of Stories

    -

  • County

    Middlesex County

  • City

    Chester

  • Neighborhood

    --

  • Year Built

    1890

  • HOA Fees

    -

  • Finished Area

    1,740 sqft

  • Lot Size

    1.03 acres lot

  • Basement Area

    - sqft

  • MLS Name

    SMART MLS

  • MLS Number

    24199280

  • MLS Status

    Under Contract - Continue to Show

  • Days on Market

    21

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Location

HOA Management

0

HOA Fees

$-/

Disclaimer: Amenities are based on third-party information and may vary; buyers must independently verify all amenities, as information is deemed reliable but not guaranteed.

Facts & Features

Rooms

  • Bedrooms & bathrooms

    Bedrooms: 3

    Bathrooms: 3

Interior

  • Sewer

    Septic

  • Appliances

    Oven/range, Refrigerator, Dishwasher

  • Exterior Features

    Barn, Deck, French Doors

  • Cooling

    Window Unit

  • Heating

    Radiant, Oil

Construction

  • Year Built

    Year Built: 1890

  • Home type

    Single Family Residence

  • Foundation Details

    Stone

  • Architectural Style

    Colonial

  • Roof

    Shingle

Utilities & Energy

  • Water Source

    Private Well

  • Laundry Features

    Lower Level

  • Basement

    Full, Partially Finished, Full With Walk Out

  • Parking Features

    Detached Garage

Other Features

  • Lot Features

    Fence Wood, Fence Partial, Fence Privacy, Borders Open Space

  • Subdivision Name

    N/a

Price History

DateEventPrice

09/24/2026

Source: mls_logoSMART MLS-CT #24199280

Contingent (Active Under Contract)

$559,000

$321/sqft

09/17/2026

Source: mls_logoSMART MLS-CT #24199280

Listed for Sale

$559,000

$321/sqft

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Based on information provided to and compiled by the SMART MLS, Inc. through Oct 09, 2026, 02:30PM. IDX information is provided exclusively for consumers’ personal, non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed accurate by the MLS. ©2026 SMART MLS, Inc. All Rights Reserved.

Advertising Broker: Derek Greene | The Greene Realty Group