12 Deep Hollow Road

Closed 1/20/26
Closed 1/20/26
Gallery Image 1
Sold
Last Sold Price
$319,900
3 beds912 sqft$351/sqft
12 Deep Hollow Rd, Chester, CT 06412
Single FamilyProperty Type
0.28 acresLot Size
1960Year Built
$351/sq ftPrice per sq ft
2 carsParking Spaces

Description

Enjoy convenient one level living on a quiet, charming dead-end street just steps from Chester Village. This home offers a full unfinished walkout basement, vinyl siding, thermal windows, and a 200-amp electrical panel. A new furnace was installed in 2019. The neighborhood is truly exceptional, residents are unbelievably kind and feel like family. With a little TLC, this property is ready for your personal updates and vision!Enjoy convenient one level living on a quiet, charming dead-end street just steps from Chester Village. This home offers a full unfinished walkout basement, vinyl siding, thermal windows, and a 200-amp electrical panel. A new furnace was installed in 2019. The neighborhood is truly exceptional, residents are unbelievably kind and feel like family. With a little TLC, this property is ready for your personal updates and vision!
  • Listed by: Craig Milton 860.391.3811 craigmilton@remax.net • Re/Max Valley Shore
Listing closed: 01/20/2026 12:00 AM • Source: SMARTMLS, MLS#: 24141147

Recent comparable sales

Median sold price

$285,000

Avg days on market

12

Sale-to-list ratio

97.5%

Chester, CT

9 comparable properties found

1

$276,000

Sold 03/05/25

3
Bedrooms
1
Bathrooms
1,200
Square Feet
0.26
Acres

4 Bates Road, Chester, CT 06412

front view of a house with a yard and garage
2

$285,000

Sold 04/09/25

3
Bedrooms
1,519
Square Feet
0.85
Acres

14 Straits Road, Chester, CT 06412

$252,500 | 21 East Liberty Street, Chester, CT 06412
3

$252,500

Sold 11/17/25

2
Bedrooms
1,012
Square Feet
0.65
Acres

21 East Liberty Street, Chester, CT 06412

4

$330,000

Sold 07/28/25

2
Bedrooms
1
Bathrooms
1,043
Square Feet
0.45
Acres

7 Kirtland Terrace, Chester, CT 06412

a front view of a house with a yard
5

$360,000

Sold 02/25/25

3
Bedrooms
1,248
Square Feet
2
Acres

261 Middlesex Avenue, Chester, CT 06412

a front view of a house with a yard
6

$220,000

Sold 04/21/26

3
Bedrooms
748
Square Feet
0.23
Acres

15 Hazen Street, Chester, CT 06412

$225,000 | 187 Middlesex Avenue, Chester, CT 06412
7

$225,000

Sold 10/25/24

3
Bedrooms
1,194
Square Feet
0.72
Acres

187 Middlesex Avenue, Chester, CT 06412

8

$325,000

Sold 11/19/25

3
Bedrooms
1.5
Bathrooms
1,368
Square Feet
0.34
Acres

54 Maple Street, Chester, CT 06412

9

$390,000

Sold 10/17/24

2
Bedrooms
1
Bathrooms
1,080
Square Feet
0.52
Acres

40 Railroad Avenue, Chester, CT 06412

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Location

Listing Courtesy of Re/Max Valley Shore, Craig Milton

Sold By Re/Max Valley Shore, Craig Milton

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$1,998 per month

30 year fixed, 6.71% Interest

Principal and Interest

$1,653

Property Taxes

$345

HOA Dues

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Property Information for 12 Deep Hollow Road

Property Details
  • Taxes: $4,142 / year
  • MLS Type: Residential
  • County: Middlesex County
  • Basement Description: Full, Unfinished
  • Direct Waterfront: No
  • Expected Active Date: 11-28-2025
  • Garages Number: 0
  • Style: Ranch
  • Garage Parking Info: Unpaved
  • Swimming Pool: No
  • Expected On Market Date: 11-28-2025
Building Information
  • Year Built: 1960
  • Lot Size: 0.28 AC / 12,196 SF
Summary
Property and Location
  • Acres Source: Public Records
  • Directions: GPS Friendly
  • Elementary School: Chester
  • High School: Per Board of Ed
  • Latitude: 41.408824
  • Longitude: -72.462516
  • Neighborhood Amenities: Library, Medical Facilities, Park, Playground/Tot Lot, Public Transportation, Shopping/Mall, Walk to Bus Lines
  • State: Connecticut
Parking
  • Parking Total Spaces: 2
HOA and Fees
  • Home Owner's Assocation: No
  • Tax Year: July 2025-June 2026
  • Property Tax: $4,142
Interior and Exterior Features
Exterior Features
  • Waterfront Description: Not Applicable
Interior Features
  • Appliances Included: Oven/Range, Refrigerator, Washer
  • Attic Description: Pull-Down Stairs
  • Cooling System: None
  • Heat Type: Baseboard
  • Attic YN: Yes
  • Fireplaces Total: 0
  • Laundry Room Info: Lower Level
  • Laundry Room Location: In Basement.
  • Rooms Total: 5
Room 1
  • Room Entry Order: 1
  • Room Length: 14.0
  • Room Level: Main
  • Room Type: Living Room
  • Room Width: 14.0
Room 2
  • Room Entry Order: 2
  • Room Length: 10.0
  • Room Level: Main
  • Room Type: Eat-In Kitchen
  • Room Width: 16.0
Room 3
  • Room Entry Order: 3
  • Room Level: Main
  • Room Type: Full Bath
Room 4
  • Room Entry Order: 4
  • Room Length: 10.0
  • Room Level: Main
  • Room Type: Bedroom
  • Room Width: 13.0
Room 5
  • Listing Key: 43F6A32DD1DB928BE0631A01100A0E5C
  • Room Entry Order: 5
  • Room Length: 8.0
  • Room Level: Main
  • Room Type: Bedroom
  • Room Width: 10.0
Room 6
  • Room Entry Order: 6
  • Room Length: 12.0
  • Room Level: Main
  • Room Type: Primary Bedroom
  • Room Width: 13.0
Property
Property and Assessments
  • Color: Grey
  • Construction Description: Frame
  • Exterior Siding: Vinyl Siding
  • Foundation Type: Concrete
  • Fuel Tank Location: In Basement
  • New Construction Type: No/Resale
  • Roof: Shingle
  • Year Built: 1960
  • Year Built Source: Public Records
  • Bank Owned Property: No
  • Living Area SQFT Per Public Records: 912
Lot Information
  • Lot Description: Sloping Lot
  • Parcel Number: 940414
  • Sq Ft Est Heated Above Grade: 912.0
  • Sq Ft Total: 912.0
  • Zoning: R-2
Utilities
  • Heat Fuel Type: Oil
  • Hot Water Description: Domestic
  • Sewage System: Septic
  • Water Source: Private Well
Multi Family
Income and Expenses
  • Occupied By: Owner

Property History for 12 Deep Hollow Road

DateEvent & SourcePriceAppreciation
Jan 20, 2026

Closed (Public Record)

Public Record #1927537794

$319,900

+3.6% / yr

Aug 31, 1998

Closed (Public Record)

Public Record #91991360

$122,500—
DateEvent & SourcePrice
01/20/2026

Closed (Public Record)

Public Record #1927537794

$319,900

+3.6% / yr

08/31/1998

Closed (Public Record)

Public Record #91991360

$122,500

For completeness, we often displays two records for one sale: the MLS record and the public record.

Public Records for 12 Deep Hollow Road

Taxable ValueLand$59,220Additions$93,730Total$152,950
Tax Record2025$4,142 ($345 / month)
Home Facts
Beds3Baths1Total Finished SqFt912 SqFtAbove Grade Finished SqFt912 SqFtUnfinished Basement SqFt462 SqFtStories1Lot Size12,197 SqFtStyleSingle Family ResidenceYear Built1960Year Renovated1992ZoningR-2CountyLOWER CONNECTICUT RIVERAPNCSTR M:9 B:350

Schools near 12 Deep Hollow Road

This home is within Regional School District 04.
Rating
School
Type
Grades
Distance
Chester Elementary School
Public - PK to 6
John Winthrop Middle School
Public - 7 to 8
Valley Regional High School
Public - 9 to 12
Rating
School
Distance
Chester Elementary School
PublicPK to 6

John Winthrop Middle School
Public7 to 8

Valley Regional High School
Public9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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Nearby home values

AddressSold priceBedsBathsSqftLot (Sqft)
This home: 12 Deep Hollow Road, Chester, CT 06412
$319,900
3
912
12,196
14 Deep Hollow Road, Chester, CT 06412
$119,000
2
1
1,032
13,504
15 Deep Hollow Road, Chester, CT 06412
$365,000
4
2,066
58,806
17 Deep Hollow Road, Chester, CT 06412
$240,000
3
1,471
66,646
16 Deep Hollow Road, Chester, CT 06412
$100,000
2
1
1,087
42,253
2 Deep Hollow Road, Chester, CT 06412
$629,000
3
2,910
81,021

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Listing Courtesy of Re/Max Valley Shore, Craig Milton

Based on information from one of the following Multiple Listing Services: Darien MLS, Smart MLS and Greenwich Multiple Listing Service. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by Darien MLS, Smart MLS and Greenwich Multiple Listing Service is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals.