Sold
Last Sold Price
3 beds2,910 sqft$216/sqft
2 Deep Hollow Rd, Chester, CT 06412
Single FamilyProperty Type
1.86 acresLot Size
1737Year Built
$216/sq ftPrice per sq ft
2 carsParking Spaces

Description

Unique home-converted former grist & saw mill-many updates-new kitch-library-master suite-liv room w/vaulted ceiling & fp-3 season porch overlooks beautiful gardens-stream-w/pond & waterfall-exceptional property near chester village chester-not a drive-byUnique home-converted former grist & saw mill-many updates-new kitch-library-master suite-liv room w/vaulted ceiling & fp-3 season porch overlooks beautiful gardens-stream-w/pond & waterfall-exceptional property near chester village chester-not a drive-by
Listing closed: 06/11/2014 12:00 AM • Source: SMARTMLS, MLS#: M9143611

Recent comparable sales

Median sold price

$675,000

Avg days on market

37

Sale-to-list ratio

97.3%

Chester, CT

9 comparable properties found

a front view of a house with large windows
1

$635,000

Sold 04/30/26

3
Bedrooms
2,752
Square Feet
1.39
Acres
$515,000 | 12 Meadow Lane, Chester, CT 06412
2

$515,000

Sold 07/27/26

3
Bedrooms
2,971
Square Feet
4.15
Acres
$582,000 | 28 Goose Hill Road, Chester, CT 06412
3

$582,000

Sold 11/21/24

3
Bedrooms
2,398
Square Feet
1.65
Acres
$810,000 | 14 Maple Street, Chester, CT 06412
4

$810,000

Sold 11/14/25

3
Bedrooms
2,322
Square Feet
1
Acres
$675,000 | 108 Middlesex Avenue, Chester, CT 06412
5

$675,000

Sold 05/01/25

4
Bedrooms
4,056
Square Feet
0.74
Acres
$750,000 | 9 Hickory Hill Drive, Chester, CT 06412
6

$750,000

Sold 02/20/26

3
Bedrooms
2,888
Square Feet
1.23
Acres
an aerial view of a house with a big yard and large trees
7

$1,135,000

Sold 06/30/25

4
Bedrooms
3,351
Square Feet
1.01
Acres
$500,000 | 5 Marina View Drive, Chester, CT 06412
8

$500,000

Sold 01/17/25

3
Bedrooms
2,037
Square Feet
11.89
Acres
$760,000 | 28 Hoop Pole Hill Road, Chester, CT 06412
9

$760,000

Sold 11/03/25

4
Bedrooms
3,396
Square Feet
2.01
Acres

Location

Listing Courtesy of Berkshire Hathaway NE Prop., Margaret Driscoll

Sold By William Raveis Real Estate, Tracey Kersteen

Add your commute

Payment Calculator

$3,891 per month

30 year fixed, 6.71% Interest

Principal and Interest

$3,250

Property Taxes

$640

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Know your buying power with a preapproval and custom rate in minutes

Rocket Mortgage1

Property Information for 2 Deep Hollow Road

Property Details
  • Taxes: $7,682 / year
  • MLS Type: Residential
  • Basement Description: Full With Walk-Out, Unfinished
  • Direct Waterfront: Yes
  • Garages Number: 2
  • Style: Colonial
  • Garage Parking Info: Attached Garage
  • Swimming Pool: No
Building Information
  • Year Built: 1737
  • Lot Size: 1.86 AC / 81,021 SF
Summary
Property and Location
  • Directions: Chester centre/w main right to pleasant right to liberty to deep hollow...1St home on right
  • Elementary School: Town
  • High School: Town
  • Latitude: 41.408436
  • Longitude: -72.46108
  • State: Connecticut
HOA and Fees
  • Property Tax: $7,682
Interior and Exterior Features
Exterior Features
  • Exterior Features: Balcony, Garden Area, Patio, Stone Wall
  • Waterfront Description: Pond, River, View, Walk to Water
Interior Features
  • Appliances Included: Cook Top, Dishwasher, Oven/Range, Refrigerator, Range Hood, Washer
  • Heat Type: Baseboard, Other
  • Attic YN: No
  • Fireplaces Total: 1
  • Interior Features: Cable - Available, Open Floor Plan
  • Laundry Room Location: First Floor
  • Room Count: 8
  • Rooms Total: 8
Room 1
  • Room Entry Order: 1
  • Room Features: Full Bath,Skylight,Upper Level
  • Room Length: 25.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 14.0
Room 2
  • Room Entry Order: 1
  • Room Features: Full Bath,Skylight,Upper Level
  • Room Length: 25.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 14.0
Room 3
  • Room Entry Order: 12
  • Room Type: Other
Room 4
  • Room Entry Order: 12
  • Room Type: Other
Room 5
  • Listing Key: DD57C721970DE948E0531401100A8539
  • Room Entry Order: 2
  • Room Features: Upper Level
  • Room Length: 13.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 11.0
Room 6
  • Room Entry Order: 2
  • Room Features: Upper Level
  • Room Length: 13.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 11.0
Room 7
  • Room Entry Order: 4
  • Room Features: Vaulted Ceiling
  • Room Length: 27.0
  • Room Type: Dining Room
  • Room Width: 13.0
Room 8
  • Room Entry Order: 4
  • Room Features: Vaulted Ceiling
  • Room Length: 27.0
  • Room Type: Dining Room
  • Room Width: 13.0
Room 9
  • Listing Key: DD57C721970DE948E0531401100A8539
  • Room Entry Order: 5
  • Room Features: Vaulted Ceiling
  • Room Length: 15.0
  • Room Level: Main
  • Room Type: Family Room
  • Room Width: 14.0
Room 10
  • Room Entry Order: 5
  • Room Features: Vaulted Ceiling
  • Room Length: 15.0
  • Room Level: Main
  • Room Type: Family Room
  • Room Width: 14.0
Room 11
  • Room Entry Order: 6
  • Room Features: Country
  • Room Length: 14.0
  • Room Type: Kitchen
  • Room Width: 11.0
Room 12
  • Room Entry Order: 6
  • Room Features: Country
  • Room Length: 14.0
  • Room Type: Kitchen
  • Room Width: 11.0
Room 13
  • Room Entry Order: 7
  • Room Features: Fireplace,Great Room,Vaulted Ceiling
  • Room Length: 26.0
  • Room Type: Living Room
  • Room Width: 16.0
Room 14
  • Room Entry Order: 7
  • Room Features: Fireplace,Great Room,Vaulted Ceiling
  • Room Length: 26.0
  • Room Type: Living Room
  • Room Width: 16.0
Room 15
  • Room Entry Order: 8
  • Room Features: Full Bath,Walk-In Closet
  • Room Length: 24.0
  • Room Type: Primary Bedroom
  • Room Width: 14.0
Room 16
  • Room Entry Order: 8
  • Room Features: Full Bath,Walk-In Closet
  • Room Length: 24.0
  • Room Type: Primary Bedroom
  • Room Width: 14.0
Property
Property and Assessments
  • Driveway Type: Crushed Stone
  • Exterior Siding: Vertical Siding, Wood
  • Fuel Tank Location: Above Ground
  • Sq Ft Source: Public Records
  • Year Built: 1737
  • Bank Owned Property: No
Lot Information
  • Lot Description: Level Lot, Professionally Landscaped
  • Parcel Number: 940131
  • Sq Ft Total: 2910.0
Utilities
  • Heat Fuel Type: Electric, Oil
  • Hot Water Description: Domestic
  • Sewage System: Septic
  • Water Source: Private Well

Property History for 2 Deep Hollow Road

DateEvent & SourcePriceAppreciation
Jun 11, 2014

Closed (Public Record)

Public Record #418609481

$629,000

+2.9% / yr

Sep 5, 1996

Closed (Public Record)

Public Record #91991529

$380,000
DateEvent & SourcePrice
06/11/2014

Closed (Public Record)

Public Record #418609481

$629,000

+2.9% / yr

09/05/1996

Closed (Public Record)

Public Record #91991529

$380,000

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

Public Records for 2 Deep Hollow Road

Taxable ValueLand$68,390Additions$315,210Total$383,600
Tax Record2025$10,388 ($866 / month)
Home Facts
Beds3Baths2.5Total Finished SqFt3,186 SqFtAbove Grade Finished SqFt3,186 SqFtUnfinished Basement SqFt650 SqFtStories2Lot Size81,022 SqFtStyleSingle Family ResidenceYear Built1992Year Renovated1996ZoningR-1CountyLOWER CONNECTICUT RIVERAPNCSTR M:9 B:352

Schools near 2 Deep Hollow Road

This home is within Regional School District 04.
Rating
School
Type
Grades
Distance
Public - PK to 6
Public - 7 to 8
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.

Similar Homes

New listings in 06412

$439,900 | 43 Goose Hill Road, Chester, CT 06412
1/39
Coming Soon

$439,900

3
Bedrooms
1,742
Square Feet
1.9
Acres
$1,900,000 | 47 East Kings Highway, Chester, CT 06412
1/40
Virtual Tour

$1,900,000

4
Bedrooms
3,957
Square Feet
3.2
Acres
$499,000 | 88 Winthrop Road, Chester, CT 06412
1/24

$499,000

3
Bedrooms
2,240
Square Feet
33.97
Acres
$824,900 | 275 West Main Street, Chester, CT 06412
1/39

$824,900

4
Bedrooms
2,706
Square Feet
2
Acres
$465,000 | 6 Castle View Drive, Chester, CT 06412
1/32

$465,000

3
Bedrooms
2,031
Square Feet
0.43
Acres
$1,350,000 | 19 Denlar Drive, Chester, CT 06412
1/40
Listed By Coldwell Banker Realty

$1,350,000

2
Bedrooms
5,886
Square Feet
0.66
Acres
$764,900 | 13 High Field Lane, Chester, CT 06412
1/40
Coming SoonOpen: 9/19 11:00AM - 02:00PM

$764,900

4
Bedrooms
2,662
Square Feet
2.24
Acres
front view of a house with a yard
1/39
Under Contract - Continue To Show

$599,900

2
Bedrooms
2,000
Square Feet
$499,900 | 55 Wig Hill Road, Chester, CT 06412
1/38

$499,900

3
Bedrooms
1,774
Square Feet
1.43
Acres

Nearby home values

AddressSold priceBedsBathsSqftLot (Sqft)
This home: 2 Deep Hollow Road, Chester, CT 06412
$629,000
3
2,910
81,021
$465,000
2
1,569
17,424
2
2
1,267
76,230
$145,000
158,558
$319,900
3
912
12,196
$265,000
3
1,232
13,503

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the seller's discretion. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties make no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of Berkshire Hathaway NE Prop., Margaret Driscoll

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.