Off Market Feb 2025 for $485K

$674,029

Est. refi paymentEst. refi $1,860/mo

•

2,338

sq ft

5 Shear Shop Rd, Litchfield, CT 06759

About this home

DRASTIC REDUCTION on this rare find! This c.1782 center chimney Colonial located on the Green in the heart of the Milton Center Historic District. Built as a single family dwelling in an era when Milton was bustling, it served the Hartford-Poughkeepsie stagecoach line as the Guild Tavern from 1833-1877. It has been a single-family residence ever since. There are 3 working fireplaces on the main level and one discontinued fireplace in the primary bedroom on the upper level. Wood floors and chestnut beams have not been painted or mistreated. Ceilings are high on both main and upper floors (8+ feet). An A2 survey of the 1.255 acre lot indicates over 400' frontage on Shear Shop Road. Also, over 400' of the very scenic Marshepaug River runs through the property. Automatic generator. Property is being sold "As-Is." Room sizes are approximate. The 2-story barn with 2-car garage is compromised and will need extensive repairs or replacement. It is left in place for the grandfathered footprint to aid a future owner and the town regarding permits for a rebuild or replacement. When viewing this property in person, please do not enter the barn/garage. ** This property may qualify for a CT State Historic Homes Rehabilitation Tax Credit up to $30,000. ** (NB A pink tape on a Shear Shop bush indicates the approximate boundary line.)

Single-familyProperty Type

1782Year Built

1.26 acresLot Size

$288Est. Price/Sq.Ft.

4 spacesParking

Listed by Ileana Santore • Marrin Santore Realty LLC

Bought with Kevin Geysen • William Pitt Sotheby's Int'l

Source:Smart MLS #24044737

Redfin Estimate

$674,029

$189K since sold in February 2025$2,000 since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 20.3% higher than the average sale price ($561K) of 5 comparable homes.

SOLD JUL 10, 2026
$610,000
A
4 beds2 baths1,788 sq ft
11 Sheldon Ln, Litchfield, CT 06759
SOLD FEB 24, 2026
$355,000
B
3 beds2 baths2,392 sq ft
552 Milton Rd, Litchfield, CT 06759
SOLD MAY 11, 2026
$850,000
C
4 beds2.5 baths2,658 sq ft
273 Bantam Lake Rd, Morris, CT 06763
SOLD JUL 31, 2026
$565,000
D
3 beds2 baths1,699 sq ft
255 Norfolk Rd, Litchfield, CT 06759
SOLD APR 9, 2026
$422,500
E
4 beds1.5 baths1,794 sq ft
204 Goodhouse Rd, Litchfield, CT 06759

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Earn from this home

Sell

$256,255

Est. take-home

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Refinance

Est. cash available

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Rent

$2,980/mo

Redfin rental estimate

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Market trends in 06759, CT

Last updated August 2026

Buyer's Market

Seller's Market

Balanced market

Sale-to-List Price

101.2%

1.3% MoM

Median sale price

$595K

$15K MoM

Avg. days on market

39d

3 days MoM

Recently sold homes

1 MoM

New listings for sale

NEW 9 HRS AGO
$2,395,000
4 beds3.5 baths4,346 sq ft
171 South St, Litchfield, CT 06759
COMING SOON
$449,000
4 beds2 baths1,790 sq ft
85 E Litchfield Rd, Litchfield, CT 06759
3D WALKTHROUGH
$875,000
3 beds3 baths2,585 sq ft
128 Sheldon Ln, Litchfield, CT 06759
$695,000
3 beds2 baths2,039 sq ft
329 Norfolk Rd, Litchfield, CT 06759
$2,500,000
5 beds4.5 baths4,145 sq ft
162 Hutchinson & Mike Road Pkwy, Litchfield, CT 06759
OPEN SEP 12, 10AM TO 12PM
$299,900
3 beds1.5 baths1,040 sq ft
14 Meadow Ridge Rd, Litchfield, CT 06759
$780,000
3 beds3.5 baths3,020 sq ft
351 Hunter Dr #351, Litchfield, CT 06759
See all

Provided by Redfin

Sale history for 5 Shear Shop Rd

Date

Event

Price

Smart MLS #24044737

Feb 14, 2025

Sold

$485,000

$207/sq ft

Feb 5, 2025

Pending

—

Jan 13, 2025

Contingent

—

Oct 8, 2024

Price Changed

$525,000

$225/sq ft

Sep 8, 2024

Listed

$575,000

$246/sq ft

Smart MLS #L148406

Jul 31, 2014

Sold

$284,500

$122/sq ft

Jan 10, 2014

Listed

$289,900

$124/sq ft

Historic milton property, guild tavern-18th c. Inn on old stagecoach line. Center chimney colonial, wood floors, chestnut beams. 400' frontage on marshepaug river. Sold as-is - building inspections for information only. Owner is co-lister. Financial programs may be available to qualified buyers to help customize this historic home into the home of their dreams. All season sun porch overlooks fieldstone patio. Country kitchen with vaulted ceiling, double sinks facing milton green. Listen to marshepaug river running through property.2-Story barn needs renovation. Milton historic district is in the national register of historic places. Sold in as_is condition-inspections for info only.

Smart MLS #L143272

Dec 31, 2013

Listing Removed

—

Jul 16, 2012

Listed

$324,900

$139/sq ft

Year

Property tax

Land + Additions

Assessment*

2022

$6,258 (−2.9%)

$118,870 + $114,630

$233,500

2021

$6,445 (−0.4%)

$118,870 + $114,630

$233,500

2020

$6,468 (−1.8%)

$118,870 + $114,630

$233,500

2019

$6,585 (−17.2%)

$118,870 + $114,630

$233,500

2018

$7,952 (+0.4%)

$149,990 + $137,080

$287,070

2017

$7,923 (+3.4%)

$149,990 + $137,080

$287,070

2016

$7,665 (+6.0%)

$149,990 + $137,080

$287,070

2014

$7,234

$149,990 + $137,080

$287,070

Tax history for 5 Shear Shop Rd

Year

Property tax

Land + Additions

Assessment*

2022

$6,258 (−2.9%)

$118,870 + $114,630

$233,500

2021

$6,445 (−0.4%)

$118,870 + $114,630

$233,500

2020

$6,468 (−1.8%)

$118,870 + $114,630

$233,500

2019

$6,585 (−17.2%)

$118,870 + $114,630

$233,500

2018

$7,952 (+0.4%)

$149,990 + $137,080

$287,070

2017

$7,923 (+3.4%)

$149,990 + $137,080

$287,070

2016

$7,665 (+6.0%)

$149,990 + $137,080

$287,070

2014

$7,234

$149,990 + $137,080

$287,070

*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.

Public record

Beds

Baths

Stories

Lot width

—

Lot depth

—

Lot size

1.26 Acres

Year renovated

—

Sq. Ft.

2,338

Year built

1782

Style

Single Family Residential

County

Litchfield County

APN

819497

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on May 25, 2023.

Property details

Parking

Garage Information
Garage & Parking: Off Street Parking, Unpaved

Parking Information
Parking Total Spaces: 4

Interior

Interior Information
Total Rooms: 8
Laundry Room Location: In main level bathroom
Laundry Room Info: Main Level
Fireplaces Total: 3
Appliances Included: Gas Range, Refrigerator, Dishwasher, Washer, Dryer

Bathroom Information
# of Baths (Full): 2

Bedroom Information
Beds Total: 4

Room Information
Basement Description: Partial, Unfinished, Partial With Hatchway
Has Attic
Attic Description: Storage Space, Pull-Down Stairs

Exterior

Exterior Features
Roof Information: Asphalt Shingle
Exterior Siding: Clapboard, Wood
Exterior Features: Gutters, French Doors, Patio

Lot Information
Lot Description: Corner Lot, Lightly Wooded, Level Lot, Historic District, Open Lot

Building Information
Foundation Type: Stone
Construction Description: Frame

Property Information
Waterfront Description: River
Property Type: Single Family For Sale
Living Area SQFT Per Public Record: 2338

Financial

Assessments Information
Assessed Value: $307,920

Utilities

Utility Information
Water Source: Private Well
Sewage System: Septic
Heat Type: Hot Water
Heat Fuel Type: Oil
Fuel Tank Location: In Basement
Energy Features: Generator

Location

School Information
Middle Jr High School: Per Board of Ed
Intermediate School: Per Board of Ed
High School: Per Board of Ed
Elementary School: Center

Location Information
State: Connecticut
Nearby Amenities: Golf Course, Health Club, Lake, Library, Medical Facilities, Private School(s)
Flood Zone
Directions: Route 202 to Milton Road to Milton Center. Property is on the corner of Milton Road and Shear Shop Road.
Direct Waterfront
County: Litchfield

Public facts

Beds: 3
Baths: 2.0
Sq. Ft.: 2,338
Stories: 2.0
Lot Size: 1.26 acres
Style: Single Family Residential
Year Built: 1782
Year Renovated: —
County: Litchfield County
APN: 819497

Home facts updated by county records on May 25, 2023

Other

Documents & Disclosures
Supplement Count Public: 6

Around this home

Schools

Litchfield Intermediate School

Public 4-5 • Assigned • 3.9mi

Plumb Hill Middle School

Public 6-8 • Assigned • 3.7mi

Region 20 High School

Public 9-12 • Assigned • 3.6mi

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

3/10 Heat Factor

7 days above 93° expected this year, 16 days in 30 years

4/10 Wind Factor

21% chance of strong winds in next 30 years

3/10 Air Factor

2 unhealthy days expected this year, 3 days in 30 years

Provided by First Street

Historical weather

Litchfield, CT • 06759

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

In this area, properties receive around 8.6 hours in June and 4.1 hours in December, placing it below the U.S. average for solar exposure.

8.6 hrs

4.1 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$641,000 – $776,000

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Home values near 5 Shear Shop Rd

Data from public records.

Address	Redfin Estimate
10 Headquarters Rd, Litchfield, CT 2 Beds \| 1 Baths \| 1033 Sq. Ft.	$307,756
543 Milton Rd, Litchfield, CT 3 Beds \| 1.5 Baths \| 2086 Sq. Ft.	$707,181

Address	Redfin Estimate
122 Saw Mill Rd, Litchfield, CT 3 Beds \| 3 Baths \| 1438 Sq. Ft.	$541,976
127 Saw Mill Rd, Litchfield, CT 5 Beds \| 2 Baths \| 2812 Sq. Ft.	$952,516

Address	Redfin Estimate
557 Milton Rd, Litchfield, CT 4 Beds \| 2 Baths \| 1923 Sq. Ft.	$675,470
566 Milton Rd, Litchfield, CT 4 Beds \| 4.5 Baths \| 4737 Sq. Ft.	$1,881,034

Property information provided by Smart MLS when last listed in 2024. This data may not match . Learn more.

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About this home

Redfin Estimate

Earn from this home

Market trends in 06759, CT

Sale history for 5 Shear Shop Rd

Tax history for 5 Shear Shop Rd

Public record

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 06759

Home values near 5 Shear Shop Rd

More real estate resources