Off Market Jun 2015 for $402K

$688,814

Est. refi paymentEst. refi $2,283/mo

•

2,300

sq ft

27 Upper Kent Hollow Rd, Kent, CT 06757

About this home

Circa 1780 two br cape meticulously restored with great attention to detail. Minutes from lake waramaug, this tiered property has stone walls and great southeastern views. The second structure is a restored vintage tobacco barn, currently a 1 br guest hsehigh ceilings and a large deck overlooking the grounds. A third structure is a pristine post & beam barn ready for conversion with electric and septic system in place. Currently, used for storage.Dutch delft tile in the kitchen, butcher block counter tops and new stainless steel appliances complete with 4 burner viking stove.

Single-familyProperty Type

1780Year Built

2.88 acresLot Size

$299Est. Price/Sq.Ft.

2 spacesParking

Listed by Toni Soule • Bain Real Estate

Bought with Stephen Pener • William Pitt Sotheby's Int'l

Source:Smart MLS #L149589

Redfin Estimate

$688,814

$287K since sold in June 2015$0 since July

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 8.4% higher than the average sale price ($635K) of 6 comparable homes.

SOLD JUL 15, 2026
$576,000
A
3 beds2 baths1,742 sq ft
7 Chimney Rock Rd, Kent, CT 06757
SOLD AUG 3, 2026
$555,000
B
3 beds2 baths1,404 sq ft
3 Edsands Farm Ln, New Milford, CT 06776
SOLD DEC 26, 2025
$425,500
C
2 beds2 baths1,290 sq ft
441 Segar Mountain Rd, South Kent, CT 06785
SOLD JUL 27, 2026
$675,000
D
3 beds2 baths1,427 sq ft
89-A N Main St, Kent, CT 06757
SOLD JUN 26, 2026
$1,050,000
E
3 beds2 baths1,540 sq ft
21 S Ellsworth Rd, Sharon, CT 06069
SOLD JUL 2, 2026
$530,000
F
3 beds2 baths1,414 sq ft
349 Litchfield Rd, New Milford, CT 06776

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Earn from this home

Sell

$405,191

Est. take-home

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Refinance

Est. cash available

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Market trends in 06785, CT

Last updated July 2026

Sale-to-List Price

100.0%

0.0% MoM

Median sale price

$1.5M

$870K MoM

Avg. days on market

24d

4 days MoM

Recently sold homes

0 MoM

New listings for sale

$1,375,000
2 beds2 baths1,316 sq ft
91 Muller Rd, Kent, CT 06757
See all

Provided by Redfin

Sale history for 27 Upper Kent Hollow Rd

Date

Event

Price

Smart MLS #L149589

Jun 30, 2015

Sold

$402,000

$175/sq ft

May 23, 2015

Listing Removed

—

Apr 21, 2014

Listed

$450,000

$196/sq ft

Smart MLS #98365258

Jul 30, 2009

Listing Removed

—

Feb 5, 2008

Listed

$595,000

$259/sq ft

Public Records

Dec 21, 2000

Sold

$350,000

$152/sq ft

Smart MLS #98063912

Feb 9, 2000

Listed

$359,000

$156/sq ft

Smart MLS #98021335

Feb 4, 2000

Listing Removed

—

Aug 4, 1998

Listed

$395,000

$172/sq ft

Smart MLS #97016774

Jun 27, 1998

Listing Removed

—

Jun 3, 1997

Listed

$459,000

$200/sq ft

Smart MLS #95067324

Jul 18, 1995

Listing Removed

—

May 13, 1994

Listed

$479,000

$208/sq ft

Year

Property tax

Land + Additions

Assessment*

2023

$5,281 (+1.0%)

$117,200 + $164,300

$281,500

2022

$5,227 (+1.6%)

$117,200 + $164,300

$281,500

2021

$5,144 (−0.2%)

$117,200 + $159,800

$277,000

2020

$5,155

$117,200 + $159,800

$277,000

2019

$5,155 (−15.0%)

$117,200 + $159,800

$277,000

2018

$6,063

$183,700 + $142,100

$325,800

2017

$6,063 (+1.5%)

$183,700 + $142,100

$325,800

2016

$5,972 (+18.5%)

$183,700 + $142,100

$325,800

2013

$5,040

$181,000 + $167,800

$348,800

Tax history for 27 Upper Kent Hollow Rd

Year

Property tax

Land + Additions

Assessment*

2023

$5,281 (+1.0%)

$117,200 + $164,300

$281,500

2022

$5,227 (+1.6%)

$117,200 + $164,300

$281,500

2021

$5,144 (−0.2%)

$117,200 + $159,800

$277,000

2020

$5,155

$117,200 + $159,800

$277,000

2019

$5,155 (−15.0%)

$117,200 + $159,800

$277,000

2018

$6,063

$183,700 + $142,100

$325,800

2017

$6,063 (+1.5%)

$183,700 + $142,100

$325,800

2016

$5,972 (+18.5%)

$183,700 + $142,100

$325,800

2013

$5,040

$181,000 + $167,800

$348,800

*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

2.5

Stories

—

Lot width

—

Lot depth

—

Lot size

125,452

Year renovated

—

Sq. Ft.

2,300

Year built

1780

Style

Single Family Residential

County

Litchfield County

APN

1944033

Parking Spaces

Basement

Yes

Accessible

HOA Dues

—

Garage

Features

Views

Last updated by owner on Mar 22, 2026.

Property details

Interior

Interior Information
Total Rooms: 4
Laundry Room Location: First Floor
Interior Features: Cable - Available

Bathroom Information
# of Baths (Full): 2

Bedroom Information
Beds Total: 2

Room Information
Room Count: 4
Basement Description: Partial

Exterior

Exterior Features
Exterior Siding: Clapboard

Lot Information
Lot Description: Open Lot, Rolling

Property Information
Property Type: Single Family For Sale
Driveway Type: Gravel

Financial

Assessments Information
Assessed Value: $325,800

Rental Information
Lease Purchase YN: No

Utilities

Utility Information
Water Source: Private Well
Sewage System: Septic
Hot Water Description: Electric
Heat Type: Other
Heat Fuel Type: Oil
Fuel Tank Location: Above Ground

Location

School Information
High School: Housatonic
Elementary School: Kent Center

Location Information
State: Connecticut
Directions: Rte 341 east to kent hollow rd on right come to fork go right and house in on left
County: Litchfield

Public facts

Beds: 3
Baths: 2.5
Sq. Ft.: 2,300
Stories: —
Parking Spaces: 2
Basement: Yes
Accessible: No
Lot Size: 2.88 acres
Style: Single Family Residential
Year Built: 1780
Year Renovated: —
County: Litchfield County
APN: 1944033
HOA Dues: —
Garage: No
Features: Views

Home facts updated by owner on Mar 22, 2026

Other

Documents & Disclosures
Supplement Count Public: 1

Around this home

Schools

Kent Center School

Public PreK-8 • Assigned • 4.0mi

7/10

Housatonic Valley Regional High School

Public 9-12 • Assigned • 15.1mi

5/10

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

3/10 Fire Factor

0.31% chance of being in a wildfire in next 30 years

3/10 Heat Factor

7 days above 95° expected this year, 16 days in 30 years

4/10 Wind Factor

17% chance of strong winds in next 30 years

2/10 Air Factor

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

Provided by First Street

Historical weather

Kent, CT • 06757

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

Try the sun simulator tool to see how light moves across the property at different times of day and year.

Provided by Shadowmap

Estimated sale price

$655,000 – $793,000

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Nearby similar homes

$1,375,000

2 beds2 baths1,316 sq ft

91 Muller Rd, Kent, CT 06757

$675,000

2 beds1.5 baths1,236 sq ft

104 Cherniske Rd, New Milford, CT 06776

$499,900

5 beds2.5 baths2,597 sq ft

28 Old Mill Rd, New Milford, CT 06776

$1,250,000

1 bed2 baths1,056 sq ft

178 Carter Rd, Warren, CT 06754

$1,139,000

4 beds4 baths4,442 sq ft

11 Stone Fences Ln, South Kent, CT 06785

$4,750,000

4 beds5 baths6,836 sq ft

90 Tinker Hill Rd, New Preston Marble Dale, CT 06777

New listings for sale in 06757

$1,375,000

2 beds2 baths1,316 sq ft

91 Muller Rd, Kent, CT 06757

Home values near 27 Upper Kent Hollow Rd

Data from public records.

Address	Redfin Estimate
7 Upper Kent Hollow Rd, Kent, CT 2 Beds \| 1.5 Baths \| 1176 Sq. Ft.	$421,456
12 Upper Kent Hollow Rd, Kent, CT 2 Beds \| 2 Baths \| 1527 Sq. Ft.	$452,938

Address	Redfin Estimate
50 Upper Kent Hollow Rd, Kent, CT 3 Beds \| 2.5 Baths \| 2612 Sq. Ft.	$746,064
11 Upper Kent Hollow Rd, Kent, CT 2 Beds \| 1 Baths \| 789 Sq. Ft.	$352,656

Address	Redfin Estimate
6 Upper Kent Hollow Rd, Kent, CT 2 Beds \| 1 Baths \| 1845 Sq. Ft.	$502,929
47 Upper Kent Hollow Rd, Kent, CT 2 Beds \| 2 Baths \| 1770 Sq. Ft.	$1,276,045

Property information provided by Smart MLS when last listed in 2014. This data may not show owner updates. Learn more.

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About this home

Redfin Estimate

Earn from this home

Market trends in 06785, CT

Sale history for 27 Upper Kent Hollow Rd

Tax history for 27 Upper Kent Hollow Rd

Public record

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 06757

Home values near 27 Upper Kent Hollow Rd

More real estate resources