395 Chestnut Hill Rd, Stamford, CT 06903

Off market jan 2019 for $777K

$1,842,719

Est. refi paymentEst. refi $5,258/mo

•

5,288

sq ft

395 Chestnut Hill Rd, Stamford, CT 06903

About this home

Welcome home! Upon entering you will be welcomed by a large foyer that leads to a large living room with 24'ceilings and a wall of windows perfect for having a drink while you admire nature outside your window. Living room leads to the enclosed sun room lined in cedar which leads out to your stone patio. First floor also features a formal dining room, very large kitchen with door to the backyard, a family room/den, a large mud room and a 5th bedroom with en suite perfect for au pair or guests. Upstairs you can put up your feet in the large master bedroom sitting room with fireplace and several closets, ensuite bathroom with bidet and stairs up to the finished attic perfect for a home office. Upstairs also features 3 bedrooms and 2 full bathrooms plus an additional walk-in attic space above the 3 car garage! Property also features a cottage with a fireplace and additional 2 car garage. Huge basement with 2 separate entrances and fireplace, finish the space and make it the perfect party/entertainment area or guest suite.

Single-familyProperty Type

1937Year Built

2.87 acresLot Size

$348Est. Price/Sq.Ft.

5 car garageParking

Listed by Cecilia Valentino • Keller Williams Prestige Prop.

Bought with Ximena Perez • Keller Williams Prestige Prop.

Source:Smart MLS #170142243

Redfin Estimate

$1,842,719

$1.1M since sold in January 2019$25K since September

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 1.1% lower than the average sale price ($1.86M) of 6 comparable homes.

SOLD APR 20, 2026
$2,410,000
A
4 beds4.5 baths5,972 sq ft
25 Wildwood Rd, Stamford, CT 06903
SOLD FEB 6, 2026
$2,150,000
B
5 beds4.5 baths5,593 sq ft
271 Hunting Ridge Rd, Stamford, CT 06903
SOLD JUN 30, 2026
$975,000
C
4 beds3.5 baths4,076 sq ft
19 Timber Mill Cir, Stamford, CT 06903
SOLD MAR 23, 2026
$1,900,000
D
4 beds3.5 baths3,812 sq ft
107 Deepwood Rd, Stamford, CT 06903
SOLD DEC 30, 2025
$2,000,000
E
5 beds4.5 baths5,528 sq ft
1616 Long Ridge Rd, Stamford, CT 06903
SOLD NOV 7, 2025
$1,749,000
F
5 beds4.5 baths6,415 sq ft
162 Wellington Dr, Stamford, CT 06903

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Earn from this home

Sell

$1,212,862

Est. take-home

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Refinance

Est. cash available

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Rent

$3,747/mo

Redfin rental estimate

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Market trends in 06903, CT

Last updated September 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

105.7%

0.7% MoM

Median sale price

$1.2M

$21K MoM

Avg. days on market

33d

2 days MoM

Recently sold homes

0 MoM

New listings for sale

$1,595,000
4 beds4.5 baths4,459 sq ft
13 Lakeside Dr, Stamford, CT 06903
COMING SOON
$1,325,000
4 beds3.5 baths4,001 sq ft
153 West Trl, Stamford, CT 06903
COMING SOON
$999,900
4 beds3 baths2,940 sq ft
45 Smoke Hill Dr, Stamford, CT 06903
$650,000
2 beds2.5 baths2,198 sq ft
137 E Hunting Ridge Rd, Stamford, CT 06903
$980,000
3 beds2.5 baths1,856 sq ft
753 Den Rd, Stamford, CT 06903
VIDEO TOUR
$1,799,000
4 beds3.5 baths3,247 sq ft
29 S Lake Dr, Stamford, CT 06903
VIDEO TOUR
$2,500,000
5 beds5.5 baths7,633 sq ft
333 Rock Rimmon Rd, Stamford, CT 06903
$2,395,000
5 beds4.5 baths6,440 sq ft
64 Huckleberry Holw, Stamford, CT 06903
$1,495,000
3 beds3.5 baths3,244 sq ft
16 Wire Mill Rd Unit K, Stamford, CT 06903
See all

Provided by Redfin

Sale history for 395 Chestnut Hill Rd

Year

Property tax

Land + Additions

Assessment*

2022

$23,472 (+1.4%)

$275,570 + $615,870

$891,440

2021

$23,151 (+2.5%)

$275,570 + $615,870

$891,440

2020

$22,580 (+3.8%)

$275,570 + $615,870

$891,440

2019

$21,760 (+3.6%)

$275,570 + $583,500

$859,070

2018

$21,004 (−1.2%)

$275,570 + $583,500

$859,070

2017

$21,256 (+3.1%)

$252,610 + $578,010

$830,620

2016

$20,616 (+6.5%)

$252,610 + $578,010

$830,620

2014

$19,362

$252,610 + $578,010

$830,620

Tax history for 395 Chestnut Hill Rd

Year

Property tax

Land + Additions

Assessment*

2022

$23,472 (+1.4%)

$275,570 + $615,870

$891,440

2021

$23,151 (+2.5%)

$275,570 + $615,870

$891,440

2020

$22,580 (+3.8%)

$275,570 + $615,870

$891,440

2019

$21,760 (+3.6%)

$275,570 + $583,500

$859,070

2018

$21,004 (−1.2%)

$275,570 + $583,500

$859,070

2017

$21,256 (+3.1%)

$252,610 + $578,010

$830,620

2016

$20,616 (+6.5%)

$252,610 + $578,010

$830,620

2014

$19,362

$252,610 + $578,010

$830,620

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

Public record

Public record
Zoning

Beds

Baths

5.5

Stories

Lot width

—

Lot depth

—

Lot size

2.87 Acres

Year renovated

—

Sq. Ft.

5,288

Year built

1937

Style

Single Family Residential

County

Fairfield County

APN

319241

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 12, 2023.

RA-1

Single Family Districts, Very Low Density

The purpose of these districts is to set aside and protect areas which have been or may be developed predominantly for single family dwellings on large Lots in a rural setting. Certain other uses are also permitted as-of-right or by Special Permit subject to adequate conditions and safeguards. It is intended that all uses permitted in these districts be compatible with single family Development and consistent with local Street characteristics, the use and protection of private water and sewer facilities (where public facilities are unavailable) and the level of other public services. it is hereby found and declared, further, that these regulations are necessary to the protection of these areas and that their protection is essential to the maintenance of a balanced community of sound residential area of diverse types.

Permitted uses

Include but are not limited to:

Housing-Single unit
Housing-Senior
Educational/school
Communications tower

Property details

Parking

Garage Information
Garage & Parking: Attached Garage, Detached Garage
Garages Number: 5

Interior

Interior Information
Total Rooms: 9
Laundry Room Info: Main Level
Interior Features: Auto Garage Door Opener, Intercom
In-Law Apartment: Possible
In-Law Access: Lower Level
Handicap Features: Bath Grab Bars
Fireplaces Total: 4
Cooling System: Central Air
Appliances Included: Electric Cooktop, Wall Oven, Compactor

Bathroom Information
# of Baths (Full): 4
# of Baths (Half): 1

Bedroom Information
Beds Total: 5

Room Information
Rooms Additional: Mud Room, Solarium, Workshop
Basement Description: Full, Full With Walk-Out, Partial
Has Attic
Attic Description: Pull-Down Stairs, Floored

Exterior

Exterior Features
Roof Information: Asphalt Shingle
Exterior Siding: Clapboard, Brick, Stone
Exterior Features: Balcony, Cabana, Deck, Garden Area, Gutters, Stone Wall, Terrace

Lot Information
Lot Description: Some Wetlands

Building Information
Foundation Type: Brick
Construction Description: Frame, Brick

Property Information
Property Type: Single Family For Sale
Living Area SQFT Per Public Record: 5288
Driveway Type: Private

Financial

Assessments Information
Assessed Value: $859,070

Utilities

Utility Information
Water Source: Private Well
Sewage System: Septic
Hot Water Description: Other
Heat Type: Baseboard, Radiator, Zoned
Heat Fuel Type: Oil
Fuel Tank Location: In Basement

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: Per Board of Ed

Location Information
State: Connecticut
Nearby Amenities: Park, Playground/Tot Lot
Directions: Long Ridge Rd make a right to Chestnut Hill Rd entrance on left side of the street across from the park
County: Fairfield

Public facts

Beds: 5
Baths: 5.5
Sq. Ft.: 5,288
Stories: 3.0
Lot Size: 2.87 acres
Style: Single Family Residential
Year Built: 1937
Year Renovated: —
County: Fairfield County
APN: 319241

Home facts updated by county records on Jul 12, 2023

Around this home

Schools

Roxbury School

Public K-5 • Assigned • 2.6mi

4/10

Cloonan School

Public 6-8 • Assigned • 4.7mi

4/10

Westhill High School

Public 9-12 • Assigned • 2.4mi

3/10

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

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

5/10 Heat Factor

7 days above 100° expected this year, 16 days in 30 years

6/10 Wind Factor

50% chance of strong winds in next 30 years

4/10 Air Factor

5 unhealthy days expected this year, 7 days in 30 years

Provided by First Street

Historical weather

Stamford, CT • 06903

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 8.7 hours in June and 4.3 hours in December, placing it below the U.S. average for solar exposure.

8.7 hrs

4.3 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$1.75M – $2.12M

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Home values near 395 Chestnut Hill Rd

Data from public records.

Address	Redfin Estimate
48 Chestnut Hill Ln, Stamford, CT 4 Beds \| 2.5 Baths \| 3317 Sq. Ft.	—
421 Chestnut Hill Rd, Stamford, CT 3 Beds \| 2.5 Baths \| 2161 Sq. Ft.	$812,044

Address	Redfin Estimate
30 Chestnut Hill Ln, Stamford, CT 4 Beds \| 2.5 Baths \| 3108 Sq. Ft.	$1,149,409
29 Chestnut Hill Ln, Stamford, CT 4 Beds \| 3.5 Baths \| 3430 Sq. Ft.	$1,304,077

Address	Redfin Estimate
340 Chestnut Hill Rd, Stamford, CT 4 Beds \| 3 Baths \| 2669 Sq. Ft.	$1,696,882
15 Chestnut Hill Ln, Stamford, CT 4 Beds \| 3.5 Baths \| 3989 Sq. Ft.	$1,490,751

Property information provided by Smart MLS when last listed in 2018. This data may not match . Learn more.

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