OPEN TODAY, 1PM TO 3PM

For sale

$725,000

Est. $4,998/mo —

•

2,161

sq ft

421 Chestnut Hill Rd, Stamford, CT 06903

About this home

Contemporary Colonial in a prime Long Ridge location! Move right into this 3-bedroom, and 2.1 bathroom home offering an open floor plan, and flexible living spaces, ideally situated just off Long Ridge Road. The main level features vaulted ceilings, oversized windows, and hardwood floors. Enjoy the modern, light and bright kitchen, a great room with a wood burning fireplace, a formal dining room, a large flex space which is ideal as an office, and a full bathroom. Upstairs offers 3 bedrooms, and a bath and a half. The lower level has a playroom, lots of storage, and an oversized 1 car garage. Step outside to your private outdoor oasis-relax on the spacious deck overlooking a serene backyard with a fire-pit, surrounded by walking trails, and a peaceful brook. Just steps away from Chestnut Hill Park, a 6.6-acre gem featuring a newly renovated playground, wide-open green spaces, and picnic areas. Minutes from shopping, dining, golf courses, and top-rated specialty hospitals, and a 2 minute drive to the Merritt Parkway makes this property ideal for buyers.

Single-familyProperty Type

1977Year Built

0.67 acresLot Size

$335Price/Sq.Ft.

1 car garageParking

Listed by Lisa Migliardi • Compass Connecticut, LLC

Contact: Agent Attribution Contact: (203) 561-7871 | Office Attribution Contact: (203) 343-0141

Source:Smart MLS #24202888

Payment calculator

$4,998 per month

Principal and interest$3,908

Property taxes

$861

HOA dues

Home insurance

$230

Utilities

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Open houses

Sunday, Sep 13

1:00pm - 3:00pm

Nearby open houses (10)

OPEN TODAY, 11AM TO 2PM
$2,500,000
4 beds3 baths2,989 sq ft
19 Tamarack Pl, Greenwich, CT 06831
REDFIN OPEN TODAY, 12PM TO 2PM3D WALKTHROUGH
$495,000
2 beds1 bath925 sq ft
5 Minerva Pl Unit 2C, White Plains, NY 10601
Listing by Redfin Real Estate
REDFIN OPEN TODAY, 12PM TO 2PM3D WALKTHROUGH
$414,900
1 bed1 bath793 sq ft
10 Ann St #209, Norwalk, CT 06854
OPEN TODAY, 12PM TO 2PM
$2,995,000
5 beds4.5 baths2,778 sq ft
16 Grace St, New Canaan, CT 06840
OPEN TODAY, 12PM TO 3PM3D WALKTHROUGH
$875,000
3 beds2 baths2,089 sq ft
89 Perry Ave, Norwalk, CT 06850
OPEN TODAY, 12PM TO 2PM3D WALKTHROUGH
$889,000
4 beds3 baths2,086 sq ft
99 Woodbury Ave, Stamford, CT 06907
REDFIN OPEN TODAY, 1PM TO 4PM3D & VIDEO TOUR
$2,100,000
6 beds4.5 baths2,990 sq ft
241 Pemberwick Rd, Greenwich, CT 06831
OPEN TODAY, 1PM TO 3PM
$609,000
2 beds3 baths1,710 sq ft
12 Willard Rd #11, Norwalk, CT 06851
OPEN TODAY, 1PM TO 3PM
$1,199,000
4 beds2.5 baths2,628 sq ft
17 Huckleberry Dr S, Norwalk, CT 06850
OPEN TODAY, 1PM TO 3PM
$485,000
3 beds2 baths1,525 sq ft
44 Strawberry Hill Ave Unit 3K, Stamford, CT 06902

Around this home

Schools

K - 12
Preschool & daycare

Roxbury School

Public K-5 • Assigned • 2.5mi

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

About North

Stamford

North Stamford, located between the Merritt Parkway and the New York state line, is a wooded and residential Stamford neighborhood with winding back roads and broad conservation land. The neighborhood’s character concentrates around the High Ridge Road and Long Ridge Road corridor, where farm stands, equestrian facilities, and low-key local shops set a country-leaning rhythm. The Bartlett Arboretum & Gardens anchors the landscape with trails and curated plant collections. Stamford Museum & Nature Center adds a cultural counterpoint with galleries, a working farm, and outdoor programs. Housing trends toward larger colonials and contemporaries set on deep lots, with stone walls and mature trees shaping the streetscape. Hiking loops and reservoir edges define weekends, while the drive into downtown Stamford stays firmly in the background.

Provided by Walk Score and Local Logic

Offer insights

421 Chestnut Hill Rd · $725,000

Strong offer

$785K and above

75% chance or better to win

Why $785K+ is a strong offer

DAYS ON MARKET

The average home goes pending in 36 days.

SALE-TO-LIST

Most homes are selling 4% above list price.

About offer insights

Property details

Interior
Exterior
Finance

Kitchen

Bathroom

Living

Dining

Interior features
8 total rooms
One fireplace
Partial basement

Bedrooms
3 bedrooms

Bathrooms
2 full bathrooms
1 half bathroom

Kitchen
Electric range
Microwave
Refrigerator
Dishwasher

Laundry & utility
Washer and electric dryer located on the main level (laundry area in a bathroom)

Heating & cooling
Hot water heating (oil)
Central air

Sale and tax history for 421 Chestnut Hill Rd

Sale History
Tax History

Date

Event

Price

GMLS #125786

Sep 10, 2026

Listed

$725,000

$335/sq ft

Sep 7, 2026

Coming Soon

$725,000

$335/sq ft

+27

Contemporary Colonial in a prime Long Ridge location! Move right into this 3-bedroom, and 2.1 bathroom home offering an open floor plan, and flexible living spaces, ideally situated just off Long Ridge Road. The main level features vaulted ceilings, oversized windows, and hardwood floors. Enjoy the modern, light and bright kitchen, a great room with a wood burning fireplace, a formal dining room, a large flex space which is ideal as an office, and a full bathroom. Upstairs offers 3 bedrooms, and a bath and a half. The lower level has a playroom, lots of storage, and an oversized 1 car garage. Step outside to your private outdoor oasis-relax on the spacious deck overlooking a serene backyard with a fire-pit, surrounded by nature trails, and a peaceful brook. Just seconds away from Chestnut Hill Park, a 6.6-acre gem featuring a newly renovated playground, wide-open green spaces, and picnic areas. Minutes from shopping, dining, golf courses, and top-rated specialty hospitals, and a 2 minute drive to the Merritt Parkway makes this property ideal for buyers.

Smart MLS #24202888

Sep 10, 2026

Listed

$725,000

$335/sq ft

Sep 7, 2026

Coming Soon

$725,000

$335/sq ft

Smart MLS #24099747

Jun 22, 2025

Listing Removed

—

Jun 5, 2025

Listed

$739,000

$342/sq ft

Jun 1, 2025

Coming Soon

GMLS #122918

Jun 5, 2025

Listed

$739,000

$342/sq ft

Jun 1, 2025

Coming Soon

Public Records

Sep 30, 2019

Sold

$471,000

$218/sq ft

Smart MLS #170177272

Sep 4, 2019

Listing Removed

—

Apr 19, 2019

Listed

$489,999

$227/sq ft

Public Records

Jul 15, 2011

Sold

$470,000

$217/sq ft

Smart MLS #98496229

Apr 7, 2011

Listed

$499,950

$231/sq ft

Smart MLS #98468542

Dec 30, 2010

Listing Removed

—

Jun 29, 2010

Listed

$559,500

$259/sq ft

Smart MLS #96009741

Mar 27, 1996

Listed

$309,900

$143/sq ft

Public Records

Mar 13, 1992

Sold

$280,000

$130/sq ft

Public record

Public record
Zoning

Beds

Baths

2.5

Stories

Lot width

—

Lot depth

—

Lot size

0.67 Acres

Year renovated

—

Finished Sq. Ft.

2,161

Unfinished Sq. Ft.

—

Total Sq. Ft.

2,161

Year built

1977

Style

Single Family Residential

County

Fairfield County

APN

312785

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

Climate risks

6/10 Flood Factor

Estimated 48-58% chance 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

53% 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

93/ 100

Exceptional sunlight

Sunscore

This home ranks in the top 16% for direct sun exposure in the zip code. There appears to be minimal shading by surrounding buildings, terrain, and vegetation.

9.1 hrs

5.3 hrs

JuneDecember

Provided by Shadowmap

Redfin Estimate for 421 Chestnut Hill Rd

$817,268

$92K over list price of $725K

Nearby comparable homes

The Redfin Estimate uses 6 recent nearby sales, priced between $775K to $1.2M.

SOLD JUL 2, 2026
$915,000 Last sold price
4 beds2.5 baths2,021 sq ft
190 Red Fox Rd, Stamford, CT 06903
$118/sq ft
larger lot
17 years older
SOLD JUN 30, 2026
$975,000 Last sold price
4 beds3.5 baths4,076 sq ft
19 Timber Mill Cir, Stamford, CT 06903
$96/sq ft
larger lot
12 years older
SOLD APR 23, 2026
$775,000 Last sold price
2 beds2 baths2,088 sq ft
14 Chestnut Hill Rd, Stamford, CT 06903
$36/sq ft
larger lot
137 years older
SOLD AUG 18, 2026
$813,709 Last sold price
2 beds2 baths1,743 sq ft
247 Chestnut Hill Rd, Stamford, CT 06903
$132/sq ft
larger lot
107 years older
SOLD JUN 23, 2026
$880,000 Last sold price
3 beds2 baths2,384 sq ft
290 Red Fox Rd, Stamford, CT 06903
$34/sq ft
larger lot
20 years older
SOLD AUG 24, 2026
$1,234,000 Last sold price
4 beds3 baths3,020 sq ft
27 Nob Hill Ln, Stamford, CT 06903
$74/sq ft
larger lot
3 years older

Rental earnings

Est. $3,250 per month, based on comparable rentals

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Early Access listings

EARLY ACCESSREDFIN COMING SOON

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4 beds4 baths5,002 sq ft

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OPEN TODAY, 1PM TO 3PM

$725,000

3 beds2.5 baths2,161 sq ft

421 Chestnut Hill Rd, Stamford, CT 06903

OPEN TODAY, 1PM TO 3PM

$769,000

4 beds2.5 baths2,416 sq ft

568 Hunting Ridge Rd, Stamford, CT 06903

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Details provided by Smart MLS and may not match the public record. Learn more.

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