299 Chestnut Hill Rd, Stamford, CT 06903

Off Market May 2022 for $1.2M

$1,545,772

Est. refi paymentEst. refi $5,802/mo

•

2,904

sq ft

299 Chestnut Hill Rd, Stamford, CT 06903

About this home

Fabulous and spacious 4 BR North Stamford Colonial is your perfect new year find! The light & bright Center hallway gleams with sunlight in the beautiful parquet floor entry foyer, flanked by oversized living room with fireplace to one side and formal dining on the other. Handsomely-appointed chefs kitchen with granite counters, stainless appliances, ceramic cooktop, glass tile backsplash and hardwood floors is as much form as function. Breakfast room/family room overlooking kitchen, with open floor plan, is perfect for cozy January suppers and snuggling by the 2nd fireplace. Generously sized master suite with hardwood floors & WIC. 3 additional bedrooms with 1 currently staged as a home office & 1 as a gym. 2nd full bathroom for flexibility on upper level, both with double marble vanities & floors and stone tub/shower enclosures. The yard is private so you can enjoy a moonlight swim in the newly resurfaced heated inground pool. Tasteful landscaping, bluestone steps, paved walkways and patio complete outdoor spaces. Extensive renovations in 2015 included new roof, boiler & hot water heater, thermal windows throughout, doors + hardware, upgraded electrical panel, refinished HW floors. Lower level/garage is unfinished space currently used for storage. Set on a private 1.09 acre off Long Ridge Rd, 5 mins drive to downtown Stamford. Walking distance to Chestnut Hill Park, complete with extensive recreational playground for all ages, walking trails and ball field.

Heated Gunite pool resurfaced in 2021, well pump serviced within past 2 years, installed irrigation system w. pressure regulation, new roof installed 2015, furnace & hot water heater replaced 2015, Andersen thermal windows & doors installed. Friendly dog.

Single-familyProperty Type

1966Year Built

1.09 acresLot Size

$532Est. Price/Sq.Ft.

2 car garageParking

Listed by Lisa Gomberg • Keller Williams Prestige Prop.

Bought with Drew Slack • ERA Insite Realty Services

Source:Smart MLS #170460922

Redfin Estimate

$1,545,772

$346K since sold in May 2022$44K since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 39.1% higher than the average sale price ($1.11M) of 6 comparable homes.

SOLD AUG 24, 2026
$1,234,000
A
4 beds3 baths3,020 sq ft
27 Nob Hill Ln, Stamford, CT 06903
SOLD OCT 27, 2025
$1,150,000
B
4 beds2.5 baths3,022 sq ft
23 Ethan Allen Ln, Stamford, CT 06903
SOLD JUL 2, 2026
$915,000
C
4 beds2.5 baths2,021 sq ft
190 Red Fox Rd, Stamford, CT 06903
SOLD MAY 21, 2026
$1,210,000
D
4 beds2.5 baths3,030 sq ft
15 Very Merry Rd, Stamford, CT 06903
SOLD DEC 2, 2025
$910,000
E
4 beds2.5 baths2,604 sq ft
21 Timber Mill Rd, Stamford, CT 06903
SOLD DEC 1, 2025
$1,250,000
F
4 beds3 baths2,736 sq ft
2 Butternut Pl, Stamford, CT 06903

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Earn from this home

Sell

$572,960

Est. take-home

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Refinance

Est. cash available

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Rent

$3,311/mo

Redfin rental estimate

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Market trends in 06903, CT

Last updated August 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

106.5%

1.2% MoM

Median sale price

$1.3M

$43K MoM

Avg. days on market

30d

4 days MoM

Recently sold homes

13 MoM

New listings for sale

$919,000
3 beds2.5 baths2,536 sq ft
70 Arrow Head Dr, Stamford, CT 06903
COMING SOON
$1,175,000
4 beds2.5 baths3,317 sq ft
48 Chestnut Hill Ln, Stamford, CT 06903
$1,225,000
4 beds4 baths3,481 sq ft
231 Skymeadow Dr, Stamford, CT 06903
$1,795,000
3 beds3 baths3,312 sq ft
58 Skymeadow Dr, Stamford, CT 06903
$1,725,000
4 beds4 baths5,002 sq ft
79 Cross Country Trl, Stamford, CT 06903
$750,000
3 beds2.5 baths2,568 sq ft
981 Rock Rimmon Rd, Stamford, CT 06903
$725,000
3 beds2.5 baths2,161 sq ft
421 Chestnut Hill Rd, Stamford, CT 06903
$769,000
4 beds2.5 baths2,416 sq ft
568 Hunting Ridge Rd, Stamford, CT 06903
3D WALKTHROUGH
$1,180,000
3 beds2.5 baths3,596 sq ft
23 Mill Stream Rd, Stamford, CT 06903
$989,000
3 beds2.5 baths2,304 sq ft
163 Cedarwood Rd, Stamford, CT 06903
See all

Provided by Redfin

Sale history for 299 Chestnut Hill Rd

Date

Event

Price

Smart MLS #170460922

May 27, 2022

Sold

$1,200,000

$413/sq ft

Mar 4, 2022

Contingent

—

Feb 10, 2022

Price Changed

$1,099,000

$378/sq ft

Jan 13, 2022

Listed

$1,199,000

$413/sq ft

Smart MLS #99121395

Apr 15, 2016

Sold

$875,000

$301/sq ft

Mar 30, 2016

Listing Removed

—

Sep 28, 2015

Listed

$899,000

$310/sq ft

This Pristine Home Spared nothing. Quality Renovated with New Roof, Exterior Cedar Clapbrd freshly painted. All New Anderson Windows,2 Sliders Drs,2 Garage Drs,Oil Heating Boiler/Hot water Heater,Electrical Panel updated. Privacy Fence & Landscaping, Blue Stone Steps, Stonewalls, Walkways, Patio. Offers Ingrd Heated Gunite Pool. Completely Brand new Kit w/Solid wood Cab, Granite Countertops, Glass/Stone Backsplash. All New Whirlpool Appliances, Dlb Oven,3 Dr Refrig, Dishwasher, Glass Cook top W/Exhaust Fan. All Hardwd Flrs Refinished Throughout, All New Baths W/Marble Flrs, Tile,Counter & Wood Vanity Cab, Porcelum Sinks. Master bath w/hot tub. All New Lite Fix, Doors & Hardware. Wireless Alarm System. Completely painted, Ready to move into.

Smart MLS #99069798

Aug 29, 2014

Sold

$544,500

$188/sq ft

Jun 16, 2014

Listed

$544,500

$188/sq ft

Public Records

Apr 4, 2007

Sold

$1,015,000

$350/sq ft

Smart MLS #98313850

Jan 4, 2007

Listed

$1,049,000

$361/sq ft

Public Records

Aug 23, 2004

Sold

$955,000

$329/sq ft

Smart MLS #98201526

Jun 13, 2004

Listed

$979,000

$337/sq ft

Public Records

Dec 18, 2001

Sold

$768,750

$265/sq ft

Smart MLS #98108044

Aug 6, 2001

Listed

$799,000

$275/sq ft

GMLS #48257

Aug 5, 2001

Listed

$799,000

$275/sq ft

Public Records

Oct 15, 1990

Sold

$487,500

$168/sq ft

Year

Property tax

Land + Additions

Assessment*

2022

$13,998 (+1.4%)

$214,000 + $317,620

$531,620

2021

$13,806 (+2.5%)

$214,000 + $317,620

$531,620

2020

$13,466

$214,000 + $317,620

$531,620

2019

$13,463 (+3.6%)

$214,000 + $317,500

$531,500

2018

$12,995 (+9.3%)

$214,000 + $317,500

$531,500

2017

$11,890 (+3.1%)

$196,160 + $268,460

$464,620

2016

$11,532 (+6.5%)

$196,160 + $268,460

$464,620

2014

$10,830

$196,160 + $268,460

$464,620

Tax history for 299 Chestnut Hill Rd

Year

Property tax

Land + Additions

Assessment*

2022

$13,998 (+1.4%)

$214,000 + $317,620

$531,620

2021

$13,806 (+2.5%)

$214,000 + $317,620

$531,620

2020

$13,466

$214,000 + $317,620

$531,620

2019

$13,463 (+3.6%)

$214,000 + $317,500

$531,500

2018

$12,995 (+9.3%)

$214,000 + $317,500

$531,500

2017

$11,890 (+3.1%)

$196,160 + $268,460

$464,620

2016

$11,532 (+6.5%)

$196,160 + $268,460

$464,620

2014

$10,830

$196,160 + $268,460

$464,620

*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

2.5

Stories

Lot width

—

Lot depth

—

Lot size

1.09 Acres

Year renovated

—

Sq. Ft.

2,904

Year built

1966

Style

Single Family Residential

County

Fairfield County

APN

318519

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, Security
Garages Number: 2

Interior

Virtual Tour Information
Has Virtual Tour

Interior Information
Total Rooms: 8
Laundry Room Location: main
Laundry Room Info: Main Level
Interior Features: Open Floor Plan, Security System
Security System
Fireplaces Total: 2
Cooling System: Attic Fan, Central Air
Appliances Included: Electric Cooktop, Wall Oven, Microwave, Range Hood, Refrigerator, Dishwasher, Washer, Dryer

Bathroom Information
# of Baths (Full): 2
# of Baths (Half): 1

Bedroom Information
Beds Total: 4

Room Information
Rooms Additional: Foyer, Laundry Room
Room Count: 11
Basement Description: Unfinished, Garage Access, Storage
Has Attic

Exterior

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

Lot Information
Lot Description: Lightly Wooded, Treed, Fence - Partial

Pool Information
Swimming Pool
Pool Description: In Ground Pool, Heated, Gunite

Building Information
Foundation Type: Block, Concrete
Construction Description: Frame, Concrete
Color: White

Property Information
Radon Mitigation Air
Property Type: Single Family For Sale
Living Area SQFT Per Public Record: 2904
Driveway Type: Paved

Financial

Assessments Information
Assessed Value: $531,620

Utilities

Utility Information
Water Source: Private Well
Sewage System: Septic
Hot Water Description: Oil
Heat Type: Baseboard, Hot Water
Heat Fuel Type: Oil
Fuel Tank Location: In Basement
Energy Features: Thermopane Windows

Location

School Information
Middle Jr High 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, Walk to Bus Lines
Directions: Long Ridge Rd. to Chestnut Hill Road.
County: Fairfield

Public facts

Beds: 4
Baths: 2.5
Sq. Ft.: 2,904
Stories: 2.0
Lot Size: 1.09 acres
Style: Single Family Residential
Year Built: 1966
Year Renovated: —
County: Fairfield County
APN: 318519

Home facts updated by county records on Jul 12, 2023

Other

Documents & Disclosures
Supplement Count Public: 1

Around this home

Schools

Roxbury School

Public K-5 • Assigned • 2.6mi

4/10

Cloonan School

Public 6-8 • Assigned • 4.8mi

4/10

Westhill High School

Public 9-12 • Assigned • 2.5mi

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, 15 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

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

$1.47M – $1.78M

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Home values near 299 Chestnut Hill Rd

Data from public records.

Address	Redfin Estimate
37 Chestnut Hill Lane, Stamford, CT 3 Beds \| 3 Baths \| 3934 Sq. Ft.	$1,349,795
276 Chestnut Hill Road, Stamford, CT 2 Beds \| 3.5 Baths \| 2866 Sq. Ft.	$999,681

Address	Redfin Estimate
331 Chestnut Hill Road, Stamford, CT 4 Beds \| 3.5 Baths \| 2812 Sq. Ft.	$1,142,449
320 Chestnut Hill Road, Stamford, CT 3 Beds \| 3 Baths \| 3342 Sq. Ft.	$1,516,553

Address	Redfin Estimate
321 Chestnut Hill Road, Stamford, CT 4 Beds \| 2.5 Baths \| 4152 Sq. Ft.	$1,205,912
340 Chestnut Hill Road, Stamford, CT 4 Beds \| 3 Baths \| 2669 Sq. Ft.	$1,668,361

Property information provided by Smart MLS when last listed in 2022. This data may not match . Learn more.

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