Built in 1840, this charming North Stamford carriage-house residence blends authentic character with an unforgettable layout across multiple levels. Enter into a generous living/family room opening to an outdoor terrace and over an acre of private landscaped grounds-an ideal setting for gathering, relaxing, and enjoying the quiet beauty North Stamford is known for. Two bedrooms are tucked on the second floor, while the home's most striking entertaining space has the homes original door entering into a former sunroom-now a dramatic dining room with cathedral ceiling, and a historic stone wall overlooking the street. Additionally there is a cottage on the property with electricity and perfect for a WFH space. Recent updates include new boiler in 2024, updated electrical system, renovated baths with new fixtures, repainted inside and outside of main house and cottage in 2023 and 2026, resurfaced and graveled drive in 2024 and added water purification system in 2025. This home has endless possibilities and is truly a rare opportunity to own a property that feels genuinely one-of-a-kind.
Listed by Molly Rubins
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NestSeekers International
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(203) 216-3111
Last updated March 15, 2026
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Source: SmartMLS #24158094
Listing Facts
TypeSingle-family
NeighborhoodNorth Stamford
Bedrooms2
Bathrooms2
Days on Prevu12
Taxes$9,234/year
Size2,088 sqft
Price per sqft$347
Location
Mortgage Calculator
Listing History
03/13/2026
Status changed to Active
$725,000
03/12/2026
Status changed to Removed from Feed
$725,000
03/04/2026
Listed by NestSeekers International
$725,000
Property Details for 14 Chestnut Hill Road
Exterior
Construction
New Construction: No/Resale
Roof: Asphalt Shingle
Year Built: 1840
Year Built Details: Public Records
Architectural Style: Colonial
Construction Materials: Stone
Features
Waterfront Features: Not Applicable
Measurements
Lot Features: Dry, Level Lot, Cleared
Lot Size Acres: 1.06
Financial
Taxes
Parcel Number: 318737
Tax Annual Amount: $9,234.00
Tax Year: 25
Interior
Features
Appliances: Gas Cooktop, Oven/Range, Microwave, Refrigerator, Washer, Dryer
Fireplaces Total: 1
Measurements
Living Area: 1,680
Rooms
Basement: Crawl Space, Hatchway Access
Bathrooms Full: 2
Bathrooms Total Integer: 2
Bedrooms Total: 2
Rooms Total: 6
Parking
Parking
Attached Garage: Attached Garage
Garage Spaces: 3
Schools
Elementary School
Elementary School: Northeast
High School
High School: Westhill
Middle or Junior School
Middle Or Junior School: Turn Of River
Utilities
Equipment
Cooling: Window Unit
Heating: Hot Water
Laundry Features: Main Level
Sewer: Septic
Water Source: Private Well
Frequently Asked Questions
How many bedrooms and bathrooms does this single-family home have?
There are 2 bedrooms and 2 bathrooms in this single-family home at 14 Chestnut Hill Road.
What schools are nearby to 14 Chestnut Hill Road?
Nearby schools include the Northeast Elementary School, Turn Of River Middle School, and Westhill High School.
Does this single-family home have parking?
Yes, there are 3 parking spaces available for 14 Chestnut Hill Road.
What are the annual taxes for 14 Chestnut Hill Road?
Annual taxes for this single-family home are estimated at $9,234.
How does 14 Chestnut Hill Road compare to other single-family homes in North Stamford?
This single-family home is listed 58% below the average price for single-family homes in North Stamford and has been on the market for 45 less days than the typical home in this area.
What is the square footage on this single-family home?
According to the MLS, this listing is 2,088 sqft.
14 Chestnut Hill Road is a 2-bedroom, 2-bath single-family home for sale in Stamford CT 06903. On Prevu for 12 days at $725,000. This residence features 2,088 square feet of living space, located in North Stamford. The median listing price for single-family homes in this area is $1,295,000. Nearby schools include Northeast Elementary School, Turn Of River Middle School, and Westhill High School. View other single-family home listings in Stamford.
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