421 Chestnut Hill Road
Stamford, Connecticut 06903
- Beds
- 3
- Baths
- 2 | 1
- SqFt
- 2,161
- Acres
- 0.67
- Year Built
- 1977
- Neighborhood
- North Stamford
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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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.
Key Facts
- City/Town
- Stamford
- Neighborhood
- North Stamford
- Property / Style
- Single Family · Colonial
- Year Built
- 1977
- Days on Market
- 49 days
- Beds
- 3
- Baths
- 2 full · 1 half
- Living Area
- 2,161 sq ft
- Lot Size
- 0.67 acres
- Garage / Parking
- 1 garage
- Property Taxes
- $10,330 / Annually
Market Snapshot
The Stamford Market
Single Family · trailing 12 months
Active Listings
96
100 under contract
Median List Price
$1.09M
96 active listings
Median Closed Price
$976,500
572 sales
Median Days on Market
34
96 active listings
Median $ / Sq Ft
$424
96 active listings
Sale-to-List Ratio
104.1%
572 sales
How this home compares
List Price
$725,000
vs $1.09M median
33.8% below median
Price / Sq Ft
$335
vs $424 median
21.0% below median
Days on Market
49 days
vs 34 days median
15 days longer than median
Based on 96 active and 572 closed sales (trailing 12 mo) of single family in Stamford. Source: SmartMLS · As of October 27, 2026.
Location
421 Chestnut Hill Road, Stamford, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Oct 22, 2026per month
- Principal & Interest$3,984
- Property Taxes$861
- Insurance$242
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Stamford
- Neighborhood
- North Stamford
- County
- Fairfield
Residence
- Property Type
- Single Family
- Style
- Colonial
- Year Built
- 1977
- New Construction
- No/Resale
- Living Area
- 2,161 sq ft
Schools
- Elementary
- Northeast
- High
- Westhill
Interior
- Heating
- Hot Water
- Heat Fuel
- Oil
- Cooling
- Central Air
- Fireplaces
- 1
- Laundry
- Main Level
- Laundry Location
- Bathroom
- Appliances
- Electric RangeMicrowaveRefrigeratorDishwasherWasherElectric Dryer
- Basement
- Partial
Exterior & Lot
- Lot Size
- 0.67 acres
- Zoning
- RA1
- Garage / Parking
- 1 garage spaceAttached Garage
- Waterfront
- Direct waterfront
- Waterfront Details
- Brook
- Water Source
- Private Well
- Sewer
- Septic
- Construction
- Wood
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Exterior Features
- Deck
- Lot Description
- Corner LotLightly Wooded
Listing & Financials
- Property Taxes
- $10,330 / Annually
- Days on Market
- 49
- MLS #
- 24202888
- MLS Status
- Under Contract
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This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 10/27/2026. This information is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing or leasing. Data is deemed reliable but is not guaranteed accurate by the MLS, the listing broker, the listing agent, or Matt Caiola. Buyers and tenants should independently verify all information that matters to their decision.
Map locations may be approximate. Any offer of compensation, if applicable, is made only to participants of the MLS where the listing is filed. ©2026 Smart MLS, Inc. All rights reserved.
Data last updated on 10/27/2026 at 12:05 AM UTC.