237 Chestnut Hill Road
Stamford, Connecticut 06903
- Beds
- 4
- Baths
- 2 | 1
- SqFt
- 2,527
- Acres
- 1.58
- Year Built
- 1966
- Neighborhood
- North Stamford
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
Request a private showing and get Matt's read on price, condition, and next steps.
About This Home
Welcome to this private North Stamford retreat set on 1.58 acres of beautiful, secluded property. This 4-bedroom Colonial offers spacious living areas and an impressive outdoor setting designed for relaxing and entertaining. A 30-foot sunroom with sliders opens to the expansive backyard and pool area. The heated gunite pool is the centerpiece of the property, featuring an expansive stone terrace and waterfall feature. Pool improvements include a new gunite floor and tile in 2021, plus a new filter and electrical box in 2025. The property also offers a pool cabana with electricity, whole-house generator, deer fencing, mature landscaping, and a newly paved and sealed driveway. Inside, the home offers a mix of classic character and updates, including renovated bathrooms, Anderson windows, French doors, updated well systems, and hardwood flooring. A rare 4-car garage setup includes two attached garages plus an oversized detached barn with heat and air conditioning, workshop space, storage, and an additional carport. The barn provides exceptional flexibility for vehicles, hobbies, equipment, or storage. With its private acreage, extensive outdoor amenities, versatile garage and barn spaces, and sought-after North Stamford location, this property offers a unique opportunity to create your own private retreat.
Key Facts
- City/Town
- Stamford
- Neighborhood
- North Stamford
- Property / Style
- Single Family · Colonial
- Year Built
- 1966
- Days on Market
- 0 days
- Beds
- 4
- Baths
- 2 full · 1 half
- Living Area
- 2,527 sq ft
- Lot Size
- 1.58 acres
- Garage / Parking
- 4 garage
- Property Taxes
- $15,548 / Annually
Market Snapshot
The Stamford Market
Single Family · trailing 12 months
Active Listings
75
105 under contract
Median List Price
$1.10M
75 active listings
Median Closed Price
$980,000
567 sales
Median Days on Market
36
75 active listings
Median $ / Sq Ft
$416
75 active listings
Sale-to-List Ratio
104.1%
567 sales
How this home compares
List Price
$1.07M
vs $1.10M median
In line with median
Price / Sq Ft
$422
vs $416 median
In line with median
Days on Market
0 days
vs 36 days median
36 days fresher than median
Based on 75 active and 567 closed sales (trailing 12 mo) of single family in Stamford. Source: SmartMLS · As of August 18, 2026.
Location
237 Chestnut Hill Road, Stamford, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Aug 13, 2026per month
- Principal & Interest$5,486
- Property Taxes$1,296
- Insurance$355
- 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
- 1966
- New Construction
- No/Resale
- Living Area
- 2,527 sq ft
Schools
- Elementary
- Roxbury
- High
- Westhill
Interior
- Heating
- Hot Air
- Heat Fuel
- Natural Gas
- Cooling
- Ceiling FansCentral Air
- Fireplaces
- 2
- Laundry Location
- Basement
- Appliances
- Cook TopWall OvenMicrowaveRefrigeratorDishwasherWasherDryer
- Basement
- Crawl SpacePartial
- Interior Features
- Auto Garage Door OpenerCable - AvailableSecurity System
Exterior & Lot
- Lot Size
- 1.58 acres
- Zoning
- RA1
- Garage / Parking
- 4 garage spacesAttached GarageDetached GarageBarn
- Waterfront Details
- Not Applicable
- Water Source
- Private Well
- Sewer
- Septic
- Pool
- GuniteIn Ground Pool
- Construction
- Vinyl Siding
- Color
- Yellow
- Roof
- Asphalt Shingle
- Foundation
- Block
- Exterior Features
- BarnCabanaGuttersLightingUnderground SprinklerPatio
- Lot Description
- Fence - PartialSome WetlandsTreed
Listing & Financials
- Property Taxes
- $15,548 / Annually
- Days on Market
- 0
- MLS #
- 24197236
- MLS Status
- Coming Soon
Similar Properties
Homes with a close match in area, property type, and price.
This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 8/18/2026. 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 8/18/2026 at 5:35 PM UTC.
