Skip to main content

237 Chestnut Hill Road

Stamford, Connecticut 06903

COMING SOON - NEW$1,066,000
Beds
4
Baths
2 | 1
SqFt
2,527
Acres
1.58
Year Built
1966
Matt Caiola

Matt Caiola

Luxury Real Estate Advisor

MCMATT CAIOLALUXURY PROPERTIES
Higgins Group Private Brokerage

Request a private showing and get Matt's read on price, condition, and next steps.

Call Matt
Pool4-Car Garage2 Fireplaces

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

View area

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

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$7,137

per 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.

Listed By

Chris Mrijaj

(203) 561-6264

Keller Williams Prestige Prop.

(203) 327-6700

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.