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Back 41 Chester Street
Off Market

41 Chester Street

Stamford CT 06905

4
4
2
3213 sq. ft.
0.34 ac.
Single-Family
Last sold for $1,455,000
Jonathan MakovskyJonathan Makovsky, last sold this property on 25 June 2026 after 64 days on market.

Overview

If you've been waiting for that classic New England Colonial that actually lives up to the charm, 41 Chester might be it. Tucked on a quiet, tree-lined street yet a short walk to grocery, coffee, gym and more, this location nails the balance of neighborhood feel and everyday convenience, with easy access to Metro-North, downtown, I-95 and the Merritt. Inside, it's the layout buyers want: true center-hall flow with a bright living room, dining room, updated kitchen, and a study with custom built-ins that works as a second living space or home office. Just off the main living space, the screened-in porch extends your living area and is the spot for morning coffee or relaxed summer nights. Upstairs, the renovated primary suite offers dual closets and an updated bath, while additional bedrooms are well-sized and an expansive walk-up attic offers great storage or future upside. Features two staircases, including a rear staircase off the kitchen for easy second-floor access and a practical everyday flow. The backyard is set up for real use with a new bluestone patio, fire pit and level yard, plus easy indoor-outdoor flow. Major upgrades include 200 amp electrical, new boiler, newer hot water tank, attic spray foam, second floor AC, exterior paint, drainage, repaved driveway with Belgium block, and French drains and sump pump in the basement. This is the one where you get all the charm and no projects.

Features

4 bedrooms
4 bathrooms
2 carspaces
2 garage spaces
3213 sq. ft. floor area
0.34 ac. lot size
Single-Family

Estimated Value

Based on this property and similar 4 bedroom single-family properties sold in Stamford over the last 12 months, the estimated median property value of 41 Chester Street is $993.13k.

Median value
$993.13k
Estimated value range
$485k - $2.25m
Median days on market
16
Estimated value trend
24%
increase over the last 12 months
Average days on market is based on recent, comparable sales in Stamford. It is only an indication of the time a property is actively listed and should not be relied upon as an accurate representation of how soon a property will be sold.

Property history for 41 Chester Street

2026
Sold
$1,455,000
25 Jun 2026 by Jonathan Makovsky, of Compass Connecticut, LLC
2020
Sold
$719,000
17 Sep 2020 by Jonathan Makovsky, of JMX Realty Group

Happy sellers in Stamford

85%
85% of sellers in Stamford reported that their sale price either exceeded or met their price expectations.

Stamford stands out for consistently delivering exceptional satisfaction and strong market results for homeowners.

This is based on voluntary sentiment collected from 4 reviews in Stamford over the last 12 months.

Local market activity for 4 bedroom single-family properties in Stamford

In the last 12 months, 52 four-bedroom single-family properties similar to 41 Chester Street, have been sold.

This represents a 8% increase in four-bedroom single-family properties sales when compared to the previous 12 months.

Nearby agents

Compare and contact these top performing agents who’ve delivered exception customer service for their clients in Stamford

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Gail Stone

Gail Stone is a recommended agent for Stamford.  They have 1 local sale and collected 2 local reviews across the last 12 months.

  •   5   (5 reviews)
  •  2 Reviews in Stamford
  •  1 Sale in Stamford
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Jeanne Bracken

Jeanne Bracken is a recommended agent for Stamford.  They have 1 local sale and collected 1 local review across the last 12 months.

  •   5   (7 reviews)
  •  1 Review in Stamford
  •  1 Sale in Stamford
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Hyleri Katzenberg

Sellers who recommend Hyleri Katzenberg have praised them for being local expert, responsive, patient, supportive, great negotiation, reliable, and dedicated

  •   5   (63 reviews)
  •  1 Review in Stamford
  •  1 Sale in Stamford
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Jamie Restivo

Jamie Restivo is a recommended agent for Stamford.  They have 1 local sale and collected 1 local review across the last 12 months.

  •   5   (3 reviews)
  •  1 Review in Stamford
  •  1 Sale in Stamford
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