21 Chickering Rd, Dedham, MA 02026
OFF MARKET

21 Chickering Rd
Dedham, MA 02026

Dexter
  • 3 Beds
  • 3 Baths
  • 2,047 sqft

$919,100

Trulia Estimate
as of Aug 17, 2026
Est. Refi. Payment $5,557/mo*
Refinance Your Home

$919,100

Trulia Estimate
as of Aug 17, 2026
Est. Refi. Payment $5,557/mo*
Refinance Your Home
3 Beds
3 Baths
2,047 sqft

Home Value

Trulia Estimate
$919K
Since last month
Decreased$27K (-2.9%)
Since last year
Increased$58K (+6.7%)
Since last sale
Increased$429K (+87.6%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +79% in the last 10 years
MonthEstimated value
2026
August 2026$919K
July 2026$939K
June 2026$946K
May 2026$956K
April 2026$928K
March 2026$922K
February 2026$886K
January 2026$864K
2025
2024
2023
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
24 Fair Oak Rd, Dedham, MA
0.16
Single-Family Home
$620,000
09/30/25
3
1.5
1,540
24 Pond Farm Rd, Dedham, MA
0.10
Single-Family Home
$700,000
11/25/25
3
1.5
1,610
24 Fay Rd, Dedham, MA
0.22
Single-Family Home
$716,400
07/07/26
3
1.5
1,560
15 Gay Street Ext, Westwood, MA
0.16
Single-Family Home
$1,079,000
06/17/26
4
3
3,229
886 Gay St, Westwood, MA
0.11
Single-Family Home
$1,000,000
11/20/25
4
2.5
2,284
14 Eldridge Pl, Westwood, MA
0.35
Single-Family Home
$935,000
05/12/26
3
2
2,048
55 Loring St, Westwood, MA
0.27
Single-Family Home
$875,000
06/25/26
4
2.5
1,935
133 Pacella Dr, Dedham, MA
0.31
Single-Family Home
$855,000
06/12/26
3
2
1,434
70 Cobleigh St, Westwood, MA
0.39
Single-Family Home
$1,010,000
06/15/26
3
1.5
2,264
45 Anthony Ln, Dedham, MA
0.30
Single-Family Home
$1,000,000
07/10/26
4
3
2,279

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
24 Pond Farm Rd, Dedham, MA 02026
0.10
$700,000
3
1.5
1,610
Recently Sold
18 Pond Farm Rd, Dedham, MA 02026
0.11
$865,400
3
2
2,138
Off Market
886 Gay St, Westwood, MA 02090
0.11
$1,000,000
4
2.5
2,284
Recently Sold
Address Not Disclosed, Dedham, MA 02026
0.09
$589,000
1
1
915
For Sale
1000 Washington St #301, Dedham, MA 02026
0.09
-
1
1
905
Off Market
1000 Washington St #214, Dedham, MA 02026
0.09
-
1
1
714
Off Market
1000 Washington St #303, Dedham, MA 02026
0.09
-
1
1
751
Off Market
1000 Washington St #305, Dedham, MA 02026
0.09
-
1
1
915
Off Market
1000 Washington St #312, Dedham, MA 02026
0.09
-
1
1
706
Off Market
1000 Washington St #310, Dedham, MA 02026
0.09
-
1
1
754
Off Market
1000 Washington St #316, Dedham, MA 02026
0.09
-
1
1
783
Off Market
1000 Washington St #203, Dedham, MA 02026
0.09
-
1
1
751
Off Market

Local Information

  • Map ViewExplore the area around 21 Chickering Rd.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1952
Living Area
2,047 sqft
Price/Sqft
$449
Parking
Garage

About this House

This single-family home is located at 21 Chickering Rd, Dedham, MA. 21 Chickering Rd is in the Dexter neighborhood in Dedham, MA and in ZIP code 02026. This property has 3 bedrooms, 3 bathrooms and approximately 2,047 sqft of floor space. This property has a lot size of 10018 sqft and was built in 1952.
21 Chickering Rd, Dedham, MA 02026 is a 3 bedroom, 3 bathroom, 2,047 sqft single-family home in Dexter, built in 1952. It last sold for $490,000 on Aug 27, 2015. It is currently off market. The Trulia Estimate is $919,100, with a rent estimate of $4,808/month.

Home Details for 21 Chickering Rd

Interior Features

Interior Details
BasementNumber of Rooms: 8
Heating & Cooling
Heating: Forced Air, GasAir ConditioningHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: OtherPatio
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 1952
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 10018 sqft

Price and Tax history

DateEventPrice
Aug 27, 2015
Source: N/A
Sold
$490,000
Jun 26, 1998
Source: N/A
Sold
$197,500
Dec 31, 1991
Source: N/A
Sold
$161,500

Market trends in Dedham

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$770K
Sale-to-List Price
102.6%
Price per sq ft
$475
Available listings
80
1MoM
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Around this home

Neighborhood Overview

Dexter
See Local Highlights
Neighborhood stats provided by third party data sources.

What Locals Say about Dexter

At least 9 Trulia users voted on each feature.

  • 92 % Say parking is easy

  • 92 % Say it's dog friendly

  • 90 % Say yards are well-kept

  • 88 % Say it's quiet

  • 82 % Say car is needed

  • 71 % Say people would walk alone at night

  • 71 % Say there's wildlife

  • 70 % Say they plan to stay for at least 5 years

  • 67 % Say it's walkable to restaurants

  • 62 % Say there's holiday spirit

  • 55 % Say there are sidewalks

  • 44 % Say there are community events

  • 38 % Say kids play outside

  • 31 % Say neighbors are friendly

  • 30 % Say streets are well-lit

  • 27 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • Trulia User
    "Farmers market. Kayaking on Charles river. Churches. Historic buildings. People know each other. Fun in Dedham square. Shopping, movie theater and restaurants "
    0
    Flag
  • scirokid
    "Positives: Extremely safe neighborhood, super convenient to I95, surrounded by amazing houses in Precinct 1, close-knit community, all houses built by the same developer in the 1950's, alot of kids around. Negatives: Houses all very similar (little architectural diversity), neighborhood is cut off from surrounding neighborhoods (big loop - need car to get places), streets need repairs (but that's all of Dedham)"
    0
    Flag

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Apartments for Rent

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Explore by feature - Pet Friendly

19 pet-friendly rentals in Dedham, MA

Explore by feature - Garage

6 rentals with a garage in Dedham, MA

Explore by feature - Air Conditioning

30 rentals with air conditioning in Dedham, MA

Explore by feature - Washer/dryer

37 rentals with a washer/dryer in Dedham, MA

Homes for sale near 21 Chickering Rd

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Off Market Homes Near 21 Chickering Rd

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Frequently asked questions about 21 Chickering Rd

  • What is 21 Chickering Rd estimated to be worth?
    Trulia's estimated value for 21 Chickering Rd in Dedham, MA is $919,100.
  • What is the price history for 21 Chickering Rd?
    21 Chickering Rd in Dedham, MA last sold for $490,000 in August 2015.
  • Is Dedham a buyer's or seller's market?
    Dedham is currently a seller's market, based on recent for-sale activity.
  • What's the median sale price in Dedham?
    The median sale price in Dedham is $770K.
  • How big is the lot at 21 Chickering Rd?
    The lot at 21 Chickering Rd in Dedham, MA is about 0.23 acres (10,018 sq ft).
  • Does 21 Chickering Rd have a garage?
    Yes, 21 Chickering Rd in Dedham, MA has a garage.