39 Chickering Rd, Dedham, MA 02026
Property image
Property image
OFF MARKET

39 Chickering Rd
Dedham, MA 02026

Dexter
  • 3 Beds
  • 3.5 Baths
  • 2,338 sqft (on 0.27 acres)

$1,009,000

Trulia Estimate
as of Aug 15, 2026
Est. Refi. Payment $6,083/mo*
Refinance Your Home

$1,009,000

Trulia Estimate
as of Aug 15, 2026
Est. Refi. Payment $6,083/mo*
Refinance Your Home
3 Beds
3.5 Baths
2,338 sqft
(on 0.27 acres)

Home Value

Trulia Estimate
$1.01M
Since last month
Decreased$30K (-2.9%)
Since last year
Increased$16K (+1.6%)
Since last sale
Increased$379K (+60.6%)
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 +256% in the last 10 years
MonthEstimated value
2026
August 2026$1M
July 2026$1.02M
June 2026$1.03M
May 2026$1.04M
April 2026$1.02M
March 2026$1.01M
February 2026$968K
January 2026$942K
2025
2024
2023
2022
2021
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
0.12
Single-Family Home
$620,000
09/30/25
3
1.5
1,540
24 Pond Farm Rd, Dedham, MA
0.07
Single-Family Home
$700,000
11/25/25
3
1.5
1,610
24 Fay Rd, Dedham, MA
0.21
Single-Family Home
$716,400
07/07/26
3
1.5
1,560
45 Anthony Ln, Dedham, MA
0.29
Single-Family Home
$1,000,000
07/10/26
4
3
2,279
886 Gay St, Westwood, MA
0.12
Single-Family Home
$1,000,000
11/20/25
4
2.5
2,284
15 Gay Street Ext, Westwood, MA
0.20
Single-Family Home
$1,079,000
06/17/26
4
3
3,229
829 Gay St, Westwood, MA
0.26
Single-Family Home
$1,150,000
05/29/26
4
2
2,360
14 Eldridge Pl, Westwood, MA
0.38
Single-Family Home
$935,000
05/12/26
3
2
2,048
130 Cobleigh St, Westwood, MA
0.48
Single-Family Home
$1,095,500
12/15/25
3
2.5
1,920
55 Loring St, Westwood, MA
0.31
Single-Family Home
$875,000
06/25/26
4
2.5
1,935

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
0.07
$700,000
3
1.5
1,610
Recently Sold
18 Pond Farm Rd, Dedham, MA 02026
0.07
$865,400
3
2
2,138
Off Market
886 Gay St, Westwood, MA 02090
0.12
$1,000,000
4
2.5
2,284
Recently Sold
Address Not Disclosed, Dedham, MA 02026
0.13
$589,000
1
1
915
For Sale
1000 Washington St #301, Dedham, MA 02026
0.13
-
1
1
905
Off Market
1000 Washington St #214, Dedham, MA 02026
0.13
-
1
1
714
Off Market
1000 Washington St #303, Dedham, MA 02026
0.13
-
1
1
751
Off Market
1000 Washington St #305, Dedham, MA 02026
0.13
-
1
1
915
Off Market
1000 Washington St #312, Dedham, MA 02026
0.13
-
1
1
706
Off Market
1000 Washington St #310, Dedham, MA 02026
0.13
-
1
1
754
Off Market
1000 Washington St #316, Dedham, MA 02026
0.13
-
1
1
783
Off Market
1000 Washington St #203, Dedham, MA 02026
0.13
-
1
1
751
Off Market

Local Information

  • Map ViewExplore the area around 39 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
1953
Lot Size
0.27 acres
Living Area
2,338 sqft
Price/Sqft
$432
Parking
Garage

About this House

Immaculate Dream Home for sale. A New second level was added to this entirely and exquisitely remodeled home. Situated in desirable Upper Dedham's Precinct One, this home has all of the bells and whistles you're looking for. Gleaming Hardwood floors throughout, 3 Bathrooms and a 1/2 bath in the partially finished basement, Central Air and Heat, A uniquely designed Open Concept kitchen with Granite counters, Breakfast Bar and Stainless Steel Appliances. A gorgeous family room that leads to a large deck for entertaining guests, a Whirlpool tub in the Master Bath inside of your Very Large Master bedroom. New Siding, Roof, Electrical and a Garage. This is a one of a kind home that MUST be seen; close to major highway and Legacy Place Mall for fun activities. Please see firm remarks regarding buyer credit.
39 Chickering Rd, Dedham, MA 02026 is a 3 bedroom, 4 bathroom, 2,338 sqft single-family home in Dexter, built in 1953. It last sold for $625,000 on May 19, 2017. It is currently off market. The Trulia Estimate is $1,009,000, with a rent estimate of $5,244/month.

Home Details for 39 Chickering Rd

Interior Features

Interior Details
BasementNumber of Rooms: 6
Heating & Cooling
Heating: Forced Air, GasAir ConditioningHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2
Fireplace & Spa
Fireplace

Exterior Features

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

Property Information

Year Built
Year Built: 1953
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 0.27 acres

Price and Tax history

DateEventPrice
May 19, 2017
Source: N/A
Sold
$625,000
Apr 8, 2017
Source: Agent Provided
Pending
$629,900
Mar 24, 2017
Source: Agent Provided
Listed For Sale
$629,900
Aug 31, 2016
Source: N/A
Sold
$300,000
Jun 28, 2016
Source: Agent Provided
Pending
$275,000

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

17 pet-friendly rentals in Dedham, MA

Explore by feature - Garage

6 rentals with a garage in Dedham, MA

Explore by feature - Air Conditioning

28 rentals with air conditioning in Dedham, MA

Explore by feature - Washer/dryer

35 rentals with a washer/dryer in Dedham, MA

Explore by feature - Outdoor Space

Homes for sale near 39 Chickering Rd

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Off Market Homes Near 39 Chickering Rd

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Frequently asked questions about 39 Chickering Rd

  • What is 39 Chickering Rd estimated to be worth?
    Trulia's estimated value for 39 Chickering Rd in Dedham, MA is $1,009,000.
  • What is the price history for 39 Chickering Rd?
    39 Chickering Rd in Dedham, MA last sold for $625,000 in May 2017.
  • 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 39 Chickering Rd?
    The lot at 39 Chickering Rd in Dedham, MA is about 0.27 acres (11,761 sq ft).
  • Does 39 Chickering Rd have a garage?
    Yes, 39 Chickering Rd in Dedham, MA has a garage.