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

$745,700

Trulia Estimate
as of Aug 25, 2026
  • 3 Beds
  • 2 Baths
  • 1,388 sqft
  • 3 Beds
  • 2 Baths
  • 1,388 sqft

20 Chickering Rd, Dedham, MA 02026

Dexter

Home Highlights

Property Type
Single-Family Home
Living Area
1,388 sqft
Price/Sqft
$537
Parking
Attached Garage

Local Information

  • Map ViewExplore the area around 20 Chickering Rd.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

Home beautiful! Sunny 3 bedroom split level home located in a desirable residential area near Westwood line. Newly renovated with brand new gourmet kitchen with quartz countertops, new windows, new heating system and central air, new 3/4 bath in lower level with shower stall. Floors have all been refinished, freshly painted throughout. Large family room in lower level can also be used as a 4rth bedroom. 1 car garage under and a large driveway. Large back yard perfect for your summer barbecues.. Great commuter location with nearby access to highways, the T, shops, Legacy Place, public transportation, town center, schools and easy access into the city...
20 Chickering Rd, Dedham, MA 02026 is a 3 bedroom, 2 bathroom, 1,388 sqft single-family home in Dexter. It last sold for $575,000 on Jan 23, 2023 (13,590% above the $4,200 asking price). More recently, it was listed as a rental in February 2025 with an asking price of $4,200 per month. That rental listing was removed on February 27, 2025. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $745,700, with a rent estimate of $4,169/month.

Home Details for 20 Chickering Rd

Property Information

Property Type / Style
Property Type: Single Family Home

Rental Terms, Policies & Fees

Lease Term: 1 YearAvailable: now

Interior Features

Appliances & Utilities
DishwasherMicrowaveRefrigerator
Levels, Entrance, & Accessibility
Floors: Hardwood, Tile

Exterior Features

Parking & Garage
Parking: Attached Off Street, On Site

Comparable Sales for 20 Chickering Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
24 Pond Farm Rd, Dedham, MA
0.13
Single-Family Home
$700,000
11/25/25
3
1.5
1,610 sqft
24 Fair Oak Rd, Dedham, MA
0.19
Single-Family Home
$620,000
09/30/25
3
1.5
1,540 sqft
24 Fay Rd, Dedham, MA
0.26
Single-Family Home
$716,400
07/07/26
3
1.5
1,560 sqft
133 Pacella Dr, Dedham, MA
0.34
Single-Family Home
$855,000
06/12/26
3
2
1,434 sqft
115 Cobleigh St, Westwood, MA
0.43
Single-Family Home
$790,000
05/15/26
3
2
1,532 sqft
14 Eldridge Pl, Westwood, MA
0.32
Single-Family Home
$935,000
05/12/26
3
2
2,048 sqft
886 Gay St, Westwood, MA
0.07
Single-Family Home
$1,000,000
11/20/25
4
2.5
2,284 sqft
8 Hillview Ter, Westwood, MA
0.29
Single-Family Home
$701,000
03/30/26
3
1
1,210 sqft
70 Cobleigh St, Westwood, MA
0.35
Single-Family Home
$1,010,000
06/15/26
3
1.5
2,264 sqft
829 Gay St, Westwood, MA
0.23
Single-Family Home
$1,150,000
05/29/26
4
2
2,360 sqft

Nearby homes

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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

LGBTQ Local Legal Protections

Price and Tax history

DateEventPrice
Feb 27, 2025
Source: Zillow Rentals
ListingRemoved
$4,200
Feb 12, 2025
Source: Zillow Rentals
Listed For Rent
$4,200
Jan 23, 2023
Source: MLS PIN #73063301
Sold
$575,000
Dec 13, 2022
Source: MLS PIN #73063301
Contingent
$589,900
Dec 6, 2022
Source: MLS PIN #73063301
Listed For Sale
$589,900

Frequently asked questions about 20 Chickering Rd

  • What is 20 Chickering Rd estimated to be worth?
    Trulia's estimated value for 20 Chickering Rd in Dedham, MA is $745,700.
  • What is the price history for 20 Chickering Rd?
    20 Chickering Rd in Dedham, MA last sold for $575,000 in January 2023.
  • 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.
  • Does 20 Chickering Rd have parking?
    Yes, 20 Chickering Rd in Dedham, MA has on-site parking.

Homes for rent near 20 Chickering Rd

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Affordability

TIP:Try to keep your rent within a third of your gross household income. Learn why in our Renter's Guide.
For this property
PER YEAR
is the suggested income
Win over prospective landlords with your smart budgeting. As a good rule of thumb, ideally you would have at least three times your monthly rent in combined household income.
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