81 Chestnut St, Dedham, MA 02026
Property image
Property image
OFF MARKET

81 Chestnut St
Dedham, MA 02026

Dexter
  • 4 Beds
  • 3 Baths
  • 3,010 sqft (on 0.30 acres)

$1,470,700

Trulia Estimate
as of Jul 5, 2026
Est. Refi. Payment $8,546/mo*
Refinance Your Home

$1,470,700

Trulia Estimate
as of Jul 5, 2026
Est. Refi. Payment $8,546/mo*
Refinance Your Home
4 Beds
3 Baths
3,010 sqft
(on 0.30 acres)

Local Information

  • Map ViewExplore the area around 81 Chestnut St.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

NEW LISTING This c.1845 Colonial, on one of the most desirable streets in Precinct 1, offers spacious rooms with architectural details and high ceilings. The first floor includes a welcoming parlor, large living room with fireplace, formal dining room, and comfortable eat-in kitchen that opens to the patio and a home office. Family room plus 4 bedrooms and 3 full baths upstairs. 2-car garage and fenced yard. An easy walk to the historic village center.   Listing and Office by  Hope McDermott,   Hope McDermott Real Estate
81 Chestnut St, Dedham, MA 02026 is a 4 bedroom, 3 bathroom, 3,010 sqft single-family home in Dexter, built in 1845. It last sold for $680,000 on Aug 31, 2011. It is currently off market. The Trulia Estimate is $1,470,700, with a rent estimate of $6,147/month.

Home Highlights

Parking
Garage
Outdoor
Patio, Deck
A/C
Heating only
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 81 Chestnut St

Interior Features

Interior Details
BasementAtticNumber of Rooms: 10
Heating & Cooling
Heating: Forced Air, GasHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 3
Fireplace & Spa
Fireplace

Exterior Features

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

Property Information

Year Built
Year Built: 1845
Property Type / Style
Property Type: Single Family HomeArchitecture: Other

Community

Units in Building: 1

Lot Information

Lot Area: 0.30 acres

Price History for 81 Chestnut St

DatePriceEventSource
08/31/2011$680,000Sold
N/A
12/15/2010$799,000ListingRemovedAgent Provided
10/24/2010$799,000Listed For SaleAgent Provided
06/13/1990$450,000Sold
N/A

Market trends in Dedham

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
86
10MoM
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Property Tax and Assessment

Year2025
Tax$14,114
Assessment$1,118,400
Home facts updated by county records

Comparable Sales for 81 Chestnut St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
42 Martin Bates St, Dedham, MA
0.11
Single-Family Home
$770,000
06/11/26
3
1.5
1,770
167 Court St, Dedham, MA
0.32
Single-Family Home
$1,031,500
01/13/26
4
3
2,241
120 Court St, Dedham, MA
0.30
Single-Family Home
$1,310,000
07/16/25
4
3.5
3,100
92 Old River Pl, Dedham, MA
0.38
Single-Family Home
$800,000
04/01/26
4
2
2,572
39 Court St, Dedham, MA
0.23
Single-Family Home
$1,775,000
08/01/25
5
2.5
4,075
1040 High St, Dedham, MA
0.49
Single-Family Home
$910,000
01/29/26
3
3
2,462
55 Dwight St, Dedham, MA
0.43
Single-Family Home
$1,065,000
02/13/26
3
2.5
2,986
21 Marsh St, Dedham, MA
0.31
Single-Family Home
$1,350,000
08/18/25
3
2.5
1,952
21 Church St, Dedham, MA
0.35
Single-Family Home
$1,270,000
06/12/26
4
2.5
2,702
35 Highland St, Dedham, MA
0.19
Single-Family Home
$1,025,000
11/13/25
3
1.5
1,671

Nearby homes

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Assigned Schools

These are the assigned schools for 81 Chestnut St.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

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

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Explore by feature - Air Conditioning

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Homes for sale near 81 Chestnut St

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Off Market Homes Near 81 Chestnut St

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