21 Chestnut St, Wakefield, MA 01880
OFF MARKET

21 Chestnut St
Wakefield, MA 01880

Downtown
  • 6 Beds
  • 6 Baths
  • 4,618 sqft

$1,406,800

Trulia Estimate
as of Aug 8, 2026
Est. Refi. Payment $8,484/mo*
Refinance Your Home

$1,406,800

Trulia Estimate
as of Aug 8, 2026
Est. Refi. Payment $8,484/mo*
Refinance Your Home
6 Beds
6 Baths
4,618 sqft

Local Information

  • Map ViewExplore the area around 21 Chestnut St.
  • Schools1 Preschool School3 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Multi-Family
Year Built
1850
Living Area
4,618 sqft
Price/Sqft
$305
Parking
Garage

About this House

This multi-family home is located at 21 Chestnut St, Wakefield, MA. 21 Chestnut St is in the Downtown neighborhood in Wakefield, MA and in ZIP code 01880. This property has 6 bedrooms, 6 bathrooms and approximately 4,618 sqft of floor space. This property has a lot size of 10018 sqft and was built in 1850.
21 Chestnut St, Wakefield, MA 01880 is a 6 bedroom, 6 bathroom, 4,618 sqft multi-family in Downtown, built in 1850. It last sold for $350,000 on Aug 6, 1999. It is currently off market. The Trulia Estimate is $1,406,800, with a rent estimate of $3,123/month.

Home Details for 21 Chestnut St

Interior Features

Interior Details
BasementNumber of Rooms: 14
Heating & Cooling
Heating: Other, OilAir ConditioningHeating Fuel: Other
Levels, Entrance, & Accessibility
Stories: 2

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Wood
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 1850Year Updated: 1952
Property Type / Style
Property Type: Multi FamilyArchitecture: Conventional

Community

Units in Building: 3

Lot Information

Lot Area: 10018 sqft

Price History for 21 Chestnut St

DatePriceEventSource
08/06/1999$350,000Sold
N/A
05/20/1988$288,000Sold
N/A

Market trends in Wakefield

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$806K
$89.83KMoM
Sale-to-List Price
—
Price per sq ft
$468
$15MoM
Available listings
54
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Property Tax and Assessment

Year2025
Tax$16,223
Assessment$1,429,300
Home facts updated by county records

Comparable Sales for 21 Chestnut St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
13 Chestnut St, Wakefield, MA
0.06
Multi-Family Home
$925,000
06/08/26
3
3.5
3,490
24 W Water St, Wakefield, MA
0.17
Multi-Family Home
$975,000
05/26/26
5
2
2,470
46 Yale Ave, Wakefield, MA
0.15
Multi-Family Home
$950,000
11/14/25
4
4
2,554
22 Armory St, Wakefield, MA
0.22
Multi-Family Home
$955,000
10/31/25
7
3
2,625
51 Crescent St, Wakefield, MA
0.28
Multi-Family Home
$850,000
01/29/26
6
3
3,278
26-26-26A Richardson Ave, Wakefield, MA
0.13
Multi-Family Home
$940,000
06/23/26
5
2
2,037
13 Highland St, Wakefield, MA
0.47
Multi-Family Home
$660,000
01/16/26
4
2
2,385
46 Richardson St, Wakefield, MA
0.54
Multi-Family Home
$1,010,000
07/20/26
7
3
2,640
30 Park St, Wakefield, MA
0.35
Multi-Family Home
$875,000
11/19/25
4
2
2,308
39 Pleasant St, Wakefield, MA
0.39
Multi-Family Home
$750,000
08/11/25
5
3
2,188

Nearby homes

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Assigned Schools

These are the assigned schools for 21 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

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

What Locals Say about Downtown

At least 14 Trulia users voted on each feature.

  • 92 % Say people would walk alone at night

  • 90 % Say it's dog friendly

  • 88 % Say yards are well-kept

  • 88 % Say streets are well-lit

  • 86 % Say there's holiday spirit

  • 86 % Say there are sidewalks

  • 84 % Say parking is easy

  • 83 % Say it's walkable to restaurants

  • 70 % Say car is needed

  • 69 % Say kids play outside

  • 61 % Say it's walkable to grocery stores

  • 59 % Say there's wildlife

  • 57 % Say they plan to stay for at least 5 years

  • 56 % Say it's quiet

  • 55 % Say there are community events

  • 55 % Say neighbors are friendly

Sourced by Trulia users. Learn more about our methodology.
  • Trulia User
    "They would love to walk the lake which many residents do. Dog park close by as well. Also, break heart reservation is close by for hiking, swimming and a dog park"
    0
    Flag
  • Tal B.
    "I have lived in Wakefield for 3 years now. The lake is really nice. The main street is up and coming. There is easy access to the city."
    0
    Flag
  • Patrick W. D.
    "Although I've only lived in wakefield 4 plus years,I'm still amazed at all the services that are here in my own town.A great walking town,a beautiful lake to picnic at , or fish or boat. there is always something going on around the lake during the summer and fall months.A farmers market.Some really great restaurants and bars to sit and sip while listening to some good music.Great Library.Shopping in town,or a short distance away. A great veterans park,and I believe that if you show respect to your local veterans you show character,and Wakefield does.Commuter Rail to Boston,and great local bus service.A lot of volunteer opportunities exist, or if you just want to blend in you can do that also.I just love my new home towm."
    0
    Flag

LGBTQ Local Legal Protections

Apartments for Rent

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Explore by feature - Pet Friendly

22 pet-friendly rentals in Wakefield, MA

Explore by feature - Garage

10 rentals with a garage in Wakefield, MA

Explore by feature - Air Conditioning

24 rentals with air conditioning in Wakefield, MA

Explore by feature - Washer/dryer

23 rentals with a washer/dryer in Wakefield, MA

Homes for sale near 21 Chestnut St

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Off Market Homes Near 21 Chestnut St

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Frequently asked questions about 21 Chestnut St

  • What is 21 Chestnut St estimated to be worth?
    Trulia's estimated value for 21 Chestnut St in Wakefield, MA is $1,406,800.
  • What is the price history for 21 Chestnut St?
    21 Chestnut St in Wakefield, MA last sold for $350,000 in August 1999.
  • Is Wakefield a buyer's or seller's market?
    Wakefield is currently a seller's market, based on recent for-sale activity.
  • What's the median sale price in Wakefield?
    The median sale price in Wakefield is $806K. That is up $89.83K from the prior month.