39 Chestnut St, Wakefield, MA 01880
OFF MARKET

$994,300

Trulia Estimate
  • 4 Beds
  • 2 Baths
  • 3,619 sqft (on 0.29 acres)

39 Chestnut St, Wakefield, MA 01880

West Side
Est. Refi. Payment $5,971/mo*
Refinance Your Home
Currently Off Market - Sold Jan 29, 1999 for $235,000

Home Value

Trulia Estimate
$994K
Since last month
Decreased$6K (-0.6%)
Since last year
Increased$54K (+5.7%)
Since last sale
Increased$759K (+323.1%)
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 +73% in the last 10 years
MonthEstimated value
2026
August 2026$994K
July 2026$1M
June 2026$1.02M
May 2026$999K
April 2026$983K
March 2026$972K
February 2026$937K
January 2026$938K
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 W Water St, Wakefield, MA
0.26
Multi-Family Home
$975,000
05/26/26
5
2
2,470
13 Chestnut St, Wakefield, MA
0.21
Multi-Family Home
$925,000
06/08/26
3
3.5
3,490
66 Gould St, Wakefield, MA
0.38
Multi-Family Home
$1,100,000
11/26/25
4
2
2,288
46 Yale Ave, Wakefield, MA
0.07
Multi-Family Home
$950,000
11/14/25
4
4
2,554
18 Bartley St, Wakefield, MA
0.43
Multi-Family Home
$825,000
08/26/26
4
2.5
2,200
13 Highland St, Wakefield, MA
0.61
Multi-Family Home
$660,000
01/16/26
4
2
2,385
26-26-26A Richardson Ave, Wakefield, MA
0.22
Multi-Family Home
$940,000
06/23/26
5
2
2,037
30 Park St, Wakefield, MA
0.48
Multi-Family Home
$875,000
11/19/25
4
2
2,308
3 Walnut St, Wakefield, MA
0.24
Multi-Family Home
$805,000
07/24/26
3
2
1,615
18-20 Jefferson Rd, Wakefield, MA
0.53
Multi-Family Home
$580,000
11/06/25
4
2
1,540

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
50 Tuttle St #5, Wakefield, MA 01880
0.03
$326,700
1
1
526
Off Market
50 Tuttle St #10, Wakefield, MA 01880
0.03
$389,700
2
1
707
Off Market
50 Tuttle St #12, Wakefield, MA 01880
0.03
$344,000
1
1
526
Recently Sold
50 Tuttle St #15, Wakefield, MA 01880
0.03
$421,200
2
1
707
Off Market
6 Avon Ct #2, Wakefield, MA 01880
0.05
$580,000
4
2
2,070
Recently Sold
47 Chestnut St, Wakefield, MA 01880
0.06
$956,900
4
3
2,088
Off Market
46 Chestnut St #2, Wakefield, MA 01880
0.06
$769,700
3
2
2,169
Off Market
46 Chestnut St #1, Wakefield, MA 01880
0.06
$805,000
3
2
1,204
Recently Sold
49-A Chestnut St- #1, Wakefield, MA 01880
0.07
-
2
2
1,230
Off Market
12 Avon Ct, Wakefield, MA 01880
0.07
$721,100
3
1
1,599
Off Market
46 Yale Ave, Wakefield, MA 01880
0.07
$950,000
4
4
2,554
Recently Sold
49A Chestnut St #3, Wakefield, MA 01880
0.09
$859,000
4
2.5
1,736
For Sale

Local Information

  • Map ViewExplore the area around 39 Chestnut St.
  • Schools2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Multi-Family
Year Built
1880
Lot Size
0.29 acres
Living Area
3,619 sqft
Price/Sqft
$275

About this House

This multi-family home is located at 39 Chestnut St, Wakefield, MA. 39 Chestnut St is in the West Side neighborhood in Wakefield, MA and in ZIP code 01880. This property has 4 bedrooms, 2 bathrooms and approximately 3,619 sqft of floor space. This property has a lot size of 0.29 acres and was built in 1880.
39 Chestnut St, Wakefield, MA 01880 is a 4 bedroom, 2 bathroom, 3,619 sqft multi-family in West Side, built in 1880. It last sold for $235,000 on Jan 29, 1999. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $994,300, with a rent estimate of $3,176/month.

Home Details for 39 Chestnut St

Interior Features

Interior Details
BasementNumber of Rooms: 8
Heating & Cooling
Heating: GasHeating Fuel: Gas
Levels, Entrance, & Accessibility
Stories: 2

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Other

Property Information

Year Built
Year Built: 1880Year Updated: 1952
Property Type / Style
Property Type: Multi FamilyArchitecture: Conventional

Community

Units in Building: 2

Lot Information

Lot Area: 0.29 acres

Price and Tax history

DateEventPrice
Jan 29, 1999
Source: N/A
Sold
$235,000

Market trends in Wakefield

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$809K
$3.25KMoM
Sale-to-List Price
—
Price per sq ft
$490
$22MoM
Available listings
56
2MoM

Around this home

Neighborhood Overview

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

What Locals Say about West Side

At least 39 Trulia users voted on each feature.

  • 98 % Say parking is easy

  • 93 % Say it's dog friendly

  • 91 % Say people would walk alone at night

  • 90 % Say there are sidewalks

  • 90 % Say there's holiday spirit

  • 86 % Say car is needed

  • 86 % Say kids play outside

  • 83 % Say yards are well-kept

  • 81 % Say streets are well-lit

  • 81 % Say it's quiet

  • 79 % Say they plan to stay for at least 5 years

  • 71 % Say neighbors are friendly

  • 67 % Say it's walkable to restaurants

  • 62 % Say there's wildlife

  • 60 % Say there are community events

  • 49 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • Trulia User
    "We love dogs, they are always welcome! Messes are cleaned up and there are plenty of dog walkers and we also have dog parks in and around the area!"
    0
    Flag
  • Casey H.
    "Best place I know. Grew up here and bought a home to raise my children. Beat area I know. The schools are great. My kids still can play outside safely and I don’t have to worry. "
    4
    Flag
  • Eileen R.
    "Independence Day Parade Italian Festival Schools events Little League Community Events...….!!!!!!!!!!!"
    0
    Flag
  • Nicole C.
    "People frequently walk their dogs and even walk here from other neighborhoods. It is a safe neighborhood that is very dog friendly"
    0
    Flag
  • Universriot
    "4th of July Parade is the biggest in New England, light up of Hanukkah Menorah at Wakefield Common, every week there is some event near the lake Quannapowitt. "
    3
    Flag
  • Khintlian
    "Not a bad commute to the city. I feel as though Wakefield is a great central location. 95 south traffic is getting worse. North is better"
    2
    Flag
  • Denise D.
    "Nothing better than walking your dog around the lake!"
    0
    Flag
  • Denise D.
    "A little congested weekday mornings with traffic coming off of Route 128 and cutting through town to avoid the highway back up."
    0
    Flag
  • Denise D.
    "Beautiful Lake Quannapowitt, and very close to the center of town."
    0
    Flag
  • Denise D.
    "Lots of families with small children, and a lot of town activities for children."
    0
    Flag
  • Ian M.
    "Leash law and dog walkers are required to pick up after their dogs. There are a number of parks and access to Lake Quannapowitt."
    0
    Flag
  • Ian M.
    "It's an easy commute by car as route 128 is easily accessed. It is also on main MBTA bus and rail routes."
    0
    Flag
  • Ian M.
    "There are older homes that are well maintained, borders lake Quannapowitt."
    0
    Flag
  • Ian M.
    "The schools are five star rated. Sidewalks are well maintained. There are several, well maintained parks and playgrounds, and the jewel, Lake Quannapowitt."
    0
    Flag
  • Kathleen M.
    "A wonderful welcoming community, everyone is kind. There’s a beautiful lake to walk around with dogs kids or by yourself!"
    0
    Flag
  • Nicole C.
    "Great family neighborhood, lots of wonderful neighbors and beautiful trees and landscaping. Will never leave!"
    0
    Flag
  • Timothy L.
    "quite several, play ground ,walking around the lake ,church ,good schools, markets ,after school activities for kids , good roads , entertainment, nice restaurant, friendly people. "
    0
    Flag
  • Ahmet O.
    "More affordable than Winchester, Arlington, Lexington and the likes. But it is really a great town to live. The lake and park significantly contribute to the quality of life. A very child friendly, family oriented community but also a lot of young and active crowd. Good school system, great access to public transportation (train), and actually very conveniently located to access i-93 and I-95. Commute to the city is easier and shorter than some other towns closer to the city from sheer distance perspective. We are very happy that we left Arlington and moved to Wakefield. Nicer house, lower taxes and just better quality of life. "
    0
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 39 Chestnut St

  • What is 39 Chestnut St estimated to be worth?
    Trulia's estimated value for 39 Chestnut St in Wakefield, MA is $994,300.
  • What is the price history for 39 Chestnut St?
    39 Chestnut St in Wakefield, MA last sold for $235,000 in January 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 $809K. That is up $3.25K from the prior month.

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Off Market Homes Near 39 Chestnut St

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