99 Chestnut St, Wakefield, MA 01880
OFF MARKET

99 Chestnut St
Wakefield, MA 01880

West Side
  • 3 Beds
  • 1.5 Baths
  • 1,843 sqft

$823,700

Trulia Estimate
as of Aug 8, 2026
Est. Refi. Payment $4,998/mo*
Refinance Your Home

$823,700

Trulia Estimate
as of Aug 8, 2026
Est. Refi. Payment $4,998/mo*
Refinance Your Home
3 Beds
1.5 Baths
1,843 sqft

Local Information

  • Map ViewExplore the area around 99 Chestnut St.
  • Schools2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1949
Living Area
1,843 sqft
Price/Sqft
$447
Parking
Garage

About this House

This single-family home is located at 99 Chestnut St, Wakefield, MA. 99 Chestnut St is in the West Side neighborhood in Wakefield, MA and in ZIP code 01880. This property has 3 bedrooms, 2 bathrooms and approximately 1,843 sqft of floor space. This property has a lot size of 8276 sqft and was built in 1949.
99 Chestnut St, Wakefield, MA 01880 is a 3 bedroom, 2 bathroom, 1,843 sqft single-family home in West Side, built in 1949. It last sold for $207,000 on Aug 3, 2020. It is currently off market. The Trulia Estimate is $823,700, with a rent estimate of $4,022/month.

Home Details for 99 Chestnut St

Interior Features

Interior Details
BasementAtticNumber of Rooms: 7Types of Rooms: OfficeCeiling Fan
Heating & Cooling
Heating: Other, OilAir ConditioningCooling System: CentralHeating Fuel: Other
Levels, Entrance, & Accessibility
Stories: 2Floors: Hardwood
Appliances & Utilities
Cable Ready
Fireplace & Spa
Fireplace
Windows, Doors, Floors & Walls
Double Paned Windows

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: WoodPatio
Parking & Garage
GarageParking Spaces: 4Parking: Garage Attached

Property Information

Year Built
Year Built: 1949Year Updated: 1965
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 8276 sqft

Price History for 99 Chestnut St

DatePriceEventSource
08/03/2020$207,000Sold
N/A
07/15/2005$22,000Sold
N/A
07/30/2002$363,400Sold
N/A
01/26/2001$310,000Sold
N/A
07/08/1994$197,500Sold
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$7,668
Assessment$675,600
Home facts updated by county records

Comparable Sales for 99 Chestnut St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
10 Converse St, Wakefield, MA
0.16
Single-Family Home
$875,000
12/30/25
3
1.5
2,309
39 Cedar St, Wakefield, MA
0.18
Single-Family Home
$825,000
04/15/26
3
2
1,350
5 Byron St, Wakefield, MA
0.32
Single-Family Home
$811,500
12/12/25
3
1
1,832
34 Cedar St, Wakefield, MA
0.22
Single-Family Home
$850,000
02/27/26
3
2
1,288
22 Eustis Ave, Wakefield, MA
0.33
Single-Family Home
$860,000
07/13/26
3
1.5
1,603
26 Curve St, Wakefield, MA
0.26
Single-Family Home
$785,000
12/19/25
2
2
1,888
47 Emerson St, Wakefield, MA
0.29
Single-Family Home
$983,000
12/18/25
3
2
1,717
40 Friend St, Wakefield, MA
0.41
Single-Family Home
$902,000
01/22/26
3
2
1,915
18 Byron St, Wakefield, MA
0.35
Single-Family Home
$975,000
09/15/25
4
2
2,081
18 Mountain Ave, Wakefield, MA
0.57
Single-Family Home
$815,000
11/19/25
3
2
1,808

Nearby homes

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Assigned Schools

These are the assigned schools for 99 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

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

What Locals Say about West Side

At least 38 Trulia users voted on each feature.

  • 98 % Say parking is easy

  • 92 % Say it's dog friendly

  • 91 % Say people would walk alone at night

  • 90 % Say there's holiday spirit

  • 89 % Say there are sidewalks

  • 86 % Say car is needed

  • 86 % Say kids play outside

  • 82 % Say it's quiet

  • 82 % Say yards are well-kept

  • 81 % Say streets are well-lit

  • 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

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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

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Homes for sale near 99 Chestnut St

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Off Market Homes Near 99 Chestnut St

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Frequently asked questions about 99 Chestnut St

  • What is 99 Chestnut St estimated to be worth?
    Trulia's estimated value for 99 Chestnut St in Wakefield, MA is $823,700.
  • What is the price history for 99 Chestnut St?
    99 Chestnut St in Wakefield, MA last sold for $207,000 in August 2020.
  • 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.
  • Does 99 Chestnut St have air conditioning?
    Yes, 99 Chestnut St in Wakefield, MA has air conditioning.
  • How big is the lot at 99 Chestnut St?
    The lot at 99 Chestnut St in Wakefield, MA is about 0.19 acres (8,276 sq ft).