39 Pleasant St, Wakefield, MA 01880
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Property image
OFF MARKET

39 Pleasant St
Wakefield, MA 01880

  • 5 Beds
  • 3 Baths
  • 2,188 sqft

$765,100

Trulia Estimate
as of Aug 7, 2026
Est. Refi. Payment $4,648/mo*
Refinance Your Home

$765,100

Trulia Estimate
as of Aug 7, 2026
Est. Refi. Payment $4,648/mo*
Refinance Your Home
5 Beds
3 Baths
2,188 sqft

Local Information

  • Map ViewExplore the area around 39 Pleasant St.
  • Schools1 Preschool School3 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Multi-Family
Year Built
1900
Living Area
2,188 sqft
Price/Sqft
$350
Parking
Garage

About this House

Attention contractors, re-habbers and investors! This two family is superbly located near Lake Quannapowitt, Wakefield Common and downtown. Three finished levels, flexible floor plan. Great potential. 10 Rooms, 4 bedrooms, 3 full baths. Separate gas and electric. Garage and offstreet parking. Convenient to bus line to Oak Grove, commuter rail to Boston and major highways. Corner lot. Bring your ideas and vision for this renovation project with fantastic upside !
39 Pleasant St, Wakefield, MA 01880 is a 5 bedroom, 3 bathroom, 2,188 sqft multi-family built in 1900. It last sold for $750,000 on Aug 11, 2025 (7% above the $699,900 asking price). It is currently off market. The Trulia Estimate is $765,100, with a rent estimate of $3,277/month.

Home Details for 39 Pleasant St

Interior Features

Interior Details
Basement: Full,Walk-Out Access,Interior EntryNumber of Rooms: 11
Beds & Baths
Number of Bedrooms: 5Number of Bathrooms: 3Number of Bathrooms (full): 3
Dimensions and Layout
Living Area: 2188 Square Feet
Appliances & Utilities
Utilities: for Gas RangeAppliances: Range, Refrigerator, Washer, DryerDryerRefrigeratorWasher
Heating & Cooling
Heating: Steam,OilHas HeatingHeating Fuel: Steam
Fireplace & Spa
No FireplaceNo Spa
Gas & Electric
Electric: Circuit Breakers
Windows, Doors, Floors & Walls
Window: Insulated WindowsFlooring: Wood, Vinyl, Hardwood
Levels, Entrance, & Accessibility
Number of Stories: 3Floors: Wood, Vinyl, Hardwood

Exterior Features

Exterior Home Features
Roof: Shingle RubberPatio / Porch: PorchFoundation: Stone
Parking & Garage
Number of Garage Spaces: 1Number of Covered Spaces: 1Open Parking Spaces: 3Has a GarageHas Open ParkingParking Spaces: 4Parking: Paved Drive,Off Street
Frontage
Road Frontage: PublicNot on Waterfront
Water & Sewer
Sewer: Public Sewer
Farm & Range
Frontage Length: 53.00
Finished Area
Finished Area (above surface): 2188

Property Information

Year Built
Year Built: 1900
Property Type / Style
Property Type: Residential IncomeProperty Subtype: Multi Family
Building
Construction Materials: FrameDoes Not Include Home Warranty
Property Information
Parcel Number: 818536

Price & Status

Price
List Price: $699,900
Status Change & Dates
Off Market Date: Fri May 30 2025

Active Status

MLS Status: Sold

Location

Direction & Address
City: Wakefield

Building

Building Area
Building Area: 2188 Square Feet

Community

Community Features: Public Transportation, Shopping, Tennis Court(s), Park, Walk/Jog Trails, Bike Path, Conservation Area, Highway Access, House of Worship, Public School, T-StationNot Senior Community

Lot Information

Lot Area: 3358 sqft

Offer

Contingencies: Pending P&S

Miscellaneous

BasementMls Number: 73372964Above Grade Unfinished Area: 2188

Additional Information

Public TransportationShoppingTennis Court(s)ParkWalk/Jog TrailsBike PathConservation AreaHighway AccessHouse of WorshipPublic SchoolT-Station
Last check for updates: about 9 hours ago
Listed by Stephen Conroy, (617) 823-4198
Boardwalk Real Estate, (781) 944-7820
Bought with: John Ross, (781) 245-4250, Coldwell Banker Realty - New England Home Office, (781) 684-6300
Source: MLS PIN, MLS#73372964

Price History for 39 Pleasant St

DatePriceEventSource
08/11/2025$750,000Sold
MLS PIN #73372964
05/19/2025$699,900ContingentMLS PIN #73372964
05/12/2025$699,900Listed For SaleMLS PIN #73372964

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$8,685
Assessment$765,200
Home facts updated by county records

Comparable Sales for 39 Pleasant St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
51 Crescent St, Wakefield, MA
0.25
Multi-Family Home
$850,000
01/29/26
6
3
3,278
30 Park St, Wakefield, MA
0.04
Multi-Family Home
$875,000
11/19/25
4
2
2,308
13 Highland St, Wakefield, MA
0.09
Multi-Family Home
$660,000
01/16/26
4
2
2,385
26-26-26A Richardson Ave, Wakefield, MA
0.43
Multi-Family Home
$940,000
06/23/26
5
2
2,037
9 Cyrus St, Wakefield, MA
0.41
Multi-Family Home
$915,000
05/01/26
5
2
2,772
22 Armory St, Wakefield, MA
0.45
Multi-Family Home
$955,000
10/31/25
7
3
2,625
46 Yale Ave, Wakefield, MA
0.49
Multi-Family Home
$950,000
11/14/25
4
4
2,554
57 Wave Ave, Wakefield, MA
0.33
Multi-Family Home
$1,070,000
05/13/26
5
2
2,433

Nearby homes

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Assigned Schools

These are the assigned schools for 39 Pleasant 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.

What Locals Say about Wakefield

At least 152 Trulia users voted on each feature.

  • 91 % Say it's dog friendly

  • 89 % Say parking is easy

  • 86 % Say there are sidewalks

  • 84 % Say people would walk alone at night

  • 84 % Say there's holiday spirit

  • 82 % Say yards are well-kept

  • 80 % Say car is needed

  • 77 % Say streets are well-lit

  • 75 % Say kids play outside

  • 73 % Say it's walkable to restaurants

  • 72 % Say they plan to stay for at least 5 years

  • 69 % Say it's quiet

  • 62 % Say neighbors are friendly

  • 62 % Say there's wildlife

  • 54 % Say it's walkable to grocery stores

  • 50 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Trulia User
    "I have lived in this town for the last 25 years. I own a business downtown here and have a great sense that a small community school system is a great safe location near major highways within 45 minutes to the beaches then an hour away to the ski area and 10 miles to downtown Boston"
    0
    Flag
  • Trulia User
    "The school system is good, especially their music department It's a great marching band too. Great parks and close to Transportation "
    0
    Flag
  • Alton Zink
    "It has good schools lots of local shopping and recreational activity? Wakefield has many highways that bring access to local beaches as well as going north to New Hampshire for skiing and hiking"
    1
    Flag
  • Trulia User
    "I live and own my own business in town, for 24 years. Great place to raise kids . Safe community Walkable, close to public transportation"
    0
    Flag
  • Trulia User
    "Let's make food for Christmas, on Valentine's Day let's make suprimes, Halloween we give sweets to all the children And many other things"
    1
    Flag
  • Trulia User
    "Safe, local kids kids-friendly parks, walking areas, public transportation, good school system Near major roads "
    0
    Flag
  • Trulia User
    "been here 6 years and my neighbors and the neighborhood is the best. We all watch out for one another. It is a very peaceful area and very safe."
    0
    Flag
  • Trulia User
    "digs and walkers are always around. very friendly and secure neighborhood. everyone looks out for each other."
    0
    Flag
  • 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
  • Trulia User
    "Dog owners love this neighborhood low traffic, and plenty of sidewalk space plenty of places to let the dog off the leash and run parks etc"
    0
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  • Trulia User
    "Many families in the area, with great fields, parks, and stores within walking distance. All this but still private little neighborhoods."
    0
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  • 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
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  • Trulia User
    "Lots of people walk their dogs around. Always friendly. Nice fields to let them loose in. Everyone is respectful"
    0
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  • Megangobeille
    "There are two bus lines through Wakefield that end at the orange line Oak Grove or Malden Center, both busses go to both train stations. Commute is 30mins on the bus to oak grove during rush hour and 30mins on the train to Downton Crossing"
    0
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  • Jennifer B.
    "Easy on commuter rail, it’s about an hour door to door. Orange line in Malden/Medford not far either."
    0
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  • Jennifercb92
    "There’s a great school system, and it’s in close enough proximity to Boston that it’s a great place to live and raise a family."
    3
    Flag
  • Kaitlyn S.
    "Halloween is a big event . Every house is a party . My husband and I know just about everyone on our street!! We have bbq and fires with the neighbors all summer ."
    0
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  • Jen M. .
    "My commute to Boston is over an hour each way. I do not recommend driving if you can take the commuter rail to get to work. "
    0
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  • Kaitlyn S.
    "I’ve lived in this area for 5 years now . It’s like it’s own tiny community. Everyone is very friendly and knows one another . The elementary school is excellent and the commuter rail in a walk away "
    0
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  • 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
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  • 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
  • Kathleen D.
    "I have lived in this neighborhood for 19 years. The neighbors are lovely & create a friendly atmosphere."
    0
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  • Sam C.
    "We are huge dog lovers and there are great places to take them for long walks."
    0
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  • Sam C.
    "The commute is very simple. There are many different ways you can use to get to the heart of Greenwood."
    0
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  • Sam C.
    "It is a small little community within a bigger town."
    0
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  • Sam C.
    "It is a GREAT place to raise kids and the school is an awesome place to learn."
    0
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  • Rebecca R.
    "We do like dogs."
    0
    Flag
  • Rebecca R.
    "It's very beautiful with nice people."
    0
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  • Denise D.
    "A little congested weekday mornings with traffic coming off of Route 128 and cutting through town to avoid the highway back up."
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  • Denise D.
    "Beautiful Lake Quannapowitt, and very close to the center of town."
    0
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  • Denise D.
    "Lots of families with small children, and a lot of town activities for children."
    0
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  • David S.
    "The rail and bus service can take you to Boston and the easy access to major highways makes commuting easy."
    0
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  • David S.
    "Quiet area, friendly neighbors, suburban bordering on rural, not crowded, lots of small businesses, but no heavy industry. Lots of trees, nice homes and scenery. Easy access to major highways, lots of places to eat or shop, no crime, fire station nearby, prompt police response if needed, & good roads. Also, local bank has a Greenwood office, and you don't have to go far to find what you need. Just a nice environment to live in. Plus, rail service to Boston, and to points North as well."
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  • Arayadiane
    "very friendly and well maintained neighborhoods. good schools, very safe close to highways. very walkable. love livinh here."
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  • Huyen N.
    "Beautiful wood areas with many hiking trails. Generally quiet and pretty safe neighborhood with nice neighbors."
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  • 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
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  • Ian M.
    "There are older homes that are well maintained, borders lake Quannapowitt."
    0
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Apartments for Rent

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Explore by feature - Pet Friendly

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Homes for sale near 39 Pleasant St

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Off Market Homes Near 39 Pleasant St

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The property listing data and information set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information are for the personal, non commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information set forth herein.
The MLS listing information displayed is deemed reliable, but is not guaranteed accurate by the MLS.