29 Pleasant St, Upton, MA 01568
Property image
Property image
OFF MARKET

29 Pleasant St
Upton, MA 01568

  • 3 Beds
  • 2.5 Baths
  • 2,092 sqft (on 0.50 acres)

$681,700

Trulia Estimate
as of Aug 6, 2026
Est. Refi. Payment $4,269/mo*
Refinance Your Home

$681,700

Trulia Estimate
as of Aug 6, 2026
Est. Refi. Payment $4,269/mo*
Refinance Your Home
3 Beds
2.5 Baths
2,092 sqft
(on 0.50 acres)

Local Information

  • Map ViewExplore the area around 29 Pleasant St.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1994
Lot Size
0.5 acres
Living Area
2,092 sqft
Price/Sqft
$326
Parking
Garage

About this House

Convenient location, walk to schools and Upton resources. Colonial 3 bedroom and 2.5 baths, two story entry foyer. New roof, new AC, lots of ceramic tile floors. Finished basement accommodates many uses. Most of first floor is hardwoods, carpet in bedrooms, eat in kitchen opens out onto the deck overlooking back yard. Fairly level yard with sizable front & back yard areas.
29 Pleasant St, Upton, MA 01568 is a 3 bedroom, 3 bathroom, 2,092 sqft single-family home built in 1994. It last sold for $550,000 on Mar 31, 2023. It is currently off market. The Trulia Estimate is $681,700, with a rent estimate of $3,509/month.

Home Details for 29 Pleasant St

Interior Features

Interior Details
BasementNumber of Rooms: 3
Heating & Cooling
Heating: Forced Air, GasAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2Floors: Tile, Carpet, Hardwood, Laminate, Linoleum Vinyl
Appliances & Utilities
Cable ReadyDishwasherRefrigerator
Fireplace & Spa
Fireplace

Exterior Features

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

Property Information

Year Built
Year Built: 1994
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 7

Lot Information

Lot Area: 0.50 acres

Price History for 29 Pleasant St

DatePriceEventSource
03/31/2023$550,000Sold
MLS PIN #73080400
02/20/2023$519,000Listed For SaleMLS PIN #73080400
11/15/2019$409,000ListingRemovedAgent Provided
10/13/2019$409,000Listed For SaleAgent Provided
05/31/2017$330,000Sold
N/A
12/06/2011$349,000ListingRemovedAgent Provided
08/21/2011$349,000Listed For SaleAgent Provided
06/04/2011$349,000ListingRemovedAgent Provided
03/24/2011$349,000PriceChange
Agent Provided
03/04/2011$1,950PriceChange
Agent Provided
09/23/2010$349,000Listed For SaleAgent Provided
11/30/2007$409,000ListingRemovedAgent Provided
11/14/2007$409,000Listed For SaleAgent Provided
02/27/1997$200,000Sold
N/A
04/03/1995$170,000Sold
N/A

Market trends in Upton

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
37
2MoM
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Property Tax and Assessment

Year2025
Tax$7,697
Assessment$585,300
Home facts updated by county records

Comparable Sales for 29 Pleasant St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
21 Warren Rd, Upton, MA
0.11
Single-Family Home
$600,000
06/30/26
3
1.5
1,789
10 Mendon St, Upton, MA
0.13
Single-Family Home
$505,000
09/29/25
3
2
1,440
20 Fiske Ave, Upton, MA
0.31
Single-Family Home
$682,000
06/26/26
3
2
1,777
72 Main St, Upton, MA
0.07
Single-Family Home
$478,000
05/13/26
2
1
1,536
4 Fiske Mill Rd, Upton, MA
0.11
Single-Family Home
$605,000
09/26/25
2
2.5
1,720
57 Plain St, Upton, MA
0.39
Single-Family Home
$525,000
07/22/26
3
2.5
1,372
35 Brooks St, Upton, MA
0.63
Single-Family Home
$501,000
05/29/26
3
2
1,762
4 Hazeltine Rd, Upton, MA
0.31
Single-Family Home
$970,000
06/02/26
4
2.5
3,000
41 Main St, Upton, MA
0.25
Single-Family Home
$460,000
06/30/26
2
1.5
1,155
20 Josiah Dr, Upton, MA
0.42
Single-Family Home
$785,000
07/20/26
4
2.5
2,408

Nearby homes

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Assigned Schools

These are the assigned schools for 29 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 Upton

At least 28 Trulia users voted on each feature.

  • 94 % Say car is needed

  • 88 % Say parking is easy

  • 83 % Say yards are well-kept

  • 75 % Say it's dog friendly

  • 73 % Say people would walk alone at night

  • 71 % Say there's wildlife

  • 68 % Say they plan to stay for at least 5 years

  • 67 % Say there's holiday spirit

  • 66 % Say it's quiet

  • 60 % Say neighbors are friendly

  • 59 % Say kids play outside

  • 48 % Say there are sidewalks

  • 30 % Say there are community events

  • 25 % Say streets are well-lit

  • 17 % Say it's walkable to restaurants

  • 13 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • Fernando M.
    "I've lived in Upton now for almost a Decade and it's an amazing town. The community is amazing, people are respectful, lots of community events, lots of recreational areas from Kiwanis beach, Upton State Park, Peppercorn Hill Conservation Area and other location, the schools are excellent, teachers care about the students, great academic and athletic departments. Upton truly is a place you can raise a family and feel safe."
    0
    Flag
  • Kristy G. B.
    "Must leave early to get to Boston or Boston area. Early is 6:30 or leave after 9 am. There is a lot of traffic going East, but is going on the other direction not as bad. There is not a lot of traffic on the town, but on the boarders of all surrounding towns there is traffic at peak hours."
    7
    Flag
  • Kristy G. B.
    "We’ve lived here for 9 years and everyone is very friendly and looks out for each other, yet you maintain your privacy. It’s a great sense of community with lots of young families."
    1
    Flag
  • Bapalladini
    "it's a nice area. my dad loves it here. nice neighborhood, good community. old time feel to the area. plenty of hiking, parks etc. good schools, overall great "
    2
    Flag
  • Kristy G. B.
    "Safe, tight knit community where everyone is looking out for each other. The community is growing and young families are moving in. It definitely has a small town feel. "
    2
    Flag
  • Lily G.
    "plenty of parks to walk dogs. big yards and land for dogs to play and have space. close to tuffs animal hospital. "
    1
    Flag
  • Paola W. O.
    "Tons of areas to walk dogs. You just have to be careful with wild animals that could attack your dogs at night. "
    2
    Flag
  • Acmalzone
    "Small, friendly neighborhood town. Great neighbors. Awesome school system. Safe town. No chain stores or chain restaurants. All Ma & Pop shops and family owned restaurants."
    2
    Flag
  • annacollari
    "I have lived here for 2 years and it has already topped all the 10 other places i lived in, it is very clean, and my kids get a great education at the two high schools and one elementary school. All the people here are so nice and friendly. There are loads of places to walk and hang out, and it is great for kids, there is one park and baseball field, and there is another public park at the Elementary school. Upton is a Great place to live!"
    0
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  • Petersonk17
    "I live here since I was born and I think it is a wonderful neighborhood to live in. Lots of kids live around so it is good for families with children."
    0
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Off Market Homes Near 29 Pleasant St

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