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

27 Pleasant St
Upton, MA 01568

  • 4 Beds
  • 2.5 Baths
  • 2,132 sqft (on 0.45 acres)

$678,100

Trulia Estimate
as of Aug 18, 2026
Est. Refi. Payment $4,221/mo*
Refinance Your Home

$678,100

Trulia Estimate
as of Aug 18, 2026
Est. Refi. Payment $4,221/mo*
Refinance Your Home
4 Beds
2.5 Baths
2,132 sqft
(on 0.45 acres)

Home Value

Trulia Estimate
$678K
Since last month
Decreased$9K (-1.4%)
Since last year
Increased$17K (+2.5%)
Since last sale
Increased$270K (+66.2%)
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 +79% in the last 10 years
MonthEstimated value
2026
August 2026$678K
July 2026$687K
June 2026$691K
May 2026$682K
April 2026$681K
March 2026$671K
February 2026$655K
January 2026$639K
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
21 Warren Rd, Upton, MA
0.12
Single-Family Home
$600,000
06/30/26
3
1.5
1,789
10 Mendon St, Upton, MA
0.15
Single-Family Home
$505,000
09/29/25
3
2
1,440
7 Hazeltine Rd, Upton, MA
0.29
Single-Family Home
$680,000
08/14/26
4
2.5
1,800
20 Fiske Ave, Upton, MA
0.31
Single-Family Home
$682,000
06/26/26
3
2
1,777
5 Pleasant St, Upton, MA
0.21
Single-Family Home
$420,000
08/14/26
3
1
1,727
4 Hazeltine Rd, Upton, MA
0.30
Single-Family Home
$970,000
06/02/26
4
2.5
3,000
72 Main St, Upton, MA
0.07
Single-Family Home
$478,000
05/13/26
2
1
1,536
35 Brooks St, Upton, MA
0.62
Single-Family Home
$501,000
05/29/26
3
2
1,762
41 Main St, Upton, MA
0.23
Single-Family Home
$460,000
06/30/26
2
1.5
1,155
84 High St, Upton, MA
0.67
Single-Family Home
$595,000
01/07/26
4
3
2,463

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
31 Pleasant St, Upton, MA 01568
0.04
$574,900
3
2
1,932
Off Market
72 Main St, Upton, MA 01568
0.07
$478,000
2
1
1,536
Recently Sold
21 Warren Rd, Upton, MA 01568
0.12
$600,000
3
1.5
1,789
Recently Sold
30 Mendon St, Upton, MA 01568
0.12
$1,125,000
4
4
3,402
For Sale
74 Main St, Upton, MA 01568
0.09
$395,800
3
1.5
1,428
Off Market
4 Fiske Mill Rd, Upton, MA 01568
0.10
$656,500
2
2.5
1,720
Off Market
15 Pleasant St, Upton, MA 01568
0.13
$560,800
3
2
1,220
Off Market
10 Mendon St, Upton, MA 01568
0.15
$644,200
3
2
1,440
Off Market
3 Central Sq, Upton, MA 01568
0.16
$605,700
4
2
1,378
Off Market
70 Grove St, Upton, MA 01568
0.16
-
5
3.5
4,682
Off Market
20 Shoemaker Ln #14, Upton, MA 01568
0.16
-
2
2.5
2,228
Off Market
5 Chickadee Way #17, Upton, MA 01568
0.16
-
2
2
1,734
Off Market

Local Information

  • Map ViewExplore the area around 27 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
0.45 acres
Living Area
2,132 sqft
Price/Sqft
$318
Parking
Garage

About this House

BEST & FINAL OFFERS DUE MONDAY, MAY 6TH AT 6PM!!! Spacious 4 bedroom Colonial in the heart of Upton! Walk to down-town & both High Schools, not to miss any of the action! First floor provides living space for all of your needs. Kitchen opens to the eat-in kitchen area, spilling into the fire-placed family room. Or, head out the French door from the eat-in kitchen area to the vast wooden deck & back yard. Kitchen has been recently updated w/ new granite counter-tops, Moen kitchen faucet, stainless steel range & refrigerator! Newer dishwasher. Generously-sized dining room & living room, both w/ wooden floors, just off the kitchen and also on first floor. Laundry room and half bath conveniently located on the first floor just off the garage entrance. Head up the newly carpeted stairs to find 4 sizable bedrooms & two full bathrooms. Master has a walk-in closet as well! 2-car garage has tons of storage space; in addition, the unfinished basement can handle the rest!
27 Pleasant St, Upton, MA 01568 is a 4 bedroom, 3 bathroom, 2,132 sqft single-family home built in 1994. It last sold for $408,000 on Jun 26, 2019. It is currently off market. The Trulia Estimate is $678,100, with a rent estimate of $3,774/month.

Home Details for 27 Pleasant St

Interior Features

Heating & Cooling
Heating: Forced Air, GasAir ConditioningHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2Floors: Tile, Laminate, Linoleum Vinyl
Interior Details
Number of Rooms: 8Types of Rooms: Dining Room, Family Room, Laundry Room
Appliances & Utilities
Cable ReadyDishwasherDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace
Security
Security System

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: Shingle Not Wood, Wood
Parking & Garage
GarageParking Spaces: 8Parking: Garage Attached

Property Information

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

Community

Units in Building: 8

Lot Information

Lot Area: 0.45 acres

Building

Fitness & Sports
Tennis Court

Price and Tax history

DateEventPrice
Jun 26, 2019
Source: C21 Commonwealth Sold #72492585_01568
Sold
$408,000
May 6, 2019
Source: Agent Provided
Pending
$409,900
May 2, 2019
Source: Agent Provided
Listed For Sale
$409,900
Oct 28, 1994
Source: N/A
Sold
$196,000

Market trends in Upton

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
41
4MoM
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Around this home

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."
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  • 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!"
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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."
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Apartments for Rent

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Homes for sale near 27 Pleasant St

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Off Market Homes Near 27 Pleasant St

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Frequently asked questions about 27 Pleasant St

  • What is 27 Pleasant St estimated to be worth?
    Trulia's estimated value for 27 Pleasant St in Upton, MA is $678,100.
  • What is the price history for 27 Pleasant St?
    27 Pleasant St in Upton, MA last sold for $408,000 in June 2019.
  • Is Upton a buyer's or seller's market?
    Upton is currently a seller's market, based on recent for-sale activity.
  • What do residents say about Upton?
    Residents describe Upton, MA as easy to park in, well-kept, and dog-friendly. Most residents say you need a car. See recently sold homes in Upton, MA.
  • Does 27 Pleasant St have laundry facilities?
    Yes, 27 Pleasant St in Upton, MA has in-unit laundry.
  • How big is the lot at 27 Pleasant St?
    The lot at 27 Pleasant St in Upton, MA is about 0.45 acres (19,602 sq ft).