27 N Main St, Upton, MA 01568
OFF MARKET

27 N Main St
Upton, MA 01568

  • 3 Beds
  • 1 Bath
  • 4,126 sqft

$547,000

Trulia Estimate
as of Aug 21, 2026
Est. Refi. Payment $3,400/mo*
Refinance Your Home

$547,000

Trulia Estimate
as of Aug 21, 2026
Est. Refi. Payment $3,400/mo*
Refinance Your Home
3 Beds
1 Bath
4,126 sqft

Home Value

Trulia Estimate
$547K
Since last month
Decreased$13K (-2.2%)
Since last year
Decreased$70K (-11.4%)
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 +99% in the last 10 years
MonthEstimated value
2026
August 2026$550K
July 2026$562K
June 2026$603K
May 2026$599K
April 2026$561K
March 2026$552K
February 2026$547K
January 2026$553K
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
3 Stoddard St, Upton, MA
0.21
Single-Family Home
$600,000
01/26/26
3
1.5
2,034
120 High St, Upton, MA
0.30
Single-Family Home
$389,000
08/29/25
3
1
913
9 River St, Upton, MA
0.05
Single-Family Home
$800,000
06/30/26
3
3.5
2,000
31 Elm St, Upton, MA
0.30
Single-Family Home
$620,000
04/06/26
3
3
2,244
5 Pleasant St, Upton, MA
0.59
Single-Family Home
$420,000
08/14/26
3
1
1,727
8 Maple St, Upton, MA
0.13
Single-Family Home
$305,000
04/02/26
2
1.5
1,438
84 High St, Upton, MA
0.39
Single-Family Home
$595,000
01/07/26
4
3
2,463
4 Hazeltine Rd, Upton, MA
0.58
Single-Family Home
$970,000
06/02/26
4
2.5
3,000
41 Main St, Upton, MA
0.55
Single-Family Home
$460,000
06/30/26
2
1.5
1,155
35 Brooks St, Upton, MA
0.64
Single-Family Home
$501,000
05/29/26
3
2
1,762

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
9 River St, Upton, MA 01568
0.05
$800,000
3
3.5
2,000
Recently Sold
36 N Main St, Upton, MA 01568
0.09
$820,000
6
3
3,725
Off Market
18 Fieldstone St #18, Upton, MA 01568
0.13
-
2
1.5
1,888
Off Market
15 River St, Upton, MA 01568
0.10
$1,208,500
4
3.5
3,374
Off Market
7 Fieldstone Dr #7, Upton, MA 01568
0.13
$515,000
3
1.5
2,182
Recently Sold
6 Fieldstone Dr #6, Upton, MA 01568
0.13
$439,500
2
1.5
2,229
Recently Sold
16 Fieldstone St #16, Upton, MA 01568
0.14
-
2
1.5
1,699
Off Market
8 Maple St, Upton, MA 01568
0.13
$305,000
2
1.5
1,438
Recently Sold
8 Fieldstone St #8, Upton, MA 01568
0.16
-
2
1.5
1,608
Off Market
51 School St #2, Upton, MA 01568
0.15
$421,200
3
2.5
1,420
Off Market
51 School St #3, Upton, MA 01568
0.15
$410,000
3
2
1,420
Recently Sold
14 Fieldstone St #14, Upton, MA 01568
0.17
-
2
2.5
2,357
Off Market

Local Information

  • Map ViewExplore the area around 27 N Main 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
1900
Living Area
4,126 sqft
Price/Sqft
$133
Parking
Garage

About this House

Adorable antique with lots to offer, new roof & windows are a few of the updates that have already been done. this home has many original features that adds to the character and charm you can only find in an antique. nice size rooms with hardwood flooring, skylights. the back deck overlooks the terrific back yard. this is a great house come and see it today!
27 N Main St, Upton, MA 01568 is a 3 bedroom, 1 bathroom, 4,126 sqft single-family home built in 1900. It is currently off market. The Trulia Estimate is $547,000, with a rent estimate of $2,419/month.

Home Details for 27 N Main St

Interior Features

Interior Details
BasementAtticNumber of Rooms: 6
Heating & Cooling
Heating: GasHeating Fuel: Gas
Levels, Entrance, & Accessibility
Stories: 2

Exterior Features

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

Property Information

Year Built
Year Built: 1900
Property Type / Style
Property Type: Single Family HomeArchitecture: Other

Community

Units in Building: 3

Lot Information

Lot Area: 10019 sqft

Price and Tax history

DateEventPrice
Aug 14, 2008
Source: Agent Provided
ListingRemoved
$219,000
Jul 26, 2008
Source: Agent Provided
Listed For Sale
$219,000

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

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."
    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
    Flag
  • 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
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 27 N Main St

  • What is 27 N Main St estimated to be worth?
    Trulia's estimated value for 27 N Main St in Upton, MA is $547,000.
  • 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.
  • What are the closest schools to 27 N Main St?
    The closest schools to 27 N Main St in Upton, MA are Memorial School (Pre-K/Elementary, rated 9/10), Miscoe Hill School (Elementary/Middle, rated 7/10), Nipmuc Regional High School (rated 6/10).
  • How big is the lot at 27 N Main St?
    The lot at 27 N Main St in Upton, MA is about 0.23 acres (10,019 sq ft).
  • Does 27 N Main St have a garage?
    Yes, 27 N Main St in Upton, MA has a garage.

Apartments for Rent

Skip to last item
Skip to first item

Off Market Homes Near 27 N Main St

Skip to last item
Skip to first item

Homes for sale near 27 N Main St

Skip to last item
Skip to first item
Skip to last item
  • Results are loading
Skip to first item