27 Main St, Upton, MA 01568
OFF MARKET

27 Main St
Upton, MA 01568

  • 3 Beds
  • 2 Baths
  • 1,314 sqft

$464,200

Trulia Estimate
as of Aug 10, 2026
Est. Refi. Payment $2,924/mo*
Refinance Your Home

$464,200

Trulia Estimate
as of Aug 10, 2026
Est. Refi. Payment $2,924/mo*
Refinance Your Home
3 Beds
2 Baths
1,314 sqft

Local Information

  • Map ViewExplore the area around 27 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
1800
Living Area
1,314 sqft
Price/Sqft
$353
Parking
Garage

About this House

Wonderful antique cape that has so much to offer. This property has many updates including the roof & skylights in 2014, new half bath, new hot water heater 2013, electric panel has been updated, new fence in back yard, This great house has a first floor master that has a vaulted ceiling with a skylight and attached 1/2 bath. Fantastic country eat in kitchen with hardwood flooring, Dining room with chair rail and the walls are freshly skim coated, another feature is the formal living room and there is a family room with a vaulted ceiling that leads out to a great oversized deck that overlooks a fantastic yard. The back yard is a nice surprise, it is a private oasis with lots of space for any outdoor activity you can think of.
27 Main St, Upton, MA 01568 is a 3 bedroom, 2 bathroom, 1,314 sqft single-family home built in 1800. It last sold for $197,700 on May 4, 2009. It is currently off market. The Trulia Estimate is $464,200, with a rent estimate of $2,799/month.

Home Details for 27 Main St

Interior Features

Interior Details
BasementNumber of Rooms: 3
Heating & Cooling
Heating: Other, GasHeating Fuel: Other
Levels, Entrance, & Accessibility
Stories: 2

Exterior Features

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

Property Information

Year Built
Year Built: 1800
Property Type / Style
Property Type: Single Family HomeArchitecture: Cape Cod

Community

Units in Building: 6

Lot Information

Lot Area: 10018 sqft

Price History for 27 Main St

DatePriceEventSource
06/13/2015$238,800ListingRemovedAgent Provided
06/12/2015$238,800PendingAgent Provided
06/11/2015$238,800Listed For SaleAgent Provided
05/04/2009$197,700Sold
N/A
08/30/2008$199,900ListingRemovedAgent Provided
08/14/2008$199,900PriceChange
Agent Provided
07/25/2008$219,000Listed For SaleAgent Provided
09/15/2000$174,000Sold
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$5,432
Assessment$413,100
Home facts updated by county records

Comparable Sales for 27 Main St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
41 Main St, Upton, MA
0.10
Single-Family Home
$460,000
06/30/26
2
1.5
1,155
35 Brooks St, Upton, MA
0.38
Single-Family Home
$501,000
05/29/26
3
2
1,762
21 Warren Rd, Upton, MA
0.37
Single-Family Home
$600,000
06/30/26
3
1.5
1,789
57 Plain St, Upton, MA
0.56
Single-Family Home
$525,000
07/22/26
3
2.5
1,372
10 Mendon St, Upton, MA
0.47
Single-Family Home
$505,000
09/29/25
3
2
1,440
20 Fiske Ave, Upton, MA
0.39
Single-Family Home
$682,000
06/26/26
3
2
1,777
3 Stoddard St, Upton, MA
0.51
Single-Family Home
$600,000
01/26/26
3
1.5
2,034
49 Grove St, Upton, MA
0.35
Single-Family Home
$494,500
06/26/26
3
1
1,300
8 Maple St, Upton, MA
0.54
Single-Family Home
$305,000
04/02/26
2
1.5
1,438
26 Hartford Ave N, Upton, MA
0.60
Single-Family Home
$445,000
06/29/26
3
1
1,140

Nearby homes

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Assigned Schools

These are the assigned schools for 27 Main 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
    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
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Apartments for Rent

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Homes for sale near 27 Main St

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Off Market Homes Near 27 Main St

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Frequently asked questions about 27 Main St

  • What is 27 Main St estimated to be worth?
    Trulia's estimated value for 27 Main St in Upton, MA is $464,200.
  • What is the price history for 27 Main St?
    27 Main St in Upton, MA last sold for $197,700 in May 2009.
  • 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.
  • How big is the lot at 27 Main St?
    The lot at 27 Main St in Upton, MA is about 0.23 acres (10,018 sq ft).
  • Does 27 Main St have a garage?
    Yes, 27 Main St in Upton, MA has a garage.