137 Chestnut St, Upton, MA 01568
Property image
Property image
OFF MARKET

137 Chestnut St
Upton, MA 01568

  • 4 Beds
  • 2 Baths
  • 2,488 sqft (on 4.29 acres)

$834,900

Trulia Estimate
as of Jul 6, 2026

$834,900

Trulia Estimate
as of Jul 6, 2026
4 Beds
2 Baths
2,488 sqft
(on 4.29 acres)

Local Information

  • Map ViewExplore the area around 137 Chestnut St.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

Cookie cutter doesnt do it for you? Come tour this well-appointed cape with contemporary features that will make you excited to work from home. A stone faade perfectly accents the woodsy vibe that this 4BR on 4+ acres exudes - enjoy apple trees, a garden area and hiking trails on site! Inside is an impressive living room with cherry floors, a stainless steel lined fireplace and tall windows to let the light shine in! The functional kitchen is a few steps away with an eat in dining area and access to the covered patio. BRs are split between the 2 floors with the master boasting a double closet and cathedral ceiling, each floor with access to a full bath. The finished lower level offers great bonus space - a media room, work out area, possibilities are endless! 4 season sunroom and wood deck round out perfect features for this peaceful home with ample privacy and yet, just a short drive from 495. Recent updates include roof 20, hybrid H20 tank 19, exterior paint '21. Serenity now!
137 Chestnut St, Upton, MA 01568 is a 4 bedroom, 2 bathroom, 2,488 sqft single-family home built in 1974. It last sold for $585,000 on Apr 27, 2021. It is currently off market. The Trulia Estimate is $834,900, with a rent estimate of $3,866/month.

Home Highlights

Parking
Garage
Outdoor
Deck
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 137 Chestnut St

Interior Features

Interior Details
BasementAtticNumber of Rooms: 4
Heating & Cooling
Heating: OilAir ConditioningHeating Fuel: Oil
Levels, Entrance, & Accessibility
Stories: 1
Fireplace & Spa
Fireplace

Exterior Features

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

Property Information

Year Built
Year Built: 1974
Property Type / Style
Property Type: Single Family HomeArchitecture: Cape Cod

Community

Units in Building: 8

Lot Information

Lot Area: 4.29 acres

Price History for 137 Chestnut St

DatePriceEventSource
04/27/2021$585,000Sold
N/A
03/27/2021$539,900PendingMLS PIN #72801265
03/25/2021$539,900Listed For SaleMLS PIN #72801265
11/17/2009$427,500Sold
N/A
06/30/1997$170,000Sold
N/A

Market trends in Upton

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
39
13MoM
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Property Tax and Assessment

Year2025
Tax$9,707
Assessment$738,200
Home facts updated by county records

Comparable Sales for 137 Chestnut St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
4 Farrar Rd, Upton, MA
0.41
Single-Family Home
$795,000
11/24/25
4
3
2,536
8 Miscoe Hill Rd, Upton, MA
0.35
Single-Family Home
$925,000
08/22/25
4
2.5
2,856
56 Shore Dr, Upton, MA
0.13
Single-Family Home
$472,800
09/05/25
3
1.5
1,320
29 Shore Dr, Upton, MA
0.28
Single-Family Home
$600,000
12/12/25
3
2.5
1,732
6 Sawmill Brook Ln, Upton, MA
0.67
Single-Family Home
$1,500,000
05/07/26
4
3.5
3,586
179 South St, Upton, MA
0.92
Single-Family Home
$1,050,000
06/22/26
3
2.5
3,237
334 Mendon St, Upton, MA
1.03
Single-Family Home
$710,000
07/11/25
3
2
2,154
7 Sawmill Brook Ln, Upton, MA
0.67
Single-Family Home
$1,763,100
04/24/26
4
4.5
3,609
19 Juniper Rd, Upton, MA
0.71
Single-Family Home
$1,327,090
07/11/25
4
4.5
3,900
177 South St, Upton, MA
0.88
Single-Family Home
$918,000
09/11/25
4
4
4,815

Nearby homes

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Assigned Schools

These are the assigned schools for 137 Chestnut 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."
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Homes for sale near 137 Chestnut St

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Off Market Homes Near 137 Chestnut St

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