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

138 Chestnut St
Upton, MA 01568

  • 4 Beds
  • 3 Baths
  • 2,992 sqft (on 1.84 acres)

$942,100

Trulia Estimate
as of Aug 11, 2026
Est. Refi. Payment $5,827/mo*
Refinance Your Home

$942,100

Trulia Estimate
as of Aug 11, 2026
Est. Refi. Payment $5,827/mo*
Refinance Your Home
4 Beds
3 Baths
2,992 sqft
(on 1.84 acres)

Local Information

  • Map ViewExplore the area around 138 Chestnut 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
2001
Lot Size
1.84 acres
Living Area
2,992 sqft
Price/Sqft
$315
Parking
Garage

About this House

Open House Sunday 10/6 from 12-2. Very spacious 3,000 Sf 4 Bedroom 2.5 Bath colonial set on 1.83 acres on a nicely landscaped country lot. Home features freshly resurfaced hard wood floors, beautiful open foyer with a tray ceiling, huge family room w/ fireplace,1st floor office, and a spacious master bedroom suite with a whirlpool tub. Full walkout basement with windows and a slider waiting to be finished.
138 Chestnut St, Upton, MA 01568 is a 4 bedroom, 3 bathroom, 2,992 sqft single-family home built in 2001. It last sold for $490,000 on Apr 1, 2003. It is currently off market. The Trulia Estimate is $942,100, with a rent estimate of $4,203/month.

Home Details for 138 Chestnut St

Interior Features

Heating & Cooling
Heating: Forced Air, OilAir ConditioningHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2
Interior Details
Number of Rooms: 4
Fireplace & Spa
Fireplace

Exterior Features

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

Property Information

Year Built
Year Built: 2001
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 8

Lot Information

Lot Area: 1.84 acres

Price History for 138 Chestnut St

DatePriceEventSource
11/02/2013$482,900ListingRemovedAgent Provided
05/16/2013$482,900PriceChange
Agent Provided
05/03/2013$492,900Listed For SaleAgent Provided
04/01/2003$490,000Sold
N/A
08/27/2002$480,000Sold
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$10,803
Assessment$821,500
Home facts updated by county records

Comparable Sales for 138 Chestnut St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
8 Miscoe Hill Rd, Upton, MA
0.30
Single-Family Home
$925,000
08/22/25
4
2.5
2,856
29 Shore Dr, Upton, MA
0.15
Single-Family Home
$600,000
12/12/25
3
2.5
1,732
154 South St, Upton, MA
0.38
Single-Family Home
$1,000,000
06/22/26
4
3.5
4,265
4 Farrar Rd, Upton, MA
0.52
Single-Family Home
$795,000
11/24/25
4
3
2,536
56 Shore Dr, Upton, MA
0.11
Single-Family Home
$472,800
09/05/25
3
1.5
1,320
177 South St, Upton, MA
0.89
Single-Family Home
$918,000
09/11/25
4
4
4,815
16 Rawson Farm Dr, Mendon, MA
1.08
Single-Family Home
$1,099,500
08/11/25
4
2.5
2,884
6 Sawmill Brook Ln, Upton, MA
0.71
Single-Family Home
$1,500,000
05/07/26
4
3.5
3,586
7 Sawmill Brook Ln, Upton, MA
0.71
Single-Family Home
$1,763,100
04/24/26
4
4.5
3,609
29 Rawson Farm Rd, Mendon, MA
1.18
Single-Family Home
$1,125,000
06/11/26
4
2.5
2,884

Nearby homes

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Assigned Schools

These are the assigned schools for 138 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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Apartments for Rent

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Homes for sale near 138 Chestnut St

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Off Market Homes Near 138 Chestnut St

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Frequently asked questions about 138 Chestnut St

  • What is 138 Chestnut St estimated to be worth?
    Trulia's estimated value for 138 Chestnut St in Upton, MA is $942,100.
  • What is the price history for 138 Chestnut St?
    138 Chestnut St in Upton, MA last sold for $490,000 in April 2003.
  • 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 138 Chestnut St?
    The lot at 138 Chestnut St in Upton, MA is about 1.8 acres.
  • Does 138 Chestnut St have a garage?
    Yes, 138 Chestnut St in Upton, MA has a garage.