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

$940,100

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

138 Chestnut St, Upton, MA 01568

Est. Refi. Payment $6,326/mo*
Refinance Your Home
Currently Off Market - Sold Apr 1, 2003 for $490,000

Home Value

Trulia Estimate
$940K
Since last month
Increased$7K (+0.8%)
Since last year
Increased$47K (+5.3%)
Since last sale
Increased$447K (+91.2%)
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 +71% in the last 10 years
MonthEstimated value
2026
October 2026$937K
September 2026$942K
August 2026$930K
July 2026$944K
June 2026$944K
May 2026$943K
April 2026$937K
March 2026$926K
February 2026$901K
January 2026$882K
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
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
324 Mendon St, Upton, MA
0.77
Single-Family Home
$460,000
08/18/26
4
2.5
2,340
4 Farrar Rd, Upton, MA
0.52
Single-Family Home
$795,000
11/24/25
4
3
2,536
236 Mendon St, Upton, MA
0.63
Single-Family Home
$635,000
08/14/26
3
1.5
1,638
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
1 South St, Upton, MA
1.33
Single-Family Home
$770,000
08/13/26
4
3
3,018
29 Rawson Farm Rd, Mendon, MA
1.18
Single-Family Home
$1,125,000
06/11/26
4
2.5
2,884
185 Prairie St, Northbridge, MA
1.33
Single-Family Home
$773,500
04/22/26
4
2.5
2,764

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
37 Shore Dr, Upton, MA 01568
0.01
$540,000
1
1.5
1,776
Off Market
136 Chestnut St, Upton, MA 01568
0.02
$1,061,900
3
2
4,214
Off Market
39 Shore Dr, Upton, MA 01568
0.03
$575,600
1
3
2,080
Off Market
134 Chestnut St, Upton, MA 01568
0.05
$898,600
4
2.5
2,792
Off Market
35 Shore Dr, Upton, MA 01568
0.06
$716,600
2
2
2,370
Off Market
41 Shore Dr, Upton, MA 01568
0.06
$555,100
2
2
1,607
Off Market
61 Shore Dr, Upton, MA 01568
0.07
$443,800
1
1
1,075
Off Market
33 Shore Dr, Upton, MA 01568
0.07
$664,600
2
2
1,732
Off Market
42 Shore Dr, Upton, MA 01568
0.08
$579,700
1
2
1,536
Off Market
38 Shore Dr, Upton, MA 01568
0.08
$380,700
1
1
1,018
Off Market
59 Shore Dr, Upton, MA 01568
0.08
$481,600
2
1
1,195
Off Market
45 Shore Dr, Upton, MA 01568
0.09
$579,000
3
1.5
1,536
Off Market
96 Shore Dr #96, Upton, MA 01568
0.09
-
-
-
-
Off Market
36 Shore Dr, Upton, MA 01568
0.10
$253,000
1
2
576
Off Market
140 Chestnut St, Upton, MA 01568
0.10
$609,700
1
2
1,522
Off Market
23 Shore Dr, Upton, MA 01568
0.10
$636,000
2
2
1,732
Off Market
31 Shore Dr, Upton, MA 01568
0.11
$637,400
3
3
1,732
Off Market
133 Chestnut St, Upton, MA 01568
0.11
$703,600
4
2.5
2,002
Off Market
47 Shore Dr, Upton, MA 01568
0.11
$349,800
1
1
744
Off Market
56 Shore Drive Taft Pond, Upton, MA 01568
0.11
-
-
-
-
Off Market

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

Single-Family Home
Built in 2001
1.84 acre lot
2,992 sqft
$314/sqft
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. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $940,100, with a rent estimate of $4,332/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 and Tax history

DateEventPrice
Nov 2, 2013
Source: Agent Provided
ListingRemoved
$482,900
May 16, 2013
Source: Agent Provided
PriceChange
$482,900
Price decreased by 2%
May 3, 2013
Source: Agent Provided
Listed For Sale
$492,900
Apr 1, 2003
Source: N/A
Sold
$490,000
Aug 27, 2002
Source: N/A
Sold
$480,000

Market trends in Upton

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
38
3MoM

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 138 Chestnut St

  • What is 138 Chestnut St estimated to be worth?
    Trulia's estimated value for 138 Chestnut St in Upton, MA is $940,100.
  • 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.

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