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

$839,700

Trulia Estimate
  • 4 Beds
  • 2.5 Baths
  • 2,772 sqft (on 1.84 acres)

106 Chestnut St, Upton, MA 01568

Est. Refi. Payment $5,331/mo*
Refinance Your Home
Currently Off Market - Sold Jun 19, 2020 for $565,000

Home Value

Trulia Estimate
$840K
Since last month
Decreased$18K (-2%)
Since last year
Increased$9K (+1.1%)
Since last sale
Increased$272K (+48.1%)
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 +81% in the last 10 years
MonthEstimated value
2026
September 2026$837K
August 2026$839K
July 2026$854K
June 2026$861K
May 2026$851K
April 2026$852K
March 2026$839K
February 2026$818K
January 2026$800K
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
236 Mendon St, Upton, MA
0.09
Single-Family Home
$635,000
08/14/26
3
1.5
1,638
324 Mendon St, Upton, MA
0.67
Single-Family Home
$460,000
08/18/26
4
2.5
2,340
4 Farrar Rd, Upton, MA
0.57
Single-Family Home
$795,000
11/24/25
4
3
2,536
29 Shore Dr, Upton, MA
0.62
Single-Family Home
$600,000
12/12/25
3
2.5
1,732
1 South St, Upton, MA
1.17
Single-Family Home
$770,000
08/13/26
4
3
3,018
154 South St, Upton, MA
0.93
Single-Family Home
$1,000,000
06/22/26
4
3.5
4,265
7 River Bend Rd, Upton, MA
1.24
Single-Family Home
$1,050,000
09/25/25
4
3.5
4,178
6 Wood St, Upton, MA
1.26
Single-Family Home
$1,090,000
08/31/26
4
2.5
3,260
36 Brooks St, Upton, MA
1.57
Single-Family Home
$800,000
06/18/26
4
3
2,598
29 Miscoe Rd, Mendon, MA
1.36
Single-Family Home
$687,000
12/17/25
3
2
2,070

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
236 Mendon St, Upton, MA 01568
0.09
$635,000
3
1.5
1,638
Recently Sold
111 Chestnut St, Upton, MA 01568
0.14
$928,300
3
2.5
3,120
Off Market
62 Chestnut St, Upton, MA 01568
0.16
$1,061,800
4
3.5
3,877
Off Market
133 Chestnut St, Upton, MA 01568
0.56
$703,700
4
2.5
2,002
Off Market
6 Farrar Rd, Upton, MA 01568
0.56
$997,500
6
3.5
3,162
Off Market
4 Farrar Rd, Upton, MA 01568
0.57
$795,000
4
3
2,536
Recently Sold
29 Shore Dr, Upton, MA 01568
0.62
$600,000
3
2.5
1,732
Recently Sold
24 Plumbley Rd, Upton, MA 01568
0.63
$791,600
4
3
2,582
Off Market
56 Shore Dr, Upton, MA 01568
0.66
$481,400
3
1.5
1,320
Off Market
324 Mendon St, Upton, MA 01568
0.67
$460,000
4
2.5
2,340
Recently Sold
21 Shore Dr, Upton, MA 01568
0.69
$691,400
3
2.5
1,732
Off Market
117 South St, Upton, MA 01568
0.82
$2,500,000
4
4
4,040
For Sale

Local Information

  • Map ViewExplore the area around 106 Chestnut St.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1997
1.84 acre lot
2,772 sqft
$303/sqft
Garage

About this House

Immaculate one owner, four-bedroom home on picturesque road. Open the front door to sun filled rooms, fresh paint and gleaming hardwood floors in the kitchen, living room/office, hall and formal dining room with double French doors. Large, welcoming gathering room has a vaulted ceiling and gas fireplace. Spacious kitchen, perfect for entertaining, features granite counters, center island and black/stainless-steel appliances. The elevated deck off the kitchen overlooks a meadowed back yard with 2 small ponds. Ducks, otters and songbirds are frequent guests to this property. A large walk-in pantry, bathroom and separate laundry complete the first floor. Master bed has tray ceiling, walk in closet and private bath with walk-in shower. Walk out basement with 88 ceiling and full windows. Recent high efficiency furnace and hybrid hot water. No worries with an automatic whole house 22 kw generator.
106 Chestnut St, Upton, MA 01568 is a 4 bedroom, 3 bathroom, 2,772 sqft single-family home built in 1997. It last sold for $565,000 on Jun 19, 2020. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $839,700, with a rent estimate of $4,267/month.

Home Details for 106 Chestnut St

Interior Features

Interior Details
BasementNumber of Rooms: 4
Heating & Cooling
Heating: Forced Air, OilAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2Floors: Tile, Carpet, Concrete, Hardwood
Appliances & Utilities
DishwasherDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: Vinyl, Wood
Parking & Garage
GarageParking Spaces: 2Parking: Garage Attached

Property Information

Year Built
Year Built: 1997
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
Jun 19, 2020
Source: N/A
Sold
$565,000
May 8, 2020
Source: Agent Provided
Pending
$575,000
Feb 25, 2020
Source: Agent Provided
PriceChange
$575,000
Price decreased by 2%
Jan 22, 2020
Source: Agent Provided
Listed For Sale
$585,000
Apr 30, 1998
Source: N/A
Sold
$285,900

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
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LGBTQ Local Legal Protections

Frequently asked questions about 106 Chestnut St

  • What is 106 Chestnut St estimated to be worth?
    Trulia's estimated value for 106 Chestnut St in Upton, MA is $839,700.
  • What is the price history for 106 Chestnut St?
    106 Chestnut St in Upton, MA last sold for $565,000 in June 2020.
  • 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.
  • Does 106 Chestnut St have air conditioning?
    Yes, 106 Chestnut St in Upton, MA has air conditioning.
  • Does 106 Chestnut St have laundry facilities?
    Yes, 106 Chestnut St in Upton, MA has in-unit laundry.

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