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

114 Chestnut St
Upton, MA 01568

  • 4 Beds
  • 3 Baths
  • 2,632 sqft (on 1.95 acres)

$862,600

Trulia Estimate
as of Aug 18, 2026
Est. Refi. Payment $5,350/mo*
Refinance Your Home

$862,600

Trulia Estimate
as of Aug 18, 2026
Est. Refi. Payment $5,350/mo*
Refinance Your Home
4 Beds
3 Baths
2,632 sqft
(on 1.95 acres)

Home Value

Trulia Estimate
$863K
Since last month
Decreased$9K (-1%)
Since last year
Increased$34K (+4%)
Since last sale
Increased$138K (+18.8%)
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 +95% in the last 10 years
MonthEstimated value
2026
August 2026$868K
July 2026$877K
June 2026$876K
May 2026$872K
April 2026$871K
March 2026$863K
February 2026$833K
January 2026$821K
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
0.28
Single-Family Home
$635,000
08/14/26
3
1.5
1,638
8 Miscoe Hill Rd, Upton, MA
0.63
Single-Family Home
$925,000
08/22/25
4
2.5
2,856
4 Farrar Rd, Upton, MA
0.49
Single-Family Home
$795,000
11/24/25
4
3
2,536
29 Shore Dr, Upton, MA
0.42
Single-Family Home
$600,000
12/12/25
3
2.5
1,732
154 South St, Upton, MA
0.73
Single-Family Home
$1,000,000
06/22/26
4
3.5
4,265
1 South St, Upton, MA
1.20
Single-Family Home
$770,000
08/13/26
4
3
3,018
56 Shore Dr, Upton, MA
0.46
Single-Family Home
$472,800
09/05/25
3
1.5
1,320
7 River Bend Rd, Upton, MA
1.17
Single-Family Home
$1,050,000
09/25/25
4
3.5
4,178
29 Rawson Farm Rd, Mendon, MA
1.42
Single-Family Home
$1,125,000
06/11/26
4
2.5
2,884
177 South St, Upton, MA
1.24
Single-Family Home
$918,000
09/11/25
4
4
4,815

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
111 Chestnut St, Upton, MA 01568
0.13
$931,700
3
2.5
3,120
Off Market
236 Mendon St, Upton, MA 01568
0.28
$635,000
3
1.5
1,638
Recently Sold
62 Chestnut St, Upton, MA 01568
0.35
$1,063,600
4
3.5
3,877
Off Market
133 Chestnut St, Upton, MA 01568
0.37
$709,200
4
2.5
2,002
Off Market
29 Shore Dr, Upton, MA 01568
0.42
$600,000
3
2.5
1,732
Recently Sold
6 Farrar Rd, Upton, MA 01568
0.45
$999,900
6
3.5
3,162
Off Market
56 Shore Dr, Upton, MA 01568
0.46
$487,500
3
1.5
1,320
Off Market
4 Farrar Rd, Upton, MA 01568
0.49
$795,000
4
3
2,536
Recently Sold
21 Shore Dr, Upton, MA 01568
0.50
$694,200
3
2.5
1,732
Off Market
24 Plumbley Rd, Upton, MA 01568
0.56
$783,200
4
3
2,582
Off Market
8 Miscoe Hill Rd, Upton, MA 01568
0.63
$954,700
4
2.5
2,856
Off Market
117 South St, Upton, MA 01568
0.65
$2,500,000
4
4
4,040
For Sale

Local Information

  • Map ViewExplore the area around 114 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
1996
Lot Size
1.95 acres
Living Area
2,632 sqft
Price/Sqft
$328
Parking
Garage

About this House

Welcome to 114 Chestnut Street. This spacious colonial features 4 bedrooms, 3 baths on almost 2 acres of wooded land. Enjoy the privacy on the large deck and explore the preserved nature area in the backyard where you will find a peaceful brook to sit by while watching and hearing wildlife. The grassy area by the deck and shed is ideal for playing or relaxing around the fire pit. Inside you are welcomed by gleaming hardwood floors and natural light shining through the large windows. The open concept kitchen features granite countertops with plenty of cabinet space and informal dining area with a nice view of the backyard. The great room features a fieldstone gas fireplace perfect for family gathering and flows into the deck. The formal dining room, office, full bath with laundry complete the first floor. Upstairs you will find 4 bedrooms including a large master bedroom complete with a spa-like full bathroom with a marble vanity, tile and modern shower. Showings start on Saturday!
114 Chestnut St, Upton, MA 01568 is a 4 bedroom, 3 bathroom, 2,632 sqft single-family home built in 1996. It last sold for $730,000 on Mar 21, 2023. It is currently off market. The Trulia Estimate is $862,600, with a rent estimate of $4,255/month.

Home Details for 114 Chestnut St

Interior Features

Heating & Cooling
Heating: Forced Air, OilAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2Floors: Tile, Hardwood
Interior Details
Number of Rooms: 8Types of Rooms: Family Room, Laundry Room
Appliances & Utilities
DishwasherRefrigerator
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: Vinyl
Parking & Garage
GarageParking Spaces: 8Parking: Garage Attached

Property Information

Year Built
Year Built: 1996
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 8

Lot Information

Lot Area: 1.95 acres

Price and Tax history

DateEventPrice
Mar 21, 2023
Source: MLS PIN #73073694
Sold
$730,000
Feb 22, 2023
Source: RE/MAX International
Pending
$730,000
Feb 22, 2023
Source: MLS PIN #73073694
Contingent
$730,000
Feb 16, 2023
Source: MLS PIN #73073694
Listed For Sale
$730,000
Oct 19, 2020
Source: N/A
Sold
$582,000

Market trends in Upton

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
41
4MoM
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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."
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  • 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!"
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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 114 Chestnut St

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Off Market Homes Near 114 Chestnut St

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Frequently asked questions about 114 Chestnut St

  • What is 114 Chestnut St estimated to be worth?
    Trulia's estimated value for 114 Chestnut St in Upton, MA is $862,600.
  • What is the price history for 114 Chestnut St?
    114 Chestnut St in Upton, MA last sold for $730,000 in March 2023.
  • 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 114 Chestnut St have air conditioning?
    Yes, 114 Chestnut St in Upton, MA has air conditioning.
  • Does 114 Chestnut St have laundry facilities?
    Yes, 114 Chestnut St in Upton, MA has laundry facilities.