114 Chestnut St, Upton, MA 01568
OFF MARKET

114 Chestnut St
Upton, MA 01568

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

$869,200

Trulia Estimate
as of May 8, 2026
Est. Refi. Payment $5,272/mo*
Refinance Your Home

$869,200

Trulia Estimate
as of May 8, 2026
Est. Refi. Payment $5,272/mo*
Refinance Your Home
4 Beds
3 Baths
2,632 sqft
(on 1.95 acres)

Homes for sale near 114 Chestnut St

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Apartments for Rent

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Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

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!
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking
Garage
Outdoor
Deck
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
No Info

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 History for 114 Chestnut St

DatePriceEventSource
03/21/2023$730,000Sold
MLS PIN #73073694
02/22/2023$730,000PendingRE/MAX International
02/22/2023$730,000ContingentMLS PIN #73073694
02/16/2023$730,000Listed For SaleMLS PIN #73073694
10/19/2020$582,000Sold
N/A
09/10/2020$599,900PendingAgent Provided
08/29/2020$599,900Listed For SaleAgent Provided
08/31/1999$295,000Sold
N/A
01/17/1997$252,900Sold
N/A
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Property Tax and Assessment

Year2025
Tax$10,521
Assessment$800,100
Home facts updated by county records

Comparable Sales for 114 Chestnut St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
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
334 Mendon St, Upton, MA
0.84
Single-Family Home
$710,000
07/11/25
3
2
2,154
2 Powers Rd, Mendon, MA
1.03
Single-Family Home
$1,100,000
06/11/25
4
3.5
3,722
4 Oak Dr, Upton, MA
1.17
Single-Family Home
$885,000
06/20/25
5
2.5
3,568
19 Juniper Rd, Upton, MA
0.97
Single-Family Home
$1,327,090
07/11/25
4
4.5
3,900
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
16 Rawson Farm Dr, Mendon, MA
1.36
Single-Family Home
$1,099,500
08/11/25
4
2.5
2,884

Assigned Schools

These are the assigned schools for 114 Chestnut St.
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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

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

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Homes for rent near 114 Chestnut St

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Off Market Homes Near 114 Chestnut St

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114 Chestnut St, Upton, MA 01568 is a 4 bedroom, 3 bathroom, 2,632 sqft single-family home built in 1996. This property is not currently available for sale. 114 Chestnut St was last sold on Mar 21, 2023 for $730,000. The current Trulia Estimate for 114 Chestnut St is $869,200.