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

149 Chestnut St
Upton, MA 01568

  • 4 Beds
  • 2.5 Baths
  • 2,252 sqft (on 3.24 acres)

$709,400

Trulia Estimate
as of Aug 10, 2026
Est. Refi. Payment $4,406/mo*
Refinance Your Home

$709,400

Trulia Estimate
as of Aug 10, 2026
Est. Refi. Payment $4,406/mo*
Refinance Your Home
4 Beds
2.5 Baths
2,252 sqft
(on 3.24 acres)

Local Information

  • Map ViewExplore the area around 149 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
1973
Lot Size
3.24 acres
Living Area
2,252 sqft
Price/Sqft
$315
Parking
Garage

About this House

Welcome to Chestnut St. A winding country road across from a great fishing pond. Seasonal views of Taft pond where neighbors canoe, fish & ice skate. Three plus acre wooded lot offers wildlife, an above ground pool w/deck, rock walls, another dining deck, a brick patio & acres to plant gardens or forge trails..a truly private natural setting. The 1st floor has hardwood flooring, a sunken living room, family room, a formal dining room, a study or 1st floor bedroom, and a screened porch with hardwood floors that over looks the expansive yard. Most of the rooms have been freshly painted with a neutral palate. The 2nd level offers a large walk in storage closet in the 2nd floor hall. The sun drenched master ensuite has a 3/4 bath, new carpets and double closets to welcome you. The finished basement offers a heated bedroom, an awesome bar area, laundry ctr and walk out to the patio. The 3 story garage has 2 garage bays plus a 3rd floor for finishing (a total of 3 levels of usable space).
149 Chestnut St, Upton, MA 01568 is a 4 bedroom, 3 bathroom, 2,252 sqft single-family home built in 1973. It last sold for $540,000 on Jul 6, 2021. It is currently off market. The Trulia Estimate is $709,400, with a rent estimate of $3,862/month.

Home Details for 149 Chestnut St

Interior Features

Heating & Cooling
Heating: Other, ElectricHeating Fuel: Other
Levels, Entrance, & Accessibility
Stories: 2Floors: Hardwood
Interior Details
Number of Rooms: 9Types of Rooms: Dining Room, Family Room
Appliances & Utilities
DryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: WoodPatio
Parking & Garage
GarageParking Spaces: 10Parking: Garage Detached

Property Information

Year Built
Year Built: 1973
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 8

Lot Information

Lot Area: 3.24 acres

Price History for 149 Chestnut St

DatePriceEventSource
07/06/2021$540,000Sold
N/A
06/21/2021$495,000PendingMLS PIN #72841516
06/08/2021$495,000ContingentMLS PIN #72841516
06/02/2021$495,000Listed For SaleMLS PIN #72841516
01/11/2018$400,000Sold
C21 Commonwealth Sold #72243795_01568
11/28/2017$408,900PendingAgent Provided
11/13/2017$408,900PendingToActiveAgent Provided
11/09/2017$408,900PendingAgent Provided
11/07/2017$408,900PendingToActiveAgent Provided
10/30/2017$408,900PendingAgent Provided
10/17/2017$408,900PriceChange
Agent Provided
09/12/2017$409,000PriceChange
Agent Provided
06/22/2017$419,000Listed For SaleAgent Provided
08/25/1995$208,000Sold
N/A
06/03/1988$223,000Sold
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$7,547
Assessment$573,900
Home facts updated by county records

Comparable Sales for 149 Chestnut St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
4 Farrar Rd, Upton, MA
0.45
Single-Family Home
$795,000
11/24/25
4
3
2,536
8 Miscoe Hill Rd, Upton, MA
0.32
Single-Family Home
$925,000
08/22/25
4
2.5
2,856
29 Shore Dr, Upton, MA
0.31
Single-Family Home
$600,000
12/12/25
3
2.5
1,732
56 Shore Dr, Upton, MA
0.13
Single-Family Home
$472,800
09/05/25
3
1.5
1,320
154 South St, Upton, MA
0.35
Single-Family Home
$1,000,000
06/22/26
4
3.5
4,265
6 Sawmill Brook Ln, Upton, MA
0.60
Single-Family Home
$1,500,000
05/07/26
4
3.5
3,586
7 Sawmill Brook Ln, Upton, MA
0.60
Single-Family Home
$1,763,100
04/24/26
4
4.5
3,609
179 South St, Upton, MA
0.85
Single-Family Home
$1,050,000
06/22/26
3
2.5
3,237
378 Moon Hill Rd, Northbridge, MA
1.07
Single-Family Home
$640,000
07/16/26
4
2.5
2,250
177 South St, Upton, MA
0.81
Single-Family Home
$918,000
09/11/25
4
4
4,815

Nearby homes

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Assigned Schools

These are the assigned schools for 149 Chestnut St.
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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
    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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Apartments for Rent

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Homes for sale near 149 Chestnut St

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Off Market Homes Near 149 Chestnut St

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Frequently asked questions about 149 Chestnut St

  • What is 149 Chestnut St estimated to be worth?
    Trulia's estimated value for 149 Chestnut St in Upton, MA is $709,400.
  • What is the price history for 149 Chestnut St?
    149 Chestnut St in Upton, MA last sold for $540,000 in July 2021.
  • 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 149 Chestnut St have laundry facilities?
    Yes, 149 Chestnut St in Upton, MA has in-unit laundry.
  • How big is the lot at 149 Chestnut St?
    The lot at 149 Chestnut St in Upton, MA is about 3.2 acres.