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

$698,400

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

149 Chestnut St, Upton, MA 01568

Est. Refi. Payment $4,673/mo*
Refinance Your Home
Currently Off Market - Sold Jul 6, 2021 for $540,000

Home Value

Trulia Estimate
$698K
Since last month
Increased$3K (+0.5%)
Since last year
Increased$23K (+3.3%)
Since last sale
Increased$155K (+28.7%)
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 +68% in the last 10 years
MonthEstimated value
2026
September 2026$695K
August 2026$692K
July 2026$713K
June 2026$715K
May 2026$707K
April 2026$705K
March 2026$695K
February 2026$679K
January 2026$665K
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
4 Farrar Rd, Upton, MA
0.45
Single-Family Home
$795,000
11/24/25
4
3
2,536
29 Shore Dr, Upton, MA
0.31
Single-Family Home
$600,000
12/12/25
3
2.5
1,732
154 South St, Upton, MA
0.35
Single-Family Home
$1,000,000
06/22/26
4
3.5
4,265
236 Mendon St, Upton, MA
0.76
Single-Family Home
$635,000
08/14/26
3
1.5
1,638
324 Mendon St, Upton, MA
0.96
Single-Family Home
$460,000
08/18/26
4
2.5
2,340
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
255 Prairie St, Northbridge, MA
1.28
Single-Family Home
$775,000
04/28/26
3
2.5
2,274

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
145 Chestnut St, Upton, MA 01568
0.04
$641,700
2
2
1,284
Off Market
Chestnut St, Upton, MA 01568
0.06
$213,200
Studio
-
-
Off Market
Chestnut St, Upton, MA 01568
0.06
-
-
-
-
Off Market
Chestnut St, Upton, MA 01568
0.06
$410,900
Studio
-
-
Off Market
134 South St, Upton, MA 01568
0.07
$687,500
2
2
2,194
Off Market
137 Chestnut St, Upton, MA 01568
0.08
$818,500
4
2
2,488
Off Market
148 Chestnut St, Upton, MA 01568
0.08
$651,800
3
2.5
2,100
Off Market
148 South St, Upton, MA 01568
0.09
$717,000
2
2
3,139
Off Market
146 Chestnut St, Upton, MA 01568
0.10
$656,100
2
2
1,666
Off Market
144 Chestnut St, Upton, MA 01568
0.11
$596,100
1
1
1,296
Off Market
140 Chestnut St, Upton, MA 01568
0.11
$605,200
1
2
1,522
Off Market
23 Shore Dr, Upton, MA 01568
0.11
$634,000
2
2
1,732
Off Market
133 Chestnut St, Upton, MA 01568
0.12
$703,600
4
2.5
2,002
Off Market
135 South St, Upton, MA 01568
0.12
$747,400
3
2.5
1,990
Off Market
2 Goss Pond Rd, Upton, MA 01568
0.12
$892,600
4
2.5
2,851
Off Market
56 Shore Drive Taft Pond, Upton, MA 01568
0.13
-
-
-
-
Off Market
56 Shore Dr, Upton, MA 01568
0.13
$483,700
3
1.5
1,320
Off Market
1 Sturdley Rd, Upton, MA 01568
0.13
$406,600
2
2
1,353
Off Market
130 South St, Upton, MA 01568
0.13
$399,400
1
1
1,201
Off Market
130 South St #1, Upton, MA 01568
0.13
-
-
-
-
Off Market

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

Single-Family Home
Built in 1973
3.24 acre lot
2,252 sqft
$310/sqft
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. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $698,400, with a rent estimate of $3,798/month.

Home Details for 149 Chestnut St

Interior Features

Heating & Cooling
Heating: ElectricHeating Fuel: Electric
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 and Tax history

DateEventPrice
Jul 6, 2021
Source: N/A
Sold
$540,000
Jun 21, 2021
Source: MLS PIN #72841516
Pending
$495,000
Jun 8, 2021
Source: MLS PIN #72841516
Contingent
$495,000
Jun 2, 2021
Source: MLS PIN #72841516
Listed For Sale
$495,000
Jan 11, 2018
Source: C21 Commonwealth Sold #72243795_01568
Sold
$400,000

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."
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LGBTQ Local Legal Protections

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 $698,400.
  • 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.

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