27 Josiah Dr, Upton, MA 01568
OFF MARKET

27 Josiah Dr
Upton, MA 01568

  • 2 Beds
  • 2 Baths
  • 2,388 sqft (on 1.94 acres)

$840,800

Trulia Estimate
as of Aug 19, 2026
Est. Refi. Payment $5,217/mo*
Refinance Your Home

$840,800

Trulia Estimate
as of Aug 19, 2026
Est. Refi. Payment $5,217/mo*
Refinance Your Home
2 Beds
2 Baths
2,388 sqft
(on 1.94 acres)

Home Value

Trulia Estimate
$841K
Since last month
Decreased$4K (-0.5%)
Since last year
Decreased$4K (-0.5%)
Since last sale
Increased$373K (+80.2%)
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 +84% in the last 10 years
MonthEstimated value
2026
August 2026$838K
July 2026$842K
June 2026$847K
May 2026$840K
April 2026$837K
March 2026$824K
February 2026$807K
January 2026$787K
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
1 South St, Upton, MA
0.40
Single-Family Home
$770,000
08/13/26
4
3
3,018
4 Fiske Mill Rd, Upton, MA
0.71
Single-Family Home
$605,000
09/26/25
2
2.5
1,720
20 Josiah Dr, Upton, MA
0.19
Single-Family Home
$785,000
07/20/26
4
2.5
2,408
27 W River St, Upton, MA
0.14
Single-Family Home
$1,200,000
08/13/26
4
2.5
3,570
21 Warren Rd, Upton, MA
0.50
Single-Family Home
$600,000
06/30/26
3
1.5
1,789
57 Plain St, Upton, MA
0.26
Single-Family Home
$525,000
07/22/26
3
2.5
1,372
10 Mendon St, Upton, MA
0.59
Single-Family Home
$505,000
09/29/25
3
2
1,440
72 Main St, Upton, MA
0.65
Single-Family Home
$478,000
05/13/26
2
1
1,536
36 Brooks St, Upton, MA
0.86
Single-Family Home
$800,000
06/18/26
4
3
2,598
26 Brooks St, Upton, MA
0.95
Single-Family Home
$680,000
09/30/25
4
1.5
1,851

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
17 Henrys Path, Upton, MA 01568
0.11
$777,800
3
2.5
2,600
Off Market
20 Josiah Dr, Upton, MA 01568
0.19
$785,000
4
2.5
2,408
Recently Sold
27 W River St, Upton, MA 01568
0.14
$1,200,000
4
2.5
3,570
Recently Sold
57 Plain St, Upton, MA 01568
0.26
$525,000
3
2.5
1,372
Recently Sold
48 Mendon St, Upton, MA 01568
0.28
$553,200
3
1.5
1,716
Off Market
40 Mendon St, Upton, MA 01568
0.34
$634,800
3
1.5
1,638
Off Market
37 Mendon St, Upton, MA 01568
0.38
$760,400
4
2.5
2,240
Off Market
44 W River St, Upton, MA 01568
0.32
$979,500
4
3.5
3,514
Off Market
6 Pease Rd, Upton, MA 01568
0.38
$832,100
4
2.5
3,420
Off Market
95 Mendon St, Upton, MA 01568
0.36
$801,600
4
3.5
3,300
Off Market
32 Mendon St, Upton, MA 01568
0.42
$1,075,000
4
2.5
2,924
For Sale
30-32 Mendon St, Upton, MA 01568
0.42
-
-
-
-
Off Market

Local Information

  • Map ViewExplore the area around 27 Josiah Dr.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1994
Lot Size
1.94 acres
Living Area
2,388 sqft
Price/Sqft
$352
Parking
Garage

About this House

This single-family home is located at 27 Josiah Dr, Upton, MA. 27 Josiah Dr is in Upton, MA and in ZIP code 01568. This property has 2 bedrooms, 2 bathrooms and approximately 2,388 sqft of floor space. This property has a lot size of 1.94 acres and was built in 1994.
27 Josiah Dr, Upton, MA 01568 is a 2 bedroom, 2 bathroom, 2,388 sqft single-family home built in 1994. It last sold for $465,000 on Apr 27, 2007. It is currently off market. The Trulia Estimate is $840,800, with a rent estimate of $2,516/month.

Home Details for 27 Josiah Dr

Interior Features

Interior Details
BasementNumber of Rooms: 3
Heating & Cooling
Heating: GasAir ConditioningHeating Fuel: Gas
Levels, Entrance, & Accessibility
Stories: 2
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: Wood
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 1994
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 9

Lot Information

Lot Area: 1.94 acres

Price and Tax history

DateEventPrice
Apr 27, 2007
Source: N/A
Sold
$465,000
Aug 31, 2001
Source: N/A
Sold
$365,000
Apr 20, 1995
Source: N/A
Sold
$224,900

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

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
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 27 Josiah Dr

  • What is 27 Josiah Dr estimated to be worth?
    Trulia's estimated value for 27 Josiah Dr in Upton, MA is $840,800.
  • What is the price history for 27 Josiah Dr?
    27 Josiah Dr in Upton, MA last sold for $465,000 in April 2007.
  • 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.
  • How big is the lot at 27 Josiah Dr?
    The lot at 27 Josiah Dr in Upton, MA is about 1.9 acres.
  • Does 27 Josiah Dr have a garage?
    Yes, 27 Josiah Dr in Upton, MA has a garage.

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Off Market Homes Near 27 Josiah Dr

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