39 Upton Rd, Westborough, MA 01581
Property image
Property image
OFF MARKET

39 Upton Rd
Westborough, MA 01581

  • 4 Beds
  • 3 Baths
  • 2,742 sqft (on 0.57 acres)

$807,200

Trulia Estimate
as of Aug 18, 2026
Est. Refi. Payment $5,012/mo*
Refinance Your Home

$807,200

Trulia Estimate
as of Aug 18, 2026
Est. Refi. Payment $5,012/mo*
Refinance Your Home
4 Beds
3 Baths
2,742 sqft
(on 0.57 acres)

Home Value

Trulia Estimate
$807K
Since last month
Decreased$12K (-1.4%)
Since last year
Decreased$11K (-1.3%)
Since last sale
Increased$234K (+40.6%)
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 +80% in the last 10 years
MonthEstimated value
2026
August 2026$809K
July 2026$820K
June 2026$845K
May 2026$839K
April 2026$837K
March 2026$824K
February 2026$803K
January 2026$778K
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
6 Piccadilly Way, Westborough, MA
0.28
Single-Family Home
$1,105,000
05/06/26
4
2.5
2,627
8 Piccadilly Way, Westborough, MA
0.28
Single-Family Home
$1,000,000
06/24/26
4
3.5
3,300
45 Piccadilly Way, Westborough, MA
0.49
Single-Family Home
$1,180,000
12/03/25
5
3
3,500
4 Upton Rd, Westborough, MA
0.50
Single-Family Home
$980,000
07/27/26
4
2.5
2,545
39 Warren St, Westborough, MA
0.26
Single-Family Home
$550,000
01/15/26
3
1
1,232
60 Ruggles St, Westborough, MA
0.87
Single-Family Home
$755,000
09/23/25
5
2.5
3,171
20 Olde Coach Rd, Westborough, MA
0.81
Single-Family Home
$1,100,000
10/16/25
4
2.5
2,806
41 Harvey Ln, Westborough, MA
0.98
Single-Family Home
$730,000
09/30/25
4
2.5
1,960
56 Ruggles St, Westborough, MA
0.88
Single-Family Home
$735,000
12/30/25
3
2
2,329
37 Oneil Dr, Westborough, MA
1.02
Single-Family Home
$735,000
03/12/26
4
2
2,103

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
56 Warren St, Westborough, MA 01581
0.12
$1,052,500
4
3.5
3,224
Off Market
54 Warren St, Westborough, MA 01581
0.13
$765,900
3
1.5
1,920
Off Market
63 Warren St, Westborough, MA 01581
0.16
$1,483,100
4
3.5
4,413
Off Market
42 Warren St, Westborough, MA 01581
0.20
$941,500
4
3
2,383
Off Market
54 Upton Rd, Westborough, MA 01581
0.19
$795,900
4
2
1,830
Off Market
39 Warren St, Westborough, MA 01581
0.26
$550,000
3
1
1,232
Recently Sold
37 Warren St, Westborough, MA 01581
0.27
$730,200
3
2
1,762
Off Market
66 Warren St, Westborough, MA 01581
0.22
$1,016,600
5
4
3,025
Off Market
58 Upton Rd, Westborough, MA 01581
0.23
$890,400
4
3
2,321
Off Market
5 Bertis Adams Way, Westborough, MA 01581
0.26
$1,375,900
4
2.5
4,322
Off Market
6 Piccadilly Way, Westborough, MA 01581
0.28
$1,105,000
4
2.5
2,627
Recently Sold
8 Piccadilly Way, Westborough, MA 01581
0.28
$1,000,000
4
3.5
3,300
Recently Sold

Local Information

  • Map ViewExplore the area around 39 Upton Rd.
  • Schools2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1962
Lot Size
0.57 acres
Living Area
2,742 sqft
Price/Sqft
$294
Parking
Garage

About this House

Exceptional, Quintessential Cape Cod exudes the charm of a Currier & Ives image with so many lovely updates & upgrades on a phenomenally large lot complemented by exceptional in-ground pool & terrific hardscape*Great Room concept FamRm opens to updated Kitchen w/rich, natural cherry cabinets & gleaming granite - truly the heart of the home allowing for grand entertaining as well as cozy evenings*Open concept formal LR/DR w/classic mantel & sconces at the wood burning fireplace provides the option to dress things up or can be the perfect welcoming spot to work or enjoy a book*Two 1st floor bdrs & full bth AND Two 2nd flr bdrs & full bth allow for flex living arrangements or amazing work-from-home spaces*Terrific Finished lower level is perfect for an in-home office or guest area w/another full bath, wet bar w/cabinets & a large open room for flex space or cozy fireplaced enjoyment*Crisp & clean in every way*Enjoy the feeling of space set pleasingly far off the road
39 Upton Rd, Westborough, MA 01581 is a 4 bedroom, 3 bathroom, 2,742 sqft single-family home built in 1962. It last sold for $575,000 on Jul 6, 2020. It is currently off market. The Trulia Estimate is $807,200, with a rent estimate of $5,352/month.

Home Details for 39 Upton Rd

Interior Features

Interior Details
BasementNumber of Rooms: 8
Heating & Cooling
Heating: Baseboard, OilHeating Fuel: Baseboard
Levels, Entrance, & Accessibility
Stories: 2Floors: Tile, Carpet, Concrete, Hardwood, Linoleum Vinyl
Appliances & Utilities
Cable ReadyDishwasherDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: Shingle Not Wood, WoodPatioPorch
Pool
Pool
Parking & Garage
GarageParking Spaces: 2Parking: Garage Attached

Property Information

Year Built
Year Built: 1962
Property Type / Style
Property Type: Single Family HomeArchitecture: Cape Cod

Community

Units in Building: 1

Lot Information

Lot Area: 0.57 acres

Price and Tax history

DateEventPrice
Jul 6, 2020
Source: N/A
Sold
$575,000
May 7, 2020
Source: Agent Provided
Listed For Sale
$575,000

Market trends in Westborough

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
80
1MoM
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Around this home

What Locals Say about Westborough

At least 96 Trulia users voted on each feature.

  • 94 % Say car is needed

  • 87 % Say parking is easy

  • 85 % Say it's dog friendly

  • 77 % Say people would walk alone at night

  • 76 % Say yards are well-kept

  • 74 % Say it's quiet

  • 73 % Say kids play outside

  • 72 % Say there's holiday spirit

  • 72 % Say there are sidewalks

  • 63 % Say they plan to stay for at least 5 years

  • 57 % Say it's walkable to restaurants

  • 57 % Say there's wildlife

  • 56 % Say streets are well-lit

  • 53 % Say neighbors are friendly

  • 48 % Say it's walkable to grocery stores

  • 45 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Trulia User
    "You can walk to everything in this downtown neighborhood. People are friendly and helpful. It’s a great place to live, and there’s a highly varied stock of housing, including multi-unit rentals and single family houses of all sizes. "
    0
    Flag
  • Kelly Roney
    "Downtown Westborough is a great place to live. There are many walkable restaurants and stores. People are friendly, too. I’m very happy to be here. "
    0
    Flag
  • Trulia User
    "Have had an amazing experience at Hastings for 1st & 2nd—and feel lucky to live in this community!! "
    0
    Flag
  • Rcjudd
    "There are good parks and paths to walk dogs, including Veterans Park. The charm bracelet is an excellent walkable trail for dogs"
    0
    Flag
  • Ashley Carie
    "There was a fenced in area for dogs in the complex I lived but for other surrounding neighborhoods there were plenty of sidewalks and safe places with less traffic "
    0
    Flag
  • Jamie Wiggins
    "Not really sure more families in the area, I work a lot, movies during the summer on the green. School events, parades on holidays. I am single so going to Worcester about 15 minutes away is very easy to get to. Movie theater in Framingham and Marlboro. Indoor athletic facilities. New athletic fields and track facilities at the high school with lights. Town beach and lake, local reservoir good for walks taking strolls. Several local bars and restaurants searching shell fish Mexican Asian cuisine and an Uno restaurant. "
    0
    Flag
  • Emily Z.
    "Really safe neighborhood to grow up in, friendly neighbors and mix of young families and older couples. Very little traffic and great neighborhood to walk in."
    2
    Flag
  • Liliana G. .
    "Great school system, safe neighborhood, great community, easy access to mayor routes like 495, mass pike, Rt. 30 and Rt 9"
    2
    Flag
  • Kristenbrown29609
    "There is Trick or treating. In my neighborhood. The loop where the sidewalks are is always a smash hit! "
    1
    Flag
  • Kristenbrown29609
    "You see people walking their dogs, a dog park near Tufts, and a trail head to the Charm Bracelet Trail system (leash law applies). "
    0
    Flag
  • Anna L.
    "been staying here since staying local at a hotel. and love the environment. the neighborhood are very nice and keep to themselves . there are a lot of beautiful natural surroundings. how can you not enjoy it. "
    2
    Flag
  • Cristinavargas2663
    "I think dog owners would feel comfortable waking theirs dogs here. It is a very safe neighborhood and I often see people either walking their dogs of jogging."
    0
    Flag
  • Slsmith508
    "Fourth of July block parties, Halloween block parties/trick or treating on most streets, public library hosts annual events, high school events"
    0
    Flag
  • John D.
    "Love Westborough. Great community and lots of things to do. Schools are one of the best in Massachusetts and everyone is always friendly. Close to Boston by car and by train with convenient parking at train station. I also have to say that the police department are on their game here, always looking out for the best of the community. If you pass through the town you gotta check out the local brewery where we stop into on our dog walk (Cold Harbor). "
    0
    Flag
  • Jossee A.
    "Westborough it's a Safe place to live!! All people are very kind...nice and quiet.. I love my neighborhood! "
    0
    Flag
  • Jessie
    "I have nothing bad to say about this area. It’s safe and I’ve lived here for 16 years. It’s a townie town. "
    0
    Flag
  • Diane C.
    "There is a YWCA daycare across the street. The people in town are very nice. I feel safe in my neighborhood My best friend who lived across the street moved back to Australia and i miss terribly. She was the first person that came over when my husband past away from a kidney disease. My world was turned upside down and the community surrounded by them."
    0
    Flag
  • RJ
    "Westborough has a great school system and is viewed as an affluent town to live in. The downtown area is typical New England and features locally owned shops and upscale restaurants "
    0
    Flag
  • Dan P.
    "Close proximity to major highways RT 9, RT 495, and RT 90. 10 min drive to two commuter rail stations. Approx 1 hour to downtown Boston."
    0
    Flag
  • Richgraiko
    "I can walk or ride a bike to several restaurants. It’s very quiet. There is a commuter rail in town. Not bad if you appreciate quiet, early nights, but still pretty pricey considering what is here. "
    3
    Flag
  • Eddy
    "It’s peaceful and quiet , and very clean neighborhood , everyone here is nice and respectful , lots of dogs in area"
    1
    Flag
  • Cindy F.
    "I work in the area and have lived in the area for 25 years. It's a great location with access to major roadways, restaurants, shopping and has very well regarded schools. "
    0
    Flag
  • mlebrisson
    "Side walks, local parks, family-oriented neighborhood."
    0
    Flag

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Apartments for Rent

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Explore by feature - Pet Friendly

16 pet-friendly rentals in Westborough, MA

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7 rentals with a garage in Westborough, MA

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Explore by feature - Pool

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Homes for sale near 39 Upton Rd

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Off Market Homes Near 39 Upton Rd

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Frequently asked questions about 39 Upton Rd

  • What is 39 Upton Rd estimated to be worth?
    Trulia's estimated value for 39 Upton Rd in Westborough, MA is $807,200.
  • What is the price history for 39 Upton Rd?
    39 Upton Rd in Westborough, MA last sold for $575,000 in July 2020.
  • Is Westborough a buyer's or seller's market?
    Westborough is currently a buyer's market, based on recent for-sale activity.
  • What do residents say about Westborough?
    Residents describe Westborough, MA as easy to park in, dog-friendly, and well-kept. Most residents say you need a car. See recently sold homes in Westborough, MA.
  • Does 39 Upton Rd have a pool?
    Yes, 39 Upton Rd in Westborough, MA has a pool.
  • Does 39 Upton Rd have laundry facilities?
    Yes, 39 Upton Rd in Westborough, MA has in-unit laundry.