38 Oak Dr, Upton, MA 01568
OFF MARKET

38 Oak Dr
Upton, MA 01568

  • 2 Beds
  • 2 Baths
  • 2,217 sqft (on 2.07 acres)

$819,400

Trulia Estimate
as of Jun 7, 2026
Est. Refi. Payment $4,970/mo*
Refinance Your Home

$819,400

Trulia Estimate
as of Jun 7, 2026
Est. Refi. Payment $4,970/mo*
Refinance Your Home
2 Beds
2 Baths
2,217 sqft
(on 2.07 acres)

Local Information

Map showing home location
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-- mins to
Commute Destination

Description

This home could be on the cover of a magazine! The curb appeal and landscaping is breathtaking! From the minute you turn into the driveway and approach the home you can't help but wish you lived there. Immaculately maintained and filled with pride of ownership, this home will not disappoint anyone. The kitchen has beautiful Granite counter tops, stainless steel appliances and tiled flooring. The step door living room has gorgeous flooring and a huge fireplace. New pellet stove in the family room will keep the home toasty warm throughout the New England Fall and Winter season. New well pump 2015, Weil McLain boiler 2014, Roof 2012. Freshly painted exterior with an inviting porch, 3 car garage and 2 separate sheds complete the exterior. Huge basement with work shop! Located on a quiet country rd in a very convenient Upton location. RANGE PRICED Seller will negotiate offers between $450,000 - $475,000
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 only
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 38 Oak Dr

Interior Features

Interior Details
BasementNumber of Rooms: 4
Heating & Cooling
Heating: OilHeating Fuel: Oil
Levels, Entrance, & Accessibility
Stories: 2
Fireplace & Spa
FireplaceHot Tub or Spa

Exterior Features

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

Property Information

Year Built
Year Built: 1978
Property Type / Style
Property Type: Single Family HomeArchitecture: Cape Cod

Community

Units in Building: 8

Lot Information

Lot Area: 2.07 acres

Price History for 38 Oak Dr

DatePriceEventSource
06/04/2021$651,000Sold
N/A
04/20/2021$580,000PendingMLS PIN #72815956
04/16/2021$580,000Listed For SaleMLS PIN #72815956
05/18/2017$446,500Sold
N/A
08/28/2009$392,500Sold
N/A
01/12/2007$365,000Sold
N/A

Market trends in Upton

Last updated April 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
26
9MoM
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Property Tax and Assessment

Year2025
Tax$9,910
Assessment$753,600
Home facts updated by county records

Comparable Sales for 38 Oak Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
255 Prairie St, Northbridge, MA
0.55
Single-Family Home
$775,000
04/28/26
3
2.5
2,274
4 Oak Dr, Upton, MA
0.33
Single-Family Home
$885,000
06/20/25
5
2.5
3,568
185 Prairie St, Northbridge, MA
0.57
Single-Family Home
$773,500
04/22/26
4
2.5
2,764
16 Rawson Farm Dr, Mendon, MA
0.38
Single-Family Home
$1,099,500
08/11/25
4
2.5
2,884
110 Northbridge Rd, Mendon, MA
0.55
Single-Family Home
$500,000
12/05/25
4
2.5
2,080
177 South St, Upton, MA
0.38
Single-Family Home
$918,000
09/11/25
4
4
4,815
7 Jewell Xing, Mendon, MA
0.54
Single-Family Home
$1,010,000
04/17/26
4
3
3,345
19 Juniper Rd, Upton, MA
0.49
Single-Family Home
$1,327,090
07/11/25
4
4.5
3,900
103 Prairie St, Northbridge, MA
0.62
Single-Family Home
$840,000
04/30/26
4
3.5
3,434
29 Miscoe Rd, Mendon, MA
1.02
Single-Family Home
$687,000
12/17/25
3
2
2,070

Nearby homes

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Assigned Schools

These are the assigned schools for 38 Oak Dr.
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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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38 Oak Dr, Upton, MA 01568 is a 2 bedroom, 2 bathroom, 2,217 sqft single-family home built in 1978. This property is not currently available for sale. 38 Oak Dr was last sold on Jun 4, 2021 for $651,000. The current Trulia Estimate for 38 Oak Dr is $819,400.