38
$1,175,000
4 bd · 4 ba · 4,116 sqft
27 Dairy Dr, Upton, MA
Sean Terrell · Redfin Corp.

No listing photos
4
Beds
4.5
Baths
3,423
Sqft
1989
Year built
Range $925,586 – $1,035,310 · as of August 30, 2026
ATTOM automated valuation model · 53 published estimates over 6.7 years · shaded band is the model's own published low-to-high range
Highest reading $1,203,536 in July 2025; lowest $630,900 in April 2020. The vertical scale starts at the series' own low, not at zero — it is drawn to show movement, not absolute size.
$196,090
Estimated monthly payment
$6,446/mo
Loan amount $784,358. Estimate only — your actual rate and payment depend on credit, location, and lender.
2025 roll
Within 2 miles of this home: 11 restaurants and cafés and 9 parks and green spaces.
Place data from OpenStreetMap.
JJ's Ice Cream
Milford Street
Rushford & Sons
Grove Street
The Country Club Sooper
Main Street
Rose Garden
Milford Street
Upton Pizza
Milford Street
Soul Fuel Café
Church Street
Main Street Pizza
Main Street
The Little Coffee Bean
Main Street
Taft Pond
Goss Pond
West Hill Wildlife Management Area
Upton State Forest
Upton Common
Zachary Pond
Mill Pond
E. Kent Swift Wildlife Management Area
School ratings (A+ to F) from HJN community data.
Nipmuc Regional High School
9-12 · Regular · Mendon-Upton School District
534 students · 11.5:1 student–teacher
Blackstone Valley
9-12 · Vocational Education · Blackstone Valley Regional Vocational Technical
1,243 students · 11.3:1 student–teacher
Miscoe Hill Middle School
5-8 · Regular · Mendon-Upton School District
647 students · 13.1:1 student–teacher
Memorial Elementary School
PK-4 · Regular · Mendon-Upton School District
493 students · 14.1:1 student–teacher
Park Street School
PK-PK · Regular · Hopedale School District
94 students · 18.4:1 student–teacher
Woodland
3-5 · Regular · Milford School District
1,036 students · 12.3:1 student–teacher
Milford High School
9-12 · Regular · Milford School District
1,316 students · 11.9:1 student–teacher
Shining Star Early Childhood Center
PK-PK · Regular · Milford School District
158 students · 17.6:1 student–teacher
MLS Property Information Network (MLS PIN)Some properties which appear for sale on this web site may subsequently have sold or may no longer be available.
38
$1,175,000
4 bd · 4 ba · 4,116 sqft
27 Dairy Dr, Upton, MA
Sean Terrell · Redfin Corp.
42$1,099,000
4 bd · 3 ba · 4,146 sqft
32 Howarth Dr, Upton, MA
Brian Connelly · Redfin Corp.
42$1,099,000
4 bd · 4 ba · 2,889 sqft
91 High, Upton, MA
Robyn Nasuti · Realty ONE Group Suburban Lifestyle
Price Reduced42$849,900
4 bd · 3 ba · 3,132 sqft
2 Brookside St, Upton, MA
Leah Burke · William Raveis R.E. & Home Services
Price Reduced42$1,050,000
4 bd · 3 ba · 2,924 sqft
32 Mendon St, Upton, MA
Luana Velame · Century 21 The Real Estate Group
40$1,079,000
4 bd · 4 ba · 3,350 sqft
165 East St, Upton, MA
Michael Stein · Redfin Corp.




