Upton, MA Homes

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  /42

  $715,000

  Open Sat 1:30PM - 3PM

  • 3 Beds
  • 3 Baths
  • 2,835 Sq Ft

  52 Elm St, Upton, MA 01568

  Tucked along a scenic country road, this beautifully preserved early 18th-century Gambrel blends timeless New England character with the comfort and updates today’s buyers seek. Rich with historic charm, the rambling floor plan offers warm, inviting spaces including a stunning 1st-floor primary suite, great room, library/den, front-to-back living room, classic keeping room with stone fireplace,

  

  Robyn Nasuti

  Realty ONE Group Suburban Lifestyle

  52 Elm St, Upton, MA 01568
• Explore Upton

• 

  

  

  /35

  Starting at $2,200

  Total Monthly Price

  • 1 Bed

  149 Main St, Upton, MA 01568

  Welcome home to 149 Main, a new luxury apartment community in the quintessential New England Town of Upton, Massachusetts. Offering smart, modern home features from designer cabinetry and color schemes to sought-after community features just outside your door. Discover the lifestyle at 149 Main.

  149 Main Street Apartments

  

  149 Main St, Upton, MA 01568
• 

  

  

  /32

  $595,000

  Sold Jan 07, 2026

  84 High St, Upton, MA 01568

  • 4 Beds
  • 3 Baths
  • 2,463 Sq Ft
  • Built 1952

  Last Sold Summary

  • 8% Below List Price
  • $242/SF
  • 136 Days On Market

  Current Estimated Value $615,644

  Last Listing Agent Ann Marie Silva Redfin Corp.

  84 High St, Upton, MA 01568
• 

  

  

  /38

  Est $687,586

  Not Listed For Sale

  23 Warren St, Upton, MA 01568

  • 3 Beds
  • 2 Baths
  • 1,924 Sq Ft
  • Built 1987

  23 Warren St, Upton, MA 01568

  Last Sold Summary

  • 40 Days On Market
• 

  

  

  /34

  $749,900

  Open Sat 11AM - 1PM

  • 2 Beds
  • 2 Baths
  • 1,734 Sq Ft

  5 Boot Shop Rd Unit 5, Upton, MA 01568

  Beautiful new construction one-level "Starling" floor plan now available at Cobbler's Creek, a vibrant 55+ community built by exceptional builders with a reputation for excellence! You're welcomed by an open & airy floor plan that seamlessly connects the sunny living room w/fireplace & built-ins, dining rm & kitchen all w/hardwood floors. The kitchen features attractive cabinets with moldings

  

  Jeffrey Germagian

  ERA Key Realty Services-Bay State Group

  5 Boot Shop Rd Unit 5, Upton, MA 01568
• 

  

  /20

  $3,900 Per Month

  • 3 Beds
  • 1.5 Baths
  • 1,320 Sq Ft
  • House for Rent

  56 Shore Dr, Upton, MA 01568

  This waterfront home has a beautiful view of Taft Pond, perfect year round vacation setting for swimming, boating, ice fishing, ice skating and more. Inside this unique post and beam home you'll walk through the living room to an outdoor patio with amazing views of the pond, venture upstairs to a master bedroom with multiple closets, attic access, and a Juliet balcony with breathtaking views of

  Rami Mitias Compass

  56 Shore Dr, Upton, MA 01568
• 

  

  /27

  $1,099,500

  Sold Aug 11, 2025

  16 Rawson Farm Rd, Mendon, MA 01756

  • 4 Beds
  • 2.5 Baths
  • 2,884 Sq Ft
  • Built 2025

  Last Sold Summary

  • 1% Below List Price
  • $381/SF
  • 230 Days On Market

  Last Listing Agent Gary Smith Mendon Area Real Estate

  16 Rawson Farm Rd, Mendon, MA 01756
• 

  

  /42

  Est $918,067

  Not Listed For Sale

  4 Oak Dr, Upton, MA 01568

  • 5 Beds
  • 2.5 Baths
  • 3,568 Sq Ft
  • Built 1988

  4 Oak Dr, Upton, MA 01568

  Last Sold Summary

  • 5 Days On Market
• 

  

  /42

  $929,000

  • 4 Beds
  • 2.5 Baths
  • 2,806 Sq Ft

  10 Sadler Rd, Upton, MA 01568

  Spacious Federal front Colonial in a desirable executive subdivision. This home offers 2,800+- sq. ft. of living space up and a large finished walkout basement. Situated on a private cul-de-sac in a sought-after neighborhood - great for kids, pets & nature. Enjoy a large open yard, garden space and a welcoming family-friendly community. The home features an open-concept kitchen and family room

  

  Bill McCormick

  McCormick Properties

  10 Sadler Rd, Upton, MA 01568
• 

  

  /19

  $4,200

  Total Monthly Price

  • 4 Beds
  • 2.5 Baths
  • 3,350 Sq Ft
  • House for Rent

  164 South St, Upton, MA 01568

  This impressive, spacious 4-bedroom, 2.5-bathroom home is nestled in a beautifully wooded area with a highly private yard. Inside, you’ll find soaring ceilings, elegant dual staircases, a 3-car garage, and fresh paint paired with brand-new carpet. There are hardwoods, and tile throughout. The expansive kitchen flows seamlessly into the family room, complemented by a formal dining room and a

  164 South St, Upton, MA 01568
• 

  

  /3

  $1,763,100

  Sold Apr 24, 2026

  7 Sawmill Brook Ln, Upton, MA 01568

  • 4 Beds
  • 4.5 Baths
  • 3,609 Sq Ft
  • Built 2025

  Last Sold Summary

  • 10% Above List Price
  • $489/SF
  • 119 Days On Market

  Last Listing Agent Team Metrowest Berkshire Hathaway HomeServices Commonwealth Real Estate

  7 Sawmill Brook Ln, Upton, MA 01568
• 

  

  /38

  Est $823,354

  Not Listed For Sale

  19 Prospect St, Upton, MA 01568

  • 3 Beds
  • 2.5 Baths
  • 2,384 Sq Ft
  • Built 1988

  19 Prospect St, Upton, MA 01568

  Last Sold Summary

  • 5 Days On Market
• 

  

  /42

  $765,000

  Pending

  • 4 Beds
  • 3 Baths
  • 3,018 Sq Ft

  1 South St, Upton, MA 01568

  Welcome home to this distinctive four-bedroom property set on a picturesque 1.84-acre lot, offering the perfect blend of charm, space, and modern updates. Enjoy peaceful mornings on the inviting farmer’s porch or unwind on the stunning new patio while taking in beautiful sunset views. Inside, this home is anything but ordinary, featuring hardwood floors, a flexible first-floor bedroom, and a

  

  Robyn Nasuti

  Realty ONE Group Suburban Lifestyle

  1 South St, Upton, MA 01568
• 

  

  /19

  $3,350 Per Month

  • 4 Beds
  • 2.5 Baths
  • 1,731 Sq Ft
  • Condo for Rent

  21 Knowlton Cir Unit 21, Upton, MA 01568

  Outstanding 4 bedroom townhome in the Samreen Villa complex. This end unit townhome offers many features, including central air, 2.5 bathrooms, a 2-car garage, a second-floor laundry, deck and much more. In terms of location, the townhome is conveniently situated near major highways, making it easily accessible. Additionally, it is close to Nipmuc Regional High School, Memorial Elementary School,

  Viviane Braganca Mega Realty Services

  21 Knowlton Cir Unit 21, Upton, MA 01568
• 

  

  /39

  $560,000

  Sold Jan 21, 2026

  127 Glenview St, Upton, MA 01568

  • 3 Beds
  • 3 Baths
  • 1,711 Sq Ft
  • Built 1954

  Last Sold Summary

  • 6% Below List Price
  • $327/SF
  • 4 Days On Market

  Current Estimated Value $570,814

  Last Listing Agent Maria Morte Berkshire Hathaway HomeServices Commonwealth Real Estate

  127 Glenview St, Upton, MA 01568
• 

  

  /42

  Est $870,048

  Not Listed For Sale

  30 Prospect St, Upton, MA 01568

  • 4 Beds
  • 2 Baths
  • 2,892 Sq Ft
  • Built 1963

  30 Prospect St, Upton, MA 01568

  Last Sold Summary

  • 7 Days On Market
• 

  

  /38

  $420,000

  $30K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,727 Sq Ft

  5 Pleasant St, Upton, MA 01568

  Bring your vision and unlock the potential of this classic Colonial set on a beautiful, level lot in desirable Upton! Offering a rare combination of major exterior updates and room to build instant equity, this home is the perfect opportunity for investors, contractors, or buyers eager to create their dream home. Significant improvements have already been completed including 9 year old vinyl

  

  Robyn Nasuti

  Realty ONE Group Suburban Lifestyle

  5 Pleasant St, Upton, MA 01568
• 

  

  /40

  $682,000

  Sold Jun 26, 2026

  20 Fiske Ave, Upton, MA 01568

  • 3 Beds
  • 2 Baths
  • 1,777 Sq Ft
  • Built 2011

  Last Sold Summary

  • 11% Above List Price
  • $384/SF
  • 5 Days On Market

  Current Estimated Value $622,315

  Last Listing Agent Megan Tolland Realty Executives Boston West

  20 Fiske Ave, Upton, MA 01568
• 

  

  /32

  Est $407,507

  Not Listed For Sale

  16 Picadilly St, Upton, MA 01568

  • 3 Beds
  • 1 Bath
  • 924 Sq Ft
  • Built 1800

  16 Picadilly St, Upton, MA 01568

  Last Sold Summary

  • 4 Days On Market
• 

  

  /41

  $799,000

  Pending

  • 4 Beds
  • 2.5 Baths
  • 2,610 Sq Ft

  1 Quail Run, Upton, MA 01568

  Stunning 4-bedroom, 2.5-bath Colonial tucked at the end of a peaceful cul-de-sac a minute from town. A sun-filled vaulted great room complements the home’s open layout as an inviting space for everyday living. The bright kitchen with center island flows seamlessly into dining, living, and den—ideal for both entertaining and work-from-home flexibility. The secluded backyard contains an elevated

  

  Robyn Nasuti

  Realty ONE Group Suburban Lifestyle

  1 Quail Run, Upton, MA 01568
• 

  

  /38

  $485,000

  Sold Jul 25, 2025

  23 Hartford Ave S, Upton, MA 01568

  • 6 Beds
  • 2 Baths
  • 2,605 Sq Ft
  • Built 1890

  Last Sold Summary

  • 5% Above List Price
  • $186/SF
  • 12 Days On Market

  Current Estimated Value $485,221

  Last Listing Agent Faina Shapiro Berkshire Hathaway Home Services Commonwealth Real Estate

  23 Hartford Ave S, Upton, MA 01568
• 

  

  /12

  Not Listed For Sale

  51 School St Unit 2, Upton, MA 01568

  • 3 Beds
  • 2.5 Baths
  • 1,420 Sq Ft
  • Built 1900

  51 School St Unit 2, Upton, MA 01568

  Last Sold Summary

  • 5 Days On Market
• 

  

  /42

  $1,300,000

  Open Sat 11AM - 1PM

  • 4 Beds
  • 2.5 Baths
  • 3,570 Sq Ft

  27 W River St, Upton, MA 01568

  Modern farmhouse-inspired luxury meets exceptional craftsmanship in this stunning custom-built ranch set on 4.8 private acres. Designed for effortless single-level living, this one-of-a-kind home offers an open-concept floor plan filled with natural light from oversized windows and accented by gleaming hardwood floors throughout the main living areas. The sleek chef’s kitchen features tall custom

  

  Robyn Nasuti

  Realty ONE Group Suburban Lifestyle

  27 W River St, Upton, MA 01568
• 

  

  /36

  $820,000

  Sold Mar 30, 2026

  13 Jonathans Way, Upton, MA 01568

  • 4 Beds
  • 2.5 Baths
  • 3,352 Sq Ft
  • Built 1994

  Last Sold Summary

  • 4% Below List Price
  • $245/SF
  • 34 Days On Market

  Current Estimated Value $821,084

  Last Listing Agent Shelly Armstrong Redfin Corp.

  13 Jonathans Way, Upton, MA 01568
• 

  

  /36

  Est $851,196

  Not Listed For Sale

  49 East St, Upton, MA 01568

  • 3 Beds
  • 2.5 Baths
  • 2,188 Sq Ft
  • Built 2017

  49 East St, Upton, MA 01568

  Last Sold Summary

  • 4 Days On Market
• 

  

  /41

  $749,000

  Pending

  • 4 Beds
  • 2.5 Baths
  • 2,256 Sq Ft

  69 Warren St, Upton, MA 01568

  Tucked away on a private, wooded lot in desirable Upton, this beautifully updated 4-bedroom, 2.5-bath Colonial invites you to truly feel at home. A granite kitchen with stainless appliances and new gas stove, accented by a cozy pellet stove, flows effortlessly into a warm, fireplaced family room—perfect for everyday living and entertaining. The spacious primary suite features hardwood flooring

  

  Robyn Nasuti

  Realty ONE Group Suburban Lifestyle

  69 Warren St, Upton, MA 01568
• 

  

  /36

  $791,900

  Sold Dec 19, 2025

  6 Hickory Ln, Upton, MA 01568

  • 4 Beds
  • 2.5 Baths
  • 2,416 Sq Ft
  • Built 1977

  Last Sold Summary

  • 7% Above List Price
  • $328/SF
  • 5 Days On Market

  Current Estimated Value $765,872

  Last Listing Agent Melissa Bonina Century 21 Custom Home Realty

  6 Hickory Ln, Upton, MA 01568
• 

  

  /42

  Est $974,337

  Not Listed For Sale

  14 Francis Dr, Upton, MA 01568

  • 4 Beds
  • 2.5 Baths
  • 3,901 Sq Ft
  • Built 2008

  14 Francis Dr, Upton, MA 01568

  Last Sold Summary

  • 0 Days On Market
• 

  

  /41

  $610,000

  Pending

  • 3 Beds
  • 1.5 Baths
  • 1,789 Sq Ft

  21 Warren Rd, Upton, MA 01568

  21 Warren Rd, Upton, MA, a meticulously maintained 1957 single-family residence spanning 1789 square feet. This attractive property, presented in great condition, offers an exceptional opportunity for discerning buyers seeking comfort and convenience. The thoughtfully designed kitchen serves as the heart of the home, featuring sophisticated stone counters, a practical peninsula, and high-end

  

  Gary Kelley

  GK Group Services, Inc.

  21 Warren Rd, Upton, MA 01568
• 

  

  /31

  $750,000

  Sold Mar 11, 2026

  27 James Rd Unit 2, Upton, MA 01568

  • 3 Beds
  • 3.5 Baths
  • 2,200 Sq Ft
  • Built 2025

  Last Sold Summary

  • $341/SF
  • 87 Days On Market

  Current Estimated Value $738,782

  Last Listing Agent Kim Kimball Kimball Property Realty Inc.

  27 James Rd Unit 2, Upton, MA 01568
• 

  

  /42

  Est $573,844

  Not Listed For Sale

  31 Conestoga Dr, Uxbridge, MA 01569

  • 3 Beds
  • 1 Bath
  • 2,245 Sq Ft
  • Built 1991

  31 Conestoga Dr, Uxbridge, MA 01569

  Last Sold Summary

  • 20 Days On Market
• 

  

  /42

  $789,000

  Pending

  • 4 Beds
  • 2.5 Baths
  • 2,824 Sq Ft

  3 Ephraims Way, Upton, MA 01568

  Welcome to this beautifully maintained Cape on a private, landscaped lot in one of Upton’s most desirable locations -featuring town water & natural gas. Extended to include an expansive addition of a primary suite over the two-car garage, this home blends comfort and function with ease... focused on entertaining. Bright, open layout with hardwood flooring and a seamless kitchen-to-dining

  

  Robyn Nasuti

  Realty ONE Group Suburban Lifestyle

  3 Ephraims Way, Upton, MA 01568
• 

  

  /5

  $297,000

  Sold Apr 14, 2026

  11 East St, Upton, MA 01568

  • Land
  • 2.23 Acres
  • $133,184 per Acre

  Last Sold Summary

  • 24% Below List Price
  • 73 Days On Market

  Current Estimated Value $911,309

  Last Listing Agent Laura Hebb ERA Key Realty Services

  11 East St, Upton, MA 01568
• 

  

  /36

  Est $502,852

  Not Listed For Sale

  113 Hecla St, Uxbridge, MA 01569

  • 4 Beds
  • 3 Baths
  • 2,340 Sq Ft
  • Built 1900

  113 Hecla St, Uxbridge, MA 01569

  Last Sold Summary

  • 18 Days On Market
• 

  

  /42

  $532,000

  Open Sat 12PM - 2PM

  • 3 Beds
  • 3.5 Baths
  • 1,731 Sq Ft

  13 Knowlton Cir Unit 13, Upton, MA 01568

  13 Knowlton Circle offers comfortable and low-maintenance townhouse living in a desirable Upton location. This 3 BEDROOM, 3.5 BTHROOMS, home features an open floor plan with hardwood floors, a spacious kitchen, and plenty of natural light throughout the main living area. The second floor includes three well-sized bedrooms, the GOOD SIZE LOFT and FINISHED lower level with a FULL BATHROOM provide

  

  Smita Sinha

  Keller Williams Pinnacle MetroWest

  13 Knowlton Cir Unit 13, Upton, MA 01568
• 

  

  /39

  $1,050,000

  Sold Jun 22, 2026

  179 South St, Upton, MA 01568

  • 3 Beds
  • 2.5 Baths
  • 3,237 Sq Ft
  • Built 1989

  Last Sold Summary

  • 5% Above List Price
  • $324/SF
  • 4 Days On Market

  Current Estimated Value $1,066,357

  Last Listing Agent Rich Hills Media Realty Group Inc.

  179 South St, Upton, MA 01568
• 

  

  /36

  Est $398,713

  Not Listed For Sale

  16 Yale St, Uxbridge, MA 01569

  • 4 Beds
  • 2 Baths
  • 1,836 Sq Ft
  • Built 1920

  16 Yale St, Uxbridge, MA 01569

  Last Sold Summary

  • 3 Days On Market
• 

  

  /31

  $500,000

  • 2 Beds
  • 2 Baths
  • 1,176 Sq Ft

  10 Hopkinton Rd, Upton, MA 01568

  Adorable Upton home ready to make your own! This charming property offers so many desirable features, including abundant natural sunlight streaming through the skylights, a convenient location just minutes from Route 495, and beautiful views of Pratt Pond. Enjoy a private backyard with endless potential for entertaining, gardening, or simply relaxing outdoors. Inside, you'll find flexible living

  

  Kathryn Amorello

  Coldwell Banker Realty - Worcester

  10 Hopkinton Rd, Upton, MA 01568
• 

  

  /37

  $900,000

  Sold May 21, 2026

  68 Pearl St, Upton, MA 01568

  • 4 Beds
  • 3.5 Baths
  • 2,472 Sq Ft
  • Built 1968

  Last Sold Summary

  • $364/SF
  • 4 Days On Market

  Current Estimated Value $876,144

  Last Listing Agent Laura Hebb ERA Key Realty Services

  68 Pearl St, Upton, MA 01568
• 

  

  /39

  Est $680,210

  Not Listed For Sale

  109 Rawson St, Uxbridge, MA 01569

  • 3 Beds
  • 2.5 Baths
  • 2,080 Sq Ft
  • Built 1992

  109 Rawson St, Uxbridge, MA 01569

  Last Sold Summary

  • 33 Days On Market

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