Upton, MA Homes

• 

  

  

  /3

  $864,900 Open Fri 11AM - 3PM

  • 2 Beds
  • 2.5 Baths
  • 2,228 Sq Ft

  18 Boot Shop Rd Unit 40, Upton, MA 01568

  Welcome to Cobblers Creek, a serene 55+ community in Upton offering detached condominiums designed for active adults seeking low-maintenance living with commuter convenience. Tucked within a peaceful tree-lined setting yet close to Route 495 and the Mass Pike, this community blends privacy with accessibility. The Cardinal townhome floor plan features open-concept living with an eat-at island

  StreamLine Communities Streamline Communities - Upton

  18 Boot Shop Rd Unit 40, Upton, MA 01568
• Explore Upton

• 

  

  

  /35

  $2,150 - $2,500 total monthly price

  149 Main Street Apartments

  1 - 2 Beds

  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 St, Upton, MA 01568
• 

  

  

  /42

  $600,000 Sold Jan 26, 2026

  3 Stoddard St, Upton, MA 01568

  • 3 Beds
  • 1.5 Baths
  • 2,034 Sq Ft
  • Built 1996

  Last Sold Summary

  • 14% Below List Price
  • $295/SF
  • 41 Days On Market

  Last Listing Agent Matheus Goncalves Mega Realty Services

  3 Stoddard St, Upton, MA 01568
• 

  

  

  /28

  Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 2,228 Sq Ft

  6 Chickadee Way Unit 21, Upton, MA 01568

  6 Chickadee Way Unit 21, Upton, MA 01568
• 

  

  

  /36

  $849,900

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

  13 Jonathans Way, Upton, MA 01568

  Beautifully maintained home featuring gleaming hardwood floors and two cozy fireplaces. The cathedral-ceiling family room offers a bright and open layout ideal for everyday living and entertaining. Includes a formal dining room and a private office. Fully renovated and modernized kitchen and bathrooms with stylish finishes and contemporary functionality. Large windows throughout the home provide

  Shelly Armstrong Redfin Corp.

  13 Jonathans Way, Upton, MA 01568
• 

  

  /24

  $3,200 total monthly price

  • 1 Bed
  • 1 Bath
  • 1,065 Sq Ft
  • House for Rent

  74 Crockett Rd, Milford, MA 01757

  Lake lovers and boaters, welcome home! Beautifully renovated single family Lake Maspenock home with handicap access & peaceful water views. This 1065 sq ft home has an extra-large main bedroom with an en-suite bath. The home is recently renovated & move-in ready. There's a handicap ramp for accessible entry to 1-floor living & access to a private boat ramp! Updates include new quartz countertops,

  Kessel Shea Team Berkshire Hathaway HomeServices Commonwealth Real Estate

  74 Crockett Rd, Milford, MA 01757
• 

  

  /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

  Last Listing Agent Ann Marie Silva Redfin Corp.

  84 High St, Upton, MA 01568
• 

  

  /36

  Est $865,677 Not Listed For Sale

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

  49 East St, Upton, MA 01568

  49 East St, Upton, MA 01568
• 

  

  /40

  $1,100,000

  • 4 Beds
  • 2.5 Baths
  • 3,260 Sq Ft

  6 Wood St, Upton, MA 01568

  Where Luxury Meets Country! Welcome to this beautifully updated 4BR, 3,000+ sq ft home in scenic Upton. Perfect for entertaining with spacious foyer, formal dining & sitting room, plus expansive family room off the remodeled gourmet kitchen with quartz countertops, stainless steel appliances, double oven, compactor & decorative cabinet lighting. Upstairs offers 4 bedrooms & 2 full baths incl. a

  Brittany Palmerino Mathieu Newton Sotheby's International Realty

  6 Wood St, Upton, MA 01568
• 

  

  /32

  $4,500 total monthly price

  • 4 Beds
  • 2.5 Baths
  • 2,682 Sq Ft
  • House for Rent

  173 East St, Upton, MA 01568

  This charming colonial home located in Upton offers 4 spacious bedrooms, fireplace living room; nice open concept. Eat in kitchen complete with a granite center island and countertops, as well as modern stainless steel appliances. The family room is highlighted by a cozy fireplace, while the dining room is tastefully appointed for formal gatherings. Beautiful hardwood floors throughot. Basement

  Kathleen Craig ERA Key Realty Services

  173 East St, 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 $984,497 Not Listed For Sale

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

  14 Francis Dr, Upton, MA 01568

  14 Francis Dr, Upton, MA 01568
• 

  

  /37

  $929,900

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

  68 Pearl St, Upton, MA 01568

  Motivated seller says this is the one you're looking for! Stunning Modern 4-bedroom, 3.5-bath masterpiece has been completely transformed from top to bottom. Perfect for multi-generational living! Featuring an open layout, designer finishes, and abundant natural light. The stunning multi-level design offers versatile living spaces for entertaining, family life, or enjoying a quiet retreat.

  Laura Hebb ERA Key Realty Services

  68 Pearl St, Upton, MA 01568
• 

  

  /17

  $2,400 total monthly price

  • 4 Beds
  • 1 Bath
  • 1,350 Sq Ft
  • Apartment for Rent

  21 Pleasant St Unit 2, Upton, MA 01568

  About 21 Pleasant St #2, UPTON, MA 01568 -1) 2nd floor unit, 2) Surrounded by single family homes, 3) Fully de-Leaded. 4) Mins walk to Memorial Elementary School 5) 1/2 (half a mile) walk to Nipmuc Regional High School & Blackstone Valley Regional Vocational Technical High School, 6) Hardwood floors in all bedrooms 7) Unit Washer-Dryer hookups 8) Spacious front & backyard for pet owners, 9)

  David Rahimian Primary Homes Realty LLC

  21 Pleasant St Unit 2, Upton, MA 01568
• 

  

  /42

  $920,000 Sold Jul 10, 2025

  175 Pleasant St, Upton, MA 01568

  • 7 Beds
  • 7 Baths
  • 5,576 Sq Ft
  • Built 1991

  Last Sold Summary

  • 15% Above List Price
  • $165/SF
  • 12 Days On Market

  Current Estimated Value $983,346

  Last Listing Agent THE LASH GROUP Keller Williams Boston MetroWest

  175 Pleasant St, Upton, MA 01568
• 

  

  /42

  Est $572,522 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 2,245 Sq Ft

  31 Conestoga Dr, Uxbridge, MA 01569

  31 Conestoga Dr, Uxbridge, MA 01569
• 

  

  /3

  $849,900 Pending

  • 4 Beds
  • 2.5 Baths
  • 2,714 Sq Ft

  11 W Main St, Upton, MA 01568

  UNDER CONSTRUCTION...Enjoy The Benefits of New Construction with Energy Efficiency & Low Future Maintenance! This stunning Colonial offers the perfect blend of classic elegance and modern convenience. Every detail has been carefully selected to provide style and functionality. 1ST floor hardwoods, Quartz countertops and GE Cafe appliances are just a few of the upgraded details that make this home

  Kim Backlund Northeast Realty + Co.

  11 W Main St, Upton, MA 01568
• 

  

  /17

  $1,900 total monthly price

  • 3 Beds
  • 1 Bath
  • 1,200 Sq Ft
  • Apartment for Rent

  21 Pleasant St Unit 3, Upton, MA 01568

  David Rahimian Primary Homes Realty LLC

  21 Pleasant St Unit 3, Upton, MA 01568
• 

  

  /42

  $849,000 Sold Jun 20, 2025

  30 Prospect St, Upton, MA 01568

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

  Last Sold Summary

  • $294/SF
  • 7 Days On Market

  Current Estimated Value $854,148

  Last Listing Agent Susan Kenney Century 21 Custom Home Realty

  30 Prospect St, Upton, MA 01568
• 

  

  /36

  Est $420,160 Not Listed For Sale

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

  16 Yale St, Uxbridge, MA 01569

  16 Yale St, Uxbridge, MA 01569
• 

  /2

  $1,206,281 Pending

  • 4 Beds
  • 2.5 Baths
  • 3,314 Sq Ft

  29 Cider Mill Ln, Upton, MA 01568

  Tucked away on a spacious lot in desirable Upton, this newly built home showcases expert craftsmanship by a seasoned local developer. Offering 3,314 square feet of thoughtfully designed living space, the open floor plan seamlessly blends comfort and style, perfect for today’s modern lifestyle. At the heart of the home, an expansive chef’s kitchen connects the dining and living areas, ideal for

  Melissa Tempesta Whitewood Real Estate, Inc.

  29 Cider Mill Ln, 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

  Last Listing Agent Maria Morte Berkshire Hathaway HomeServices Commonwealth Real Estate

  127 Glenview St, Upton, MA 01568
• 

  

  /37

  Not Listed For Sale

  • 7 Beds
  • 3 Baths
  • 2,548 Sq Ft

  12 Hartford Ave E, Uxbridge, MA 01569

  12 Hartford Ave E, Uxbridge, MA 01569
• 

  

  /4

  $829,900 Pending

  • 4 Beds
  • 3 Baths
  • 2,496 Sq Ft

  10 Mechanic St, Upton, MA 01568

  UNDER CONSTRUCTION...Enjoy The Benefits of New Construction with Energy Efficiency & Low Future Maintenance! This stunning Colonial offers the perfect blend of classic elegance and modern convenience. Every detail has been carefully selected to provide style and functionality. 1ST floor hardwoods, Quartz countertops and GE Cafe appliances are just a few of the upgraded details that make this home

  Kim Backlund Northeast Realty + Co.

  10 Mechanic St, 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 $525,728

  Last Listing Agent Faina Shapiro Berkshire Hathaway HomeServices Page Realty

  23 Hartford Ave S, Upton, MA 01568
• 

  

  /39

  Est $677,617 Not Listed For Sale

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

  109 Rawson St, Uxbridge, MA 01569

  109 Rawson St, Uxbridge, MA 01569
• 

  

  /3

  $1,600,000 Pending

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

  7 Sawmill Brook Ln, Upton, MA 01568

  Perched on 3 acres of beautifully wooded land, Lot 3 features a spacious 3,609-square-foot home that perfectly balances modern elegance with classic architectural charm. The original rendering showcased stone accents on the front facade, but the final design will feature a stylish combination of board & batten siding with traditional clapboard, offering a timeless look. Inside, this home is

  Team Metrowest Berkshire Hathaway HomeServices Commonwealth Real Estate

  7 Sawmill Brook Ln, Upton, MA 01568
• 

  

  /30

  $881,301 Sold May 16, 2025

  12 Chickadee Way Unit 26, Upton, MA 01568

  • 2 Beds
  • 2.5 Baths
  • 2,228 Sq Ft
  • Built 2024

  Last Sold Summary

  • 12% Above List Price
  • $396/SF
  • 0 Days On Market

  Last Listing Agent StreamLine Communities Streamline Communities - Upton

  12 Chickadee Way Unit 26, Upton, MA 01568
• 

  

  /32

  Est $499,492 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,560 Sq Ft

  29 Hartford Ave N, Upton, MA 01568

  29 Hartford Ave N, Upton, MA 01568
• 

  

  /5

  $389,000 Pending

  • Land
  • 2.23 Acres
  • $174,439 per Acre

  11 East St, Upton, MA 01568

  Looking for the perfect place for your next home? This 2.23 acre buildable lot with a 4-bedroom designed septic plan is being broken off from current farmland. Located on East St, minutes from the Hopkinton line in an area of newer homes, it's the perfect place to build your dream home, convenient to conservation/hiking trails, highways and T stations for a great commuter location in a rural

  Laura Hebb ERA Key Realty Services

  11 East St, Upton, MA 01568
• 

  

  /41

  $725,000 Sold May 30, 2025

  139 Warren St, Upton, MA 01568

  • 3 Beds
  • 2.5 Baths
  • 2,756 Sq Ft
  • Built 1995

  Last Sold Summary

  • 7% Above List Price
  • $263/SF
  • 7 Days On Market

  Current Estimated Value $736,065

  Last Listing Agent Aliesha Noonan Noonan/Lombardi, REALTORS® LLC

  139 Warren St, Upton, MA 01568
• 

  

  /41

  Est $641,303 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,528 Sq Ft

  53 Warren St, Upton, MA 01568

  53 Warren St, Upton, MA 01568
• 

  

  /42

  $764,900 Pending

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

  27 James Rd Unit 1, Upton, MA 01568

  Exceptional New Construction at an Incredible Value! 2 brand new homes ready for immediate delivery on a dead-end street close to the center of town. Each home features 3 bedrooms, 3.5 baths, & an oversized one-car garage. The main level offers a bright, open floor plan with a dining area & a stunning granite kitchen with a waterfall island,stainless steel appliances, & lots of cabinets. The

  Kim Kimball Kimball Property Realty Inc.

  27 James Rd Unit 1, Upton, MA 01568
• 

  

  /41

  $411,000 Sold Jun 11, 2025

  26 Hartford Ave N, Upton, MA 01568

  • 3 Beds
  • 1 Bath
  • 1,140 Sq Ft
  • Built 1957

  Last Sold Summary

  • 8% Above List Price
  • $361/SF
  • 6 Days On Market

  Current Estimated Value $417,079

  Last Listing Agent Sara Pellegrini Afonso Real Estate

  26 Hartford Ave N, Upton, MA 01568
• 

  

  /31

  Est $461,526 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,008 Sq Ft

  48 Hartford Ave N, Upton, MA 01568

  48 Hartford Ave N, Upton, MA 01568
• 

  /2

  $269,000

  • Land
  • 3.19 Acres
  • $84,326 per Acre

  74 Warren St, Upton, MA 01568

  Here's your opportunity to build your dream home in the quaint and serene town of Upton. Over 3 acre wooded lot located on a scenic country road yet close to downtown. Potential to build a home with views of Boston! Zoned for a single family. Perc test done. Excellent access to I-495 and the Mass Pike for commuters. Can be purchased on its own or as a package with 12 Breton Road listing MLS #:

  Melissa Ellison Mathieu Newton Sotheby's International Realty

  74 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

  Last Listing Agent Melissa Bonina Century 21 Custom Home Realty

  6 Hickory Ln, Upton, MA 01568
• 

  

  /40

  Est $527,670 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,614 Sq Ft

  2 Breton Rd, Upton, MA 01568

  2 Breton Rd, Upton, MA 01568
• 

  

  /25

  $599,000

  • 5 Beds
  • 3 Baths
  • 2,887 Sq Ft

  130 High St, Upton, MA 01568

  Finishing touches were completed after the photos. This beautifully updated 2,887 sq. ft. single-family home offers stunning views of Pratt Pond and easy access to I-495. Renovated in 2024–2025, it features all-new siding and windows, a brand-new asphalt driveway and parking area, and a commercial-grade fire safety system. Inside, enjoy spacious, flexible living areas perfect for remote work or

  Jacob Greasley eXp Realty

  130 High St, Upton, MA 01568
• 

  

  /42

  $1,350,000 Sold Oct 03, 2025

  5 Azalea Ln, Upton, MA 01568

  • 5 Beds
  • 3.5 Baths
  • 4,647 Sq Ft
  • Built 2016

  Last Sold Summary

  • 4% Above List Price
  • $291/SF
  • 16 Days On Market

  Current Estimated Value $1,323,839

  Last Listing Agent Neil Fredette Keller Williams Realty-Merrimack

  5 Azalea Ln, Upton, MA 01568

Showing Results 1 - 40, Page 1 of 18