3,745

Upton, MA Homes

Section Image
    • 62 Chestnut St, Upton, MA 01568
      62 Chestnut St, Upton, MA 01568
      62 Chestnut St, Upton, MA 01568
      /36

      Est $1,102,972

      Not Listed For Sale

      62 Chestnut St, Upton, MA 01568

      • 4 Beds
      • 3.5 Baths
      • 3,877 Sq Ft
      • Built 1990
      62 Chestnut St, Upton, MA 01568

      Last Sold Summary

      • 16 Days On Market

  • 90 Glenview St, Upton, MA 01568
    90 Glenview St, Upton, MA 01568
    90 Glenview St, Upton, MA 01568
    /39

    $675,000

    Open Sat 9:30AM - 12PM
    • 5 Beds
    • 2 Baths
    • 2,534 Sq Ft

    90 Glenview St, Upton, MA 01568

    WOW! This two-family home has had major systems updated in the last two years: Oil-fired boiler w/oil-fired hot water tank, new well pump & piping, all appliances less than 2 years except for one 8-9 year old refrigerator, exterior of fireplace just repointed, updated electrical. First floor unit has a large foyer, generously sized living room with stunning hardwoods and fireplace, oversize

    Laura Hebb ERA Key Realty Services

    90 Glenview St, Upton, MA 01568
  • 244 North St, Upton, MA 01568
    244 North St, Upton, MA 01568
    244 North St, Upton, MA 01568
    /39

    $810,000

    Sold Aug 01, 2025

    244 North St, Upton, MA 01568

    • 4 Beds
    • 2.5 Baths
    • 2,426 Sq Ft
    • Built 2002

    Last Sold Summary

    • 5% Above List Price
    • $334/SF
    • 7 Days On Market

    Current Estimated Value $837,060

    Last Listing Agent Team ROVI Real Broker MA, LLC

    244 North St, Upton, MA 01568
    • 111 Chestnut St, Upton, MA 01568
      111 Chestnut St, Upton, MA 01568
      111 Chestnut St, Upton, MA 01568
      /42

      Est $925,734

      Not Listed For Sale

      111 Chestnut St, Upton, MA 01568

      • 3 Beds
      • 2.5 Baths
      • 3,120 Sq Ft
      • Built 1997
      111 Chestnut St, Upton, MA 01568

      Last Sold Summary

      • 66 Days On Market

  • 12 Pinecrest Rd Unit B, Uxbridge, MA 01569
    12 Pinecrest Rd Unit B, Uxbridge, MA 01569
    12 Pinecrest Rd Unit B, Uxbridge, MA 01569
    /14

    $392,000

    Pending
    • 2 Beds
    • 1.5 Baths
    • 1,144 Sq Ft

    12 Pinecrest Rd Unit B, Uxbridge, MA 01569

    NEW FURNACE, NEW ROOF, NEWER HOT WATER HEATER!!!! Discover the ease of condominium living at 12 Pinecrest Road, Uxbridge, MA—a fantastic opportunity for buyers looking to transition from renting to homeownership. Constructed in 1989, this 1,144 sq ft residence offers a harmonious blend of comfort and convenience across two well-appointed stories. This inviting home features two spacious bedrooms

    Euridices Dolores DeJesus StartPoint Realty

    12 Pinecrest Rd Unit B, Uxbridge, MA 01569
  • Lot 1 Sawmill Brook Ln, Upton, MA 01568
    Lot 1 Sawmill Brook Ln, Upton, MA 01568
    Lot 1 Sawmill Brook Ln, Upton, MA 01568
    /3

    $350,000

    Sold Dec 02, 2025

    Lot 1 Sawmill Brook Ln, Upton, MA 01568

    • Land
    • 5.6 Acres
    • $62,500 per Acre

    Last Sold Summary

    • 39 Days On Market

    Last Listing Agent Team Metrowest Berkshire Hathaway HomeServices Commonwealth Real Estate

    Lot 1 Sawmill Brook Ln, Upton, MA 01568
    • 6 Farrar Rd, Upton, MA 01568
      6 Farrar Rd, Upton, MA 01568
      6 Farrar Rd, Upton, MA 01568
      /42

      Est $990,765

      Not Listed For Sale

      6 Farrar Rd, Upton, MA 01568

      • 6 Beds
      • 3.5 Baths
      • 3,162 Sq Ft
      • Built 1997
      6 Farrar Rd, Upton, MA 01568

      Last Sold Summary

      • 5 Days On Market

  • 51 School St Unit 3, Upton, MA 01568
    51 School St Unit 3, Upton, MA 01568
    51 School St Unit 3, Upton, MA 01568
    /17

    $419,000

    Open Sun 11AM - 12PM
    • 3 Beds
    • 2 Baths
    • 1,420 Sq Ft

    51 School St Unit 3, Upton, MA 01568

    Welcome to this beautifully maintained 3 bedroom, 2 bath condominium in the desirable town of Upton. This bright and inviting home features an open concept layout designed for comfortable living and effortless entertaining. The modern kitchen is highlighted by elegant quartz countertops, ample cabinetry, and a seamless flow into the dining and living areas.Enjoy year round comfort with central

    Daniel DiBiasio DiBiasio Realty LLC

    51 School St Unit 3, Upton, MA 01568
  • 22 Cider Mill Ln, Upton, MA 01568
    22 Cider Mill Ln, Upton, MA 01568
    22 Cider Mill Ln, Upton, MA 01568
    /39

    $925,000

    Sold Aug 05, 2025

    22 Cider Mill Ln, Upton, MA 01568

    • 4 Beds
    • 2.5 Baths
    • 2,149 Sq Ft
    • Built 1974

    Last Sold Summary

    • $430/SF
    • 17 Days On Market

    Current Estimated Value $950,156

    Last Listing Agent Caroline Caira RE/MAX On the Charles

    22 Cider Mill Ln, Upton, MA 01568
    • 24 Plumbley Rd, Upton, MA 01568
      24 Plumbley Rd, Upton, MA 01568
      24 Plumbley Rd, Upton, MA 01568
      /39

      Est $800,864

      Not Listed For Sale

      24 Plumbley Rd, Upton, MA 01568

      • 4 Beds
      • 3 Baths
      • 2,582 Sq Ft
      • Built 1996
      24 Plumbley Rd, Upton, MA 01568

      Last Sold Summary

      • 46 Days On Market

  • 99 W River St, Upton, MA 01568
    99 W River St, Upton, MA 01568
    99 W River St, Upton, MA 01568
    /21

    $1,100,000

    • 4 Beds
    • 3.5 Baths
    • 3,487 Sq Ft

    99 W River St, Upton, MA 01568

    This beautifully designed custom home offers the perfect blend of privacy, space, and modern functionality. Set back from the street and positioned on an elevated lot, the home delivers both curb appeal and a sense of seclusion. Inside, you’ll find a thoughtfully designed floor plan featuring 4 spacious bedrooms and 3.5 bathrooms. The heart of the home is ideal for both everyday living and

    Diana Afonso Afonso Real Estate

    99 W River St, Upton, MA 01568
  • 17 Old Grafton Rd, Upton, MA 01568
    17 Old Grafton Rd, Upton, MA 01568
    17 Old Grafton Rd, Upton, MA 01568
    /20

    $952,500

    Sold Oct 31, 2025

    17 Old Grafton Rd, Upton, MA 01568

    • 4 Beds
    • 2.5 Baths
    • 2,770 Sq Ft
    • Built 2025

    Last Sold Summary

    • 1% Above List Price
    • $344/SF
    • 68 Days On Market

    Last Listing Agent Kim Backlund Northeast Realty + Co.

    17 Old Grafton Rd, Upton, MA 01568
    • 8 Plumbley Rd, Upton, MA 01568
      8 Plumbley Rd, Upton, MA 01568
      8 Plumbley Rd, Upton, MA 01568
      /42

      Est $890,915

      Not Listed For Sale

      8 Plumbley Rd, Upton, MA 01568

      • 3 Beds
      • 2.5 Baths
      • 3,623 Sq Ft
      • Built 1992
      8 Plumbley Rd, Upton, MA 01568

      Last Sold Summary

      • 53 Days On Market

  • 149 Glenview St, Upton, MA 01568
    149 Glenview St, Upton, MA 01568
    149 Glenview St, Upton, MA 01568
    /42

    $639,900

    Open Sat 10:30AM - 12:30PM
    • 3 Beds
    • 2 Baths
    • 1,546 Sq Ft

    149 Glenview St, Upton, MA 01568

    Bursting with charm and set on 1.84 picturesque acres, this white antique Cape offers standout curb appeal on a scenic country road. Designed for easy living, the first floor features the primary bedroom, full bath, laundry, and an open-concept living, dining, and kitchen area with beautiful backyard views and direct access to the deck. Outside, the freshly painted red barn and smaller white

    Team Metrowest Berkshire Hathaway HomeServices Commonwealth Real Estate

    149 Glenview St, Upton, MA 01568
  • 6 Fieldstone Dr Unit 6, Upton, MA 01568
    6 Fieldstone Dr Unit 6, Upton, MA 01568
    6 Fieldstone Dr Unit 6, Upton, MA 01568
    /42

    $439,500

    Sold May 08, 2026

    6 Fieldstone Dr Unit 6, Upton, MA 01568

    • 2 Beds
    • 1.5 Baths
    • 2,229 Sq Ft
    • Built 1987

    Last Sold Summary

    • $197/SF
    • 39 Days On Market

    Last Listing Agent Robyn Nasuti Realty ONE Group Suburban Lifestyle

    6 Fieldstone Dr Unit 6, Upton, MA 01568
    • 41 South St, Upton, MA 01568
      41 South St, Upton, MA 01568
      41 South St, Upton, MA 01568
      /41

      Est $870,858

      Not Listed For Sale

      41 South St, Upton, MA 01568

      • 4 Beds
      • 2.5 Baths
      • 2,630 Sq Ft
      • Built 1992
      41 South St, Upton, MA 01568

      Last Sold Summary

      • 5 Days On Market

  • 45 Mendon St, Upton, MA 01568
    45 Mendon St, Upton, MA 01568
    45 Mendon St, Upton, MA 01568
    /37

    $879,900

    • 3 Beds
    • 2.5 Baths
    • 3,076 Sq Ft

    45 Mendon St, Upton, MA 01568

    Custom-built Colonial set on a picturesque 1.55-acre lot. Showcasing exceptional craftsmanship, quality construction and a thoughtfully designed floor plan, this home offers the perfect blend of comfort and functionality for today's lifestyle. The spacious family room features a soaring ceiling and striking stone fireplace, creating a warm and inviting gathering space. The kitchen offers

    Mary Wood Lamacchia Realty, Inc.

    45 Mendon St, Upton, MA 01568
  • 16 Fieldstone St Unit 16, Upton, MA 01568
    16 Fieldstone St Unit 16, Upton, MA 01568
    16 Fieldstone St Unit 16, Upton, MA 01568
    /28

    $439,900

    Sold Oct 02, 2025

    16 Fieldstone St Unit 16, Upton, MA 01568

    • 2 Beds
    • 1.5 Baths
    • 1,699 Sq Ft
    • Built 1987

    Last Sold Summary

    • $259/SF
    • 26 Days On Market

    Current Estimated Value $446,558

    Last Listing Agent Karole O'Leary Lamacchia Realty, Inc.

    16 Fieldstone St Unit 16, Upton, MA 01568
    • 68 Glenview St, Upton, MA 01568
      68 Glenview St, Upton, MA 01568
      68 Glenview St, Upton, MA 01568
      /42

      Est $1,175,800

      Not Listed For Sale

      68 Glenview St, Upton, MA 01568

      • 4 Beds
      • 2.5 Baths
      • 4,875 Sq Ft
      • Built 2003
      68 Glenview St, Upton, MA 01568

      Last Sold Summary

      • 1 Day On Market

  • 11 James Rd, Upton, MA 01568
    11 James Rd, Upton, MA 01568
    11 James Rd, Upton, MA 01568
    /42

    $819,900

    Open Sat 10:30AM - 12:30PM
    • 3 Beds
    • 3 Baths
    • 1,304 Sq Ft

    11 James Rd, Upton, MA 01568

    Upton Horse Haven: Iconic 3-Bed, 3-Bath Retreat on 3.75 Acres. Discover one of Upton’s most beloved properties, a premier estate where timeless charm meets outdoor living. This home features modern upgrades including 200-amp electrical system, a new oil tank, and town water for seamless reliability. A newly finished basement for entertaining or retreat. Property offers direct access to miles of

    Team ROVI Real Broker MA, LLC

    11 James Rd, Upton, MA 01568
  • 10 Mendon St, Upton, MA 01568
    10 Mendon St, Upton, MA 01568
    10 Mendon St, Upton, MA 01568
    /11

    $505,000

    Sold Sep 29, 2025

    10 Mendon St, Upton, MA 01568

    • 3 Beds
    • 2 Baths
    • 1,440 Sq Ft
    • Built 1993

    Last Sold Summary

    • 1% Above List Price
    • $351/SF
    • 74 Days On Market

    Current Estimated Value $539,400

    Last Listing Agent Nathan Clark Your Home Sold Guaranteed Realty, The Nathan Clark Team

    10 Mendon St, Upton, MA 01568
    • 30 Glenview St, Upton, MA 01568
      30 Glenview St, Upton, MA 01568
      30 Glenview St, Upton, MA 01568
      /25

      Est $738,008

      Not Listed For Sale

      30 Glenview St, Upton, MA 01568

      • 3 Beds
      • 2.5 Baths
      • 2,127 Sq Ft
      • Built 1986
      30 Glenview St, Upton, MA 01568

      Last Sold Summary

      • 25 Days On Market

  • 175 Pleasant St, Upton, MA 01568
    175 Pleasant St, Upton, MA 01568
    175 Pleasant St, Upton, MA 01568
    /39

    $1,875,000

    • 8 Beds
    • 6 Baths
    • 6,030 Sq Ft

    175 Pleasant St, Upton, MA 01568

    ABSOLUTELY STUNNING. Enormous 8 Bedroom Home with over 6000 square feet of living on 5.5 acres bordering the Shining Rock Golf Course. Privacy abounds on this special property that has been completely updated. Septic System, Roof, Heat/AC, Kitchen, 6 Bathrooms, Windows, Flooring, Well....All NEW. First floor has kitchen, dining room, TWO front to back family/living rooms, full bath, pantry and an

    Matthew Sousa Bullseye Realty Group

    175 Pleasant St, Upton, MA 01568
  • 24 Fowler St, Upton, MA 01568
    24 Fowler St, Upton, MA 01568
    24 Fowler St, Upton, MA 01568
    /42

    $765,000

    Sold Jun 26, 2026

    24 Fowler St, Upton, MA 01568

    • 3 Beds
    • 2.5 Baths
    • 2,627 Sq Ft
    • Built 1985

    Last Sold Summary

    • 2% Above List Price
    • $291/SF
    • 2 Days On Market

    Current Estimated Value $755,372

    Last Listing Agent Erika Steele REMAX Executive Realty

    24 Fowler St, Upton, MA 01568
    • 1 Centerbrook Way, Upton, MA 01568
      1 Centerbrook Way, Upton, MA 01568
      1 Centerbrook Way, Upton, MA 01568
      /39

      Est $803,888

      Not Listed For Sale

      1 Centerbrook Way, Upton, MA 01568

      • 4 Beds
      • 2.5 Baths
      • 2,660 Sq Ft
      • Built 1996
      1 Centerbrook Way, Upton, MA 01568

      Last Sold Summary

      • 6 Days On Market

  • Lot 108 W Main St, Upton, MA 01568
    Lot 108 W Main St, Upton, MA 01568
    Lot 108 W Main St, Upton, MA 01568
    /3

    $550,000

    • Land
    • 5.45 Acres
    • $100,917 per Acre

    Lot 108 W Main St, Upton, MA 01568

    5.45± acres zoned General Business (GB) located along West Main Street (Route 140) in Upton. This versatile parcel offers strong road frontage, visibility, and flexibility for a variety of commercial, professional, mixed-use, or investment opportunities, subject to Town approvals. The GB zoning district supports a broad range of business and service uses, making this an ideal site for

    John Miller Keller Williams Pinnacle Central

    Lot 108 W Main St, Upton, MA 01568
  • 7 Fieldstone Dr Unit 7, Upton, MA 01568
    7 Fieldstone Dr Unit 7, Upton, MA 01568
    7 Fieldstone Dr Unit 7, Upton, MA 01568
    /30

    $515,000

    Sold Apr 22, 2026

    7 Fieldstone Dr Unit 7, Upton, MA 01568

    • 3 Beds
    • 1.5 Baths
    • 2,182 Sq Ft
    • Built 1987

    Last Sold Summary

    • 3% Above List Price
    • $236/SF
    • 4 Days On Market

    Last Listing Agent Linda Tolman Andrew J. Abu Inc., REALTORS®

    7 Fieldstone Dr Unit 7, Upton, MA 01568
    • 44 W River St, Upton, MA 01568
      44 W River St, Upton, MA 01568
      44 W River St, Upton, MA 01568
      /41

      Est $945,302

      Not Listed For Sale

      44 W River St, Upton, MA 01568

      • 4 Beds
      • 3.5 Baths
      • 3,514 Sq Ft
      • Built 1988
      44 W River St, Upton, MA 01568

      Last Sold Summary

      • 9 Days On Market

  • 9 River St, Upton, MA 01568
    9 River St, Upton, MA 01568
    9 River St, Upton, MA 01568
    /36

    $800,000

    Pending
    • 3 Beds
    • 3.5 Baths
    • 2,000 Sq Ft

    9 River St, Upton, MA 01568

    Custom-built expanded cape privately set on an acre-plus lot overlooking picturesque Mill Pond. This unique property offers exceptional space, flexibility, and endless potential. The updated open-concept kitchen with beamed ceilings flows into a cozy dining area with pellet stove, followed by a dramatic lodge-style living room featuring a stunning floor-to-ceiling stone fireplace. Sliders lead to

    Danelle Morris eXp Realty LLC

    9 River St, Upton, MA 01568
  • 1 Tyler Rd, Upton, MA 01568
    1 Tyler Rd, Upton, MA 01568
    1 Tyler Rd, Upton, MA 01568
    /12

    $800,000

    Sold Dec 16, 2025

    1 Tyler Rd, Upton, MA 01568

    • 4 Beds
    • 5 Baths
    • 3,406 Sq Ft
    • Built 2006

    Last Sold Summary

    • 4% Above List Price
    • $235/SF
    • 4 Days On Market

    Current Estimated Value $805,286

    Last Listing Agent Lisa Hammes REMAX Executive Realty

    1 Tyler Rd, Upton, MA 01568
    • 46 W River St, Upton, MA 01568
      46 W River St, Upton, MA 01568
      46 W River St, Upton, MA 01568
      /42

      Est $934,356

      Not Listed For Sale

      46 W River St, Upton, MA 01568

      • 4 Beds
      • 3 Baths
      • 3,797 Sq Ft
      • Built 1989
      46 W River St, Upton, MA 01568

      Last Sold Summary

      • 43 Days On Market

  • 215 North St, Upton, MA 01568
    215 North St, Upton, MA 01568
    215 North St, Upton, MA 01568
    /38

    $850,000

    $100K PRICE DROP Pending
    • 3 Beds
    • 2.5 Baths
    • 3,300 Sq Ft

    215 North St, Upton, MA 01568

    Set at the end of a dead-end road, this expanded custom contemporary offers over 10 acres of private land—a rare blend of space, flexibility, and future potential. This well-maintained 3-bed, 2.5-bath home is filled with natural light from expansive windows and skylights, creating an open, inviting layout. A standout 30x24 heated bonus room above the garage provides exceptional space for

    Campos Homes RE/MAX Real Estate Center

    215 North St, Upton, MA 01568
  • 7 River Bend Rd, Upton, MA 01568
    7 River Bend Rd, Upton, MA 01568
    7 River Bend Rd, Upton, MA 01568
    /39

    $1,050,000

    Sold Sep 25, 2025

    7 River Bend Rd, Upton, MA 01568

    • 4 Beds
    • 3.5 Baths
    • 4,178 Sq Ft
    • Built 1999

    Last Sold Summary

    • 5% Below List Price
    • $251/SF
    • 8 Days On Market

    Current Estimated Value $1,083,724

    Last Listing Agent Murray/Gresenz Group Compass

    7 River Bend Rd, Upton, MA 01568
    • 95 Mendon St, Upton, MA 01568
      95 Mendon St, Upton, MA 01568
      95 Mendon St, Upton, MA 01568
      /42

      Est $835,694

      Not Listed For Sale

      95 Mendon St, Upton, MA 01568

      • 4 Beds
      • 3.5 Baths
      • 3,300 Sq Ft
      • Built 1992
      95 Mendon St, Upton, MA 01568

      Last Sold Summary

      • 36 Days On Market

  • 74 High St, Upton, MA 01568
    74 High St, Upton, MA 01568
    74 High St, Upton, MA 01568
    /40

    $739,900

    Pending
    • 3 Beds
    • 2 Baths
    • 2,912 Sq Ft

    74 High St, Upton, MA 01568

    Discover the perfect blend of privacy and convenience on 6 wooded acres! Set back from the road and surrounded by mature trees, this property offers a peaceful setting while remaining close to local amenities, recreation, and commuter routes. Enter through double front doors into a spacious living room with hardwood floors, a bow window, and a cozy wood stove. The kitchen features stainless steel

    Mary Wood Lamacchia Realty, Inc.

    74 High St, Upton, MA 01568
  • 5 North St, Upton, MA 01568
    5 North St, Upton, MA 01568
    5 North St, Upton, MA 01568
    /41

    $1,281,500

    Sold Oct 17, 2025

    5 North St, Upton, MA 01568

    • 4 Beds
    • 3.5 Baths
    • 3,404 Sq Ft
    • Built 2025

    Last Sold Summary

    • 1% Below List Price
    • $376/SF
    • 35 Days On Market

    Last Listing Agent THE LASH GROUP Keller Williams Boston MetroWest

    5 North St, Upton, MA 01568
    • 2 Plumbley Rd, Upton, MA 01568
      2 Plumbley Rd, Upton, MA 01568
      2 Plumbley Rd, Upton, MA 01568
      /25

      Est $915,751

      Not Listed For Sale

      2 Plumbley Rd, Upton, MA 01568

      • 4 Beds
      • 2.5 Baths
      • 2,816 Sq Ft
      • Built 1995
      2 Plumbley Rd, Upton, MA 01568

      Last Sold Summary

      • 3 Days On Market

  • 32 Mendon St, Upton, MA 01568
    32 Mendon St, Upton, MA 01568
    32 Mendon St, Upton, MA 01568
    /42

    $1,150,000

    Open Sun 11AM - 1PM
    • 4 Beds
    • 2.5 Baths
    • 2,924 Sq Ft

    32 Mendon St, Upton, MA 01568

    32 Mendon St, Upton, MA. Where modern sophistication meets timeless design. This newly constructed 2026 residence offers 2,924 square feet of impeccably curated living space, blending contemporary elegance with refined modern farmhouse architecture. Every detail has been intentionally selected — from premium finishes to elevated craftsmanship — creating a home that feels both luxurious and

    Luana Velame Century 21 The Real Estate Group

    32 Mendon St, Upton, MA 01568
  • 334 Mendon St, Upton, MA 01568
    334 Mendon St, Upton, MA 01568
    334 Mendon St, Upton, MA 01568
    /41

    $710,000

    Sold Jul 11, 2025

    334 Mendon St, Upton, MA 01568

    • 3 Beds
    • 2 Baths
    • 2,154 Sq Ft
    • Built 1984

    Last Sold Summary

    • 9% Above List Price
    • $330/SF
    • 3 Days On Market

    Current Estimated Value $715,518

    Last Listing Agent Paul Harkey Paul Harkey Real Estate

    334 Mendon St, Upton, MA 01568
    • 4 South St, Upton, MA 01568
      4 South St, Upton, MA 01568
      4 South St, Upton, MA 01568
      /31

      Est $558,211

      Not Listed For Sale

      4 South St, Upton, MA 01568

      • 2 Beds
      • 1.5 Baths
      • 1,659 Sq Ft
      • Built 1951
      4 South St, Upton, MA 01568

      Last Sold Summary

      • 6 Days On Market

Showing Results 121 - 160, Page 4 of 18

Massachusetts Worcester County Upton

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