3,718

Upton, MA Homes

Section Image
    • /42

      Est $1,064,486

      Not Listed For Sale

      158 South St, Upton, MA 01568

      • 4 Beds
      • 4.5 Baths
      • 3,757 Sq Ft
      • Built 1999
      158 South St, Upton, MA 01568

      Last Sold Summary

      • 48 Days On Market

      Last Listing Agent Team Metrowest Berkshire Hathaway HomeServices Commonwealth Real Estate

  • /39

    $675,000

    • 4 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. Updated windows. First floor unit has a large foyer, generously sized living room with stunning hardwoods and

    Laura Hebb ERA Key Realty Services

    90 Glenview St, Upton, MA 01568
  • /41

    $720,000

    Sold Jun 29, 2026

    8 Jackson Dr Unit 8, Upton, MA 01568

    • 2 Beds
    • 3 Baths
    • 2,214 Sq Ft
    • Built 2021

    Last Sold Summary

    • 1% Below List Price
    • $325/SF
    • 16 Days On Market

    Current Estimated Value $681,938

    Last Listing Agent Team Metrowest Berkshire Hathaway HomeServices Commonwealth Real Estate

    8 Jackson Dr Unit 8, Upton, MA 01568
    • /42

      Est $1,183,091

      Not Listed For Sale

      9 Juniper Rd, Upton, MA 01568

      • 4 Beds
      • 3.5 Baths
      • 4,456 Sq Ft
      • Built 2001
      9 Juniper Rd, Upton, MA 01568

      Last Sold Summary

      • 42 Days On Market

      Last Listing Agent Robyn and Sean Sold My House Team Realty ONE Group Suburban Lifestyle

  • /33

    $950,000

    Open Sat 1PM - 3PM
    • 4 Beds
    • 3 Baths
    • 3,100 Sq Ft

    33 Milford St, Upton, MA 01568

    Stunning fully renovated luxury home offering three finished levels of sophisticated living with high-end finishes and designer details throughout. This turnkey home features an open-concept floor plan, a custom chef's kitchen with premium appliances, spa-inspired bathrooms, modern lighting, and beautifully updated living spaces. Thoughtfully renovated with exceptional craftsmanship, it

    Wendy Solano Lamacchia Realty, Inc.

    33 Milford St, Upton, MA 01568
  • /40

    $785,000

    Sold Jul 20, 2026

    20 Josiah Dr, Upton, MA 01568

    • 4 Beds
    • 2.5 Baths
    • 2,408 Sq Ft

    Last Sold Summary

    • 1% Below List Price
    • $326/SF
    • 3 Days On Market

    Current Estimated Value $826,580

    Last Listing Agent Walsh Fine Homes Team eXp Realty LLC

    20 Josiah Dr, Upton, MA 01568
    • /40

      Est $758,219

      Not Listed For Sale

      133 Chestnut St, Upton, MA 01568

      • 4 Beds
      • 2.5 Baths
      • 2,002 Sq Ft
      • Built 1974
      133 Chestnut St, Upton, MA 01568

      Last Sold Summary

      • 17 Days On Market

      Last Listing Agent Mike DeLuca Coldwell Banker Realty - Worcester

  • /42

    $789,900

    Pending
    • 4 Beds
    • 3 Baths
    • 2,668 Sq Ft

    218 Mechanic St, Upton, MA 01568

    This exceptional 3.7 acre country estate blends luxury living with outstanding outdoor amenities. The Colonial home features hardwood floors, soaring ceilings, multiple fireplaces, wood stoves, new central heat, mini-splits, and a gourmet kitchen with granite counters and stainless appliances. The main level offers formal and casual living spaces, a bright dinning room, living room, family room,

    Amy Bedard Transitions Realty

    218 Mechanic St, 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
    • /31

      Est $646,740

      Not Listed For Sale

      165 W River St, Upton, MA 01568

      • 3 Beds
      • 2.5 Baths
      • 1,680 Sq Ft
      • Built 1989
      165 W River St, Upton, MA 01568

      Last Sold Summary

      • 15 Days On Market

      Last Listing Agent Bruce Bisbee Redfin Corp.

  • /40

    $879,900

    Open Sat 12:30PM - 2PM
    • 4 Beds
    • 2.5 Baths
    • 3,132 Sq Ft

    2 Brookside St, Upton, MA 01568

    Stately Colonial offering a rare combination of natural beauty, modern updates, and everyday tranquility. Every window captures peaceful views of the surrounding landscape, creating a vacation-at-home feeling year-round. This spacious home features beautiful hardwood floors throughout the 1st floor & a versatile floor plan designed for easy everyday living & entertaining. The stunning kitchen is

    Leah Burke William Raveis R.E. & Home Services

    2 Brookside St, Upton, MA 01568
  • /2

    $835,000

    Sold Jun 29, 2026

    1 Quail Run, Upton, MA 01568

    • 4 Beds
    • 2.5 Baths
    • 2,610 Sq Ft
    • Built 2002

    Last Sold Summary

    • 5% Above List Price
    • $320/SF
    • 7 Days On Market

    Current Estimated Value $804,902

    Last Listing Agent Robyn Nasuti Realty ONE Group Suburban Lifestyle

    1 Quail Run, Upton, MA 01568
    • /37

      Est $592,531

      Not Listed For Sale

      185 W River St, Upton, MA 01568

      • 3 Beds
      • 1.5 Baths
      • 1,916 Sq Ft
      • Built 1875
      185 W River St, Upton, MA 01568

      Last Sold Summary

      • 22 Days On Market

      Last Listing Agent Robyn and Sean Sold My House Team Realty ONE Group Suburban Lifestyle

  • /42

    $639,900

    Pending
    • 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
  • /42

    $1,100,000

    Sold Jun 26, 2026

    46 Rockwood Ln Unit 46, Upton, MA 01568

    • 2 Beds
    • 3.5 Baths
    • 3,925 Sq Ft
    • Built 2018

    Last Sold Summary

    • 2% Above List Price
    • $280/SF
    • 7 Days On Market

    Last Listing Agent Bill Gassett REMAX Executive Realty

    46 Rockwood Ln Unit 46, Upton, MA 01568
    • /36

      Est $1,172,570

      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

      Last Listing Agent John Coutinho Berkshire Hathaway HomeServices Commonwealth Real Estate

  • /38

    $779,900

    • 2 Beds
    • 2 Baths
    • 1,743 Sq Ft

    41 Rockwood Ln Unit 41, Upton, MA 01568

    Impressive Like New Freestanding Ranch Home in Highly Sought-After Rockwood Meadows Over 55 Community on The Hopkinton Line Just A Few Miles Away From 495/MA Pike Exits. Premium Lot Which Backs up Conservation Area Offering Miles Hiking, Biking and Running Trails. Features an Open Plan With Gorgeous Cherry Cabinet Kitchen, Granite Counters, Stainless Appliances, Center Island and Access to

    Bill Gassett REMAX Executive Realty

    41 Rockwood Ln Unit 41, 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
    • /42

      Est $1,010,865

      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

      Last Listing Agent THE LASH GROUP Keller Williams Boston MetroWest

  • /37

    $879,900

    Pending
    • 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
  • /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
    • /42

      Est $1,056,925

      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

      Last Listing Agent Robyn and Sean Sold My House Team Realty ONE Group Suburban Lifestyle

  • /42

    $760,000

    $60K PRICE DROP
    • 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
  • /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 $443,702

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

    16 Fieldstone St Unit 16, Upton, MA 01568
    • /39

      Est $878,932

      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

      Last Listing Agent The Highland Group Keller Williams South Watuppa

  • /39

    $1,699,000

    $176K PRICE DROP
    • 8 Beds
    • 6 Baths
    • 6,850 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
  • /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 $551,596

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

    10 Mendon St, Upton, MA 01568
    • /42

      Est $984,031

      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

      Last Listing Agent Chris Mehr Full Circle Realty LLC

  • /42

    $499,000

    Pending
    • 3 Beds
    • 1 Bath
    • 1,316 Sq Ft

    71 School St, Upton, MA 01568

    ***OPEN HOUSE CANCELED***Stunning views with the ability to enjoy time on the water for under $500K. Welcome home to this beautiful single-family ranch in Upton MA across the street from Pratt Pond. Enjoy kayaking, canoeing, boating, and fishing just steps from your front door. This well maintained 3-bedroom 1-bath home sits on a flat 0.75-acre lot perfect for spending time outside entertaining,

    Matthew McLaughlin Premeer Real Estate Inc.

    71 School St, Upton, MA 01568
  • /42

    $1,100,000

    Sold Jul 30, 2026

    11 Howarth Dr, Upton, MA 01568

    • 4 Beds
    • 3.5 Baths
    • 3,768 Sq Ft
    • Built 2008

    Last Sold Summary

    • $292/SF
    • 5 Days On Market

    Current Estimated Value $1,098,168

    Last Listing Agent Mary Wood Lamacchia Realty, Inc.

    11 Howarth Dr, Upton, MA 01568
    • /41

      Est $919,590

      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

      Last Listing Agent Robyn and Sean Sold My House Team Realty ONE Group Suburban Lifestyle

  • /33

    $625,000

    • 4 Beds
    • 2.5 Baths
    • 2,548 Sq Ft

    24 Main St, Upton, MA 01568

    This rare antique in town colonial awaits a new owner. Wait until you see all the character this home exudes. Freshly painted throughout! Bright and sunny layout, hardwood flooring, gorgeous woodwork, nooks and crannies, tin ceilings, built ins, sun filled corner glassed in porch & white picket fence. This is truly a special home. Large dining area with pellet stove is perfect for entertaining. A

    Jeanne Leombruno Century 21 Custom Home Realty

    24 Main 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 $765,866

    Last Listing Agent Erika Steele REMAX Executive Realty

    24 Fowler St, Upton, MA 01568
    • /42

      Est $1,267,946

      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

      Last Listing Agent Lisa Aron Williams Coldwell Banker Realty - Sudbury

  • /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
  • /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
    • /25

      Est $779,807

      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

      Last Listing Agent Anne Oakman Media Realty Group Inc.

  • /42

    $639,900

    Pending
    • 4 Beds
    • 2.5 Baths
    • 1,800 Sq Ft

    7 Hazeltine Rd, Upton, MA 01568

    This one owner home awaits!! Wait until you see this four bedroom colonial - located is a desirable in town location, super close to Memorial School and downtown, yet on a quiet neighborhood cul de sac. Town water, Town sewer, and gas!! All the big ticket items have been done. Replacement windows, roof, water heater, updated electrical, A/C, Garage doors, newer appliances, sealed driveway. Nice

    Jeanne Leombruno Century 21 Custom Home Realty

    7 Hazeltine Rd, Upton, MA 01568
  • /42

    $1,375,000

    Sold Aug 10, 2026

    8 Stearns Rd, Upton, MA 01568

    • 5 Beds
    • 5 Baths
    • 4,395 Sq Ft
    • Built 1985

    Last Sold Summary

    • 5% Below List Price
    • $313/SF
    • 64 Days On Market

    Current Estimated Value $1,426,220

    Last Listing Agent Kathleen Nicoloro Ferrari + Co. Real Estate

    8 Stearns Rd, Upton, MA 01568
    • /39

      Est $854,248

      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

      Last Listing Agent Sara Furtado Remax Revolution

Showing Results 121 - 160, Page 4 of 18

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