3,745

Upton, MA Homes

Section Image
  • /39

    $680,000

    Sold Sep 30, 2025

    26 Brooks St, Upton, MA 01568

    • 4 Beds
    • 1.5 Baths
    • 1,851 Sq Ft
    • Built 1900

    Last Sold Summary

    • 4% Below List Price
    • $367/SF
    • 72 Days On Market

    Current Estimated Value $690,854

    Last Listing Agent Alissa Tosches Lamacchia Realty, Inc.

    26 Brooks St, Upton, MA 01568
    • /30

      Est $410,515

      Not Listed For Sale

      74 Main St, Upton, MA 01568

      • 3 Beds
      • 1.5 Baths
      • 1,428 Sq Ft
      • Built 1850
      74 Main St, Upton, MA 01568

      Last Sold Summary

      • 75 Days On Market

  • /37

    $919,900

    $20K PRICE DROP Pending
    • 4 Beds
    • 2.5 Baths
    • 3,956 Sq Ft

    145 W River St, Upton, MA 01568

    Prepare to be enchanted by this stunning, perfectly designed home. One level living at its finest. Crafted with the utmost precision and meticulous design. Every inch of the home was carefully thought of – from a perfectly situated mudroom, to a seamlessly flowing open concept living area, four generously sized bedrooms, a large study, a wonderful oversized four-season porch and an outdoor patio.

    Mia Fisher Berkshire Hathaway HomeServices Commonwealth Real Estate

    145 W River St, Upton, MA 01568
  • /42

    $1,475,000

    Sold Oct 01, 2025

    105 Crockett Rd, Upton, MA 01568

    • 3 Beds
    • 2.5 Baths
    • 2,852 Sq Ft
    • Built 1917

    Last Sold Summary

    • 1% Below List Price
    • $517/SF
    • 17 Days On Market

    Last Listing Agent Paul Neavyn Gibson Sotheby's International Realty

    105 Crockett Rd, Upton, MA 01568
    • /31

      Est $528,458

      Not Listed For Sale

      15 Pleasant St, Upton, MA 01568

      • 3 Beds
      • 2 Baths
      • 1,220 Sq Ft
      • Built 1970
      15 Pleasant St, Upton, MA 01568

      Last Sold Summary

      • 3 Days On Market

  • /36

    $729,000

    Open Sun 1PM - 3PM
    • 2 Beds
    • 2.5 Baths
    • 1,930 Sq Ft

    87 Shannon Way Unit 86, Upton, MA 01568

    Enjoy low-maintenance living at Upton Ridge, a desirable 55+ community just a short stroll from the renowned Shining Rock Golf Course. This beautiful Milan-style two-story home offers a spacious, thoughtfully designed floor plan featuring a first-floor primary suite and open-concept living. The oversized kitchen is perfect for entertaining, complete with upgraded cabinetry, quartz countertops,

    Shane Brady Keller Williams Realty

    87 Shannon Way Unit 86, Upton, MA 01568
  • /28

    $389,000

    Sold Aug 29, 2025

    120 High St, Upton, MA 01568

    • 3 Beds
    • 1 Bath
    • 913 Sq Ft
    • Built 1875

    Last Sold Summary

    • 3% Below List Price
    • $426/SF
    • 46 Days On Market

    Current Estimated Value $397,442

    Last Listing Agent Clifton LaPorte Berkshire Hathaway HomeServices Commonwealth Real Estate

    120 High St, Upton, MA 01568
    • /36

      Est $570,560

      Not Listed For Sale

      31 Pleasant St, Upton, MA 01568

      • 3 Beds
      • 2 Baths
      • 1,932 Sq Ft
      • Built 1969
      31 Pleasant St, Upton, MA 01568

      Last Sold Summary

      • 6 Days On Market

  • /40

    $1,090,000

    $35K PRICE DROP Pending
    • 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
  • /36

    $689,500

    Sold Nov 14, 2025

    41 Shannon Way Unit 41, Upton, MA 01568

    • 2 Beds
    • 2.5 Baths
    • 1,875 Sq Ft
    • Built 2021

    Last Sold Summary

    • 1% Below List Price
    • $368/SF
    • 10 Days On Market

    Last Listing Agent Derek Greene The Greene Realty Group

    41 Shannon Way Unit 41, Upton, MA 01568
    • /42

      Est $664,541

      Not Listed For Sale

      13 Plain St, Upton, MA 01568

      • 3 Beds
      • 2.5 Baths
      • 1,728 Sq Ft
      • Built 1996
      13 Plain St, Upton, MA 01568

      Last Sold Summary

      • 24 Days On Market

  • /14

    $349,000

    $20K PRICE DROP
    • 2 Beds
    • 1.5 Baths
    • 1,304 Sq Ft

    10 Pinecrest Rd, Uxbridge, MA 01569

    Just intime for summer to lounge by this well maintained home in the quaint town of Uxbridge! This tucked away 1/2 duplex featuring 2 bedrooms, 1.5 baths, front to back family/dining area with vaulted ceilings and slider leading to deck and pool! newer roof & water heater. Great opportunity for a first-time buyer! No condo fees! Washer, dryer and Fridge stay! Schedule your private showing today!

    Rosanna Blanchard Afonso Real Estate

    10 Pinecrest Rd, Uxbridge, MA 01569
  • /2

    $838,000

    Sold Oct 09, 2025

    49 Warren St, Upton, MA 01568

    • 4 Beds
    • 3.5 Baths
    • 2,604 Sq Ft
    • Built 2022

    Last Sold Summary

    • 9% Above List Price
    • $322/SF
    • 4 Days On Market

    Current Estimated Value $861,191

    Last Listing Agent Deb Kotlarz Keller Williams Realty Boston Northwest

    49 Warren St, Upton, MA 01568
    • /18

      Est $569,460

      Not Listed For Sale

      3 Central Square, Upton, MA 01568

      • 4 Beds
      • 2 Baths
      • 1,378 Sq Ft
      • Built 1835
      3 Central Square, Upton, MA 01568

      Last Sold Summary

      • 4 Days On Market

  • /19

    $7,500,000

    • 46 Beds
    • 34 Baths
    • 22,233 Sq Ft

    135 Main St, Upton, MA 01568

    135 Main St contains 34 units comprised of (22) 1-Bed/1-Bath units and (12) 2-Bed/1-Bath units. The Property, previously known as The Upton Inn, has undergone significant renovations since its acquisition in August of 2024. This has included renovations of most units including new kitchens and bathrooms with condo quality finishes, updated flooring and painting of the units’ interiors. 135 Main

    Kelleher - Pentore Team Horvath & Tremblay

    135 Main St, Upton, MA 01568
  • /31

    $305,000

    Sold Apr 02, 2026

    8 Maple St, Upton, MA 01568

    • 2 Beds
    • 1.5 Baths
    • 1,438 Sq Ft
    • Built 1855

    Last Sold Summary

    • 24% Below List Price
    • $212/SF
    • 1 Day On Market

    Current Estimated Value $381,785

    Last Listing Agent June Hillier REMAX Executive Realty

    8 Maple St, Upton, MA 01568
    • /40

      Est $728,471

      Not Listed For Sale

      29 Warren St, Upton, MA 01568

      • 5 Beds
      • 3 Baths
      • 2,688 Sq Ft
      • Built 1980
      29 Warren St, Upton, MA 01568

      Last Sold Summary

      • 36 Days On Market

  • /16

    $439,000

    Open Sat 11:30AM - 1PM $61K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 2,110 Sq Ft

    17 N Main St, Upton, MA 01568

    Antique Greek Revival single-family home in the heart of Upton’s historic district. The Thomas McFarland House (1810) is set on the right side of a 1.14-acre lot that slopes down to scenic Mill Pond. Offering four bedrooms, two full baths, 2100 sq ft living space and a two-car garage. The home is rich in character but does require significant renovation. Features include, abundant natural light,

    Michael O'Dea Coldwell Banker Realty - Brookline

    17 N Main St, Upton, MA 01568
  • /30

    $525,000

    Sold Oct 28, 2025

    26 Fowler St, Upton, MA 01568

    • 2 Beds
    • 2 Baths
    • 1,632 Sq Ft
    • Built 1983

    Last Sold Summary

    • 9% Below List Price
    • $322/SF
    • 20 Days On Market

    Current Estimated Value $551,871

    Last Listing Agent Jennifer French REMAX Executive Realty

    26 Fowler St, Upton, MA 01568
    • /29

      Est $657,874

      Not Listed For Sale

      21 Shore Dr, Upton, MA 01568

      • 3 Beds
      • 2.5 Baths
      • 1,732 Sq Ft
      • Built 2001
      21 Shore Dr, Upton, MA 01568

      Last Sold Summary

      • 50 Days On Market

  • /7

    $799,000

    Open Sat 11AM - 1PM
    • 2 Beds
    • 2.5 Baths
    • 2,228 Sq Ft

    12 Boot Shop Rd Unit 12, Upton, MA 01568

    New amazing price at Cobbler's Creek, a premier 55+ community of detached condominiums by the renowned Black Brook Realty builder group! Enjoy a Storybook setting of homes nestled in a serene landscape where every day feels like a retreat! The popular "Cardinal" model offers 2-story living with everything you need handy on the 1st floor such as a covered front porch, foyer, powder rm, laundry rm

    The Kattman Team ERA Key Realty Services-Bay State Group

    12 Boot Shop Rd Unit 12, Upton, MA 01568
  • /2

    $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

    Current Estimated Value $606,931

    Last Listing Agent Matheus Goncalves Mega Realty Services

    3 Stoddard St, Upton, MA 01568
    • /42

      Est $992,233

      Not Listed For Sale

      129 South St, Upton, MA 01568

      • 4 Beds
      • 3.5 Baths
      • 3,120 Sq Ft
      • Built 1989
      129 South St, Upton, MA 01568

      Last Sold Summary

      • 157 Days On Market

  • /42

    $600,000

    • 3 Beds
    • 2.5 Baths
    • 1,792 Sq Ft

    110B High St, Upton, MA 01568

    Nestled on a 6-acre lot, this private retreat offers the perfect blend of country charm and endless potential. Surrounded by nature and set 1/3 of a mile back from the road, this 3-bedroom home provides a peaceful setting with sweeping views of the expansive front lawn. Inside, the open-concept design creates a warm and inviting atmosphere. The family room features a vaulted ceiling, hardwood

    Melissa Ellison Mathieu Newton Sotheby's International Realty

    110B High St, Upton, MA 01568
  • /36

    $555,000

    Sold Jun 22, 2026

    43 Knowlton Cir, Upton, MA 01568

    • 3 Beds
    • 2.5 Baths
    • 2,331 Sq Ft
    • Built 2003

    Last Sold Summary

    • 4% Above List Price
    • $238/SF
    • 7 Days On Market

    Current Estimated Value $541,831

    Last Listing Agent Lioce Properties Group

    43 Knowlton Cir, Upton, MA 01568
    • /42

      Est $975,394

      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

  • /42

    $1,095,000

    Pending
    • 4 Beds
    • 3.5 Baths
    • 3,768 Sq Ft

    11 Howarth Dr, Upton, MA 01568

    OPEN HOUSE CANCELLED. Stunning move-in ready home in highly desirable Glen Echo Estates near the Upton/Westborough line! This beautifully designed property offers sun-drenched living spaces, hardwood flooring & an open-concept layout perfect for today’s lifestyle. Dramatic two-story foyer, elegant dining room, private home office & an inviting family room with wood-burning fireplace create

    Mary Wood Lamacchia Realty, Inc.

    11 Howarth Dr, Upton, MA 01568
  • /42

    $825,000

    Sold Sep 17, 2025

    1 Summers Cir, Upton, MA 01568

    • 4 Beds
    • 3.5 Baths
    • 2,470 Sq Ft
    • Built 2019

    Last Sold Summary

    • 5% Below List Price
    • $334/SF
    • 46 Days On Market

    Current Estimated Value $865,339

    Last Listing Agent Michael Colombo Realty ONE Group Suburban Lifestyle

    1 Summers Cir, Upton, MA 01568
    • /42

      Est $1,057,305

      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

  • /26

    $499,000

    Open Sun 12:30PM - 2PM $61K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,228 Sq Ft

    1 Knowlton Cir Unit 1, Upton, MA 01568

    Back on market due to buyer's home sale contingency and priced to sell! A rare opportunity to own a four-bedroom, two and a half bath residence in the desirable Samreen Villas. This private end unit offers exceptional natural light and a thoughtfully designed layout ideal for both everyday living and entertaining. The main level features hardwood and ceramic tile flooring, an open-concept kitchen

    Leah Tringale Longwood Residential, LLC

    1 Knowlton Cir Unit 1, Upton, MA 01568
  • /36

    $725,000

    Sold Jan 14, 2026

    27 Fowler St, Upton, MA 01568

    • 4 Beds
    • 2.5 Baths
    • 2,729 Sq Ft
    • Built 1992

    Last Sold Summary

    • 9% Below List Price
    • $266/SF
    • 51 Days On Market

    Current Estimated Value $724,782

    Last Listing Agent Vasilina Waldron Berkshire Hathaway HomeServices Commonwealth Real Estate

    27 Fowler St, Upton, MA 01568
    • /40

      Est $670,000

      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

  • /42

    $1,450,000

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

    8 Stearns Rd, Upton, MA 01568

    Nestled at the end of a private cul-de-sac on nearly two acres, this meticulously renovated Colonial estate offers a premier multi-generational layout featuring main residence & fully equipped accessory dwelling. Beautiful main house boasts a mahogany deck, chef’s kitchen complete w/ quartz countertops, double wall ovens, gas cooktop, & an oversized butcher-block island, all adjacent to a coffee,

    Kathleen Nicoloro Ferrari + Co. Real Estate

    8 Stearns Rd, Upton, MA 01568
  • /42

    $512,700

    Sold Nov 21, 2025

    3 Knowlton Cir Unit 3, Upton, MA 01568

    • 3 Beds
    • 2.5 Baths
    • 1,731 Sq Ft
    • Built 2003

    Last Sold Summary

    • 4% Below List Price
    • $296/SF
    • 73 Days On Market

    Last Listing Agent Shripad Nandurbarkar Coldwell Banker Realty - Worcester

    3 Knowlton Cir Unit 3, Upton, MA 01568
    • /31

      Est $587,892

      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

  • /42

    $1,175,000

    • 4 Beds
    • 3.5 Baths
    • 4,054 Sq Ft

    35 Howarth Dr, Upton, MA 01568

    Glen Echo is a most desirable neighborhood close to Rt 495, MA Pike & Westborough. This pristine & spacious 4 bedroom, 3.5 bath Chatsworth Model Colonial has been impeccably maintained by its original owners. Enter to dramatic 2 story foyer w/ wainscoting & balcony. Open floor plan, 9 ft ceilings & tons of windows give this home an airy & roomy feel. Main level boasts hardwoods throughout.

    Gerald Simone Mathieu Newton Sotheby's International Realty

    35 Howarth Dr, Upton, MA 01568
  • /38

    $600,000

    Sold Dec 12, 2025

    29 Shore Dr, Upton, MA 01568

    • 3 Beds
    • 2.5 Baths
    • 1,732 Sq Ft
    • Built 2001

    Last Sold Summary

    • $346/SF
    • 21 Days On Market

    Current Estimated Value $603,757

    Last Listing Agent Maribeth McCauley Lynch Lamacchia Realty, Inc.

    29 Shore Dr, Upton, MA 01568
    • /37

      Est $561,302

      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

  • /41

    $1,199,000

    Open Sun 11AM - 1PM
    • 4 Beds
    • 4 Baths
    • 3,402 Sq Ft

    30 Mendon St, Upton, MA 01568

    30 Mendon St, Upton, MA Experience modern luxury in this newly constructed 2026 single-family home over 3,000 square feet of thoughtfully designed living space. Blending timeless elegance with contemporary comfort, this exceptional residence is crafted for today’s lifestyle. Featuring four spacious bedrooms and four full bathrooms, the home provides both privacy and convenience with high-end

    Luana Velame Century 21 The Real Estate Group

    30 Mendon St, Upton, MA 01568
  • /42

    $1,500,000

    Sold Jun 18, 2026

    72 Glenview St, Upton, MA 01568

    • 4 Beds
    • 7 Baths
    • 5,476 Sq Ft
    • Built 2012

    Last Sold Summary

    • $274/SF
    • 9 Days On Market

    Current Estimated Value $1,397,148

    Last Listing Agent Team Metrowest Berkshire Hathaway HomeServices Commonwealth Real Estate

    72 Glenview St, Upton, MA 01568

Showing Results 81 - 120, Page 3 of 18

How to Buy a Home How to Finance a Home How to Sell a Home