3,718

Upton, MA Homes

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  • /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 $548,719

      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

      Last Listing Agent Christine Newell LAER Realty Partners

  • /23

    $399,900

    Pending
    • 4 Beds
    • 2.5 Baths
    • 2,340 Sq Ft

    324 Mendon St, Upton, MA 01568

    Calling All Contractors, Investors & Flippers! Exceptional opportunity to transform this 4-bedroom Coln, privately sited on nearly 2 acres in desirable Upton. Featuring an impressive family room, 2 full baths, first-floor laundry, an unfinished LL & a 2-car under garage, this home offers a fantastic floor plan and tremendous potential. The property is in need of a complete renovation due to burst

    Marilyn Green RE/MAX Signature Properties

    324 Mendon St, 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 $411,815

    Last Listing Agent Clifton LaPorte Berkshire Hathaway HomeServices Commonwealth Real Estate

    120 High St, Upton, MA 01568
    • /36

      Est $621,647

      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

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

  • /42

    $1,340,000

    Open Sat 12PM - 1:30PM
    • 5 Beds
    • 3.5 Baths
    • 4,498 Sq Ft

    66 Glenview St, Upton, MA 01568

    Set amid park-like grounds with a private wooded backdrop, this expansive Upton home stands out for its generous living space, thoughtful updates and remarkable flexibility. Updated kitchens and baths throughout bring a fresh, polished feel to the home, while impressive architectural details begin in the soaring two-story foyer and continue into the dramatic family room, where a vaulted ceiling,

    Lisa Aron Williams Coldwell Banker Realty - Sudbury

    66 Glenview 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 $682,283

      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

      Last Listing Agent Giselle Pajazetovic P&Co Real Estate

  • /16

    $439,000

    $61K PRICE DROP Pending
    • 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
  • /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 $878,993

    Last Listing Agent Deb Kotlarz Keller Williams Realty Boston Northwest

    49 Warren St, Upton, MA 01568
    • /31

      Est $295,877

      Not Listed For Sale

      1 Nelson St Unit C, Upton, MA 01568

      • 1 Bed
      • 1 Bath
      • 786 Sq Ft
      • Built 1790
      1 Nelson St Unit C, Upton, MA 01568

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Catherine Carrara Realty ONE Group Suburban Lifestyle

  • /36

    $709,000

    $16K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,950 Sq Ft

    56 Shannon Way Unit 56, Upton, MA 01568

    Welcome to this beautifully maintained two-story townhouse in the highly desirable 55+ Upton Ridge community, where comfort, style, and low-maintenance living come together. Built in 2023 this floor plan features a first-floor primary suite, offering both privacy and ease of living. Upstairs features a generously sized second bedroom with walk in closet, full bath and a spacious second-floor loft

    The Semple and Hettrich Team Coldwell Banker Realty - Sudbury

    56 Shannon Way Unit 56, 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 $375,023

    Last Listing Agent June Hillier REMAX Executive Realty

    8 Maple St, Upton, MA 01568
    • /18

      Est $560,722

      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

      Last Listing Agent My House Partners Team REMAX Executive Realty

  • /41

    $449,000

    $150K PRICE DROP
    • 5 Beds
    • 3 Baths
    • 2,887 Sq Ft

    130 High St, Upton, MA 01568

    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 entertaining. A fully renovated backyard shed adds

    Jacob Greasley eXp Realty LLC

    130 High 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 $591,161

    Last Listing Agent Jennifer French REMAX Executive Realty

    26 Fowler St, Upton, MA 01568
    • /38

      Est $694,337

      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

      Last Listing Agent Brian O'keefe Redfin Corp.

  • /28

    $799,000

    Open Fri 1PM - 3PM
    • 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 $608,620

    Last Listing Agent Matheus Goncalves Mega Realty Services

    3 Stoddard St, Upton, MA 01568
    • /40

      Est $722,684

      Not Listed For Sale

      25 Warren St, Upton, MA 01568

      • 4 Beds
      • 2 Baths
      • 2,476 Sq Ft
      • Built 1955
      25 Warren St, Upton, MA 01568

      Last Sold Summary

      • 12 Days On Market

      Last Listing Agent Lisa Giunta Conway - Walpole

  • /42

    $600,000

    Pending
    • 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 $543,642

    Last Listing Agent Lioce Properties Group Lamacchia Realty, Inc.

    43 Knowlton Cir, Upton, MA 01568
    • /40

      Est $781,244

      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

      Last Listing Agent Judy Leonelli Mendon Local Realty

  • /42

    $519,999

    • 3 Beds
    • 3.5 Baths
    • 2,091 Sq Ft

    13 Knowlton Cir Unit 13, Upton, MA 01568

    Welcome to this WEST-FACING townhouse in the desirable SAMREEN VILLAS community. 13 KNOWLTON CIRCLE offers low-maintenance living in a convenient Upton location.This 3-BEDROOM, 3.5-BATH home features an OPEN-CONCEPT FLOOR PLAN with HARDWOOD FLOORS, a SPACIOUS KITCHEN, and abundant natural light throughout the main living area. The second floor includes THREE GENEROUSLY SIZED BEDROOMS and a LARGE

    Smita Sinha Keller Williams Pinnacle MetroWest

    13 Knowlton Cir Unit 13, 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 $897,013

    Last Listing Agent Michael Colombo Realty ONE Group Suburban Lifestyle

    1 Summers Cir, Upton, MA 01568
    • /42

      Est $1,372,551

      Not Listed For Sale

      19 Juniper Rd, Upton, MA 01568

      • 4 Beds
      • 4.5 Baths
      • 3,900 Sq Ft
      • Built 2001
      19 Juniper Rd, Upton, MA 01568

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Team Metrowest Berkshire Hathaway HomeServices Commonwealth Real Estate

  • /26

    $499,000

    $61K PRICE DROP Pending
    • 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 $737,373

    Last Listing Agent Vasilina Waldron Berkshire Hathaway HomeServices Commonwealth Real Estate

    27 Fowler St, Upton, MA 01568
    • /42

      Est $1,006,519

      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

      Last Listing Agent Sandra Copley RE/MAX Real Estate Center

  • /33

    $699,000

    Pending
    • 6 Beds
    • 3 Baths
    • 2,617 Sq Ft

    78 Main St, Upton, MA 01568

    Rare 2-Family Gem with Historic Charm & Modern Luxury. Discover this meticulously renovated two-family home, perfectly situated on 2 sprawling acres near the heart of town. Gutted to the studs in 2015 and updated with a new roof, windows, and high-end finishes, this property offers the peace of mind of a new build with the character of a classic estate. Both units are fully de-leaded,

    Beth Byrne Gibson Sotheby's International Realty

    78 Main St, 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
    • /41

      Est $721,559

      Not Listed For Sale

      334 Mendon St, Upton, MA 01568

      • 3 Beds
      • 2 Baths
      • 2,154 Sq Ft
      • Built 1984
      334 Mendon St, Upton, MA 01568

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Paul Harkey Paul Harkey Real Estate

  • /42

    $1,125,000

    $50K PRICE DROP
    • 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
  • /14

    $340,000

    Sold Aug 03, 2026

    10 Pinecrest Rd, Uxbridge, MA 01569

    • 2 Beds
    • 1.5 Baths
    • 1,304 Sq Ft
    • Built 1989

    Last Sold Summary

    • 8% Below List Price
    • $261/SF
    • 26 Days On Market

    Current Estimated Value $362,422

    Last Listing Agent Rosanna Blanchard Afonso Real Estate

    10 Pinecrest Rd, Uxbridge, MA 01569
    • /29

      Est $695,017

      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

      Last Listing Agent Amanda Salazar Realty ONE Group Suburban Lifestyle

  • /27

    $649,900

    Pending
    • 4 Beds
    • 2.5 Baths
    • 2,324 Sq Ft

    30 Pearl St, Upton, MA 01568

    **OFFER DEADLINE - Tues, 8/4, 3PM** Welcome to this beautifully crafted 2006-built Colonial offering 2,324 square feet of thoughtfully designed living space. With 4 bedrooms and 2.5 bathrooms, this home blends timeless New England style with modern updates throughout.The spacious kitchen features upgraded quartz countertops and custom cabinetry and shelving with abundant storage, perfect for

    Michael O'Brien ERA Key Realty Services- Fram

    30 Pearl St, 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 $611,990

    Last Listing Agent Maribeth McCauley Lynch Lamacchia Realty, Inc.

    29 Shore Dr, Upton, MA 01568
    • /42

      Est $1,114,011

      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

      Last Listing Agent Team Metrowest Berkshire Hathaway HomeServices Commonwealth Real Estate

  • /41

    $1,125,000

    $74K PRICE DROP
    • 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 $1,478,286

    Last Listing Agent Team Metrowest Berkshire Hathaway HomeServices Commonwealth Real Estate

    72 Glenview St, Upton, MA 01568

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