3,718

Upton, MA Homes

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  • /12

    $989,900

    New Construction
    • 4 Beds
    • 4 Baths
    • 2,990 Sq Ft

    19 W Main St, Upton, MA 01568

    UNDER CONSTRUCTION...Enjoy The Benefits of New Construction with Energy Efficiency & Low Future Maintenance! This stunning home offers the perfect blend of classic elegance and modern convenience with a spacious 1st FLOOR PRIMARY SUITE and laundry and 3 additional bedrooms on the 2nd level. The partially finished basement with finished half bath provides extra square footage plus access to the

    Kim Backlund Northeast Realty + Co.

    19 W Main St, Upton, MA 01568
  • /22

    $501,000

    Sold May 29, 2026

    35 Brooks St, Upton, MA 01568

    • 3 Beds
    • 2 Baths
    • 1,762 Sq Ft
    • Built 1956

    Last Sold Summary

    • 2% Above List Price
    • $284/SF
    • 5 Days On Market

    Current Estimated Value $509,578

    Last Listing Agent Melissa Bonina Century 21 Custom Home Realty

    35 Brooks St, Upton, MA 01568
    • /41

      Est $690,070

      Not Listed For Sale

      53 Warren St, Upton, MA 01568

      • 3 Beds
      • 2 Baths
      • 1,528 Sq Ft
      • Built 1955
      53 Warren St, Upton, MA 01568

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent David Ladner RE/MAX Harmony

  • /41

    $1,300,000

    • 4 Beds
    • 3.5 Baths
    • 3,556 Sq Ft

    9 South St, Upton, MA 01568

    Room to grow......inside and out! Expansive 4 bedroom 2 1/2 bath home with separate IN-LAW in finished basement all nestled on a picturesque 8.3 acres! This gem boasts a 2 story foyer, hardwoods throughout the first floor and newer carpet throughout the second floor. Oversized primary suite with cathedral ceiling, large walk-in closet, jacuzzi tub, stand up shower/double vanity. Huge family room

    Robin Haddad Mendon Local Realty

    9 South St, Upton, MA 01568
  • /30

    $620,000

    Sold Apr 06, 2026

    31 Elm St, Upton, MA 01568

    • 3 Beds
    • 3 Baths
    • 2,244 Sq Ft
    • Built 1957

    Last Sold Summary

    • 4% Above List Price
    • $276/SF
    • 5 Days On Market

    Current Estimated Value $608,467

    Last Listing Agent Maria Fraser Keller Williams Realty Boston Northwest

    31 Elm St, Upton, MA 01568
    • /31

      Est $485,389

      Not Listed For Sale

      48 Hartford Ave N, Upton, MA 01568

      • 3 Beds
      • 1 Bath
      • 1,008 Sq Ft
      • Built 1960
      48 Hartford Ave N, Upton, MA 01568

      Last Sold Summary

      • 4 Days On Market

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

  • /42

    $2,500,000

    • 4 Beds
    • 5 Baths
    • 4,040 Sq Ft

    117 South St, Upton, MA 01568

    75-Acre Elite Equestrian & Wellness Sanctuary. Ultimate private retreat with a 4,040 SF luxury Cape, world-class horse facilities, and resort backyard. Trail access to West Hill Dam. RESIDENCE: Chef's kitchen (Jade 6-burner, Sub-Zero, granite waterfall island). 1st-floor primary suite with vaulted ceilings & spa bath. 3 upper bedrooms, office, large bonus room + finished walkout lower level.

    Beth Byrne Gibson Sotheby's International Realty

    117 South St, Upton, MA 01568
  • /40

    $494,500

    Sold Jun 26, 2026

    49 Grove St, Upton, MA 01568

    • 3 Beds
    • 1 Bath
    • 1,300 Sq Ft
    • Built 1950

    Last Sold Summary

    • 1% Below List Price
    • $380/SF
    • 27 Days On Market

    Current Estimated Value $493,721

    Last Listing Agent Robyn Nasuti Realty ONE Group Suburban Lifestyle

    49 Grove St, Upton, MA 01568
    • /35

      Est $586,808

      Not Listed For Sale

      10 Breton Rd, Upton, MA 01568

      • 3 Beds
      • 2 Baths
      • 1,740 Sq Ft
      • Built 1958
      10 Breton Rd, Upton, MA 01568

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent The Mitchell-Gat Team Berkshire Hathaway Home Services Commonwealth Real Estate

  • /41

    $1,159,000

    • 4 Beds
    • 2.5 Baths
    • 3,360 Sq Ft

    33 Dairy Dr, Upton, MA 01568

    NEIGHBORHOOD SETTING WITH COMMUTER CONVENIENCE! This North-facing colonial offers over an acre of mature, professionally landscaped yard space that abuts trails and conservation land. Inside, the open layout is anchored by an incredibly spacious family room and modern chef’s kitchen with a double oven, 5-burner gas cooktop and oversized island to use for casual dining eating or as a homework hub.

    Erika Steele REMAX Executive Realty

    33 Dairy Dr, Upton, MA 01568
  • /29

    $445,000

    Sold Jun 29, 2026

    26 Hartford Ave N, Upton, MA 01568

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

    Last Sold Summary

    • 3% Below List Price
    • $390/SF
    • 22 Days On Market

    Current Estimated Value $445,196

    Last Listing Agent Scott Driscoll Redfin Corp.

    26 Hartford Ave N, Upton, MA 01568
    • /40

      Est $567,265

      Not Listed For Sale

      2 Breton Rd, Upton, MA 01568

      • 3 Beds
      • 1 Bath
      • 1,614 Sq Ft
      • Built 1985
      2 Breton Rd, Upton, MA 01568

      Last Sold Summary

      • 12 Days On Market

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

  • /42

    $899,900

    • 4 Beds
    • 2.5 Baths
    • 2,806 Sq Ft

    10 Sadler Rd, Upton, MA 01568

    Tucked away on a quiet cul-de-sac with 2 acres of wooded bliss, this Federal-front Colonial is pure serenity with an incredibly spacious layout to boot. It's 3000+ square feet that feels warm and homey with New England charm oozing from every room. The kitchen has NEW quartz countertops and a massive eat-in area with a downdraft gas stove. It flows seamlessly into a sun-drenched family room with

    Erika Steele REMAX Executive Realty

    10 Sadler Rd, Upton, MA 01568
  • /38

    $535,000

    Sold Jun 10, 2026

    36 Knowlton Cir Unit 1, Upton, MA 01568

    • 3 Beds
    • 2.5 Baths
    • 2,381 Sq Ft
    • Built 2003

    Last Sold Summary

    • 3% Below List Price
    • $225/SF
    • 19 Days On Market

    Last Listing Agent Karen Richardson LAER Realty Partners

    36 Knowlton Cir Unit 1, Upton, MA 01568
    • /27

      Est $581,509

      Not Listed For Sale

      12 Knowlton Cir, Upton, MA 01568

      • 3 Beds
      • 2.5 Baths
      • 2,184 Sq Ft
      • Built 2003
      12 Knowlton Cir, Upton, MA 01568

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Mary Ann Tecce Gibson Sotheby's International Realty

  • /26

    $489,999

    $10K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,785 Sq Ft

    140 Main St Unit B, Upton, MA 01568

    Presenting an exceptional condominium residence at 140 Main St U:B, Upton, MA, a meticulously maintained property constructed in 2020. This 1785 square foot unit offers a refined living experience across three stories, embodying an attractive and contemporary aesthetic. The culinary space features an open-plan design seamlessly integrating with the living room, equipped with stainless steel

    Mike Dagilis ERA Key Realty Services- Milf

    140 Main St Unit B, 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 $1,348,064

    Last Listing Agent Neil Fredette Keller Williams Realty-Merrimack

    5 Azalea Ln, Upton, MA 01568
    • /28

      Est $538,625

      Not Listed For Sale

      39 Knowlton Cir, Upton, MA 01568

      • 4 Beds
      • 2.5 Baths
      • 1,731 Sq Ft
      • Built 2003
      39 Knowlton Cir, Upton, MA 01568

      Last Sold Summary

      • 14 Days On Market

      Last Listing Agent Alan Yanofsky RE/MAX Real Estate Center

  • /7

    $999,900

    New Construction
    • 4 Beds
    • 2.5 Baths
    • 2,780 Sq Ft

    17 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.

    17 W Main St, Upton, MA 01568
  • /26

    $875,000

    Sold Nov 13, 2025

    95 Crockett Rd, Upton, MA 01568

    • 2 Beds
    • 1 Bath
    • 864 Sq Ft
    • Built 1950

    Last Sold Summary

    • 9% Above List Price
    • $1,013/SF
    • 9 Days On Market

    Current Estimated Value $811,096

    Last Listing Agent Campos Homes RE/MAX Real Estate Center

    95 Crockett Rd, Upton, MA 01568
    • /42

      Est $819,045

      Not Listed For Sale

      20 Maple Ave, Upton, MA 01568

      • 5 Beds
      • 2.5 Baths
      • 3,291 Sq Ft
      • Built 1880
      20 Maple Ave, Upton, MA 01568

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Danielle McCarthy Berkshire Hathaway HomeServices Commonwealth Real Estate

  • /32

    $744,900

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

    27 James Rd Unit 4, Upton, MA 01568

    LAST UNIT AVAILABLE NEW CONSTRUCTION. Free standing unit no age restrictions in 4 lot subdivision. Kitchen is spacious with eat in dining area, hardwood floors, granite, kitchen island, stainless steel appliances. Opens to a family room with access to backyard. Upstairs has a 3 bedroom layout but deeded as a 2 bedroom dwelling 3rd room could be in home office/den/playroom. Ensuite primary with

    Kim Kimball Kimball Property Realty Inc.

    27 James Rd Unit 4, Upton, MA 01568
  • /23

    $472,800

    Sold Sep 05, 2025

    56 Shore Dr, Upton, MA 01568

    • 3 Beds
    • 1.5 Baths
    • 1,320 Sq Ft
    • Built 1974

    Last Sold Summary

    • 5% Below List Price
    • $358/SF
    • 6 Days On Market

    Current Estimated Value $480,276

    Last Listing Agent Samantha Edwards Prime Time Real Estate Inc.

    56 Shore Dr, Upton, MA 01568
    • /6

      Est $430,105

      Not Listed For Sale

      52 Pleasant St, Upton, MA 01568

      • 2 Beds
      • 2 Baths
      • 816 Sq Ft
      • Built 1952
      52 Pleasant St, Upton, MA 01568

      Last Sold Summary

      • 127 Days On Market

      Last Listing Agent James Pham RE/MAX Partners

  • /42

    $799,900

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

    158 Main St, Upton, MA 01568

    Don't miss this well-maintained multifamily property offering an excellent opportunity for both investors and owner-occupants. Whether you're looking to generate rental income, build long-term wealth, or offset your mortgage by living in one unit while renting the other, this property offers outstanding flexibility.Each unit features spacious living areas, comfortable bedrooms, functional

    Rita Silva-Martins eXp Realty LLC - Corporate Office

    158 Main St, Upton, MA 01568
  • /38

    $1,160,000

    Sold Nov 24, 2025

    47 Fiske Mill Rd, Upton, MA 01568

    • 4 Beds
    • 2.5 Baths
    • 4,514 Sq Ft
    • Built 2020

    Last Sold Summary

    • 7% Below List Price
    • $257/SF
    • 19 Days On Market

    Current Estimated Value $1,196,518

    Last Listing Agent The Arienti Group REMAX Executive Realty

    47 Fiske Mill Rd, Upton, MA 01568
    • /38

      Est $480,982

      Not Listed For Sale

      23 Hartford Ave S, Upton, MA 01568

      • 6 Beds
      • 2 Baths
      • 2,605 Sq Ft
      • Built 1890
      23 Hartford Ave S, Upton, MA 01568

      Last Sold Summary

      • 12 Days On Market

      Last Listing Agent Faina Shapiro Berkshire Hathaway Home Services Commonwealth Real Estate

  • /42

    $1,225,000

    $25K PRICE DROP
    • 4 Beds
    • 5.5 Baths
    • 5,736 Sq Ft

    12 Breton Rd, Upton, MA 01568

    With a flexible layout that supports multigenerational living, this gorgeous custom-built colonial has ample space and is situated on 3+ private acres. From the moment you step into the grand two-story foyer adorned w/ granite flooring, you’ll be captivated by the attention to detail & luxurious features throughout, incl 9ft+ ceilings & gleaming hardwoods. Spacious fam rm is a true showpiece w/

    Melissa Ellison Mathieu Newton Sotheby's International Realty

    12 Breton Rd, Upton, MA 01568
  • /41

    $525,000

    Sold Jul 22, 2026

    57 Plain St, Upton, MA 01568

    • 3 Beds
    • 2.5 Baths
    • 1,372 Sq Ft
    • Built 1956

    Last Sold Summary

    • $383/SF
    • 6 Days On Market

    Current Estimated Value $514,669

    Last Listing Agent Team ROVI Real Broker MA, LLC

    57 Plain St, Upton, MA 01568
    • /36

      Est $487,688

      Not Listed For Sale

      21 Maple Ave, Upton, MA 01568

      • 3 Beds
      • 2.5 Baths
      • 1,520 Sq Ft
      • Built 2004
      21 Maple Ave, Upton, MA 01568

      Last Sold Summary

      • 42 Days On Market

      Last Listing Agent The Jenkins Group Keller Williams Realty

  • /42

    $1,495,000

    Pending
    • 3 Beds
    • 2 Baths
    • 2,052 Sq Ft

    94 Rawson St, Uxbridge, MA 01569

    Dutch Hill Farm is an established equestrian property on 40± acres, including approximately 18 acres of open fields and productive hayfields. The updated farmhouse offers 3 bedrooms, 2 baths, exposed beams, a welcoming kitchen, porch, deck, attached 2-car garage, and 19 kW solar array. Designed for an active equestrian lifestyle, the residence, barn, arenas, paddocks, and pastures are

    Stanley Edwards LandVest, Inc., Concord

    94 Rawson St, Uxbridge, MA 01569
  • /41

    $478,000

    Sold May 13, 2026

    72 Main St, Upton, MA 01568

    • 2 Beds
    • 1 Bath
    • 1,536 Sq Ft
    • Built 1981

    Last Sold Summary

    • 14% Above List Price
    • $311/SF
    • 39 Days On Market

    Current Estimated Value $462,658

    Last Listing Agent Ryan Wilson Keller Williams Realty

    72 Main St, Upton, MA 01568
    • /40

      Est $508,697

      Not Listed For Sale

      4 Hartford Ave S, Upton, MA 01568

      • 4 Beds
      • 1.5 Baths
      • 2,082 Sq Ft
      • Built 1860
      4 Hartford Ave S, Upton, MA 01568

      Last Sold Summary

      • 54 Days On Market

      Last Listing Agent Laura Hebb ERA Key Realty Services

  • /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
  • /41

    $740,000

    Sold Oct 21, 2025

    10 Prospect St, Upton, MA 01568

    • 4 Beds
    • 2.5 Baths
    • 2,872 Sq Ft
    • Built 1986

    Last Sold Summary

    • 1% Below List Price
    • $258/SF
    • 18 Days On Market

    Current Estimated Value $777,231

    Last Listing Agent Jeanne Leombruno Century 21 Custom Home Realty

    10 Prospect St, Upton, MA 01568
    • /37

      Est $455,759

      Not Listed For Sale

      124 Main St, Upton, MA 01568

      • 2 Beds
      • 1.5 Baths
      • 1,712 Sq Ft
      • Built 1828
      124 Main St, Upton, MA 01568

      Last Sold Summary

      • 12 Days On Market

      Last Listing Agent Amber Cadorette Keller Williams Elite

  • /36

    $699,900

    $29K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,950 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
  • /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 $705,142

    Last Listing Agent Alissa Tosches Lamacchia Realty, Inc.

    26 Brooks St, Upton, MA 01568
    • /30

      Est $441,544

      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

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

  • /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

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