Upton, MA Homes

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  /42

  $699,000

  $16K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,835 Sq Ft

  52 Elm St, Upton, MA 01568

  Tucked along a scenic country road, this beautifully preserved early 18th-century Gambrel blends timeless New England character with the comfort and updates today’s buyers seek. Rich with historic charm, the rambling floor plan offers warm, inviting spaces including a stunning 1st-floor primary suite, great room, library/den, front-to-back living room, classic keeping room with stone fireplace,

  

  Robyn Nasuti

  Realty ONE Group Suburban Lifestyle

  52 Elm St, Upton, MA 01568
• Explore Upton

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  /17

  $3,500 Per Month

  • 3 Beds
  • 2 Baths
  • 1,576 Sq Ft
  • House for Rent

  32 Station St, Upton, MA 01568

  Rental Home available soon. Three bedrooms, 2 car garage, central air, quiet setting. Can be semi furnished - depends on what have or need. New painted interior, unfinished basement with concrete floor for storage - kids can ride bikes in there! Over 1/2 acre lot. Close to Upton schools and playgrounds. Easy commute to 495/Mass Poke

  

  Bill McCormick

  McCormick Properties

  32 Station St, Upton, MA 01568
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  /39

  $480,000

  Sold Sep 16, 2026

  4 Picadilly St, Upton, MA 01568

  • 3 Beds
  • 1 Bath
  • 1,080 Sq Ft
  • Built 1976

  Last Sold Summary

  • 3% Below List Price
  • $444/SF
  • 10 Days On Market

  Current Estimated Value $468,185

  Last Listing Agent Robyn Nasuti Realty ONE Group Suburban Lifestyle

  4 Picadilly St, Upton, MA 01568
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  /39

  Est $1,140,765

  Not Listed For Sale

  7 River Bend Rd, Upton, MA 01568

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

  7 River Bend Rd, Upton, MA 01568

  Last Sold Summary

  • 8 Days On Market

  Last Listing Agent Murray/Gresenz Group Compass
• 

  

  

  /35

  $749,900

  Open Sun 1PM - 3PM

  • 2 Beds
  • 2 Baths
  • 1,734 Sq Ft

  5 Boot Shop Rd Unit 5, Upton, MA 01568

  Beautiful new construction one-level "Starling" floor plan now available at Cobbler's Creek, a vibrant 55+ community built by exceptional builders with a reputation for excellence! You're welcomed by an open & airy floor plan that seamlessly connects the sunny living room w/fireplace & built-ins, dining rm & kitchen all w/hardwood floors. The kitchen features attractive cabinets with moldings

  

  Jeffrey Germagian

  ERA Key Realty Services-Bay State Group

  5 Boot Shop Rd Unit 5, Upton, MA 01568
• 

  

  /35

  Starting at $2,039

  Total Monthly Price

  • 1 - 2 Beds

  149 Main St, Upton, MA 01568

  Welcome home to 149 Main, a new luxury apartment community in the quintessential New England Town of Upton, Massachusetts. Offering smart, modern home features from designer cabinetry and color schemes to sought-after community features just outside your door. Discover the lifestyle at 149 Main.*311-This apartment is part of the 40B program, apartment 311, 2-bedroom, 2 bathrooms available for

  149 Main Street Apartments

  

  149 Main St, Upton, MA 01568
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  /32

  $595,000

  Sold Jan 07, 2026

  84 High St, Upton, MA 01568

  • 4 Beds
  • 3 Baths
  • 2,463 Sq Ft
  • Built 1952

  Last Sold Summary

  • 8% Below List Price
  • $242/SF
  • 136 Days On Market

  Current Estimated Value $632,504

  Last Listing Agent Ann Marie Silva Redfin Corp.

  84 High St, Upton, MA 01568
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  /42

  Est $902,106

  Not Listed For Sale

  1 Summers Cir, Upton, MA 01568

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

  1 Summers Cir, Upton, MA 01568

  Last Sold Summary

  • 46 Days On Market

  Last Listing Agent Michael Colombo Realty ONE Group Suburban Lifestyle
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  /42

  $1,099,000

  Open Sun 12PM - 2PM

  • 4 Beds
  • 4.5 Baths
  • 2,889 Sq Ft

  91 High St, Upton, MA 01568

  Be the first to call this exceptional new-construction Colonial home! Ideally situated near the heart of downtown Upton, this 2,889 -square-foot residence pairs timeless farmhouse charm with modern finishes and a flexible layout designed for today’s lifestyle. Enjoy the character of small-town living with convenient access to Upton’s town beach, parks, library, post office, local shops, and even

  

  Robyn Nasuti

  Realty ONE Group Suburban Lifestyle

  91 High St, Upton, MA 01568
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  /12

  $2,000 Per Month

  • 1 Bed
  • 1 Bath
  • 900 Sq Ft
  • Apartment for Rent

  112 Main St Unit B, Upton, MA 01568

  Location !! West Upton Center: 5 minutes to 495, 15 minutes to Mass Pike. LARGE 2 level ,1 bedroom and 1office, perfect for a couple ! Kitchen opens to a sun porch and patio area. Newer windows, hardwood floors, new economical mini split heat and AC both levels. Office and full bath is near the bedroom on the second floor. Best suited for single that wants space or couple. Park at your door !

  

  Bill McCormick

  McCormick Properties

  112 Main St Unit B, Upton, MA 01568
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  /41

  $635,000

  Sold Aug 14, 2026

  236 Mendon St, Upton, MA 01568

  • 3 Beds
  • 1.5 Baths
  • 1,638 Sq Ft
  • Built 1788

  Last Sold Summary

  • 6% Below List Price
  • $388/SF
  • 19 Days On Market

  Current Estimated Value $664,889

  Last Listing Agent Laura Hebb ERA Key Realty Services

  236 Mendon St, Upton, MA 01568
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  /12

  Not Listed For Sale

  51 School St Unit 2, Upton, MA 01568

  • 3 Beds
  • 2.5 Baths
  • 1,420 Sq Ft
  • Built 1900

  51 School St Unit 2, Upton, MA 01568

  Last Sold Summary

  • 5 Days On Market

  Last Listing Agent Daniel DiBiasio DiBiasio Realty LLC
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  /28

  $799,000

  Open Sun 1PM - 3PM

  • 2 Beds
  • 2.5 Baths
  • 2,228 Sq Ft

  10 Boot Shop Rd Unit 10, Upton, MA 01568

  New offering 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 surrounded by nature where every day feels like a retreat! The popular "Cardinal" model offers two-story living with everything you need handy on the first floor such as a covered front porch, foyer,

  

  Jeffrey Germagian

  ERA Key Realty Services-Bay State Group

  10 Boot Shop Rd Unit 10, Upton, MA 01568
• 

  

  /15

  $2,700 Per Month

  • 2 Beds
  • 1.5 Baths
  • 1,600 Sq Ft
  • Apartment for Rent

  76 Main St Unit A, Upton, MA 01568

  Upton Duplex Renovation is complete . This is the lifestyle you want!!! Fastidious attention to detail though out this "better than new" Townhouse Style Apartment. 1600sq ft including 3rd floor office/ kids space. Walk to Restaurants , parks, and beaches. Close to 495 , 90, and Commuter rail. Gorgeous Country sized kitchen with timeless top of the line Cherry Cabinetry, Stainless Steal

  Cori Oehley Century 21 Custom Home Realty

  76 Main St Unit A, Upton, MA 01568
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  /41

  $1,000,000

  Sold Jun 22, 2026

  154 South St, Upton, MA 01568

  • 4 Beds
  • 3.5 Baths
  • 4,265 Sq Ft
  • Built 2001

  Last Sold Summary

  • 5% Below List Price
  • $234/SF
  • 7 Days On Market

  Current Estimated Value $1,030,528

  Last Listing Agent David Hill Central MA Homes

  154 South St, Upton, MA 01568
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  /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
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  /13

  $789,900

  Pending

  • 2 Beds
  • 2 Baths
  • 1,734 Sq Ft

  14 Boot Shop Rd Unit 14, Upton, MA 01568

  Come view our beautiful, new construction "Starling" model offering one-level at Cobbler's Creek, a vibrant 55+ community built by exceptional builders with a reputation for excellence! Enjoy a welcoming, open & airy floor plan that seamlessly connects bright living and dining areas to the stylish kitchen all with hardwood floors. The well-appointed kitchen features attractive cabinets with

  

  Jeffrey Germagian

  ERA Key Realty Services-Bay State Group

  14 Boot Shop Rd Unit 14, Upton, MA 01568
• 

  

  /19

  $4,500

  Total Monthly Price

  • 4 Beds
  • 2.5 Baths
  • 3,350 Sq Ft
  • House for Rent

  164 South St, Upton, MA 01568

  This impressive, spacious 4-bedroom, 2.5-bathroom home is nestled in a beautifully wooded area with a highly private yard. Inside, you’ll find soaring ceilings, elegant dual staircases, a 3-car garage, and fresh paint paired with brand-new carpet. There are hardwoods, and tile throughout. The expansive kitchen flows seamlessly into the family room, complemented by a formal dining room and a

  164 South St, Upton, MA 01568
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  /3

  $1,763,100

  Sold Apr 24, 2026

  7 Sawmill Brook Ln, Upton, MA 01568

  • 4 Beds
  • 4.5 Baths
  • 3,609 Sq Ft
  • Built 2025

  Last Sold Summary

  • 10% Above List Price
  • $489/SF
  • 119 Days On Market

  Last Listing Agent Team Metrowest Berkshire Hathaway HomeServices Commonwealth Real Estate

  7 Sawmill Brook Ln, Upton, MA 01568
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  /36

  Est $889,302

  Not Listed For Sale

  49 East St, Upton, MA 01568

  • 3 Beds
  • 2.5 Baths
  • 2,188 Sq Ft
  • Built 2017

  49 East St, Upton, MA 01568

  Last Sold Summary

  • 4 Days On Market

  Last Listing Agent Ellen Koswick REMAX Executive Realty
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  /31

  $484,900

  $15K PRICE DROP Pending

  • 3 Beds
  • 2 Baths
  • 1,176 Sq Ft

  10 Hopkinton Rd, Upton, MA 01568

  Adorable Upton home ready to make your own! This charming property offers so many desirable features, including abundant natural sunlight streaming through the skylights, a convenient location just minutes from Route 495, and beautiful views of Pratt Pond. Enjoy a private backyard with endless potential for entertaining, gardening, or simply relaxing outdoors. Inside, you'll find flexible living

  

  Kathryn Amorello

  Coldwell Banker Realty - Worcester

  10 Hopkinton Rd, Upton, MA 01568
• 

  

  /39

  $560,000

  Sold Jan 21, 2026

  127 Glenview St, Upton, MA 01568

  • 3 Beds
  • 3 Baths
  • 1,711 Sq Ft
  • Built 1954

  Last Sold Summary

  • 6% Below List Price
  • $327/SF
  • 4 Days On Market

  Current Estimated Value $580,555

  Last Listing Agent Maria Morte Berkshire Hathaway HomeServices Commonwealth Real Estate

  127 Glenview St, Upton, MA 01568
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  /42

  Est $1,075,638

  Not Listed For Sale

  14 Francis Dr, Upton, MA 01568

  • 4 Beds
  • 2.5 Baths
  • 3,901 Sq Ft
  • Built 2008

  14 Francis Dr, Upton, MA 01568

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent Gerald Simone Mathieu Newton Sotheby's International Realty
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  /40

  $1,079,000

  • 4 Beds
  • 3.5 Baths
  • 3,350 Sq Ft

  165 East St, Upton, MA 01568

  Pride of ownership abounds at this exceptional 4-bedroom, 3.5 bath custom contemporary home set on 3.50 beautifully maintained acres offering privacy and endless opportunities to enjoy the outdoors. Enter through the two-story foyer and be greeted by sunlight pouring into the home through an abundance of windows, skylights, and sliders creating a bright and welcoming atmosphere throughout. The

  Michael Stein Redfin Corp.

  165 East St, Upton, MA 01568
• 

  

  /40

  $682,000

  Sold Jun 26, 2026

  20 Fiske Ave, Upton, MA 01568

  • 3 Beds
  • 2 Baths
  • 1,777 Sq Ft
  • Built 2011

  Last Sold Summary

  • 11% Above List Price
  • $384/SF
  • 5 Days On Market

  Current Estimated Value $673,479

  Last Listing Agent Megan Tolland Realty Executives Boston West

  20 Fiske Ave, Upton, MA 01568
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  /42

  Est $576,840

  Not Listed For Sale

  31 Conestoga Dr, Uxbridge, MA 01569

  • 3 Beds
  • 1 Bath
  • 2,245 Sq Ft
  • Built 1991

  31 Conestoga Dr, Uxbridge, MA 01569

  Last Sold Summary

  • 20 Days On Market

  Last Listing Agent Cheryl Eidinger-Taylor ERA Key Realty Services
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  /14

  $1,499,999

  New Construction Pending

  • 5 Beds
  • 4 Baths
  • 3,875 Sq Ft

  9 Kiwanis Beach Rd, Upton, MA 01568

  ***UNDER CONSTRUCTION*** Location Location Location!! Perfect timing to snatch a brand-new house while it's still under construction and have a chance to pick your own finishes and be ready to move in by the new school year. Perched up on a hill overlooking Pratt Pond. Steps away from Kiwanis Beach Park and enjoy the public beach, baseball+soccer fields, tennis/pickleball+basketball courts.

  Luciano Souza Pinto Real Estate

  9 Kiwanis Beach Rd, Upton, MA 01568
• 

  

  /36

  $820,000

  Sold Mar 30, 2026

  13 Jonathans Way, Upton, MA 01568

  • 4 Beds
  • 2.5 Baths
  • 3,352 Sq Ft
  • Built 1994

  Last Sold Summary

  • 4% Below List Price
  • $245/SF
  • 34 Days On Market

  Current Estimated Value $829,637

  Last Listing Agent Shelly Armstrong Redfin Corp.

  13 Jonathans Way, Upton, MA 01568
• 

  

  /36

  Est $507,543

  Not Listed For Sale

  113 Hecla St, Uxbridge, MA 01569

  • 4 Beds
  • 3 Baths
  • 2,340 Sq Ft
  • Built 1900

  113 Hecla St, Uxbridge, MA 01569

  Last Sold Summary

  • 18 Days On Market

  Last Listing Agent Paula Sullivan Century 21 Custom Home Realty
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  /12

  $989,900

  New Construction Pending

  • 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
• 

  

  /31

  $460,000

  Sold Jun 30, 2026

  41 Main St, Upton, MA 01568

  • 2 Beds
  • 1.5 Baths
  • 1,155 Sq Ft
  • Built 1860

  Last Sold Summary

  • 2% Above List Price
  • $398/SF
  • 8 Days On Market

  Current Estimated Value $442,974

  Last Listing Agent John Herrera Ownit a Real Estate Firm

  41 Main St, Upton, MA 01568
• 

  

  /39

  Est $684,837

  Not Listed For Sale

  109 Rawson St, Uxbridge, MA 01569

  • 3 Beds
  • 2.5 Baths
  • 2,080 Sq Ft
  • Built 1992

  109 Rawson St, Uxbridge, MA 01569

  Last Sold Summary

  • 33 Days On Market

  Last Listing Agent Margaret Vosburgh Fine Properties, Inc.
• 

  

  /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
• 

  

  /36

  $791,900

  Sold Dec 19, 2025

  6 Hickory Ln, Upton, MA 01568

  • 4 Beds
  • 2.5 Baths
  • 2,416 Sq Ft
  • Built 1977

  Last Sold Summary

  • 7% Above List Price
  • $328/SF
  • 5 Days On Market

  Current Estimated Value $798,942

  Last Listing Agent Melissa Bonina Century 21 Custom Home Realty

  6 Hickory Ln, Upton, MA 01568
• 

  

  /24

  Est $528,690

  Not Listed For Sale

  35 Hartford Ave N, Upton, MA 01568

  • 3 Beds
  • 1 Bath
  • 1,040 Sq Ft
  • Built 1969

  35 Hartford Ave N, Upton, MA 01568

  Last Sold Summary

  • 6 Days On Market

  Last Listing Agent Omar Regalado Serhant
• 

  

  /41

  $1,159,000

  Pending

  • 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
• 

  

  /31

  $750,000

  Sold Mar 11, 2026

  27 James Rd Unit 2, Upton, MA 01568

  • 3 Beds
  • 3.5 Baths
  • 2,200 Sq Ft
  • Built 2025

  Last Sold Summary

  • $341/SF
  • 87 Days On Market

  Current Estimated Value $737,011

  Last Listing Agent Kim Kimball Kimball Property Realty Inc.

  27 James Rd Unit 2, 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
• 

  

  /36

  $1,147,900

  • 4 Beds
  • 2.5 Baths
  • 2,884 Sq Ft

  Lot 12 Rawson Farm, Mendon, MA 01756

  The Modified Hampton is one of our most popular plans in the Miscoe Springs neighborhood. Now building this 4 bedroom, 2.5 bath home with professional designer finishes to be included. Featuring a beautiful cathedral family room complete with fireplace and adjacent to a great entertaining kitchen you can dine casually around the quartz island or in the breakfast area. Enhanced cabinets to the

  Gary Smith Mendon Area Real Estate

  Lot 12 Rawson Farm, Mendon, MA 01756
• 

  

  /5

  $297,000

  Sold Apr 14, 2026

  11 East St, Upton, MA 01568

  • Land
  • 2.23 Acres
  • $133,184 per Acre

  Last Sold Summary

  • 24% Below List Price
  • 73 Days On Market

  Current Estimated Value $970,896

  Last Listing Agent Laura Hebb ERA Key Realty Services

  11 East St, Upton, MA 01568

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