Upton, MA Homes

• 

  

  

  /35

  $749,900

  Open Fri 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
• Explore Upton

• 

  

  

  /35

  Starting at $2,200

  Total Monthly Price

  • 1 Bed

  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.

  149 Main Street Apartments

  

  149 Main St, Upton, MA 01568
• 

  

  

  /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
• 

  

  

  /39

  Est $979,772

  Not Listed For Sale

  22 Cider Mill Ln, Upton, MA 01568

  • 4 Beds
  • 2.5 Baths
  • 2,149 Sq Ft
  • Built 1974

  22 Cider Mill Ln, Upton, MA 01568

  Last Sold Summary

  • 17 Days On Market

  Last Listing Agent Caroline Caira RE/MAX On the Charles
• 

  

  

  /37

  $495,000

  Open Fri 5PM - 6:30PM

  • 3 Beds
  • 1 Bath
  • 1,080 Sq Ft

  4 Picadilly St, Upton, MA 01568

  Welcome to this 3-bedroom split-level home offering a wonderful opportunity to build equity and create the home you’ve always envisioned. The main level features a bright living room, a spacious eat-in kitchen with access to the rear deck, and three comfortable bedrooms. The finished lower-level family room provides additional living space ideal for a playroom, home office, media room, or gym. An

  

  Robyn Nasuti

  Realty ONE Group Suburban Lifestyle

  4 Picadilly St, Upton, MA 01568
• 

  

  /27

  $2,600 Per Month

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Apartment for Rent

  5 W Main St Unit 4, Upton, MA 01568

  Super clean, nicely updated, in town apartment in a four family, ready for occupancy. First floor offers a fully applianced kitchen, complete with microwave, refrigerator, dishwasher, and gas stove. Good size dining room and living room each with hardwood flooring, and a full bath with tub. Carpeted Second floor is offers two good size bedrooms and a full bath with walk in shower and your own

  Jeanne Leombruno Century 21 Custom Home Realty

  5 W Main St Unit 4, Upton, MA 01568
• 

  

  /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 $1,039,484

  Last Listing Agent David Hill Central MA Homes

  154 South St, Upton, MA 01568
• 

  

  /42

  Est $832,287

  Not Listed For Sale

  290 Westboro Rd, Upton, MA 01568

  • 4 Beds
  • 3.5 Baths
  • 2,774 Sq Ft
  • Built 1986

  290 Westboro Rd, Upton, MA 01568

  Last Sold Summary

  • 66 Days On Market

  Last Listing Agent Paul Clifford The Neighborhood Realty Group
• 

  

  /42

  $765,000

  Pending

  • 4 Beds
  • 3 Baths
  • 3,018 Sq Ft

  1 South St, Upton, MA 01568

  Welcome home to this distinctive four-bedroom property set on a picturesque 1.84-acre lot, offering the perfect blend of charm, space, and modern updates. Enjoy peaceful mornings on the inviting farmer’s porch or unwind on the stunning new patio while taking in beautiful sunset views. Inside, this home is anything but ordinary, featuring hardwood floors, a flexible first-floor bedroom, and a

  

  Robyn Nasuti

  Realty ONE Group Suburban Lifestyle

  1 South St, 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
• 

  

  /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
• 

  

  /39

  Est $863,717

  Not Listed For Sale

  244 North St, Upton, MA 01568

  • 4 Beds
  • 2.5 Baths
  • 2,426 Sq Ft
  • Built 2002

  244 North St, Upton, MA 01568

  Last Sold Summary

  • 7 Days On Market

  Last Listing Agent Team ROVI Real Broker MA, LLC
• 

  

  /38

  $420,000

  $30K PRICE DROP Pending

  • 3 Beds
  • 1 Bath
  • 1,727 Sq Ft

  5 Pleasant St, Upton, MA 01568

  Bring your vision and unlock the potential of this classic Colonial set on a beautiful, level lot in desirable Upton! Offering a rare combination of major exterior updates and room to build instant equity, this home is the perfect opportunity for investors, contractors, or buyers eager to create their dream home. Significant improvements have already been completed including 9 year old vinyl

  

  Robyn Nasuti

  Realty ONE Group Suburban Lifestyle

  5 Pleasant St, Upton, MA 01568
• 

  

  /36

  $3,300 Per Month

  • 3 Beds
  • 2.5 Baths
  • 1,900 Sq Ft
  • House for Rent

  14 Depot St, Upton, MA 01568

  Spacious three bedroom colonial for rent. Smaller yard with nice deck. Quiet side street just outside out of town with great access to schools, shopping, major routes, ECT. Unfinished basement great for gym set up or storage. Fully applianced with washer/dryer/refrigerator/Dishwasher/Microwave. Hardwood flooring throughout. Nicely updated kitchen with center island. Primary bedroom with TWO large

  Jeanne Leombruno Century 21 Custom Home Realty

  14 Depot St, 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
• 

  

  /27

  Not Listed For Sale

  16 Rawson Farm Rd, Mendon, MA 01756

  • 4 Beds
  • 2.5 Baths
  • 2,884 Sq Ft
  • Built 2025

  16 Rawson Farm Rd, Mendon, MA 01756

  Last Sold Summary

  • 230 Days On Market

  Last Listing Agent Gary Smith Mendon Area Real Estate
• 

  

  /42

  $1,300,000

  Pending

  • 4 Beds
  • 2.5 Baths
  • 3,570 Sq Ft

  27 W River St, Upton, MA 01568

  Modern farmhouse-inspired luxury meets exceptional craftsmanship in this stunning custom-built ranch set on 4.8 private acres. Designed for effortless single-level living, this one-of-a-kind home offers an open-concept floor plan filled with natural light from oversized windows and accented by gleaming hardwood floors throughout the main living areas. The sleek chef’s kitchen features tall custom

  

  Robyn Nasuti

  Realty ONE Group Suburban Lifestyle

  27 W River 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 $637,001

  Last Listing Agent Megan Tolland Realty Executives Boston West

  20 Fiske Ave, Upton, MA 01568
• 

  

  /18

  Est $501,776

  Not Listed For Sale

  140 Main St Unit A, Upton, MA 01568

  • 3 Beds
  • 2.5 Baths
  • 1,485 Sq Ft
  • Built 2020

  140 Main St Unit A, Upton, MA 01568

  Last Sold Summary

  • 46 Days On Market

  Last Listing Agent Diane Luong RE/MAX Vision
• 

  

  /42

  $699,000

  $16K PRICE DROP Pending

  • 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
• 

  

  /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
• 

  

  /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
• 

  

  /34

  $799,000

  Open Fri 1PM - 3PM

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

  21 Boot Shop Rd Unit 21, Upton, MA 01568

  Are you looking for low-maintenance single-level living in a thoughtfully designed new construction condo located in an amazing 55+ community? Come check out the "Starling" floor plan at Cobbler's Creek, built by exceptional builders with a reputation for excellence. As you step inside, you're welcomed by an open and airy floor plan that seamlessly connects the sunny living room, dining room &

  

  Jeffrey Germagian

  ERA Key Realty Services-Bay State Group

  21 Boot Shop Rd Unit 21, 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
• 

  

  /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
• 

  

  /31

  $484,900

  $15K PRICE DROP

  • 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
• 

  

  /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
• 

  

  /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
• 

  

  /23

  $749,900

  Open Fri 1PM - 3PM

  • 2 Beds
  • 2.5 Baths
  • 2,245 Sq Ft

  19 Boot Shop Rd Unit 19, Upton, MA 01568

  Welcome to the fabulous free-standing Blue Bird Model at Cobbler's Creek! Enjoy a distinctive townhouse with 2,200+ square feet of great space easily adaptable to your decor & lifestyle. From a welcoming front porch, enter a foyer with custom moldings & closet open to a spacious open floor plan including a living room & door to a deck, dining area & stylish kitchen w/white cabinets, Quartz

  

  Jeffrey Germagian

  ERA Key Realty Services-Bay State Group

  19 Boot Shop Rd Unit 19, 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
• 

  

  /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
• 

  

  /41

  $855,900

  Open Fri 1PM - 3PM

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

  7 Boot Shop Rd Unit 7, Upton, MA 01568

  Come see what's new 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 two-story living with everything you need handy on the first floor such as a covered front porch, foyer, powder room,

  The Kattman Team ERA Key Realty Services-Bay State Group

  7 Boot Shop Rd Unit 7, Upton, MA 01568
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /39

  $1,050,000

  Sold Jun 22, 2026

  179 South St, Upton, MA 01568

  • 3 Beds
  • 2.5 Baths
  • 3,237 Sq Ft
  • Built 1989

  Last Sold Summary

  • 5% Above List Price
  • $324/SF
  • 4 Days On Market

  Current Estimated Value $1,035,038

  Last Listing Agent Rich Hills Media Realty Group Inc.

  179 South 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.
• 

  

  /41

  $675,000

  Pending

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

  236 Mendon St, Upton, MA 01568

  The charm of yesteryear with moden conveniences. This meticulously maintained and updated 3 bed, 1.5 bath Antique home has been loved by same family for 93 years and is now looking for the next family to welcome home. Pride of ownership shows in custom laid hardwoods and buit-ins. Light-filled large rooms, 4 working fireplaces in the living room, first-floor bedroom, and two upstairs bedrooms.

  Laura Hebb ERA Key Realty Services

  236 Mendon St, Upton, MA 01568
• 

  

  /37

  $900,000

  Sold May 21, 2026

  68 Pearl St, Upton, MA 01568

  • 4 Beds
  • 3.5 Baths
  • 2,472 Sq Ft
  • Built 1968

  Last Sold Summary

  • $364/SF
  • 4 Days On Market

  Current Estimated Value $894,658

  Last Listing Agent Laura Hebb ERA Key Realty Services

  68 Pearl St, 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

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