Upton, MA Homes

• 

  

  

  /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
• 

  

  

  /42

  Est $1,183,091

  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

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

  

  

  /42

  $649,900

  Open Wed 4:30PM - 6:30PM

  • 3 Beds
  • 1.5 Baths
  • 1,806 Sq Ft

  4 Florence Cir, Upton, MA 01568

  Welcome to this charming 3-bedroom, 1.5-bath Colonial ideally situated in a desirable neighborhood with an unbeatable in-town location. Just moments from the local High School and Vocational School, the home offers convenient access to the schools' expansive fields for recreation, walking, track and outdoor activities. Inside, the main level features a bright, open kitchen and dining area that

  Team Metrowest Berkshire Hathaway HomeServices Commonwealth Real Estate

  4 Florence Cir, 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
• 

  

  

  /40

  Est $985,606

  Not Listed For Sale

  8 Miscoe Hill Rd, Upton, MA 01568

  • 4 Beds
  • 2.5 Baths
  • 2,856 Sq Ft
  • Built 2000

  8 Miscoe Hill Rd, Upton, MA 01568

  Last Sold Summary

  • 5 Days On Market

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

  

  /39

  $1,699,000

  $176K PRICE DROP

  • 8 Beds
  • 6 Baths
  • 6,850 Sq Ft

  175 Pleasant St, Upton, MA 01568

  ABSOLUTELY STUNNING. Enormous 8 Bedroom Home with over 6000 square feet of living on 5.5 acres bordering the Shining Rock Golf Course. Privacy abounds on this special property that has been completely updated. Septic System, Roof, Heat/AC, Kitchen, 6 Bathrooms, Windows, Flooring, Well....All NEW. First floor has kitchen, dining room, TWO front to back family/living rooms, full bath, pantry and an

  Matthew Sousa Bullseye Realty Group

  175 Pleasant St, Upton, MA 01568
• 

  

  /23

  $460,000

  Sold Aug 18, 2026

  324 Mendon St, Upton, MA 01568

  • 4 Beds
  • 2.5 Baths
  • 2,340 Sq Ft
  • Built 1979

  Last Sold Summary

  • 15% Above List Price
  • $197/SF
  • 4 Days On Market

  Current Estimated Value $782,081

  Last Listing Agent Marilyn Green RE/MAX Signature Properties

  324 Mendon St, Upton, MA 01568
• 

  

  /40

  Est $758,219

  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

  Last Listing Agent Mike DeLuca Coldwell Banker Realty - Worcester
• 

  

  /42

  $499,000

  Pending

  • 3 Beds
  • 1 Bath
  • 1,316 Sq Ft

  71 School St, Upton, MA 01568

  ***OPEN HOUSE CANCELED***Stunning views with the ability to enjoy time on the water for under $500K. Welcome home to this beautiful single-family ranch in Upton MA across the street from Pratt Pond. Enjoy kayaking, canoeing, boating, and fishing just steps from your front door. This well maintained 3-bedroom 1-bath home sits on a flat 0.75-acre lot perfect for spending time outside entertaining,

  Matthew McLaughlin Premeer Real Estate Inc.

  71 School 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 $1,490,744

  Last Listing Agent Team Metrowest Berkshire Hathaway HomeServices Commonwealth Real Estate

  72 Glenview St, Upton, MA 01568
• 

  

  /31

  Est $646,740

  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

  Last Listing Agent Bruce Bisbee Redfin Corp.
• 

  

  /42

  $650,000

  • 3 Beds
  • 2 Baths
  • 2,055 Sq Ft

  24B River St, Upton, MA 01568

  Imagine summer days spent at nearby Kiwanis Beach and evenings under the stars in your private backyard Jacuzzi. Beautifully maintained home offers an exceptional setting just a short walk from Upton Center, the beach, ballfield and courts, and approximately four miles from the Hopkinton I-495 exit and Price Chopper Plaza. Inside, the open kitchen and family room create a warm, inviting place to

  Katie McBride REMAX Executive Realty

  24B River St, Upton, MA 01568
• 

  

  /41

  $720,000

  Sold Jun 29, 2026

  8 Jackson Dr Unit 8, Upton, MA 01568

  • 2 Beds
  • 3 Baths
  • 2,214 Sq Ft
  • Built 2021

  Last Sold Summary

  • 1% Below List Price
  • $325/SF
  • 16 Days On Market

  Current Estimated Value $714,369

  Last Listing Agent Team Metrowest Berkshire Hathaway HomeServices Commonwealth Real Estate

  8 Jackson Dr Unit 8, Upton, MA 01568
• 

  

  /37

  Est $592,531

  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

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

  

  /33

  $550,000

  Open Sun 12PM - 1:30PM $75K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,548 Sq Ft

  24 Main St, Upton, MA 01568

  Previously relocated owners say it's time to sell! This rare antique in town colonial awaits a new owner. Wait until you see all the character this home exudes. Freshly painted throughout! Bright and sunny layout, hardwood flooring, gorgeous woodwork, nooks and crannies, tin ceilings, built ins, sun filled corner glassed in porch & white picket fence. This is truly a special home. Large dining

  Jeanne Leombruno Century 21 Custom Home Realty

  24 Main St, Upton, MA 01568
• 

  

  /40

  $785,000

  Sold Jul 20, 2026

  20 Josiah Dr, Upton, MA 01568

  • 4 Beds
  • 2.5 Baths
  • 2,408 Sq Ft

  Last Sold Summary

  • 1% Below List Price
  • $326/SF
  • 3 Days On Market

  Current Estimated Value $826,580

  Last Listing Agent Walsh Fine Homes Team eXp Realty LLC

  20 Josiah Dr, Upton, MA 01568
• 

  

  /36

  Est $1,172,570

  Not Listed For Sale

  62 Chestnut St, Upton, MA 01568

  • 4 Beds
  • 3.5 Baths
  • 3,877 Sq Ft
  • Built 1990

  62 Chestnut St, Upton, MA 01568

  Last Sold Summary

  • 16 Days On Market

  Last Listing Agent John Coutinho Berkshire Hathaway HomeServices Commonwealth Real Estate
• 

  

  /3

  $500,000

  $50K PRICE DROP

  • Land
  • 5.45 Acres
  • $91,743 per Acre

  Lot 108 W Main St, Upton, MA 01568

  5.45± acres zoned General Business (GB) located along West Main Street (Route 140) in Upton. This versatile parcel offers strong road frontage, visibility, and flexibility for a variety of commercial, professional, mixed-use, or investment opportunities, subject to Town approvals. The GB zoning district supports a broad range of business and service uses, making this an ideal site for

  John Miller Keller Williams Pinnacle Central

  Lot 108 W Main St, Upton, MA 01568
• 

  

  /3

  $350,000

  Sold Dec 02, 2025

  Lot 1 Sawmill Brook Ln, Upton, MA 01568

  • Land
  • 5.6 Acres
  • $62,500 per Acre

  Last Sold Summary

  • 39 Days On Market

  Last Listing Agent Team Metrowest Berkshire Hathaway HomeServices Commonwealth Real Estate

  Lot 1 Sawmill Brook Ln, Upton, MA 01568
• 

  

  /42

  Est $1,010,865

  Not Listed For Sale

  111 Chestnut St, Upton, MA 01568

  • 3 Beds
  • 2.5 Baths
  • 3,120 Sq Ft
  • Built 1997

  111 Chestnut St, Upton, MA 01568

  Last Sold Summary

  • 66 Days On Market

  Last Listing Agent THE LASH GROUP Keller Williams Boston MetroWest
• 

  

  /42

  $955,000

  $20K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,941 Sq Ft

  161 South St, Upton, MA 01568

  Price Improvement on this truly exceptional Colonial where timeless elegance meets modern comfort. Meticulously maintained and thoughtfully updated, this stunning 4-bedroom, 2.5-bath home offers generous living spaces, 9-foot ceilings, and abundant natural light, creating a warm and inviting atmosphere throughout. The beautifully appointed kitchen is a cook’s dream, featuring upgraded granite

  Laura Hebb ERA Key Realty Services

  161 South St, Upton, MA 01568
• 

  

  /42

  $770,000

  Sold Aug 13, 2026

  1 South St, Upton, MA 01568

  • 4 Beds
  • 3 Baths
  • 3,018 Sq Ft
  • Built 1988

  Last Sold Summary

  • 1% Above List Price
  • $255/SF
  • 6 Days On Market

  Current Estimated Value $733,112

  Last Listing Agent Robyn Nasuti Realty ONE Group Suburban Lifestyle

  1 South St, Upton, MA 01568
• 

  

  /39

  Est $878,932

  Not Listed For Sale

  24 Plumbley Rd, Upton, MA 01568

  • 4 Beds
  • 3 Baths
  • 2,582 Sq Ft
  • Built 1996

  24 Plumbley Rd, Upton, MA 01568

  Last Sold Summary

  • 46 Days On Market

  Last Listing Agent The Highland Group Keller Williams South Watuppa
• 

  

  /24

  $449,000

  • 4 Beds
  • 2 Baths
  • 1,392 Sq Ft

  68 School St, Upton, MA 01568

  Custom built in 1980 for members of a long term, multigenerational Upton family. This expanded ranch will now change hands for the first time! This home features 4 bedrooms and 2 full baths spread out over close to 1,400 sq. ft. Perfectly set off the road on a 25,000+ sq. ft. level lot, this home features a private primary bedroom with its own full bath and jacuzzi tub and direct access to its

  Bill Glanton Berkshire Hathaway HomeServices Stephan Real Estate

  68 School St, Upton, MA 01568
• 

  

  /38

  $420,000

  Sold Aug 14, 2026

  5 Pleasant St, Upton, MA 01568

  • 3 Beds
  • 1 Bath
  • 1,727 Sq Ft
  • Built 1810

  Last Sold Summary

  • 7% Below List Price
  • $243/SF
  • 27 Days On Market

  Current Estimated Value $425,640

  Last Listing Agent Robyn Nasuti Realty ONE Group Suburban Lifestyle

  5 Pleasant St, Upton, MA 01568
• 

  

  /42

  Est $984,031

  Not Listed For Sale

  8 Plumbley Rd, Upton, MA 01568

  • 3 Beds
  • 2.5 Baths
  • 3,623 Sq Ft
  • Built 1992

  8 Plumbley Rd, Upton, MA 01568

  Last Sold Summary

  • 53 Days On Market

  Last Listing Agent Chris Mehr Full Circle Realty LLC
• 

  

  /5

  $499,000

  • 3 Beds
  • 2.5 Baths
  • 3,217 Sq Ft

  15 W Main St, Upton, MA 01568

  After being cherished by the same family for approximately 170 years, 15 West Main Street presents an extraordinary opportunity to become the next steward of a truly special historic property. Known as the Arba Thayer Wood House and Barn, this distinguished homestead was built in 1855 by Arba Thayer Wood and retains the character, craftsmanship, and gracious proportions of a bygone era. Rich with

  Kim Backlund Northeast Realty + Co.

  15 W Main St, Upton, MA 01568
• 

  /2

  $835,000

  Sold Jun 29, 2026

  1 Quail Run, Upton, MA 01568

  • 4 Beds
  • 2.5 Baths
  • 2,610 Sq Ft
  • Built 2002

  Last Sold Summary

  • 5% Above List Price
  • $320/SF
  • 7 Days On Market

  Current Estimated Value $804,902

  Last Listing Agent Robyn Nasuti Realty ONE Group Suburban Lifestyle

  1 Quail Run, Upton, MA 01568
• 

  

  /41

  Est $919,590

  Not Listed For Sale

  41 South St, Upton, MA 01568

  • 4 Beds
  • 2.5 Baths
  • 2,630 Sq Ft
  • Built 1992

  41 South St, Upton, MA 01568

  Last Sold Summary

  • 5 Days On Market

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

  

  /41

  $1,199,900

  $100K PRICE DROP

  • 4 Beds
  • 4.5 Baths
  • 3,543 Sq Ft

  8 Juniper Rd, Upton, MA 01568

  LOWER YOUR RATE BY UP TO 3% @ SELLERS SOLE COST!!! Welcome to 8 Juniper Road, where impressive space, thoughtful updates, and a truly spectacular backyard oasis come together in one exceptional home. Offering approximately 3,600 sq. ft. of living space, 4 bedrooms, 4.5 bathrooms, and a 3-car garage, this beautifully maintained and updated property is designed for both comfortable everyday living

  Amy Bisson Lamacchia Realty, Inc.

  8 Juniper Rd, Upton, MA 01568
• 

  

  /42

  $1,100,000

  Sold Jun 26, 2026

  46 Rockwood Ln Unit 46, Upton, MA 01568

  • 2 Beds
  • 3.5 Baths
  • 3,925 Sq Ft
  • Built 2018

  Last Sold Summary

  • 2% Above List Price
  • $280/SF
  • 7 Days On Market

  Last Listing Agent Bill Gassett REMAX Executive Realty

  46 Rockwood Ln Unit 46, Upton, MA 01568
• 

  

  /42

  Est $1,267,946

  Not Listed For Sale

  68 Glenview St, Upton, MA 01568

  • 4 Beds
  • 2.5 Baths
  • 4,875 Sq Ft
  • Built 2003

  68 Glenview St, Upton, MA 01568

  Last Sold Summary

  • 1 Day On Market

  Last Listing Agent Lisa Aron Williams Coldwell Banker Realty - Sudbury
• 

  

  /42

  $1,075,000

  $75K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,924 Sq Ft

  32 Mendon St, Upton, MA 01568

  32 Mendon St, Upton, MA. Where modern sophistication meets timeless design. This newly constructed 2026 residence offers 2,924 square feet of impeccably curated living space, blending contemporary elegance with refined modern farmhouse architecture. Every detail has been intentionally selected — from premium finishes to elevated craftsmanship — creating a home that feels both luxurious and

  Luana Velame Century 21 The Real Estate Group

  32 Mendon St, Upton, MA 01568
• 

  

  /20

  $952,500

  Sold Oct 31, 2025

  17 Old Grafton Rd, Upton, MA 01568

  • 4 Beds
  • 2.5 Baths
  • 2,770 Sq Ft
  • Built 2025

  Last Sold Summary

  • 1% Above List Price
  • $344/SF
  • 68 Days On Market

  Last Listing Agent Kim Backlund Northeast Realty + Co.

  17 Old Grafton Rd, Upton, MA 01568
• 

  

  /25

  Est $779,807

  Not Listed For Sale

  30 Glenview St, Upton, MA 01568

  • 3 Beds
  • 2.5 Baths
  • 2,127 Sq Ft
  • Built 1986

  30 Glenview St, Upton, MA 01568

  Last Sold Summary

  • 25 Days On Market

  Last Listing Agent Anne Oakman Media Realty Group Inc.
• 

  

  /42

  $439,500

  Sold May 08, 2026

  6 Fieldstone Dr Unit 6, Upton, MA 01568

  • 2 Beds
  • 1.5 Baths
  • 2,229 Sq Ft
  • Built 1987

  Last Sold Summary

  • $197/SF
  • 39 Days On Market

  Last Listing Agent Robyn Nasuti Realty ONE Group Suburban Lifestyle

  6 Fieldstone Dr Unit 6, Upton, MA 01568
• 

  

  /39

  Est $854,248

  Not Listed For Sale

  1 Centerbrook Way, Upton, MA 01568

  • 4 Beds
  • 2.5 Baths
  • 2,660 Sq Ft
  • Built 1996

  1 Centerbrook Way, Upton, MA 01568

  Last Sold Summary

  • 6 Days On Market

  Last Listing Agent Sara Furtado Remax Revolution
• 

  

  /28

  $439,900

  Sold Oct 02, 2025

  16 Fieldstone St Unit 16, Upton, MA 01568

  • 2 Beds
  • 1.5 Baths
  • 1,699 Sq Ft
  • Built 1987

  Last Sold Summary

  • $259/SF
  • 26 Days On Market

  Current Estimated Value $443,702

  Last Listing Agent Karole O'Leary Lamacchia Realty, Inc.

  16 Fieldstone St Unit 16, Upton, MA 01568
• 

  

  /41

  Est $1,082,927

  Not Listed For Sale

  44 W River St, Upton, MA 01568

  • 4 Beds
  • 3.5 Baths
  • 3,514 Sq Ft
  • Built 1988

  44 W River St, Upton, MA 01568

  Last Sold Summary

  • 9 Days On Market

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

  

  /11

  $505,000

  Sold Sep 29, 2025

  10 Mendon St, Upton, MA 01568

  • 3 Beds
  • 2 Baths
  • 1,440 Sq Ft
  • Built 1993

  Last Sold Summary

  • 1% Above List Price
  • $351/SF
  • 74 Days On Market

  Current Estimated Value $551,596

  Last Listing Agent Nathan Clark Your Home Sold Guaranteed Realty, The Nathan Clark Team

  10 Mendon St, Upton, MA 01568

Showing Results 121 - 160, Page 4 of 18