Upton, MA Homes

• 

  

  

  /37

  $669,000

  $56K 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
• 

  

  

  /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
• 

  

  

  /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
• 

  

  

  /41

  $549,000

  $50K 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
• 

  

  

  /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
• 

  

  /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
• 

  

  /28

  $799,000

  Pending

  • 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
• 

  

  /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
• 

  

  /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.
• 

  

  /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
• 

  

  /37

  $910,000

  Sold Aug 14, 2026

  145 W River St, Upton, MA 01568

  • 4 Beds
  • 2.5 Baths
  • 3,956 Sq Ft
  • Built 1973

  Last Sold Summary

  • 3% Below List Price
  • $230/SF
  • 21 Days On Market

  Current Estimated Value $925,313

  Last Listing Agent Mia Fisher Berkshire Hathaway HomeServices Commonwealth Real Estate

  145 W River 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

  $1,099,000

  Open Sun 11AM - 1PM

  • 4 Beds
  • 2.5 Baths
  • 4,146 Sq Ft

  32 Howarth Dr, Upton, MA 01568

  Located in the exclusive Glen Echo Estates community in Upton, this impressive 2008-built Colonial showcases an ideal lot & yard all within a tranquil neighborhood setting. As you move inside the home, you are greeted by a regal two-story foyer, which receives fantastic morning sunlight via an Eastern Exposure. The sunlight reflects beautifully off the oak hardwood floors that extend throughout

  Brian Connelly Redfin Corp.

  32 Howarth Dr, 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
• 

  

  /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
• 

  

  /41

  $1,125,000

  $74K PRICE DROP Pending

  • 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
• 

  /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 $898,075

  Last Listing Agent Deb Kotlarz Keller Williams Realty Boston Northwest

  49 Warren St, 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
• 

  

  /39

  $649,900

  $25K PRICE DROP Pending

  • 4 Beds
  • 2 Baths
  • 2,534 Sq Ft

  90 Glenview St, Upton, MA 01568

  Price improvement by motivated seller ~ New 4-Bed Septic being installed! Fabulous Turn-Key Cape home has a number of custom touches not found in new construction. Home has had major systems updated in the last two years: Viessmann 42-gallon indirect hot water heater, highly-efficient Williamson boiler, new well pump & piping ~ all with long-term warranties. All appliances less than 2 years

  Laura Hebb ERA Key Realty Services

  90 Glenview St, 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
• 

  

  /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

  $919,900

  $30K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 3,100 Sq Ft

  33 Milford St, Upton, MA 01568

  Stunning fully renovated luxury home offering three finished levels of sophisticated living with high-end finishes and designer details throughout. This turnkey home features an open-concept floor plan, a custom chef's kitchen with premium appliances, spa-inspired bathrooms, modern lighting, and beautifully updated living spaces. Thoughtfully renovated with exceptional craftsmanship, it

  Wendy Solano Lamacchia Realty, Inc.

  33 Milford 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 $604,232

  Last Listing Agent Jennifer French REMAX Executive Realty

  26 Fowler St, Upton, MA 01568
• 

  

  /30

  Est $1,011,159

  Not Listed For Sale

  177 South St, Upton, MA 01568

  • 4 Beds
  • 5 Baths
  • 4,815 Sq Ft
  • Built 1987

  177 South St, Upton, MA 01568

  Last Sold Summary

  • 50 Days On Market

  Last Listing Agent Brian Wotton Brian Wotton Realty Inc.
• 

  

  /40

  $849,900

  $30K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 3,132 Sq Ft

  2 Brookside St, Upton, MA 01568

  Stately Colonial offering a rare combination of privacy, natural beauty & modern updates in one exceptional property. Every window captures peaceful views of the surrounding landscape, creating a vacation-at-home feeling year-round. This spacious home features beautiful hardwood floors throughout the 1st floor & a versatile floor plan designed for easy everyday living & entertaining. The stunning

  Leah Burke William Raveis R.E. & Home Services

  2 Brookside St, 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
• 

  

  /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
• 

  

  /40

  $899,000

  • 4 Beds
  • 5 Baths
  • 4,242 Sq Ft

  96 Fowler St, Upton, MA 01568

  Exceptional Colonial on 3.21 Private Acres. Discover the perfect blend of comfort and lifestyle in this exceptional colonial, set on 3.21 acres of stunning, pastoral landscape. Designed to inspire, the home is bathed in natural light and offers breathtaking sunset views—providing the perfect backdrop for working from home. The open-concept floor plan flows seamlessly, featuring a spacious family

  Isaac Alvarenga Property Investors & Advisors, LLC

  96 Fowler 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 $557,079

  Last Listing Agent Lioce Properties Group Lamacchia Realty, Inc.

  43 Knowlton Cir, Upton, MA 01568
• 

  

  /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
• 

  

  /37

  $575,000

  Open Wed 4:30PM - 6PM

  • 3 Beds
  • 1.5 Baths
  • 1,556 Sq Ft

  40 Hartford Ave N, Upton, MA 01568

  Welcome to this charming Colonial Style home, offering warmth, character, and modern comfort throughout. The inviting open floor plan creates a seamless flow between the living, dining, and kitchen areas, making the home feel spacious and welcoming. Beautiful hardwood flooring runs throughout the home. The living room is complemented by a cozy fireplace with an elegant marble surround. The

  Cindy Donati Century 21 Custom Home Realty

  40 Hartford Ave N, Upton, MA 01568
• 

  

  /40

  $1,090,000

  Sold Aug 31, 2026

  6 Wood St, Upton, MA 01568

  • 4 Beds
  • 2.5 Baths
  • 3,260 Sq Ft
  • Built 2003

  Last Sold Summary

  • 3% Below List Price
  • $334/SF
  • 263 Days On Market

  Current Estimated Value $1,054,421

  Last Listing Agent Brittany Palmerino Mathieu Newton Sotheby's International Realty

  6 Wood St, Upton, MA 01568
• 

  

  /23

  Est $480,276

  Not Listed For Sale

  56 Shore Dr, Upton, MA 01568

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

  56 Shore Dr, Upton, MA 01568

  Last Sold Summary

  • 6 Days On Market

  Last Listing Agent Samantha Edwards Prime Time Real Estate Inc.
• 

  

  /38

  $779,900

  Pending

  • 2 Beds
  • 2 Baths
  • 1,743 Sq Ft

  41 Rockwood Ln Unit 41, Upton, MA 01568

  Impressive Like New Freestanding Ranch Home in Highly Sought-After Rockwood Meadows Over 55 Community on The Hopkinton Line Just A Few Miles Away From 495/MA Pike Exits. Premium Lot Which Backs up Conservation Area Offering Miles Hiking, Biking and Running Trails. Features an Open Plan With Gorgeous Cherry Cabinet Kitchen, Granite Counters, Stainless Appliances, Center Island and Access to

  Bill Gassett REMAX Executive Realty

  41 Rockwood Ln Unit 41, 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 $1,114,011

  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
• 

  

  /37

  $599,000

  • 3 Beds
  • 2 Baths
  • 1,496 Sq Ft

  15 North St, Upton, MA 01568

  Discover the perfect blend of timeless character and modern convenience in this spacious 3-bedroom, 2-full-bath home set on more than 3 acres of private, classic grounds complete with traditional stone walls. With generously sized rooms, high ceilings, and a highly livable floor plan, this home offers plenty of space to relax, entertain, and enjoy the best of country living. The recently

  Laura Hebb ERA Key Realty Services

  15 North 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
• 

  

  /42

  Est $1,064,486

  Not Listed For Sale

  158 South St, Upton, MA 01568

  • 4 Beds
  • 4.5 Baths
  • 3,757 Sq Ft
  • Built 1999

  158 South St, Upton, MA 01568

  Last Sold Summary

  • 48 Days On Market

  Last Listing Agent Team Metrowest Berkshire Hathaway HomeServices Commonwealth Real Estate
• 

  

  /42

  $720,000

  $100K PRICE DROP Pending

  • 3 Beds
  • 3 Baths
  • 1,304 Sq Ft

  11 James Rd, Upton, MA 01568

  Upton Horse Haven: Iconic 3-Bed, 3-Bath Retreat on 3.75 Acres. Discover one of Upton’s most beloved properties, a premier estate where timeless charm meets outdoor living. This home features modern upgrades including 200-amp electrical system, a new oil tank, and town water for seamless reliability. A newly finished basement for entertaining or retreat. Property offers direct access to miles of

  Team ROVI Real Broker MA, LLC

  11 James Rd, Upton, MA 01568

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