Upton, MA Homes

• 

  

  

  /19

  $8,100,000

  • 46 Beds
  • 34 Baths
  • 22,233 Sq Ft

  135 Main St, Upton, MA 01568

  135 Main St contains 34 units comprised of (22) 1-Bed/1-Bath units and (12) 2-Bed/1-Bath units. The Property, previously known as The Upton Inn, has undergone significant renovations since its acquisition in August of 2024. This has included renovations of most units including new kitchens and bathrooms with condo quality finishes, updated flooring and painting of the units’ interiors. 135 Main

  Kelleher - Pentore Team Horvath & Tremblay

  135 Main St, Upton, MA 01568
• Selling your home? Sell it faster and for more with a Homes.com Boost.

  Learn More
• 

  

  

  /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

  Last Listing Agent The Arienti Group REMAX Executive Realty

  47 Fiske Mill Rd, Upton, MA 01568
• 

  

  

  /28

  Est $539,702 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 1,731 Sq Ft

  39 Knowlton Cir, Upton, MA 01568

  39 Knowlton Cir, Upton, MA 01568
• 

  

  

  /31

  $750,000

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

  27 James Rd Unit 2, Upton, MA 01568

  SEE THIS GREAT NEW CONSTRUCTION. This home is 3 Bedroom, 3 1/2 bath, with an open first floor plan kitchen is spacious with eat in dining area, hardwood floors, water fall granite kitchen island, stainless steel kitchen appliances, Opens to a family room with balcony to private wooded backyard, 3 large bedrooms including an ensuite primary with tiled shower and glass enclosure with double vanity

  Kim Kimball Kimball Property Realty Inc.

  27 James Rd Unit 2, Upton, MA 01568
• 

  

  

  /42

  $735,000 Sold Apr 30, 2025

  80 Shannon Way Unit 80, Upton, MA 01568

  • 2 Beds
  • 2.5 Baths
  • 2,160 Sq Ft
  • Built 2022

  Last Sold Summary

  • $340/SF
  • 3 Days On Market

  Last Listing Agent Team Metrowest Berkshire Hathaway HomeServices Commonwealth Real Estate

  80 Shannon Way Unit 80, Upton, MA 01568
• 

  

  /29

  Est $760,329 Not Listed For Sale

  • 6 Beds
  • 1.5 Baths
  • 3,218 Sq Ft

  100 Main St, Upton, MA 01568

  100 Main St, Upton, MA 01568
• 

  

  /37

  $929,900

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

  68 Pearl St, Upton, MA 01568

  Motivated seller says be home for the holidays! Stunning Modern 4-bedroom, 3.5-bath masterpiece has been completely transformed from top to bottom .Perfect for multi-generational living!! Featuring an ope layout, designer finishes, and abundant natural light ~ every detail has been carefully curated for style and comfort. The multi-level design offers versatile living spaces perfect for

  Laura Hebb ERA Key Realty Services

  68 Pearl St, Upton, MA 01568
• 

  

  /40

  $1,195,000 Sold Jul 31, 2025

  12 Stoddard St, Upton, MA 01568

  • 4 Beds
  • 4.5 Baths
  • 5,202 Sq Ft
  • Built 2025

  Last Sold Summary

  • $230/SF
  • 14 Days On Market

  Current Estimated Value $1,218,511

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

  12 Stoddard St, Upton, MA 01568
• 

  

  /6

  Est $380,936 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 816 Sq Ft

  52 Pleasant St, Upton, MA 01568

  52 Pleasant St, Upton, MA 01568
• 

  

  /10

  $1,550,000

  • 5 Beds
  • 3.5 Baths
  • 3,568 Sq Ft

  6 Sawmill Brook Ln, Upton, MA 01568

  A timeless New England farmhouse-style under construction on Lot 2, sitting on 4.3 scenic acres & offering 3,586 square feet of living space. Facing east, the home is perfectly positioned to capture fantastic sunrises—best enjoyed from the inviting farmer’s porch, which adds curb appeal & serves as the perfect place to start your day w/ a morning coffee or unwind in the evening. Designed for

  Team Metrowest Berkshire Hathaway HomeServices Commonwealth Real Estate

  6 Sawmill Brook Ln, Upton, MA 01568
• 

  

  /31

  $555,000 Sold Dec 27, 2024

  165 W River St, Upton, MA 01568

  • 3 Beds
  • 2.5 Baths
  • 1,680 Sq Ft
  • Built 1989

  Last Sold Summary

  • $330/SF
  • 15 Days On Market

  Current Estimated Value $572,418

  Last Listing Agent Bruce Bisbee Redfin Corp.

  165 W River St, Upton, MA 01568
• 

  

  /36

  Est $456,680 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,520 Sq Ft

  21 Maple Ave, Upton, MA 01568

  21 Maple Ave, Upton, MA 01568
• 

  /2

  $350,000

  • Land
  • 4.5 Acres
  • $77,778 per Acre

  5 Sawmill Brook Ln, Upton, MA 01568

  Incredible and rare opportunity to build your dream home on a stunning 4.5 acre lot in the new Sawmill Brook Lane subdivision. Work with a highly respected local builder, to create your custom luxury home. This fully approved subdivision includes completed road access, utilities, and approvals for a home of up to 6 bedrooms. Choose from available home plans or bring your own design. Don’t miss

  Team Metrowest Berkshire Hathaway HomeServices Commonwealth Real Estate

  5 Sawmill Brook Ln, Upton, MA 01568
• 

  

  /42

  $775,000 Sold Aug 11, 2025

  290 Westboro Rd, Upton, MA 01568

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

  Last Sold Summary

  • 3% Below List Price
  • $279/SF
  • 66 Days On Market

  Current Estimated Value $777,346

  Last Listing Agent Paul Clifford The Neighborhood Realty Group

  290 Westboro Rd, Upton, MA 01568
• 

  

  /42

  Est $480,794 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,532 Sq Ft

  13 Maple Ave, Upton, MA 01568

  13 Maple Ave, Upton, MA 01568
• 

  

  /28

  $855,900 Open Sun 11AM - 3PM

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

  5 Boot Shop Rd Unit 31, Upton, MA 01568

  Introducing Cobblers Creek, a new 55+ community of detached condominiums from Black Brook Realty. This serene neighborhood is hidden within the viridian tree line yet easily accessible to the Mass Pike in Westborough and Route 495 in Hopkinton. Designed for active adults, Cobblers Creek is a collection of two-bedroom floorplans, including single-level and townhome styles. Our Starling single

  StreamLine Communities Streamline Communities - Upton

  5 Boot Shop Rd Unit 31, 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

  Last Listing Agent Jeanne Leombruno Century 21 Custom Home Realty

  10 Prospect St, Upton, MA 01568
• 

  

  /40

  Est $434,422 Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 2,082 Sq Ft

  4 Hartford Ave S, Upton, MA 01568

  4 Hartford Ave S, Upton, MA 01568
• 

  

  /28

  $739,900 Open Sun 11AM - 3PM

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

  15 Shoemaker Ln Unit 7, Upton, MA 01568

  Introducing Cobblers Creek, a new 55+ community of detached condominiums from Black Brook Realty. This serene neighborhood is hidden within the viridian tree line yet easily accessible to the Mass Pike in Westborough and Route 495 in Hopkinton. Designed for active adults, Cobblers Creek is a collection of two-bedroom floorplans, including single-level and townhome styles. Our Bluebird townhome

  StreamLine Communities Streamline Communities - Upton

  15 Shoemaker Ln Unit 7, Upton, MA 01568
• 

  

  /10

  $317,500 Sold Jun 27, 2025

  Lot B Kiwanis Beach Rd, Upton, MA 01568

  • Land
  • 3.11 Acres
  • $102,090 per Acre

  Last Sold Summary

  • 2% Below List Price
  • 15 Days On Market

  Last Listing Agent Justin Jarboe Keller Williams Pinnacle Central

  Lot B Kiwanis Beach Rd, Upton, MA 01568
• 

  

  /37

  Est $385,848 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,712 Sq Ft

  124 Main St, Upton, MA 01568

  124 Main St, Upton, MA 01568
• 

  

  /39

  $499,900 Pending

  • 2 Beds
  • 1 Bath
  • 1,120 Sq Ft

  49 Grove St, Upton, MA 01568

  Welcome to this beautifully renovated Garrison set on a spacious, picturesque lot in Upton. Updated in 2018, this home features dark walnut hardwood flooring, an updated kitchen with granite countertops, and modern finishes throughout. Major improvements include the 2018 roof, vinyl siding, and windows, offering efficiency and peace of mind. The oversized 2-car garage is a standout, with an

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

  49 Grove 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

  Last Listing Agent Alissa Tosches Lamacchia Realty, Inc.

  26 Brooks St, Upton, MA 01568
• 

  

  /31

  Est $507,374 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,220 Sq Ft

  15 Pleasant St, Upton, MA 01568

  15 Pleasant St, Upton, MA 01568
• 

  

  /28

  $859,900 Pending

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

  16 Boot Shop Rd Unit 39, Upton, MA 01568

  Introducing Cobblers Creek, a new 55+ community of detached condominiums from Black Brook Realty. This serene neighborhood is hidden within the viridian tree line yet easily accessible to the Mass Pike in Westborough and Route 495 in Hopkinton. Designed for active adults, Cobblers Creek is a collection of two-bedroom floorplans, including single-level and townhome styles. Our Starling single

  StreamLine Communities Streamline Communities - Upton

  16 Boot Shop Rd Unit 39, 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
• 

  

  /36

  Est $651,810 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,000 Sq Ft

  29 Pleasant St, Upton, MA 01568

  29 Pleasant St, Upton, MA 01568
• 

  

  /27

  $675,000

  • 3 Beds
  • 2.5 Baths
  • 1,728 Sq Ft

  13 Plain St, Upton, MA 01568

  PREPARE TO FALL IN LOVE! Relocating Executive Seller is sad to leave this meticulously maintained DREAM home, loaded with UPDATES throughout, including a BRAND NEW HEATING SYSTEM! Plus a private, FENCED & FLAT backyard! Step inside to an inviting OPEN CONCEPT floorplan, with beautiful BRAND NEW FLOORING & an abundance of natural light throughout. A large kitchen offers plenty of space for the

  The Tabassi Team RE/MAX Partners Relocation

  13 Plain St, Upton, MA 01568
• 

  

  /26

  $530,000 Sold May 23, 2025

  79 Fowler St, Upton, MA 01568

  • 5 Beds
  • 2 Baths
  • 1,600 Sq Ft
  • Built 1973

  Last Sold Summary

  • 13% Below List Price
  • $331/SF
  • 197 Days On Market

  Current Estimated Value $548,224

  Last Listing Agent Allison Atwood Mendon Local Realty

  79 Fowler St, Upton, MA 01568
• 

  

  /36

  Est $565,780 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,932 Sq Ft

  31 Pleasant St, Upton, MA 01568

  31 Pleasant St, Upton, MA 01568
• 

  

  /35

  $700,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 2,276 Sq Ft

  4 Jonathans Way, Upton, MA 01568

  Nestled in a sought-after Upton location, this classic 3-bed, 2.5-bath Colonial is ready for its next owners. The 1st floor greets you w/ a cozy living room featuring HW floors & a fireplace, perfect for chilly New England evenings. The well appointed kitchen boasts SS appliances, gas cooking, a dining area, & a slider leading to a delightful 3-season room. A formal dining room & a family room

  Andrew Bruce Lamacchia Realty, Inc.

  4 Jonathans Way, Upton, MA 01568
• 

  

  /28

  $389,000 Sold Aug 29, 2025

  120 High St, Upton, MA 01568

  • 3 Beds
  • 1 Bath
  • 913 Sq Ft
  • Built 1875

  Last Sold Summary

  • 3% Below List Price
  • $426/SF
  • 46 Days On Market

  Current Estimated Value $391,980

  Last Listing Agent Clifton LaPorte Berkshire Hathaway HomeServices Commonwealth Real Estate

  120 High St, Upton, MA 01568
• 

  

  /41

  Est $545,548 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,789 Sq Ft

  21 Warren Rd, Upton, MA 01568

  21 Warren Rd, Upton, MA 01568
• 

  

  /42

  $899,999 Pending

  • 4 Beds
  • 2.5 Baths
  • 3,454 Sq Ft

  1 Jonathans Way, Upton, MA 01568

  Nestled on a beautifully landscaped acre with forest views and stunning sunsets, this move-in-ready home offers a perfect blend of comfort and charm. Located in a desirable development near Upton State Forest with no HOA, it features a welcoming wraparound porch, cathedral ceilings in the great room and sunroom, with oversized bedrooms & 4 walk-in closets. Hidden butler’s pantry is a true gem.

  Shelly Armstrong Redfin Corp.

  1 Jonathans Way, Upton, MA 01568
• 

  

  /12

  $404,000 Sold May 12, 2025

  51 School St Unit 2, Upton, MA 01568

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

  Last Sold Summary

  • 1% Above List Price
  • $285/SF
  • 5 Days On Market

  Last Listing Agent Daniel DiBiasio DiBiasio Realty LLC

  51 School St Unit 2, Upton, MA 01568
• 

  

  /42

  Est $675,774 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,150 Sq Ft

  24 Warren Rd, Upton, MA 01568

  24 Warren Rd, Upton, MA 01568
• 

  

  /11

  $350,000

  • 2 Beds
  • 1 Bath
  • 1,058 Sq Ft

  3 Driscoll Ln, Upton, MA 01568

  Step into the warmth and character of this two bedroom antique home built in 1890. You'll love the gleaming hardwood floors, updated heating system, and a screened front porch entry. The home's layout provides cozy yet functional living space, with plenty of natural light. Driveway behind the house. Located just minutes to route 495. This Upton home is a must see!

  Heather McKeon Mawn Lamacchia Realty, Inc.

  3 Driscoll Ln, 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 $661,272 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,792 Sq Ft

  4 Hazeltine Rd, Upton, MA 01568

  4 Hazeltine Rd, Upton, MA 01568
• 

  /2

  $1,206,281 Pending

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

  29 Cider Mill Ln, Upton, MA 01568

  Tucked away on a spacious lot in desirable Upton, this newly built home showcases expert craftsmanship by a seasoned local developer. Offering 3,314 square feet of thoughtfully designed living space, the open floor plan seamlessly blends comfort and style, perfect for today’s modern lifestyle. At the heart of the home, an expansive chef’s kitchen connects the dining and living areas, ideal for

  Melissa Tempesta Whitewood Real Estate, Inc.

  29 Cider Mill Ln, Upton, MA 01568

Showing Results 41 - 80, Page 2 of 18