Upton, MA Homes

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  /42

  $1,350,000 Sold Oct 03, 2025

  5 Azalea Ln, Upton, MA 01568

  • 5 Beds
  • 3.5 Baths
  • 4,647 Sq Ft
  • Built 2016

  Last Sold Summary

  • 4% Above List Price
  • $291/SF
  • 16 Days On Market

  Current Estimated Value $1,330,779

  Last Listing Agent Neil Fredette Keller Williams Realty-Merrimack

  5 Azalea Ln, Upton, MA 01568
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  /40

  Est $529,525 Not Listed For Sale

  2 Breton Rd, Upton, MA 01568

  • 3 Beds
  • 1 Bath
  • 1,614 Sq Ft
  • Built 1985

  2 Breton Rd, Upton, MA 01568

  Last Sold Summary

  • 6% Above List Price
  • $311/SF
  • 12 Days On Market

  Last Sold Price $501,900

  Last Listing Agent Robyn and Sean Sold My House Team Realty ONE Group Suburban Lifestyle
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  /41

  $419,000 Pending

  • 2 Beds
  • 1 Bath
  • 1,536 Sq Ft

  72 Main St, Upton, MA 01568

  72 Main Street in Upton has a whole new look, and it's just waiting for YOU to make it HOME! This ADORABLE, bright and newly renovated 2/3 bed, 1 Bath Ranch will charm you upon entry. You will fall in LOVE with the sweet front porch, the sun-filled living area, the renovated eat-in kitchen with stainless-steel appliances, the brand-new bathroom, and the lovely back deck. But... just WAIT until

  Ryan Wilson Keller Williams Realty

  72 Main St, Upton, MA 01568
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  /24

  $693,000 Sold Jul 09, 2025

  7 Sienna Cir Unit 7, Upton, MA 01568

  • 2 Beds
  • 2 Baths
  • 1,500 Sq Ft
  • Built 2022

  Last Sold Summary

  • 1% Below List Price
  • $462/SF
  • 25 Days On Market

  Last Listing Agent Shelly Armstrong Redfin Corp.

  7 Sienna Cir Unit 7, Upton, MA 01568
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  /27

  Est $553,277 Not Listed For Sale

  12 Knowlton Cir, Upton, MA 01568

  • 3 Beds
  • 2.5 Baths
  • 2,184 Sq Ft
  • Built 2003

  12 Knowlton Cir, Upton, MA 01568

  Last Sold Summary

  • 2% Below List Price
  • $259/SF
  • 4 Days On Market

  Last Sold Price $565,000

  Last Listing Agent Mary Ann Tecce Gibson Sothebys International Realty
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  /2

  $250,000

  • Land
  • 3.19 Acres
  • $78,370 per Acre

  74 Warren St, Upton, MA 01568

  Here's your opportunity to build your dream home in the quaint and serene town of Upton. Over 3 acre wooded lot located on a scenic country road yet close to downtown. Potential to build a home with views of Boston! Zoned for a single family. Perc test done for septic. Per town, public water connection is possible. Excellent access to I-495 and the Mass Pike for commuters. Can be purchased on its

  Melissa Ellison Mathieu Newton Sotheby's International Realty

  74 Warren St, Upton, MA 01568
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  /26

  $875,000 Sold Nov 13, 2025

  95 Crockett Rd, Upton, MA 01568

  • 2 Beds
  • 1 Bath
  • 864 Sq Ft
  • Built 1950

  Last Sold Summary

  • 9% Above List Price
  • $1,013/SF
  • 9 Days On Market

  Current Estimated Value $768,932

  Last Listing Agent Campos Homes RE/MAX Real Estate Center

  95 Crockett Rd, Upton, MA 01568
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  /28

  Est $546,583 Not Listed For Sale

  39 Knowlton Cir, Upton, MA 01568

  • 4 Beds
  • 2.5 Baths
  • 1,731 Sq Ft
  • Built 2003

  39 Knowlton Cir, Upton, MA 01568

  Last Sold Summary

  • 16% Above List Price
  • $272/SF
  • 14 Days On Market

  Last Sold Price $470,000

  Last Listing Agent Alan Yanofsky RE/MAX
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  /31

  $399,900 Pending

  • 2 Beds
  • 1.5 Baths
  • 1,438 Sq Ft

  8 Maple St, Upton, MA 01568

  Nestled at 8 Maple Street, Upton this Ole girl needs a handy homeowner or investor ready to bring their ideas and updates into a property with remarkable potential. Title V Failed - cesspool.(see disclosures) This property is an investment opportunity. Within the dwelling, the 1438 square feet of living space includes Livingroom with a reading nook, Dining room, Kitchen, 2 bedrooms, small room

  June Hillier REMAX Executive Realty

  8 Maple St, Upton, MA 01568
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  /23

  $472,800 Sold Sep 05, 2025

  56 Shore Dr, Upton, MA 01568

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

  Last Sold Summary

  • 5% Below List Price
  • $358/SF
  • 6 Days On Market

  Current Estimated Value $456,909

  Last Listing Agent Samantha Edwards Prime Time Real Estate Inc.

  56 Shore Dr, Upton, MA 01568
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  /29

  Est $742,398 Not Listed For Sale

  100 Main St, Upton, MA 01568

  • 6 Beds
  • 1.5 Baths
  • 3,218 Sq Ft
  • Built 1900

  100 Main St, Upton, MA 01568

  Last Sold Summary

  • 103% Above List Price
  • $114/SF
  • 5 Days On Market

  Last Sold Price $366,466

  Last Listing Agent Custom Home Team Century 21 Custom Home Realty
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  /19

  $7,500,000

  • 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
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  /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

  Current Estimated Value $1,151,808

  Last Listing Agent The Arienti Group REMAX Executive Realty

  47 Fiske Mill Rd, Upton, MA 01568
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  /6

  Est $377,169 Not Listed For Sale

  52 Pleasant St, Upton, MA 01568

  • 2 Beds
  • 2 Baths
  • 816 Sq Ft
  • Built 1952

  52 Pleasant St, Upton, MA 01568

  Last Sold Summary

  • 6% Above List Price
  • $435/SF
  • 127 Days On Market

  Last Sold Price $355,000

  Last Listing Agent James Pham The Carroll Team
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  /40

  $899,900

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

  6 Chickadee Way Unit 23, Upton, MA 01568

  A unique opportunity unfolds at 6 Chickadee Way, Upton, Adult Community 55+ where an attractive condominium in stellar condition stands to invite you in to the comforts of Home! Front porch entry. Popular open floor concept with an expansive 2228 square feet of living area. Livingroom with a fireplace, dining area open to an impressive kitchen layout with custom cabinets, large eat at island,

  June Hillier REMAX Executive Realty

  6 Chickadee Way Unit 23, Upton, MA 01568
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  /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
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  /36

  Est $463,792 Not Listed For Sale

  21 Maple Ave, Upton, MA 01568

  • 3 Beds
  • 2.5 Baths
  • 1,520 Sq Ft
  • Built 2004

  21 Maple Ave, Upton, MA 01568

  Last Sold Summary

  • 19% Above List Price
  • $257/SF
  • 42 Days On Market

  Last Sold Price $390,000

  Last Listing Agent The Jenkins Group Keller Williams Realty
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  /25

  $599,000

  • 5 Beds
  • 3 Baths
  • 2,887 Sq Ft

  130 High St, Upton, MA 01568

  Finishing touches were completed after the photos. 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

  Jacob Greasley eXp Realty

  130 High St, Upton, MA 01568
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  /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 $1,256,090

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

  12 Stoddard St, Upton, MA 01568
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  /42

  Est $451,811 Not Listed For Sale

  13 Maple Ave, Upton, MA 01568

  • 3 Beds
  • 2.5 Baths
  • 1,532 Sq Ft
  • Built 2005

  13 Maple Ave, Upton, MA 01568

  Last Sold Summary

  • 10% Above List Price
  • $268/SF
  • 136 Days On Market

  Last Sold Price $410,000

  Last Listing Agent Robyn Nasuti Realty ONE Group Suburban Lifestyle
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  /28

  $560,000

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

  1 Knowlton Cir Unit 1, Upton, MA 01568

  A rare opportunity to own a four-bedroom, two and a half bath residence in the desirable Samreen Villas. This private end unit offers exceptional natural light and a thoughtfully designed layout ideal for both everyday living and entertaining. The main level features hardwood and ceramic tile flooring, an open-concept kitchen and dining area, and a dramatic living room with soaring ceilings and

  Leah Tringale Longwood Residential, LLC

  1 Knowlton Cir Unit 1, Upton, MA 01568
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  /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 $786,977

  Last Listing Agent Paul Clifford The Neighborhood Realty Group

  290 Westboro Rd, Upton, MA 01568
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  /40

  Est $437,824 Not Listed For Sale

  4 Hartford Ave S, Upton, MA 01568

  • 4 Beds
  • 1.5 Baths
  • 2,082 Sq Ft
  • Built 1860

  4 Hartford Ave S, Upton, MA 01568

  Last Sold Summary

  • 7% Above List Price
  • $197/SF
  • 54 Days On Market

  Last Sold Price $410,000

  Last Listing Agent Laura Hebb ERA Key Realty Services
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  /30

  $499,900 Pending

  • 3 Beds
  • 1.5 Baths
  • 2,182 Sq Ft

  7 Fieldstone Dr Unit 7, Upton, MA 01568

  This meticulously maintained distinguished four level townhome presents an opportunity for refined living. The expansive living area features a remodeled sun-splashed kitchen with granite counters and stainless appliances. Within this generous footprint, 3 dedicated bedrooms with abundant closet space provide individual retreats, with the expansive 3rd bedroom/in-home office w/15 X 8 attic access

  Linda Tolman Andrew J. Abu Inc., REALTORS®

  7 Fieldstone Dr Unit 7, Upton, MA 01568
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  /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 $748,337

  Last Listing Agent Jeanne Leombruno Century 21 Custom Home Realty

  10 Prospect St, Upton, MA 01568
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  /37

  Est $425,182 Not Listed For Sale

  124 Main St, Upton, MA 01568

  • 2 Beds
  • 1.5 Baths
  • 1,712 Sq Ft
  • Built 1828

  124 Main St, Upton, MA 01568

  Last Sold Summary

  • 33% Above List Price
  • $187/SF
  • 12 Days On Market

  Last Sold Price $320,000

  Last Listing Agent Amber Cadorette Keller Williams Elite
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  /42

  $1,500,000 Pending

  • 4 Beds
  • 3.5 Baths
  • 3,586 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
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  /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
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  /31

  Est $499,759 Not Listed For Sale

  15 Pleasant St, Upton, MA 01568

  • 3 Beds
  • 2 Baths
  • 1,220 Sq Ft
  • Built 1970

  15 Pleasant St, Upton, MA 01568

  Last Sold Summary

  • 5% Above List Price
  • $389/SF
  • 3 Days On Market

  Last Sold Price $475,000

  Last Listing Agent Christine Newell LAER Realty Partners
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  /36

  $949,900 Pending

  • 2 Beds
  • 2.5 Baths
  • 2,392 Sq Ft

  63 Rockwood Ln Unit 63, Upton, MA 01568

  Enjoy owning a single family home with all of the benefits of community living! Stunning open first floor includes spacious kitchen with SS appliances, cherry cabinetry and 10 foot island fantastic for entertaining. Living room features gas fireplace, dining room overlooking private back yard, patio and deck. Built in patio table and benches for outside dining. Crown molding throughout the first

  Linda Mossman Realty Executives Boston West

  63 Rockwood Ln Unit 63, Upton, MA 01568
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  /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 $665,269

  Last Listing Agent Alissa Tosches Lamacchia Realty, Inc.

  26 Brooks St, Upton, MA 01568
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  /36

  Est $645,561 Not Listed For Sale

  29 Pleasant St, Upton, MA 01568

  • 3 Beds
  • 2.5 Baths
  • 2,000 Sq Ft
  • Built 1994

  29 Pleasant St, Upton, MA 01568

  Last Sold Summary

  • 17% Above List Price
  • $275/SF
  • 1 Day On Market

  Last Sold Price $550,000

  Last Listing Agent Mark Peris Andrew J. Abu Inc., REALTORS®
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  /28

  $855,900 Open Fri 11AM - 3PM

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

  5 Boot Shop Rd Unit 31, Upton, MA 01568

  Discover townhome living in 5 Boot Shop Road U:31, Upton, MA. 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. Ask about our 20k developer incentive. Designed for active adults, Cobblers Creek is a

  StreamLine Communities Streamline Communities - Upton

  5 Boot Shop Rd Unit 31, Upton, MA 01568
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  /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
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  /36

  Est $550,561 Not Listed For Sale

  31 Pleasant St, Upton, MA 01568

  • 3 Beds
  • 2 Baths
  • 1,932 Sq Ft
  • Built 1969

  31 Pleasant St, Upton, MA 01568

  Last Sold Summary

  • 9% Above List Price
  • $261/SF
  • 6 Days On Market

  Last Sold Price $505,000

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

  

  /28

  $699,900 New Construction

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

  15 Shoemaker Ln Unit 7, Upton, MA 01568

  Discover townhome living in 15 Shoemaker Lane U:7, Upton, MA. 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,

  StreamLine Communities Streamline Communities - Upton

  15 Shoemaker Ln Unit 7, Upton, MA 01568
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  /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 $541,778

  Last Listing Agent Allison Atwood Mendon Local Realty

  79 Fowler St, Upton, MA 01568
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  /42

  Est $675,656 Not Listed For Sale

  24 Warren Rd, Upton, MA 01568

  • 3 Beds
  • 2 Baths
  • 2,150 Sq Ft
  • Built 1967

  24 Warren Rd, Upton, MA 01568

  Last Sold Summary

  • 2% Above List Price
  • $307/SF
  • 6 Days On Market

  Last Sold Price $660,000

  Last Listing Agent Team Metrowest Berkshire Hathaway HomeServices Commonwealth Real Estate
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  /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
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  /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 $390,418

  Last Listing Agent Clifton LaPorte Berkshire Hathaway HomeServices Commonwealth Real Estate

  120 High St, Upton, MA 01568

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