Upton, MA Homes

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  /38

  $850,000

  • 3 Beds
  • 2.5 Baths
  • 3,300 Sq Ft

  215 North St, Upton, MA 01568

  Set at the end of a dead-end road, this expanded custom contemporary offers over 10 acres of private land—a rare blend of space, flexibility, and future potential. This well-maintained 3-bed, 2.5-bath home is filled with natural light from expansive windows and skylights, creating an open, inviting layout. A standout 30x24 heated bonus room above the garage provides exceptional space for

  Campos Homes RE/MAX Real Estate Center

  215 North St, 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 $962,485

  Last Listing Agent Laura Hebb ERA Key Realty Services

  11 East St, Upton, MA 01568
• 

  

  

  /35

  Est $545,119 Not Listed For Sale

  10 Breton Rd, Upton, MA 01568

  • 3 Beds
  • 2 Baths
  • 1,740 Sq Ft
  • Built 1958

  10 Breton Rd, Upton, MA 01568

  Last Sold Summary

  • 5% Below List Price
  • $330/SF
  • 5 Days On Market

  • Last Sold Price $575,000
  • Feb 18, 2025

  Last Listing Agent The Mitchell-Gat Team Berkshire Hathaway HomeServices Page Realty
• 

  

  

  /14

  $1,499,999 New Construction

  • 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
• 

  

  

  /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 $1,360,703

  Last Listing Agent Neil Fredette Keller Williams Realty-Merrimack

  5 Azalea Ln, Upton, MA 01568
• 

  

  /40

  Est $528,932 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

  • 5% Above List Price
  • $311/SF
  • 12 Days On Market

  • Last Sold Price $501,900
  • Nov 21, 2024

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

  

  /40

  $615,000

  • 3 Beds
  • 2 Baths
  • 1,777 Sq Ft

  20 Fiske Ave, Upton, MA 01568

  Meticulously maintained, young split-level home set in a beautiful Upton neighborhood. Light-filled main level features hardwood floors, a vaulted living room with ceiling fan and gas fireplace, and an open kitchen with island seating—ideal for everyday living and entertaining—with a separate space for dining. Step out to a deck overlooking a large, level backyard, perfect for outdoor enjoyment.

  Megan Tolland Realty Executives Boston West

  20 Fiske Ave, Upton, MA 01568
• 

  

  /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
• 

  

  /27

  Est $552,886 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
  • Aug 05, 2024

  Last Listing Agent Mary Ann Tecce Gibson Sothebys International Realty
• 

  

  /31

  $449,900 Pending

  • 2 Beds
  • 1.5 Baths
  • 1,155 Sq Ft

  41 Main St, Upton, MA 01568

  Beautifully updated Cape, rebuilt from the studs in 2007, offering a bright, welcoming interior and flexible layout. The sun-filled living room features hardwood floors and a cozy gas stove (not currently used). A versatile dining room can also serve as additional living space. The kitchen includes ample cabinetry, updated appliances, and access to a covered porch—perfect for relaxing or

  John Herrera Ownit a Real Estate Firm

  41 Main St, Upton, MA 01568
• 

  

  /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 $791,475

  Last Listing Agent Campos Homes RE/MAX Real Estate Center

  95 Crockett Rd, Upton, MA 01568
• 

  

  /28

  Est $542,465 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

  • 15% Above List Price
  • $272/SF
  • 14 Days On Market

  • Last Sold Price $470,000
  • Nov 22, 2023

  Last Listing Agent Alan Yanofsky RE/MAX
• 

  

  /26

  $499,900

  • 3 Beds
  • 2.5 Baths
  • 1,785 Sq Ft

  140 Main St Unit B, Upton, MA 01568

  Situated at 140 Main St U:B in Upton, MA, United States, this condominium represents a contemporary residence crafted in 2020. This property offers a refined living experience within a recently constructed setting, presenting an opportunity for sophisticated comfort. Within its generous layout, discover three private sanctuaries, each offering a tranquil retreat for personal repose and

  Mike Dagilis ERA Key Realty Services- Milf

  140 Main St Unit B, Upton, MA 01568
• 

  

  /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 $471,397

  Last Listing Agent Samantha Edwards Prime Time Real Estate Inc.

  56 Shore Dr, Upton, MA 01568
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  /29

  Est $747,288 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

  • 104% Above List Price
  • $114/SF
  • 5 Days On Market

  • Last Sold Price $366,466
  • Jul 26, 2023

  Last Listing Agent Custom Home Team Century 21 Custom Home Realty
• 

  

  /29

  $447,000

  • 3 Beds
  • 1 Bath
  • 1,140 Sq Ft

  26 Hartford Ave N, Upton, MA 01568

  This charming, meticulously kept three-bedroom residence offers a serene retreat in the heart of sought-after Upton. Curb appeal abounds with a classic farmer's porch and professional landscaping, while the expansive composite deck provides a premier setting for outdoor gatherings within the lush, private yard. Inside, the home stays warm and inviting thanks to a cozy gas fireplace and efficient

  Scott Driscoll Redfin Corp.

  26 Hartford Ave N, Upton, MA 01568
• 

  

  /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 $1,165,707

  Last Listing Agent The Arienti Group REMAX Executive Realty

  47 Fiske Mill Rd, Upton, MA 01568
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  /6

  Est $382,427 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

  • 8% Above List Price
  • $435/SF
  • 127 Days On Market

  • Last Sold Price $355,000
  • Aug 22, 2024

  Last Listing Agent James Pham The Carroll Team
• 

  /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
• 

  

  /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 $1,225,703

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

  12 Stoddard St, Upton, MA 01568
• 

  

  /36

  Est $463,209 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
  • Jan 12, 2024

  Last Listing Agent The Jenkins Group Keller Williams Realty
• 

  

  /36

  $535,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 2,331 Sq Ft

  43 Knowlton Cir, Upton, MA 01568

  Welcome to this 3-bedroom end-unit townhome in the desirable Samreen Villa community. This open and airy floor plan is perfect for entertaining, featuring gleaming hardwood floors throughout the first floor and a bright family room with a gas fireplace, large windows & high ceilings. The spacious kitchen is updated with beautiful finishes offering plenty of room for cooking and gathering, while

  Lioce Properties Group

  43 Knowlton Cir, 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 $796,432

  Last Listing Agent Paul Clifford The Neighborhood Realty Group

  290 Westboro Rd, Upton, MA 01568
• 

  

  /40

  Est $518,102 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

  • 26% Above List Price
  • $197/SF
  • 54 Days On Market

  • Last Sold Price $410,000
  • Dec 11, 2024

  Last Listing Agent Laura Hebb ERA Key Realty Services
• 

  

  /42

  $1,500,000 Pending

  • 4 Beds
  • 7 Baths
  • 5,476 Sq Ft

  72 Glenview St, Upton, MA 01568

  Exceptional custom-built home offering over 5,000 sq ft of refined living space with 4 bedrooms, 5 full and 2 half baths, & a 3-car garage. Thoughtfully designed w/ high-end finishes throughout, this home blends luxury w/ warmth. The stunning kitchen features stone countertops, a large island, wood pizza oven & premium SS appliances, opening to a fire-placed family room. A coffered ceiling formal

  Team Metrowest Berkshire Hathaway HomeServices Commonwealth Real Estate

  72 Glenview St, 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 $756,047

  Last Listing Agent Jeanne Leombruno Century 21 Custom Home Realty

  10 Prospect St, Upton, MA 01568
• 

  

  /37

  Est $429,097 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

  • 34% Above List Price
  • $187/SF
  • 12 Days On Market

  • Last Sold Price $320,000
  • Jan 05, 2024

  Last Listing Agent Amber Cadorette Keller Williams Elite
• 

  

  /41

  $729,000

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

  8 Jackson Dr Unit 8, Upton, MA 01568

  Built in 2021, this bright end-unit “Florence” model offers easy single-level living with an open-concept layout perfect for entertaining. The kitchen features granite countertops, tile backsplash, large island, stainless steel appliances, stylish lighting, and a pantry, flowing seamlessly into the dining and living areas. Enjoy a cozy gas fireplace and backyard views from the living room. The

  Team Metrowest Berkshire Hathaway HomeServices Commonwealth Real Estate

  8 Jackson Dr Unit 8, 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
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  /30

  Est $395,041 Not Listed For Sale

  74 Main St, Upton, MA 01568

  • 3 Beds
  • 1.5 Baths
  • 1,428 Sq Ft
  • Built 1850

  74 Main St, Upton, MA 01568

  Last Sold Summary

  • 4% Above List Price
  • $266/SF
  • 75 Days On Market

  • Last Sold Price $380,000
  • Mar 28, 2025

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

  

  /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
• 

  

  /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 $680,032

  Last Listing Agent Alissa Tosches Lamacchia Realty, Inc.

  26 Brooks St, Upton, MA 01568
• 

  

  /31

  Est $516,422 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

  • 9% Above List Price
  • $389/SF
  • 3 Days On Market

  • Last Sold Price $475,000
  • Aug 23, 2023

  Last Listing Agent Christine Newell LAER Realty Partners
• 

  

  /16

  $500,000

  • 4 Beds
  • 2 Baths
  • 2,110 Sq Ft

  17 N Main St, Upton, MA 01568

  Antique Greek Revival single-family home in the heart of Upton’s historic district. The Thomas McFarland House (1810) is set on the right side of a 1.14-acre lot that slopes down to scenic Mill Pond. Offering four bedrooms, two full baths, 2100 sq ft living space and a two-car garage. The home is rich in character but does require significant renovation. Features include, abundant natural light,

  Michael O'Dea Coldwell Banker Realty - Brookline

  17 N Main St, 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 $559,830 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

  • 11% Above List Price
  • $261/SF
  • 6 Days On Market

  • Last Sold Price $505,000
  • Nov 02, 2023

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

  

  /41

  $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
• 

  

  /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 $538,929

  Last Listing Agent Allison Atwood Mendon Local Realty

  79 Fowler St, Upton, MA 01568
• 

  

  /42

  Est $688,796 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

  • 4% Above List Price
  • $307/SF
  • 6 Days On Market

  • Last Sold Price $660,000
  • Jun 12, 2023

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

  

  /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

Showing Results 41 - 80, Page 2 of 18