14

Upton, MA Houses for Sale

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  • /38

    $975,000

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

    68 Pearl St, Upton, MA 01568

    This 4-bedroom, 3.5-bath masterpiece has been completely transformed from top to bottom. Featuring an open, modern 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 entertaining, family life, or quiet retreat. Enjoy a stunning kitchen with high-end appliances,

    Laura Hebb ERA Key Realty Services

    68 Pearl St, Upton, MA 01568
  • /23

    $949,900

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

    17 Old Grafton Rd, Upton, MA 01568

    Enjoy The Benefits of New Construction with Energy Efficiency & Low Future Maintenance! This stunning Colonial offers the perfect blend of classic elegance and modern convenience. Including over $50,000 in builder upgrades, every detail has been carefully selected to provide style and functionality. The cozy gas fireplace, hardwood floors, Quartz countertops, luxury tile and plush carpets are

    Kim Backlund Northeast Realty + Co.

    17 Old Grafton Rd, Upton, MA 01568
  • /3

    $864,900 Open Fri 11AM - 4PM

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

    18 Boot Shop Rd Unit 40, 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 treeline 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 Cardinal townhome

    StreamLine Communities Streamline Communities - Upton

    18 Boot Shop Rd Unit 40, Upton, MA 01568
  • /28

    $855,900 New Construction

    • 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
  • /3

    $949,900 New Construction

    • 4 Beds
    • 2.5 Baths
    • 2,714 Sq Ft

    11 W Main St, Upton, MA 01568

    Kim Backlund Northeast Realty + Co.

    11 W Main St, Upton, MA 01568
  • /41

    $1,399,000

    • 3 Beds
    • 1 Bath
    • 1,201 Sq Ft

    130 South St, Upton, MA 01568

    Charming Country Retreat on 11.97 Acres – 3 Parcels 1.09 acres, 1.84 acres, 9.04 acres w/ Development Potential. Beautifully maintained 3BR home (4BR septic) Town approval expected in September for 3 buildable lots located directly behind the home,—offering rare potential for expansion, development, or multi-generational living. The home features a bright, welcoming layout with clear pride of

    Kerry Parker Equine Homes Real Estate, LLC

    130 South St, Upton, MA 01568
  • /42

    $764,900

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

    27 James Rd Unit 1, Upton, MA 01568

    NEW CONSTRUCTION for such a GREAT price! 2 Homes are ready for delivery. Both homes are 3 Bedroom, 3 1/2 bath, oversized one car garage, spacious granite kitchen with waterfall kitchen island, stainless steel appliances, open floor plan with dinning area in kitchen which opens to family room with balcony to private backyard. Upstairs is 3 large bedrooms, primary private full bath double vanity

    Kim Kimball Kimball Property Realty Inc.

    27 James Rd Unit 1, Upton, MA 01568
  • /26

    $414,900

    • 2 Beds
    • 1 Bath
    • 1,008 Sq Ft

    4 Depot St, Upton, MA 01568

    One level living and a great condo alternative in a quiet, friendly neighborhood. Perfect starter home or for seniors looking to downsize. Freshly painted interior and fully applianced including washer/dryer. Central air was added and the furnace was replaced in 2008. The roof was replaced in 2022. Slider in family room leads to charming patio overlooking pretty backyard and a tranquil

    Patricia Palmer Jack Walker Realtor®

    4 Depot St, Upton, MA 01568
  • /11

    $499,900

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

    10 Mendon St, Upton, MA 01568

    Own Your Dream Home with Zero Money Down! Unlock the door to your future with an exclusive offer: Purchase this home and receive $4,999 back in closing cost credits OR $2,367 per month at an exceptional financing rate of 5.88% APR with ZERO down payment available for those who qualify. Your Private Oasis Awaits Best Deal in Sought-After Upton!Don't miss this incredible opportunity to own a

    Nathan Clark Your Home Sold Guaranteed Realty, The Nathan Clark Team

    10 Mendon St, Upton, MA 01568
  • /33

    $629,900

    • 4 Beds
    • 3 Baths
    • 2,463 Sq Ft

    84 High St, Upton, MA 01568

    Welcome to this beautifully updated 4-bedroom, 3-bath home in the highly desirable town of Upton. Tucked away on a peaceful lot, this spacious residence offers a flexible floor plan with plenty of room to live, work, and relax. The kitchen features modern updates with ample cabinetry, newer appliances, and a large dining area perfect for gatherings. The bright living room and additional family

    Ann Marie Silva Redfin Corp.

    84 High St, Upton, MA 01568
  • /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
  • /13

    $1,600,000

    • 4 Beds
    • 3.5 Baths
    • 3,842 Sq Ft

    5 Sawmill Brook Ln, Upton, MA 01568

    Nestled within a private 4-lot subdivision, this brand-new custom home offers 3,842 sq ft of thoughtfully designed living space, with an additional 1,721 sq ft in the unfinished basement—ideal for storage or future expansion. Set on Lot 4, a generous 4.5-acre parcel, this property delivers the perfect balance of seclusion, space, and luxury. Still time remains to personalize finishes and make

    Team Metrowest Berkshire Hathaway HomeServices Commonwealth Real Estate

    5 Sawmill Brook Ln, Upton, MA 01568
  • /31

    $750,000

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

    27 James Rd Unit 2, Upton, MA 01568

    NEW CONSTRUCTION for such a GREAT price! 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

    Kim Kimball Kimball Property Realty Inc.

    27 James Rd Unit 2, Upton, MA 01568
  • /28

    $751,340 New Construction

    • 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

Why Live in Upton

Upton, Massachusetts, is a small town southeast of Worcester that appeals to families and commuters with its suburban living and convenient access to Boston’s outer beltway. The town features spacious lots, often shaded by mature trees, with homes ranging from modest ranch-style houses to preserved Victorians and classic colonials. The rustic layout includes winding two-lane roads and well-manicured yards, providing a tucked-away feel. Upton’s housing market is currently in high demand, with homes listing between $325,000 and $1 million. The Mendon-Upton Regional School District includes highly rated schools like Memorial Elementary and Nipmuc Regional High, offering programs such as Spanish Immersion and the Massachusetts Seal of Biliteracy. Recreational opportunities abound with multiple ponds like Pratt Pond and Dean Pond in Upton State Forest, which offers fishing, hiking, and winter sports. The Upton Community Center provides playgrounds and fitness classes, while the town center features local dining and shopping options, including Rose Garden Restaurant & Pub and The Little Coffee Bean. Upton is safer than the national average, contributing to its appeal. Residents rely on nearby Interstates 495 and 90 for commuting, with Boston about 40 miles away and Worcester 14 miles away. The town also hosts various houses of worship, including The United Parish of Upton and other nearby religious centers.

Home Trends in Upton, MA

Housing Trends

Median Sale Price
$730,000
Median Single Family Sale Price
$745,000
Median Townhouse Sale Price
$490,000
Median 2 Bedroom Sale Price
$769,865
Median 1 Bedroom Sale Price
$299,000
Average Price Per Sq Ft
$337
Number of Homes for Sale
16
Last 12 months Home Sales
88
Months of Supply
2.20
Median List Price
$750,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
6%
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