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Upton, MA Homes for Sale

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  • 18 Boot Shop Rd Unit 40, Upton, MA 01568
    18 Boot Shop Rd Unit 40, Upton, MA 01568
    18 Boot Shop Rd Unit 40, Upton, MA 01568
    /3

    $864,900 Open Fri 11AM - 3PM

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

    18 Boot Shop Rd Unit 40, Upton, MA 01568

    Welcome to Cobblers Creek, a serene 55+ community in Upton offering detached condominiums designed for active adults seeking low-maintenance living with commuter convenience. Tucked within a peaceful tree-lined setting yet close to Route 495 and the Mass Pike, this community blends privacy with accessibility. The Cardinal townhome floor plan features open-concept living with an eat-at island

    StreamLine Communities Streamline Communities - Upton

    18 Boot Shop Rd Unit 40, Upton, MA 01568
  • 13 Jonathans Way, Upton, MA 01568
    13 Jonathans Way, Upton, MA 01568
    13 Jonathans Way, Upton, MA 01568
    /36

    $849,900

    • 4 Beds
    • 2.5 Baths
    • 3,352 Sq Ft

    13 Jonathans Way, Upton, MA 01568

    Beautifully maintained home featuring gleaming hardwood floors and two cozy fireplaces. The cathedral-ceiling family room offers a bright and open layout ideal for everyday living and entertaining. Includes a formal dining room and a private office. Fully renovated and modernized kitchen and bathrooms with stylish finishes and contemporary functionality. Large windows throughout the home provide

    Shelly Armstrong Redfin Corp.

    13 Jonathans Way, Upton, MA 01568
  • 74 Warren St, Upton, MA 01568
    74 Warren St, Upton, MA 01568
    /2

    $269,000

    • Land
    • 3.19 Acres
    • $84,326 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. Excellent access to I-495 and the Mass Pike for commuters. Can be purchased on its own or as a package with 12 Breton Road listing MLS #:

    Melissa Ellison Mathieu Newton Sotheby's International Realty

    74 Warren St, Upton, MA 01568
  • 6 Wood St, Upton, MA 01568
    6 Wood St, Upton, MA 01568
    6 Wood St, Upton, MA 01568
    /40

    $1,100,000

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

    6 Wood St, Upton, MA 01568

    Where Luxury Meets Country! Welcome to this beautifully updated 4BR, 3,000+ sq ft home in scenic Upton. Perfect for entertaining with spacious foyer, formal dining & sitting room, plus expansive family room off the remodeled gourmet kitchen with quartz countertops, stainless steel appliances, double oven, compactor & decorative cabinet lighting. Upstairs offers 4 bedrooms & 2 full baths incl. a

    Brittany Palmerino Mathieu Newton Sotheby's International Realty

    6 Wood St, Upton, MA 01568
  • 130 High St, Upton, MA 01568
    130 High St, Upton, MA 01568
    130 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
  • 135 Main St, Upton, MA 01568
    135 Main St, Upton, MA 01568
    135 Main St, Upton, MA 01568
    /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
  • 6 Sawmill Brook Ln, Upton, MA 01568
    6 Sawmill Brook Ln, Upton, MA 01568
    6 Sawmill Brook Ln, Upton, MA 01568
    /42

    $1,500,000 Open Sat 12PM - 2PM

    • 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
  • 5 Boot Shop Rd Unit 31, Upton, MA 01568
    5 Boot Shop Rd Unit 31, Upton, MA 01568
    5 Boot Shop Rd Unit 31, Upton, MA 01568
    /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
  • 15 Shoemaker Ln Unit 7, Upton, MA 01568
    15 Shoemaker Ln Unit 7, Upton, MA 01568
    15 Shoemaker Ln Unit 7, Upton, MA 01568
    /28

    $699,900 Open Fri 11AM - 3PM

    • 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
  • 13 Plain St, Upton, MA 01568
    13 Plain St, Upton, MA 01568
    13 Plain 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
  • Lot 108 W Main St, Upton, MA 01568
    Lot 108 W Main St, Upton, MA 01568
    Lot 108 W Main St, Upton, MA 01568
    /3

    $550,000

    • Land
    • 5.45 Acres
    • $100,917 per Acre

    Lot 108 W Main St, Upton, MA 01568

    5.45± acres zoned General Business (GB) located along West Main Street (Route 140) in Upton. This versatile parcel offers strong road frontage, visibility, and flexibility for a variety of commercial, professional, mixed-use, or investment opportunities, subject to Town approvals. The GB zoning district supports a broad range of business and service uses, making this an ideal site for

    John Miller Keller Williams Pinnacle Central

    Lot 108 W Main St, Upton, MA 01568
  • 186 Spring St, Hopkinton, MA 01748
    186 Spring St, Hopkinton, MA 01748
    186 Spring St, Hopkinton, MA 01748
    /35

    $3,750,000

    • 4 Beds
    • 2.5 Baths
    • 3,014 Sq Ft

    186 Spring St, Hopkinton, MA 01748

    Prime Investment Opportunity: 20.9-Acre Private Estate in Top-Rated Hopkinton School District Nestled on an expansive 20.9-acre wooded lot bordering the Upton State Forest (one of the largest in Hopkinton), 186 Spring Street offers exceptional privacy, tucked deep in the forest with mature trees and natural seclusion. This rare parcel provides significant development potential — including the

    Brendon Sullivan-Monson StartPoint Realty

    186 Spring St, Hopkinton, MA 01748
  • 185 Prairie St, Northbridge, MA 01534
    185 Prairie St, Northbridge, MA 01534
    185 Prairie St, Northbridge, MA 01534
    /42

    $819,900

    • 4 Beds
    • 2.5 Baths
    • 2,764 Sq Ft

    185 Prairie St, Northbridge, MA 01534

    Welcome home to this classic Colonial nestled in one of the area’s sought-after neighborhoods! With 4 bedrooms and 2.5 baths, this home offers space & comfort for everyday living. You’ll love gathering in the stunning family room w/ cathedral ceilings & a cozy gas fireplace, just off the kitchen featuring newer stainless steel appliances, granite counter-tops and walk-in pantry. Host dinners in

    Team Metrowest Berkshire Hathaway HomeServices Commonwealth Real Estate

    185 Prairie St, Northbridge, MA 01534
Massachusetts Worcester County Upton

Real Estate & Homes for Sale in Upton, MA

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.

Learn more about living in Upton

Frequently Asked Questions

What is the average home price in Upton, MA?
Homes for sale in Upton, MA have an average home price of $804,168.
How many homes have sold over the last 12 months in Upton, MA?
92 homes have sold in Upton, MA over the last 12 months.
What are the most popular zip codes in Upton, MA?
The most popular zip codes in Upton, MA include 01568, 01748, 01534, 01757 and 01519.
How much do you need to make to afford a house in Upton?
The median home price in Upton is $752,370. If you put a 20% down payment of $150,500 and had a 30-year fixed mortgage with an interest rate of 6.11%, your estimated principal and interest payment would be $3,650 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $156K a year to afford the median home price in Upton. Learn how much home you can afford with our Home Affordability Calculator.
How are the schools in Upton, MA?
Upton, MA has highly rated public and private schools. Some of the best schools in Upton based on Niche Grades are Elmwood Elementary School, Hopkinton High School and Hopkins Elementary School. Browse all the schools in Upton, MA to learn more.

Home Trends in Upton, MA

On average, homes in Upton, MA sell after 34 days on the market compared to the national average of 53 days. The median sale price for homes in Upton, MA over the last 12 months is $774,252, up 16% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$774,252
Median Single Family Sale Price
$785,950
Median Townhouse Sale Price
$490,000
Median 2 Bedroom Sale Price
$784,489
Median 1 Bedroom Sale Price
$299,000
Average Price Per Sq Ft
$335
Number of Homes for Sale
8
Last 12 months Home Sales
92
Months of Supply
1.00
Median List Price
$752,370
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
16%
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