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Upton, MA Homes for Sale

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  • /40

    $925,000

    • 4 Beds
    • 2.5 Baths
    • 3,193 Sq Ft

    4 Phylmor Dr, Westborough, MA 01581

    Nestled in one of Westborough’s beloved neighborhoods, this well-maintained Colonial blends classic design in a natural, peaceful setting. The spacious living room w/hardwood floors welcomes quiet moments or conversation, while the dining room, also w/hardwoods, plus freshly painted kitchen w/granite counters, pantry & dining nook are perfect for gatherings. Custom cabinetry & a fireplace adorn

    Agent Photo

    Jennifer Juliano

    Keller Williams Boston MetroWest

    (844) 585-1531

    4 Phylmor Dr, Westborough, MA 01581
  • /42

    $1,175,000

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

    6 Wood St, Upton, MA 01568

    Rhapsody Hill Farm offers the perfect blend of family living and equestrian lifestyle. With an established and active lesson program it offers a rare turnkey opportunity for horse lovers. This 4-bed, 2.5-bath home on 2.88 acres is beautifully updated and thoughtfully designed for both comfortable living and hands-on horse care. The home features a spacious family room, formal dining & a chef’s

    Kerry Parker Equine Homes Real Estate, LLC

    6 Wood St, Upton, MA 01568
  • /42

    $1,049,000 Open Fri 5PM - 6:30PM

    • 2 Beds
    • 3.5 Baths
    • 4,139 Sq Ft

    23 Rockwood Ln Unit 23, Upton, MA 01568

    Exceptional home in highly sought-after Rockwood Meadows blends style, comfort & ease of condo living in a premier 55+ community. Nestled by conservation land & mature evergreens, this retreat offers privacy & nature views. Main living stuns w/open flr plan, pristine hardwds, family rm w/gas FP, sunlit dining rm, 4 season sunrm leading to a lovely, tranquil deck & sophisticated kitchen

    Sandra Lucchesi RE/MAX Executive Realty

    23 Rockwood Ln Unit 23, Upton, MA 01568
  • /23

    $949,900

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

    17 Old Grafton Rd, Upton, MA 01568

    The ASHLEY Plan is a great family home with dedicated Dining Room and Study as well as a spacious, light filled Breakfast Room. 4 bedrooms & Laundry on the 2nd floor. Open concept living, perfect for the modern lifestyle. Enjoy The Benefits of New Construction with Energy Efficiency & Low Future Maintenance! Don't Miss Out On This Great Opportunity To Own a BRAND NEW HOME Scheduled for Nov/Dec

    Kim Backlund Northeast Realty + Co.

    17 Old Grafton Rd, Upton, MA 01568
  • /42

    $850,000

    • 4 Beds
    • 3.5 Baths
    • 2,470 Sq Ft

    1 Summers Cir, Upton, MA 01568

    Get ready for some summer fun at this unique Farmhouse style Colonial, the "Elegance" model, in Whitney Farms, a newer cul-de-sac neighborhood located close to downtown and under 5 miles to Route 495 in Hopkinton. This home has a unique and versatile floorplan featuring a primary bedroom suite on the first floor and a guest suite on the second floor, perfect for multi-generational families. The

    Michael Colombo Suburban Lifestyle Real Estate

    1 Summers Cir, Upton, MA 01568
  • /42

    $1,285,000

    • 4 Beds
    • 5.5 Baths
    • 5,736 Sq Ft

    12 Breton Rd, Upton, MA 01568

    With a flexible layout that supports multigenerational living, this gorgeous custom-built colonial has ample space and is situated on 3+ private acres. From the moment you step into the grand two-story foyer adorned w/ granite flooring, you’ll be captivated by the attention to detail & luxurious features throughout, incl 9ft+ ceilings & gleaming hardwoods. Spacious fam rm is a true showpiece w/

    Melissa Ellison Mathieu Newton Sotheby's International Realty

    12 Breton 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
  • /27

    $1,099,500 Open Sun 1PM - 3PM

    • 4 Beds
    • 2.5 Baths
    • 2,884 Sq Ft

    16 Rawson Farm Rd, Mendon, MA 01756

    The Modified Hampton is one of our most popular plans in the Miscoe Springs neighborhood. Now building this 4 bedroom, 2.5 bath home with professional designer finishes to be included. Featuring a beautiful cathedral family room complete with fireplace and adjacent to a great entertaining kitchen you can dine casually around the quartz island or in the breakfast area. Enhanced cabinets to the

    Gary Smith Mendon Area Real Estate

    16 Rawson Farm Rd, Mendon, MA 01756
  • /41

    $599,000

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

    130 South St, Upton, MA 01568

    Charming Country Retreat w/ Barn, Garage & Expansion Potential. Discover the perfect blend of comfort, charm & opportunity in this beautifully maintained 3-bedroom, 1-bath home, nestled on 1.84 scenic acres. Pride of ownership is evident throughout, making this move-in ready property an ideal haven for those seeking peace, space, & flexibility. Enjoy the serenity of mature trees & open skies

    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
  • /28

    $439,900 Open Sun 12PM - 1:30PM

    • 2 Beds
    • 1.5 Baths
    • 1,699 Sq Ft

    16 Fieldstone St Unit 16, Upton, MA 01568

    Welcome home to this large and inviting townhome in Upton with a comfortable, well-designed layout. Step inside to discover multiple built-ins, including a beautiful entry bench with storage and hooks that adds both style and function.The spacious, sunken living room is perfect for entertaining and features sliding doors that lead to the back deck overlooking nicely maintained grounds. An

    Karole O'Leary Lamacchia Realty, Inc.

    16 Fieldstone St Unit 16, Upton, MA 01568
  • /3

    $250,000

    • Land
    • 1.87 Acres
    • $133,690 per Acre

    3 South St, Upton, MA 01568

    Prime Development Opportunity – One of Three lot Subdivision Pending Final Approval. An exceptional opportunity awaits builders, families, or equestrian enthusiasts on this picturesque parcel tucked away from the road in a peaceful, semi-rural setting. Currently part of a proposed 3-lot subdivision, this land is set to receive final town approval next month. Soil testing has already been

    Kerry Parker Equine Homes Real Estate, LLC

    3 South St, Upton, MA 01568
  • /3

    $250,000

    • Land
    • 1.85 Acres
    • $135,135 per Acre

    1 South St, Upton, MA 01568

    Prime Development Opportunity – One of three lot Subdivision Pending Final Approval. An exceptional opportunity awaits builders, families, or equestrian enthusiasts on this picturesque parcel tucked away from the road in a peaceful, semi-rural setting. Currently part of a proposed 3-lot subdivision, this land is set to receive final town approval next month. Soil testing has already been

    Kerry Parker Equine Homes Real Estate, LLC

    1 South St, Upton, MA 01568
  • /3

    $350,000

    • Land
    • 5 Acres
    • $65,543 per Acre

    2 South St, Upton, MA 01568

    Prime Development Opportunity – One of Three lot Subdivision Pending Final Approval. An exceptional opportunity awaits builders, families, or equestrian enthusiasts on this picturesque parcel tucked away from the road in a peaceful, semi-rural setting. Currently part of a proposed 3-lot subdivision, this land is set to receive final town approval next month. Soil testing has already been

    Kerry Parker Equine Homes Real Estate, LLC

    2 South St, Upton, MA 01568
  • /26

    $424,900

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

    4 Depot St, Upton, MA 01568

    Terrific new listing! One level living with six rooms and freshly painted interior! Central air was added and the furnace was replaced in 2008. The roof was replaced in 2022. Slider in family room leads to patio overlooking pretty backyard and a babbling brook. Behind the house is a storage shed with electricity. Great commuting location with easy access to Routes 140, 495, and the MA Pike!

    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

    $649,900 Open Sun 1PM - 2:30PM

    • 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
  • /41

    $1,297,500

    • 4 Beds
    • 3.5 Baths
    • 3,404 Sq Ft

    5 North St, Upton, MA 01568

    Luxury Looks Better on North Street - A triumph of modern design and architectural refinement, this newly constructed residence is gracefully sited on 3.5 pristine acres near the state forest. From the moment you enter, exquisite details captivate—9’ ceilings, intricate coffered millwork, and sensational hardwoods set the tone for elevated living. The heart of the home-the kitchen, is a culinary

    THE LASH GROUP Keller Williams Boston MetroWest

    5 North 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
  • /41

    $1,395,000

    • 4 Beds
    • 3.5 Baths
    • 3,613 Sq Ft

    2 Sawmill Brook Ln, Upton, MA 01568

    Introducing an exceptional opportunity: NEW BUILD by MORRELL CONSTRUCTION on Lot 1! This expansive 5.6-acre homesite is the largest in Sawmill Brook Lane, featuring a beautifully designed 3,613 SF custom home that radiates warmth & character. The charming exterior boasts a welcoming covered front entry, setting the tone for this stunning residence. Inside, the thoughtfully crafted layout includes

    Team Metrowest Berkshire Hathaway HomeServices Commonwealth Real Estate

    2 Sawmill Brook Ln, Upton, MA 01568
  • /42

    $685,000

    • 4 Beds
    • 2 Baths
    • 2,165 Sq Ft

    23 Westboro Rd, Upton, MA 01568

    Discover this enchanting farmhouse retreat blending timeless charm with modern updates. Spanning 2,165 sqft, this charming home offers 4 bedrooms and 2 baths,perfect for family living. Enjoy an expansive farmers porch ideal for relaxing and entertaining. The renovated kitchen adds contemporary flair, while a newer roof and fully paid solar panels enhance energy efficiency. Hobby farm enthusiasts

    Team ROVI Real Broker MA, LLC

    23 Westboro Rd, Upton, MA 01568
  • /42

    $570,000

    • 3 Beds
    • 2.5 Baths
    • 2,231 Sq Ft

    36 Knowlton Cir Unit 36, Upton, MA 01568

    Location! Location! Location!~ This lovely end-unit townhouse features 3 bedrooms plus a loft, 2 1/2 baths and a large room in the lower level. The unit is light and bright with hardwood floors throughout. The 2nd floor features a large MBR with a ceiling fan and full bath. The 2 additional bedrooms are good sized and share the 2nd full bath and the laundry with recent W&D is in the hallway. The

    Karen Richardson LAER Realty Partners

    36 Knowlton Cir Unit 36, 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
  • /39

    $695,000

    • 4 Beds
    • 1.5 Baths
    • 1,851 Sq Ft

    26 Brooks St, Upton, MA 01568

    This beautifully renovated Colonial blends classic New England charm with stylish modern updates. Originally built in 1900, the home was fully redone in 2021, offering the appeal of a newer home with timeless character. Located in Upton near the town center and new community center, this 4-bedroom, 1.5-bath home sits on 2.19 acres at the end of a quiet dead-end street. Inside, you'll find Cali

    Alissa Tosches Keller Williams Pinnacle Central

    26 Brooks St, Upton, MA 01568
  • /10

    $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! 3 BRAND NEW HOMES for sale being constructed. This home is 3 Bedroom, 3 1/2 bath, one car garage, finished room and bath in basement, storage area in basement, walk out basement with full door no bulkhead, hardwood floors, kitchen island, fully applianced stainless steel kitchen, third floor walk up area for storage or future finished space, cover front

    Kim Kimball Kimball Property Realty Inc.

    27 James Rd Unit 2, Upton, MA 01568
  • /9

    $325,000

    • Land
    • 1.84 Acres
    • $176,630 per Acre

    0 Ridge Rd, Upton, MA 01568

    Tucked away on scenic Ridge Road in Upton, this stunning 1.84-acre parcel offers the perfect blend of peaceful seclusion and everyday convenience. Surrounded by natural beauty with no visible neighbors and exceptional privacy, this rare offering is just minutes from Upton State Forest, reservoirs, and preserved conservation land. Zoned “Residential Developable Land,” it’s brimming with

    Elisha Lynch Lamacchia Realty, Inc.

    0 Ridge Rd, 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
  • /42

    $649,900

    • 3 Beds
    • 2.5 Baths
    • 2,170 Sq Ft

    204 Sand Trap Ct Unit 204, Northbridge, MA 01534

    OTHER BUYERS' LOSS IS NOW YOUR GAIN! STUNNING & SO WELL-LOVED TOWNHOME ON THE 18th HOLE AT SHINING ROCK GOLF COURSE & SITS ACROSS THE STREET FROM THE 19th HOLE / CLUBHOUSE! This Morgan model has all the upgrades as seller spared no expense throughout ownership! 1st flr boasts dramatic 2-story entry foyer, open concept, 9 ft ceilings, Hardwoods & 1st floor Master Suite w/tray ceiling, crown

    Alison Zorovich RE/MAX Vision

    204 Sand Trap Ct Unit 204, Northbridge, MA 01534
  • /30

    $2,249,000

    • Land
    • 21 Acres
    • $107,608 per Acre

    186 Spring St, Hopkinton, MA 01748

    Opportunity to develop a 5 lot luxury subdivision abutting the Upton State Forest in one of the most beautiful settings in town. Keep, expand, or tear down the existing house being offered "as is." The home has been updated and is currently being rented for $4,930 per month through the end of November. Do your due diligence with the town to update the driveway entrance and seek approvals for one

    Amy Rutkowski A. Rutkowski Realty, Inc.

    186 Spring St, Hopkinton, MA 01748

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.

Frequently Asked Questions

What is the average home price in Upton, MA?
Homes for sale in Upton, MA have an average home price of $781,130.
Are home prices dropping in Upton?
Yes, home prices in Upton are down 10% in the last 12 months.
How many homes have sold over the last 12 months in Upton, MA?
30 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, 01757, 01534, 01748 and 01560.
How much do you need to make to afford a house in Upton?
The median home price in Upton is $749,900. If you put a 20% down payment of $150,000 and had a 30-year fixed mortgage with an interest rate of 6.72%, your estimated principal and interest payment would be $3,880 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $166K a year to afford the median home price in Upton.
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 Hopkinton High School, Elmwood Elementary School and Hopkins Elementary School. Browse all the schools in Upton, MA to learn more.

Home Trends in Upton, MA

Housing Trends

Median Sale Price
$705,000
Median Single Family Sale Price
$1,075,000
Median Townhouse Sale Price
$475,000
Median 2 Bedroom Sale Price
$807,861
Average Price Per Sq Ft
$327
Number of Homes for Sale
5
Last 12 months Home Sales
30
Months of Supply
2.00
Median List Price
$749,900
Median Change From 1st List Price
-1%
Median Home Sale Price YoY Change
-11%
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