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Upton, MA Homes for Sale

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  • /41

    $799,000

    • 4 Beds
    • 2.5 Baths
    • 2,610 Sq Ft

    1 Quail Run, Upton, MA 01568

    Stunning 4-bedroom, 2.5-bath Colonial tucked at the end of a peaceful cul-de-sac a minute from town. A sun-filled vaulted great room complements the home’s open layout as an inviting space for everyday living. The bright kitchen with center island flows seamlessly into dining, living, and den—ideal for both entertaining and work-from-home flexibility. The secluded backyard contains an elevated

    Agent Photo

    Robyn Nasuti

    Realty ONE Group Suburban Lifestyle

    (508) 927-1889

    1 Quail Run, Upton, MA 01568
  • /42

    $749,000

    • 4 Beds
    • 2.5 Baths
    • 2,256 Sq Ft

    69 Warren St, Upton, MA 01568

    Tucked away on a private, wooded lot in desirable Upton, this beautifully updated 4-bedroom, 2.5-bath Colonial invites you to truly feel at home. A granite kitchen with stainless appliances and new gas stove, accented by a cozy pellet stove, flows effortlessly into a warm, fireplaced family room—perfect for everyday living and entertaining. The spacious primary suite features hardwood flooring

    Agent Photo

    Robyn Nasuti

    Realty ONE Group Suburban Lifestyle

    (508) 231-9130

    69 Warren St, Upton, MA 01568
  • /41

    $610,000

    • 3 Beds
    • 1.5 Baths
    • 1,789 Sq Ft

    21 Warren Rd, Upton, MA 01568

    21 Warren Rd, Upton, MA, a meticulously maintained 1957 single-family residence spanning 1789 square feet. This attractive property, presented in great condition, offers an exceptional opportunity for discerning buyers seeking comfort and convenience. The thoughtfully designed kitchen serves as the heart of the home, featuring sophisticated stone counters, a practical peninsula, and high-end

    Agent Photo

    Gary Kelley

    GK Group Services, Inc.

    (508) 456-8198

    21 Warren Rd, Upton, MA 01568
  • /42

    $789,000

    • 4 Beds
    • 2.5 Baths
    • 2,824 Sq Ft

    3 Ephraims Way, Upton, MA 01568

    Welcome to this beautifully maintained Cape on a private, landscaped lot in one of Upton’s most desirable locations -featuring town water & natural gas. Extended to include an expansive addition of a primary suite over the two-car garage, this home blends comfort and function with ease... focused on entertaining. Bright, open layout with hardwood flooring and a seamless kitchen-to-dining

    Agent Photo

    Robyn Nasuti

    Realty ONE Group Suburban Lifestyle

    (508) 545-7188

    3 Ephraims Way, Upton, MA 01568
  • /23

    $749,900 Open Fri 1PM - 3PM

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

    19 Boot Shop Rd Unit 19, Upton, MA 01568

    Welcome to the fabulous free-standing Blue Bird Model at Cobbler's Creek! Enjoy a distinctive townhouse with 2,200+ square feet of great space easily adaptable to your decor & lifestyle. From a welcoming front porch, enter a foyer with custom moldings & closet open to a spacious open floor plan including a living room & door to a deck, dining area & stylish kitchen w/white cabinets, Quartz

    Agent Photo

    Jeffrey Germagian

    ERA Key Realty Services-Bay State Group

    (508) 590-9785

    19 Boot Shop Rd Unit 19, Upton, MA 01568
  • /34

    $799,000 Open Fri 1PM - 3PM

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

    21 Boot Shop Rd Unit 21, Upton, MA 01568

    Are you looking for low-maintenance single-level living in a thoughtfully designed new construction condo located in an amazing 55+ community? Come check out the "Starling" floor plan at Cobbler's Creek, built by exceptional builders with a reputation for excellence. As you step inside, you're welcomed by an open and airy floor plan that seamlessly connects the sunny living room, dining room &

    Agent Photo

    Jeffrey Germagian

    ERA Key Realty Services-Bay State Group

    (508) 625-9207

    21 Boot Shop Rd Unit 21, Upton, MA 01568
  • /41

    $855,900 Open Fri 1PM - 3PM

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

    7 Boot Shop Rd Unit 7, Upton, MA 01568

    Come see what's new at Cobbler's Creek, a premier 55+ community of detached condominiums by the renowned Black Brook Realty builder group! Enjoy a Storybook setting of homes nestled in a serene landscape where every day feels like a retreat! The popular "Cardinal" model offers two-story living with everything you need handy on the first floor such as a covered front porch, foyer, powder room,

    The Kattman Team ERA Key Realty Services-Bay State Group

    7 Boot Shop Rd Unit 7, Upton, MA 01568
  • /42

    $1,138,000

    • 4 Beds
    • 3.5 Baths
    • 3,768 Sq Ft

    11 Howarth Dr, Upton, MA 01568

    Welcome to Glen Echo Estates near the Upton/Westborough line. This sought-after Wellington design offers spacious rooms, an open floor plan, abundant natural light & hardwood in key living areas. A dramatic two-story foyer opens to formal living & dining rooms. The chef’s kitchen features exotic quartzite counters, SS appliances & large island, flowing into a bright sunroom—perfect for

    Mary Wood Lamacchia Realty, Inc.

    11 Howarth Dr, Upton, MA 01568
  • /42

    $1,250,000

    • 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
  • /40

    $1,090,000

    • 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
  • /21

    $1,100,000

    • 4 Beds
    • 3.5 Baths
    • 3,487 Sq Ft

    99 W River St, Upton, MA 01568

    This beautifully designed custom home offers the perfect blend of privacy, space, and modern functionality. Set back from the street and positioned on an elevated lot, the home delivers both curb appeal and a sense of seclusion. Inside, you’ll find a thoughtfully designed floor plan featuring 4 spacious bedrooms and 3.5 bathrooms. The heart of the home is ideal for both everyday living and

    Diana Afonso Afonso Real Estate

    99 W River St, Upton, MA 01568
  • /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
  • /38

    $949,999

    • 4 Beds
    • 2.5 Baths
    • 2,454 Sq Ft

    9 Jewell Crossing, Mendon, MA 01756

    Welcome to this stunning 2018 Colonial positioned on a peaceful cul-de-sac in one of Mendon's premier neighborhoods. Nestled on a private elevated 1.38-acre lot framed by beautiful stone walls, this home effortlessly blends modern elegance with everyday warmth. The heart of the home is a large eat-in kitchen with stainless appliances and granite countertops and peninsula, flowing into a

    Christopher Rapacioli Coldwell Banker Realty - Franklin

    9 Jewell Crossing, Mendon, MA 01756
  • /35

    $1,077,845 New Construction

    • 4 Beds
    • 2.5 Baths
    • 2,751 Sq Ft

    20 Rawson Farm Rd, Mendon, MA 01756

    Framing starting soon. Foundation is in! Close to Schools and commuter routes. Welcome to the Ashford plan our most popular floor plan with the heart of the home featuring a quartz island, dining area, stainless steel appliances gleaming hardwood flooring. Fireplaced great room, dining room and study are complete with Hardwood floors & crown molding. Your master bedroom get away features an en

    Gary Smith Mendon Area Real Estate

    20 Rawson Farm Rd, Mendon, MA 01756
  • /42

    $965,000

    • 4 Beds
    • 3.5 Baths
    • 4,216 Sq Ft

    8 Leah Ln, Milford, MA 01757

    Southern-style custom Colonial with signature double front porches, ideally set at the end of a cul-de-sac in one of Milford’s premier neighborhoods. This beautifully maintained home offers expansive living space and exceptional craftsmanship throughout. A welcoming foyer opens to formal living and dining rooms, a spacious fireplaced family room, playroom, and a custom kitchen designed for

    David Restic Property Services Network

    8 Leah Ln, Milford, MA 01757
  • /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
  • /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
  • /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
  • /29

    $447,000 Open Sat 2PM - 3:30PM

    • 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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /42

    $1,450,000

    • 5 Beds
    • 5 Baths
    • 3,995 Sq Ft

    8 Stearns Rd, Upton, MA 01568

    Nestled at the end of a private cul-de-sac on nearly two acres, this meticulously renovated Colonial estate offers a premier multi-generational layout featuring a main residence & a fully equipped Accessory Dwelling. Beautiful main house boasts a mahogany deck, chef’s kitchen complete w/ quartz countertops, double wall ovens, a gas cooktop, & an oversized butcher-block island, all adjacent to a

    Kathleen Nicoloro Ferrari + Co. Real Estate

    8 Stearns Rd, Upton, MA 01568
  • /14

    $392,000

    • 2 Beds
    • 1.5 Baths
    • 1,144 Sq Ft

    12 Pinecrest Rd Unit B, Uxbridge, MA 01569

    New Furnace, new roof, newer water heater! Discover the ease of condominium living at 12 Pinecrest Road, Uxbridge, MA—a fantastic opportunity for buyers looking to transition from renting to homeownership. Constructed in 1989, this 1,144 sq ft residence offers a harmonious blend of comfort and convenience across two well-appointed stories. This inviting home features two spacious bedrooms and a

    Euridices Dolores DeJesus StartPoint Realty

    12 Pinecrest Rd Unit B, Uxbridge, MA 01569
  • /27

    $675,000

    • 3 Beds
    • 2.5 Baths
    • 1,728 Sq Ft

    13 Plain St, Upton, MA 01568

    BRAND NEW ROOF with *50 year* warranty just installed! 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, w/ beautiful newer flooring & an abundance of natural light throughout. A large kitchen offers

    The Tabassi Team RE/MAX Partners Relocation

    13 Plain 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
  • /35

    $2,950,000

    • 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
  • /42

    $570,000

    • 2 Beds
    • 2.5 Baths
    • 1,800 Sq Ft

    91 Buttercup Ln Unit 91, South Grafton, MA 01560

    Welcome to Hilltop Farm, a serene retreat on a quiet cul-de-sac. This Pulte-built home features a bright, open floor plan with HW floors, crown molding, and a gas fireplace. The upgraded kitchen boasts SS appliances and ample workspace.The 1st-floor primary suite offers a private escape with a tray ceiling and great natural light. Flexible living areas and extra BRs easily accommodate guests or a

    Kiran Kumar Gundavarapu Key Prime Realty LLC

    91 Buttercup Ln Unit 91, South Grafton, MA 01560

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. Residential areas offer spacious lots shaded by mature trees and homes ranging from modest ranch-style houses to preserved Victorians and classic colonials. The local 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, which offer offer Spanish Immersion programs and the Massachusetts Seal of Biliteracy. Pratt Pond and Dean Pond in Upton State Forest are hubs for fishing, hiking and winter sports. The Upton Community Center has playgrounds and fitness classes, while the town center features local dining and shopping options, including Rose Garden Restaurant & Pub and The Little Coffee Bean. Residents rely on nearby Interstates 495 and 90 for commuting, with Boston about 40 miles away and Worcester 14 miles away.

Frequently Asked Questions

What is the average home price in Upton, MA?
Homes for sale in Upton, MA have an average home price of $794,542.
How many homes have sold over the last 12 months in Upton, MA?
95 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, 01748, 01560 and 01534.
How much do you need to make to afford a house in Upton?
The median home price in Upton is $769,900. If you put a 20% down payment of $154,000 and had a 30-year fixed mortgage with an interest rate of 6.37%, your estimated principal and interest payment would be $3,840 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $165K 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 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
$791,900
Median Single Family Sale Price
$791,900
Median Townhouse Sale Price
$490,000
Median 2 Bedroom Sale Price
$803,430
Median 1 Bedroom Sale Price
$299,000
Average Price Per Sq Ft
$327
Number of Homes for Sale
22
Last 12 months Home Sales
95
Months of Supply
2.80
Median List Price
$769,900
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
16%
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