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Upton, MA Houses for Sale

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  • /42

    $699,000

    $16K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,835 Sq Ft

    52 Elm St, Upton, MA 01568

    Tucked along a scenic country road, this beautifully preserved early 18th-century Gambrel blends timeless New England character with the comfort and updates today’s buyers seek. Rich with historic charm, the rambling floor plan offers warm, inviting spaces including a stunning 1st-floor primary suite, great room, library/den, front-to-back living room, classic keeping room with stone fireplace,

    Agent Photo

    Robyn Nasuti

    Realty ONE Group Suburban Lifestyle

    52 Elm St, Upton, MA 01568
  • /42

    $1,099,000

    Open Fri 4:30PM - 6PM
    • 4 Beds
    • 4.5 Baths
    • 2,889 Sq Ft

    91 High St, Upton, MA 01568

    Be the first to call this exceptional new-construction Colonial home! Ideally situated near the heart of downtown Upton, this 2,889 -square-foot residence pairs timeless farmhouse charm with modern finishes and a flexible layout designed for today’s lifestyle. Enjoy the character of small-town living with convenient access to Upton’s town beach, parks, library, post office, local shops, and even

    Agent Photo

    Robyn Nasuti

    Realty ONE Group Suburban Lifestyle

    91 High St, Upton, MA 01568
  • /40

    $1,079,000

    • 4 Beds
    • 3.5 Baths
    • 3,350 Sq Ft

    165 East St, Upton, MA 01568

    Pride of ownership abounds at this exceptional 4-bedroom, 3.5 bath custom contemporary home set on 3.50 beautifully maintained acres offering privacy and endless opportunities to enjoy the outdoors. Enter through the two-story foyer and be greeted by sunlight pouring into the home through an abundance of windows, skylights, and sliders creating a bright and welcoming atmosphere throughout. The

    Michael Stein Redfin Corp.

    165 East St, Upton, MA 01568
  • /42

    $2,500,000

    • 4 Beds
    • 5 Baths
    • 4,040 Sq Ft

    117 South St, Upton, MA 01568

    75-Acre Elite Equestrian & Wellness Sanctuary. Ultimate private retreat with a 4,040 SF luxury Cape, world-class horse facilities, and resort backyard. Trail access to West Hill Dam. RESIDENCE: Chef's kitchen (Jade 6-burner, Sub-Zero, granite waterfall island). 1st-floor primary suite with vaulted ceilings & spa bath. 3 upper bedrooms, office, large bonus room + finished walkout lower level.

    Beth Byrne Gibson Sotheby's International Realty

    117 South St, Upton, MA 01568
  • /36

    $1,147,900

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

    Lot 12 Rawson Farm, 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

    Lot 12 Rawson Farm, Mendon, MA 01756
  • /41

    $875,000

    $25K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,806 Sq Ft

    10 Sadler Rd, Upton, MA 01568

    *** ALL CARPET IS BEING REPLACED IN OCTOBER 2026 **Tucked away on a quiet cul-de-sac with 2 acres of wooded bliss, this Federal-front Colonial is pure serenity with an incredibly spacious layout to boot. It's 3000+ square feet that feels warm and homey with New England charm oozing from every room. The kitchen has NEW quartz countertops and a massive eat-in area with a downdraft gas stove. It

    Erika Steele REMAX Executive Realty

    10 Sadler Rd, Upton, MA 01568
  • /7

    $999,900

    New Construction
    • 4 Beds
    • 2.5 Baths
    • 2,780 Sq Ft

    17 W Main St, Upton, MA 01568

    UNDER CONSTRUCTION...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. Every detail has been carefully selected to provide style and functionality. 1ST floor hardwoods, Quartz countertops and GE Cafe appliances are just a few of the upgraded details that make this home

    Kim Backlund Northeast Realty + Co.

    17 W Main St, Upton, MA 01568
  • /42

    $974,900

    Open Sun 11AM - 1PM $23K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 3,332 Sq Ft

    27 Juniper Rd, Upton, MA 01568

    Siting majestically in one of Upton's most desired neighborhoods, this gorgeous Colonial commands attention with its gracious presence, impressive scale and beautifully designed spaces. Step through the soaring two story foyer and into a home created for memorable living and effortless entertaining. The wonderful kitchen is a culinary delight, complete with a generous island, gourmet appliances

    THE LASH GROUP Keller Williams Boston MetroWest

    27 Juniper Rd, Upton, MA 01568
  • /42

    $1,165,000

    Open Fri 4:30PM - 6:30PM
    • 4 Beds
    • 3.5 Baths
    • 4,843 Sq Ft

    3 Dairy Dr, Upton, MA 01568

    Welcome to the Preserve at Lake Wildwood. Stately ,4BR, 3.5BA Center Hall Colonial featuring 4,000+ sq ft of living space in a desirable suburban neighborhood. Set at the beginning of a cul de sac this grand two-story foyer opens to formal living and dining rooms. Gourmet eat-in kitchen with center island and stainless steel appliances flows into an expansive family room with gas fireplace and

    Lisa Anzede Mathieu Newton Sotheby's International Realty

    3 Dairy Dr, Upton, MA 01568
  • /41

    $695,000

    • 4 Beds
    • 2.5 Baths
    • 2,108 Sq Ft

    5 Elm St, Upton, MA 01568

    Timeless charm & modern comfort describe this renovated Colonial originally built in 1828 on a scenic, quiet country road. Fully reframed in 1988, with a kitchen/family room addition in 1994, this spacious home is in excellent condition. This saltbox-style home blends historic character with contemporary living. The kitchen/family room & the primary bedroom suite have cathedral ceilings &

    Lisa Pezzoni Andrew J. Abu Inc., REALTORS®

    5 Elm St, Upton, MA 01568
  • /42

    $1,320,000

    $20K PRICE DROP
    • 5 Beds
    • 3.5 Baths
    • 4,498 Sq Ft

    66 Glenview St, Upton, MA 01568

    Set amid park-like grounds with a private wooded backdrop, this expansive Upton home stands out for its generous living space, thoughtful updates and remarkable flexibility. Updated kitchens and baths throughout bring a fresh, polished feel to the home, while impressive architectural details begin in the soaring two-story foyer and continue into the dramatic family room, where a vaulted ceiling,

    Lisa Aron Williams Coldwell Banker Realty - Sudbury

    66 Glenview St, Upton, MA 01568
  • /41

    $549,000

    $50K PRICE DROP
    • 5 Beds
    • 3 Baths
    • 2,887 Sq Ft

    130 High St, Upton, MA 01568

    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 entertaining. A fully renovated backyard shed adds

    Jacob Greasley eXp Realty LLC

    130 High St, Upton, MA 01568
  • /42

    $1,099,000

    Open Fri 5PM - 6:30PM
    • 4 Beds
    • 2.5 Baths
    • 4,146 Sq Ft

    32 Howarth Dr, Upton, MA 01568

    Located in the exclusive Glen Echo Estates community in Upton, this impressive 2008-built Colonial showcases an ideal lot & yard all within a tranquil neighborhood setting. As you move inside the home, you are greeted by a regal two-story foyer, which receives fantastic morning sunlight via an Eastern Exposure. The sunlight reflects beautifully off the oak hardwood floors that extend throughout

    Brian Connelly Redfin Corp.

    32 Howarth Dr, Upton, MA 01568
  • /33

    $919,900

    $30K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 3,100 Sq Ft

    33 Milford St, Upton, MA 01568

    Stunning fully renovated luxury home offering three finished levels of sophisticated living with high-end finishes and designer details throughout. This turnkey home features an open-concept floor plan, a custom chef's kitchen with premium appliances, spa-inspired bathrooms, modern lighting, and beautifully updated living spaces. Thoughtfully renovated with exceptional craftsmanship, it

    Wendy Solano Lamacchia Realty, Inc.

    33 Milford St, Upton, MA 01568
  • /40

    $849,900

    $30K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 3,132 Sq Ft

    2 Brookside St, Upton, MA 01568

    Stately Colonial offering a rare combination of privacy, natural beauty & modern updates in one exceptional property. Every window captures peaceful views of the surrounding landscape, creating a vacation-at-home feeling year-round. This spacious home features beautiful hardwood floors throughout the 1st floor & a versatile floor plan designed for easy everyday living & entertaining. The stunning

    Leah Burke William Raveis R.E. & Home Services

    2 Brookside St, Upton, MA 01568
  • /40

    $899,000

    • 4 Beds
    • 5 Baths
    • 4,242 Sq Ft

    96 Fowler St, Upton, MA 01568

    Exceptional Colonial on 3.21 Private Acres. Discover the perfect blend of comfort and lifestyle in this exceptional colonial, set on 3.21 acres of stunning, pastoral landscape. Designed to inspire, the home is bathed in natural light and offers breathtaking sunset views—providing the perfect backdrop for working from home. The open-concept floor plan flows seamlessly, featuring a spacious family

    Isaac Alvarenga Property Investors & Advisors, LLC

    96 Fowler St, Upton, MA 01568
  • /37

    $575,000

    • 3 Beds
    • 1.5 Baths
    • 1,556 Sq Ft

    40 Hartford Ave N, Upton, MA 01568

    Welcome to this charming Colonial Style home, offering warmth, character, and modern comfort throughout. The inviting open floor plan creates a seamless flow between the living, dining, and kitchen areas, making the home feel spacious and welcoming. Beautiful hardwood flooring runs throughout the home. The living room is complemented by a cozy fireplace with an elegant marble surround. The

    Cindy Donati Century 21 Custom Home Realty

    40 Hartford Ave N, Upton, MA 01568
  • /37

    $599,000

    • 3 Beds
    • 2 Baths
    • 1,496 Sq Ft

    15 North St, Upton, MA 01568

    Discover the perfect blend of timeless character and modern convenience in this spacious 3-bedroom, 2-full-bath home set on more than 3 acres of private, classic grounds complete with traditional stone walls. With generously sized rooms, high ceilings, and a highly livable floor plan, this home offers plenty of space to relax, entertain, and enjoy the best of country living. The recently

    Laura Hebb ERA Key Realty Services

    15 North St, Upton, MA 01568
  • /39

    $1,699,000

    $176K PRICE DROP
    • 8 Beds
    • 6 Baths
    • 6,850 Sq Ft

    175 Pleasant St, Upton, MA 01568

    ABSOLUTELY STUNNING. Enormous 8 Bedroom Home with over 6000 square feet of living on 5.5 acres bordering the Shining Rock Golf Course. Privacy abounds on this special property that has been completely updated. Septic System, Roof, Heat/AC, Kitchen, 6 Bathrooms, Windows, Flooring, Well....All NEW. First floor has kitchen, dining room, TWO front to back family/living rooms, full bath, pantry and an

    Matthew Sousa Bullseye Realty Group

    175 Pleasant St, Upton, MA 01568
  • /42

    $650,000

    • 3 Beds
    • 2 Baths
    • 2,055 Sq Ft

    24B River St, Upton, MA 01568

    Imagine summer days spent at nearby Kiwanis Beach and evenings under the stars in your private backyard Jacuzzi. Beautifully maintained home offers an exceptional setting just a short walk from Upton Center, the beach, ballfield and courts, and approximately four miles from the Hopkinton I-495 exit and Price Chopper Plaza. Inside, the open kitchen and family room create a warm, inviting place to

    Katie McBride REMAX Executive Realty

    24B River St, Upton, MA 01568
  • /33

    $550,000

    Open Sun 12PM - 1:30PM $75K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,548 Sq Ft

    24 Main St, Upton, MA 01568

    Previously relocated owners say it's time to sell! This rare antique in town colonial awaits a new owner. Wait until you see all the character this home exudes. Freshly painted throughout! Bright and sunny layout, hardwood flooring, gorgeous woodwork, nooks and crannies, tin ceilings, built ins, sun filled corner glassed in porch & white picket fence. This is truly a special home. Large dining

    Jeanne Leombruno Century 21 Custom Home Realty

    24 Main St, Upton, MA 01568
  • /42

    $955,000

    $20K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,941 Sq Ft

    161 South St, Upton, MA 01568

    Price Improvement on this truly exceptional Colonial where timeless elegance meets modern comfort. Meticulously maintained and thoughtfully updated, this stunning 4-bedroom, 2.5-bath home offers generous living spaces, 9-foot ceilings, and abundant natural light, creating a warm and inviting atmosphere throughout. The beautifully appointed kitchen is a cook’s dream, featuring upgraded granite

    Laura Hebb ERA Key Realty Services

    161 South St, Upton, MA 01568
  • /24

    $449,000

    • 4 Beds
    • 2 Baths
    • 1,392 Sq Ft

    68 School St, Upton, MA 01568

    Custom built in 1980 for members of a long term, multigenerational Upton family. This expanded ranch will now change hands for the first time! This home features 4 bedrooms and 2 full baths spread out over close to 1,400 sq. ft. Perfectly set off the road on a 25,000+ sq. ft. level lot, this home features a private primary bedroom with its own full bath and jacuzzi tub and direct access to its

    Bill Glanton Berkshire Hathaway HomeServices Stephan Real Estate

    68 School St, Upton, MA 01568
  • /5

    $499,000

    • 3 Beds
    • 2.5 Baths
    • 3,217 Sq Ft

    15 W Main St, Upton, MA 01568

    After being cherished by the same family for approximately 170 years, 15 West Main Street presents an extraordinary opportunity to become the next steward of a truly special historic property. Known as the Arba Thayer Wood House and Barn, this distinguished homestead was built in 1855 by Arba Thayer Wood and retains the character, craftsmanship, and gracious proportions of a bygone era. Rich with

    Kim Backlund Northeast Realty + Co.

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

    $1,199,900

    $100K PRICE DROP
    • 4 Beds
    • 4.5 Baths
    • 3,543 Sq Ft

    8 Juniper Rd, Upton, MA 01568

    Welcome to 8 Juniper Road, where impressive space, thoughtful updates, and a truly spectacular backyard oasis come together in one exceptional home. Offering approximately 3,600 sq. ft. of living space, 4 bedrooms, 4.5 bathrooms, and a 3-car garage, this beautifully maintained and updated property is designed for both comfortable everyday living and unforgettable entertaining. Inside, a spacious

    Amy Bisson Lamacchia Realty, Inc.

    8 Juniper Rd, Upton, MA 01568
  • /42

    $1,075,000

    $75K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,924 Sq Ft

    32 Mendon St, Upton, MA 01568

    32 Mendon St, Upton, MA. Where modern sophistication meets timeless design. This newly constructed 2026 residence offers 2,924 square feet of impeccably curated living space, blending contemporary elegance with refined modern farmhouse architecture. Every detail has been intentionally selected — from premium finishes to elevated craftsmanship — creating a home that feels both luxurious and

    Luana Velame Century 21 The Real Estate Group

    32 Mendon St, 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. 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.

Single Family Home Price Trends

Median Home Price
$791,900
Median 3-Bedroom Home Price
$620,000
Median 4-Bedroom Home Price
$875,000
Median 5-Bedroom Home Price
$1,335,000
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