Upton MA Homes for Sale - Live MLS Listings

- - - Scroll Down for Current Listings on the Market - - -

Why Buy a Home in Upton, MA?

Upton is a scenic, rural-feeling town in the Blackstone Valley, located between Hopkinton, Westborough, Grafton, Milford, Hopedale and Mendon. With its white-steepled town center, rolling hills, ponds and large tracts of forest, Upton appeals to buyers looking for elbow room, newer homes on generous lots and a strong sense of community, while staying close to the I-495 corridor.

Easy Commuter Access

Route 140 runs through the center of town, with Interstate 495, Route 146 and the Mass Pike all a short drive away. Commuter rail riders can use the MBTA Framingham/Worcester Line stations in nearby Westborough and Grafton, or the Franklin Line at Forge Park/495.

Outdoor Lifestyle and Recreation

Upton State Forest offers miles of woodland trails for hiking, mountain biking and cross-country skiing. Pratt Pond and its town beach are a summer favorite, and the town's conservation lands add even more trails to explore close to home.

Schools and Education

Upton is part of the Mendon-Upton Regional School District, which includes the Memorial School in Upton, Miscoe Hill School in Mendon and Nipmuc Regional High School in Upton. Blackstone Valley Regional Vocational Technical High School is also located in Upton. Buyers should confirm school assignments and programs directly with the districts.

Upton Real Estate Market Insights

Upton is known for larger homes on spacious lots, from antique farmhouses to newer colonials and new construction, along with a limited number of condominiums. As of early November 2026, about 32 single-family homes and condos were listed for sale in Upton, from roughly $450,000 to about $1.65 million, with an average list price near $891,000. Market figures change daily, so contact us for the latest numbers and recent sales.

Ready to explore homes in Upton? Contact the realinsyghts group today at (508) 686-0940.

Photo credits: First Unitarian Church, Upton MA by John Phelan, CC BY 4.0, via Wikimedia Commons.

Select any listing for more information

$1,649,000

8 Beds ⋅ 6 Baths ⋅ 73520686 MLS

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 office. Second floor has primary bedroom, with a gorgeous bathroom complete w/ a soaking tub, a changing room and his and her walk in closets. Laundry room, another 2 full bathrooms and 3 additional bedrooms round out the second floor. 3rd floor has a full bath and four bedrooms. Basement is finished w/ numerous rooms including a full bath. Outside there's a large inground pool with decorative water feature, patios, and all sorts of plantings surrounded by a huge yard and acres of forest. Unique is a understatement. You've got to see it to believe it.

175 Pleasant St, Upton

Listing courtesy of Listing Agent: Matthew S. Sousa from Listing Office: Bullseye Realty Group.

$1,499,999

5 Beds ⋅ 4 Baths ⋅ 73594520 MLS

Location Location Location!! Perched up on a hill overlooking Pratt Pond. Steps away from Kiwanis Beach Park and a public beach with baseball+soccer fields, tennis, pickleball+basketball courts. Featuring an open concept kitchen/family room, with an oversized island, family room with 20' ceiling height, flexibility with a 1st floor primary and a private office. 2nd floor features the other 4 bedrooms, all en-suite including a jack-n-jill. Retreat to an oversized master bedroom with his and hers walk-in closets and a spa like bathroom. Laundry room conveniently on the 2nd floor.

9 Kiwanis Beach Rd, Upton

Listing courtesy of Listing Agent: Luciano Souza from Listing Office: Pinto Real Estate.

$1,320,000

5 Beds ⋅ 4 Baths ⋅ 73562275 MLS

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, fireplace and an extraordinary collection of windows fill the space with natural light and views of the surrounding landscape. At the center of the main level, the updated kitchen features quartz counters, extensive cabinetry, stainless appliances, gas/propane cooking and an oversized island. Its open connection to the breakfast area and family room creates an inviting gathering space, while the generous dining room provides plenty of room for larger occasions. A private office or library with built-in bookshelves offers a quiet, distinctive space away from the main gathering areas. The home's generous proportions continue upstairs, where the exceptionally spacious primary suite features two walk-in closets and a beautifully updated, spa-like private bath. Three additional bedrooms, another updated full bath and conveniently located laundry complete the bedroom level. One of the property's greatest advantages is the finished lower level. With its own updated kitchen, bedroom, full bath, living/guest space and recreation room, it offers an outstanding setup for multigenerational living or extended family, while also providing tremendous flexibility for recreation, guests, a home gym or additional living space. Outdoors, a heated inground pool with newer liner, expansive deck with pergola, raised garden beds, brick walkways, fire pit, flowering shrubs and perennials create a wonderful setting for summer gatherings and time at home. Tucked within mature landscaping and a wooded setting, the backyard feels like its own retreat while remaining convenient to Upton's town center, schools, recreation and major commuting routes. An oversized garage provides exceptional vehicle and storage space, while fully owned solar and a newer 5-bedroom septic system are significant improvements for the next owner.

66 Glenview St, Upton

Listing courtesy of Listing Agent: Lisa Aron Williams from Listing Office: Coldwell Banker Realty - Sudbury.

$1,200,000

4 Beds ⋅ 4 Baths ⋅ 73592698 MLS

Your own backyard retreat awaits at 30 Juniper Road. Set on nearly three private acres in Upton’s Taft Mill Estates, this custom-designed home pairs exceptional outdoor living with an expansive layout and extensive recent improvements. A brick-front farmer’s porch creates a memorable welcome, opening to inviting spaces with clear maple flooring throughout the first floor, a beautifully appointed cook’s kitchen, and an open flow ideal for gathering and entertaining. Four bedrooms and 3½ baths offers room to spread out, while the spacious primary bedroom includes an exercise area. The finished daylight walkout lower level adds versatile space for recreation, hobbies, or entertaining. Fresh neutral interior paint and new carpeting, completed in October 2026, give the home a beautifully refreshed feel. The backyard is the showstopper: professionally landscaped grounds, manicured lawn, surrounding woodlands, and a gorgeous inground pool framed by stamped concrete. Enjoy summer afternoons by the water, dinner on the composite deck, or quiet mornings in the enclosed rear porch overlooking this remarkable setting. Installed in 2012, the pool received a new heater and salt cell in 2026, and the pool deck was resealed that August. Significant 2026 improvements include a new main roof and front porch roof, generator, water softener, emergency water shut-off, and upgraded irrigation with a rain sensor. The driveway was sealed in September, complementing the season’s professional landscaping. Additional updates include the A/C system in 2019, well pump in 2023, and garage door openers in 2024. Yard fencing, an electronic dog fence serviced in 2026, and a composite deck round out the outdoor amenities. From its welcoming porch and custom details to its thoughtfully maintained grounds and exceptional poolside setting, this home offers space to entertain, room to unwind, and the privacy of an estate-size lot—all in a beautiful Upton neighborhood.

30 Juniper Rd, Upton

Listing courtesy of Listing Agent: Robyn Nasuti from Listing Office: Realty ONE Group Suburban Lifestyle.

$1,175,000

4 Beds ⋅ 4 Baths ⋅ 73587562 MLS

If you have been looking for a new place to call "home" then welcome to 27 Dairy Dr in Upton. This beautifully appointed 4-bedroom, 3.5-bath home, with 4,116 sq/ft of exceptional space, thoughtful details, and a private backyard oasis is the one you have been waiting for. The main level features a first-floor office, chef’s kitchen with a large island, a formal dining room, living room with soaring ceiling and loads of natural light, elegant crown moldings, and beautiful architectural details. The second-floor features a spacious primary en suite along with 3 other generous size bedrooms and 2 full baths that offers a flexible layout perfect for multi-generational living, plus the laundry room adds everyday convenience. The finished basement provides versatile space for entertaining with a wet bar and media room area perfect for gaming, recreation and hobbies. Outside, enjoy an inground heated saltwater pool, hot tub and a private setting ideal for relaxing or entertaining. Additional highlights include a 3-car garage, 2 year old central heating and A/C system, and a new hot water tank installed in 2024. With scenic views out the front and tranquility in the private back yard this is truly an inviting home with space, comfort, and style throughout nestled in the amazing town of Upton and all it has to offer. Great commuter location with close proximity to 495 and the MA Pike, highly regarded school systems, and local amenities such as, award winning Shining Rock Golf Club, Kiwanis Beach and much more. Schedule your appointment today to start making your new memories.

27 Dairy Dr, Upton

Listing courtesy of Listing Agent: Sean Terrell from Listing Office: Redfin Corp..

$1,149,900

4 Beds ⋅ 5 Baths ⋅ 73566681 MLS

Welcome to 8 Juniper Road, where generous living space, extensive updates, and a spectacular backyard come together. Set on 2.04 acres, this Upton home offers approximately 3,700 sq. ft., 4 bedrooms, 4.5 bathrooms, and a 3-car garage. Step inside and immediately feel welcomed by the warmth of every day living and entertaining. The backyard is a standout feature of this incredible home with a heated in-ground pool, integrated hot tub, expansive composite deck, landscaping, and irrigation system. Significant improvements include a new boiler, well tank, and well pump in 2021; composite deck, pool liner, heater, and pump in 2022; irrigation in 2023; first-floor AC condenser in 2024; and a sealed driveway in 2026. Additional updates include exterior painting and trim, kitchen slider, backsplash, and appliances.

8 Juniper Road, Upton

Listing courtesy of Listing Agent: Amy Bisson from Listing Office: Lamacchia Realty, Inc..

$1,115,000

4 Beds ⋅ 4 Baths ⋅ 73579210 MLS

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 remote start. Main level also features a private home office. Upstairs, the primary suite offers a walk-in closet and office area and a spa bath with a jetted tub and double vanity, alongside 3 additional generous bedrooms and laundry room The finished walk-out basement includes a bonus room and flexible space for entertaining, recreation and fitness. Step outside to an impressive outdoor gathering space complete with patio and pergola overlooking a private yard with an oversized storage shed. Includes multi-car attached garage, central A/C, and hardwood floors. Conveniently located near top-rated schools, shopping, and commuter routes.

3 Dairy Drive, Upton

Listing courtesy of Listing Agent: Lisa Anzede from Listing Office: Mathieu Newton Sotheby's International Realty.

$1,099,000

4 Beds ⋅ 4 Baths ⋅ 73580900 MLS

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 your morning coffee at Dunkin’. Step inside to discover beautiful hardwood flooring, elegant crown molding, and custom details that make this home feel truly special. At the heart of the home is a showstopping kitchen featuring quartz countertops, a dramatic waterfall island, a gas range, and a walk-in pantry with custom shelving. Whether you’re hosting a holiday celebration or enjoying a quiet morning at the island, this is a space designed for gathering. The kitchen opens directly to the patio, creating an effortless connection for outdoor dining, entertaining, or simply unwinding at the end of the day. The inviting living room is anchored by a fireplace and custom built-in shelving, adding warmth, character, and a polished finishing touch. Upstairs, you’ll find three beautifully appointed bedrooms, including a serene primary suite with a spacious walk-in tiled shower. Decorative tile elevates the bathrooms, while custom built-in shelving in every bedroom adds both style and practical storage. The finished lower level expands the possibilities with a fourth bedroom, full bathroom, and kitchenette. This versatile space is ideal for an au pair suite, home gym, media room, home office, or can accommodate overnight guests, multigenerational living, or a private retreat. Even the garage reflects the same attention to detail found throughout the residence. The garage features durable waterproof flooring and has is a dedicated EV electrical outlet in place for electric-vehicle charging—an intentional modern amenity designed for the future of luxury homeownership. With four bedrooms, four-and-a-half bathrooms, thoughtful craftsmanship, and spaces created for both everyday comfort and memorable occasions, this stunning home offers the opportunity to enjoy brand-new construction and the welcoming lifestyle that makes Upton such a special place to call home.

91 High, Upton

Listing courtesy of Listing Agent: Robyn Nasuti from Listing Office: Realty ONE Group Suburban Lifestyle.

$1,099,000

4 Beds ⋅ 3 Baths ⋅ 73578851 MLS

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 the first floor, leading past a dedicated home office behind private French doors. The formal dining room offers classic entertaining space, while the eat-in kitchen serves as the heart of the home, equipped with granite countertops, a center island, induction cooking, vent hood, kitchen desk, plenty of cabinetry, and upgraded appliances replaced in 2020. Seamlessly connected to the kitchen is a sizable family room featuring hardwood floors installed in 2022, as well as a bright Florida room with sliders leading outdoors. Upstairs, you will find second-floor hardwoods added in 2022, a full laundry room with 2020 washer/dryer, a full bathroom, three bedrooms, and the primary suite—notable for its generous size, walk-in closet, and spacious bath. The lower level features a fully finished basement (2019) complete with a built-in bar, bonus area, versatile living and entertaining space, and separate storage. Outside, the property truly shines with a full-yard irrigation system installed in 2020. Beautiful stonework and pavers lead to a nicely sized deck, a custom patio build, and a spacious 10x18 shed added in 2018. Mature trees line the rear for privacy, while the front yard offers a perfect setback with a three-car garage providing ample parking and storage. All located near Upton State Forest, local farms, restaurants, and convenient commuting options along the Westborough line.

32 Howarth Dr, Upton

Listing courtesy of Listing Agent: Brian Connelly from Listing Office: Redfin Corp..

$1,079,000

4 Beds ⋅ 4 Baths ⋅ 73574514 MLS

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 kitchen includes two pantry closets, Sub Zero refrigerator and stylish concrete sink and flows to a step-down dining/living area with gorgeous stone fireplace and slider access to the peaceful screened in porch and amazing deck. A laundry room, half bath and vaulted ceiling living room with French doors complete the floor. Upstairs a large bedroom with en-suite bath acts as a second primary and is complemented by two additional bedrooms and full bath on the way to the huge primary bedroom with vaulted ceilings, double closets, a separate room currently being used as a makeup area and an exquisite bathroom with jetted tub and separate shower. The walk out lower level includes a climate controlled wine cellar and access to the heated two car garage. Outdoor living is truly a highlight, with a beautiful stone patio featuring a pizza oven, pergola and a fire pit, plus a deck with newer composite decking and railings and high end built-in grill and additional pergola—perfect for entertaining, dining, or relaxing. Additional features include a new roof with solar panels, a beautifully repaved driveway with a distinctive paver border, and lushly landscaped grounds. With its combination of generous living space, unique amenities, and spectacular indoor-outdoor living, this Upton property offers a rare opportunity to enjoy comfort, in a serene environment yet only a short distance to Routes 495 and 90 and the shops and restaurants nearby.

165 East St, Upton

Listing courtesy of Listing Agent: Michael Stein from Listing Office: Redfin Corp..

$1,050,000

4 Beds ⋅ 3 Baths ⋅ 73522448 MLS

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 enduring. Designed for elevated living, the expansive floor plan features 4 spacious bedrooms, 2 full baths, and 1 half bath, seamlessly balancing comfort and style. The two-car garage adds convenience, while the gracious front porch delivers a distinguished first impression. Generously sized basement with full build-out opportunity. Set on a property with exceptional outdoor potential, this residence presents a rare opportunity to own a home defined by quality, sophistication, and architectural presence.

32 Mendon St, Upton

Listing courtesy of Listing Agent: Luana Velame from Listing Office: Century 21 The Real Estate Group.

$999,900

4 Beds ⋅ 3 Baths ⋅ 73547384 MLS

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 full of beauty and comfort. The composite decking provides a low-maintenance space for relaxing or entertaining. Located in a highly sought-after school district, this home is within close proximity to Route 495 and train stations, providing easy access to commuting routes and conveniences. This home is a must-see for anyone seeking modern living in a peaceful, well-connected location! Scheduled for a November 2026 Closing.

17 West Main Street, Upton

Listing courtesy of Listing Agent: Kim Backlund from Listing Office: Northeast Realty + Co..

$974,900

4 Beds ⋅ 3 Baths ⋅ 73573687 MLS

Sitting majestically in one of Upton’s most desired neighborhoods, this gorgeous Colonial commands attention with its gracious presence, impressive scale and beautifully designed spaces. A soaring two story foyer opens to a home made for memorable living and exceptional entertaining. The kitchen is a culinary delight with a generous island, gourmet appliances, a large cooktop, double wall oven and charming banquette seating. Just beyond, the dramatic cathedral family room with its beautiful fireplace sets the scene for holiday mornings and evenings fireside, while the oversized dining room brings elegance to every gathering. The fabulous three season porch offers a peaceful escape for morning coffee and evenings overlooking the beautiful surroundings. Upstairs, the oversized primary retreat invites you to unwind with a favorite book in the window seat, while the luxurious bath features a spacious walk in shower and oversized Jacuzzi tub. A huge walkout basement offers exceptional potential for future living space, entertaining or a fitness room. A new heating system and hot water heater add to the appeal of this impressive home, offering the space to celebrate, the comfort to unwind and a setting worthy of it all.

27 Juniper Road, Upton

Listing courtesy of Listing Agent: THE LASH GROUP from Listing Office: Keller Williams Boston MetroWest.

$940,000

4 Beds ⋅ 3 Baths ⋅ 73566169 MLS

Price Improvement so you can be home for the holidays!! A 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 countertops, stainless-steel appliances, a double oven, an approximately two-year-old refrigerator, and an oversized walk-in pantry. The first floor also offers convenient laundry, a half bath, a spacious dining room with French doors—perfect for holiday gatherings—and an additional sitting room that provides an ideal home office or flex space. The 23x23 cathedral-ceiling living room offers a cozy retreat with a pellet stove, perfect for relaxing on chilly winter evenings. Quality finishes and thoughtful upgrades throughout the home showcase a level of character, warmth, and established charm that new construction simply cannot replicate. Upstairs, the spacious primary suite features an en-suite bath with newer quartz countertops, double sinks, a walk-in shower, and a generous walk-in closet. Three additional well-sized bedrooms and a full bath with tub/shower and newer quartz countertops complete the second floor. The unfinished walk-out basement, with 9-foot ceilings and large windows, offers incredible potential for additional living space, a recreation room, home gym, or whatever your needs may be. The oversized two-car garage, complete with a negotiable car lift, provides exceptional flexibility for car enthusiasts, hobbyists, or additional storage. Adding to the home’s appeal is an extremely reasonable solar lease at just $137.15 per month, offering the potential for significant energy cost savings. All of this is set in an amazing location, making this exceptional Colonial a wonderful place to call home. With its spacious layout, thoughtful upgrades, abundant potential, and timeless character, this is a home you won’t want to miss!

161 South St, Upton

Listing courtesy of Listing Agent: Laura Hebb from Listing Office: .

$909,900

4 Beds ⋅ 3 Baths ⋅ 73557408 MLS

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 seamlessly blends timeless charm with contemporary elegance. Move-in ready and designed for today's lifestyle, this exceptional home offers comfort, style, and quality in every detail.

33 Milford St, Upton

Listing courtesy of Listing Agent: Wendy Solano from Listing Office: Lamacchia Realty, Inc..

$899,000

4 Beds ⋅ 5 Baths ⋅ 73564539 MLS

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 room, a bright four-season sunroom, and an expansive deck, making it an ideal space for family gatherings and entertaining. You will appreciate the versatility of both first and second-floor primary suites, all complemented by beautiful hardwood flooring throughout. For the equestrian enthusiast, this property is a true standout. It features a 4–6 stall barn, a 140’x70’ sand arena, and direct trail access to the Upton State Forest. Additional amenities include a detached three-car garage and a sparkling in-ground pool for refreshing summer days. With a newer furnace (2019) and a functional, spacious layout, this home offers incredible potential. Bring your vision and a few updates to make this unique property your own.

96 Fowler St, Upton

Listing courtesy of Listing Agent: Isaac Alvarenga from Listing Office: Property Investors & Advisors, LLC.

$859,900

3 Beds ⋅ 3 Baths ⋅ 73589810 MLS

ONE-OF-A-KIND LOG HOME RETREAT One owner! Set on nearly 4.5 private acres, this extraordinary 3-bedroom, 2.5-bath custom log home showcases rustic luxury, exceptional craftsmanship, and unforgettable character. Hand-peeled logs, two dramatic stone fireplaces featuring stones sourced from the property, radiant floor heating, and stunning wide yellow pine plank floors accented with antique nails create timeless warmth and charm. The kitchen features an impressive 8-burner chef’s stove, while the first-floor primary suite, sunroom, spacious living and dining areas, and open loft offer comfort and versatility. Upstairs are two additional bedrooms and a full bath with Jacuzzi tub. The finished lower level surprises with 10-foot ceilings, half bath, laundry, workshop, and a custom bookcase concealing a hidden room! Outside, enjoy professional landscaping, irrigation, privacy, and room to roam. Additional features include a 16x20 storage shed, 8x10 wood shed and a chicken coop complete with chickens. A rare opportunity to own a truly distinctive log home offering acreage, rustic elegance, and extraordinary details at every turn!

55 Fiske Mill Rd, Upton

Listing courtesy of Listing Agent: Christine Lawrence from Listing Office: ERA Key Realty Services- Milf.

$829,900

4 Beds ⋅ 4 Baths ⋅ 73595051 MLS

Beautiful sunsets, an amazing backyard, and extensive updates create an inviting place to call home in Warren Woods, one of Upton’s most desirable neighborhoods. Offering four bedrooms, two full baths, and two half baths, this thoughtfully improved home combines generous living spaces with town water, natural gas, and convenient access to major routes. The expansive family room is a standout, with soaring cathedral ceilings and a fireplace that brings warmth and character to everything from quiet evenings to lively gatherings. An updated kitchen, spacious bedrooms, and a dedicated office offer comfortable spaces for everyday living, working, and entertaining. The finished basement adds even more versatility, with room for recreation, hobbies, or relaxing, plus a conveniently added half bath. Outside, a beautiful backyard invites you to unwind and enjoy the natural surroundings. Composite decking and a lovely patio provide welcoming spaces for outdoor dining, summer get-togethers, and taking in the sunset, creating a picturesque backdrop. Numerous improvements reflect the care invested throughout the home. In 2026, three bedrooms, the office, foyer, and hallway were freshly painted, and all hardwood flooring was refinished. Additional updates since 2020 include kitchen improvements, new vinyl windows and sliders, replacement carpeting in the bedrooms and office, a new front door, and granite front steps. A new electrical panel, updated switches and outlets throughout, added air-conditioning, and LeafGuard gutters enhance everyday comfort and convenience. The exterior has also been repainted, completing the home’s refreshed appearance. With its sought-after neighborhood setting, inviting indoor and outdoor spaces, and thoughtful improvements, this Warren Woods home is ready for its next chapter.

9 Jonathans Way, Upton

Listing courtesy of Listing Agent: Robyn Nasuti from Listing Office: Realty ONE Group Suburban Lifestyle.

$810,000

4 Beds ⋅ 3 Baths ⋅ 73597534 MLS

Beautifully appointed and full of character, this four-bedroom, 2.5-bath expanded Cape on a corner lot on Church Street offers more than 2,500 square feet of inviting living space. A flexible layout, gorgeous kitchen, and first-floor primary suite make this Upton home a standout. The kitchen pairs granite countertops with modern stainless steel appliances, offering a stylish setting for everyday cooking and entertaining. A bright dining area provides a welcoming gathering space, while the fireplace adds warmth and charm. The home’s expanded footprint includes a distinctive step-down bedroom addition, providing added space and versatility. Enjoy the convenience of a first-floor primary suite and first-floor laundry, with three additional bedrooms offering room for guests, work, or hobbies. A two-car garage beneath the primary suite adds practical storage and sheltered parking. Outdoor living is equally inviting, with a spacious deck overlooking the corner-lot setting—an ideal spot for morning coffee or relaxing at the end of the day. Close to Upton’s town beach, downtown shops, dining, and local amenities, this beautiful home brings together comfort, character, and convenience.

36 Church St, Upton

Listing courtesy of Listing Agent: Robyn Nasuti from Listing Office: Realty ONE Group Suburban Lifestyle.

$799,000

2 Beds ⋅ 3 Baths ⋅ 73577353 MLS ⋅ ['Cobblers Creek'] BLDG.

New offering 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 surrounded by nature 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, laundry room & entry to your 2-car garage. An airy open floor plan offers a vaulted living room w/fireplace & hardwood floors accessing a deck with tranquil wooded views perfect for enjoying your morning coffee surrounded by nature, mature trees, and local wildlife. Enjoy a dining area and kitchen featuring beautiful white cabinets, large center island & stainless-steel appliances. Primary bedroom suite includes spacious closet & full bath w/double sinks & tiled shower. 2nd floor offers has a terrific loft, second bedroom & full bath. Walk out lower level. Energy efficient systems. Be part of a wonderful community w/access to a clubhouse & trails. * HOA Fee Includes Water/ Sewer/ Spectrum Internet & Cable & more. Designed for comfort and sophistication, this home lets you trade yard work for walking trails and quiet afternoons listening to the rustle of the trees. Come visit today!

10 Boot Shop Road Unit 10, Upton

Listing courtesy of Listing Agent: Jeffrey Germagian from Listing Office: ERA Key Realty Services-Bay State Group.

$749,900

2 Beds ⋅ 2 Baths ⋅ 73535220 MLS ⋅ ["Cobbler's Creek"] BLDG.

Beautiful new construction one-level "Starling" floor plan now available at Cobbler's Creek, a vibrant 55+ community built by exceptional builders with a reputation for excellence! You're welcomed by an open & airy floor plan that seamlessly connects the sunny living room w/fireplace & built-ins, dining rm & kitchen all w/hardwood floors. The kitchen features attractive cabinets with moldings above, ample Quartz counter space, modern SS appliances, tile backsplash & center island that can double as a breakfast bar or casual gathering spot. The living room accesses a deck & patio. Off the main living space, a dedicated office provides a quiet area to work from home. Primary bedroom is a comfortable retreat including en-suite bathroom w/double sinks, tiled shower w/glass door & large closet. Second bdrm for guests & full bath. Laundry & 2-car garage. Enjoy a serene & convenient location close to everything. ** HOA Fee Includes Water/ Sewer/ Spectrum Internet & Cable & more ** Ready now!

5 Boot Shop Road Unit 5, Upton

Listing courtesy of Listing Agent: Jeffrey Germagian from Listing Office: ERA Key Realty Services-Bay State Group.

$699,000

2 Beds ⋅ 3 Baths ⋅ 73592075 MLS ⋅ ['Upton Ridge'] BLDG.

Now that I Got Your Attention! IF THE PRICE IS RIGHT, THIS CLASSIC CAR and AMAZING TOWNHOME CAN BE YOURS! OPEN HOUSE Sunday 11/8, 12 to 2. "Coveted Upton Ridge" This customized Bright, Sunny Tuscan style with oversized windows and has 2800+- square feet of elegant living. Over $100,000 in extras for the lot premium and Quality upgrades. Welcoming entry with custom decorative molding. French doors to office/den. Fabulous cooks’ kitchen with large Granite island and lots of Granite counters, upgraded cabinets with custom lighting, stainless steel appliances, six burner gas countertop range, built in cabinet oven and microwave, spacious French door refrigerator. Open floor plan, 9 ft. ceilings, inviting living room with oversized windows and sliders to tranquil deck overlooking acres of wooded privacy. First floor bedroom suite with loads of windows, private full bath with double granite top vanity and walk-in closet. First floor laundry. Turned hardwood staircase leads to second floor suite with 22 ft. family room, large bedroom, walk in closet, full bath and second home office/craft room. Fantastic $41,000 lower-level upgrade with exercise and game rooms and wall of windows with a walk out to the rear yard. Quality two zone Gas Lennox heating, Rinnai on demand gas hot water, central air conditioning, and lots of storage. Two car garage. Enjoy all the amenities this peaceful community offers. Walk to Shining Rock Golf course. Fast access to conservation land, Town forest, biking, hiking, public beach and access to dining, shopping, and highways. Vehicle conveyed by separate title after property deed recording.

72 Shannon Way Unit 72, Upton

Listing courtesy of Listing Agent: Matt Cuddy from Listing Office: CUDDY Real Estate.

$675,000

4 Beds ⋅ 3 Baths ⋅ 73565350 MLS

$20,000 PRICE IMPROVEMENT! 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 & skylights. The open-concept kitchen is designed for entertaining featuring new stainless steel appliances & a convenient peninsula. The adjacent front-to-back living room creates an inviting space for relaxing with a charming fireplace, perfect for cozy evenings. This home provides four comfortable bedrooms & two full baths, with the primary bath offering a jetted tub with shower. The floorplan offers flexibility for multiple home office options. Once you step outside the privacy of the large, level lot and heated in-ground pool designed for leisurely summer days, leaves you imagining the wonderful memories to be made. This much-loved property is the perfect blend of historic elegance and modern amenities. Kiwanis Beach (1/2 mi), Upton Heritage Park (1/4 mi), Upton State Forest (3 mi away), all offer passive recreation opportunities. UPDATES TO PROPERTY: New 4BR septic 2026; Indirect hot water heater 2025; 200 AMP electric 2023; SS kitchen appliances 2025; Chimney repointing 2026; Roof 2023.

5 Elm Street, Upton

Listing courtesy of Listing Agent: Lisa Pezzoni from Listing Office: Andrew J. Abu Inc., REALTORS®.

$649,000

3 Beds ⋅ 2 Baths ⋅ 73586877 MLS

A true home in the forest! Come visit this diamond in the rough and all it's potential, on the market for the first time after 50 years of original ownership. Set back over 100' from the road, this sprawling property is situated on a 2.5 acre tree-lined lot. Featuring 3 large bedrooms, 2 full baths and endless possibilities, all within nearly 2300 sq/ft of living space. Walk through the vaulted ceilings in the oversized great room, out to the massive cedar lined sunroom. Unfinished basement offers an additional 1100+ sq/ft with 7'7" ceilings...perfect for a bonus room, man cave, playroom, workshop, etc. Big ticket items like asphalt roof, wood frame Andersen windows, boiler, hot water heater and oil tank all replaced within 10 years. Seller to install new 3-bedroom septic prior to close. OH 10/9 from 5-7pm and 10/10 from 11-1pm. Don't miss out on this gem with great bones!

23 Forest St, Upton

Listing courtesy of Listing Agent: Drew Jacobs from Listing Office: Jacobs Real Estate.

$649,000

2 Beds ⋅ 3 Baths ⋅ 73546012 MLS ⋅ ['Upton Ridge'] BLDG.

Welcome to this beautifully maintained two-story townhouse in the highly desirable 55+ Upton Ridge community, where comfort, style, and low-maintenance living come together. Built in 2023 this floor plan features a first-floor primary suite, offering both privacy and ease of living. Upstairs features a generously sized second bedroom with walk in closet, full bath and a spacious second-floor loft perfect for a home office, or additional living space. The open-concept design seamlessly connects the living room, dining area, a chef’s kitchen, beautiful hardwood floors creating an ideal setting for both everyday living and effortless entertaining. Expansive windows fill the home with natural light while showcasing peaceful wooded views that provide a tranquil backdrop. The expansive walk-out unfinished basement presents exceptional potential for future living space, a home gym, workshop, or abundant storage. Easy access to major routes, shopping and boarders Shining Rock Golf Club!

56 Shannon Way Unit 56, Upton

Listing courtesy of Listing Agent: The Semple & Hettrich Team from Listing Office: Coldwell Banker Realty - Sudbury.

$640,000

2 Beds ⋅ 3 Baths ⋅ 73524427 MLS ⋅ ['Upton Ridge'] BLDG.

Enjoy low-maintenance living at Upton Ridge, a desirable 55+ community just a short stroll from the renowned Shining Rock Golf Course. This beautiful Milan-style two-story home offers a spacious, thoughtfully designed floor plan featuring a first-floor primary suite and open-concept living. The oversized kitchen is perfect for entertaining, complete with upgraded cabinetry, quartz countertops, and a large center island. The light-filled gathering room opens through a slider to the rear deck, with remote controlled awning, creating a seamless indoor-outdoor space to relax and enjoy the peaceful surroundings. Upstairs, you’ll find a spacious loft, a generously sized second bedroom with a full bath and walk-in closet. Experience the beauty and tranquility of Upton Ridge while enjoying convenient access to Boston, Providence, New Hampshire, Route 9, I-90, I-495, and the commuter rail.

87 Shannon Way Unit 86, Upton

Listing courtesy of Listing Agent: Shane Brady from Listing Office: Keller Williams Realty.

$549,000

5 Beds ⋅ 3 Baths ⋅ 73400838 MLS

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 valuable storage or workshop space. Located on a convenient main road just minutes from downtown Upton.

130 High St, Upton

Listing courtesy of Listing Agent: Jacob Greasley from Listing Office: eXp Realty LLC.

$519,899

3 Beds ⋅ 3 Baths ⋅ 73574288 MLS

Move right into this beautifully maintained, 2020-built end-unit townhouse in the heart of Upton. Set at the rear of the building and open on three sides, the home enjoys abundant natural light throughout. Three finished levels offer a flexible, well-designed layout. The open main level features a sun-filled living room and a stylish kitchen with a large island, stainless steel Samsung appliances, farmhouse sink and tile backsplash, plus a convenient half bath. The second floor offers two spacious bedrooms with double closets, a full tiled bath and in-unit laundry. The entire third floor is dedicated to a private primary suite with a generous closet and en-suite bath. Additional highlights include hardwood flooring throughout, gas heat, central air, a full basement for storage and two exclusive use parking spaces. Enjoy a five-unit association with a low monthly fee, close to Upton Town Center, walking trails, Route 140, I-495 and the Grafton commuter rail.

140 Main St Unit E, Upton

Listing courtesy of Listing Agent: Bhargavi Thaduri from Listing Office: Coldwell Banker Realty - Newton.

$499,000

4 Beds ⋅ 3 Baths ⋅ 73579649 MLS

PRICE IMPROVEMENT, freshly painted and professionally cleaned carpets!** A rare opportunity to own a four-bedroom, two and a half bath residence in the desirable Samreen Villas. This private end unit offers exceptional natural light and a thoughtfully designed layout ideal for both everyday living and entertaining. The main level features hardwood and ceramic tile flooring, an open-concept kitchen and dining area, and a dramatic living room with soaring ceilings and an oversized window that fills the space with natural light. A convenient half bath completes the first floor. Upstairs you'll find three generously sized bedrooms that share a full bath, along with a spacious primary suite featuring a vaulted ceiling and private en-suite bath. Laundry is conveniently located on the second floor. The lower level offers additional flexible space-perfect for a home office or playroom. A wonderful combination of privacy, space, and functionality in a highly desirable community.

1 Knowlton Circle Unit 1, Upton

Listing courtesy of Listing Agent: Leah Tringale from Listing Office: Longwood Residential, LLC.

$489,000

2 Beds ⋅ 3 Baths ⋅ 73583734 MLS ⋅ ['Fieldstone Condos'] BLDG.

Welcome to the Fieldstone Condominiums, where comfort, style, and low-maintenance living come together in one of Upton’s most desirable communities. This beautifully maintained, highly coveted end-unit townhouse offers an open-concept floor plan filled with natural light and thoughtfully designed living spaces. The spacious custom kitchen features granite countertops, stainless steel appliances, and ample cabinetry, flowing seamlessly into the dining area and soaring cathedral-ceiling living room. A desirable first-floor primary suite provides convenience and privacy, while the second level offers additional bedroom space, full bath, and versatile spacious loft area perfect for a home office or reading nook. The partially finished lower level adds flexible living space ideal for a family room, fitness area, or guest accommodations. Enjoy outdoor relaxation on the private deck overlooking professionally landscaped grounds. Complete with garage and additional surface lot space with easy access to major routes, shopping, dining, and top-rated schools, this exceptional home delivers the perfect blend of elegance, functionality, and carefree condominium living.

13 Fieldstone St Unit 13, Upton

Listing courtesy of Listing Agent: Leavitt + Co Team from Listing Office: Compass.

$474,900

3 Beds ⋅ 3 Baths ⋅ 73500996 MLS

Welcome to 140 Main St U:B in Upton, Massachusetts. Constructed in 2020, this 1,785-square-foot condominium stands in great condition, offering a sophisticated living experience across its three-story architectural design. Positioned on the first floor, this residence provides a seamless blend of modern functionality and refined living, defining a new standard for elevated residential comfort. The kitchen serves as the heart of the home, equipped with high-end stainless steel appliances and advanced smart refrigerator technology. The workspace is defined by elegant stone counters, providing both durability and a sleek aesthetic for culinary preparation. This space is designed to support both daily routines and seamless entertaining with modern efficiency. The bathrooms reflect a commitment to a spa-inspired routine. One bathroom features a luxurious walk-in shower, which incorporates multiple shower heads and an overhead rainfall shower system, offering a tailored and refreshing bathing experience. Beyond the interior living spaces, the property provides a dedicated porch area, offering an ideal setting for relaxation or extending your living environment into the fresh air. With its thoughtful layout and contemporary appointments, this residence offers an exceptional opportunity for those seeking a move-in ready home in a prime location. We invite you to schedule a private tour to experience the quality and refined atmosphere of this exceptional Upton residence firsthand.

140 Main St Unit B, Upton

Listing courtesy of Listing Agent: Michael Dagilis from Listing Office: ERA Key Realty Services- Milf.

$449,900

3 Beds ⋅ 2 Baths ⋅ 73589345 MLS

Some photos are virtually staged for marketing purposes. This charming Colonial-style home blends timeless New England character with modern conveniences. The first floor features beautiful wide-plank wood floors in the living and dining rooms, along with a cozy fireplace that adds warmth and character. The updated kitchen boasts tile flooring, granite countertops, and stainless steel appliances. A full bathroom on the main level adds convenience. Upstairs, you'll find three bedrooms with wood flooring throughout, along with a newly updated full bathroom featuring tile floors and an expansive jetted tub-perfect for unwinding at the end of the day. Step outside onto the deck and relax while enjoying peaceful views of Warren Brook. With its classic charm, thoughtful updates, and inviting outdoor space, this home offers a wonderful blend of comfort and character.

6 Glen Ave, Upton

Listing courtesy of Listing Agent: Paul Murphy from Listing Office: Keller Williams South Watuppa.

Start Your Search

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non commercial use of consumers having a good faith interest in purchasing, leasing or renting listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing, leasing or renting. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.

Ready to explore homes in Upton? Contact the realinsyghts group today at (508) 686-0940.

Select any listing for more information

How much is your home worth?

How much is your home worth?