Upton Real Estate

Welcome to Upton, Massachusetts—a hidden gem nestled in the heart of Worcester County. With its picturesque landscapes and charming small-town atmosphere, Upton offers a delightful blend of rural serenity and modern convenience. This vibrant community is characterized by its rich history, friendly residents, and a strong sense of belonging.

Founded in 1735, Upton boasts a captivating historical backdrop, with several well-preserved buildings and landmarks that tell the story of its past. Residents and visitors alike can explore the town’s heritage through its quaint downtown area, featuring local shops, eateries, and the iconic Upton Town Common, a perfect spot for a leisurely stroll or a family picnic.

Nature enthusiasts will find plenty to love in Upton, as the town is surrounded by lush greenery and scenic trails. The Upton State Forest offers miles of hiking and biking paths, making it an ideal destination for outdoor activities. Additionally, the nearby Lake Nipmuc provides a tranquil setting for fishing, kayaking, and enjoying summer days by the water.

Upton is also known for its excellent school system, making it a sought-after location for families. With a close-knit community feel and numerous local events throughout the year, residents enjoy a vibrant social life that fosters connections and friendships.

Conveniently located just a short drive from Worcester and other major cities, Upton offers the perfect balance of peaceful living and accessibility. Whether you’re looking for your first home or seeking a serene retreat, Upton is a wonderful place to call home. Discover the charm of Upton and experience the warmth of this remarkable community today!

Newest Listings in Upton

$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.

$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.

$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.

$1,200,000

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.

$699,000

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

"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.

72 Shannon Way Unit 102, Upton

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

$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.

$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.

$575,000

6 Beds ⋅ 3 Baths ⋅ 73588692 MLS

Two homes under one roof on a level 0.65-acre corner lot just off Main Street! Owned by the same family for decades, this classic c.1890 two-family offers 2,974 sq ft and rare flexibility. Unit 1 features 3 bedrooms, 1.5 baths, a bright bay-windowed living room, a dining room with a decorative ceiling, an updated white kitchen, and laundry. Unit 2 offers 2 bedrooms, a full bath, living room, family room, and eat-in kitchen. Each unit lives on two levels, like a home of its own. Enjoy screened porches, a deck, perennial gardens, and a yard with room to play, grow, and gather. Ideal for multigenerational living, owner-occupying one unit while rent from the other helps offset your mortgage, or adding a solid investment to your portfolio. Full basement, vinyl siding, parking for 4, and a lake/pond beach within a mile. Two-families like this rarely come to market in Upton. Schedule your showing today!

55 School Street, Upton

Listing courtesy of Listing Agent: Miller Real Estate Group from Listing Office: Keller Williams Pinnacle Central.

$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..

$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.

$1,400,000

1 Baths ⋅ 73585871 MLS

RARE INVESTMENT OPPORTUNITY IN DOWNTOWN UPTON! Bring your business, your tenants or your vision to this oversized commercial property offering serious potential for an owner user or investor. The building is in good condition and features five large overhead doors with room for trucks, campers, commercial vehicles and equipment, plus interior space with the potential to accommodate 6 automotive lifts. Ideal for an automotive garage, service business, contractor operation, fleet use, storage or a creative commercial concept. Excellent frontage and visibility create even more opportunity to grow, expand or reposition the property for future use. Properties with this kind of size, access and versatility are difficult to find. Whether you are looking to operate your own business, create multiple revenue streams or add a flexible commercial asset to your portfolio, this is one worth seeing. Bring the ideas. Bring the business. Bring the possibilities.

90-92-94 Main Street, Upton

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

$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.

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Upton Real Estate

Newest Listings in Upton

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