Upton Homes under $600,000

Welcome to Upton, Massachusetts – a charming town nestled in Worcester County, where quaint New England charm meets modern convenience. Known for its picturesque landscapes, Upton boasts a rich history and a tight-knit community that makes it an ideal place to call home. With its lush parks, scenic trails, and vibrant local culture, Upton offers a serene escape from the hustle and bustle of city life, while still providing easy access to major highways and nearby urban centers.

One of the most appealing aspects of Upton is its diverse range of homes available for under $600,000. Whether you’re a first-time homebuyer or looking to downsize, this budget-friendly market offers a variety of options to suit your needs. From charming colonial-style houses with classic architecture to modern builds that feature open floor plans and energy-efficient designs, you’ll find something that captures your heart. Many properties come with spacious yards, perfect for family gatherings or enjoying a quiet afternoon outdoors.

Upton is also renowned for its excellent school system, making it an attractive destination for families. The town hosts various community events throughout the year, fostering a welcoming atmosphere where neighbors become friends. With its blend of natural beauty, community spirit, and affordable housing options, Upton is truly a hidden gem in Massachusetts. Come explore this delightful town and discover the perfect home that awaits you!

Newest Upton Homes under $600,000

$410,000

4 Beds ⋅ 3 Baths ⋅ 73584424 MLS

Land, Location and Upside! Calling all investors, developers and DIYers! 23 North St in Upton is the value-add opportunity you've been waiting for. Priced at $410,000 and sold strictly as-is, this one is ready for your vision and some sweat equity. Set on a rare 5.8 acres, the property gives you options: renovate and restore the existing home, redevelop the site, or build new. The home was used as a multifamily, so you could rework the layout, reconfigure the space, or take it in a completely new direction. The land leaves plenty of room to expand the footprint, add outbuildings or garages, or create a private retreat set well apart from the neighbors, with the kind of privacy and space that's increasingly hard to find. Opportunities with this much land and upside don't come along often. Bring your vision, your contractor and your plans, and see what 23 North St can become. Schedule your showing today! Sold as-is. Buyer to perform own due diligence regarding zoning, permitted use, and development potential.

23 North St, Upton

Listing courtesy of Listing Agent: Nick Hanney from Listing Office: eXp Realty 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.

$599,000

3 Beds ⋅ 2 Baths ⋅ 73581868 MLS

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 remodeled, oversized eat-in kitchen is truly the heart of the home, featuring a propane fireplace, grill/smoker, two ceiling fans, and ample room for gatherings. Numerous updates provide modern peace of mind, including newer windows, roof, exterior paint, and a Generac whole-house generator. The main level offers exceptional flexibility, with a spacious living room highlighted by a dramatic floor-to-ceiling stone fireplace, two additional bedrooms, a full bath, and a convenient laundry room. The inviting family room features a wood stove and opens directly to a 17.9' x 9.2' screened composite porch with cathedral ceiling and ceiling fan ~ the perfect spot for enjoying peaceful summer evenings. Just beyond, an additional 13' x 23' composite deck overlooks the stunning private yard, complete with fruit trees and mature plantings. Upstairs, the expansive primary bedroom provides a private retreat with its own ensuite bath and plenty of room to unwind. Additional features include an oil-fired boiler, Viessmann indirect hot water heater, updated electrical panel for the Generac generator, oversized parking, and an additional barn/garage/shed offering abundant storage and space for hobbies, equipment, or your favorite grown-up toys. Ideally located just minutes from Westborough Center and less than 10 miles from the Westborough MBTA station, this home offers the tranquility of a private 3+ acre setting with convenient access to commuting, shopping, dining, and everyday amenities. Experience your own slice of heaven in Upton, home to award-winning schools and a wonderful sense of community. Your next chapter—and perhaps the perfect place to be home for the holidays awaits!

15 North St, Upton

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

$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.

$449,000

4 Beds ⋅ 2 Baths ⋅ 73577739 MLS

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 own deck. The expanded kitchen and dining area also offer access to an additional large deck. Another 3 bedrooms and full bath round out the remainder of the main level. The lower level of this home is perfectly set up for future expansion of your choosing. The benefits of Upton are numerous: Pratt Pond, easy proximity to 495 and great schools to name a few. This is a fantastic opportunity to buy a solid home in a great community!

68 School St, Upton

Listing courtesy of Listing Agent: William Glanton from Listing Office: Berkshire Hathaway HomeServices Stephan Real Estate.

$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.

$569,000

3 Beds ⋅ 2 Baths ⋅ 73573230 MLS

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 kitchen features Stainless Steele appliances, durable granite countertops, and a breakfast bar, flowing naturally to the main living spaces, perfect for everyday living and entertaining.On the second floor you will find three generously sized bedrooms all with hard-wood flooring. The bathroom offers a double-bowl vanity for added convenience and functionality. This delightful property combines charm, functionality, and thoughtful updates in a comfortable and convenient setting. Central air conditioning provides year-round comfort.The finished lower level of the home offers an ideal space to gather to watch a movie, the big game, or just a place for quiet time. Private deck overlooking a fenced in back yard, complete with a firepit. One car garage and a circular driveway add to the overall comfort of this home While the home's classic colonial design adds timeless appeal its location provides easy access to major highways, all for under $600,000

40 Hartford Ave N, Upton

Listing courtesy of Listing Agent: Cindy Donati from Listing Office: Century 21 Custom Home Realty.

$499,000

3 Beds ⋅ 3 Baths ⋅ 73569379 MLS

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 history and remarkably preserved original details, the property is ideally suited for an antique home enthusiast, preservationist, or skilled restorer with the vision to thoughtfully renovate and bring this significant residence into its next chapter. Seller has installed a new 4 bedroom Septic System. The property is being sold in AS-IS condition. Buyers and buyers' agents are responsible for performing their own due diligence regarding the property, its condition, systems, permitted uses, renovation requirements, historical significance, and any other matters important to them. Other than new septic and town water, Seller makes no representations of any type or kind as to condition.

15 W Main St, Upton

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

$550,000

4 Beds ⋅ 3 Baths ⋅ 73559135 MLS

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 area with pellet stove is perfect for entertaining. A spectacular third floor addition encompasses a large primary suite with a spectacular, spa like bathroom. Three/four more bedrooms on the second floor - One with an attached room makes a perfect in home office or nursery. Private back yard with a huge deck complete with a pergola. Above ground pool, fire pit, and storage shed, all surrounded by mature gardens, and perennials. Come take a look - you'll fall in love!!

24 Main St, Upton

Listing courtesy of Listing Agent: Jeannie Leombruno from Listing Office: Century 21 Custom Home Realty.

$489,000

3 Beds ⋅ 3 Baths ⋅ 73500996 MLS

Discover unmatched sophistication, style & elegance living at 140 Main St U:B, Upton, MA! A COMMUTER'S DREAM -- RE-IMAGINED in 2020, this 1785 square foot residence presents an attractive property in near-flawless condition, offering an exceptional opportunity for discerning buyers. The meticulously designed kitchen serves as the heart of the home, equipped with stainless steel appliances, elegant stone counters, and an integrated smart refrigerator, catering to both culinary enthusiasts and modern lifestyle demands. The bathrooms are conceived as private sanctuaries, with select spaces featuring a walk-in shower, enhanced by multiple shower heads, and a rainfall shower, providing a spa-like experience. This condominium, spanning three stories and situated on the first floor, offers three bedrooms and two full bathrooms, complemented by a convenient half bathroom. An inviting porch extends the living space outdoors, perfect for relaxation or entertaining. We invite you to experience the refined elegance of this property firsthand.

140 Main St Unit B, Upton

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

$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.

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