Upton Homes under $500,000

Welcome to Upton, Massachusetts – a hidden gem nestled in Worcester County that perfectly balances small-town charm with modern conveniences. Known for its picturesque landscapes and friendly community, Upton offers a serene lifestyle just a short drive from the hustle and bustle of larger cities. With a rich history dating back to the 1700s, this quaint town is characterized by its beautiful parks, scenic walking trails, and a vibrant downtown area filled with local shops and eateries.

For those seeking a place to call home, Upton presents an enticing opportunity with a selection of homes available for under $500,000. Whether you're a first-time homebuyer, a growing family, or someone looking to downsize, Upton has something for everyone. From charming single-family homes with spacious backyards to cozy townhouses in welcoming neighborhoods, you'll find a diverse range of properties that cater to various lifestyles and budgets.

The community spirit in Upton is palpable, with local events and activities that bring residents together throughout the year. Families will appreciate the excellent school system, while nature enthusiasts can enjoy the nearby Upton State Forest, perfect for hiking, biking, and exploring the great outdoors.

With its affordable housing options and a strong sense of community, Upton is not just a place to live; it’s a place to thrive. Discover your dream home in this delightful town, where comfort meets convenience, and every day feels like a breath of fresh air. Come explore Upton, where your next chapter awaits!

Newest Upton Homes under $500,000

$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

$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

$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

$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

$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

$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

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