Upton Homes under $2 million

**Discover Upton, MA: Your Ideal New Home Awaits!**

Nestled in the heart of Worcester County, Upton, Massachusetts, is a charming town that beautifully blends small-town charm with modern conveniences. Known for its picturesque landscapes and friendly community spirit, Upton offers a tranquil escape from the hustle and bustle of city life while remaining conveniently close to major urban centers. With a rich history dating back to the 1700s, Upton is filled with character and a sense of belonging that makes it a wonderful place to call home.

One of the most appealing aspects of Upton is its diverse range of homes available for under $2 million. Whether you're a first-time homebuyer, looking to downsize, or seeking a spacious family residence, Upton has something to suit every lifestyle. From charming colonial-style houses with lush yards to modern new constructions boasting open floor plans, the real estate market here is vibrant and varied.

Families will appreciate the top-rated schools and abundant recreational opportunities, including parks, walking trails, and community events that foster a strong sense of togetherness. The town’s commitment to preserving its natural beauty is evident in its many conservation areas, making it a haven for outdoor enthusiasts.

With its welcoming atmosphere, excellent amenities, and an array of homes under $2 million, Upton is not just a place to live; it’s a community to thrive in. Come explore what this delightful town has to offer, and find your dream home in Upton today!

Newest Upton Homes under $2 million

$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.

$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.

$700,000

3 Beds ⋅ 2 Baths ⋅ 73584356 MLS

Welcome to 192 Westboro Rd, a beautifully maintained Upton home offering the perfect balance of modern comfort, classic character and a natural setting. Thoughtfully updated over the years, this move-in-ready home features an updated kitchen with quartz countertops, renovated baths, windows, stone hearth, hardwood flooring and a brand-new ducted heat pump providing efficient heating and cooling. Two spacious storage sheds, including a workshop, offer ample storage and versatile workspace. With thoughtful improvements throughout, there is so much to appreciate both inside and out. The setting is what makes this property truly unique. Conservation land surrounds the property, with Upton State Forest just across the street, offering miles of trails for hiking, mountain biking and cross-country skiing right outside your door. Enjoy fishing, kayaking and beautiful New England foliage, with Westborough Reservoir and Whitehall Reservoir both less than 10 minutes away. For commuters, the location offers convenient access to major routes and nearby communities, making it easy to enjoy privacy and nature while being connected to work, shopping, dining and everyday amenities. Enjoy the best of both worlds: a beautifully updated, move-in-ready home surrounded by nature, with outdoor recreation and convenient access. Come see all that 192 Westboro Rd has to offer.

192 Westboro Rd, Upton

Listing courtesy of Listing Agent: Ian Teng from Listing Office: Redfin Corp..

$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: .

$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.

$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.

$1,165,000

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 ⋅ 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..

$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.

$649,900

3 Beds ⋅ 2 Baths ⋅ 73571939 MLS

Welcome to this charming 3-bedroom, 1.5-bath Colonial ideally situated in a desirable neighborhood with an unbeatable in-town location. Just moments from the local High School and Vocational School, the home offers convenient access to the schools' expansive fields for recreation, walking, track and outdoor activities. Inside, the main level features a bright, open kitchen and dining area that flows seamlessly into a comfortable living room anchored by a fireplace with a wood-burning insert, providing warmth throughout the home. Kitchen offers ample cabinet space, granite counter-tops, hardwood flooring and stainless steel appliances. A versatile first-floor room adds flexibility — currently used as a home office yet well-suited to serve as a formal dining room. A thoughtfully added mudroom off the garage entry provides abundant closet space, an updated half bath, and conveniently houses the laundry. Upstairs there are three bedrooms and a spacious full bathroom. Primary bedroom has 2 walk in closets. The finished, heated lower-level family room offers additional living and recreation space, with added shelving providing ample storage alongside this inviting retreat. Rounding out the property is an attached two-car garage equipped with MyQ smart garage door openers and a private backyard with added patio and a shed. Less than 5 miles to Rt. 495 - Don't miss your chance with this wonderful opportunity!

4 Florence Cir, Upton

Listing courtesy of Listing Agent: TEAM Metrowest from Listing Office: Berkshire Hathaway HomeServices Commonwealth Real Estate.

$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.

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