Upton Homes for Sale

Welcome to Upton, Massachusetts – a hidden gem nestled in Worcester County, where small-town charm meets modern convenience. This picturesque town, known for its friendly community and scenic landscapes, offers an ideal setting for families, young professionals, and retirees alike. With its rich history dating back to the 1700s, Upton boasts a blend of historic charm and contemporary living, making it a wonderful place to call home.

Upton is characterized by its lush green spaces, including the stunning Upton State Forest, which provides ample opportunities for hiking, picnicking, and enjoying the great outdoors. The town is also home to a variety of local shops, eateries, and community events that foster a strong sense of belonging among residents. The highly-rated schools in the area ensure that families have access to quality education, while the town's proximity to major highways and commuter rail lines makes it easy to reach nearby cities like Worcester and Boston.

For those considering a move to Upton, you’ll be pleased to discover a diverse selection of homes for sale. From charming colonial-style houses to modern new builds, there’s something to suit every taste and budget. Many properties feature spacious yards, updated interiors, and convenient amenities. Whether you’re looking for a cozy starter home or a larger residence for your growing family, Upton’s real estate market has plenty to offer.

Explore the inviting neighborhoods of Upton and find your dream home in this delightful community. Discover the perfect blend of tranquility and accessibility in Upton, where your new life awaits!

Newest Upton Homes for Sale

$625,000

4 Beds ⋅ 3 Baths ⋅ 73559135 MLS

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.

$950,000

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..

$399,900

4 Beds ⋅ 3 Baths ⋅ 73557327 MLS

Calling All Contractors, Investors & Flippers! Exceptional opportunity to transform this 4-bedroom Coln, privately sited on nearly 2 acres in desirable Upton. Featuring an impressive family room, 2 full baths, first-floor laundry, an unfinished LL & a 2-car under garage, this home offers a fantastic floor plan and tremendous potential. The property is in need of a complete renovation due to burst pipes and subsequent professional remediation. All damaged materials have been removed, leaving the home ready for its next chapter. Please note that there is currently no active plumbing or functioning bathrooms. The roof is Sept 2022 and furnace is approximately 10 years old. Cash buyers only. This property will not qualify for conventional financing. Open House Sun 2-4

324 Mendon Street, Upton

Listing courtesy of Listing Agent: Marilyn Green from Listing Office: RE/MAX Signature Properties.

$649,900

4 Beds ⋅ 3 Baths ⋅ 73556199 MLS

**OFFER DEADLINE - Tues, 8/4, 3PM** Welcome to this beautifully crafted 2006-built Colonial offering 2,324 square feet of thoughtfully designed living space. With 4 bedrooms and 2.5 bathrooms, this home blends timeless New England style with modern updates throughout.The spacious kitchen features upgraded quartz countertops and custom cabinetry and shelving with abundant storage, perfect for everyday living and entertaining. The primary suite includes a private en-suite bathroom for a comfortable retreat. A brand-new deck at the rear of the home overlooks more than two acres of land that abuts conservation land, offering exceptional privacy and natural surroundings. The walkout basement presents excellent potential for additional finished living space.Additional highlights include a massive 2-car garage with extra storage capacity, central air conditioning installed in 2014 and solar panels that help reduce utility costs. This home has plenty of potential for its next owner to make it their own.Don't miss this opportunity to own a well-maintained Colonial on a private, oversized lot in Upton, MA — conveniently located near local roadways, schools, and town amenities.

30 Pearl St, Upton

Listing courtesy of Listing Agent: Michael O'Brien from Listing Office: ERA Key Realty Services- Fram.

$499,000

3 Beds ⋅ 1 Baths ⋅ 73555450 MLS

***OPEN HOUSE CANCELED***Stunning views with the ability to enjoy time on the water for under $500K. Welcome home to this beautiful single-family ranch in Upton MA across the street from Pratt Pond. Enjoy kayaking, canoeing, boating, and fishing just steps from your front door. This well maintained 3-bedroom 1-bath home sits on a flat 0.75-acre lot perfect for spending time outside entertaining, gardening, and more. Inside you are met with a beautiful living room with vaulted ceilings and a scenic view of the water. Your comfortable kitchen flows nicely into the dining room which is well sized to host your next get-together. Down the hall your full bathroom and three bedrooms await (one with your washer and dryer) all with hardwood flooring. Additional highlights include a heated 2-car detached garage with plenty of storage space, a fenced-in backyard and plenty of off-street parking. Homes that offer scenic views, a usable yard, and this much value are hard to find. Don't miss this opportunity to make this charming Upton home your own! Call to schedule your showing today!

71 School St, Upton

Listing courtesy of Listing Agent: Matthew McLaughlin from Listing Office: Premeer Real Estate Inc..

$1,159,000

4 Beds ⋅ 3 Baths ⋅ 73553629 MLS

NEIGHBORHOOD SETTING WITH COMMUTER CONVENIENCE! This North-facing colonial offers over an acre of mature, professionally landscaped yard space that abuts trails and conservation land. Inside, the open layout is anchored by an incredibly spacious family room and modern chef’s kitchen with a double oven, 5-burner gas cooktop and oversized island to use for casual dining eating or as a homework hub. There’s even a custom wet bar with a wine fridge! Other 1st floor features include a private office with details you can't miss - crown molding and French doors - plus a gorgeous, sun-lit living room, elegant dining room, and laundry. Upstairs, the primary suite features walk-in closets alongside three additional bedrooms, all with hardwood floors. You’ll beat the heat with BRAND NEW AC condensers (’26). EV charger stays. Outside, spend your summers on the composite deck and custom patio overlooking a tranquil fish pond - all fenced in with a shed for storage. This is move-in-ready luxury!

33 Dairy Drive, Upton

Listing courtesy of Listing Agent: Erika Steele from Listing Office: REMAX Executive Realty.

$899,900

4 Beds ⋅ 3 Baths ⋅ 73551967 MLS

Tucked away on a quiet cul-de-sac with 2 acres of wooded bliss, this Federal-front Colonial is pure serenity with an incredibly spacious layout to boot. It's 3000+ square feet that feels warm and homey with New England charm oozing from every room. The kitchen has NEW quartz countertops and a massive eat-in area with a downdraft gas stove. It flows seamlessly into a sun-drenched family room with exposed beams, NEW skylights and a NEW ceiling fan. A second living space, formal dining, and powder room round out the main floor. Upstairs, the primary suite boasts a beautiful NEW bathroom and three spacious bedrooms. Outside, a NEW composite deck overlooks a massive backyard where you can grow your own fruit! You'll love the established pear and cherry trees, blueberry bushes, plus there’s a fenced garden area ready for someone with a green thumb. Additional UPDATES include vinyl siding, front steps, garage doors and the finished lower level. Opportunity is knocking—don’t wait to answer!!

10 Sadler Road, Upton

Listing courtesy of Listing Agent: Erika Steele from Listing Office: REMAX Executive Realty.

$1,300,000

4 Beds ⋅ 4 Baths ⋅ 73550062 MLS

Room to grow......inside and out! Expansive 4 bedroom 2 1/2 bath home with separate IN-LAW in finished basement all nestled on a picturesque 8.3 acres! This gem boasts a 2 story foyer, hardwoods throughout the first floor and newer carpet throughout the second floor. Oversized primary suite with cathedral ceiling, large walk-in closet, jacuzzi tub, stand up shower/double vanity. Huge family room with floor to ceiling fireplace , hardwoods and tons of natural light. Electrolux Central Vacuum, Leafguard gutters, hot water heater with booster are just some of the many amenities. 4 Room IN-LAW in finished basement with separate entrance and full bath. Time to get in before school starts!

9 South Street, Upton

Listing courtesy of Listing Agent: Robin Haddad from Listing Office: Mendon Local Realty.

$989,900

4 Beds ⋅ 4 Baths ⋅ 73547396 MLS

UNDER CONSTRUCTION...Enjoy The Benefits of New Construction with Energy Efficiency & Low Future Maintenance! This stunning home offers the perfect blend of classic elegance and modern convenience with a spacious 1st FLOOR PRIMARY SUITE and laundry and 3 additional bedrooms on the 2nd level. The partially finished basement with finished half bath provides extra square footage plus access to the spacious backyard. 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 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 Sept 2026 Closing

19 West Main Street, Upton

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

$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 September 2026 Closing.

17 West Main Street, Upton

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

$789,900

4 Beds ⋅ 3 Baths ⋅ 73546600 MLS

This exceptional 3.7 acre country estate blends luxury living with outstanding outdoor amenities. The Colonial home features hardwood floors, soaring ceilings, multiple fireplaces, wood stoves, new central heat, mini-splits, and a gourmet kitchen with granite counters and stainless appliances. The main level offers formal and casual living spaces, a bright dinning room, living room, family room, full bath, and bonus room. Upstairs are four bedrooms, including a spacious primary suite with 3/4 bath and a custom California Closet. The finished lower level adds 2 rooms for more flexible living space. Solar panels, updated well equipment, and a new boiler improve efficiency. Outside, enjoy a hot tub, screened porch, fire pit, pond, barn/gym and large recreation area with a soccer/basketball half court. Located across from Upton State Forest with direct access to miles of trails.

218 Mechanic, Upton

Listing courtesy of Listing Agent: Amy Bedard from Listing Office: Transitions Realty.

$2,500,000

4 Beds ⋅ 5 Baths ⋅ 73541742 MLS

75-Acre Elite Equestrian & Wellness Sanctuary. Ultimate private retreat with a 4,040 SF luxury Cape, world-class horse facilities, and resort backyard. Trail access to West Hill Dam. RESIDENCE: Chef's kitchen (Jade 6-burner, Sub-Zero, granite waterfall island). 1st-floor primary suite with vaulted ceilings & spa bath. 3 upper bedrooms, office, large bonus room + finished walkout lower level. 2-car garage with EV charger & generator backup. EQUESTRIAN: Professional 9-stall barn, heated tack room, wash stall & blanket laundry. 12,384 SF indoor arena (172'x72') + 130'x80' outdoor arena. 60' round pen & 15 turnout paddocks. Roof solar array on barn supplies powers to the property. WELLNESS & RESORT: Detached climate-controlled gym & solar yoga "She Shed." Heated, saltwater, gunite pool, hot tub, 6-person barrel sauna. Outdoor kitchen with pizza oven. Meditation labyrinth, organic fruit orchards, and berry patches.

117 South Street, Upton

Listing courtesy of Listing Agent: Beth Byrne from Listing Office: Gibson Sotheby's International Realty.

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