Upton Real Estate

Welcome to Upton, Massachusetts, a hidden gem nestled in Worcester County that perfectly balances small-town charm with modern conveniences. With a rich history dating back to the 18th century, Upton offers residents a unique blend of scenic beauty and a tight-knit community atmosphere.

Surrounded by lush greenery and picturesque landscapes, Upton is an ideal location for nature lovers. The town is home to several parks and recreational areas, including the beautiful Upton State Forest, where residents can enjoy hiking, biking, and picnicking amidst the serene woods. The nearby Lake Hiawatha provides a tranquil spot for fishing and kayaking, making it a perfect getaway for outdoor enthusiasts.

Upton's vibrant community is reflected in its local events and activities. From farmers' markets to seasonal festivals, there’s always something happening that brings residents together. The town boasts a strong sense of community spirit, with friendly neighbors and a welcoming atmosphere that make newcomers feel right at home.

Families will appreciate Upton's top-rated schools, which are part of the Mendon-Upton Regional School District. These institutions are dedicated to fostering a supportive and enriching environment for students, ensuring a bright future for the children of Upton.

Conveniently located near major highways, Upton offers easy access to neighboring towns and cities, including Worcester and Boston, making it an ideal spot for commuters. With its charming downtown area filled with local shops, restaurants, and cafes, Upton is not just a place to live; it’s a place to thrive. Come discover the warmth and beauty of Upton, MA—your new home awaits!

Newest Listings in Upton

$1,300,000

4 Beds ⋅ 5 Baths ⋅ 73566681 MLS

Open House: Saturday and Sunday 11:00-12:30! Welcome to 8 Juniper Road, where impressive space, thoughtful updates, and a truly spectacular backyard oasis come together in one exceptional home. Offering approximately 3,600 sq. ft. of living space, 4 bedrooms, 4.5 bathrooms, and a 3-car garage, this beautifully maintained and updated property is designed for both comfortable everyday living and unforgettable entertaining. Inside, a spacious and thoughtfully designed floor plan offers generous room sizes, abundant natural light, and plenty of space to gather, work, relax, and entertain. The kitchen serves as the heart of the home and features an updated backsplash, newer appliances, kitchen vent, and a newer slider providing seamless access to the outdoor living areas. Upstairs, the spacious primary bedroom features its own private en suite bath, while an additional bedroom also offers a private full bathroom, an ideal setup for a live-in nanny, guests, extended family, or anyone looking for added privacy. Step outside and prepare to fall in love! The backyard is a true private oasis featuring a stunning heated in-ground pool, hot tub that flows directly into the pool, expansive composite deck, professional landscaping, and irrigation system. Whether hosting summer gatherings, relaxing in the hot tub, dining outdoors, or spending the afternoon poolside, this incredible setting feels like your own private resort. The extensive list of improvements adds tremendous value and peace of mind, including a new boiler, well tank and well pump in 2021; composite deck, pool liner, pool heater and pool pump in 2022; irrigation system in 2023; first-floor AC condenser in 2024; and newly repaved driveway in 2026. Additional improvements include exterior painting and replaced trim, kitchen slider, dishwasher, microwave, kitchen backsplash, venting and more.Set in a desirable Upton neighborhood, this property offers privacy and tranquility while remaining convenient to schools, shopping, dining, recreation, and major commuter routes. With approximately 3,700 sq. ft., 4 bedrooms, 4.5 baths, two bedrooms with private en suite baths, a 3-car garage, extensive updates, and an incredible resort-inspired backyard, 8 Juniper Road offers an exceptional combination of space, amenities, and outdoor living that is difficult to find!

8 Juniper Road, Upton

Listing courtesy of Listing Agent: Amy Bisson from Listing Office: Lamacchia Realty, Inc..

$975,000

4 Beds ⋅ 3 Baths ⋅ 73566169 MLS

Welcome to a truly exceptional Colonial where timeless elegance meets modern comfort. Meticulously maintained and thoughtfully updated, this stunning 4-bedroom, 2.5-bath home offers generous living spaces, 9-foot ceilings, and abundant natural light, creating a warm and inviting atmosphere throughout. The beautifully appointed kitchen is a cook’s dream, featuring upgraded granite countertops, stainless-steel appliances, a double oven, an approximately two-year-old refrigerator, and an oversized walk-in pantry. The first floor also offers convenient laundry, a half bath, a spacious dining room with French doors—perfect for holiday gatherings—and an additional sitting room that provides an ideal home office or flex space. The 23x23 cathedral-ceiling living room offers a cozy retreat with a pellet stove, perfect for relaxing on chilly winter evenings. Quality finishes and thoughtful upgrades throughout the home showcase a level of character, warmth, and established charm that new construction simply cannot replicate. Upstairs, the spacious primary suite features an en-suite bath with newer quartz countertops, double sinks, a walk-in shower, and a generous walk-in closet. Three additional well-sized bedrooms and a full bath with tub/shower and newer quartz countertops complete the second floor. The unfinished walk-out basement, with 9-foot ceilings and large windows, offers incredible potential for additional living space, a recreation room, home gym, or whatever your needs may be. The oversized two-car garage, complete with a negotiable car lift, provides exceptional flexibility for car enthusiasts, hobbyists, or additional storage. Adding to the home’s appeal is an extremely reasonable solar lease at just $137.15 per month, offering the potential for significant energy cost savings. All of this is set in an amazing location, making this exceptional Colonial a wonderful place to call home. With its spacious layout, thoughtful upgrades, abundant potential, and timeless character, this is a home you won’t want to miss!

161 South St, Upton

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

$695,000

4 Beds ⋅ 3 Baths ⋅ 73565350 MLS

Timeless charm & modern comfort describe this renovated Colonial originally built in 1828 on a scenic, quiet country road. Fully reframed in 1988, with a kitchen/family room addition in 1994, this spacious home is in excellent condition. This saltbox-style home blends historic character with contemporary living. The kitchen/family room & the primary bedroom suite have cathedral ceilings & skylights. The open-concept kitchen is designed for entertaining featuring new stainless steel appliances & a convenient peninsula. The adjacent front-to-back living room creates an inviting space for relaxing with a charming fireplace, perfect for cozy evenings. This home provides four comfortable bedrooms & two full baths, with the primary bath offering a jetted tub with shower. The floorplan offers flexibility for multiple home office options. Once you step outside the privacy of the large, level lot and heated in-ground pool designed for leisurely summer days, leaves you imagining the wonderful memories to be made. This much-loved property is the perfect blend of historic elegance and modern amenities. Kiwanis Beach (1/2 mi), Upton Heritage Park (1/4 mi), Upton State Forest (3 mi away), all offer passive recreation opportunities. UPDATES TO PROPERTY: New 4BR septic 2026; Indirect hot water heater 2025; 200 AMP electric 2023; SS kitchen appliances 2025; Chimney repointing 2026; Roof 2023.

5 Elm Street, Upton

Listing courtesy of Listing Agent: Lisa Pezzoni from Listing Office: Andrew J. Abu Inc., REALTORS®.

$899,000

4 Beds ⋅ 5 Baths ⋅ 73564539 MLS

Exceptional Colonial on 3.21 Private Acres. Discover the perfect blend of comfort and lifestyle in this exceptional colonial, set on 3.21 acres of stunning, pastoral landscape. Designed to inspire, the home is bathed in natural light and offers breathtaking sunset views—providing the perfect backdrop for working from home. The open-concept floor plan flows seamlessly, featuring a spacious family room, a bright four-season sunroom, and an expansive deck, making it an ideal space for family gatherings and entertaining. You will appreciate the versatility of both first and second-floor primary suites, all complemented by beautiful hardwood flooring throughout. For the equestrian enthusiast, this property is a true standout. It features a 4–6 stall barn, a 140’x70’ sand arena, and direct trail access to the Upton State Forest. Additional amenities include a detached three-car garage and a sparkling in-ground pool for refreshing summer days. With a newer furnace (2019) and a functional, spacious layout, this home offers incredible potential. Bring your vision and a few updates to make this unique property your own.

96 Fowler St, Upton

Listing courtesy of Listing Agent: Isaac Alvarenga from Listing Office: Property Investors & Advisors, LLC.

$675,000

4 Beds ⋅ 2 Baths ⋅ 73563625 MLS

Fabulous Turn-Key Cape home has a number of custom touches not found in new construction. Home has had major systems updated in the last two years: Viessmann 42-gallon indirect oil-fired hot water heater, highly-efficient Williamson oil-fired boiler, new well pump & piping ~ all with long-term warranties. All appliances less than 2 years including washer, dryer, refrigerators, stoves. Exterior of fireplace just cleaned, repointed and new cap. Updated electrical and windows. First floor has a large foyer, generously sized living room with stunning hardwoods and fireplace, oversize eat-in kitchen, laundry, full bath & 3 good-size bedrooms. Second floor ADU accessed by totally separate entrance to the rear has an eat-in kitchen, pantry, full bath, living room, good-size bedroom, and additional room perfect for a home office. Town-approved 4 bed new septic system to be installed. Gorgeous lot on just under an acre, tons of parking in horseshoe driveway. Garage under. Move-in ready ~ perhaps do some minor cosmetic upgrades to make it your own. Great for income property or first-time buyer looking to have rental income or space for extended family. Come enjoy all Upton has to offer ~ award-winning schools, conservation lands, convenient commuter location to Rt. 495, 140, and the local T stations ~ located near Hopkinton, Hopedale, Milford lines!! Property is vacant and easy to show! This is a Must See!!

90 Glenview, Upton

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

$879,900

4 Beds ⋅ 3 Baths ⋅ 73562333 MLS

Stately Colonial offering a rare combination of natural beauty, modern updates, and everyday tranquility. Every window captures peaceful views of the surrounding landscape, creating a vacation-at-home feeling year-round. This spacious home features beautiful hardwood floors throughout the 1st floor & a versatile floor plan designed for easy everyday living & entertaining. The stunning kitchen is the heart of the home, offering abundant cabinetry, a walk-in pantry & opens to the oversize cathedral-ceiling family room. 1st floor laundry/mudroom adds everyday convenience. Private primary suite includes a flexible bonus room ideal for another home office, fitness space or sitting area. A plethora of windows fills the home with bright, natural lighting. Thoughtfully sited for maximum privacy, the inviting farmer’s porch & expansive composite deck provide ideal spaces to relax or entertain. Taft Mill & Goss Pond are just a short walk away, offering kayaking, fishing, hiking & year-round recreation, with convenient access to I-495, the Mass Pike, Worcester, Providence & Boston. A rare opportunity to enjoy privacy, natural beauty & modern updates in one exceptional property. Welcome Home!

2 Brookside St, Upton

Listing courtesy of Listing Agent: Leah Burke from Listing Office: William Raveis R.E. & Home Services.

$1,340,000

5 Beds ⋅ 4 Baths ⋅ 73562275 MLS

Set amid park-like grounds with a private wooded backdrop, this expansive Upton home stands out for its generous living space, thoughtful updates and remarkable flexibility. Updated kitchens and baths throughout bring a fresh, polished feel to the home, while impressive architectural details begin in the soaring two-story foyer and continue into the dramatic family room, where a vaulted ceiling, fireplace and an extraordinary collection of windows fill the space with natural light and views of the surrounding landscape. At the center of the main level, the updated kitchen features quartz counters, extensive cabinetry, stainless appliances, gas/propane cooking and an oversized island. Its open connection to the breakfast area and family room creates an inviting gathering space, while the generous dining room provides plenty of room for larger occasions. A private office or library with built-in bookshelves offers a quiet, distinctive space away from the main gathering areas. The home's generous proportions continue upstairs, where the exceptionally spacious primary suite features two walk-in closets and a beautifully updated, spa-like private bath. Three additional bedrooms, another updated full bath and conveniently located laundry complete the bedroom level. One of the property's greatest advantages is the finished lower level. With its own updated kitchen, bedroom, full bath, living/guest space and recreation room, it offers an outstanding setup for multigenerational living or extended family, while also providing tremendous flexibility for recreation, guests, a home gym or additional living space. Outdoors, a heated inground pool with newer liner, expansive deck with pergola, raised garden beds, brick walkways, fire pit, flowering shrubs and perennials create a wonderful setting for summer gatherings and time at home. Tucked within mature landscaping and a wooded setting, the backyard feels like its own retreat while remaining convenient to Upton's town center, schools, recreation and major commuting routes. An oversized garage provides exceptional vehicle and storage space, while fully owned solar and a newer 5-bedroom septic system are significant improvements for the next owner. See for yourself at our open house on August 15th, 2026 from 12-1:30 PM.

66 Glenview St, Upton

Listing courtesy of Listing Agent: Lisa Aron Williams from Listing Office: Coldwell Banker Realty - Sudbury.

$519,999

3 Beds ⋅ 4 Baths ⋅ 73560822 MLS

Welcome to this WEST-FACING townhouse in the desirable SAMREEN VILLAS community. 13 KNOWLTON CIRCLE offers low-maintenance living in a convenient Upton location.This 3-BEDROOM, 3.5-BATH home features an OPEN-CONCEPT FLOOR PLAN with HARDWOOD FLOORS, a SPACIOUS KITCHEN, and abundant natural light throughout the main living area. The second floor includes THREE GENEROUSLY SIZED BEDROOMS and a LARGE LOFT that can be used as a HOME OFFICE, SITTING AREA, OR FLEX SPACE.The FINISHED LOWER LEVEL with a FULL BATHROOM provides additional living space suitable for a FAMILY ROOM, GUEST SUITE, HOME GYM, OR OFFICE. A PRIVATE DECK extends the living area outdoors, and the attached 2-CAR GARAGE adds convenience.Recent updates include GARAGE DOORS (APPROXIMATELY 1.5 YEARS OLD), WATER HEATER (2026), NEWER WASHER, NEWER DISHWASHER, AND NEWER CARPETING IN THE FINISHED BASEMENT.Conveniently located near MAJOR ROUTES, SHOPPING, DINING, AND LOCAL AMENITIES, this home offers a FUNCTIONAL LAYOUT with VERSATILE LIVING SPACES.

13 Knowlton Cir Unit 13, Upton

Listing courtesy of Listing Agent: Smita Sinha from Listing Office: Keller Williams Pinnacle MetroWest.

$495,000

3 Beds ⋅ 1 Baths ⋅ 73560760 MLS

Welcome to this 3-bedroom (with brand NEW 3 Bedroom Septic being installed) split-level home offering a wonderful opportunity to build equity and create the home you’ve always envisioned. The main level features a bright living room, a spacious eat-in kitchen with access to the rear deck, and three comfortable bedrooms. The finished lower-level family room provides additional living space ideal for a playroom, home office, media room, or gym. An attached one-car garage offers convenient parking and extra storage. Step outside to enjoy the level backyard, perfect for entertaining, gardening, pets, or outdoor activities. A brand-new septic system is currently being installed, providing added value and peace of mind for the next owner. While the home does need flooring, paint, and updating, it offers solid bones and endless potential. Bring your ideas, creativity, and vision to transform this property into your dream home. Conveniently located in the highly desirable town of Upton with easy access to schools, parks, shopping, and major commuter routes, this is a fantastic opportunity for investors, contractors, or buyers looking to customize a home and make it truly their own. Don’t miss your chance to unlock the potential this property has to offer!

4 Picadilly St, Upton

Listing courtesy of Listing Agent: Robyn Nasuti from Listing Office: Realty ONE Group Suburban Lifestyle.

$599,900

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.

$929,900

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..

$774,900

7 Beds ⋅ 4 Baths ⋅ 73552661 MLS

Don't miss this well-maintained multifamily property offering an excellent opportunity for both investors and owner-occupants. Whether you're looking to generate rental income, build long-term wealth, or offset your mortgage by living in one unit while renting the other, this property offers outstanding flexibility.Each unit features spacious living areas, comfortable bedrooms, functional layouts, and abundant natural light. The property provides ample parking, outdoor space, and the convenience of separate living areas, making it attractive to tenants and homeowners alike.Ideally located in the heart of Upton, you'll enjoy easy access to local shops, restaurants, schools, parks, and major commuter routes while experiencing the charm of a welcoming New England community.This is a rare opportunity to own an income-producing property in a desirable location with strong rental already.

158 Main St, Upton

Listing courtesy of Listing Agent: Rita Silva Martins from Listing Office: eXp Realty LLC - Corporate Office.

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