Upton Homes with Colonial Style

Welcome to Upton, Massachusetts, a hidden gem nestled in Worcester County that perfectly blends small-town charm with modern conveniences. Known for its picturesque landscapes and tight-knit community, Upton offers an inviting atmosphere for families, professionals, and retirees alike. With its rich history dating back to the 18th century, Upton boasts a variety of recreational activities, including scenic parks, hiking trails, and community events that foster a sense of belonging.

One of the most appealing aspects of Upton is its stunning array of Colonial-style homes. These architectural treasures reflect the town’s historical roots while providing the comfort and functionality that today’s homeowners desire. With their classic symmetry, elegant facades, and inviting front porches, Colonial homes in Upton exude timeless charm. Many of these residences feature spacious interiors, hardwood floors, and beautifully landscaped yards, making them perfect for both entertaining and everyday living.

Living in Upton means enjoying a peaceful suburban lifestyle while being conveniently located near major highways, allowing for easy access to nearby cities like Worcester and Boston. Residents appreciate the top-rated schools, vibrant local businesses, and a strong sense of community that make Upton a wonderful place to call home.

Whether you’re searching for a charming Colonial to raise your family or a serene retreat to enjoy your golden years, Upton offers a diverse selection of homes that cater to various tastes and preferences. Discover the beauty of Upton and find your dream home in this delightful Massachusetts town!

Newest Upton Homes with Colonial Style

$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.

$849,900

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.Roof & gutters (2026), low maintenance oversized Trexdeck (2026), HVAC, heat/ac pump & hot water tank (2024), newer kitchen fridge & microwave. Desirable induction oven. Welcome home! OPEN HOUSES Sat 8/29 & Sun 8/30 12:30-2:00.

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.

$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.

$875,000

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.

$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..

$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.

$1,125,000

4 Beds ⋅ 4 Baths ⋅ 73541292 MLS

Glen Echo is a most desirable neighborhood close to Rt 495, MA Pike & Westborough. This pristine & spacious 4 bedroom, 3.5 bath Chatsworth Model Colonial has been impeccably maintained by its original owners. Enter to dramatic 2 story foyer w/ wainscoting & balcony. Open floor plan, 9 ft ceilings & tons of windows give this home an airy & roomy feel. Main level boasts hardwoods throughout. Gourmet eat-in kitchen is a cook's dream - granite, SS appliances, dbl oven, vented out hood vent, walk-in pantry, expansive island, butler's nook, desk area & sliders to composite deck overlooking private yard w/ woodland views. Spacious family room w/ FP. Large office w/ French doors, living room, dining room & laundry/mud room complete 1st floor. Added convenience - a 2nd staircase. Spectacular Primary Suite w/ sitting area, gorgeous bath, jetted tub & updated tiled shower. Jack & Jill bath connects two good size bedrooms. 3rd full bath in 4th bedroom. ~2000 sq ft unfinished basement w/ sliders.

35 Howarth Dr, Upton

Listing courtesy of Listing Agent: Gerald Simone from Listing Office: Mathieu Newton Sotheby's International Realty.

$1,075,000

4 Beds ⋅ 3 Baths ⋅ 73522448 MLS

32 Mendon St, Upton, MA. Where modern sophistication meets timeless design. This newly constructed 2026 residence offers 2,924 square feet of impeccably curated living space, blending contemporary elegance with refined modern farmhouse architecture. Every detail has been intentionally selected — from premium finishes to elevated craftsmanship — creating a home that feels both luxurious and enduring. Designed for elevated living, the expansive floor plan features 4 spacious bedrooms, 2 full baths, and 1 half bath, seamlessly balancing comfort and style. The two-car garage adds convenience, while the gracious front porch delivers a distinguished first impression. Generously sized basement with full build-out opportunity. Set on a property with exceptional outdoor potential, this residence presents a rare opportunity to own a home defined by quality, sophistication, and architectural presence.

32 Mendon St, Upton

Listing courtesy of Listing Agent: Luana Velame from Listing Office: Century 21 The Real Estate Group.

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