Upton Homes with Colonial Style

Welcome to Upton, Massachusetts—a charming town nestled in the heart of Worcester County, where history meets modern living. With its picturesque landscapes, friendly community, and rich New England heritage, Upton offers an idyllic setting for families and individuals alike. Known for its beautiful parks, top-rated schools, and a strong sense of community, Upton is a perfect blend of small-town charm and suburban convenience.

One of the standout features of Upton is its stunning array of Colonial-style homes. These timeless residences, characterized by their symmetrical facades, gabled roofs, and elegant detailing, reflect the town's historical roots while providing modern comforts. Whether you’re strolling through tree-lined streets or exploring the lush greenery of local parks, you’ll find that these homes exude a sense of warmth and character that is hard to resist.

Living in a Colonial-style home in Upton means embracing a lifestyle steeped in tradition. These homes often feature spacious layouts, inviting front porches, and classic architectural elements that make them perfect for both entertaining and everyday living. Many have been lovingly updated to include modern amenities, ensuring that you can enjoy the best of both worlds.

Upton’s vibrant community offers a plethora of activities, from farmers' markets to local festivals, making it a wonderful place to call home. Experience the charm of Upton and discover your dream Colonial-style home today—where history and modernity come together in perfect harmony!

Newest Upton Homes with Colonial Style

$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.

$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.

$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.

$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.

$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.

$1,100,000

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.

$1,150,000

4 Beds ⋅ 4 Baths ⋅ 73521066 MLS

30 Mendon St, Upton, MA Experience modern luxury in this newly constructed 2026 single-family home over 3,000 square feet of thoughtfully designed living space. Blending timeless elegance with contemporary comfort, this exceptional residence is crafted for today’s lifestyle. Featuring four spacious bedrooms and four full bathrooms, the home provides both privacy and convenience with high-end finishes throughout. The open and inviting layout is ideal for both everyday living and entertaining. A two-car built-in garage offers secure parking and additional storage, while the welcoming front porch adds charm and curb appeal to this stunning new construction. Located in desirable Upton, this home presents a rare opportunity to own a beautifully designed residence in impeccable condition.

30 Mendon St, Upton

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

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