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15 North St, Upton
$599,000
3 Beds ⋅ 2 Baths ⋅ SOLD Status ⋅ 73581868 MLS ⋅ 1,496 SqFt.
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

68 School St, Upton
$449,000
4 Beds ⋅ 2 Baths ⋅ SOLD Status ⋅ 73577739 MLS ⋅ 1,392 SqFt.
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

24B River Street, Upton
$670,000
3 Beds ⋅ 2 Baths ⋅ SOLD Status ⋅ 73571380 MLS ⋅ 2,055 SqFt.
Imagine summer days spent at nearby Kiwanis Beach and evenings under the stars in your private backyard Jacuzzi. Beautifully maintained home offers an exceptional setting just a short walk from Upton Center, the beach, ballfield and courts, and approximately four miles from the Hopkinton I-495 exit and Price Chopper Plaza. Inside, the open kitchen and family room create a warm, inviting place to entertain family and friends. The kitchen features granite countertops and hardwood floors, with a pretty eat in area with slider to the deck, while the cathedral family room is enhanced by a fireplace, hardwood flooring and new skylights. Three bedrooms, two full baths and a two-car garage add everyday comfort. The bedrooms are nicely sized and the baths and kitchen are in great condition. Upstairs, an open loft makes a wonderful office or sitting area, with access to a generous storage area offering potential for additional living space. The finished lower level adds even more room to enjoy. A spacious deck, outdoor shower and shed complement the gorgeous backyard. Sellers have completed many updates in the past 3 years including new carpet and paint, mini splits, furnace, skylights, washer, dryer and fridge. See updates and additional information attached. They also installed a radon mitigation system. This home is truly "move in ready" and a place you can come home to after a long day and just relax. These sellers hope the next owners love this home as much as they have! Don't miss this excellent opportunity to own this lovely home with seasonal water views and within walking distance to so many great places!

24B River Street, Upton

90 Glenview St, Upton
$590,000
4 Beds ⋅ 2 Baths ⋅ SOLD Status ⋅ 73540925 MLS ⋅ 2,534 SqFt.
Price improvement by motivated seller ~ New 4-Bed Septic being installed! 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 hot water heater, highly-efficient Williamson 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 chimney cap installed. 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.Gorgeous lot offers privacy on just under an acre, mature plantings, and tons of parking in horseshoe driveway. Garage under. Move-in ready ~ some minor cosmetic upgrades will make it your own.Amazing legal 2-family home for income property or first-time buyer looking to have mortgage help or space for extended family. Come enjoy all Upton has to offer ~ award-winning schools, conservation lands, local produce, 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!! Also listed as a single family with ADU MLS:73563625,

90 Glenview St, Upton

71 School St, Upton
$515,000
3 Beds ⋅ 1 Baths ⋅ SOLD Status ⋅ 73555450 MLS ⋅ 1,316 SqFt.
***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

10 Hopkinton Rd, Upton
$445,000
3 Beds ⋅ 2 Baths ⋅ SOLD Status ⋅ 73538093 MLS ⋅ 1,176 SqFt.
Adorable Upton home ready to make your own! This charming property offers so many desirable features, including abundant natural sunlight streaming through the skylights, a convenient location just minutes from Route 495, and beautiful views of Pratt Pond. Enjoy a private backyard with endless potential for entertaining, gardening, or simply relaxing outdoors. Inside, you'll find flexible living space to fit a variety of needs. The finished lower level offers excellent possibilities as a guest suite, in-law space, home office, recreation room, or additional family living area. Whether you're a first-time homebuyer, looking to downsize, or searching for a home with room to grow, this property provides comfort, convenience, and opportunity. Don't miss your chance to enjoy all that Upton has to offer in this inviting home!

10 Hopkinton Rd, Upton

11 James Rd, Upton
$735,000
3 Beds ⋅ 3 Baths ⋅ SOLD Status ⋅ 73537714 MLS ⋅ 1,304 SqFt.
Upton Horse Haven: Iconic 3-Bed, 3-Bath Retreat on 3.75 Acres. Discover one of Upton’s most beloved properties, a premier estate where timeless charm meets outdoor living. This home features modern upgrades including 200-amp electrical system, a new oil tank, and town water for seamless reliability. A newly finished basement for entertaining or retreat. Property offers direct access to miles of trails in the Upton State Forest—perfect for hikers, riders, and nature lovers. The BOH allows boarding for 2-3 horses, making it a dream for equestrians. Set on 3.75 lush acres and just minutes from I-495, it combines suburban serenity with effortless access to city conveniences. According to town zoning regulations the property is subdividable offering flexibility for future development. Don’t miss this iconic, horse-friendly haven—bring your vision and schedule your tour today.

11 James Rd, Upton

33 Dairy Drive, Upton
$1,100,000
4 Beds ⋅ 3 Baths ⋅ SOLD Status ⋅ 73553629 MLS ⋅ 3,360 SqFt.
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

78 Main Street, Upton
$677,500
6 Beds ⋅ 3 Baths ⋅ SOLD Status ⋅ 73552323 MLS ⋅ 2,617 SqFt.
Rare 2-Family Gem with Historic Charm & Modern Luxury. Discover this meticulously renovated two-family home, perfectly situated on 2 sprawling acres near the heart of town. Gutted to the studs in 2015 and updated with a new roof, windows, and high-end finishes, this property offers the peace of mind of a new build with the character of a classic estate. Both units are fully de-leaded, light-filled, and feature gorgeous wide-plank and hardwood floors, granite countertops, and stainless steel appliances. Unit 1 (822 sq. ft.): A comfortable first-floor layout with direct access to a full basement featuring private laundry hook-ups. Unit 2 (1,811 sq. ft.): A stunning two-story retreat (levels 2 & 3) boasting 4 spacious bedrooms, 2 full baths, a dedicated laundry room, and a massive walk-in closet. Mechanicals are top-tier with separate utilities, including two new boilers, 2022, 2023 and tankless hot water heaters. Outside, the property shines with exceptional curb appeal, 8 parking spaces

78 Main Street, Upton

4 Picadilly St, Upton
$480,000
3 Beds ⋅ 1 Baths ⋅ SOLD Status ⋅ 73560760 MLS ⋅ 1,080 SqFt.
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

41 Rockwood Ln Unit 41, Upton
$779,900
2 Beds ⋅ 2 Baths ⋅ SOLD Status ⋅ 73561608 MLS ⋅ 1,743 SqFt.
Impressive Like New Freestanding Ranch Home in Highly Sought-After Rockwood Meadows Over 55 Community on The Hopkinton Line Just A Few Miles Away From 495/MA Pike Exits. Premium Lot Which Backs up Conservation Area Offering Miles Hiking, Biking and Running Trails. Features an Open Plan With Gorgeous Cherry Cabinet Kitchen, Granite Counters, Stainless Appliances, Center Island and Access to Private Deck, Gas Fireplaced Family Room, Hardwood Floors Throughout, Crown Moldings and Tons of Natural Light in Every Room! Large Primary Suite Features His/Her Closets and Fantastic Bath With Granite, Spacious Second Bedroom With Adjacent Full Bath Also With Granite, Laundry Room With Cherry Cabinets, Huge Basement With Excellent Finishing Potential For Lots of Extra Living Space, Low HOA Fees Include Access to The Awesome Clubhouse With Fitness Center and Entertainment Space For Large Gatherings + Year Round Exterior Maintenance!, Affordable FHA Gas Heat, Central Air, Lowest-Priced One Owner Home Offers The Opportunity to Be Among Much Higher Priced Homes! Come Take a Look at This Detached Home That Shows Mint - You Will Feel Like You Entered a Model Home.

41 Rockwood Ln Unit 41, Upton

149 Glenview St, Upton
$640,000
3 Beds ⋅ 2 Baths ⋅ SOLD Status ⋅ 73540194 MLS ⋅ 1,546 SqFt.
Bursting with charm and set on 1.84 picturesque acres, this white antique Cape offers standout curb appeal on a scenic country road. Designed for easy living, the first floor features the primary bedroom, full bath, laundry, and an open-concept living, dining, and kitchen area with beautiful backyard views and direct access to the deck. Outside, the freshly painted red barn and smaller white barn, both with electricity, add character, versatility, and exciting potential, with the larger barn ready for restoration and future possibilities. Ideally located near the Hopkinton line, this property is a commuter’s dream—just over 3 miles to I-495—while still convenient to shopping, dining, and everyday amenities. A rare opportunity to enjoy classic New England charm, usable acreage, and a sought-after location.

149 Glenview St, Upton

218 Mechanic, Upton
$751,500
4 Beds ⋅ 3 Baths ⋅ SOLD Status ⋅ 73546600 MLS ⋅ 2,668 SqFt.
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

30 Pearl St, Upton
$680,000
4 Beds ⋅ 3 Baths ⋅ SOLD Status ⋅ 73556199 MLS ⋅ 2,324 SqFt.
**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

6 Wood St, Upton
$1,090,000
4 Beds ⋅ 3 Baths ⋅ SOLD Status ⋅ 73428709 MLS ⋅ 3,260 SqFt.
Where Luxury Meets Country! Welcome to this beautifully updated 4BR, 3,000+ sq ft home in scenic Upton. Perfect for entertaining with spacious foyer, formal dining & sitting room, plus expansive family room off the remodeled gourmet kitchen with quartz countertops, stainless steel appliances, double oven, compactor & decorative cabinet lighting. Upstairs offers 4 bedrooms & 2 full baths incl. a primary suite with sitting area, double walk-in closets & spa-like en suite with soaking jet tub. Finished lower level is heated/cooled with bonus room, craft/workshop & mudroom with garage access. Enjoy the new front porch & composite back deck overlooking premier equestrian facilities: 2 barns with 7 stalls, 4 fenced paddocks, 90’x110’ riding ring & 50’ round pen, & tack/grain room. Energy-efficient upgrades include Tesla solar panels (owned), new hot water tank, new condenser & more. Surrounded by fruit trees & gardens, this rare horse property blends luxury living with top-notch amenities.

6 Wood St, Upton

45 Mendon Street, Upton
$866,900
3 Beds ⋅ 3 Baths ⋅ SOLD Status ⋅ 73537667 MLS ⋅ 3,076 SqFt.
Custom-built Colonial set on a picturesque 1.55-acre lot. Showcasing exceptional craftsmanship, quality construction and a thoughtfully designed floor plan, this home offers the perfect blend of comfort and functionality for today's lifestyle. The spacious family room features a soaring ceiling and striking stone fireplace, creating a warm and inviting gathering space. The kitchen offers beautifully crafted cabinetry, generous counter space and seamless flow to the formal dining room, ideal for entertaining. A home office, first-floor laundry, and versatile living room or den complete the main level. Upstairs, the expansive primary suite includes two walk-in closets and a private bath, while 2 additional bedrooms complete the 2nd floor. Enjoy the charming front porch and spacious rear deck with Trex decking overlooking the private yard. A partially fenced area is perfect for four-legged friends. Two-car garage, walk-out basement, timeless design, meticulous upkeep, & solid construction

45 Mendon Street, Upton

324 Mendon Street, Upton
$460,000
4 Beds ⋅ 3 Baths ⋅ SOLD Status ⋅ 73557327 MLS ⋅ 2,340 SqFt.
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

236 Mendon St, Upton
$635,000
3 Beds ⋅ 2 Baths ⋅ SOLD Status ⋅ 73537386 MLS ⋅ 1,638 SqFt.
The charm of yesteryear with moden conveniences. This meticulously maintained and updated 3 bed, 1.5 bath Antique home has been loved by same family for 93 years and is now looking for the next family to welcome home. Pride of ownership shows in custom laid hardwoods and buit-ins. Light-filled large rooms, 4 working fireplaces in the living room, first-floor bedroom, and two upstairs bedrooms. Home offers expansion potential with 15.3 x 14.7 unfinished wing, adjacent to kitchen, waiting for your imagination. Central air, furnace, water heater, roof, and updated baths all newer and installed since 2013. Detached garage/shed for projects, storage, or parking. Stunning level lot has been the ideal setting for weddings, parties, and story hours throughout the generations. This home is truly a must-see!! Located convenient to Upton's many conservation land/trails, schools, highways, and all Upton has to offer! Sellers willing to sell completely furnished.

236 Mendon St, Upton

5 Pleasant St, Upton
$420,000
3 Beds ⋅ 1 Baths ⋅ SOLD Status ⋅ 73530168 MLS ⋅ 1,727 SqFt.
Bring your vision and unlock the potential of this classic Colonial set on a beautiful, level lot in desirable Upton! Offering a rare combination of major exterior updates and room to build instant equity, this home is the perfect opportunity for investors, contractors, or buyers eager to create their dream home. Significant improvements have already been completed including 9 year old vinyl siding & roof. Inside, you’ll find hardwood floors, an updated kitchen, generous room sizes and abundant natural light throughout. While the interior is ready for cosmetic improvements and renovation, the possibilities are endless. The spacious yard provides plenty of room for entertaining, gardening, recreation, or future enhancements. Conveniently located near schools, parks, shopping, restaurants, and commuter routes. A solid home with great bones, valuable updates already in place, and tremendous upside in one of Upton’s most sought-after communities.

5 Pleasant St, Upton

145 W River Street, Upton
$910,000
4 Beds ⋅ 3 Baths ⋅ SOLD Status ⋅ 73525258 MLS ⋅ 3,956 SqFt.
Prepare to be enchanted by this stunning, perfectly designed home. One level living at its finest. Crafted with the utmost precision and meticulous design. Every inch of the home was carefully thought of – from a perfectly situated mudroom, to a seamlessly flowing open concept living area, four generously sized bedrooms, a large study, a wonderful oversized four-season porch and an outdoor patio. The finest materials & finishes enhance every element of this home. Beautiful engineered wood floors throughout. Sophisticated designer kitchen, complete with an oversized island, quartz countertops, and top of the line stainless steel appliances. The primary suite offers expansive walk-in closets with an en-suite bath. This exceptional property is nestled in beautiful grounds on a 5.5 acre lot. Deadline for offers is 5:00 pm Tuesday, June 16, 2026. Please make offers good for 24 hours.

145 W River Street, Upton

27 W River St, Upton
$1,200,000
4 Beds ⋅ 3 Baths ⋅ SOLD Status ⋅ 73532182 MLS ⋅ 3,570 SqFt.
Modern farmhouse-inspired luxury meets exceptional craftsmanship in this stunning custom-built ranch set on 4.8 private acres. Designed for effortless single-level living, this one-of-a-kind home offers an open-concept floor plan filled with natural light from oversized windows and accented by gleaming hardwood floors throughout the main living areas. The sleek chef’s kitchen features tall custom cabinetry, quartz countertops, premium finishes, and a spacious layout ideal for entertaining. The luxurious primary suite serves as a private retreat with a spa-inspired bath and expansive walk-in closet. Three additional bedrooms & 2.5 baths. The beautifully finished walkout lower level dramatically expands the living space and is ideal for a media room, game room, home office, gym, or guest accommodations. Outside, a spectacular hardscape patio overlooks the private grounds. Abutting state forest with great walking trails.

27 W River St, Upton

27 James Road Unit 4, Upton
$752,000
2 Beds ⋅ 4 Baths ⋅ SOLD Status ⋅ 73525704 MLS ⋅ 2,200 SqFt.
LAST UNIT AVAILABLE NEW CONSTRUCTION. Free standing unit no age restrictions in 4 lot subdivision. Kitchen is spacious with eat in dining area, hardwood floors, granite, kitchen island, stainless steel appliances. Opens to a family room with access to backyard. Upstairs has a 3 bedroom layout but deeded as a 2 bedroom dwelling 3rd room could be in home office/den/playroom. Ensuite primary with tiled shower and glass enclosure with double vanity sinks and soaking tub. Second full bath for bedroom 2 and bonus room. Finished room and full bath in walk out basement with full egress door no bulkhead, plus storage area. Third floor walk up also has an area for storage or future finished space. House is on a dead end street close to center of town! Home are less than 5 miles to RT495, making it a great commuter location. Less than a 1/2 mile to boat ramp on Pratt Pond and 1 mile to Kiwanis Beach on Pratt Pond where you can enjoy swimming, boating and fishing. It truly is the perfect location!

27 James Road Unit 4, Upton

1 South St, Upton
$770,000
4 Beds ⋅ 3 Baths ⋅ SOLD Status ⋅ 73500985 MLS ⋅ 3,018 SqFt.
Welcome home to this distinctive four-bedroom property set on a picturesque 1.84-acre lot, offering the perfect blend of charm, space, and modern updates. Enjoy peaceful mornings on the inviting farmer’s porch or unwind on the stunning new patio while taking in beautiful sunset views. Inside, this home is anything but ordinary, featuring hardwood floors, a flexible first-floor bedroom, and a dramatic second-floor fireplaced family room that adds warmth and character. The expansive primary suite serves as a private retreat with an ensuite bath, bonus space for a reading nook or exercise area, and access to a walk-up attic with future potential. Numerous major updates—including heating system, roof, windows, oil tank, hot water heater, fresh paint, carpets, slider, and new D-box—provide true move-in readiness. Additional highlights include a finished lower-level room ideal for a gym or hobby space. Located in desirable Upton with top-rated schools and easy access to major routes.

1 South St, Upton

8 Stearns Road, Upton
$1,375,000
5 Beds ⋅ 5 Baths ⋅ SOLD Status ⋅ 73508751 MLS ⋅ 4,395 SqFt.
Nestled at the end of a private cul-de-sac on nearly two acres, this meticulously renovated Colonial estate offers a premier multi-generational layout featuring main residence & fully equipped accessory dwelling. Beautiful main house boasts a mahogany deck, chef’s kitchen complete w/ quartz countertops, double wall ovens, gas cooktop, & an oversized butcher-block island, all adjacent to a coffee, wine bar & dining area w/attached deck. 2 fireplaced living rooms & 1/2 bath. New great room above the garage. Second floor hosts 4 bedrooms including luxurious primary suite w/ spa-like bath & walk-in closet. A newly finished walk-up attic game room. Connected by a breezeway, the self-contained ADU, perfect for an Au Pair or InLaw, boasts its own full kitchen, fireplaced living area, office, and a bedroom overlooking serene nature views. This expansive property has 2/two car garages, is pro landscaped and hardscaped and full main house generator. Main house lovingly renovated, ADU is new!

8 Stearns Road, Upton

51 School St Unit 3, Upton
$410,000
3 Beds ⋅ 2 Baths ⋅ SOLD Status ⋅ 73526517 MLS ⋅ 1,420 SqFt.
Welcome to this beautifully maintained 3 bedroom, 2 bath condominium in the desirable town of Upton. This bright and inviting home features an open concept layout designed for comfortable living and effortless entertaining. The modern kitchen is highlighted by elegant quartz countertops, ample cabinetry, and a seamless flow into the dining and living areas.Enjoy year round comfort with central heating and air conditioning throughout the home. The spacious primary bedroom offers a private retreat, while two additional bedrooms provide flexibility for family, guests, or a home office. Additional highlights include a washer and dryer conveniently located in the unit and the ease of low maintenance condominium living.

51 School St Unit 3, Upton

215 North St, Upton
$810,000
3 Beds ⋅ 3 Baths ⋅ SOLD Status ⋅ 73488757 MLS ⋅ 3,300 SqFt.
Set at the end of a dead-end road, this expanded custom contemporary offers over 10 acres of private land—a rare blend of space, flexibility, and future potential. This well-maintained 3-bed, 2.5-bath home is filled with natural light from expansive windows and skylights, creating an open, inviting layout. A standout 30x24 heated bonus room above the garage provides exceptional space for recreation, entertaining, or extended living. Additional features include a deck, indoor jacuzzi, wood stove, mini-splits (2 yrs), newer windows and roof (~10 yrs), boiler (2014), 200 amp electrical, generator hookup, and private well. Passing Title V with oversized 4-bed septic allows for expansion or ADU potential. Preliminary subdivision plans (subject to approvals). Convenient to major highways with access to Westborough, Framingham, and Natick, offering easy commute to Boston.

215 North St, Upton

11 Howarth Drive, Upton
$1,100,000
4 Beds ⋅ 4 Baths ⋅ SOLD Status ⋅ 73516986 MLS ⋅ 3,768 SqFt.
OPEN HOUSE CANCELLED. Stunning move-in ready home in highly desirable Glen Echo Estates near the Upton/Westborough line! This beautifully designed property offers sun-drenched living spaces, hardwood flooring & an open-concept layout perfect for today’s lifestyle. Dramatic two-story foyer, elegant dining room, private home office & an inviting family room with wood-burning fireplace create exceptional living spaces throughout. The chef’s kitchen features exotic quartzite countertops, stainless steel appliances, oversized island & flows seamlessly into a bright sunroom ideal for entertaining. Luxurious primary suite with tray ceiling, spa-like bath & walk-in closet. Flexible bonus space perfect for media room, gym or potential 5th bedroom. Expansive deck overlooks a peaceful wooded backyard offering privacy & relaxation. Walkout basement, 3-car garage & convenient commuter location with easy access to major routes complete this exceptional offering.

11 Howarth Drive, Upton

57 Plain St, Upton
$525,000
3 Beds ⋅ 3 Baths ⋅ SOLD Status ⋅ 73528006 MLS ⋅ 1,372 SqFt.
Experience effortless single-level living in this beautifully updated Ranch on a level corner lot at 57 Plain St. The main level features two bedrooms with pristine hardwood floors, plus a bright sun-filled kitchen boasting stainless steel appliances, a skylight, new tile flooring, fresh cabinets, and stone countertops. Thoughtful layout includes a full and a half bath on the main floor and a welcoming living room. The finished lower level adds flexible space—perfect as a third bedroom option or a cozy family room. Peace of mind comes with a newer 3-bedroom septic system installed in 2018. Just moments from all Upton has to offer, this home is turnkey and ready for you to enjoy. Extra perks include a fully fenced yard, a new heating system, an oversized storage shed & sauna. All the heavy lifting is complete—welcome home.

57 Plain St, Upton

20 Josiah Drive, Upton
$785,000
4 Beds ⋅ 3 Baths ⋅ SOLD Status ⋅ 73538003 MLS ⋅ 2,408 SqFt.
Welcome to 20 Josiah Drive, a beautifully maintained Colonial in one of Upton’s most desirable neighborhoods. This spacious 4-bedroom, 2.5-bath home offers over 2,200 sq ft of sun-filled living space with newly refinished hardwood floors and an open layout ideal for everyday living and entertaining. The vaulted-ceiling great room and fireplaced family room create warm and inviting spaces, while the formal dining room and additional living area offer flexibility for today’s lifestyle. All four bedrooms are located on the second floor, including a spacious primary suite with a walk-in closet and private en-suite bath. The main level features a large kitchen with granite countertops, hardwood flooring, dining area, a fully heated & insulated sunroom, and composite deck overlooking the private backyard with mature landscaping and peaceful seasonal views. Additional highlights include central air, fenced yard, 2-car garage, and excellent curb appeal.

20 Josiah Drive, Upton

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