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$1,763,100
4 Beds ⋅ 5 Baths ⋅ 73355665 MLS
Perched on 3 acres of beautifully wooded land, Lot 3 features a spacious 3,609-square-foot home that perfectly balances modern elegance with classic architectural charm. The original rendering showcased stone accents on the front facade, but the final design will feature a stylish combination of board & batten siding with traditional clapboard, offering a timeless look. Inside, this home is designed with five generously sized bedrooms and 5.5 bathrooms, providing ample space for family and guests. A standout feature of this home is its walk-out lower level, which presents incredible potential for additional finished space, whether you envision a home theater, playroom, or fitness area. For those who enjoy indoor-outdoor living, there is an optional screened porch upgrade, allowing homeowners to take full advantage of the serene surroundings while adding a cozy retreat to the home. Thoughtfully crafted with high-end finishes and a flexible floor plan, this home offers a sophisticated li

7 Sawmill Brook Lane, Upton

Listing courtesy of Listing Agent: TEAM Metrowest from Listing Office: Berkshire Hathaway HomeServices Commonwealth Real Estate.
$1,500,000
4 Beds ⋅ 7 Baths ⋅ 73508003 MLS
Exceptional custom-built home offering over 5,000 sq ft of refined living space with 4 bedrooms, 5 full and 2 half baths, & a 3-car garage. Thoughtfully designed w/ high-end finishes throughout, this home blends luxury w/ warmth. The stunning kitchen features stone countertops, a large island, wood pizza oven & premium SS appliances, opening to a fire-placed family room. A coffered ceiling formal living room & a 3-season porch w/ fireplace, bar sink, & mini-split add to the appeal. Every bedroom includes a private en-suite bath, primary has chromo therapy shower. The bonus room above the garage offers half bath & future expansion potential. The walk-out lower level offers over 1200 sq. ft. & includes radiant heat, a bedroom, ¾ bath, & laundry hookups. Enjoy outdoor living on the beautiful stone patio w/ fire pit overlooking a flat, expansive yard. Loaded w/ upgrades (see FEATURES list attached to MLS) incl. radiant heat flooring, Sonos, central vac, water filtration, EV charger & more!

72 Glenview St, Upton

Listing courtesy of Listing Agent: TEAM Metrowest from Listing Office: Berkshire Hathaway HomeServices Commonwealth Real Estate.
$1,500,000
4 Beds ⋅ 4 Baths ⋅ 73443069 MLS
A timeless New England farmhouse-style under construction on Lot 2, sitting on 4.3 scenic acres & offering 3,586 square feet of living space. Facing east, the home is perfectly positioned to capture fantastic sunrises—best enjoyed from the inviting farmer’s porch, which adds curb appeal & serves as the perfect place to start your day w/ a morning coffee or unwind in the evening. Designed for versatility, this home includes 4 or 5 bedrooms & 3.5 bathrooms, w/ a thoughtfully planned layout that adapts to your needs.The 1st floor office can easily serve as a 5th bedroom. Inside, an open floor plan maximizes natural light, while high-end finishes & thoughtful details create a sophisticated yet comfortable living environment. The walk-out lower level offers the possibility of addt finished space, ideal for a recreation room, gym, or guest suite. W/ its adaptable design & generous lot size, Lot 2 is a fantastic opportunity for buyers looking for a customizable luxury home. Ready Feb 2026!

6 Sawmill Brook Lane, Upton

Listing courtesy of Listing Agent: TEAM Metrowest from Listing Office: Berkshire Hathaway HomeServices Commonwealth Real Estate.
$1,375,000
5 Beds ⋅ 5 Baths ⋅ 73508751 MLS
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

Listing courtesy of Listing Agent: Kathleen Nicoloro from Listing Office: Ferrari + Co. Real Estate.
$1,206,281
4 Beds ⋅ 3 Baths ⋅ 73436185 MLS
Tucked away on a spacious lot in desirable Upton, this newly built home showcases expert craftsmanship by a seasoned local developer. Offering 3,314 square feet of thoughtfully designed living space, the open floor plan seamlessly blends comfort and style, perfect for today’s modern lifestyle. At the heart of the home, an expansive chef’s kitchen connects the dining and living areas, ideal for entertaining and everyday living. Wide plank hardwood floors flow throughout, enhancing the home’s warm and inviting feel. Upstairs, the luxurious primary suite features dual walk-in closets and a spa-inspired bath w/ an oversized tile shower. Three additional generously sized bedrooms, a full bath w/ tub & tile surround, and convenient laundry room complete the 2nd level. The finished walkout basement provides additional living space and opens to a private outdoor area. Additional highlights include a charming farmer’s porch and a screened-in porch for enjoying warm evenings.

29 Cider Mill, Upton

Listing courtesy of Listing Agent: Melissa Tempesta from Listing Office: Whitewood Real Estate, Inc..
$1,200,000
4 Beds ⋅ 3 Baths ⋅ 73532182 MLS
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

Listing courtesy of Listing Agent: Robyn Nasuti from Listing Office: Realty ONE Group Suburban Lifestyle.
$1,100,000
4 Beds ⋅ 4 Baths ⋅ 73516986 MLS
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

Listing courtesy of Listing Agent: Mary G. Wood from Listing Office: Lamacchia Realty, Inc..
$1,100,000
2 Beds ⋅ 4 Baths ⋅ 73493433 MLS ⋅ ['Rockwood Meadows'] BLDG.
Absolutely Stunning Home in Rockwood Meadows Neighborhood - Detached 55+ Condo Loaded With Tens Of Thousands of Upgrades and Amenities - Lives and Feels Like a Single Family Home. A Spacious & Bright Open Floor Plan Includes First and Second Floor Master Suites With Lavish Baths, Exquisite White Cabinet Chef's Kitchen With Center Island, Granite Counters W/Leather Finish, Stainless Appliances Open to A Family Room With Gas-Fired Fireplace, Beautiful Sun Room With High Ceilings & Tall Windows, 1st Floor Study, Mostly Hardwood Throughout 1st Floor, Second Floor is Its Own Suite With a to Die For Walk-in Closet + Additional Walk-in Closets on Each Floor With Built-Ins Offering Exceptional Storage, Finished Lower Level Includes an Additional Family Room, Office, "Flex Room" and Another Full Bath! The Setting Is Outstanding ~ Only a Few Miles to 495 in Hopkinton. Use The Clubhouse Daily or For Planned Events, Walking Trails. Impeccable Home You'll Fall in Love With!

46 Rockwood Lane Unit 46, Upton

Listing courtesy of Listing Agent: Bill Gassett from Listing Office: REMAX Executive Realty.
$1,090,000
4 Beds ⋅ 3 Baths ⋅ 73428709 MLS
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

Listing courtesy of Listing Agent: Brittany Palmerino from Listing Office: Mathieu Newton Sotheby's International Realty.
$1,050,000
3 Beds ⋅ 3 Baths ⋅ 73519143 MLS
Magnificent and truly one-of-a-kind, this privately set Mid-Atlantic–style custom estate spans 5+ acres of landscaped grounds, featuring perennial gardens, mature plantings, and handcrafted stone walls. Meticulously maintained with a new septic system and water filtration, the home blends timeless elegance with modern updates. The fireplaced kitchen offers granite countertops, a custom wood island, and sunlit dining area, while the formal dining room features its own fireplace and bespoke built-ins. A dramatic living room with cathedral ceilings and a striking floor-to-ceiling window fills the home with natural light. The grand staircase leads to a luxurious primary suite with fireplace and spa-like bath with double vanity, granite, custom tile shower, and jacuzzi. Complementing the main residence is a 964 sq ft carriage house with kitchen, 1.5 baths, and flexible space. Resort-like grounds include a deck, in-ground pool, outdoor fireplace, gazebo, and shed. a rare, private retreat.

179 South St, Upton

Listing courtesy of Listing Agent: Richard Hills from Listing Office: Media Realty Group Inc..
$1,000,000
4 Beds ⋅ 4 Baths ⋅ 73507328 MLS
Impeccable Upton 4-5 Beds, 3.5 Baths. Everything has been done. Features over 4,200 sq. ft. of finished living space, this stunning property features an amazing open floor plan, high ceilings, and a large granite kitchen with high-end appliances. Major updates include a 2025 heat pump system, paid-off solar, 2023 roof, and water heater less than one year old. Full lower level expansion provides incredible additional living space. Outside, enjoy a flat yard with irrigation, an amazing heated pool, and a beautiful patio system perfect for entertaining. Three-car garage. This home is in exceptional condition, and true turnkey living in a desirable Upton location. This one won’t last! No showings until open house May 2nd

154 South Street, Upton

Listing courtesy of Listing Agent: David Hill from Listing Office: Central MA Homes.
$970,000
4 Beds ⋅ 3 Baths ⋅ 73489095 MLS
Completely renovated in 2024, this stunning 4-bedroom, 2.5-bath home blends modern luxury with thoughtful design in a highly desirable neighborhood close to schools and town. A spacious new addition features a large primary suite with a spa-like bath and two walk-in closets, offering a true private retreat. The heart of the home is the beautifully renovated kitchen, equipped with premium Bosch appliances, perfect for both everyday living and entertaining. Throughout the home, you’ll find new hardwood floors, all new windows and doors, and high-quality finishes at every turn. The addition also introduced a gorgeous mudroom/entry with floor-to-ceiling cabinetry, providing exceptional storage and organization, along with a stylish new half bath. Central air conditioning ensures year-round comfort .Move-in ready and meticulously updated, this home offers the perfect combination of modern convenience, elegant upgrades, and an unbeatable location. Some photos have been virtually staged.

4 Hazeltine Rd, Upton

Listing courtesy of Listing Agent: Beth A. Feather from Listing Office: William Raveis R.E. & Home Services.
$949,900
2 Beds ⋅ 3 Baths ⋅ 73478671 MLS ⋅ ['Rockwood Meadows'] BLDG.
Enjoy owning a single family home with all of the benefits of community living! Stunning open first floor includes spacious kitchen with SS appliances, cherry cabinetry and 10 foot island fantastic for entertaining. Living room features gas fireplace, dining room overlooking private back yard, patio and deck. Built in patio table and benches for outside dining. Crown molding throughout the first floor. Primary suite on the main level has a walk in closet, full bath with double sink vanity, soaking tub and shower. First floor laundry. Second floor features some great spaces! Additional bedroom with two closets, full bath, loft and sitting room leading to a fully finished craft room Well maintained home. Furnace, a/c, generator and fireplace serviced in 2025. Clubhouse has a fireplaced gathering room, kitchenette, exercise room and mailroom. Shopping, restaurants nearby with easy access to 495.

63 Rockwood Ln Unit 63, Upton

Listing courtesy of Listing Agent: Linda Mossman from Listing Office: Realty Executives Boston West.
$910,000
4 Beds ⋅ 3 Baths ⋅ 73525258 MLS
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

Listing courtesy of Listing Agent: Mia Fisher from Listing Office: Berkshire Hathaway HomeServices Commonwealth Real Estate.
$900,000
4 Beds ⋅ 4 Baths ⋅ 73498867 MLS
This modern multi-Level 4-bedroom 3.5-bath masterpiece is a must see! Stunning open layout with designer finishes and abundant natural light throughout. Open kitchen with stainless appliances & quartz waterfall island flows to a fabulous dining room. Solid hardwoods throughout Luxurious sized living room with cathedral ceiling, floor-to ceiling fireplace, and double slider opening to a 20x10 composite deck is a focal point for family gatherings. 4 total bedrooms include a generous primary suite with 6x23 walk-in closet & fabulous bath with walk-in shower, double vanity, and jetted soaking tub. 2nd floor laundry room. Lower level second en-suite is perfect for guests/extended family with a heated bathroom floor. Oversize 2-car garage has electric car charger and storage space. Great commuter location near Hopkinton line, close to highways and various T stations. Horses allowed. Award-winning schools. Come enjoy this peaceful, private setting convenient to all Upton has to offer!

68 Pearl St, Upton

Listing courtesy of Listing Agent: Laura Hebb from Listing Office: .
$866,900
3 Beds ⋅ 3 Baths ⋅ 73537667 MLS
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

Listing courtesy of Listing Agent: Mary G. Wood from Listing Office: Lamacchia Realty, Inc..
$864,900
2 Beds ⋅ 3 Baths ⋅ 73347131 MLS ⋅ ['Cobblers Creek'] BLDG.
Welcome to Cobblers Creek, a serene 55+ community in Upton offering detached condominiums designed for active adults seeking low-maintenance living with commuter convenience. Tucked within a peaceful tree-lined setting yet close to Route 495 and the Mass Pike, this community blends privacy with accessibility. The Cardinal townhome floor plan features open-concept living with an eat-at island kitchen, quartz countertops, stainless steel appliances, and hardwood flooring throughout the main living areas. The primary suite includes a tiled shower and double vanity, while abundant windows and a slider open to your private deck or patio overlooking conservation land. Enjoy future amenities including walking trails, a clubhouse, and the convenience of a two-car garage. Ask about our 20k developer incentive. #CobblersCreek #UptonMA #55PlusCommunity #LowMaintenanceLiving

18 Boot Shop Road Unit 40, Upton

Listing courtesy of Listing Agent: John Konevich from Listing Office: StreamLine Communities.
$855,000
4 Beds ⋅ 3 Baths ⋅ 73511968 MLS
Welcome to this beautifully maintained Cape on a private, landscaped lot in one of Upton’s most desirable locations -featuring town water & natural gas. Extended to include an expansive addition of a primary suite over the two-car garage, this home blends comfort and function with ease... focused on entertaining. Bright, open layout with hardwood flooring and a seamless kitchen-to-dining flow—perfect for everyday living and socializing. Formal living room with classic chair rail and crown molding. First-floor laundry adds convenience. Items to note: new windows, interior painted ‘24, exterior painted in ‘21, 9 zone irrigation. Finished lower level offers flexible space and storage. The showstopper? A stunning hardscape backyard with pergola, hot tub, and inviting spaces to relax or gather with friends and enjoy sunsets, wine and laughs. Close to major routes. This is THE HOME you have to see!

3 Ephraims Way, Upton

Listing courtesy of Listing Agent: Robyn Nasuti from Listing Office: Realty ONE Group Suburban Lifestyle.
$850,000
3 Beds ⋅ 3 Baths ⋅ 73524039 MLS
Set on nearly an acre in a sought-after Upton neighborhood, this stately Colonial offers timeless appeal and thoughtful updates throughout. Major recent improvements include a renovated kitchen with creamy white cabinetry, farmhouse hardware, quartz countertops, and LG appliances, Buderus boiler, Heat Flo water tank, Roth oil tank, Carrier A/C system, energy-efficient windows, garage doors, bulkhead and newly paved expanded driveway. The spacious primary suite offers an en-suite bath, walk-in California Closet & new hardwood flooring plus 2 additional generous bedrooms. The finished lower level provides flexible space for home offices, guests or recreation, plus abundant storage. Outside, enjoy a beautifully landscaped multi-tiered backyard with a beautiful heated Gunite pool, 2 new generator ready propane tanks, a relaxing 3 season porch and low-maintenance grounds. Convenient access to Route 495 and Mass Pike for commuting to Boston, Worcester and Providence.This home is turnkey.

3 Jonathans Way, Upton

Listing courtesy of Listing Agent: The Macchi Group from Listing Office: William Raveis R.E. & Home Services.
$835,000
4 Beds ⋅ 3 Baths ⋅ 73511970 MLS
Stunning 4-bedroom, 2.5-bath Colonial tucked at the end of a peaceful cul-de-sac a minute from town. A sun-filled vaulted great room complements the home’s open layout as an inviting space for everyday living. The bright kitchen with center island flows seamlessly into dining, living, and den—ideal for both entertaining and work-from-home flexibility. The secluded backyard contains an elevated porch overlooking tree-covered hillsides, gardens, and a charming orchard with apple and plum trees. Shielded from the street by natural elevation and mature woods. The spacious master suite features a walk-in closet and master bath. 3 bonus bedrooms and 1 more bath complete the upstairs. A large unfinished basement is perfect for storage, a home gym, or future expansion. Central AC, pellet stove, fireplace, and first-floor laundry provide comfort and peace of mind. Easily accessible hiking trails complete this exceptional offering—a tranquil escape with a rare balance of privacy and convenience.

1 Quail Run, Upton

Listing courtesy of Listing Agent: Robyn Nasuti from Listing Office: Realty ONE Group Suburban Lifestyle.
$835,000
4 Beds ⋅ 3 Baths ⋅ 73468566 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 April 2026 Closing.

10 Mechanic St, Upton

Listing courtesy of Listing Agent: Kim Backlund from Listing Office: Northeast Realty + Co..
$832,000
4 Beds ⋅ 3 Baths ⋅ 73485301 MLS
Set back from the road for privacy & woodsy exploration, yet conveniently located near area amenities, this 4-bed, 2.5-bath Colonial w/ an abundance of windows/natural light, sits on 5.5 acres, w/ a beautifully landscaped yard, incl. a newly fenced back-yard & separate raised-bed garden. Owned solar panels & a new heat pump provide energy-efficient heating & cooling. Recent updates incl. fresh interior paint, Brazilian cherry flooring, epoxied garage floor, upgraded electrical panel, irrigation system, water purification system, driveway lighting, & detailed wainscoting w/ crown molding. The spacious eat-in kitchen w/ granite c-tops & SS appliances has sliders leading to the back deck & opens to a dramatic family room w/ a floor-to-ceiling brick fireplace. A private office, formal DR, & 1/2 bath w/ laundry complete the 1st floor. Upstairs offers 4 beds, all w/ HWs & ceiling fans & 2 full baths. Just under 4 miles to Shaw's Plaza, just over 4 miles to Rt 495 in Hopkinton/shopping plaza

78 Milford St, Upton

Listing courtesy of Listing Agent: TEAM Metrowest from Listing Office: Berkshire Hathaway HomeServices Commonwealth Real Estate.
$820,000
4 Beds ⋅ 3 Baths ⋅ 73468744 MLS
Beautifully maintained home featuring gleaming hardwood floors and two cozy fireplaces. The cathedral-ceiling family room offers a bright and open layout ideal for everyday living and entertaining. Includes a formal dining room and a private office. Fully renovated and modernized kitchen and bathrooms with stylish finishes and contemporary functionality. Large windows throughout the home provide abundant natural light and a strong connection to nature with scenic four-season views. Finished walkout basement offers flexible additional living space. Set on a generous lot with an expansive backyard, peaceful babbling brook, and mature trees. Additional highlights include a young roof, ample parking, and a quiet neighborhood setting.

13 Jonathans Way, Upton

Listing courtesy of Listing Agent: Shelly A. Armstrong from Listing Office: Redfin Corp..
$810,000
3 Beds ⋅ 3 Baths ⋅ 73488757 MLS
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

Listing courtesy of Listing Agent: Campos Homes from Listing Office: RE/MAX Real Estate Center.
$800,000
3 Beds ⋅ 4 Baths ⋅ 73518665 MLS
Custom-built expanded cape privately set on an acre-plus lot overlooking picturesque Mill Pond. This unique property offers exceptional space, flexibility, and endless potential. The updated open-concept kitchen with beamed ceilings flows into a cozy dining area with pellet stove, followed by a dramatic lodge-style living room featuring a stunning floor-to-ceiling stone fireplace. Sliders lead to a wraparound deck and peaceful outdoor space, perfect for entertaining and relaxing. The primary suite offers a private bath, beamed ceilings, while two additional oversized bedrooms feature large walk-in closets. Bright 700+sq ft direct outdoor access LL, includes a summer kitchen, media room, full bath, family room, and flexible exercise /play space not inc. in GLA. Approx. 2000 sq ft unfinished addition offers expansion or in-law potential. Close to Routes 495 & 140, on-site access to kayaking, canoeing and fishing, oversized two car garage, great storage, this property has it all!

9 River St, Upton

Listing courtesy of Listing Agent: Danelle Morris from Listing Office: eXp Realty LLC.
$800,000
4 Beds ⋅ 3 Baths ⋅ 73514244 MLS
**Offers due by Saturday 5/23 at NOON*** Welcome to ONE floor living in this fabulous custom ranch. Situated on a two plus acre lot, at the end of a quiet side street ,close to the center of town. Large open living room with gas log fireplace and hardwood flooring & cathedral ceilings, opens to a beautiful kitchen with stainless appliances, center island, granite counter tops. Side entrance to mud room with pantry closets Large dining area that leads to a spacious screened in sun porch and a large open deck area. Laundry on the first floor. Large Primary suite with large closets, complete with build ins, access to the deck, tiled walk in shower in the primary bath. Two other flex rooms for extra sleeping or office space. The fully finished basement space offers a multitude of different opportunities, With a full bath, and two large rooms. Buderus boiler. Two separate areas offer amazing storage and workshop space. Town water available at the street.

36 Brooks St, Upton

Listing courtesy of Listing Agent: Jeannie Leombruno from Listing Office: Century 21 Custom Home Realty.
$785,000
4 Beds ⋅ 3 Baths ⋅ 73538003 MLS
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

Listing courtesy of Listing Agent: Walsh Fine Homes Team from Listing Office: eXp Realty LLC.
$770,000
4 Beds ⋅ 3 Baths ⋅ 73500985 MLS
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

Listing courtesy of Listing Agent: Robyn Nasuti from Listing Office: Realty ONE Group Suburban Lifestyle.
$766,700
3 Beds ⋅ 2 Baths ⋅ 73528914 MLS
Discover the perfect blend of privacy and convenience on 6 wooded acres! Set back from the road and surrounded by mature trees, this property offers a peaceful setting while remaining close to local amenities, recreation, and commuter routes. Enter through double front doors into a spacious living room with hardwood floors, a bow window, and a cozy wood stove. The kitchen features stainless steel appliances, wall oven, center island, and dining area with skylight. The expansive family room showcases hardwood floors, vaulted ceilings with skylights, a pellet stove, oversized picture window, and French doors leading to the backyard. A formal dining room and ¾ bath complete the main level. Upstairs offers a spacious primary bedroom with generous closet space, two additional bedrooms, and a full bath. Enjoy room for entertaining, gardening, and outdoor recreation just minutes from Pratt Pond, Kiwanis Beach, shopping, dining, and major routes. Open Houses this Friday evening & Saturday!

74 High Street, Upton

Listing courtesy of Listing Agent: Mary G. Wood from Listing Office: Lamacchia Realty, Inc..
$765,000
3 Beds ⋅ 3 Baths ⋅ 73522253 MLS
COMFORT MEETS COUNTRY SERENITY! Tucked away on a peaceful country road with 2+ acres of wooded privacy, this home suits all lifestyles. A true open-concept 1st floor creates a seamless flow. The remodeled kitchen has quartz countertops, white cabinetry and a 4-top seating island with a built-in bookshelf. Hardwood floors carry through to the dining room and bright living room, anchored by a 2-sided gas fireplace that opens to a stunning sunroom. Practicality meets luxury with a farmhouse powder room and a remodeled guest bath that compliments the prevalent modern flair. “Romeo, oh Romeo” – fall in LOVE with the private balcony in the primary bedroom, complete with the vaulted ceilings and skylights. Every level feels move-in ready with NEW carpet and fresh paint (various). Outside is your oasis: inground pool, a screened-in TREK porch, firepit and wood deck. With energy-efficient mini-splits and a finished walkout family room, this home is as smart as it is beautiful!

24 Fowler Street, Upton

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

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