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Beautiful sunsets, an amazing backyard, and extensive updates create an inviting place to call home in Warren Woods, one of Upton’s most desirable neighborhoods. Offering four bedrooms, two full baths, and two half baths, this thoughtfully improved home combines generous living spaces with town water, natural gas, and convenient access to major routes. The expansive family room is a standout, with soaring cathedral ceilings and a fireplace that brings warmth and character to everything from quiet evenings to lively gatherings. An updated kitchen, spacious bedrooms, and a dedicated office offer comfortable spaces for everyday living, working, and entertaining. The finished basement adds even more versatility, with room for recreation, hobbies, or relaxing, plus a conveniently added half bath. Outside, a beautiful backyard invites you to unwind and enjoy the natural surroundings. Composite decking and a lovely patio provide welcoming spaces for outdoor dining, summer get-togethers, and taking in the sunset, creating a picturesque backdrop. Numerous improvements reflect the care invested throughout the home. In 2026, three bedrooms, the office, foyer, and hallway were freshly painted, and all hardwood flooring was refinished. Additional updates since 2020 include kitchen improvements, new vinyl windows and sliders, replacement carpeting in the bedrooms and office, a new front door, and granite front steps. A new electrical panel, updated switches and outlets throughout, added air-conditioning, and LeafGuard gutters enhance everyday comfort and convenience. The exterior has also been repainted, completing the home’s refreshed appearance. With its sought-after neighborhood setting, inviting indoor and outdoor spaces, and thoughtful improvements, this Warren Woods home is ready for its next chapter.

4 Beds ⋅ 4 Baths ⋅ 73595051 MLS

Beautiful sunsets, an amazing backyard, and extensive updates create an inviting place to call home in Warren Woods, one of Upton’s most desirable neighborhoods. Offering four bedrooms, two full baths, and two half baths, this thoughtfully improved home combines generous living spaces with town water, natural gas, and convenient access to major routes. The expansive family room is a standout, with soaring cathedral ceilings and a fireplace that brings warmth and character to everything from quiet evenings to lively gatherings. An updated kitchen, spacious bedrooms, and a dedicated office offer comfortable spaces for everyday living, working, and entertaining. The finished basement adds even more versatility, with room for recreation, hobbies, or relaxing, plus a conveniently added half bath. Outside, a beautiful backyard invites you to unwind and enjoy the natural surroundings. Composite decking and a lovely patio provide welcoming spaces for outdoor dining, summer get-togethers, and taking in the sunset, creating a picturesque backdrop. Numerous improvements reflect the care invested throughout the home. In 2026, three bedrooms, the office, foyer, and hallway were freshly painted, and all hardwood flooring was refinished. Additional updates since 2020 include kitchen improvements, new vinyl windows and sliders, replacement carpeting in the bedrooms and office, a new front door, and granite front steps. A new electrical panel, updated switches and outlets throughout, added air-conditioning, and LeafGuard gutters enhance everyday comfort and convenience. The exterior has also been repainted, completing the home’s refreshed appearance. With its sought-after neighborhood setting, inviting indoor and outdoor spaces, and thoughtful improvements, this Warren Woods home is ready for its next chapter.

9 Jonathans Way, Upton

$1,499,999

Location Location Location!! Perched up on a hill overlooking Pratt Pond. Steps away from Kiwanis Beach Park and a public beach with baseball+soccer fields, tennis, pickleball+basketball courts. Featuring an open concept kitchen/family room, with an oversized island, family room with 20' ceiling height, flexibility with a 1st floor primary and a private office. 2nd floor features the other 4 bedrooms, all en-suite including a jack-n-jill. Retreat to an oversized master bedroom with his and hers walk-in closets and a spa like bathroom. Laundry room conveniently on the 2nd floor.

5 Beds ⋅ 4 Baths ⋅ 73594520 MLS

Location Location Location!! Perched up on a hill overlooking Pratt Pond. Steps away from Kiwanis Beach Park and a public beach with baseball+soccer fields, tennis, pickleball+basketball courts. Featuring an open concept kitchen/family room, with an oversized island, family room with 20' ceiling height, flexibility with a 1st floor primary and a private office. 2nd floor features the other 4 bedrooms, all en-suite including a jack-n-jill. Retreat to an oversized master bedroom with his and hers walk-in closets and a spa like bathroom. Laundry room conveniently on the 2nd floor.

9 Kiwanis Beach Rd, Upton

$1,200,000

Your own backyard retreat awaits at 30 Juniper Road. Set on nearly three private acres in Upton’s Taft Mill Estates, this custom-designed home pairs exceptional outdoor living with an expansive layout and extensive recent improvements. A brick-front farmer’s porch creates a memorable welcome, opening to inviting spaces with clear maple flooring throughout the first floor, a beautifully appointed cook’s kitchen, and an open flow ideal for gathering and entertaining. Four bedrooms and 3½ baths offers room to spread out, while the spacious primary bedroom includes an exercise area. The finished daylight walkout lower level adds versatile space for recreation, hobbies, or entertaining. Fresh neutral interior paint and new carpeting, completed in October 2026, give the home a beautifully refreshed feel. The backyard is the showstopper: professionally landscaped grounds, manicured lawn, surrounding woodlands, and a gorgeous inground pool framed by stamped concrete. Enjoy summer afternoons by the water, dinner on the composite deck, or quiet mornings in the enclosed rear porch overlooking this remarkable setting. Installed in 2012, the pool received a new heater and salt cell in 2026, and the pool deck was resealed that August. Significant 2026 improvements include a new main roof and front porch roof, generator, water softener, emergency water shut-off, and upgraded irrigation with a rain sensor. The driveway was sealed in September, complementing the season’s professional landscaping. Additional updates include the A/C system in 2019, well pump in 2023, and garage door openers in 2024. Yard fencing, an electronic dog fence serviced in 2026, and a composite deck round out the outdoor amenities. From its welcoming porch and custom details to its thoughtfully maintained grounds and exceptional poolside setting, this home offers space to entertain, room to unwind, and the privacy of an estate-size lot—all in a beautiful Upton neighborhood.

4 Beds ⋅ 4 Baths ⋅ 73592698 MLS

Your own backyard retreat awaits at 30 Juniper Road. Set on nearly three private acres in Upton’s Taft Mill Estates, this custom-designed home pairs exceptional outdoor living with an expansive layout and extensive recent improvements. A brick-front farmer’s porch creates a memorable welcome, opening to inviting spaces with clear maple flooring throughout the first floor, a beautifully appointed cook’s kitchen, and an open flow ideal for gathering and entertaining. Four bedrooms and 3½ baths offers room to spread out, while the spacious primary bedroom includes an exercise area. The finished daylight walkout lower level adds versatile space for recreation, hobbies, or entertaining. Fresh neutral interior paint and new carpeting, completed in October 2026, give the home a beautifully refreshed feel. The backyard is the showstopper: professionally landscaped grounds, manicured lawn, surrounding woodlands, and a gorgeous inground pool framed by stamped concrete. Enjoy summer afternoons by the water, dinner on the composite deck, or quiet mornings in the enclosed rear porch overlooking this remarkable setting. Installed in 2012, the pool received a new heater and salt cell in 2026, and the pool deck was resealed that August. Significant 2026 improvements include a new main roof and front porch roof, generator, water softener, emergency water shut-off, and upgraded irrigation with a rain sensor. The driveway was sealed in September, complementing the season’s professional landscaping. Additional updates include the A/C system in 2019, well pump in 2023, and garage door openers in 2024. Yard fencing, an electronic dog fence serviced in 2026, and a composite deck round out the outdoor amenities. From its welcoming porch and custom details to its thoughtfully maintained grounds and exceptional poolside setting, this home offers space to entertain, room to unwind, and the privacy of an estate-size lot—all in a beautiful Upton neighborhood.

30 Juniper Rd, Upton

$859,900

ONE-OF-A-KIND LOG HOME RETREAT One owner! Set on nearly 4.5 private acres, this extraordinary 3-bedroom, 2.5-bath custom log home showcases rustic luxury, exceptional craftsmanship, and unforgettable character. Hand-peeled logs, two dramatic stone fireplaces featuring stones sourced from the property, radiant floor heating, and stunning wide yellow pine plank floors accented with antique nails create timeless warmth and charm. The kitchen features an impressive 8-burner chef’s stove, while the first-floor primary suite, sunroom, spacious living and dining areas, and open loft offer comfort and versatility. Upstairs are two additional bedrooms and a full bath with Jacuzzi tub. The finished lower level surprises with 10-foot ceilings, half bath, laundry, workshop, and a custom bookcase concealing a hidden room! Outside, enjoy professional landscaping, irrigation, privacy, and room to roam. Additional features include a 16x20 storage shed, 8x10 wood shed and a chicken coop complete with chickens. A rare opportunity to own a truly distinctive log home offering acreage, rustic elegance, and extraordinary details at every turn!

3 Beds ⋅ 3 Baths ⋅ 73589810 MLS

ONE-OF-A-KIND LOG HOME RETREAT One owner! Set on nearly 4.5 private acres, this extraordinary 3-bedroom, 2.5-bath custom log home showcases rustic luxury, exceptional craftsmanship, and unforgettable character. Hand-peeled logs, two dramatic stone fireplaces featuring stones sourced from the property, radiant floor heating, and stunning wide yellow pine plank floors accented with antique nails create timeless warmth and charm. The kitchen features an impressive 8-burner chef’s stove, while the first-floor primary suite, sunroom, spacious living and dining areas, and open loft offer comfort and versatility. Upstairs are two additional bedrooms and a full bath with Jacuzzi tub. The finished lower level surprises with 10-foot ceilings, half bath, laundry, workshop, and a custom bookcase concealing a hidden room! Outside, enjoy professional landscaping, irrigation, privacy, and room to roam. Additional features include a 16x20 storage shed, 8x10 wood shed and a chicken coop complete with chickens. A rare opportunity to own a truly distinctive log home offering acreage, rustic elegance, and extraordinary details at every turn!

55 Fiske Mill Rd, Upton

$449,900

Some photos are virtually staged for marketing purposes. This charming Colonial-style home blends timeless New England character with modern conveniences. The first floor features beautiful wide-plank wood floors in the living and dining rooms, along with a cozy fireplace that adds warmth and character. The updated kitchen boasts tile flooring, granite countertops, and stainless steel appliances. A full bathroom on the main level adds convenience. Upstairs, you'll find three bedrooms with wood flooring throughout, along with a newly updated full bathroom featuring tile floors and an expansive jetted tub-perfect for unwinding at the end of the day. Step outside onto the deck and relax while enjoying peaceful views of Warren Brook. With its classic charm, thoughtful updates, and inviting outdoor space, this home offers a wonderful blend of comfort and character.

3 Beds ⋅ 2 Baths ⋅ 73589345 MLS

Some photos are virtually staged for marketing purposes. This charming Colonial-style home blends timeless New England character with modern conveniences. The first floor features beautiful wide-plank wood floors in the living and dining rooms, along with a cozy fireplace that adds warmth and character. The updated kitchen boasts tile flooring, granite countertops, and stainless steel appliances. A full bathroom on the main level adds convenience. Upstairs, you'll find three bedrooms with wood flooring throughout, along with a newly updated full bathroom featuring tile floors and an expansive jetted tub-perfect for unwinding at the end of the day. Step outside onto the deck and relax while enjoying peaceful views of Warren Brook. With its classic charm, thoughtful updates, and inviting outdoor space, this home offers a wonderful blend of comfort and character.

6 Glen Ave, Upton

$1,175,000

If you have been looking for a new place to call "home" then welcome to 27 Dairy Dr in Upton. This beautifully appointed 4-bedroom, 3.5-bath home, with 4,116 sq/ft of exceptional space, thoughtful details, and a private backyard oasis is the one you have been waiting for. The main level features a first-floor office, chef’s kitchen with a large island, a formal dining room, living room with soaring ceiling and loads of natural light, elegant crown moldings, and beautiful architectural details. The second-floor features a spacious primary en suite along with 3 other generous size bedrooms and 2 full baths that offers a flexible layout perfect for multi-generational living, plus the laundry room adds everyday convenience. The finished basement provides versatile space for entertaining with a wet bar and media room area perfect for gaming, recreation and hobbies. Outside, enjoy an inground heated saltwater pool, hot tub and a private setting ideal for relaxing or entertaining. Additional highlights include a 3-car garage, 2 year old central heating and A/C system, and a new hot water tank installed in 2024. With scenic views out the front and tranquility in the private back yard this is truly an inviting home with space, comfort, and style throughout nestled in the amazing town of Upton and all it has to offer. Great commuter location with close proximity to 495 and the MA Pike, highly regarded school systems, and local amenities such as, award winning Shining Rock Golf Club, Kiwanis Beach and much more. Schedule your appointment today to start making your new memories.

4 Beds ⋅ 4 Baths ⋅ 73587562 MLS

If you have been looking for a new place to call "home" then welcome to 27 Dairy Dr in Upton. This beautifully appointed 4-bedroom, 3.5-bath home, with 4,116 sq/ft of exceptional space, thoughtful details, and a private backyard oasis is the one you have been waiting for. The main level features a first-floor office, chef’s kitchen with a large island, a formal dining room, living room with soaring ceiling and loads of natural light, elegant crown moldings, and beautiful architectural details. The second-floor features a spacious primary en suite along with 3 other generous size bedrooms and 2 full baths that offers a flexible layout perfect for multi-generational living, plus the laundry room adds everyday convenience. The finished basement provides versatile space for entertaining with a wet bar and media room area perfect for gaming, recreation and hobbies. Outside, enjoy an inground heated saltwater pool, hot tub and a private setting ideal for relaxing or entertaining. Additional highlights include a 3-car garage, 2 year old central heating and A/C system, and a new hot water tank installed in 2024. With scenic views out the front and tranquility in the private back yard this is truly an inviting home with space, comfort, and style throughout nestled in the amazing town of Upton and all it has to offer. Great commuter location with close proximity to 495 and the MA Pike, highly regarded school systems, and local amenities such as, award winning Shining Rock Golf Club, Kiwanis Beach and much more. Schedule your appointment today to start making your new memories.

27 Dairy Dr, Upton

$649,000

A true home in the forest! Come visit this diamond in the rough and all it's potential, on the market for the first time after 50 years of original ownership. Set back over 100' from the road, this sprawling property is situated on a 2.5 acre tree-lined lot. Featuring 3 large bedrooms, 2 full baths and endless possibilities, all within nearly 2300 sq/ft of living space. Walk through the vaulted ceilings in the oversized great room, out to the massive cedar lined sunroom. Unfinished basement offers an additional 1100+ sq/ft with 7'7" ceilings...perfect for a bonus room, man cave, playroom, workshop, etc. Big ticket items like asphalt roof, wood frame Andersen windows, boiler, hot water heater and oil tank all replaced within 10 years. Seller to install new 3-bedroom septic prior to close. OH 10/9 from 5-7pm and 10/10 from 11-1pm. Don't miss out on this gem with great bones!

3 Beds ⋅ 2 Baths ⋅ 73586877 MLS

A true home in the forest! Come visit this diamond in the rough and all it's potential, on the market for the first time after 50 years of original ownership. Set back over 100' from the road, this sprawling property is situated on a 2.5 acre tree-lined lot. Featuring 3 large bedrooms, 2 full baths and endless possibilities, all within nearly 2300 sq/ft of living space. Walk through the vaulted ceilings in the oversized great room, out to the massive cedar lined sunroom. Unfinished basement offers an additional 1100+ sq/ft with 7'7" ceilings...perfect for a bonus room, man cave, playroom, workshop, etc. Big ticket items like asphalt roof, wood frame Andersen windows, boiler, hot water heater and oil tank all replaced within 10 years. Seller to install new 3-bedroom septic prior to close. OH 10/9 from 5-7pm and 10/10 from 11-1pm. Don't miss out on this gem with great bones!

23 Forest St, Upton

$1,099,000

Be the first to call this exceptional new-construction Colonial home! Ideally situated near the heart of downtown Upton, this 2,889 -square-foot residence pairs timeless farmhouse charm with modern finishes and a flexible layout designed for today’s lifestyle. Enjoy the character of small-town living with convenient access to Upton’s town beach, parks, library, post office, local shops, and even your morning coffee at Dunkin’. Step inside to discover beautiful hardwood flooring, elegant crown molding, and custom details that make this home feel truly special. At the heart of the home is a showstopping kitchen featuring quartz countertops, a dramatic waterfall island, a gas range, and a walk-in pantry with custom shelving. Whether you’re hosting a holiday celebration or enjoying a quiet morning at the island, this is a space designed for gathering. The kitchen opens directly to the patio, creating an effortless connection for outdoor dining, entertaining, or simply unwinding at the end of the day. The inviting living room is anchored by a fireplace and custom built-in shelving, adding warmth, character, and a polished finishing touch. Upstairs, you’ll find three beautifully appointed bedrooms, including a serene primary suite with a spacious walk-in tiled shower. Decorative tile elevates the bathrooms, while custom built-in shelving in every bedroom adds both style and practical storage. The finished lower level expands the possibilities with a fourth bedroom, full bathroom, and kitchenette. This versatile space is ideal for an au pair suite, home gym, media room, home office, or can accommodate overnight guests, multigenerational living, or a private retreat. Even the garage reflects the same attention to detail found throughout the residence. The garage features durable waterproof flooring and has is a dedicated EV electrical outlet in place for electric-vehicle charging—an intentional modern amenity designed for the future of luxury homeownership. With four bedrooms, four-and-a-half bathrooms, thoughtful craftsmanship, and spaces created for both everyday comfort and memorable occasions, this stunning home offers the opportunity to enjoy brand-new construction and the welcoming lifestyle that makes Upton such a special place to call home.

4 Beds ⋅ 4 Baths ⋅ 73580900 MLS

Be the first to call this exceptional new-construction Colonial home! Ideally situated near the heart of downtown Upton, this 2,889 -square-foot residence pairs timeless farmhouse charm with modern finishes and a flexible layout designed for today’s lifestyle. Enjoy the character of small-town living with convenient access to Upton’s town beach, parks, library, post office, local shops, and even your morning coffee at Dunkin’. Step inside to discover beautiful hardwood flooring, elegant crown molding, and custom details that make this home feel truly special. At the heart of the home is a showstopping kitchen featuring quartz countertops, a dramatic waterfall island, a gas range, and a walk-in pantry with custom shelving. Whether you’re hosting a holiday celebration or enjoying a quiet morning at the island, this is a space designed for gathering. The kitchen opens directly to the patio, creating an effortless connection for outdoor dining, entertaining, or simply unwinding at the end of the day. The inviting living room is anchored by a fireplace and custom built-in shelving, adding warmth, character, and a polished finishing touch. Upstairs, you’ll find three beautifully appointed bedrooms, including a serene primary suite with a spacious walk-in tiled shower. Decorative tile elevates the bathrooms, while custom built-in shelving in every bedroom adds both style and practical storage. The finished lower level expands the possibilities with a fourth bedroom, full bathroom, and kitchenette. This versatile space is ideal for an au pair suite, home gym, media room, home office, or can accommodate overnight guests, multigenerational living, or a private retreat. Even the garage reflects the same attention to detail found throughout the residence. The garage features durable waterproof flooring and has is a dedicated EV electrical outlet in place for electric-vehicle charging—an intentional modern amenity designed for the future of luxury homeownership. With four bedrooms, four-and-a-half bathrooms, thoughtful craftsmanship, and spaces created for both everyday comfort and memorable occasions, this stunning home offers the opportunity to enjoy brand-new construction and the welcoming lifestyle that makes Upton such a special place to call home.

91 High, Upton

$1,165,000

Welcome to the Preserve at Lake Wildwood. Stately ,4BR, 3.5BA Center Hall Colonial featuring 4,000+ sq ft of living space in a desirable suburban neighborhood. Set at the beginning of a cul de sac this grand two-story foyer opens to formal living and dining rooms. Gourmet eat-in kitchen with center island and stainless steel appliances flows into an expansive family room with gas fireplace and remote start. Main level also features a private home office. Upstairs, the primary suite offers a walk-in closet and office area and a spa bath with a jetted tub and double vanity, alongside 3 additional generous bedrooms and laundry room The finished walk-out basement includes a bonus room and flexible space for entertaining, recreation and fitness. Step outside to an impressive outdoor gathering space complete with patio and pergola overlooking a private yard with an oversized storage shed. Includes multi-car attached garage, central A/C, and hardwood floors. Conveniently located near top-rated schools, shopping, and commuter routes.

4 Beds ⋅ 4 Baths ⋅ 73579210 MLS

Welcome to the Preserve at Lake Wildwood. Stately ,4BR, 3.5BA Center Hall Colonial featuring 4,000+ sq ft of living space in a desirable suburban neighborhood. Set at the beginning of a cul de sac this grand two-story foyer opens to formal living and dining rooms. Gourmet eat-in kitchen with center island and stainless steel appliances flows into an expansive family room with gas fireplace and remote start. Main level also features a private home office. Upstairs, the primary suite offers a walk-in closet and office area and a spa bath with a jetted tub and double vanity, alongside 3 additional generous bedrooms and laundry room The finished walk-out basement includes a bonus room and flexible space for entertaining, recreation and fitness. Step outside to an impressive outdoor gathering space complete with patio and pergola overlooking a private yard with an oversized storage shed. Includes multi-car attached garage, central A/C, and hardwood floors. Conveniently located near top-rated schools, shopping, and commuter routes.

3 Dairy Drive, Upton

$1,099,000

Located in the exclusive Glen Echo Estates community in Upton, this impressive 2008-built Colonial showcases an ideal lot & yard all within a tranquil neighborhood setting. As you move inside the home, you are greeted by a regal two-story foyer, which receives fantastic morning sunlight via an Eastern Exposure. The sunlight reflects beautifully off the oak hardwood floors that extend throughout the first floor, leading past a dedicated home office behind private French doors. The formal dining room offers classic entertaining space, while the eat-in kitchen serves as the heart of the home, equipped with granite countertops, a center island, induction cooking, vent hood, kitchen desk, plenty of cabinetry, and upgraded appliances replaced in 2020. Seamlessly connected to the kitchen is a sizable family room featuring hardwood floors installed in 2022, as well as a bright Florida room with sliders leading outdoors. Upstairs, you will find second-floor hardwoods added in 2022, a full laundry room with 2020 washer/dryer, a full bathroom, three bedrooms, and the primary suite—notable for its generous size, walk-in closet, and spacious bath. The lower level features a fully finished basement (2019) complete with a built-in bar, bonus area, versatile living and entertaining space, and separate storage. Outside, the property truly shines with a full-yard irrigation system installed in 2020. Beautiful stonework and pavers lead to a nicely sized deck, a custom patio build, and a spacious 10x18 shed added in 2018. Mature trees line the rear for privacy, while the front yard offers a perfect setback with a three-car garage providing ample parking and storage. All located near Upton State Forest, local farms, restaurants, and convenient commuting options along the Westborough line.

4 Beds ⋅ 3 Baths ⋅ 73578851 MLS

Located in the exclusive Glen Echo Estates community in Upton, this impressive 2008-built Colonial showcases an ideal lot & yard all within a tranquil neighborhood setting. As you move inside the home, you are greeted by a regal two-story foyer, which receives fantastic morning sunlight via an Eastern Exposure. The sunlight reflects beautifully off the oak hardwood floors that extend throughout the first floor, leading past a dedicated home office behind private French doors. The formal dining room offers classic entertaining space, while the eat-in kitchen serves as the heart of the home, equipped with granite countertops, a center island, induction cooking, vent hood, kitchen desk, plenty of cabinetry, and upgraded appliances replaced in 2020. Seamlessly connected to the kitchen is a sizable family room featuring hardwood floors installed in 2022, as well as a bright Florida room with sliders leading outdoors. Upstairs, you will find second-floor hardwoods added in 2022, a full laundry room with 2020 washer/dryer, a full bathroom, three bedrooms, and the primary suite—notable for its generous size, walk-in closet, and spacious bath. The lower level features a fully finished basement (2019) complete with a built-in bar, bonus area, versatile living and entertaining space, and separate storage. Outside, the property truly shines with a full-yard irrigation system installed in 2020. Beautiful stonework and pavers lead to a nicely sized deck, a custom patio build, and a spacious 10x18 shed added in 2018. Mature trees line the rear for privacy, while the front yard offers a perfect setback with a three-car garage providing ample parking and storage. All located near Upton State Forest, local farms, restaurants, and convenient commuting options along the Westborough line.

32 Howarth Dr, Upton

$1,079,000

Pride of ownership abounds at this exceptional 4-bedroom, 3.5 bath custom contemporary home set on 3.50 beautifully maintained acres offering privacy and endless opportunities to enjoy the outdoors. Enter through the two-story foyer and be greeted by sunlight pouring into the home through an abundance of windows, skylights, and sliders creating a bright and welcoming atmosphere throughout. The kitchen includes two pantry closets, Sub Zero refrigerator and stylish concrete sink and flows to a step-down dining/living area with gorgeous stone fireplace and slider access to the peaceful screened in porch and amazing deck. A laundry room, half bath and vaulted ceiling living room with French doors complete the floor. Upstairs a large bedroom with en-suite bath acts as a second primary and is complemented by two additional bedrooms and full bath on the way to the huge primary bedroom with vaulted ceilings, double closets, a separate room currently being used as a makeup area and an exquisite bathroom with jetted tub and separate shower. The walk out lower level includes a climate controlled wine cellar and access to the heated two car garage. Outdoor living is truly a highlight, with a beautiful stone patio featuring a pizza oven, pergola and a fire pit, plus a deck with newer composite decking and railings and high end built-in grill and additional pergola—perfect for entertaining, dining, or relaxing. Additional features include a new roof with solar panels, a beautifully repaved driveway with a distinctive paver border, and lushly landscaped grounds. With its combination of generous living space, unique amenities, and spectacular indoor-outdoor living, this Upton property offers a rare opportunity to enjoy comfort, in a serene environment yet only a short distance to Routes 495 and 90 and the shops and restaurants nearby.

4 Beds ⋅ 4 Baths ⋅ 73574514 MLS

Pride of ownership abounds at this exceptional 4-bedroom, 3.5 bath custom contemporary home set on 3.50 beautifully maintained acres offering privacy and endless opportunities to enjoy the outdoors. Enter through the two-story foyer and be greeted by sunlight pouring into the home through an abundance of windows, skylights, and sliders creating a bright and welcoming atmosphere throughout. The kitchen includes two pantry closets, Sub Zero refrigerator and stylish concrete sink and flows to a step-down dining/living area with gorgeous stone fireplace and slider access to the peaceful screened in porch and amazing deck. A laundry room, half bath and vaulted ceiling living room with French doors complete the floor. Upstairs a large bedroom with en-suite bath acts as a second primary and is complemented by two additional bedrooms and full bath on the way to the huge primary bedroom with vaulted ceilings, double closets, a separate room currently being used as a makeup area and an exquisite bathroom with jetted tub and separate shower. The walk out lower level includes a climate controlled wine cellar and access to the heated two car garage. Outdoor living is truly a highlight, with a beautiful stone patio featuring a pizza oven, pergola and a fire pit, plus a deck with newer composite decking and railings and high end built-in grill and additional pergola—perfect for entertaining, dining, or relaxing. Additional features include a new roof with solar panels, a beautifully repaved driveway with a distinctive paver border, and lushly landscaped grounds. With its combination of generous living space, unique amenities, and spectacular indoor-outdoor living, this Upton property offers a rare opportunity to enjoy comfort, in a serene environment yet only a short distance to Routes 495 and 90 and the shops and restaurants nearby.

165 East St, Upton

$974,900

Siting majestically in one of Upton's most desired neighborhoods, this gorgeous Colonial commands attention with its gracious presence, impressive scale and beautifully designed spaces. Step through the soaring two story foyer and into a home created for memorable living and effortless entertaining. The wonderful kitchen is a culinary delight, complete with a generous island, gourmet appliances with large cooktop, double wall oven, and charming banquette seating that invites everyone to gather. Just beyond, the dramatic cathedral family room is anchored by a beautiful fireplace, creating an incredible backdrop for holiday mornings, celebrations and evenings spent fireside. An oversized dining room elevates every occasion, from elegant dinners to treasured nights gathered with family and friends. The fabulous three season porch offers a front row seat to nature and a peaceful escape to enjoy morning coffee, quiet afternoons or evenings overlooking the beautiful surroundings. Upstairs, the oversized primary retreat feels wonderfully indulgent, featuring a beautiful window seat made for curling up with a favorite book and enjoying a rare quiet moment. The luxurious primary bath completes the experience with a spacious walk in shower and oversized Jacuzzi tub worthy of a private spa. And there is still more to imagine. A huge walkout basement offers exceptional potential for future living space, entertaining areas, a fitness room or whatever comes next. Impressive yet inviting, elegant without feeling untouchable, this is a home designed for the moments that matter and a truly special opportunity in one of Upton's most coveted settings.

4 Beds ⋅ 3 Baths ⋅ 73573687 MLS

Siting majestically in one of Upton's most desired neighborhoods, this gorgeous Colonial commands attention with its gracious presence, impressive scale and beautifully designed spaces. Step through the soaring two story foyer and into a home created for memorable living and effortless entertaining. The wonderful kitchen is a culinary delight, complete with a generous island, gourmet appliances with large cooktop, double wall oven, and charming banquette seating that invites everyone to gather. Just beyond, the dramatic cathedral family room is anchored by a beautiful fireplace, creating an incredible backdrop for holiday mornings, celebrations and evenings spent fireside. An oversized dining room elevates every occasion, from elegant dinners to treasured nights gathered with family and friends. The fabulous three season porch offers a front row seat to nature and a peaceful escape to enjoy morning coffee, quiet afternoons or evenings overlooking the beautiful surroundings. Upstairs, the oversized primary retreat feels wonderfully indulgent, featuring a beautiful window seat made for curling up with a favorite book and enjoying a rare quiet moment. The luxurious primary bath completes the experience with a spacious walk in shower and oversized Jacuzzi tub worthy of a private spa. And there is still more to imagine. A huge walkout basement offers exceptional potential for future living space, entertaining areas, a fitness room or whatever comes next. Impressive yet inviting, elegant without feeling untouchable, this is a home designed for the moments that matter and a truly special opportunity in one of Upton's most coveted settings.

27 Juniper Road, Upton

$569,000

LENDER FUNDED RATE BUY DOWN Offered on this property will help lower your monthly payments. Welcomes om this this charming Colonial Style home, offering warmth, character, and modern comfort throughout. The inviting open floor plan creates a seamless flow between the living, dining, and kitchen areas, making the home feel spacious and welcoming. Beautiful hardwood flooring runs throughout the home. The living room is complemented by a cozy fireplace with an elegant marble surround. The kitchen features Stainless Steele appliances, durable granite countertops, and a breakfast bar, flowing naturally to the main living spaces, perfect for everyday living and entertaining.On the second floor you will find three generously sized bedrooms all with hard-wood flooring. The bathroom offers a double-bowl vanity for added convenience and functionality. This delightful property combines charm, functionality, and thoughtful updates in a comfortable and convenient setting. Central air conditioning provides year-round comfort.The finished lower level of the home offers an ideal space to gather to watch a movie, the big game, or just a place for quiet time. Private deck overlooking a fenced in back yard, complete with a firepit. One car garage and a circular driveway add to the overall comfort of this home While the home's classic colonial design adds timeless appeal its location provides easy access to major highways, all for under $600,000. Seller will entertain all offers.

3 Beds ⋅ 2 Baths ⋅ 73573230 MLS

LENDER FUNDED RATE BUY DOWN Offered on this property will help lower your monthly payments. Welcomes om this this charming Colonial Style home, offering warmth, character, and modern comfort throughout. The inviting open floor plan creates a seamless flow between the living, dining, and kitchen areas, making the home feel spacious and welcoming. Beautiful hardwood flooring runs throughout the home. The living room is complemented by a cozy fireplace with an elegant marble surround. The kitchen features Stainless Steele appliances, durable granite countertops, and a breakfast bar, flowing naturally to the main living spaces, perfect for everyday living and entertaining.On the second floor you will find three generously sized bedrooms all with hard-wood flooring. The bathroom offers a double-bowl vanity for added convenience and functionality. This delightful property combines charm, functionality, and thoughtful updates in a comfortable and convenient setting. Central air conditioning provides year-round comfort.The finished lower level of the home offers an ideal space to gather to watch a movie, the big game, or just a place for quiet time. Private deck overlooking a fenced in back yard, complete with a firepit. One car garage and a circular driveway add to the overall comfort of this home While the home's classic colonial design adds timeless appeal its location provides easy access to major highways, all for under $600,000. Seller will entertain all offers.

40 Hartford Ave N, Upton

$1,149,900

Welcome to 8 Juniper Road, where generous living space, extensive updates, and a spectacular backyard come together. Set on 2.04 acres, this Upton home offers approximately 3,700 sq. ft., 4 bedrooms, 4.5 bathrooms, and a 3-car garage. Step inside and immediately feel welcomed by the warmth of every day living and entertaining. The backyard is a standout feature of this incredible home with a heated in-ground pool, integrated hot tub, expansive composite deck, landscaping, and irrigation system. Significant improvements include a new boiler, well tank, and well pump in 2021; composite deck, pool liner, heater, and pump in 2022; irrigation in 2023; first-floor AC condenser in 2024; and a sealed driveway in 2026. Additional updates include exterior painting and trim, kitchen slider, backsplash, and appliances.

4 Beds ⋅ 5 Baths ⋅ 73566681 MLS

Welcome to 8 Juniper Road, where generous living space, extensive updates, and a spectacular backyard come together. Set on 2.04 acres, this Upton home offers approximately 3,700 sq. ft., 4 bedrooms, 4.5 bathrooms, and a 3-car garage. Step inside and immediately feel welcomed by the warmth of every day living and entertaining. The backyard is a standout feature of this incredible home with a heated in-ground pool, integrated hot tub, expansive composite deck, landscaping, and irrigation system. Significant improvements include a new boiler, well tank, and well pump in 2021; composite deck, pool liner, heater, and pump in 2022; irrigation in 2023; first-floor AC condenser in 2024; and a sealed driveway in 2026. Additional updates include exterior painting and trim, kitchen slider, backsplash, and appliances.

8 Juniper Road, Upton

$940,000

Price Improvement so you can be home for the holidays!! 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!

4 Beds ⋅ 3 Baths ⋅ 73566169 MLS

Price Improvement so you can be home for the holidays!! 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

$675,000

$20,000 PRICE IMPROVEMENT! 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.

4 Beds ⋅ 3 Baths ⋅ 73565350 MLS

$20,000 PRICE IMPROVEMENT! 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

$899,000

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.

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

$1,320,000

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.

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.

66 Glenview St, Upton

$909,900

Stunning fully renovated luxury home offering three finished levels of sophisticated living with high-end finishes and designer details throughout. This turnkey home features an open-concept floor plan, a custom chef's kitchen with premium appliances, spa-inspired bathrooms, modern lighting, and beautifully updated living spaces. Thoughtfully renovated with exceptional craftsmanship, it seamlessly blends timeless charm with contemporary elegance. Move-in ready and designed for today's lifestyle, this exceptional home offers comfort, style, and quality in every detail.

4 Beds ⋅ 3 Baths ⋅ 73557408 MLS

Stunning fully renovated luxury home offering three finished levels of sophisticated living with high-end finishes and designer details throughout. This turnkey home features an open-concept floor plan, a custom chef's kitchen with premium appliances, spa-inspired bathrooms, modern lighting, and beautifully updated living spaces. Thoughtfully renovated with exceptional craftsmanship, it seamlessly blends timeless charm with contemporary elegance. Move-in ready and designed for today's lifestyle, this exceptional home offers comfort, style, and quality in every detail.

33 Milford St, Upton

$999,900

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 November 2026 Closing.

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 November 2026 Closing.

17 West Main Street, Upton

$699,000

BACK ON MARKET due to BUYER not being able to sell their home. A rare opportunity to own a beautifully preserved antique Gambrel, thoughtfully updated for modern living while retaining the craftsmanship and character of its New England heritage. Set along a scenic country road, this distinctive residence is surrounded by storybook grounds, mature landscaping and a sense of privacy that is increasingly difficult to find. A gracious first-floor primary suite offers a serene retreat, while the expansive, rambling floor plan provides exceptional flexibility for gathering, entertaining, working and relaxing. The interiors include a welcoming room, library/den, front-to-back living room and classic keeping room with a stone fireplace. A warm, inviting kitchen with natural wood cabinetry complements the home’s historic character, while three fireplaces, charming nooks and carefully preserved period details lend depth and authenticity throughout.The setting is equally compelling. Mature trees, flowering shrubs, open lawn and meadow frame a tranquil pond and distinctive New England stone walls. A beautiful patio, crafted with reclaimed Worcester brick and reached by a stone walkway, creates an elegant setting for morning coffee, outdoor dining or evening entertaining. The detached two-car garage includes a loft well suited to creative pursuits, hobbies or additional storage.Recent improvements include restored mid-1800s windows with storm windows, central air, a metal roof, a renovated second-floor bath, fresh exterior paint and a regraded driveway accented with cobblestone pavers. Each update enhances comfort and function while respecting the home’s original materials, proportions and enduring appeal.With its rare combination of architectural integrity, pastoral beauty and thoughtful livability, this exceptional property offers a lifestyle rooted in history, craftsmanship and quiet enjoyment. Schedule a private showing to experience its singular character firsthand.

4 Beds ⋅ 3 Baths ⋅ 73523806 MLS

BACK ON MARKET due to BUYER not being able to sell their home. A rare opportunity to own a beautifully preserved antique Gambrel, thoughtfully updated for modern living while retaining the craftsmanship and character of its New England heritage. Set along a scenic country road, this distinctive residence is surrounded by storybook grounds, mature landscaping and a sense of privacy that is increasingly difficult to find. A gracious first-floor primary suite offers a serene retreat, while the expansive, rambling floor plan provides exceptional flexibility for gathering, entertaining, working and relaxing. The interiors include a welcoming room, library/den, front-to-back living room and classic keeping room with a stone fireplace. A warm, inviting kitchen with natural wood cabinetry complements the home’s historic character, while three fireplaces, charming nooks and carefully preserved period details lend depth and authenticity throughout.The setting is equally compelling. Mature trees, flowering shrubs, open lawn and meadow frame a tranquil pond and distinctive New England stone walls. A beautiful patio, crafted with reclaimed Worcester brick and reached by a stone walkway, creates an elegant setting for morning coffee, outdoor dining or evening entertaining. The detached two-car garage includes a loft well suited to creative pursuits, hobbies or additional storage.Recent improvements include restored mid-1800s windows with storm windows, central air, a metal roof, a renovated second-floor bath, fresh exterior paint and a regraded driveway accented with cobblestone pavers. Each update enhances comfort and function while respecting the home’s original materials, proportions and enduring appeal.With its rare combination of architectural integrity, pastoral beauty and thoughtful livability, this exceptional property offers a lifestyle rooted in history, craftsmanship and quiet enjoyment. Schedule a private showing to experience its singular character firsthand.

52 Elm St, Upton

$1,050,000

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.

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

$1,649,000

ABSOLUTELY STUNNING. Enormous 8 Bedroom Home with over 6000 square feet of living on 5.5 acres bordering the Shining Rock Golf Course. Privacy abounds on this special property that has been completely updated. Septic System, Roof, Heat/AC, Kitchen, 6 Bathrooms, Windows, Flooring, Well....All NEW. First floor has kitchen, dining room, TWO front to back family/living rooms, full bath, pantry and an office. Second floor has primary bedroom, with a gorgeous bathroom complete w/ a soaking tub, a changing room and his and her walk in closets. Laundry room, another 2 full bathrooms and 3 additional bedrooms round out the second floor. 3rd floor has a full bath and four bedrooms. Basement is finished w/ numerous rooms including a full bath. Outside there's a large inground pool with decorative water feature, patios, and all sorts of plantings surrounded by a huge yard and acres of forest. Unique is a understatement. You've got to see it to believe it.

8 Beds ⋅ 6 Baths ⋅ 73520686 MLS

ABSOLUTELY STUNNING. Enormous 8 Bedroom Home with over 6000 square feet of living on 5.5 acres bordering the Shining Rock Golf Course. Privacy abounds on this special property that has been completely updated. Septic System, Roof, Heat/AC, Kitchen, 6 Bathrooms, Windows, Flooring, Well....All NEW. First floor has kitchen, dining room, TWO front to back family/living rooms, full bath, pantry and an office. Second floor has primary bedroom, with a gorgeous bathroom complete w/ a soaking tub, a changing room and his and her walk in closets. Laundry room, another 2 full bathrooms and 3 additional bedrooms round out the second floor. 3rd floor has a full bath and four bedrooms. Basement is finished w/ numerous rooms including a full bath. Outside there's a large inground pool with decorative water feature, patios, and all sorts of plantings surrounded by a huge yard and acres of forest. Unique is a understatement. You've got to see it to believe it.

175 Pleasant St, Upton

$549,000

This beautifully updated 2,887 sq. ft. single-family home offers stunning views of Pratt Pond and easy access to I-495. Renovated in 2024–2025, it features all-new siding and windows, a brand-new asphalt driveway and parking area, and a commercial-grade fire safety system. Inside, enjoy spacious, flexible living areas perfect for remote work or entertaining. A fully renovated backyard shed adds valuable storage or workshop space. Located on a convenient main road just minutes from downtown Upton.

5 Beds ⋅ 3 Baths ⋅ 73400838 MLS

This beautifully updated 2,887 sq. ft. single-family home offers stunning views of Pratt Pond and easy access to I-495. Renovated in 2024–2025, it features all-new siding and windows, a brand-new asphalt driveway and parking area, and a commercial-grade fire safety system. Inside, enjoy spacious, flexible living areas perfect for remote work or entertaining. A fully renovated backyard shed adds valuable storage or workshop space. Located on a convenient main road just minutes from downtown Upton.

130 High St, Upton

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