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2 Brookside St, Upton
$849,900
4 Beds ⋅ 3 Baths ⋅ UNDER AGREEMENT Status ⋅ 73562333 MLS ⋅ 3,132 SqFt.
Stately Colonial offering a rare combination of privacy, natural beauty & modern updates in one exceptional property. Every window captures peaceful views of the surrounding landscape, creating a vacation-at-home feeling year-round. This spacious home features beautiful hardwood floors throughout the 1st floor & a versatile floor plan designed for easy everyday living & entertaining. The stunning kitchen is the heart of the home, offering abundant cabinetry, a walk-in pantry & opens to the oversize cathedral-ceiling family room. 1st floor laundry/mudroom adds everyday convenience. Generous sized primary suite includes a flexible bonus room ideal for another home office, fitness space or sitting area. A plethora of windows fills the home with bright, natural lighting. Thoughtfully sited for maximum privacy, the inviting farmer’s porch & expansive composite deck provide ideal spaces to relax or entertain. Taft Mill & Goss Pond are just a short walk away, offering kayaking, fishing, hiking & year-round recreation. Convenient access to I-495, the Mass Pike, Worcester, Providence & Boston. Your search is over - welcome home!

2 Brookside St, Upton

66 Glenview St, Upton
$1,320,000
5 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 73562275 MLS ⋅ 4,498 SqFt.
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

24 Main St, Upton
$550,000
4 Beds ⋅ 3 Baths ⋅ UNDER AGREEMENT Status ⋅ 73559135 MLS ⋅ 2,548 SqFt.
Previously relocated owners say it's time to sell! This rare antique in town colonial awaits a new owner. Wait until you see all the character this home exudes. Freshly painted throughout! Bright and sunny layout, hardwood flooring, gorgeous woodwork, nooks and crannies, tin ceilings, built ins, sun filled corner glassed in porch & white picket fence. This is truly a special home. Large dining area with pellet stove is perfect for entertaining. A spectacular third floor addition encompasses a large primary suite with a spectacular, spa like bathroom. Three/four more bedrooms on the second floor - One with an attached room makes a perfect in home office or nursery. Private back yard with a huge deck complete with a pergola. Above ground pool, fire pit, and storage shed, all surrounded by mature gardens, and perennials. Come take a look - you'll fall in love!!

24 Main St, Upton

10 Sadler Road, Upton
$875,000
4 Beds ⋅ 3 Baths ⋅ UNDER AGREEMENT Status ⋅ 73551967 MLS ⋅ 2,806 SqFt.
*** A NEW, NEUTRAL COLOR, COZY CARPET IS COMING THIS MONTH ** Come for the privacy, stay for the home! It’s hard to beat the setting of this expansive Federal-front Colonial. Set on 2 acres of wooded bliss at the end of a cul-de-sac, mature trees and thoughtfully designed landscaping create an incredible ambiance that will make you feel lucky to wake up to it every day. It is pure serenity with an incredibly spacious layout to boot. 3000+ square feet feels warm and homey - New England charm oozes in every room. The kitchen is HUGE and has NEW quartz countertops with a massive eat-in area that overlooks that stunning background. The first floor has a seamless flow to it with details like exposed beams, NEW skylights and a NEW ceiling fan in the family room. A second living space, formal dining and powder room round out the first floor. Upstairs, the primary suite boasts a beautiful NEW modern bathroom. Three spacious bedrooms with that NEW carpet (photos coming) and a guest bath provide space for everyone. Outside, a NEW composite deck overlooks a massive backyard where you can grow your own fruit! *chef’s kiss* You'll love the established pear and cherry trees, blueberry bushes, plus there’s a fenced garden area. Additional UPDATES include vinyl siding, front steps, garage doors and a finished lower level. Get in before the holidays and make this your home sweet home!

10 Sadler Road, Upton

19 West Main Street, Upton
$989,900
4 Beds ⋅ 4 Baths ⋅ UNDER AGREEMENT Status ⋅ 73547396 MLS ⋅ 2,990 SqFt.
UNDER CONSTRUCTION...Enjoy The Benefits of New Construction with Energy Efficiency & Low Future Maintenance! This stunning home offers the perfect blend of classic elegance and modern convenience with a spacious 1st FLOOR PRIMARY SUITE and laundry and 3 additional bedrooms on the 2nd level. The partially finished basement with finished half bath provides extra square footage plus access to the spacious backyard. 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 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 Nov 2026 Closing

19 West Main Street, Upton

17 West Main Street, Upton
$999,900
4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 73547384 MLS ⋅ 2,780 SqFt.
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

56 Shannon Way Unit 56, Upton
$649,000
2 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 73546012 MLS ⋅ 1,950 SqFt.
Welcome to this beautifully maintained two-story townhouse in the highly desirable 55+ Upton Ridge community, where comfort, style, and low-maintenance living come together. Built in 2023 this floor plan features a first-floor primary suite, offering both privacy and ease of living. Upstairs features a generously sized second bedroom with walk in closet, full bath and a spacious second-floor loft perfect for a home office, or additional living space. The open-concept design seamlessly connects the living room, dining area, a chef’s kitchen, beautiful hardwood floors creating an ideal setting for both everyday living and effortless entertaining. Expansive windows fill the home with natural light while showcasing peaceful wooded views that provide a tranquil backdrop. The expansive walk-out unfinished basement presents exceptional potential for future living space, a home gym, workshop, or abundant storage. Easy access to major routes, shopping and boarders Shining Rock Golf Club!

56 Shannon Way Unit 56, Upton

117 South Street, Upton
$2,500,000
4 Beds ⋅ 5 Baths ⋅ UNDER AGREEMENT Status ⋅ 73541742 MLS ⋅ 4,040 SqFt.
75-Acre Elite Equestrian & Wellness Sanctuary. Ultimate private retreat with a 4,040 SF luxury Cape, world-class horse facilities, and resort backyard. Trail access to West Hill Dam. RESIDENCE: Chef's kitchen (Jade 6-burner, Sub-Zero, granite waterfall island). 1st-floor primary suite with vaulted ceilings & spa bath. 3 upper bedrooms, office, large bonus room + finished walkout lower level. 2-car garage with EV charger & generator backup. EQUESTRIAN: Professional 9-stall barn, heated tack room, wash stall & blanket laundry. 12,384 SF indoor arena (172'x72') + 130'x80' outdoor arena. 60' round pen & 15 turnout paddocks. Roof solar array on barn supplies powers to the property. WELLNESS & RESORT: Detached climate-controlled gym & solar yoga "She Shed." Heated, saltwater, gunite pool, hot tub, 6-person barrel sauna. Outdoor kitchen with pizza oven. Meditation labyrinth, organic fruit orchards, and berry patches.

117 South Street, Upton

12 Boot Shop Road Unit 12, Upton
$799,000
2 Beds ⋅ 3 Baths ⋅ UNDER AGREEMENT Status ⋅ 73535231 MLS ⋅ 2,228 SqFt.
New amazing price at Cobbler's Creek, a premier 55+ community of detached condominiums by the renowned Black Brook Realty builder group! Enjoy a Storybook setting of homes nestled in a serene landscape where every day feels like a retreat! The popular "Cardinal" model offers 2-story living with everything you need handy on the 1st floor such as a covered front porch, foyer, powder rm, laundry rm & entry to your 2-car garage. An open floor plan offers a living & dining area w/ fireplace & hardwood floors accessing a deck with tranquil wooded views, plus kitchen featuring beautiful white cabinets, large center island & stainless-steel appliances. Primary bedroom suite includes h/w floors, spacious closet & full bath w/double sinks & tiled shower. 2nd floor offers has a terrific loft w/hrdwd, second bedroom & full bath. Energy efficient systems. Be part of a wonderful community w/access to a clubhouse & trails. * HOA Fee Includes Water/ Sewer/ Spectrum Internet & Cable & more. Ready now!

12 Boot Shop Road Unit 12, Upton

5 Boot Shop Road Unit 5, Upton
$749,900
2 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 73535220 MLS ⋅ 1,734 SqFt.
Beautiful new construction one-level "Starling" floor plan now available at Cobbler's Creek, a vibrant 55+ community built by exceptional builders with a reputation for excellence! You're welcomed by an open & airy floor plan that seamlessly connects the sunny living room w/fireplace & built-ins, dining rm & kitchen all w/hardwood floors. The kitchen features attractive cabinets with moldings above, ample Quartz counter space, modern SS appliances, tile backsplash & center island that can double as a breakfast bar or casual gathering spot. The living room accesses a deck & patio. Off the main living space, a dedicated office provides a quiet area to work from home. Primary bedroom is a comfortable retreat including en-suite bathroom w/double sinks, tiled shower w/glass door & large closet. Second bdrm for guests & full bath. Laundry & 2-car garage. Enjoy a serene & convenient location close to everything. ** HOA Fee Includes Water/ Sewer/ Spectrum Internet & Cable & more ** Ready now!

5 Boot Shop Road Unit 5, Upton

110B High Street, Upton
$600,000
3 Beds ⋅ 3 Baths ⋅ UNDER AGREEMENT Status ⋅ 73530257 MLS ⋅ 1,792 SqFt.
Nestled on a 6-acre lot, this private retreat offers the perfect blend of country charm and endless potential. Surrounded by nature and set 1/3 of a mile back from the road, this 3-bedroom home provides a peaceful setting with sweeping views of the expansive front lawn. Inside, the open-concept design creates a warm and inviting atmosphere. The family room features a vaulted ceiling, hardwood floors and a wood-burning fireplace. Charming kitchen w/ dining area open to the family room—ideal for everyday living and entertaining. A 1st floor bedroom offers flexibility for one-level living or as an office or guest rm. Upstairs, you’ll find two generously sized bedrooms, including a primary bedroom complete w/ensuite bath and a Juliette balcony. Whether you’re looking for privacy, acreage, or the opportunity to customize a home to your personal style, this property is a rare find. Passing Title V for 4 bedrooms.

110B High Street, Upton

87 Shannon Way Unit 86, Upton
$640,000
2 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 73524427 MLS ⋅ 1,950 SqFt.
Enjoy low-maintenance living at Upton Ridge, a desirable 55+ community just a short stroll from the renowned Shining Rock Golf Course. This beautiful Milan-style two-story home offers a spacious, thoughtfully designed floor plan featuring a first-floor primary suite and open-concept living. The oversized kitchen is perfect for entertaining, complete with upgraded cabinetry, quartz countertops, and a large center island. The light-filled gathering room opens through a slider to the rear deck, with remote controlled awning, creating a seamless indoor-outdoor space to relax and enjoy the peaceful surroundings. Upstairs, you’ll find a spacious loft, a generously sized second bedroom with a full bath and walk-in closet. Experience the beauty and tranquility of Upton Ridge while enjoying convenient access to Boston, Providence, New Hampshire, Route 9, I-90, I-495, and the commuter rail.

87 Shannon Way Unit 86, Upton

52 Elm St, Upton
$699,000
4 Beds ⋅ 3 Baths ⋅ UNDER AGREEMENT Status ⋅ 73523806 MLS ⋅ 2,835 SqFt.
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

32 Mendon St, Upton
$1,050,000
4 Beds ⋅ 3 Baths ⋅ CONTINGENT Status ⋅ 73522448 MLS ⋅ 2,924 SqFt.
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

30 Mendon St, Upton
$1,125,000
4 Beds ⋅ 4 Baths ⋅ UNDER AGREEMENT Status ⋅ 73521066 MLS ⋅ 3,402 SqFt.
30 Mendon St, Upton, MA Experience modern luxury in this newly constructed 2026 single-family home over 3,000 square feet of thoughtfully designed living space. Blending timeless elegance with contemporary comfort, this exceptional residence is crafted for today’s lifestyle. Featuring four spacious bedrooms and four full bathrooms, the home provides both privacy and convenience with high-end finishes throughout. The open and inviting layout is ideal for both everyday living and entertaining. A two-car built-in garage offers secure parking and additional storage, while the welcoming front porch adds charm and curb appeal to this stunning new construction. Located in desirable Upton, this home presents a rare opportunity to own a beautifully designed residence in impeccable condition.

30 Mendon St, Upton

175 Pleasant St, Upton
$1,649,000
8 Beds ⋅ 6 Baths ⋅ ACTIVE Status ⋅ 73520686 MLS ⋅ 6,850 SqFt.
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

140 Main St Unit B, Upton
$474,900
3 Beds ⋅ 3 Baths ⋅ REACTIVATED Status ⋅ 73500996 MLS ⋅ 1,785 SqFt.
Welcome to 140 Main St U:B in Upton, Massachusetts. Constructed in 2020, this 1,785-square-foot condominium stands in great condition, offering a sophisticated living experience across its three-story architectural design. Positioned on the first floor, this residence provides a seamless blend of modern functionality and refined living, defining a new standard for elevated residential comfort. The kitchen serves as the heart of the home, equipped with high-end stainless steel appliances and advanced smart refrigerator technology. The workspace is defined by elegant stone counters, providing both durability and a sleek aesthetic for culinary preparation. This space is designed to support both daily routines and seamless entertaining with modern efficiency. The bathrooms reflect a commitment to a spa-inspired routine. One bathroom features a luxurious walk-in shower, which incorporates multiple shower heads and an overhead rainfall shower system, offering a tailored and refreshing bathing experience. Beyond the interior living spaces, the property provides a dedicated porch area, offering an ideal setting for relaxation or extending your living environment into the fresh air. With its thoughtful layout and contemporary appointments, this residence offers an exceptional opportunity for those seeking a move-in ready home in a prime location. We invite you to schedule a private tour to experience the quality and refined atmosphere of this exceptional Upton residence firsthand.

140 Main St Unit B, Upton

Lot 108 W Main St, Upton
$400,000
ACTIVE Status ⋅ 73471805 MLS
5.45± acres zoned General Business (GB) located along West Main Street (Route 140) in Upton. This versatile parcel offers strong road frontage, visibility, and flexibility for a variety of commercial, professional, mixed-use, or investment opportunities, subject to Town approvals. The GB zoning district supports a broad range of business and service uses, making this an ideal site for owner-users, developers, or long-term investors. Conveniently located near Old Grafton Road with access to surrounding communities. The property abuts the Baker Pond area, offering a unique natural setting alongside commercial potential. Buyers to perform all due diligence with the Town of Upton regarding permitted uses, dimensional requirements, wetlands, and approvals. Zoning: General Business (GB).

Lot 108 W Main St, Upton

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