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$919,900
4 Beds 3 Baths UNDER AGREEMENT Status 73525258 MLS 3,956 SqFt.
Prepare to be enchanted by this stunning, perfectly designed home. One level living at its finest. Crafted with the utmost precision and meticulous design. Every inch of the home was carefully thought of – from a perfectly situated mudroom, to a seamlessly flowing open concept living area, four generously sized bedrooms, a large study, a wonderful oversized four-season porch and an outdoor patio. The finest materials & finishes enhance every element of this home. Beautiful engineered wood floors throughout. Sophisticated designer kitchen, complete with an oversized island, quartz countertops, and top of the line stainless steel appliances. The primary suite offers expansive walk-in closets with an en-suite bath. This exceptional property is nestled in beautiful grounds on a 5.5 acre lot. Deadline for offers is 5:00 pm Tuesday, June 16, 2026. Please make offers good for 24 hours.

145 W River Street, Upton

$699,900
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

$699,000
4 Beds 3 Baths ACTIVE Status 73523806 MLS 2,835 SqFt.
Tucked along a scenic country road, this beautifully preserved early 18th-century Gambrel blends timeless New England character with the comfort and updates today’s buyers seek. Rich with historic charm, the rambling floor plan offers warm, inviting spaces including a stunning 1st-floor primary suite, great room, library/den, front-to-back living room, classic keeping room with stone fireplace, cozy natural wood kitchen, and countless nooks and period details throughout. Three fireplaces add warmth and ambiance. Outside, enjoy a storybook setting with mature trees, flowering shrubs, open lawn, meadow, tranquil pond, and iconic stone walls. Detached 2-car garage with loft and natural light offers endless possibilities. Recent updates include restored mid-1800s windows with storm windows, central air, metal roof, renovated 2nd-floor bath, fresh exterior paint, regraded driveway with cobblestone pavers, and stunning patio with reclaimed brick from Worcester with stone walkway.

52 Elm St, Upton

$1,100,000
4 Beds 3 Baths ACTIVE 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

$1,150,000
4 Beds 4 Baths ACTIVE 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

$1,699,000
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

$675,000
4 Beds 3 Baths ACTIVE Status 73518303 MLS 2,548 SqFt.
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

$1,499,999
5 Beds 4 Baths UNDER AGREEMENT Status 73516179 MLS 3,875 SqFt.
***UNDER CONSTRUCTION*** Location Location Location!! Perfect timing to snatch a brand-new house while it's still under construction and have a chance to pick your own finishes and be ready to move in by the new school year. Perched up on a hill overlooking Pratt Pond. Steps away from Kiwanis Beach Park and enjoy the public beach, 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 bath. 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

$749,900
2 Beds 3 Baths ACTIVE Status 73510750 MLS 2,245 SqFt.
Welcome to the fabulous free-standing Blue Bird Model at Cobbler's Creek! Enjoy a distinctive townhouse with 2,200+ square feet of great space easily adaptable to your decor & lifestyle. From a welcoming front porch, enter a foyer with custom moldings & closet open to a spacious open floor plan including a living room & door to a deck, dining area & stylish kitchen w/white cabinets, Quartz counters & stainless-steel appliances. Primary bedroom suite has double closets plus full bath with tiled shower & laundry. Upstairs, there's a large second bedroom, full bath & bonus room. Unfinished lower-level space is ideal for storage. Attached two-car garage. Enjoy living in Upton's most popular 55+ community of 59 townhomes that will have access to a club house & more. Easy access to routes 495, train, shopping & restaurants. Don't miss out on this amazing price in a fabulous community! *** HOA Fee Includes Water/ Sewer/ Spectrum Internet & Cable plus more *** Great opportunity!

19 Boot Shop Road Unit 19, Upton

$1,450,000
5 Beds 5 Baths UNDER AGREEMENT Status 73508751 MLS 4,395 SqFt.
Nestled at the end of a private cul-de-sac on nearly two acres, this meticulously renovated Colonial estate offers a premier multi-generational layout featuring main residence & fully equipped accessory dwelling. Beautiful main house boasts a mahogany deck, chef’s kitchen complete w/ quartz countertops, double wall ovens, gas cooktop, & an oversized butcher-block island, all adjacent to a coffee, wine bar & dining area w/attached deck. 2 fireplaced living rooms & 1/2 bath. New great room above the garage. Second floor hosts 4 bedrooms including luxurious primary suite w/ spa-like bath & walk-in closet. A newly finished walk-up attic game room. Connected by a breezeway, the self-contained ADU, perfect for an Au Pair or InLaw, boasts its own full kitchen, fireplaced living area, office, and a bedroom overlooking serene nature views. This expansive property has 2/two car garages, is pro landscaped and hardscaped and full main house generator. Main house lovingly renovated, ADU is new!

8 Stearns Road, Upton

$799,000
2 Beds 2 Baths ACTIVE Status 73503206 MLS 1,734 SqFt.
Are you looking for low-maintenance single-level living in a thoughtfully designed new construction condo located in an amazing 55+ community? Come check out the "Starling" floor plan at Cobbler's Creek, built by exceptional builders with a reputation for excellence. As you step inside, you're welcomed by an open and airy floor plan that seamlessly connects the sunny living room, dining room & kitchen. The kitchen features a clean, contemporary layout w/attractive cabinets, ample Quartz counter space, modern SS appliances & a center island that can double as a breakfast bar or casual gathering spot. Off the main living space, a dedicated office provides a quiet area to work from home. Primary bedroom is a comfortable retreat includes en-suite bathroom w/double sinks, tiled shower & large closet. Ideal 2nd bdrm for guests & full bath. Laundry & 2-car garage. Enjoy a serene yet convenient location. ** HOA Fee Includes Water/ Sewer/ Spectrum Internet & Cable plus more ** Terrific value!!

21 Boot Shop Road Unit 21, Upton

$855,900
2 Beds 3 Baths ACTIVE Status 73502176 MLS 2,228 SqFt.
Come see what's new 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 two-story living with everything you need handy on the first floor such as a covered front porch, foyer, powder room, laundry rm & entry to your 2-car garage. An open floor plan offers a living & dining area w/ fireplace & access to a deck or patio, plus kitchen featuring beautiful cabinets, center island w/quartz countertops & stainless-steel appliances. Primary bedroom suite includes a spacious closet & full bath w/double sinks & tiled shower. Second floor offers has a terrific loft space, second bedroom & full bath. Energy efficient systems. Be part of a wonderful community with access to a clubhouse & trails. ** HOA Fee Includes Water/ Sewer/ Spectrum Internet & Cable plus more **

7 Boot Shop Road Unit 7, Upton

$489,999
3 Beds 3 Baths PRICE CHANGED Status 73500996 MLS 1,785 SqFt.
Welcome to 140 Main St U:B in Upton, MA!! This 2020-built condominium presents an attractive property in great condition, offering 1785 square feet of refined living space. This is a three-story residence, w/expansion potential in LL. Situated on the first floor, you'll find a sophisticated & relaxed living space. The kitchen is thoughtfully designed for both culinary pursuits & social engagement, featuring stainless steel appliances & granite counters. An open-plan layout seamlessly connects it w/the living room, fostering an expansive & inviting atmosphere. The integration of a SMART REFRIDGERATOR further enhances its modern functionality. The primary bathroom offers a luxurious retreat, equipped w/a walk-in shower that includes multiple shower heads, & rainfall shower feature, providing a spa-like experience. With three bedrooms and two full bathrooms, complemented by an additional half bathroom, this condominium accommodates luxury lifestyle wants & needs. Great commuter spot!

140 Main St Unit B, Upton

$765,000
4 Beds 3 Baths UNDER AGREEMENT Status 73500985 MLS 3,018 SqFt.
Welcome home to this distinctive four-bedroom property set on a picturesque 1.84-acre lot, offering the perfect blend of charm, space, and modern updates. Enjoy peaceful mornings on the inviting farmer’s porch or unwind on the stunning new patio while taking in beautiful sunset views. Inside, this home is anything but ordinary, featuring hardwood floors, a flexible first-floor bedroom, and a dramatic second-floor fireplaced family room that adds warmth and character. The expansive primary suite serves as a private retreat with an ensuite bath, bonus space for a reading nook or exercise area, and access to a walk-up attic with future potential. Numerous major updates—including heating system, roof, windows, oil tank, hot water heater, fresh paint, carpets, slider, and new D-box—provide true move-in readiness. Additional highlights include a finished lower-level room ideal for a gym or hobby space. Located in desirable Upton with top-rated schools and easy access to major routes.

1 South St, Upton

$1,225,000
4 Beds 6 Baths ACTIVE Status 73498932 MLS 5,736 SqFt.
With a flexible layout that supports multigenerational living, this gorgeous custom-built colonial has ample space and is situated on 3+ private acres. From the moment you step into the grand two-story foyer adorned w/ granite flooring, you’ll be captivated by the attention to detail & luxurious features throughout, incl 9ft+ ceilings & gleaming hardwoods. Spacious fam rm is a true showpiece w/ stunning floor-to-ceiling stone fireplace & interior balcony. The expansive gourmet kitchen boasts a huge island w/ vegetable sink, abundant counter space, cabinetry & gas cooktop. An inviting eat-in area is bathed in natural light w/numerous windows. 1st floor, open concept guest suite w/ full bath & exterior access. Upstairs, spacious primary suite w/ lg walk-in closet & spa-like bath w/ jetted tub & tiled shower w/glass door. 3 addt'l good-sized bedrooms, 2 full baths & convenient 2nd flr laundry. Finished walkout lower level has food prep area and full bath. Perfect home for entertaining!

12 Breton Road, Upton

$439,000
4 Beds 2 Baths UNDER AGREEMENT Status 73494800 MLS 2,110 SqFt.
Antique Greek Revival single-family home in the heart of Upton’s historic district. The Thomas McFarland House (1810) is set on the right side of a 1.14-acre lot that slopes down to scenic Mill Pond. Offering four bedrooms, two full baths, 2100 sq ft living space and a two-car garage.  The home is rich in character but does require significant renovation. Features include, abundant natural light, an antique fireplace, wide plank flooring, ample attic storage, and pond views from all rear-facing windows. Gas cooking and gas furnace (2009) Partitioned basement, one with walk-out access. With 265’ of street frontage, the expansive lot presents unique development potential, buyers to do their own due diligence. House is serviced by Town Water & Sewer and Natural Gas. This property is ideal for buyers seeking a rewarding restoration project in an idyllic setting. Great commuter location with quick and easy access to 495 and the Mass Pike. Showings by appointment only.

17 N Main St, Upton

$1,100,000
4 Beds 4 Baths ACTIVE Status 73490363 MLS 3,487 SqFt.
This beautifully designed custom home offers the perfect blend of privacy, space, and modern functionality. Set back from the street and positioned on an elevated lot, the home delivers both curb appeal and a sense of seclusion. Inside, you’ll find a thoughtfully designed floor plan featuring 4 spacious bedrooms and 3.5 bathrooms. The heart of the home is ideal for both everyday living and entertaining, with open, flowing spaces and quality craftsmanship throughout. Upstairs, convenience meets luxury with a dedicated second-floor laundry room—perfectly located near all bedrooms. The oversized primary suite serves as a true retreat, offering generous proportions, ample closet space, and a private en-suite bath designed for comfort and relaxation. With its custom layout, elevated setting, and attention to detail, this home is a standout opportunity for buyers seeking both style and functionality in a serene setting.

99 W River St, Upton

$850,000
3 Beds 3 Baths UNDER AGREEMENT Status 73488757 MLS 3,300 SqFt.
Set at the end of a dead-end road, this expanded custom contemporary offers over 10 acres of private land—a rare blend of space, flexibility, and future potential. This well-maintained 3-bed, 2.5-bath home is filled with natural light from expansive windows and skylights, creating an open, inviting layout. A standout 30x24 heated bonus room above the garage provides exceptional space for recreation, entertaining, or extended living. Additional features include a deck, indoor jacuzzi, wood stove, mini-splits (2 yrs), newer windows and roof (~10 yrs), boiler (2014), 200 amp electrical, generator hookup, and private well. Passing Title V with oversized 4-bed septic allows for expansion or ADU potential. Preliminary subdivision plans (subject to approvals). Convenient to major highways with access to Westborough, Framingham, and Natick, offering easy commute to Boston.

215 North St, Upton

$499,000
4 Beds 3 Baths CONTINGENT Status 73487287 MLS 2,228 SqFt.
Back on market due to buyer's home sale contingency and priced to sell! A rare opportunity to own a four-bedroom, two and a half bath residence in the desirable Samreen Villas. This private end unit offers exceptional natural light and a thoughtfully designed layout ideal for both everyday living and entertaining. The main level features hardwood and ceramic tile flooring, an open-concept kitchen and dining area, and a dramatic living room with soaring ceilings and an oversized window that fills the space with natural light. A convenient half bath completes the first floor. Upstairs you’ll find three generously sized bedrooms that share a full bath, along with a spacious primary suite featuring a vaulted ceiling and private en-suite bath. Laundry is conveniently located on the second floor. The lower level offers additional flexible space—perfect for a home office or playroom. A wonderful combination of privacy, space, and functionality in a highly desirable community.

1 Knowlton Circle Unit 1, Upton

$550,000
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

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

6 Wood St, Upton

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