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$484,900
3 Beds 2 Baths CONTINGENT Status 73538093 MLS 1,176 SqFt.
Adorable Upton home ready to make your own! This charming property offers so many desirable features, including abundant natural sunlight streaming through the skylights, a convenient location just minutes from Route 495, and beautiful views of Pratt Pond. Enjoy a private backyard with endless potential for entertaining, gardening, or simply relaxing outdoors. Inside, you'll find flexible living space to fit a variety of needs. The finished lower level offers excellent possibilities as a guest suite, in-law space, home office, recreation room, or additional family living area. Whether you're a first-time homebuyer, looking to downsize, or searching for a home with room to grow, this property provides comfort, convenience, and opportunity. Don't miss your chance to enjoy all that Upton has to offer in this inviting home!

10 Hopkinton Rd, Upton

$720,000
3 Beds 3 Baths UNDER AGREEMENT Status 73537714 MLS 1,304 SqFt.
Upton Horse Haven: Iconic 3-Bed, 3-Bath Retreat on 3.75 Acres. Discover one of Upton’s most beloved properties, a premier estate where timeless charm meets outdoor living. This home features modern upgrades including 200-amp electrical system, a new oil tank, and town water for seamless reliability. A newly finished basement for entertaining or retreat. Property offers direct access to miles of trails in the Upton State Forest—perfect for hikers, riders, and nature lovers. The BOH allows boarding for 2-3 horses, making it a dream for equestrians. Set on 3.75 lush acres and just minutes from I-495, it combines suburban serenity with effortless access to city conveniences. According to town zoning regulations the property is subdividable offering flexibility for future development. Don’t miss this iconic, horse-friendly haven—bring your vision and schedule your tour today.

11 James Rd, Upton

$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

$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

$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

$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 UNDER AGREEMENT 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

$1,075,000
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

$1,125,000
4 Beds 4 Baths CONTINGENT 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

$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

$489,999
3 Beds 3 Baths ACTIVE Status 73500996 MLS 1,785 SqFt.
Presenting an exceptional condominium residence at 140 Main St U:B, Upton, MA, a meticulously maintained property constructed in 2020. This 1785 square foot unit offers a refined living experience across three stories, embodying an attractive and contemporary aesthetic. The culinary space features an open-plan design seamlessly integrating with the living room, equipped with stainless steel appliances and a smart refrigerator, facilitating both everyday living and sophisticated entertaining. The bathrooms are appointed with luxurious elements, including a walk-in shower enhanced by multiple shower heads and a rainfall shower, providing a spa-like experience within the comfort of home. Additional property features include a private porch, extending the living space outdoors. To fully appreciate the sophisticated design and functional elegance of this property, we invite your private viewing.

140 Main St Unit B, Upton

$500,000
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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