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$799,900
7 Beds 4 Baths ACTIVE Status 73552661 MLS 3,314 SqFt.
Don't miss this well-maintained multifamily property offering an excellent opportunity for both investors and owner-occupants. Whether you're looking to generate rental income, build long-term wealth, or offset your mortgage by living in one unit while renting the other, this property offers outstanding flexibility.Each unit features spacious living areas, comfortable bedrooms, functional layouts, and abundant natural light. The property provides ample parking, outdoor space, and the convenience of separate living areas, making it attractive to tenants and homeowners alike.Ideally located in the heart of Upton, you'll enjoy easy access to local shops, restaurants, schools, parks, and major commuter routes while experiencing the charm of a welcoming New England community.This is a rare opportunity to own an income-producing property in a desirable location with strong rental already.

158 Main St, Upton

$789,900
4 Beds 3 Baths CONTINGENT Status 73546600 MLS 2,668 SqFt.
This exceptional 3.7 acre country estate blends luxury living with outstanding outdoor amenities. The Colonial home features hardwood floors, soaring ceilings, multiple fireplaces, wood stoves, new central heat, mini-splits, and a gourmet kitchen with granite counters and stainless appliances. The main level offers formal and casual living spaces, a bright dinning room, living room, family room, full bath, and bonus room. Upstairs are four bedrooms, including a spacious primary suite with 3/4 bath and a custom California Closet. The finished lower level adds 2 rooms for more flexible living space. Solar panels, updated well equipment, and a new boiler improve efficiency. Outside, enjoy a hot tub, screened porch, fire pit, pond, barn/gym and large recreation area with a soccer/basketball half court. Located across from Upton State Forest with direct access to miles of trails.

218 Mechanic, Upton

$709,000
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

$800,000
3 Beds 3 Baths ACTIVE 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 ACTIVE 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

$744,900
2 Beds 4 Baths UNDER AGREEMENT Status 73525704 MLS 2,200 SqFt.
LAST UNIT AVAILABLE NEW CONSTRUCTION. Free standing unit no age restrictions in 4 lot subdivision. Kitchen is spacious with eat in dining area, hardwood floors, granite, kitchen island, stainless steel appliances. Opens to a family room with access to backyard. Upstairs has a 3 bedroom layout but deeded as a 2 bedroom dwelling 3rd room could be in home office/den/playroom. Ensuite primary with tiled shower and glass enclosure with double vanity sinks and soaking tub. Second full bath for bedroom 2 and bonus room. Finished room and full bath in walk out basement with full egress door no bulkhead, plus storage area. Third floor walk up also has an area for storage or future finished space. House is on a dead end street close to center of town! Home are less than 5 miles to RT495, making it a great commuter location. Less than a 1/2 mile to boat ramp on Pratt Pond and 1 mile to Kiwanis Beach on Pratt Pond where you can enjoy swimming, boating and fishing. It truly is the perfect location!

27 James Road Unit 4, 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

$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

$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

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