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$499,000
3 Beds 1 Baths NEW Status 73555450 MLS 1,316 SqFt.
Stunning views with the ability to enjoy time on the water for under $500K. Welcome home to this beautiful single-family ranch in Upton MA across the street from Pratt Pond. Enjoy kayaking, canoeing, boating, and fishing just steps from your front door. This well maintained 3-bedroom 1-bath home sits on a flat 0.75-acre lot perfect for spending time outside entertaining, gardening, and more. Inside you are met with a beautiful living room with vaulted ceilings and a scenic view of the water. Your comfortable kitchen flows nicely into the dining room which is well sized to host your next get-together. Down the hall your full bathroom and three bedrooms await (one with your washer and dryer) all with hardwood flooring. Additional highlights include a heated 2-car detached garage with plenty of storage space, a fenced-in backyard and plenty of off-street parking. Homes that offer scenic views, a usable yard, and this much value are hard to find. Don't miss this opportunity to make this charming Upton home your own! Call to schedule your showing today!

71 School St, Upton

$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

$699,000
6 Beds 3 Baths CONTINGENT Status 73552323 MLS 2,617 SqFt.
Rare 2-Family Gem with Historic Charm & Modern Luxury. Discover this meticulously renovated two-family home, perfectly situated on 2 sprawling acres near the heart of town. Gutted to the studs in 2015 and updated with a new roof, windows, and high-end finishes, this property offers the peace of mind of a new build with the character of a classic estate. Both units are fully de-leaded, light-filled, and feature gorgeous wide-plank and hardwood floors, granite countertops, and stainless steel appliances. Unit 1 (822 sq. ft.): A comfortable first-floor layout with direct access to a full basement featuring private laundry hook-ups. Unit 2 (1,811 sq. ft.): A stunning two-story retreat (levels 2 & 3) boasting 4 spacious bedrooms, 2 full baths, a dedicated laundry room, and a massive walk-in closet. Mechanicals are top-tier with separate utilities, including two new boilers, 2022, 2023 and tankless hot water heaters. Outside, the property shines with exceptional curb appeal, 8 parking spaces

78 Main Street, Upton

$675,000
5 Beds 2 Baths ACTIVE Status 73540925 MLS 2,534 SqFt.
WOW! This two-family home has had major systems updated in the last two years: Oil-fired boiler w/oil-fired hot water tank, new well pump & piping, all appliances less than 2 years except for one 8-9 year old refrigerator, exterior of fireplace just repointed, updated electrical. First floor unit has a large foyer, generously sized living room with stunning hardwoods and fireplace, oversize eat-in kitchen, laundry, full bath & 3 bedrooms. Second floor accessed by totally separate entrance to the rear has an eat-in kitchen, pantry, full bath, living room, and 2 bedrooms. There's engineering being done for a new 4-bed septic system. Gorgeous lot on just under an acre, tons of parking in horseshoe driveway. Garage under. Move-in ready, could use some cosmetics. Great for income property or first-time buyer looking to have rental income. Come enjoy all Upton has to offer ~ award-winning schools, conservation lands, convenient commuter location!! Some photos virtually "decluttered"

90 Glenview St, Upton

$639,900
3 Beds 2 Baths ACTIVE Status 73540194 MLS 1,546 SqFt.
Bursting with charm and set on 1.84 picturesque acres, this white antique Cape offers standout curb appeal on a scenic country road. Designed for easy living, the first floor features the primary bedroom, full bath, laundry, and an open-concept living, dining, and kitchen area with beautiful backyard views and direct access to the deck. Outside, the freshly painted red barn and smaller white barn, both with electricity, add character, versatility, and exciting potential, with the larger barn ready for restoration and future possibilities. Ideally located near the Hopkinton line, this property is a commuter’s dream—just over 3 miles to I-495—while still convenient to shopping, dining, and everyday amenities. A rare opportunity to enjoy classic New England charm, usable acreage, and a sought-after location.

149 Glenview St, Upton

$484,900
3 Beds 2 Baths PRICE CHANGED 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

$675,000
3 Beds 2 Baths UNDER AGREEMENT Status 73537386 MLS 1,638 SqFt.
The charm of yesteryear with moden conveniences. This meticulously maintained and updated 3 bed, 1.5 bath Antique home has been loved by same family for 93 years and is now looking for the next family to welcome home. Pride of ownership shows in custom laid hardwoods and buit-ins. Light-filled large rooms, 4 working fireplaces in the living room, first-floor bedroom, and two upstairs bedrooms. Home offers expansion potential with 15.3 x 14.7 unfinished wing, adjacent to kitchen, waiting for your imagination. Central air, furnace, water heater, roof, and updated baths all newer and installed since 2013. Detached garage/shed for projects, storage, or parking. Stunning level lot has been the ideal setting for weddings, parties, and story hours throughout the generations. This home is truly a must-see!! Located convenient to Upton's many conservation land/trails, schools, highways, and all Upton has to offer! Sellers willing to sell completely furnished.

236 Mendon St, Upton

$420,000
3 Beds 1 Baths UNDER AGREEMENT Status 73530168 MLS 1,727 SqFt.
Bring your vision and unlock the potential of this classic Colonial set on a beautiful, level lot in desirable Upton! Offering a rare combination of major exterior updates and room to build instant equity, this home is the perfect opportunity for investors, contractors, or buyers eager to create their dream home. Significant improvements have already been completed including 9 year old vinyl siding & roof. Inside, you’ll find hardwood floors, an updated kitchen, generous room sizes and abundant natural light throughout. While the interior is ready for cosmetic improvements and renovation, the possibilities are endless. The spacious yard provides plenty of room for entertaining, gardening, recreation, or future enhancements. Conveniently located near schools, parks, shopping, restaurants, and commuter routes. A solid home with great bones, valuable updates already in place, and tremendous upside in one of Upton’s most sought-after communities.

5 Pleasant St, Upton

$419,000
3 Beds 2 Baths UNDER AGREEMENT Status 73526517 MLS 1,420 SqFt.
Welcome to this beautifully maintained 3 bedroom, 2 bath condominium in the desirable town of Upton. This bright and inviting home features an open concept layout designed for comfortable living and effortless entertaining. The modern kitchen is highlighted by elegant quartz countertops, ample cabinetry, and a seamless flow into the dining and living areas.Enjoy year round comfort with central heating and air conditioning throughout the home. The spacious primary bedroom offers a private retreat, while two additional bedrooms provide flexibility for family, guests, or a home office. Additional highlights include a washer and dryer conveniently located in the unit and the ease of low maintenance condominium living.

51 School St Unit 3, 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

$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

$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

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