Browse All Upton MA Between $500K - $600K Properties for Sale

6 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 73588692 MLS ⋅ 2,974 SqFt.

Two homes under one roof on a level 0.65-acre corner lot just off Main Street! Owned by the same family for decades, this classic c.1890 two-family offers 2,974 sq ft and rare flexibility. Unit 1 features 3 bedrooms, 1.5 baths, a bright bay-windowed living room, a dining room with a decorative ceiling, an updated white kitchen, and laundry. Unit 2 offers 2 bedrooms, a full bath, living room, family room, and eat-in kitchen. Each unit lives on two levels, like a home of its own. Enjoy screened porches, a deck, perennial gardens, and a yard with room to play, grow, and gather. Ideal for multigenerational living, owner-occupying one unit while rent from the other helps offset your mortgage, or adding a solid investment to your portfolio. Full basement, vinyl siding, parking for 4, and a lake/pond beach within a mile. Two-families like this rarely come to market in Upton. Schedule your showing today!

55 School Street, Upton

$599,000

3 Beds ⋅ 2 Baths ⋅ UNDER AGREEMENT Status ⋅ 73581868 MLS ⋅ 1,496 SqFt.

Discover the perfect blend of timeless character and modern convenience in this spacious 3-bedroom, 2-full-bath home set on more than 3 acres of private, classic grounds complete with traditional stone walls. With generously sized rooms, high ceilings, and a highly livable floor plan, this home offers plenty of space to relax, entertain, and enjoy the best of country living. The recently remodeled, oversized eat-in kitchen is truly the heart of the home, featuring a propane fireplace, grill/smoker, two ceiling fans, and ample room for gatherings. Numerous updates provide modern peace of mind, including newer windows, roof, exterior paint, and a Generac whole-house generator. The main level offers exceptional flexibility, with a spacious living room highlighted by a dramatic floor-to-ceiling stone fireplace, two additional bedrooms, a full bath, and a convenient laundry room. The inviting family room features a wood stove and opens directly to a 17.9' x 9.2' screened composite porch with cathedral ceiling and ceiling fan ~ the perfect spot for enjoying peaceful summer evenings. Just beyond, an additional 13' x 23' composite deck overlooks the stunning private yard, complete with fruit trees and mature plantings. Upstairs, the expansive primary bedroom provides a private retreat with its own ensuite bath and plenty of room to unwind. Additional features include an oil-fired boiler, Viessmann indirect hot water heater, updated electrical panel for the Generac generator, oversized parking, and an additional barn/garage/shed offering abundant storage and space for hobbies, equipment, or your favorite grown-up toys. Ideally located just minutes from Westborough Center and less than 10 miles from the Westborough MBTA station, this home offers the tranquility of a private 3+ acre setting with convenient access to commuting, shopping, dining, and everyday amenities. Experience your own slice of heaven in Upton, home to award-winning schools and a wonderful sense of community. Your next chapter—and perhaps the perfect place to be home for the holidays awaits!

15 North St, Upton

$519,899

3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 73574288 MLS ⋅ 1,760 SqFt.

Move right into this beautifully maintained, 2020-built end-unit townhouse in the heart of Upton. Set at the rear of the building and open on three sides, the home enjoys abundant natural light throughout. Three finished levels offer a flexible, well-designed layout. The open main level features a sun-filled living room and a stylish kitchen with a large island, stainless steel Samsung appliances, farmhouse sink and tile backsplash, plus a convenient half bath. The second floor offers two spacious bedrooms with double closets, a full tiled bath and in-unit laundry. The entire third floor is dedicated to a private primary suite with a generous closet and en-suite bath. Additional highlights include hardwood flooring throughout, gas heat, central air, a full basement for storage and two exclusive use parking spaces. Enjoy a five-unit association with a low monthly fee, close to Upton Town Center, walking trails, Route 140, I-495 and the Grafton commuter rail.

140 Main St Unit E, Upton

$569,000

3 Beds ⋅ 2 Baths ⋅ CONTINGENT Status ⋅ 73573230 MLS ⋅ 1,556 SqFt.

LENDER FUNDED RATE BUY DOWN Offered on this property will help lower your monthly payments. Welcomes om this this charming Colonial Style home, offering warmth, character, and modern comfort throughout. The inviting open floor plan creates a seamless flow between the living, dining, and kitchen areas, making the home feel spacious and welcoming. Beautiful hardwood flooring runs throughout the home. The living room is complemented by a cozy fireplace with an elegant marble surround. The kitchen features Stainless Steele appliances, durable granite countertops, and a breakfast bar, flowing naturally to the main living spaces, perfect for everyday living and entertaining.On the second floor you will find three generously sized bedrooms all with hard-wood flooring. The bathroom offers a double-bowl vanity for added convenience and functionality. This delightful property combines charm, functionality, and thoughtful updates in a comfortable and convenient setting. Central air conditioning provides year-round comfort.The finished lower level of the home offers an ideal space to gather to watch a movie, the big game, or just a place for quiet time. Private deck overlooking a fenced in back yard, complete with a firepit. One car garage and a circular driveway add to the overall comfort of this home While the home's classic colonial design adds timeless appeal its location provides easy access to major highways, all for under $600,000. Seller will entertain all offers.

40 Hartford Ave N, 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

$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

$549,000

5 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 73400838 MLS ⋅ 2,887 SqFt.

This beautifully updated 2,887 sq. ft. single-family home offers stunning views of Pratt Pond and easy access to I-495. Renovated in 2024–2025, it features all-new siding and windows, a brand-new asphalt driveway and parking area, and a commercial-grade fire safety system. Inside, enjoy spacious, flexible living areas perfect for remote work or entertaining. A fully renovated backyard shed adds valuable storage or workshop space. Located on a convenient main road just minutes from downtown Upton.

130 High St, Upton

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Between $500K - $600K Upton Real Estate

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Browse All Upton MA Between $500K - $600K Properties for Sale

Between $500K - $600K Upton Real Estate

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