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6 Glen Ave, Upton
$449,900
3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 73589345 MLS ⋅ 1,450 SqFt.
Some photos are virtually staged for marketing purposes. This charming Colonial-style home blends timeless New England character with modern conveniences. The first floor features beautiful wide-plank wood floors in the living and dining rooms, along with a cozy fireplace that adds warmth and character. The updated kitchen boasts tile flooring, granite countertops, and stainless steel appliances. A full bathroom on the main level adds convenience. Upstairs, you'll find three bedrooms with wood flooring throughout, along with a newly updated full bathroom featuring tile floors and an expansive jetted tub-perfect for unwinding at the end of the day. Step outside onto the deck and relax while enjoying peaceful views of Warren Brook. With its classic charm, thoughtful updates, and inviting outdoor space, this home offers a wonderful blend of comfort and character.

6 Glen Ave, Upton
55 School Street, Upton
$575,000
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
90-92-94 Main Street, Upton
$1,400,000
1 Baths ⋅ ACTIVE Status ⋅ 73585871 MLS ⋅ 5,040 SqFt.
RARE INVESTMENT OPPORTUNITY IN DOWNTOWN UPTON! Bring your business, your tenants or your vision to this oversized commercial property offering serious potential for an owner user or investor. The building is in good condition and features five large overhead doors with room for trucks, campers, commercial vehicles and equipment, plus interior space with the potential to accommodate 6 automotive lifts. Ideal for an automotive garage, service business, contractor operation, fleet use, storage or a creative commercial concept. Excellent frontage and visibility create even more opportunity to grow, expand or reposition the property for future use. Properties with this kind of size, access and versatility are difficult to find. Whether you are looking to operate your own business, create multiple revenue streams or add a flexible commercial asset to your portfolio, this is one worth seeing. Bring the ideas. Bring the business. Bring the possibilities.

90-92-94 Main Street, Upton
23 North St, Upton
$410,000
4 Beds ⋅ 3 Baths ⋅ UNDER AGREEMENT Status ⋅ 73584424 MLS ⋅ 2,424 SqFt.
Land, Location and Upside! Calling all investors, developers and DIYers! 23 North St in Upton is the value-add opportunity you've been waiting for. Priced at $410,000 and sold strictly as-is, this one is ready for your vision and some sweat equity. Set on a rare 5.8 acres, the property gives you options: renovate and restore the existing home, redevelop the site, or build new. The home was used as a multifamily, so you could rework the layout, reconfigure the space, or take it in a completely new direction. The land leaves plenty of room to expand the footprint, add outbuildings or garages, or create a private retreat set well apart from the neighbors, with the kind of privacy and space that's increasingly hard to find. Opportunities with this much land and upside don't come along often. Bring your vision, your contractor and your plans, and see what 23 North St can become. Schedule your showing today! Sold as-is. Buyer to perform own due diligence regarding zoning, permitted use, and development potential.

23 North St, Upton
15 W Main St, Upton
$499,000
3 Beds ⋅ 3 Baths ⋅ UNDER AGREEMENT Status ⋅ 73569379 MLS ⋅ 3,217 SqFt.
After being cherished by the same family for approximately 170 years, 15 West Main Street presents an extraordinary opportunity to become the next steward of a truly special historic property. Known as the Arba Thayer Wood House and Barn, this distinguished homestead was built in 1855 by Arba Thayer Wood and retains the character, craftsmanship, and gracious proportions of a bygone era. Rich with history and remarkably preserved original details, the property is ideally suited for an antique home enthusiast, preservationist, or skilled restorer with the vision to thoughtfully renovate and bring this significant residence into its next chapter. Seller has installed a new 4 bedroom Septic System. The property is being sold in AS-IS condition. Buyers and buyers' agents are responsible for performing their own due diligence regarding the property, its condition, systems, permitted uses, renovation requirements, historical significance, and any other matters important to them. Other than new septic and town water, Seller makes no representations of any type or kind as to condition.

15 W Main St, Upton
5 Elm Street, Upton
$675,000
4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 73565350 MLS ⋅ 2,108 SqFt.
$20,000 PRICE IMPROVEMENT! Timeless charm & modern comfort describe this renovated Colonial originally built in 1828 on a scenic, quiet country road. Fully reframed in 1988, with a kitchen/family room addition in 1994, this spacious home is in excellent condition. This saltbox-style home blends historic character with contemporary living. The kitchen/family room & the primary bedroom suite have cathedral ceilings & skylights. The open-concept kitchen is designed for entertaining featuring new stainless steel appliances & a convenient peninsula. The adjacent front-to-back living room creates an inviting space for relaxing with a charming fireplace, perfect for cozy evenings. This home provides four comfortable bedrooms & two full baths, with the primary bath offering a jetted tub with shower. The floorplan offers flexibility for multiple home office options. Once you step outside the privacy of the large, level lot and heated in-ground pool designed for leisurely summer days, leaves you imagining the wonderful memories to be made. This much-loved property is the perfect blend of historic elegance and modern amenities. Kiwanis Beach (1/2 mi), Upton Heritage Park (1/4 mi), Upton State Forest (3 mi away), all offer passive recreation opportunities. UPDATES TO PROPERTY: New 4BR septic 2026; Indirect hot water heater 2025; 200 AMP electric 2023; SS kitchen appliances 2025; Chimney repointing 2026; Roof 2023.

5 Elm Street, Upton
24 Main St, 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
33 Milford St, Upton
$909,900
4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 73557408 MLS ⋅ 3,100 SqFt.
Stunning fully renovated luxury home offering three finished levels of sophisticated living with high-end finishes and designer details throughout. This turnkey home features an open-concept floor plan, a custom chef's kitchen with premium appliances, spa-inspired bathrooms, modern lighting, and beautifully updated living spaces. Thoughtfully renovated with exceptional craftsmanship, it seamlessly blends timeless charm with contemporary elegance. Move-in ready and designed for today's lifestyle, this exceptional home offers comfort, style, and quality in every detail.

33 Milford St, Upton
52 Elm St, Upton
$699,000
4 Beds ⋅ 3 Baths ⋅ UNDER AGREEMENT Status ⋅ 73523806 MLS ⋅ 2,835 SqFt.
BACK ON MARKET due to BUYER not being able to sell their home. A rare opportunity to own a beautifully preserved antique Gambrel, thoughtfully updated for modern living while retaining the craftsmanship and character of its New England heritage. Set along a scenic country road, this distinctive residence is surrounded by storybook grounds, mature landscaping and a sense of privacy that is increasingly difficult to find. A gracious first-floor primary suite offers a serene retreat, while the expansive, rambling floor plan provides exceptional flexibility for gathering, entertaining, working and relaxing. The interiors include a welcoming room, library/den, front-to-back living room and classic keeping room with a stone fireplace. A warm, inviting kitchen with natural wood cabinetry complements the home’s historic character, while three fireplaces, charming nooks and carefully preserved period details lend depth and authenticity throughout.The setting is equally compelling. Mature trees, flowering shrubs, open lawn and meadow frame a tranquil pond and distinctive New England stone walls. A beautiful patio, crafted with reclaimed Worcester brick and reached by a stone walkway, creates an elegant setting for morning coffee, outdoor dining or evening entertaining. The detached two-car garage includes a loft well suited to creative pursuits, hobbies or additional storage.Recent improvements include restored mid-1800s windows with storm windows, central air, a metal roof, a renovated second-floor bath, fresh exterior paint and a regraded driveway accented with cobblestone pavers. Each update enhances comfort and function while respecting the home’s original materials, proportions and enduring appeal.With its rare combination of architectural integrity, pastoral beauty and thoughtful livability, this exceptional property offers a lifestyle rooted in history, craftsmanship and quiet enjoyment. Schedule a private showing to experience its singular character firsthand.

52 Elm St, Upton
130 High St, 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

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non commercial use of consumers having a good faith interest in purchasing, leasing or renting listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing, leasing or renting. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.

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