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Homes for Sale near Nipmuc Regional High School

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  • /38

    $420,000

    $30K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,727 Sq Ft

    5 Pleasant St, Upton, MA 01568

    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

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    Robyn Nasuti

    Realty ONE Group Suburban Lifestyle

    (508) 978-5782

    5 Pleasant St, Upton, MA 01568
  • /42

    $1,300,000

    • 4 Beds
    • 2.5 Baths
    • 3,570 Sq Ft

    27 W River St, Upton, MA 01568

    Modern farmhouse-inspired luxury meets exceptional craftsmanship in this stunning custom-built ranch set on 4.8 private acres. Designed for effortless single-level living, this one-of-a-kind home offers an open-concept floor plan filled with natural light from oversized windows and accented by gleaming hardwood floors throughout the main living areas. The sleek chef’s kitchen features tall custom

    Agent Photo

    Robyn Nasuti

    Realty ONE Group Suburban Lifestyle

    (508) 257-7981

    27 W River St, Upton, MA 01568
  • /42

    $715,000

    • 3 Beds
    • 3 Baths
    • 2,835 Sq Ft

    52 Elm St, Upton, MA 01568

    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,

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    Robyn Nasuti

    Realty ONE Group Suburban Lifestyle

    (508) 231-9273

    52 Elm St, Upton, MA 01568
  • /39

    $1,299,900

    • 4 Beds
    • 4.5 Baths
    • 4,338 Sq Ft

    28 Vincent Rd, Mendon, MA 01756

    Welcome to 28 Vincent Road in Mendon, a truly unique architect-designed colonial. Enter through the mahogany front door surrounded by English ivy and into a grand entryway. This 4 bed, 4.5 bath home features a breathtaking living room with cathedral ceilings, skylights, exposed brick fireplace, and full-panel wainscoting, a spacious eat-in kitchen w/ granite countertops and stainless steel

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    Michael Giovangelo

    Better Living Real Estate, LLC

    (508) 785-7741

    28 Vincent Rd, Mendon, MA 01756
  • /23

    $749,900

    Open Fri 1PM - 3PM
    • 2 Beds
    • 2.5 Baths
    • 2,245 Sq Ft

    19 Boot Shop Rd Unit 19, Upton, MA 01568

    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

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    Jeffrey Germagian

    ERA Key Realty Services-Bay State Group

    (508) 590-9785

    19 Boot Shop Rd Unit 19, Upton, MA 01568
  • /34

    $799,000

    Open Fri 1PM - 3PM
    • 2 Beds
    • 2 Baths
    • 1,734 Sq Ft

    21 Boot Shop Rd Unit 21, Upton, MA 01568

    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 &

    Agent Photo

    Jeffrey Germagian

    ERA Key Realty Services-Bay State Group

    (508) 625-9207

    21 Boot Shop Rd Unit 21, Upton, MA 01568
  • /40

    $789,900

    • 4 Beds
    • 2.5 Baths
    • 2,408 Sq Ft

    20 Josiah Dr, Upton, MA 01568

    Welcome to 20 Josiah Drive, a beautifully maintained Colonial in one of Upton’s most desirable neighborhoods. This spacious 4-bedroom, 2.5-bath home offers over 2,200 sq ft of sun-filled living space with newly refinished hardwood floors and an open layout ideal for everyday living and entertaining. The vaulted-ceiling great room and fireplaced family room create warm and inviting spaces, while

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    Walsh Fine Homes Team

    eXp Realty LLC

    (508) 458-8983

    20 Josiah Dr, Upton, MA 01568
  • /42

    $532,000

    • 3 Beds
    • 3.5 Baths
    • 1,731 Sq Ft

    13 Knowlton Cir Unit 13, Upton, MA 01568

    13 Knowlton Circle offers comfortable and low-maintenance townhouse living in a desirable Upton location. This 3 BEDROOM, 3.5 BTHROOMS, home features an open floor plan with hardwood floors, a spacious kitchen, and plenty of natural light throughout the main living area. The second floor includes three well-sized bedrooms, the GOOD SIZE LOFT and FINISHED lower level with a FULL BATHROOM provide

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    Smita Sinha

    Keller Williams Pinnacle MetroWest

    (508) 794-8490

    13 Knowlton Cir Unit 13, Upton, MA 01568
  • /34

    $749,900

    Open Fri 1PM - 3PM
    • 2 Beds
    • 2 Baths
    • 1,734 Sq Ft

    5 Boot Shop Rd Unit 5, Upton, MA 01568

    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

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    Jeffrey Germagian

    ERA Key Realty Services-Bay State Group

    (774) 352-5793

    5 Boot Shop Rd Unit 5, Upton, MA 01568
  • /31

    $500,000

    • 2 Beds
    • 2 Baths
    • 1,176 Sq Ft

    10 Hopkinton Rd, Upton, MA 01568

    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

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    Kathryn Amorello

    Coldwell Banker Realty - Worcester

    (508) 504-8939

    10 Hopkinton Rd, Upton, MA 01568
  • /41

    $855,900

    Open Fri 1PM - 3PM
    • 2 Beds
    • 2.5 Baths
    • 2,228 Sq Ft

    7 Boot Shop Rd Unit 7, Upton, MA 01568

    Come see what's new 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 two-story living with everything you need handy on the first floor such as a covered front porch, foyer, powder room,

    The Kattman Team ERA Key Realty Services-Bay State Group

    7 Boot Shop Rd Unit 7, Upton, MA 01568
  • /14

    $1,499,999

    New Construction
    • 5 Beds
    • 4 Baths
    • 3,875 Sq Ft

    9 Kiwanis Beach Rd, Upton, MA 01568

    ***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.

    Luciano Souza Pinto Real Estate

    9 Kiwanis Beach Rd, Upton, MA 01568
  • /41

    $675,000

    • 3 Beds
    • 1.5 Baths
    • 1,638 Sq Ft

    236 Mendon St, Upton, MA 01568

    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.

    Laura Hebb ERA Key Realty Services

    236 Mendon St, Upton, MA 01568
  • /36

    $639,900

    • 3 Beds
    • 2 Baths
    • 1,920 Sq Ft

    34 George St, Mendon, MA 01756

    Perfect blend of historic farmhouse character and major modern updates.** Gutted and extensively renovated in 2017, this charming Colonial preserves the front façade and character of the original farmhouse while adding today’s comfort and functionality. The interior was fully renovated while maintaining many original details, including wide-plank flooring, woodwork, doors, banisters, and two

    David Restic Property Services Network

    34 George St, Mendon, MA 01756
  • /42

    $1,075,000

    • 4 Beds
    • 2.5 Baths
    • 2,974 Sq Ft

    29 Thornton St, Mendon, MA 01756

    Welcome to this beautifully crafted custom new construction home set on a generous 1.3-acre lot, offering both privacy and plenty of space to enjoy outdoors. A charming front porch leads into a welcoming foyer that opens to an expansive open-concept layout, featuring a spacious living room, dining area, and kitchen—perfect for everyday living and effortless entertaining. The living room is

    Joe Alves Better Living Real Estate, LLC

    29 Thornton St, Mendon, MA 01756
  • /9

    $489,000

    $297K PRICE DROP
    • Land
    • 8.54 Acres
    • $57,260 per Acre

    183 Blackstone St, Mendon, MA 01756

    Attention builders, developers, and end-users, explore the possibilities on 8.54 wooded acres in Mendon. This expansive parcel offers privacy and a peaceful country setting while still providing convenient access to major routes. With substantial acreage, the property presents a variety of potential uses, subject to town approvals and buyer due diligence. A site plan and sewage disposal system

    Tara Sullivan Century 21 Custom Home Realty

    183 Blackstone St, Mendon, MA 01756
  • /42

    $699,900

    • 3 Beds
    • 2.5 Baths
    • 1,917 Sq Ft

    35 North Ave, Mendon, MA 01756

    Welcome home to this beautifully updated ranch, perfectly set on over 4 peaceful acres. With single-floor living, 3 bedrooms, 2 full and 1 half baths, this move-in-ready home offers comfort, privacy, and space to enjoy every season. The fenced backyard and wooded surroundings create a wonderful setting for play, pets, gardening, or simply relaxing on the deck off the family room. Inside, you’ll

    Team Metrowest Berkshire Hathaway HomeServices Commonwealth Real Estate

    35 North Ave, Mendon, MA 01756
  • /26

    $499,899

    • 3 Beds
    • 2.5 Baths
    • 1,785 Sq Ft

    140 Main St Unit B, Upton, MA 01568

    Welcome to 140 Main St U:B in Upton, MA!! This 2020-built condominium presents an attractive property in great condition, offering 1785 square feet of refined living space. This is a three-story residence, w/expansion potential in LL. Situated on the first floor, you'll find a sophisticated & relaxed living space. The kitchen is thoughtfully designed for both culinary pursuits & social

    Mike Dagilis ERA Key Realty Services- Milf

    140 Main St Unit B, Upton, MA 01568
  • /32

    $744,900

    • 2 Beds
    • 3.5 Baths
    • 2,200 Sq Ft

    27 James Rd Unit 4, Upton, MA 01568

    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

    Kim Kimball Kimball Property Realty Inc.

    27 James Rd Unit 4, Upton, MA 01568
  • /41

    $825,000

    • 4 Beds
    • 4 Baths
    • 2,449 Sq Ft

    9 White Rd, Mendon, MA 01756

    Welcome home to this beautifully updated Colonial set on 1.38+ acres. This spacious home features an open floor plan with knotty oak pine flooring throughout the first floor. The entry flows into the living room, dining area, and an updated kitchen with granite countertops, stainless steel appliances, and a half bath. Enjoy first-floor laundry and a deck (2018) perfect for entertaining.Upstairs

    Gina Ronci HomeSmart Professionals Real Estate

    9 White Rd, Mendon, MA 01756
  • /42

    $1,225,000

    $25K PRICE DROP
    • 4 Beds
    • 5.5 Baths
    • 5,736 Sq Ft

    12 Breton Rd, Upton, MA 01568

    With a flexible layout that supports multigenerational living, this gorgeous custom-built colonial has ample space and is situated on 3+ private acres. From the moment you step into the grand two-story foyer adorned w/ granite flooring, you’ll be captivated by the attention to detail & luxurious features throughout, incl 9ft+ ceilings & gleaming hardwoods. Spacious fam rm is a true showpiece w/

    Melissa Ellison Mathieu Newton Sotheby's International Realty

    12 Breton Rd, Upton, MA 01568
  • /40

    $699,800

    • 4 Beds
    • 2.5 Baths
    • 2,548 Sq Ft

    24 Main St, Upton, MA 01568

    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

    Jeanne Leombruno Century 21 Custom Home Realty

    24 Main St, Upton, MA 01568
  • /36

    $729,000

    Open Wed 5:30PM - 7PM
    • 2 Beds
    • 2.5 Baths
    • 1,930 Sq Ft

    87 Shannon Way Unit 86, Upton, MA 01568

    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,

    Shane Brady Keller Williams Realty

    87 Shannon Way Unit 86, Upton, MA 01568
  • /19

    $7,500,000

    • 46 Beds
    • 34 Baths
    • 22,233 Sq Ft

    135 Main St, Upton, MA 01568

    135 Main St contains 34 units comprised of (22) 1-Bed/1-Bath units and (12) 2-Bed/1-Bath units. The Property, previously known as The Upton Inn, has undergone significant renovations since its acquisition in August of 2024. This has included renovations of most units including new kitchens and bathrooms with condo quality finishes, updated flooring and painting of the units’ interiors. 135 Main

    Kelleher - Pentore Team Horvath & Tremblay

    135 Main St, Upton, MA 01568
  • /16

    $475,000

    $25K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 2,110 Sq Ft

    17 N Main St, Upton, MA 01568

    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,

    Michael O'Dea Coldwell Banker Realty - Brookline

    17 N Main St, Upton, MA 01568
  • /7

    $799,000

    Open Fri 1PM - 3PM
    • 2 Beds
    • 2.5 Baths
    • 2,228 Sq Ft

    12 Boot Shop Rd Unit 12, Upton, MA 01568

    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

    The Kattman Team ERA Key Realty Services-Bay State Group

    12 Boot Shop Rd Unit 12, Upton, MA 01568
  • /35

    $1,077,845

    New Construction
    • 4 Beds
    • 2.5 Baths
    • 2,751 Sq Ft

    20 Rawson Farm Rd, Mendon, MA 01756

    Framing starting soon. Foundation is in! Close to Schools and commuter routes. Welcome to the Ashford plan our most popular floor plan with the heart of the home featuring a quartz island, dining area, stainless steel appliances gleaming hardwood flooring. Fireplaced great room, dining room and study are complete with Hardwood floors & crown molding. Your master bedroom get away features an en

    Gary Smith Mendon Area Real Estate

    20 Rawson Farm Rd, Mendon, MA 01756
  • /41

    $849,900

    • 4 Beds
    • 2.5 Baths
    • 3,931 Sq Ft

    88 Northbridge Rd, Mendon, MA 01756

    Welcome to this stunning, fully renovated 4-bed, 2.5-bath colonial nestled on a private lot in one of Mendon's most desirable settings. From the grand two-story foyer and elegant staircase to the beautifully updated kitchen featuring quartz countertops, stainless steel appliances, a large center island, and dining area, every detail has been thoughtfully designed. The main level offers an

    Tariq Fayyad Fayyad Realty Advisors

    88 Northbridge Rd, Mendon, MA 01756
  • /42

    $1,450,000

    • 5 Beds
    • 5 Baths
    • 4,395 Sq Ft

    8 Stearns Rd, Upton, MA 01568

    Nestled at the end of a private cul-de-sac on nearly two acres, this meticulously renovated Colonial estate offers a premier multi-generational layout featuring main residence & fully equipped accessory dwelling. Beautiful main house boasts a mahogany deck, chef’s kitchen complete w/ quartz countertops, double wall ovens, gas cooktop, & an oversized butcher-block island, all adjacent to a coffee,

    Kathleen Nicoloro Ferrari + Co. Real Estate

    8 Stearns Rd, Upton, MA 01568
  • /41

    $1,199,000

    Open Sun 11AM - 1PM
    • 4 Beds
    • 4 Baths
    • 3,402 Sq Ft

    30 Mendon St, Upton, MA 01568

    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

    Luana Velame Century 21 The Real Estate Group

    30 Mendon St, Upton, MA 01568
  • /17

    $419,000

    • 3 Beds
    • 2 Baths
    • 1,420 Sq Ft

    51 School St Unit 3, Upton, MA 01568

    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

    Daniel DiBiasio DiBiasio Realty LLC

    51 School St Unit 3, Upton, MA 01568
  • /21

    $1,100,000

    • 4 Beds
    • 3.5 Baths
    • 3,487 Sq Ft

    99 W River St, Upton, MA 01568

    This beautifully designed custom home offers the perfect blend of privacy, space, and modern functionality. Set back from the street and positioned on an elevated lot, the home delivers both curb appeal and a sense of seclusion. Inside, you’ll find a thoughtfully designed floor plan featuring 4 spacious bedrooms and 3.5 bathrooms. The heart of the home is ideal for both everyday living and

    Diana Afonso Afonso Real Estate

    99 W River St, Upton, MA 01568
  • /37

    $879,900

    • 3 Beds
    • 2.5 Baths
    • 3,076 Sq Ft

    45 Mendon St, Upton, MA 01568

    Custom-built Colonial set on a picturesque 1.55-acre lot. Showcasing exceptional craftsmanship, quality construction and a thoughtfully designed floor plan, this home offers the perfect blend of comfort and functionality for today's lifestyle. The spacious family room features a soaring ceiling and striking stone fireplace, creating a warm and inviting gathering space. The kitchen offers

    Mary Wood Lamacchia Realty, Inc.

    45 Mendon St, Upton, MA 01568
  • /42

    $819,900

    • 3 Beds
    • 3 Baths
    • 1,304 Sq Ft

    11 James Rd, Upton, MA 01568

    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

    Team ROVI Real Broker MA, LLC

    11 James Rd, Upton, MA 01568
  • /39

    $1,875,000

    • 8 Beds
    • 6 Baths
    • 6,030 Sq Ft

    175 Pleasant St, Upton, MA 01568

    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

    Matthew Sousa Bullseye Realty Group

    175 Pleasant St, Upton, MA 01568
  • /3

    $550,000

    • Land
    • 5.45 Acres
    • $100,917 per Acre

    Lot 108 W Main St, Upton, MA 01568

    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

    John Miller Keller Williams Pinnacle Central

    Lot 108 W Main St, Upton, MA 01568
  • /3

    $1,199,999

    • 3 Beds
    • 2.5 Baths
    • 2,799 Sq Ft

    14 Lundvall Rd, Mendon, MA 01756

    Brand New Construction in the Spring Brook Subdivision.This stunning 2,800 sq ft new build offers modern living with thoughtful design. The finished main and upper levels include a first-floor primary suite with private full bath and two walk-in closets. The open-concept main level features a spacious kitchen with pantry, living and dining areas, a dedicated study/office, and a convenient half

    Lawney Tinio Century 21 Custom Home Realty

    14 Lundvall Rd, Mendon, MA 01756
  • /42

    $1,150,000

    Open Sun 11AM - 1PM
    • 4 Beds
    • 2.5 Baths
    • 2,924 Sq Ft

    32 Mendon St, Upton, MA 01568

    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

    Luana Velame Century 21 The Real Estate Group

    32 Mendon St, Upton, MA 01568
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