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Homes for Sale near Nipmuc Regional High School

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  • /35

    $495,000

    Open Sat 12PM - 2PM
    • 3 Beds
    • 1.5 Baths
    • 1,080 Sq Ft

    4 Picadilly St, Upton, MA 01568

    Welcome to this 3-bedroom split-level home offering a wonderful opportunity to build equity and create the home you’ve always envisioned. The main level features a bright living room, a spacious eat-in kitchen with access to the rear deck, and three comfortable bedrooms. The finished lower-level family room provides additional living space ideal for a playroom, home office, media room, or gym. An

    Agent Photo

    Robyn Nasuti

    Realty ONE Group Suburban Lifestyle

    4 Picadilly St, Upton, MA 01568
  • /35

    $749,900

    Open Sat 11AM - 1PM
    • 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

    Agent Photo

    Jeffrey Germagian

    ERA Key Realty Services-Bay State Group

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

    $484,900

    $15K PRICE DROP
    • 3 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

    Agent Photo

    Kathryn Amorello

    Coldwell Banker Realty - Worcester

    10 Hopkinton Rd, Upton, MA 01568
  • /39

    $1,200,000

    $100K PRICE DROP
    • 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

    Agent Photo

    Michael Giovangelo

    Better Living Real Estate, LLC

    28 Vincent Rd, Mendon, MA 01756
  • /23

    $749,900

    Open Sat 11AM - 1PM
    • 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

    Agent Photo

    Jeffrey Germagian

    ERA Key Realty Services-Bay State Group

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

    $799,000

    Open Sat 11AM - 1PM
    • 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

    21 Boot Shop Rd Unit 21, Upton, MA 01568
  • /41

    $855,900

    Open Sat 11AM - 1PM
    • 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
  • /12

    $989,900

    New Construction
    • 4 Beds
    • 4 Baths
    • 2,990 Sq Ft

    19 W Main St, Upton, MA 01568

    UNDER CONSTRUCTION...Enjoy The Benefits of New Construction with Energy Efficiency & Low Future Maintenance! This stunning home offers the perfect blend of classic elegance and modern convenience with a spacious 1st FLOOR PRIMARY SUITE and laundry and 3 additional bedrooms on the 2nd level. The partially finished basement with finished half bath provides extra square footage plus access to the

    Kim Backlund Northeast Realty + Co.

    19 W Main St, Upton, MA 01568
  • /34

    $619,900

    $20K PRICE DROP
    • 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
  • /41

    $1,300,000

    • 4 Beds
    • 3.5 Baths
    • 3,556 Sq Ft

    9 South St, Upton, MA 01568

    Room to grow......inside and out! Expansive 4 bedroom 2 1/2 bath home with separate IN-LAW in finished basement all nestled on a picturesque 8.3 acres! This gem boasts a 2 story foyer, hardwoods throughout the first floor and newer carpet throughout the second floor. Oversized primary suite with cathedral ceiling, large walk-in closet, jacuzzi tub, stand up shower/double vanity. Huge family room

    Robin Haddad Mendon Local Realty

    9 South St, Upton, MA 01568
  • /42

    $2,500,000

    • 4 Beds
    • 5 Baths
    • 4,040 Sq Ft

    117 South St, Upton, MA 01568

    75-Acre Elite Equestrian & Wellness Sanctuary. Ultimate private retreat with a 4,040 SF luxury Cape, world-class horse facilities, and resort backyard. Trail access to West Hill Dam. RESIDENCE: Chef's kitchen (Jade 6-burner, Sub-Zero, granite waterfall island). 1st-floor primary suite with vaulted ceilings & spa bath. 3 upper bedrooms, office, large bonus room + finished walkout lower level.

    Beth Byrne Gibson Sotheby's International Realty

    117 South St, Upton, MA 01568
  • /41

    $1,159,000

    • 4 Beds
    • 2.5 Baths
    • 3,360 Sq Ft

    33 Dairy Dr, Upton, MA 01568

    NEIGHBORHOOD SETTING WITH COMMUTER CONVENIENCE! This North-facing colonial offers over an acre of mature, professionally landscaped yard space that abuts trails and conservation land. Inside, the open layout is anchored by an incredibly spacious family room and modern chef’s kitchen with a double oven, 5-burner gas cooktop and oversized island to use for casual dining eating or as a homework hub.

    Erika Steele REMAX Executive Realty

    33 Dairy Dr, Upton, MA 01568
  • /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

    $899,900

    • 4 Beds
    • 2.5 Baths
    • 2,806 Sq Ft

    10 Sadler Rd, Upton, MA 01568

    Tucked away on a quiet cul-de-sac with 2 acres of wooded bliss, this Federal-front Colonial is pure serenity with an incredibly spacious layout to boot. It's 3000+ square feet that feels warm and homey with New England charm oozing from every room. The kitchen has NEW quartz countertops and a massive eat-in area with a downdraft gas stove. It flows seamlessly into a sun-drenched family room with

    Erika Steele REMAX Executive Realty

    10 Sadler Rd, Upton, MA 01568
  • /26

    $489,999

    Open Sun 10:30AM - 11:30AM $10K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,785 Sq Ft

    140 Main St Unit B, Upton, MA 01568

    Presenting an exceptional condominium residence at 140 Main St U:B, Upton, MA, a meticulously maintained property constructed in 2020. This 1785 square foot unit offers a refined living experience across three stories, embodying an attractive and contemporary aesthetic. The culinary space features an open-plan design seamlessly integrating with the living room, equipped with stainless steel

    Mike Dagilis ERA Key Realty Services- Milf

    140 Main St Unit B, Upton, MA 01568
  • /7

    $999,900

    New Construction
    • 4 Beds
    • 2.5 Baths
    • 2,780 Sq Ft

    17 W Main St, Upton, MA 01568

    UNDER CONSTRUCTION...Enjoy The Benefits of New Construction with Energy Efficiency & Low Future Maintenance! This stunning Colonial offers the perfect blend of classic elegance and modern convenience. Every detail has been carefully selected to provide style and functionality. 1ST floor hardwoods, Quartz countertops and GE Cafe appliances are just a few of the upgraded details that make this home

    Kim Backlund Northeast Realty + Co.

    17 W Main St, Upton, MA 01568
  • /42

    $799,900

    Open Sun 12PM - 1PM
    • 7 Beds
    • 4 Baths
    • 3,314 Sq Ft

    158 Main St, Upton, MA 01568

    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

    Rita Silva-Martins eXp Realty LLC - Corporate Office

    158 Main St, Upton, MA 01568
  • /41

    $825,000

    Open Sat 10AM - 12PM
    • 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 Remax Revolution

    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
  • /36

    $699,900

    Open Sat 11:30AM - 1PM $29K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,950 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
  • /36

    $709,000

    Open Sat 11:30AM - 1PM $16K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,950 Sq Ft

    56 Shannon Way Unit 56, Upton, MA 01568

    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

    The Semple and Hettrich Team Coldwell Banker Realty - Sudbury

    56 Shannon Way Unit 56, Upton, MA 01568
  • /41

    $449,000

    $150K PRICE DROP
    • 5 Beds
    • 3 Baths
    • 2,887 Sq Ft

    130 High St, Upton, MA 01568

    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

    Jacob Greasley eXp Realty LLC

    130 High St, Upton, MA 01568
  • /28

    $799,000

    Open Sat 11AM - 1PM
    • 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
  • /42

    $744,900

    Open Sat 1PM - 3PM
    • 3 Beds
    • 3.5 Baths
    • 2,300 Sq Ft

    7 Daniels Rd, Mendon, MA 01756

    Discover an exceptional living experience at 7 Daniels Road, Mendon, MA. Built in 1985, this single-family residence offers 2300 square feet of thoughtfully designed living space, promising a lifestyle of comfort and tranquility. The property features an open floor plan with additional family room, office, three generously proportioned bedrooms, providing ample private retreats for relaxation.

    Jodi Kairit Berkshire Hathaway Home Services Commonwealth Real Estate

    7 Daniels Rd, Mendon, MA 01756
  • /42

    $519,999

    • 3 Beds
    • 3.5 Baths
    • 2,091 Sq Ft

    13 Knowlton Cir Unit 13, Upton, MA 01568

    Welcome to this WEST-FACING townhouse in the desirable SAMREEN VILLAS community. 13 KNOWLTON CIRCLE offers low-maintenance living in a convenient Upton location.This 3-BEDROOM, 3.5-BATH home features an OPEN-CONCEPT FLOOR PLAN with HARDWOOD FLOORS, a SPACIOUS KITCHEN, and abundant natural light throughout the main living area. The second floor includes THREE GENEROUSLY SIZED BEDROOMS and a LARGE

    Smita Sinha Keller Williams Pinnacle MetroWest

    13 Knowlton Cir Unit 13, Upton, MA 01568
  • /42

    $1,125,000

    $50K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 4,054 Sq Ft

    35 Howarth Dr, Upton, MA 01568

    Glen Echo is a most desirable neighborhood close to Rt 495, MA Pike & Westborough. This pristine & spacious 4 bedroom, 3.5 bath Chatsworth Model Colonial has been impeccably maintained by its original owners. Enter to dramatic 2 story foyer w/ wainscoting & balcony. Open floor plan, 9 ft ceilings & tons of windows give this home an airy & roomy feel. Main level boasts hardwoods throughout.

    Gerald Simone Mathieu Newton Sotheby's International Realty

    35 Howarth Dr, Upton, MA 01568
  • /41

    $1,150,000

    $49K PRICE DROP
    • 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
  • /39

    $675,000

    Open Sun 11:30AM - 1PM
    • 4 Beds
    • 2 Baths
    • 2,534 Sq Ft

    90 Glenview St, Upton, MA 01568

    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. Updated windows. First floor unit has a large foyer, generously sized living room with stunning hardwoods and

    Laura Hebb ERA Key Realty Services

    90 Glenview St, Upton, MA 01568
  • /33

    $950,000

    • 4 Beds
    • 3 Baths
    • 3,100 Sq Ft

    33 Milford St, Upton, MA 01568

    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

    Wendy Solano Lamacchia Realty, Inc.

    33 Milford St, Upton, MA 01568
  • /37

    $679,000

    Open Sat 12:30PM - 2PM
    • 3 Beds
    • 2 Baths
    • 2,328 Sq Ft

    62 Millville Rd, Mendon, MA 01756

    Stunning Quality Minded full-scale renovation in Mendon. This beautifully updated 2,100 sq ft home sits on an acre+ corner lot within walking distance to the lake. The kitchen features new cabinets, granite counters, recessed lighting, tile flooring, and a new slider to the brand-new deck. The living room offers refinished hardwoods and a new gas fireplace. The main bath includes a new

    Susan Dicks ERA Key Realty Services

    62 Millville Rd, Mendon, MA 01756
  • /42

    $775,000

    $45K PRICE DROP
    • 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
  • /33

    $599,000

    Open Fri 5PM - 7PM
    • 3 Beds
    • 2 Baths
    • 1,606 Sq Ft

    45 Neck Hill Rd, Mendon, MA 01756

    Nestled on a peaceful .93-acre corner lot surrounded by nature, this beautiful raised ranch offers the perfect blend of comfort, convenience, and tranquility. Step into a spacious living room featuring a generous picture window overlooking beautifully landscaped and wooded surroundings. The open-concept dining and kitchen area flows seamlessly to an elevated deck through a sliding glass door —

    Peter Alemian Keller Williams Realty Boston Northwest

    45 Neck Hill Rd, Mendon, MA 01756
  • /39

    $1,699,000

    $176K PRICE DROP
    • 8 Beds
    • 6 Baths
    • 6,850 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
  • /33

    $625,000

    Open Sun 12PM - 1:30PM
    • 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
  • /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
  • /34

    $699,000

    • 3 Beds
    • 2.5 Baths
    • 2,336 Sq Ft

    187 Blackstone St, Mendon, MA 01756

    Picture-perfect Colonial on a scenic country road! A brick walk and stone steps lead to this charming, immaculately maintained home. The main level features a living room with wide pine floors, a family room with bar, wood floors, and a raised-hearth fireplace, a remodeled kitchen, and a half bath with laundry. Upstairs offers three bedrooms and a full bath with a custom tile shower and updated

    The Biega + Kilgore Team Compass

    187 Blackstone St, Mendon, MA 01756
  • /42

    $1,100,000

    $50K PRICE DROP
    • 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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