20

Upton, MA Homes for Sale with Acreage

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  • /42

    $699,000

    $16K PRICE DROP
    • 4 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,

    Agent Photo

    Robyn Nasuti

    Realty ONE Group Suburban Lifestyle

    52 Elm St, Upton, MA 01568
  • /42

    $1,099,000

    Open Fri 4:30PM - 6PM
    • 4 Beds
    • 4.5 Baths
    • 2,889 Sq Ft

    91 High St, Upton, MA 01568

    Be the first to call this exceptional new-construction Colonial home! Ideally situated near the heart of downtown Upton, this 2,889 -square-foot residence pairs timeless farmhouse charm with modern finishes and a flexible layout designed for today’s lifestyle. Enjoy the character of small-town living with convenient access to Upton’s town beach, parks, library, post office, local shops, and even

    Agent Photo

    Robyn Nasuti

    Realty ONE Group Suburban Lifestyle

    91 High St, Upton, MA 01568
  • /40

    $1,079,000

    • 4 Beds
    • 3.5 Baths
    • 3,350 Sq Ft

    165 East St, Upton, MA 01568

    Pride of ownership abounds at this exceptional 4-bedroom, 3.5 bath custom contemporary home set on 3.50 beautifully maintained acres offering privacy and endless opportunities to enjoy the outdoors. Enter through the two-story foyer and be greeted by sunlight pouring into the home through an abundance of windows, skylights, and sliders creating a bright and welcoming atmosphere throughout. The

    Michael Stein Redfin Corp.

    165 East 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
  • /36

    $1,147,900

    • 4 Beds
    • 2.5 Baths
    • 2,884 Sq Ft

    Lot 12 Rawson Farm, Mendon, MA 01756

    The Modified Hampton is one of our most popular plans in the Miscoe Springs neighborhood. Now building this 4 bedroom, 2.5 bath home with professional designer finishes to be included. Featuring a beautiful cathedral family room complete with fireplace and adjacent to a great entertaining kitchen you can dine casually around the quartz island or in the breakfast area. Enhanced cabinets to the

    Gary Smith Mendon Area Real Estate

    Lot 12 Rawson Farm, Mendon, MA 01756
  • /41

    $875,000

    $25K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,806 Sq Ft

    10 Sadler Rd, Upton, MA 01568

    *** ALL CARPET IS BEING REPLACED IN OCTOBER 2026 **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

    Erika Steele REMAX Executive Realty

    10 Sadler Rd, 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

    $974,900

    Open Sun 11AM - 1PM $23K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 3,332 Sq Ft

    27 Juniper Rd, Upton, MA 01568

    Siting majestically in one of Upton's most desired neighborhoods, this gorgeous Colonial commands attention with its gracious presence, impressive scale and beautifully designed spaces. Step through the soaring two story foyer and into a home created for memorable living and effortless entertaining. The wonderful kitchen is a culinary delight, complete with a generous island, gourmet appliances

    THE LASH GROUP Keller Williams Boston MetroWest

    27 Juniper Rd, Upton, MA 01568
  • /42

    $1,320,000

    $20K PRICE DROP
    • 5 Beds
    • 3.5 Baths
    • 4,498 Sq Ft

    66 Glenview St, Upton, MA 01568

    Set amid park-like grounds with a private wooded backdrop, this expansive Upton home stands out for its generous living space, thoughtful updates and remarkable flexibility. Updated kitchens and baths throughout bring a fresh, polished feel to the home, while impressive architectural details begin in the soaring two-story foyer and continue into the dramatic family room, where a vaulted ceiling,

    Lisa Aron Williams Coldwell Banker Realty - Sudbury

    66 Glenview St, Upton, MA 01568
  • /40

    $849,900

    $30K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 3,132 Sq Ft

    2 Brookside St, Upton, MA 01568

    Stately Colonial offering a rare combination of privacy, natural beauty & modern updates in one exceptional property. Every window captures peaceful views of the surrounding landscape, creating a vacation-at-home feeling year-round. This spacious home features beautiful hardwood floors throughout the 1st floor & a versatile floor plan designed for easy everyday living & entertaining. The stunning

    Leah Burke William Raveis R.E. & Home Services

    2 Brookside St, Upton, MA 01568
  • /40

    $899,000

    • 4 Beds
    • 5 Baths
    • 4,242 Sq Ft

    96 Fowler St, Upton, MA 01568

    Exceptional Colonial on 3.21 Private Acres. Discover the perfect blend of comfort and lifestyle in this exceptional colonial, set on 3.21 acres of stunning, pastoral landscape. Designed to inspire, the home is bathed in natural light and offers breathtaking sunset views—providing the perfect backdrop for working from home. The open-concept floor plan flows seamlessly, featuring a spacious family

    Isaac Alvarenga Property Investors & Advisors, LLC

    96 Fowler St, Upton, MA 01568
  • /37

    $599,000

    • 3 Beds
    • 2 Baths
    • 1,496 Sq Ft

    15 North St, Upton, MA 01568

    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

    Laura Hebb ERA Key Realty Services

    15 North St, Upton, MA 01568
  • /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
  • /3

    $500,000

    $50K PRICE DROP
    • Land
    • 5.45 Acres
    • $91,743 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
  • /42

    $955,000

    $20K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,941 Sq Ft

    161 South St, Upton, MA 01568

    Price Improvement on this truly exceptional Colonial where timeless elegance meets modern comfort. Meticulously maintained and thoughtfully updated, this stunning 4-bedroom, 2.5-bath home offers generous living spaces, 9-foot ceilings, and abundant natural light, creating a warm and inviting atmosphere throughout. The beautifully appointed kitchen is a cook’s dream, featuring upgraded granite

    Laura Hebb ERA Key Realty Services

    161 South St, Upton, MA 01568
  • /5

    $499,000

    • 3 Beds
    • 2.5 Baths
    • 3,217 Sq Ft

    15 W Main St, Upton, MA 01568

    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

    Kim Backlund Northeast Realty + Co.

    15 W Main St, Upton, MA 01568
  • /41

    $1,199,900

    $100K PRICE DROP
    • 4 Beds
    • 4.5 Baths
    • 3,543 Sq Ft

    8 Juniper Rd, Upton, MA 01568

    Welcome to 8 Juniper Road, where impressive space, thoughtful updates, and a truly spectacular backyard oasis come together in one exceptional home. Offering approximately 3,600 sq. ft. of living space, 4 bedrooms, 4.5 bathrooms, and a 3-car garage, this beautifully maintained and updated property is designed for both comfortable everyday living and unforgettable entertaining. Inside, a spacious

    Amy Bisson Lamacchia Realty, Inc.

    8 Juniper Rd, Upton, MA 01568
  • /42

    $1,075,000

    $75K 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
  • /42

    $568,800

    $41K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,810 Sq Ft

    44 Cherry Ln Unit 44, South Grafton, MA 01560

    FIRST-FLOOR PRIMARY SUITE & LAUNDRY! Enjoy a flexible floor plan designed for easy living in this spacious Pulte-built townhouse at desirable Hilltop Farms. The bright, open main level features 9' ceilings, hardwood flooring, a dramatic two-story foyer, gas fireplace and transom windows that bring in plenty of natural light. The kitchen offers oak cabinetry, Corian countertops and updated

    Claire Rainville REMAX Executive Realty

    44 Cherry Ln Unit 44, South Grafton, MA 01560
  • /14

    $6,229,000

    • Land
    • 20.9 Acres
    • $298,038 per Acre

    186 Spring St, Hopkinton, MA 01748

    Premium location in a top Hopkinton school district, surrounded by Upton State Forest. This property aligns with a 10–12 lot subdivision concept supported by the new Massachusetts variance reforms and NFPA ( dead end Road) access standards. With the upcoming By-Right Duplex rules and 90-100 day state approval guidance, values are expected to increase. Current pricing reflects a cash-only purchase

    Brendon Sullivan-Monson StartPoint Realty

    186 Spring St, Hopkinton, MA 01748

Home Price Trends

Median Sale Price
$758,500
Median Single Family Sale Price
$791,900
Median Townhouse Sale Price
$519,000
Median 2 Bedroom Sale Price
$699,900
Average Price Per Sq Ft
$322
Number of Homes for Sale
20
Last 12 months Home Sales
96
Months of Supply
4.10
Median List Price
$751,340
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
4%
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