14

Colonial Homes for Sale in Upton, MA

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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

    Agent Photo

    Robyn Nasuti

    Realty ONE Group Suburban Lifestyle

    (508) 978-5782

    5 Pleasant St, 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

    Agent Photo

    Walsh Fine Homes Team

    eXp Realty LLC

    (508) 458-8983

    20 Josiah Dr, 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
  • /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
  • /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

    • 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
  • /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. This Free standing home has a very flexible floor plan. 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 tiled

    Kim Kimball Kimball Property Realty Inc.

    27 James Rd Unit 4, 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
  • /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
  • /42

    $1,150,000

    • 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
  • /36

    $2,950,000

    $800K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 3,014 Sq Ft

    186 Spring St, Hopkinton, MA 01748

    Prime Investment Opportunity: 20.9-Acre Private Estate in Top-Rated Hopkinton School District Nestled on an expansive 20.9-acre wooded lot bordering the Upton State Forest (one of the largest in Hopkinton), 186 Spring Street offers exceptional privacy, tucked deep in the forest with mature trees and natural seclusion. This rare parcel provides significant development potential — including the

    Brendon Sullivan-Monson StartPoint Realty

    186 Spring St, Hopkinton, MA 01748
  • /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

Home Prices in Upton, MA

Home Price Trends

Median Sale Price
$791,900
Median Single Family Sale Price
$802,500
Median Townhouse Sale Price
$494,949
Median 2 Bedroom Sale Price
$744,900
Median 1 Bedroom Sale Price
$299,000
Average Price Per Sq Ft
$333
Number of Homes for Sale
28
Last 12 months Home Sales
87
Months of Supply
3.90
Median List Price
$769,900
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
12%
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