Upton, MA Homes

/40
$815,000 Sold May 15, 2025
- 3,408 Sq Ft
- $239/SF
- 7 Days On Market
- 3 Beds
- 2.5 Baths
- Built 1992
4 Bradish Farm Rd, Upton, MA 01568

Welcome to this charming 3-bed, 2.5-bath Cape-style home tucked away on a cul-de-sac street in Upton! The farmers porch welcomes you as you enter inside. The living room boasts soaring cathedral ceilings w/ exposed beams & a cozy wood-burning fireplace. The kitchen is a chef’s delight, featuring granite countertops, an electric range, a 2nd wood-burning fireplace, & a dining area. Through French

Andrew Bruce Lamacchia Realty, Inc.

4 Bradish Farm Rd, Upton, MA 01568

/36
Est $434,700 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,520 Sq Ft
21 Maple Ave, Upton, MA 01568

21 Maple Ave, Upton, MA 01568

/42
$925,000 Pending
- 4 Beds
- 2.5 Baths
- 3,372 Sq Ft
136 Glenview St, Upton, MA 01568

Breathtaking Country Estate with distant views of Great Blue Hill! Set atop a scenic hill near the Hopkinton town line, this custom-designed colonial offers the perfect blend of elegance and comfort in a stunning natural setting. The grand two-story foyer welcomes you into a sun-filled great room with soaring ceilings—ideal for entertaining. A sprawling eat-in kitchen with a butler’s pantry is

Robyn and Sean Sold My House Team Suburban Lifestyle Real Estate

136 Glenview St, Upton, MA 01568
/28
$795,475 Sold May 15, 2025
- 1,734 Sq Ft
- $459/SF
- 183 Days On Market
- 2 Beds
- 2 Baths
- Built 2024
10 Chickadee Way Unit 25, Upton, MA 01568

Introducing Cobblers Creek, a new 55+ community of detached condominiums from Black Brook Realty. This serene neighborhood is hidden within the viridian tree line yet easily accessible to the Mass Pike in Westborough and Route 495 in Hopkinton. Designed for active adults, Cobblers Creek is a collection of two-bedroom floorplans, including single-level and townhome styles. Our Starling single

StreamLine Communities Streamline Communities - Upton

10 Chickadee Way Unit 25, Upton, MA 01568

/42
Est $444,747 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,532 Sq Ft
13 Maple Ave, Upton, MA 01568

13 Maple Ave, Upton, MA 01568

/42
$799,700 Pending
- 7 Beds
- 7 Baths
- 5,576 Sq Ft
175 Pleasant St, Upton, MA 01568

Welcome to Your Dream Oasis: An Exquisite 7 Bedroom, 7 Bath Estate Awaits. Ascend the grand widow’s walk staircase, spanning 3 elegant levels, & let your imagination take flight. The noble family room, adorned w/ a magnificent English fireplace, seamlessly connects to a bright sunroom, setting the stage for gatherings worthy of royalty. The expansive sunken dining room accommodates large family

THE LASH GROUP Keller Williams Boston MetroWest

175 Pleasant St, Upton, MA 01568
/12
$404,000 Sold May 12, 2025
- 1,420 Sq Ft
- $285/SF
- 5 Days On Market
- 3 Beds
- 2.5 Baths
- Built 1900
51 School St Unit 2, Upton, MA 01568

FHA Approved! Completely renovated in 2024, this open floorplan 3 Bed/2.5 Bath highlights a modern kitchen with high-end appliances, quartz countertops and plenty of space. First floor also includes a large sun-filled living room alongside a small bedroom or home office. Second Floor boasts a Master Suite with walk-in closet and spectacular Master Bathroom. 2nd Bedroom is bright and spacious

Daniel DiBiasio DiBiasio Realty LLC

51 School St Unit 2, Upton, MA 01568

/37
Est $359,118 Not Listed For Sale
- 2 Beds
- 1.5 Baths
- 1,712 Sq Ft
124 Main St, Upton, MA 01568

124 Main St, Upton, MA 01568

/42
$849,900 Pending
- 4 Beds
- 2 Baths
- 2,892 Sq Ft
30 Prospect St, Upton, MA 01568

Your opportunity to own a very unique Upton home! One of only a few off-the-road lots on Prospect Street with 5.24 pastoral and private acres overlooking beautiful westerly views. This classic New England cape features a large 2-car detached garage with an electric car charger included, stone patio, a small horse barn, stone walls, new septic in 2022, and tons of perennial plantings. The inside

Susan Kenney Century 21 Custom Home Realty

30 Prospect St, Upton, MA 01568
/42
$735,000 Sold Apr 30, 2025
- 2,160 Sq Ft
- $340/SF
- 3 Days On Market
- 2 Beds
- 2.5 Baths
- Built 2022
80 Shannon Way Unit 80, Upton, MA 01568

Welcome to this beautiful 2-story townhouse located in the vibrant 55+Upton Ridge community, offering both comfort & style. This well maintained Milan features a desirable first-floor primary suite, providing convenience & privacy. With a total of 2 bedrooms, 2.5 bathrooms & spacious loft, there’s ample space for you & your guests.The open-concept floor plan is perfect for modern living, w/ a

Team Metrowest Berkshire Hathaway HomeServices Commonwealth Real Estate

80 Shannon Way Unit 80, Upton, MA 01568

/31
Est $506,954 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,220 Sq Ft
15 Pleasant St, Upton, MA 01568

15 Pleasant St, Upton, MA 01568

/3
$875,000 Pending
- 2 Beds
- 2.5 Baths
- 2,228 Sq Ft
6 Boot Shop Rd Unit 34, Upton, MA 01568

Introducing Cobblers Creek, a new 55+ community of detached condominiums from Black Brook Realty. This serene neighborhood is hidden within the viridian treeline yet easily accessible to the Mass Pike in Westborough and Route 495 in Hopkinton. Designed for active adults, Cobblers Creek is a collection of two-bedroom floorplans, including single-level and townhome styles. Our Cardinal townhome

StreamLine Communities Streamline Communities - Upton

6 Boot Shop Rd Unit 34, Upton, MA 01568
/25
$903,000 Sold Apr 29, 2025
- 2,816 Sq Ft
- $321/SF
- 3 Days On Market
- 4 Beds
- 2.5 Baths
- Built 1995
2 Plumbley Rd, Upton, MA 01568

OFFER DEADLINE SUNDAY 3/9 5PM!! Welcome to this beautifully maintained 4 bedroom 2 1/2 bath colonial nestled in a serene neighborhood of Upton. This home boasts a spacious layout, with a bright and inviting kitchen featuring upgraded counter tops and gleaming hardwood floors, a perfect space for cooking and entertaining as it flows into the oversized family room. Both full bathrooms feature

Tricia Basquiat Berkshire Hathaway HomeServices Commonwealth Real Estate

2 Plumbley Rd, Upton, MA 01568

/36
Est $639,980 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,000 Sq Ft
29 Pleasant St, Upton, MA 01568

29 Pleasant St, Upton, MA 01568

/42
$575,000 Open Sun 3PM - 4:30PM
- 3 Beds
- 2.5 Baths
- 2,231 Sq Ft
36 Knowlton Cir Unit 36, Upton, MA 01568

~ OPEN HOUSE SUNDAY JUNE 22 3:00-4:30PM ~ This lovely end-unit townhouse features 3 bedrooms plus a loft, 2 1/2 baths and a large room in the lower level. The unit is light and bright with hardwood floors throughout. The 2nd floor features a large MBR with a ceiling fan and full bath. The 2 additional bedrooms are good sized and share the 2nd full bath and the laundry with recent W&D is in the

Karen Richardson LAER Realty Partners

36 Knowlton Cir Unit 36, Upton, MA 01568
/39
$690,000 Sold Apr 29, 2025
- 1,656 Sq Ft
- $417/SF
- 16 Days On Market
- 2 Beds
- 2 Baths
- Built 2022
59 Shannon Way Unit 59, Upton, MA 01568

Like NEW, this sought after, SINGLE LEVEL, Trentino home w/ loads of upgrades is waiting for you at Upton Ridge! A 55+ community, conveniently located a short distance from the Shining Rock Golf Course & Restaurant! This single-level, corner-unit residence w/ HW floors & custom blinds throughout features an expansive layout, just perfect for entertaining in the upgraded GOURMET kitchen! Included

Team Metrowest Berkshire Hathaway HomeServices Commonwealth Real Estate

59 Shannon Way Unit 59, Upton, MA 01568

/36
Est $549,595 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,932 Sq Ft
31 Pleasant St, Upton, MA 01568

31 Pleasant St, Upton, MA 01568

/14
$1,600,000
- 4 Beds
- 3.5 Baths
- 3,842 Sq Ft
Lot 4 Sawmill Brook Ln, Upton, MA 01568

Nestled within a private 4-lot subdivision, this brand-new custom home offers 3,842 sq ft of thoughtfully designed living space, with an additional 1,721 sq ft in the unfinished basement—ideal for storage or future expansion. Set on Lot 4, a generous 4.5-acre parcel, this property delivers the perfect balance of seclusion, space, and luxury. Still time remains to personalize finishes and make

Team Metrowest Berkshire Hathaway HomeServices Commonwealth Real Estate

Lot 4 Sawmill Brook Ln, Upton, MA 01568
/42
$445,000 Sold Apr 11, 2025
- 1,888 Sq Ft
- $236/SF
- 6 Days On Market
- 2 Beds
- 1.5 Baths
- Built 1987
18 Fieldstone St Unit 18, Upton, MA 01568

Welcome to Fieldstone Condominiums! This beautiful and meticulously maintained townhouse offers a picturesque setting as well as an open floor plan. Enter into a bright and sunny living room with custom built-in shelving and bench, gleaming hardwood floors, and glass sliders leading to the large deck. The dining room has ceramic tile floors and flows seamlessly into the stunning cathedral

Karole O'Leary Lamacchia Realty, Inc.

18 Fieldstone St Unit 18, Upton, MA 01568

/41
Est $637,482 Not Listed For Sale
- 4 Beds
- 2 Baths
- 2,164 Sq Ft
34 Mendon St, Upton, MA 01568

34 Mendon St, Upton, MA 01568

/39
$710,000
- 4 Beds
- 1.5 Baths
- 1,851 Sq Ft
26 Brooks St, Upton, MA 01568

This beautifully renovated Colonial blends classic New England charm with stylish modern updates. Originally built in 1900, the home was fully redone in 2021, offering the appeal of a newer home with timeless character. Located in Upton near the town center and new community center, this 4-bedroom, 1.5-bath home sits on 2.19 acres at the end of a quiet dead-end street. Inside, you'll find Cali

Alissa Tosches Keller Williams Pinnacle Central

26 Brooks St, Upton, MA 01568
/42
$785,000 Sold Mar 31, 2025
- 3,725 Sq Ft
- $211/SF
- 30 Days On Market
- 6 Beds
- 3 Baths
- Built 1760
36 N Main St, Upton, MA 01568

NOTE: Seller willing to pay $5000 closing cost credit & take 2nd position mortgage for 1st $50,000. Terms to be negotiated. This stunning home blends old-world colonial charm with modern style, just 3 miles from 495 and 1 exit to the Pike. Enjoy a stocked trout pond (Pratts) and beach nearby. The ¾-acre yard features apple, pear, grapevines, and blueberry/raspberry bushes. Relax by the giant

Team Tom Truong eXp Realty

36 N Main St, Upton, MA 01568

/40
Est $549,714 Not Listed For Sale
- 3 Beds
- 3 Baths
- 2,133 Sq Ft
30 Pleasant St, Upton, MA 01568

30 Pleasant St, Upton, MA 01568

/10
$750,000
- 3 Beds
- 3.5 Baths
- 2,200 Sq Ft
27 James Rd Unit 2, Upton, MA 01568

NEW CONSTRUCTION for such a GREAT price! 3 BRAND NEW HOMES for sale being constructed. This home is 3 Bedroom, 3 1/2 bath, one car garage, finished room and bath in basement, storage area in basement, walk out basement with full door no bulkhead, hardwood floors, kitchen island, fully applianced stainless steel kitchen, third floor walk up area for storage or future finished space, cover front

Kim Kimball Kimball Property Realty Inc.

27 James Rd Unit 2, Upton, MA 01568
/34
$640,000 Sold Mar 31, 2025
- 1,870 Sq Ft
- $342/SF
- 30 Days On Market
- 2 Beds
- 2.5 Baths
- Built 2022
89 Shannon Way Unit 1, Upton, MA 01568

Come enjoy low maintenance living at Upton Ridge! A 55+ community located just a short stroll away from the renowned Shining Rock Golf Course. This Tuscan is a beautiful 2-story home offering a spacious floor plan with a first floor primary suite, an open floor plan, and room for a home office or den. The oversized kitchen has upgraded cabinets, granite countertops and a large island - perfect

Shane Brady Keller Williams Realty

89 Shannon Way Unit 1, Upton, MA 01568

/41
Est $542,697 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,789 Sq Ft
21 Warren Rd, Upton, MA 01568

21 Warren Rd, Upton, MA 01568

/9
$299,900
- Land
- 1.62 Acres
- $185,123 per Acre
12-B Milford St, Upton, MA 01568

Exceptional Opportunity – Tear-Down Property with Scenic Views of Mill Pond. Nestled well back from the road in a peaceful and private setting, this unique property offers a rare opportunity to build your dream home in a truly serene environment. The existing structure is a tear-down, providing a blank canvas for new construction tailored to your vision. The home is accessed by a charming

Lisa Paulette Coldwell Banker Realty - Framingham

12-B Milford St, Upton, MA 01568
/30
$380,000 Sold Mar 28, 2025
- 1,428 Sq Ft
- $266/SF
- 75 Days On Market
- 3 Beds
- 1.5 Baths
- Built 1850
74 Main St, Upton, MA 01568

A Timeless Treasure. Step back in time with this enchanting 3-bedroom, 1.5-bath antique located in the heart of Upton. Built in the 1800s, this home boasts period details and craftsmanship. As you enter through the beautiful double wooden entry doors, you’ll be greeted by the warmth of hardwood floors throughout, including stunning wide pine floors on the second floor that evoke a sense of

Robyn and Sean Sold My House Team Suburban Lifestyle Real Estate

74 Main St, Upton, MA 01568

/42
Est $681,657 Not Listed For Sale
- 3 Beds
- 2 Baths
- 2,150 Sq Ft
24 Warren Rd, Upton, MA 01568

24 Warren Rd, Upton, MA 01568

/9
$299,900
- 4 Beds
- 2 Baths
- 1,430 Sq Ft
12 Milford St, Upton, MA 01568

Exceptional Opportunity – Tear-Down Property with Scenic Views of Mill Pond. Nestled well back from the road in a peaceful and private setting, this unique property offers a rare opportunity to build your dream home in a truly serene environment. The existing structure is a tear-down, providing a blank canvas for new construction tailored to your vision. The home is accessed by a charming

Lisa Paulette Coldwell Banker Realty - Framingham

12 Milford St, Upton, MA 01568
/41
$860,000 Sold Mar 25, 2025
- 3,076 Sq Ft
- $280/SF
- 4 Days On Market
- 3 Beds
- 2.5 Baths
- Built 1997
45 Mendon St, Upton, MA 01568

Custom built Colonial home set on a picturesque 1.55 acre lot. One owner home since its construction, showcasing impeccable craftsmanship & attention to detail. Spacious family room, w/soaring ceiling & stunning stone fireplace, provides a warm & inviting atmosphere. Custom designed kitchen boasts beautifully crafted cabinetry, ample counter space leading to formal dining room, perfect for

Mary Wood Lamacchia Realty, Inc.

45 Mendon St, Upton, MA 01568

/40
Est $643,776 Not Listed For Sale
- 4 Beds
- 2 Baths
- 1,792 Sq Ft
4 Hazeltine Rd, Upton, MA 01568

4 Hazeltine Rd, Upton, MA 01568

/28
$399,000
- 3 Beds
- 1 Bath
- 913 Sq Ft
120 High St, Upton, MA 01568

Don't miss this opportunity! This charming and well cared for antique sits on a hillside with views of Pratt Pond from the enclosed front porch and the dining room. The first floor features a somewhat open concept arrangement of living room, dining room and kitchen. The openness coupled with all the windows gives the space a larger feel. The home has a 3 bedroom septic and all three bedrooms are

Clifton LaPorte Berkshire Hathaway HomeServices Commonwealth Real Estate

120 High St, Upton, MA 01568
/12
$199,000 Sold Mar 20, 2025
- Land
- 9 Acres
- $22,588 per Acre
- 24 Days On Market
0 Orchard St, Upton, MA 01568

This is an excellent opportunity to build your dream home in a beautiful rural setting. The 8.81-acre wooded lot on Orchard Street offers significant privacy. The seller has conducted a perc test and a wetlands study, with findings accessible in the MLS. Take advantage of this perfect chance to establish your ideal residence in the serene town of Upton, where you can enjoy a peaceful country

Shelly Armstrong Redfin Corp.

0 Orchard St, Upton, MA 01568

/42
Est $816,611 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,334 Sq Ft
14 N Main St, Upton, MA 01568

14 N Main St, Upton, MA 01568

/42
$775,000 Open Sun 10:30AM - 11:30AM
- 4 Beds
- 3.5 Baths
- 2,774 Sq Ft
290 Westboro Rd, Upton, MA 01568

MAJOR PRICE ADJUSTMENT ON THIS FANTASTIC HOME! **SHOWINGS START AT OPEN HOUSE SUNDAY 10:30-11:30** IMMACULATE 4 BEDROOM, 3 1/2 BATH, 2,775 Sq.Ft. Colonial! PRIMARY BEDROOM 3 ROOM SUITE With En-Suite Full Bath, Lots of Closet Space & Separate Living Room! RECENTLY REMODLED FIRST FLOOR BEDROOM with En-Suite FULL BATH! Bright & Open Kitchen W/ beautiful GRANITE COUNTERTOPS & TONS Of CABINETS!

Paul Clifford 1 Worcester Homes

290 Westboro Rd, Upton, MA 01568
/28
$773,504 Sold Feb 28, 2025
- 2,228 Sq Ft
- $347/SF
- 156 Days On Market
- 2 Beds
- 2.5 Baths
- Built 2024
1 Chickadee Way Unit 15, Upton, MA 01568

Introducing Cobblers Creek, a new 55+ community of detached condominiums from Black Brook Realty. This serene neighborhood is hidden within the viridian treeline yet easily accessible to the Mass Pike in Westborough and Route 495 in Hopkinton. Designed for active adults, Cobblers Creek is a collection of two-bedroom floorplans, including single-level and townhome styles. Our Cardinal townhome

StreamLine Communities Streamline Communities - Upton

1 Chickadee Way Unit 15, Upton, MA 01568

/18
Est $582,245 Not Listed For Sale
- 4 Beds
- 2 Baths
- 1,378 Sq Ft
3 Central Square, Upton, MA 01568

3 Central Square, Upton, MA 01568

/42
$1,595,000 Open Sat 11AM - 12:30PM
- 4 Beds
- 2.5 Baths
- 2,880 Sq Ft
105 Crockett Rd, Upton, MA 01568

Rare opportunity to own a fully revitalized lakefront home plus a newly approved buildable lot for future 1,300+/- sq ft of pristine lofted living & 3-4 car garage ideal for high rental income or guest space. Situated on a private 0.5-acre lot along Lake Maspenock, this 2024-renovated oasis features panoramic water views from every room, updated systems, and parking for 8–10 cars

The WP Group Smith and Oak Real Estate Co.

105 Crockett Rd, Upton, MA 01568
/24
$480,000 Sold Feb 19, 2025
- 1,040 Sq Ft
- $462/SF
- 6 Days On Market
- 3 Beds
- 1 Bath
- Built 1969
35 Hartford Ave N, Upton, MA 01568

Charming 3-Bedroom, 1-Bath Ranch in Upton – Recently Updated! This beautifully updated ranch-style home features a spacious and inviting layout, with many modern upgrades throughout. The kitchen, renovated in 2019, boasts sleek updated cabinetry, quartz countertops, and newer appliances – perfect for cooking and entertaining. The bathroom has also been updated for a fresh, contemporary look.

Omar Regalado eXp Realty

35 Hartford Ave N, Upton, MA 01568

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