Upton, MA Homes

/42
$799,700 Open Sun 1PM - 3PM
- 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
/35

$2,250 per month

149 Main Street Apartments

1 Bed

149 Main St, Upton, MA 01568

Welcome home to 149 Main, a new luxury apartment community in the quintessential New England Town of Upton, Massachusetts. Offering smart, modern home features from designer cabinetry and color schemes to sought-after community features just outside your door. Discover the lifestyle at 149 Main.

149 Main St, Upton, MA 01568
/2
$3,195,000 Sold May 01, 2025
- 4,770 Sq Ft
- $670/SF
- 364 Days On Market
- 3 Beds
- 3.5 Baths
- Built 1992
332 Mendon St, Upton, MA 01568

Susan Marzo Equine Homes Real Estate, LLC

332 Mendon St, Upton, MA 01568

/29
Est $661,644 Not Listed For Sale
- 3 Beds
- 3 Baths
- 1,698 Sq Ft
36 Brooks St, Upton, MA 01568

36 Brooks St, Upton, MA 01568

/42
$875,000 Open Sun 1PM - 2:30PM
- 5 Beds
- 2.5 Baths
- 3,568 Sq Ft
4 Oak Dr, Upton, MA 01568

How do you put a price on "Happily-Ever-After"? That's what beckons you at this lovely colonial perched atop a country knoll surrounded by layers of woodlands. This 3500+ sq ft home offers a smooth blend of classic charm & modern comfort. The spacious layout includes 5 bedrooms plus a finished lower level, ideal for the growing or blended family with room to spare for hosting guests. The heart

Sandra Copley RE/MAX Real Estate Center

4 Oak Dr, Upton, MA 01568
/5
$1,975 per month
- 1 Bed
- 1 Bath
- 800 Sq Ft
- Apartment for Rent
112 Main St Unit J, Upton, MA 01568

Great location in West Upton Center: 5 minutes to 495, 15 minutes to Mass Pike. Perfect for single/quiet type. New flooring, new paint, new lighting. Park at your door. Well maintained property with other residential units and professional office space. Heat, electric and trash included! Must have good income and good credit - no pets, Questions? ask agent/owner.

Bill McCormick McCormick Properties

112 Main St Unit J, 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

/42
Est $1,005,303 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 4,564 Sq Ft
16 Francis Dr, Upton, MA 01568

16 Francis Dr, Upton, MA 01568

/40
$1,100,000
- 4 Beds
- 2.5 Baths
- 3,465 Sq Ft
5 Briarwood Ln, Upton, MA 01568

This exquisite Post & Beam home seamlessly blends elegance/functionality for today's modern lifestyle. Designed w/custom high end finishes, three levels of luxurious living w/many recent tasteful updates. Beautifully landscaped on a private cul de sac on the east side of town. The heart of the home, a spacious updated gourmet chef's kitchen w/all the bells & whistles, sub zero fridge, an

Bernie Calvario Coldwell Banker Realty - Northborough

5 Briarwood Ln, Upton, MA 01568
/21
$2,800 per month
- 3 Beds
- 1 Bath
- 2,044 Sq Ft
- Apartment for Rent
156A Main St Unit A, Upton, MA 01568

New Rental in Upton. Large 3 level Townhouse with 3 bedrooms ,updated kitchen, hardwood floors, granite counters and SS Appliances. Large deck off the back overlooking conservation area. Hardwood floors in living, dining and 2 bedrooms. Bonus 3rd floor space great for an office or playroom. Open walk out basement. Off street parking behind the unit. Tenant responsible for all utilities,

Kara Capalucci Afonso Real Estate

156A Main St Unit A, 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

/42
Est $963,586 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 3,901 Sq Ft
14 Francis Dr, Upton, MA 01568

14 Francis Dr, Upton, MA 01568

/3
$864,900 New Construction
- 2 Beds
- 2.5 Baths
- 2,228 Sq Ft
18 Boot Shop Rd Unit 40, 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

18 Boot Shop Rd Unit 40, 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

/41
Est $359,336 Not Listed For Sale
- 2 Beds
- 1.5 Baths
- 1,144 Sq Ft
12 Pinecrest Rd Unit B, Uxbridge, MA 01569

12 Pinecrest Rd Unit B, Uxbridge, MA 01569

/28
$855,900 New Construction
- 2 Beds
- 2 Baths
- 1,734 Sq Ft
5 Boot Shop Rd Unit 31, 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

5 Boot Shop Rd Unit 31, 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

/36
Est $387,343 Not Listed For Sale
- 4 Beds
- 2 Baths
- 1,836 Sq Ft
16 Yale St, Uxbridge, MA 01569

16 Yale St, Uxbridge, MA 01569

/27
$1,109,500 New Construction
- 4 Beds
- 2.5 Baths
- 2,884 Sq Ft
16 Rawson Farm Rd, 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

16 Rawson Farm Rd, Mendon, MA 01756
/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

/37
Not Listed For Sale
- 7 Beds
- 3 Baths
- 2,548 Sq Ft
12 Hartford Ave E, Uxbridge, MA 01569

12 Hartford Ave E, Uxbridge, MA 01569

/28
$751,340 Open Sun 11AM - 4PM
- 2 Beds
- 2.5 Baths
- 2,245 Sq Ft
15 Shoemaker Ln Unit 7, 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 Bluebird townhome

StreamLine Communities Streamline Communities - Upton

15 Shoemaker Ln Unit 7, 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

/32
Est $508,351 Not Listed For Sale
- 3 Beds
- 1.5 Baths
- 1,560 Sq Ft
29 Hartford Ave N, Upton, MA 01568

29 Hartford Ave N, 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
/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

/41
Est $610,020 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,528 Sq Ft
53 Warren St, Upton, MA 01568

53 Warren St, Upton, MA 01568

/24
$780,000 Pending
- 4 Beds
- 2.5 Baths
- 2,659 Sq Ft
9 Thayer St, Upton, MA 01568

Nestled in a private, tucked-away neighborhood with cul-de-sacs at both ends, this stunning Colonial is a nature lover’s dream. Set back from the street, this home boasts great curb appeal & an abundance of natural light. Experience indoor-outdoor living with a large fenced yard, in-ground pool, & an expansive 1.8-acre property surrounded by the Upton State Forest. Follow a trail from the

Chris Vietor eXp Realty

9 Thayer 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

/31
Est $445,119 Not Listed For Sale
- 3 Beds
- 1 Bath
- 1,008 Sq Ft
48 Hartford Ave N, Upton, MA 01568

48 Hartford Ave N, Upton, MA 01568

/28
$795,475 Pending
- 2 Beds
- 2 Baths
- 1,734 Sq Ft
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
/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

/28
Est $555,066 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 1,731 Sq Ft
39 Knowlton Cir, Upton, MA 01568

39 Knowlton Cir, Upton, MA 01568

/40
$829,900 Pending
- 3 Beds
- 2.5 Baths
- 3,408 Sq Ft
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
/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

/29
Est $711,675 Not Listed For Sale
- 6 Beds
- 1.5 Baths
- 3,218 Sq Ft
100 Main St, Upton, MA 01568

100 Main St, Upton, MA 01568

/28
$769,900 Pending
- 2 Beds
- 2.5 Baths
- 2,245 Sq Ft
8 Chickadee Way Unit 24, 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 Bluebird townhome

StreamLine Communities Streamline Communities - Upton

8 Chickadee Way Unit 24, 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

/42
Est $789,845 Not Listed For Sale
- 7 Beds
- 3.5 Baths
- 4,197 Sq Ft
128 Main St, Upton, MA 01568

128 Main St, Upton, MA 01568

/30
$784,900 Pending
- 2 Beds
- 2.5 Baths
- 2,228 Sq Ft
12 Chickadee Way Unit 26, 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

12 Chickadee Way Unit 26, Upton, MA 01568

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