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$650,000
3 Beds 2 Baths 73571380 MLS
Imagine summer days spent at nearby Kiwanis Beach and evenings under the stars in your private backyard Jacuzzi. Beautifully maintained home offers an exceptional setting just a short walk from Upton Center, the beach, ballfield and courts, and approximately four miles from the Hopkinton I-495 exit and Price Chopper Plaza. Inside, the open kitchen and family room create a warm, inviting place to entertain family and friends. The kitchen features granite countertops and hardwood floors, with a pretty eat in area with slider to the deck, while the cathedral family room is enhanced by a fireplace, hardwood flooring and new skylights. Three bedrooms, two full baths and a two-car garage add everyday comfort. The bedrooms are nicely sized and the baths and kitchen are in great condition. Upstairs, an open loft makes a wonderful office or sitting area, with access to a generous storage area offering potential for additional living space. The finished lower level adds even more room to enjoy. A spacious deck, outdoor shower and shed complement the gorgeous backyard. Sellers have completed many updates in the past 3 years including new carpet and paint, mini splits, furnace, skylights, washer, dryer and fridge. See updates and additional information attached. They also installed a radon mitigation system. This home is truly "move in ready" and a place you can come home to after a long day and just relax. These sellers hope the next owners love this home as much as they have! Don't miss this excellent opportunity to own this lovely home with seasonal water views and within walking distance to so many great places!

24B River Street, Upton

$1,079,000
4 Beds 4 Baths 73574514 MLS
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 kitchen includes two pantry closets, Sub Zero refrigerator and stylish concrete sink and flows to a step-down dining/living area with gorgeous stone fireplace and slider access to the peaceful screened in porch and amazing deck. A laundry room, half bath and vaulted ceiling living room with French doors complete the floor. Upstairs a large bedroom with en-suite bath acts as a second primary and is complemented by two additional bedrooms and full bath on the way to the huge primary bedroom with vaulted ceilings, double closets, a separate room currently being used as a makeup area and an exquisite bathroom with jetted tub and separate shower. The walk out lower level includes a climate controlled wine cellar and access to the heated two car garage. Outdoor living is truly a highlight, with a beautiful stone patio featuring a pizza oven, pergola and a fire pit, plus a deck with newer composite decking and railings and high end built-in grill and additional pergola—perfect for entertaining, dining, or relaxing. Additional features include a new roof with solar panels, a beautifully repaved driveway with a distinctive paver border, and lushly landscaped grounds. With its combination of generous living space, unique amenities, and spectacular indoor-outdoor living, this Upton property offers a rare opportunity to enjoy comfort, in a serene environment yet only a short distance to Routes 495 and 90 and the shops and restaurants nearby.

165 East St, Upton

$549,000
3 Beds 3 Baths 73574288 MLS
Move right into this beautifully maintained, 2020-built end-unit townhouse in the heart of Upton. Set at the rear of the building and open on three sides, the home enjoys abundant natural light throughout. Three finished levels offer a flexible, well-designed layout. The open main level features a sun-filled living room and a stylish kitchen with a large island, stainless steel Samsung appliances, farmhouse sink and tile backsplash, plus a convenient half bath. The second floor offers two spacious bedrooms with double closets, a full tiled bath and in-unit laundry. The entire third floor is dedicated to a private primary suite with a generous closet and en-suite bath. Additional highlights include hardwood flooring throughout, gas heat, central air, a full basement for storage and two exclusive use parking spaces. Enjoy a five-unit association with a low monthly fee, close to Upton Town Center, walking trails, Route 140, I-495 and the Grafton commuter rail. Open house Saturday, September 12, from 10:30 a.m. to noon.

140 Main St Unit E, Upton

$997,500
4 Beds 3 Baths 73573687 MLS
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 with large cooktop, double wall oven, and charming banquette seating that invites everyone to gather. Just beyond, the dramatic cathedral family room is anchored by a beautiful fireplace, creating an incredible backdrop for holiday mornings, celebrations and evenings spent fireside. An oversized dining room elevates every occasion, from elegant dinners to treasured nights gathered with family and friends. The fabulous three season porch offers a front row seat to nature and a peaceful escape to enjoy morning coffee, quiet afternoons or evenings overlooking the beautiful surroundings. Upstairs, the oversized primary retreat feels wonderfully indulgent, featuring a beautiful window seat made for curling up with a favorite book and enjoying a rare quiet moment. The luxurious primary bath completes the experience with a spacious walk in shower and oversized Jacuzzi tub worthy of a private spa. And there is still more to imagine. A huge walkout basement offers exceptional potential for future living space, entertaining areas, a fitness room or whatever comes next. Impressive yet inviting, elegant without feeling untouchable, this is a home designed for the moments that matter and a truly special opportunity in one of Upton's most coveted settings.

27 Juniper Road, Upton

$575,000
3 Beds 2 Baths 73573230 MLS
Welcome to this charming Colonial Style home, offering warmth, character, and modern comfort throughout. The inviting open floor plan creates a seamless flow between the living, dining, and kitchen areas, making the home feel spacious and welcoming. Beautiful hardwood flooring runs throughout the home. The living room is complemented by a cozy fireplace with an elegant marble surround. The kitchen features Stainless Steele appliances, durable granite countertops, and a breakfast bar, flowing naturally to the main living spaces, perfect for everyday living and entertaining.On the second floor you will find three generously sized bedrooms all with hard-wood flooring. The bathroom offers a double-bowl vanity for added convenience and functionality. This delightful property combines charm, functionality, and thoughtful updates in a comfortable and convenient setting. Central air conditioning provides year-round comfort.The finished lower level of the home offers an ideal space to gather to watch a movie, the big game, or just a place for quiet time. Private deck overlooking a fenced in back yard, complete with a firepit. One car garage and a circular driveway add to the overall comfort of this home While the home's classic colonial design adds timeless appeal its location provides easy access to major highways, all for under $600,000

40 Hartford Ave N, Upton

$499,000
3 Beds 3 Baths 73569379 MLS
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 history and remarkably preserved original details, the property is ideally suited for an antique home enthusiast, preservationist, or skilled restorer with the vision to thoughtfully renovate and bring this significant residence into its next chapter. Seller has installed a new 4 bedroom Septic System. The property is being sold in AS-IS condition. Buyers and buyers' agents are responsible for performing their own due diligence regarding the property, its condition, systems, permitted uses, renovation requirements, historical significance, and any other matters important to them. Other than new septic and town water, Seller makes no representations of any type or kind as to condition.

15 W Main St, Upton

$779,900
4 Beds 3 Baths 73569332 MLS
Beautifully updated Dutch-style colonial on nearly 2 acres offers, space, charm and functionality. The home includes an ADU with separate entrance for growing families or friends with it's own living room, kitchen, bedroom, full bath and laundry room. The front entry opens to a central staircase with a spacious fireplaced family room on one side and a formal dining room on the other. The family room is enhanced by a brick fireplace with a wood burning insert, exposed wood beams and original wide pine floors .This level also includes a full bath and an office with plenty of custom built-ins. A door from this room leads out to a large screened porch equipped with all new lighting and screening. Three bedrooms and another full bath occupy the home's second floor. The expansive main bedroom provides great light and extra closet space. Step out from the slider to the expansive rebuilt roof deck overlooking the nicely manicured and fenced in back yard. A new storage shed has been added to the grounds providing added space and functionality. So many thoughtful upgrades (see attached) for the complete list. Centrally located between Boston and Worcester - close to 495 and the Mass Pike. A commuter's dream. This home is very convenient to Upton's highly rated local schools and shopping. Come and make this house your new HOME!

69 Walnut St, Upton

$1,300,000
4 Beds 5 Baths 73566681 MLS
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 and thoughtfully designed floor plan offers generous room sizes, abundant natural light, and plenty of space to gather, work, relax, and entertain. The kitchen serves as the heart of the home and features an updated backsplash, newer appliances, kitchen vent, and a newer slider providing seamless access to the outdoor living areas. Upstairs, the spacious primary bedroom features its own private en suite bath, while an additional bedroom also offers a private full bathroom, an ideal setup for a live-in nanny, guests, extended family, or anyone looking for added privacy. Step outside and prepare to fall in love! The backyard is a true private oasis featuring a stunning heated in-ground pool, hot tub that flows directly into the pool, expansive composite deck, professional landscaping, and irrigation system. Whether hosting summer gatherings, relaxing in the hot tub, dining outdoors, or spending the afternoon poolside, this incredible setting feels like your own private resort. The extensive list of improvements adds tremendous value and peace of mind, including a new boiler, well tank and well pump in 2021; composite deck, pool liner, pool heater and pool pump in 2022; irrigation system in 2023; first-floor AC condenser in 2024; and newly repaved driveway in 2026. Additional improvements include exterior painting and replaced trim, kitchen slider, dishwasher, microwave, kitchen backsplash, venting and more.Set in a desirable Upton neighborhood, this property offers privacy and tranquility while remaining convenient to schools, shopping, dining, recreation, and major commuter routes. With approximately 3,700 sq. ft., 4 bedrooms, 4.5 baths, two bedrooms with private en suite baths, a 3-car garage, extensive updates, and an incredible resort-inspired backyard, 8 Juniper Road offers an exceptional combination of space, amenities, and outdoor living that is difficult to find!

8 Juniper Road, Upton

$975,000
4 Beds 3 Baths 73566169 MLS
Welcome to a 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 countertops, stainless-steel appliances, a double oven, an approximately two-year-old refrigerator, and an oversized walk-in pantry. The first floor also offers convenient laundry, a half bath, a spacious dining room with French doors—perfect for holiday gatherings—and an additional sitting room that provides an ideal home office or flex space. The 23x23 cathedral-ceiling living room offers a cozy retreat with a pellet stove, perfect for relaxing on chilly winter evenings. Quality finishes and thoughtful upgrades throughout the home showcase a level of character, warmth, and established charm that new construction simply cannot replicate. Upstairs, the spacious primary suite features an en-suite bath with newer quartz countertops, double sinks, a walk-in shower, and a generous walk-in closet. Three additional well-sized bedrooms and a full bath with tub/shower and newer quartz countertops complete the second floor. The unfinished walk-out basement, with 9-foot ceilings and large windows, offers incredible potential for additional living space, a recreation room, home gym, or whatever your needs may be. The oversized two-car garage, complete with a negotiable car lift, provides exceptional flexibility for car enthusiasts, hobbyists, or additional storage. Adding to the home’s appeal is an extremely reasonable solar lease at just $137.15 per month, offering the potential for significant energy cost savings. All of this is set in an amazing location, making this exceptional Colonial a wonderful place to call home. With its spacious layout, thoughtful upgrades, abundant potential, and timeless character, this is a home you won’t want to miss!

161 South St, Upton

$695,000
4 Beds 3 Baths 73565350 MLS
Timeless charm & modern comfort describe this renovated Colonial originally built in 1828 on a scenic, quiet country road. Fully reframed in 1988, with a kitchen/family room addition in 1994, this spacious home is in excellent condition. This saltbox-style home blends historic character with contemporary living. The kitchen/family room & the primary bedroom suite have cathedral ceilings & skylights. The open-concept kitchen is designed for entertaining featuring new stainless steel appliances & a convenient peninsula. The adjacent front-to-back living room creates an inviting space for relaxing with a charming fireplace, perfect for cozy evenings. This home provides four comfortable bedrooms & two full baths, with the primary bath offering a jetted tub with shower. The floorplan offers flexibility for multiple home office options. Once you step outside the privacy of the large, level lot and heated in-ground pool designed for leisurely summer days, leaves you imagining the wonderful memories to be made. This much-loved property is the perfect blend of historic elegance and modern amenities. Kiwanis Beach (1/2 mi), Upton Heritage Park (1/4 mi), Upton State Forest (3 mi away), all offer passive recreation opportunities. UPDATES TO PROPERTY: New 4BR septic 2026; Indirect hot water heater 2025; 200 AMP electric 2023; SS kitchen appliances 2025; Chimney repointing 2026; Roof 2023.

5 Elm Street, Upton

$899,000
4 Beds 5 Baths 73564539 MLS
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 room, a bright four-season sunroom, and an expansive deck, making it an ideal space for family gatherings and entertaining. You will appreciate the versatility of both first and second-floor primary suites, all complemented by beautiful hardwood flooring throughout. For the equestrian enthusiast, this property is a true standout. It features a 4–6 stall barn, a 140’x70’ sand arena, and direct trail access to the Upton State Forest. Additional amenities include a detached three-car garage and a sparkling in-ground pool for refreshing summer days. With a newer furnace (2019) and a functional, spacious layout, this home offers incredible potential. Bring your vision and a few updates to make this unique property your own.

96 Fowler St, Upton

$649,900
4 Beds 2 Baths 73563625 MLS
Price improvement by motivated seller ~ New 4-Bed Septic being installed! Fabulous Turn-Key Cape home has a number of custom touches not found in new construction. Home has had major systems updated in the last two years: Viessmann 42-gallon indirect hot water heater, highly-efficient Williamson boiler, new well pump & piping ~ all with long-term warranties. All appliances less than 2 years including washer, dryer, refrigerators, stoves. Exterior of fireplace just cleaned, repointed, and new chimney cap installed. Updated electrical and windows.First floor has a large foyer, generously sized living room with stunning hardwoods and fireplace, oversize eat-in kitchen, laundry, full bath & 3 good-size bedrooms. Second floor ADU accessed by totally separate entrance to the rear has an eat-in kitchen, pantry, full bath, living room, good-size bedroom, and additional room perfect for a home office.Gorgeous lot offers privacy on just under an acre, mature plantings, and tons of parking in horseshoe driveway. Garage under. Move-in ready ~ some minor cosmetic upgrades will make it your own.Amazing legal 2-family home for income property or first-time buyer looking to have mortgage help or space for extended family. Come enjoy all Upton has to offer ~ award-winning schools, conservation lands, local produce, convenient commuter location to Rt. 495, 140, and the local T stations ~ located near Hopkinton, Hopedale, Milford lines!! Property is vacant and easy to show! This is a Must See!!

90 Glenview, Upton

$849,900
4 Beds 3 Baths 73562333 MLS
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 kitchen is the heart of the home, offering abundant cabinetry, a walk-in pantry & opens to the oversize cathedral-ceiling family room. 1st floor laundry/mudroom adds everyday convenience. Generous sized primary suite includes a flexible bonus room ideal for another home office, fitness space or sitting area. A plethora of windows fills the home with bright, natural lighting. Thoughtfully sited for maximum privacy, the inviting farmer’s porch & expansive composite deck provide ideal spaces to relax or entertain. Taft Mill & Goss Pond are just a short walk away, offering kayaking, fishing, hiking & year-round recreation. Convenient access to I-495, the Mass Pike, Worcester, Providence & Boston. Your search is over - welcome home!

2 Brookside St, Upton

$1,340,000
5 Beds 4 Baths 73562275 MLS
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, fireplace and an extraordinary collection of windows fill the space with natural light and views of the surrounding landscape. At the center of the main level, the updated kitchen features quartz counters, extensive cabinetry, stainless appliances, gas/propane cooking and an oversized island. Its open connection to the breakfast area and family room creates an inviting gathering space, while the generous dining room provides plenty of room for larger occasions. A private office or library with built-in bookshelves offers a quiet, distinctive space away from the main gathering areas. The home's generous proportions continue upstairs, where the exceptionally spacious primary suite features two walk-in closets and a beautifully updated, spa-like private bath. Three additional bedrooms, another updated full bath and conveniently located laundry complete the bedroom level. One of the property's greatest advantages is the finished lower level. With its own updated kitchen, bedroom, full bath, living/guest space and recreation room, it offers an outstanding setup for multigenerational living or extended family, while also providing tremendous flexibility for recreation, guests, a home gym or additional living space. Outdoors, a heated inground pool with newer liner, expansive deck with pergola, raised garden beds, brick walkways, fire pit, flowering shrubs and perennials create a wonderful setting for summer gatherings and time at home. Tucked within mature landscaping and a wooded setting, the backyard feels like its own retreat while remaining convenient to Upton's town center, schools, recreation and major commuting routes. An oversized garage provides exceptional vehicle and storage space, while fully owned solar and a newer 5-bedroom septic system are significant improvements for the next owner.

66 Glenview St, Upton

$519,899
3 Beds 4 Baths 73560822 MLS
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 LOFT that can be used as a HOME OFFICE, SITTING AREA, OR FLEX SPACE.The FINISHED LOWER LEVEL with a FULL BATHROOM provides additional living space suitable for a FAMILY ROOM, GUEST SUITE, HOME GYM, OR OFFICE. A PRIVATE DECK extends the living area outdoors, and the attached 2-CAR GARAGE adds convenience.Recent updates include GARAGE DOORS (APPROXIMATELY 1.5 YEARS OLD), WATER HEATER (2026), NEWER WASHER, NEWER DISHWASHER, AND NEWER CARPETING IN THE FINISHED BASEMENT.Conveniently located near MAJOR ROUTES, SHOPPING, DINING, AND LOCAL AMENITIES, this home offers a FUNCTIONAL LAYOUT with VERSATILE LIVING SPACES.

13 Knowlton Cir Unit 13, Upton

$575,000
4 Beds 3 Baths 73559135 MLS
Previously relocated owners say it's time to sell! 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 spectacular third floor addition encompasses a large primary suite with a spectacular, spa like bathroom. Three/four more bedrooms on the second floor - One with an attached room makes a perfect in home office or nursery. Private back yard with a huge deck complete with a pergola. Above ground pool, fire pit, and storage shed, all surrounded by mature gardens, and perennials. Come take a look - you'll fall in love!!

24 Main St, Upton

$774,900
7 Beds 4 Baths 73552661 MLS
Motivated seller:Presenting an exceptional multi-family residence at 158 Main St, Upton, MA, a meticulously maintained property originally constructed in 1900. This inviting home encompasses a generous 3314 square feet of living space, offering a ready-to-move-in condition for discerning buyers. The kitchen is thoughtfully appointed with smart refrigerator technology, enhancing modern convenience and culinary experiences. With 7 bedrooms and 2 full bathrooms complemented by 2 half bathrooms, this two-story property provides ample accommodation. A functional basement offers additional utility, while a welcoming porch enhances the exterior appeal. To truly appreciate the refined character and investment potential of this distinguished multi-family property, we invite your professional inquiry and a private viewing.

158 Main St, Upton

$875,000
4 Beds 3 Baths 73551967 MLS
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 exposed beams, NEW skylights and a NEW ceiling fan. A second living space, formal dining, and powder room round out the main floor. Upstairs, the primary suite boasts a beautiful NEW bathroom and three spacious bedrooms. Outside, a NEW composite deck overlooks a massive backyard where you can grow your own fruit! You'll love the established pear and cherry trees, blueberry bushes, plus there’s a fenced garden area ready for someone with a green thumb. Additional UPDATES include vinyl siding, front steps, garage doors and the finished lower level. Opportunity is knocking—don’t wait to answer!!

10 Sadler Road, Upton

$989,900
4 Beds 4 Baths 73547396 MLS
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 spacious backyard. 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 full of beauty and comfort. The composite decking provides a low-maintenance space for relaxing or entertaining. Located in close proximity to Route 495 and train stations, providing easy access to commuting routes and conveniences. This home is a must-see for anyone seeking modern living in a peaceful, well-connected location! Scheduled for Nov 2026 Closing

19 West Main Street, Upton

$999,900
4 Beds 3 Baths 73547384 MLS
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 full of beauty and comfort. The composite decking provides a low-maintenance space for relaxing or entertaining. Located in a highly sought-after school district, this home is within close proximity to Route 495 and train stations, providing easy access to commuting routes and conveniences. This home is a must-see for anyone seeking modern living in a peaceful, well-connected location! Scheduled for a November 2026 Closing.

17 West Main Street, Upton

$689,000
2 Beds 3 Baths 73546012 MLS ['Upton Ridge'] BLDG.
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 perfect for a home office, or additional living space. The open-concept design seamlessly connects the living room, dining area, a chef’s kitchen, beautiful hardwood floors creating an ideal setting for both everyday living and effortless entertaining. Expansive windows fill the home with natural light while showcasing peaceful wooded views that provide a tranquil backdrop. The expansive walk-out unfinished basement presents exceptional potential for future living space, a home gym, workshop, or abundant storage. Easy access to major routes, shopping and boarders Shining Rock Golf Club!

56 Shannon Way Unit 56, Upton

$2,500,000
4 Beds 5 Baths 73541742 MLS
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. 2-car garage with EV charger & generator backup. EQUESTRIAN: Professional 9-stall barn, heated tack room, wash stall & blanket laundry. 12,384 SF indoor arena (172'x72') + 130'x80' outdoor arena. 60' round pen & 15 turnout paddocks. Roof solar array on barn supplies powers to the property. WELLNESS & RESORT: Detached climate-controlled gym & solar yoga "She Shed." Heated, saltwater, gunite pool, hot tub, 6-person barrel sauna. Outdoor kitchen with pizza oven. Meditation labyrinth, organic fruit orchards, and berry patches.

117 South Street, Upton

$649,900
4 Beds 2 Baths 73540925 MLS
Price improvement by motivated seller ~ New 4-Bed Septic being installed! Fabulous Turn-Key Cape home has a number of custom touches not found in new construction. Home has had major systems updated in the last two years: Viessmann 42-gallon indirect hot water heater, highly-efficient Williamson boiler, new well pump & piping ~ all with long-term warranties. All appliances less than 2 years including washer, dryer, refrigerators, stoves. Exterior of fireplace just cleaned, repointed, and new chimney cap installed. Updated electrical and windows.First floor has a large foyer, generously sized living room with stunning hardwoods and fireplace, oversize eat-in kitchen, laundry, full bath & 3 good-size bedrooms. Second floor ADU accessed by totally separate entrance to the rear has an eat-in kitchen, pantry, full bath, living room, good-size bedroom, and additional room perfect for a home office.Gorgeous lot offers privacy on just under an acre, mature plantings, and tons of parking in horseshoe driveway. Garage under. Move-in ready ~ some minor cosmetic upgrades will make it your own.Amazing legal 2-family home for income property or first-time buyer looking to have mortgage help or space for extended family. Come enjoy all Upton has to offer ~ award-winning schools, conservation lands, local produce, convenient commuter location to Rt. 495, 140, and the local T stations ~ located near Hopkinton, Hopedale, Milford lines!! Property is vacant and easy to show! This is a Must See!! Also listed as a single family with ADU MLS:73563625,

90 Glenview St, Upton

$484,900
3 Beds 2 Baths 73538093 MLS
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 space to fit a variety of needs. The finished lower level offers excellent possibilities as a guest suite, in-law space, home office, recreation room, or additional family living area. Whether you're a first-time homebuyer, looking to downsize, or searching for a home with room to grow, this property provides comfort, convenience, and opportunity. Don't miss your chance to enjoy all that Upton has to offer in this inviting home!

10 Hopkinton Rd, Upton

$749,900
2 Beds 2 Baths 73535220 MLS ["Cobbler's Creek"] BLDG.
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 above, ample Quartz counter space, modern SS appliances, tile backsplash & center island that can double as a breakfast bar or casual gathering spot. The living room accesses a deck & patio. Off the main living space, a dedicated office provides a quiet area to work from home. Primary bedroom is a comfortable retreat including en-suite bathroom w/double sinks, tiled shower w/glass door & large closet. Second bdrm for guests & full bath. Laundry & 2-car garage. Enjoy a serene & convenient location close to everything. ** HOA Fee Includes Water/ Sewer/ Spectrum Internet & Cable & more ** Ready now!

5 Boot Shop Road Unit 5, Upton

$699,900
2 Beds 3 Baths 73524427 MLS ['Upton Ridge'] BLDG.
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, and a large center island. The light-filled gathering room opens through a slider to the rear deck, with remote controlled awning, creating a seamless indoor-outdoor space to relax and enjoy the peaceful surroundings. Upstairs, you’ll find a spacious loft, a generously sized second bedroom with a full bath and walk-in closet. Experience the beauty and tranquility of Upton Ridge while enjoying convenient access to Boston, Providence, New Hampshire, Route 9, I-90, I-495, and the commuter rail.

87 Shannon Way Unit 86, Upton

$1,075,000
4 Beds 3 Baths 73522448 MLS
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 enduring. Designed for elevated living, the expansive floor plan features 4 spacious bedrooms, 2 full baths, and 1 half bath, seamlessly balancing comfort and style. The two-car garage adds convenience, while the gracious front porch delivers a distinguished first impression. Generously sized basement with full build-out opportunity. Set on a property with exceptional outdoor potential, this residence presents a rare opportunity to own a home defined by quality, sophistication, and architectural presence.

32 Mendon St, Upton

$1,125,000
4 Beds 4 Baths 73521066 MLS
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 finishes throughout. The open and inviting layout is ideal for both everyday living and entertaining. A two-car built-in garage offers secure parking and additional storage, while the welcoming front porch adds charm and curb appeal to this stunning new construction. Located in desirable Upton, this home presents a rare opportunity to own a beautifully designed residence in impeccable condition.

30 Mendon St, Upton

$1,699,000
8 Beds 6 Baths 73520686 MLS
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 office. Second floor has primary bedroom, with a gorgeous bathroom complete w/ a soaking tub, a changing room and his and her walk in closets. Laundry room, another 2 full bathrooms and 3 additional bedrooms round out the second floor. 3rd floor has a full bath and four bedrooms. Basement is finished w/ numerous rooms including a full bath. Outside there's a large inground pool with decorative water feature, patios, and all sorts of plantings surrounded by a huge yard and acres of forest. Unique is a understatement. You've got to see it to believe it.

175 Pleasant St, Upton

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