Upton MA 4 Bedroom Real Estate, Homes, Condos for Sale

4 Beds ⋅ 4 Baths ⋅ NEW Status ⋅ 73574514 MLS ⋅ 3,350 SqFt.

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

$997,500

4 Beds ⋅ 3 Baths ⋅ NEW Status ⋅ 73573687 MLS ⋅ 3,332 SqFt.

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

$779,900

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 73569332 MLS ⋅ 2,422 SqFt.

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 ⋅ ACTIVE Status ⋅ 73566681 MLS ⋅ 3,543 SqFt.

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 ⋅ ACTIVE Status ⋅ 73566169 MLS ⋅ 2,941 SqFt.

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 ⋅ ACTIVE Status ⋅ 73565350 MLS ⋅ 2,108 SqFt.

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 ⋅ ACTIVE Status ⋅ 73564539 MLS ⋅ 4,242 SqFt.

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 ⋅ PRICE CHANGED Status ⋅ 73563625 MLS ⋅ 2,534 SqFt.

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 ⋅ ACTIVE Status ⋅ 73562333 MLS ⋅ 3,132 SqFt.

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

$575,000

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 73559135 MLS ⋅ 2,548 SqFt.

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

$929,900

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 73557408 MLS ⋅ 3,100 SqFt.

Stunning fully renovated luxury home offering three finished levels of sophisticated living with high-end finishes and designer details throughout. This turnkey home features an open-concept floor plan, a custom chef's kitchen with premium appliances, spa-inspired bathrooms, modern lighting, and beautifully updated living spaces. Thoughtfully renovated with exceptional craftsmanship, it seamlessly blends timeless charm with contemporary elegance. Move-in ready and designed for today's lifestyle, this exceptional home offers comfort, style, and quality in every detail.

33 Milford St, Upton

$1,159,000

4 Beds ⋅ 3 Baths ⋅ UNDER AGREEMENT Status ⋅ 73553629 MLS ⋅ 3,360 SqFt.

NEIGHBORHOOD SETTING WITH COMMUTER CONVENIENCE! This North-facing colonial offers over an acre of mature, professionally landscaped yard space that abuts trails and conservation land. Inside, the open layout is anchored by an incredibly spacious family room and modern chef’s kitchen with a double oven, 5-burner gas cooktop and oversized island to use for casual dining eating or as a homework hub. There’s even a custom wet bar with a wine fridge! Other 1st floor features include a private office with details you can't miss - crown molding and French doors - plus a gorgeous, sun-lit living room, elegant dining room, and laundry. Upstairs, the primary suite features walk-in closets alongside three additional bedrooms, all with hardwood floors. You’ll beat the heat with BRAND NEW AC condensers (’26). EV charger stays. Outside, spend your summers on the composite deck and custom patio overlooking a tranquil fish pond - all fenced in with a shed for storage. This is move-in-ready luxury!

33 Dairy Drive, Upton

$875,000

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 73551967 MLS ⋅ 2,806 SqFt.

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 ⋅ ACTIVE Status ⋅ 73547396 MLS ⋅ 2,990 SqFt.

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 ⋅ ACTIVE Status ⋅ 73547384 MLS ⋅ 2,780 SqFt.

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

$2,500,000

4 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 73541742 MLS ⋅ 4,040 SqFt.

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 ⋅ PRICE CHANGED Status ⋅ 73540925 MLS ⋅ 2,534 SqFt.

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

$699,000

4 Beds ⋅ 3 Baths ⋅ UNDER AGREEMENT Status ⋅ 73523806 MLS ⋅ 2,835 SqFt.

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, cozy natural wood kitchen, and countless nooks and period details throughout. Three fireplaces add warmth and ambiance. Outside, enjoy a storybook setting with mature trees, flowering shrubs, open lawn, meadow, tranquil pond, and iconic stone walls. Detached 2-car garage with loft and natural light offers endless possibilities. Recent updates include restored mid-1800s windows with storm windows, central air, metal roof, renovated 2nd-floor bath, fresh exterior paint, regraded driveway with cobblestone pavers, and stunning patio with reclaimed brick from Worcester with stone walkway.

52 Elm St, Upton

$1,075,000

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 73522448 MLS ⋅ 2,924 SqFt.

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 ⋅ ACTIVE Status ⋅ 73521066 MLS ⋅ 3,402 SqFt.

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

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