The Preserve at Dean Pond Real Estate, Homes, Condos for Sale in Upton, MA

3 Beds ⋅ 2 Baths ⋅ NEW Status ⋅ 73571380 MLS ⋅ 2,055 SqFt.

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 ⋅ 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

$549,000

3 Beds ⋅ 3 Baths ⋅ NEW Status ⋅ 73574288 MLS ⋅ 1,760 SqFt.

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 ⋅ 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

$575,000

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 73573230 MLS ⋅ 1,556 SqFt.

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 ⋅ CONTINGENT Status ⋅ 73569379 MLS ⋅ 3,217 SqFt.

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 ⋅ 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

$789,900

2 Beds ⋅ 2 Baths ⋅ UNDER AGREEMENT Status ⋅ 73567391 MLS ⋅ 1,734 SqFt.

Come view our beautiful, new construction "Starling" model offering one-level at Cobbler's Creek, a vibrant 55+ community built by exceptional builders with a reputation for excellence! Enjoy a welcoming, open & airy floor plan that seamlessly connects bright living and dining areas to the stylish kitchen all with hardwood floors. The well-appointed kitchen features attractive cabinets with moldings above, ample Quartz counter space, tile backsplash, modern SS appliances & center island that can double as a breakfast bar or casual gathering spot. Off the living room, there's a deck & patio. From the main living space, the hallway accesses a dedicated office providing quiet space to work from home, second bedroom for guests, full bath and laundry. Primary bedroom is a comfortable retreat including en-suite bathroom w/double sinks, tiled shower w/glass door & large closet. Two-car garage with entry into hall w/closet. Enjoy a serene setting in a convenient location near everything. ** HOA Fee Includes Water/ Sewer/ Spectrum Internet & Cable & more **

14 Boot Shop Road Unit 14, 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

$1,340,000

5 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 73562275 MLS ⋅ 4,498 SqFt.

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

$779,900

2 Beds ⋅ 2 Baths ⋅ UNDER AGREEMENT Status ⋅ 73561608 MLS ⋅ 1,743 SqFt.

Impressive Like New Freestanding Ranch Home in Highly Sought-After Rockwood Meadows Over 55 Community on The Hopkinton Line Just A Few Miles Away From 495/MA Pike Exits. Premium Lot Which Backs up Conservation Area Offering Miles Hiking, Biking and Running Trails. Features an Open Plan With Gorgeous Cherry Cabinet Kitchen, Granite Counters, Stainless Appliances, Center Island and Access to Private Deck, Gas Fireplaced Family Room, Hardwood Floors Throughout, Crown Moldings and Tons of Natural Light in Every Room! Large Primary Suite Features His/Her Closets and Fantastic Bath With Granite, Spacious Second Bedroom With Adjacent Full Bath Also With Granite, Laundry Room With Cherry Cabinets, Huge Basement With Excellent Finishing Potential For Lots of Extra Living Space, Low HOA Fees Include Access to The Awesome Clubhouse With Fitness Center and Entertainment Space For Large Gatherings + Year Round Exterior Maintenance!, Affordable FHA Gas Heat, Central Air, Lowest-Priced One Owner Home Offers The Opportunity to Be Among Much Higher Priced Homes! Come Take a Look at This Detached Home That Shows Mint - You Will Feel Like You Entered a Model Home.

41 Rockwood Ln Unit 41, Upton

$519,899

3 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 73560822 MLS ⋅ 2,091 SqFt.

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

$495,000

3 Beds ⋅ 1 Baths ⋅ UNDER AGREEMENT Status ⋅ 73560760 MLS ⋅ 1,080 SqFt.

Welcome to this 3-bedroom (with brand NEW 3 Bedroom Septic being installed) split-level home offering a wonderful opportunity to build equity and create the home you’ve always envisioned. The main level features a bright living room, a spacious eat-in kitchen with access to the rear deck, and three comfortable bedrooms. The finished lower-level family room provides additional living space ideal for a playroom, home office, media room, or gym. An attached one-car garage offers convenient parking and extra storage. Step outside to enjoy the level backyard, perfect for entertaining, gardening, pets, or outdoor activities. A brand-new septic system is currently being installed, providing added value and peace of mind for the next owner. While the home does need flooring, paint, and updating, it offers solid bones and endless potential. Bring your ideas, creativity, and vision to transform this property into your dream home. Conveniently located in the highly desirable town of Upton with easy access to schools, parks, shopping, and major commuter routes, this is a fantastic opportunity for investors, contractors, or buyers looking to customize a home and make it truly their own. Don’t miss your chance to unlock the potential this property has to offer!

4 Picadilly 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

$460,000

4 Beds ⋅ 3 Baths ⋅ SOLD Status ⋅ 73557327 MLS ⋅ 2,340 SqFt.

Calling All Contractors, Investors & Flippers! Exceptional opportunity to transform this 4-bedroom Coln, privately sited on nearly 2 acres in desirable Upton. Featuring an impressive family room, 2 full baths, first-floor laundry, an unfinished LL & a 2-car under garage, this home offers a fantastic floor plan and tremendous potential. The property is in need of a complete renovation due to burst pipes and subsequent professional remediation. All damaged materials have been removed, leaving the home ready for its next chapter. Please note that there is currently no active plumbing or functioning bathrooms. The roof is Sept 2022 and furnace is approximately 10 years old. Cash buyers only. This property will not qualify for conventional financing. Open House Sun 2-4

324 Mendon Street, Upton

$680,000

4 Beds ⋅ 3 Baths ⋅ SOLD Status ⋅ 73556199 MLS ⋅ 2,324 SqFt.

**OFFER DEADLINE - Tues, 8/4, 3PM** Welcome to this beautifully crafted 2006-built Colonial offering 2,324 square feet of thoughtfully designed living space. With 4 bedrooms and 2.5 bathrooms, this home blends timeless New England style with modern updates throughout.The spacious kitchen features upgraded quartz countertops and custom cabinetry and shelving with abundant storage, perfect for everyday living and entertaining. The primary suite includes a private en-suite bathroom for a comfortable retreat. A brand-new deck at the rear of the home overlooks more than two acres of land that abuts conservation land, offering exceptional privacy and natural surroundings. The walkout basement presents excellent potential for additional finished living space.Additional highlights include a massive 2-car garage with extra storage capacity, central air conditioning installed in 2014 and solar panels that help reduce utility costs. This home has plenty of potential for its next owner to make it their own.Don't miss this opportunity to own a well-maintained Colonial on a private, oversized lot in Upton, MA — conveniently located near local roadways, schools, and town amenities.

30 Pearl St, Upton

$499,000

3 Beds ⋅ 1 Baths ⋅ UNDER AGREEMENT Status ⋅ 73555450 MLS ⋅ 1,316 SqFt.

***OPEN HOUSE CANCELED***Stunning views with the ability to enjoy time on the water for under $500K. Welcome home to this beautiful single-family ranch in Upton MA across the street from Pratt Pond. Enjoy kayaking, canoeing, boating, and fishing just steps from your front door. This well maintained 3-bedroom 1-bath home sits on a flat 0.75-acre lot perfect for spending time outside entertaining, gardening, and more. Inside you are met with a beautiful living room with vaulted ceilings and a scenic view of the water. Your comfortable kitchen flows nicely into the dining room which is well sized to host your next get-together. Down the hall your full bathroom and three bedrooms await (one with your washer and dryer) all with hardwood flooring. Additional highlights include a heated 2-car detached garage with plenty of storage space, a fenced-in backyard and plenty of off-street parking. Homes that offer scenic views, a usable yard, and this much value are hard to find. Don't miss this opportunity to make this charming Upton home your own! Call to schedule your showing today!

71 School 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

$774,900

7 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 73552661 MLS ⋅ 3,314 SqFt.

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

$699,000

6 Beds ⋅ 3 Baths ⋅ UNDER AGREEMENT Status ⋅ 73552323 MLS ⋅ 2,617 SqFt.

Rare 2-Family Gem with Historic Charm & Modern Luxury. Discover this meticulously renovated two-family home, perfectly situated on 2 sprawling acres near the heart of town. Gutted to the studs in 2015 and updated with a new roof, windows, and high-end finishes, this property offers the peace of mind of a new build with the character of a classic estate. Both units are fully de-leaded, light-filled, and feature gorgeous wide-plank and hardwood floors, granite countertops, and stainless steel appliances. Unit 1 (822 sq. ft.): A comfortable first-floor layout with direct access to a full basement featuring private laundry hook-ups. Unit 2 (1,811 sq. ft.): A stunning two-story retreat (levels 2 & 3) boasting 4 spacious bedrooms, 2 full baths, a dedicated laundry room, and a massive walk-in closet. Mechanicals are top-tier with separate utilities, including two new boilers, 2022, 2023 and tankless hot water heaters. Outside, the property shines with exceptional curb appeal, 8 parking spaces

78 Main Street, 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

$680,000

4 Beds ⋅ 3 Baths ⋅ SOLD Status ⋅ 73549886 MLS ⋅ 1,800 SqFt.

This one owner home awaits!! Wait until you see this four bedroom colonial - located is a desirable in town location, super close to Memorial School and downtown, yet on a quiet neighborhood cul de sac. Town water, Town sewer, and gas!! All the big ticket items have been done. Replacement windows, roof, water heater, updated electrical, A/C, Garage doors, newer appliances, sealed driveway. Nice size back yard with deck. Four carpeted bedrooms on the second floor. Fireplaced family room with carpet, formal living and dining room, eat in kitchen. Basement could easily be finished for extra space. This is one you'll want to call home!!!

7 Hazeltine Rd, 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

$751,500

4 Beds ⋅ 3 Baths ⋅ SOLD Status ⋅ 73546600 MLS ⋅ 2,668 SqFt.

This exceptional 3.7 acre country estate blends luxury living with outstanding outdoor amenities. The Colonial home features hardwood floors, soaring ceilings, multiple fireplaces, wood stoves, new central heat, mini-splits, and a gourmet kitchen with granite counters and stainless appliances. The main level offers formal and casual living spaces, a bright dinning room, living room, family room, full bath, and bonus room. Upstairs are four bedrooms, including a spacious primary suite with 3/4 bath and a custom California Closet. The finished lower level adds 2 rooms for more flexible living space. Solar panels, updated well equipment, and a new boiler improve efficiency. Outside, enjoy a hot tub, screened porch, fire pit, pond, barn/gym and large recreation area with a soccer/basketball half court. Located across from Upton State Forest with direct access to miles of trails.

218 Mechanic, Upton

$689,000

2 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 73546012 MLS ⋅ 1,950 SqFt.

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 ⋅ 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

$640,000

3 Beds ⋅ 2 Baths ⋅ SOLD Status ⋅ 73540194 MLS ⋅ 1,546 SqFt.

Bursting with charm and set on 1.84 picturesque acres, this white antique Cape offers standout curb appeal on a scenic country road. Designed for easy living, the first floor features the primary bedroom, full bath, laundry, and an open-concept living, dining, and kitchen area with beautiful backyard views and direct access to the deck. Outside, the freshly painted red barn and smaller white barn, both with electricity, add character, versatility, and exciting potential, with the larger barn ready for restoration and future possibilities. Ideally located near the Hopkinton line, this property is a commuter’s dream—just over 3 miles to I-495—while still convenient to shopping, dining, and everyday amenities. A rare opportunity to enjoy classic New England charm, usable acreage, and a sought-after location.

149 Glenview St, Upton

$484,900

3 Beds ⋅ 2 Baths ⋅ CONTINGENT Status ⋅ 73538093 MLS ⋅ 1,176 SqFt.

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

$785,000

4 Beds ⋅ 3 Baths ⋅ SOLD Status ⋅ 73538003 MLS ⋅ 2,408 SqFt.

Welcome to 20 Josiah Drive, a beautifully maintained Colonial in one of Upton’s most desirable neighborhoods. This spacious 4-bedroom, 2.5-bath home offers over 2,200 sq ft of sun-filled living space with newly refinished hardwood floors and an open layout ideal for everyday living and entertaining. The vaulted-ceiling great room and fireplaced family room create warm and inviting spaces, while the formal dining room and additional living area offer flexibility for today’s lifestyle. All four bedrooms are located on the second floor, including a spacious primary suite with a walk-in closet and private en-suite bath. The main level features a large kitchen with granite countertops, hardwood flooring, dining area, a fully heated & insulated sunroom, and composite deck overlooking the private backyard with mature landscaping and peaceful seasonal views. Additional highlights include central air, fenced yard, 2-car garage, and excellent curb appeal.

20 Josiah Drive, Upton

$720,000

3 Beds ⋅ 3 Baths ⋅ UNDER AGREEMENT Status ⋅ 73537714 MLS ⋅ 1,304 SqFt.

Upton Horse Haven: Iconic 3-Bed, 3-Bath Retreat on 3.75 Acres. Discover one of Upton’s most beloved properties, a premier estate where timeless charm meets outdoor living. This home features modern upgrades including 200-amp electrical system, a new oil tank, and town water for seamless reliability. A newly finished basement for entertaining or retreat. Property offers direct access to miles of trails in the Upton State Forest—perfect for hikers, riders, and nature lovers. The BOH allows boarding for 2-3 horses, making it a dream for equestrians. Set on 3.75 lush acres and just minutes from I-495, it combines suburban serenity with effortless access to city conveniences. According to town zoning regulations the property is subdividable offering flexibility for future development. Don’t miss this iconic, horse-friendly haven—bring your vision and schedule your tour today.

11 James Rd, Upton

$866,900

3 Beds ⋅ 3 Baths ⋅ SOLD Status ⋅ 73537667 MLS ⋅ 3,076 SqFt.

Custom-built Colonial set on a picturesque 1.55-acre lot. Showcasing exceptional craftsmanship, quality construction and a thoughtfully designed floor plan, this home offers the perfect blend of comfort and functionality for today's lifestyle. The spacious family room features a soaring ceiling and striking stone fireplace, creating a warm and inviting gathering space. The kitchen offers beautifully crafted cabinetry, generous counter space and seamless flow to the formal dining room, ideal for entertaining. A home office, first-floor laundry, and versatile living room or den complete the main level. Upstairs, the expansive primary suite includes two walk-in closets and a private bath, while 2 additional bedrooms complete the 2nd floor. Enjoy the charming front porch and spacious rear deck with Trex decking overlooking the private yard. A partially fenced area is perfect for four-legged friends. Two-car garage, walk-out basement, timeless design, meticulous upkeep, & solid construction

45 Mendon Street, Upton

$635,000

3 Beds ⋅ 2 Baths ⋅ SOLD Status ⋅ 73537386 MLS ⋅ 1,638 SqFt.

The charm of yesteryear with moden conveniences. This meticulously maintained and updated 3 bed, 1.5 bath Antique home has been loved by same family for 93 years and is now looking for the next family to welcome home. Pride of ownership shows in custom laid hardwoods and buit-ins. Light-filled large rooms, 4 working fireplaces in the living room, first-floor bedroom, and two upstairs bedrooms. Home offers expansion potential with 15.3 x 14.7 unfinished wing, adjacent to kitchen, waiting for your imagination. Central air, furnace, water heater, roof, and updated baths all newer and installed since 2013. Detached garage/shed for projects, storage, or parking. Stunning level lot has been the ideal setting for weddings, parties, and story hours throughout the generations. This home is truly a must-see!! Located convenient to Upton's many conservation land/trails, schools, highways, and all Upton has to offer! Sellers willing to sell completely furnished.

236 Mendon St, Upton

$799,000

2 Beds ⋅ 3 Baths ⋅ UNDER AGREEMENT Status ⋅ 73535231 MLS ⋅ 2,228 SqFt.

New amazing price at Cobbler's Creek, a premier 55+ community of detached condominiums by the renowned Black Brook Realty builder group! Enjoy a Storybook setting of homes nestled in a serene landscape where every day feels like a retreat! The popular "Cardinal" model offers 2-story living with everything you need handy on the 1st floor such as a covered front porch, foyer, powder rm, laundry rm & entry to your 2-car garage. An open floor plan offers a living & dining area w/ fireplace & hardwood floors accessing a deck with tranquil wooded views, plus kitchen featuring beautiful white cabinets, large center island & stainless-steel appliances. Primary bedroom suite includes h/w floors, spacious closet & full bath w/double sinks & tiled shower. 2nd floor offers has a terrific loft w/hrdwd, second bedroom & full bath. Energy efficient systems. Be part of a wonderful community w/access to a clubhouse & trails. * HOA Fee Includes Water/ Sewer/ Spectrum Internet & Cable & more. Ready now!

12 Boot Shop Road Unit 12, Upton

$749,900

2 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 73535220 MLS ⋅ 1,734 SqFt.

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

$1,200,000

4 Beds ⋅ 3 Baths ⋅ SOLD Status ⋅ 73532182 MLS ⋅ 3,570 SqFt.

Modern farmhouse-inspired luxury meets exceptional craftsmanship in this stunning custom-built ranch set on 4.8 private acres. Designed for effortless single-level living, this one-of-a-kind home offers an open-concept floor plan filled with natural light from oversized windows and accented by gleaming hardwood floors throughout the main living areas. The sleek chef’s kitchen features tall custom cabinetry, quartz countertops, premium finishes, and a spacious layout ideal for entertaining. The luxurious primary suite serves as a private retreat with a spa-inspired bath and expansive walk-in closet. Three additional bedrooms & 2.5 baths. The beautifully finished walkout lower level dramatically expands the living space and is ideal for a media room, game room, home office, gym, or guest accommodations. Outside, a spectacular hardscape patio overlooks the private grounds. Abutting state forest with great walking trails.

27 W River St, Upton

$600,000

3 Beds ⋅ 3 Baths ⋅ UNDER AGREEMENT Status ⋅ 73530257 MLS ⋅ 1,792 SqFt.

Nestled on a 6-acre lot, this private retreat offers the perfect blend of country charm and endless potential. Surrounded by nature and set 1/3 of a mile back from the road, this 3-bedroom home provides a peaceful setting with sweeping views of the expansive front lawn. Inside, the open-concept design creates a warm and inviting atmosphere. The family room features a vaulted ceiling, hardwood floors and a wood-burning fireplace. Charming kitchen w/ dining area open to the family room—ideal for everyday living and entertaining. A 1st floor bedroom offers flexibility for one-level living or as an office or guest rm. Upstairs, you’ll find two generously sized bedrooms, including a primary bedroom complete w/ensuite bath and a Juliette balcony. Whether you’re looking for privacy, acreage, or the opportunity to customize a home to your personal style, this property is a rare find. Passing Title V for 4 bedrooms.

110B High Street, Upton

$420,000

3 Beds ⋅ 1 Baths ⋅ SOLD Status ⋅ 73530168 MLS ⋅ 1,727 SqFt.

Bring your vision and unlock the potential of this classic Colonial set on a beautiful, level lot in desirable Upton! Offering a rare combination of major exterior updates and room to build instant equity, this home is the perfect opportunity for investors, contractors, or buyers eager to create their dream home. Significant improvements have already been completed including 9 year old vinyl siding & roof. Inside, you’ll find hardwood floors, an updated kitchen, generous room sizes and abundant natural light throughout. While the interior is ready for cosmetic improvements and renovation, the possibilities are endless. The spacious yard provides plenty of room for entertaining, gardening, recreation, or future enhancements. Conveniently located near schools, parks, shopping, restaurants, and commuter routes. A solid home with great bones, valuable updates already in place, and tremendous upside in one of Upton’s most sought-after communities.

5 Pleasant St, Upton

$766,700

3 Beds ⋅ 2 Baths ⋅ SOLD Status ⋅ 73528914 MLS ⋅ 2,912 SqFt.

Discover the perfect blend of privacy and convenience on 6 wooded acres! Set back from the road and surrounded by mature trees, this property offers a peaceful setting while remaining close to local amenities, recreation, and commuter routes. Enter through double front doors into a spacious living room with hardwood floors, a bow window, and a cozy wood stove. The kitchen features stainless steel appliances, wall oven, center island, and dining area with skylight. The expansive family room showcases hardwood floors, vaulted ceilings with skylights, a pellet stove, oversized picture window, and French doors leading to the backyard. A formal dining room and ¾ bath complete the main level. Upstairs offers a spacious primary bedroom with generous closet space, two additional bedrooms, and a full bath. Enjoy room for entertaining, gardening, and outdoor recreation just minutes from Pratt Pond, Kiwanis Beach, shopping, dining, and major routes. Open Houses this Friday evening & Saturday!

74 High Street, Upton

$525,000

3 Beds ⋅ 3 Baths ⋅ SOLD Status ⋅ 73528006 MLS ⋅ 1,372 SqFt.

Experience effortless single-level living in this beautifully updated Ranch on a level corner lot at 57 Plain St. The main level features two bedrooms with pristine hardwood floors, plus a bright sun-filled kitchen boasting stainless steel appliances, a skylight, new tile flooring, fresh cabinets, and stone countertops. Thoughtful layout includes a full and a half bath on the main floor and a welcoming living room. The finished lower level adds flexible space—perfect as a third bedroom option or a cozy family room. Peace of mind comes with a newer 3-bedroom septic system installed in 2018. Just moments from all Upton has to offer, this home is turnkey and ready for you to enjoy. Extra perks include a fully fenced yard, a new heating system, an oversized storage shed & sauna. All the heavy lifting is complete—welcome home.

57 Plain St, Upton

$410,000

3 Beds ⋅ 2 Baths ⋅ SOLD Status ⋅ 73526517 MLS ⋅ 1,420 SqFt.

Welcome to this beautifully maintained 3 bedroom, 2 bath condominium in the desirable town of Upton. This bright and inviting home features an open concept layout designed for comfortable living and effortless entertaining. The modern kitchen is highlighted by elegant quartz countertops, ample cabinetry, and a seamless flow into the dining and living areas.Enjoy year round comfort with central heating and air conditioning throughout the home. The spacious primary bedroom offers a private retreat, while two additional bedrooms provide flexibility for family, guests, or a home office. Additional highlights include a washer and dryer conveniently located in the unit and the ease of low maintenance condominium living.

51 School St Unit 3, Upton

$752,000

2 Beds ⋅ 4 Baths ⋅ SOLD Status ⋅ 73525704 MLS ⋅ 2,200 SqFt.

LAST UNIT AVAILABLE NEW CONSTRUCTION. Free standing unit no age restrictions in 4 lot subdivision. Kitchen is spacious with eat in dining area, hardwood floors, granite, kitchen island, stainless steel appliances. Opens to a family room with access to backyard. Upstairs has a 3 bedroom layout but deeded as a 2 bedroom dwelling 3rd room could be in home office/den/playroom. Ensuite primary with tiled shower and glass enclosure with double vanity sinks and soaking tub. Second full bath for bedroom 2 and bonus room. Finished room and full bath in walk out basement with full egress door no bulkhead, plus storage area. Third floor walk up also has an area for storage or future finished space. House is on a dead end street close to center of town! Home are less than 5 miles to RT495, making it a great commuter location. Less than a 1/2 mile to boat ramp on Pratt Pond and 1 mile to Kiwanis Beach on Pratt Pond where you can enjoy swimming, boating and fishing. It truly is the perfect location!

27 James Road Unit 4, Upton

$910,000

4 Beds ⋅ 3 Baths ⋅ SOLD Status ⋅ 73525258 MLS ⋅ 3,956 SqFt.

Prepare to be enchanted by this stunning, perfectly designed home. One level living at its finest. Crafted with the utmost precision and meticulous design. Every inch of the home was carefully thought of – from a perfectly situated mudroom, to a seamlessly flowing open concept living area, four generously sized bedrooms, a large study, a wonderful oversized four-season porch and an outdoor patio. The finest materials & finishes enhance every element of this home. Beautiful engineered wood floors throughout. Sophisticated designer kitchen, complete with an oversized island, quartz countertops, and top of the line stainless steel appliances. The primary suite offers expansive walk-in closets with an en-suite bath. This exceptional property is nestled in beautiful grounds on a 5.5 acre lot. Deadline for offers is 5:00 pm Tuesday, June 16, 2026. Please make offers good for 24 hours.

145 W River Street, Upton

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