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161 South St, Upton
$940,000
4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 73566169 MLS ⋅ 2,941 SqFt.
Price Improvement so you can be home for the holidays!! 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

5 Elm Street, Upton
$675,000
4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 73565350 MLS ⋅ 2,108 SqFt.
$20,000 PRICE IMPROVEMENT! 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

96 Fowler St, 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

2 Brookside St, Upton
$849,900
4 Beds ⋅ 3 Baths ⋅ UNDER AGREEMENT 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

66 Glenview St, Upton
$1,320,000
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

41 Rockwood Ln Unit 41, Upton
$779,900
2 Beds ⋅ 2 Baths ⋅ SOLD 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

4 Picadilly St, Upton
$480,000
3 Beds ⋅ 1 Baths ⋅ SOLD 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

24 Main St, Upton
$550,000
4 Beds ⋅ 3 Baths ⋅ UNDER AGREEMENT 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

324 Mendon Street, 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

30 Pearl St, 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

71 School St, Upton
$515,000
3 Beds ⋅ 1 Baths ⋅ SOLD 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

33 Dairy Drive, Upton
$1,100,000
4 Beds ⋅ 3 Baths ⋅ SOLD 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

78 Main Street, Upton
$677,500
6 Beds ⋅ 3 Baths ⋅ SOLD 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

10 Sadler Road, Upton
$875,000
4 Beds ⋅ 3 Baths ⋅ UNDER AGREEMENT Status ⋅ 73551967 MLS ⋅ 2,806 SqFt.
*** A NEW, NEUTRAL COLOR, COZY CARPET IS COMING THIS MONTH ** Come for the privacy, stay for the home! It’s hard to beat the setting of this expansive Federal-front Colonial. Set on 2 acres of wooded bliss at the end of a cul-de-sac, mature trees and thoughtfully designed landscaping create an incredible ambiance that will make you feel lucky to wake up to it every day. It is pure serenity with an incredibly spacious layout to boot. 3000+ square feet feels warm and homey - New England charm oozes in every room. The kitchen is HUGE and has NEW quartz countertops with a massive eat-in area that overlooks that stunning background. The first floor has a seamless flow to it with details like exposed beams, NEW skylights and a NEW ceiling fan in the family room. A second living space, formal dining and powder room round out the first floor. Upstairs, the primary suite boasts a beautiful NEW modern bathroom. Three spacious bedrooms with that NEW carpet (photos coming) and a guest bath provide space for everyone. Outside, a NEW composite deck overlooks a massive backyard where you can grow your own fruit! *chef’s kiss* You'll love the established pear and cherry trees, blueberry bushes, plus there’s a fenced garden area. Additional UPDATES include vinyl siding, front steps, garage doors and a finished lower level. Get in before the holidays and make this your home sweet home!

10 Sadler Road, Upton

19 West Main Street, Upton
$989,900
4 Beds ⋅ 4 Baths ⋅ UNDER AGREEMENT 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

17 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

218 Mechanic, 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

56 Shannon Way Unit 56, Upton
$649,000
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

117 South Street, Upton
$2,500,000
4 Beds ⋅ 5 Baths ⋅ UNDER AGREEMENT 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

90 Glenview St, Upton
$590,000
4 Beds ⋅ 2 Baths ⋅ SOLD 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

149 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

10 Hopkinton Rd, Upton
$445,000
3 Beds ⋅ 2 Baths ⋅ SOLD 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

20 Josiah Drive, 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

11 James Rd, Upton
$735,000
3 Beds ⋅ 3 Baths ⋅ SOLD 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

45 Mendon Street, 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

236 Mendon St, 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

12 Boot Shop Road Unit 12, 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

5 Boot Shop Road Unit 5, 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

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