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$1,159,000
4 Beds 3 Baths ACTIVE 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

$899,900
4 Beds 3 Baths ACTIVE Status 73551967 MLS 2,806 SqFt.
Tucked away on a quiet cul-de-sac with 2 acres of wooded bliss, this Federal-front Colonial is pure serenity with an incredibly spacious layout to boot. It's 3000+ square feet that feels warm and homey with New England charm oozing from every room. The kitchen has NEW quartz countertops and a massive eat-in area with a downdraft gas stove. It flows seamlessly into a sun-drenched family room with exposed beams, NEW skylights and a NEW ceiling fan. A second living space, formal dining, and powder room round out the main floor. Upstairs, the primary suite boasts a beautiful NEW bathroom and three spacious bedrooms. Outside, a NEW composite deck overlooks a massive backyard where you can grow your own fruit! You'll love the established pear and cherry trees, blueberry bushes, plus there’s a fenced garden area ready for someone with a green thumb. Additional UPDATES include vinyl siding, front steps, garage doors and the finished lower level. Opportunity is knocking—don’t wait to answer!!

10 Sadler Road, Upton

$989,900
4 Beds 4 Baths ACTIVE Status 73547396 MLS 2,990 SqFt.
UNDER CONSTRUCTION...Enjoy The Benefits of New Construction with Energy Efficiency & Low Future Maintenance! This stunning home offers the perfect blend of classic elegance and modern convenience with a spacious 1st FLOOR PRIMARY SUITE and laundry and 3 additional bedrooms on the 2nd level. The partially finished basement with finished half bath provides extra square footage plus access to the spacious backyard. Every detail has been carefully selected to provide style and functionality. 1ST floor hardwoods, Quartz countertops and GE Cafe appliances are just a few of the upgraded details that make this home full of beauty and comfort. The composite decking provides a low-maintenance space for relaxing or entertaining. Located in close proximity to Route 495 and train stations, providing easy access to commuting routes and conveniences. This home is a must-see for anyone seeking modern living in a peaceful, well-connected location! Scheduled for Sept 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 September 2026 Closing.

17 West Main Street, Upton

$789,900
4 Beds 3 Baths CONTINGENT 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

$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

$1,125,000
4 Beds 4 Baths ACTIVE Status 73541292 MLS 4,054 SqFt.
Glen Echo is a most desirable neighborhood close to Rt 495, MA Pike & Westborough. This pristine & spacious 4 bedroom, 3.5 bath Chatsworth Model Colonial has been impeccably maintained by its original owners. Enter to dramatic 2 story foyer w/ wainscoting & balcony. Open floor plan, 9 ft ceilings & tons of windows give this home an airy & roomy feel. Main level boasts hardwoods throughout. Gourmet eat-in kitchen is a cook's dream - granite, SS appliances, dbl oven, vented out hood vent, walk-in pantry, expansive island, butler's nook, desk area & sliders to composite deck overlooking private yard w/ woodland views. Spacious family room w/ FP. Large office w/ French doors, living room, dining room & laundry/mud room complete 1st floor. Added convenience - a 2nd staircase. Spectacular Primary Suite w/ sitting area, gorgeous bath, jetted tub & updated tiled shower. Jack & Jill bath connects two good size bedrooms. 3rd full bath in 4th bedroom. ~2000 sq ft unfinished basement w/ sliders.

35 Howarth Dr, Upton

$1,300,000
4 Beds 3 Baths UNDER AGREEMENT 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

$919,900
4 Beds 3 Baths UNDER AGREEMENT 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

$699,000
4 Beds 3 Baths ACTIVE Status 73523806 MLS 2,835 SqFt.
Tucked along a scenic country road, this beautifully preserved early 18th-century Gambrel blends timeless New England character with the comfort and updates today’s buyers seek. Rich with historic charm, the rambling floor plan offers warm, inviting spaces including a stunning 1st-floor primary suite, great room, library/den, front-to-back living room, classic keeping room with stone fireplace, cozy natural wood kitchen, and countless nooks and period details throughout. Three fireplaces add warmth and ambiance. Outside, enjoy a storybook setting with mature trees, flowering shrubs, open lawn, meadow, tranquil pond, and iconic stone walls. Detached 2-car garage with loft and natural light offers endless possibilities. Recent updates include restored mid-1800s windows with storm windows, central air, metal roof, renovated 2nd-floor bath, fresh exterior paint, regraded driveway with cobblestone pavers, and stunning patio with reclaimed brick from Worcester with stone walkway.

52 Elm St, Upton

$1,100,000
4 Beds 3 Baths ACTIVE Status 73522448 MLS 2,924 SqFt.
32 Mendon St, Upton, MA. Where modern sophistication meets timeless design. This newly constructed 2026 residence offers 2,924 square feet of impeccably curated living space, blending contemporary elegance with refined modern farmhouse architecture. Every detail has been intentionally selected — from premium finishes to elevated craftsmanship — creating a home that feels both luxurious and enduring. Designed for elevated living, the expansive floor plan features 4 spacious bedrooms, 2 full baths, and 1 half bath, seamlessly balancing comfort and style. The two-car garage adds convenience, while the gracious front porch delivers a distinguished first impression. Generously sized basement with full build-out opportunity. Set on a property with exceptional outdoor potential, this residence presents a rare opportunity to own a home defined by quality, sophistication, and architectural presence.

32 Mendon St, Upton

$1,150,000
4 Beds 4 Baths ACTIVE Status 73521066 MLS 3,402 SqFt.
30 Mendon St, Upton, MA Experience modern luxury in this newly constructed 2026 single-family home over 3,000 square feet of thoughtfully designed living space. Blending timeless elegance with contemporary comfort, this exceptional residence is crafted for today’s lifestyle. Featuring four spacious bedrooms and four full bathrooms, the home provides both privacy and convenience with high-end finishes throughout. The open and inviting layout is ideal for both everyday living and entertaining. A two-car built-in garage offers secure parking and additional storage, while the welcoming front porch adds charm and curb appeal to this stunning new construction. Located in desirable Upton, this home presents a rare opportunity to own a beautifully designed residence in impeccable condition.

30 Mendon St, Upton

$675,000
4 Beds 3 Baths ACTIVE Status 73518303 MLS 2,548 SqFt.
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

$1,095,000
4 Beds 4 Baths UNDER AGREEMENT Status 73516986 MLS 3,768 SqFt.
OPEN HOUSE CANCELLED. Stunning move-in ready home in highly desirable Glen Echo Estates near the Upton/Westborough line! This beautifully designed property offers sun-drenched living spaces, hardwood flooring & an open-concept layout perfect for today’s lifestyle. Dramatic two-story foyer, elegant dining room, private home office & an inviting family room with wood-burning fireplace create exceptional living spaces throughout. The chef’s kitchen features exotic quartzite countertops, stainless steel appliances, oversized island & flows seamlessly into a bright sunroom ideal for entertaining. Luxurious primary suite with tray ceiling, spa-like bath & walk-in closet. Flexible bonus space perfect for media room, gym or potential 5th bedroom. Expansive deck overlooks a peaceful wooded backyard offering privacy & relaxation. Walkout basement, 3-car garage & convenient commuter location with easy access to major routes complete this exceptional offering.

11 Howarth Drive, Upton

$765,000
4 Beds 3 Baths UNDER AGREEMENT Status 73500985 MLS 3,018 SqFt.
Welcome home to this distinctive four-bedroom property set on a picturesque 1.84-acre lot, offering the perfect blend of charm, space, and modern updates. Enjoy peaceful mornings on the inviting farmer’s porch or unwind on the stunning new patio while taking in beautiful sunset views. Inside, this home is anything but ordinary, featuring hardwood floors, a flexible first-floor bedroom, and a dramatic second-floor fireplaced family room that adds warmth and character. The expansive primary suite serves as a private retreat with an ensuite bath, bonus space for a reading nook or exercise area, and access to a walk-up attic with future potential. Numerous major updates—including heating system, roof, windows, oil tank, hot water heater, fresh paint, carpets, slider, and new D-box—provide true move-in readiness. Additional highlights include a finished lower-level room ideal for a gym or hobby space. Located in desirable Upton with top-rated schools and easy access to major routes.

1 South St, Upton

$1,225,000
4 Beds 6 Baths ACTIVE Status 73498932 MLS 5,736 SqFt.
With a flexible layout that supports multigenerational living, this gorgeous custom-built colonial has ample space and is situated on 3+ private acres. From the moment you step into the grand two-story foyer adorned w/ granite flooring, you’ll be captivated by the attention to detail & luxurious features throughout, incl 9ft+ ceilings & gleaming hardwoods. Spacious fam rm is a true showpiece w/ stunning floor-to-ceiling stone fireplace & interior balcony. The expansive gourmet kitchen boasts a huge island w/ vegetable sink, abundant counter space, cabinetry & gas cooktop. An inviting eat-in area is bathed in natural light w/numerous windows. 1st floor, open concept guest suite w/ full bath & exterior access. Upstairs, spacious primary suite w/ lg walk-in closet & spa-like bath w/ jetted tub & tiled shower w/glass door. 3 addt'l good-sized bedrooms, 2 full baths & convenient 2nd flr laundry. Finished walkout lower level has food prep area and full bath. Perfect home for entertaining!

12 Breton Road, Upton

$439,000
4 Beds 2 Baths UNDER AGREEMENT Status 73494800 MLS 2,110 SqFt.
Antique Greek Revival single-family home in the heart of Upton’s historic district. The Thomas McFarland House (1810) is set on the right side of a 1.14-acre lot that slopes down to scenic Mill Pond. Offering four bedrooms, two full baths, 2100 sq ft living space and a two-car garage.  The home is rich in character but does require significant renovation. Features include, abundant natural light, an antique fireplace, wide plank flooring, ample attic storage, and pond views from all rear-facing windows. Gas cooking and gas furnace (2009) Partitioned basement, one with walk-out access. With 265’ of street frontage, the expansive lot presents unique development potential, buyers to do their own due diligence. House is serviced by Town Water & Sewer and Natural Gas. This property is ideal for buyers seeking a rewarding restoration project in an idyllic setting. Great commuter location with quick and easy access to 495 and the Mass Pike. Showings by appointment only.

17 N Main St, Upton

$1,100,000
4 Beds 4 Baths ACTIVE Status 73490363 MLS 3,487 SqFt.
This beautifully designed custom home offers the perfect blend of privacy, space, and modern functionality. Set back from the street and positioned on an elevated lot, the home delivers both curb appeal and a sense of seclusion. Inside, you’ll find a thoughtfully designed floor plan featuring 4 spacious bedrooms and 3.5 bathrooms. The heart of the home is ideal for both everyday living and entertaining, with open, flowing spaces and quality craftsmanship throughout. Upstairs, convenience meets luxury with a dedicated second-floor laundry room—perfectly located near all bedrooms. The oversized primary suite serves as a true retreat, offering generous proportions, ample closet space, and a private en-suite bath designed for comfort and relaxation. With its custom layout, elevated setting, and attention to detail, this home is a standout opportunity for buyers seeking both style and functionality in a serene setting.

99 W River St, Upton

$499,000
4 Beds 3 Baths ACTIVE Status 73487287 MLS 2,228 SqFt.
Back on market due to buyer's home sale contingency and priced to sell! A rare opportunity to own a four-bedroom, two and a half bath residence in the desirable Samreen Villas. This private end unit offers exceptional natural light and a thoughtfully designed layout ideal for both everyday living and entertaining. The main level features hardwood and ceramic tile flooring, an open-concept kitchen and dining area, and a dramatic living room with soaring ceilings and an oversized window that fills the space with natural light. A convenient half bath completes the first floor. Upstairs you’ll find three generously sized bedrooms that share a full bath, along with a spacious primary suite featuring a vaulted ceiling and private en-suite bath. Laundry is conveniently located on the second floor. The lower level offers additional flexible space—perfect for a home office or playroom. A wonderful combination of privacy, space, and functionality in a highly desirable community.

1 Knowlton Circle Unit 1, Upton

$1,090,000
4 Beds 3 Baths UNDER AGREEMENT Status 73428709 MLS 3,260 SqFt.
Where Luxury Meets Country! Welcome to this beautifully updated 4BR, 3,000+ sq ft home in scenic Upton. Perfect for entertaining with spacious foyer, formal dining & sitting room, plus expansive family room off the remodeled gourmet kitchen with quartz countertops, stainless steel appliances, double oven, compactor & decorative cabinet lighting. Upstairs offers 4 bedrooms & 2 full baths incl. a primary suite with sitting area, double walk-in closets & spa-like en suite with soaking jet tub. Finished lower level is heated/cooled with bonus room, craft/workshop & mudroom with garage access. Enjoy the new front porch & composite back deck overlooking premier equestrian facilities: 2 barns with 7 stalls, 4 fenced paddocks, 90’x110’ riding ring & 50’ round pen, & tack/grain room. Energy-efficient upgrades include Tesla solar panels (owned), new hot water tank, new condenser & more. Surrounded by fruit trees & gardens, this rare horse property blends luxury living with top-notch amenities.

6 Wood St, Upton

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