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$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 ACTIVE 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

$699,900
2 Beds 3 Baths ACTIVE Status 73524427 MLS 1,950 SqFt.
Enjoy low-maintenance living at Upton Ridge, a desirable 55+ community just a short stroll from the renowned Shining Rock Golf Course. This beautiful Milan-style two-story home offers a spacious, thoughtfully designed floor plan featuring a first-floor primary suite and open-concept living. The oversized kitchen is perfect for entertaining, complete with upgraded cabinetry, quartz countertops, and a large center island. The light-filled gathering room opens through a slider to the rear deck, with remote controlled awning, creating a seamless indoor-outdoor space to relax and enjoy the peaceful surroundings. Upstairs, you’ll find a spacious loft, a generously sized second bedroom with a full bath and walk-in closet. Experience the beauty and tranquility of Upton Ridge while enjoying convenient access to Boston, Providence, New Hampshire, Route 9, I-90, I-495, and the commuter rail.

87 Shannon Way Unit 86, Upton

$850,000
3 Beds 3 Baths SOLD Status 73524039 MLS 2,568 SqFt.
Set on nearly an acre in a sought-after Upton neighborhood, this stately Colonial offers timeless appeal and thoughtful updates throughout. Major recent improvements include a renovated kitchen with creamy white cabinetry, farmhouse hardware, quartz countertops, and LG appliances, Buderus boiler, Heat Flo water tank, Roth oil tank, Carrier A/C system, energy-efficient windows, garage doors, bulkhead and newly paved expanded driveway. The spacious primary suite offers an en-suite bath, walk-in California Closet & new hardwood flooring plus 2 additional generous bedrooms. The finished lower level provides flexible space for home offices, guests or recreation, plus abundant storage. Outside, enjoy a beautifully landscaped multi-tiered backyard with a beautiful heated Gunite pool, 2 new generator ready propane tanks, a relaxing 3 season porch and low-maintenance grounds. Convenient access to Route 495 and Mass Pike for commuting to Boston, Worcester and Providence.This home is turnkey.

3 Jonathans Way, Upton

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

52 Elm St, Upton

$1,075,000
4 Beds 3 Baths ACTIVE Status 73522448 MLS 2,924 SqFt.
32 Mendon St, Upton, MA. Where modern sophistication meets timeless design. This newly constructed 2026 residence offers 2,924 square feet of impeccably curated living space, blending contemporary elegance with refined modern farmhouse architecture. Every detail has been intentionally selected — from premium finishes to elevated craftsmanship — creating a home that feels both luxurious and enduring. Designed for elevated living, the expansive floor plan features 4 spacious bedrooms, 2 full baths, and 1 half bath, seamlessly balancing comfort and style. The two-car garage adds convenience, while the gracious front porch delivers a distinguished first impression. Generously sized basement with full build-out opportunity. Set on a property with exceptional outdoor potential, this residence presents a rare opportunity to own a home defined by quality, sophistication, and architectural presence.

32 Mendon St, Upton

$765,000
3 Beds 3 Baths SOLD Status 73522253 MLS 2,627 SqFt.
COMFORT MEETS COUNTRY SERENITY! Tucked away on a peaceful country road with 2+ acres of wooded privacy, this home suits all lifestyles. A true open-concept 1st floor creates a seamless flow. The remodeled kitchen has quartz countertops, white cabinetry and a 4-top seating island with a built-in bookshelf. Hardwood floors carry through to the dining room and bright living room, anchored by a 2-sided gas fireplace that opens to a stunning sunroom. Practicality meets luxury with a farmhouse powder room and a remodeled guest bath that compliments the prevalent modern flair. “Romeo, oh Romeo” – fall in LOVE with the private balcony in the primary bedroom, complete with the vaulted ceilings and skylights. Every level feels move-in ready with NEW carpet and fresh paint (various). Outside is your oasis: inground pool, a screened-in TREK porch, firepit and wood deck. With energy-efficient mini-splits and a finished walkout family room, this home is as smart as it is beautiful!

24 Fowler Street, Upton

$1,125,000
4 Beds 4 Baths CONTINGENT 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

$1,699,000
8 Beds 6 Baths EXTENDED Status 73520686 MLS 6,850 SqFt.
ABSOLUTELY STUNNING. Enormous 8 Bedroom Home with over 6000 square feet of living on 5.5 acres bordering the Shining Rock Golf Course. Privacy abounds on this special property that has been completely updated. Septic System, Roof, Heat/AC, Kitchen, 6 Bathrooms, Windows, Flooring, Well....All NEW. First floor has kitchen, dining room, TWO front to back family/living rooms, full bath, pantry and an office. Second floor has primary bedroom, with a gorgeous bathroom complete w/ a soaking tub, a changing room and his and her walk in closets. Laundry room, another 2 full bathrooms and 3 additional bedrooms round out the second floor. 3rd floor has a full bath and four bedrooms. Basement is finished w/ numerous rooms including a full bath. Outside there's a large inground pool with decorative water feature, patios, and all sorts of plantings surrounded by a huge yard and acres of forest. Unique is a understatement. You've got to see it to believe it.

175 Pleasant St, Upton

$1,050,000
3 Beds 3 Baths SOLD Status 73519143 MLS 3,237 SqFt.
Magnificent and truly one-of-a-kind, this privately set Mid-Atlantic–style custom estate spans 5+ acres of landscaped grounds, featuring perennial gardens, mature plantings, and handcrafted stone walls. Meticulously maintained with a new septic system and water filtration, the home blends timeless elegance with modern updates. The fireplaced kitchen offers granite countertops, a custom wood island, and sunlit dining area, while the formal dining room features its own fireplace and bespoke built-ins. A dramatic living room with cathedral ceilings and a striking floor-to-ceiling window fills the home with natural light. The grand staircase leads to a luxurious primary suite with fireplace and spa-like bath with double vanity, granite, custom tile shower, and jacuzzi. Complementing the main residence is a 964 sq ft carriage house with kitchen, 1.5 baths, and flexible space. Resort-like grounds include a deck, in-ground pool, outdoor fireplace, gazebo, and shed. a rare, private retreat.

179 South St, Upton

$800,000
3 Beds 4 Baths SOLD Status 73518665 MLS 2,000 SqFt.
Custom-built expanded cape privately set on an acre-plus lot overlooking picturesque Mill Pond. This unique property offers exceptional space, flexibility, and endless potential. The updated open-concept kitchen with beamed ceilings flows into a cozy dining area with pellet stove, followed by a dramatic lodge-style living room featuring a stunning floor-to-ceiling stone fireplace. Sliders lead to a wraparound deck and peaceful outdoor space, perfect for entertaining and relaxing. The primary suite offers a private bath, beamed ceilings, while two additional oversized bedrooms feature large walk-in closets. Bright 700+sq ft direct outdoor access LL, includes a summer kitchen, media room, full bath, family room, and flexible exercise /play space not inc. in GLA. Approx. 2000 sq ft unfinished addition offers expansion or in-law potential. Close to Routes 495 & 140, on-site access to kayaking, canoeing and fishing, oversized two car garage, great storage, this property has it all!

9 River St, Upton

$1,100,000
4 Beds 4 Baths SOLD 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

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