Hopkinton MA 5 Bedroom Real Estate, Homes, Condos for Sale

Welcome home to this exclusive property where charm, character & major updates come together beautifully on 1.4 acres! This 5-bedroom home offers 3 fireplaces, sunroom with sliders and skylights, formal dining room & warm family room with exquisite brick and beam highlights. This flexible floor plan with a first-floor spa inspired primary suite offers a gas fireplace, large walk-in closet & thoughtfully renovated bathroom featuring updated lighting, faucets, hardware, jetted tub & skylights. The bright kitchen extends to the outside with 2 sliders to your private 2 tiered oversized solid deck! Three generously sized bedrooms with luxury plank flooring (no carpet) are located on the second level, along with 2 versatile loft spaces, a private office & balcony overlooking the family room & brick fireplace. The exposed railing & open staircase to the lower level enhance the home's open flow & distinctive character. A true standout is the full walkout lower level, offering its own guest quarters with luxury plank flooring thruout an oversized bedroom, full bathroom, wet bar, gameroom & wood-burning brick fireplace—ideal for guests, extended family, au pair or additional living space. The fully fenced-in backyard is magical with perennial gardens, rock walls, sweeping trees and a variety of 4 season foliage. From the covered front porch, stone walkways, perennial gardens, 2-tiered back deck to the inviting interior, soaring cathedral ceilings, exposed beams, hardwood floors, exposed brick & 3 fireplaces, this home exudes warmth & architectural appeal, while skylights, new lighting & fresh paint throughout bring an additional bright, updated feel. Major improvements include 5 bedroom septic system, new heating & AC system (2024), hot water heater (2025), new water filtration system (2025), luxury plank flooring (2025), roof (2011), driveway & stone walkways (2022), front & back decks (2021) & vinyl siding (2008). Custom blinds & plantation shutters add a polished finishing touch. Conveniently located near Valleywood Estates, Hopkinton Trails, Lake Whitehall, Lake Maspenock, tow beach, shopping, town amenities & major commuter routes Rte 495/Rte9/Mass Pike. Top ranked schools!

7 Pond St, Hopkinton

$1,449,900

5 Beds ⋅ 4 Baths ⋅ 73563646 MLS

Welcome to 176 Spring Street, a home where nearly every space has been thoughtfully improved with an incredible list of updates inside and out. At the heart of the home is the beautiful kitchen, centered around a large island and fireplace with Wolf gas range, Sub-Zero refrigeration, Miele appliances and soapstone countertops. The island features 4 pull out beverage or snack refrigerator drawers. A generous eat-in area offers plenty of room to gather, with a separate formal dining room just off the kitchen.The bright living room opens through sliders to the deck, while an adjoining flex room—currently used as a fifth bedroom—works beautifully as an office, playroom or guest space. Upstairs, the completely remodeled primary suite is a standout, featuring a stunning new bath and expansive walk-in closet. 2 additional bedrooms and a remodel full bathroom complete the second floor. The third floor offers exceptional versatility with the fourth bedroom, its own living area and private full bath. The expansive basement adds another dimension to the home, with abundant space, an impressive organized workshop with outdoor access, added cabinetry, new recessed lighting and a mini split for year-round comfort.The improvements extend far beyond what you see: brand-new HVAC and water heater, new attic heating and cooling with full insulation, new gutters, six replacement windows, updated plumbing for water filtration, new recessed and exterior lighting, Cat 6 internet wiring, and a whole-home generator. Even the garage has been transformed with epoxy flooring, Trex steps, wall storage and an EV charger. Set on 4.11 private acres of professionally landscaped living areas with approximately two acres of usable yard plus wooded acreage and ATV trails, the property offers space, privacy and nature. From major systems to beautiful living spaces and thoughtful functional upgrades, the owners have truly left no stone unturned. First floor has a full bath and a guest room

176 Spring St, Hopkinton

$1,750,000

5 Beds ⋅ 4 Baths ⋅ 73562644 MLS

Gorgeous curb appeal on this elegant 5 Bedroom Colonial constructed by one of Hopkinton’s finest builders, Hallmark Construction, nestled on 1.21 acres and sited on a cul-de-sac with a private backyard oasis complete with a heated inground pool abutting acres of conservation land! This bright and airy home offers a fantastic open floor plan with a two-story Foyer, 1st Floor Office, Front-to-Back Living Room/Dining Room, expansive Kitchen with extensive cabinetry with a casual dining area leading to a stunning two story fireplaced Family Room with windows galore and back staircase! Built-ins and moldings throughout. Pretty Half Bath with pedestal, crown molding and granite floor. Ideal side entry Mud Room with a 2nd half Bath just for the kids! Back hall easy access to lower-level finished Playroom! Primary Suite offers spacious Bedroom with lighted trey ceiling; Full Bathroom with double vanities, tiled shower, jacuzzi, private commode, radiant heated marble floor & 2 walk-in organized closets! 4 additional secondary Bedrooms each with custom built-ins & closet. Hall Full Bath with a private commode, separate tub with pedestal sink and a separate shower with pedestal sink. Finished lower-level carpeted Playroom with rough plumbing for a future Bathroom. Large unfihished storage space with walkout. Mature, well-landscaped expansive grounds with sprinkler system. Quick easy access to sought after highly ranked public schools, downtown & train station!

5 Wellington Way, Hopkinton

$635,000

5 Beds ⋅ 3 Baths ⋅ 73559824 MLS

Charming antique Colonial in the heart of Hopkinton! This well-maintained single-family home offers 4–5 bedrooms and 2.5 baths, blending classic character with modern updates. Ideally located just steps from the historic Boston Marathon starting line and Hopkinton Town Common. Enjoy walking distance to schools, restaurants, coffee shops, library, farmers market, and downtown amenities. Situated on a quiet side street with a spacious yard, this home also offers easy access to Routes 495 and the Mass Pike, plus convenient commuter rail access via Southborough and Ashland stations. A rare opportunity to own a centrally located home with charm, space, and convenience.

8 Pike St, Hopkinton

$1,550,000

5 Beds ⋅ 5 Baths ⋅ 73549488 MLS

Fall in love with this Queen Anne elegance that new construction simply cannot match! Nestled in a premier Hopkinton neighborhood with award-winning schools, this architectural masterpiece is the ultimate estate for luxury, entertaining and true multigenerational living. The breathtaking grand foyer welcomes you with a dramatic 3 story staircase, custom moldings, transom windows and stained glass. A sophisticated main level features a private office, formal dining, a grand family room with a marble fireplace and a luxurious first-floor primary suite. The designer kitchen and 4-season sunroom flow effortlessly to an upper deck overlooking a private backyard oasis. Need space for extended family or a premium home business? The finished walk-out lower level is a complete second dwelling, boasting a full kitchen with double ovens/gas cooktop, family room, sunroom, full bath and laundry. Roof 2010 w 30 yr shingles.

2 Country Way, Hopkinton

$1,999,800

5 Beds ⋅ 4 Baths ⋅ 73544458 MLS

New construction in the heart of downtown! Bring your vision to life w this stunning, modern Colonial, to be built, featuring 4-5 beds, 3.5+ baths across ~4,800 sq. ft. of meticulously planned, customizable space. The versatile floor plan can be tailored to your preferred size and lifestyle, offering options for 1st-floor bedroom suite or a home/business office w separate entry, mudroom, a chef’s dream kitchen w walk-in pantry, expansive family room & elegant dining room. Upstairs, 4 huge bedrooms w hardwood floors. Primary en suite w dual walk-ins. Options for finished basement w bed/ bath, perfect for entertainment & guests. Conceptual renderings allow you to visualize optional high-end finishes & flow of this dream home before construction even begins! Situated on flat & private 0.67-acre lot close to top-rated schools, shops & restaurants. The front of the home beautifully faces Maple Street Ext & offers unique ADU potential w 2 driveways & 2+ car garage.

9 Montana Road, Hopkinton

$2,599,900

5 Beds ⋅ 5 Baths ⋅ 73542699 MLS

Master craftsman Brian Gassett has done what few people could do. While maintaining the original historic 1790 colonial home, he has brought it up to the highest 2026 standards while being faithfull to the architectural style of the home. Filled with daylight this 4422 sq ft home has first and second floor primary BR’s. 5 BR total each with walk in closet and 4 full baths. A gorgeous kitchen suitable for entertaining and some serious cooking. FR open to patio and 3 season sun room, DR, pantry, and much more. A stone’s throw from the historic town common this lot is level and totally useable. Ample 3 car garage. Accompanied showings only. Some exterior photos of the lawn have been digitally enhanced. For more photos please go to https://drive.google.com/drive/folders/1bmm7xamJG-ronPTWwdy2KmVd33hTld_T?usp=drive_link

27 Ash St, Hopkinton

$1,495,000

5 Beds ⋅ 3 Baths ⋅ 73541688 MLS

An exceptional opportunity to own a beautifully sited waterfront property in one of Hopkinton's most desirable neighborhoods. Nestled on a picturesque pond and surrounded by mature landscaping, 28 South Mill Street offers a rare combination of privacy, natural beauty, and convenience. Pride of ownership is evident throughout the property, with extensive renovations and improvements made over the years that have enhanced both its functionality and long-term appeal. The home's striking exterior presence is complemented by outdoor spaces designed to take full advantage of the serene water views. Enjoy morning coffee overlooking the pond, entertain guests outdoors, or simply appreciate the changing seasons from this special setting. Featuring owned solar panels for long-term energy savings and sustainability, the property is also located near top-rated schools, shopping, dining, recreation, and major commuting routes.

28 S Mill St, Hopkinton

$1,589,000

5 Beds ⋅ 4 Baths ⋅ 73538849 MLS

Exquisite Colonial in Hopkinton’s Forestside neighborhood. This 5-bed, 4-bath beauty sits on a level lot with a circular driveway & mature landscaping. Hardwoods flow through the first level, connecting an open eat-in kitchen, spacious family room, and formal living & dining areas. Need quiet? There’s also a private office. Two fireplaces add warmth, and a rear staircase leads to a bonus room over garage perfect for a game room or home office retreat. Upstairs, a primary suite is your sanctuary, featuring a walk-in closet & a luxurious skylighted, cathedral bath. Two more beds, a quiet study, & full bath complete the second floor. The third floor offers incredible flexibility: two bedrooms, study area, & full bath—ideal for teens, guests, or an au pair. Below, a massive lower level offers 600 sq ft of potential for a gym or media room. Step outside on to a huge new deck & 3 season porch overlooking a flat, manicured backyard. Minutes to 495 & the Pike. Move-in ready luxury awaits you.

4 David Joseph Rd, Hopkinton

$2,550,000

5 Beds ⋅ 6 Baths ⋅ 73531001 MLS

Experience the pinnacle of luxury in this stunning, high-performance custom-built home featuring 7,802 finished square feet of living space, grand-sized rooms, and a spectacular, unique floor plan situated at the end of a private cul-de-sac. This rare offering presents a special opportunity to customize your dream home and add your personal touches—including custom appliance selections—using the builder's generous allowances. Engineered for superior efficiency, low maintenance, and high quality, the home is equipped with a rare and highly sought-after NATURAL GAS heating system alongside an exceptionally tight envelope insulation package, supreme HERS score, ERV fresh air system with 4" HEPA filters, and a balanced Make-Up Air system for ultimate climate control. Set on a bright and sunny lot surrounded by serene open space at the end of a private cul-de-sac, you are just minutes from the commuter rail, Hopkinton State Park, and top-rated schools—all just 26 miles from Boston. The heart of the home is a custom chef's kitchen complete with a separate pantry, handmade cabinetry, double wall ovens, an elegant octagonal breakfast room, and space for a professional 48" natural gas range and 36" French door refrigerator. The open-concept family room showcases classic design elements like white oak wood flooring, a stone fireplace mantel, deck access, and a wet bar with a paneled beverage fridge. With 5 oversized bedrooms, 5.5 designer baths, a giant primary suite with double closets and a spa-like bath, and a sprawling finished WALKOUT basement, there is incredible room for everyone. Enjoy a bright setting with direct access to 10 acres of protected Sudbury River trails in this extraordinary value for discerning luxury buyers. Open Houses: Sat., 8/22 from 11-1 and Thu., 8/27 from 4:30-6:30.

Lot 6 Lincoln Street, Hopkinton

$2,000,000

5 Beds ⋅ 5 Baths ⋅ 73517327 MLS

Exceptional 2023 built ready for pool in Edgewood of Hopkinton, offering 5 bedrooms, 4.5 baths & over $150K curated upgrades. Charming, covered porch welcomes you into dramatic two-story foyer flanked by elegant sun-filled living & dining rooms. Breathtaking two-story great room opens to chef’s kitchen showcases custom white cabinetry, quartz counters, oversized breakfast bar, 6-burner gas cooking, designer backsplash, walk-in pantry, mudroom & office nook. Opens to Trex deck, patio & private backyard retreat. 1st fl guest suite w walk-in closet & adjacent bath offers flexibility for guests/ multi-gen living. Luxe primary suite w sitting room, office, 2 walk-in closets & spa bath w soaking tub, dual vanities & oversized shower. Three more bedroom/bath en suites. ~1500 sqft in lower level can be finished for ~$75K w full bath. Solar panels, EV charger, smart home tech, gas lines for grill/firepit, custom closets & more. Home is next to trail to schools! Quick to commuter rails & 90/495.

60 Chamberlain Street, Hopkinton

$3,350,000

5 Beds ⋅ 8 Baths ⋅ 73510972 MLS

Experience unparalleled architectural grandeur in this majestic Cranberry Cove residence w deeded access to Lake Whitehall. Hallmark-built home showcases intricate craftsmanship, blending European refinement, grand-scale entertaining & everyday comfort. Transport yourself to Italy in the Tuscan gourmet kitchen, host in the tasting room & wine cellar, enjoy billiards, or relax in the award-winning media room & library. Retreat to a palatial primary suite w fireplace, balcony views & Roman spa-inspired bath. Five additional luxurious ensuites. Guests/in-laws enjoy a bedroom en suite w kitchen, family room & sauna. Outdoor sanctuary features kitchen, heated saltwater pool, hot tub, surrounded by elegant gardens. Modern luxuries include radiant floors, smart systems, 4-car heated garage & EV charger. Near top Hopkinton schools as well as renown St. Mark’s, Fay Schools & quick access to Boston & airport via 495/90 in under 45 min. A rare combination of luxury, community & convenience await!

9 Wescott Drive, Hopkinton

$2,499,000

5 Beds ⋅ 3 Baths ⋅ 1408974 MLS

Escape to your own New England sanctuary! Rarely does a property of this scale and caliber hit the market. Currently one of only ten homes listed with over 25 acres, this stunning 70-acre estate ranks as the third-largest parcel available. From the classic red barn to the sweeping hilltop views, this is the ultimate "Gentlemen's Farm" or add some fencing for an equestrian dream. PROPERTY HIGHLIGHTS: The Land: 70 pristine acres featuring open pastures, historic stone walls, and total privacy. The Main House: 5 spacious bedrooms in an immaculate, light-filled layout designed for classic New England living. The Arrival: A tree-lined driveway leads you past lower fields to a beautiful circular drive with a mature center apple tree. Bonus Spaces: A detached 2-car garage featuring a dedicated yoga/hobby studio and a private 1-bed/1-bath guest suite above. Outdoor Living: Relax by the in-ground pool overlooking the upper pastures and wooded hills. Location: Complete seclusion and peace, yet just a short drive to I-95 for easy commuting. A little bit of polish will make this gem shine. Interior pics to follow. Currently in Farms Forest and Open Space program for taxes purposes. SEE THE VIRTUAL TOUR: Experience it! See the wooded trails. #RealEstate #NewEnglandLiving #LuxuryListing #Farmhouse #HorseProperty #HomeTour #DreamHome

58 Dye Hill Road, Hopkinton

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