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

An inviting rhododendron-lined drive introduces this beautifully renovated Colonial sanctuary on 1.77 acres of meticulously landscaped, park-like grounds near Lake Whitehall and scenic trails. The home and 2-story timber-frame barn offer 3 potential living spaces fearuring 5+ bedrooms, 4 full & 2 half baths across 6,225 sq ft with 4 car garage. Nestled amoung our most exclusive Cranberry Cove neighborhood, this distinctive property offers refined living and remarkable versatility. More than $550,000 invested in 3 new kitchens and 5 new baths curated by Mitchell & Company brings thoughtful design throughout. Hardwood floors and walnut accents in the kitchen and mudroom add warmth and sophistication. The main kitchen features Bosch appliances, induction cooking, and pantry. Two-sided fireplaces add character to the living and family rooms, while a first-floor bedroom suite with full bath offers flexibility for extended guests. The refreshed finished walkout lower level features new shiplap, luxury vinyl plank flooring, a Jøtul wood stove and half bath, ideal for a game room or gym. French doors open to a brick patio. A skylit screened porch with exotic hardwood decking opens to tiered bluestone patios overlooking the heated saltwater pool, with a high-efficiency pump, heat-pump heater and LED lighting. Stone walls, a poolside trellis, perennial gardens, irrigation, gardening space and a built-in trampoline create an enchanting outdoor retreat. The insulated and heated barn offers two living areas, both with stunning kitchens, dining and living rooms, sleeping areas, baths, timber-frame ceilings and mini-split heating/cooling. Potential for two accessory dwelling units for guests or rental use, subject to applicable approvals. An owned 18-kW, 75-panel solar system offers estimated annual electricity savings of about $4,200, per seller. Celect Premium siding, newer windows & roof, insulation, a high-efficiency boiler (2017), water filtration. House is wired with a 22kw Generac generator. 5-bedroom septic system. Four garage bays, including an oversized attached two-car garage and two in the barn, plus additional parking provide room for vehicles and visitors. Ask about the 5.625% interest rate for 7/1 ARM or 6.25% interest rate for 15/1 ARM (15 years fixed on 30 year loan!) Your retreat awaits!

226 Pond Street, Hopkinton

$1,950,000

5 Beds ⋅ 5 Baths ⋅ 73592625 MLS

Welcome to beautiful 26 Whalen Road, with its East facing private lot. This modern farmhouse style home has a covered front entry porch which is perfect for watching the sunrise. The open and spacious plan includes an elegant two story entry way with a first floor office with french doors to the right and a large dining area to the left which includes a lovely butler's pantry and walk in storage. The sun filled family room across the back includes a gas fireplace with tasteful mantle, a wall of soaring windows, and sliders to a large deck. There is a second office with built-in cabinetry and desk just off this family room. The kitchen is the heart of this home with its bright, white cabinets, elegant backsplash, gas range with vent, huge center island, SS appliances and a second walk in pantry. Buyers will appreciate the mudroom area with direct access to the attached three car garage. A first floor guest bedroom with full bath complete the first floor. Four additional bedrooms, each with its own bath, are on the second floor. Primary bathroom is spacious, with lavish tile shower, two vanity sinks, two walk in closets and soaking tub. There is a convenient laundry room with tile floor and sink. Plus, a second family room/loft area just off the primary bedroom! A finished lower level offers great flex space for exercise, TV, play room space. This home has all the finishing touches that make it move in ready. Closet systems, ceiling fans, whole house filtration system, irrigation system, flood lights for the rear yard, EV charger, and whole house generator. Easy out for commuting plus Hopkinton's highly rated schools!

26 Whalen Rd, Hopkinton

$1,175,000

5 Beds ⋅ 3 Baths ⋅ 73588792 MLS

Don't miss this circa 1880 single family residence with a unique business opportunity conveniently located close to downtown with approximately 4250 square feet of space on a 1/2 acre lot with a detached garage. An addition was added to the home for a hair salon and a primary suite both with bathrooms, closets and extra storage and a walk-up attic. The five bedrooms provides lots of personal space for everyone. The front porch welcomes you to the living room and the dining with tons of natural lighting. There are Anderson windows throughout. The kitchen has a commercial stove and hood, with a 12x17 dining area, pantry, and an island. The large wood deck has 2x12 framing to accommodate a hot tub. Enjoy the sunsets from your deck. In 2001 the first-floor bonus room with 567 square feet which currently is a hair salon with a nail room, color room/storage area, both with sinks, and a 3/4 bathroom. This property offers so many business options for the owner; keep it as a salon, make the area an attached ADU, offices, a multi-generational room, a catering space, perhaps a first-floor primary bedroom. The choice is yours! See document "other" regarding the zoning. The primary bedroom was also added in 2001 with oak hardwood floors and a beautiful en-suite with a large tiled shower, soaking tub, and a double vanity. It has an office and a large walk-in closet. There are stairs leading to the unfinished attic The yard has garden areas and a chicken coop that can serve as a shed. Hopkinton offers so many beautiful areas to enjoy including the Town Common, Lake Whitehall, Lake Maspenock with its town beach known as Sandy Island and the Hopkinton State Park. Enjoy the nearby walking trails! The start of the Boston Marathon is down the street at the beautiful Town Common. Hopkinton is rated as a safe community and a great school system. Quick closing possible, be in for the holidays.

12 Wood Street, Hopkinton

$2,300,000

5 Beds ⋅ 5 Baths ⋅ 73588664 MLS

Move into your beautiful new home in spring 2027! This home is framed, windows are in, roof is on! There is still time to personalize this exceptional residence by selecting some finishes and making it truly your own. Whisper Way is an exclusive enclave of just 10 bucolic homesites, thoughtfully carved into a spectacular natural landscape and surrounded by more than 200 acres of protected open space and miles of scenic walking trails. Mature trees, varying topography, and careful neighborhood planning allow each home to enjoy its own distinctive setting while blending seamlessly with the surrounding conservation land. This home offers an ideal combination of quality, luxury, comfort, and personalization, with generous finish allowances that include engineered wood flooring throughout. The thoughtfully designed floor plan features five bedrooms, four-and-a-half baths, and spacious, light-filled living areas perfectly suited for both everyday life. At the heart of the home, the sun-filled kitchen opens to a generous dining area and expansive family room, a wonderfully spacious area for entertaining. A private first-floor ensuite bedroom offers exceptional flexibility for guests, extended family, or multigenerational living. A dedicated home office provides a quiet place to work, while the oversized mudroom offers the organization and functionality today’s lifestyle demands. The second floor includes a luxurious primary suite and well-proportioned additional bedrooms, thoughtfully designed to provide comfort and privacy for everyone. Built by 20th Century Homes, a highly respected local builder with more than 40 years of experience, this home reflects a longstanding commitment to superior craftsmanship, timeless design, and attention to detail. The builder has created some of Hopkinton’s most sought-after neighborhoods, including Springwood Estates, Connelly Hill Estates, Ravenwood, Hunter’s Ridge, and other distinguished communities throughout the surrounding area. Whisper Way represents the continuation of that trusted legacy in one of Hopkinton’s most naturally beautiful settings. Enjoy the rare opportunity to customize a home tailored to your style while becoming part of an extraordinary neighborhood surrounded by nature. Only 3 homesites remain. Some details of the floor plan have been changed. Showings are accompanied, do not visit the site without an appointment.

Lot 4 3 Whisper Way, Hopkinton

$1,950,000

5 Beds ⋅ 4 Baths ⋅ 73581176 MLS

Imagine coming home this holiday season to welcome family & friends in this breathtaking residence! Distinctive luxury living in Hopkinton Highlands—exceptional spaces to entertain, unwind, and feel at home. Nestled on 1.2 acres w ability to add pool, this impeccably designed five-bedroom, 3.5 bath EAST facing, brick-front Colonial residence pairs timeless architectural appeal w beautifully updated interiors & an extraordinary collection of lifestyle amenities. 2020 gourmet eat-in kitchen features Wolf induction cooktop w a telescopic downdraft vent hood in the oversized breakfast island & flows seamlessly into an inviting family room w new plush carpet & a gas, floor-to-ceiling stone fireplace that creates a dramatic focal point for gatherings & quiet evenings alike. Refinished floors & designer lighting enhance the home’s polished presentation, while a handsome office provides an ideal setting for focused work. Retreat upstairs to the elegant primary suite, complete w its own dedicated office & new spa-inspired bathroom featuring dual vanities, standalone tub, & glass-enclosed tiled shower. Three additional generously sized bedrooms & updated full bath complete 2nd floor. Exceptional walkout lower-level transforms entertaining into an experience. Welcome guests at the wet bar, gather for billiards, or settle into the family room beneath tray ceilings accented by ambient cove lighting and a second gas fireplace. A sunny workout area brings fitness into your daily routine, while a dedicated music studio offers space to create & pursue your passions. A separate en suite bedroom provides a comfortable retreat for overnight & long stay guests. Over $400,000 of thoughtful improvements over the last decade w new kitchen & primary bath, air handlers, new 2-tier decking, paver walkway & extensive backyard patio w built-in propane firepit & stone walls accented w exterior lighting. Smart-home technology w electronics media package including wired Ethernet throughout complement the home’s modern conveniences, while the 3-car garage offers 2 EV charging stations. Professionally landscaped gardens w up-lighting & irrigation enhance the expansive grounds. PLUS newer roof, skylights & 5-bedroom septic system! Enjoy convenient access to Hopkinton State Park, Southboro Commuter rail & top schools! Call on 5.625% interest rate on 7/1 arm or 6.25% 15/1 arm on 30-year loan! The magic of the holiday season awaits you to call this home!

53 Greenwood Road, Hopkinton

$2,100,000

5 Beds ⋅ 6 Baths ⋅ 73576325 MLS

Set on nearly an acre in one of Hopkinton’s newest upscale neighborhoods, Lot 8 Emerald Drive is a home designed to be enjoyed. Picture summer evenings on the deck, coffee on the farmer’s porch and a house filled with family and friends. Inside, rich hardwood floors, custom molding and thoughtfully designed spaces create a warm yet sophisticated feel. The kitchen takes center stage with Wolf and Sub-Zero appliances, an oversized island, coffee bar and butler’s pantry, opening naturally to the family room and outdoor living beyond.A spacious first-floor suite offers wonderful versatility as a grand guest suite, playroom or luxurious in-home office. Upstairs, the impressive primary retreat is joined by 3 additional bedrooms and an open loft. The finished basement, with sliders and full-size windows overlooking the backyard, feels like an extension of the home rather than a lower level, with room for movies, games, exercise and entertaining, plus a wet bar and full bath.Outside, a generously sized deck and level backyard provide plenty of space to relax, entertain or simply enjoy the setting. For those who love the outdoors, College Rock and nearby trails offer miles of recreation practically outside your door—no need to get in the car. Yet restaurants, shopping and everyday conveniences are only minutes away. A 3-car garage and public water and sewer complete this remarkable Hopkinton home.

Lot 8 Emerald Drive, Hopkinton

$1,050,000

5 Beds ⋅ 4 Baths ⋅ 73573828 MLS

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

$1,999,800

5 Beds ⋅ 4 Baths ⋅ 73544458 MLS

***+Check out our newest 3D virtual floor plan plus a option for a two-story family room…With option to add on a grand primary suite or ADU at a later date to fit the budget!!****Call for pricing! 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. Ask about 5.625% interest rate on 7/1 arm or 6.25% interest rate on 15/1 arm, both on 30 year loan!

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

$1,450,000

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

$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

$1,899,900

5 Beds ⋅ 5 Baths ⋅ 73517327 MLS

HUGE $75K price drop!! Call on how you can save huge interest on this home with special lender financing offering 5.625% on 7/1 ARM and 6.25% interest rate on 15/1 arm for 30 year loan! 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

Call on how you can save 1.5% interest on this home with special lender financing offering 6.25% interest rate on 15/1 ARM for 30 year loan! 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 en suites. 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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