Browse All Hopkinton MA Properties with Pool for Sale

Welcome home to this very well maintained & thoughtfully updated hip roof colonial in a beautiful tree lined neighborhood. This expansive & sun-filled home, reflects great pride of ownership & features a floor plan perfect for entertaining. The well appointed, eat-in kitchen, w/granite countertops, SS appliances, tons of cabinets & 2-tiered island is the heart of this beautiful home. It opens to the warm & inviting family room w/gas fireplace, floor to ceiling shelving & window seats overlooking the beautifully landscaped front yard. The formal dining room features crown molding, wainscotting & gleaming hardwoods. The welcoming living room is appointed with a gas fireplace, chair rail and oversized mantel. The oversized office features a wall of windows overlooking the mature and well cared for landscaping in the back yard. The 2nd floor features a spacious primary suite w/fireplace, custom designed walk-in closet & renovated full bath. 3 nicely sized bedrooms, a renovated 2nd full bath & a sitting room round out the 2nd floor. This home is set on a spectacular private acre lot w/beautiful landscaping, trex deck, patio, outdoor shower & in-ground pool - with newer liner, water heater & pump. Recent updates include new carpet, refinished hardwoods, interior paint & updated lighting. This well loved & desired neighborhood is located near top-rated schools, shopping, dining, recreation, and major commuting routes. This home is truly one of a kind.

11 Dicarlo Rd, Hopkinton

$1,749,000

4 Beds ⋅ 5 Baths ⋅ 73565351 MLS

Custom built by one of Hopkinton's most respected luxury builders, this extraordinary Victorian-inspired Colonial is a rare offering where exceptional craftsmanship, timeless architecture, and meticulous care come together. Purchased directly from the builder by the current original owners, the home has been lovingly maintained and thoughtfully updated while preserving its character and quality. Recent improvements include a freshly painted exterior (2025), new heat pumps (2024), all-new Marvin windows and doors (2021), new kitchen appliances (2021), and a lifetime metal roof (2019). At the heart of the home is a beautifully renovated chef's kitchen featuring premium Sub-Zero double refrigerator/freezers, luxury Miele appliances, custom cabinetry, and views of the backyard oasis. Step outside to an expansive patio overlooking a spectacular Pebbl-Tec in-ground pool with waterfall, beautifully landscaped grounds, and a generous level lawn for play and entertaining. The first floor offers elegant yet comfortable living spaces, including a dramatic living room with soaring ceilings, formal dining room, private wood paneled study w/ private porch, inviting family room with stone fireplace, butler's pantry, laundry, and a bright kitchen designed for gathering. The finished lower level offers a home theater, full bath, sauna, home gym, and abundant recreation space. Upstairs, the luxurious primary suite is a private retreat with a spa-inspired bath, oversized walk-in closet, cedar closet and sitting room. Two additional bedrooms share a beautifully appointed bath, while the third-floor suite features a bedroom, sleeping loft, and full bath—ideal for guests, multigenerational living, or an au pair. Ideally located minutes from I-495, shopping, dining, Trader Joe's, HomeGoods, TJ Maxx, Lowe's, and everyday conveniences, this remarkable property enjoys all that Hopkinton is known for, including highly acclaimed schools, a vibrant community, and an outstanding commuter location. More than a beautiful home, this is a truly special property built to an exceptional standard and designed to be treasured for generations.

5 Queen Anne Rd, 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

$1,399,000

4 Beds ⋅ 3 Baths ⋅ 73551486 MLS

Fall in love with this meticulously maintained 4-bedroom, 3-bath home which is set in one of Hopkinton's most desirable neighborhoods. It offers the perfect blend of luxury and casual comfort with access to top-rated schools. More than $600,000 in upgrades including a 2017 furnace, an incredible 2019 walk-in dressing room and large office or bonus room. Stunning gourmet kitchen with Sub Zero fridge, Viking stove, Fisher Paykel dishwasher and a 2020 dining addition with 11' vaulted ceilings, bar area with beverage fridge. A finished basement with private entrance and man cave. Renovated bathrooms, gas fireplace, 3-season porch, two-tier composite deck, beautiful and unique in-ground pool with fire pit area and plenty of space to entertain. Other recent improvements include a new driveway, garage door, pool lighting, liner and filter system, interior and exterior painting, generator connection and roof upgrades. Too many updates to list—this exceptional home is truly move-in ready.

4 Dicarlo Rd, Hopkinton

$1,395,000

4 Beds ⋅ 3 Baths ⋅ 73550202 MLS

Welcome to the brick house on Hidden Brick Road in Hopkinton's most desired neighborhood, Ravenwood. This stunning Colonial sits on 1.39 acres of well-manicured landscape offering privacy as well as fantastic outdoor living space for entertaining friends & family. The pool area is complemented by beautiful & lush woodlands providing a natural retreat in your own backyard. Bright & airy Kitchen offers ss appliances, granite, brick detail & dining area slider to backyard deck. Huge cathedral ceiling skylit Family Room fireplace & built-ins. Playroom w/ Fr Doors & wainscoting. Front-to-back fireplaced Dining Room. Office fireplace & built-ins! Half Bath & Laundry. Hardwood floors galore! Curved Foyer stairs. Primary Suite offers balcony, 2 walk-in closets & cathedral Bath double sink vanity, tiled shower & tub! 3 good-size secondary Bedrooms. Hall Bath Shower Remodel. Lower-level Office, Bonus Room & Exercise Room. Tesla EV Outlet. Close to highly ranked schools, downtown & train station!

14 Hidden Brick Road, Hopkinton

$1,195,000

4 Beds ⋅ 4 Baths ⋅ 73544232 MLS

Tucked away on over 2 private acres of land along a quiet country road, this inviting home offers comfortable living across three finished levels. The country kitchen features a beautiful stone fireplace, quartz countertops, and a warm atmosphere perfect for casual living and entertaining. Pine floors, thoughtful updates, and a unique floor plan create a home that feels both relaxed and timeless. The first floor offers a full bath, while the finished lower level includes a media room, additional full bath, and oversized mudroom with direct access from the rare tandem 3-car garage. Upstairs, the renovated primary bath provides a private retreat, and the walk-up attic offers excellent storage or future expansion potential. Enjoy your private backyard oasis with an in-ground pool and expansive level yard. With a new 4-bedroom septic system (2020), this property offers the perfect blend of country living, modern comfort, and convenience to schools, commuter rail, and major routes.

10 N Mill St, Hopkinton

$1,699,000

6 Beds ⋅ 6 Baths ⋅ 73545245 MLS

This home truly has room for EVERYONE! Spacious yet each room has warmth and a human scale. Set on 1.65 A – has 3 tiered back yard with gorgeous pergola, deck, patio and large pool. 6 BRs 5.5 baths with first floor suite. Great Kitchen/FR for serious cooking and entertaining. Library, Office, DR, covered 3 season porch. Lower level walk out with game area, gym, private office and full bath. Close to Mill Creek Trails, great for hiking and pets. Can close as soon as you are ready – in time for school year!

31 Tammer Ln, Hopkinton

$2,025,000

4 Beds ⋅ 5 Baths ⋅ 73543624 MLS

Connelly Hill Estates! Beautiful Brick Front Colonial & 3 car garage sited on a rare, truly private, backyard oasis offering an inground Gunite heated pool, hot tub, expansive patio & stonewall surrounded by mature trees & plantings! The bright & airy open floor plan defines the home’s elegant yet comfortable atmosphere with the 2-story Family Rm, gas fireplace, built-ins, beverage fridge, wine fridge, oversized windows & split stair. Kitchen offers 2 walkout bays, lots of cabinetry, granite and ss appliances! Side entry back hall Mudroom/Laundry with chic barn door. Two 1st floor Offices with Fr Doors. Moldings & Hardwood floors galore! Primary Suite trey ceiling, lighted crown molding, walkout bay window seat, organized closets & Exercise Room. New Primary Bath double sink vanity, tiled shower, commode room, linen & tiled floor. Bedroom 2 with ensuite Bathroom. Bedroom 3 & 4 with refreshed Hall Bath. Finished lower level with Full Bath. Minutes to schools, town center & train station

3 Bowker Road, Hopkinton

$1,260,000

4 Beds ⋅ 3 Baths ⋅ 73518670 MLS

Welcome to 65 Hayden Rowe Street, a sun-drenched Victorian nestled on 1.98 acres in the heart of downtown Hopkinton. This thoughtfully updated home offers the perfect blend of character, charm and modern convenience with its stunning renovated Kitchen and Breakfast Room designed for both style and function. Kitchen leads directly to the spacious Family Room w/ woodstove and triple slider leading to expansive grounds! The 1st floor is complete with an elegant Dining room, curved archways & stairways; fireplaced Living Room; fireplaced Office w/ built-ins galore and a Half Bath. Expanded Primary Suite w/ Office, Bath tiled shower, double sink vanity, tile floor and walk-in closet. 3 Large secondary bedrooms. Hall Bath w/ two pedestal sinks, soaking tub and tiled shower. Lounge in the 3rd floor Cupola! Step outside to your private backyard oasis with Gunite pool, Carriage House, stone wall and gazebo seating areas. See Seller's Capital Improvement List, ensuring comfort & peace of mind!

65 Hayden Rowe 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

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Hopkinton Homes with Pool

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