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$3,995,000
4 Beds ⋅ 8 Baths ⋅ 73527289 MLS
A private garden estate overlooking the Upton State Forest, where a winding paver driveway meanders through mature gardens before arriving at an extraordinary custom home. Created by combining three lots into one remarkable homesite, this custom-built residence offers exceptional privacy while remaining just minutes from Route 495, the Mass Pike, shopping, and dining. Nearly two years in the making, every aspect of the home was carefully planned, from its architectural details to its placement on the property to maximize views of the mature gardens and the Upton State Forest beyond. Beautifully landscaped grounds create a remarkable sense of arrival and a peaceful retreat in every season.

10 Andrea Dr, Hopkinton

Listing courtesy of Listing Agent: Stephanie Archung from Listing Office: Gibson Sotheby's International Realty.
$3,489,900
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

Listing courtesy of Listing Agent: Kim Foemmel from Listing Office: Foemmel Fine Homes.
$3,450,000
4 Beds ⋅ 3 Baths ⋅ 73467585 MLS
Prime Investment Opportunity: 20.9-Acre Private Estate in Top-Rated Hopkinton School District Nestled on an expansive 20.9-acre wooded lot bordering the Upton State Forest (one of the largest in Hopkinton), 186 Spring Street offers exceptional privacy, tucked deep in the forest with mature trees and natural seclusion. This rare parcel provides significant development potential — including the possibility of subdividing or building additional homes. Enjoy the prestigious Hopkinton Public Schools district, consistently ranked among Massachusetts' best. The charming 4-bedroom, 2.5-bath Colonial (3,014 sq ft, built 1986) features an attached 2-car garage, spacious layout, and basement for expansion. Convenient access to I-495/I-90! This property is about 2 Miles from the Lake Whitehall boat ramp and beach. Enjoy all sorts of outdoor activities nearby! Buyer to perform Due Diligence on developing the land.

186 Spring St, Hopkinton

Listing courtesy of Listing Agent: Brendon Sullivan-Monson from Listing Office: StartPoint Realty.
$2,749,900
5 Beds ⋅ 6 Baths ⋅ 73432355 MLS
Whisper Way’s signature model home! The difference is in the details! Inviting farmer’s porch welcomes you into a stunning foyer adorned w herringbone hardwood floors. Expansive chef’s kitchen, featuring top-of-the-line Wolf & Sub-Zero appliances, seamlessly flows into a sun-drenched family room w stone-clad gas fireplace. Indulge in the lavish 1,250 sq ft primary suite, complete w dual walk-in closets, posh dressing room & spa-inspired bath. First-floor bedroom suite is perfect for multigen living, while the handsome home office boasts custom built-ins. Walkout lower level is an entertainer’s dream, featuring bar, home theater, workout room & bath. Hardie cement siding, 4-car garage, Trex deck, high-efficiency gas heat & town water. Welcoming town, top schools & easy access to I90/495 & commuter rails! Private setting bordered by 200 scenic acres of conserved land w direct via Cameron Woods trail. A true custom-built sanctuary of elegance nestled in tranquility...

2 Whisper Way, Hopkinton

Listing courtesy of Listing Agent: Kim Foemmel from Listing Office: Foemmel Fine Homes.
$2,700,000
5 Beds ⋅ 6 Baths ⋅ 73531001 MLS
An absolute masterpiece of design and elite engineering by an award-winning local builder. As the crown jewel of the collection, this premier, unique floorplan is fully customizable. The high-performance, energy-efficient home features a supreme HERS score, an incredibly tight envelope insulation package, an ERV fresh air system, and a balanced Make-Up Air system. Inside, 4" white oak floors lead to a magnificent family room with coffered ceilings and a custom front-and-back kitchen boasting the Thermador Professional Collection, a 48" gas range, and handmade cabinetry. High-end, insulated Pella EnergyStar windows flood the massive 7,800+ SF layout with light, highlighting 5 bedrooms, 5.5 baths, an octagonal breakfast room, and a wet bar. The expansive finished walkout lower level is ideal for a future golf simulator or theater. Enjoy neighborhood access to 10 acres of protected Sudbury River trails. Walk to the commuter rail; 26 miles to Boston. Ask about builder incentives!

Lot 6 Lincoln Street, Hopkinton

Listing courtesy of Listing Agent: Adam Boyce from Listing Office: Mathieu Newton Sotheby's International Realty.
$2,650,000
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

Listing courtesy of Listing Agent: My House Partners Team from Listing Office: REMAX Executive Realty.
$2,550,000
4 Beds ⋅ 6 Baths ⋅ 73530998 MLS
Builder incentive through July: Choose 1 of 5 FREE builder luxury upgrade packages—Entertainment, Theater, Gym, Golf Lounge/Simulator, or Outdoor Living! Best of all, the builder provides, installs, and completes the package prior to closing. An absolute masterpiece of design and elite engineering by an award-winning local MA builder. This high-performance, energy-efficient home features a tight envelope insulation package, supreme HERS score, ERV fresh air system with 4" HEPA filters, and balanced Make-Up Air. Inside, 4" white oak floors lead to a family room with coffered ceilings and a chef's kitchen boasting handmade custom cabinetry. High-end Pella windows flood the flexible plan with light, highlighting a 1st-floor office. This home is set back from the road for maximum privacy near 10 acres of protected trails and the commuter rail. Schedule your private showing before this incredible July deadline expires!

Lot 8 Lincoln Street, Hopkinton

Listing courtesy of Listing Agent: Maria Romero Vagnini from Listing Office: Mathieu Newton Sotheby's International Realty.
$2,388,888
4 Beds ⋅ 5 Baths ⋅ 73513206 MLS
RARE OFFERING set atop a premium hilltop lot at the end of a quiet cul-de-sac, this elegant Georgian Colonial is beautifully sited on an acre in one of Hopkinton’s most sought-after neighborhoods. Ideally located near the commuter rail to Boston, major routes, shopping, and top-rated schools, the true value lies in this exceptional specific lot and premier location. Offering 6,400 square feet of living space, with the potential for an additional 3,200+ square feet in the expansive lower level - largest home in the neighborhood. A dramatic two-story foyer with a stunning double spiral staircase, soaring ceilings, hardwood floors throughout, and a sun-filled two-story family room create an impressive yet inviting atmosphere. A thoughtfully designed floor plan provides both grand entertaining spaces and comfortable everyday living.The beautifully appointed chef’s kitchen is ideal for gathering and entertaining, while the spacious layout features a luxurious primary suite.

4 Summit Way, Hopkinton

Listing courtesy of Listing Agent: Fred Hoang from Listing Office: The Minuteman Realty Group.
$2,299,900
4 Beds ⋅ 6 Baths ⋅ 73514725 MLS
Better than new at sought-after Turkey Ridge, this spectacular 2-year-young custom home offers every premium upgrade without the wait. Exceptional curb appeal showcases striking architectural details, Hardie Plank siding, black framed windows, stone accents, and a welcoming front porch with metal roof detail. Inside, refined finishes and thoughtful design define the open-concept layout featuring a dramatic two-story family room with gas fireplace, elegant dining room, study, and expansive mudroom. The chef’s kitchen is appointed with Thermador appliances, custom cabinetry, oversized island, walk-in pantry, and wet bar. Upstairs, the luxurious primary suite offers a custom walk-in closet and spa-inspired bath, while additional bedrooms include a Jack-and-Jill and private en suite. The finished walkout lower level adds 1,300+ sq ft with full bath and abundant natural light. The garage is immaculate with epoxy floors! All of this with top rated schools, commuting, MBTA and the Marathon!

1 Honeybee Pass, Hopkinton

Listing courtesy of Listing Agent: Jennifer Green Thompson from Listing Office: RE/MAX Signature Properties.
$2,275,000
5 Beds ⋅ 6 Baths ⋅ 73532570 MLS
Gracious living on private, wooded lot set back from the road but within a subdivision of beautiful newer homes. This open plan has soaring ceilings and two story windows with views to the deck yard. A stunning family room with gas fireplace opens to both kitchen and dining areas for amplified spaciousness. The white kitchen features two huge center islands plus an eating area. Gold faucets and hardware, SS appliances, wall ovens, and lovely tile backsplash. Added bonus of a butlers' pantry with a second gas stove, dishwasher and microwave and sink for behind the scenes food prep and clean up. The open staircases to both upper and lower levels invite you to enjoy all of the spaces in the home. First floor full bath and bedroom. Second floor offers four more bedrooms plus lavish primary suite with two walk in closets, office and gorgeous bath with soaking tub and fabulous tile shower. Second floor laundry with sink. Lower level has huge flex space plus another full bath. A dream home!

51 Chamberlain St, Hopkinton

Listing courtesy of Listing Agent: My House Partners Team from Listing Office: REMAX Executive Realty.
$2,199,900
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

Listing courtesy of Listing Agent: Kim Foemmel from Listing Office: Foemmel Fine Homes.
$2,199,000
5 Beds ⋅ 5 Baths ⋅ 73454277 MLS
Move into your beautiful new home in spring 2027! There is still time to personalize this exceptional residence by selecting 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 to-be-built home offers an ideal combination of quality, luxury, comfort, and personalization, with generous finish allowances that include hardwood 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 living and entertaining. At the heart of the home, the sun-filled kitchen opens to a generous dining area and expansive family room, creating a warm and inviting gathering space. 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 build a home tailored to your style while becoming part of an extraordinary neighborhood surrounded by nature. Schedule an appointment to walk the property and begin planning your dream home today.

3 Whisper Way, Hopkinton

Listing courtesy of Listing Agent: The Macchi Group from Listing Office: William Raveis R.E. & Home Services.
$2,199,000
5 Beds ⋅ 6 Baths ⋅ 73364459 MLS
Welcome to Emerald Drive, an exclusive enclave of 8 exquisite modern farmhouse-style homes on a private cul-de-sac in sought-after Hopkinton. This breathtaking 5,248 SF residence is a masterpiece of craftsmanship, blending timeless elegance with contemporary luxury. Step into a sunlit open floor plan featuring designer millwork, soaring ceilings, and rich hardwood floors. The gourmet chef’s kitchen showcases custom cabinetry, quartz countertops, top-tier appliances, a spacious pantry, and a grand island that flows effortlessly into the inviting family room. A versatile layout includes an additional study or formal dining room. With five bedrooms—including primary suites on both the first and second levels—and 5.5 baths, this home offers exceptional comfort and flexibility. A loft area as well as a finished walk out lower level with sleek wet bar, media space, and gym enhance every lifestyle need. Near top-rated schools, trails, and commuter routes—this is luxury living at its finest!

2 Emerald Drive, Hopkinton

Listing courtesy of Listing Agent: Katie McBride from Listing Office: REMAX Executive Realty.
$2,149,000
4 Beds ⋅ 4 Baths ⋅ 73442918 MLS
Toll Brothers NEW Construction! The Dickinson Modern Craftsman floorplan—an open-concept design tailored to your lifestyle. The kitchen features a large island and walk-in pantry, flowing into a casual dining area and a two-story great room with abundant windows and a cozy fireplace. Flexible spaces offer options for two home offices and a bonus workspace. The first-floor bathroom has been upgraded to a full bathroom. Upstairs, the private primary suite includes a sitting area and a spa-inspired bath with dual vanities, a soaking tub, upgraded walk-in shower with bench, and private water closet. Three additional bedrooms and two full baths complete the upper level. The finished basement adds extra space for relaxing with family or entertaining friends. Design Choices completed!

4 Myrtle Ave Unit 20, Hopkinton

Listing courtesy of Listing Agent: Jillian Alcott from Listing Office: Toll Brothers Real Estate.
$2,095,000
4 Beds ⋅ 7 Baths ⋅ 73531003 MLS
An absolute masterpiece of design and elite engineering by an award-winning local MA builder. This high-performance, energy-efficient home features a supreme HERS score, ERV fresh air system, and balanced Make-Up Air. Inside, 4" white oak floors lead to a magnificent family room with coffered ceilings and a chef's kitchen with handmade custom cabinetry. High-end Pella windows flood the sprawling 5,450 SF plan with light, highlighting 4 bedrooms—each with its own private en-suite bath! This weekend only: reserve by the end of June and choose 1 of 5 FREE builder luxury upgrade packages—Entertainment, Theater, Gym, Golf Lounge/Simulator, or Outdoor Living! Best of all, the builder provides, installs, and completes the entire package prior to closing. Positioned for beautiful scenic views with direct access to 10 acres of protected Sudbury River trails, yet just 26 miles from Boston and a short walk to the commuter rail. See firm remarks for incentive details!

Lot 7 Lincoln Street, Hopkinton

Listing courtesy of Listing Agent: Adam Boyce from Listing Office: Mathieu Newton Sotheby's International Realty.
$1,999,900
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

Listing courtesy of Listing Agent: Kim Foemmel from Listing Office: Foemmel Fine Homes.
$1,995,000
4 Beds ⋅ 6 Baths ⋅ 73475172 MLS
STUNNING 4+ bedroom Colonial on over an acre of land in one of Hopkinton’s premier neighborhoods. A grand two-story foyer welcomes you into sun-filled, open spaces enhanced by designer finishes and hardwood flooring. The KITCHEN IS FLOODED IN NATURAL LIGHT featuring a center oversized island w/wood & stone counters & custom cabinetry, WOLF range, walk-in pantry, dining area & direct access to the back patio! A sophisticated family room with a dramatic, color changing LED FIREPLACE creates a show-stopping focal point! With four en-suite bedrooms including a versatile first-floor suite the home offers exceptional living. Primary bedroom retreat includes a full bath and impressive walk-in closet with a washer & dryer. Finished lower level with a full bath, and custom mudroom. This exceptional home combines architectural sophistication with modern conveniences. 2025-NEW fenced in yard. High end builder with HIGH end finishes - a must see!

1 Whisper Way, Hopkinton

Listing courtesy of Listing Agent: Sandra Naroian from Listing Office: Keller Williams Realty North Central.
$1,975,000
3 Beds ⋅ 5 Baths ⋅ 73540103 MLS
First time availability for this E. W. Tarca Builders designed custom built, original owner unit with over 5000sf of Bespoke Elegance. The home features a designer kitchen with Taj Mahal Marble Island, Thermador appliances and built in details. Radiant heating in floors and walls on the main level and radiant heating in the garage and basement as well. Massive great room with soaring ceilings open to second floor loft. First floor master suite with walk in closet and expansive bath. Wet bar with filtered hot and cold water, a separate coffee bar and half bath round out the first floor. Second floor features a large loft area and two bedrooms set up with two half baths and a shared shower area adjoining them. The lower level features a large finished space and a wine room with humidity control. A more extensive description of the features and upgrades which are too numerous to list here is attached to the listing for review, along with floor plans and condo information.

13 Davenport Ln Unit 13, Hopkinton

Listing courtesy of Listing Agent: The Real Team from Listing Office: Berkshire Hathaway HomeServices Commonwealth Real Estate.
$1,975,000
3 Beds ⋅ 5 Baths ⋅ 73539697 MLS ⋅ ['Davenport Village'] BLDG.
First time availability for this E. W. Tarca Builders designed custom built, original owner unit with over 5000sf of Bespoke Elegance. The home features a designer kitchen with Taj Mahal Marble Island, Thermador appliances and built in details. Radiant heating in floors and walls on the main level and radiant heating in the garage and basement as well. Massive great room with soaring ceilings open to second floor loft. First floor master suite with walk in closet and expansive bath. Wet bar with filtered hot and cold water, a separate coffee bar and half bath round out the first floor. Second floor features a large loft area and two bedrooms set up with two half baths and a shared shower area adjoining them. The lower level features a large finished space and a wine room with humidity control. A more extensive description of the features and upgrades which are too numerous to list here is attached to the listing for review, along with floor plans and condo information.

13 Davenport Ln Unit 13, Hopkinton

Listing courtesy of Listing Agent: The Real Team from Listing Office: Berkshire Hathaway HomeServices Commonwealth Real Estate.
$1,890,000
4 Beds ⋅ 4 Baths ⋅ 73519926 MLS
Stunning new construction set on almost 2 acres of wooded land directly across from entrance to a desirable Hopkinton neighborhood. Beautiful chef’s kitchen featuring counter-to-ceiling quartz, 6-burner gas stove, Thermador appliances, ample storage, and a coffee/wet bar, opening to the dining area& living room with a gas fireplace. Sliders open to expansive covered back porch. Private office overlooks front porch on the first level. Upstairs offers 4 spacious bedrooms with 3 attached full bathrooms. Laundry room with pet washing station conveniently located outside the primary suite. Primary suite features vaulted ceilings, a resort-style bathroom, and an expansive walk-in closet ready to be customized to the buyer’s needs. Finished basement perfect for additional living space with 2 sump pumps for added peace of mind. This home is a rare fine with custom upscale finishes throughout, including smart toilets in every bathroom. Space, privacy, and amenities in ideal Hopkinton location!

150 Fruit St, Hopkinton

Listing courtesy of Listing Agent: Jeannine Coburn from Listing Office: REMAX Executive Realty.
$1,765,000
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

Listing courtesy of Listing Agent: My House Partners Team from Listing Office: REMAX Executive Realty.
$1,700,000
3 Beds ⋅ 4 Baths ⋅ 73530391 MLS
Grand Brick Colonial sited on 2.64 acres overlooking picturesque Hopkinton Country Club with 3 Car attached Garage and 3 Car detached Garage! Potential for ADU! New White Dove interior paint: Family Room, Foyer and Office! Beautiful interior finish details throughout! Sweeping bridal staircase, curved archways, wainscoting and moldings galore. Entertainment-sized Dining Room. Cathedral Great Room with beautiful fireplace surround. Skylit Sunroom encased in glass with brick accent wall. Spacious Kitchen with skylights, center island, ss appliances, walk-in Pantry, cozy wood stove and walkout bay dining area leads to back deck. Back hall Mud Room, Office and Half Bath. Back stairs lead to cathedral Primary Suite with built-ins, closets and Large Bath with vanities, tiled shower and jacuzzi. Two oversized secondary Bedrooms with hardwood floors; Hall Bath and 2nd floor Laundry Room. Finished lower-level Family Room, Game Room with Wet Bar, Full Bath and unfinished storage space. Great Location! Quick access to Train Station, Route 9, 495 & MA Pike!

211 Saddle Hill Road, Hopkinton

Listing courtesy of Listing Agent: Kathleen Williamson from Listing Office: Berkshire Hathaway HomeServices Commonwealth Real Estate.
$1,600,000
6 Beds ⋅ 4 Baths ⋅ 73544112 MLS
Perfectly sited on 1.4 private acres this thoughtfully updated, bright, open, and energy-efficient home offers the perfect balance of elegance, comfort, and everyday functionality. Bathed in natural light, the open floor plan creates an inviting atmosphere designed for both relaxed living and effortless entertaining. At the heart of the home, the beautifully appointed kitchen features timeless white cabinetry, granite countertops, premium appliances, coffee bar, an impressive wall of pantry storage, and an expansive dining area where family and friends naturally gather. The kitchen flows seamlessly into the formal living and dining rooms, while the spacious family room, anchored by a wood-burning fireplace, opens through French doors to an oversized deck overlooking the private backyard. Whether enjoying morning coffee, hosting summer dinners al fresco, or simply taking in the peaceful surroundings, this outdoor space is destined to become a favorite retreat. A private first-floor study offers an ideal work-from-home space. Upstairs, the luxurious primary suite is joined by four additional generously sized bedrooms, a spacious guest bath, and a convenient laundry room, providing five bedrooms on one level. The exceptional walk-out lower level lives like a private guest residence, complete with its own ensuite bedroom, comfortable living area, home theater, fitness space, and second office, making it ideal for multi-generational living, long-term guests, or an au pair. Outside, the beautifully landscaped backyard provides abundant space for recreation, entertaining, and future outdoor amenities, while the three-car garage and oversized shed offer exceptional storage. Beyond the property itself, the neighborhood is one of its greatest treasures, with quiet streets, welcoming neighbors, and children playing outside, creating a true sense of community that's increasingly hard to find. Miles of hiking, biking, and nature trails begin just beyond your backyard in Upton State Forest, offering year-round outdoor recreation. Recent improvements provide exceptional peace of mind and include a new six-bedroom septic system (2023), new roof and solar panels (2021), freshly painted exterior (2025), and many additional updates throughout the home. Please refer to the attached feature sheet for a complete list of improvements. This is more than a beautiful home—it's a place where memories are made and every day feels just a little more peaceful.

23 Falcon Ridge Dr, Hopkinton

Listing courtesy of Listing Agent: The Macchi Group from Listing Office: William Raveis R.E. & Home Services.
$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

Listing courtesy of Listing Agent: John Coutinho from Listing Office: Berkshire Hathaway HomeServices Commonwealth Real Estate.
$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

Listing courtesy of Listing Agent: Laura Wauters from Listing Office: Century 21 Custom Home Realty.
$1,549,000
4 Beds ⋅ 3 Baths ⋅ 73537135 MLS
Perfectly sited on a picturesque level corner lot in one of Hopkinton's most coveted and bucolic neighborhoods, this exceptional residence offers an enviable lifestyle just moments from Whitehall Reservoir, where miles of scenic trails, kayaking, fishing, boating, cross-country skiing, and winter ice skating provide year-round outdoor recreation. Thoughtfully designed for both elegant entertaining and comfortable everyday living, the chef's kitchen is beautifully appointed with premium Wolf and Sub-Zero appliances, custom cabinetry, and generous gathering space, flowing seamlessly into what may become your favorite room in the house—a spectacular four-season sunroom with radiant heated floors, walls of windows, and a cozy gas fireplace. Whether you're enjoying morning coffee while watching the sunrise, admiring the brilliant fall foliage, or relaxing by the fire as snow falls outside, this space is simply magical in every season. The dramatic cathedral family room with a wood-burning fireplace creates a warm and inviting gathering place, while the formal dining room and private study offer sophistication and flexibility. The luxurious primary suite is a true retreat, featuring soaring ceilings, abundant natural light, a two-sided gas fireplace, and a spa-inspired bath with radiant heated floors and a soaking tub you'll never want to leave. Four additional spacious bedrooms provide room for family, guests, or a second home office, while the finished lower level offers a spacious family room and dedicated fitness area. Outdoors, an expansive deck, stone patio, and inviting firepit overlook private grounds designed for impromptu barbecues, evenings under the stars, and making lifelong memories with family and friends. Located in one of Hopkinton's most desirable neighborhoods, yet just minutes to top-rated schools, shopping, dining, the commuter rail, and major routes, this home offers the perfect balance of luxury, comfort, and connection to nature. More than simply a beautiful home, 23 Longwood Drive is a place where every season brings something to enjoy and every space invites you to slow down, gather with the people you love, and truly feel at home.

23 Longwood Dr, Hopkinton

Listing courtesy of Listing Agent: The Macchi Group from Listing Office: William Raveis R.E. & Home Services.
$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

Listing courtesy of Listing Agent: The Shulkin Wilk Group from Listing Office: Compass.
$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

Listing courtesy of Listing Agent: Campos Homes from Listing Office: RE/MAX Real Estate Center.
$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

Listing courtesy of Listing Agent: Kathleen Williamson from Listing Office: Berkshire Hathaway HomeServices Commonwealth Real Estate.
$1,279,900
3 Beds ⋅ 4 Baths ⋅ 73549814 MLS
Discover refined living in this elegant Sheffield model in Legacy Farms, one of Hopkinton's most sought-after communities. Built in 2014, this beautifully designed and meticulously maintained home offers approximately 3,822 sq ft of thoughtfully crafted living space with 3 bedrooms, 3.5 baths, 2 private flex/office rooms, formal living and dining rooms, a spacious family room, multiple lofts, open living areas, and a media room that can also serve as a bedroom. Recent updates include premium Thermador kitchen appliances, refreshed interior paint, upgraded cabinetry, custom closets in every bedroom, new HVAC heat exchangers, and an upgraded garage. Extensive builder upgrades include a stone front elevation, side-entry garage, hardwood floors on the main level, hardwood stairs with open railings, recessed lighting, a fireplace, custom kitchen cabinetry, and upgraded countertops. Upgrades list attached.

14 Autumn Ridge Dr, Hopkinton

Listing courtesy of Listing Agent: Vijaya Bhaskar Yelchuru from Listing Office: StartPoint Realty.

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