luxury properties for sale Holliston, United States

**One-Owner, Meticulously Maintained 3-Family — A Rare Find! **Pride of ownership shines throughout this exceptional three-family home, lovingly cared for by the same owner since day one. The spacious owner's unit offers three bedrooms and two full baths, gleaming hardwood floors, a cozy fireplace, and a large exterior deck perfect for entertaining or relaxing outdoors. Two additional one-bedroom units round out this versatile property — ideal for extended family or strong rental income. Every unit features the sought-after convenience of in-unit laundry. Whether you're an investor seeking a turnkey income property or an owner-occupant looking to offset your mortgage, this well-maintained gem checks every box. Properties like this rarely come to market — don't miss it! Multiple out buildings for storage. PLEASE NOTE: Some photos taken prior to current tenant on main level. One central forced air gas heating system for entire building, separate electric for each unit. 24 HOUR NOTICE REQUIRED FOR A SHOWINGS.

A rare opportunity to become the next steward of an exceptional home or investment property in one of Southborough's most convenient locations. Set on an oversized 1.4-acre lot along a quiet neighborhood street, this versatile five bedroom, three and a half bath property (2,586 sq. ft. total) offers two attached living spaces — a four bedroom + office, two and a half bath main residence (approx. 2,078 sq. ft.) and a one bedroom, one bath in-law suite/ADU (approx. 508 sq. ft.). The configuration is nicely suited for multi-generational living, an au pair suite, income property potential, or whatever flexible arrangement fits your plans. The main residence offers a traditional floor plan with an eat-in kitchen with stainless steel appliances, dedicated first floor laundry room/pantry, a large formal dining room, separate family and living rooms, a primary suite with attached ensuite bath, three additional generously sized bedrooms with hardwood floors sharing a full hall bath with double vanity, and a bonus room perfect as home office, gym, or flex space of your choosing. The in-law unit includes an eat-in kitchenette, living room, bedroom, and full bath with tub. Outside, a composite deck overlooks the in-ground pool (in good working order), and the expansive lot leaves plenty of room to garden, play, entertain, or simply spread out. With this much space, land, and flexibility in a convenient Southborough location, there is significant upside for the right buyer ready to bring their vision to life. Ideally located with proximity and access to top-ranked schools and easy access to the Commuter Rail, Rt. 9, 495, and the Mass Pike.

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. three upper bedrooms, office, large bonus room + finished walkout lower level. two-car garage with EV charger and generator backup. EQUESTRIAN: Professional nine-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, six-person barrel sauna. Outdoor kitchen with pizza oven. Meditation labyrinth, organic fruit orchards, and berry patches.

Motivated seller! Don't miss this fantastic opportunity to own a spacious multi-level two-family home in the heart of West Roxbury. Set on a large lot with fenced-in yard, this property has seen many recent updates while still offering the chance to add your own finishing touches and build instant equity. The first-floor unit features 2 bedrooms and 1 full bath, while the upper unit offers 3 bedrooms and 1 full bath. Parking for 2+ cars. Whether you're an owner-occupant or investor, this property offers outstanding potential in a sought-after neighborhood.

Beautifully maintained two-family home situated on a desirable, level lot, offering an excellent combination of comfort, outdoor space, and investment potential. The property features great curb appeal with a welcoming front porch, spacious yard, mature fruit trees, backyard patio with fire pit, paved driveway, and detached one-car garage—providing plenty of space for entertaining, gardening, or relaxing outdoors. Inside, both units feature bright and inviting living spaces with generous natural light and functional layouts. The first-floor unit offers two bedrooms, one full bath, a bright kitchen, enclosed three season porch and comfortable living room with recessed lighting and a ceiling fan. Direct basement access provides additional storage space and laundry. The second unit features two bedrooms, one full bath, kitchen with granite counter tops, mudroom/pantry, bright living room with recessed lighting and office space. Whether you're an owner-occupant looking to offset your mortgage, an investor seeking a well-cared-for income property, or a multigenerational household in need of flexible living arrangements, this two-family home presents an excellent opportunity. Conveniently located near shopping, cafes, restaurants, parks, trails, schools, and major commuter routes, this property offers the perfect blend of comfort, convenience, and long-term potential. A wonderful opportunity to own a versatile and well-cared-for two-family home in a desirable location.

Welcome to this spacious two-family home, filled with natural sunlight and offering plenty of room to spread out! This property features a large yard, abundant parking, and the flexibility that makes multi-family living a great opportunity. Whether you're looking to owner-occupy while generating rental income, or expand your investment portfolio, this property offers plenty of possibilities. Conveniently located just minutes from Main Street and Route 1, you'll have easy access to shopping, dining, commuting routes, and everyday amenities. With generous space inside and out, ample parking, and an excellent location, this two-family home is an opportunity worth exploring! Landscape virtually enhanced.

35 Middle Street offers an exceptional development opportunity in a prime Newton location. Located on a quiet side street in the heart of Nonantum, this property is being offered “AS IS.". The site presents project potential for almost 8000 square feet of mixed-use business or residential development. Alternatively, a buyer could simply renovate the existing structure into a lovely home or income producing property. Located between Washington and Watertown Streets, the property offers convenient access to the Mass Pike (east to downtown Boston and west to Route 95/128), Newton Corner, Newton North High School, the MBTA commuter rail, and other transit options. This highly accessible corridor supports strong visibility and access to Newton’s shops, restaurants, and major employment centers.

Tucked away on a serene cul-de-sac at 62 Pinsonnault Lane, this stunning modern Cape embodies updated elegance in one of North Attleboro's most sought-after neighborhoods. Outside, a picturesque picket fence welcomes you to an outdoor oasis featuring a spacious patio and a cozy fire pit ideal for entertaining. Step inside to discover a thoughtfully designed 3,237 sq. ft. interior that seamlessly blends modern amenities with classic charm. The main level boasts a bright, open-concept layout engineered for effortless entertaining and everyday living. The heart of the home is the chef-inspired kitchen, fully equipped with stainless steel appliances, a large center island, and ample cabinetry. Directly adjacent, the warm and inviting living room features a striking fireplace as its focal point, while a formal dining room provides a sophisticated space for special occasions. This expansive home features 4 bedrooms and 3.5 bathrooms, highlighted by a luxurious primary suite complete with a spa-like ensuite bath and massive double walk-in closets. A major highlight is the completely renovated, fully finished basement, which expands your living space with an additional bedroom, full bath and a full kitchen creating the perfect space for a guest retreat or flexible space for extended family living. Don't miss the chance to own this versatile, turnkey masterpiece.

Completely renovated and deleaded two-family home offering an exceptional opportunity for both owner-occupants and investors! Each spacious unit features two bedrooms, a dedicated study/flex space, two full bathrooms, and an open-concept layout with a beautifully appointed kitchen, dining area, and living room, perfect for modern living and entertaining. The kitchens are finished with granite countertops, while hardwood flooring extends throughout each unit, creating a warm and elegant feel. Both units also enjoy private front and rear decks with low-maintenance composite flooring, providing the perfect outdoor space to relax. Additional features include durable vinyl siding, separate utilities with two 100-amp electrical panels, two gas meters, and a convenient coin-operated laundry area. Ideally located just minutes from major highways, public transportation, shopping, dining, and everyday conveniences, this turnkey property offers the perfect combination of style, functionality, and location. Don't miss this outstanding investment or owner-occupied opportunity!

Absolute perfection awaits in this exceptional custom-built and masterfully remodeled residence. Reminiscent of a refined Nantucket shingled Cape Cod, this extraordinary home pairs timeless architecture with impeccable craftsmanship and luxurious modern amenities.A manicured lawn, stone wall, lush landscaping, and elegant bluestone path welcome you to the charming front porch. Inside, gleaming hardwood floors,Pella Architectural windows, custom millwork, and abundant natural light create an atmosphere of sophistication.The gracious foyer opens to a formal living room with fireplace and custom built-ins, leading to a stunning office surrounded by windows. The elegant dining room flows seamlessly into the spectacular chef's kitchen, outfitted with custom cabinetry, Sub-Zero and Thermador appliances, wine refrigeration, and an oversized center island. The adjoining breakfast area opens to a beautiful bluestone patio.The inviting family room features a magnificent stone fireplace, built-ins, and walls of windows overlooking the grounds.A sunroom, mudroom, first floor bedroom and full bath complete the first level.Upstairs, the luxurious primary suite offers a private balcony, spa-inspired bath, and two 11' x 9' walk-in closets, along with two additional bedrooms, w/versatile sleeping courters.Beautifully appointed inside and out, this exceptional property offers timeless elegance, extraordinary craftsmanship,and an effortless lifestyle all with convenient highway access.

Look no further...this beautifully maintained side-by-side bilevel two-family home is a rare offering in a desirable location. Thoughtfully cared for and uniquely versatile, it’s ideal for multi-generational living, owner-occupancy with supplemental income, or a strong investment portfolio addition. Tucked on a quiet side street just off Rt. 117, the property offers exceptional convenience with walkable access to Center Elementary School and Randall Library, plus close proximity to local farms, the Assabet River, Lake Boon, scenic hiking trails, and dining destinations. Unit 6 delivers a classic, well-designed layout with exceptional functionality. The kitchen offers generous cabinet storage and efficient workspace, flowing seamlessly into a formal dining room ideal for hosting or everyday meals. The living room provides a warm, inviting atmosphere with hardwood flooring and natural light. Two spacious bedrooms offer versatility for sleeping, office, or hobby use. Additional features include hardwood floors throughout, gas heat, attic and basement access for storage or future expansion potential, a two-car driveway, and a private rear yard that enhances outdoor enjoyment. This unit is perfect for an owner-occupant seeking comfort and practicality or an investor looking for strong rental appeal.Unit 8 stands out with a stylish, modern renovation that creates a truly impressive living experience. The first level showcases a granite kitchen/dining area with updated cabinetry, sleek finishes, and excellent flow for cooking and entertaining. The fireplaced living room adds architectural charm and a focal point for gatherings. The updated bath features contemporary fixtures and a clean, polished aesthetic. Upstairs, the loft-style second level offers dramatic ceiling height, exposed beams, and abundant natural light. This flexible space can function as a one- or two-bedroom layout, a studio-style retreat, or a creative workspace. Ample closet storage, hardwood flooring, and thoughtful design elements make this unit feel both modern and timeless. Two dedicated parking spaces complete the offering The grounds are a standout, featuring professional landscaping and fruit trees that elevate the property’s charm and curb appeal. Whether you’re seeking a refined residence, a flexible living arrangement, or a smart investment opportunity, this home delivers exceptional value and character. A truly special property for the discerning buyer. Don’t miss out

Open House moved to Saturday (10/3). Welcome to 12 Howard Road a twelve-acre bucolic retreat minutes from everything, yet feeling worlds away. Set along the serene shores of Howard Pond and the Abbott Run across four parcels sold together, this extraordinary Cumberland estate was lovingly cultivated by a Master Gardener of Rhode Island. Giant oaks and pines span the property on all sides, wild native plants emerge in glorious succession along the shoreline each spring and summer, and spectacular sunsets reflect across the water each evening. Magnificent blooming Dogwood trees, Japanese maples, and established gardens complete a setting of breathtaking, ever-changing beauty. The classic Colonial delivers five bedrooms and three-and-a-half baths with hardwood floors throughout, stone countertops throughout, and all bathrooms retiled within the last five years. A wood-paneled living room with exposed beams flows into an unexpectedly oversized eat-in kitchen, while a distinguished cherry office with built-in bookshelves and cherry floors adds a rare finishing touch. The fully self-contained in-law suite features a private entrance, full kitchen, bedroom, full bath, and a three-season porch with panoramic pond and backyard views. Outside, large bluestone patios, ample off-street parking across two driveways, and a four-car garage round out this truly rare Cumberland offering.

Exceptional two-family opportunity in Boston's highly desirable Brighton neighborhood. This beautifully maintained and landscaped property is ideal for an owner-occupant seeking rental income or for investors looking for a strong portfolio addition. The second-floor unit features four spacious bedrooms and two full bathrooms, offering generous living space, abundant natural light, and a flexible layout ideal for larger households or roommates. The first-floor unit offers three bedrooms and two full bathrooms, featuring comfortable accommodations and well-proportioned living areas. Additional highlights include lower-level laundry, a private backyard, driveway parking for up to six vehicles with individual access, and a detached two-car garage. A rare Brighton convenience: street parking on Donnybrook Road does not require a resident permit. Quick access to the Mass Pike, Storrow Dr, and downtown Boston. A rare opportunity to own a versatile income-producing property.

A rare opportunity to own an original Sears & Roebuck Craftsman in the popular Thoreau school neighborhood. This distinctive home showcases the enduring quality & craftsmanship of a bygone era while offering exceptional potential for its next chapter. Authentic architectural details abound; including redwood beams, cedar shingles, pocket doors, high ceilings, hardwood floors, classic farmhouse sink, cast-iron tub, & beautiful moldings. Thoughtful updates completed in 2023 include a new roof w/metal accents, updated electrical & plumbing systems, & renovated bathrooms. The spacious yard w/fruit trees, Concord grapes & flowers is perfect for enjoyment. An impressive two-story barn offers endless possibilities for hobbyists, artists, or storage. The extended garage is accented by the original hayloft door & pulley—a charming reminder of the property's historic roots. Close to trails, shopping, restaurants and train. Rich in history, craftsmanship, and character, make this home your own.

Four condo quality rental units and first level commercial space current use tavern/restaurant. Three story plus basement building originally built in 1930 with multi floor addition of residential units constructed in 2021. All residential units have large living rooms, hardwood floors, custom kitchens with white cabinets, quartz counters, GE stainless appliances, in unit laundry, each unit is self contained for heating/cooling/hot water, custom tile baths, generous size bedrooms and closet space. Delivered vacant. Liquor and entertainment licenses NOT included in the sale.

Welcome to 27 Woodleigh Rd, a well-maintained two-family home offering approximately 2,416 sq. ft. of living space in a desirable Watertown location. The property features two spacious units with separate entrances. One unit offers 2 bedrooms and 1 full bathroom, while the second features 3 bedrooms and 1 full bathroom. Both units offer updated kitchens and bathrooms and comfortable, functional layouts.Recent improvements include a newer roof (2021), two newer composite decks, and two gas hot water tanks installed in 2025. The property also offers an impressive driveway with parking for up to 10 cars.Additional space in both the basement and attic provides exciting future possibilities. The property is equipped with three electrical panels, including an additional panel that may support future expansion. The basement offers potential for an ADU, while the attic also presents potential for additional use and has independent exterior access currently enclosed within one of the bedrooms. Any ADU, expansion, or future use is subject to buyer due diligence and all required permits and municipal approvals.Conveniently located near shops, restaurants, public transportation and major routes, this property offers an excellent opportunity for an owner-occupant, investor, or multi-generational living. Easy to show.

Tucked off one of Concord’s most prestigious streets, this fully renovated colonial sits on a private 1-acre lot set 250' from the road, steps to historic Concord Center. Meticulously updated with new systems and roof, the home offers turnkey living with an open plan chef’s kitchen featuring quartz counters, oversized island, breakfast nook with beverage fridge, and seamless flow to an outdoor kitchen, patio and screened porch. Oversized family room with coffered ceiling and French doors, cozy living room with stone-surround gas fireplace, mudroom, hardwood floors and refined millwork. Four bedrooms upstairs (two en-suites) plus a generous primary suite with spa bath and a second-floor laundry. Finished lower level includes recreation space and guest suite. New three-car garage with finished loft—kitchenette, full bath and exercise/lounge—ideal for guests or home office. Easy commuter access, sidewalks to Concord Center and miles of riverside conservation trails.

Welcome to 5 Walnut St, a refined young Arts & Crafts Colonial blending European elegance with modern luxury. Offering 5,200 sq ft, this thoughtfully designed home features five spacious bedrooms and five full baths, ideal for comfortable, flexible living. Sunlit interiors showcase hardwood floors, custom millwork, 9' ceilings, and an open layout. The chef’s kitchen includes Thermador appliances, a Sub-Zero paneled fridge, induction cooktop, large island, and walk-in pantry, flowing into inviting living and dining spaces with a wood-burning fireplace. The main level offers an office and guest suite; upstairs includes three bedrooms, laundry, and a luxurious primary suite with spa bath and dual closets. A finished walkout lower level adds versatile space. Set on a beautifully landscaped ¾-acre lot abutting conservation land with a deep backyard, two-car garage, and expansion potential in the walk-up attic. Just about 1 mile to Lexington Center with easy access to Boston, Routes 2 and 95

Situated along Watertown’s Mt. Auburn Street improvement corridor, this two family home blends classic charm with thoughtful updates, including newer gas boilers, hot water heaters, and replacement windows throughout. Each unit features refreshed kitchens with original breakfast nooks. The second-floor unit includes a bonus office, in-unit laundry, and an enclosed sun room. The basement offers dedicated laundry for the first floor, ample storage for both units, direct access to the side yard and potential for additional living space. Outside, enjoy a private level yard, paver patio, newer rear decks, improved driveway, and one-car garage. A durable slate roof adds lasting value to this exceptional investment or owner-occupant opportunity. Ideally located near the Cambridge line, this well-maintained property offers easy access to Harvard Square, Arsenal Yards, Watertown Square, the Charles River, Storrow Drive. Both units are vacant. Easy to show.

Discover a premier real estate opportunity minutes from the UMass Medical main campus, major highways, and the vibrant shopping and acclaimed restaurants of Shrewsbury Street. Located at 17 Tampa Street, this versatile two-family property is perfect for savvy investors or buyers seeking a smart house-hack. Each distinct unit—one upstairs and one downstairs—features a flexible 2-to-3 bedroom layout and one full bathroom, highlighted by spacious kitchens designed for comfortable living.The property is highly efficient with completely separate metering for both water and gas. Currently occupied by reliable tenants-at-will, this turnkey property offers immediate rental income and long-term potential. Fall in love with the welcoming front porch, a fully fenced, flat, and lush backyard perfect for outdoor enjoyment, and a basement with a convenient covered door with access to the backyard. Showings are available exclusively during the open houses on Saturday and Sunday from 11:00 AM to 1:00.