luxury houses with terrace for sale Winchester, United States

Everything you've been looking for if you're downsizing or upsizing. Beautifully renovated and expanded Cape, this stunning Morningside home offers the rare convenience of one-level living on a dead-end street near the Stratton School. Thoughtfully redesigned by a well-known local builder, the main level features a spacious primary suite, second bedroom, full guest bath, and a gorgeous open-concept kitchen flowing seamlessly into the dining and family rooms. A lovely fireplace and oversized picture window create a warm and inviting living space filled with natural light. The second floor offers two generously sized bedrooms and an additional full bath, perfect for family or guests. Enjoy the privacy of the spacious rear yard with mature trees and a large deck ideal for entertaining or relaxing outdoors. A special opportunity in one of Arlington’s most sought-after neighborhoods.

Not every home needs to be finished on day one. Sometimes the best houses are the ones that already live well and leave room for your ideas later. This ranch makes life simple from the start with everything you need on one level. Step into a comfortable living room that opens into a dining area or bonus space depending on your needs. The large eat-in kitchen has room to gather today and provides opportunity to reimagine over time. Three bedrooms and a full bath complete the main floor with an easy, practical layout. Downstairs changes the conversation. High ceilings, a walkout family room, kitchenette, laundry, and direct garage access create space, whether that means movie nights, hobbies, guest space, or simply spreading out. Outside, a deck overlooks the backyard while the fenced area gives pets room to roam. Nearby parks, easy access to the 67 bus to Alewife, and a location that keeps daily routines manageable make this a home that works now and leaves space for what comes next.

60% SOLD OUT! Introducing The Mary Kenney Collection: 10 new single-family homes in a private cul-de-sac on the Winchester line. Secure your lot now and enjoy the rare ability to customize floor plans and finishes to fit your lifestyle. Each home offers an oversized 2-car garage, grand foyer & flex space perfect for a gym, theatre, or guest suite. The open-concept main level is designed for entertaining with oversized windows, patio access, wet bar, office, and a chefs kitchen with custom cabinetry, high end Thermador paneled appliances & pantry. Upstairs hosts 3 bedrooms including a primary suite with walk-in closet, spa bath with a dual shower and deep soaking tub & balcony. Minutes to Middlesex Fells trails, Mystic Valley Pkwy, Somerville & Cambridge hubs, and quick access to downtown Boston. This exclusive offering, rarely available in Medford, presents an opportunity to own new construction that balances luxury, community, and convenience. A new sub-division located at 545 Winthrop St, Medford MA 02155 - Winthrop St & Mary Kenny Way

Some homes offer extra space, but this one offers extra possibilities. Need room for cars, motorcycles, a workshop, home business, gym, or creative studio? The detached four-car garage with finished bonus space above opens the door to possibilities that are hard to find in Arlington. Use it as an office, entertaining space, hobby room, or explore future ADU potential. The wraparound porch welcomes you into a home designed for everyday living with a fireplaced living room, spacious kitchen with island, dining area opening to a large deck, and convenient half bath. The second floor features two bedrooms and a full bath, while the entire third floor is dedicated to a private primary suite with vaulted ceilings, walk-in closet, sitting area, and spa-like bath. The finished lower level adds a family room and half bath. Just 0.1 mile to the Minuteman Bike Path and under 0.3 mile to the Arlington Reservoir and Mass Ave, this home gives you a unique opportunity to live, work, create, and grow.

Thoughtfully redesigned during a complete renovation and expansion in 2007, 9 Bonad Road seamlessly blends timeless style and functionality for complete ease of living in a fantastic location near Menotomy Rocks Park, Robbins Farm Park and Brackett Elementary. The main level greets you with an elegant living room, with beamed ceilings and custom built-in storage, that flows into a meticulously designed kitchen, highlighted by Italian marble counters, cherry cabinets, coffee bar and cathedral ceilings with two skylights. This leads to a formal dining room and a stunning first-floor primary suite with walk-in closet and full bath, allowing for simple one-level living. Upstairs, there are three more bedrooms, another full bath and an office that provides access to an unfinished walk-up attic with future expansion potential. Outside, unwind in the professionally designed, serene backyard featuring a sprawling patio, covered porch, small pond and beautifully curated landscaping.

Some streets just have a certain magic about them. Neighbors linger outside, block parties still happen, and there’s a true sense of community. Set on a quaint, tree-lined street in the beloved Brackett neighborhood, this lovingly maintained home has been truly cared for, and it shows! Inside, the charm of the 1930s steals the show with custom woodwork, detailed moldings, and original built-ins, while nicely proportioned rooms create a natural, easy flow. Southeast morning light pours into the fireplaced living room, followed by a 1993 addition where a den became the perfect spot for a home office, playroom, or TV room. Sliders off the dining room open to a back deck overlooking a flat, lush green yard with plenty of room to relax, garden, or entertain. Upstairs are three bedrooms, a tiled bath, and a walk-up attic. All of this + garage parking and a lower-level mudroom/bonus space, just a short stroll from Arlington's most treasured destination - Skyline Park for sweeping views of the city!

A quick three blocks from the Minuteman Bikeway, bordering Lexington's most treasured green space, this custom-built Cape offers the best value in Lexington! This gem presents a rare opportunity to enjoy space, flexibility and value in one of Massachusetts' most sought-after communities, celebrated for its exceptional school system and lively, quaint New England town center. Lovingly maintained by its original owners, this home blends vintage charm with quality upgrades which equals endless potential. Highlights include a retro eat-in kitchen with nicely preserved custom-built cabinetry and a versatile, grade-level walkout lower level that's perfect for today's rec room or tomorrow's guest suite, in-law apartment, or future au pair suite. Upstairs, mid-century-inspired design adds personality with step-up/down living spaces, a cozy fireplaced family room, an essential little half bath, generous eave and closet storage, and three spacious bedrooms. Hit the easy button...the big-ticket items are already complete, including insulated windows, vinyl siding, a gas heating system, newer chimney liner, and a newer gas water heater. If lifestyle is just as important as location, you'll love starting your mornings on the peaceful back deck, surrounded by greenery and pretty stone walls, listening to the birds chirp before taking a short stroll to the bike-path to explore Great Meadows Nature Preserve or continue on to Lexington Center for the local farmers market, cafés, restaurants, and charming boutique shops.

Set at the end of a cul-de-sac on a generous .28-acre lot, this beautifully updated home offers exceptional space, light and versatility. Designed for everyday living and entertaining, the main level flows effortlessly from a formal living room to an inviting sitting area and elegant dining room. At the heart of the home, the newly renovated chef’s kitchen features quartz counters, stainless appliances, a center island with seating and storage and spacious dining area that opens to a lovely patio and expansive backyard. The oversized family room impresses with cathedral ceilings, a pellet-stove fireplace and wet bar, creating the perfect gathering space. Upstairs, the primary suite has cathedral ceilings, walk-in closet and spa-like bathroom. Two well-sized bedrooms and a full bathroom complete the second floor. The beautifully finished lower level adds remarkable flexibility with ¾ bathroom, laundry and bonus rooms ideal for guests or extra living areas. Convenient to schools, town center, parks and public transportation.

Just imagine waking up on Follen Hill. Custom built in 2005 to evoke a turn-of-century Boston brownstone - turned bannister, oversized windows, exquisite molding around every window, door, and ceiling. Five bedrooms, four and a half baths, three finished floors. Double pocket doors open the formal living and dining rooms to a fireplaced family room. A chef's kitchen with oversized island, walk-in pantry, double ovens, built-in refrigerator, gas range with griddle. French doors and sliders open to a covered bluestone patio - the room you entertain in doubles when the weather agrees. The primary suite has a fireplace, walk-in closet, and spa bath. The second floor adds an en-suite second bedroom as well. The third floor has a play room, a large office, and a fifth bedroom. Moments from Lexington Center, Battle Green, and the Minuteman Bikeway. Bowman Elementary. Now imagine the dining room set for ten, pocket doors open, fire lit. This is not a starter home. This is the home you stop at.

Welcome to this beautifully refreshed Colonial tucked away at the end of a peaceful cul-de-sac, offering the perfect blend of comfort, space, and convenience. Designed for both everyday living and effortless entertaining, the expansive main level features spacious gathering areas and a seamless flow throughout. Retreat to the impressive primary suite complete with a cozy fireplace, oversized walk-in closet, and private space to unwind. The finished lower level offers exceptional flexibility with potential for multigenerational living, guest accommodations, or an in-law setup. Step outside to enjoy a private backyard retreat featuring a basketball court and plenty of space for recreation, entertaining, or simply relaxing. Recent updates include fresh interior paint (2026), refinished hardwood throughout the main level (2026), and new carpeting in the bedrooms (2026). Ideally situated just minutes from major highways. A rare opportunity to own a move-in ready home in a prime location.

New construction in Watertown! This meticulously built 5-bedroom, 4.5-bath home offers modern design and high-end finishes perfectly situated in one of Watertown's most convenient locations. The home features an open and inviting floor plan w/ hardwood floors throughout, soaring ceilings, decorative molding, and abundant natural light that fills the space. The kitchen is equipped w/ premium Bosch appliances, custom cabinetry, and large kitchen island. Sliders to the exterior make this house perfect for entertaining. 2nd floor boasts a primary suite with full bath and walk-in closet. A secondary primary with full bath, and 2 add'l generous bedrooms and main bath. Andersen windows/doors and 3 electric heat pumps allow efficient heating/cooling throughout the home. Stunning private deck and patio and a large fenced-in yard. Full attic for storage. Bonus attached heated garage for convenience. Ideally located just minutes from Waverley Square, shops, restaurants, schools, Cambridge/Boston.

A masterpiece by Cafasso Design Group, this architectural work of art redefines luxury living. Tucked within a coveted enclave off Brattle Street, this home unfolds across lush, sculpted grounds framed by mature trees, offering an unparalleled serene retreat. A striking sculptural staircase serves as the dramatic centerpiece, while interiors masterfully blend contemporary Japanese, Scandinavian, Italian, and French influences.The eat-in chef’s kitchen features custom Italian walnut cabinetry, Calacatta Gold marble counters, dual sinks & dishwashers, a Gaggenau 400 Series double oven, and walls of glass. Generous bedrooms and spa-inspired baths deliver sanctuary, complemented by a glass-enclosed office and a family room featuring a floating gas fireplace. A dedicated lifestyle level boasts a gym, guest suite, and inviting spa with a Western Red Cedar sauna & steam shower. Outside, manicured grounds surround an outdoor kitchen, expansive deck, and inviting patio perfect for entertaining.

Meticulously maintained Colonial in a desirable West End neighborhood. Thoughtfully redesigned, the first floor features an open-concept layout that seamlessly connects the kitchen to the sun-filled living and dining areas. The kitchen with updated appliances and breakfast bar offer direct access to a private deck overlooking the backyard with a seller-added sport court—perfect for basketball. The walk-out lower level adds exceptional living space with a mudroom, beautifully renovated full bath, and spacious family/recreation room. Major improvements include updated heating and central air conditioning, a new driveway, retaining wall, and many additional updates (see attached improvement list). Conveniently located near the elementary school, parks, shopping, dining, and major commuting routes.

This boutique 1-bed-plus-den duplex is tucked between Marlborough and Beacon St. The upper level commands attention with soaring ceilings, rich hardwood floors, elegant wainscoting, crown molding, a wood-burning fireplace and motorized electric shades. A chef's kitchen appointed in marble countertops, white cabinetry, and stainless appliances sits beneath a picturesque window. The copper sink wet bar adds a touch of bespoke luxury. A custom glass stair gate leads to the lower level, where you'll discover a generous second entertaining space and a bonus den. Your primary suite offers a spa-caliber bathroom with a Kallista sink and glassed-in tub/shower. This brownstone ensures no modern luxury is sacrificed with central AC, in-unit laundry and a custom California Closet. Bask in the morning sunshine on your private patio. Conveniently located near green space, public transportation, restaurants, retail, renowned hospitals and prestigious universities.

10,000 OFF CLOSING COSTS! Palazzo 51, Boston's Iconic North End, Where history is lived and culture preserved. These 4 newly constructed residences-with direct elevator access and garage parking-offer a rare opportunity to own something timeless. Set among storied cobblestone streets and generations of tradition, this luxury home honors the soul of classic North End living while delivering the refinement and ease of modern design. This 2-bd, 2-bath home with an added den/office showcases refined details, herringbone flooring in the hallway, thoughtful finishes, a sophisticated mini bar, an oversized kitchen island and fireplace, reflecting craftsmanship designed for both comfort and elegance. The residence balances classic character with contemporary appeal. Unit 2 features a private deck and outdoor space, which provides an exceptional setting for entertaining. Step outside to world-renowned dining, beloved neighborhood cafes, and iconic landmarks and unmatched energy that defines North End living.

$10,000 off closing costs! Palazzo 51, Boston's Iconic North End, Where history is lived and culture preserved. These 4 newly constructed residences-with elevator and garage parking-offer a rare opportunity to own something timeless. Set among storied cobblestone streets and generations of tradition, this luxury home honors the soul of classic North End living while delivering the refinement and ease of modern design. This 2-bed, 2-bath home with an added den/office showcases refined details, herringbone flooring in the hallway, thoughtful finishes, a sophisticated mini bar, an oversized kitchen island and fireplace, reflecting craftsmanship designed for both comfort and elegance. The residence balances classic character with contemporary appeal. Unit 3 features a private deck and outdoor space, which provides an exceptional setting for entertaining. Step outside to world-renowned dining, beloved neighborhood cafes, and iconic landmarks and unmatched energy that defines North End living. Build generational wealth

Presenting 55 Commonwealth Avenue, a rare opportunity to acquire one of Back Bay's finest turnkey single-family homes, an address that rarely, if ever, comes to market. Spanning nearly 11,000 SF on the sunny side, this exceptional home offers a combination of scale, natural light, and turnkey living. Designed for both entertaining and everyday living, the home features formal living and dining rooms, an expansive family room, chefs kitchen, library, multiple offices,media room, catering kitchen, and a wellness level with fitness studio, and sauna. The residence offers 5+ bedrooms with multiple ensuite baths, three private terraces, nine fireplaces, temperature-controlled wine room, multiple laundry rooms, and a best-in-class elevator with access to every level. Complete with 2 private garage spaces and 1 gated outdoor space, this home stands as the only turnkey single-family residence available on the sunny side of the second block of Comm Ave, a genuine once-in-a-generation offering. Second block of Commonwealth Avenue

Situated on 38 acres (18 and 20 acre parcels) with more land available, this very comfortable, 4 bedroom country house can be found at the end of a very long, tree-lined drive to perfect privacy. It features tremendous charm such as 10 foot ceilings on the first floor, many archways between rooms, abundant light throughout, and 2 large, screened porches. There is a parlor with fireplace, large dining room, family room with fireplace, a deluxe, fully equipped kitchen and a bright breakfast café that opens to a screened porch, and a half bath. Primary suites – pick one: first floor with huge walk-in closet, private bath plus walk-in bay window; upstairs is a very large bedroom with a quiet, private nook for a desk, walk-in closet and full bath. Also upstairs, the other bedroom has a private bath, walk-in and best of all – a large, screened porch with views of the 50 foot pool and gardens … what a way to say goodnight to a moonlit countryside or greet your morning. On the lower level one finds a spacious recreation room with French doors to the patio and pool and a bedroom with walk-in and bath. There is plumbing roughed-in for a kitchen. Double garage with large storage attic. The stable has ten stalls, 2 wash racks, 2 grooming stalls, tack room, laundry and the extra wide center aisle. There are five board fenced paddocks, a lunging ring and an outdoor arena 300' by 180' with stone dust footing.

Positioned one of Skyline's most desirable streets with stunning jetliner views. This captivating 2-story home, built in 2020 and finished with an extensive amount of builder upgrades. A perfect blend of modern amenities and detailed craftsmanship. Featuring 3,546 square feet of living space, 5 bedrooms and 5 bathrooms .The two story entry opens with a direct view of the stunning backyard oasis. The modern chef’s kitchen features an oversized island with breakfast bar, stainless steel appliances, double ovens, and a walk-in pantry. The kitchen overlooks the dedicated dining room, and opens seamlessly to a spacious family room. A large multi-slide door connects the living space to the covered patio, creating effortless indoor-outdoor flow. A downstairs guest wing with it’s own private entrance offers versatility and perfect for multigenerational living or separate home office. A bonus room behind French doors—ideal as a home study or den.Upstairs, a bright loft anchors the secondary living space and two generously sized bedrooms with a shared bath along with an additional junior suite filled with natural light. The oversized primary retreat is a standout, complete with an expansive private balcony, spa-inspired bath with freestanding tub, walk-in shower, dual sinks, and a massive walk-in closet.Outside, the fully upgraded entertainers backyard offers an in-ground pool with custom lighting, built-in BBQ, and sweeping city-light views. Other features include fully paid-off solar panels, exterior lighting, and select areas prewired for sound, offering potential for integrated audio.Skyline residents enjoy access to two beautiful clubhouses with resort-style pools, a state of the art gym, spa, fire pits, and more. Close to award winning and highly coveted private and public schools, many shops and restaurants, and hiking trails with easy freeway access.

Set on nearly an acre within Brooklines coveted Estate Section, this extraordinary 2015-built residence offers a rare blend of privacy, scale, & exceptional construction rarely found in todays market. Spanning nearly 8,000 sq ft including a finished lower level, the home features solid mahogany floors,marble baths, custom granite stonework, 7 bedrooms, 9 bathrooms, a steam room, and multiple fireplaces including a striking outdoor granite fireplace on the covered rear deck for year-round entertaining. A fully restored original Carriage House provides two additional floors ideal for a gym, studio, or guest quarters, while a separate private office or nanny suite offers its own entrance. Built to an impressive standard with geothermal heating and cooling across six zones, radiant floor heating, Andersen Architectural Series windows, 600-amp electrical service, EV charging, and extensive CAT5 wiring. Minutes to The Country Club, Dexter Southfield, Larz Anderson Park, and downtown Boston https://maps.app.goo.gl/tJD9RCiqeG5rjJ7z6

Traverse over a mile of pristine State Park land above Pearrygin Lake to arrive at Hilltop; a 3600+ sf Prentiss-Balance-Wickline Architects masterpiece offering forever views, rare privacy, and a front row seat to nature’s majesty. Chef’s kitchen, expansive living spaces, two offices, primary suite on its own level, and an attached apartment are among the spaces to discover. Large sliding doors and a screened sitting area with hot tub just outside encourage indoor-outdoor living, and views of the lake far below. Custom details such as a built-in yoga wall, artistic metal shade screens, abundant water storage and a massive 35 kilovolt autostart generator blend practicality with luxury. Architecture and setting in perfect harmony.

Designed for elevated everyday living and effortless entertaining, this exceptional residence at 132 Country Drive in Weston offers the perfect blend of luxury, comfort, and convenience. Set in one of Weston’s most desirable neighborhoods—known for its top-ranked schools and peaceful surroundings—the home is just minutes from Boston and major commuter routes. Inside, an oversized chef’s kitchen with a large center island and walk-in pantry anchors the open-concept layout. Expansive living and dining spaces are filled with natural light, creating an inviting atmosphere throughout. Upstairs, four spacious bedrooms each feature en-suite baths and custom closets, including a luxurious primary suite with a private deck, spa-like bath, and walk-in closet. The lower level is designed for entertaining and wellness, complete with a second living area, home theater, golf simulator, gym, sauna, and more. Outdoors, the walk-out backyard offers a fire pit, dining space, and room for a future pool.

Rare Oceanfront Queen Anne Victorian Estate , Beachhurst , Boston Skyline Views directly on the ocean just 11 miles from Boston, this magnificent shingle-style home offers an unparalleled oceanfront lifestyle. Featuring 8 bedrooms (4 ensuite), & multiple outdoor spaces, the home is designed for grand entertaining and relaxed coastal living. Wake to sweeping views of Boston's glittering skyline, harbor islands, and open sea from nearly every room. Direct access to Eisen Beach puts sand and surf at your doorstep. The chef's kitchen opens via French doors straight to the water, while the wraparound covered porch and pergola invite endless hours of coastal enjoyment. The original craftsmanship designed by Richard Morris Hunt shines with inlaid hardwood floors, hand-carved balusters, stained-glass entry doors, rich wood paneling & multiple ornate fireplaces. Swampscott's most iconic oceanfront home with green lawn, all just minutes from the commuter rail with direct service to Boston.