luxury houses for sale Winchester, United States

Looking for a home that works beautifully whether you’re upsizing, downsizing, or simply ready for something special? This renovated and expanded Cape is full of surprises! Tucked away on a dead-end street in Arlington’s coveted Morningside neighborhood near Stratton School, it was thoughtfully reimagined by a respected local builder to offer the rare luxury of true one-level living. The sun-filled main level features a spacious primary suite, second bedroom, guest bath, and a showstopping open-concept kitchen that flows effortlessly into the dining and family rooms. A charming fireplace and oversized picture window create an inviting setting for cozy evenings and memorable gatherings. Upstairs, two generously sized bedrooms and another full bath offer wonderful flexibility for guests, hobbies, or working from home. Outside, a large deck overlooks a private backyard framed by mature trees, perfect for summer dinners, weekend entertaining, gardening, or simply unwinding. Stylish, spacious, and incredibly versatile, this is the Morningside home you’ve been waiting for!

Thoughtfully updated and offering exceptional flexibility, this spacious Arlington ranch combines the ease of one-level living with a finished lower level and a location close to many of the town’s most sought-after amenities. The main level features hardwood floors and a bright, open layout with three bedrooms and a full bath. At the heart of the home, the updated kitchen features quartz counters, stainless steel appliances and an island, opening to the living/dining room with a wood stove and seasonal views of Lower Mystic Lake. A large family room at the rear of the home adds another impressive gathering space, highlighted by cathedral ceilings, another wood stove and amazing natural light, making this the coziest room in the house. The updates continue throughout with freshly painted interior and exterior and a remodeled lower level that significantly expands the home’s versatility, complemented by a fully renovated bathroom featuring a tiled walk-in shower. Whether used as an office, home gym, playroom or guest space, the lower level provides valuable flexibility beyond the main living areas. Outside, enjoy a spacious backyard and large deck with plenty of room to relax, entertain or dine outdoors. An attached garage with direct interior access, central air and walk-up attic storage add to the home’s everyday functionality. Set in a convenient location just moments from Bishop Elementary School, this home also provides easy access to Mass Ave, Arlington Center, the Minuteman Bikeway, shops, restaurants, public transportation and everything that makes Arlington such a great place to call home. Move right in and enjoy a home that brings together space, updates, versatility and location.

Welcome to 81 Ridge Street, where timeless charm, comfortable living, and beautiful outdoor spaces come together in a wonderful Arlington setting! Lovingly maintained and thoughtfully updated by the same family for over 60 years, this inviting brick home seamlessly blends classic character with modern-day comfort. A welcoming living room featuring a beautiful marble fireplace flows into the formal dining room, while the adjoining family room offers additional space for gathering, entertaining, or simply relaxing. Three bedrooms and a full bath complete the main level, while the finished lower level provides versatile space for recreation, hobbies, or a home office. Step outside to discover a private backyard retreat, where a charming patio nestled among established gardens invites peaceful mornings and memorable evenings. The expansive 10,606-square-foot lot, comprised of two formerly separate parcels, offers exceptional outdoor space for gardening, recreation, and endless possibilities. Complete with a two-car garage and convenient access to Arlington's shops, restaurants, parks, and commuter routes, this move-in-ready home is ready for its next chapter. A special place where cherished memories are made and new beginnings await! Showings begin at the Open House 10/29 4-530pm.

There’s more to this ranch than you might expect from the street. The main level keeps daily life straightforward, with great natural light in the fireplaced living room and adjoining dining or bonus area. Sliders lead to a deck with treetop views overlooking the yard, giving the main living areas a welcome connection to the outdoors. The eat-in kitchen is ready for its next update, but its size gives you something worth working with rather than working around. Three bedrooms and a full bath keep everything you need on one floor. Downstairs is where the house starts to separate itself. High ceilings and a walkout family room create a substantial second living area, complemented by a kitchenette and laundry. Use it for movie nights, guests, hobbies, or simply the extra room that becomes increasingly valuable over time. Direct access to the extended garage provides room for cars, a workshop, equipment, or storage. The backyard deserves some attention of its own. A second deck brings you down to the yard, where a fenced area works well for pets and the remaining space leaves plenty of room to garden, play, or spend an afternoon outside. When you’re heading out, the 67 bus offers direct service to Alewife and nearby parks give you more places to explore. This isn’t a finished renovation with someone else’s choices built into the price. It’s a useful, surprisingly roomy home that you can live in now and improve at your own pace.

Welcome to 10 Governor Road, where 1927 character, wooded privacy and thoughtful updates come together on a quiet cul-de-sac. Sun-drenched living and dining spaces overlook a dappled pollinator garden alive with wildlife. Refinished hardwood floors add warmth, while the renovated kitchen blends style and function. A charming office with French doors overlooks neighborhood green space, a mudroom adds convenience, and three bedrooms and a renovated full bath complete the living space. Since 2023, significant improvements include a new roof, heat pumps, 200-amp electrical service, plumbing and water-pressure upgrades, and stainless steel appliances. Outside, new fencing, established fruit trees and berry bushes, and a pea-stone patio with firepit create a backyard oasis. Enjoy easy access to the Minuteman Bikeway, shops, restaurants, Arlington Reservoir, Great Meadows, parks, MBTA and Route 2. Showings begin Thursday. Offers due Tuesday, 9/29 at 10am. Home is where hearts gather and dreams take root!

OPPORTUNITY KNOCKS IN ARLINGTON! Bring your vision, creativity and imagination to this unique offering of TWO adjoining parcels being sold together, totaling approximately 8,340 square feet. of land! Whether you're a developer, builder, investor or end user dreaming of creating your ideal home, the possibilities are worth exploring. Original owner home offered for the first time, the existing 1958 Cape features three bedrooms plus first floor bonus room, for a total of seven rooms with nearly 1,500 square feet. of living space, hardwood flooring, an unfinished basement and attached garage. Ready for significant updates and renovation, the home offers an opportunity to restore, reimagine or explore expansion and redevelopment possibilities. The adjoining vacant parcel at 0 Lot Rockland Avenue adds valuable land area and flexibility to this offering. Conveniently located near Arlington's shops, restaurants, parks, public transportation and commuter routes, this property presents an exciting opportunity in a sought-after community. Two parcels, one offering and a chance to bring your vision to life! Buyers and their agents to perform their own due diligence regarding permitted uses, zoning and development potential. Offers are due Wed. 10/21 at 10am.

Well maintained two family located on a lovely tree lined street just one block from the Mystic River offers wonderful expansion potential. The property features a two car garage and double wide driveway offering plenty of parking. Unit 1: two bedrooms one bath, renovated kitchen, inviting living room, formal dining room with built in hutch and a back porch. Unit 2: has two levels, three bedrooms, one bath, renovated kitchen, living room with window seats, formal dining room, sitting room, enclosed front porch and back porch. The front to back heated third floor provides two additional rooms. Both units offer separate systems, updated eat-in-kitchens w quartz counters and SS appliances. hardwood floors, original gumwood, wood accents and back porches overlooking a fenced yard. Walking distance to public transportation and the Commuter Rail, Arlington Center, West Medford Square, parks, conservation land and major routes. Offers if any will be reviewed Monday by 1 PM. Please allow 24 hours for responses.

A great place to call home! Lovely single-family Colonial in pristine condition, near the Lexington line, offers a sun-filled living room, new, eat-in kitchen with stainless steel appliances, and spacious work area. Beautiful family room with half bath, fireplace and adjacent deck overlooking Whipple Hill Conservation. The second floor offers a flexible floor plan with an option for a fourth bedroom, which is presently used as a playroom, and new full bath. Great potential to finish 600 plus square feet on the lower level. Nice secluded backyard with tranquil setting. Near McClennen Park, Town Beach, Minuteman Bike Path, transportation, and shops. Do not miss this wonderful opportunity!!

Step inside and this home immediately shows what over 4,000 square feet of thoughtful new construction can do. Four finished levels offer 13 rooms, more than five bedrooms, and four and a half baths, with a layout designed to flex with the way you live. The main level features open-concept living, dining, and kitchen area anchored by a custom feature wall, wood mantle, and electric fireplace. The chef’s kitchen shines with custom soft-close cabinetry, under-cabinet lighting, oversized island with pendant lighting, quartz counters, designer marble backsplash, and a full Energy Star-rated Bosch™ appliance suite, including a wine fridge. Entertain seamlessly with direct access to the composite deck and cement paver patio.Upstairs, the private primary suite includes a custom walk-in closet, spa-inspired en-suite bath with double vanity, glass-enclosed shower, dual showerheads, and bench seating. The standout feature is an expansive covered cathedral porch with recessed lighting and composite decking, accessed directly from the bedroom. Three additional bedrooms, a second full bath with custom porcelain tile, and second-floor laundry complete the level.The third floor offers three finished rooms plus a full bath, creating flexible space for bedrooms, a family room, home office, guest suite, playroom, or au pair setup. The fully finished lower level adds luxury vinyl plank flooring, a full bath, utility room—ideal for a gym, media room, or guest space.Set on a prime corner lot at Winthrop Street and Franklin Avenue, the property pairs exceptional square footage with a rare three car oversized garage that is heated and cooled, plus driveway parking for six more vehicles. Additional highlights include a 4-zone Bosch™ heat pump system, spray foam insulation, and 400 AMP electrical service.Enjoy a location steps from the West Medford Commuter Rail, walkable to West Medford Square’s shops and restaurants, minutes from the Middlesex Fells Reservation, and convenient to Route 93 and downtown Boston—all within the historic, tree-lined charm of one of Medford’s most sought-after locations.

This classic West Medford two-family offers incredible potential and a rare opportunity for investors, multi-generational buyers, or end users looking to create their own vision. Perfect for those seeking a home with income, each unit is thoughtfully laid out with two bedrooms, a full bathroom, a large kitchen, open living and dining rooms, plus a bright office/sunroom—ideal for working from home or relaxing with morning coffee. The second-floor unit also includes a generous foyer, perfect for a mudroom or additional office space. With its timeless wood siding, welcoming decks, and a great yard ready for play space or a vegetable garden, the home has both charm and versatility. Practical updates include a newer roof and oil tank, while the sizable driveway provides ample off-street parking. Tucked into a neighborhood near the commuter train, the Fells, schools, and everything West Medford has to offer! This is an outstanding chance to invest, live, and grow in a prime location.

This is the kind of property that can look very different depending on who owns it. One person may see two comfortable homes under one roof. Another may see rental income helping offset the cost of ownership. Someone else may be thinking about extended family, long-term investment, or a future conversion to condominiums. Each unit offers two bedrooms, one bath, open living and dining areas, and a large updated kitchen with enough room for everyday life to feel comfortable rather than compressed. The second unit continues onto the third floor, adding two more bedrooms, another full bath, a work-from-home or studio area, and generous storage. Outside, composite decks and a screened porch create places to enjoy the property beyond the interior walls. Mini splits in both units, electrical upgrades, a two car garage and an EV charger bring useful improvements to a classic Arlington two-family. Then there is the location. Mass Ave, Menotomy Rocks Park, Robbins Farm Park, the bike path, and bus service to Alewife and Harvard Square all sit within reach, which means the property works just as well for someone who wants to stay close to home as it does for someone moving between Arlington and the city. The appeal here is not one specific use. It is having a property that can keep making sense even as your plans change.

Thoughtfully conceived and beautifully executed, this exceptional new construction residence offers more than 7,600 square feet of impeccably designed living space in Lexington’s coveted Sun Valley neighborhood. A two-story foyer makes an immediate impression, introducing sun-filled interiors with generous ceiling heights, large-scale windows, and wide-plank hardwood floors throughout. Elegant formal living and dining rooms lead to a spectacular chef’s kitchen centered around an oversized island, complemented by a walk-in pantry, service bar with wine refrigeration, and breakfast area opening to a private deck. The adjoining fireplaced family room is framed by custom built-ins and flows into a striking window-wrapped sitting room with a vaulted tongue-and-groove ceiling, creating one of the home’s signature architectural moments. A first-floor bedroom suite or office adds flexibility. Upstairs, the primary includes two boutique-style dressing rooms with tailored built-ins and a spa-quality bathroom. Four additional bedrooms—two en suites and a Jack-and-Jill suite—accommodate family and guests with privacy and ease. The walk-out lower level extends the living space with a recreation lounge, dedicated theatre room, home gym, and private bedroom suite. Outside, professionally landscaped grounds unfold across nearly an acre of level lawn with classic stone walls and lush, layered plantings. Rows of Green Giant arborvitae establish an attractive year-round privacy screen, while a granite patio and deck enhance a sprawling backyard with ample room for a future pool. Natural gas service—an increasingly rare amenity in Lexington’s newest luxury homes—adds to the property’s distinction. A truly custom residence where refined finishes, timeless character, and an unparalleled setting come together to create a legacy home to be treasured for generations.

Robbins Farm, Menotomy Rocks Park, and Mass Ave all sit within easy reach, giving you a part of Arlington where the outdoors and the activity of town can both be part of the same day. Cared for by the same owners for more than 50 years, this is a home with a long history of thoughtful upkeep and everyday use. Inside, the first floor is comfortable and straightforward. The living room centers around a fireplace, and the dining room opens through sliding doors to a deck overlooking the private backyard. Mature landscaping gives the yard an established feel, making the deck an appealing spot for dinner outside, morning coffee, or a quiet end to the day. The updated kitchen adds useful storage with a large pantry that keeps everyday items from crowding the counters. Upstairs are three bedrooms and a full bath, keeping the sleeping areas together and separate from the main living floor. Downstairs, the basement provides laundry along with plenty of storage for bikes, seasonal gear, tools, and everything else that tends to follow you home. Set in the Brackett School neighborhood, this is a house that has been well cared for over time and makes it easy to enjoy both the tranquil and more active sides of Arlington without having to choose between them.

Classic Tudor character meets a sought-after Arlington location. Set in the Brackett School neighborhood just moments from Robbins Farm Park, this charming home offers period details, comfortable living spaces, and convenient access to Route 2 and Alewife. The first floor features a welcoming fireplaced living room with beautiful natural woodwork, along with a versatile sunroom/den ideal for a home office, playroom, or quiet retreat. The dining room includes a built-in cabinet and opens to a screened porch, creating a wonderful spot to relax or enjoy warmer months. A spacious eat-in kitchen with skylights brings in abundant natural light, and a half bath completes the main level. Upstairs are three bedrooms and a full bathroom. Additional features include an unfinished basement offering useful storage and future potential, plus a one-car garage. With classic Tudor architecture, flexible living spaces, and easy access to parks, schools, commuting routes, and Arlington amenities, this is a wonderful opportunity to make a distinctive home your own.

Rare opportunity in a magnificent Menotomy Rocks Park neighborhood! Tucked away on a dead-end street, this six room, three bedroom, two bath single-family home offers an exceptional opportunity to create something special in one of Arlington’s most desirable locations. Just minutes from Menotomy Rocks Park and Brackett School, the setting offers the perfect combination of neighborhood charm, privacy, and convenient access to some of Arlington’s most treasured amenities. This property will require extensive updating and renovation, making it an ideal opportunity for a buyer with vision who is looking to build equity and create a home tailored to their own style and needs. The existing floor plan provides a solid starting point, with three bedrooms and two bathrooms, while the property offers exciting potential for thoughtful improvements and modernization. Opportunities to purchase a single-family home in this neighborhood at this price point are exceptionally rare. Whether you're a first-time buyer looking to transform a home over time, an investor, or a developer seeking a property with upside, this is a chance to create value in a truly special location. The home will be sold as-is and requires significant renovation. Bring your ideas, vision, and creativity and take advantage of this rare opportunity to establish a home in the highly sought-after Menotomy Rocks Park neighborhood.