luxury real estate 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.

Rare waterfront living on the Mystic Lakes. This exceptional, secluded residence offers a lifestyle centered around nature, relaxation, and creating generations of memories. Filled with natural light and stunning water views, the home features spacious living and dining areas ideal for everyday living and entertaining. The family room showcases a dramatic picture window overlooking the water with access to a deck perfect for gatherings. A well-appointed kitchen and dedicated home office add comfort and functionality. Upstairs are more than four spacious bedrooms including a beautiful primary suite retreat. A third-floor artist studio and expansive basement workshop offer exceptional flexibility. For the car enthusiast there is a four car garage . Enjoy decades of memories and a legacy lifestyle steps to the water invite kayaking, paddleboarding, boating, fishing, and year-round enjoyment of this extraordinary waterfront setting. Convenient to Cambridge and beyond.

Perched high atop an Arlington Hill, this custom home invites a slower rhythm. Think sunsets from the farmer’s porch, chirping birds in the garden, and light that moves beautifully throughout every space. Built in 2008 and thoughtfully elevated since, its construction and solar efficiency shine in both form and function. Soaring ceilings in the entryway and a natural sense of balance reflect throughout the open floor plan. The kitchen invites gatherings with friends and family, opening seamlessly to a deck and dreamy side yard. The main level offers a harmonious balance between connection and retreat, while upstairs features four bedrooms, including a primary suite with spacious sitting area and bathroom featuring a soaking tub, with laundry room nearby. An unfinished lower level is ripe with potential, third-floor attic offers additional opportunity for expansion and the two car garage keeps life organized. Set on a quiet cul-de-sac, lifestyle and location align, just minutes to the bike path and Mass Ave!

Adorned with timeless details and character at every turn, 82 Richfield Road is a truly distinguished property that has been meticulously cared for by the same owners for nearly 30 years. Original wood detailing and archways immediately set the stage upon entry into the foyer, with its elegant staircase, and into a sophisticated library with rows of built-in bookshelves, beamed ceilings and electric fireplace. The main level continues to an updated kitchen with high-end appliances, double oven, granite counters, large center island and a versatile wet bar with additional storage before leading into a formal dining room and an oversized living room with wood-burning fireplace. The second floor features three bedrooms, a modern full bath and an office, but it does not end there. A fully finished third level has two additional bedrooms with cathedral ceilings and a full bath with double vanity. Enjoy the outdoors on your back patio, covered side porch or on the nearby bike path.

Tucked along a dead-end street in the beloved Peirce School neighborhood, this home offers the kind of community people rarely want to leave. Neighbors genuinely care for one another, front porch conversations are part of daily life and there’s a true sense of connection. Raised in this very home, the current owner holds decades of cherished memories, from holidays to block parties ...any reason to bring neighbor friends together. Ready for its next chapter, this diamond-in-the-rough will require substantial renovation but presents a wonderful opportunity to create something special. The main level offers a comfortable floor plan including bedrooms and a fireplaced living room while upstairs offers two additional bedrooms + a loft. The lower level, once used as in-law space features excellent ceiling height and an older kitchen. Nature lovers will enjoy the short stroll to McClennan Park, Whipple Hill trails and the Minuteman Bike-path! Renovate as is? Start fresh? Second level? You decide!

Builders, contractors and investors, this single-family home resides in an R-2 zoning district on a sizable, level lot, creating potential expansion options alongside Lower Mystic Lake in a prime neighborhood that provides easy access to Mass. Ave, the Mystic River Path, Alewife Greenway Bike Path, the bus route and the Medford Center commuter rail station. Please contact listing agent to confirm appointment prior to visiting property. Interior access allowed only through scheduled group showings.

Stunning, turn-key townhome offering scenic views of Mystic Lake. The open concept living, dining, and culinary spaces are expertly designed for effortless entertaining. The gourmet kitchen is a masterpiece, featuring sleek countertops, high-end appliances, and an expansive seven-foot island. A dedicated sitting area or office nook overlook your private patio and spacious yard which is a perfect retreat for quiet moments. The second level hosts two generous bedrooms, convenient side by side laundry and a beautifully appointed full bath. Ascend to the top-floor primary suite, a true haven of tranquility. This expansive suite features an elegant full bath with a separate soaking tub. Sliding glass doors reveal a private enclosed deck which is the ultimate setting for morning coffee overlooking the lake. Pristine hardwood floors, and custom closets throughout. Close to Arlington Center with shops, restaurants, trails, and playgrounds. Truly an exceptional home in a premier location!

Stunning, turn-key townhome offering scenic views of Mystic Lake. The open concept living, dining, and culinary spaces are expertly designed for effortless entertaining. The gourmet kitchen is a masterpiece, featuring sleek countertops, high-end appliances, and an expansive seven-foot island. A dedicated sitting area or office nook overlook your private patio and spacious yard which is a perfect retreat for quiet moments. The second level hosts two generous bedrooms, convenient side by side laundry and a beautifully appointed full bath. Ascend to the top-floor primary suite, a true haven of tranquility. This expansive suite features an elegant full bath with a separate soaking tub. Sliding glass doors reveal a private enclosed deck which is the ultimate setting for morning coffee overlooking the lake. Pristine hardwood floors, and custom closets throughout. Close to Arlington Center with shops, restaurants, trails, and playgrounds. Truly an exceptional home in a premier location!

Thoughtfully designed, energy-efficient three-bedroom, two-and-a-half-bath new construction townhome blending modern style with everyday functionality. Enter to a sun-filled, open-concept main level where the kitchen, living, and dining areas flow seamlessly together. Designed with today’s trends in mind, the space features sleek countertops, generous island, white cabinetry, stainless steel appliances, recessed lighting, and hardwood floors with a natural finish. The second floor offers two spacious bedrooms with ample closet space one with a balcony, a full family bathroom, and a dedicated laundry area. The top floor primary suite serves as a private retreat, highlighted by cathedral ceilings and a private balcony The ensuite bath is well-appointed with a double vanity and walk-in shower. Additional features - finish lower level offering flexible space for a media room, gym or playroom, a yard and two off street parking spaces.

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!!

Beautifully renovated & sunlit three bed / two bath upper-level condo on a quiet street in desirable West Medford moments from the trails, water views, and green space of the Lower Mystic Lake. This thoughtfully converted home offers modern finishes throughout, including new oak HW floors, white cabinetry, quartz countertops, central HVAC and upgraded 200-amp elec. service. The well-designed layout is the ideal entertaining space for dinner parties and more plus an expansive full walk-up finished attic is perfect as a media room, home office, fitness space, or guest den. In-unit washer/dryer and bonus basement flex space adds everyday convenience. Rare offering w/ one garage space plus one additional outdoor spot and a private rear deck. Ideally located near the commuter rail station for easy access to Downtown Boston, with close proximity to Winchester and Arlington steps away. Turnkey opportunity offering the dream of lifestyle, luxury and convenience, all set in a highly sought after neighborhood

Beautifully renovated & sunlit two bed / two bath condo on a quiet street in desirable West Medford moments from the trails, water views, and green space of the Lower Mystic Lake. This thoughtfully converted home offers modern finishes throughout, including new oak hardwood floors, white cabinetry, quartz countertops, central HVAC, and upgraded 200-amp electrical service. The well-designed layout is the ideal entertaining space for dinner parties and more plus the finished lower level is perfect as a media room, home office, fitness space, or guest den. In-unit washer/dryer and extra storage adds everyday convenience. Rare offering with one garage space plus one additional outdoor spot and a private rear deck. Ideally located near the West Medford commuter rail station for easy access to Downtown Boston, with close proximity to Winchester and Arlington steps away. Turnkey opportunity offering the dream of lifestyle, luxury and convenience, all set within a highly sought after neighborhood.

Beautifully renovated & sunlit three bed / two bath upper-level condo on a quiet street in desirable West Medford moments from the trails, water views, and green space of the Lower Mystic Lake. This thoughtfully converted home offers modern finishes throughout, including new oak HW floors, white cabinetry, quartz countertops, central HVAC and upgraded 200-amp elec. service. The well-designed layout is the ideal entertaining space for dinner parties and more plus an expansive full walk-up finished attic is perfect as a media room, home office, fitness space, or guest den. In-unit washer/dryer and bonus basement flex space adds everyday convenience. Rare offering w/ one garage space plus one additional outdoor spot and a private rear deck. Ideally located near the commuter rail station for easy access to Downtown Boston, with close proximity to Winchester and Arlington steps away. Turnkey opportunity offering the dream of lifestyle, luxury & convenience, all set in a highly sought after neighborhood

Located in the heart of Arlington Center, this charming two bed, two and a half-bath townhouse-style condo offers the perfect blend of comfort and convenience. Just moments to the Bike Path, shops, restaurants, and all that Arlington Center has to offer. The main level features an open-concept layout w/ vaulted ceilings, hardwood floors, and a spacious living and dining area that flows seamlessly into a well-appointed kitchen w/ stainless steel appliances. The first floor bedroom includes its own en-suite bath, offering flexibility for guests or a convenient primary option. Upstairs, you’ll find a second bedroom suite w/ its own full bath and access to a private balcony, perfect for morning coffee or unwinding at the end of the day. Additional highlights include excellent natural light, in-unit laundry, one deeded parking space and lovely updated patio area. A fantastic opportunity to own a well-located, move-in ready home in Arlington Center!

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

Opportunity awaits in Arlington Heights! Ideally located just off Mass Ave within the MBTA overlay district, 15 Howard Street is a classic two-family home rich in character and full of potential. Offering a total of six beds and two full baths across two spacious units, each level features hardwood floors, a wood-burning fireplace, and inviting layouts that feel both comfortable and full of possibility. From the moment you enter, you’ll appreciate the warmth and history throughout. Generous living and dining areas, original details, and a traditional floor plan to create the perfect canvas, whether you’re looking to restore its timeless charm or bring a fresh, modern vision to life. The property also includes a two car garage and is set in a location that offers both everyday convenience and a strong sense of community. A rare opportunity for investors, end-users, or anyone looking to create something truly special in Arlington.