luxury houses 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!

Ever heard of the phrase “business in the front, party in the back?” This home understood the assignment. Built into the hillside on a beautifully landscaped 10,000+ square feet lot, this 1967 gem has a vibe all its own, serving up a little post-mid-century personality with room to make it shine. From the street, a sweet bungalow/ranch welcomes you to the main level, where a garage, den, dining room, updated kitchen, three generous bedrooms and a fully tiled bath complete the floor. Then head downstairs, this is when it really gets interesting! Designed for gathering, the walkout lower level features a generous fireplaced living room, separate bar area and sliders to a gorgeous deck overlooking the lush green backyard. An optional primary suite with full bath, second garage bay and additional level of storage add flexibility. Cool, quirky, practical and full of potential, if you like it then you'll LOVE it! All on a quiet, dead-end street near the bike path and loads of shops and restaurants on 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!

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!!

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

Rare opportunity in the heart of West Medford! This traditional Colonial, set on a large private lot, offers exceptional potential for developers, investors, or buyers with vision. Currently zoned GR, the property presents the strong possibility for 2 units with street frontage on both Sharon and Sherman Streets. Historic Commission approval for removal has already been obtained by the owners. Ideally located with easy access to Cambridge, Boston, and Tufts University, while also convenient to the MBTA Commuter Rail with direct access to North Station. Enjoy nearby shops, restaurants, and the vibrant West Medford neighborhood. Whether restoring the existing home or pursuing redevelopment, this is a unique opportunity in a prime location.

Thoughtfully designed, energy-efficient three-bedroom, two-and-a-half-bath new construction townhome blending modern style with everyday functionality. The sun-filled open-concept main level features a spacious kitchen, living, and dining area with sleek countertops, a generous island, white cabinetry, stainless steel appliances, recessed lighting, and hardwood floors throughout. The second floor offers two spacious bedrooms, including one with a private balcony, a full family bathroom, and a dedicated laundry area. The top-floor primary suite is a private retreat with cathedral ceilings, a private balcony, generous closet space, and an ensuite bath featuring a double vanity and walk-in shower. Additional highlights include a finished lower level ideal for a media room, gym, playroom, or home office, a shared yard, and the convenience of a one-car garage. Ideally located on Lewis Avenue, close to Arlington centre's shops, restaurants, parks, and commuter routes.

Perched high above the treetops on a horseshoe street in coveted Jason Heights, life here feels calmer, prettier and deeply connected to nature. With Menotomy Rocks Park at the end of the street, morning walks, birdwatching, skating on the pond and sunset strolls become part of your daily rhythm. Thoughtfully redesigned, this gracious 1930’s home beautifully blends timeless charm with today’s modern lifestyle. The sunny kitchen is the heart of the home, featuring crisp white cabinetry, an island, SS appliances and seamless flow into the dining room. A fireplaced living room invites cozy evenings while the screened slate porch and outdoor hot tub feel like a private retreat! Upstairs are four spacious bedrooms including a primary suite with spa-like bath and custom walk-in closet + a very cool teen suite that feels like a treehouse with bedroom, sitting room and remodeled bath. Owned solar panels, a 2023 roof and 12,000+ square feet make this spot ideal + just mins to the amenities that the Center has to offer!

Exceptional opportunity for investors, developers, or owner occupants in a prime Lexington location just a short stroll to Mass Ave shopping, restaurants, the bike path, Arlington Reservoir Beach, and public transportation. This three-family property offers strong potential and versatility. The first floor unit features two bedrooms, a living room, full bath, and an updated kitchen with granite countertops. Unit two spans two levels with a living room, kit and bath on one level and a bedroom and additional bath on the second. The third unit is the largest and includes two bedrooms, a sunroom/family room, living room, kitchen, and bath. Utilities are separately metered except for water and sewer. Additional highlights include Navien high-efficiency heating systems, coin-operated laundry, ample parking with three garage spaces and six additional spots, a small yard, and a roof deck. Ideally situated on a side street just off Mass Ave, this is a rare and compelling opportunity.

Terrific Lexington home! This pristine Colonial on a side street has been meticulously maintained by the current owners and it shows! From pretty hardwood floors to newer systems, replacement windows throughout, newer roof, insulation added, renovated baths, AC added with mini-splits, and so much more. Enjoy the welcoming living room with cozy fireplace, formal dining room, remodeled kitchen and powder room leading to 3 good size bedrooms and an updated bath on the second level. You’ll appreciate the bonus flexible living space in the finished lower level family room, office area, full bath and storage. Enjoy summer activities and relax on the deck in your private backyard. A welcoming home in a quiet Lexington neighborhood with easy access to the bike path, Great Meadows trails, swimming at the Arlington Res Beach, shopping, restaurants and public transportation. Welcome to your new home!

Set in an idyllic location abutting Robbins Farm/Skyline Park, this exceptional three bedroom, two and a half bath home offers a rare combination of privacy, beauty and modern convenience. Inside, a stunningly renovated kitchen anchors the home, complemented by a sweet mudroom, full bath and the warm inviting living room with fireplace and charming dining. Upstairs, three well-appointed bedrooms and a full bath are surrounded by serene treetop views from every window, creating a peaceful retreat. The semi finished basement offers added versatility with a 1/2 bath, ideal for a home office, playroom, or workout space. Great storage in huge attic and basement. From your backyard, enjoy breathtaking sunrises, front-row views of seasonal fireworks and direct access through your own private gate to the park’s beloved sledding hill, playground, and park activities - an extension of your own outdoor space. Close to Brackett School, Mass. Ave. busses, and all the shops and eclectic eateries of the Heights and Center.