luxury houses for sale Winchester, United States

Welcome to this well-cared-for Colonial in desirable West Medford! Offering a wonderful combination of classic charm, comfortable living space (with central air), and versatile bonus areas, this home is ready to welcome its next owners. The first floor is designed for both everyday living and entertaining, with a spacious living room with fireplace, dining room, remodeled kitchen (2018), and inviting family room. An enclosed deck extends the living space and provides a great spot for relaxing, entertaining, or enjoying the outdoors in a more private setting. The second floor features three bedrooms and a family bath, providing a comfortable and functional bedroom level. The finished lower level adds even more versatility and offers numerous possibilities to suit today's lifestyle. With its own bathroom, laundry, and partial kitchen, this space could work beautifully as a game room, recreation area, home office, guest space, or an ideal setup for extended family. The thoughtful layout and additional amenities make the lower level a valuable extension of the home. The spacious and private yard offers plenty of room to enjoy the outdoors, whether you're an avid gardener, love to entertain, or simply want a place to unwind. Mature landscaping creates a wonderful sense of privacy, while two sheds provide excellent storage for gardening equipment, tools, and outdoor belongings. A hot tub adds another opportunity to relax and enjoy your own private outdoor retreat. A great opportunity to own a well-maintained Colonial in a sought-after West Medford location (restaurants, shops, commuter rail and access to major routes), with generous living space and the flexibility to adapt to a variety of needs. Come see all this special home has to offer!

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!

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.

Terrific opportunity to own in the heart of Arlington! Lovingly maintained and tucked into a wonderful Turkey Hill neighborhood, this classic Colonial offers the perfect blend of charm, space, and convenience. Enjoy a peaceful setting that feels tucked away, yet is just moments from the bike trail, skating rink, bike park, public transportation, and local amenities. Inside, you’ll find a spacious and flexible layout with three comfortable bedrooms, two baths, and plenty of room for both everyday living and working from home. The unfinished attic presents exciting potential for future expansion, while the basement provides excellent storage space. Set on a desirable corner lot, the home also offers multiple outdoor spaces to relax and unwind, including a sunny patio and a private deck off the main bedroom. Whether you’re looking to move right in and enjoy its warmth or add your own personal updates over time, this is a special opportunity in a sought after Arlington neighborhood.

Thoughtfully reimagined through a complete renovation and expansion in 2018, this exceptional home brings modern design and functionality to a convenient location. Sun-drenched living spaces unfold across four finished levels, anchored by an expansive open-concept main level with a beautifully appointed kitchen featuring stone countertops, stainless steel appliances and a large center island designed for everyday living and effortless entertaining. The second level features two large bedrooms and a full bath, while the entire third floor is devoted to a luxurious primary suite with a walk-in closet and private bath. The finished walk-out lower level offers flexible space for a family room, home office or gym. Enjoy the relaxing outdoor space from the private deck and backyard, or head around the corner to Turkey Hill Reservation. Perfectly positioned just moments from Mass Ave, the Minuteman Bike Path and Stratton Elementary, this home delivers a quintessential Arlington lifestyle.

For the price of a condo, you can have your very own slice of paradise, yet with a yard, a deck, a ridiculously cute shed + room to dream! Custom built in 1956 and lovingly maintained by the same family ever since, it has that easy, comfortable, “just feels right” vibe that makes you want to kick off your shoes and unwind. With loads of updates over the years, one stands out: the 2014 kitchen redesign was a clever one, with granite counters, updated appliances and a stylish peninsula that doubles as prep space + the daily dining spot. After dinner, step out onto the deck and enjoy the mature trees and the lush, green, fenced in yard. Relax after a long day as the main level bath offers a separate shower + soaking tub, because sometimes you deserve to soak like royalty! Four bedrooms…two up, two down…give you plenty of flexibility for bedrooms, an office, guests, a playroom or whatever life throws your way! And here’s where this one really starts to shine: you can hit the easy button. Vinyl siding, updated windows + central air mean fewer things to worry about and more time to enjoy the lifestyle that Arlington offers. With its 7,200 square feet lot + 60 feet of frontage, there are plenty of options…maybe expand down the road, finish the lower level that already has nice ceiling height for a bonus retreat or add an ADU for an aging relative or home office? All of this in a location that makes everyday life easy, too. Just two blocks off the bike path, near McClennan Park/trails + close to all the Mass Ave fun, including restaurants, shops, coffee, errands and more. Commuting to Cambridge and Boston is easy, too, with the 77 bus to Alewife nearby. Cute, comfortable, practical + full of possibilities, this one is a gem!

Well maintained 2 family located on a lovely tree lined street just one block from the Mystic River offers wonderful expansion potential. The property features a 2 car garage and double wide driveway offering plenty of parking. Unit 1: 2 bedrooms 1 bath, renovated kitchen, inviting living room, formal dining room with built in hutch and a back porch. Unit 2: has 2 levels, 3 bedrooms, 1 bath, renovated kitchen, living room with window seats, formal dining room, sitting room, enclosed front porch and back porch. The front to back heated 3rd floor provides 2 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!!

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, an office nook 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.

This cherished classic two-family has been lovingly owned by the same family for over 50 years. Original, preserved gumwood moulding runs throughout, complemented by high ceilings and incredibly bright rooms. First and second floor units each offer two bedroom and one bath, large living and dining rooms with China cabinet, sunroom/office, and kitchen with granite. Beautiful hardwood floors run throughout — preserved beneath the first floor carpet and ready to be uncovered. Upper unit adds a third level with two more BRs (one with mini-split), half bath and family room. Enclosed back porches, a sweet, level backyard, and basement storage offer extra space to relax, play, or stash your gear. New windows on the second and third floors, both heating systems replaced about four years ago. Two garage spaces + extra parking. A wonderful opportunity for owner-occupants, multi-generational families, or investors seeking rental income. Nestled in a friendly neighborhood where block parties are still a thing, just steps to the serene Menotomy Rocks Park and Robbins Farm/Skyline Park, convenient to Mass Ave, and in the district for the award-winning Brackett School. A true Arlington gem!

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.

Welcome to 21 Valentine Road, a gracious Tudor-style home filled with natural light, timeless character, and inviting spaces inside and out. Cherished by the same family for 35 years, this special home has been lovingly cared for and is now ready to welcome a new generation to create memories of their own. Set on a beautiful, level lot in a desirable Arlington location, this spacious home offers four bedrooms, two and a half baths, hardwood floors, beautiful moldings, and charming built-ins throughout. The first floor features generously sized living and dining rooms, a spacious kitchen, a convenient rear mudroom entry, and a sunny room—an inviting spot for reading, relaxing, or working from home. Upstairs are four well-proportioned bedrooms and two full baths, including a private primary suite with an oversized window and skylight that fill the space with natural light. Outside, enjoy a large, fully fenced backyard with a level lawn, established planting areas, and plenty of room for outdoor dining, entertaining, gardening, and play. A garage and electric vehicle charger add everyday convenience. Ideally located near Dallin Elementary School, parks, the Minuteman Bikeway, restaurants, shopping, and all that Arlington has to offer, 21 Valentine Road is a wonderful opportunity to own a character-filled home with generous living space, a fabulous yard, and an exceptional location.

Stunning New Construction Home just completed by a well-established Lexington builder, thoughtfully designed for today’s lifestyle. This 6 BR, 5.5-bath home offers exceptional flexibility with two primary suites, including a sought-after first-floor bedroom. A chef’s kitchen is highlighted by custom cabinetry and a walk-in white oak pantry just off the kitchen, combining style and everyday function. Multiple office and flex spaces provide options for work, study, or additional living needs. The 2nd floor features five bedrooms, including a primary suite, along with a convenient second-floor laundry room. The finished lower level includes a wet bar, full bath, spacious rec room, and bonus room suitable for a gym, playroom, or additional living space. Beautiful professional landscaping enhances curb appeal. Ideally located near Harrington Elementary School and adjacent to the future Harrington School Athletic Complex, offering access to new recreational fields!

Welcome to this beautifully maintained 3–4 bedroom, 1.5-bath home located in one of the most desirable neighborhoods in town. This spacious home features a large, generously sized kitchen, original hardwood floors, and an enclosed porch overlooking a beautiful, private backyard—perfect for relaxing, entertaining, or enjoying your morning coffee.Additional highlights include an attached garage with convenient access to the basement, offering ample storage and added functionality. With its spacious layout, charming original details, desirable location, and inviting outdoor space, this home presents a wonderful opportunity to own a property in a highly sought-after neighborhood.Market price of the home includes the buyer assuming the existing solar lease. Home comes as is.