luxury real estate 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!

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.

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!

Welcome to this charming Arlington home, offering space, comfort, and an exceptional location. With four bedrooms, two baths, and flexible space for working from home or everyday living, this house is designed to grow with your needs. Close to bus lines, parks, playgrounds, the off-road bike park, schools, and the Minuteman Bike Trail, the perfect balance of convenience and neighborhood charm. The fireplaced living room flows into the dining room, creating inviting spaces for gathering and entertaining. There is one bedroom on the first floor, great for a guest bedroom, office or den, and three on the second floor. The kitchen features solid wood cabinetry, newer appliances, and wonderful potential for future updates. Hardwood floors run throughout much of the home. Outside, the generous yard is ideal for gardening, play, or relaxing outdoors. With updated 200-amp electric, gas heat, a one-car garage, and off-street parking, this well-loved Colonial is ready for its next chapter.

Welcome to sought-after Village Heights! This beautifully maintained end-unit townhouse offers the comfort and feel of single-family living with the ease of condominium ownership. Encompassing 1,335 square feet of sun-filled living space, this inviting home features six well-designed rooms and two dedicated pkg spaces just outside your door. The open-concept main level, ideal for everyday living and effortless entertaining, showcases hardwood floors, spacious living/dining areas and updated kitchen w/granite counters and SS appliances. French doors open to a private patio—perfect for morning coffee, afternoon sunshine, or evening cocktails. Upstairs are two-three generous bedrooms and updated bath, while the lower level provides in-unit laundry and abundant storage both basement and attic! Easy bus service to Alewife and Harvard Sq, along with nearby Arlington Heights' eclectic eateries and shops. The Minuteman Bikeway, Reservoir Beach and many outdoor recreation opportunities complete this exceptional lifestyle in the Town of Arlington!

Welcome to this beautifully maintained residence nestled in the coveted Brooks Estate neighborhood. Step inside to a lovely spiral staircase and a welcoming foyer, opening to a formal living-room with a fireplace and rich period details, including wood-paneled walls, built-in bookcases and beveled glass windows. Just beyond the living-room, find a fabulous screened-in porch and French-glass doors leading to the spacious kitchen and dining room featuring abundant cabinets and premium appliances. Sliding glass doors open to a private, fenced backyard with mature plantings, a patio, and a newer deck with awning. A half-bath completes the main level. The second floor offers four spacious bedrooms, a full bath, and a hallway with built-in linen cabinets and drawers. The lower-level family room is perfect for movie nights. This level has a wet bar and full bath. Prime location: close to the Mystic Lakes, commuter rail, Whole Foods, and West Medford Square. Lovely home with many updates!

Tucked away on a private road and directly abutting Arlington's beloved Minuteman Bikeway, this exceptional townhouse offers a lifestyle few homes can match. Enjoy miles of scenic walking, running, and biking just outside your door, or leave the car behind for an easy commute—all while surrounded by peaceful natural beauty. Built in 2018, this sun-filled home features quality craftsmanship, an open-concept floor plan, hardwood floors, wainscoting, recessed lighting, and oversized windows. The chef's kitchen showcases quartz countertops, stainless steel appliances, abundant cabinetry, and generous workspace, flowing seamlessly into the dining and living areas. The second floor offers two spacious bedrooms and a beautifully appointed full bath, while the entire third level is dedicated to a private primary suite with a walk-in closet and elegant en-suite bath. Two-zone heating and central air provide year-round comfort. The attached oversized tandem two-car garage includes direct home access and a separate utility room. Low condo fee, healthy reserves. Ideally located near parks, highly regarded schools, public transportation, Arlington Center, Arlington Heights, acclaimed restaurants, cafés, and boutique shopping, this home perfectly blends luxury, tranquility, and convenience. Showings begin immediately. Offers, if any, are due Tuesday, August 18 at 10:00 AM. Home is where hearts gather and dreams take root!

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 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

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.

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.

Not every two-family lives the same way. Here, each unit has its own personality while still feeling connected by the care that's gone into the property over the years. The first-floor unit follows a traditional layout with a sunny front porch, living room, dining room with original built-ins, two bedrooms, a full bath, and an enclosed rear porch. Upstairs, the second unit opens up with an updated layout, with a large living room, a combined kitchen and dining area and a bedroom and full bath on the main level, while two additional bedrooms occupy the third floor. An enclosed back porch finishes the second unit. Separate laundry in each unit and an unfinished basement provide practical storage without sacrificing living space. Set on a side street just moments from Mass Ave and the Minuteman Bike Path, the location makes everyday errands, commuting, and weekend rides equally convenient. Positioned within the MBTA Communities Overlay District, the property also offers future possibilities while remaining an exceptional home to enjoy today.

Perched above the street and surrounded by mature greenery, this elevated setting creates a sense of privacy that's unexpected for such a convenient location. The front mudroom is a practical everyday landing spot before opening into a welcoming foyer that introduces the warmth and character found throughout the home. Hardwood floors, natural light, and thoughtfully proportioned spaces create an immediate feeling of home with a layout that feels both comfortable and functional. The living room is the kind of space where conversations linger, while the adjoining dining room is equally suited for holiday dinners or casual weeknight meals. At the heart of the home, the spacious kitchen provides generous cabinet storage, abundant countertop space with a kitchen island, and room to cook, gather, and entertain without feeling crowded. Just beyond, a bright family room overlooks the backyard and offers remarkable flexibility. Whether it's a home office, playroom, reading room, art studio, or simply your favorite place to enjoy a morning coffee, it's a space you'll find yourself using every day. A convenient half bath completes the main level, while the private stone patio creates an easy extension of the home for grilling, outdoor dining, or relaxing on warm summer evenings. Upstairs, the home continues to impress with three comfortable bedrooms, including an oversized primary bedroom complete with a walk-in closet. Two additional bedrooms provide space for guests or work from home needs, while the full bathroom is thoughtfully positioned to serve the second floor. The unfinished basement provides abundant storage and room for future possibilities such as a gym or home office with a separate entrance. The location is equally compelling. Whether you're commuting via the West Medford commuter rail or I-93, trips to Boston are straightforward. Weekends can be spent exploring the trails of the Middlesex Fells, spending the afternoon at Mystic Lakes, or enjoying the restaurants, cafes and local businesses of West Medford. This location makes it easy to enjoy everything that gives West Medford its distinctive character, while coming home to a peaceful setting that's tucked away from it all.

Stunning rear-facing new construction townhome featuring an exclusive fenced backyard and private patio. Thoughtfully designed with four spacious bedrooms, each with its own en-suite bath, plus a stylish half bath at the end of the mudroom on the first floor. High-end finishes include custom cabinetry, quartz countertops, tiled backsplash, and a waterfall island. Smart glass exterior door panels provide switchable privacy with the touch of a button. Deeded garage parking. Exceptional East Arlington location just blocks from Arlington Center, offering convenient access to shops, restaurants, and public transportation. Enjoy nearby Mystic River Reservation with scenic walking trails, parks, and river views. Just two blocks to a playground and dog park, and approximately 1 mile to Shannon Beach for swimming and recreation.