This beautifully renovated, light-filled condo blends classic charm with modern updates in an ideal Winchester location. Completely gutted and converted in 2017, the home features an open-concept layout, highlighted by a spacious kitchen with granite countertops and a generous island—perfect for casual dining and entertaining. The finished basement adds versatile living space, while the primary bedroom offers a walk-in closet for optimal storage.With four bedrooms and two full baths, this home provides room to grow, all set on a charming side street just moments from shops and major roadways. Enjoy outdoor living on the private patio with newer custom fencing, surrounded by peace and convenience in equal measure.
Located in the TOP neighborhood that everyone wants! Welcome to the Flats, where elegance and charm abound. A gorgeous foyer welcomes you and flows easily into the living room and dining room, both impressively lit with natural light. A fireplace and custom built-ins add warmth and charm, beckoning for dinner parties and entertaining. A huge kitchen offers ample counter space, a sweet banquet, custom Kidder Blaisdell cherry cabinets & easy flow to the attached family room. There is an impressively large mudroom with cabinets, laundry, and plenty of room for sports gear. Upstairs, a large primary site offers a quiet retreat, with double closets, hardwood floors, and a spa-like bath. There are 4 other large bedrooms with high ceilings plus two home offices. The lower level offers an expansive playroom, home gym, storage room, and plenty of closets. A wonderful front porch, fenced yard, and two-car garage complete this pretty picture, all on one of the Flats most desirable streets.
Stunning Absolutely! Custom-built 6-bedroom house on a large and tranquil lot. This beautiful home welcomes you with a magnificent 18" foyer and features an amazing family room with 18” high coffered ceilings and 3 sides tall and bright windows and a large gourmet kitchen with a big island and double ovens. Traditional living and dining room maintain its good sense of typical New England Colonial style. Curved front stair case add one more layer of beauty. Second floor and third floor offer total 6 bedrooms, suites and walk-in closets. Master bedroom is with cathedral ceilings, a sprawling master closet and an office/sitting area. Smooth flow of the spacious and walk out lower level enables rich life style with billiard room, media room, art room and exercise room -- all designed for a modern lifestyle, with an open layout that is perfect for entertaining. State of the art systems with total 6 heating and cooling zones and central vacuum system.
Stunning waterfront home on Little Winter Pond offers the perfect blend of modern design and serene natural beauty! Thoughtfully updated, the home welcomes you with a striking entry, soaring vaulted ceilings, and walls of windows that flood the space with natural light and frame breathtaking pond views. The stylish kitchen with adjacent dining area featuring custom bench seating flows seamlessly into the spacious living and family rooms—ideal for everyday living & entertaining. The main level offers three generously sized bedrooms and two full baths, including a peaceful primary suite with panoramic views, a walk-in closet, and beautifully renovated bath with two individual vanities. The lower level adds fantastic flexibility with a media room, additional bedroom, full bath, and flexible multipurpose space. Step outside to enjoy a wraparound deck and lower-level patio with direct access to the pond—perfect for kayaking, fishing, and ice skating. This is a rare and special opportunity!
Luxury and location converge in this stunning 5-bedroom, 5.5-bathroom home nestled in one of Winchester’s most coveted Westside neighborhoods. Beautifully rehabbed and thoughtfully expanded, this turnkey residence offers over 4,600 sq. ft. of refined living space, just steps from Ambrose School, one block from the Alewife bus stop, & a short ½-mile stroll to the commuter rail. Every detail has been curated for style & comfort in this stunning home. White oak hardwood floors and imported tile run throughout. The kitchen features Viking stainless steel appliances, custom cabinetry, and a large center island. A living room w/ gas fireplace wrapped in natural stone adds warmth and elegance. 1st & 2nd floor primary bedrooms with spa-like en-suite bathrooms. Finished lower level w/ home gym, family room, full bath and mudroom. An oversized double-bay garage w/ direct mudroom access adds everyday ease. Lot is large enough for a pool or AUD/in-law! A must see with a prime location!
Discover the perfect blend of luxury and comfort in this stunning 6-bedroom home. Sunlight pours into the open-concept layout, highlighting a gourmet kitchen with stone countertops, an oversized island, and high-end Viking appliances. The inviting living room, featuring a shiplap fireplace, opens to a spacious composite deck. The primary suite is a private retreat with a walk-in closet, dual vanity, and a spa-like tiled shower. Three additional bedrooms, including two with walk-in closets, plus a shared bath and convenient second-floor laundry, complete the upper level. The unfinished attic offers potential for future living space. The finished lower level offers versatility, with full-size windows, a sixth bedroom, a bath, a recreation room, and a mudroom with garage access .Outside, enjoy a beautifully landscaped yard with a sprinkler system and privacy fencing. Nestled in a sought-after neighborhood with top-rated schools and easy access to nearby town amenities.
Enjoy breathtaking Boston skyline views from nearly every room of this meticulously maintained home, offering the ultimate private retreat for peace and tranquility. The owners have thoughtfully upgraded the property, including a 2020 expansion that added an en-suite with a private bathroom and enlarged the open-concept kitchen. With 5 bedrooms and 5 bathrooms, including four en-suites, this home combines style with functionality. The spacious dining room, with its cathedral ceiling and fireplace, sets an elegant tone, while the inviting living room, featuring a second fireplace, offers the perfect spot for relaxation. The luxurious master suite is a spa-like sanctuary with Carrera marble, a jetted tub, and radiant heat. Additional features include Hunter Douglas electric shades, Ethan Allen custom interiors, a two-car garage, tiered decks, central A/C, central vacuum, and passive solar heating. Conveniently located near top-rated schools and the MBTA for easy access to Boston.
Welcome to this well loved 4-bedroom expanded Cape, on quiet cul-de-sac, cared for by the original owners for nearly 65 years! Located in the brand new Lynch Elementary School district, just steps from Winchester HS, Skillings Field, less than a mile from the Commuter Rail and downtown Winchester. Great for commuters. First floor features mudroom with laundry, front-to-back fire-placed living room, formal dining room,eat-in kitchen, full bath, 2 bedrooms, and vaulted sunroom with slider to back deck. Upstairs 2 large bedrooms, walk-in storage room, and full bath. Partially finished basement includes fire-placed flex space, full bath, and workshop + storage room. Situated on a flat, private 9,121 sq ft lot, the outdoor potential is endless. Sold AS-IS, buyers encouraged to do their own due diligence. Neither sellers nor seller’s agent make any warranties or representations. An incredible opportunity in the competitive Winchester market. Don't miss out!
Located in a very desirable East Hill neighborhood, this one owner Circa 1929 Dutch Colonial offers a wonderful opportunity for the next owners to bring their ideas and make this home their own. The interior features many generous sized rooms, hardwood floors, crown molding, built in China cabinet, French doors, a brick fireplace and many more original details. This home is traditional with the kitchen, dining room, living room and an ideal home office/den and a half bath on the first floor and 3 bedrooms and a full bath on the second floor. Beautiful natural sun light shines throughout. Outside, there is a detached one car garage and a lovely yard perfect for relaxing, gardening and entertaining. Within a short distance to Winchester Center, schools, commuter rail and major routes, don't miss this charming antique home with lots of potential!
Completely renovated in 2023/2024! This is one of the most distinguished homes on Everett Avenue, with preeminent siting on more than half an acre. This residence combines the magnificence of early 1900s architecture with today's modern amenities., this home features hallmark architectural details including Tudor-style balusters and high ceilings. Large rooms, coffered ceilings, original crown moldings, mantels, and decorative trim are enhanced by the beauty of restored hardwood floors. The new kitchen is a chef's dream w/ a walk-in pantry w/laundry and refrigerator drawers plus a butler's pantry with a wine fridge. A large island, gleaming induction range and gorgeous cabinetry complete this look. A huge family room is flanked by floor to ceiling windows. Upstairs, a magnificent primary wing boasts a new spa-like bath with custom walk-in closets plus an adjacent study with extra closets. The lawn is one of the biggest you can find, with magnificent old oak trees & an ample driveway.
Exceptional Home nestled in one of Winchester's most desirable West Side Neighborhoods and on a Cul de Sac! Open Floor Plan, Very Spacious Granite and Stainless Chef's Kitchen w/Breakfast Bar and Sun-filled Family Room featuring Floor to Ceiling Windows w/ French Doors open to Deck, Serene Level Backyard w/ Stone Patio, Lush Perennials and Mature Trees to Relax and Enjoy! Elegant Dining Room open to Grand Entry Foyer and Gorgeous Sunken Living Room w/ Beautiful Fireplace and Custom Stained Glass Window. Primary Suite with Sitting Area & Luxurious Ensuite Bath. Oversized Great Room w/Stone Fireplace, Office, 2nd Kitchen/Laundry Room, In-Law/AUD Potential, & Steam Shower. Lower Level Recreation/Game Room, Exercise Space, Cedar Closet, Wine Storage, Workshop & Storage Room. New/Upgraded H2O & Heating Systems, Vinson-Owen School District, Convenient to All Major Routes, Perfect Family Home!
Prepare to be captivated by the elegance of 11 Viking Rd. This magnificent home, boasting over 7,000 square feet of luxurious living space, offers an unparalleled opportunity for discerning buyers seeking the ultimate in comfort, style, and sophistication.Step inside and discover a world of meticulous details and thoughtful design. With 7 generously sized bedrooms and 7.5 exquisitely appointed bathrooms, this home provides ample space for family and guests alike. The expansive layout is perfect for both grand entertaining and intimate family moments.Offering exceptional features from a custom designed kitchen that will inspire your inner chef to comfortable living areas bathed in natural light. Enjoy the convenience of a 3-car attached garage, expansive private lot & four levels of living. Flexible space perfect for guest suites, play areas, fitness and work from home. Located in a prime neighborhood, offers convenient access to top-rated schools, local shops, a beautiful farm & dining
Nestled in the heart of Winchester, this charming 4-bedroom, 1.5-bathroom single-family home offers 2,202 square feet of living space on a 7,126-square-foot lot. Built in 1927, the home exudes timeless character with its spacious rooms, abundant natural light, and original architectural details. Perfect for homeowners and developers alike, the property offers endless potential for renovation, expansion, or redevelopment. Located in a highly desirable neighborhood, it provides easy access to top-rated schools, parks, shops, dining, and convenient commuting options to Boston. This is a rare opportunity to own a piece of Winchester’s charm with unlimited possibilities.
Step into a piece of history with this incredibly charming 1895 Colonial Revival, a home that exudes elegance, character, and masterful craftsmanship at every turn. From the moment you arrive, you’ll be captivated by its stately presence, classic architectural details, and warm, inviting ambiance. Inside, you’ll find an extraordinary blend of historic charm and modern livability.The craftsmanship is remarkable—gleaming hardwood floors, intricate leaded glass windows and cabinet fronts, and graceful moldings showcase the artistry of a bygone era. Sweet window seats offer the perfect place to relax with a book or head to the very large screened-in porch for an al-fresco dinner.The home’s spacious layout includes 6 bedrooms and 3.5 baths, each infused with character and period charm. Outside, the home is nestled in a fantastic neighborhood known for its tree-lined streets, friendly community, and historic appeal. Nice flat yard and a 2-car garage, close to the center, schools and train!
Welcome to this oversized Cape in a lovely west side neighborhood of Winchester. Opportunity for a little TLC or a significant renovation, the flexible layout of this 1952 gem offers many possibilities. Attention savvy buyers, contractors and builders! Sited on a 10,703sf lot within the Vinson-Owen school district. First floor offers living room, dining room, kitchen, sunroom/porch, 2 bedrooms and a bath. Second floor has 2 large bedrooms and a full bath. Family room and laundry are in the walk-out lower level. 2-car garage under. Great location for commuting to Rt 2, Rt 3, 128, 93 and the Commuter Rail. Sold AS-IS. Buyers please do your own due diligence. Seller and Seller’s agent make no warranties or representations. This property offers TREMENDOUS OPPORTUNITY FOR UPDATING to make your forever home. Sellers prefer closing at end of June.
Nestled on a peaceful street surrounded by trees, this beautifully updated Cape home offers a perfect blend of comfort and character. Located just moments from the scenic Middlesex Fells Conservation Area, you'll have miles of trails for outdoor exploration right at your doorstep. With a commuter-friendly location, this home is ideal for those seeking both tranquility and convenience. A welcoming front porch greets you, setting the tone for the warmth and charm inside. The first-floor primary suite provides convenience, while two fireplaces offer cozy spots for relaxation. The eat-in kitchen features radiant heat floors with an enclosed porch to the side complete with exposed beams and skylights, creating a serene space to unwind and enjoy the view of the natural surroundings. Upstairs, a versatile suite awaits, featuring a spacious bedroom, full bath, office space, and a cozy reading nook — ideal for guests, a home office, or a quiet retreat with a possibility of an expansion.
NEW CONSTRUCTION! This stunning 7-bed, 5.5-bath luxury home boasts high-end finishes and a thoughtfully designed open floor plan, perfect for entertaining and modern living. The chef’s kitchen features an oversized quartz island, pro appliances, and a breakfast nook, with sliders leading to a private backyard. The spacious family room offers a gas fireplace, while the 1st floor includes a formal dining room and a 7th bed/home office with a full bath. The lavish primary suite has a spa-like bath, and dual walk-in closets. Four additional beds, 2 baths, and laundry complete the 2nd floor. The finished lower level includes a media/rec room, extra bedroom, and full bath. Oversized 2-car garage, ample off-street parking, and prime location near town—this home has it all!
Experience the perfect blend of timeless elegance & modern luxury in this stunning 5-6-bedroom home, set on one of the town’s most picturesque streets. The stunning state of art chef’s kitchen was just completed & seamlessly connects to a butler’s pantry w/ wet bar & wine chiller, leading to an elegant dining room w/ fireplace. The oversized family room is bathed in natural light w/walls of striking arched windows & a screen porch leading to a deck & custom stone patio overlooking a large level yard. The second floor showcases 4 spacious bedrooms, 2 baths including a generously sized primary/currently using BR 4 for walk in closet. The 3rd floor offers 2 additional bedrooms, office & full bath. The finished walk-out lower level offers great space for movie nights, a gym & storage w/direct entry 2 car+ garage & mudroom. Close to the town center, train to Boston, Mystic Lakes beach, playgrounds & scenic trails, this exceptional home offers both charm & convenience in a top neighborhood!
Welcome to The Ledges! This is a desirable end unit located in a fabulous cul de sac location. Freshly painted first level makes this unit ready to move in.This is a perfect floor plan with living room, dining room and family room with fireplace and bookcases opening up to expansive kitchen with pantry. Enjoy the serenity of a private deck off family room. Primary suite on first floor.with large updated bath.Second floor has a large loft office and full bath and bedroom. Finished lower level has third bedroom with updated bath and spacious media room with built in bookcases.There is plentiful storage areas in hall and cedar closet.Heating system has been updated.Put your finishing touches on the beautiful home with hardwood floors on first and second level. This is a rare opportunity to own this north facing property which receives consistent indirect light throughout the day with sunny south facing kitchen and family room overlooking private woods.
Welcome to 160 Swanton Street—a stunning Ron Roy new construction townhome blending modern design with unparalleled craftsmanship and attention to detail in the heart of Winchester. The first floor features an open-concept living, dining, and kitchen area with gleaming hardwood floors and a cozy fireplace, creating a warm and inviting ambiance. The chef-inspired kitchen boasts stainless steel appliances, a spacious island, and an adjacent mudroom with a half bath. The second floor offers two bedrooms and a full bath, while the third floor is a private primary suite with a spa-like en-suite. The finished lower level provides a versatile space—ideal as a great room, office, or gym—with its own full bathroom. This home includes two off-street parking spaces with an EV charger. Conveniently located near Winchester’s shops, dining, parks, & commuter rail. Home designed for today's lifestyle with guidance from Louis Ashman.
This expansive contemporary residence exudes elegance & sophistication and offers the perfect layout for gatherings & everyday living. This gorgeous home, nestled into a cul-de-sac on the West side was custom designed with soaring ceilings & large scale rooms offering unparalleled views! Enjoy meals in the updated kitchen w/ high end appliances & direct access to deck overlooking private yard. The breathtaking living & dining rooms serve as the heart of the home, complemented by an oversized family room & elegant home office, offering multiple inviting spaces w/4 fireplaces to enjoy in various wings of the home. Retreat to the spacious primary suite, a true sanctuary with its large closets, fireplace & tranquil views. The remaining bedrooms are all generous in size w/ ample closets. Full laundry room, oversized 2 car garage & plenty of storage. This home offers a lovely yard & privacy; a serene outdoor escape. Experience modern living in this impressive home drenched in sunshine!
This stunning Colonial Revival home, situated on one of Winchester’s most desirable streets, is just moments from the train station, town center, and Ambrose School. The kitchen features radiant floor heating. The first floor includes a chef-designed kitchen, expansive living and family rooms, a formal dining room, a half bath, and a mudroom. On the second floor, you'll find a luxurious master suite with walk-in closets and a Jacuzzi bath, along with two additional bedrooms and an updated bathroom. The third floor offers a variety of flexible living spaces: one separate bedroom with an en suite, one study that can share the en suite as a separate bedroom, and one suite/bedroom with a bath, morning kitchen area, and living room. The finished basement is equipped with a wet bar and wine cellar. Outside, a new two-car garage, storage shed, and patio/deck enhance the generous lot. Recent upgrades include kitchen, porch, HVAC, electrical systems, IT wiring, and beautiful wood flooring.
This stunning, freshly painted, home is located in a picturesque and unique setting, elevated on a small hill with a private half-acre lot in a tranquil cul-de-sac, near the Winchester/Lexington border. It’s far from road traffic, offering exceptional privacy. The residence spans four levels, featuring 5 bedrooms, 3.5 bathrooms, and two separate laundry areas. The expansive grounds showcase beautiful front and back yards, a large deck, and a gazebo. The property borders a serene forest with a pond (Whipple Hill/Smith Pond). It’s just a short walk to Wright-Locke Farm and a quick drive to shopping centers, malls, and major roads, providing easy access to business districts. Nearby, you’ll find plenty of recreational options, including swimming pools, tennis courts, golf courses, ice skating rinks, gyms, and restaurants. Additionally, this home is located in one of the top-rated school districts, and the Town of Winchester is known for its charm and exceptional quality of life.
Stunning 8800 sq ft brand-new contemporary in one of Winchester's favorite neighborhoods. A gracious foyer w/ high ceiling welcomes you to this elegant home loaded with natural light and architectural detail. Custom features include a gourmet eat-in kitchen w/ granite countertops, high-end appliances, secondary prep area, and fabulous outside dining options from the oversized deck. The fire-placed family room, banquet-size dining room w/ wine-column, private home office and bedroom w/ en-suite bath complete the first floor. Luxurious primary suite w/a large balcony, expansive walk-in closets & spa-like bath w/ dual vanities and a lavish soaking tub on upper level, along w/ 3 additional en-suite bedrooms and an oversized laundry room. Finished lower level features additional entertainment areas, gym&en suite-bedroom. BOSCH A/C units can switch between propane/electric heating. Fantastic location just up the hill from top-rated Vinson Owen School. Enjoy all that Winchester has to offer.
This European-inspired estate is a masterpiece of design and craftsmanship. Every detail has been meticulously curated, blending timeless elegance with state-of-the-art amenities.Step into a grand foyer, where a striking curved staircase sets the stage for the home’s sophisticated ambiance. Expansive living and entertaining spaces flow seamlessly, featuring soaring ceilings, custom millwork, and exquisite finishes. The Bespoke chef’s kitchen, outfitted with professional-grade appliances, a fireplace, and an adjoining mudroom, is both a culinary dream and a warm gathering place.The opulent primary suite is a private retreat, reminiscent of the world’s finest resorts, boasting a spa-inspired bath and serene views. Three additional en-suite bedrooms provide refined comfort for family or guests. Designed for effortless indoor-outdoor living, eight sets of French doors opening to a breathtaking loggia with marble columns and sparkling heated saltwater pool. Shown by appointment only.
Winchester is located in Massachusetts. Winchester, Massachusetts has a population of 22,875. Winchester is more family-centric than the surrounding county with 48.34% of the households containing married families with children. The county average for households married with children is 35.9%.
The median household income in Winchester, Massachusetts is $184,844. The median household income for the surrounding county is $111,790 compared to the national median of $69,021. The median age of people living in Winchester is 42.4 years.
The average high temperature in July is 82.3 degrees, with an average low temperature in January of 19 degrees. The average rainfall is approximately 46.9 inches per year, with 52.7 inches of snow per year.
