Classic Victorian charm in a convenient Winchester location close to shops, the commuter rail, library, Farmers’ Market, and the Middlesex Fells. An inviting entry opens to a bright living room with a built-in window seat offering hidden storage. The main level flows into the dining room with an attached office alcove and half bath, providing flexible work-from-home space. The renovated eat-in kitchen features granite counters, a custom peninsula, and built-in pantry, with a mudroom just off the back entry. Upstairs are three bedrooms with generous closet space, including a custom walk-in in the primary bedroom. A finished walk-up attic offers bonus space for a playroom, office, or guest area. Hardwood floors throughout, fenced yard for outdoor enjoyment, and owned solar panels for added efficiency and long-term savings. A home that blends character, comfort, and everyday convenience.
Classic New England charm defines this pristine 3-bedroom, 2.5-bath Colonial set on a generous, level corner lot with a beautiful stone wall in a sought-after neighborhood. Lovingly maintained by the same owners for over 50 years, the home is neat as a pin and filled with warmth and character. Hardwood floors, a traditional Colonial layout, and a fireplaced living room create comfortable living spaces, while a lovely sunroom brings in abundant natural light. Spacious bedrooms offer comfort, and the partially finished basement provides bonus space for work or play. An attached two-car garage adds everyday convenience. Ideally located just about .5 mile to the MBTA Wedgemere commuter rail station for easy Boston access, with quick connections to I-93 and nearby outdoor recreation at the Middlesex Fells Reservation. Move right in and enjoy, with the option to make thoughtful updates over time in a home that truly reflects pride of ownership.
Magnificent newer sun filled colonial w/oversized rooms offering over 8,000 sq ft of beautifully finished living space featuring 7 grand BR's, 7.5 BA across 4 levels w/a 3-car direct entry garage. This expansive home showcases exceptional craftsmanship including custom built-ins, fine cabinetry, decorative moldings, 4 fplc & a great layout. The newly renovated kitchen features sleek quartz countertops, oversized island, 2 dishwashers & butler’s pantry w/ice maker & wine fridge flowing into formal DR & LR plus a fireplaced FMRM overlooking a meticulously maintained yard. Each oversized bedroom offers an en-suite bath, sitting area & walk-in closet, providing comfort & privacy throughout. The 1st flr includes a private office w/wet bar plus a lavish bedroom wing ideal for guests or multi-generational living. The 3rd floor suite features a full BA & 2 closets, while the finished lower level adds media/game/gym areas w/access to stunning gunite pool, complimented by lush outdoor landscape!
This STUNNING newly constructed home facing Old Village Drive redefines modern luxury! Designed w/ both elegance & everyday comfort in mind, this residence blends style w/ ease of living. The 8’ arched, handcrafted wrought-iron front doors open to a grand 20' foyer, showcasing soaring 10' ceilings, custom rift-sawn beams, and expansive floor-to-ceiling windows. With 25 years of expertise, the master builders commitment to exceptional quality & craftsmanship shines through every detail. Spanning four meticulously finished levels, this home leaves nothing to be desired. Highlights include a chef's kitchen w/ dual islands, vaulted ceilings, wine fridge, coffee bar, charming breakfast nook, butler's & dry pantries, a direct entry first-floor office or in-law suite & full third floor w/ hardwood floors & bath. The expansive lower level offers a family room, movie theatre, game room, gym plus private entry separate living quarters w/full in-law/au-pair suite w/ kitchen, 2nd laundry,BR & bath
Discover a stunningly reimagined home nestled in one of Winchester’s most sought after neighborhoods—an exceptional opportunity to own a beautifully crafted, completely transformed residence. Expanded and rebuilt with intention, 15 Mayflower delivers the space, layout, and flexibility today’s lifestyle demands, with a thoughtful floor plan that balances open concept living and well defined spaces. One of the home’s most compelling features is a private two bedroom retreat complete with its own living area, wet bar, office and bath—perfect as a hangout space, teen suite, guest quarters, or an ideal setup for extended family. Just moments from Wright-Locke Farm and Mullen Field, the location offers everyday access to outdoor recreation while remaining firmly rooted in a classic neighborhood setting. Featuring high end finishes and adaptable living spaces throughout, this exceptional property offers comfort, functionality, and convenience in a truly prime location.
Updated / move in ready 3 bed, 2.5 bath home *Set on a generous 11K lot* in a fantastic Winchester location/ Lincoln Elementary close to town, schools, train & Boston. The first floor offers an ideal layout w gleaming hardwood floors, updated kitchen w/stainless steel appliances & island seating open to a lovely family room flooded with sunlight, plus a spacious living room w fplc & dining room. A 3 season sunroom in the rear provides bonus living space w/direct access to large back & side yards, perfect for outdoor enjoyment. The second floor features three spacious bedrooms, 2 new baths incl. a primary suite w/ bath. The partially finished basement offers flexible space for a playroom, office, gym, or media area. With a wonderful yard and convenient location, this home presents an excellent opportunity in a highly desirable neighborhood. Enjoy the cul-de-sac location & 1 car garage! Don't miss this move in ready home with plenty of room on the lot for expansion down the road!
A timeless home of exceptional craftsmanship on the coveted slope of Myopia Hill, offering tranquil views of lush gardens and rolling hills. Thoughtful architectural details enrich every space, while multiple patios and wrap-around porch create an effortless flow between indoor& outdoor. The gracious main level unfolds into beautifully connected living spaces, featuring an office, elegant dining room, chef’s kitchen adorned by enchanting breakfast area and an inviting living &family room anchored by a stone fireplace. The upstairs primary suite is a private retreat w/ its own balcony, dressing rooms, cedar closet & a spa-inspired bath. The private backyard—with its historic stone hunter gazebo, fire pit, mature trees and layered plantings—offers both openness and seclusion. Within close proximity to Winchester Country Club and offering a swift commute to Boston & major highways, this exceptional property delivers privacy and prestige in one of Winchester’s most desirable enclave.
Experience the perfect blend of luxury and effortless living in this stunning custom-built residence, thoughtfully rebuilt and expanded to offer a sophisticated, maintenance-free lifestyle. Bathed in natural light, the flexible floor plan begins with a magnificent first-floor primary suite featuring a marble-clad bath, soaking tub, and walk-in shower. The heart of the home is a chef’s kitchen anchored by a granite island and premium Bosch appliances. Entertaining is seamless, whether hosting formal dinners by the wood-burning fireplace or relaxing in the spacious family room with its sleek gas fireplace and glass doors to the yard. A bright four-season sunroom offers a peaceful retreat year-round. The second level provides four additional bedrooms, two full baths, and a convenient second laundry. Downstairs, a heated bonus room with a third fireplace full bath serves as a gym or media room. Sited on a flat lot steps from Wedgemere station, this is suburban living at its best.
This exceptional Everett Avenue residence stands among the street’s most distinguished offerings, commanding a premier setting on over half an acre. Renovated in 2023-2025, timeless architecture is seamlessly married to today’s most coveted amenities. Hallmark architectural details abound. Balusters, soaring ceilings, coffered rooms, original crown moldings, mantels, and decorative trim are beautifully preserved, elevated by the warm glow of restored hardwood floors. Generous, light-filled rooms unfold with grace and scale throughout. A newly designed chef's kitchen, new baths, walk-in pantry w/laundry and a classic butler’s pantry with wine refrigerator are some of the highlights. Anchoring the home is an expansive family room, framed by floor-to-ceiling windows overlooking a park-like lawn. A rare offering where architectural pedigree, thoughtful architecture and renovation, and exceptional land converge.
Experience the perfect blend of craftsmanship & modern luxury in this stunning custom-built brick ranch. From the moment you enter the spacious front foyer, you’re greeted by soaring cathedral beamed ceilings & an inviting open-concept layout that seamlessly connects the living, dining, & family areas—ideal for effortless entertaining & comfort. A thoughtfully designed private wing includes 4 spacious bedrooms & two full baths, offering both privacy & convenience. The expansive mudroom provides access to the two-car garage & side entrance, blending practicality with elegant design. The fully finished lower level is an entertainer’s dream, complete with an open game & playroom, large gym, full bath, & generous laundry room. Pet owners will appreciate the custom-designed dog kennel with exterior access & a private wash area—every detail has been considered. Impeccably maintained & beautifully appointed, this exceptional home offers a rare combination of style, space, & sophistication.
Welcome home to this completely renovated gem, ideally situated on a corner lot in the highly sought-after Lincoln Elementary School district. Warm, inviting, and truly move-in ready, this home offers the open-concept first floor buyers dream of—featuring a beautiful kitchen flowing seamlessly into the dining and living areas, plus a sunken family room perfect for relaxing or entertaining. Enjoy the practicality of a mudroom located directly off the driveway, along with multiple off-street parking spaces and a two-car garage. The finished lower level includes a full bathroom and flex space ideal for a recreation room, home gym, playroom, or media room. Upstairs, you’ll find three bedrooms, including a lovely primary suite with a spacious bedroom, walk-in closet, and full bath. This home has been thoughtfully renovated from top to bottom, featuring all new systems for peace of mind and modern living. Located just a short walk to Winchester’s vibrant town center and commuter rail.
Exceptional Victorian era gem, steps from Town Center, schools, commuter rail, and the Fells! This spacious period home seamlessly blends modern elegance with timeless charm. It’s special features include: an inviting farmer’s porch, generous living and dining rooms well-suited for entertaining, first floor family room, covered porch for al fresco dining, primary suite with ensuite bath, home office, sun room, central AC (8 mini-splits), Lochinvar heating sys (2025), hardwood floors, 3 fireplaces, and more. The stunning kitchen combines function, design, and quality showcasing custom cabinets, granite countertops, stainless appliances, and tasteful lighting. Bring your design ideas for the third floor and personalize the space for your needs. The lower level, with an outside entrance and a half bath, is well suited for an in-law suite, or au pair accommodations. The lovely backyard with its Zen Garden includes many thoughtfully organized plantings and flowering trees. Welcome home!
NEWER CONSTRUCTION! This 2020 home showcases 5 beds, 4 baths-4300sf of style & luxury situated on the corner of Loring Ave. The home features high ceilings, hardwood floors & a stunning sunny open floor plan w/ eat in kitchen, center island, custom cabinetry, stainless appliances & walk-in pantry. Formal dining room & dramatic oversized family room will impress, featuring vaulted ceilings, gas fireplace and plenty of windows.The first floor also includes a bedroom suite w/ full bath! Upstairs you'll find 3 spacious bedrooms, including the primary suite w/ walk-in closet & beautiful en-suite bath w/ large shower, tub & double vanity sinks. Additional BR5 & bath on the 3rd fl. The finished lower level offers a family room w/ bar & large media/playroom. A fenced in yard, deck/ patio & direct entry two-car garage complete this home. Enjoy all the area has to offer including McDonald field playground, restaurants, shops, schools, train to Boston, Bike-paths & more! Only 7 miles from Boston!
1-bedroom condo at Parkview Condominiums in Winchester. This bright unit features an open layout with peaceful views overlooking the pond. The low HOA fee includes heat, hot water, electricity, and air conditioning—an exceptional value. Highlights include a spacious living area, updated kitchen with new stainless steel appliances, a large bedroom with excellent closet space, and on-site laundry. Enjoy community amenities such as an in-ground pool, clubhouse, landscaped grounds, and on-site security. Conveniently located near shopping, schools, restaurants, and major highways.
Welcome to a stunning new-construction home in Winchester’s coveted Lincoln Elementary district, where thoughtful design and refined style come together effortlessly. Every detail has been curated to create a warm, inviting vibe, from the gorgeous family room with custom walnut built-ins and artful lighting to the seamless flow of the open yet intentionally defined floor plan. The impressive kitchen and dining area form the heart of the home—perfectly suited for lively entertaining, relaxed gatherings, and everyday living. Upstairs, the primary suite offers a luxurious retreat, while the spacious third-floor teen suite provides comfort, privacy, and versatility. The finished lower level—with its full bath—adds tremendous bonus space for play, guests, or hobbies. Blending modern craftsmanship with timeless appeal, this home delivers exceptional living just a stone’s throw from the Middlesex Fells Reservation, where nature’s beauty is right at your doorstep.
1 bedroom condo in Winchester. This garden-level unit offers tranquil pond views and direct patio access just outside the pond. The condo features a bright, open layout with large windows bringing in natural light. HOA fee includes heat, hot water, electricity, and air conditioning—making it easy and affordable to maintain. Enjoy a peaceful setting with access to the community pool and well-kept grounds, all within a short distance of Winchester Center, shops, and public transportation.
Spacious newly gut renovated colonial set back on a cul-de-sac! Unbeatable location in quiet neighborhood less than a mile from all Winchester's amazing public schools and Wedge Pond. Hardwood floors throughout with gorgeous kitchen featuring huge island, large living and dining rooms. A vaulted family room with authentic barn board detailing sits adjacent to the kitchen, opening to a large private deck for seamless indoor-outdoor living. Offering 6 beds, 3 full baths, and 2 half baths, the primary suite boasts a soaring vaulted ceiling and a walk-in closet nearly the same size, while spa-like modern baths complement generously sized bedrooms. The lower-level recreation room, complete with sliders to a large patio, provides additional space for entertaining or relaxing. Two car garage complements this ideal location, with short drives to Whole Foods, H-Mart, Burlington Mall, nature at Middlesex Fells and Mystic Lakes state parks, and easy access to Boston and surrounding areas.
Discover this brand-new custom-built home featuring 6 bedrooms and 7 full baths, located in a highly desirable neighborhood just steps from VO Elementary School. The expansive 1st floor welcomes you with soaring ceilings and an elegant layout, including a sophisticated living room, family room, and private home office. The chef’s kitchen is a true centerpiece, boasting premium Thermador appliances, custom cabinetry, and a large island that flows seamlessly to an oversized deck—perfect for entertaining or relaxing. Upstairs, the 2nd floor offers spacious ensuite bedrooms, the luxurious primary suite with a walk-in closet and direct access to a private deck. Additional highlights include a butler’s pantry, mudroom, central air, and a tankless water heater for comfort and efficiency. The finished walkout lower level provides versatile space for a gym, entertainment area, and additional suite. Don’t miss the opportunity to own a residence designed with both comfort and style in mind.
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.
