Winchester MA Real Estate & Homes for Sale

Discover the warmth and charm of this inviting New England Colonial, newly built in 2004. This sun-filled home features three bedrooms, 3.5 bathrooms, and a flexible floor plan. First floor features a large family room, dining room, updated kitchen with SS appliances, abundant custom cabinetry, a half bath, mudroom, and a separate living room. Second floor offers a sizable primary suite with a walk-in closet, a luxurious private bathroom featuring a double vanity and soaking tub, 2 additional bedrooms, and full bath. The lower level invites you into a bonus/media room wired for surround sound and projector, a full wall of built-ins, a full bath, a large storage space, and laundry room; this space would make a great in-law apartment for long-term visitors filled with light and walk-out access to the yard. Other features, hardwood floors, sprinkler system, Nest thermostats, and a new deck. Close to town center, the new Lynch School, train station, restaurants, and shops. Don't miss it.

Welcome to 21 Shepard Court, a beautifully renovated townhouse nestled in a quiet cul-de-sac. This 2+ bedroom, 1-bathroom home offers four levels of living space with modern upgrades & timeless charm. Renovated features: The main level boasts a high-end kitchen with new quartz countertops stainless steel appliances, custom cabinetry, & eat in island. The bathroom has been fully upgraded with elegant tile work & fixtures. The 3rd floor bonus room, perfect as an office or additional bedroom, has also been tastefully renovated. Basement: Energy source upgraded from Oil to new Gas-line, new water heater, and electric baseboard added for heating in basement with plenty of storage space. Outdoor Amenities: Backyard with patio and a garden area, ideal for outdoor gatherings. Parking: Exclusive driveway with 2 parking spaces. Education Excellence: Benefit from access to Winchester's highly-rated schools, including Lynch Elementary & Winchester High (rank among the top in Massachusetts)

Welcome to the highly-coveted Westside of Winchester, MA. This meticulously maintained Colonial-style home is set on 20,000 sqft lot with professional landscaping. The inviting living room features a charming wood-burning fireplace, while the sun-filled formal dining room is centered with an elegant chandelier. The kitchen has granite countertops, stainless steel appliances, and an adjacent eat-in area with a modern electric fireplace. A large bay window offers an abundance of light and views of lush tree-lined yard.This lovely home has 5 bedrooms and 3.5 bathrooms, including a primary bedroom with an en-suite bathroom. The walk-out finished lower level includes a family room with the third fireplace and a versatile room that could serve as a gym/In-law/au-pair suite with a full bathroom. Central AC, attached two-car garage, a large deck and backyard. Walk to Vinson-Owen Elementary, the Swim & Tennis Club, and Whipple Hill Conservation Area. 3mins drive to Winchester Country Club.

Nicely updated home in desirable Muraco district! This home has been meticulously maintained & features many recent updates including newer windows, central air conditioning & updated systems. Enjoy the sun drenched spaces from the spacious living room w/ fplc & bay window to the charming dining room w/ china cabinet, sunny eat-in kitchen, office, plus 3 season porch & 1/2 bath complete the first level. Upstairs there are 4 rooms 3 bedrooms one being a 2 room suite and a newly renovated full bath. The lower level offers laundry plus great space for family/game room /gym with great ceiling height, plus plenty of storage. The rear yard offers privacy and plenty of space for gatherings and for children to play. This home also features 2 driveways, plenty of parking!! Easy access to the town center, parks, bike path, Fells trails, highways & more... don't miss out on this great home in a top neighborhood!

Delightful home in Rangeley Estates, just outside Winchester Center! Featuring 5 bedrooms & 4.5 baths; 2 primary bedroom options w/ en-suite baths. A unique layout w/ a California vibe w/open airy spaces perfect for modern day living & just steps from the vibrant downtown. Enjoy easy access to Train, schools, shops, coffee, dining & more, while being tucked away in a gem of a neighborhood. Inside, natural light fills every room, skylights in the renovated kitchen showcase the heart of the home which offers plenty of storage, stainless appliances & a large island for family gatherings. The dining room & living room w fplc offer a flowing floor plan w/many windows & french door access to a serene patio & large, private backyard complete w/a relaxing hot tub, play area & shed. 2 car attached garage direct into mudroom, family room, 2 room finished basement w/ bath & more! Thoughtfully updated throughout, this home provides both comfort, style & is move-in ready. An unbeatable location!

Discover the perfect blend of charm & modern elegance in this beautiful home, nestled on one of the most highly desired streets in town. A stunning fire-placed foyer welcomes you into the home, enhanced by a new chefs kitchen w/ 10' island, custom cabinetry, & adjacent family room overlooking yard. With four floors of beautifully finished spaces, there's room for every lifestyle need. Enjoy entertaining in the large dining room, relax in the inviting living room w/ fplc, the sunroom is perfect for home office. The primary boasts a newly constructed/ tastefully renovated suite w/designer bath & large closet. The other bedrooms are generous in size & offer ample closet space. Enjoy Movie nights & workouts in the renovated lower level. The private level yard w/ patio is perfect for kids to play, BBQs, gardening, or simply enjoying the serenity of your surroundings. 2 car garage & more! This home truly offers a unique opportunity to live in a sought-after location w/ all the modern updates

Just completed!! New construction! Energy star rated, high efficiency 5 bed 4.5 bath home perfectly situated in a prime East Side location! The first floor welcomes you w/ an open, airy layout, featuring a stylish mudroom, pantry, bath & home office. The gourmet, high-end kitchen flows seamlessly into the living room, complete w/ a cozy fireplace, open dining leads to sitting room & out to a deck & huge private patio and yard great for entertaining! The second floor boasts four spacious bedrooms & three full baths, including a lavish primary suite w/ a spa like bathroom. A well-appointed laundry room is also conveniently located on this floor. The third-floor suite is a true retreat, offering two versatile rooms ideal for extended family, office, or lounge, complete w/ a wet bar, an oversized bath & a 5th bedroom with abundant closet space. The lower level adds even more living space, featuring a large family room w/ full bath & full access door to yard. Easy access to Boston!

Nestled in the heart of Myopia Hill, this custom-built home is sure to impress! Live your best life at 26 Swan Road offering 6 bedrooms, 6.5 bathrooms with a first floor primary suite. This magnificent residence boasts expansive living spaces, elevator & indoor pool! Exquisite craftsmanship is shown throughout this home including a newly renovated gourmet kitchen w/custom cherry cabinetry & high end appliances leading to adj. family room w/ fireplace. A handsome library w/ fireplace offers a warm and inviting space to relax. The highlight of this extraordinary home is the 16x32 indoor freshwater pool & jacuzzi set within a breathtaking atrium room w/soaring vaulted ceilings, perfect for year round exercise and entertainment. Each of the spacious bedrooms provides a retreat-like atmosphere, complete w/ensuite baths for ultimate comfort & privacy. The home also features 4 fireplaces, 2 home offices, a newly finished 3 room basement w/ rec room, fplc, BR & full bath, plus 3 car garage.

Introducing 74 Hillcrest Parkway! This spacious, modern 5-bedroom home is nestled across the breathtaking Middlesex Fells Reservation on one of Winchester's most picturesque streets! First floor seamlessly blends living, dining, & kitchen areas. Living room has wood burning fireplace & custom built-in shelves. Dining room offers delightful space for cozy gatherings and the spacious eat-in kitchen has french doors to wooded back yard & oversized stone patio. Above the garage a huge family room with vaulted ceilings & fireplace. 2nd fl has 4 bedrooms incl. a tranquil primary suite w/ private deck. Completing this serene suite is a custom designed walk in closet, spa-like bath w/ double sink vanity, a brand new soaking tub, and double shower. 5th br on 3rd floor. Lower level has additional family room w/gas fireplace, and storage room w custom cabinets.Enjoy all that Winchester has to offer while coming home to this true gem of a home - this is the market offering you've been waiting for!

Newly constructed 5,366 sq ft luxury home with attached 2 car garage! Featuring 5 bedrooms, 4 full and 2 half bath, and 4 levels of living, discover thoughtful elegance at every turn . The designer kitchen offers high-end appliances including a gas stove, double oven, and wet-bar with beverage fridge. Featuring an open-concept, the kitchen effortlessly flows into the sun-drenched living and dining areas, with home office, first floor bedroom, and large mudroom nearby. Ascend to the 2nd floor to find the spacious primary suite with walk-in closet, stunning bath with soaking tub, and attached deck, along with 3 other bedrooms and laundry. The 3rd floor features a bonus room with 1/2 bath, along with additional flexible space in the finished basement. Outside, the beautifully landscaped yard with cozy fire pit and patio creates the ultimate oasis. Winchester center and commuter rail less than 1 mile away. Don't miss the chance to make 8 Chestnut home!

Step into this beautifully renovated historic townhouse that seamlessly blends classic charm with modern updates. This welcoming 3-bedroom, 2.5-bathroom home features elegant finishes, high ceilings and thoughtful details throughout. The main level boasts an open kitchen/family room plan, plus a large dining room and living room, great for entertaining. Upstairs, you'll find generous bedrooms, including a master suite with a walk-in plus 2 additional closets & full bath. The finished 3rd floor adds versatility, offering the perfect space for an office, playroom, or additional living area. The large, unfinished basement with high ceilings presents endless possibilities for customization or additional living space. Enjoy the convenience of a 2-car tandem garage, providing plenty of parking and storage space. Relax and unwind on the patio, or take a stroll through the nearby walking trails. Enjoy the convenience of condo living in a unit that lives like a single family home!

Step into this beautifully renovated historic townhouse that seamlessly blends classic charm with modern updates. This welcoming 3-bedroom, 2.5-bathroom home features elegant finishes, high ceilings and thoughtful details throughout. The main level boasts an open kitchen/family room plan, plus a large dining room and living room, great for entertaining. Upstairs, you'll find generous bedrooms, including a master suite with a walk-in plus 2 additional closets & full bath. The finished 3rd floor adds versatility, offering the perfect space for an office, playroom, or additional living area. The large, unfinished basement with high ceilings presents endless possibilities for customization or additional living space. Enjoy the convenience of a 2-car tandem garage, providing plenty of parking and storage space. Relax and unwind on the patio, or take a stroll through the nearby walking trails. Enjoy the convenience of condo living in a unit that lives like a single family home!

Welcome to this warm & inviting home nestled amidst the serene landscapes of the Winchester Country Club. A Royal Barry Wills design, showcasing 5-beds, 3.5-baths, w/4 fireplaces & attached direct entry 2 car garage! This home has w/ an abundance of charm in every room; the spacious living areas are warm and inviting & flooded with natural light, showcasing original woodwork & oversized wood burning fireplaces. The updated custom kitchen has vaulted ceilings w/ arched window showcasing views of the Country club & perennial gardens; the kitchen is an absolute delight and the heart of the home. Each of the 5 bedrooms are spacious w/ great closets incl. the primary suite, with luxurious en-suite bath, offering a private retreat w/ soaking tub & tiled shower. Lower level features a cozy family room w fplc, gym, storage and full bath. Outside, the glorious fenced yard w/ mature perennial gardens & scenery of the Winchester Country Club is sure to impress. This is a one of a kind home!

LOCATION, LOCATION, LOCATION This has it.....Current building is a 2 bedroom ranch with lr,dr,k.needing TLC..Great potential for a Complete rebuild and/or restoration All offers must be on attached OFFER TO PURCHASE form and prior to entering property the attached " Hold Harmless" agreement must be signed. All offers must include the OTP, Proof of funds and/or preapproval and copy of $1,000.00 deposit check...An additional $50,000.00 will be required with P&S.Property is being sold :".AS IS".Sellers make no warranties or representations of any kind...Buyers to do their own due diligences'

Beautifully renovated first-floor condo in the highly sought-after "Willows at Winchester" complex. This expansive, single-level unit features an open-concept living area with new hardwood flooring, a versatile space that can be used as a dining room, home office or home entertainment alcove and a cozy gas fireplace. The updated kitchen features fresh granite countertops and brand new appliances. Delight in the spacious primary bedroom that features a refreshed en-suite bath and full walk-in closet. The amply sized second bedroom also has a walk-in closet. The unit is complete with a second enhanced full bathroom, central AC, in-unit laundry, and an enclosed patio. The detached garage and attic are directly across from the unit. Enjoy the complex's upscale amenities, including a pool, fitness center, and clubhouse with a full kitchen and entertaining area. Ideally located in the heart of Winchester, convenient to shops, restaurants, the commuter rail, and schools. Don't miss out!

Welcome to 158 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 stunning 4-bedroom, 4-bath modern home offers the perfect blend of luxury and tranquility. Featuring soaring vaulted ceilings, a floor-to-ceiling fireplace and an open-concept design, this spacious home is bathed in natural beauty. The gourmet kitchen is pristine and boasts high-end appliances, quartz countertops, a prep sink and secondary dishwasher, and a large island"ideal for entertaining.! Hardwood floors highlight the main living area and bedrooms, working as a perfect offset to all the natural light this home enjoys. There's a cozy den with a wet bar/entertainment area plus a huge family room in the lower level. The primary suite is a private retreat with a spa-like bath and walk-in closet. Step outside to a serene backyard oasis with a large deck, set against pristine conservation land for ultimate privacy. A rare find combining contemporary elegance with nature's beauty!

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!

This newly constructed home faces Old Village Dr. & 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, a 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, bedroom& bath!

Welcome to 4 Norwood St, a stunning custom-built home by Mark Stephen Development. Just a short walk to Winchester town center with easy access to Boston, this home features exquisite millwork, custom built-ins, and premium finishes throughout. The main home offers 4 bedrooms, 3.5 bathrooms, a living room, dining room, sitting room, pantry, and a bar alcove, along with an expansive second-floor office/flex space. A separate but attached wing"perfect for extended family or guests"boasts soaring 13'6" ceilings, a grand entertaining area with chandeliers, a full kitchen, and a private guest primary suite. With every imaginable bell and whistle, this home is truly one of a kind.

Welcome to 2 Chestnut Street, an exquisite new construction home in progress by Mark Stephen Development. Situated off coveted Main Street in one of Winchester's most sought-after neighborhoods, this residence is thoughtfully designed to blend timeless charm with modern conveniences. The home will feature five spacious bedrooms, five full bathrooms, a first-floor office, and a basement offering flexible space for an additional office, playroom, exercise room, or living area. The open-concept kitchen will include premium appliances, a grand nine-foot island, and custom cabinetry, while the primary suite will boast luxurious his-and-her closets and a spa-like bathroom with a soaking tub and marble-tiled shower. A third-floor bonus space adds versatility. With mature landscaping providing privacy and a spacious patio for outdoor living, this property is conveniently located near Winchester town center, top-rated schools, offers easy access to Boston, and promises an unparalleled lifestyle

Nestled in a coveted location just moments from the heart of downtown Winchester, the stunning Barstow House boasts a unique Mansard roof & timeless colonial architecture. This historic gem features a versatile floorplan designed for modern living while preserving its classic charm. The first level beautifully blends form & function; the home office, mudroom, a dedicated laundry room & a convenient half bath, all complimenting the formal living room, dining room, family room & spacious kitchen - perfect for entertaining. Ascend to the second and third floors, where you'll find three spacious bedrooms on each level, offering ample space for family & guests. A back staircase provides private access to a second-floor bedroom, making it perfect for extended family or added privacy. Watch the bustle of the town center from the spacious front porch & view the expansive yard. Don't miss this rare opportunity to own a piece of Winchester's history!

Nestled on a cul-de-sac in Winchester's desirable west side, this brand-new construction redefines modern luxury living. Spanning 7,500 sq. ft., this exquisite 6-bedroom, 7.5-bathroom home combines style, comfort, and functionality. Discover an open-concept floor plan bathed in natural light, perfect for entertaining and everyday living. The kitchen features top-of-the-line Wolf appliances, Sub-Zero refrigerator, custom cabinetry, and an oversized island. Adjacent living and dining areas offer ample space for gatherings. The primary suite is a retreat with a spa-like bath, large walk-in closet, and serene atmosphere. Each additional bedroom boasts its own en-suite bathroom for privacy and convenience. The finished lower level offers endless possibilities"a home gym, golf simulator room, or private theater. The walk-out basement leads to a beautifully landscaped backyard, ideal for outdoor activities. A three-car garage completes this exceptional home. Schedule your showing today!

Welcome to The Ledges! This is a desirable end unit located in a fabulous cul de sac location. Freshly painted first level make this unit in move in condition.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.

Nestled in a sought-after neighborhood, this stunningly reimagined home combines timeless charm and modern comfort, just a short walk to downtown. The inviting foyer welcomes you from a wrap-around porch into an open yet intimate layout connecting the kitchen, dining, and family rooms. A mudroom with marble checkered flooring and a walk-in pantry with a beverage fridge add practical luxury. The second floor offers three spacious bedrooms, including a serene primary suite with a walk-in closet and luxurious en-suite, plus a second bathroom and adjacent laundry room. The third floor features a private retreat with a bedroom, full bath, and flexible space for an office or sitting area. The lower level provides options for a playroom, exercise room, or office. Outdoor living shines with a bluestone patio accessed from the family room, perfect for entertaining. A detached two-car garage completes this exceptional property.