Winchester MA Real Estate & Homes for Sale

This Graystone expansive townhouse is among the 50 unit 2010 development located in gorgeous Winchester. Too many energy efficient and high-end finishes to mention: a spacious light filled open floor plan with soaring ceilings and an abundance of recessed lighting, sky lights, oversized windows. Featuring large marble bathrooms, custom built walk in closets, kitchen has gorgeous granite countertops and copious cabinetry storage including pull out pantry. Bask in the warm glow of the fireplace in soaring cathedral living room with built in bookcases, and create visitor/ office/ den space up stairs, which includes a full bath with soaking tub. There's a full deck for morning sun bathing or entertaining as well as two-car garage parking and in-unit laundry. 24 Hour professional management, landscaping is no longer your "must do" weekend chore! This townhouse is tucked into the quiet enclave at the back edge of the property. Freshly painted, quick close ready! Showings start Wed 17th OH

Welcome home to this spacious townhome in the coveted community, "The Village." This is a sought-after end unit featuring an attached garage with direct entry inside. Upon entering, you will find a tidy kitchen with granite counters and breakfast bar and stainless steel appliances, which opens to a bright dining area with a skylight and access to a private patio overlooking a grassy courtyard. On this level you will also find an expansive living room with gas fireplace, and a half bath. Head upstairs to find the primary suite which features a walk-in closet, additional closet and full bathroom. One more bedroom, a bonus room/office, a second full bathroom, dedicated laundry area and additional closets complete this floor. Unit #63, with an extra driveway for added parking, is located in close proximity to the association's swimming pool, clubhouse and tennis court. The Village is a short distance from Winchester's vibrant town center, schools, and commuter rail stop.

Get ready to swoon over this exquisite, completely renovated "C" Unit townhouse at "The Ledges" which is truly unlike any other you've seen. Enter into the sleek, open-concept kitchen w/ lacquered custom cabinetry w/ Italian pulls, Wolf cooktop & double wall ovens, Subzero refrigerator & wine fridge, double thick quartzite island, pantry cabinets, beverage station & glam light fixtures. The main level also features a dining area, living room w/ linear gas fireplace & sliders to a deck, half bath, & primary suite. The glamorous primary suite boasts a bedroom w/ vaulted ceiling, stunning quartz bath w/ double vanity, 2 custom closets, and laundry. The second floor features a loft area/office, two large bedrooms & a full bath. The expansive lower level features a huge family room w/ sliders to a patio, beverage station, gym/bedroom, & full bath w/ infrared sauna. There are too many luxurious features & amenities to list - you simply must see it.

Welcome to this charming Winchester home! Nestled amidst lush greenery, it exudes classic ranch style and is located in the sought-after Muraco School District, near Horn Pond and Middlesex Fells Reservation. Just a 20-minute drive to downtown Boston, this location offers both convenience and tranquility. Renovated in 2022, it consists of modern upgrades including stainless steel appliances, an updated AC system, and a new gas water heating system. Step into the beautiful garden leading to the spacious kitchen with new quartz countertops and Imitation wood grain tiles. The open-concept living room features gleaming hardwood floors. Two bright bedrooms and an office/den provide cozy spaces, while the expansive basement offers endless possibilities. Outside, stone pathways lead to the well-maintained backyard with a swing and picnic area, perfect for outdoor gatherings. Don't miss the chance to make this dream home yours!

Step into refined living with this gorgeous 5-bedroom, 4.5-bathroom colonial home tucked away on a quiet cul-de-sac. You'll be greeted by a spacious layout with a chef's kitchen featuring a top-of-the-line 48" Sub Zero refrigerator/freezer, a gas range topped with a stylish hood, and a cozy breakfast bar. The dining area, boasting cathedral ceilings and a double-sided fireplace, seamlessly flows into the sunlit living room and onto a convenient deck. Relax in the luxurious first-floor primary suite with a marble bathroom featuring an oversized jacuzzi and a separate sauna. The 2nd level has two additional bedrooms, two full bathrooms, and a cozy family room. The finished basement adds even more space with two extra bedrooms and a full bath, which is ideal for entertaining or as a play area. Enjoy radiant heat throughout the entire home and garage. Outside, the professionally landscaped yard offers a peaceful retreat, which is all walkable to the Town Center and nearby walking trails.

Welcome to this charming 4 bd, 3 br home situated on a gorgeous oversized lot on the desirable East side! Step inside this updated home to discover a warm & inviting layout designed for both family time & entertaining. The open floor plan seamlessly connects the kitchen & dining to a stunning family rm w/built ins, fireplace & french doors to fabulous deck! The blended kitchen & dining room are perfect w/ modern appliances, great storage, & a center island for culinary creations. The 1st flr also offers one private bedroom w/ adjacent bath plus a sun-drenced living room w/ add'l fplc. Two additional very spacious bedrooms on 2nd floor w/ full bathroom. The walk out lower level offers a 4th bedroom suite/great in law or au pair w/ full bathroom and walk in closet. The finished lower level also offers a family/media game room, laundry & spacious mudroom that leads to garage & oversized yard w/ 2 sheds. Easy access to the Fells, Winchester center, Lincoln school, Boston & highways!

Imagine living at the foot of the Fells, surrounded by a natural setting while being close to the Muraco School, trains, and the town center. This gorgeous Colonial sits high on a hill, surrounded by custom rock walls, a stone patio, and mature landscaping. With 5 bedrooms, including a first-floor guest suite, there's room for everyone and options for live-in nannies, in-laws, or aging in place. A stunning open kitchen awaits, featuring leathered granite and stainless-steel appliances. Large-scale rooms, including a front-to-back dining room, enormous family room, and lovely living room are offset with a sweet outdoor porch where you can have dinner and catch the incredible sunsets over Winchester Valley. The second floor features a large private primary suite, a huge walk-in closet, and a vaulted ceiling. 3 other bedrooms have big closets plus there is a storage and laundry room. There is also a 3rd floor study, an oversized 2-car garage, and a basement that can easily be finished!

Yes you can have it all. Winchester Flats, corner of Yale Street location. Exquisite move in ready gracious home, that will truly impress. Excellent layout, with a first floor bedroom and bath, walk in shower and double sink vanity. Spacious and sunny living room with a fireplace, dining room, and a first floor office. Family Room off the updated, eat-in Kitchen with sliders to the Patio and private back yard, ideal for indoor, outdoor entertaining, garden and play. Second floor primary bedroom suite with sunset views, 3rd bedroom and full Bath. Ample Storage and closets with expansion possibilities, easy to Dormer or expand if your desire. BONUS fireplace recreation room, bath with Stall shower on the low-level. SELLER PREFERS TO CLOSE AFTER THE End of SCHOOL YEAR. Offers due by 4/21- 7:00PM

Welcome to this adorable 4 bed, 2.5 bath home with a fenced in yard! ~ This property features a large family room with a beautiful fireplace, an attached sunroom or perfect home office, spacious dining room & updated kitchen w/ gleaming hardwood floors and high ceilings throughout the home. For guests, or a 1st floor primary option there is a first floor bedroom w/ adjacent full bath.The second floor has 3 generously sized bedrooms w/ vaulted ceilings & full hall bath.The lower level is the perfect spot to watch a movie. Garage access, mud room, half bath, laundry and storage complete this home. Conveniently located close to highways,Winchester Hospital, Winch.Center, Muraco school & Leonard field. Enjoy coffee & muffins at your new home, w/ Winchesters beloved Gingerbread factory right across the street! With this homes great price, prime location & potential to make it your own, you won't want to miss this opportunity. 1 garage & 2 driveways for extra parking! $10k SELLER CREDIT

Perfectly situated in one of Winchester's most prestigious neighborhoods, "The Flats," this 7 bedroom home has an expansive lot w/ welcoming patio, fire pit & large level yard perfect for family fun! The 1st floor is stunning w/an abundance of picturesque windows that flood the living space w/ natural light. An exquisite mahogany wood-burning fireplace graces this inviting living rm complemented by bay window seating & garden views. Adjacent family rm & elegant dining rm lead to a butler's pantry & spacious updated kitchen w/granite counters, stainless appliances, cherry cabinets & dining area. The mudroom offers access to side entry & 2 car garage. The spacious 2nd floor offers 5 generously proportioned bedrooms and home office. The 3rd floor boasts 2 add'l bedrooms or home office & bath. Newly renovated lower level media room w/surround sound & wine cellar. Entire house renovated to 200 amps, recessed lighting, zoned sound system, new bath. Perfect blend of tech and timeless beauty.

A Brand New Townhouse with a modern stylish feel is nearing completion and will soon be ready for a new owner to make it Home! Located just minutes away from all the amenities in Winchester Center you could not ask for a more convenient location. You will be wowed as you cross the farmer's porch into the well designed open 1st floor that features a custom FP in the living room, built-in bench seating in the dining room and a dream kitchen with ample cabinetry and an island with a waterfall edge. You will also find a half bath off the mudroom and a slider to the private fenced in rear yard. The 2nd floor features the main suite with custom bath and walk-in closet, 2 additional bedrooms and another full bath. The finished LL has the 4th bedroom, a full bath and sitting room. Exterior access is also provided. This must be seen to be appreciated! (More photos coming soon)

Presenting Winchester's newest luxury new construction home, 4 Abby Road. The first floor features a formal dining room, fireplaced family room, and an eat-in kitchen with a gorgeous island & wet bar. The large mudroom, conveniently located off the garage, provides seamless access to the home. Additionally, a private home office just off the mudroom makes a serene space for work or study. The finished lower level boasts a glass enclosed gym with rubber floor, full bath, & media room. As you make your way to the second floor, you'll find four bedrooms, each exuding comfort & style. The primary bedroom is a true retreat, complete with a spa-like bath, oversized walk-in closet, & a separate den/nursery, offering a true sanctuary within the home. The location offers the perfect blend of tranquility & outdoor adventure. Residents can enjoy the convenience of walking to the Fells Reservation, where hiking, biking, & other outdoor activities await, while still being close to both I-93 & I-95!

Welcome to your dream home nestled on highly sought-after Glen Road! This charming 1910 house boasts modern updates while showcasing timeless elegance. With 6 BR, 2 BA, & over 1/2 acre of picturesque land, this property has it all.The 1st floor boasts a grand entryway opening to an updated eat-in kitchen w/ granite countertops & SS appliances. An elegant living room, featuring a graceful fireplace, opens to a beautiful dining room w/ detailed moldings, a ceiling medallion, & glass cabinetry. The highlight of this level is the inviting family room, w/ a vaulted ceiling, fireplace, built-in bookcases & abundant natural light streaming in through numerous windows & glass sliders. 6 spacious bedrooms, including a main bedroom w/ oversized walk-in closet. The vast backyard features lush landscaping, mature trees & serene flower gardens which create a magical oasis. Located near the town center and the elementary school, this home combines the charm of a bygone era w/ modern conveniences.

Sunny, bright and spacious! This residence is tailor-made for hosting gatherings. The open concept living and dining room is adjacent to the chef's kitchen, complete with high end appliances, ample counter space and 2 skylights. But the real gem is the 4 season room just off the kitchen offering a tranquil retreat to enjoy your morning coffee while enjoying the beauty of the changing seasons. Upstairs include a primary bedroom with ensuite plus three additional spacious bedrooms. Connecting directly to the two car garage, you'll find a generous family room, laundry room, and a full bath. The lower level has a finished basement with working fireplace and tons of storage. Outside enjoy hosting barbecues in your expansive level backyard with stone patio. Located within the Vinson-Owen school district and near Wright-Locke Farms, hiking trails, and Mullen Field. 4 yr old roof!

Top location close to Winchester Center! This 4 bd, 3.5 br home is situated on a generous lot, offering abundance of space & functional floor plan for multi-generational or au-pair living. Greeted by a sunlit interior, showcasing hardwood floors & a cozy fireplace, creating a warm & inviting atmosphere. Enjoy the well-appointed kitchen w granite countertops & breakfast bar w/seating open into the spacious dining room. This home has 2 primary suite options as well as a recent 3rd floor addition w a secondary family room or office space plus a large bedroom suite w full bath! You will love the fenced in yard & 2 car garage with direct entry into the mudroom & the lower level family room w fireplace and wall of windows. The lower level also offers a full br/laundry room. Enjoy all the space this great home offers w/ close proximity to town, schools, dining, shopping, the fells & more! LAN upgrade & little to no electricity bill w solar panels! Don't miss out on this highly desirable home!

This is one of the most notable and distinguished homes on Everett Avenue, with preeminent siting and curb appeal. Designed by famous architect Robert Coit, this residence combines the magnificence of early 1900s architecture with today's modern amenities. Completely renovated in 2023/2024, this residence features hallmark architectural details including Tudor-style balusters, high ceilings throughout, and a beautiful floor plan centered with a large entrance hall. Large-scale rooms, coffered ceilings, original crown moldings, mantels and decorative trim are enhanced by the beauty of restored hardwood floors. The brand new kitchen is a chef's dream, and includes a walk-in pantry with laundry and refrigerator drawers plus a butler's pantry with a wine fridge. Floor to ceiling windows flank the huge family room, overlooking park-like flat grounds. The huge lawn, magnificent old oak trees, beautiful birches and an ample driveway are some of the distinguishing exterior features.

This home evokes a fresh, breezy, coastal vibe-making everyday feel like vacation. Located on the MOST PRIVATE homesite within this Award Winning 55+ Community. It is a modern, entertainer's dream house which boasts an open concept plan, TOP OF THE LINE CHEF'S KITCHEN + a buffet & bev. center in the adjacent dining room - which is "topped off" by a masterfully built coffered ceiling. All rooms look to the 2 story family rm, where a toasty fireplace wall is flanked by windows. The 1st floor also features a jaw dropping home office with French Doors & another coffered ceiling! For easy living: the primary suite is on the 1st flr, as well your covered deck & outside lounging area. Upstairs features: 2 bdrms, guest bath, sitting rm & loft. The FINISHED lower level has rm for a home gym + dinner & a movie. Enjoy indoor/outdoor 180 private wooded views, walking trails...Located near Winchester Center & the NEW Rail Station taking you to heart of Boston, just 8 mls away. A must see-must own

Located on one of the most desirable streets in Winchester is this 5 bedroom home with amazing views of Mystic Lake close to Wedgemere Station, Shannon Beach, and restaurants downtown. Through the front door you'll be impressed with beautiful in-laid hardwood floors that flow through the dining room and formal fireplaced livingroom. Top of the line appliances include a subzero refrigerator, gas Wolf oven with grill and a wine island with it's own dishwasher, sink, two sub-zero refrigerators, and plenty of room for seating. French doors off the kitchen lead to the beautiful wrap around deck with a partially covered area for shade, perfect for entertaining family and friends. Plenty of considerably large windows throughout the home allow for bright light in every room. The lower level consists of a den with access to the patio, a wine cellar, and interior access to the 3 car garage. Private well for irrigation and peaceful sitting areas with perennial blooms all season. Sold as-is

Welcome home! Nestled on a huge, fenced-in lot in a sought-after neighborhood, this picturesque 4 bed, 2 bath home has it all. A spacious eat-in-kitchen with granite peninsula opens to a sun-filled family room boasting French sliders out to an elegant bluestone patio. The first floor also features a front-to-back, fireplaced living room, a bright home office, and a mudroom/playroom. Head upstairs to a stunning primary suite with soaring ceilings, a large, updated bath with glass shower and oversized tub, generous closets, laundry hookup, and French doors opening to a charming balcony. The second floor also features three additional bedrooms, an updated family bath, and additional closets. The partially finished basement includes an exercise room and a spacious storage area with additional laundry hookups. The backyard oasis with seasonal water views is perfect for outdoor enthusiasts. This home seamlessly blends comfort and style. Don't miss this gem!

Welcome to 50 Lorena Rd, a stunning custom-build Colonial home in Winchester, MA. Step inside and admire the architectural grandeur of an elegant foyer, hardwood flrs, french doors, custom built-ins, custom millwork and high ceilings. The chef's kitchen is a culinary delight, large island, pantry, granite counters,SS appliances, and a sun filled dining nook. 2nd floor includes 5 bedrooms (2 ensuite bathrooms), walk-in-closets, and bespoke staircase w/ large windows. The house also offers a large finished lower level for entertainment, play, exercise and storage. Outside, enjoy the private yard, patio and deck, perfect for al fresco dining. Additional outdoor features include a covered porch, gorgeous plantings, stone-work and sports court with basketball hoop. Tree views from every room - including views of the fells - and the most amazing sunsets. This home presents a rare opportunity to experience luxurious living 8 miles from Boston. Walk to Center, MBTA train and schools.

Welcome to Winchester's premier 55+ community, a luxurious enclave nestled on the coveted west side. This unit is a perfect blend of modernity and comfort, all while enjoying the utmost privacy in this premiere location within the development. Step into a world of sophistication, where 10' ceilings, rich hardwood floors, & an abundance of natural light create an inviting ambiance. The open concept floor plan showcases a first-floor primary bedroom, complete w/ expansive walk-in closets and a lavish en-suite. The chef's kitchen features quartz countertops & high-end stainless steel appliances. Spacious living area w/ a gas fireplace, custom built-ins and coffered ceilings. Sliders from the dining room lead to your private covered deck, offering a serene retreat for relaxation. A versatile bonus room awaits your personal touch, ideal for a home office! Second level features 2 additional bedrooms and full bathroom along with a loft. Conveniently located near downtown Winchester & Boston!

NEW CONSTRUCTION!! Must see this gorgeous 6 bedroom home w/ thoughtful design & high end finishes! This home is spacious & inviting, offering a grand open flr plan ideal for entertaining & modern day family living. The kitchen features an oversized island w/ seating/ quartz countertops, high-end appliances, & breakfast nook/dining area. Off the kitchen is a spacious family room w/gas fireplace & direct exterior access w/ sliders leading to large deck or patio & nice rear and side yard. The first floor also offers a formal dining room and guest bedroom w/ bath plus a home office & 1/2 ba. The second level primary suite is luxurious, offering a sitting area, sleeping area, huge walk-in closet, lavish bath w/double vanities, oversized shower & soaking tub! Three additional beds incl. junior suite w/ bath, full hall bath & laundry room finish this level. Finished lower level media/ rec room w/ full bath. 2 car garage direct entry to great mudroom! Quick & easy access only 6 miles to Boston

Welcome to this exquisite WATERFRONT PENTHOUSE nestled in the heart of Winchester. Upon entering, you'll be captivated by the seamless flow of the open concept kitchen, living, and dining area, complemented by not 1 but 2 private balconies that offer breathtaking water views. The primary suite is a true haven, featuring an expansive walk-in closet (large enough for exercise equipment), vast storage, a 3RD private balcony, and a luxurious spa-like bath. The kitchen is a culinary delight, boasting a large center island, marble tops, and high-end appliances. With its stunning style and finishes, this condo is sure to impress even the most discerning buyer. Practicality meets luxury with abundant storage. A large pantry off of the kitchen has built-ins, a 2nd fridge, and a washer and dryer. There are lots of options in this additional room! 2-car garage parking with you guessed it - more storage space! Downtown location within walking distance of shops, restaurants, commuter rail and more!

This fabulous house is in a beautiful and unique location, perched on a small hill with a secluded half-acre lot in a very quiet cul-de-sac area near the Winchester/Lexington line, far away from any road traffic and offering excellent privacy. There are 4 floors of living space containing 5 bedrooms and 3.5 bathrooms with two separate laundry areas. The grounds offer stunning front and back yards with a large deck and a gazebo. The property is adjacent to a lovely forest with a pond (Whipple Hill/Smith Pond). A short walk away from Wright-Locke farm and a short drive to shops, malls, and major routes with an easy commute to main business areas. Plenty of leisure facilities nearby including swimming pools, tennis courts, golf courses, skating rinks, gyms, restaurants, etc. Importantly, this house is in one of the best school districts anywhere and the Town of Winchester is renowned for its charm and the quality of life it offers.

NEW CONSTRUCTION! This spacious 6 bed, 6.5 bath home by a top local builder has it all! With over 6,300sf of living space you won't want to miss this stunning home. The first flr offers a gourmet kitchen w/ oversized island w/ seating/ quartz countertops, high-end appliances, & breakfast nook/dining area. Off the kitchen is a spacious family rm w/gas fireplace & direct exterior access w/ sliders leading to a large patio & great yard. The first floor also offers a guest bedrm or home office w/ full bath, mudroom and powder rm. The second level primary suite includes huge walk-in closet, lavish bath w/double vanities, oversized shower & soaking tub! Three additional beds, 2 full baths & laundry room finish this level. The finished third flr is a large loft/playroom/gym w/ full bath. Finished lower level media/ rec room, additional bedroom w/ full bath and wine cellar. 2 car garage direct entry to great mudroom! Conveniently located just 7 miles north of Boston nr Hospital & the Fells!