The median home value in Winchester, MA is $1,225,000.
This is
higher than
the county median home value of $638,000.
The national median home value is $308,980.
The average price of homes sold in Winchester, MA is $1,225,000.
Approximately 79% of Winchester homes are owned,
compared to 17% rented, while
4% are vacant.
Winchester real estate listings include condos, townhomes, and single family homes for sale.
Commercial properties are also available.
If you like to see a property, contact Winchester real estate agent to arrange a tour today!
Learn more about Winchester.
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)
Welcome to 7 Wolcott Rd, a truly iconic French country colonial, carefully designed to embrace its incredible location at the edge of the Fells nature preserve. Every detail has been thoughtfully engineered to respect and reflect the beautiful natural setting. This home takes its inspiration from the original 1934 stone cottage. With the completion of the addition in 2015 it is now a gorgeous 10 room estate featuring a sun filled country kitchen, a dining room that opens to a blue stone patio surrounded by a stone wall, a sunroom with stone fireplace and teak floor. There are 2 primary suites, 1 on each level, for a total of 5 bedrooms, 3 full baths w radiant floors, 4 fireplaces, chevron patterned white oak flooring and custom cabinetry throughout. The garden landscape features a heated pool with a potable water system, mature perennials and stone walls and patios. The home is heated and cooled using a geo- thermal system. All this within easy access to Winchester Center.
AMAZING NEW PRICE. Nestled near the Fells and waiting to welcome you home! This stunning 5-bedroom, 3.5-bathroom haven effortlessly combines modern luxury with natural charm. The landscaping, custom stone walls, and gardens are PARADISE!! The heart of this home is the open-design chef's kitchen. Equipped with gorgeous sleek appliances and ample counter space, it's a culinary haven. Large-scale rooms, including a front-to-back dining room with a fireplace, offer easy living and flow. Relax in the huge family room with a gas-burning fireplace or escape to the third-floor study and read. There's a first-floor bedroom suite plus a home office & ample storage throughout. The Fells are just minutes away & the views of the entire Winchester Valley & sunsets are gorgeous. Expertly crafted rock walls and cultivated gardens create a perfect blend of sophistication & nature, close to the town center, schools, and train. A stone patio, treehouse, and dining porch complete this beautiful residence!
This custom-built and brand-new residence, completed in 2024, is located within the prestigious Winchester School District. Surrounded by pristine natural landscapes, the neighborhood exudes tranquility, while the house itself boasts a southeast orientation with large windows, ensuring optimal natural light throughout the day. Convenience abounds with amenities such as shopping centers, tennis courts, parks, walk/jog trails, and medical facilities in close proximity. Transportation is effortless, with easy access to Boston, as well as commuter rail services facilitating daily travel needs. The finished basement has been fully equipped with moisture prevention measures, including drainage pipes and moisture-resistant materials. Heating options include electric and gas, with the ability to control heating remotely via smartphone. The house offers ample storage space, and the basement is fully finished, with a walk-out door for direct access to the outdoors.
Welcome to this spacious home nestled in a cul-de-sac in top neighborhood featuring 6 large bedrooms & 4 full bathrooms. An inviting living room w/fireplace & picture window showcases the great views & allows sunlight to flow through into the formal dining room. Updated kitchen w/views of great yard, dining area & direct access to deck plus sunroom.The main floor also offers 2 large bedrooms & full bath; 2 primary bedroom options plus space for 2 home offices, or in law/ au-pair! Discover the great layout on the 2nd floor w/ 4 beds & 2 baths including an oversized primary suite w/vaulted ceilings & full bath incl. new oversized tiled shower. The 3 add'l beds are spacious w/ generous closets & share a full bath; offering great options for family & guests. The finished basement w/fplc. is great bonus space & grants even more space for family & entertaining w/ bath, laundry, storage w/direct entry into the 2 car garage. Great yard and patio close to town and the commuter rail to Boston!!
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 unique and lovingly maintained home offers tremendous potential and is awaiting your personal touch! Situated in one of Winchesters most desired neighborhoods close to town, this is an opportunity not to be missed. A gorgeous farmers porch welcomes you into this warm, inviting home where you will find large flowing rooms w/ high ceilings, parquet floors & original detail throughout the first floor. Enjoy the beautiful sun-drenched formal living room w/ bay windows & wood burning fireplace, grand dining room, family room w/ walls of windows overlooking a great yard, a versatile den/office space, eat in kitchen & half bath. This home offers an ideal layout for both everyday living and entertaining. The 2nd floor features 3 spacious bedrooms & one full bathroom. Two additional rooms on the 3rd floor. Renovate or expand as you wish, the neighborhood is filled with 2M+ homes, just minutes from downtown Winchester, the train to Boston, Mystic lakes and just 7 miles north of Boston!
Incredibly charming 3 bedroom 2 bath home w/ stunning rear addition nestled on a fabulous oversized lot in a prime location! As you enter you'll be greeted by a warm & inviting floor plan showcasing historic charm & modern day style. The rear addition boasts a stunning family room w/ stone gas fireplace, vaulted ceiling & wall of windows overlooking spectacular yard w/ large patio, beautiful perennial plantings & flowering trees. This home is truly one of a kind offering many cozy and unique spaces w/ an abundance of natural light creating a serene and airy feel throughout. The kitchen offers a perfect blend of vintage charm & contemporary convenience, making it a delightful space for culinary enthusiasts. Fabulous office w/ pocket doors & bookshelves w/sliding ladder, formal LR w/ built ins & 2 dining areas w/picturesque views overlooking the lush yard w/ plenty of space for outdoor activities, gardening & even a pool! Amazing expansion potential on this oversized lot ~ Must see!
Nestled in the heart of Winchester, 44 Cabot Street presents an unparalleled opportunity for luxurious suburban living. The interior features hardwood floors, crown moldings, and a family room that is the perfect place to relax and unwind, with a cozy fireplace and abundant natural light streaming in through the oversized windows. Sliding door leads out to the expansive deck, where you can enjoy al fresco dining or simply soak in the serene surroundings. Outside, the fenced-in backyard provides a great space for entertaining and gardening with a patio and mature landscaping. There is also a detached 2-car garage and off street parking. This well-maintained home is situated a short distance from the Winchester town center with boutiques, restaurants, parks and public transportation access. A wonderful antique home with charm in a premier location!
In Development, New Colonial Construction with 2500 sq ft, 4 bedroom, 3.5 bath. Completion October/November. PICTURES ARE REPRESENTATIVE OF OTHER HOMES FINISHED BY THE DEVELOPER.
Welcome to Parkview, one of Winchester's most well-known residences. Upon entering the cozy unit, you'll feel right at home noticing hardwood flooring throughout, recently updated kitchen with granite counter tops, stainless steel appliances and ample cabinet storage. Just off the kitchen, you'll see a perfect spot for a dinette set or kitchen table. Sun shines into the living room through floor to ceiling windows and sliding doors that lead to your private balcony. Sit and enjoy the wonderful views/sounds of the man-made pond, home to fish and ducks all year round. In the summer months, relax by the pool and nicely landscaped recreation area. Recently renovated bathroom with modern vanity and beautifully tiled backsplash and shower. Heat, A/C, hot water, electric and storage are included in the HOA fee! Nearby to downtown Winchester, shops, restaurants, parks and more.
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
Waterfield Square Condominium, located across from the North Reservoir and the Middlesex Fells Reservation, miles of hiking and bike trails. This turnkey unit has large new windows with remote driven blinds and faces the reservoir on the sunny side of the building. The floor plan is open and the high ceilings make it feel spacious. Designated one parking space and storage in the common basement area. Tennis court, picnic area, communal outdoor grille and firepit. Easy access to Route 93. Beautiful! Please park on the street, not in resident parking lot when viewing the unit. Entry on Appalachian side of the building.
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!
A private estate nestled in one of Winchester's hidden gem locales! The first floor open floor plan showcases a kitchen replete with luxury ~ Quartz counters, Laurier Max cabinetry, walk-in pantry & the culinary technology of Gagganeau appliances. An expansive living room with gas fireplace & custom built-ins flows into a sunroom and outdoor patio surrounded by a canopy of trees. Coffered ceilings & wainscoting accent the dining room with large windows to usher in natural light. FIVE spacious bedrooms with built-in closets, plus convenient 1st floor bedroom suite and sumptuous 2nd FL Primary Suite with vaulted ceilings & rear-facing deck! Family room in LL for movie & game nights with half bath. Lower Level walkout to compact outdoor refuge and a front yard to play hoops or catch. Crafted with attention to modern desires, tucked in a slice of serenity w/easy access to Town Forest Trails, Commuter Rail, Bus, and Winchester's beloved Town Center. Welcome Home!
Located in the most coveted neighborhoods in Winchester, this 3 story townhouse needs updating but has huge potential! It features a large basement that could be refinished, a nice yard, and in walking distance to downtown, both commuter rail stops and the Elementary,Middle and High School.
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!