Winchester MA Real Estate & Homes for Sale
The median home value in Winchester, MA is $1,055,000.
This is
higher than
the county median home value of $454,300.
The national median home value is $185,800.
The average price of homes sold in Winchester, MA is $1,055,000.
Approximately 80.39% of Winchester homes are owned,
compared to 15.01% rented, while
4.6% are vacant.
Winchester real estate listings include condos, townhomes, and single family homes for sale.
Commercial properties are also available.
If you see a property you’re interested in, contact a Winchester real estate agent to arrange a tour today! $1,449,00038 White Street Winchester, MA 01890
ADDITIONAL INFORMATIONCOMPLETE GUT RENOVATION! Originally built in 1880 and having gone through an extensive renovation, this house will be fit for a family soon. Currently under construction . Within walking distance to public transportation. In the Lynch School district. Approximately 3500 square feet, with 5 bedrooms and 3.5 bathrooms. Easy access to downtown Winchester and the Commuter Rail. 7 Miles north of Boston. $1,399,90016 Marshall Road Winchester, MA 01890
ADDITIONAL INFORMATIONStunning mid century modern home meticulously maintained and improved during the past year. Custom designer finishes throughout the open, sun-filled floor plan. Main level feat. a dramatic stone FP, high ceilings w/skylights, HW floors, fully appointed kitchen w/marble island, new high-end Sub-zero refrigerator & JennAir range, formal dining & sitting area w/direct access to screened porch and expansive deck overlooking the lush private backyard retreat w/tranquility waterfall & koi pond. Spacious master suite w/vaulted ceiling, walk-in closet w/center island, inviting FP, private BA & access to private deck. Two addâl BRs & spectacular full BA w/cathedral ceiling & skylight. Lower level makes an ideal guest suite with BR, full BA & media room w/direct access to 2 car gar & storage. 2019 improvements of approx. $100k include new heating & cooling systems & appliances just to mention a few. Easy access to Wedgemere train station, Winchester Ctr, commuter routes and Lincoln Elem. $1,679,000256 Forest St Winchester, MA 01890
ADDITIONAL INFORMATION~New Construction in Winchester~ Under Construction for Summer Occupancy! This 11room, 5 bedroom home is the 2nd of 3 brand new homes by prominent local builder. Thoughtfully designed with an open yet traditional feel. The 1st floor features open concept kitchen and family room w/fireplace, formal dining room, gorgeous kitchen with quartz counters & center island, 1/2 bath & mud room. The 2nd flr features 4 bedrooms, hall way open to foyer below, a large laundry room w/sink, large master bedroom has a luxurious bath with soaking tub, separate fully tiled walk-in shower, double sink vanity and private water closet . The 3rd floor has a bonus room plus a 5th bedroom w/full bath perfect for au-pair, in-law or teen suite. This home is perfect for the family looking for convenient access to the Middlesex Fells, Rt 93 and in the popular Muraco School District. Because this is New Construction and unoccupied, showings ARE allowed and we are adhering to Covid-19 showing guidelines. 
ADDITIONAL INFORMATIONWELCOME HOME! Come see this Charming Central Entrance Colonial! The elegant wood molding and beautiful maple hardwood floors add style and warmth throughout the home. Spacious living room has beautiful fireplace to enjoy with french doors leading to deck. The dining room is accented with a pretty custom built in cabinet. The kitchen with new stainless steel appliances has an inviting built in table area surrounded by bright windows allowing great views of the large deck and gorgeous fenced in yard; all just perfect for entertaining and enjoying with family and friends. A great bonus is the lower level living space complete with 3/4 bath. This inviting home is complimented by the fantastic walkability to so much; Short walk to Horn Pond and trails, to Lynch School and Winchester Center! Enjoy days summer fishing & winter ice skating at near by Twin Ponds. Exterior of home painted 2019. A must see home! Offers to be reviewed June 3rd at 4:00pm. $1,250,0007 Buckman Drive Winchester, MA 01890
ADDITIONAL INFORMATIONPicturesque home on nearly half acre lot close to Vinson-Owen school. Get ready for the savings youâll enjoy from owned solar panels installed with new roof in 2016. Terrific layout features a first floor master suite and 3 bedrooms on the 2nd floor . The walkout lower level has a large finished rec room and a guest room (currently used as an exercise room), a full bath and laundry. Enjoy fireplaces in the living, family and play rooms. Kitchen and dining room have access to deck overlooking the large and private yard. Beautiful southern exposure across the back of the home. Ample closet/storage space and hardwood floors. Come winter, youâll be grateful for the flat driveway and 2 car garage. Enjoy proximity to Rts 2, 128 and 93; Wright-Locke Farm, Whipple Hill, Middlesex Fells, great schools, lovely downtown and more. 3D tour available. Shown by appointment and virtually ANY DAY. "Open WITH appointment" Saturday 5/30 starting at 11am. Don't wait! 
ADDITIONAL INFORMATIONWelcome to The Ledges! This C unit is located in a private wooded setting with a deck off the rear. This well-maintained unit has a first-floor master suite and an updated kitchen with breakfast nook overlooking the sunny courtyard. Lovely hardwood floors in dining and living room. Two additional bedrooms and a bath are on the second level. Potential to finish out lower level with ample storage .This is a perfect opportunity to afford The Ledges and enjoy the Clubhouse , pool, tennis courts and the beauty and serenity of this desirable location. In addition the roof and 4 skylights have just been replaced.A new brick walkway will be coming soon. $785,00056 Salem Street Winchester, MA 01890
ADDITIONAL INFORMATIONWow! This gem of a home boasts soaring 9 1/2 ft ceilings on the first floor - a bright and light open floor plan, gleeming hardwood flooring, Stainless Steel Appliances, granite countertops & island on the first floor. Additionally there is the full bath, den & enclosed porch.The second floor is home to the Master Suite/Office area plus another bedroom and full bathroom. If that isn't enough - check out the third floor which has another two bedrooms, talk about space galore! Gorgeous flat outdoor space perfect for BBQ's - serene and tranquil. Close to all schools, shopping & the town Center. Come check out why Winchester is consecutively ranked one of the best places to live in Massachusetts! 
ADDITIONAL INFORMATIONDesigned by architect John G. Danielson, this custom built Mid-Century Modern style home is sited on .4 acres and set far above the road amidst a bucolic wooded setting ideal for birdwatchers & hikers. The most stunning feature upon entry is the vast open living room and dining room with soaring ceilings boasting exposed solid mahogany beams and rafters, & a floor to ceiling fireplace surrounded by rare pecan wood paneling, & walls of windows flooding the rooms with natural light. Simply breathtaking! Other amenities include solid oak hardwood floors in formal rooms, hallway & bedrooms. Lower level has a fireplaced family room with pecan paneling, office, laundry, & heated 1 car garage. Building's exterior has redwood siding. Updated electrical. Heating cables under the driveway. This home is being sold AS-IS, but has had critical recent updates: e.g., in 2019, new roof, hot water heater, chimney cap & fireplace dampers. Vinson Owen Elementary. Make this your dream home in Winchester! $699,00032 Tremont St Winchester, MA 01890
ADDITIONAL INFORMATIONAntique Colonial with front porch and back deck on a quiet side street of Winchester. Home has 3 bedrooms with 1.5 baths and is situated in a friendly neighborhood walking distance to Winchester center and commuter rail. The first floor is freshly painted and features hardwood floors . The kitchen features new lighting and a center island perfect for preparing meals. The kitchen has a space set up for use as computer station or work space . A half bath is also on the first floor .You will love the charm of built in China cabinet in the the dining room . Family room completes the first floor.As you go up the stairs you will pass a stained glass window on your way to three bedrooms . One bedroom has washer /dryer which can stay or be removed.Washer /Dryer hook up in the basement as well . The bathroom is updated with new fixtures and paint . This is a great home in a great town. $999,000237 High St Winchester, MA 01890
ADDITIONAL INFORMATIONWelcome to 237 High Street, a nature loverâs dream tucked in a serene location surrounded by beautiful conservation land, hiking trails and pond views. Relax in the living room next to the fireplace or, on a warm day, in the enclosed 3 season sun porch surrounded by sights and sounds of nature. A beautiful family room features dramatic cathedral ceilings, skylight & cozy wood stove, plus sliders to a private deck and sprawling backyard. Contemporary kitchen with stainless steel appliances & granite counters. Formal dining room & half bath complete the 1st floor. Three generously sized bedrooms and 1 full bath on 2nd floor. Lower level features a large entertainment room with dry bar, laundry, storage & exterior access. Additional highlights include Nest thermostats, insulated attic, outdoor motion lights, recessed lighting. 1 car garage and off-street parking for 6 cars. Situated on a large lot in desirable West End neighborhood near VO Elementary. PRIVATE SHOWINGS SUNDAY 5/31 11-12 PM $1,499,9001 Thornton Rd Winchester, MA 01890
ADDITIONAL INFORMATIONOpen Showings Sunday 1:30PM- 3:00PM. A Master piece of Style and Elegance in this Spanish Style Colonial offering curb appeal like none other. Exquisite & detailed woodwork warms when you enter this charming residence. The property features 9 very unique Rooms, 4 Beds and 2.5 Baths including a romantic Master En Suite w/ abundant custom built storage and 2 Double Closets & FP! 2 more spacious bedrooms, a perfectly designed office, and another full bath finish off the 2nd Floor. Main Level features a Custom Built kitchen, stainless appliances, additional prep sink w/filter, & breakfast nook. Enjoy the view in the Formal Dinning Room overlooking outside Pergola. Custom woodwork and cabinetry detail Back to back Living Rooms, Pella Windows & Gas FP. Finished basement w/another Lvng RM & bedroom, Laundry, and utility closet. Abundance of storage in Attic and top Floor in oversized 2 Car Garage. Fenced yd protects luscious gardens, mature plantings w/ multiple seating areas wired for sound $2,275,00015 Grove Street Winchester, MA 01890
ADDITIONAL INFORMATIONOld world charm and satisfaction perfectly blended with all the comforts and luxuries of today's new construction. Manicured grounds invite you up onto the quintessential New England front porch. Open the front door and instantly take in the grand foyer, beautiful moldings and detailed wood work. On the first floor, you will find a classic front parlor to one side and a front to back living room both swimming in natural light. Dining room with fireplace and built-in china cabinet perfectly located off the large, brand new eat-in kitchen makes entertaining a breeze. The beautiful bright kitchen boasts an over-sized quartz island with seating, stainless steel appliances, large pantry, kitchen table for 6+ and access to the exterior patio, back entry or 2-car garage. The expansive second floor features 5 large bedrooms, plus a home office/guest room, 2 laundry rooms and master suite. Lower level offers great flex space for a home gym, teen get-away etc. Winchester at its finest.! $1,995,0009 Everett Ave Winchester, MA 01890
ADDITIONAL INFORMATIONElegant and meticulously cared for 1911 Craftsman Colonial with a premier Winchester address. Set on a 3rd of an acre with mature trees and hedging, across from Upper Mystic Lake and 0.4 miles from Wedgemere Commuter Rail. Enter through the original lead glass French Door into the entry with quarter-sawn oak floors + refined, original Craftsman moldings. The graceful staircase turns twice in front of an oversized window that lets in an abundance of light. Entertain in the well-proportioned dining room with original fireplace, natural stained oak beams that opens to the European kitchen. The Living Room on the opposite side of the entry mirrors the Dining Roomâs craftsman details + has a second original fireplace. Off both the living and dining rooms are twin sun rooms, giving the floor plan balance and symmetry. The second floor offers three bedrooms, two with en-suite baths and an additional sitting room. The 3rd floor master suite completes this beautiful home. Virtual tour available 
ADDITIONAL INFORMATIONGreat opportunity to owns stunning duplex home nestled in a quiet cul-de-sac. It recently has many updates: newer kitchen cabinets, center island, granite counter top, stainless appliances, new bathroom vanities. Exterior has new roof, siding, decks, railing. This sun filled home offers 3 bedroom, 1.5 bath with 1 car garage, first floor featuring bright living room, open concept kitchen and dining area leading to the back deck, hard wood floor throughout.The second floor offering 3 bedroom and 1 bath. By the way, if you need more space, the high ceiling lower level is ready for you to finish. Extra storage space in the attic. Laundry in the lower level, garage access to lower level as well. This home has Central AC and electricity supports all utilities. Step to the Tri Community Bikeway. Close to school, town center, public transportation, and major highway and much more... Don't miss this opportunity to move in and make it your own home 
ADDITIONAL INFORMATIONGreat opportunity to owns stunning duplex home nestled in a quiet cul-de-sac. It recently has many updates: newer kitchen cabinets, center island, granite counter top, stainless appliances, new bathroom vanities. Exterior has new roof, siding, decks, railing. This sun filled home offers 3 bedroom, 1.5 bath with 1 car garage, first floor featuring bright living room, open concept kitchen and dining area leading to the back deck, hard wood floor throughout.The second floor offering 3 bedroom and 1 bath. By the way, if you need more space, the high ceiling lower level is ready for you to finish. Extra storage space in the attic. Laundry in the lower level, garage access to lower level as well. This home has Central AC and electricity supports all utilities. Step to the Tri Community Bikeway. Close to school, town center, public transportation, and major highway and much more... Don't miss this opportunity to move in and make it your own home 
ADDITIONAL INFORMATIONGreat location corner of Brookside Ave! Charming bungalow style home with many recent updates including completed renovated full bath, refinished hardwood floors and freshly painted interior walls. Move-in by summer and enjoy the wonderful amenities of Winchester! Charming home located on oversized corner lot and in desirable Muraco school neighborhood! Lovely front porch welcomes you into this sun-drenched home offering formal living room w/ wood burning fireplace open to dining room w/ built in hutch, updated kitchen with breakfast dining area and door to back yard. Potential to finish the basement with direct entry from garage. Enjoy the neighborhood park across the street and the tri-town bike path right around the corner! Don't miss out! $1,400,0008 Gershon Way UNIT 8 Winchester, MA 01890
ADDITIONAL INFORMATIONWINCHESTER'S 1ST 55+ COMMUNITY! This new construction development is the proud winner of The National Association of Home Builders gold award recipient for design (2018). Imagine luxury finishes throughout, including 10' ceilings, hardwood floors and plenty of natural light. The open concept floor plan boasts a 1st floor master suite with oversized walk-in closets and luxurious bathroom. The kitchen is adorned with ceiling height cabinets, granite countertops and a top of the line stainless steel appliance package. Cozy up to the gas fireplace with a hot cider. The dining room has a beautiful coffered ceiling and sliders to a private, covered deck. The bonus room could be a home office, library or studio for your beloved hobbies. 1st floor also features a powder room and laundry. Upstairs you'll find 2 additional spacious bedrooms, a full bath and an open loft area. 2 Car garage. ***PRIVATE SHOWINGS SUN 12AM-2PM BY APPOINTMENT ONLY***SEE ATTACHED SAFETY GUIDELINES*** $998,00028 Johnson Rd Winchester, MA 01890
ADDITIONAL INFORMATIONThis lovely split-level home situated in the sought-after West Side is a hard to find gem. An expertly planned 2005 addition adds to the classic 3 bedroom, 2.5 bath layout providing a stunning great room off the newly renovated kitchen featuring a Palladian picture window and access to two decks overlooking a charming and very private backyard.The traditional living and dining rooms offer a fireplace, pristine built in china and access to a breezy and bright three season room. The lower level boasts a generous fireplaced Family/Rec room with adjoining snack/kitchenette area, mud room,laundry room,walk in closet and a versatile home office or gym space. The convenience of an oversized two car garage and practical circular drive providing ample parking for family and guests are a bonus.In the Vinson Owen elementary school district which is an award winning âBlue Ribbonâ school!Great room surround sound system, exterior security cameras and solid wrought iron 3 season furniture included! $2,249,00018 Brooks Street Winchester, MA 01890
ADDITIONAL INFORMATIONOpen Sunday 12-2, masks and gloves must be worn. Imagine a Back Bay mansion set in bucolic Winchester...this home personifies the look and feel.This is one of those homes that just stop you in your tracks, in an A++ location. It's all about the soaring ceilings, incredible moldings and trim. The original leaded glass windows that beckon from all over the house, a spectacular foyer that embraces with beauty, numerous windows seats, pocket doors and huge fireplaces. Spectacularly oversized custom French doors highlight the front of the house and open onto a stone porch that wraps around the house and creates an amazing entertaining flow. The living room is bathed in light and across the extra large entry hall is a matching parlor, currently being used as a study. The dining room can hold 30 for dinner! The kitchen is enormous with a big walk in pantry, and leads to a large family room. $2,149,0005 Dean Road Winchester, MA 01890
ADDITIONAL INFORMATIONNot all new construction is created equal. 5 Dean Road has been meticulously constructed with warm tones, modern highlights, and exquisite fixtures that will have you mesmerized from the moment you enter. The 1st floor is an entertainers dream. The designer kitchen is equipped with Thermador appliances, sophisticated wet bar, full eat-in, and oversized island. It's sure to make cooking fun again! The family room, with linear fireplace, boasts tall ceilings and exterior access to the lush green yard. A home office, 1st floor bed, full bath, parlor, formal living room, and dining room are all found on this level! Yes, this home IS expansive! The dramatic bridal staircase leads you to the 2nd floor. There you'll find 4 additional bedrooms including the master suite. This spa-like oasis offers a marble drenched bathroom AND his and hers closets! The lower level has a gym area, rec room, media room, bedroom, and full bath. With a 3 car garage this home truly has it all, and more! 
ADDITIONAL INFORMATIONWelcome to this refreshing home! The entrance hall transitions to a front to back fireplace living room with hardwood floors and a built in book case. You will actually enjoy working from home in the office with views to the front plantings and access to a two-tiered, mahogany deck. The entrance hall also leads to an efficient kitchen with a separate dining room as well as a full bath and master bedroom. The lower level walks out to the expansive yard and includes 2 bedrooms, a large full bath, laundry room and utility room. The spacious backyard with beautiful plantings makes this a truly tranquil setting. The size of this home is perfect for those seeking ease of living in under 1,600 sq. feet. $2,695,00010 Hillside Avenue Winchester, MA 01890
ADDITIONAL INFORMATIONLOCATION...LOCATION...LOCATION Magnificent Historic VICTORIAN HOME, originally- The "John Mason House" with a touch of modernist flair. High style structural exterior boasts its original facade. Perfectly situated on a hill, this captivating home offers magnificent skyline views of the city, hills & serenity. Grand entrance with immaculate double doors welcomes you to grandiosity, soaring ceilings with rich carved moldings around windows & doors, ornate chandeliers, deep archways set the stage for interior opulence. Luxurious ITALINATE MANSION carefully & painstakingly modernized for efficiency & functionality (smart HVAC system), offers a spacious boastful gourmet kitchen with GE Monogram SS appliances, exclusive media (cinema) room with AV ($100k) surround system, custom-built office, renovated recreation/game room, skylights, formal dining & tranquil meditation area facing views. OPEN FLOOR PLAN. Minutes to school & train.Ready to Move in. Look no further to own a piece of history! $2,650,00065 Myopia Road Winchester, MA 01890
ADDITIONAL INFORMATIONA stately Colonial set atop Myopia Hill in one of Bostonâs most desired suburbs, 65 Myopia Road is a tranquil & immaculate estate well adapted to modern family living. Beyond the grand entry foyer are graciously scaled living & entertaining rooms with oversized windows highlighting beautiful views of the private outdoors. These include the double height living/family room with impressive stone fireplace, chefâs kitchen with vaulted breakfast nook, & formal dining room with elegant fireplace. The homeâs 4 generous bedrooms are all located on the 2nd level. The Master suite is breathtaking with spacious walk-in closet and luxurious bath. Additional features of this residence include the 2nd floor mezzanine game room, home gym, expansive outdoor mahogany deck, & heated outdoor pool. This home is only 9 miles north of Boston, accessible to the commuter rail to North Station, within ½ mile +/- of Ambrose School, & within close proximity to all the shops & restaurants of downtown Winchester. $2,999,99934 Everett Avenue Winchester, MA 01890
ADDITIONAL INFORMATIONItâs been almost 45 years since this iconic lakefront property has been available to own. For Winchester aficionados, you know the home in which weâre referring to. From the moment you turn onto the highly acclaimed Everett Avenue this stately 6 bedroom, mediterranean style mansion, captures your eye and doesnât let it go until you approach. Once proudly featured as âTHEâ home on Everett Ave in the Boston Globe Magazine, âTop Spots to Liveâ addition, here is your chance to make it âYOURâ home. From the moment you enter into the foyer the water views will captivate you. 4 levels of living, including a walk-out basement with access to level green space overlooking the Mystic Lake. Boating, fishing, and fun right in your backyard! Stunning period detail can be found throughout including mahogany woodwork, coffered ceilings, and multiple fireplaces. Fall in love with this idyllic location. Walk to the Winchester Boat Club, Winchester Country Club, Winchester Center, AND the commuter rail. $1,649,00092 Bacon Street Winchester, MA 01890
ADDITIONAL INFORMATIONMotivated seller! This stately Colonial Revival has been beautifully maintained and is a charmer. Located at the corner of Bacon Street and Stratford Road, this property has ten rooms, six bedrooms and three and a half baths. Upon entering the front door, one can enjoy an enclosed porch. (partial screens in summer). The stunning center entrance hallway has a ten foot coffered ceiling with quartersawn oak. Natural light flows through the leaded glass windows in the Dining Room which has a built in china cabinet. A gas fireplace invites you into the Living Room. Through the pantry area is a spacious eat in kitchen.The inviting Den completes the first floor. The second floor has four bedrooms and two baths and the third, two bedrooms and a bath. The spacious two car garage faces Stratford Road for easy exiting. A good part of the backyard is patioed, perfect for shooting hoops and playing street hockey. There is a grassed area as well. Close to town, commuter rail, schools, and parks.
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