Winchester MA Real Estate & Homes for Sale
The median home value in Winchester, MA is $938,500.
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 $938,500.
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! $1,885,000432 South Border Rd Winchester, MA 01890
ADDITIONAL INFORMATIONWelcome to 2019 and Winchester's first UNDER CONSTRUCTION home of the year. Breaking ground soon and for Summer! Truly spectacular, beautifully designed, custom built, Shingle Style colonial with 5 bedrooms and 5.5 baths situated on a large, 23,927 square foot lot. Nestled adjacent to the serene 2,600 acre Middlesex Fells, sought after by bikers, joggers, and hikers, and only minutes from downtown Boston. Highest quality finishes with crown molding and hardwood floors, this beautiful home offers all of today's amenities with two car garage, direct entry into mudroom, high end chefs kitchen, great room with fireplace, and dining room. First floor offers guest bedroom with full bath and office. Second floor includes master suite with walk-in closets, master bath, laundry room and three additional bedrooms. Large, private yard with deck and atrium doors from kitchen. This home is less than one mile from Winchester Center, restaurants, shopping and 2 commuter rail stations. 
Open House: Friday, 1/18 11:00-12:00PM ADDITIONAL INFORMATIONStep into the welcoming foyer of this stately 1940's Colonial to find beautiful character and a versatile layout with extra space on each floor. Fireplaced living room with beamed ceilings and bright oversized windows flanked by sunroom. Updated kitchen with granite countertops and cozy breakfast nook with access to side yard. Office and full bath complete this floor. The second floor spacious master bedroom has a walk in closet and an en-suite bath with an additional room that could be used as a nursery, office, or even a guest room. There are two more abundant bedrooms, full family bath, and a generous landing with closet space. Lower level includes an unheated family room with unique decorative fireplace, laundry and access to 2 car garage. Beautiful, spacious fenced backyard. Proximity to The Fells, make this home one to cherish! $1,199,0009 Eugene Dr Winchester, MA 01890
Open House: Saturday, 1/19 1:00-3:00PM ADDITIONAL INFORMATIONMove right in and enjoy all that Winchester offers in this thoughtfully designed and renovated home in the sought-after Muraco school district. The living room is bright and inviting, with pocket doors leading to the dining room. The renovated eat-in kitchen is a chef's dream, with granite counters, stainless appliances, and built-in pantry. The spacious adjoining family room with fireplace is a perfect retreat. 4 generous bedrooms, including en suite master, each with ample closet. Expanded deck is the perfect place to enjoy outdoor dining and entertaining. Lower level family room, and access to garage. Hardwood floors throughout, custom blinds, recessed lighting, beautiful wainscoting, laundry on the first level, excellent storage space, attached 2-car garage, central AC. Enjoy easy access to Winchester's many amenities: award-winning schools, Middlesex Fells, shopping and dining, Farmer's Market, and access to highways and commuter rail to downtown Boston. $1,050,00027 S Gateway Winchester, MA 01890
Open House: Friday, 1/18 11:00-1:00PM ADDITIONAL INFORMATIONExcellent opportunity to not only beat the spring rush but move into a fantastic Winchester Neighborhood! This well Maintained 4 bedroom Brick faced Expanded Cape features a first floor Master suite that offers a full Bath with Tiled Shower. The Beautiful Fireplaced Living room easily flows into the Dining room which then opens up to a Large Family room that Boasts an additional Fireplace and Indoor BBQ Grill! The Spacious Kitchen offers Granite Counter Tops with plenty of Cabinet space. Upstairs you'll find 3 Spacious Bedrooms another Full bath and plenty of Closet Space! There is also a Bonus Teen/Recreation room in the Basement! Conveniently Located Close to a Cozy Yet Vibrant Downtown and with the Commuter Rail just a few blocks away the value this home offers is unmatched!*****First Showings at the Open Houses Saturday 1/19 11a-12:30p & Sunday 1/20 1:30p-3p******* 
Open House: Sunday, 1/20 11:30-1:00PM ADDITIONAL INFORMATIONThe meticulously remodeled townhouse you have been waiting for at White Horse Commons has finally come available. Excellent location just steps from the Wedgemere MBTA Commuter Rail Station. This magnificent end unit boasts two generous bedrooms, one and a half baths, a sun filled living room, dining room, family room, and chefâs kitchen. The kitchen comes complete with new stainless steel appliances, tasteful white cabinets, gorgeous granite countertops, breakfast bar, and recessed lighting throughout. New high efficiency heating system with stainless steel hot water tank. Enjoy all the amazing features and recent updates! Donât let this home pass you by. $3,400,0006 Ledgewood Road Winchester, MA 01890
ADDITIONAL INFORMATIONExquisite turn-of-the-century details abound inside and outside this architect-designed estate in one of Winchesterâs most desirable neighborhoods. Prominently sited on a premier level parcel within the new French Hill neighborhood. With 6 bedrooms, 7 full Baths and one Powder Room, this stately home offers elegance and flexibility. Open floorplan with enormous gas Kitchen with Subzero and Wolf appliances. The fieldstone detail, gracious wrap-around front porch, and shingled exterior command attention. Deep three-car Garage. Enjoy a scenic stroll into both Winchesterâs charming downtown and the âœFells,â with acres of hiking and cross country ski trails. Walk to the commuter rail, play grounds and schools. Sited on a gorgeous 1/2-acre lot just 11 minutes to downtown Boston! $2,495,00030 Brooks Street Winchester, MA 01890
Open House: Saturday, 1/19 12:00-2:00PM ADDITIONAL INFORMATIONTimeless and Majestic Residence! Located in the exclusive and desirable "Brooks Estates Neighborhood". Great ambience, spacious easy living 4-5 bedroom home. Bright and sunny with many large windows. A fantastic gas fireplace family room is next to the magnificent large eat-in kitchen with Sub-zero and top of the line appliances. Multi sinks, 2 dishwashers, stone counters and an island to truly enjoy and gather pre-dinner & at half-time. Lower level au-pair or guest suite area with full bath, playroom, media & recreation room. First floor home office, formal living room with fireplace and dining room with views and access to the large park like flat backyard, not easily found. Ideal for entertaining friends & family. Top floor, Bedrooms and Master Suite. Abuts the town forest to enjoy leisurely walks or hikes and add to the privacy of your great yard. Must see to appreciate ! Yes, you can have it all ! Easy walk to Wedgemere train station and town center. 7 miles to Boston. $1,629,0003 Stonefield Circle Winchester, MA 01890
ADDITIONAL INFORMATIONInstagram-Ready Curb Appeal! Nearly new, but far from cookie-cutter! Once featured on House Hunters, this beautiful home now boasts a 5-figure interior paint makeover. Stunning!!! Perfect layout for the discerning host. Strikes the hard-to-find balance between open space and cozy hideaways. Rare 3 CAR GARAGE. Spacious rooms with dramatic cathedral ceilings and architectural interest. Master bath with shower enclosure & soaking tub. 3rd-floor suite -- perfect for au pair or adult kids. 2nd-floor laundry. 2 large pantries. California Closets. 4 state-of-the-art high-efficiency heating & cooling zones. Potential for home office w/separate entrance. Lead-free. Located on a cul-de-sac, perfect for playing outside! Invisible dog fence. Sprinkler system. ~1 mile to commuter rail, steps to Alewife/Red Line bus, Ambrose Elementary, downtown Winchester. Visit this wooded, retreat-like setting -- on a street of beautiful homes -- and you won't believe how close you are to everything! 
ADDITIONAL INFORMATIONExquisite condo conveniently located just one mile from downtown Winchester! Donât miss this opportunity to move to Winchester with its many wonderful amenities and easy access to routes 93, 95 and two commuter rail stops into Boston! This updated condo features an entryway which leads into the inviting, sun-drenched living room. With an elegant formal dining room, ½ bath and spacious updated eat-in kitchen, featuring granite countertops and a gas stove; this unit is perfect for all of your entertaining needs. Upstairs you will find two generously sized bedrooms with stunning hardwood floors and recessed lighting, as well as an updated full bathroom. The 3rd level features a third bedroom, which could also serve as an office or playroom. This unit has extra storage space in the lower level, which could be finished for future expansion. With a spacious fenced-in backyard and ample off-street parking, you donât want to miss out on this opportunity! $1,425,00030 Amberwood Drive Winchester, MA 01890
ADDITIONAL INFORMATIONSprawling brick style home on The West Side of Winchester walking distance from the Vinson Owen Elementary School! A very special home offering superb curb appeal; an open airy floor plan & lush professional landscaped grounds on a half acre corner lot. A few of the best features of this 4000 sq ft home are 2 master suites; multi car attached garages; updated eat in kitchen adjacent to family room; finished lower level perfect for gym, home office or additional family room & fenced in rear yard with heated pool, stone patio, wood deck & 6 person outdoor hot tub. Amenities include 3 zone gas heat; central air; steam shower; 2 fireplaces & generous storage including outdoor shed. This is the home you will never want to leave. $1,139,500310 Main St Winchester, MA 01890
ADDITIONAL INFORMATIONBUILDER/OWNER WILLING TO WORK WITH BUYER ON CUSTOM RENOVATION on this Great in-town location 3200+ sq ft colonial on a 10,000+ sq ft lot. Expansive front porch with gazebo-style roof welcomes you to this home. First floor features charming foyer with curved staircase, office/bedroom that connects to full bath, entertainment-sized living room with fireplace and French doors, formal dining room, cozy den loaded with windows, and kitchen with granite counter tops and stainless steel appliances. Second floor has 3+ bedrooms and full bath. Walk-up third floor has bedroom/office as well as ample storage space. Hardwood floors throughout most of first and second floors. Don't miss your opportunity to raise your family in this great house within walking distance to everything this great town has to offer. 
ADDITIONAL INFORMATIONWelcome to Winchester! Calling all first-time home buyers, down-sizers or looking for an alternative to renting. This is a wonderful first floor condo, turn-key newer construction with two-bedroom, two full bathrooms. The open floor plan offers an impressive eat-in kitchen, finished with granite counter tops, gas for cooking and stainless-steel appliances. The lower level is that perfect get away family room / den to watch Sunday afternoon football, or just catch up with that book. Storage room and the washer and dryer are included in the sale. Irving Street is close to the outstanding Winchester center, which offers the commuter rail to Boston, coffee houses, artisan stores and several local restaurants. Easy access to Routes 93 & 95. Taking the back roads through West Medford is a great alternative to commute to Cambridge. $1,799,00019 Royalston Avenue Winchester, MA 01890
ADDITIONAL INFORMATIONWhen the weather gets cold, the trees are bare, and there's snow falling down around us, don't you just want to hibernate? When New England hits us hard isn't it less important to go out for a night on the town, and more important to whip up a scrumptious dinner in your own home and curl up on the couch with a glass of wine and a movie? What make these pastimes even more desirable is when you can do them in a place like 19 Royalston. This 5 bedroom, 4.5 bathroom property with stunning kitchen featuring top of the line appliances will make you never want to leave home again! The 1st floor boasts a family room with fireplace, kitchen with SubZero refrigeration and Wolf cooking, dining room with wet bar, 1/2 bath, and home office with exterior access. A favorite feature consistently done by this developer is having all 5 bedrooms on the 2nd level! The vast 3rd level may be best of all! This space can easily be used as a playroom, media room, or au-pair quarters as it offers a full bath! $1,589,900512 South Border Road Winchester, MA 01890
ADDITIONAL INFORMATIONThis beautiful new construction, three level Colonial home in Winchester is a must see, with a 60-90 day delivery! Located across the street from Middlesex Fells Reservation, this is the perfect location for everything Winchester has to offer. This home will feature gorgeous finishes including eat-in kitchen with new quartz counters, stainless steel appliances and formal dining room. The spacious rooms through-out the home include a finished basement with full size windows, and finished 3rd floor with a 5th bedroom and bonus room! 
ADDITIONAL INFORMATIONNO CONDO FEES!! This charming DELEADED turn-key home is in pristine condition and is full of character and personality. Everything has been beautifully and tastefully updated, including new kitchen appliances, beautiful quartz countertops, and many cosmetic upgrades. Enjoy breakfast in the sun-filled dining area with skylight and sliders out to the deck, which overlooks a STUNNING fenced in back yard that features mature fruit trees, gorgeous landscaping, storage shed, and a SPRINKLER SYSTEM. Enjoy cozy evenings in front of the beautiful gas fireplace. Hardwood floors, high ceilings, ample closet and storage space (including potential expansion in the partially finished basement), and second floor laundry top off the list to make this home perfect. All in Winchester for under $600K! $1,599,99915 Royalston Ave Winchester, MA 01890
Open House: Saturday, 1/19 1:00-2:30PM ADDITIONAL INFORMATIONThis distinctive, updated colonial accents todayâs more casual lifestyle with a spacious, open floor plan, hardwood floors, and a kitchen youâll fall in love with - maple cabinets, granite counters, a huge island to seat 6+, & breakfast counter overlooking the fireplace living room. Immense dining room w/butlerâs pantry/2nd sink & dishwasher. The amenities continue with a 1/2 bath, 1st floor guest room, & office w/pocket doors to provide solitude from a busy household. The 2nd floor has 3 bedrooms, bath, huge laundry room, & a truly luxurious master suite w/large walk-in closet & cathedral ceilinged bath w/soaking tub, double sinks, make-up table, and large glass shower. The lower level has a huge mudroom off the 2 car garage, & large family room & bath. But wait, thereâs more â“ sliders from the kitchen lead out to a mahogany deck & a gorgeous built-in pool. A truly great Winchester home in which to live, to entertain, and to enjoy for many years to come! Muraco School! $1,295,00016 Marshall Rd Winchester, MA 01890
Open House: Saturday, 1/19 11:30-1:00PM ADDITIONAL INFORMATIONLive in one of the most sought after neighborhoods in Winchester and just 10 minutes from Boston. This Mid Century Modern home offers beautiful designer finishes inside and out, with it's lush landscaping, breathtaking deck and water feature. The open and airy living space is flooded with light all day from many skylights thru out. Fully appointed kitchen with marble breakfast bar, sub zero refrigerator and gold accents. The truly enormous master suite includes cathedral ceilings, window seat, it's own fireplace, incredible walk in closet with island, and exquisite master bath. Two additional bedrooms and full bath on main living level, French doors to office/study, a large media room and full bath on lower level is ideal for extended stay guests. Direct access from two car garage, additional storage. Just a quick walk to Wedgemere Station or delightful downtown Winchester and all schools. 
Open House: Saturday, 1/19 11:00-12:30PM ADDITIONAL INFORMATIONCONSTRUCTION COMPLETE!! NEW PRICE-- Brand new construction! Three bedroom two bathroom condo with open concept kitchen and family room for easy entertaining. Kitchen boasts beautiful white cabinets with granite counters, stainless steel appliances including 5 burner gas range with exhaust hood fan. Master bedroom has walk in closet and spacious master bathroom with subway tile shower. Two additional bedrooms with spacious double closets. Bonus additional recreation room in lower level and full laundry room. Home features gleaming hardwood floors throughout, central air, 6 panel shaker style doors, private driveway, patio, and farmers porch. Close to charming Winchester Center with great restaurants, coffee shops, boutiques, and commuter rail station for easy commute into the city. Nearby to brand new tri-town bike path and highly sought after schools. Routes 93 and 95 close by! Truly a commuters dream! OFFERS IF ANY ARE DUE BY MONDAY, JANUARY 21ST BY 5:00 PM. $2,050,00047 Arlington St Winchester, MA 01890
ADDITIONAL INFORMATIONGorgeous Colonial in move-in condition. Impeccable Myopia Hill location overlooking the Winchester Country Club with stunning light & serene golf course views, beautiful landscaping. Sweeping open floor plan is perfect for both relaxed daily living & luxurious entertaining. Outstanding craftsmanship include: high ceilings, large windows, oversized doors, exquisite bridal staircase. The sun-drenched front to back kitchen with large island & dining area opens to a covered porch - the perfect spot to enjoy your morning coffee overlooking the 4th hole. The two story foyer leads to the cathedral ceiling fireplace family room, fireplace living room & large dining room. The back entry provides easy access to the 1st floor guest room & fireplace study. The second floor includes the front to back master bedroom suite with three additional bedrooms, 2 baths & large laundry room. Spend your weekends enjoying the media room, exercise room & spacious play room or game room. $1,949,0004 Town Way Winchester, MA 01890
ADDITIONAL INFORMATIONCurrently Under Construction and ready for Spring occupancy!! Amazing 6000sf casual/ open concept colonial offering a great opportunity to customize and create your dream home! This beautiful home offers all of today's amenities with an oversized 2-car garage, direct entry into mudroom, gourmet kitchen w/ island, adjacent family room with fireplace, formal living and dining with crown moldings and wainscoting. Second floor features include Master suite with walk-in closets, luxurious master bath, laundry room with custom cabinetry and wash sink, four oversized corner bedrooms filled with lots of light & hardwood floors. 3rd floor with 2 add'l rooms & full bath~Great rear yard w/deck & sliders from kitchen. This home is located in sought after East side of town, convenient to the center, Lincoln school district, and is truly a great neighborhood! Basement family/media w/fireplace, kitchenette/ full bath &-plenty of space for gym or guest suite~ Call today for private showing! $1,929,00011 Meadowcroft Road Winchester, MA 01890
Open House: Saturday, 1/19 12:00-1:30PM ADDITIONAL INFORMATIONUNBEATABLE LOCATION, SITUATED IN THE HEART OF WINCHESTER!!! Completely renovated property in The Rangeley Estates. The first floor features an open floor plan for today's modern lifestyle, with a fireplaced living room, dining room and spacious kitchen. Enjoy entertaining your guests in the oversized kitchen, boasting a top of the line SS appliance package, granite counters and a slider with direct access to a large wooden deck. 4 bedrooms are located on the second floor, including the master and an additional en-suite, along with laundry and plentiful closets. The third floor is finished with a 5th bedroom, bathroom and large sitting room. Walk to the common and explore Winchester's boutiques, restaurants & coffee shops or take the commuter rail to North Station for a day in the city. Within the Ambrose school district and 7 miles North of Boston. 
ADDITIONAL INFORMATIONThis 2 bed 2.5 bath end/corner unit has great light, with extra windows, and sliders to THREE balconies, off Living Room & each Bedroom. The Foyer opens to the LivRm with gas FP and contemporary mantel, a bright Dining Area, and turning staircase to the sleeping Level. Stove & microwave, oak cabinets, refrigerator. Master Bedroom, with private bath; main bath w/spa-jet tub. Carpeted bedroom floors, professionally painted walls. Plenty of closet space. Large bonus storage area in basement & attic.It is building 3, level 2. $1,450,0007 Gardner Pl Winchester, MA 01890
Open House: Saturday, 1/19 12:00-1:30PM ADDITIONAL INFORMATIONThe Gardner-Swan Ell House is a rarity, an intact Pre-Revolutionary structure whose tasteful updates and versatility make it timeless. Dating back to 1764 and originally connected to 89 Cambridge St as a shoe shop, architect Frank Patterson Smith moved the historic Ell to its present location in 1931. The Middlesex Canal ran along the property line and the land was the site of âœGardner Locksâ. The present owners lovingly maintained and updated the original home with an addition in 1997 â“ an expansive family room, entry hall and eat-in kitchen. Beamed ceilings in the living and dining room, a home office with a separate entrance, fireplaces and charming butlerâs pantry add to its unique character. The second floor includes a master bedroom suite with fireplace plus 3 additional bedrooms and two baths. Spacious front and back yards, front patio and water gardens provide great space for outdoor play and entertaining. This welcoming home will delight and surprise you for years to come! $1,850,0005 Allen Rd Winchester, MA 01890
Open House: Saturday, 1/19 12:00-1:30PM ADDITIONAL INFORMATIONNew construction in Winchesters popular East Side. This 11 room, 5 bedroom home is perfect for todayâs buyer. Thoughtfully designed with an open yet traditional feel with coffered ceilings & rich millwork. The 1st floor has a formal living room w/fireplace, formal dining room, front to back family room, gorgeous kitchen with high-end appliances, quartz counters & center island, 1/2 bath & mud room. The 2nd floor features 4 bedrms, laundry room & 3 full baths. The master bedroom has two walk-in closets, a luxurious bath & sitting area. The 3rd floor has a bonus room plus a 5th bedroom with full bath perfect for au-pair, in-law or teen suite. The basement is partially finished with a bonus/play room, space for a gym/office and plenty of storage. This home is perfect for the family looking for a quiet neighborhood, with all the benefits of owning a brand new home. Lincoln School District less than a mile from Wedgemere train station and shops & restaurants OPEN HOUSE Sat Jan 12th 12-1:30 $2,199,99931 Swan Road Winchester, MA 01890
ADDITIONAL INFORMATIONWhat does it mean to have a Swan Road address? It means youâve arrived! Give yourself the gift of owning 31 Swan Road. A stately Tudor style home with magnificent grounds, situated on one of the finest roads that Winchester has to offer. The stunning brick exterior, adorned with slate roof, will impress you from moment one. As you enter, the beautiful foyer will leave you breathless. The sunken living room with Bath Stone fireplace and hand crafted wood walls is something straight out of a magazine. Enjoy the opulence and grandeur of a time gone by, seamlessly combined with a sensible layout and amenities of today such as a renovated kitchen with Wolf, Viking, and SubZero appliances. The second level is home to four bedrooms, and 3 full baths, including the master suite drenched with natural light, thanks in part to the homes South facing direction. Should you venture off these park-like grounds you'll find yourself within walking distance to both Winchester Country Club and Boat Club.
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