Winchester MA Real Estate & Homes for Sale
The median home value in Winchester, MA is $1,072,500.
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 $1,072,500.
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! $1,375,00076 North Border Road Winchester, MA 01890
ADDITIONAL INFORMATIONHas there ever been a better time to live in the suburbs? And yet downtown Boston is just 10 miles away! Enjoy both worlds in this charming craft home located directly across from The Fells!!! So much space, inside and out! A versatile floor plan with a first floor bedroom and bath (in law/nanny potential) plus three bedrooms and full bath on the second floor. Large living room with beamed ceiling and working fireplace. The dining room with beamed ceiling looks out onto a private patio. Recently renovated eat in kitchen opens into an enormous family room with stone fireplace - overlooking the half acre lot and a 'bonus' shed. Need a home office? This home has one!! Attached two car garage completes this perfect picture! $1,249,0003 Sunset Road Winchester, MA 01890
ADDITIONAL INFORMATIONYou wonât want to miss this great home in top neighborhood! With the perfect blend of location, space, price and renovation; this home is a gem! Situated on over a half acre lot with expansive private back yard, beautiful oversized kitchen with dining area & french doors leading to deck and fire pit area overlooking yard. Dining room or addâl living room w/ wood burning fplc, spacious and sunny cathedral ceiling family room, first floor optional master suite with newly renovated bath, adj. sunroom/ office or gym area, second floor features 3 bedrooms w/additional master & full bath. Lower level will not disappoint and offers beautifully finished playroom/ family room area with custom built in shelving/ wainscoting, laundry room and storage area. House is in beautiful condition with new roof recently installed. Enjoy beautiful weather in your private backyard oasis, room for a play structure, skating rink or whatever you desire! $1,225,00094 Thornberry Rd Winchester, MA 01890
ADDITIONAL INFORMATIONWelcome home! Opportunity knocks on the very desirable Thornberry Road. This property is set on 20,000 sqft. with over 3000sqft of living space. 4-bed, 3-bath split entry home in the West side of Winchester, Beautiful open concept on main level; sun-filled kitchen offers bar seating that opens to the large family room complete with a gas stove and skylights, perfect for entertaining friends and family. The dining room opens to your very own private deck and after dinner you can relax in the fireplaced living room. The 3 bedrooms on the main level have hardwood floors and ample closet space, and the master comes with an en-suite bathroom. The Garden level/lower level boasts fireplaced family playroom/game room, bedroom, full bathroom, full laundry room and your own home office, Spacious garage & storage. Easy access to Winchester and Lexington town centers, Whipple Hill Nature Preserve, Wright-Locke Farm, Winchester Swim & Tennis Club, and major routes and commuter rail Stations. $1,100,0001 Lantern Lane Winchester, MA 01890
ADDITIONAL INFORMATIONNEW kitchen and baths! Close to town, tennis courts and Winchester amenities. This sunny cape offers a new kitchen with island and bay window, first floor family room with gas fireplace, dining room with built in hutches and a large front-to-back living room with fireplace. Upstairs there are 3 bedrooms, a new master bath and a new shared bath - each with tiled tub and shower. On the basement level, find plenty of storage and a play room. Enjoy living "on the lane". This is NOT an association. Each single family home has a distinctly separate lot and is situated in an oval. Incredible yard with beautiful plantings. Less than a mile to Winchester Center train, shops, restaurants. Enjoy all Winchester has to offer including Packer-Ellis Tennis Courts, Middlesex Fells, Wright-Locke Farm and so much more. This is the perfect spot for the buyer looking for community. PLEASE park on Palmer Street when visiting. Follow COVID19 protocol - wear masks and gloves. $1,349,00017 Cranston Rd Winchester, MA 01890
ADDITIONAL INFORMATIONWelcome to this stylish and very versatile East Hill Cape home. Whether you choose to enjoy sunrise from the expansive front porch or fires in the back yard hearth and patio or exercise in the nearby Middlesex Fells, this home will beckon you inside. The spacious living room with a beautiful stone hearth as the focal point and french doors flows into the recently renovated kitchen with gathering island, quartz counter tops and a large dining area. The first floor offers and addition 2 bedrooms which can used as 1st floor family room and office for flex space. The second floor features one large possible master bedroom with 2 additional bedrooms, 2nd full bath and laundry area. The garage with direct entry to the finished recreation room, half bath and plentiful storage makes this a forever home. showings start Tuesday, 7/7. Click on ShowingTime link, not a phone service subscriber. $2,550,00011 Lorena Rd Winchester, MA 01890
ADDITIONAL INFORMATIONSteeped in history, 11 Lorena Road features 7,549 square feet of living space & is a quintessential New England home in both setting & style. Originally designed by renowned architect Miles Standish, a 1960s addition by Richard Wills of the elite Royal Barry Wills architecture firmâfeatured in Life Magazine in both 1938 & 1946 for his classic Cape Cod & Colonial home designsâadded an early American pub w/ beautiful pine-paneled walls, full bar, fireplace & abundant seating as well as a country living room. In 1999 Richardâs son, also of RBW, added an updated kitchen, family room & second floor bedrooms. All of this is set on 1.5+ acres of terraced land w/ patio spaces, embedded mill stones & spectacular gardens with a number of rare & unusual plantings including a certified Dawn Redwood that is one of the oldest in the US & believed to be from the original batch of seeds brought to the US from China by the Arnold Arboretum. Additional details abound in this unique, special home! $2,225,00019 Windemere Road Winchester, MA 01890
ADDITIONAL INFORMATIONStunning Colonial with contemporary flair! As you enter the spacious foyer,you will appreciate many custom features. Bathed in natural light, with high ceilings,each room flows into the next. Open concept eat-in gourmet kitchen with island is perfect for entertaining, with easy access to backyard and patio. Enjoy family gatherings in spacious formal dining room. As the unique layout continues with formal living room and generous size family room each boasting its own fireplace. The second floor stairwell with Brazilian Cherry flooring leads to four bedrooms and separate laundry. Private master suite on third level will wow you in every way! High ceilings, fireplace, walk-in closet and designer bath with double vanity, separate shower and soaking tub makes this space feel like a Spa get-away. Adjacent room with balcony is great for home office etc.Large finished basement with cedar storage, bar area and more,,This beautiful home is is ideal for extended family, au pair or in laws. $899,9009 Holton Street Winchester, MA 01890
ADDITIONAL INFORMATIONAs soon as you enter you will be wowed by the sun drenched 2-story foyer. Immediately on your left is the formal living room which flows into the dining room which flows seamlessly into the kitchen. Open to the kitchen is the family room with a gas fireplace and sliders which over look the brand new deck and large, level backyard. Upstairs you will find 3 well sized bedrooms including the master complete with a walk in closet and bath. No need to lug dirty clothing up and down the stairs because the laundry room (with a rinsing sink!) is located on the second floor for ultimate laundry convenience! Hardwood through out first floor, walk out basement with plumbing roughed in for bathroom, new boiler, deck and back stairs. Your new home is waiting! 
ADDITIONAL INFORMATIONWelcome to this Luxurious Living, Top floor, End unit, Bright and Sunny 2 Bedrooms, 2 full Baths Townhouse at "The Willows at Winchester". Inviting Living room with gas fireplace, recessed lighting with sliding door to a private deck. HUGE walking closets. Open floor plan with Dinning room and Gorgeous Modern kitchen with breakfast bar, Granite counter, SS Appliances and beautiful tiled backsplash. Huge Master bedroom with walking closet and Master bathroom with shower and double vanity with granite counter. Big size bedroom and another full bath with bathtub. Laundry in the unit with washer and dryer. Central A/C. Freshly painted walls and ceilings. Garage with attic for storage. Club House, Work out Facilities and Heated Pool make the picture perfect. Easy access to downtown Winchester, Shops, Restaurants, Commuter Rail to Boston and Routes I-93 & I-95. This home has it all! $1,499,00011 Cabot St Winchester, MA 01890
ADDITIONAL INFORMATIONLovely colonial revival designed by architect Robert Coit boasting traditional elegance and classic charm. Set on a quiet street in Winchesterâs desirable neighborhood âThe Flats,â this home is in a coveted location close to Winchester Center with its many shops, restaurants, commuter rail, top rated schools, Fells and Horn Pond Reservations. As you walk through a grand entryway, the first floor features a formal dining room, inviting living room with fireplace and bright kitchen with breakfast nook. Study with fireplace, secluded 3-season porch and half bath complete the first level. Two staircases lead to the second level with 4 bedrooms and 2 full bathrooms. Enjoy a spacious and sunny fifth bedroom on the third level. The generous lower level offers immense opportunity to become a grand entertainment space, gym or kids area. Hardwood floors throughout, 2 car garage and plenty of off street parking, this is an amazing opportunity to take advantage of all that Winchester has to offer. $1,150,0007 Blossom Hill Rd Winchester, MA 01890
ADDITIONAL INFORMATIONOpportunity knocks! This large West Side colonial has been owned by the same family for almost 70 years and awaits its new owners. Entering the home from the front door, find a large family room to the right complete with beamed ceilings. To the left, you find the fire-placed living room full of natural light. Then move to the traditional dining room with a screened patio off of it, and into the kitchen that features hardwood cabinets, a Sub Zero refrigerator, and a door leading out to the backyard. Completing the first floor are 2 full bathrooms and 2 bedrooms. Upstairs, the large landing with built-ins has been used as a study. Three big bedrooms, a full bath, and a walk-in closet complete this level. In the basement is an entry from the 2-car garage where you could finish a mudroom, together with a large L-shaped family room. The neighborhood is known for potlucks, block parties, and impromptu gatherings of friends. Don't miss the opportunity to make this house your dream home. $1,275,000406 Highland Ave Winchester, MA 01890
ADDITIONAL INFORMATIONGracious center entrance colonial with distinctive charm and custom features.Grand front to back living room with fireplace and through french doors is a sunny family room. Beamed ceiling dining room has custom built in cabinets..Master suite and two additional bedrooms.are on second floor. Third floor has two rooms which could be an office and a bedroom.Separate au pair suite in basement with walk out.Lovely private rear yard. with new fence. Central air with air purifying system and new roof. Conveniently located in East Hill, this home is a short distance to Lincoln School and McCall Middle School and town center and transportation. Train station is less than a mile away and highways are close by as well. Enjoy the Winchester Music School across the street or go enjoy the beauty of the Fells Reservation which is located offf Highland Avenue. Landscaping has just been improved on front of house so new plantings and light abounds in living room and dining room $859,0004 Hinds Rd Winchester, MA 01890
ADDITIONAL INFORMATIONThis three bedroom home is ready for its new family. The open floor plan is ideal for entertaining. The spacious living room features a fireplace and leads into the dining room, and small family room. The large deck is perfect for outdoor dining, and overlooks a large flat lot. The mid level features an office, half bath with laundry and direct access to garage. The basement level offers a large playroom with a fireplace, storage room with shelving and exercise area. Updates include newer heating system, newer roof, replacement windows. Desirable neighborhood located in the award winning Muraco School district. Enjoy all that Winchester has to offer: Middlesex Fells Reservation, Farmer's Market, Tri-Community Greenway, and easy access to downtown Boston. This home has been virtually staged. All visitors must wear masks, gloves and booties while inside the building. Only 3 people per showing. $2,349,00019 Wedgemere Ave Winchester, MA 01890
ADDITIONAL INFORMATIONWedgemere Avenues very first home! Situated in desirable Ambrose elementary district, this magnificent property offers timeless grandeur blended with many updates desired for todays living & is truly one of a kind! Stunning entry foyer with grand staircase welcomes you into the home, flanked by a front to back living room and formal dining room each with fireplaces and gorgeous handcrafted millwork. Expanded Kitchen w/ original butlers pantry and adjacent family room/den w fireplace overlook sprawling fenced rear yard w/in-ground gunite pool and plenty of lawn space. Second features Grand Master suite complete with fireplace, coffered ceiling, sitting room, walk in closet and private bath. Three additional rooms and 2 baths on 2nd . Full third floor with 2 bedrooms, recreation room and full bath. Lower level walk out with wine cellar, full laundry room, family/game room and a utility room with all updated systems including central A/C.** With additional updates this is a 3M+ home!!** $1,299,00049 Amberwood Drive Winchester, MA 01890
ADDITIONAL INFORMATIONBEAUTIFUL CONTEMPORARY HOME IN WINCHESTER'S DESIRABLE WEST SIDE! Meticulously maintained and recently painted in neutral BM colors PLUS freshly sanded and stained hardwood floors! Nothing to do but move in. This gorgeous home, on a very quiet street, has an inviting layout featuring a 1st floor master suite with exceptional ceiling height. The kitchen has a breakfast nook, an open concept family room, with adjacent laundry and full bathroom. The dining room, living room combination make up the rest of this floor. Upstairs are 3 large bedrooms with ample closet space, a full bathroom and bonus room which could be an office. The exterior features a deck and stone stairs leading to 2 other levels with exceptional views. WITHIN WALKING DISTANCE TO THE 3 YEAR OLD VINSON OWEN SCHOOL! A short drive to downtown Winchester bustling with restaurants, boutiques, coffee shops and the commuter rail to North Station. Easy access to major highways and just 7 miles from Boston! 
ADDITIONAL INFORMATIONCall/text for showings, open houses by appointment due to COVID-19 restrictions. Rarely available 6th floor 2-bedroom unit in desirable Winchester. Spacious living room with sliding patio doors opens onto a private terrace with lovely high-level park and pond views! Updated kitchen with ceramic tile back splash and floor. Gleaming hardwood in bedrooms and living areas. A brand-new, fresh coat of paint throughout. Master bedroom with 2 closets. Extra storage in the basement. Building has an elevator, coin-operated laundry. Condo fee has you covered, it even includes heat, hot water, air conditioning, electric, water, sewer, master insurance, swimming pool, parking. Convenient to downtown Winchester's shopping, restaurants, bus lines and train to North Station. For the eco-conscious, imagine life without a car at this unique geothermal building. 3D Virtual Tour and photos: https://www.seetheproperty.com/story/348947/b 
ADDITIONAL INFORMATIONResidence 2 at allegro is located on floor one and offers a one of kind 40 foot, private patio with access from the living room and master suite. It is a beautiful, open concept layout with bedrooms flocking on either side of the living room. allegro Winchester is a boutique style building consisting of 11 unique homes in an intimate setting off the beaten path yet steps from market shopping & the MBTA Winchester Commuter Rail Station. All residences are one level with designer kitchen; well appointed master suite; multi zone gas heating & cooling; elevator access to garage parking & additional storage room. Your dream home at allegro will be ready for you by end summer 2020. NEW CONSTRUCTION IN TOWN CENTER! 
ADDITIONAL INFORMATIONIntroducing Residence 10 at allegro! This is The Penthouse and largest unit at allegro. This unique, one of a kind, floor plan is the entire back of the building and offers 2 master suites, half bath, 2 car parking and 2 decks overlooking picturesque Vine St. It is a beautiful, open concept layout with bedrooms flocking on either side of the living room. allegro Winchester is a boutique style building consisting of 11 unique homes in an intimate setting off the beaten path yet steps from market shopping & the MBTA Winchester Commuter Rail Station. All residences are one level with designer kitchen; well appointed master suite; multi zone gas heating & cooling; elevator access to garage parking & additional storage room. Your dream home at allegro will be ready for you by end summer 2020. NEW CONSTRUCTION IN TOWN CENTER! 
ADDITIONAL INFORMATIONAttention Winchester enthusiast!! Fantastic opportunity!! Welcome to 119 FOREST STREET, WINCHESTER!! Stately Colonial on sought after Forest Street area. This home is for the time home buyer making their way into Winchester. Bring your cosmetic touches and ideas and make this your home. And the contractor, investor or builder can do what others have done on the street and turn this gem into a Million Dollar+ opportunity. 7-8 Rooms, 3 bedrooms and 2 baths. Some updates to the roof, heating system and oil tank. Fully appliance kitchen with 1st Floor laundry and 2nd bath just off to the side. Enjoy the Fireplaced Living Room and formal Dining Room with classic Built In Cabinets. Hard wood floors on the first floor and under the carpets on 2nd floor (Buyer should verify they are under carpeting). Enjoy the 11,000+ yard from the side deck off the kitchen. This property will not last. $1,425,00016 Gershon Way UNIT 16 Winchester, MA 01890
ADDITIONAL INFORMATIONWINCHESTER'S 1ST 55+ COMMUNITY! Designed by national, award-winning, architect Gary Snider. 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. 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.***MODEL HOME NOW OPEN SEVEN DAYS A WEEK***SEE ATTACHED SHOWING INSTRUCTIONS*** $2,475,000432 South Border Rd Winchester, MA 01890
ADDITIONAL INFORMATIONNEW CONSTRUCTION Step right into this beautifully designed custom home and make it yours. This spectacular home offers 5 bedrooms and 6.5 baths, and is situated on a large lot across from the Middlesex Fells, just minutes from downtown Boston. This beautiful home offers today's amenities with two car garage, direct entry into mudroom, high-end chefâs kitchen, great room with fireplace, and office, all with luxury finishes such as coffered ceilings and hardwood floors. First floor offers guest bedroom with full bath. Second floor includes master suite with walk-in closet and master bath with soaking tub, laundry room and three additional bedrooms. Expansive finished basement with full bath, perfect for exercise space or media. Large, flat backyard offers ideal space for outdoor dining and entertaining. Enjoy all that Winchester offers, including award-winning schools, quaint Winchester Center with restaurants, shopping, Farmerâs Market, and library, and two commuter rail stations. 
ADDITIONAL INFORMATIONCOMPLETELY RENOVATED HOME!!! Within the Lynch School district & walking distance to McDonald field. This cozy 3 bed, 1 bath home is in need of a new owner to share its life with. The 1st floor includes the living room, perfect for lounging, watching sports or snuggling up with a good read. The dining room / kitchen open concept plan is made for hosting your next dinner party & allowing you to be part of the conversation while preparing drinks for your guests. Adorned with stainless appliances, Quartz counters & a door that leads to a large, level, fenced back yard. Work from home in your quiet, private study. The 2nd Floor has a generous master bedroom with a separate sitting area & two additional bedrooms. The custom bathroom makes excellent use of the space, boasting a gorgeous walk-in shower. Nothing to do but move in & enjoy everything the town has to offer. A short drive to downtown Winchester bustling with coffee houses, boutiques & the commuter rail to Boston. $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. Showings ARE allowed and we are adhering to Covid-19 showing guidelines. Live open house Sat 6-27-20 12:30-2:00pm 
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!
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