Winchester MA Real Estate & Homes for Sale
The median home value in Winchester, MA is $1,228,850.
This is
higher than
the county median home value of $567,300.
The national median home value is $219,700.
The average price of homes sold in Winchester, MA is $1,228,850.
Approximately 82.15% of Winchester homes are owned,
compared to 13.25% 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! $1,800,00011 Cox Road Winchester, MA 01890
Open House: Sunday, 5/16 1:00-2:30PM ADDITIONAL INFORMATIONSpectacular Colonial farmhouse built in 2000 by David Pywell. Flooded with natural light, brimming with character and detail. Newly installed, freshly finished hardwood floors and freshly painted interiors. Living and dining rooms feature high ceilings, exquisite moulding, French doors, custom built-in bookcases and fireplace. Formal dining room and open family room. Granite and stainless kitchen complete w/ a Viking stove. Gorgeous French doors open to expansive deck and screened in porch overlooking landscaped backyard abutting Smith Pond and conservation land. Mudroom area features built-in cubbies and leads to private office, full bath, and 2-car garage w/ Tesla charger. Finished basement complete with new carpet, recessed lighting, full bath and outdoor access. Brand new primary bath features a soaking tub, glass shower and private outdoor balcony. Lovingly and meticulously maintained for 20 years by original owner. $1,029,00058 Loring Ave Winchester, MA 01890
Open House: Sunday, 5/16 12:00-1:30PM ADDITIONAL INFORMATIONLovingly maintained colonial situated on an oversized fenced in lot in a great location! An open airy first floor with hardwood floors, high ceilings with welcoming foyer, formal dining room with built-ins, upgraded kitchen, spacious living room, full bathroom and a lovely sunroom/office complete the first floor; The second floor has 4 spacious bedrooms, all with hardwood flooring, overhead lighting and generously sized closets. A beautiful sunny back yard awaits with lot of space to add a pool, or create a garden, play area or use as a sports field! Easy access to downtown schools, shopping,restaurants, McDonald Field playground around the corner! Located just 9 miles north of Boston! Don't miss this great home! 
Open House: Sunday, 5/16 12:00-2:00PM ADDITIONAL INFORMATIONEnjoy Winchester. This colonial has been owned by the same family since 1916. Over the years it has been improved with a 1/2 bath, hardwood floors, new windows and updated kitchen cabinets. This home has 3 bedrooms and full bath with an extra third floor playroom. Living room, dining room large kitchen with 1/2 bath all floors are hardwood. Gas heating and one car garage, the basement is 1/2 finished with an office . You can walk to restaurants and stores and train to Boston $1,350,00028 Maxwell Rd Winchester, MA 01890
Open House: Sunday, 5/16 12:00-1:30PM ADDITIONAL INFORMATIONStep into this magical 20th century colonial w/ a storybook neighborhood to match its idyllic charm! Coming in from the full front porch, the secluded parlor w/ its 3 windowed walls is a cozy space w/ lots of natural light- perfect for a reading room! The kitchen w/ custom cherry cabinets leads into both the fireplace dining rm & family rm w/ matching cherry entertainment center- anchored by the wainscotting foyer to create a circular flow thatâs perfect for entertaining! 2nd floor features a front to back master suite w/ private bath & dressing rm on one half, & 2nd bdrm & family bath w/ clawfoot bathtub/shower on the other. Avid readers & storage lovers rejoice as the 3rd floor, w/ its great office space & 2 more bdrms, features the original built-in cabinetry & storage drawers + built-in bookshelves to match! The finished basement is truly a treat- ample amounts of light, a laundry/office area, pantry closet & 2nd family rm w/ walkout to the backyard makes this space bright & unique $1,249,90050 Water Street Unit 50 Winchester, MA 01890
Open House: Sunday, 5/16 10:30-12:00PM ADDITIONAL INFORMATIONWelcome to Water Street! Step right into this beautifully designed custom home and make it yours. This sun-drenched townhouse offers 4 bedrooms and 3.5 baths. With more than 2,500 square feet spread out on 3 levels of living, this impressive NEW townhouse has extreme attention to detail and a level of finish that is unlike anything else on the market in Winchester. The expansive open floor plan is excellently laid out for the hustle and bustle of today's modern lifestyle. The chef's kitchen offers stainless steel appliances, including a Verona gas range, white cabinetry, quartz countertops, and a wine cooler. The owner's suite features a walk-in closet, a spa-like bathroom, and a private balcony. Two off-street parking spots, and a private yard, round off this offering. Enjoy all that Winchester has to offer, including award-winning schools, quaint Winchester Center with restaurants, shopping, Farmerâs Markets, a public library, and the commuter rail station. $2,099,0001 Robinson Park Winchester, MA 01890
Open House: Sunday, 5/16 1:00-3:00PM ADDITIONAL INFORMATIONIf 2020 taught us anything, it's that you should love where you live! A top ranked neighborhood, gorgeous water views, newer construction, 3 car garage and an amazing layout is waiting...what's not to love? This sprawling home has space to the max and glows with warmth. The open and airy kitchen lets you cook up a storm, hunker over homework or entertain your friends. It's got an eat-in dining area and is open to a cozy family room, highlighted by a beautiful fireplace and plenty of windows. Or, make it formal in the dining room and living room. The first floor study is a must-have these days! Light abounds in this home; retreat to your huge master suite and private sitting room, turn on the fireplace and enjoy your lake views. Want some bonus space? There is a huge in-law suite with a private entrance, ensuite bedroom and enormous media room with vaulted ceilings. The third floor offers a bonus spare bedroom and playroom. Brand new deck, freshly painted exterior, beautiful landscaping 
ADDITIONAL INFORMATIONSought after cul-de-sac Location! This unique oversized center hall Cape Cod style home, with a few modifications to the Library/Study could function as a 4 bedroom home if a 1st floor bedroom were desired. Amazing space abounds in this well thought out expanded home which includes an oversized front to back EI kitchen with incredible storage, cozy open Family Room, and a separate staircase accessing the MBR Suite with a full tub/shower bath, dressing area, an enormous walk-in closet, an additional oversized closet and ample eave storage, all with its own AC and heat zone. Five rooms on the main floor provide plenty of room to spread out for the entire family including: a 22â fireplaced Living Room and a formal Dining Room with custom built-in hutch and double French doors. Incredible basement storage! Nicely landscaped yard with mature bushes and perennials, yet ample space for all your family's outdoor activities! Short walk to commuter rail and one block from the Town Forest! $950,00091 Johnson Rd Winchester, MA 01890
Open House: Sunday, 5/16 12:00-2:00PM ADDITIONAL INFORMATIONWelcome to 91 Johnson Road! Located in Winchester's West Side neighborhood just steps away from Vinson-Owen Elementary School. This well-maintained split entry has great bones, beautiful hardwood floors and awaits its new owner. First floor features a 3/4 bath, a bedroom w/ walkout that could also be used as a home office/study. Lower level has a partially finished basement that is spacious with high ceilings and a fireplace. Second floor formal living room area is spacious with a large bay window bringing in plenty of natural light and a fireplace. Dining room located to the left of the living room area flows into the Kitchen. Kitchen has original cabinetry that is in great condition with ample counter space for cooking. Upper level features three bedrooms including the master with an en-suite master bath. Attic storage that can be finished for bonus room. Close to Winchester's downtown center for dining, shopping and commuter rail. Bring your ideas to this home and make it your own! $1,699,00022 Ginn Rd Winchester, MA 01890
Open House: Sunday, 5/16 12:30-2:00PM ADDITIONAL INFORMATIONOPEN HOUSE Sunday 5/16 12:30-2 This unique home in TOP location, is perfectly sited on a gorgeous, beautifully landscaped lot set between Ginn Road and Rangeley Estates with access to both downtown neighborhoods! This quality built 3 level home is constructed mainly of brick and offers unique marble sills and extraordinary craftsmanship; the quality of this construction is superior! This gracious home offers all of the updates todays buyers desire including new kitchen with island seating, gas cooking, central A/C, new roof, updated systems. First floor features an open concept with kitchen/ mudroom adjacent to living room w/ fplc, formal dining room, butlers pantry, and family room/den w/ 1/2 bath. Second floor features 4 rooms including a spacious master, sitting area, and three additional bedrooms. Enjoy the lower level gym/media room & laundry room complete with full bath, walk out to rear yard! Close to Winchester center, Wedgemere train station direct to North Station- 
Open House: Sunday, 5/16 12:00-1:30PM ADDITIONAL INFORMATIONDon't miss this rare two-bedroom terrace unit at the desirable Parkview. Enjoy the ease of a ground level entrance, making access to the gardens, parking, or pool a breeze: no elevator required. This light-filled, open concept home includes an abundant living room/dining area and kitchen. There are two spacious bedrooms, each with double, oversized closets plus more storage in the hall. From your private patio, enjoy a peaceful environment with lovely plantings and landscaping. This condo overlooks courtyards with bridges spanning duck ponds, flowering trees, a shady trellis, and an in-ground pool. All utilities, common laundry and basement storage are included in a low condo fee. One off-street parking space included, as well as a large guest parking lot. Access the highly ranked Winchester Public Schools, Middlesex Fells, nearby shops and restaurants, commuter rail and farmerâs market- while living less than 10 miles from Boston. $1,899,0007 Samoset Rd Winchester, MA 01890
Open House: Sunday, 5/16 12:00-1:00PM ADDITIONAL INFORMATIONPristine Colonial in desirable Ambrose School district! This impressively spacious home boasts six bedrooms with three full and one half bath. Welcome into a grand entrance leading to the formal dining room with tray ceiling and hardwood floors. The recently updated kitchen includes stainless steel appliances, Wolf range, designer backsplash with a eat-in kitchen. Newly built exterior deck is perfect for entertaining. Formal living and family rooms both have fireplaces! Bedroom/office is located on the main level. Half bath and spacious laundry room with plenty of storage complete the first level. Second floor includes a master bedroom with en-suite bathroom and walk-in closet. Three additional bedrooms and a full bathroom complete the second level. Finished lower level includes library/media/office and another full bathroom complete with a steam shower! This wonderful home with mature landscaping is waiting for you! $1,749,000254 Main St Winchester, MA 01890
ADDITIONAL INFORMATIONThis updated and remodeled Colonial is ideally located near the heart of Winchester, convenient to schools, restaurants, shopping, parks, commuter rail, Fells Reservation and Mystic Lakes! Featuring 4 spacious bedrooms & 2 full and one half baths, the open concept chefâs kitchen and expansive Great Room featuring vaulted ceilings, gleaming hardwood floors, double gas fireplaces, wet bar, skylights & direct access to a deck make entertaining a delight. Kitchen features stainless steel appliances, Bosch double wall ovens, Subzero Fridge, DCS gas cooktop, breakfast bar, dining area and large walk-in pantry. An adjacent, spacious laundry room with ample storage and mudroom with access from farmerâs porch, as well as formal dining room with built-in hutch, formal living room with fireplace & access to exterior deck and comfy family room round-out the main level. A finished, walkout basement with fireplace and direct access to oversized 2 car heated garage. This stunning home awaits you! 
ADDITIONAL INFORMATIONHOME OFFICE!! Must see this spectacular home with carriage house completely renovated & restored inside and out! This spacious home offers a prime downtown location with 4 floors of space featuring 5+bedrooms, 3.5 baths complete with private ELEVATOR! This recently renovated custom designed town home lives like a single family and offers all the luxuries todays buyers desire, close to town, shops, schools, train to Boston. Stunning kitchen with cherry cabinets, stainless appliances, dining area flooded with sunlight, and family room with walls of windows overlooking beautifully manicured grounds. Formal LR with gas fireplace and detailed moldings. Spacious Master suite with w/fplc, walk in closet & marble bath w/ soaking tub. Third floor w/ 4 addl. beds and full bath. EXCLUSIVE to this unit is also a 3 CAR GARAGE/ CARRIAGE HOUSE w/ full in-law apartment above. The carriage house is handicapped accessible equipped with chair lift, full bath, laundry, kitchenette, living and bedroom area $1,825,00013 Gershon Way Unit 13 Winchester, MA 01890
ADDITIONAL INFORMATIONLuxurious and sophisticated best describe this new 3 bed, 2.5 bath end unit townhome at Winchesterâs Winning Farm, a gold medal award winner from NAHB for best 55+ community in the US. The layout offers great flexibility for todayâs lifestyle with superior quality and charm. The first floorâs open concept features living room with gas fireplace and large windows to let in loads of natural light and great views. The dining room has coffered ceiling and door to outside deck. The office/den is accessed through double French doors. The custom chefâs kitchen has high-end appliances, quartz countertops, and large island. The 1st fl master suite has walk-in closet with custom shelving, door to outside patio, and bathroom with double vanity, walk-in shower with bench, and separate soaking tub. The second floor has two large bedrooms, full bath with walk-in shower, and loft/open space. There is a two-car attached garage and basement with high ceilings that offers many options for future use. $2,850,00028 Surrey Road Winchester, MA 01890
ADDITIONAL INFORMATIONFabulous new construction opportunity awaits you in Winchester. Spectacular floorplan with 14 magnificent rooms, 5 bedrooms, 5 1/2 baths. Winchester luxury living encompassing choice materials and tasteful design by well known Master Builder from Winchester. Casual elegance with features such as beautifully appointed culinary grade kitchen, large finished family room and office with full bath in basement, primary bedroom with den, tasteful mudroom, heated 2 car garage, and more! Exceptional 31,800 square foot lot capable of an optional pool and pool house with striking optics overlooking the Ledges of Winchester. Quiet, popular neighborhood. Unmistakable benefits of New construction in a classic New England town with TOP rated schools. Built with perfection as a goal, and excellence as a result for a fortunate family to enjoy for many years to come. 
Open House: Sunday, 5/16 12:00-1:00PM ADDITIONAL INFORMATIONMove right into this beautifully updated Winchester condo! This 2 bedroom with 2 full bathroom unit has a spacious layout and allows for plenty of natural sunlight. The living room has hardwood floors and a gas fireplace with an adjacent full bathroom. A modern kitchen features granite countertops, breakfast bar, and ample cabinet storage. The dining room completes the 1st level. As you make your way to the upper level, the master bedroom and 2nd bedroom are connected by a full bathroom making this an easy access. Office nook for your zoom meetings and desirable in-unit laundry. Private access to a roof deck is perfect for entertaining and overlooking the surrounding neighborhood. This unit is pet friendly and offers two deeded off-street parking spaces and a manicured garden. Conveniently located near the bustling town center, shopping, restaurants and commuter rail. Make this condo your next best move! $2,599,00022 McCall Road Winchester, MA 01890
ADDITIONAL INFORMATIONNewer construction, custom built shingle style home in top Myopia/ Winchester Country Club location! Designed for ease of living with direct entry garage into mudroom, 1/2 bath leading into sun-drenched kitchen/ family room spanning the rear of the home, oversized windows overlooking conservation & providing an abundance of privacy and tranquility. Top of the line finishes both inside and out with natural cedar shake roof, natural stone accents, copper gutters & high end Andersen aluminum clad windows. First floor w/ high ceilings, family room w/ sliders to oversized deck, gas FP, formal dining room and living room with cathedral ceilings can also serve as second master suite w/ full bath! 2nd level features 4 beds, 2 ensuite; gorgeous master with high ceil, spa- like bath, 2nd fl. laundry. Full walk out lower level w/ private entry featuring full summer kitchen, bedroom, living room and full bath complete with full size windows leading to stone patio. Elevator shaft in place B-2nd Fl $2,499,00021 Laurel Hill Lane Winchester, MA 01890
ADDITIONAL INFORMATIONUNDER CONSTRUCTION~Must see this stunning 4/5 bedroom home with luxurious design & high end finishes. This custom home is spacious and inviting, offering a grand open floor plan ideal for entertaining and modern day family living. The kitchen will feature an 8' island with seating/ quartz countertops, high-end Thermador/SUB-ZERO appliances, wine bar w/fridge, breakfast/ morning /dining area, spacious family room with gas FP off the kitchen w/ direct exterior access w/ sliders leading out to deck & large private rear yard; first floor also has formal dining room & 5th bed OR home office w/ 3/4 bath. The 2nd level master suite is a dream, offering a spacious master bedroom, with separate sitting room, dual walk-in closets, lavish bath with tiled shower/glass encl. double vanities & soaking tub! Three add'l beds incl. junior suite w/ bath, full hall bath and laundry room finish this level. Lower level full walk out w/ oversized media/game w/ kitchenette & full bath! 2 car garage/ mudroom $2,050,00027 Gershon Way Unit 27 Winchester, MA 01890
Open House: Sunday, 5/16 11:30-2:30PM ADDITIONAL INFORMATION2021 Winner for BEST NEW 55+ COMMUNITY IN THE COUNTRY. ONLY 2 HOMES REMAIN out of 29! Live surrounded by luxurious finishes, soaring ceilings, hardwood throughout & plenty of natural sunlight. This open concept plan boasts a 1st floor master suite with tray ceiling, a super-sized walk-in closet and luxurious en suite bath. The eat in kitchen is adorned with ceiling height cabinets, quartz countertops and top of the line stainless steel appliance package featuring Sub*Zero, Bosch, Wolf... The dining room has a stately coffered ceiling, bay window and sliders to a private, covered deck. The flex room can be a home office or studio for your beloved hobbies. 1st floor also features a powder room, mudroom and laundry. Upstairs you'll find 2 additional spacious bedrooms, a full bath, a library and a large open loft for movie watching or game night. The icing on the cake: attached 2 Car garage with electric car charging station AND a 1,500 SF Walkout basement! MODEL HOME OPEN DAILY 11-4 $1,795,0006 Fairfield Place Winchester, MA 01890
ADDITIONAL INFORMATIONNew construction home with details complete such as mature landscaping & fencing; custom window treatments; bathroom fixtures & so much more. It is tucked away in a quiet neighborhood yet steps to town center, The Flats, schools, pond, tennis courts & train. A residence offering over 4,500 sq ft of luxurious living on 4 levels; has 5 large sunny bedrooms & 4 full baths. An inviting floor plan for all family members to enjoy with a blend of formal & informal spaces such as dining & living rooms; large 3rd fl playroom with full bath; exquisite oversized kitchen/family room that has direct access to paver patio & fenced in rear yard~ perfect for kids & pets; grand master suite & a finished lower level ideal for out or town guests or au pair suite. Amenities include hardwood floors; multi zone gas heating & cooking; attached garage; generous storage & so much more. Truly an urban oasis 7 miles from Boston.
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