Hot on the Market in Winchester!

Below you will find listings hot on the market in Winchester, Massachusetts! All of these listing have been on the market for 7 days or less. For other listings “hot on the market” in other communities, visit our “Communities” page. Don’t see your town listed? Contact us directly to get the latest info!

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372 Cambridge Street Winchester, MA 01890

$749,999 - 5Br/2Ba -  for Sale in Winchester
Open House
New
$749,999
5 Beds
2 Baths
1,925 SqFt
Status New
MLS # 72706984
Property Type Single Family
Price Type --
Discreetly set back from the road is this TWO OWNER hidden treasure! As you approach you will be immediately greeted by an oversized and secluded courtyard. Surrounded by lush greenery, you will truly feel like you're relaxing in your own private retreat every day. Morning coffee, or your evening dinner, will be enjoyed tenfold here! The main level of this property is where you will find the open concept living room and kitchen. A beautiful brick wood burning fireplace is the focal point of this space which also boasts an eat-in dining area. With treetop views from every window you’ll feel tranquil energy from each room in 372 Cambridge Street. On the upper level you will find 3 bedrooms, and your first full bath. This bath has been beautifully renovated with current tile, frameless glass shower door, and stone countertops. As you make your way down a level you'll find 2 additional bedrooms, a play room, and another tastefully renovated full bath. Located in the desirable VO district!

11 Trinity Road Winchester, MA 01890

$1,199,000 - 4Br/3Ba -  for Sale in Winchester
New
$1,199,000
4 Beds
2.5 Baths
2,633 SqFt
Status New
MLS # 72706409
Property Type Single Family
Price Type --
Welcome to Winchester! Never before offered to the public - this spacious multi-level home offers sprawling grounds, oversized living space and the opportunity to customize and renovate to make this your own!! Located on cul-de-sac in desirable Vinsen Owen neighborhood - this 4 bed 2.5 bath home has been meticulously maintained by the same family for over 50+ years. The main level offers a cozy living room w/ FP & oversized windows, dining room and eat-in kitchen with direct access to the yard/patio. Four oversized bedrooms with a master suite equipped with walk-in closet and full bath. The lower level features 2-car attached, mudroom/laundry area, family room and half bath. Located minutes from Wright-Locke Farm, Whipple Hill, Winchester Country Club and Turkey Hill hiking trails this home is a must see!!

24 Surrey Road Winchester, MA 01890

$1,699,999 - 4Br/3Ba -  for Sale in Winchester
Open House
New
$1,699,999
4 Beds
3 Baths
4,158 SqFt
Status New
MLS # 72706012
Property Type Single Family
Price Type --
This may seem like your typical split-level home from the exterior but my, oh, my, would you be WRONG! As you enter a dramatic foyer with stunning crystal orbital chandelier will lead you to the living room with cathedral ceilings and floor to ceiling ledger stone fireplace. To say this section of the home is impressive would be an understatement! But it gets better from there; the dining room offers majestic views of the Boston city skyline. The beautifully renovated kitchen with eat-in area boasts a stainless farmers sink and Bosch appliances including a 36 induction cooktop. Three bedrooms, including the master suite, are also found on this level. Access to the rear deck and a stunning spa-like bathroom with body sprays, linear drain, and steam shower are just a few of this masters special features. The lower level has an expansive family room, play room, bed #4, a full bath, kitchenette, and access to the 2 car garage. Quite possibly the in-law you've been searching for! Come see!

29 Dunster Lane Winchester, MA 01890

$1,749,000
5 Beds
5.5 Baths
7,756 SqFt
Status Active
MLS # 72704942
Property Type Single Family
Price Type --
Come experience the peace & casual elegance unique to this residence! Meant for a family seeking a lifetime of precious memories & located on a quiet street. This inviting home offers all the bells & whistles today’s savvy buyer seeks. Lovingly designed with 5 bedrooms (3 of which are en-suite), boasting 5.5 bathrooms & many heated floors. Ideal for entertaining friends & family, featuring a true Chef's kitchen & an open concept great room with fireplace & espresso bar. Plenty of space for all to enjoy, including a stunning back yard for playing catch with Rover-the-dog! Several rooms could be dedicated as an art studio or home office to accommodate your working demands. Around the corner from Wright Locke Farm for strawberry picking with the children. Dreaming of your own private roof deck ? A place to soak up some rays, host a BBQ, observe the starry nights through a telescope? Look no further! A short drive to bustling downtown Winchester featuring many coffee shops & boutiques.

32 Cambridge St Winchester, MA 01890

$999,000
4 Beds
2 Baths
2,092 SqFt
Status Active
MLS # 72705066
Property Type Single Family
Price Type --
Looking to live in the idyllic Winchester community? Now you can! This charming move-in ready ranch is located just a short drive to the highly acclaimed Ambrose Elementary School, Winchester Boat Club and golf course. Featuring hardwood floors throughout its spacious open concept layout on the main floor, a beautiful kitchen with recessed lighting, granite countertops and an incredible island, this home has a modern touch while still maintaining its exquisite original design. Separated by beautiful French doors, an inviting living with fireplace plus a large family room with soaring cathedral ceilings offer beautiful spaces for relaxation and intimate gatherings. Finished lower level with additional bedroom and bath perfect for in-laws or an au pair suite. Two car garage, plenty of off-street parking and a beautiful deck and patio overlooking a peaceful and private backyard. This home truly has it all!

17 Squire Rd Winchester, MA 01890

$1,255,000
4 Beds
2 Baths
2,532 SqFt
Status Active
MLS # 72704513
Property Type Single Family
Price Type --
Bright & beautifully renovated home with a unique 4-level-open-layout. The inviting entry foyer leads to the primary bedroom suite with double closets & private bath. Spacious main level has a fully applianced kitchen with cherry cabinetry, granite counters & breakfast bar that opens to the dining & living rooms, a perfect layout for easy living or entertaining. The upper level offers 3 large bedrooms, full bath with linen closet & has hardwood floors throughout. There is excellent easily accessible attic storage in two locations. The lower level offers a rec room & office area with glass doors leading to the multi-level patio. The 1/2 acre lot has multiple perennial plantings, offering privacy & space for expansion. Close to Winchester Swim & Tennis Club, Wright Locke Farm & the Vinson-Owen elementary school, shopping, the commuter rail, easy highway access, and all the wonderful things that Winchester has to offer.

19 Allen Road Winchester, MA 01890

$1,099,000
3 Beds
2 Baths
2,021 SqFt
Status Active
MLS # 72704804
Property Type Single Family
Price Type --
CALL FOR PRIVATE SHOWING! Move right into this picture perfect, lovely East side expanded cape with full rear dormer. This charming home is the perfect blend of location, size and price, a rare offering on this desirable side of town! with land value alone here at 850k+ this home is a great investment and has tons of future expansion potential. Sun-filled front to back living room with fireplace & french doors leading to gorgeous oversized deck with dining area & grilling area overlooking private rear yard. Sun-room, or first floor office makes working from home a pleasure.. Sunny country kitchen w/ room for breakfast table, adjacent dining room~ Second floor features two large bedrooms and full bath. Lower level is full walk out and offers a great space for an additional bedroom 3rd / au-pair, or guest suite complete with full bath! Lincoln school district, close to town center and train to Boston! Don't miss out on this great home! Offers will be reviewed by Tuesday 5pm.

46 Johnson Rd Winchester, MA 01890

$899,999
4 Beds
2 Baths
3,018 SqFt
Status Active
MLS # 72703329
Property Type Single Family
Price Type --
A lovely split raised ranch located in the much sought after West side of Winchester. Move in ready and just in time for the new Winchester school year. Two levels of spacious living with a glorious sun room and finished basement. The lower level has the fourth bedroom, full bathroom, office and a large family room. Walk out to the back yard from the basement. .Easy access to downtown Winchester, Library, 2 commuter rail stations to Boston, 2 stops to North Station and few miles drive to downtown Boston. Be a Winchester resident and enjoy the exquisite facilities that Winchester has to offer. Please contact now for appointments

29 Grove Place Winchester, MA 01890

$650,000
3 Beds
1 Bath
1,823 SqFt
Status Active
MLS # 72703661
Property Type Single Family
Price Type --
Meticulously renovated and maintained over the years, this beautiful colonial needs nothing but the next great owner! Updated kitchen with oversized windows featuring quartz counters & stainless steel appliances, gorgeous dining room with built-ins & picture window, and large living room with refinished hardwood floors! Newly updated bathroom with tile floor/tub surround & new vanity. Brand new carpet in bedrooms and bonus space on the 3rd floor; great for an office, playroom and/or extra sleeping area...all with great views! Beautiful patio area, perfect fenced side yard and upgraded landscaping throughout. Inside & out completely repainted, new gutters, new lighting fixtures & plenty of basement storage (potential to finish). All this nearby Wedgemere train station, Winchester Center & Upper Mystic Lake! Don't miss out!

263 Cambridge St Unit 263 Winchester, MA 01890

$1,389,000
3 Beds
3.5 Baths
3,197 SqFt
Status Active
MLS # 72703231
Property Type Condominium/co-op
Price Type --
This Old Graystone Farmhouse of 1885 has been taken down to the studs, & rejuvenated into the certified Silver Level Green architectural masterpiece of luxurious living. Listed on the National Register of Historic Places is now 2 townhouse condos. This unit has three floors completely renovated from top to bottom. Present owners for the last three years have spent their time in Florida.. You even have a full hardwood floor staircase to the attic with ample room to make yet another bedroom or study. High ceilings throughout, plenty of storage, private patio and yard area. All Nest thermostats, LED lighting throughout, Rinnai on demand hot water, gas stove, with gas fireplace in familyroom. A W/D closet on 2nd floor for convenience, and all gas; furnace, dryer, and direct connect to a BBQ unit on the deck off the family room. Easy access to downtown Winchester, public transportation, highways, & shopping. A beautiful all entertainment level for the whole family and private master suite!

33 Hemingway St Winchester, MA 01890

$1,199,000
5 Beds
3.5 Baths
2,761 SqFt
Status Active
MLS # 72702706
Property Type Single Family
Price Type --
Almost a brand new home! First floor contains a living room, dining room, family room and bright sunny den as well as a half bath and kitchen. Kitchen has beautiful custom made cabinets with large pantry cupboards and lots of counter space. Samsung brand name stainless steel appliances, Beautiful quartz countertops: There are five large bedrooms including the Large Master bedroom with walk-in his and hers closets, lovely textured tiled master bath with jacuzzi tub and handmade honey locust wood counter on double sink vanity. Two other bedrooms, another guest bathroom and laundry complete the second floor. The third floor upstairs portion contains a great kid space with its own full bathroom, two bedrooms and large playroom with a great secret room your kids will love. Built in bookshelves complete this floor. Beautiful huge teak deck overlooking a large level backyard great for entertaining and bbq’s. Conveniently located near the town center. Open house Sunday August 9th from 12-2