About 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!

27 Everett Ave Winchester, MA 01890

$4,199,000
6 Beds
5.5 Baths
7,431 SqFt
Status Active
MLS # 73208958
Property Type Single Family Residence
Price Type --
This is one of the most notable and distinguished homes on Everett Avenue, with preeminent siting and curb appeal. Designed by famous architect Robert Coit, this residence combines the magnificence of early 1900s architecture with today's modern amenities. Completely renovated in 2023/2024, this residence features hallmark architectural details including Tudor-style balusters, high ceilings throughout, and a beautiful floor plan centered with a large entrance hall. Large-scale rooms, coffered ceilings, original crown moldings, mantels and decorative trim are enhanced by the beauty of restored hardwood floors. The brand new kitchen is a chef's dream, and includes a walk-in pantry with laundry and refrigerator drawers plus a butler's pantry with a wine fridge. Floor to ceiling windows flank the huge family room, overlooking park-like flat grounds. The huge lawn, magnificent old oak trees, beautiful birches and an ample driveway are some of the distinguishing exterior features.

19 Gershon Way Unit 19 Winchester, MA 01890

$2,249,000
3 Beds
2.5 Baths
3,938 SqFt
Status Active Under Contract
MLS # 73208722
Property Type Condominium
Price Type --
This home evokes a fresh, breezy, coastal vibe-making everyday feel like vacation. Located on the MOST PRIVATE homesite within this Award Winning 55+ Community. It is a modern, entertainer's dream house which boasts an open concept plan, TOP OF THE LINE CHEF'S KITCHEN + a buffet & bev. center in the adjacent dining room - which is topped off by a masterfully built coffered ceiling. All rooms look to the 2 story family rm, where a toasty fireplace wall is flanked by windows. The 1st floor also features a jaw dropping home office with French Doors & another coffered ceiling! For easy living: the primary suite is on the 1st flr, as well your covered deck & outside lounging area. Upstairs features: 2 bdrms, guest bath, sitting rm & loft. The FINISHED lower level has rm for a home gym + dinner & a movie. Enjoy indoor/outdoor 180° private wooded views, walking trails...Located near Winchester Center & the NEW Rail Station taking you to heart of Boston, just 8 mls away. A must see-must own

6 Lakeview Rd Winchester, MA 01890

$2,449,000 - 5Br/4Ba -  for Sale in Winchester
Open House
$2,449,000
5 Beds
3.5 Baths
4,300 SqFt
Status Active
MLS # 73206498
Property Type Single Family Residence
Price Type --
Amazing views of Mystic Lake! Two blocks to Wedgemere Station, Shannon Beach, and restaurants downtown. Through the front door of this 5 bedroom home you'll be impressed with beautiful in-laid hardwood floors that flow through the dining room and formal fireplaced livingroom. Top of the line appliances include a subzero refrigerator, gas Wolf oven with grill and a wine island with it's own dishwasher, sink, two sub-zero refrigerators, and plenty of room for seating. French doors off the kitchen lead to the beautiful wrap around deck with a partially covered area for shade, perfect for entertaining family and friends. Plenty of considerably large windows throughout the home allow for bright light in every room. The lower level consists of a den with access to the patio, a wine cellar, and interior access to the 3 car garage. Private well for irrigation and peaceful sitting areas with perennial blooms all season. Sold as-is

37 Canterbury Road Winchester, MA 01890

$1,599,000
4 Beds
2.5 Baths
3,527 SqFt
Status Active
MLS # 73205687
Property Type Single Family Residence
Price Type --
Welcome home! Nestled on a huge, fenced-in lot in a sought-after neighborhood, this picturesque 4 bed, 2 ½ bath home has it all. A spacious eat-in-kitchen with granite peninsula opens to a sun-filled family room boasting French sliders out to an elegant bluestone patio. The first floor also features a front-to-back, fireplaced living room, a bright home office, and a mudroom/playroom. Head upstairs to a stunning primary suite with soaring ceilings, a large, updated bath with glass shower and oversized tub, generous closets, laundry hookup, and French doors opening to a charming balcony. The second floor also features three additional bedrooms, an updated family bath, and additional closets. The partially finished basement includes an exercise room and a spacious storage area with additional laundry hookups. The backyard oasis with seasonal water views is perfect for outdoor enthusiasts. This home seamlessly blends comfort and style. Don’t miss this gem!

5 Gershon Way Unit 5 Winchester, MA 01890

$1,699,000
3 Beds
2.5 Baths
2,549 SqFt
Status Active Under Contract
MLS # 73202646
Property Type Condominium
Price Type --
Welcome to Winchester's premier 55+ community, a luxurious enclave nestled on the coveted west side. This unit is a perfect blend of modernity and comfort, all while enjoying the utmost privacy in this premiere location within the development. Step into a world of sophistication, where 10' ceilings, rich hardwood floors, & an abundance of natural light create an inviting ambiance. The open concept floor plan showcases a first-floor primary bedroom, complete w/ expansive walk-in closets and a lavish en-suite. The chef's kitchen features quartz countertops & high-end stainless steel appliances. Spacious living area w/ a gas fireplace, custom built-ins and coffered ceilings. Sliders from the dining room lead to your private covered deck, offering a serene retreat for relaxation. A versatile bonus room awaits your personal touch, ideal for a home office! Second level features 2 additional bedrooms and full bathroom along with a loft. Conveniently located near downtown Winchester & Boston!

1 Alice Lane Winchester, MA 01890

$2,699,000 - 6Br/6Ba -  for Sale in Cul- De- Sac Off South Border/ Near Town, Winchester
Open House
$2,699,000
6 Beds
5.5 Baths
5,524 SqFt
Status Active
MLS # 73198529
Property Type Single Family Residence
Price Type --
NEW CONSTRUCTION!! Must see this gorgeous 6 bedroom home w/ thoughtful design & high end finishes! This home is spacious & inviting, offering a grand open flr plan ideal for entertaining & modern day family living. The kitchen features an oversized island w/ seating/ quartz countertops, high-end appliances, & breakfast nook/dining area. Off the kitchen is a spacious family room w/gas fireplace & direct exterior access w/ sliders leading to large deck or patio & nice rear and side yard. The first floor also offers a formal dining room and guest bedroom w/ bath plus a home office & 1/2 ba. The second level primary suite is luxurious, offering a sitting area, sleeping area, huge walk-in closet, lavish bath w/double vanities, oversized shower & soaking tub! Three additional beds incl. junior suite w/ bath, full hall bath & laundry room finish this level. Finished lower level media/ rec room w/ full bath. 2 car garage direct entry to great mudroom! Quick & easy access only 6 miles to Boston

15 Dix Street Unit 10 Winchester, MA 01890

$1,599,000
2 Beds
2 Baths
2,066 SqFt
Status Active
MLS # 73195760
Property Type Condominium
Price Type --
Welcome to this exquisite WATERFRONT PENTHOUSE nestled in the heart of Winchester. Upon entering, you'll be captivated by the seamless flow of the open concept kitchen, living, and dining area, complemented by not 1 but 2 private balconies that offer breathtaking water views. The primary suite is a true haven, featuring an expansive walk-in closet (large enough for exercise equipment), vast storage, a 3RD private balcony, and a luxurious spa-like bath. The kitchen is a culinary delight, boasting a large center island, marble tops, and high-end appliances. With its stunning style and finishes, this condo is sure to impress even the most discerning buyer. Practicality meets luxury with abundant storage. A large pantry off of the kitchen has built-ins, a 2nd fridge, and a washer and dryer. There are lots of options in this additional room! 2-car garage parking with you guessed it - more storage space! Downtown location within walking distance of shops, restaurants, commuter rail and more!

276 High Street Winchester, MA 01890

$2,870,000 - 5Br/4Ba -  for Sale in Winchester
Open House
$2,870,000
5 Beds
3.5 Baths
6,595 SqFt
Status Active
MLS # 73170437
Property Type Single Family Residence
Price Type --
This fabulous house is in a beautiful and unique location, perched on a small hill with a secluded half-acre lot in a very quiet cul-de-sac area near the Winchester/Lexington line, far away from any road traffic and offering excellent privacy. There are 4 floors of living space containing 5 bedrooms and 3.5 bathrooms with two separate laundry areas. The grounds offer stunning front and back yards with a large deck and a gazebo. The property is adjacent to a lovely forest with a pond (Whipple Hill/Smith Pond). A short walk away from Wright-Locke farm and a short drive to shops, malls, and major routes with an easy commute to main business areas. Plenty of leisure facilities nearby including swimming pools, tennis courts, golf courses, skating rinks, gyms, restaurants, etc. Importantly, this house is in one of the best school districts anywhere and the Town of Winchester is renowned for its charm and the quality of life it offers.

20 Bellevue Avenue Winchester, MA 01890

$2,699,000
6 Beds
6.5 Baths
6,300 SqFt
Status Active
MLS # 73160636
Property Type Single Family Residence
Price Type --
NEW CONSTRUCTION! This spacious 6 bed, 6.5 bath home by a top local builder has it all! With over 6,300sf of living space you won't want to miss this stunning home. The first flr offers a gourmet kitchen w/ oversized island w/ seating/ quartz countertops, high-end appliances, & breakfast nook/dining area. Off the kitchen is a spacious family rm w/gas fireplace & direct exterior access w/ sliders leading to a large patio & great yard. The first floor also offers a guest bedrm or home office w/ full bath, mudroom and powder rm. The second level primary suite includes huge walk-in closet, lavish bath w/double vanities, oversized shower & soaking tub! Three additional beds, 2 full baths & laundry room finish this level. The finished third flr is a large loft/playroom/gym w/ full bath. Finished lower level media/ rec room, additional bedroom w/ full bath and wine cellar. 2 car garage direct entry to great mudroom! Conveniently located just 7 miles north of Boston nr Hospital & the Fells!

89 Wildwood Street Winchester, MA 01890

$2,499,000
7 Beds
5.5 Baths
4,800 SqFt
Status Active
MLS # 73160639
Property Type Single Family Residence
Price Type --
NEW CONSTRUCTION!! Must see this gorgeous 7 bed 5.5 bath home w/ thoughtful design & high end finishes! This luxury home is spacious and inviting, offering a grand open floor plan ideal for entertaining and modern day family living. The kitchen features an oversized island with seating/ quartz countertops, high-end professional appliances, breakfast nook/morning dining area. Direct access off the kitchen w/ sliders leading out to the large & private rear yard. Off the kitchen is a spacious family room with gas fireplace. The first floor also has a formal dining room & 7th bed OR home office with 3/4 bath. The second level master suite is spacious & offers an oversized walk-in closet, a lavish bath with tiled shower/glass enclosure, double vanities & soaking tub! The 2nd level also includes 3 additional beds & 2 baths; two beds with adjoining bath plus laundry room. Finished lower level media/ rec room and additional bedroom w/ full bath. Oversized 2 car garage, mudroom~ close to town!

15&lot227 Vinson Circle Winchester, MA 01890

$6,500,000
6 Beds
6.5 Baths
8,805 SqFt
Status Active
MLS # 73134071
Property Type Single Family Residence
Price Type --
Visionary New Construction has begun! Quality and 1st class design define this rare legacy residence.Spectacular interpretation of a modern colonial designed by acclaimed architect & built by Master Builder.Impeccably positioned on one of the highest points in Winchester & commanding seasonal skyline vistas.Start your tour with the Grand 23' Entrance Hall.Sail under fabulous 10' ceilings throughout the main floor as they carry you past the library,dining room,into the living room, stunning kitchen & breakfast room.2nd floor provides 3 generous en suite BR's,Gallery,and the Grand Primary Suite with sensational dressing room & bathroom.Lower living/play space enhanced with magnificent family room,kitchenette,glass enclosed gym,game room,wine lounge,connecting wine cellar,and au pair suite with adjacent full bath.Close to an acre on 2 lots,home will be majestically oriented boasting a deep 85' setback from the street while providing rear entertaining grounds of magazine quality. No equal.

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