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!

18 Stone Ave Winchester, MA 01890

$1,599,000 - 5Br/4Ba -  for Sale in Winchester
Open House
New
$1,599,000
5 Beds
3.5 Baths
3,175 SqFt
Status Active
MLS # 73239587
Property Type Single Family Residence
Price Type --
Cherished home located on a quiet side street in Winchester Highlands, close to the popular Fells Reservation. Flexible layout perfect for today's living with 5 beds & 3.5 baths. The 1st floor features a formal living room with fireplace, expansive family room & open concept dining room/kitchen with new appliances, cherry cabinets and beverage cooler. Two 1st floor bedrooms and a full bath provide options for an amazing in-law suite, hosting guests or as a home office. The 2nd floor has 3 beds, the primary features cathedral ceilings, gas fireplace, an en-suite bath with a soaking tub and a glass-enclosed tiled shower. Oversized rear deck overlooks a private back yard, perfect for summer entertaining. Two-car side entry garage leads to a finished basement great for home gym or playroom. Convenient access to I-93, and minutes from Muraco, McCall, the High School & Winchester center with boutique shops, restaurants, cafes and commuter rail. Showings start at Open Houses Sat/Sun 12-2pm.

400 Cross Street Unit 401 Winchester, MA 01890

$778,000 - 2Br/3Ba -  for Sale in Winchester
Open House
New
$778,000
2 Beds
2.5 Baths
1,523 SqFt
Status Active
MLS # 73238956
Property Type Condominium
Price Type --
Experience unparalleled charm in the CORNER and BIGGEST unit at Winchester Crossing. Step into an inviting atmosphere with an open-concept living area, adorned with abundant natural light. Relax in the expansive living room, complete with a cozy fireplace and direct access to a private balcony, ideal for enjoying serene evenings. The kitchen features a breakfast nook, which always offers a peaceful mind for the owner. On the third floor, there are two well-sized bedrooms situated at opposite ends of this level, each complemented by ideal floor plans. Don't miss the bonus area next to the HEATED garage, which can be used as a gym or entertainment area. Garage also offers direct access to the backyard, providing additional outdoor space for relaxation or play. Commuting is a breeze with easy access to the commuter rail, making travel to nearby areas convenient. The location is also close to Macdonald Field, Horn Pond, various enrichment classes, and a host of other fun activities.

7 Plymouth Road Winchester, MA 01890

$1,899,000 - 4Br/4Ba -  for Sale in Birchknoll, Winchester
Open House
New
$1,899,000
4 Beds
4 Baths
2,770 SqFt
Status Active
MLS # 73239052
Property Type Single Family Residence
Price Type --
Prepare to swoon over this exquisite colonial offering a sprawling backyard oasis in one of Winchester's most desired neighborhoods. This home boasts luxurious renovations, thoughtful design, and magazine-worthy aesthetic. The main level features posh mud and powder rooms, a sunlit living room with a fireplace, and a stunning dream kitchen with a peninsula breakfast bar that opens to the dining room. Glass sliders lead to the deck overlooking the sophisticated private landscape. The second floor reveals 4 bedrooms and 2 full bathrooms, including an expansive primary suite with ensuite, custom walk-in closet for her, and separate closet for him. The lower level includes a versatile play area, family room, or gym, complete with half bath, laundry and direct walkout to an oversized entertainers’ patio. The magnificent outdoor space features a sun-drenched heated pool, irrigated gardens, mature trees, elegant fieldstone walls, and a charming pool house- it's the ultimate outdoor retreat!

134 Johnson Road Winchester, MA 01890

$1,149,900 - 4Br/3Ba -  for Sale in Winchester
Open House
New
$1,149,900
4 Beds
2.5 Baths
2,430 SqFt
Status Active
MLS # 73239366
Property Type Single Family Residence
Price Type --
Extraordinary opportunity to own this updated 4 bedroom, 2.5 bath Colonial abutting the 120 acre Whipple Hill Conservation Area. This home boasts a wonderful-for-entertaining first floor layout, including a spacious living room, dining room with wainscoting, eat-in kitchen, 1/2 bath and family room with beautiful wide-board flooring and fireplace. Access the deck off of the family room. The second floor has the main bath and 4 bedrooms including the front to back primary bedroom with en suite 3/4 bath and 2 double closets. The large finished room in the lower level, well lit by 5 windows, has a direct walk-out to the back yard. The oversized, attached 2 car garage leads directly into the side hall with double entry closet and half-bath. The interior of the home has been recently painted throughout and had new hardwood floors installed on the 2nd floor. All of this sitting on a 1/2 acre lot and next to 1.39 miles of hiking trails. Don't miss this one!

99 Ridge St Winchester, MA 01890

$1,899,000 - 5Br/4Ba -  for Sale in Winchester
Open House
New
$1,899,000
5 Beds
3.5 Baths
4,567 SqFt
Status Active
MLS # 73239172
Property Type Single Family Residence
Price Type --
Discover this spacious custom colonial on Winchester's coveted west side! Built in 2004, it's a short walk to Vinson Owen School and Wright Locke Farm. Enjoy abundant natural light in the south-facing great room, flowing layout to dining area and breakfast nook overlooking the patio. The kitchen features ample counter space, a double oven, and a large island to entertain. Adjacent to the kitchen, is a private office with tree canopy views. French doors lead to the sunny family room. Upstairs find a primary bedroom with ensuite bath and walk-in closet, plus three more bedrooms with ample storage. On the 3rd floor, a play space. The finished lower level has a bonus room and full bath. The attached and heated two car garage is accessed via the basement. The level professionally landscaped yard wraps around the side leading to the second patio and more parking. Recent upgrades include exterior painting and new central air. Don't miss this opportunity for comfortable living in Winchester!

7 Stevens St Winchester, MA 01890

$2,299,000 - 5Br/4Ba -  for Sale in Winchester
Open House
New
$2,299,000
5 Beds
3.5 Baths
4,091 SqFt
Status Active
MLS # 73239409
Property Type Single Family Residence
Price Type --
Circa 1865,this spectacular Mansard roof Victorian home blends timeless elegance with the modern conveniences of modern family life.Exquisite period detail and appeal abound with leaded and stained glass windows and grand staircase all lovingly maintained. In town location is perfect for shopping and transportation but the private estate like setting has maginificent gardens .large private yard with two patio areas.Inviting oversized front porch has also a screened in porch perfect for entertaining. Gracious formal living room and dining room. Kitchen has a six seat island with granite and stainless steel and also has a dining area and French doors to the patio. Right off the kitchen is a gorgeous family room with a fireplace. Second floor has primary suite with large bath and two additional bedrooms plus washer/dryer area, bath and sunroom.Third floor suite has two additional bedrooms ,office area and a large bath. Enjoy sunset views and walks to Fells Reservation

4 Stratton Drive Unit 104 Woburn, MA 01801

$830,720 - 2Br/2Ba -  for Sale in Woburn
New
$830,720
2 Beds
2 Baths
1,667 SqFt
Status Active
MLS # 73238590
Property Type Condominium
Price Type --
Welcome to Highland at Vale in Woburn! The Ashford home design is ideal for your everyday lifestyle. The corner unit allows for an abundance of light to pour through the windows. The kitchen is built for you inner chef with stainless steel appliances, an oversized kitchen island, and beautiful cabinets. The open floor plan makes entertaining a breeze! Relax with family and friends in the spacious gathering room. Owner's can escape to their private bedroom with large walk-in closet and spa-like bath attached. There's plenty of space for guests in the second bedroom!

20 Bacon Street Winchester, MA 01890

$1,369,000 - 5Br/4Ba -  for Sale in Winchester
Open House
New
$1,369,000
5 Beds
4 Baths
3,206 SqFt
Status Active
MLS # 73238071
Property Type Single Family Residence
Price Type --
Beautifully maintained & filled w/character & charm! This beautifully renovated home offers high ceilings, stunning updated kitchen flooded w/sunlight, quartz countertops, built ins & cozy dining nook w/ access to spacious private deck overlooking the yard. A Large bow front dining room w/ hardwood floors china cabinet & fire-placed living room create the perfect setting for family & entertaining. The second level has a large primary bedroom w/ floor to ceiling book shelves, newly renovated bathroom w/ double sinks, a second bedroom, home office & laundry area. The third floor offers two additional bedrooms & full updated bath. The basement is nicely finished w/a cozy game/family room, half bath plus work out area, w/ second fridge & plenty of storage. Close to Winchester town center, schools, restaurants, shops & Wedgemere train to Boston, Mystic Lakes beach & walking paths. Enjoy all the amenities of this charming home in top location, w/private entry & the feel of a single family!

20 Bacon Street Unit A Winchester, MA 01890

$1,369,000 - 5Br/4Ba -  for Sale in Winchester
Open House
New
$1,369,000
5 Beds
4 Baths
3,206 SqFt
Status Active
MLS # 73238365
Property Type Condominium
Price Type --
Beautifully maintained & filled w/character & charm! This beautifully renovated home offers high ceilings, stunning updated kitchen flooded w/sunlight, quartz countertops, built ins & cozy dining nook w/ access to spacious private deck overlooking the yard. A Large bow front dining room w/ hardwood floors china cabinet & fire-placed living room create the perfect setting for family & entertaining. The second level has a large primary bedroom w/ floor to ceiling book shelves, newly renovated bathroom w/ double sinks, a second bedroom, home office & laundry area. The third floor offers two additional bedrooms & full updated bath. The basement is nicely finished w/a cozy game/family room, half bath plus work out area, w/ second fridge & plenty of storage. Close to Winchester town center, schools, restaurants, shops & Wedgemere train to Boston, Mystic Lakes beach & walking paths. Enjoy all the amenities of this charming home in top location, w/private entry & the feel of a single family!

7 Conant Rd Unit 27 Winchester, MA 01890

$700,000 - 2Br/2Ba -  for Sale in Winchester
New
$700,000
2 Beds
2 Baths
1,160 SqFt
Status Active
MLS # 73237216
Property Type Condominium
Price Type --
Step into luxury living with this meticulously renovated single-level condo. No detail has been overlooked in this exquisite residence. Hardwood floors that flow seamlessly throughout the open concept floor plan, creating a warm and inviting ambiance. Brand new tiled bathrooms, featuring new fixtures, stylish vanities, and pristine finishes. Entertain with ease in the spacious living area complete with a gas fireplace. Benefit from the added convenience of a private garage, providing secure parking and additional storage space for your belongings. Indulge in the exceptional amenities offered by this complex, featuring a well-equipped fitness room, a welcoming clubhouse, and a heated pool. Open House Saturday May 18, 2024, 12:00pm- 2:00pm Sunday May 19, 2024,12:00pm- 2:00pm. Offers are due Tuesday May 21, 2024, at 5:00pm

26 Stowell Rd Winchester, MA 01890

$1,799,000 - 4Br/4Ba -  for Sale in Winchester
Open House
New
$1,799,000
4 Beds
3.5 Baths
2,816 SqFt
Status Active
MLS # 73237108
Property Type Single Family Residence
Price Type --
Nestled in an idyllic neighborhood, this stunning property underwent complete renovation/addition in 2016, ensuring modern comfort & space. As you step through the entry, you're greeted by an abundance of natural light & a sense of airiness that permeates every corner of the home. The open-concept layout seamlessly connects the living, dining, & kitchen, creating an ideal space for both family gatherings & entertaining guests. 1st floor also features home office, walk-in pantry, & mudroom to help keep life neat and organized! Upstairs, a primary suite w/walk in closet & lavish bath, 2 additional bedrms, & a family bath await, along w/2nd flr laundry. 3rd flr provides a private retreat with its own bath & walk-in closet. Finished basement offers xtra space for family rm, exercise area, & storage. Outside, a lush yard w/fire pit, brick patio, & pergola beckons outdoor enjoyment. Conveniently located just .75 miles to Lincoln Elementary, McCall Middle, & downtown Winchester. Welcome home!

12 Everell Rd Winchester, MA 01890

$1,589,000 - 3Br/3Ba -  for Sale in Symmes Corner, Winchester
Open House
New
$1,589,000
3 Beds
2.5 Baths
2,212 SqFt
Status Active
MLS # 73237312
Property Type Single Family Residence
Price Type --
Nestled in sought-after Symmes neighborhood this timeless home was renovated in 2019-2020 providing a refreshed layout and modern amenities while keeping the home's original charm. The gracious foyer leads to a front to back living room with fireplace, window seat and French doors opening to a new family room with a walkout to the patio and backyard. The dining room with bow window flows into the refurbished butler’s pantry and new modern kitchen complete with new mudroom, half bath, and back entrance to the driveway. The second floor was completely redesigned to include a primary suite with full bathroom, office, two additional corner bedrooms, main bathroom and W/D area for convenience. The partially finished basement offers a versatile space with a recreation room and ample storage, while the full staircase to the unfinished attic presents expansion possibilities. Detached garage with electric is EV ready. Solar panels are a modern touch. Convenient to train, schools and downtown.

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