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!

7 Wainwright Rd 29 Unit 29 Winchester, MA 01890

$1,299,000 - 3Br/4Ba -  for Sale in Winchester
Open House
New
$1,299,000
3 Beds
3.5 Baths
3,350 SqFt
Status Active
MLS # 73301274
Property Type Condominium
Price Type --
Great opportunity! Imagine coming home to peace & serenity at The Ledges. Perched on a hilltop on the West side of Winchester, this oasis offers tranquility & carefree living. Day-lilies greet you leading to your private sanctuary with gleaming hardwood floors. Fireplace living room with sliders to your private deck. The main bedroom en suite on the first floor. The second level boasts loft, skylit bonus room for a home office, cedar closet, guest bedroom and full bath. The lower level walk-out features natural light, a guest bedroom and a kitchenette for your extended stays guests or entertaining. After tennis or a long walk, unwind by the pool. Perfect for downsizing without sacrificing space, enjoy stunning views throughout the community. The open floor plan with cathedral ceilings enhances spaciousness and light. Customize this home with your personal touch, start living the life you've always imagined. Don’t delay – seize the opportunity to own a piece of The Ledges today!

7 Conant Rd Unit 20 Winchester, MA 01890

$729,900 - 2Br/2Ba -  for Sale in Winchester
New
$729,900
2 Beds
2 Baths
1,168 SqFt
Status Active
MLS # 73300946
Property Type Condominium
Price Type --
Beautifully maintained first-floor condo in the highly sought-after Willows at Winchester complex. This expansive, single-level home features an open-concept living and dining area with a cozy gas fireplace, a modern kitchen with granite countertops, and a spacious primary suite with a walk-in closet and en-suite bath. The second bedroom also offers a walk-in closet. The unit is complete with central AC, in-unit laundry, and a private, enclosed patio. Additional perks include an attached garage with dedicated entry and attic storage. Enjoy the complex’s upscale amenities, including a heated pool, fitness center, and clubhouse with a full kitchen and entertaining area. Ideally located in the heart of Winchester, convenient to shops, restaurants, the commuter rail, and schools. This opportunity won’t last!

49 Wendell Street Winchester, MA 01890

$1,650,000 - 5Br/5Ba -  for Sale in Winchester
Open House
New
$1,650,000
5 Beds
4.5 Baths
2,944 SqFt
Status Active
MLS # 73300709
Property Type Single Family Residence
Price Type --
Extraordinary design, craftsmanship & space in stunning, one-of-a-kind exquisitely expanded home. Offering a unique in-law/au pair/teen suite with soaring cathedral ceiling, open living space, kitchenette, bedroom & full bath, this exceptional beauty perfectly balances custom luxury with lifestyle flexibility. All 3 levels offer impeccable space highlighted by distinctive, fine features: maple floors & stairs, French doors, bay windows, coffered ceiling & more (see list). Gracious living room w/bay window & fireplace; elegant dining room leads to cozy sitting area & eat-in kitchen w/cherry cabinets, granite counters, stainless steel appliances, chef’s stove & doors to mahogany deck overlooking gorgeous fenced yard with 3 patios, walkways & shed. Primary suite has large walk-in closet & sleek bath w/quartz double sinks & heated floor. Laundry, plus 3 bedrooms & full bath also on 2nd level. Lower level boasts family room & office. Add to the list: fab 2 car garage & convenient location.

3 Mason Way Unit 67 Woburn, MA 01801

$1,227,705 - 3Br/3Ba -  for Sale in Woburn
Open House
$1,227,705
3 Beds
2.5 Baths
2,143 SqFt
Status Active
MLS # 73299372
Property Type Condominium
Price Type --
New construction townhome at Highland at Vale in Woburn. The Jackson floor plan offers 2,100+ square feet on two levels. The kitchen is bright and spacious with tons of cabinets for storage, stainless steel appliances, and a large kitchen island. The oversized gathering room is the perfect space for entertaining or relaxing with your family. The many windows along the first floor fill the home with natural light and the bay window in the separate octagon shaped dining room adds light and space. The first floor is completed with a large outdoor deck for friends and family to enjoy. The second floor features 3 bedrooms, one of which is an oversized owner's suite adorned with seven windows, a lovely sitting area, double walk-in closets and a spa-like owner's bath with large window over soaking tub. All three bedrooms have large closets with an abundance of storage. Hillside community with amazing views and neighborhood feel, located minutes off routes 93 & 95.

115 Washington St Unit 2d Winchester, MA 01890

$549,900
2 Beds
1 Bath
1,036 SqFt
Status Active Under Contract
MLS # 73298669
Property Type Condominium
Price Type --
Discover a unique opportunity to live in the heart of downtown Winchester at the Church Place Condominium! This inviting residence features high ceilings and large windows, allowing abundant natural light to fill the space. Enjoy the convenience of in-unit laundry. The versatile second room can serve as a bedroom or home office, perfect for today’s work-from-home lifestyle. Additionally, this unit comes with two designated parking spaces, which can be used or rented out, adding even more value to your living experience. Nearby, you'll find a variety of amenities, including shops, parks, and dining options that cater to all tastes. Commuters will appreciate the close proximity to the commuter rail, ensuring easy access to surrounding areas. This condo perfectly blends comfort and convenience, making it an ideal choice for those looking to embrace a vibrant downtown lifestyle!

15 Churchill Road Winchester, MA 01890

$2,699,000 - 4Br/5Ba -  for Sale in Winchester
Open House
$2,699,000
4 Beds
4.5 Baths
5,501 SqFt
Status Active
MLS # 73298854
Property Type Single Family Residence
Price Type --
Indulge in modern luxury with this 2024 masterpiece, set on a double 1/2 acre lot. This 4 bedroom, 4.5-bathroom home seamlessly blends chic style with an abundance of functional space. The architectural design is dramatic, showcasing soaring ceilings, a stunning contemporary fireplace, state of the art kitchen & sun filled living room which opens to a fabulous deck, creating a perfect indoor-outdoor space. The gourmet kitchen features a sleek design w/ a large island, high end appliances, & stylish open shelving. Upstairs, the lavish primary suite features a spa like bath & large custom closet. The 3 additional bedrooms offer ensuite baths. The walk out LL family room w/ wet bar is the perfect space to unwind. This property also features a 2 gar attached garage, mud room, office & laundry room. The double lot offers many possibilities ~ level w/ patio. This home is located near conservation trails, top-rated schools & Boston offering a lifestyle of convenience, luxury & tranquility!

78 Middlesex Street Winchester, MA 01890

$1,595,000 - 3Br/3Ba -  for Sale in Winchester
Open House
$1,595,000
3 Beds
2.5 Baths
2,650 SqFt
Status Active
MLS # 73298334
Property Type Single Family Residence
Price Type --
Amazing transformation of a Classic Colonial carefully reimagined for today's busy lifestyle. Living room with gas fireplace opens to the family room, oversized hi-end kitchen with island, stainless & granite, dining room with sliders to the yard with a stone patio for outside entertaining, a mud room & 1/2 bath. Upstairs has a primary bedroom suite, bath with 2 separate vanities, walk-in custom closet, skylights, & 2 more bedrooms, bath & laundry. The lower level front to back 26' x12' recreation room has lots of possibilities & also has a home office, closet & large basement storage. Just a short walk along Wedge Pond through Elliot Park be amazed by all Winchester Town Center has to offer with its mix of bustling quaint shops & trendy restaurants, Commuter Rail just 2 stops to North Station, EV charging station or bike rental, & Packer-Ellis Town Tennis Courts, & let's not forget its Winchester's award-winning schools! *Open houses: Sat 11am-12:30pm, Sun 12:30-1:30pm (12th/13th Oct)

20 Amberwood Dr Winchester, MA 01890

$3,898,000
6 Beds
7 Baths
8,866 SqFt
Status Active
MLS # 73297360
Property Type Single Family Residence
Price Type --
Stunning 8800 sq ft brand-new contemporary in one of Winchester's favorite neighborhoods. A gracious foyer w/ high ceiling welcomes you to this elegant home loaded with natural light and architectural detail. Custom features include a gourmet eat-in kitchen w/ granite countertops, high-end appliances, secondary prep area, and fabulous outside dining options from the oversized deck. The spacious fire-placed family room, banquet-size dining room w/ wine-column, private home office and bedroom w/ en-suite bath complete the first floor. Luxurious primary suite w/a large balcony, expansive walk-in closets & spa-like bath w/ dual vanities, an oversized shower, and a lavish soaking tub on upper level, along w/ 3 additional en-suite bedrooms and an oversized laundry room. Finished lower level features additional entertainment areas, gym & en suite-bedroom. Fantastic location just up the hill from top-rated Vinson Owen School. Enjoy all that Winchester has to offer.

201 Washington Unit 201 Winchester, MA 01890

$1,050,000
3 Beds
2 Baths
2,018 SqFt
Status Active Under Contract
MLS # 73297482
Property Type Condominium
Price Type --
Grand residence in a restored 1880 Victorian. Expertly renovated with premium finishes throughout yet still retains elegant period details. Generous ceiling height and hardwood floors. Central a/c. Open plan 1st level has a spacious living room with gas fireplace and dining room with a wall of windows opens to the front balcony. Kitchen island with space for all (and storage below). Useful mudroom at the kitchen entrance. Second level has a primary bedroom with a walk-in closet and laundry. Two additional bedrooms, excellent storage space, and a stylish bath complete this level. Newer systems. Tons of basement storage. Proactive & collaborative association is 100% owner-occupied. Pet friendly. Roof and exterior work done in 2021 with Historic colors and superb workmanship. Garage with easy potential for EV charging. 4 pkg. Huge level lot with majestic trees is delightful for entertaining & gardening. Convenient to all that the Center offers; schools, parks, library, and commuter rail.

11 Plymouth Road Winchester, MA 01890

$2,200,000
4 Beds
3.5 Baths
4,787 SqFt
Status Active
MLS # 73297163
Property Type Single Family Residence
Price Type --
Magnificent Brick Colonial, perfectly situated at the end of a quite dead-end street, abutting conservation that offers unmatched privacy and tranquility. The gorgeous, spacious foyer leads into the beautiful front to back living room with a warm and inviting fireplace. The well-appointed dining room with custom built-in China cabinet is perfect for large family gatherings. The chef's kitchen has SS appliances, quartz counter tops and an oversized island with seating. An inviting wet bar leads into amazing family room and another fireplace. Kitchen sliders lead to an expansive deck that overlooks a truly majestic half acre with mature plantings and rolling green lawn. HW floors and decorative molding enhance this gorgeous first floor. Second floor offers 4 large bedrooms and HW floors. The primary's stunning ensuite is all Carrera marble. Lower level offers a game room, playroom, office and full bath. V-O school district, close to Mullen Field and Wright-Locke Farm.

666 Main Unit 411 Winchester, MA 01890

$729,000
2 Beds
2 Baths
1,170 SqFt
Status Active
MLS # 73296416
Property Type Condominium
Price Type --
Located in Prime Winchester Town Center ! Great Condo Opportunity for Retirees , Downsizing Folks or Young Professionals within short walking distance to the New State the Art MBTA Train Station currently being built and Projected to open Fall of 2024 .This top floor unit with Elevator has been tastefully updated with engineered Bamboo Wood floors , Beautiful Updated Bathrooms , Fireplace living room , Open Dining Area , Balcony , Association Pool , Garage Parking , Central Heat and Air conditioned . Convenient walk to all that Winchester Center has to offer like Fabulous Restaurants , Supermarket , Bakeries , Boutique Shopping , Hair/Nail Salons , Parks and walking trails.

18 Town Way Winchester, MA 01890

$2,200,000
4 Beds
3.5 Baths
4,026 SqFt
Status Active Under Contract
MLS # 73296209
Property Type Single Family Residence
Price Type --
Stunning 2006 Colonial, meticulously maintained & decorator-perfect. A grand entry with high ceilings and elegant archways welcomes you into this sun-filled home. The charming living & dining rooms showcase custom details throughout. The gourmet granite kitchen features an oversized island with seating for four, dining area & high-end amenities. A mudroom with ample storage is conveniently located off the kitchen, with sliders leading to a private bluestone patio. The family room offers built-ins & a gas fireplace. Private office with built-ins is tucked off the main hallway with a half bath. Upstairs are 4 bedrooms, including a guest suite with its own bath, plus a laundry room. The serene primary suite offers soothing colors, soft uplighting, and a spacious bath. The lower level includes a media room with a gas fireplace. This exceptional home is in a prime location, close to town, transportation, and Fells Reservation.

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