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!

6 Stratton Drive Unit 312 Woburn, MA 01801

$1,021,530
2 Beds
2 Baths
1,582 SqFt
Status Active
MLS # 73304936
Property Type Condominium
Price Type --
Welcome to the Ivywood at Highland at Vale, a stunning corner-unit home designed for both comfort and style. The sun-drenched interior boasts a gourmet kitchen with stainless steel appliances, an oversized island, and soft-closing cabinets, perfect for your culinary creations. The open floor plan effortlessly connects the kitchen to the gathering room, making it ideal for entertaining. Enjoy meals in the private dining area, then unwind in the spacious gathering room. The luxurious owner's suite features an extra-large walk-in closet and a spa-like bath, providing a serene escape. Guests will feel right at home in the generously sized second bedroom. Don’t miss this chance to own a beautiful, light-filled home with modern conveniences in a prime Woburn location!

7 Conant Rd Unit 20 Winchester, MA 01890

$699,900
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!

15 Churchill Road Winchester, MA 01890

$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!

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 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 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. BOSH A/C units can switch between propane/electric heating. Fantastic location just up the hill from top-rated Vinson Owen School. Enjoy all that Winchester has to offer

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 of 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.

9 S Gateway Winchester, MA 01890

$2,149,000
5 Beds
3.5 Baths
3,450 SqFt
Status Active
MLS # 73294195
Property Type Single Family Residence
Price Type --
Completely renovated colonial style home on a quiet cul-de-sac within walking distance to downtown Winchester! This home features 5 bedrooms, 3.5 bathrooms and an attached 2 car garage. The first floor offers kitchen, dining, living room and den/study. The flexible first floor also has a bedroom with en suite bath and an office/additional bedroom. Completing the first floor are a half bath and full mudroom. The second floor has 3 generous bedrooms with ample closet space. The primary bedroom has a large walk in closet and spacious bathroom with dual sink vanity. Excellent yard space and back patio for exterior living. Home will be complete towards end of October.

20 Goodwin Drive Unit 38 Woburn, MA 01801

$1,074,995
3 Beds
2.5 Baths
2,300 SqFt
Status Active
MLS # 73293478
Property Type Condominium
Price Type --
Price reflects Limited Time Incentive! Act Fast!! New construction in Woburn at Highland at Vale! The Southbrook is a beautiful townhome with open-flowing rooms and an abundance of natural light. The large kitchen, gathering room and private deck are perfect for entertaining guests. This plan features a convenient first-floor Owner's Suite with an attached spa-like bath for a relaxing escape. On the second floor you'll find a spacious loft with 2 guest bedrooms, walk-in closets, and a full bath. Just 12 miles to Boston as well as various options for local dining and entertainment. The innovative floor plan along with the unbeatable location makes this the perfect home! New hillside community and neighborhood with amazing views.

6 Lakeview Road Winchester, MA 01890

$3,769,000
5 Beds
4.5 Baths
5,768 SqFt
Status Active
MLS # 73290640
Property Type Single Family Residence
Price Type --
Experience the epitome of luxury living in this exceptional, high-end renovation of a breathtaking Winchester gem, located in one of the town’s most coveted neighborhoods. Enjoy stunning lake views from numerous rooms & the expansive 1000SF deck! Reconstructed and designed by RENEW, a company committed to blending historical integrity with modern amenities, paying meticulous attention to every detail. This home boasts a new floor plan w/ fabulous kitchen featuring a LaCornue 5 burner stove, 9' Calacatta marble island & fplc w/ adj family rm. 5 spacious bedrooms & 4.5 baths, including a magnificent primary suite w/ marble turret shower. The finished lower level offers a custom wine cellar, perfect for entertaining w/direct entry access to yard. Showcasing hand-picked and crafted specialty items that cannot be found in new builds. 3-car attached garage, & close proximity to Winchester's town center, the commuter train to Boston, Mystic Lakes beach, playgrounds & scenic walking trails.

50 Winford Way Winchester, MA 01890

$2,599,000
5 Beds
4.5 Baths
4,270 SqFt
Status Active
MLS # 73288818
Property Type Single Family Residence
Price Type --
Stunning new construction! Energy star rated, high efficiency 5 bed 4.5 bath home perfectly situated in a prime East Side location! The first floor welcomes you w/ an open, airy layout, featuring a stylish mudroom, pantry, bath & home office. The gourmet, high-end kitchen flows seamlessly into the living room, complete w/ a cozy fireplace; the dining area extends out to a deck, overlooking a beautifully landscaped yard & patio. The second floor boasts four spacious bedrooms & three full baths, including a lavish primary suite w/ a spa like bathroom. A well-appointed laundry room is also conveniently located on this floor. The third-floor suite is a true retreat, offering two versatile rooms ideal for extended family, office, or lounge, complete w/ a wet bar, an oversized bath & a 5th bedroom with abundant closet space. The expansive lower level adds even more living space, featuring a large family room and an additional full bath, perfect for entertaining. This home truly has it all

92 Hillcrest Pkwy Winchester, MA 01890

$2,499,999
5 Beds
4.5 Baths
4,048 SqFt
Status Active
MLS # 73279517
Property Type Single Family Residence
Price Type --
This exquisite, custom-built home from local master builder boasts a grand two-story foyer, a spacious chef's kitchen seamlessly flows into a vaulted ceiling family room, & an open concept living room & dining room perfect for entertaining. Upstairs, discover a luxurious primary bedroom suite w/expansive walk-in closet & a primary bath featuring double vanities, jacuzzi tub, & a large tiled shower. Two additional well-appointed bedrooms and bathroom complete the 2nd floor, while the 3rd floor offers expansive living w/two ensuite bedrooms, each with a full bath and walk-in closet. Enjoy the high ceilings, detailed custom woodwork, and elegant trim throughout. Additional amenities include central air, central vacuum, deck, & a spacious three-car garage. This stunning home epitomizes elegance and functionality in a prime Winchester location. Nestled near the scenic Fells reservation for outdoor enjoyment & vibrant Winchester center with it's restaurants, shops, farmer's market and more!

7 Wainwright Rd Unit 22 Winchester, MA 01890

$1,595,000
2 Beds
2.5 Baths
3,350 SqFt
Status Active
MLS # 73274235
Property Type Condominium
Price Type --
Welcome to a luxurious, turn-key residence at The Ledges, where elegance blends seamlessly with tranquility. Enter through a charming courtyard that welcomes you into this refined condo. The beautifully updated kitchen is a chef's delight, featuring granite countertops, cherry cabinetry, and premium stainless steel appliances. The open-concept layout flows effortlessly into the dining area and an inviting living room, complete with custom built-ins, a soaring ceiling with skylights, and a spacious deck that overlooks a serene creek and vibrant wildlife. The primary suite, conveniently located on the first floor, offers a walk-in closet and an updated en-suite bath for ultimate relaxation. Upstairs, discover a versatile den/bedroom, an additional bedroom, a full bath, and a loft with custom cabinetry. Expansive lower level includes a family room with walkout access, a private office/flex space, and a generous walk-in closet. Experience sophistication and tranquility in this exquisite.

28 Thornberry Road Winchester, MA 01890

$1,375,000
4 Beds
2 Baths
2,245 SqFt
Status Active Under Contract
MLS # 73274439
Property Type Single Family Residence
Price Type --
Welcome to 28 Thornberry! Located in the highly sought-after West Side. Situated on .34 acres, this home has been fully remodeled and is ready for its new owner. The home features four bedrooms plus a bonus room that works perfectly as an office or exercise room, and two full bathrooms. Since the home sits high above the road, you can enjoy complete privacy in your open-concept living, dining, kitchen, and family room spaces. The kitchen features all brand-new appliances as well as quartz countertops. Directly off of the living room, you have a generous-sized, peaceful balcony overlooking your front yard - perfect for coffee in the mornings, or unwinding after a long day at work. Off of the family room to the back of the house, you have a tranquil outdoor patio area. New roof, upgraded electrical and all new windows - this home needs nothing. Get into one of Winchester's top neighborhoods before the school year starts!

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