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!

11 Alden Lane Winchester, MA 01890

$2,199,000
4 Beds
3.5 Baths
3,431 SqFt
Status Active
MLS # 73313015
Property Type Single Family Residence
Price Type --
This stunning new 4 Bed 3.5 BA home in Winchester’s sought-after East Side is a must see! The first floor boasts a dramatic contemporary design with high ceilings and designer finishes with oversized windows drawing attention to the setting w/ large rear yard & oversized deck, great for entertaining and family enjoyment.The open airy layout features a great entry w/ mud room, high-end kitchen with high end appliances incl. a double fridge, beverage cooler w/custom pantry, living room with an eye catching modern fireplace, dining area, and a large deck leading to the back yard. This home also features a first-floor bedroom suite or office with bath. Upstairs, the expansive second floor includes three additional spacious bedrooms w/ large windows, vaulted ceilings and 8' doors along two full baths, laundry room & includes a luxurious primary suite w/ spa-like bath & generous custom closet. The lower level offers a large space for family room/ game room or gym w/ direct garage entry.

666 Main St Unit L3 Winchester, MA 01890

$699,000
2 Beds
2 Baths
1,160 SqFt
Status Active
MLS # 73312551
Property Type Condominium
Price Type --
Welcome to 666 Main St Unit L3- Ground level 2 Bedroom Unit with Sliders to Patio overlooking Wedge Pond-Kitchen Totally Updated with Custom Cabinets and Quartz Countertop and Back Splash. Stainless Steel Appliances- Fire Place Living Room with Hardwood Floors-Spacious Dining Area with Hardwood Floors- Open Concept-Master Bedroom with Full Bath, Walk in Closet and Hardwood Floors-2nd Bedroom with Hardwood Floors-2nd Bath has a Ceramic Tile Walk-In Shower. Garage Parking and Association Swimming Pool . Easy access to Points Boston and Points North

22 Grove Pl Unit 30 Winchester, MA 01890

$999,000
3 Beds
3 Baths
3,045 SqFt
Status Active Under Contract
MLS # 73312550
Property Type Condominium
Price Type --
Welcome to 22 Grove Place Unit 30, a 3-bedroom, 3-bathroom townhouse in Winchester, MA, that combines single-family privacy with the ease of townhouse living. This home just had the walls and ceilings freshly painted, along with new light fixtures that add a modern touch. The main level offers a spacious living room with high ceilings, a cozy double sided gas fireplace, a home office, first floor bedroom, full bath and a spacious kitchen. Bedrooms on the top floor come with generous size walk-in closets. The large basement provides flexible space, ideal for a media room, kids’ playroom, or home gym. Enjoy two outdoor decks for private relaxation—making this an ideal home with room to add your own cosmetic touches! Just 1 mile away from Winchester's vibrant downtown center you will find plenty of dining options, shopping and a brand new commuter rail station!

9 Robinson Park Winchester, MA 01890

$1,779,000
4 Beds
3.5 Baths
3,224 SqFt
Status Active
MLS # 73312013
Property Type Single Family Residence
Price Type --
Classic Colonial 4 bedroom 3+1/2 bath on quiet street overlooking the Mystic Lake. Awaits buyers with vision prepared to renovate. Freshly painted interior gleaming hardwood floors. Gracious front to back fireplaced living room w/custom shelves & built-ins & picture windows. Formal dining room w/2 china closets adjacent to large open eat-in light filled kitchen. French doors to back deck. Den/office w/book shelves & slider to another deck. 2nd floor features spacious primary bed ensuite oversized bath vanity w/double sinks & white marble shower, fireplace, and walk-in cedar closet. Family bath tiled with tub & shower in hallway. Two equal sized bedrooms. Back bedroom with armoire. 1st floor mudroom off the kitchen affords direct access to 2-car garage. Stairs lead to 4th huge guest/nanny bedroom ensuite bath, balcony, and large front facing picture windows with lake views. Partially finished basement features wood paneled recreation room w/3rd fireplace & 2 built-in desks.

36 Oneida Road Winchester, MA 01890

$1,699,000 - 3Br/4Ba -  for Sale in Winchester
Open House
$1,699,000
3 Beds
4 Baths
2,376 SqFt
Status Active
MLS # 73312376
Property Type Single Family Residence
Price Type --
TOTAL RENOVATION! Thoughtfully crafted to create a warm and inviting abode. Step inside to discover the completely reimagined first floor with an open concept dining room, sitting room, and show-stopping brand new kitchen with a center island, and a slider leading to a patio, ideal for alfresco dining and entertaining. The first floor also hosts a versatile family room with access to a private deck, a laundry area, and a tastefully designed full bathroom. Venture upstairs to find 3 bedrooms, including a lovely primary suite. The lower level of this home is a true retreat, featuring a rec room with a wine closet, a full bathroom, and access to a covered patio. The fenced-in yard, two patios, and deck provide wonderful outdoor space for leisure and recreation. With brand new electrical, plumbing, windows, and systems, 36 Oneida is truly MOVE-IN READY! Just FOOTSTEPS away from Ambrose Elementary School and playground, and 1 mile from Winchester town center!

64 Wildwood St Winchester, MA 01890

$2,985,000 - 5Br/5Ba -  for Sale in Winchester
Open House
$2,985,000
5 Beds
4.5 Baths
4,400 SqFt
Status Active
MLS # 73310488
Property Type Single Family Residence
Price Type --
Exquisitely restored brick Colonial situated in the sought-after Flats neighborhood of Winchester. Boasting refinished hardwood floors, beautiful moldings and trim, & high ceilings throughout, no detail has been overlooked in this meticulous renovation. The gourmet kitchen, featuring high end appliances, is perfect for culinary enthusiasts, while the formal dining room, complete w/ wood-burning fireplace, creates an ideal setting for gatherings. Just off the kitchen, a bar area creates an inviting space for entertaining, while the large working pantry enhances functionality. A newly designed living room w/gas fireplace offers a cozy retreat, & the master suite provides a tranquil escape, boasting a lavish bath & spacious walk-in closet. A 2 car garage, slate roof, copper gutters, patio, & professionally landscaped yard further enhance the property’s appeal. This home showcases thoughtful design & superior craftsmanship, offering a perfect blend of historic character & modern comfort!

189 Mystic Valley Pkwy Winchester, MA 01890

$1,899,900 - 6Br/3Ba -  for Sale in Winchester
Open House
$1,899,900
6 Beds
2.5 Baths
3,543 SqFt
Status Active
MLS # 73307438
Property Type Single Family Residence
Price Type --
Nestled in a coveted location just moments from the heart of downtown Winchester, the stunning Barstow House boasts a unique Mansard roof & timeless colonial architecture. This historic gem features a versatile floorplan designed for modern living while preserving its classic charm. The first level beautifully blends form & function; the home office, mudroom, a dedicated laundry room & a convenient half bath, all complimenting the formal living room, dining room, family room & spacious kitchen - perfect for entertaining. Ascend to the second and third floors, where you'll find three spacious bedrooms on each level, offering ample space for family & guests. A back staircase provides private access to a second-floor bedroom, making it perfect for generational living or added privacy. Watch the bustle of the town center from the spacious front porch & enjoy the expansive yard. Don’t miss this rare opportunity to own a piece of Winchester’s history!

15 Dix Street Unit 9 Winchester, MA 01890

$995,000
1 Bed
2 Baths
1,275 SqFt
Status Active Under Contract
MLS # 73310174
Property Type Condominium
Price Type --
Get ready to enjoy one level living with elevator access from heated garage with 2 exclusive use parking spots. This is the place to be for LOCATION, LOCATION, LOCATION AND GARAGE PARKING!!! Inviting, open floor plan features hardwood flooring, large windows, and a generous amount of storage space. Kitchen features large marble topped island with counter seating, gas range and Sub Zero refrigerator. Bedroom has ample storage space (much more than meets the eye!), view of Wedge Pond and large en-suite bathroom with laundry. Office also has full en-suite bathroom. Elegant layout with quality details throughout including a skylight at the entrance. More storage space in garage. Live in town with easy access to commuter rail, shops, restaurants and services. Enjoy everything this great community has to offer: Middlesex Fells Reservation, Wright-Locke Farm, annual community events, Saturday Farmer's Market, a vibrant arts community and more!

64 Highland Avenue Unit 18 Winchester, MA 01890

$425,000
1 Bed
1 Bath
758 SqFt
Status Active Under Contract
MLS # 73308991
Property Type Condominium
Price Type --
DON'T MISS THIS ONE! Ideal location at Waterfield Square - This spacious one bedroom is a diamond-in-the-rough waiting for your upgrades. High ceilings and huge windows bring in lots of sun and light. Open floor plan. Lots of closet space. Washer & Dryer in unit. Deeded parking, basement storage, tennis court, picnic area with grill, fire pit, located across from the North Reservoir and Middlesex Fells Reservation with miles of trails for biking and hiking. Easy access to Rt. 93 and commuter rail to Boston. Enjoy all the fine restaurants and shops. This is an opportunity to move to Winchester at an incredible price. Please note: This unit may NOT be rented out. Pets and smoking not allowed.

6 Governors Avenue Winchester, MA 01890

$1,199,000
3 Beds
1.5 Baths
1,883 SqFt
Status Active
MLS # 73307706
Property Type Single Family Residence
Price Type --
Welcome to this impeccably maintained & beautifully updated Colonial on large lot near the town center. This home blends charm w/ modern convenience, featuring 3 spacious bedrooms & 1.5 baths w/ a great floor plan. The first level features a sun-drenched living room that flows into an inviting dining room; updated kitchen overlooks the rear yard & is equipped w/ ample storage, stainless steel appliances, gas cooking & granite counters. The large family room is the perfect space for family & media. This home has great flow & also offers fantastic expansion potential to add a primary suite above the first floor family room. The second floor currently has 3 nicely sized bedrooms & a full hall bath. The oversized level yard is a rare find & relaxing place to unwind & enjoy w/family & friends; complete w/ a patio, storage shed & direct entry 2-car garage. Located just outside the town center, close to schools, restaurants, shopping & the Train to Boston! Don't miss this great home!

7 Conant Rd Unit 60 Winchester, MA 01890

$749,000
2 Beds
2.5 Baths
1,634 SqFt
Status Active
MLS # 73307969
Property Type Condominium
Price Type --
Welcome to the highly coveted condominium living in Winchester: the Willows. With over 1,600 sq. ft., these two stories, 2 beds, and 2.5 baths condominium, is one of the larger unit in the complex. The unit features modern amenities such as: hardwood floor in the living area, three balconies, in-unit washer/dryer, gas fireplace, , and Central A/C & heating with Nest thermostat. You will also fall in love with additional amenities such as: 2 Parking Spots (One GARAGE + One Exterior space), deeded storage area in the basement, along with building amenities such as: in-ground heated pool, exercise room, and clubhouse. Conveniently located in one of the most highly rated school system in Massachusetts, less than two miles drive to Downtown Winchester & MBTA Commuter Rail, this unit is not to be missed!!

25 Hemingway St Winchester, MA 01890

$979,900
3 Beds
2 Baths
1,890 SqFt
Status Active Under Contract
MLS # 73305986
Property Type Single Family Residence
Price Type --
Discover the potential of this charming and well-maintained 2-story Cape-style home, offering both comfort and privacy in a highly desirable Winchester location. Conveniently situated near a public elementary school, public transportation, healthcare services, and a variety of dining options, this home ensures easy access to everything you need. Featuring 3 spacious bedrooms and 2 full baths, the home also includes a versatile walk-out basement with its own heating zone. The first floor boasts hardwood floors in the living areas and stairway, with parquet tiles in the hallway and first-floor bedroom. The second-floor bedrooms offer large closets and additional attic space, providing ample storage. This is your chance to make this charming home your own and bring your vision to life. Don’t miss the opportunity to claim this exceptional Winchester address!

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