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!

22 Baldwin St Winchester, MA 01890

$999,000 - 3Br/2Ba -  for Sale in Winchester
New
$999,000
3 Beds
2 Baths
1,678 SqFt
Status Active
MLS # 73228100
Property Type Single Family Residence
Price Type --
Meticulously cared for by the same family for a half century and its pride speaks loudly for itself. This sound and charming HOME sits on an extremely level 9500 sq ft lot affording its new owner a myriad of options in both indoor and outdoor future living options. Located on a small dead end provides that community feel and a limited amount of traffic. Tall mature plantings provide privacy for outdoor activities and entertaining. Inside you will find brand new kitchen recently updated with gas stove, Second floor is where you will find three bedrooms and a full bath. Finished room in basement provides additional space. Easy access to major transportation routes and walking distance to downtown with its diverse options for shopping, dining, as well as one of Winchester's two commuter rails.

29 Kenwin Road Winchester, MA 01890

$1,150,000 - 4Br/2Ba -  for Sale in Highlands, Winchester
Open House
New
$1,150,000
4 Beds
2 Baths
2,132 SqFt
Status Active
MLS # 73228043
Property Type Single Family Residence
Price Type --
Charming 1930's Cape with arched doorways, built-ins, period details and several recent updates. Located in the desirable Highlands section of Winchester and within walking distance of the Muraco Elementary School, Leonard Field, the Fells Reservation and Winchester Hospital . Enjoy spacious rooms with several improvements including a striking remodeled eat in kitchen with white cabinets, granite countertops, and stainless steel appliances. Featuring gleaming hardwood floors and a three season porch on the first floor as well as a formal dining room, renovated bath, and 2 bedrooms. Flexible 2nd floor offers 2 large bedrooms and a remodeled bath. Enjoy outdoor fun in the private backyard with a newer patio, privacy fence, and room for future expansion. All of this and more in a convenient commuter location. It's time to make this welcoming home your own!

9 Robinson Park Winchester, MA 01890

$1,599,000 - 4Br/4Ba -  for Sale in Winchester
Open House
New
$1,599,000
4 Beds
3.5 Baths
3,224 SqFt
Status Active
MLS # 73227121
Property Type Single Family Residence
Price Type --
Bring your vision & transform this diamond in the rough into the jewel of Mystic Lake! Nestled on a quiet street outlining the lake shores, this spacious 4-bedroom, 3.5-bathroom home offers breathtaking views & endless potential. The 1st floor includes a large, light-filled kitchen primed for a modern makeover with an abundance of windows & french doors opening to a deck. A front-to-back living room w/ fireplace, large dining room w/ two china cabinets, mudroom, half bath, & office/playroom w/ sliders to a deck complete this floor. The 2nd floor features two wings. On one side you will find a primary bedroom w/ fireplace, full bath, & walk-in cedar closet. Two additional bedrooms & another full bath are also on this level. On the other wing above the attached garage you will find another suite w/ vaulted ceiling, full bath & large picture window framing views of the lake beyond. Partially finished basement w/ a 3rd fireplace. This home is your canvas to create a spectacular retreat.

50 Allen Road Winchester, MA 01890

$1,429,000 - 3Br/3Ba -  for Sale in East Side, Winchester
Open House
New
$1,429,000
3 Beds
3 Baths
2,769 SqFt
Status Active
MLS # 73226935
Property Type Single Family Residence
Price Type --
Top East side neighborhood! Don't miss this renovated & expanded 3BR home offering a great layout, flooded w/natural light. Spacious Living room w/wood burning fireplace, adjacent sun room, office/play room plus a stunning eat in kitchen w/ ample storage, prep space, large island & dining area w/ vaulted ceilings & picture window overlooking the well manicured yard. The main floor also includes a formal dining room & half bath w/ direct access to patio/yard. Upstairs the 2nd floor has 3 nicely sized bedrooms & full hall bath. The finished lower makes for great recreation space w/ large open room w/ built in desk, half bath, gym area, an adorable kids play room w/hand crafted club house door, laundry & plenty of storage! This home is equipped with a new AC system, 1 car garage w/EV hookup. Located on a great street in top location close to Winchester center! Hardwood floors & nice ceiling height throughout. A perfectly sized yard & patio complete this ideal home. *Offers Due 4/30 3pm*

7 Chisholm Rd Winchester, MA 01890

$899,000 - 3Br/1Ba -  for Sale in Winchester
Open House
New
$899,000
3 Beds
1 Bath
1,227 SqFt
Status Active
MLS # 73227059
Property Type Single Family Residence
Price Type --
Welcome to your next home! Classic 1930s Colonial nestled just steps away from the serene Middlesex Fells Reservation. Convenient access to 93 & 95, minutes from downtown Boston & within close proximity to town center, commuter rail & schools. Plenty of upside and possibilities here. Live in as-is or create your own vision for this lovely 3 bed, 1 bath home. Upon entry, a lovely foyer invites you inside, setting the tone for the warmth and character that permeate throughout. The first level offers a sun-filled living room with fireplace that flows into the dining room which boasts a built in China cabinet, and eat in kitchen with direct access to the private backyard. Three bedrooms with generously size closets, a full bath and linen closet are upstairs. The basement offers additional space for recreation, a workshop, or storage, catering to your evolving needs and lifestyle. Don't miss this chance to make your mark on this Winchester residence.

28 Garfield Ave Winchester, MA 01890

$999,000 - 4Br/2Ba -  for Sale in Winchester
Open House
New
$999,000
4 Beds
1.5 Baths
1,696 SqFt
Status Active
MLS # 73227028
Property Type Single Family Residence
Price Type --
This spacious home with thoughtful design details was carefully maintained through the years by original owner/builder. On first floor, be welcomed to a large living room with fireplace (plenty of space for multiple seating zones/uses), the dining room has custom built in storage that can be removed, half bath, enclosed porch and beautifully designed kitchen with eating area and bright sunny windows. On 2nd floor-find 4 ample bedrooms with hardwood floors and a full bathroom with double sinks and linen closet. The walkup attic has plenty of room for storage and might offer expansion potential. In the basement, you'll say WOW! High ceilings and a fireplace make it obvious that finishing a space similar to the living room would be an investment with great return! What else? A shed outside and a large flat back yard. Possibly space to build a detached garage and/or expand the kitchen and add a family room. Central AC 2021. Lovely enough to move right-in and improve in years ahead.

41 White St Winchester, MA 01890

$1,549,900
4 Beds
4 Baths
2,442 SqFt
Status Active
MLS # 73225512
Property Type Single Family Residence
Price Type --
Stunning young colonial house on a quiet street meticulously designed for modern living complete with a charming front porch. The bright and spacious open concept main level boosts hardwood flooring, detailed woodwork, expansive windows bathing the space in natural light. Central A/C. Modern kitchen showcases Bosch Stainless Steel appliances and granite counters. Second floor features a luxurious master suite with walk-in closet and beautifully tiled master bath with oversized shower. Two good size bedrooms with ample closet space and share a family bath. Finished basement comes with an additional bedroom along with flexible space ideal for recreation, exercise or a home office, accompanied by a convenient half bath. The detached, oversized two-car garage includes attic space with a pull-down staircase and plenty of room for a work area or storage. Move right in and enjoy everything Winchester has to offer. Easy highway access, public transportation, parks, and excellent schools!

83 Church Street Unit 6 Winchester, MA 01890

$985,000
2 Beds
2 Baths
1,493 SqFt
Status Active
MLS # 73225753
Property Type Condominium
Price Type --
Luxury living at its best at Unit 6 at 83 Church Street condominium complex. On the first floor there is a full-sized kitchen, dining area, living room with cathedral ceiling and large palladian window, second bedroom with full bath and large closet (now being used as a den). One of the highlights of this unit is an exterior door which allows entrance directly into the unit. Also, it allows for easy access to outdoor seating The custom moldings and architectural details add a special touch throughout along with hardwood floors. It includes a deeded garage and an additional parking place. Winchester offers a strong school system, two commuter rail stations, a vibrant downtown shopping area with restaurants, and the Middlesex Fells, a hiker's delight.

94 Lawson Road Winchester, MA 01890

$1,969,000
5 Beds
4 Baths
5,484 SqFt
Status Active Under Contract
MLS # 73225549
Property Type Single Family Residence
Price Type --
Incredibly deceptive from the front, this ideally located home is great at keeping a secret about what's behind the front door...Space, space & more space. W/well over 5000sf over 3 fls, this home sits in a neighborhood that is often described as the BEST STREET IN DOWNTOWN WINCHESER. It's exactly where you want to be. Often sought, but rarely found is a home in this MOST DESIRED NEIGHBORHOOD. A large family was raised here since 1988, & it's been loved AND lived in! The rooms are generous, the floor plan unique, the possibilities...endless! Newly removed, miles & miles of wall to wall carpet revealed ALL HW floors...even on both the front & back staircases. The grand two story foyer will one day be elegant & welcoming...paint, shined floors & a stunning chandelier will bring this fabulous home to life! W/plenty of bdrms for the growing family, the MASSIVE LL offers excellent potential for in-law or au pair quarters. Savvy buyers will know THIS is an opportunity NOT to be missed!

350 South Border Road Winchester, MA 01890

$1,150,000
3 Beds
2.5 Baths
2,240 SqFt
Status Active Under Contract
MLS # 73226090
Property Type Single Family Residence
Price Type --
This stunning 3-bedroom/2.5-bath home blends indoor comfort and outdoor charm. The main floor is an open concept design with cathedral ceilings and a striking floor-to-ceiling fireplace. Large windows offer abundant light and impressive views of nature’s beauty. The kitchen has stainless-steel appliances and a large island with extra storage and seating, the ideal spot for gatherings. Sunset views from the dining room make dinners delightful. A multi-level layout separates the bedrooms from the living areas. There are three spacious bedrooms including a primary bedroom and bath with a jacuzzi tub, plus ample closet space for easy organization. The flexible family room can also be a potential fourth bedroom or a space for your in-laws/extended family. The yard, complete with deck, is perfect for BBQs and outdoor fun. Set across from the Fells, endless outdoor activities await. Close to downtown Winchester with an easy commute to Boston, this home is a standout. No open houses, appt only

40 Wainwright Road Winchester, MA 01890

$1,699,000
4 Beds
2.5 Baths
2,853 SqFt
Status Active
MLS # 73225470
Property Type Single Family Residence
Price Type --
Discover the allure of this beautiful home nestled on an oversized 21,000sf private lot abutting conservation! This exceptional and meticulously maintained home boasts a flawless layout designed for comfort and functionality with large flowing rooms perfect for hosting parties & family gatherings. The stylish eat in kitchen offers granite countertops, espresso cabinetry and high end appliances w/island, a culinary enthusiasts dream! A fabulous screened porch off kitchen, large rear deck, plus a gorgeous patio all offer great places to unwind while enjoying the privacy & stunning conservation views. The sun drenched family room is beautiful w/ fplc & vaulted ceilings, the formal living & dining rooms complete this floor. The second floor offers 4 generously sized bedrooms & 2 full baths including the primary bedroom w/ walk in closet and spa like bath. Lower level gym/ rec room w/ direct entry to 2 car garage. Vinson Owen elementary school, Don't miss all this great home has to offer!

171 Swanton St Unit 63 Winchester, MA 01890

$699,000
2 Beds
2.5 Baths
1,823 SqFt
Status Active Under Contract
MLS # 73224255
Property Type Condominium
Price Type --
Welcome home to this spacious townhome in the coveted community, “The Village.” This is a sought-after end unit featuring an attached garage with direct entry inside. Upon entering, you will find a tidy kitchen with granite counters and breakfast bar and stainless steel appliances, which opens to a bright dining area with a skylight and access to a private patio overlooking a grassy courtyard. On this level you will also find an expansive living room with gas fireplace, and a half bath. Head upstairs to find the primary suite which features a walk-in closet, additional closet and full bathroom. One more bedroom, a bonus room/office, a second full bathroom, dedicated laundry area and additional closets complete this floor. Unit #63, with an extra driveway for added parking, is located in close proximity to the association’s swimming pool, clubhouse and tennis court. The Village is a short distance from Winchester’s vibrant town center, schools, and commuter rail stop.

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