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!

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5 W Chardon Rd Winchester, MA 01890

$1,749,900 - 6Br/4Ba -  for Sale in Winchester
New
$1,749,900
6 Beds
4 Baths
4,198 SqFt
Status New
MLS # 72520138
Property Type Single Family
Well maintained custom colonial in desirable neighborhood. Corner lot w/mature plantings & great curb appeal. This sun-filled home boasts six bedrooms & three fireplaces, completely renovated approx. 2008. First floor offers two generous sized bedrooms w/versatility; office, au pair or in-law w/full bathroom & shower. Large eat in kitchen flows into family room w/gorgeous stone fireplace. French doors lead to dining room with double sided fireplace shared with living room. Second floor offers a grand oversized master bedroom suite w/high ceilings, large walk in closet, spacious master bathroom w/tub, separate shower & double vanity sinks. Add'l three bedrooms one en-suite, plus a jack & jill bathroom shared by other bedrooms . Walk up attic with plenty of storage or choose to finish space. Oversized two car garage with direct entry to mudroom. High velocity A/C. New boiler/manifold/pump 2018. Radiant flooring throughout entire home. 75 gal hot water tank. Close to train and town.

10 Sussex Road Winchester, MA 01890

$969,000 - 3Br/2Ba -  for Sale in Winchester
New
$969,000
3 Beds
2 Baths
2,043 SqFt
Status New
MLS # 72520218
Property Type Single Family
10 Sussex Road, Winchester, MA 01890 Desirable location, this lovely ranch has been renovated from top to bottom and meticulously maintained - it's sunny and spacious. Open floor plan with updated kitchen and baths, roof updated, tilt-in windows, central air, 30 x 12 deck off the kitchen, irrigation system, insultation, updated heat and electric and shed. A beautiful home at a great price - 2 car under garage with door openers and direct access. Situated on a spectacular corner lot with mature plantings and a great neighborhood.

15 Tanglewood Lane Winchester, MA 01890

$1,630,000 - 5Br/6Ba -  for Sale in Winchester
New
$1,630,000
5 Beds
5.5 Baths
4,880 SqFt
Status New
MLS # 72520252
Property Type Single Family
Sprawling custom contemporary home on the West Side with a beautiful 30,536 sq ft lot. This one owner home circa 1982, offers luscious gardens and spacious privacy on a cul de sac in the VO school district. This home provides great space inside and out for busy lives, entertaining, celebrating and relaxing. There are 5 bedrooms including a spacious Master, en suite baths, a full finished Lower Level and open and flexible first floor plan with direct access to the back yard. The first floor also features beautiful and thoughtfully designed architectural details, 2 fireplaces, a family room overlooking the gardens and a spa bath for some very special down time.

336 Cambridge St Winchester, MA 01890

$720,000 - 7Br/3Ba -  for Sale in Winchester
New
$720,000
7 Beds
2.5 Baths
3,265 SqFt
Status New
MLS # 72520348
Property Type Single Family
A fabulous opportunity in Winchester. This massive colonial is ready for the savvy buyer or handyman looking for some sweat equity. Over 3,000 square feet of living area to work with. This house has gas, forced hot water heat on multiple zones and loads of parking. The hardwood floors have just been refinished and look incredible. All of the rugs were cleaned and are looking good. There are 2 wood burning fireplaces (unknown if they are working or not) and the location is incredibly convenient - just a stone's throw from the Whole Foods Market and right on the bus line. The lot is incredible with the house set high on the hill, well above and away from Cambridge Street.

993 Main Street Winchester, MA 01890

$1,225,000
5 Beds
2.5 Baths
4,383 SqFt
Status Active
MLS # 72518876
Property Type Single Family
Welcome to the “Charles Russell House”, a stunning Greek Revival in the heart of Winchester! Established in 1841 & recently updated for modern living, the 3-story home maintains much of its original historic charm. With a grand tri-level spiral staircase, 6 fireplaces (1 with gas insert), beautiful woodwork & a private outdoor oasis, the Charles Russell House embodies a quintessential New England home. Features include 5 spacious bedrooms (3 with fireplaces and walk-in closets), 2 full/1 half baths, sunlit kitchen with island & stainless steel appliances, playroom/rec room area & more! The serene master suite includes a celeb-style closet with custom built-ins & ensuite bath with double vanity, large soaking tub & steam shower. The home sits back from the road on a corner lot with lush gardens that bloom with the seasons. The back of the home faces a quiet one-way road, and is conveniently located close to downtown, transportation, restaurants and Horn Pond’s walking/biking trails.

6 Skyline Dr Winchester, MA 01890

$875,000
4 Beds
2.5 Baths
1,927 SqFt
Status Active
MLS # 72519177
Property Type Single Family
Welcome to 6 Skyline. Pride of ownership shows in this well-maintained home. Very clean very comfortable. Good sized, modern, eat-in kitchen with easy access to the spacious deck and gazebo for those outdoor summertime breakfasts or luncheons. This 4 bed and 2.5 bath house is located on a nicely landscaped lot, off of a private dead end way ending at and with access to Lexington Conservation land (Whipple Hill). Extra gravel parking area located just past the house will easily hold large camper and or boat or work vehicle(s). Great outside area for play or entertaining. Stone patio below, along with an expansive, level, fenced in backyard with your own basketball court. Enjoy your privacy.

38 Charles Unit 38 Winchester, MA 01890

$449,000
3 Beds
1.5 Baths
968 SqFt
Status Active
MLS # 72518011
Property Type Condominium/co-op
Affordable 3 bedrooms 1.5 bathrooms townhouse at The Residences in Winchester! Here is your chance to move into a wonderful community with Top Rated Schools, only a short drive or train ride to Boston. A half bath is located on the first floor, and 3 bedrooms and a full bath on the 2nd. Ability to finish LL with expansion possibility. Private Back yard with accessed from the kitchen. Off-street parking for 2 cars. Low Condo Fee. Short distance to downtown Winchester, schools, hospital, restaurants, shops, etc.

26 Oneida Road Winchester, MA 01890

$899,900
3 Beds
2.5 Baths
2,089 SqFt
Status Active
MLS # 72518463
Property Type Single Family
Welcome home to this wonderful Colonial in the sought after Ambrose Elementary School neighborhood. This sunny 8 room, 3 bedroom, 2.5 bath well cared for home features central air, natural woodwork, an updated kitchen with cherry cabinets, soapstone countertops, fireplace living room, hardwood floors throughout, dining room with built ins and sunroom/office. Extra space abounds in the lower level ~ great for playroom or office. Fabulous outdoor space with deck overlooking spacious backyard, great for entertaining! 1 car garage with a bonus storage area. Nothing to do but move right in!

5 Cutting St Winchester, MA 01890

$789,900 - 3Br/2Ba -  for Sale in Winchester
Open House
$789,900
3 Beds
1.5 Baths
1,271 SqFt
Status Active
MLS # 72517349
Property Type Single Family
Charming move in ready home very close to town and the commuter rail! Gleaming hardwood floors, original details, high ceilings, and abundant natural light from the large windows greet you. There is a stunning modern eat-in kitchen featuring granite counters, SS appliances, and crisp white cabinetry. The sun filled living room is accented by a gas fireplace and statement mantle with built in shelving. Entertain in the formal dining room with elegant wainscoting. A convenient half bath with the laundry completes the main level. Upstairs are the bright master with a walk-in closet and two more bedrooms with an adjacent full bath. Enjoy outdoor living on the large tree shaded side patio. Or relax on the lovely front porch overlooking the green front yard. The exterior was repainted in 2018 and there is a new hot water heater. Move right into this immaculate and charismatic home!

3 Myrtle St Unit 1 Winchester, MA 01890

$549,900
2 Beds
1 Bath
1,075 SqFt
Status Active
MLS # 72517545
Property Type Condominium/co-op
OFFERS DUE TUESDAY AT NOON. This gorgeous first floor condo unit is directly across from Chefalo Park and just steps to all that downtown Winchester has to offer. Walk to the Commuter Rail, schools, restaurants, library, shops, and Middlesex Fells. This coveted location is in the sought after Lincoln school district and offers easy access to I-93 (just 8 miles from downtown Boston). It has just been beautifully and tastefully renovated, including stunning custom cabinetry, new stainless steel appliances, beautifully refinished hardwood floors, in-unit laundry, new AC units, new exterior paint, new roof and systems. Basement has a second laundry and ample dry storage space, or potential to finish for extra living space. This unit comes with one deeded parking space and a private patio in a beautifully landscaped fenced-in yard. This one has it all. Don't miss it!

37 Lockeland Road Winchester, MA 01890

$920,000
4 Beds
2.5 Baths
2,562 SqFt
Status Active
MLS # 72518395
Property Type Single Family
Spacious and sunny oversized Cape situated in coveted west side Winchester neighborhood! Sprawling 4 bedroom 2.5 bathroom home with gleaming hardwood floors throughout. Newly updated gas heating system. Boasting 3 season sunroom overlooking multi level backyard with garden. Located in desirable Vinson Owen school district. Close to historic Wright Locke Farm with hiking trails and conservation land. Enjoy playground and park across the street. Close to Routes 93,95, & 2. Truly a must see!