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!

246 Washington Street Unit 246 Winchester, MA 01890

$1,175,000
4 Beds
1.5 Baths
2,660 SqFt
Status Active
MLS # 73159657
Property Type Condominium
Price Type --
Move right in and enjoy this lovely home close to downtown with incredible curb appeal and feel of a single family! You will love to call this great property home, with beautiful flowing first floor, high ceilings & original detail blended with tasteful updates throughout. Spacious bedrooms, updated bath and finished lower level offers a cozy bonus /family room. The lush back yard is private with a lovely yard & patio surrounded by perennial plantings plus a 1 car garage and plenty of parking. Located just minutes away from the towns center, train, restaurants, Fells Reservation and more! Don't miss this sunny & happy home!

9 Upland Rd Winchester, MA 01890

$998,000 - 3Br/3Ba -  for Sale in Winchester
Open House
$998,000
3 Beds
2.5 Baths
1,468 SqFt
Status Active
MLS # 73158950
Property Type Single Family Residence
Price Type --
Welcome to 9 Upland Rd, a beautiful and newly renovated colonial. As you enter the home, you’ll be greeted by the dining room, which flows effortlessly into the renovated white kitchen- featuring stainless steel appliances and an island that separates the two rooms. On your way to the spacious fireplaced living room, you’ll find a half bath with laundry, featuring a new washer and dryer. From the living room, enter the attached study/office space. On the second floor, you’ll find the primary bedroom with a beautifully redone ensuite bath, along with two more large bedrooms and a second renovated bath. The finished lower level has a versatile recreation space, and the level backyard provides the perfect space for outdoor activities.

10 North Gateway Winchester, MA 01890

$2,899,000 - 5Br/6Ba -  for Sale in Winchester
Open House
$2,899,000
5 Beds
5.5 Baths
6,067 SqFt
Status Active
MLS # 73158946
Property Type Single Family Residence
Price Type --
Welcome to the market 10 North Gateway, a stunning new construction property in a neighborhood that everyone in Winchester LOVES! Enter in and immediately be greeted by a gorgeous 2 story foyer with access to your formal living room. The kitchen features an oversized island and is open to the fireplaced family room. A formal dining room with slider to the patio, first floor bed/office with private full bath, pantry, and mudroom with 1/2 bath are also found on this main level. The second floor is home to 4 bedrooms including the expansive primary suite. The finished basement offers a recreation room, gym, a potential 6th bedroom, and full bath! For the outdoor enthusiast, this is where you want to live! Take advantage of the Town Forest being just outside your door for hiking, biking, bird watching, or just a simple after dinner stroll. This property is located less than 1 mile from our beautiful Town Center. Take advantage of an opportunity for a home AND location as special as this!

2 Hillside Ave Winchester, MA 01890

$1,495,000
4 Beds
4 Baths
2,672 SqFt
Status Active Under Contract
MLS # 73155199
Property Type Single Family Residence
Price Type --
Lovely Colonial Revival in pristine condition, located in one of Winchester's most desirable neighborhoods. Close to schools, library, train, downtown and Middlesex Fells. Enter the home through a charming arched porch offering sunset views. Extensively updated, this home features high ceilings, abundant light and classic period details-stained glass window, bullseye moldings, decorative trim and HW floors. The 1st floor open concept floor plan includes a living room with gas fireplace, dining room, kitchen and half bath. Three light filled bedrooms, an office and full bath complete the 2nd floor. The 3rd floor features a private ensuite bedroom with sitting area. The lower-level offers a family room, 2nd office, half bath, laundry and exterior door. The spacious corner lot features a partially fenced yard, mature perennial plantings, majestic beech tree, 2-car garage, paved driveway for 6 cars and rear deck. Enjoy this beautiful home so close to all that Winchester has to offer.

11 Priscilla Lane Winchester, MA 01890

$2,598,000 - 6Br/6Ba -  for Sale in Winchester
Open House
$2,598,000
6 Beds
5.5 Baths
6,323 SqFt
Status Active
MLS # 73159121
Property Type Single Family Residence
Price Type --
Stunning 6 bed, 5.5 bath NEW CONSTRUCTION Colonial. on quiet side st, minutes to Rte 3, I-93, Winchester Center & The Middlesex Fells. Thoughtfully designed with first floor suite style bedroom off main living area plus expansive second floor primary suite. Gorgeous transomed windows welcome sun throughout formal dining room and living room with custom shelving & gas fireplace. Impressive kitchen w/center island, extensive quartz counter space & high-end appliances plus a large walk-in pantry, bev center, home office & 1/2 bth complete this level. 4 Bedrooms on 2nd flr including an expansive primary bedroom suite w/cathedral ceilings, large walk in closet & luxurious bath w/shower, soaking tub & double vanity. Tiled laundry room on this level w/sink & shelving. 6th BDRM on 3rd floor, w/full bth & private sitting room perfect for in-laws or teen suite. Finished lower level w/family room, exercise room, media room & mudroom lead to attached 2 car garage. OH Fri 5:30-7pm, Sat/Sun 1130-1pm

25 Ledgewood Rd Winchester, MA 01890

$5,800,000
7 Beds
4.5 Baths
4,231 SqFt
Status Active
MLS # 73159196
Property Type Single Family Residence
Price Type --
Opportunity abounds on a picturesque estate on a private road 7 miles from Boston and half mile from Winchester’s center. Custom built home on 3 heavily wooded acres and meticulously maintained by one family. This unique offering is an opportunity to create a private family compound or develop the approved 3 separate lots. A winding driveway leads to a mid-century modern masterpiece hidden from the road, offering unparalleled privacy. Floor plan is perfectly suited for entertaining as the large kitchen provides direct views into the family room with built-in bar. Generous dining room and formal living room offer views of the pastoral setting. High ceilings, a main floor study with access to one of 2 patios and en-suite bedroom on the main level. Upstairs 6 bedrooms each with dramatic views of the wooded grounds including owner’s suite with dressing room. Main house sits on over 1.6 acres with two additional lots measuring 0.5 acres each. A special property, looking for its next owner.

1 Orient St Winchester, MA 01890

$1,120,000
3 Beds
1.5 Baths
2,664 SqFt
Status Active Under Contract
MLS # 73159277
Property Type Single Family Residence
Price Type --
Welcome to this recently renovated, charming 3 bedroom 1.5 bath home centrally located in a desirable side-walked neighborhood! Providing the perfect balance of city and suburban living, walking distance to schools, downtown, parks, playgrounds, and the bike path, with easy access to 93 + Commuter Rail. This lovingly maintained home includes an oversized family room with fireplace and attached all seasons porch, perfect for an office, reading room, or play space. The sunny upgraded kitchen features a cozy breakfast nook, while the adjacent dining room and outdoor stone patio offer additional meal and entertaining options. 2nd floor features a king-sized primary bedroom with 2 closets and a roof deck overlooking the beautifully manicured yard, adjacent full bathroom, and 2 more perfectly sized bedrooms. Complete with a finished lower level that has been beloved for family movie nights, and outside offering an enchanting fenced-in yard with mature trees, bluestone patio + attached garage

11 Brooks St. Winchester, MA 01890

$3,099,000
5 Beds
4.5 Baths
5,208 SqFt
Status Active
MLS # 73158209
Property Type Single Family Residence
Price Type --
Embrace elegance, relish a private setting & enjoy one of Winchester's finest neighborhoods! Main level open floor plan showcases a kitchen replete w/luxury ~ Quartz counters, Laurier Max cabinetry, walk-in pantry & the culinary technology of Gagganeau appliances. An expansive LR w/gas fpl & custom built-ins flows into a sunrm surrounded by a canopy of trees & outdoor patio ~ sure to make entertaining exciting! Coffered ceiling & wainscoting details accent the DR plus large windows bring in natural light and the beauty of the outdoors. FIVE spacious bedrms w/built-in closets, incl. 1st FL suite & sumptuous 2nd FL Primary Suite w/vaulted ceilings & rear-facing deck! Family Rm in LL for movie & game nights w/half bath & walkout to outdoor space plus front yard to play hoops or catch. Crafted w/attention to modern desires, nestled in a slice of serenity w/easy access to Town Forest Trails, Commuter Rail, Bus and Winchester's beloved Town Center. Private financing may be available!

27 Brooks Street Winchester, MA 01890

$2,599,000
4 Beds
4 Baths
4,650 SqFt
Status Active
MLS # 73158073
Property Type Single Family Residence
Price Type --
This gorgeous custom home in coveted Brooks neighborhood features a fabulous floor plan with stunning finishes! Thoughtfully designed w/ a dramatic living room featuring vaulted ceilings & floor to ceiling windows w/ fplc, formal dining, open concept sun-drenched kitchen w/ custom cabinetry, chefs applc’s & large island w/seating leading to family room & direct access to glorious fenced yard/patio. A convenient home office space, plus 1/2 bath & direct access to garage w/ lift complete this floor. The striking primary suite boasts vaulted ceilings, a reading nook, large walk in closet and en-suite bath. The 2nd floor includes 3 additional spacious bedrooms, a full hall bath & laundry room. Enjoy working out, movie nights & more in this homes fabulous finished basement incl. a home office w/ built in desks & a half bath. Fenced back yard w/ beautiful bluestone patio, lush landscape & turf area perfect for a play-set or pets! Across from town forest trails & close to town center / train.

18 Forest Street Winchester, MA 01890

$1,399,000
3 Beds
2.5 Baths
2,365 SqFt
Status Active
MLS # 73158206
Property Type Single Family Residence
Price Type --
Welcome to this custom built home w/ a fabulous yard abutting town field/conservation! Stunning open floor plan, ideal for hosting gatherings, seamlessly connecting all of your spaces for modern living! The kitchen is a chefs dream which boasts custom cabinetry, high-end GE appliances, quartz countertops & a generously sized island, perfect for culinary enthusiasts. On the first floor you will also love the private deck off the kitchen, a built in bench / mudroom, the office and half bath. As you ascend up the stunning staircase to the second floor, you'll discover a primary bedroom with beautiful designer bath that features an oversized shower & double vanity w/ a large walk in closet. 2 additional bedrooms, a full bath and 2nd floor laundry complete this level which is all illuminated by a hallway skylight. The versatile lower level with a wet bar is the perfect spot to enjoy a movie, or workout, or both! Located close to town, bike path, popular parks & the train into Boston!

19 Socrates Way Winchester, MA 01890

$3,299,000 - 5Br/6Ba -  for Sale in West Side, Winchester
Open House
$3,299,000
5 Beds
6 Baths
5,678 SqFt
Status Active
MLS # 73156754
Property Type Single Family Residence
Price Type --
ULTIMATE DESIRABLE LOCATION - CUSTOM BUILT HOME - PRISTINE CONDITION - 7 MILES to BOSTON - HALF ACRE LOT - PERFECT FLAT LOT - RARE FIND in WINCHESTER - SPACE for YOUR EVERY DESIRE . Having 14 Rooms - 5+ Bedrooms, 4 Full Bathrooms and 2 Half Bathrooms - 3 floors of finished living space with a magnificent Grand Two-Story Foyer large enough to host your holidays and family celebrations. Lower Level has four spacious rooms - including a large Family/Recreation Room - perfect for a Nanny/In-Law Suite. Professionally landscaped yard and an oversized three-car Garage. Located a short distance to Schools - Winchester Center - Library - Restaurants -Coffee Shops, Town Taverns - Boutiques - Salons and two Commuter Rail stations to Boston. Do not miss this rare opportunity to own a true dream home and become part of the Winchester Community and all it has to offer.

36 Elmwood Ave Unit 11 Winchester, MA 01890

$1,274,000
2 Beds
2.5 Baths
1,573 SqFt
Status Active
MLS # 73155578
Property Type Condominium
Price Type --
SELLER FINANCING AVAILABLE!!!!! Best in class! Loads of upgrades! Introducing an exquisite new condominium that sets the bar for modern luxury living right in Winchester Center. This exceptional penthouse at Allegro boasts a plethora of upgrades, ensuring an unparalleled level of comfort, style, and sophistication. The open-concept layout seamlessly blends functionality and elegance. A gorgeous living room wall has custom wood detailing; designer lighting has been added and custom closet systems installed. Big bonus: custom made plantation shutters on the windows, offering an elegant and expensive upgrade. The kitchen is a chef's dream, with plenty of counter space and sleek appliances. This home offers the very best layout at Allegro, plus it comes with two parking spaces, washer and dryer and extra garage storage. A secure building has an intercom and camera, heated garage and an elevator. Walk to the brand new train, shops, restaurants and come back home to easy living and beauty.

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