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!

* Separate multiple values with comma.

Sort by:

71 Myopia Road Winchester, MA 01890

$1,749,000 - 4Br/4Ba -  for Sale in Myopia Hill, Winchester
New
$1,749,000
4 Beds
4 Baths
3,951 SqFt
Status New
MLS # 72350473
Property Type Single Family
ATTENTION WINCHESTER AFICIONADO'S: Do we have the home for you! Available for the first time in more than 45 years! Nestled in ever so nicely on its wooded and oversized lot is this 4 bed, 4 full bath home located in the highly acclaimed Myopia Hill. Imagine homeownership on one of the finest streets that Winchester has to offer. Within walking distance to the prestigious Winchester Country Club, this property will lure you in from moment one. Enter in to the main level which boasts a new kitchen, beautiful formal dining room with built ins, sunroom beaming with natural light from every angle, a fireplaced family room, a fireplaced library, AND the first of two master suites. Want MORE? The second level provides two beds that share a bathroom and a second master suite. The lower level, walk out, recreation room with bar area and additional fireplace is the icing on the cake to this amazing home. Come see how you can live everyday as if you were in a private retreat here at 71 Myopia.

11 Hutchinson Rd Winchester, MA 01890

$2,150,000 - 6Br/6Ba -  for Sale in Winchester
New
$2,150,000
6 Beds
5.5 Baths
5,939 SqFt
Status New
MLS # 72350177
Property Type Single Family
Gorgeous family home located in Winchester by the Winchester country club and the Vinson Owen School District. This home is meticulously cared for and looking for a large family to call it home. This home features stunning cherry floors throughout the 1st & 2nd floor. The first floor consists of an office/den, dining room, large open concept kitchen that flows to the eating area and family room. The second floor houses a large master suite w/ master bath and two walk-in closets, two large bedrooms, laundry room and bathroom. The Au Paire Suite is quite large with it's own sitting area, work space and full bath. The third floor is fully finished with two more bedrooms and a full bath. The basement is nicely finished with a great work out area, kids game room and classroom/office area with a full bath to finish it off. Don't miss the 3 car heated garaged for those car enthusiasts. The backyard is HUGE! Half acre just ready for an in-ground pool to finish it off......

983 Main St Unit 983 Winchester, MA 01890

$724,900 - 3Br/3Ba -  for Sale in Winchester
New
$724,900
3 Beds
2.5 Baths
1,815 SqFt
Status New
MLS # 72349265
Property Type Condominium/co-op
Welcome to a move-in ready & low-maintenance, freshly painted 3 bed/2.5 bath newer townhouse! The open concept 1st floor living, dining & kitchen area features hardwood floors, large windows & high ceilings. Wooden staircase leads to the large master bedroom & master bath with double vanities & walk-in closet, a bonus bay window allows for lots of natural light. 2nd floor includes a 2nd bedroom, full bath and balcony access. The 3rd floor has a study area and 3rd bedroom with French doors, two walk-in closets, skylight & additional storage. Benefit from a finished basement with large family room & a mudroom space off the attached garage. Enjoy the comfort of central heat & AC and tankless hot water heater. A private backyard patio is perfect for BBQs and entertaining, and balcony and front porch allow for additional outdoor space. Located less than 1/2 a mile to Lynch Elementary and Horn Pond, approx. 1 mile to Winchester Center, middle & high schools, and train, & near major highways.

1 Woodside Road Winchester, MA 01890

$1,349,000 - 6Br/4Ba -  for Sale in Flats, Winchester
Open House
New
$1,349,000
6 Beds
3.5 Baths
3,690 SqFt
Status New
MLS # 72349385
Property Type Single Family
Welcome to the Flats! Beautiful 1895 Colonial on a 12,000sqft lot, just 1mile from the town center. Private and serene back yard with a blue stone patio and new 6ft cedar fence located directly off the kitchen. Sprinkler system and NEW 2-car garage with a 22x14 2nd floor just waiting for your imagination to finish. An inviting front porch opens into the grand foyer with a classic staircase. Bright, sun-drenched double parlor with lovely built-in details. Formal dining room, kitchen with granite counters/island, gas stove, stainless steal appliances and half bath complete the 1st floor. The second floor offers a master bedroom with new wood floor, walk-in closet, beautifully updated master bath, three additional bedrooms and large family bath. Third floor is wonderful space with full bath, 2 bedrooms and ample storage. The partially finished lower level is great flex space with even more storage options. Great home in a fantastic location...come enjoy all Winchester has to offer!

7 Wainwright Road Unit 58 Winchester, MA 01890

$999,000 - 3Br/3Ba -  for Sale in Winchester
Open House
New
$999,000
3 Beds
3 Baths
2,900 SqFt
Status New
MLS # 72349598
Property Type Condominium/co-op
Welcome to The Ledges town home community. Winchester's most desirable town home complex surrounded by nature and mature landscape. This unit has been meticulously maintained and has a lovely front yard. Hardwood floors on the first floor with doors leading to the deck from the fireplace living room. Open floor plan for easy living and entertaining. Updated Kitchen with a bright and lovely eat in Area overlooks your garden. Dining room opens to Living room for easy entertaining. 1st floor master bedroom has cathedral ceilings, spacious bath and 2 walk-in closets, additional Bedroom on the 1st floor and a full Bath with Tub and Shower. 2nd floor has a loft ideal for home office or media room. 3rd bedroom with bath allows privacy for your guests or extended family. Lower Level is a walk out, consists of a Family Recreation Room with Sliding glass doors, and a finished Bonus Room with a spacious closet. Large Storage area with built ins. Open House Sunday 11-1.

4 Rangeley Ridge Winchester, MA 01890

$1,049,000 - 3Br/2Ba -  for Sale in Winchester
Open House
New
$1,049,000
3 Beds
1.5 Baths
1,884 SqFt
Status New
MLS # 72349904
Property Type Single Family
A superb residence situated in the heart of downtown Winchester that is impeccably decorated & designed to the highest standard on an absolutely exquisite 18,0000 sq ft lot with garage parking! This home offers 3 bedrooms, 1.5 baths & is perfect for today’s busy lifestyle. Outstanding architectural detail, materials & finishes are displayed inside & outside this absolutely magnificent home. Main level offers a traditional colonial style layout with beautifully appointed eat in kitchen overlooking the spectacular fenced in rear yard including a brick patio with steps down to a terraced garden with mature plantings & seasonal views of town from this esteemed “Rangeley” neighborhood; a fireplaced living room; formal dining room; sunny home office & half bath. The 2nd floor is adorned with 3 corner bedrooms, a well appointed full bath & plentiful closets. Walk to town, commuter rail, schools, restaurants & all downtown has to offer. Absolutely turnkey!

18 Chester St Winchester, MA 01890

$1,288,000 - 6Br/4Ba -  for Sale in Winchester
Open House
New
$1,288,000
6 Beds
3.5 Baths
2,943 SqFt
Status New
MLS # 72348257
Property Type Single Family
Just Listed! First Open House this Sunday from 11-12:30. Luxury Colonial Style Home located on a quiet tree lined street just a short distance to Winchester Center, Town Schools, MBTA Commuter Rail & Middlesex Fells Reservation. You'll love the Spacious Open Concept first floor as it features an Amazing Chef's kitchen with lots of Natural Light, Frigidaire SS Appliances and Granite Counters! With 3 levels of living this home does not disappoint as there is room for everyone!

203 Highland Avenue Winchester, MA 01890

$979,000 - 4Br/3Ba -  for Sale in Winchester
Open House
New
$979,000
4 Beds
3 Baths
2,152 SqFt
Status New
MLS # 72349022
Property Type Single Family
Charming Farmhouse style home within walking distance of Town Center, Schools, Commuter Rail, Middlesex Fells Reservations, and amenities! This bright and sunny property offers many features that are sure to appeal to today's buyers: beautifully remodeled kitchen with granite countertops & stainless appliances, generous master bedroom suite with a fireplace and ensuite bath, a home office/study on the 2nd floor, 3 full bathrooms, Central AC, tasteful lighting, lovely hardwood floors, 1st floor laundry, ample closets, and much more. The 4th bedroom/Family Room on the 1st floor adds flexibility of living arrangements. The landscaped backyard, front porch, and 1-car attached garage complete the setting for this picturesque property located on a large corner lot. Convenient access to the highways allows for ease of commuting. Open House Saturday & Sunday: 12-1:30 pm.

185 Mystic Valley Pkwy Winchester, MA 01890

$749,900 - 4Br/2Ba -  for Sale in Winchester
Open House
$749,900
4 Beds
1.5 Baths
1,449 SqFt
Status Active
MLS # 72347765
Property Type Single Family
With its premier downtown location, enjoy all that Winchester has to offer just out your front door! Beautifully situated on a picturesque, tree lined street, the home is just minutes from Winchester’s Victorian downtown’s shops and restaurants, award-winning schools, and Commuter Rail station. Built in the 1850s, this historic Colonial features high ceilings, wide pine flooring, and newer windows. This is the perfect opportunity for a savvy buyer to modernize and restore the property to its original glory. Enjoy summer barbecues on the secluded backyard patio and near-limitless outdoor activities are yours to explore in the Middlesex Fells Reservation. A unique opportunity to own a special home.

20 Mason St Winchester, MA 01890

$1,299,000 - 4Br/5Ba -  for Sale in Winchester
Open House
$1,299,000
4 Beds
5 Baths
2,853 SqFt
Status Active
MLS # 72348031
Property Type Single Family
Welcome to 20 Mason St, Winchester. This stunning colonial, circa 1928 has been beautifully, meticulously and expertly expanded, updated and renovated. Featuring a new kitchen addition with quartz and walnut counters, black stainless steel appliances and custom cabinetry.From here the new deck, portico and garden are easily accessed.The front to back living room is the perfect gathering space with a wood burning fireplace and original mill work restored to perfection. On the 2nd level the Master bedroom has a beautiful new en suite bath with heated marble floors and dual head tile shower. New custom closets complete this lovely suite. On this level there are 2 other bedrooms and a family bath. Upstairs on the 3rd level there is a home office, another full renovated bath and the 4th bedroom. Perfectly landscaped to embrace the natural woodland setting, this lovely property is close to the town center, commuter rail, Lincoln Elementary and McCall Middle School.

4 Ravine Road Winchester, MA 01890

$2,499,000 - 5Br/7Ba -  for Sale in Winchester
Open House
$2,499,000
5 Beds
7 Baths
6,032 SqFt
Status Active
MLS # 72348070
Property Type Single Family
UNBEATABLE LOCATION, SITUATED IN THE HEART OF DOWNTOWN WINCHESTER!!! Enter into the dramatic 2-story foyer featuring one of three Swarovski Crystal Chandeliers! Host a dinner party in the Chefs kitchen boasting granite counters, a 48SUBZERO refrigerator, a 60gas WOLF range & 2 BOSCH dishwashers. Step out into the pristine garden with built in BBQ and outdoor pizza oven! The dining room has built-in china cabinets, a fireplace and is surrounded with beautiful windows. 5 bed suites, each w/private bath. A Master bed fit for a King & Queen! Seamless flow throughout provides unparalleled luxury living on 4 levels. Gorgeous media room on lower level, featuring a home theatre and bar. Newly finished hardwood floors , and many rooms recently painted. Walk to the farmer's market on the common and explore Winchester's boutiques, restaurants & coffee shops or take the commuter rail to North Station for a day in the city. Within the Ambrose school district and 7 miles North of Boston.

26 York Rd Winchester, MA 01890

$1,350,000 - 4Br/4Ba -  for Sale in Winchester
Open House
$1,350,000
4 Beds
4 Baths
4,375 SqFt
Status Active
MLS # 72348139
Property Type Single Family
A spacious Colonial on a cul-de-sac in a sought after neighborhood within the Ambrose school district! This updated/expanded home is perfect for every lifestyle and wonderful for entertaining, especially by the pool in the summertime! The first floor boasts a step down Living Room and Dining Room, a wonderful Kitchen with an island, skylight, fireplace and dining area overlooking a patio and the pool. A bedroom, full bath and a bedroom with en suite and walk in closet complete this floor. Walk upstairs to a Master Bedroom with en suite, walk in closet and office/nursery as well as a dressing room/home office and additional bedroom. The lower level, with garage access, offers tiled playroom/family room space, laundry and a full bath. Enjoy hardwood floors throughout, central air, newer systems and roof in a location 1.3 miles from the shops and restaurants of Winchester Center, close to Wedgemere Commuter Rail Station and Rte 93. Must see! Open Houses Sat 6/23 & Sun 6/24 1-2:30