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!

6 Cambridge Street Winchester, MA 01890

$2,150,000 - 4Br/4Ba -  for Sale in Winchester
Open House
New
$2,150,000
4 Beds
4 Baths
4,925 SqFt
Status Active
MLS # 73269324
Property Type Single Family Residence
Price Type --
Nestled on Myopia Hill, close to the Winchester Country Club this grand colonial is unparalleled and is an entertainer's dream! Its unique design with large scale rooms caters to both family gatherings and lavish parties. The sun-drenched Great Room, boasting 16ft cathedral ceilings, majestic windows, and a towering stone fireplace is the focal point of this fabulous home w/ French doors leading to a gorgeous stone patio & rear yard. The bright and cheery kitchen overlooking the rear yard offers a casual dining area w/ plenty of cabinetry, w/adjacent mudroom, pantry & 2 half baths. A stunning home office, formal LR w/ fplc, and formal dining w/ 9' ceilings, crown molding & hardwood floors completes this floor. The Primary suite offers a spa like bath, fplc & 2 walk in closets w/ views of the mystic lakes & Boston skyline! 3 additional large bedrooms & full hall bath. Lower level offers a home gym plus kids dream playroom, mudroom & direct entry to oversized 4 car garage!

7 Wainwright Rd Unit 29 Winchester, MA 01890

$1,349,000 - 3Br/4Ba -  for Sale in Winchester
New
$1,349,000
3 Beds
3.5 Baths
3,350 SqFt
Status Active
MLS # 73268672
Property Type Condominium
Price Type --
Imagine coming home to peace and serenity at The Ledges. Perched on a hilltop on the West side of Winchester, this oasis offers tranquility & carefree living. Day-lilies greet you leading to your private sanctuary with gleaming hardwood floors. Fireplace living room with sliders to your private deck. The main bedroom en suite on the first floor. The second level boasts loft, skylit bonus room for a home office, cedar closet, guest bedroom and full bath. The lower level walk-out features natural light, a guest bedroom and a kitchenette for your extended stays guests or entertaining. After tennis or a long walk, unwind by the pool. Perfect for downsizing without sacrificing space, enjoy stunning views throughout the community. The open floor plan with cathedral ceilings enhances spaciousness and light. Customize this home with your personal touch, start living the life you've always imagined. Don’t delay – seize the opportunity to own a piece of The Ledges today!

200 Swanton St Unit 640 Winchester, MA 01890

$285,000 - 1Br/1Ba -  for Sale in Winchester
Open House
New
$285,000
1 Bed
1 Bath
394 SqFt
Status Active
MLS # 73268387
Property Type Condominium
Price Type --
Welcome to your new home in sought after Winchester. This great studio condo offers a perfect blend of comfort and convenience. With 394 square feet of thoughtfully laid-out living space, this unit maximizes every inch to provide a cozy and efficient living experience. The modern kitchen offers ample cabinet space, open living area is spacious and bright, featuring a slider that leads to a private balcony. Building amenities include an inground pool, and a nice area for a picnic and barbecue. Don't miss this exceptional opportunity!

27 Ledyard Rd Winchester, MA 01890

$1,200,000 - 3Br/2Ba -  for Sale in Winchester
Open House
New
$1,200,000
3 Beds
1.5 Baths
2,364 SqFt
Status Active
MLS # 73268304
Property Type Single Family Residence
Price Type --
Discover the endless potential of this charming 3-bedroom, 1.5-bathroom home, perfectly positioned on a sought-after Winchester lot with excellent frontage and a generously sized yard. The finished lower level features a convenient walkout to a private backyard, creating additional living space and ample opportunities for outdoor enjoyment. This property presents a fantastic opportunity for a full renovation or teardown, allowing you to design and construct your dream home from the ground up. Situated near top-tier schools, a variety of convenient amenities, and the scenic Middlesex Fells Conservation area, this location offers the best of both worlds—serenity and accessibility. Don't miss the chance to create a custom living space in a prime location that caters to your lifestyle and preferences. Embrace this unique opportunity to bring your vision to life and make this desirable Winchester address your own.

6 Robinson Park Winchester, MA 01890

$4,299,000
5 Beds
4.5 Baths
6,900 SqFt
Status Active
MLS # 73264918
Property Type Single Family Residence
Price Type --
Stunning Waterfront Estate on Upper Mystic Lake! This exceptional 5-bedroom, 4.5-bathroom home features a brand new chef's kitchen, a spacious family room with high ceilings, a gas fireplace, built-ins, and direct access to a stone patio overlooking a fenced-in level yard with a private dock. Enjoy breathtaking lake views from nearly every room of this beautifully crafted estate. Designed for seamless entertaining, the main level leads into a versatile walk-out lower level, perfect for a home gym, office, or media room, complete with ample storage. The second floor boasts a luxurious primary suite and three additional corner bedrooms, providing an ideal family living environment. This home combines luxury with a tranquil setting, making it ideal for both peaceful family life and vibrant gatherings. Just minutes from Boston, this property offers a rare opportunity to own a spectacular waterfront estate that truly has it all!

7 Thornberry Road Winchester, MA 01890

$1,559,900 - 5Br/2Ba -  for Sale in Winchester
Open House
$1,559,900
5 Beds
2 Baths
3,033 SqFt
Status Active
MLS # 73263803
Property Type Single Family Residence
Price Type --
Welcome to this newly renovated contemporary home, nestled in the highly sought-after West-side neighborhood with surprising space! This 3+ level home boasts 4-5 spacious bedrooms and 2 full stylish baths, this home offers versatile space for multiple home offices, in law/ au-pair space plus comfortable family spaces all great for entertaining. The main level features a beautiful open-concept kitchen w/ high end appliances & quartz counters w/ island seating, adjacent dining w/ soaring ceilings, step down the living room w/fplc & walls of glass overlooking large lot w/ patio & fire pit. 4 spacious BR's plus finished LL perfect family/playroom, plus BR #5 or office. Enjoy the convenience of a 2-car garage and additional driveway parking, with ready connections for EV's. Located just minutes from top-rated schools, parks, conservation land, shopping, and a variety of dining options, this home offers the best of suburban living with easy access to downtown Boston in just 15 min! Must see!

7 Ardley Road Winchester, MA 01890

$1,799,000
4 Beds
3.5 Baths
3,143 SqFt
Status Active
MLS # 73262706
Property Type Single Family Residence
Price Type --
Uniquely charming and beautifully landscaped four bedroom Colonial on an oversized lot sited in a cul-de-sac neighborhood. Originally built in 1939, it was vastly expanded in 1998, by the current owners, to the current floor plan in a renovation that also preserved architectural details of the original cottage. Some of the features include first floor family room with sliders leading to backyard patio, and custom built-ins flanking a gas fireplace; private primary suite on second floor with vaulted ceilings, window seat, sitting area, built-ins, and large bath with soaking tub and separate shower; and skylit dining room with beamed cathedral ceiling and pretty views to side yard and s/he shed, along with sliders leading to a second patio. Amenities include 2-car garage, updated HVAC, freshly painted interior, and fireplaced rec room in lower level. Wonderful location just a block from an elementary school (currently being rebuilt,) close to a bike path, Horn Pond, and hiking trails.

10 Briarwood Ln Winchester, MA 01890

$2,599,000
6 Beds
5.5 Baths
5,171 SqFt
Status Active Under Contract
MLS # 73262529
Property Type Single Family Residence
Price Type --
Experience the perfect blend of nature and luxury in this custom-built Colonial! Private home with a resort like backyard abuts Brooks Parkhurst Town Forest. This stunning 6-bedroom home offers a dramatic layout and design that's sure to impress. A elegant & captivating buttress staircase greets you upon entry. The heart of the home is an updated open-concept kitchen, complete with pantry & half bath, which flows seamlessly into the family room featuring a cozy fireplace & an adjoining sunroom. The formal living room transitions smoothly into the dining room, offering a versatile space ideal for entertaining guests. Home office provides a perfect setting for focused work. The primary w/ en-suite is a luxurious haven, boasting a cathedral ceiling, fireplace, & 2 walk-in closets. Additional 5 bedrooms & 3 full baths complete upper levels. Lower level includes media room, gym, home office & full bathroom. Don't miss this unique blend of privacy, luxury, and nature in a premier location!

9 Brooks Street Winchester, MA 01890

$2,499,000
4 Beds
2.5 Baths
4,278 SqFt
Status Active
MLS # 73262863
Property Type Single Family Residence
Price Type --
Stunning home in wonderful Brooks neighborhood convenient to Commuter Rail, town center, walking trails and Fells. All living space is above grade with huge potential to finish basement as your heart desires. Kitchen, bathrooms RENOVATED by current owners with attention to details. You'll love how the kitchen eating area is the perfect spot to hang out adjacent to the family room with fireplace and access to the lovely deck that fits a dining table. Up a few steps, you'll find the great room with custom built-ins with plenty of space for movie nights and games. Need a home office? Got that. Formal LR and DR complete the first floor. Upstairs the main bedroom boasts a luxurious bath with soaking tub, tiled shower, storage and a private water closet. 3 additional bedrooms, all with double closets, share a hall bath next to a terrific laundry room. Other details include custom shades on many windows numerous built-ins. Step inside and fall in love with this beautiful home!

50 Lake Street Unit I Winchester, MA 01890

$669,000 - 2Br/2Ba -  for Sale in Winchester
Open House
$669,000
2 Beds
1.5 Baths
1,461 SqFt
Status Active
MLS # 73262932
Property Type Condominium
Price Type --
Brick townhouse in desireable downtown location situated on Wedge Pond! Watch the swans float by from your patio as you enjoy the tranquil setting and gorgeous view! Recently renovated kitchen with island peninsula; full dining room with bow window, 13 x 18 living room (and master bedroom), 2 Bedrooms; 1.5 Baths; spacious family rm (or home office), extra storage in basement and/attic, in unit laundry, lots of closet space. One deeded parking space - 2nd space available for rent - $40 monthly. Walk to shopping, public transportation, tennis, Farmers' Market and many fantastic restaurants. Easy access to Rts. 93 and 95/128. Commuter rail to Boston. Come see all that Winchester has to offer in addition to their fabulous school system (New Lynch elementary school to open in 2025!) Open House Saturday and Sunday 12-2pm - call for private showings. Small dog OK - No smoking. All offers, if any, due by 5pm Tuesday - July 16th.

20 Amberwood Dr Winchester, MA 01890

$3,988,000
6 Beds
7 Baths
8,866 SqFt
Status Active
MLS # 73261491
Property Type Single Family Residence
Price Type --
Stunning 8800 sq ft brand-new contemporary in one of Winchester's favorite neighborhoods. A gracious foyer w/ high ceiling welcomes you to this elegant home loaded with natural light and architectural detail. Custom features include a gourmet eat-in kitchen w/ granite countertops, high-end appliances, secondary prep area, and fabulous outside dining options from the oversized deck. The spacious fire-placed family room, banquet-size dining room w/ wine-column, private home office and bedroom w/ en-suite bath complete the first floor. Luxurious primary suite w/a large balcony, expansive walk-in closets & spa-like bath w/ dual vanities, an oversized shower, and a lavish soaking tub on upper level, along w/ 3 additional en-suite bedrooms and an oversized laundry room. Finished lower level features additional entertainment areas, gym & en suite-bedroom. Fantastic location just up the hill from top-rated Vinson Owen School. Enjoy all that Winchester has to offer.

253 Pond St Winchester, MA 01890

$1,199,000 - 3Br/2Ba -  for Sale in Winchester
Open House
$1,199,000
3 Beds
1.5 Baths
1,788 SqFt
Status Active
MLS # 73260439
Property Type Single Family Residence
Price Type --
Opportunity is Knocking! Attention savvy buyers and investors looking to bring their updates and personal style and make this custom one owner ranch style home their own in the much-anticipated brand new Lynch Elementary School District. You will surely appreciate the large scale of this home with a beautiful fireplace and mantel, hardwood floors and custom moldings throughout. This home flows wonderfully with kitchen, dining room complete with a custom cabinet and a family room all connecting to the super-sized living room and 3 generous bedrooms all on one floor. Additionally, the attic is partially finished with stairs, electric heat and hardwood floors. Complete this project and you can enjoy 2 additional bedrooms or home office and media room. The picturesque backyard oasis includes a 20x40 inground pool which will surely be enjoyed in this beautiful private setting abutting the Lynch School field. Very convenient location and right across the coveted Horn Pond Recreation Area.

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