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!

26 Swan Road Winchester, MA 01890

$4,399,000 - 6Br/7Ba -  for Sale in Myopia Hill/ Winchester Country Club Area, Winchester
New
$4,399,000
6 Beds
6.5 Baths
8,463 SqFt
Status Active
MLS # 73344473
Property Type Single Family Residence
Price Type --
Nestled in the heart of Myopia Hill, this custom-built home is sure to impress! Live your best life at 26 Swan Road offering 6 bedrooms, 6.5 bathrooms with a first floor primary suite. This magnificent residence boasts expansive living spaces, elevator & indoor pool! Exquisite craftsmanship is shown throughout this home including a newly renovated gourmet kitchen w/custom cherry cabinetry & high end appliances leading to adj. family room w/ fireplace. A handsome library w/ fireplace offers a warm and inviting space to relax. The highlight of this extraordinary home is the 16x32 indoor freshwater pool & jacuzzi set within a breathtaking atrium room w/soaring vaulted ceilings, perfect for year round exercise and entertainment. Each of the spacious bedrooms provides a retreat-like atmosphere, complete w/ensuite baths for ultimate comfort & privacy. The home also features 4 fireplaces, 2 home offices, a newly finished 3 room basement w/ rec room, fplc, BR & full bath, plus 3 car garage.

74 Hillcrest Parkway Winchester, MA 01890

$2,498,000 - 5Br/4Ba -  for Sale in Winchester
Open House
New
$2,498,000
5 Beds
4 Baths
4,468 SqFt
Status Active
MLS # 73344253
Property Type Single Family Residence
Price Type --
Introducing 74 Hillcrest Parkway! This spacious, modern 5-bedroom home is nestled across the breathtaking Middlesex Fells Reservation on one of Winchester's most picturesque streets! First floor seamlessly blends living, dining, & kitchen areas. Living room has wood burning fireplace & custom built-in shelves. Dining room offers delightful space for cozy gatherings and the spacious eat-in kitchen has french doors to wooded back yard & oversized stone patio. Above the garage a huge family room with vaulted ceilings & fireplace. 2nd fl has 4 bedrooms incl. a tranquil primary suite w/ private deck. Completing this serene suite is a custom designed walk in closet, spa-like bath w/ double sink vanity, a brand new soaking tub, and double shower. 5th br on 3rd floor. Lower level has additional family room w/gas fireplace, and storage room w custom cabinets.Enjoy all that Winchester has to offer while coming home to this true gem of a home - this is the market offering you've been waiting for!

29 Allen Rd Winchester, MA 01890

$1,599,000 - 4Br/3Ba -  for Sale in Winchester
Open House
New
$1,599,000
4 Beds
2.5 Baths
2,810 SqFt
Status Active
MLS # 73343610
Property Type Single Family Residence
Price Type --
This expanded 4-bedroom, 2.5-bath colonial is a true gem in the heart of a serene Lincoln School neighborhood. Impeccably maintained by the same family for over 40 years, this home has been thoughtfully updated w/ modern comforts, incl. AC throughout. The 1st floor features a remodeled kitchen w/ stainless steel appliances, granite countertops & breakfast bar, flowing into a spacious family room w/ sliders to a sunny deck. An elegant dining room w/ two china cabinets & formal living room w/ fireplace & french doors offer ideal entertaining spaces for your largest gatherings. Upstairs, the generous primary suite boasts high ceilings, radiant heat, arched windows, dual walk-in closets & a full bath. Three additional bedrooms & a full bath provide abundant space. The partially finished basement w/ fireplace offers endless possibilities. Enjoy a heated garage, fenced backyard area & charming covered porch. This turnkey jewel is convenient to Symmes Corner, commuter rail, & town center.

261 Cambridge St Unit 261 Winchester, MA 01890

$1,299,000
3 Beds
2.5 Baths
2,705 SqFt
Status Active
MLS # 73342258
Property Type Single Family Residence
Price Type --
Step into this beautifully renovated historic townhouse that seamlessly blends classic charm with modern updates. This welcoming 3-bedroom, 2.5-bathroom home features elegant finishes, high ceilings and thoughtful details throughout. The main level boasts an open kitchen/family room plan, plus a large dining room and living room, great for entertaining. Upstairs, you'll find generous bedrooms, including a master suite with a walk-in plus 2 additional closets & full bath. The finished 3rd floor adds versatility, offering the perfect space for an office, playroom, or additional living area. The large, unfinished basement with high ceilings presents endless possibilities for customization or additional living space. Enjoy the convenience of a 2-car tandem garage, providing plenty of parking and storage space. Relax and unwind on the patio, or take a stroll through the nearby walking trails. Enjoy the convenience of condo living in a unit that lives like a single family home!

31 Coolidge Road Winchester, MA 01890

$2,049,000
4 Beds
4 Baths
4,650 SqFt
Status Active
MLS # 73342076
Property Type Single Family Residence
Price Type --
Set against a serene woodland backdrop, this beautifully maintained colonial blends formal spaces with open, airy rooms designed for both grand entertaining and cozy everyday living. In the foyer, a staircase is flanked by the dining and living rooms on either sides. The kitchen, with center island and full dining area, flows into a showstopping family room that transitions to a private office with cathedral ceilings. United by a dual-sided fireplace, these rooms are highlighted by floor-to-ceiling windows, French doors, and skylights, which flood the space with natural light. The second floor offers four bedrooms and two bathrooms, including a fabulous primary suite. The ultimate game room awaits in the finished basement with endless room for recreation and fun- complete with a wet bar, storage, and full bath. Striking stone walls, a welcoming porch, and refined landscape lighting give way to a sprawling back patio surrounded by lush, mature greenery in a secluded picturesque setting

261 Cambridge St Unit 261 Winchester, MA 01890

$1,299,000
3 Beds
2.5 Baths
2,705 SqFt
Status Active
MLS # 73342253
Property Type Condominium
Price Type --
Step into this beautifully renovated historic townhouse that seamlessly blends classic charm with modern updates. This welcoming 3-bedroom, 2.5-bathroom home features elegant finishes, high ceilings and thoughtful details throughout. The main level boasts an open kitchen/family room plan, plus a large dining room and living room, great for entertaining. Upstairs, you'll find generous bedrooms, including a master suite with a walk-in plus 2 additional closets & full bath. The finished 3rd floor adds versatility, offering the perfect space for an office, playroom, or additional living area. The large, unfinished basement with high ceilings presents endless possibilities for customization or additional living space. Enjoy the convenience of a 2-car tandem garage, providing plenty of parking and storage space. Relax and unwind on the patio, or take a stroll through the nearby walking trails. Enjoy the convenience of condo living in a unit that lives like a single family home!

19 Rangeley Rd Winchester, MA 01890

$4,799,000
5 Beds
7 Baths
7,779 SqFt
Status Active Under Contract
MLS # 73341968
Property Type Single Family Residence
Price Type --
A treasure. That's how this residence is viewed, throughout town, throughout the decades. One family had the vision to bring this cherished home back to life with a renovation that bestowed the best of everything. On Rangeley Road, gentle rolling lawns fold softly into a private, winding road. Gorgeous architecture graces every lot and ancient oaks stand sentry. Located just steps to the town center, you feel like you're a world away. This home is equally unlike anything else. Details abound, ceilings soar and it's simply breathtakingly beautiful. An extraordinary top of the line kitchen with marble counters and a walk in pantry opens to a cozy family room with a gas fireplace. Relax in a huge media room; there's also a custom bar & wine room, a home gym plus a full bath, sauna and steam shower. There are two home offices, a primary suite unlike any other and a newly built two-car garage. Plus, there's a wrap-around porch and an Artesian well for watering the spectacular grounds.

18 Pine Grove Park Winchester, MA 01890

$975,000
3 Beds
2 Baths
2,873 SqFt
Status Active Under Contract
MLS # 73342281
Property Type Single Family Residence
Price Type --
Beautifully maintained one owner Cape, ideally located near Winchester Center. Nestled on a neighborhood street, with Horn Pond, bike paths, local schools, commuter rail, & downtown shops just moments away, this home offers a terrific location. Three bedrooms, two full baths, with a bonus room offer flexibility and space to make it your own. Gleaming hardwood floors throughout, with built-ins in the bedrooms and dining room, Garage under. Close to major highways.

8 Chestnut St Winchester, MA 01890

$2,999,000 - 5Br/6Ba -  for Sale in In Town Location, Winchester
Open House
$2,999,000
5 Beds
6 Baths
5,354 SqFt
Status Active
MLS # 73342518
Property Type Single Family Residence
Price Type --
Newly constructed 5,366 sq ft luxury home with attached 2 car garage! Featuring 5 bedrooms, 4 full and 2 half bath, and 4 levels of living, discover thoughtful elegance at every turn . The designer kitchen offers high-end appliances including a gas stove, double oven, and wet-bar with beverage fridge. Featuring an open-concept, the kitchen effortlessly flows into the sun-drenched living and dining areas, with home office, first floor bedroom, and large mudroom nearby. Ascend to the 2nd floor to find the spacious primary suite with walk-in closet, stunning bath with soaking tub, and attached deck, along with 3 other bedrooms and laundry. The 3rd floor features a bonus room with 1/2 bath, along with additional flexible space in the finished basement. Outside, the beautifully landscaped yard with cozy fire pit and patio creates the ultimate oasis. Winchester center and commuter rail less than 1 mile away. Don’t miss the chance to make 8 Chestnut home!

79 Sylvester Ave Winchester, MA 01890

$869,900
3 Beds
2 Baths
1,469 SqFt
Status Active Under Contract
MLS # 73341343
Property Type Single Family Residence
Price Type --
Discover where form meets function in this beautifully maintained home, ideally located near Winchester Center. Nestled on a neighborhood street, with Horn Pond, bike paths, local schools, commuter rail, & downtown shops just moments away, this home offers a quintessential location. Thoughtfully updated, the kitchen, exterior, and bedrooms reflect pride of ownership, showcasing care and attention to detail. Sunlight pours through bay windows into the separate office, offering a bright and welcoming workspace. The updated kitchen, featuring sleek stone countertops, stainless steel appliances, and ample cabinetry, flows seamlessly into the dining room. Step outside to your spacious deck & patio, set within a private, fenced-in yard. Three well-appointed bedrooms, two updated full baths, and a finished bonus room offer flexibility and space to make it your own. Enjoy proximity to Winchester's best—all set within a charming, tree-lined neighborhood.

12 Prospect St Winchester, MA 01890

$3,199,000
7 Beds
5 Baths
6,694 SqFt
Status Active
MLS # 73340671
Property Type Single Family Residence
Price Type --
Exuding elegant luxury, this fully renovated Victorian boasts a carriage house and extraordinary grounds, in one of Winchester’s most coveted neighborhoods! A show-stopping chef's kitchen boasts state-of-the-art Thermador appliances, wine tower, 42'' fridge, a 6-burner gas range, a quartzite island with seating for 4, & a breakfast nook overlooking a beautifully landscaped large yard with rock walls, perennials, and gardens. The graceful interior includes a casual sitting area/den with a beverage bar and wine fridge, a formal dining room with double crown moldings, wainscoting, 2 chandeliers, and a bay window seating area. One of the most beautiful rooms is the formal living room, with a large fireplace and oversized windows that allow it to flood with natural light. The family room is also flanked by large windows & built-ins. The newly rebuilt front porch provides enough room for outside dining & seating. The carriage house has an upper-level loft plus it can accommodate 3 cars.

88 Arlington Street Winchester, MA 01890

$2,399,000
5 Beds
3.5 Baths
4,097 SqFt
Status Active
MLS # 73341084
Property Type Single Family Residence
Price Type --
Welcome to this warm & inviting home nestled amidst the serene landscapes of the Winchester Country Club. A Royal Barry Wills design, showcasing 5-beds, 3.5-baths, w/4 fireplaces & attached direct entry 2 car garage! This home has w/ an abundance of charm in every room; the spacious living areas are warm and inviting & flooded with natural light, showcasing original woodwork & oversized wood burning fireplaces. The updated custom kitchen has vaulted ceilings w/ arched window showcasing views of the Country club & perennial gardens; the kitchen is an absolute delight and the heart of the home. Each of the 5 bedrooms are spacious w/ great closets incl. the primary suite, with luxurious en-suite bath, offering a private retreat w/ soaking tub & tiled shower. Lower level features a cozy family room w fplc, gym, storage and full bath. Outside, the glorious fenced yard w/ mature perennial gardens & scenery of the Winchester Country Club is sure to impress. This is a one of a kind home!

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