Winchester Homes for Sale

Winchester Homes for Sale

Welcome to Winchester, a charming city located in Middlesex County, Massachusetts. Known for its picturesque landscapes, rich history, and excellent quality of life, Winchester is a highly sought-after place to call home.

With a population of approximately 22,000 residents, Winchester offers a close-knit community feel while still providing easy access to the amenities of larger cities. Its prime location just 8 miles north of Boston makes it an ideal choice for those seeking a suburban lifestyle with convenient proximity to the city.

Winchester boasts a variety of architectural styles, from historic Victorian homes to modern new constructions. The real estate market in Winchester is thriving, with a range of options to suit different tastes and budgets. Whether you're looking for a cozy single-family home, a spacious townhouse, or a luxurious estate, Winchester has something to offer.

In addition to its beautiful homes, Winchester offers a plethora of recreational activities and amenities. Residents can enjoy the scenic Middlesex Fells Reservation, which provides opportunities for hiking, biking, and picnicking. The city also boasts excellent schools, making it an attractive choice for families.

If you're considering a move to Winchester, now is a great time to explore the available homes for sale. With a real estate market that offers a mix of traditional and contemporary properties, you're sure to find your dream home in this charming New England city.

Newest Winchester Homes for Sale

$2,699,000
4 Beds ⋅ 5 Baths ⋅ 73298854 MLS
Indulge in modern luxury with this 2024 masterpiece, set on a double 1/2 acre lot. This 4 bedroom, 4.5-bathroom home seamlessly blends chic style with an abundance of functional space. The architectural design is dramatic, showcasing soaring ceilings, a stunning contemporary fireplace, state of the art kitchen & sun filled living room which opens to a fabulous deck, creating a perfect indoor-outdoor space. The gourmet kitchen features a sleek design w/ a large island, high end appliances, & stylish open shelving. Upstairs, the lavish primary suite features a spa like bath & large custom closet. The 3 additional bedrooms offer ensuite baths. The walk out LL family room w/ wet bar is the perfect space to unwind. This property also features a 2 gar attached garage, mud room, office & laundry room. The double lot offers many possibilities ~ level w/ patio. This home is located near conservation trails, top-rated schools & Boston offering a lifestyle of convenience, luxury & tranquility!

15 Churchill Road, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
$549,000
3 Beds ⋅ 2 Baths ⋅ 73298552 MLS
Looking for a wonderful hideaway with loads of privacy, well look no further than 20 Seminary Rd. Eight room split level home, built in 1988 on 68acres awaits a new owner. Entry foyer with tile floor, three bedrooms, one full bath, one 3/4 bath, and finished lower level. Living room/dining room combination opens to kitchen with gas cooking and sliders to wraparound deck. Upstairs loft with primary bedroom and storage in the eaves. Hardwood floors, cathedral ceilings, electric heat and central A/C. Family room, office and utility room in the lower level with slider to the back yard. Tract I on deed contains house, garages and 3.10 acres, Tract II contains 64.10 acres. A 60 X 40 (approx) garage with 10 ft and 12 ft garage doors, electric door openers, work benches, 200 amp electrical, heated and A/C with upstairs loft for additional storage. A second garage 34 X 28 (approx) with 10' garage door is unheated/no electric. Private water and sewer, Generac generator.

20 Seminary Rd, Winchester

Listing courtesy of Listing Agent: Carol A. Lenox from Listing Office: Compass.
$1,595,000
3 Beds ⋅ 3 Baths ⋅ 73298334 MLS
Amazing transformation of a Classic Colonial carefully reimagined for today's busy lifestyle. Living room with gas fireplace opens to the family room, oversized hi-end kitchen with island, stainless & granite, dining room with sliders to the yard with a stone patio for outside entertaining, a mud room & 1/2 bath. Upstairs has a primary bedroom suite, bath with 2 separate vanities, walk in custom closet, skylights, & 2 more bedrooms, bath & laundry. The lower level front to back 26' x12' Recreation room has lots of possibilities & also has a home office, closet & large basement storage. Just a short walk along Wedge Pond through Elliot Park be amazed by all Winchester Town Center has to offer with it's mix of bustling quaint shops & trendy restaurants, Commuter Rail just 2 stops to North Station, EV charging station or bike rental, & Packer-Ellis Town Tennis Courts, & let's not forget it's Winchester's award winning schools! *Open houses: Fri & Sat 11-12:30pm, Sun 1-2:30pm (Oct 4,5,6th)

78 Middlesex Street, Winchester

Listing courtesy of Listing Agent: Marjie and Phil from Listing Office: Advisors Living - Arlington.
$3,898,000
6 Beds ⋅ 7 Baths ⋅ 73297360 MLS
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.

20 Amberwood Dr, Winchester

Listing courtesy of Listing Agent: Sino-US Realty Team from Listing Office: Keller Williams Realty.
$2,200,000
4 Beds ⋅ 4 Baths ⋅ 73297163 MLS
Magnificent Brick Colonial, perfectly situated at the end of a quite dead-end street, abutting conservation that offers unmatched privacy and tranquility. The gorgeous, spacious foyer leads into the beautiful front to back living room with a warm and inviting fireplace. The well-appointed dining room with custom built-in China cabinet is perfect for large family gatherings. The chef's kitchen has SS appliances, quartz counter tops and an oversized island with seating. An inviting wet bar leads into amazing family room and another fireplace. Kitchen sliders lead to an expansive deck that overlooks a truly majestic half acre with mature plantings and rolling green lawn. HW floors and decorative molding enhance this gorgeous first floor. Second floor offers 4 large bedrooms and HW floors. The primary's stunning ensuite is all Carrera marble. Lower level offers a game room, playroom, office and full bath. V-O school district, close to Mullen Field and Wright-Locke Farm.

11 Plymouth Road, Winchester

Listing courtesy of Listing Agent: Darryl E. Brian from Listing Office: RE/MAX Bentley's.
$2,250,000
4 Beds ⋅ 5 Baths ⋅ 73296741 MLS
Exceptionally designed & meticulously maintained 2015 Contemporary Colonial. Elegant farmers porch welcomes you into a magnificent layout w/ exquisite mouldings, wainscotting, oak hardwoods, custom fixtures/millwork, & plantation shutters. Spectacular, open-concept main level boasts dual island, granite/stainless chef’s kitchen w/ 2 ovens, butler’s pantry, built-in buffet, walk-in pantry, & abundant cabinetry. Lovely living/dining rm w/charming fireplace, oversized windows, & 10ft ceilings. Easy, walk-out access to 350+ sqft covered mahogany deck overlooking fenced, wooded yard. Home office w/built-ins, full bath, & reading rm complete main level. Upstairs primary bed offers extraordinary dual vanity bath w/ soaking tub + shower, spacious walk-in closet, & built-ins dresser. 3 add’l ensuite beds w/ walk-in closets & laundry rm. Finished bsmt w/ large windows, ½ bath, gym, & sauna. Covered walkout patio w/ firepit, 2 car garage w/ mudrm. Minutes to the Fells, i93/95 & Commuter Rail.

7 Bellevue Ave, Winchester

Listing courtesy of Listing Agent: CS Luxury Group from Listing Office: Keller Williams Realty Boston-Metro | Back Bay.
$2,199,000
7 Beds ⋅ 4 Baths ⋅ 73296573 MLS
*Open house cancelled / offer accepted* Welcome to this wonderful "Flats" home showcasing a beautiful blend of modern finishes & timeless allure. This spacious home boasts 12 rooms, 6/7 bedrooms, 3.5 baths & offers an abundance of space for family enjoyment & fabulous entertaining. The recently renovated kitchen offers custom cabinetry, large center island & top-of-the-line appliances. The craftsmanship showcased here is unique w/ gorgeous woodwork, quarter sewn oak details, beautiful staircase & high ceilings which add a touch of warmth & historic charm to its contemporary upgrades.The oversized dining room w/ nook is breathtaking, the living room w fireplace offers the perfect space for family gatherings. The 2 room primary suite features an updated bath & adjacent dressing room. Enjoy the 1st floor heated sunroom w/ private outdoor entry, an ideal spot for morning coffee or an inspiring home office. A fenced in level yard with patio & garage complete this picturesque home!

33 Oxford Street, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
$2,200,000
4 Beds ⋅ 4 Baths ⋅ 73296209 MLS
Stunning 2006 Colonial, meticulously maintained & decorator-perfect. A grand entry with high ceilings and elegant archways welcomes you into this sun-filled home. The charming living & dining rooms showcase custom details throughout. The gourmet granite kitchen features an oversized island with seating for four, dining area & high-end amenities. A mudroom with ample storage is conveniently located off the kitchen, with sliders leading to a private bluestone patio. The family room offers built-ins & a gas fireplace. Private office with built-ins is tucked off the main hallway with a half bath. Upstairs are 4 bedrooms, including a guest suite with its own bath, plus a laundry room. The serene primary suite offers soothing colors, soft uplighting, and a spacious bath. The lower level includes a media room with a gas fireplace. This exceptional home is in a prime location, close to town, transportation, and Fells Reservation.

18 Town Way, Winchester

Listing courtesy of Listing Agent: Nannette Shanahan from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.
$3,099,000
5 Beds ⋅ 5 Baths ⋅ 73294420 MLS
Welcome to this stunning, brand-new construction in Winchester's most desired neighborhood. This home offers modern luxury and timeless elegance. The custom kitchen features two-toned countertops with a Pegasus marble island and Jet Mist granite perimeter, along with brass accents. The pantry provides for ample additional storage with floor to ceiling cabinets, jet mist counters and a wine fridge. The dining room is adorned with double crown molding and wall detailing. A 1st floor study, a mudroom with custom arched bays, 5 bedrooms, and 4.5 bathrooms provide ample space. The 3rd floor bonus space includes a dedicated bedroom and bath. Enjoy seamless indoor-outdoor living with a professionally designed landscape. Other highlights include checkerboard marble flooring in the laundry room and a custom wallpapered entry room. Coming soon to completion, this home's timeless design, thoughtful details, and modern amenities make it truly one of a kind.

39 Everett Ave, Winchester

Listing courtesy of Listing Agent: Mark Donnellan from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.
$2,249,000
5 Beds ⋅ 4 Baths ⋅ 73294195 MLS
Completely renovated colonial style home on a quiet cul-de-sac within walking distance to downtown Winchester! This home features 5 bedrooms, 3.5 bathrooms and an attached 2 car garage. The first floor offers kitchen, dining, living room and den/study. The flexible first floor also has a bedroom with en suite bath and an office/additional bedroom. Completing the first floor are a half bath and full mudroom. The second floor has 3 generous bedrooms with ample closet space. The primary bedroom has a large walk in closet and spacious bathroom with dual sink vanity. Excellent yard space and back patio for exterior living. Home will be complete towards end of October.

9 S Gateway, Winchester

Listing courtesy of Listing Agent: Mark Donnellan from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.
$2,399,000
5 Beds ⋅ 3 Baths ⋅ 73293355 MLS
Welcome to this stunning English Tudor with incredible curb appeal situated on desirable Wedgemere Avenue! Nestled on a lush oversized lot with gorgeous flowering trees & perennial gardens; this enchanting home has been lovingly maintained & nicely updated inside and out. The first level features a sunny living room w/ beamed ceilings & fireplace, beautiful dining room w/ original woodwork, an updated custom kitchen overlooking the beautifully manicured yard plus a home office, cozy TV room or 5th bedroom, 1/2 bath & sun drenched terrace. The second story includes 4 spacious bedrooms & 2 baths including a guest suite w/ private entry & bath. The lower level offers a family room w/ stone fplc., laundry & storage. Many updates including a newer synthetic slate roof, kitchen, baths, all new windows, updated heating system, central A/C, pristine hardwood floors, w/many unique details & charm found only in older homes. Plenty of expansion potential if you wish with the oversized rear yard.

58 Wedgemere Avenue, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
$2,150,000
4 Beds ⋅ 4 Baths ⋅ 73293157 MLS
UNDER CONSTRUCTION to be completed by 11/24! Desirable 4+ bedroom home w/ thoughtful design & high end finishes! This home is spacious & inviting, offering a grand open floor plan ideal for entertaining & modern day family living. The kitchen features an oversized island w/ seating, quartz countertops, high-end appliances and walk in pantry. Off the kitchen is a spacious family room w/gas fireplace & direct exterior access w/ sliders leading to large deck & nice rear yard. The first floor also offers a formal dining room w/ wainscoting and tray ceiling, a full mudroom w/ closet & bench seat plus a stylish 1/2 bath. The second level primary suite is oversized & very luxurious, offering 2 spacious walk-in closets, a lavish bath w/double vanities, large shower & soaking tub! Three additional beds, full bath & laundry room finish this level. Finished lower level media/ rec rm w/ full bath & plenty of storage. 2 car garage, direct entry to mudroom! Quick & easy access only 7 miles to Boston

LOT 2 Loring Court, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
Start Your Search

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non commercial use of consumers having a good faith interest in purchasing, leasing or renting listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing, leasing or renting. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.