Winchester Real Estate

Winchester Real Estate

Winchester: A Charming Town in Middlesex County, Massachusetts

Nestled in Middlesex County, Massachusetts, Winchester is a picturesque town that offers a perfect blend of small-town charm and urban convenience. Known for its beautiful neighborhoods, excellent schools, and close-knit community, Winchester is a highly sought-after place to call home.

With its prime location just eight miles north of downtown Boston, Winchester provides residents with easy access to the city's vibrant cultural scene, renowned universities, and job opportunities. Commuting is a breeze, thanks to the town's well-connected transportation system, including nearby highways and commuter rail stations.

Winchester boasts a rich history and is dotted with historic landmarks and architectural gems. The town center features a delightful mix of locally-owned shops, restaurants, and cafes, perfect for leisurely strolls and exploring. Residents can also enjoy the outdoors at the Middlesex Fells Reservation, a nearby nature reserve offering hiking trails, scenic views, and recreational activities.

Families are drawn to Winchester for its exceptional school system, which consistently ranks among the top in the state. The town's commitment to education is evident in its state-of-the-art facilities and dedicated faculty, providing students with a solid foundation for their future.

Real estate options in Winchester are diverse, with a range of architectural styles and property types to suit different preferences and budgets. From charming historic homes to modern condominiums, there is something for everyone in this vibrant community.

Whether you are looking for a peaceful suburban retreat or a place to raise a family, Winchester offers a welcoming and thriving community with all the amenities one could desire. Discover the charm of this Middlesex County gem and make Winchester your next home.

Newest Listings in Winchester

$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.
$549,900
2 Beds ⋅ 1 Baths ⋅ 73298669 MLS
Discover a unique opportunity to live in the heart of downtown Winchester at the Church Place Condominium! This inviting residence features high ceilings and large windows, allowing abundant natural light to fill the space. Enjoy the convenience of in-unit laundry. The versatile second room can serve as a bedroom or home office, perfect for today’s work-from-home lifestyle. Additionally, this unit comes with two designated parking spaces, which can be used or rented out, adding even more value to your living experience. Nearby, you'll find a variety of amenities, including shops, parks, and dining options that cater to all tastes. Commuters will appreciate the close proximity to the commuter rail, ensuring easy access to surrounding areas. This condo perfectly blends comfort and convenience, making it an ideal choice for those looking to embrace a vibrant downtown lifestyle!

115 Washington St Unit 2D, Winchester

Listing courtesy of Listing Agent: Andersen Group Realty from Listing Office: Keller Williams Realty Boston Northwest.
$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.
$1,050,000
3 Beds ⋅ 2 Baths ⋅ 73297482 MLS
Grand residence in a restored 1880 Victorian. Expertly renovated with premium finishes throughout yet still retains elegant period details. Generous ceiling height and hardwood floors. Central a/c. Open plan 1st level has a spacious living room with gas fireplace and dining room with a wall of windows opens to the front balcony. Kitchen island with space for all (and storage below). Useful mudroom at the kitchen entrance. Second level has a primary bedroom with a walk-in closet and laundry. Two additional bedrooms, excellent storage space, and a stylish bath complete this level. Newer systems. Tons of basement storage. Proactive & collaborative association is 100% owner-occupied. Pet friendly. Roof and exterior work done in 2021 with Historic colors and superb workmanship. Garage with easy potential for EV charging. 4 pkg. Huge level lot with majestic trees is delightful for entertaining & gardening. Convenient to all that the Center offers; schools, parks, library, and commuter rail.

201 Washington Unit 201, Winchester

Listing courtesy of Listing Agent: The Petrowsky Jones Group from Listing Office: Compass.
$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.
$549,000
3 Beds ⋅ 2 Baths ⋅ 73297307 MLS ⋅ ['Winchester Green'] BLDG.
Welcome to 247 Washington St Unit 9, just a short walk to the center of town where you will find, boutiques, restaurants and the newly renovated commuter rail! In addition, the High School, Middle School and top-rated Muraco elementary are all nearby! Entering the first floor, you will find a bright, open concept kitchen, dining and living room.  On the second floor, there are two bedrooms, each with professionally designed closets, along with an updated bathroom with custom cabinetry and a stunning tile floor. The third floor boasts a sun-drenched primary suite with a cathedral ceiling, skylight and updated bathroom with beautiful tiles and fixtures. Storage abounds in the suite with 2 sets of built-in drawers and 2 large closets. Beautiful hardwood floors add to the charm of this home. Finished basement provides an area for a gym, family room or home office - your choice! Laundry room with more storage completes the space. Come see for yourself what this lovely home has to offer!

247 Washington Street Unit 9, Winchester

Listing courtesy of Listing Agent: Vita Realty Group from Listing Office: Compass.
$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.
$729,000
2 Beds ⋅ 2 Baths ⋅ 73296416 MLS ⋅ ['Wedgewood Place Condominiums'] BLDG.
Located in Prime Winchester Town Center ! Great Condo Opportunity for Retirees , Downsizing Folks or Young Professionals within short walking distance to the New State the Art MBTA Train Station currently being built and Projected to open Fall of 2024 .This top floor unit with Elevator has been tastefully updated with engineered Bamboo Wood floors , Beautiful Updated Bathrooms , Fireplace living room , Open Dining Area , Balcony , Association Pool , Garage Parking , Central Heat and Air conditioned . Convenient walk to all that Winchester Center has to offer like Fabulous Restaurants , Supermarket , Bakeries , Boutique Shopping , Hair/Nail Salons , Parks and walking trails.

666 Main Unit 411, Winchester

Listing courtesy of Listing Agent: Stephen Latzanakis from Listing Office: Stephen Latzanakis.
$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.
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