Properties listed in Winchester

Welcome to 2 Chestnut Street, an exquisite new construction home in progress by Mark Stephen Development. Situated off coveted Main Street in one of Winchester’ ...

Welcome to 21 Shepard Court, a beautifully renovated townhouse nestled in a quiet cul-de-sac. This 2+ bedroom, 1-bathroom home offers four levels of living spac ...

Located in the TOP neighborhood that everyone wants! Welcome to the Flats, where elegance and charm abound. A gorgeous foyer welcomes you and flows easily into ...

Tucked away on a quiet sought after neighborhood, just steps away from the Wedgemere Station and Winchester Center, this meticulously maintained 5-bedroom home ...

Experience the perfect blend of timeless elegance & modern luxury in this stunning 5-6-bedroom home, set on one of the town’s most picturesque streets. The ...

NEW CONSTRUCTION! This stunning 7-bed, 5.5-bath luxury home boasts high-end finishes and a thoughtfully designed open floor plan, perfect for entertaining and m ...

Beautifully updated 4-bed, 2.5-bath ranch on a landscaped half-acre lot with attached 2-car garage. Enjoy single-level living with an open floor plan, cathedral ...

Nestled on a cul-de-sac in Winchester's desirable west side, this brand-new construction redefines modern luxury living. Spanning 7,500 sq. ft., this exquisite ...

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 ...

Welcome to this well loved 4-bedroom expanded Cape, on quiet cul-de-sac, cared for by the original owners for nearly 65 years! Located in the brand new Lynch El ...

This stunning Colonial Revival home, situated on one of Winchester’s most desirable streets, is just moments from the train station, town center, and Ambrose Sc ...

Welcome to your private retreat at Chez Brazo. Nestled on a spacious 1+ acre lot, this property offers a serene environment that is hidden from passersby. Upon ...

Welcome to 4 Norwood St, a stunning custom-built home by Mark Stephen Development. Just a short walk to Winchester town center with easy access to Boston, this ...

Discover the warmth and charm of this inviting New England Colonial, newly built in 2004. This sun-filled home features three bedrooms, 3.5 bathrooms, and a fle ...

Beautifully updated 5 bed, 3.5 bath Colonial on Winchester's West Side with over 3400 sq ft of living space located on a quiet cul-de-sac in the coveted Vinson- ...

Beautiful & magnificent, this colonial single family offers a perfect blend of timeless elegance and contemporary amenities. Situated at the end of a serene ...

This recently renovated Victorian blends historic charm with modern luxury in a prime in-town location-minutes to the shops, Common, train and Wedge Pond. Step ...

Nestled on a peaceful street surrounded by trees, this beautifully updated Cape home offers a perfect blend of comfort and character. Located just moments from ...

Exceptional colonial on Myopia Hill showcasing an expansive rear family room addition, perfectly situated on an idyllic lot surrounded by lush gardens & mat ...

Welcome to this stunning 4-bedroom, 3.5-bath townhouse, thoughtfully designed and built in 2016. 1st fl features an open-concept layout, the living room seamles ...

Discover the prestige of owning a home at 30 Swan Road, a distinguished Tudor-style residence on one of Winchester's most esteemed streets. Offering magnificent ...

Great value in Town! Discover the perfect blend of luxury and comfort in this stunning 6-bedroom home. Sunlight pours into the open-concept layout, highlighting ...

Incredibly well maintained, nicely updated 3-4 bedroom Colonial in a wonderful neighborhood in desirable VO School district! The first floor has an oversized ki ...

Welcome to Winchester ! This townhouse with large shared backyard is located on lovely tree lined street . The front porch welcomes you as you can sit and watch ...

Experience the timeless charm of this stunning English Tudor in Winchester’s coveted Flats neighborhood. Set on an oversized lot with mature landscaping, this h ...

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 ...

Welcome home to this picture-perfect Colonial, tucked away in a quiet, sought-after neighborhood just steps from Ambrose! Boasting gorgeous curb appeal & a ...

Welcome to 666 Main Street, Unit LV2, Winchester. This beautiful well maintained 2 bedroom, 2 bathroom condominium on the desirable ground level, features a Pri ...

This stunning 4-bedroom, 4-bath modern home offers the perfect blend of luxury and tranquility. Featuring soaring vaulted ceilings, a floor-to-ceiling fireplace ...

Sprawling expanded cape set on stunning private 1/2 acre lot in coveted Brooks neighborhood! The curb appeal alone will draw you in to this spacious 4300+ sf 4B ...

Stately elegance resides on one of the most desirable streets in the “Flats". This sprawling home details fine craftsmanship & modern finishes that a home o ...

A DESIGNER DREAM! Welcome to 19 Johnson Road, a pristine 5-bedroom colonial-style home located in the highly sought-after Vinson Owen School district! As you en ...

Introducing 74 Hillcrest Parkway! This spacious, modern 5-bedroom home is nestled across the breathtaking Middlesex Fells Reservation on one of Winchester's mos ...

Situated on a picturesque corner lot, this exceptional home is nestled in a very desirable neighborhood! Step into a light-filled, open-concept 1st floor, where ...

Enjoy the best of Winchester living in this spacious 2-bed, 1.5-bath townhouse at Wedge Pond Condominium, set along scenic Wedge Pond. The main level features h ...

Welcome to this impeccably maintained & beautifully updated Colonial on large lot near the town center. This home blends charm w/ modern convenience, featur ...

This elegant 1914 Revival home combines timeless charm w/ exceptional architectural details. Located on a highly sought-after, picturesque street in "The Flats, ...

This European-inspired estate is a masterpiece of design and craftsmanship. Every detail has been meticulously curated, blending timeless elegance with state-of ...

Welcome to your dream home! This brand-new, meticulously crafted residence offers the perfect blend of luxury & comfort in Winchester’s newest neighborhood. ...

Embrace elegance and convenience with this exquisite townhouse that's been meticulously designed. This residence presents a generous 4-bedroom, 3.5-bathroom, am ...

Welcome to 158 Swanton Street—a stunning Ron Roy new construction townhome blending modern design with unparalleled craftsmanship and attention to detail in the ...

Exceptional Home nestled in one of Winchester's most desirable West Side Neighborhoods and on a Cul de Sac! Open Floor Plan, Very Spacious Granite and Stainless ...

*** OPEN HOUSE CANCELLED**** OFFER ACCEPTED Presenting 12 Olde Lyme Rd, where classic Colonial charm meets modern style + convenience. Nestled at the end of a p ...

Welcome to The Residences at Winchester! A perfect move-in ready single-family alternative without the hassle of yard work. Fantastic chance to own this 2 bedro ...

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 2 pr ...

Welcome home to 19 Yale, where elegance and charm embrace, located in the TOP neighborhood that everyone wants! A gorgeous foyer welcomes you and flows easily i ...

Welcome to 666 Main St Unit L3- Ground level 2 Bedroom Unit with Sliders to Patio overlooking Wedge Pond-Kitchen Totally Updated with Custom Cabinets and Quartz ...

Nearing completion! Welcome to this exquisite 6-bedroom, 5-1/2 bath residence nestled in one of Winchesters most prestigious neighborhoods. This completely rebu ...

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 loa ...

Explore this pristine newer construction, freshly updated home just outside the center!! Situated on a gorgeous level lot with slider to patio & expansive r ...

Nestled at the end of a peaceful cul-de-sac in Winchester, this charming 3-bedroom, 1.5-bath home is a must-see. Recently updated with fresh paint, modern floor ...

Nestled in a desirable neighborhood, this home offers the opportunity to embrace the timeless elegance of the mid-century era. Lovingly maintained in its origin ...

Welcome 35 Lawson where elegance meets modern luxury in this exquisite 6-bedroom 4F, 2H bathroom residence. A stunning marble mudroom welcomes you into the home ...

Experience exceptional living in this stunning Wedgemere Ave home w/ spectacular resort style back yard! Thoughtfully updated throughout with custom high end fi ...

Welcome to this charming Colonial, thoughtfully maintained by its owners! Nestled on a peaceful, tree-lined street, this beautifully updated colonial home exude ...

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 wi ...

Stunning Absolutely! Custom-built 6-bedroom house on a large and tranquil lot. This beautiful home welcomes you with a magnificent 18" foyer and features an ama ...

Now is the time to make a move! Step into a sophisticated lifestyle as you enter through a charming courtyard into this elegant condo. The beautifully updated k ...

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 abunda ...

This stunning Colonial Revival home, situated on one of Winchester’s most desirable streets, is just moments from the train station, town center, and Ambrose Sc ...

Discover this stunning, flats location ~ fully gut-renovated 3-bedroom, 2.5 bath home~ perfectly situated close to downtown Winchester! W its breathtaking desig ...

Classic Colonial 4 bedroom 3+1/2 bath on quiet street overlooking the Mystic Lake. Awaits buyers with vision prepared to renovate. Freshly painted interior glea ...

Beautifully renovated first-floor condo in the highly sought-after "Willows at Winchester" complex. This expansive, single-level unit features an open-concept l ...

Nestled in the heart of Winchester, this charming 4-bedroom, 1.5-bathroom single-family home offers 2,202 square feet of living space on a 7,126-square-foot lot ...

Don't miss your opportunity to own on Canterbury Road! This sun-drenched, 4-bedroom home with hardwood flooring offers an open and classic layout. Enjoy the spa ...

Tucked away on a dead-end street, 6 Ardley Place blends classic character with modern comforts. Beautifully expanded with a complete renovation & redesign i ...

Just completed!! New construction! Energy star rated, high efficiency 5 bed 4.5 bath home perfectly situated in a prime East Side location! The first floor welc ...

Stunning waterfront home on Little Winter Pond offers the perfect blend of modern design and serene natural beauty! Thoughtfully updated, the home welcomes you ...

Exquisite 6-bed, 6.5-bath residence offers 6,300 sq ft of sophisticated design and luxurious features. The chef’s kitchen boasts dual islands, quartz countertop ...

This newly constructed home faces Old Village Dr. & redefines modern luxury! Designed w/ both elegance & everyday comfort in mind, this residence blends ...

This stunning, freshly painted, home is located in a picturesque and unique setting, elevated on a small hill with a private half-acre lot in a tranquil cul-de- ...

With its coveted setting, elegant bones, and enduring charm, this Royal Barry Wills home awaits your personal design statement, and the chance to build instant ...

Charming, updated carriage house on a private lot, where form meets function in an in-town location. The expansive living room with a fireplace and beam ceiling ...

LOCATION, LOCATION, LOCATION This has it.....Current building is a 2 bedroom ranch with lr,dr,k.needing TLC..Great potential for a Complete rebuild and/or resto ...

This distinguished residence, built by premier local developer, represents the pinnacle of elegant living! Soaring ~9' ceilings & pristine hardwood floors s ...

NEWER CONSTRUCTION 4 bed 3.5 bath colonial located in a great neighborhood right outside Winchester center! Enjoy all the area has to offer just outside your do ...

Nestled in a coveted location just moments from the heart of downtown Winchester, the stunning Barstow House boasts a unique Mansard roof & timeless colonia ...

Discover the perfect blend of charm & modern elegance in this beautiful home, nestled on one of the most highly desired streets in town. A stunning fire-pla ...

Welcome to this oversized Cape in a lovely west side neighborhood of Winchester. Opportunity for a little TLC or a significant renovation, the flexible layout o ...

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 ...

Welcome to a rare opportunity to select the final finishes in your dream home right within Winchester’s most coveted neighborhoods. 5 Clearwater presents a luxu ...

This expansive contemporary residence exudes elegance & sophistication and offers the perfect layout for gatherings & everyday living. This gorgeous hom ...

Welcome to the highly coveted condominium living in Winchester: the Willows. This unit has over 1,600 sq. ft., with two stories/duplex style condo, 2 beds, and ...

Picture perfect cape style home across from the Lynch Elementary School. This beautiful home on a corner lot checks all the boxes with 4/5 bedrooms on 2 floors ...

Exuding elegant luxury, this fully renovated Victorian boasts a carriage house and extraordinary grounds, in one of Winchester’s most coveted neighborhoods! A s ...

This inviting ranch house is cheerful and functional. Sunlight floods the open living and dining rooms, while custom plantation shutters offer privacy. Hardwood ...

Nestled in a desirable Westside neighborhood, this stunning California contemporary/colonial home sits on a quiet cul-de-sac and offers 5 bedrooms, 3.5 baths, a ...

Nestled in a sought-after neighborhood, this stunningly reimagined home combines timeless charm and modern comfort, just a short walk to downtown. The inviting ...

Nicely updated home in desirable Muraco district! This home has been meticulously maintained & features many recent updates including newer windows, central ...

Step into this beautifully renovated historic townhouse that seamlessly blends classic charm with modern updates. This welcoming 3-bedroom, 2.5-bathroom home fe ...

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 loa ...

Nestled in the heart of The Flats, this stately 1932 brick Colonial has been fully renovated to perfection. Offering 2,900 sq. ft., this 4-bedroom, 3.5-bath hom ...

Welcome to The Ledges! This is a desirable end unit located in a fabulous cul de sac location. Freshly painted first level makes this unit ready to move in.This ...

Tucked away on a private cul-de-sac shared with just two lucky neighbors, this classic New England Colonial is the total package. With 4 bedrooms, 3 baths, and ...

Exquisitely restored brick Colonial situated in the sought-after Flats neighborhood of Winchester. Boasting refinished hardwood floors, beautiful moldings and t ...

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 ...

Located in a very desirable East Hill neighborhood, this one owner Circa 1929 Dutch Colonial offers a wonderful opportunity for the next owners to bring their i ...

Move right into this 5 b/r 4 bth colonial steps to Ambrose School! This picture perfect colonial features high ceilings,hdwd floors & an open first floor pl ...

Stunning Two-Family home in idyllic Winchester - Ideal for multi-generational living, investors or buyers looking for a top rated School District. This home is ...

Welcome to the highly-coveted Westside of Winchester, MA. This meticulously maintained Colonial-style home is set on 20,000 sqft lot with professional landscapi ...