A true 'Diamond in the Rough'! This 2 bedroom colonial is perfect for a contractor or the handyman in you. Although it needs major renovations, it offers an excellent opportunity to rehab or rebuild and get your foot in the door in Winchester! First floor has an enclosed front porch leading into th...

Location, Location describes this Charming Single Family Winchester Colonial. 7 Rooms, 3 Bedrooms, 1 Bath, access to the Attic through third bedroom pull down ladder, along with an additional Sun Room off the First Floor living room. Beautifully landscaped corner lot. Access to Tri-Community Greenw...

Welcoming and charming Garrison style home located on a cul-de-sac in desirable Winchester! This quaint home has been well maintained and updated with all the modern conveniences of today including central AC. Enter into a cozy living room featuring gorgeous hardwood floors throughout. Just off the ...

Open Houses Sat and Sun 12-2.This sunny Cape offers a flexible floor plan with two full bathrooms, 3 bedrooms, and an office/den. An adorable mud room leads to an open kitchen with brand-new cabinets, quartz countertops and recent stainless appliances. Current owners have replaced the roof, installe...

Move right into this adorable 3 bedroom,1.5 bath home perfectly sited on a spacious lot close to town w/ an oversized deck and private level rear yard with many perennial plantings and sweet garden areas. Enter from the inviting front porch into the bright and cheery foyer w/open concept living room...

Stylish and spacious, townhouse near Winchester Center. Completely renovated within the last 5 years with chic amenities including stunning hardwood floors. The open concept first floor includes a gas fireplace, high ceilings, crown moulding. The second floor boasts 2 generous bedrooms, with full ba...

Welcome to this lovely 3 bedroom townhouse near Winchester Center and The Flats. This spacious home lives and feels like a single with private fenced-in landscaped garden area, private entrance and plenty of parking. This home features a sparkling newly updated kitchen with quartz counters and all n...

Enjoy all of Winchester with this lovely 4bedroom, 1.5bath Colonial style home close to everything. Leonard Field is directly at the end of the street, Fells reservation with over 100 miles of mixed-use trails is one block away and the town center is just one mile away allowing you take part in shop...

Lovingly maintained colonial, 2004 renovation, situated on an oversized fenced in lot in a great location! An open airy first floor with hardwood floors, high ceilings with welcoming foyer, formal dining room with built-ins, upgraded kitchen, spacious living room, full bathroom and a lovely sunroom...

Lovely 4 bedroom, 2.5 bath, Colonial Revival home, with loads of period detail and charm, within a short walk of Winchester Town Center. This 4 level home offers lots of great living space, including a bonus playroom in the basement. Beautiful crown molding and hardwood floors are throughout this h...

Sun bathed single family in Winchester Estates area w/versatile and open floor plan. Large windows throughout provide panoramic views of beautifully landscaped front, side and back yards. En suite master bedroom w/custom-built wall cabinets/closet and sliders to deck connecting to sunroom is ideal ...

A great home in an exceptional neighborhood situated on one of the best lots around. The yard is perfect for entertaining and enjoying the lush greenery. This 3 bedroom 2.5 bath home offers so much.The living room, kitchen and dining room flow perfectly on the first floor. A brand new deck completed...

Welcome to this charming ranch with such curb appeal in a desirable Westside Ambrose School neighborhood. Enjoy one floor living with a pretty fireplace living room upon entering from front door. Dining area opens up to family room with built in bookcases. French doors open up to a deck overlooking...

Welcome home to this charming Alfred Eliot English Tudor! Enjoy the scenic view and convenience of both Winter and Horn Pond. Meticulously maintained, with a mix of preserving the integrity of the era while featuring many updates for modern living.The sunny living room boasts hardwood floors, fields...

Top Westside location ! This home has been loved and cared for the last 50 years by its present owner. Mayflower Road is a dead end street so traffic belongs to residents. Sitting on a lovely half acre lot, the property boasts Nine Rooms, Four Bedrooms (4TH on lower level, perfect for Nannie), and ...

Home sweet home in one of Winchester's best locations! 3500 sq ft, 4 beds, 4 baths, 4 fireplaces with a well landscaped yard and a waterfall! Desirable open living concept features a spacious kitchen filled with custom cabinets and SS appliances, leading to a family room with a gas fireplace, cathed...

Best value in Winchester!!!Must see this 2012 renovation/expansion! Move right in to this thoughtfully designed West Side colonial with 4/5 bedrooms close to Vinson Owen school. The home offers large flowing rooms, high ceilings and a floor plan that will meet your every need! Living room & dining...

This updated and remodeled Colonial is ideally located near the heart of Winchester, convenient to schools, restaurants, shopping, parks, commuter rail, Fells Reservation and Mystic Lakes! Featuring 4 spacious bedrooms & 2 full and one half baths, the open concept chef's kitchen and expansive Great ...

Beautiful full renovation and redesign of an original Queen Anne Victorian-right in the center of downtown Winchester! This home has a wonderful combination of original character and modern style. The first floor boasts a spacious foyer, living room with original pocket doors and newly added frenc...

Welcome to 44 Glen Road - where old meets new with stunning results! Updated eleven room Antique Colonial fashioned for today's comfortable living. Beautifully renovated chef's kitchen with large, granite center island. A bonus breakfast area with fireplace and large dining room make the 'heart of t...

OPEN HOUSE Sunday 5/16 12:30-2 This unique home in TOP location, is perfectly sited on a gorgeous, beautifully landscaped lot set between Ginn Road and Rangeley Estates with access to both downtown neighborhoods! This quality built 3 level home is constructed mainly of brick and offers unique marb...

A rare offering in a beautiful setting- welcome to 33 McCall Road! This extraordinary mid century modern property is a perfect combination of updates, smart home technology and location. Situated in the heart of Myopia Hill, this home features a renovated kitchen with high end Miele appliances, Subz...

Pristine Colonial in desirable Ambrose School district! This impressively spacious home boasts six bedrooms with three full and one half bath. Welcome into a grand entrance leading to the formal dining room with tray ceiling and hardwood floors. The recently updated kitchen includes stainless steel...

AMAZING VALUE! Must see this spectacular home with carriage house completely renovated & restored inside and out! This spacious home offers a prime downtown location with 4 floors of space featuring 5+bedrooms, 3.5 baths complete with private ELEVATOR! This recently renovated custom designed town ho...

This Majestic home close to town offers all the modern amenities you desire blended with old world detail and craftsmanship beyond compare. This stunning home was completely redesigned, expanded & renovated inside and out with high end systems & finishes and a offers a gracious flowing layout that l...

This Custom built home is one of a kind! The moment you enter this wonderful property, you will want to call it your forever home! Sited on one of the most beautiful lots in town, w/ hand selected mature plantings, new Ipe deck and privacy galore! The elegant front entry foyer welcomes you and draws...

UNDER CONSTRUCTION~Must see this stunning 4/5 bedroom home with luxurious design & high end finishes. This custom home is spacious and inviting, offering a grand open floor plan ideal for entertaining and modern day family living. The kitchen will feature an 8' island with seating/ quartz countertop...

Newer construction, custom built shingle style home in top Myopia/ Winchester Country Club location! Designed for ease of living with direct entry garage into mudroom, 1/2 bath leading into sun-drenched kitchen/ family room spanning the rear of the home, oversized windows overlooking conservation & ...

For the first time in over 25 years presents the rare opportunity to acquire one of the most exclusive and private lots in Winchester. The 1 acre property sits on an immaculately manicured landscape. Laid out with a wide open floor plan, creating endless opportunity for any family. Floor to ceiling ...

Fabulous new construction opportunity awaits you in Winchester. Spectacular floorplan with 14 magnificent rooms, 5 bedrooms, 5 1/2 baths. Winchester luxury living encompassing choice materials and tasteful design by well known Master Builder from Winchester. Casual elegance with features such as bea...