The town of Winchester is located 8 miles north of Boston off Route 93. At one time, Winchester was much larger, encompassing parts of nearby Medford, Arlington and Cambridge. Winchester real estate is made up of picturesque residential neighborhoods with mostly single family homes that range from mid-sized to grand estates. Downtown has condominiums and multifamily homes mixed in with its shops. Residents enjoy Winchester's restaurants, the local pub and boutique stores.
New construction custom built home-walk to downtown. While the floor plan has been finalized, there is still opportunity to customize the home of your dreams. The finis...
Listing courtesy of Mark Donnellan from Better Homes and Gardens Real Estate - The Shanahan Group
This gorgeous colonial is located in a popular neighborhood on a sylvan side street. As you enter the home, you’re greeted by the fireplace living room with its wall of w...
Listing courtesy of Anne Spry from Barrett Sotheby's International Realty
Attention contractors, builders, and DIY enthusiasts! Looking for a hidden gem in Winchester with many possibilities. Property is in the RG zone and is a conforming lot w...
Listing courtesy of Danielle Storella from Berkshire Hathaway HomeServices Commonwealth Real Estate
Move in Ready! Freshly painted with many updates including new hardwood floors. This END UNIT has an extra family room. Only end units have this bonus space. The first fl...
Listing courtesy of Stephanie Singer from William Raveis R.E. & Home Services
Welcome to easy living! This is the home you’ve been looking for. There’s nothing to do but move right in and enjoy this meticulously maintained home. This beautifully up...
Listing courtesy of Paula R. Sughrue from Better Homes and Gardens Real Estate - The Shanahan Group
Nestled on Winchester, East Hill location much sought after Jefferson Road. Close to the Fells Reservation, as well as Winchester Center, restaurants and the commuter ra...
Listing courtesy of Mary Price from Better Homes and Gardens Real Estate - The Shanahan Group
Lovely home in delightful Ambrose neighborhood. Move right in to this immaculate cape with two bedrooms on the first floor and an office. Third bedroom is located on the...
Listing courtesy of Nannette Shanahan from Better Homes and Gardens Real Estate - The Shanahan Group
Quiet cul-de-sac living in a beautiful neighborhood, meticulously maintained & updated Colonial with an exceptionally large level yard. An entertainer’s dream, this home...
Listing courtesy of Andersen Group Realty from Keller Williams Realty Boston Northwest
Charming, spacious & inviting 3 bedroom, 3.5 bath ranch in much loved neighborhood . A welcoming entry foyer with sky lite leads to a large living room with fireplace. E...
Listing courtesy of Karen Piedra from Realty Executives Boston West
Completely renovated "smart" colonial within walking distance of Lynch elementary school! With seasonal views of Winter Pond, this beautiful sunny home boasts Jerome Bail...
Listing courtesy of Seeme Moreira from Coldwell Banker Realty - Winchester
Attention contractors, builders, and DIY enthusiasts! Looking for a hidden gem in Winchester with many possibilities. Convenient one-floor living in this ranch style home...
Listing courtesy of Danielle Storella from Berkshire Hathaway HomeServices Commonwealth Real Estate
Awesome opportunity to own a meticulously maintained, one level living 2-BR 2-Bath in the sought after “The Willows” condominium! This south-facing, spacious corner unit ...
Listing courtesy of Wei Fu from Phoenix Real Estate
Welcome to 45 Winford Way, a beautiful full dormered Cape overlooking the Fells on the Winchester/Medford border that gives you the best of both worlds! Cozy up next to t...
Listing courtesy of Anne Spry from Barrett Sotheby's International Realty
Prepare to fall in love w/this luxurious 6-bedroom dream home. Modern, open layout, perfect for today’s lifestyle. Comfortably work at home, entertain, & spend time w/fam...
Listing courtesy of The Laura Baliestiero Team from Coldwell Banker Realty - Concord
HISTORIC HOME & WALK TO TOWN! Spectacular location with plenty of vintage characteristics like the floor to ceiling windows and original hardwood flooring. Generous kitch...
Listing courtesy of The Marrocco Group from Coldwell Banker Realty - Winchester
Come see this beautiful 2400 square feet two unit complex townhouse in lovely Winchester. Built in 2011. This home is on 3 levels plus the basement. It has 4 bedrooms and...
Listing courtesy of Fintan Doherty from Berkshire Hathaway HomeServices Commonwealth Real Estate
Meticulously cared for Colonial with picture perfect golf course views! This stunning "Smart" home has been designed with incredible craftsmanship and to suit today's mod...
Listing courtesy of Andersen Group Realty from Keller Williams Realty Boston Northwest
Beautiful, highly sought after Church Place Condominium! Centrally located, you will enjoy all of the amenities you would expect of in town living! Just a hop, skip, and...
Listing courtesy of Kerrilynn Yemma from RE/MAX On The River, Inc.
OPEN HOUSE 6/17~4-6PM beautifully RENOVATED townhome that lives and feels like a single family is the perfect location to enjoy all Winchester has to offer; barely a 1/4 ...
Listing courtesy of Chrisanne Connolly from Wilson Wolfe Real Estate
OPEN HOUSE 6/17~4-6PM beautifully RENOVATED townhome that lives and feels like a single family is the perfect location to enjoy all Winchester has to offer; barely a 1/4 ...
Listing courtesy of Chrisanne Connolly from Wilson Wolfe Real Estate
VERY SPACIOUS updated 1925 Colonial in incredible location! This thoughtfully designed 6 bed, 5.5 bath home is ideal for family living on 4 finished levels. The main floo...
Listing courtesy of The Marrocco Group from Coldwell Banker Realty - Winchester
Classic ranch style home with room to grow and expand. Freshly painted inside and out. Family friendly neighborhood in the esteemed Vinson Owen School district. Readi...
Listing courtesy of Dave White from OwnerEntry.com
Quaint Colonial located in close proximity to schools, Horn Pond Bikeway, downtown Winchester Center and the train station for destinations beyond! Nestled in a wonderful...
Listing courtesy of Andersen Group Realty from Keller Williams Realty Boston Northwest
Beautifully renovated 3 bedroom with thoughtful and functional details. The first floor has a spacious open floor plan with a brand new kitchen at the center and convenie...
Listing courtesy of Edward Dudley from Clockhouse Realty
Ready to create your dream home? Situated on a dead-end street – this home offers a multitude of opportunities. Live in as-is or create your own vision for this lovely 3 ...
Listing courtesy of Pirani & Wile Group from Leading Edge Real Estate
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 4 bed 4 bath ...
Listing courtesy of Kim Covino & Co. Team from Compass
Stunning custom-built 6-bedroom house on a large and tranquil lot. This beautiful home welcomes you with a magnificent 18" foyer and features an amazing family room with ...
Listing courtesy of Weidong Li from WINN Real Estate & Consulting
Stunning 4 bedroom 3.5 bath Colonial home from premier builder resides in a desirable neighborhood is a must see! Only a few minutes walk to Horn Pond. This beautiful hom...
Listing courtesy of Alina Wang from Coldwell Banker Realty - Lexington
Don't miss this hidden split-level gem located in the Muraco school district and near the wonderful town center of Winchester. Tucked at the end of a long driveway this ...
Listing courtesy of Team Patti Brainard from Compass
NEW CONSTRUCTION!! Must see this gorgeous 4/5 bedroom home with thoughtful design & high end finishes! This luxurious home is spacious and inviting, offering a grand open...
Listing courtesy of Kim Covino & Co. Team from Compass
Presenting a new construction masterpiece that's a refreshing break from the ordinary, it's extraordinary! This exceptional home was designed to be beautiful yet casual, ...
Listing courtesy of Team Suzanne and Company from Compass
Stunningly renovated with curated items from around the world, this renovation project was done thoughtfully for peaceful moments. Whether you have a large family, a mult...
Listing courtesy of Beth Sager Group from Keller Williams Realty Boston Northwest
Magnificent oversized lot! This spacious 4/5 bedroom home was recently updated and expanded & offers a new direct entry 2 car garage w/mudroom! Open airy kitchen with map...
Listing courtesy of Kim Covino & Co. Team from Compass
MUST SEE this delightful WATERFRONT home nestled alongside Little Winter (skating) pond with fabulous views! This updated contemporary designed home features a stunning e...
Listing courtesy of Kim Covino & Co. Team from Compass
Refined, elegant and turnkey, this Colonial Revival is on one of Winchester’s premier streets. Steps to train, town, and the desirable Ambrose school. Designed for entert...
Listing courtesy of Andersen Group Realty from Keller Williams Realty Boston Northwest
Adorable 4 bedroom 2 bath cape in top East side neighborhood! Situated across from the fells, this nicely updated home is a nature lovers dream! Offering an optional fir...
Listing courtesy of Kim Covino & Co. Team from Compass
ATTENTION: THIS IS THE ONLY UNIT REMAINING AT ALLEGRO!! Spring has sprung! After a long winter we all get restless and are ready to be enjoying the outdoors! We can’t thi...
Listing courtesy of Vita Realty Group from Compass
TOP Waterside neighborhood! This custom, impeccably renovated and re-designed home offers a top location across from Mystic lake with direct private/ deeded water access ...
Listing courtesy of Kim Covino & Co. Team from Compass
Price Reduced!. Charming Colonial is within walking distance to Horn Pond. Exceptionally well cared for home with LANDSCAPED YARD. The 1st floor has a four-season enclose...
Listing courtesy of Boston RE Group from Coldwell Banker Realty - Back Bay
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