Winchester MA Real Estate & Homes for Sale

This stunning 3-bedroom/2.5-bath home blends indoor comfort and outdoor charm. The main floor is an open concept design with cathedral ceilings and a striking floor-to-ceiling fireplace. Large windows offer abundant light and impressive views of nature's beauty. The kitchen has stainless-steel appliances and a large island with extra storage and seating, the ideal spot for gatherings. Sunset views from the dining room make dinners delightful. A multi-level layout separates the bedrooms from the living areas. There are three spacious bedrooms including a primary bedroom and bath with a jacuzzi tub, plus ample closet space for easy organization. The flexible family room can also be a potential fourth bedroom or a space for your in-laws/extended family. The yard, complete with deck, is perfect for BBQs and outdoor fun. Set across from the Fells, endless outdoor activities await. Close to downtown Winchester with an easy commute to Boston, this home is a standout. No open houses, appt only

Luxury living at its best at Unit 6 at 83 Church Street condominium complex. On the first floor there is a full-sized kitchen, dining area, living room with cathedral ceiling and large palladian window, second bedroom with full bath and large closet (now being used as a den). One of the highlights of this unit is an exterior door which allows entrance directly into the unit. Also, it allows an area for private outdoor seating. The custom moldings and architectural details add a special touch throughout along with hardwood floors. It includes a deeded garage and parking place. Winchester offers a strong school system, two commuter rail stations, a vibrant downtown shopping area with restaurants, and the Middlesex Fells, a hiker's delight.

Incredibly deceptive from the front, this ideally located home is great at keeping a secret about what's behind the front door...Space, space & more space. W/well over 5000sf over 3 fls, this home sits in a neighborhood that is often described as the "BEST STREET IN DOWNTOWN WINCHESER." It's exactly where you want to be. Often sought, but rarely found is a home in this MOST DESIRED NEIGHBORHOOD. A large family was raised here since 1988, & it's been loved AND lived in! The rooms are generous, the floor plan unique, the possibilities...endless! Newly removed, "miles & miles" of wall to wall carpet revealed ALL HW floors...even on both the front & back staircases. The grand two story foyer will one day be elegant & welcoming...paint, shined floors & a stunning chandelier will bring this fabulous home to life! W/plenty of bdrms for the growing family, the MASSIVE LL offers excellent potential for in-law or au pair quarters. Savvy buyers will know THIS is an opportunity NOT to be missed!

Stunning young colonial house on a quiet street meticulously designed for modern living complete with a charming front porch. The bright and spacious open concept main level boosts hardwood flooring, detailed woodwork, expansive windows bathing the space in natural light. Central A/C. Modern kitchen showcases Bosch Stainless Steel appliances and granite counters. Second floor features a luxurious master suite with walk-in closet and beautifully tiled master bath with oversized shower. Two good size bedrooms with ample closet space and share a family bath. Finished basement comes with an additional bedroom along with flexible space ideal for recreation, exercise or a home office, accompanied by a convenient half bath. The detached, oversized two-car garage includes attic space with a pull-down staircase and plenty of room for a work area or storage. Move right in and enjoy everything Winchester has to offer. Easy highway access, public transportation, parks, and excellent schools!

Discover the allure of this beautiful home nestled on an oversized 21,000sf private lot abutting conservation! This exceptional and meticulously maintained home boasts a flawless layout designed for comfort and functionality with large flowing rooms perfect for hosting parties & family gatherings. The stylish eat in kitchen offers granite countertops, espresso cabinetry and high end appliances w/island, a culinary enthusiasts dream! A fabulous screened porch off kitchen, large rear deck, plus a gorgeous patio all offer great places to unwind while enjoying the privacy & stunning conservation views. The sun drenched family room is beautiful w/ fplc & vaulted ceilings, the formal living & dining rooms complete this floor. The second floor offers 4 generously sized bedrooms & 2 full baths including the primary bedroom w/ walk in closet and spa like bath. Lower level gym/ rec room w/ direct entry to 2 car garage. Vinson Owen elementary school, Don't miss all this great home has to offer!

Welcome to the Willows at Winchester! This desirable townhome community includes a clubhouse with gym, community space, a stunning inground pool, elevators and walkable sidewalks surrounding lush professional landscaping. Unit 41 has a freshly painted main floor with a desirable floor plan with an open concept main floor that includes a living room with a gas burning fireplace, dining room, kitchen, 1/2 bathroom, a walk in pantry, and a large walk out composite material balcony with a nice view. The second floor includes 2 large bedrooms that both have their own full bathroom and the primary bedroom even includes a large walk in closet and a walk out composite material balcony. This unit also includes a large storage unit in basement of building as well. Nicely located close to downtown Winchester shops and restaurants, schools, the Fells and highway access. Don't miss out!

This Graystone expansive townhouse is among the 50 unit 2010 development located in gorgeous Winchester. Too many energy efficient and high-end finishes to mention: a spacious light filled open floor plan with soaring ceilings and an abundance of recessed lighting, sky lights, oversized windows. Featuring large marble bathrooms, custom built walk in closets, kitchen has gorgeous granite countertops and copious cabinetry storage including pull out pantry. Bask in the warm glow of the fireplace in soaring cathedral living room with built in bookcases, and create visitor/ office/ den space up stairs, which includes a full bath with soaking tub. There's a full deck for morning sun bathing or entertaining as well as two-car garage parking and in-unit laundry. 24 Hour professional management, landscaping is no longer your "must do" weekend chore! This townhouse is tucked into the quiet enclave at the back edge of the property. Freshly painted, quick close ready! Showings start Wed 17th OH

Welcome home to this spacious townhome in the coveted community, "The Village." This is a sought-after end unit featuring an attached garage with direct entry inside. Upon entering, you will find a tidy kitchen with granite counters and breakfast bar and stainless steel appliances, which opens to a bright dining area with a skylight and access to a private patio overlooking a grassy courtyard. On this level you will also find an expansive living room with gas fireplace, and a half bath. Head upstairs to find the primary suite which features a walk-in closet, additional closet and full bathroom. One more bedroom, a bonus room/office, a second full bathroom, dedicated laundry area and additional closets complete this floor. Unit #63, with an extra driveway for added parking, is located in close proximity to the association's swimming pool, clubhouse and tennis court. The Village is a short distance from Winchester's vibrant town center, schools, and commuter rail stop.

Get ready to swoon over this exquisite, completely renovated "C" Unit townhouse at "The Ledges" which is truly unlike any other you've seen. Enter into the sleek, open-concept kitchen w/ lacquered custom cabinetry w/ Italian pulls, Wolf cooktop & double wall ovens, Subzero refrigerator & wine fridge, double thick quartzite island, pantry cabinets, beverage station & glam light fixtures. The main level also features a dining area, living room w/ linear gas fireplace & sliders to a deck, half bath, & primary suite. The glamorous primary suite boasts a bedroom w/ vaulted ceiling, stunning quartz bath w/ double vanity, 2 custom closets, and laundry. The second floor features a loft area/office, two large bedrooms & a full bath. The expansive lower level features a huge family room w/ sliders to a patio, beverage station, gym/bedroom, & full bath w/ infrared sauna. There are too many luxurious features & amenities to list - you simply must see it.

Welcome to this charming Winchester home! Nestled amidst lush greenery, it exudes classic ranch style and is located in the sought-after Muraco School District, near Horn Pond and Middlesex Fells Reservation. Just a 20-minute drive to downtown Boston, this location offers both convenience and tranquility. Renovated in 2022, it consists of modern upgrades including stainless steel appliances, an updated AC system, and a new gas water heating system. Step into the beautiful garden leading to the spacious kitchen with new quartz countertops and Imitation wood grain tiles. The open-concept living room features gleaming hardwood floors. Two bright bedrooms and an office/den provide cozy spaces, while the expansive basement offers endless possibilities. Outside, stone pathways lead to the well-maintained backyard with a swing and picnic area, perfect for outdoor gatherings. Don't miss the chance to make this dream home yours!

Welcome to this exquisite townhouse nestled in Pepper Hill Estates.This home boasts a complete renovation featuring an open floor plan with stunning hardwood floor. Bathed in natural light, it feel spacious and airy. Updated kitchen showcases SS appliances, a stylish backsplash and spacious drawers.Dining room seamlessly flows into the expansive living room. A bathroom with shower on the first floor adds practicality to the layout. Lower level currently is utilized as a bedroom.The second floor hosts a generously sized main bedroom with walk-in closet and a beautiful bathroom with double vanity. Additionally, there is another bedroom, office, a full bathroom and laundry.One car garage is equipped with new garage door.Recent upgrades within the past two years including kitchen, flooring, painting and all three bathrooms with high-quality materials and well maintained.Insulation has been added to the attic and walls in the bedrooms. Great location with easy access to town.

Imagine living at the foot of the Fells, surrounded by a natural setting while being close to the Muraco School, trains, and the town center. This gorgeous Colonial sits high on a hill, surrounded by custom rock walls, a stone patio, and mature landscaping. With 5 bedrooms, including a first-floor guest suite, there's room for everyone and options for live-in nannies, in-laws, or aging in place. A stunning open kitchen awaits, featuring leathered granite and stainless-steel appliances. Large-scale rooms, including a front-to-back dining room, enormous family room, and lovely living room are offset with a sweet outdoor porch where you can have dinner and catch the incredible sunsets over Winchester Valley. The second floor features a large private primary suite, a huge walk-in closet, and a vaulted ceiling. 3 other bedrooms have big closets plus there is a storage and laundry room. There is also a 3rd floor study, an oversized 2-car garage, and a basement that can easily be finished!

Yes you can have it all. Winchester Flats, corner of Yale Street location. Exquisite move in ready gracious home, that will truly impress. Excellent layout, with a first floor bedroom and bath, walk in shower and double sink vanity. Spacious and sunny living room with a fireplace, dining room, and a first floor office. Family Room off the updated, eat-in Kitchen with sliders to the Patio and private back yard, ideal for indoor, outdoor entertaining, garden and play. Second floor primary bedroom suite with sunset views, 3rd bedroom and full Bath. Ample Storage and closets with expansion possibilities, easy to Dormer or expand if your desire. BONUS fireplace recreation room, bath with Stall shower on the low-level. SELLER PREFERS TO CLOSE AFTER THE End of SCHOOL YEAR. Offers due by 4/21- 7:00PM

Welcome to this adorable 4 bed, 2.5 bath home with a fenced in yard! ~10K seller credit!! This property features a large family room with a beautiful fireplace, an attached sunroom or perfect home office, spacious dining room & updated kitchen w/ gleaming hardwood floors and high ceilings throughout the home. For guests, or a 1st floor primary option there is a first floor bedroom w/ adjacent full bath.The second floor has 3 generously sized bedrooms w/ vaulted ceilings & full hall bath.The lower level is the perfect spot to watch a movie. Garage access, mud room, half bath, laundry and storage complete this home. Conveniently located close to highways,Winchester Hospital, Winch.Center, Muraco school & Leonard field. Enjoy coffee & muffins at your new home, w/ Winchesters beloved Gingerbread factory right across the street! With this homes great price, prime location & potential to make it your own, you won't want to miss this opportunity. 1 garage & 2 driveways for extra parking!

Perfectly situated in one of Winchester's most prestigious neighborhoods, "The Flats," this 7 bedroom home has an expansive lot w/ welcoming patio, fire pit & large level yard perfect for family fun! The 1st floor is stunning w/an abundance of picturesque windows that flood the living space w/ natural light. An exquisite mahogany wood-burning fireplace graces this inviting living rm complemented by bay window seating & garden views. Adjacent family rm & elegant dining rm lead to a butler's pantry & spacious updated kitchen w/granite counters, stainless appliances, cherry cabinets & dining area. The mudroom offers access to side entry & 2 car garage. The spacious 2nd floor offers 5 generously proportioned bedrooms and home office. The 3rd floor boasts 2 add'l bedrooms or home office & bath. Newly renovated lower level media room w/surround sound & wine cellar. Entire house renovated to 200 amps, recessed lighting, zoned sound system, new bath. Perfect blend of tech and timeless beauty.

A Brand New Townhouse with a modern stylish feel is nearing completion and will soon be ready for a new owner to make it Home! Located just minutes away from all the amenities in Winchester Center you could not ask for a more convenient location. You will be wowed as you cross the farmer's porch into the well designed open 1st floor that features a custom FP in the living room, built-in bench seating in the dining room and a dream kitchen with ample cabinetry and an island with a waterfall edge. You will also find a half bath off the mudroom and a slider to the private fenced in rear yard. The 2nd floor features the main suite with custom bath and walk-in closet, 2 additional bedrooms and another full bath. The finished LL has the 4th bedroom, a full bath and sitting room. Exterior access is also provided. This must be seen to be appreciated! (More photos coming soon)

Presenting Winchester's newest luxury new construction home, 4 Abby Road. The first floor features a formal dining room, fireplaced family room, and an eat-in kitchen with a gorgeous island & wet bar. The large mudroom, conveniently located off the garage, provides seamless access to the home. Additionally, a private home office just off the mudroom makes a serene space for work or study. The finished lower level boasts a glass enclosed gym with rubber floor, full bath, & media room. As you make your way to the second floor, you'll find four bedrooms, each exuding comfort & style. The primary bedroom is a true retreat, complete with a spa-like bath, oversized walk-in closet, & a separate den/nursery, offering a true sanctuary within the home. The location offers the perfect blend of tranquility & outdoor adventure. Residents can enjoy the convenience of walking to the Fells Reservation, where hiking, biking, & other outdoor activities await, while still being close to both I-93 & I-95!

Sunny, bright and spacious! This residence is tailor-made for hosting gatherings. The open concept living and dining room is adjacent to the chef's kitchen, complete with high end appliances, ample counter space and 2 skylights. But the real gem is the 4 season room just off the kitchen offering a tranquil retreat to enjoy your morning coffee while enjoying the beauty of the changing seasons. Upstairs include a primary bedroom with ensuite plus three additional spacious bedrooms. Connecting directly to the two car garage, you'll find a generous family room, laundry room, and a full bath. The lower level has a finished basement with working fireplace and tons of storage. Outside enjoy hosting barbecues in your expansive level backyard with stone patio. Located within the Vinson-Owen school district and near Wright-Locke Farms, hiking trails, and Mullen Field. 4 yr old roof!

This is one of the most notable and distinguished homes on Everett Avenue, with preeminent siting and curb appeal. Designed by famous architect Robert Coit, this residence combines the magnificence of early 1900s architecture with today's modern amenities. Completely renovated in 2023/2024, this residence features hallmark architectural details including Tudor-style balusters, high ceilings throughout, and a beautiful floor plan centered with a large entrance hall. Large-scale rooms, coffered ceilings, original crown moldings, mantels and decorative trim are enhanced by the beauty of restored hardwood floors. The brand new kitchen is a chef's dream, and includes a walk-in pantry with laundry and refrigerator drawers plus a butler's pantry with a wine fridge. Floor to ceiling windows flank the huge family room, overlooking park-like flat grounds. The huge lawn, magnificent old oak trees, beautiful birches and an ample driveway are some of the distinguishing exterior features.

Amazing views of Mystic Lake! Two blocks to Wedgemere Station, Shannon Beach, and restaurants downtown. Through the front door of this 5 bedroom home you'll be impressed with beautiful in-laid hardwood floors that flow through the dining room and formal fireplaced livingroom. Top of the line appliances include a subzero refrigerator, gas Wolf oven with grill and a wine island with it's own dishwasher, sink, two sub-zero refrigerators, and plenty of room for seating. French doors off the kitchen lead to the beautiful wrap around deck with a partially covered area for shade, perfect for entertaining family and friends. Plenty of considerably large windows throughout the home allow for bright light in every room. The lower level consists of a den with access to the patio, a wine cellar, and interior access to the 3 car garage. Private well for irrigation and peaceful sitting areas with perennial blooms all season. Sold as-is

Welcome home! Nestled on a huge, fenced-in lot in a sought-after neighborhood, this picturesque 4 bed, 2 bath home has it all. A spacious eat-in-kitchen with granite peninsula opens to a sun-filled family room boasting French sliders out to an elegant bluestone patio. The first floor also features a front-to-back, fireplaced living room, a bright home office, and a mudroom/playroom. Head upstairs to a stunning primary suite with soaring ceilings, a large, updated bath with glass shower and oversized tub, generous closets, laundry hookup, and French doors opening to a charming balcony. The second floor also features three additional bedrooms, an updated family bath, and additional closets. The partially finished basement includes an exercise room and a spacious storage area with additional laundry hookups. The backyard oasis with seasonal water views is perfect for outdoor enthusiasts. This home seamlessly blends comfort and style. Don't miss this gem!

NEW CONSTRUCTION!! Must see this gorgeous 6 bedroom home w/ thoughtful design & high end finishes! This home is spacious & inviting, offering a grand open flr plan ideal for entertaining & modern day family living. The kitchen features an oversized island w/ seating/ quartz countertops, high-end appliances, & breakfast nook/dining area. Off the kitchen is a spacious family room w/gas fireplace & direct exterior access w/ sliders leading to large deck or patio & nice rear and side yard. The first floor also offers a formal dining room and guest bedroom w/ bath plus a home office & 1/2 ba. The second level primary suite is luxurious, offering a sitting area, sleeping area, huge walk-in closet, lavish bath w/double vanities, oversized shower & soaking tub! Three additional beds incl. junior suite w/ bath, full hall bath & laundry room finish this level. Finished lower level media/ rec room w/ full bath. 2 car garage direct entry to great mudroom! Quick & easy access only 6 miles to Boston

Welcome to this exquisite WATERFRONT PENTHOUSE nestled in the heart of Winchester. Upon entering, you'll be captivated by the seamless flow of the open concept kitchen, living, and dining area, complemented by not 1 but 2 private balconies that offer breathtaking water views. The primary suite is a true haven, featuring an expansive walk-in closet (large enough for exercise equipment), vast storage, a 3RD private balcony, and a luxurious spa-like bath. The kitchen is a culinary delight, boasting a large center island, marble tops, and high-end appliances. With its stunning style and finishes, this condo is sure to impress even the most discerning buyer. Practicality meets luxury with abundant storage. A large pantry off of the kitchen has built-ins, a 2nd fridge, and a washer and dryer. There are lots of options in this additional room! 2-car garage parking with you guessed it - more storage space! Downtown location within walking distance of shops, restaurants, commuter rail and more!

This fabulous house is in a beautiful and unique location, perched on a small hill with a secluded half-acre lot in a very quiet cul-de-sac area near the Winchester/Lexington line, far away from any road traffic and offering excellent privacy. There are 4 floors of living space containing 5 bedrooms and 3.5 bathrooms with two separate laundry areas. The grounds offer stunning front and back yards with a large deck and a gazebo. The property is adjacent to a lovely forest with a pond (Whipple Hill/Smith Pond). A short walk away from Wright-Locke farm and a short drive to shops, malls, and major routes with an easy commute to main business areas. Plenty of leisure facilities nearby including swimming pools, tennis courts, golf courses, skating rinks, gyms, restaurants, etc. Importantly, this house is in one of the best school districts anywhere and the Town of Winchester is renowned for its charm and the quality of life it offers.

NEW CONSTRUCTION! This spacious 6 bed, 6.5 bath home by a top local builder has it all! With over 6,300sf of living space you won't want to miss this stunning home. The first flr offers a gourmet kitchen w/ oversized island w/ seating/ quartz countertops, high-end appliances, & breakfast nook/dining area. Off the kitchen is a spacious family rm w/gas fireplace & direct exterior access w/ sliders leading to a large patio & great yard. The first floor also offers a guest bedrm or home office w/ full bath, mudroom and powder rm. The second level primary suite includes huge walk-in closet, lavish bath w/double vanities, oversized shower & soaking tub! Three additional beds, 2 full baths & laundry room finish this level. The finished third flr is a large loft/playroom/gym w/ full bath. Finished lower level media/ rec room, additional bedroom w/ full bath and wine cellar. 2 car garage direct entry to great mudroom! Conveniently located just 7 miles north of Boston nr Hospital & the Fells!