Winchester MA Real Estate & Homes for Sale

Bring your vision & transform this diamond in the rough into the jewel of Mystic Lake! Nestled on a quiet street outlining the lake shores, this spacious 4-bedroom, 3.5-bathroom home offers breathtaking views & endless potential. The 1st floor includes a large, light-filled kitchen primed for a modern makeover with an abundance of windows & french doors opening to a deck. A front-to-back living room w/ fireplace, large dining room w/ two china cabinets, mudroom, half bath, & office/playroom w/ sliders to a deck complete this floor. The 2nd floor features two wings. On one side you will find a primary bedroom w/ fireplace, full bath, & walk-in cedar closet. Two additional bedrooms & another full bath are also on this level. On the other wing above the attached garage you will find another suite w/ vaulted ceiling, full bath & large picture window framing views of the lake beyond. Partially finished basement w/ a 3rd fireplace. This home is your canvas to create a spectacular retreat.

Welcome to your next home! Classic 1930s Colonial nestled just steps away from the serene Middlesex Fells Reservation. Convenient access to 93 & 95, minutes from downtown Boston & within close proximity to town center, commuter rail & schools. Plenty of upside and possibilities here. Live in as-is or create your own vision for this lovely 3 bed, 1 bath home. Upon entry, a lovely foyer invites you inside, setting the tone for the warmth and character that permeate throughout. The first level offers a sun-filled living room with fireplace that flows into the dining room which boasts a built in China cabinet, and eat in kitchen with direct access to the private backyard. Three bedrooms with generously size closets, a full bath and linen closet are upstairs. The basement offers additional space for recreation, a workshop, or storage, catering to your evolving needs and lifestyle. Don't miss this chance to make your mark on this Winchester residence.

This spacious home with thoughtful design details was carefully maintained through the years by original owner/builder. On first floor, be welcomed to a large living room with fireplace (plenty of space for multiple seating zones/uses), the dining room has custom built in storage that can be removed, half bath, enclosed porch and beautifully designed kitchen with eating area and bright sunny windows. On 2nd floor-find 4 ample bedrooms with hardwood floors and a full bathroom with double sinks and linen closet. The walkup attic has plenty of room for storage and might offer expansion potential. In the basement, you'll say WOW! High ceilings and a fireplace make it obvious that finishing a space similar to the living room would be an investment with great return! What else? A shed outside and a large flat back yard. Possibly space to build a detached garage and/or expand the kitchen and add a family room. Central AC 2021. Lovely enough to move right-in and improve in years ahead.

Top East side neighborhood! Don't miss this renovated & expanded 3BR home offering a great layout, flooded w/natural light. Spacious Living room w/wood burning fireplace, adjacent sun room, office/play room plus a stunning eat in kitchen w/ ample storage, prep space, large island & dining area w/ vaulted ceilings & picture window overlooking the well manicured yard. The main floor also includes a formal dining room & half bath w/ direct access to patio/yard. Upstairs the 2nd floor has 3 nicely sized bedrooms & full hall bath. The finished lower makes for great recreation space w/ large open room w/ built in desk, half bath, gym area, an adorable kids play room w/hand crafted club house door, laundry & plenty of storage! This home is equipped with a new AC system, 1 car garage w/EV hookup. Located on a great street in top location close to Winchester center! Hardwood floors & nice ceiling height throughout. A perfectly sized yard & patio complete this ideal home. *Offers Due 4/30 3pm*

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

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.

Back on. market, buyers got cold feet! Welcome to 18 Krik In the beautiful town of Winchester, just 9 miles from Boston and only 26 miles to NH! The best of both worlds. This home includes 2 bedrooms on the upper level, 1 on the main and 1 in the basement, all floors having a full bath and with the basement having its own exterior door and water pipes behind the bar ready for tie ins, this makes a perfect spot for extended family or an older child to have their own little space. When entering you will notice the beautifully freshly painted walls, fireplaces and ceilings. Accompanied by stainless steel appliances all throughout the kitchen, which will finally bring you to the sunken family room in the rear of the home, leading out to the deck. This home is just minutes away from Winchester high, horn pond in Woburn, and directly across the street from McDonald field which includes a playground, baseball/soccer fields and a basketball/tennis court. *Some photos have been virtually staged

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.

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 has just been completed and is ready for a new owner to make it their 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!

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