Winchester MA Real Estate & Homes for Sale

Nestled in sought-after Symmes neighborhood this timeless home was renovated in 2019-2020 providing a refreshed layout and modern amenities while keeping the home's original charm. The gracious foyer leads to a front to back living room with fireplace, window seat and French doors opening to a new family room with a walkout to the patio and backyard. The dining room with bow window flows into the refurbished butler's pantry and new modern kitchen complete with new mudroom, half bath, and back entrance to the driveway. The second floor was completely redesigned to include a primary suite with full bathroom, office, two additional corner bedrooms, main bathroom and W/D area for convenience. The partially finished basement offers a versatile space with a recreation room and ample storage, while the full staircase to the unfinished attic presents expansion possibilities. Detached garage with electric is EV ready. Solar panels are a modern touch. Convenient to train, schools and downtown.

Step into luxury living with this meticulously renovated single-level condo. No detail has been overlooked in this exquisite residence. Hardwood floors that flow seamlessly throughout the open concept floor plan, creating a warm and inviting ambiance. Brand new tiled bathrooms, featuring new fixtures, stylish vanities, and pristine finishes. Entertain with ease in the spacious living area complete with a gas fireplace. Benefit from the added convenience of a private garage, providing secure parking and additional storage space for your belongings. Indulge in the exceptional amenities offered by this complex, featuring a well-equipped fitness room, a welcoming clubhouse, and a heated pool. Open House Saturday May 18, 2024, 12:00pm- 2:00pm Sunday May 19, 2024,12:00pm- 2:00pm. Offers are due Tuesday May 21, 2024, at 5:00pm

Nestled in an idyllic neighborhood, this stunning property underwent complete renovation/addition in 2016, ensuring modern comfort & space. As you step through the entry, you're greeted by an abundance of natural light & a sense of airiness that permeates every corner of the home. The open-concept layout seamlessly connects the living, dining, & kitchen, creating an ideal space for both family gatherings & entertaining guests. 1st floor also features home office, walk-in pantry, & mudroom to help keep life neat and organized! Upstairs, a primary suite w/walk in closet & lavish bath, 2 additional bedrms, & a family bath await, along w/2nd flr laundry. 3rd flr provides a private retreat with its own bath & walk-in closet. Finished basement offers xtra space for family rm, exercise area, & storage. Outside, a lush yard w/fire pit, brick patio, & pergola beckons outdoor enjoyment. Conveniently located just .75 miles to Lincoln Elementary, McCall Middle, & downtown Winchester. Welcome home!

Unparalleled masterpiece nestled on prestigious Myopia Hill, just 7 miles from Boston! With its awe inspiring architecture and exquisite design this majestic home is sure to captivate you! From the grandeur of the facade, to the breathtaking all new interior set on meticulously manicured grounds w/ carriage house, this home is like nothing you've ever seen. Boasting 15 oversized rooms spanning over 10,000 sf with 13' ceilings, 7 beds/ 8.5 exquisite lavish marble baths w/ oversized showers & indulgent soaking tubs w/ high end bath fixtures. The kitchen offers a 12' island, top of the line appliances, 48' gas range, w/dual dishwashers, custom cabinetry, wine fridge & pantry w/ dining area & stunning family room w/ sliders to the fabulous stone courtyard featuring a built in outdoor kitchen/w grilling station. Enjoy dinner parties for 20 in the grand dining room, step down formal LR, handsome home office, au-pair quarters & and more. A distinguished home for the most discerning buyer!

This impeccably renovated Cape located just minutes from Winchester town center and the Middlesex Fells Reservation offers modern amenities with charming design. Originally built in 1898, the home underwent a significant renovation in 2021 consisting of a redesigned floor plan to accommodate an elegant chefs kitchen, spacious mud room and powder room as well as an updated primary bath. The renovation included the addition of full home heating and cooling via high efficiency mini-spilts, all new electrical wiring and LED lighting throughout, as well as updated plumbing, ensuring safety and efficiency while offering energy savings and comfortable contemporary touches. The sun soaked bedrooms all offer ample closet space supplemented by addition storage in the attic and partially finished basement. The home features a utility shed with electricity and lighting. Off-street parking able to accommodate three cars! Lincoln School District.

Elegant blend of traditional and modern. This smart home has the conveniences of automated thermostats, doorbell, bedroom and stair lighting system. The chef's kitchen boasts top-of-the-line Viking appliances and commercial-grade fixtures. The spacious walk-in pantry ensures ample storage for all your essentials. The primary bedroom suite is a true retreat, with soaring ceilings, a luxurious freestanding bathtub, dual vanity, radiant heated floors, and an oversized walk-in shower. Venture downstairs to the finished lower-level basement, with built-in wet bar, ideal for hosting guests or enjoying a night in. This versatile space offers the potential for a home theater or gym, tailored to your needs. Outdoor living reaches new heights with the pergola-covered patio, complete with a built-in Blaze grill and outdoor refrigerator, making alfresco dining and entertaining a breeze. With its perfect blend of style, functionality, and amenities, this home sets a new standard for modern living.

Winchester Estate on Lexington line with your choice of Schools! This Mediterranean inspired home provides the ultimate in large,private,charming space!15 rooms on three living levels.Generous rooms throughout.2 car attached garage with lots of outdoor parking.Large,well appointed 2-tier kitchen ideal for large gatherings and entertaining.Over-sized Dining room with beamed ceiling and connecting bright breakfast room.Dramatic Catherdral Living room with Grand 2-story fireplace leads to 3rd level,upper loft style Study complementing an adjacent home office.6 large bedrooms on both first and second levels.Comfortable,huge first floor family room with oversized stone fireplace.An unequaled space for family,friends,and years of enjoyment.Abutting 100 acres of private,lush conservation land only minutes to beautiful downtown Winchester.Close proximity to corporate hubs in Burlington,Woburn,Waltham and Wilmington.#1 Vinson Owen Elementary School district.Rare lifetime opportunity awaits you!

Nestled in Winchester's esteemed WEST SIDE, this Colonial gem epitomizes modern luxury. This includes an iPad-operated control system for sound, heat, alarm, and property security camera! Spanning 4 floors, the main level invites with a grand living and family room adorned with a gas fireplace and soaring ceilings. Culinary delights await in the oversized kitchen boasting granite counters, SS appliances, and a wine fridge. Work from home in the stylish office, with a full bath and bedroom nearby. Ascend to the master suite oasis, with fireplace, dual walk-in closets, and a spa-like bathroom. Discover a junior en-suite and 2 additional bedrooms, 2 baths, & laundry on this level. The 3rd floor retreat offers versatile space for teens or an au pair, complemented by a full bath. Abundant storage throughout. The finished lower level boasts a media room and wet bar for entertaining. A spacious 3-car garage and entirely fenced in yard, this home beckons you to live luxuriously! WELCOME HOME!

Opportunity knocks in Winchester to own a beautifully maintained South facing home on a Sun-drenched corner lot! Gorgeous landscaping surrounds the large front yard and private fenced in backyard, an oasis for entertainment! Features include a 2-car garage with additional off-street driveway parking and irrigation system. The 1st level offers an updated kitchen/dining room with radiant floor heat and living room open concept with a large glass sliding door providing bright open views of the outdoor living space. It also includes a renovated full bath and a large bonus room that can be used as an office or main level bedroom equipped with loads of closet space. On the 2nd floor there are three large bedrooms that include a primary with a great walk-in closet, and large renovated bathroom. Conveniently located minutes from downtown, walking distance to the commuter rail, Middlesex Fells, blocks away from the newly renovated High School, and an expedient route to downtown Boston!

This captivating colonial home is designed to embrace openness and natural light. The first floor welcomes you into a spacious fireplaced living room, complemented by an adjacent private office space. French doors lead you into the family room- featuring skylit cathedral beamed ceilings, a pristine view of the backyard and an open floor plan that seamlessly extends into the kitchen/dining area. The dining room completes the first floor, creating a harmonious living space with a great circular flow. On the second floor, discover the primary bedroom with an en-suite full bath and walk-in closet, plus two add'l spacious bedrooms and a second full bath. Venture to the third floor, where two more bedrooms await, offering endless options for private spaces or other accommodations. The lower level provides ample storage and a game room, complete with a beautiful cedar closet. Outside, enjoy the expansive two-car garage and inviting backyard, providing ample space for some summer relaxation!

Nestled on Myopia Hill, close to the Winchester Country Club this grand colonial is unparalleled and is an entertainer's dream! Its unique design with large scale rooms caters to both family gatherings and lavish parties. The sun-drenched Great Room, boasting 16ft cathedral ceilings, majestic windows, and a towering stone fireplace is the focal point of this fabulous home w/ French doors leading to a gorgeous stone patio & rear yard. The bright and cheery kitchen overlooking the rear yard offers a casual dining area w/ plenty of cabinetry, w/adjacent mudroom, pantry & 2 half baths. A stunning home office, formal LR w/ fplc, and formal dining w/ 9' ceilings, crown molding & hardwood floors completes this floor. The Primary suite offers a spa like bath, fplc & 2 walk in closets w/ views of the mystic lakes & Boston skyline! 3 additional large bedrooms & full hall bath. Lower level offers a home gym plus kids dream playroom, mudroom & direct entry to oversized 4 car garage!

Step into the epitome of family living with this expansive Winchester colonial. Featuring 4 bedrooms and 2.5 baths, this home is nestled in an ideal family-friendly neighborhood within the prestigious Ambrose school district. The heart of the home is the renovated kitchen, boasting stainless appliances and ample storage, seamlessly integrated into the open floor family area. Enjoy direct access to the rear deck, overlooking the stunning fenced-in flat yard, perfect for outdoor gatherings and play. The inviting living room and sunroom offer versatility, ideal for a home office or relaxation space. Retreat to the primary en-suite, flooded with sunlight, complete with a full bath, laundry & ample storage. Three well-appointed bedrooms feature walk-in closets for added convenience. The finished lower level provides expansion opportunities. With proximity to Wedgemere Train Station, Upper Mystic, and just a short 15-minute commute to downtown Boston, this home offers convenience & comfort!

New! A carefully crafted Colonial that has an original birthdate in 1938 is transformed with new construction with all the 2024 amenities you are looking for. A location at the end of a cul de sac is a private hilltop retreat around the corner from the soon to be new Lynch Elementary School under construction, ready in Fall 2025. A short hop to Horn Pond recreation areas, seasonal views of Winter Pond. Included in the 11 rooms are 5 bedrooms, 6 baths, 4 full & 2 half, with 2 ensuite, a bonus 3rd floor open space with bedroom and bath, lower level game room with half bath. A breezeway connects the heated 2 car garage to the kitchen and provides a large mudroom entry. The bright, open kitchen with farmhouse sink, center island, separate drink bar and frig, and stainless and paneled appliances overlooks the large, level back yard with stone patio. Traditional details, too, like crown moldings, gorgeous hardwood floors. State of the art heating and cooling. Home Energy Rating Certified.

Your dream home in the perfect location awaits! This brand-new construction residence has an unparalleled blend of luxury, convenience & comfort. Be a part of the Ginn/Rangeley/Central community, close to the vibrant town center, schools & train. The stunning open floor plan offers a high-end kitchen anchored by a large island with seating, a dining area & a wet bar. This flows easily to the spectacular family room with high vaulted ceilings, loads of natural light, a fireplace & access to a spacious deck. A formal dining room, living room, mudroom & powder room complete this floor. Upstairs, the large primary suite is an oasis with an elegant large bath, a big walk-in closet & soaking tub. 3 other bedrooms complete this floor, including an en-suite guest room. The third floor is sure to be a hit with a 5th bedroom & bath, plus a spacious study or playroom. The basement has a massive media room, wet bar, gym & full bath! Oversized 2-car garage, large landscaped yard and a big deck.

Introducing 19 Churchill Road! This inviting home offers 3-4 bedrooms, 2 bathrooms, and 2 levels of spacious living area. The cozy living room and family room each boast a wood-burning fireplace, perfect for creating a warm and inviting atmosphere for every member of the family. The dining room is ideal for hosting intimate gatherings, while the eat-in kitchen offers a delightful space for casual meals. With exterior access to a deck, you can easily enjoy al fresco dining or simply bask in the tranquility of the backyard. Speaking of the backyard, nature lovers will adore the gorgeous wooded setting. It's the perfect spot to unwind and connect with the beauty of the outdoors. Convenience is key at 19 Churchill Road, with its amazing location providing easy access to I-93 and I-95, making commuting an absolute breeze. Whether you're heading to work or venturing into Boston, you'll appreciate the seamless connectivity this location offers.

Your chance to be the 2nd proud owner of this meticulously maintained home in the heart of Winchester, where luxury living meets timeless elegance. This magnificent property offers unparalleled comfort & sophistication, boasting 5 bedrooms, 5 full & 2 half bathrooms across its sprawling 6,700+ floor plan. As you step in, you are greeted by a beautiful bridal staircase and marble flooring. The 3 fireplaces add a touch of ambiance and charm to each floor. Entertain guests in style in the spacious living areas, which seamlessly flow into the gourmet kitchen, complete with sub-zero refrigerator, Thermador oven, wolf induction cooktop, custom cabinetry, and granite countertops. The master suite is a true sanctuary, featuring a spa-like ensuite bathroom. Four additional bedrooms offer ample space for family and guests, ensuring everyone has their own oasis to retreat to. The basement offers additional space for a entertaining, workshop, gym and plenty of storage.

This is not an opportunity you want to miss! You'll be in awe of the LR with massive wall length window, brick accent wall with fireplace, and vaulted ceiling. Formal DR leads into the kitchen with lovely cabinetry & plenty of natural light. Boasting 3 bedrooms and 2 full bathrooms great for hosting guests, friends and family. Gorgeous sunroom offer brick accents, wood ceiling and walks out to the brick patio. Finished basement expands the living area even further great for a family room, home office, gym... whatever you need! Settled on over half an acre so you have plenty of lawn space to make yours all Summer long! Settled minutes from Whipple Hill Nature Preserve with walking trails, golf courses, Medford Boat Club, schools, Rt 2A and more.

SO much POTENTIAL!! Build equity with this charming 3-4 bedroom, 1.5 bath property perfectly situated in a desirable location close to town and Horn Pond. This cozy home features an oversized living room with a wood burning fireplace, an inviting formal dining room and a bright and cheery kitchen. A rear addition with bath offers versatile space for a 4th bedroom or family room w/vaulted ceilings, and peaceful views with the walls of windows. The 2nd floor offers 3 bedrooms plus a home office space. Hardwood floors and generous ceiling height throughout. Enjoy relaxing on the picturesque front porch or on the private patio w/ great rear yard, perfect for family gatherings! With a light renovation, you can make this special house your home! Located on desirable Woodside Rd. w/ close proximity to the soon to be NEW Lynch Elementary school, downtown Winchester, Whole foods, restaurants, shops, Winter pond for skating & fishing and so much more! 1 car attached garage with storage & parking

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 loaded with natural light and architectural detail. Custom features include a gourmet eat-in kitchen w/ granite countertops, high-end appliances, secondary prep area, and fabulous outside dining options from the oversized deck. The spacious fire-placed family room, banquet-size dining room w/ wine-column, private home office and bedroom w/ en-suite bath complete the first floor. Luxurious primary suite w/a large balcony, expansive walk-in closets & spa-like bath w/ dual vanities, an oversized shower, and a lavish soaking tub on upper level, along w/ 3 additional en-suite bedrooms and an oversized laundry room. Finished lower level features additional entertainment areas, gym & en suite-bedroom. Fantastic location just up the hill from top-rated Vinson Owen School. Enjoy all that Winchester has to offer.

Stunning cedar shingle and stone Craftsman home nestled in the sought-after East Hill neighborhood. As you step inside, you are greeted by an elegant foyer leading to a chef's kitchen with center island, pantry, granite counters, SS appliances and a sun-filled dining area.The kitchen seamlessly flows to a stone deck, perfect for grilling and alfresco dining. Large family room wrapped with windows featuring a stone fireplace, while the dining room with wainscoting and butler's pantry provides a touch of sophistication. The living room offers a fireplace and a wet bar leading to a study with French doors opening to a stone patio in your private back yard. The second floor offers 5 nicely appointed bedrooms with built-out closets, the private primary suite has walk-in closets and a large bath. Finished lower level provides additional flexible living space with a full bath and storage. Views from every room and the most amazing sunsets on the front porch. Private yard and 3 bay garage.

: This NEW RENOVATION HOME sits on an extremely level 9500 sq ft lot affording its new owner a myriad of options in both indoor and outdoor future living options. Moving in condition. Located on a small dead end provides that community feel and a limited amount of traffic. Tall mature plantings provide privacy for outdoor activities and entertaining. Inside you will find well maintained hardwood on both levels, a spotless kitchen with gas stove, a generous living room, and a dining room. Open kitchen offers wood burning fireplace and full bath with its own heating zone. Second floor is where you will find three bedrooms and a full bath. Easy access to major transportation routes and walking distance to downtown with its diverse options for shopping, dining, as well as one of Winchester's two commuter rails..

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*

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.

NEW PRICE...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 (now being used as a den) with full bath and large closet . One of the highlights of this unit is an exterior door which allows entrance directly into the unit. Also, it allows for easy access to outdoor seating The custom moldings and architectural details add a special touch throughout along with hardwood floors. It includes a deeded garage and an additional 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.

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!