Winchester MA Real Estate & Homes for Sale

Cherished home located on a quiet side street in Winchester Highlands, close to the popular Fells Reservation. Flexible layout perfect for today's living with 5 beds & 3.5 baths. The 1st floor features a formal living room with fireplace, expansive family room & open concept dining room/kitchen with new appliances, cherry cabinets and beverage cooler. Two 1st floor bedrooms and a full bath provide options for an amazing in-law suite, hosting guests or as a home office. The 2nd floor has 3 beds, the primary features cathedral ceilings, gas fireplace, an en-suite bath with a soaking tub and a glass-enclosed tiled shower. Oversized rear deck overlooks a private back yard, perfect for summer entertaining. Two-car side entry garage leads to a finished basement great for home gym or playroom. Convenient access to I-93, and minutes from Muraco, McCall, the High School & Winchester center with boutique shops, restaurants, cafes and commuter rail. Showings start at Open Houses Sat/Sun 12-2pm.

Circa 1865,this spectacular Mansard roof Victorian home blends timeless elegance with the modern conveniences of modern family life.Exquisite period detail and appeal abound with leaded and stained glass windows and grand staircase all lovingly maintained. In town location is perfect for shopping and transportation but the private estate like setting has maginificent gardens .large private yard with two patio areas.Inviting oversized front porch has also a screened in porch perfect for entertaining. Gracious formal living room and dining room. Kitchen has a six seat island with granite and stainless steel and also has a dining area and French doors to the patio. Right off the kitchen is a gorgeous family room with a fireplace. Second floor has primary suite with large bath and two additional bedrooms plus washer/dryer area, bath and sunroom.Third floor suite has two additional bedrooms ,office area and a large bath. Enjoy sunset views and walks to Fells Reservation

Extraordinary opportunity to own this updated 4 bedroom, 2.5 bath Colonial abutting the 120 acre Whipple Hill Conservation Area. This home boasts a wonderful-for-entertaining first floor layout, including a spacious living room, dining room with wainscoting, eat-in kitchen, 1/2 bath and family room with beautiful wide-board flooring and fireplace. Access the deck off of the family room. The second floor has the main bath and 4 bedrooms including the front to back primary bedroom with en suite 3/4 bath and 2 double closets. The large finished room in the lower level, well lit by 5 windows, has a direct walk-out to the back yard. The oversized, attached 2 car garage leads directly into the side hall with double entry closet and half-bath. The interior of the home has been recently painted throughout and had new hardwood floors installed on the 2nd floor. All of this sitting on a 1/2 acre lot and next to 1.39 miles of hiking trails. Don't miss this one!

Discover this spacious custom colonial on Winchester's coveted west side! Built in 2004, it's a short walk to Vinson Owen School and Wright Locke Farm. Enjoy abundant natural light in the south-facing great room, flowing layout to dining area and breakfast nook overlooking the patio. The kitchen features ample counter space, a double oven, and a large island to entertain. Adjacent to the kitchen, is a private office with tree canopy views. French doors lead to the sunny family room. Upstairs find a primary bedroom with ensuite bath and walk-in closet, plus three more bedrooms with ample storage. On the 3rd floor, a play space. The finished lower level has a bonus room and full bath. The attached and heated two car garage is accessed via the basement. The level professionally landscaped yard wraps around the side leading to the second patio and more parking. Recent upgrades include exterior painting and new central air. Don't miss this opportunity for comfortable living in Winchester!

Prepare to swoon over this exquisite colonial offering a sprawling backyard oasis in one of Winchester's most desired neighborhoods. This home boasts luxurious renovations, thoughtful design, and magazine-worthy aesthetic. The main level features posh mud and powder rooms, a sunlit living room with a fireplace, and a stunning dream kitchen with a peninsula breakfast bar that opens to the dining room. Glass sliders lead to the deck overlooking the sophisticated private landscape. The second floor reveals 4 bedrooms and 2 full bathrooms, including an expansive primary suite with ensuite, custom walk-in closet for her, and separate closet for him. The lower level includes a versatile play area, family room, or gym, complete with half bath, laundry and direct walkout to an oversized entertainers' patio. The magnificent outdoor space features a sun-drenched heated pool, irrigated gardens, mature trees, elegant fieldstone walls, and a charming pool house- it's the ultimate outdoor retreat!

Experience unparalleled charm in the CORNER and BIGGEST unit at Winchester Crossing. Step into an inviting atmosphere with an open-concept living area, adorned with abundant natural light. Relax in the expansive living room, complete with a cozy fireplace and direct access to a private balcony, ideal for enjoying serene evenings. The kitchen features a breakfast nook, which always offers a peaceful mind for the owner. On the third floor, there are two well-sized bedrooms situated at opposite ends of this level, each complemented by ideal floor plans. Don't miss the bonus area next to the HEATED garage, which can be used as a gym or entertainment area. Garage also offers direct access to the backyard, providing additional outdoor space for relaxation or play. Commuting is a breeze with easy access to the commuter rail, making travel to nearby areas convenient. The location is also close to Macdonald Field, Horn Pond, various enrichment classes, and a host of other fun activities.

Rare opportunity in Winchester to buy a large two-family at a great price! This property offers the ideal blend of investment potential & comfortable living. Each unit features 3 bds,1.5 br & extra-large, separated level lot, providing a perfect setup for rental income or multi-gen living. Top-tier schools & public transportation. This is a must see and won't last! Showings limited to open houses ONLY.

Beautifully maintained & filled w/character & charm! This beautifully renovated home offers high ceilings, stunning updated kitchen flooded w/sunlight, quartz countertops, built ins & cozy dining nook w/ access to spacious private deck overlooking the yard. A Large bow front dining room w/ hardwood floors china cabinet & fire-placed living room create the perfect setting for family & entertaining. The second level has a large primary bedroom w/ floor to ceiling book shelves, newly renovated bathroom w/ double sinks, a second bedroom, home office & laundry area. The third floor offers two additional bedrooms & full updated bath. The basement is nicely finished w/a cozy game/family room, half bath plus work out area, w/ second fridge & plenty of storage. Close to Winchester town center, schools, restaurants, shops & Wedgemere train to Boston, Mystic Lakes beach & walking paths. Enjoy all the amenities of this charming home in top location, w/private entry & the feel of a single family!

Beautifully maintained & filled w/character & charm! This beautifully renovated home offers high ceilings, stunning updated kitchen flooded w/sunlight, quartz countertops, built ins & cozy dining nook w/ access to spacious private deck overlooking the yard. A Large bow front dining room w/ hardwood floors china cabinet & fire-placed living room create the perfect setting for family & entertaining. The second level has a large primary bedroom w/ floor to ceiling book shelves, newly renovated bathroom w/ double sinks, a second bedroom, home office & laundry area. The third floor offers two additional bedrooms & full updated bath. The basement is nicely finished w/a cozy game/family room, half bath plus work out area, w/ second fridge & plenty of storage. Close to Winchester town center, schools, restaurants, shops & Wedgemere train to Boston, Mystic Lakes beach & walking paths. Enjoy all the amenities of this charming home in top location, w/private entry & the feel of a single family!

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. Call for offers by 5pm on Monday, May 20th.

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!

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!

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.

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.

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.