Winchester MA Homes for Sale & Real Estate

Home for Sale in Winchester

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 natures 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.

Home for Sale in Winchester

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

Home for Sale in Winchester

A home like no other for the true nature lover! Feel the love at 22 Fells Road perched up high on a pretty street in the Highlands area of Winchester that is tucked away yet close to area amenities. A true sanctuary that one can only dream of just steps from The Middlesex Fells Reservation (bike or hike on endless trails that go on for miles) & offers the most magnificent sunsets from the treetop living room. This wonderful home high a top the road has undergone a 2nd floor addition, updated systems & offers two 1st floor bedrooms & full bath as well as a fantastic primary suite with bonus space perfect for a nursery/home office on the upper floor. This comfortable home showcases casual dining/living rooms with a wonderful wood burning fireplace; finished basement flex space with half bath & a well appointed kitchen (with a built in desk) that seamlessly leads to the rear yard that is fully fenced in & has patio seating, mature trees & gardening opportunity. Welcome home!

Home for Sale in Winchester

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!

Home for Sale in Winchester

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.

Home for Sale in Winchester

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.

Home for Sale in Winchester

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.

Home for Sale in Winchester

WATERFRONT BUILDABLE LOT! Expansive 37,522 Sqft lot (0.86 acres) on the peaceful upper Mystic Lake, home of the Winchester Boat Club and Medford Boat Club. Build your dream home with serene lake views and the distant Boston Skyline. This sprawling lot is located across the street from the Winchester Country Club, minutes from Shannon Beach and Mystic Lakes State Park. Located in both Winchester and Arlington, enjoy all that both towns have to offer from highly rated school systems to bustling town centers with boutique shops, restaurants, cafes and salons. Arlington bodes endless entertainment options such as the historical Capital Theater, and a multitude of recreation activities including the Minuteman Bikeway, used both for leisure and commute. This property is located 1 mile from Ambrose Elementary School, John A. Bishop Elementary School, Stratton Elementary School, and just over a mile from the Wedgemare MBTA Station and Wright-Locke Farm Conservatory.

Home for Sale in Winchester

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 butlers 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.

Home for Sale in Winchester

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 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.

Home for Sale in Winchester

Absolutely charming! Dont miss this elegant condo on a dead-end street just outside of the town center. The heart of the home is a stunning eat-in kitchen with marble counters, stainless steel appliances, breakfast bar and stylish banquet dining area. The spacious living room featuring a fireplace with marble surround, expansive picture window, window seat, and a wall of built-in bookshelves is the perfect place to entertain or relax. Retreat to one of two well-appointed bedrooms, each with beautiful built-ins, large closets, and sumptuous wool carpets. A sunny office/bonus room is located off of the second bedroom. The full bath features marble tile, a tub/shower and ample storage space. Dont miss the private and serene screened-in porch, which provides the perfect spot to unwind. Common features include a landscaped yard, deck, driveway with doorless garage, and basement.

Home for Sale in Winchester

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, theres 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!