Winchester MA Homes for Sale & Real Estate

Home for Sale in Winchester

A timeless home of exceptional craftsmanship on the coveted slope of Myopia Hill, offering tranquil views of lush gardens and rolling hills. Thoughtful architectural details enrich every space, while multiple patios and wrap-around porch create an effortless flow between indoor& outdoor. The gracious main level unfolds into beautifully connected living spaces, featuring an office, elegant dining room, chef?s kitchen adorned by enchanting breakfast area and an inviting living &family room anchored by a stone fireplace. The upstairs primary suite is a private retreat w/ its own balcony, dressing rooms, cedar closet & a spa-inspired bath. The private backyard?with its historic stone hunter gazebo, fire pit, mature trees and layered plantings?offers both openness and seclusion. Within close proximity to Winchester Country Club and offering a swift commute to Boston & major highways, this exceptional property delivers privacy and prestige in one of Winchester?s most desirable enclave.

Home for Sale in Winchester

Experience the perfect blend of craftsmanship & modern luxury in this stunning custom-built brick ranch. From the moment you enter the spacious front foyer, you?re greeted by soaring cathedral beamed ceilings & an inviting open-concept layout that seamlessly connects the living, dining, & family areas?ideal for effortless entertaining & comfort. A thoughtfully designed private wing includes 4 spacious bedrooms & two full baths, offering both privacy & convenience. The expansive mudroom provides access to the two-car garage & side entrance, blending practicality with elegant design. The fully finished lower level is an entertainer?s dream, complete with an open game & playroom, large gym, full bath, & generous laundry room. Pet owners will appreciate the custom-designed dog kennel with exterior access & a private wash area?every detail has been considered. Impeccably maintained & beautifully appointed, this exceptional home offers a rare combination of style, space, & sophistication.

Home for Sale in Winchester

Discover this brand-new custom-built home featuring 6 bedrooms and 7 full baths, located in a highly desirable neighborhood just steps from VO Elementary School. The expansive 1st floor welcomes you with soaring ceilings and an elegant layout, including a sophisticated living room, family room, and private home office. The chef?s kitchen is a true centerpiece, boasting premium Thermador appliances, custom cabinetry, and a large island that flows seamlessly to an oversized deck?perfect for entertaining or relaxing. Upstairs, the 2nd floor offers spacious ensuite bedrooms, the luxurious primary suite with a walk-in closet and direct access to a private deck. Additional highlights include a butler?s pantry, mudroom, central air, and a tankless water heater for comfort and efficiency. The finished walkout lower level provides versatile space for a gym, entertainment area, and additional suite. Don?t miss the opportunity to own a residence designed with both comfort and style in mind.

Home for Sale in Winchester

Lovingly maintained and tastefully renovated, this spacious three bedroom, two bath ranch with 3 car garage will impress! This remodeled open concept home is set on an oversized 16k lot and features a beautiful kitchen with custom cabinetry & dining island ideal for both every day living and entertaining. The main level also offers an inviting living room with bay window & fireplace, dining room & access to three season porch and deck.This home includes three spacious bedrooms and an updated full bath on the main level. The finished lower level provides additional living space featuring a large family room w/fireplace & walls of windows overlooking yard, a home office, a full bathroom and a dedicated workshop. The expansive lot is stunning, offering peace and tranquility just moments from the town center. Enjoy the convenience of an attached garage plus a second oversized 2 car garage, a rare find in Winchester! Don't miss this gem close to Boston & all major routes, move right in!

Home for Sale in Winchester

Situated at the corner of Ginn Road neighborhood, this home was custom built by a premier local builder- with its dramatic design, it is a must see! Ideally located near town center w/ easy access to the commuter rail, Mystic lakes trails & beach, Ginn playground & the vibrant town center. This 7000sf, 7 BR home is perfectly designed for todays living w/ au-pair & multi generational options. A dramatic two-story foyer with stunning lit cove ceiling welcomes you into the home & flows into the formal living and dining spaces. The oversized chef?s kitchen features high end cabinetry, top-tier stainless appliances, large granite island w/dining area & fireplace. The inviting family room is just off the kitchen;The primary suite offers a lavish walk-in closet, large bath w/radiant heat & steam shower. Four additional bedrooms include en-suite baths, plus a separate-entry au pair suite. The finished lower level includes a bar, flexible family room/bonus space, gym & storage. Floor plan att'd

Home for Sale in Winchester

Step into timeless charm in this STUNNING, impeccably maintained Dutch Colonial Revival home, where historic character meets modern living! Thoughtfully updated with 4 bedrooms and 4 baths, including TWO ENSUITE RETREATS?one private and perfect as a 4th bedroom, au pair suite, studio, or office. Endless flexibility! The updated kitchen shines with abundant cabinetry, center island, granite countertops, gas range, and stainless-steel appliances. First-floor laundry! Soaring ceilings and sun-filled rooms with ALL DAY NATURAL LIGHT deliver effortless comfort. Original balusters and custom built-ins preserve the home?s classic soul. Outside, enjoy a FENCED YARD, lush, curated landscaping, and raised garden beds with rich soil. An aluminum one-car garage and off-street parking add ease. Set in a coveted Winchester location just 0.4 miles to the vibrant town center, farmers market, and train?this is a rare blend of space, charm, walkability, and convenience. Get ready to fall in love!

Home for Sale in Winchester

Expanded Cape blends timeless charm with thoughtful updates, offering inviting living spaces designed for comfort and connection. A fireplaced living room with hardwood floors and French doors sets a warm tone, flowing into an elegant dining area accented by custom built-ins and refined detailing. The kitchen serves as the heart of the home, featuring stone countertops, stainless appliances, and a generous island that opens to a sunny dining area with direct access to outdoor living?ideal for everyday enjoyment and entertaining. The main-level primary suite, along with a versatile family room or optional 5th bedroom, provides flexibility for a variety of living needs. Upstairs, 3 additional bedrooms offer comfortable retreats with excellent closet space and natural light. A finished lower level extends the living area with adaptable space and walk-out access to the garage. Outdoor spaces include a welcoming porch, deck, & patio, creating a peaceful setting for gatherings & relaxation.

Home for Sale in Winchester

Cleverly reimagined for modern living, this energy-efficient Craftsman bungalow is ideally located in Winchester with close proximity to the natural beauty of the Middlesex Fells and the shops, dining and commuter rail of the town center. Thoughtfully expanded and renovated, the home features newer systems, windows and roof, among too many other updates to list. A functional mudroom with custom storage welcomes you inside, where the living room flows seamlessly into an exquisite chef?s kitchen with premium appliances, dual sinks and a dining room overlooking the landscaped, fully fenced yard. A spacious bedroom and full bath complete this level. Upstairs offers three additional bedrooms, two full baths and laundry, highlighted by a generous primary suite with walk-in closet and spa-like bath, complete with soaking tub and extra large shower. Owned solar panels, EV charging, a one-car garage, and a versatile lower level with bonus room complete this exceptional offering.

Home for Sale in Winchester

Timeless architecture blends beautifully with curated updates designed for modern living in this classic Colonial. Sunlight pours into the newly renovated gourmet kitchen, where beautiful cabinetry, premium appliances, and thoughtful design create an inviting heart of the home for both everyday living and elegant entertaining. A gracious front-to-back living room offers exceptional scale and flow, anchored by a fireplace and an abundance of natural light. Attached, a charming three-season sunroom provides a tranquil retreat, seamlessly connecting indoor comfort with the beauty of the outdoors. 4 bedrooms and 2 baths complete the second floor. Bonus: extra 900 unfinished square feet in the attic just waiting for your ideas! The basement offers one of the best finished areas we've seen, with vintage hardwood floors and a fireplace. A thoughtfully landscaped yard feels like a private oasis, with room for play or private mornings. Impeccably maintained, in a prime Flats location.

Home for Sale in Winchester

Nicely renovated & GREAT price!! This unique 3 bed, 1.5 bath townhouse offers a spacious layout and has a private level large back yard, and 2 car parking! This home offers a spacious open living/ dining room with hardwood floors and plenty of natural light. The second floor offers 3 spacious bedrooms with large closets and a full bath. The updated interior makes this home move in ready. Gleaming hardwood floors run throughout, and ductless mini splits provide AC and heat. The basement offers excellent potential to be finished, creating the perfect space for a family room, home office, or gym. Numerous windows create a bright and inviting feel. Low condo fee and close to everything Winchester has to offer. Located in the Lynch School district, brand new as of the 2025 school year. Easy commuter rail access into Boston with convenient access to Routes 93 and 95. Just minutes from Winchester Center and only 7 miles from Boston.

Home for Sale in Winchester

Spacious newly gut renovated colonial set back on a cul-de-sac! Unbeatable location in quiet neighborhood less than a mile from all Winchester's amazing public schools and Wedge Pond. Hardwood floors throughout with gorgeous kitchen featuring huge island, large living and dining rooms. A vaulted family room with authentic barn board detailing sits adjacent to the kitchen, opening to a large private deck for seamless indoor-outdoor living. Offering 6 beds, 3 full baths, and 2 half baths, the primary suite boasts a soaring vaulted ceiling and a walk-in closet nearly the same size, while spa-like modern baths complement generously sized bedrooms. The lower-level recreation room, complete with sliders to a large patio, provides additional space for entertaining or relaxing. Two car garage complements this ideal location, with short drives to Whole Foods, H-Mart, Burlington Mall, nature at Middlesex Fells and Mystic Lakes state parks, and easy access to Boston and surrounding areas.

Home for Sale in Winchester

Magnificent newer sun filled colonial w/oversized rooms offering over 8,000 sq ft of beautifully finished living space featuring 7 grand BR's, 7.5 BA across 4 levels w/a 3-car direct entry garage. This expansive home showcases exceptional craftsmanship including custom built-ins, fine cabinetry, decorative moldings, 4 fplc & a great layout. The newly renovated kitchen features sleek quartz countertops, oversized island, 2 dishwashers & butler?s pantry w/ice maker & wine fridge flowing into formal DR & LR plus a fireplaced FMRM overlooking a meticulously maintained yard. Each oversized bedroom offers an en-suite bath, sitting area & walk-in closet, providing comfort & privacy throughout. The 1st flr includes a private office w/wet bar plus a lavish bedroom wing ideal for guests or multi-generational living. The 3rd floor suite features a full BA & 2 closets, while the finished lower level adds media/game/gym areas w/access to stunning gunite pool, complimented by lush outdoor landscape!