A quintessential New England Colonial offers timeless charm and a welcome presence, introduced by an inviting front porch that sets the tone for what lies within. The gracious foyer opens to a sunlit living room with warm wood floors and classic details, creating an inviting space for easy living. Pocket doors lead seamlessly into the dining room, where a fireplace and a beautifully curved bow window add architectural character and a sense of tradition. The kitchen connects effortlessly to cascading decks and a picturesque backyard that abuts conservation land with Horn Pond Brook, providing a peaceful and natural backdrop. Upstairs offers comfortable bedrooms and a full bath arranged for privacy and ease. The walk-up attic features a finished room and a separate foyer -awaiting heat for expansion potential. A walk-out basement offers additional flexibility for storage or future use. Outdoor living is enhanced by multiple decks and porch spaces designed for enjoying the serene setting
Exceptional Colonial Revival in one of Winchester’s most sought-after Sheffield neighborhoods, known for its tree-lined streets and a shared community green. Timeless architecture meets modern livability across four finished levels. The chef’s kitchen features a large island, walk-in pantry, wet bar, and custom cabinetry, opening to a spacious family room with gas fireplace. Formal living and dining rooms offer hardwood floors, crown molding, and abundant natural light. The primary suite includes walk-in closets and a spa-like bath, with additional generously sized bedrooms and baths. The 3rd floor provides flexible living with bedroom, study, bonus room, and full bath, while the finished lower level adds recreation space. Recent improvements include exterior paint (2024), perimeter fencing with gated driveway, ornamental landscaping, enclosed mudroom storage, and a custom Dutch door. Detached 2-car garage and private yard. Close proximity to Winchester Center and Wedgemere Stations.
Designed for modern living and effortless entertaining, this home’s exceptional open-concept main level sets it apart from the moment you enter. Anchored by a chef’s kitchen with stone countertops, an oversized island, and premium Viking appliances, the space flows seamlessly into the family room with a striking shiplap fireplace and direct access to a spacious composite deck. Set in a desirable neighborhood, this fabulous 6-bedroom, 3.5 bath home offers luxury finishes at an exceptional value. The primary suite provides a private escape with a walk-in closet and dual vanity, complemented by three additional second-floor bedrooms—two with walk-in closets—a shared bath, and laundry. A large unfinished attic offers future expansion potential, while the finished lower level adds flexibility with full-size windows, a sixth bedroom, full bath, recreation space, and a mudroom with direct garage entry. Enjoy a landscaped, fenced yard with irrigation, close to top-rated schools.
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.
Experience the perfect blend of luxury and effortless living in this stunning custom-built residence, thoughtfully rebuilt and expanded to offer a sophisticated, maintenance-free lifestyle. Bathed in natural light, the flexible floor plan begins with a magnificent first-floor primary suite featuring a marble-clad bath, soaking tub, and walk-in shower. The heart of the home is a chef’s kitchen anchored by a granite island and premium Bosch appliances. Entertaining is seamless, whether hosting formal dinners by the wood-burning fireplace or relaxing in the spacious family room with its sleek gas fireplace and glass doors to the yard. A bright four-season sunroom offers a peaceful retreat year-round. The second level provides four additional bedrooms, two full baths, and a convenient second laundry. Downstairs, a heated bonus room with a third fireplace full bath serves as a gym or media room. Sited on a flat lot steps from Wedgemere station, this is suburban living at its best.
Fantastic opportunity to own in Winchester! This inviting home is move-in ready and offers a flexible layout. The bright living room with picture window opens to the dining area, with a kitchen and a convenient half bath with laundry just beyond. Upstairs features a comfortable primary bedroom, sunny home office, additional bedroom, and a full bath. The third-floor bedroom spans the length of the home with windows at both ends, ideal for a playroom, lounge, or guest suite. The lower level presents useful space for storage, a workshop, or playroom with direct access to the backyard. Located near Winchester High School and less than half a mile to Winchester Center with shops, dining, commuter rail, conservation trails, and only 8 miles to Boston.
This exceptional Everett Avenue residence stands among the street’s most distinguished offerings, commanding a premier setting on over half an acre. Renovated in 2023-2025, timeless architecture is seamlessly married to today’s most coveted amenities. Hallmark architectural details abound. Balusters, soaring ceilings, coffered rooms, original crown moldings, mantels, and decorative trim are beautifully preserved, elevated by the warm glow of restored hardwood floors. Generous, light-filled rooms unfold with grace and scale throughout. A newly designed chef's kitchen, new baths, walk-in pantry w/laundry and a classic butler’s pantry with wine refrigerator are some of the highlights. Anchoring the home is an expansive family room, framed by floor-to-ceiling windows overlooking a park-like lawn. A rare offering where architectural pedigree, thoughtful architecture and renovation, and exceptional land converge.
Rarely available ground-floor townhouse at The Willows with easy access to a private garage. This bright and sunny 2-bedroom, 2-bath condo offers the convenience and comfort today’s buyers are seeking. Open concept kitchen with a breakfast bar, and an adjacent dining area—perfect for everyday living or entertaining. The expansive living room is highlighted by a gas fireplace and slider that opens to a private patio area.The generous primary suite includes a walk-in closet and an ensuite bath with double vanity. A large second bedroom also offers a walk-in closet, while the hallway bath features a tub and shower, there is an in-unit laundry and extra basement storage. Amenities include a clubhouse with community room, fitness center, restrooms, and a heated outdoor saltwater pool. Enjoy all that Winchester has to offer, the 2,600 acre Middlesex Fells, vibrant downtown, restaurants, shops, library, farmers market and commuter rail service to Boston.
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.
Welcome home to this completely renovated gem, ideally situated on a corner lot in the highly sought-after Lincoln Elementary School district. Warm, inviting, and truly move-in ready, this home offers the open-concept first floor buyers dream of—featuring a beautiful kitchen flowing seamlessly into the dining and living areas, plus a sunken family room perfect for relaxing or entertaining. Enjoy the practicality of a mudroom located directly off the driveway, along with multiple off-street parking spaces and a two-car garage. The finished lower level includes a full bathroom and flex space ideal for a recreation room, home gym, playroom, or media room. Upstairs, you’ll find three bedrooms, including a lovely primary suite with a spacious bedroom, walk-in closet, and full bath. This home has been thoughtfully renovated from top to bottom, featuring all new systems for peace of mind and modern living. Located just a short walk to Winchester’s vibrant town center and commuter rail.
Exceptional Victorian era gem, steps from Town Center, schools, commuter rail, and the Fells! This spacious period home seamlessly blends modern elegance with timeless charm. It’s special features include: an inviting farmer’s porch, generous living and dining rooms well-suited for entertaining, first floor family room, covered porch for al fresco dining, primary suite with ensuite bath, home office, sun room, central AC (8 mini-splits), Lochinvar heating sys (2025), hardwood floors, 3 fireplaces, and more. The stunning kitchen combines function, design, and quality showcasing custom cabinets, granite countertops, stainless appliances, and tasteful lighting. Bring your design ideas for the third floor and personalize the space for your needs. The lower level, with an outside entrance and a half bath, is well suited for an in-law suite, or au pair accommodations. The lovely backyard with its Zen Garden includes many thoughtfully organized plantings and flowering trees. Welcome home!
NEWER CONSTRUCTION! This 2020 home showcases 5 beds, 4 baths-4300sf of style & luxury situated on the corner of Loring Ave. The home features high ceilings, hardwood floors & a stunning sunny open floor plan w/ eat in kitchen, center island, custom cabinetry, stainless appliances & walk-in pantry. Formal dining room & dramatic oversized family room will impress, featuring vaulted ceilings, gas fireplace and plenty of windows.The first floor also includes a bedroom suite w/ full bath! Upstairs you'll find 3 spacious bedrooms, including the primary suite w/ walk-in closet & beautiful en-suite bath w/ large shower, tub & double vanity sinks. Additional BR5 & bath on the 3rd fl. The finished lower level offers a family room w/ bar & large media/playroom. A fenced in yard, deck/ patio & direct entry two-car garage complete this home. Enjoy all the area has to offer including McDonald field playground, restaurants, shops, schools, train to Boston, Bike-paths & more! Only 7 miles from Boston!
Beautifully maintained and freshly painted 1-bedroom condo at Parkview Condominiums in Winchester. This bright unit features an open layout with peaceful views overlooking the pond. The low HOA fee includes heat, hot water, electricity, and air conditioning—an exceptional value. Highlights include a spacious living area, updated kitchen with new stainless steel appliances, a large bedroom with excellent closet space, and on-site laundry. Enjoy community amenities such as an in-ground pool, clubhouse, landscaped grounds, and on-site security. Conveniently located near shopping, schools, restaurants, and major highways.
Beautiful 2BR/2BA waterfront condo at Wedgewood Place located at 666 Main Street. This open-concept corner unit features a bright living/dining area with private balcony, granite counter-tops in the kitchen, and hardwood floors. The primary bedroom is bright with lots of windows and offers a walk-in closet and en-suite bath. Additional highlights include in-unit laundry, assigned parking, elevator and access to an in-ground pool. Enjoy the landscaped waterfront grounds or take a short walk to Winchester Center, coffee shops, restaurants, and the commuter rail. Move-in ready and perfectly located! Sold in As-Is condition.
Beautiful newer-construction home in a wonderful Muraco school location! This meticulous 4-bed, 3.5-bath property offers modern living with an inviting open-concept layout & high ceilings spanning across 4 finished levels with attached garage! The stunning chef’s kitchen features high-end appliances, large island & abundant storage, flowing seamlessly into the dining area & living room with a gas fireplace, perfect for everyday living and entertaining. A slider leads out to the expansive fenced yard w/ patio for outdoor enjoyment. The second level offers 3 spacious BR’s& 2 BA including the primary suite w/ spa-like bath & great closet space. The finished 3rd floor.provides a fantastic bonus/media room, home office, fitness space, or guest suite w/ a full bath!.. the finished LL adds more family space! Central air & thoughtful finishes throughout make this home truly turn-key.Enjoy easy access to schools, town center & commuter rail all nearby!—don’t miss this exceptional opportunity
Beautiful newer-construction home in a wonderful Muraco school location! This meticulous 4-bed, 3.5-bath property offers modern living with an inviting open-concept layout & high ceilings spanning across 4 finished levels with attached garage! The stunning chef’s kitchen features high-end appliances, large island & abundant storage, flowing seamlessly into the dining area & living room with a gas fireplace, perfect for everyday living and entertaining. A slider leads out to the expansive fenced yard w/ patio for outdoor enjoyment. The second level offers 3 spacious BR’s& 2 BA including the primary suite w/ spa-like bath & great closet space. The finished 3rd floor.provides a fantastic bonus/media room, home office, fitness space, or guest suite w/ a full bath!.. the finished LL adds more family space! Central air & thoughtful finishes throughout make this home truly turn-key.Enjoy easy access to schools, town center & commuter rail all nearby!—don’t miss this exceptional opportunity
This is a great opportunity for a moderate-income eligible family to purchase a home in this beautiful town of Winchester. The duplex has 3 levels of finished living space. Third level is newly finished with a main bedroom suite. Amazing stained-glass windows on the first level, also includes fireplaces in 4 rooms. Loaded with character and charm. See attached application with details regarding deed restrictions.
Welcome to a stunning new-construction home in Winchester’s coveted Lincoln Elementary district, where thoughtful design and refined style come together effortlessly. Every detail has been curated to create a warm, inviting vibe, from the gorgeous family room with custom walnut built-ins and artful lighting to the seamless flow of the open yet intentionally defined floor plan. The impressive kitchen and dining area form the heart of the home—perfectly suited for lively entertaining, relaxed gatherings, and everyday living. Upstairs, the primary suite offers a luxurious retreat, while the spacious third-floor teen suite provides comfort, privacy, and versatility. The finished lower level—with its full bath—adds tremendous bonus space for play, guests, or hobbies. Blending modern craftsmanship with timeless appeal, this home delivers exceptional living just a stone’s throw from the Middlesex Fells Reservation, where nature’s beauty is right at your doorstep.
Beautiful terrace-level 1-bedroom condo in Winchester! This garden-level unit offers tranquil pond views and direct patio access just outside the pond. The condo features a bright, open layout with large windows bringing in natural light. HOA fee includes heat, hot water, electricity, and air conditioning—making it easy and affordable to maintain. Enjoy a peaceful setting with access to the community pool and well-kept grounds, all within a short distance of Winchester Center, shops, and public transportation.
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.
Property to be sold in as is condition. This unit is subject to the Winchester Housing Corp resale procedures. See document section for additional details. Buyer is responsible for any and all inspections needed for the sale of this unit. This unit is vacant and easy to show. See attachment for qualification calculations.
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.
Winchester is located in Massachusetts. Winchester, Massachusetts has a population of 22,875. Winchester is more family-centric than the surrounding county with 48.34% of the households containing married families with children. The county average for households married with children is 35.9%.
The median household income in Winchester, Massachusetts is $184,844. The median household income for the surrounding county is $111,790 compared to the national median of $69,021. The median age of people living in Winchester is 42.4 years.
The average high temperature in July is 82.3 degrees, with an average low temperature in January of 19 degrees. The average rainfall is approximately 46.9 inches per year, with 52.7 inches of snow per year.
