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.
Prime location near town center! This renovated 4-bed, 3-bath home is nestled in a private setting, walking distance to Winchester center and commuter rail to downtown Boston, nearby Middlesex Fells Reservation, High School, shops, and restaurants. Recent upgrades include new basement vinyl flooring (2025), stunning kitchen and second-floor bath renovation (2021), and new Bosch boiler and hot water heater (2018) and more. The sunlit kitchen dazzles with quartz countertops, stainless steel appliances, custom cabinetry, and a generous island. A warm living room with a wood-burning fireplace, elegant dining room with access to sunroom, 1st floor bedroom, and full bath complete the main level. Upstairs offers three inviting bedrooms and a beautifully updated bath with a double-sink vanity. Walk-out lower level provides entertaining family room, a flexible bonus room for office/guest, wet bar, full bath and laundry. Outside enjoy a spacious flat backyard, patio, and electric car charger.
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
Welcome to 46 Church Street. This spacious, beautifully maintained, Paul Whitney built home is just outside the heart of Winchester center with easy access to the commuter rail, schools, restaurants, and shopping. Offering flexible living areas and abundant room throughout, the residence features four bedrooms, three and a half bathrooms, two dedicated home offices, and a generously sized bonus room that can be adapted to serve a variety of purposes – including conversion to an additional primary suite. An additional guest suite on the lower level provides even more versatility. This property also includes an attached two-car garage, owned solar panels that can help lower electric costs, and an inviting outdoor space with a private backyard and patio. With its thoughtful layout and extensive living area, this home can accommodate a wide range of lifestyle needs. Don’t miss this opportunity to enjoy downtown living!
Another Tree Top Group masterpiece –Welcome to 6 Wyman Court! New full gut renovation townhome with 2,722 sq. ft., 3 beds, 4.5 baths & 4 levels of sun-drenched living space. Located in a prime end of cul-de-sac & moments from the vibrant Winchester Center including shops, dining & commuter rail. Main level features a thoughtfully designed kitchen w/ stainless steel appliances, a large center island, opening to bright living & dining areas w/ custom cabinetry & hardwood floors. The 2nd level offers a serene en-suite primary w/ private deck, a spacious 2nd bedroom, full bathroom, 2nd floor laundry, & includes a versatile loft ideal for office or lounge. The 3rd floor hosts a 2nd en-suite primary w/ double closets. Finished lower level boasts a home office/flex space, full bathroom, family room w/ built-ins, & wet bar! Additional highlights include a 1-car garage, an extra off-street parking space, & EV charger readiness. Luxury, location & design—your perfect Winchester townhome awaits!
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.
This stately Victorian offers an exceptional blend of preserved character and modern functionality across its generous, well-appointed layout. Sunlit rooms highlight hardwood floors, detailed millwork, bay windows, and a graceful fireplace, creating a warm and elegant flow throughout the main level. The expansive kitchen features stone counters, a central island, French doors, and direct access to the porch and patio for effortless indoor-outdoor living. Upper levels provide inviting bedrooms, including a spacious primary suite with its own bath, walk-in closet and balcony. A versatile third-floor retreat/ legal apartment with treetop views—complete with additional kitchen, living area, full bath, and its own exterior deck—enhances the home’s flexibility. Set on a beautifully landscaped lot with mature trees, stone accents, and abundant outdoor space, this remarkable property offers a standout combination of scale, charm, and convenience near local amenities.
Sunny studio unit overlooking the pond and courtyard at Parkview Condos in Winchester. Unit features include large private balcony with large sliding door that lets in lots of natural sun light. New LVP flooring in the living room/bedroom area and hallway. Freshly painted all throughout. Kitchen has granite countertops and a new refrigerator and electric range. The condominium amenities include an in-ground swimming pool, barbecue area, large parking area with additional overnight guest parking, on-site laundry, on-site management, and private storage units. Ideally located near downtown Winchester, the commuter rail, and major highways.
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.
From the moment you enter this European-style Victorian, you’ll be charmed. The first level features an eat-in kitchen with quartz countertops, LG Café appliances, wine fridge, island, and large windows, plus a living room, den, and half bath. The second floor offers a primary suite with skylight, ceiling fan, two walk-in closets, balcony, jacuzzi bath, and steam shower. Two more bedrooms and a sitting area complete this level. The third floor provides space for additional bedrooms or an office. The finished lower level includes a family room, wine cellar, sauna, gym, and full bath. Enjoy a tree-lined backyard with deck and hot tub, perfect for entertaining. The home office opens to the yard and attached two-car garage with Level 2 EV charger. Central A/C and a Tesla solar roof with 27 KW battery storage complete this stunning home.
Welcome to 89 Wildwood — Winchester’s best new value, where modern design meets classic New England charm! This new construction home offers a flexible layout with spaces for hosting, relaxing & everyday living. The chef’s kitchen impresses with an oversized island, stylish finishes, ample cabinetry & opens to a designated dining area. Fireplaced family room, bedroom/office with ensuite & half bath complete the first level. Upstairs, find five bedrooms, three full bathrooms & a laundry room outfitted with custom cabinetry & sink. The front to back primary suite has double walk in closets & an ensuite with dual vanities. Finished lower level features an additional guest suite & playroom, hangout space or gym. Conveniently located close to town, 89 Wildwood offers the best of Winchester living. Showings begin at first Open House Saturday 11/15 12:30-2!
Mid Century Side Hall Colonial w Attached Garage on an Attractive Corner Lot in Winchester. Available for the first time in more than fifty years, this inviting home awaits its next owners' vision and personal touch. Exceptional opportunity to add immediate value with the right repairs and upgrades. Main floor features an open living room with fireplace, adjoining dining room with southwest exposure, eat-in kitchen, half bath, and access to the garage. Four bedrooms and full bath upstairs. Above grade finished basement with full windows walks out onto a natural backyard. Desirable west end location on Thornberry Hill. Vinson-Owen Elementary School and Winchester Swim & Tennis Club in the neighborhood. Close proximity to Winchester Center, surrounding towns, shopping, dining, area businesses, events and culture, parks, trails, and conservation lands. Convenient to Downtown Boston.
This charming Cape style home on a half-acre lot combines classic character with modern updates. Step inside to find newly refinished hardwood floors throughout the inviting fireplaced living room, dining room, and bedrooms. The recently updated kitchen and bathrooms blend style and function with contemporary finishes. The dining room with built-in China cabinet provides an inviting space to entertain. Enjoy morning coffee or evening relaxation on the unheated 3-season porch overlooking the yard, with seasonal views of the Boston skyline. The lower level features high ceilings with a heating and cooling unit already installed, offering great potential for 200+ sqft of future finished space. Additional highlights include a one-car garage under and a convenient layout with timeless appeal. Nestled beside conservation land, this home provides a peaceful, natural setting where you can enjoy watching birds and local wildlife right from the yard. Make this one yours for 2026!
Nestled in one of Winchester's most picturesque cul-de-sacs, this elegant English Tudor is available for the first time in 60 years. Passed quietly through word of mouth, this is a rare opportunity to own a piece of Winchester's architectural history. Located near Lincoln School & Winchester Fells' scenic trails, the setting is both serene and convenient. Designed by renowned architect Harry M. Ramsay, this home blends timeless Tudor charm with modern updates. Features include 4 bedrooms, 2.5 baths, renovated kitchen, cozy family area, & a spacious living room with a striking fireplace. The finished third floor adds extra living space, along with the finished lower level, currently set up as a home gym. Built in 1929, the home boasts exceptional craftsmanship, with steel I-beams & wire lath plaster walls. A detached two-car garage & peaceful yard complete the property, making this a once-in-a-lifetime chance to own a historic home in one of Winchester's most sought-after neighborhoods.
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 hook-ups, garage 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. Currently leased "Tenant At Will" paying $3200/month. Possible to deliver vacant.
Welcome to this beautifully updated home! The interior boasts fresh interior paint, all new lighting with refinished hardwood flooring. The living room features a cozy fireplace, perfect for relaxing evenings. The kitchen is a chef's dream with all new stainless steel appliances, new cabinets, and new counter tops with an accent backsplash adding a touch of elegance. The primary bathroom is designed for convenience with double sinks and new shower. The exterior of the home is just as impressive with fresh exterior paint and a deck for outdoor enjoyment. This home is a must-see!. Included 100-Day Home Warranty with buyer activation.
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.
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.
NEW PRICE & UPDATES BEAUTIFULLY REIMAGINED!Welcome home to this stunning brick ranch tucked on a quiet cul-de-sac in Winchester’s coveted West Side. Every space has been thoughtfully designed, blending classic craftsmanship with distinct elegance. The bright open layout invites you in with a chef’s granite and stainless kitchen, sun-filled family room framed by floor-to-ceiling windows, and French doors opening to a new composite deck and tranquil backyard. Gather in the elegant dining room and sunken living room with fireplace, or retreat to the serene primary suite with sitting area and spa-inspired bath. A flexible fifth bedroom or office with private entrance is perfect for guests or in-laws. The finished lower level offers a game room, gym, wine storage, cedar closet, and more. Spectacular & unbeatable location and neighborhood awaits you! Move-in ready, moments to Winchester Center, top schools, and commuter access—where timeless style meets effortless living.
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.
Welcome to 44 Cabot Street, a newly built home in one of Winchester’s most desirable neighborhoods. Offering over 6,000 square feet of beautifully crafted space, this residence features 6 bedrooms, 6.5 bathrooms, and a layout designed for modern living. Thoughtfully selected finishes, high ceilings, and an abundance of natural light create a warm and inviting atmosphere throughout. The open-concept living and entertaining spaces flow seamlessly, anchored by a stunning kitchen and elegant central gathering areas. Featuring a Viking 8-burner range, Viking commercial grade fridge, double dishwasher, and under counter microwave. Each bedroom includes its own private bath, while additional flexible space accommodates a variety of lifestyle needs. With attention to detail inside and out, this home offers a rare opportunity to enjoy new construction in a prime location close to town, brand new elementary school, and commuter access.
Amazing custom-built 6-bedroom / 5+ bathroom house on a quiet neighborhood in Winchester. This beautiful home welcomes you with a magnificent 18" foyer and features an amazing family room with 18” high coffered ceilings and 3 sides tall and bright windows and a large gourmet kitchen with a big island and double ovens. Traditional living and dining room maintain its good sense of typical New England Colonial style. Curved front stair case add one more layer of beauty. Second floor and third floor offer total 6 bedrooms, suites and walk-in closets. Master bedroom is with cathedral ceilings, a sprawling master closet and an office/sitting area. Smooth flow of the spacious and walk out lower level enables rich life style with billiard room, media room, art room and exercise room -- all designed for a modern lifestyle, with an open layout that is perfect for entertaining. State of the art systems with total 6 heating and cooling zones and central vacuum system.
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.
