This charming home abounds in style and character. It is Steps to downtown Winchester, where you can enjoy a variety of fine restaurants, easy commute to Boston in less than 15 minutes and be able to walk to all the public schools & St. Mary's .Beautiful natural wood trim & hdwd floors throughou, grace this home. A spacious & sunny kitchen w/ center island, great for entertaining & a built-in desk. Large pantry for storage. Lots of cabinets, and stainless steel appliances. The dining room showcases a boxed bay window & a built-in display china cabinet. Formal living room with a gas f.p. and french doors leading to an informal family room. A wrap around screened- in porch which will expand your lifestyle in the summer, overlooking a front yard with beautiful forever perennials. Upstairs: 3 bedrooms plus a small office space w/built-ins. Spacious tile bathroom with soaking tub, shower and double sinks. Parking for 3-4 cars. 4th B/R on 3rd floor. EV charger .Full basement.
Location, location, location! Enjoy one-level living in this charming Ranch-style home, beautifully situated on a cul-de-sac, within walking distance to the vibrant Town Center. This exceptional property, lovingly maintained by the same owners for 50+ years, offers a large fireplaced living room with ample natural light, gracious dining room with built-in cabinets, tasteful new kitchen with quartz countertops and stainless appliances (2025), spacious primary bedroom with en-suite bath and cedar closet, 3 additional good-sized bedrooms, beautiful hardwood floors, central airconditioning, sunroom overlooking private backyard, mudroom, abundant storage space, and more. Bring your creative ideas for the large space in the lower level to personalize for your needs. The 2-car garage, motion-sensor lights, and the landscaped yard complete the picture. Welcome to Winchester with its highly rated schools, two commuter rail stations, Mystic Lakes, and the much-treasured Fells Reservation.
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 heated pool, complimented by lush outdoor landscape
Set in one of Winchester’s most coveted neighborhoods, this distinguished Robert Coit-designed residence seamlessly blends timeless architecture with exceptional modern living. Rich in original detail and brimming with character, this 4-bedroom, 2.5-bath home is a true testament to enduring craftsmanship. Gracious living spaces are anchored by three fireplaces, creating warmth and elegance throughout. The expansive kitchen is a showpiece—generous in scale and thoughtfully designed for both everyday living and entertaining. A cypress-paneled den with a fireplace is located on the first floor. The top floor offers 1 room with sink and a large open gallery space, perfect for a home office. Outside, the property unfolds into spectacular, professionally curated gardens and lush landscaping, offering a private oasis that changes beautifully with the seasons. There is a full unfinished basement for additional space. Large welcoming front porch, close to the center and top-rated schools.
Located in the highly sought-after, newly done Lynch School district, this home shines with fresh paint throughout and beautifully refinished hardwood floors. The first floor offers a functional layout with a dedicated dining area that flows seamlessly to the kitchen and spacious living room—ideal for everyday living and entertaining. The upper level features two generously sized bedrooms and two full bathrooms. Both equip with excellent closet space and ample sunlight through multiple windows. An unfinished basement of roughly 400 square feet provides excellent potential to add living space and value. Enjoy a large and leveled yard professionally maintained by management. Trash removal and exterior maintenance included in the management fee. This attached single family is complete with a private driveway in a convenient location.
Rarely available top-floor (7th floor) condo at the Parkview Condominium Complex! Enjoy easy living in highly desirable Winchester. Well-maintained 1-bedroom condo offers a bright, open-layout, spacious bedroom with an oversized closet. Full bathroom with tiled shower/tub. The Kitchen offers ample cabinet and counter-top space, breakfast bar style which opens to the living area- perfect for dining and entertaining. Large living room with a glass slider leading to a private balcony overlooking a view of beautifully landscaped grounds. Unit also includes 1 parking space, storage space in the basement, and on-site laundry room. Condo fee includes; heat. hot water, electric, A/C, water/sewer, landscape, & snow removal. Other amenities include gated entry, on-site management, plus the swimming pool with picnic/BBQ area. minutes away from town center, shops, restaurants, bus stop, & the commuter rail t-stop. Close to outdoor trails, major highways, and easy access to the city of Boston
Grand custom-built 6 bedroom / 7 bathroom house in a quiet Winchester neighborhood. 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.
Charming, beautifully updated town home in prime downtown Winchester neighborhood! This 4 bed 2 bath home offers living space across 3 levels, blending classic character w/ everyday functionality. The layout features a welcoming main level with high ceilings, oversized windows & a nice open flow between the living room, dining room, family room & kitchen, creating an ideal setup for both daily living and entertaining. Upstairs, you’ll find 4 large bedrooms w/ flexibility for guest space or home offices. Generous room sizes, hardwood flooring, and great natural light carry throughout the home, enhancing its warm and inviting feel. Timeless architectural details add to this great home. Enjoy private spaces with room to spread out, all while being conveniently located close to Winchester center, commuter rail, top-rated schools, and local shops and restaurants. A great opportunity for both commuters and those looking to enjoy all the town has to offer.
Charming, beautifully updated town home in prime downtown Winchester neighborhood! This 4 bed 2 bath home offers living space across 3 levels, blending classic character w/ everyday functionality. The layout features a welcoming main level with high ceilings, oversized windows & a nice open flow between the living room, dining room, family room & kitchen, creating an ideal setup for both daily living and entertaining. Upstairs, you’ll find 4 large bedrooms w/ flexibility for guest space or home offices. Generous room sizes, hardwood flooring, and great natural light carry throughout the home, enhancing its warm and inviting feel. Timeless architectural details add to this great home. Enjoy private spaces with room to spread out, all while being conveniently located close to Winchester center, commuter rail, top-rated schools, and local shops and restaurants. A great opportunity for both commuters and those looking to enjoy all the town has to offer.
The most idyllic setting in town! This beautifully renovated and expanded Colonial blends timeless charm with modern sophistication. Perfectly sited on an 18,000 sq ft lot abutting conservation land, it offers exceptional privacy in one of the town’s most coveted neighborhoods. This stunning home features 5+ bedrooms and 4.5 baths, with new windows, updated systems, an expanded kitchen, and beautifully appointed baths throughout. The elegant kitchen overlooks a large, level backyard with direct access to a bluestone patio—ideal for entertaining—set against acres of serene conservation. The second floor offers a gracious primary suite with bath, plus four additional bedrooms and two full baths. The finished lower level features high ceilings, a fireplace, full bath, sauna, and direct yard access.
A quiet cul-de-sac near the Mystic Lakes sets the stage for this exceptional Royal Barry Wills residence, masterfully reimagined. Every inch reflects elevated craftsmanship and a refined sense of luxury, with bespoke finishes and thoughtfully curated amenities throughout. The main level unfolds with effortless elegance, anchored by a state-of-the-art chef’s kitchen featuring custom cabinetry, Thermador appliances, dual ovens and wet bar. An inviting family room with soaring cathedral ceilings and sliders to the deck creates a seamless indoor-outdoor flow. Multiple dining areas offer versatility for both intimate gatherings and grand entertaining, complemented by a stunning gas fireplaced living room with a sunlit bay window. A private office, study, sunroom and 4 beautifully appointed bedroom suites complete the interior. Outside, a newly renovated yard w/ an outdoor living room, play space, rock walls and secondary patio offer natural sanctuary. Top location, close to town & Ambrose.
This Expanded Cape features a fireplace living room, built in bookcases, and glistening hardwood floors throughout. The spacious kitchen has a dining area which opens to the living room for an entertaining atmosphere. The 2nd floor Master bedroom suite has a balcony to enjoy your morning coffee. The inviting 3 season porch with flagstone floor is a nice place for family to congregate and get to gather. The living room, graced with crown molding, offers a welcoming space for relaxation and entertainment. The home features four bedrooms and two full bathrooms, providing ample space for a comfortable lifestyle. The inclusion of a walk-in closet adds a practical and desirable element, offering generous storage and organization. Please come and visit this fine home close to shops, highways and schools!
Discover a beautifully reimagined home in one of Winchester’s most sought-after neighborhoods, offering exceptional space, comfort, and convenience in a truly prime location. With 7 bedrooms, 7 full baths, and 1 half bath, 1 Plymouth has been thoughtfully expanded and rebuilt with high-end finishes throughout to suit today’s lifestyle. At the heart of the home is a stunning fireplaced family room just off the chef’s kitchen, featuring soaring cathedral ceilings and a gas fireplace, perfect for everyday living and entertaining. The flexible layout balances open-concept living with defined spaces, including a private two-bedroom retreat with its own living area, wet bar, office, and full bath, ideal for guests, extended family, or a separate suite. Just moments from Wright-Locke Farm and Mullen Field, this exceptional property offers the best of location, design, and livability.
This quintessential Colonial blends timeless charm with modern updates, offering a truly move-in ready home in a unique location! Directly across the street, the Winchester Swim and Tennis Club presents a rare opportunity for immediate membership—enjoy your own private club lifestyle just in time for summer! Just a few doors from Vinson-Owen Elementary, morning drop-offs couldn’t be easier. Wright-Locke Farm is just up the road! Inside, you’ll find a highly desirable layout with four spacious bedrooms on the second floor and two modern bathrooms. The renovated kitchen flows seamlessly into a formal dining room, perfect for entertaining, while the bright living room and cozy fireplaced family room provide inviting spaces for everyday living. A beautiful bathroom on the first floor adds convenience and flexibility. Set back gracefully from the road for added privacy and curb appeal, this home also features a two-car garage, a fantastic three-season sunroom, and a gorgeous oversized lot!
Stunning corner unit, fully renovated 2 BR,1.5 BA condo offering an exceptional blend of elegance & modern updates in a prime in-town location.Soaring ceilings, dramatic arched openings, & oversized windows flood the space w/natural light.French doors open to charming private balcony.Main living area showcases beautifully refinished marble flooring, gas FP, & designer lighting including crystal chandeliers & wall sconces. The thoughtfully renovated kitchen features granite countertops, custom cabinetry, stainless steel appliances, & opens to a stylish butler’s pantry complete w/wine fridge, sink, & in-unit washer/dryer. Upstairs, both bedrooms offer HW flooring, updated lighting, & skylight w/shade. Bathrooms have been tastefully updated. Additional highlights include updated electrical, gas line connection, & integrated sound wiring.Includes one car garage, an additional outdoor parking space & basement storage w/bonus cedar closet.Turnkey home near town center, shops & commuter rail.
SPRING TIME IS COMING! Welcome to this Stunning 2 BR unit on Terrace level with amazing view of duck pond and flowering garden area from private outdoor patio at Parkview Condominiums. Spacious open LR/DR with updated kitchen and bath. Kitchen to include stainless steel appliances, glass tile backsplash, very nice countertops and huge peninsula great for parties. 2 huge bedrooms with lots of closet spaces. Private storage space and laundry in the building. In ground pool and beautiful out door spaces. One off street parking space and huge guest parking lot. Easy access to Rte. I95, Rte. I93, "T" and Boston. Walking distance to shopping, Winchester town center and many more. HEAT , HOT WATER AND ELECTRICITY ARE INCLUDED IN THE CONDOMINIUM FEE. EASY TO SHOW! OPEN HOUSE ON SATURDAY 11: 00 -- 1:00 PM AND SUNDAY 12:00--1:30 PM OFFERS DEADLINE : MONDAY APRIL 20, 2026
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!
Newly Renovated! 2 Bd at Church Place in Winchester Center! This stunning corner unit renovation was just completed & is ideally located in the heart of the center. Perfect for down-sizers or anyone seeking easy living w/ access to the train, restaurants, shops & top-rated schools - all the conveniences right outside your door! This bright & airy unit offers an open floor plan w/ beautiful arched windows, new wide plank wood floors, updated electrical, new kitchen & updated bath w/washer dryer in unit! The newly renovated kitchen offers plenty of cabinetry & a dining peninsula. The BR's offer generous closet space ~ enjoy low-maintenance living including trash & snow removal making this home as practical as it is charming. Take the elevator up to your private entrance hall or use a quick set of stairs. Enjoy stunning views of the town and unbeatable convenience. Rare offering with two deeded parking spaces just steps from the building's side entry. A true gem in a sought-after location
Winchester's premiere location! This stunning waterfront gem is perfectly situated on Winter Pond, offering over 80 feet of direct water frontage with expansive yard and breathtaking views from nearly every room. Located in the exclusive Flats neighborhood, this property presents a rare opportunity to enjoy water activities such as kayaking, paddleboarding, fishing, ice skating and hockey all while being just minutes from Winchester Center and the train to Boston; homes like this rarely come to market. Custom designed and lovingly owned by the original family, this home is now ready for its next chapter. Offering a beautiful flowing layout w/large rooms, featuring floor-to-ceiling bay windows with stunning views, 5 bedrooms, 2 full & 2 half baths, 4 fireplaces, hardwood floors, a walk-out lower level, & a gorgeous fenced yard with steps to the water. Truly a special setting that seamlessly combines privacy, views & accessibility in Winchesters top neighborhood. This home is a must see!
Discover this beautiful home with all the space you've been looking for! Set on a private half-acre lot in a serene cul-de-sac near the Winchester/Lexington border. This residence offers unparalleled privacy & is surrounded by nature. This home includes 5 bedrooms, 3.5 bathrooms & an oversized 3 car garage! The spacious grounds feature delightful front & back yards, a generous deck, & a charming gazebo, all beside Whipple Hill & Smith Pond w/ miles of walking trails nearby! Inside you will find a thoughtfully designed floor plan for every day living & entertaining featuring a sunken living room, sunny home office, lovely formal dining room & oversized family kitchen w dining area showcasing walls of windows overlooking the stunning rear yard & an adjacent family room w/ wood burning fireplace. The oversized primary suite incudes a walk in closet & spacious bath. Just 7 miles from Boston, Winchester is known for top-rated schools & great quality of life. Don't miss this fabulous home!
Move in ready & nicely remodeled ranch on a fabulous 10K fenced lot! This 3-4bedroom, 2 full bath home w/full lower level including office, family room/bedroom & full bath offers a sunny, functional layout w/ tasteful updates throughout.The main living spaces flow seamlessly, highlighted by a newer eat-in kitchen w/ access to deck & great yard; perfect for indoor/outdoor living & entertaining. Spacious living room offers a fireplace, bay window & opens to dining area. Generously sized bedrooms & updated full bath complete the 1st floor. You will love the large lower level w/ high ceilings, a nice family room/ bedroom/office and full bath. The fenced yard w/ lush grass & large deck offer a private outdoor retreat. This home is ideally situated in a central location, just moments to town, Whole Foods & Horn Pond, w/ easy access to major highways for an easy commute. Enjoy all that Winchester has to offer, including its highly rated schools, the train to Boston & the vibrant town center!
Welcome to one of Winchester’s most extraordinary residences. This one-of-a-kind Center Entrance Colonial Revival sits on a beautifully landscaped, private lot complete with in-ground swimming pool and ample outdoor space perfect for relaxation or entertaining. A grand foyer welcomes you in where you can entertain with ease throughout the expansive first floor. Here you will find a high-end eat-in kitchen with large island & granite countertops as well as a formal dining room with gas fireplace. A living room with custom built-ins & window seat, a family room overlooking the yard, and a bar complete this level. This distinguished residence offers 7 bedrooms and 6 bathrooms, blending timeless architectural details with luxurious modern amenities. Additional highlights include a primary suite with walk-in closet and sitting room, large entertainment room, 3 car garage, and close proximity to downtown and commuter rail. Don’t miss this rare opportunity to own a truly remarkable estate.
40 Foxcroft Road presents exceptional new construction in the highly desirable Flats of Winchester. This 6BR, 4.5BA residence spans 6,460 sqft and showcases thoughtfully curated design with an open concept floor plan ideal for modern living and entertaining. The sun-filled living room features soaring vaulted ceilings with exposed wood beams and a gas fireplace, framed by expansive Pella windows. The chef’s kitchen is appointed with a premium Thermador appliance package and an elegant dry bar with integrated lighting. Custom millwork throughout adds warmth and architectural detail. A home office is located on the main level. The luxurious primary suite offers a custom walk-in closet with built-in lighting and a spa-inspired bath with steam shower. The top level offers two additional bedrooms ideal for guests or play space. The finished lower level includes a media room and home gym. A spacious deck overlooks the backyard, creating the perfect setting for outdoor entertaining.
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.
Winchester is located in Massachusetts. Winchester, Massachusetts 01890has a population of 22,875. Winchester 01890 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 01890 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 01890 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.
