Step into this beautifully maintained 2004 townhouse that has the feel of a single-family home, perfectly blending comfort, convenience, and modern living. The house features high ceilings, crown molding, hardwood floors and a spacious kitchen. Master bedroom includes a walk-in closet and en-suite bathroom with double vanity and jacuzzi. Finished basement provides a flex space for a cozy family/game room with a built-in home theater, perfect for creating memories. Additional highlights include freshly painted interior, 3-car parking, large fenced backyard and a whole house water filtration system. The home is within walking distance to the brand-new Lynch Elementary school, MBTA bus stop, daycares and is located within minutes to Winchester downtown making commuting and daily routines effortless. Enjoy peaceful mornings or evening walks just steps away at Horn Pond, offering scenic trails and a wonderful outdoor lifestyle. This is more than just a house—it’s a place to feel at home.
This well-maintained colonial is tucked at the end of a cul-de-sac in a very desirable neighborhood. Upon entering, the bright foyer with hardwood floors opens to a spacious front to back living room. The formal dining room leads to the eat in kitchen, perfect for entertaining and gatherings. Just off the kitchen the family room features a stone fireplace and sliding doors leading to the deck and backyard - perfect for relaxing and entertaining. A convenient half bath with laundry hookups completes the first floor. Upstairs are four generously sized bedrooms and two full baths, including a primary suite with access to an open loft overlooking the family room - ideal for a home office or bonus space. The home also offers a large, dry basement high ceilings and potential for additional living space. Many updates including newer roof, heating system, A/C, windows, siding and more! Close to the shops and restaurants of Winchester Center, commuter rail access, and the Fells Reservation.
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.
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!
Welcome to 15 Wildwood Street — a quintessential Winchester residence offering timeless character, modern amenities & endless potential. Ideally situated on a beautiful lot close to the town center. This charming home is impeccably maintained & move-in ready, while providing the opportunity for thoughtful updates to further enhance its value. Step inside to a sun-filled living room w/oversized windows, rich architectural details, 10’ft ceilings & original crown molding. The kitchen combines function & style with Sub-Zero fridge leading to the elegant dining room w/ fireplace, china pantry, original marble sink & more. Upstairs, 6 bedrooms await, featuring hardwood floors, large closets & beautiful natural light. The stunning walk out lower level also features extremely high ceilings w/teak parquet floors. This property also includes a 3 story, 2200 sf barn with parking for 7 cars and potential for ADU / living space /home office/ gym & more! Close to downtown Winchester!
Rarely available 3 bedroom 2 full bathrooms Townhouse at The Residences at Winchester, located in the most coveted and brand new Lynch School district. Updated kitchen with stainless steel appliances, spacious and sun-filled living room with large picture window, gleaming hardwood floor throughout. Upstairs features 3 bright bedrooms and an updated full bath. Finished lower level boasts a laundry room, Family room and full bath, heated on a separate zone. New boiler in 2020. Fenced back yard access from kitchen, parking for 2 cars, low condo fees. Easy commuter rail access into Boston with convenient access to Routes 93 and 95. Just minutes from Winchester Center and a short drive to Boston.
Charming antique Colonial perfectly blending old world detail with modern updates- ideally located just moments from Winchester Center, Wedge pond, tennis courts, all schools, bike path, the commuter rail, shops & restaurants! This lovingly maintained home w/ central A/C features a spacious, flowing layout, high ceilings & newly refinished hardwood floors. The main level offers a welcoming enclosed entry porch, leading to sun-filled living & dining rooms w/ bay windows. The updated expanded kitchen w/ pantry opens to a bright breakfast room & connects seamlessly to the spacious family rm w/ closets & sliders providing direct access to the expansive multi-tiered decks & private level fenced yard, perfect for entertaining. Upstairs you will find 3 large bedrooms & 2 full baths including a generous primary bedroom w/ walk-in closet. The lower level can be finished for add'l space & includes laundry & storage options. Don't miss this great home complete with EV charger!
This spacious four bedroom Colonial is located in the desirable westside neighborhood and Ambrose school. The first level has a fully applianced kitchen followed by a oversized dining room. There is a wood burning fireplace in the spacious living room. A family room is off the kitchen and also an office and half-bath completes this level. The second level has four very large bedrooms. The main bedroom has a walk-in closet and bath. A second bathroom on this level.. Pull down stairs to the attic in the hallway. the lower level has a finished room currently used as a bedroom but has multi uses. Direct access to the 2-car garage. The heated Gunite pool was installed by the current owners along with the enclosed fencing. Home sited on a large level lot. Great location near Whole Foods and Mahoney's. Short ride to the center of town.
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.
Tucked at the end of a cul-de-sac and bordering the Fells, this classic brick-and-wood Colonial blends generous living spaces with comfortable, easy flow. The fireplaced living room and spacious dining room are filled with natural light and framed by peaceful woodland views. The kitchen features stone counters, stainless appliances, and a peninsula that connects to the dining area and opens to a vaulted, beamed family room with fireplace and French doors to the outdoors. A home office offers added flexibility. Upstairs, four inviting bedrooms include a tranquil primary suite with walk-in, cedar closet and private bath, and a second bedroom with its own ensuite bath. The walk-out lower level offers additional living space with a playroom, wet bar, and full bath. Porch, patio, and fenced yard create welcoming outdoor areas, complemented by central air and an attached 2 car garage. With its thoughtful layout and cul-de-sac setting near the Fells, this home offers enduring appeal.
Fantastic! The best value in Winchester in a desired neighborhood. The sunny first floor flows nicely from room to room, with hardwood floors in the living areas and a hallway leading to the 3 original bedrooms. Ideal for an office, guests, or visiting in-laws. A screen porch and patio off the dining room ideal for al fresco dining. The generous second-floor renovation features a full bath with double sinks, an exclusive-use laundry room, and 3 bedrooms, each with 3 windows for generous natural light. The backyard is private and level for grilling, gardening, and entertaining. The huge 1,165 sq ft basement is your creative space for a playroom, gym, and media room. Great school system (Ambros), and downtown convenience for commuter rail, shops, and restaurants. An amazingly beautiful backyard that's perfect for outdoor recreation. The seller will gift a pool and a ping-pong table to the new buyer in the playroom.
Gracefully positioned along Winter Pond, this exceptional waterfront residence offers a rare opportunity to own one of the Flats most desirable addresses. A true legacy property, it has been beautifully maintained and updated, blending classic architecture with modern comfort. This 5 bedroom, 5.5 bath classic provides generous, well-proportioned rooms designed for both refined entertaining and relaxed daily living. Water views serve as a serene backdrop to the kitchen, family room and study, while several curated outdoor dining and gathering areas invite entertaining overlooking the pond. The expansive living and dining rooms complete the first floor. A generous primary suite is a private retreat with a spacious bath and ample closets. 4 other ample bedrooms and a second floor laundry complete this floor. The basement has a huge media and game room, sauna, gym, wine cellar and direct access through a mudroom to a covered patio. Kayak, skate, go fishing and enjoy life on the water!
Brand new high end construction in prime Winchester location! Currently under construction w/ completion expected late spring 2026. A thoughtfully designed home with immense curb appeal showcasing stunning living spaces across three finished levels. This 6+ bedroom, 5.5 bath transitional style home blends classic architecture with modern finishes -The main level features an open concept designer kitchen w/vaulted ceilings, skylights, oversized island, sliders to large deck & a fire-placed family room, along with formal living and dining rooms & a first floor bedroom suite. The 2nd floor offers 4 generous BR's including a luxurious primary suite, 2 additional full baths, and convenient second floor laundry. The above grade/ walk-out lower level adds exceptional flexibility with au- pair or in law space media room, home office, exercise room, bedroom & full bath Enjoy all the area has to offer including restaurants, shops, schools, train to Boston, Bike-paths & more! 7 miles from Boston
Stunning new construction in highly sought-after Winchester! This thoughtfully designed home blends modern style with everyday functionality. The first floor features an open-concept kitchen, dining area, and sun-filled living and family rooms with soaring ceilings open to the second floor and a cozy fireplace, perfect for entertaining or relaxing. A first-floor bedroom, full bath, and convenient laundry add flexibility for guests or multigenerational living. Upstairs, the luxurious master retreat boasts a cozy gas fireplace, expansive walk-in closet, and spa-like bath, followed by another bedroom with an ensuite bath, and two additional bedrooms sharing a Jack and Jill bath. A finished basement provides versatile space for a gym, media room, or playroom. Enjoy a charming front porch, private back deck, durable Hardy Plank exterior, and attached two-car garage. Exceptional craftsmanship and timeless curb appeal make this a must-see home!
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
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
Picture-perfect Cape Cod single family home on a corner lot across the street from the brand new Lynch Elementary School. This special residence is much larger than it looks & has 4–5 spacious bedrooms across two levels & two full baths on each floor. Such space offers versatility with 2 beds on main level & 3 bedrooms on the upper floor. The sun-filled living room flows nicely to a charming eat-in kitchen. The partially finished lower level adds valuable bonus space for a home office, gym or family room & has direct access to yard. Great basement storage & whole house generator powered by propane. Minutes from Winchester Center & Horn Pond. Commuter friendly location, close to the Winchester Center train Station.
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!
This STUNNING newly constructed home facing Old Village Drive redefines modern luxury! Designed w/ both elegance & everyday comfort in mind, this residence blends style w/ ease of living. The 8’ arched, handcrafted wrought-iron front doors open to a grand 20' foyer, showcasing soaring 10' ceilings, custom rift-sawn beams, and expansive floor-to-ceiling windows. With 25 years of expertise, the master builders commitment to exceptional quality & craftsmanship shines through every detail. Spanning four meticulously finished levels, this home leaves nothing to be desired. Highlights include a chef's kitchen w/ dual islands, vaulted ceilings, wine fridge, coffee bar, charming breakfast nook, butler's & dry pantries, a direct entry first-floor office or in-law suite & full third floor w/ hardwood floors & bath. The expansive lower level offers a family room, movie theatre, game room, gym plus private entry separate living quarters w/full in-law/au-pair suite w/ kitchen, 2nd laundry,BR & bath
Discover a stunningly reimagined home nestled in one of Winchester’s most sought after neighborhoods—an exceptional opportunity to own a beautifully crafted, completely transformed residence. Expanded and rebuilt with intention, 15 Mayflower delivers the space, layout, and flexibility today’s lifestyle demands, with a thoughtful floor plan that balances open concept living and well defined spaces. One of the home’s most compelling features is a private two bedroom retreat complete with its own living area, wet bar, office and bath—perfect as a hangout space, teen suite, guest quarters, or an ideal setup for extended family. Just moments from Wright-Locke Farm and Mullen Field, the location offers everyday access to outdoor recreation while remaining firmly rooted in a classic neighborhood setting. Featuring high end finishes and adaptable living spaces throughout, this exceptional property offers comfort, functionality, and convenience in a truly prime location.
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.
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.
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.
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.
