Picture Perfect! The crown jewel of Winning Farm, a 55+ community ideally situated in the heart of Winchester. Step inside to find a bright, open-concept living space. Soaring ceilings, gleaming hardwood floors and refined architectural details create an airy, elevated atmosphere. Beautiful private office. Gourmet kitchen with premium appliances, stone countertops and oversized island for casual dining and entertaining. Dining area with coffered ceilings, fireplaced living room, and bonus screened porch to enjoy the view of the lush conservation land and walking trails. The luxurious primary retreat offering a spa-like bath with double vanities .Laundry room and 1/2 bath round out the main level. Upper level boasts 2 additional bedrooms, a full bath and flexible, cozy loft space. Amazing, walk out lower level includes a full gym, patio for grilling, built in cabinets, full bath and spectacular, custom built wine cellar Two car garage. This opportunity is not to be missed!
Picture Perfect! The crown jewel of Winning Farm, a 55+ community ideally situated in the heart of Winchester. Step inside to find a bright, open-concept living space. Soaring ceilings, gleaming hardwood floors and refined architectural details create an airy, elevated atmosphere. Beautiful private office. Gourmet kitchen with premium appliances, stone countertops and oversized island for casual dining and entertaining. Dining area with coffered ceilings, fireplaced living room, and bonus screened porch to enjoy the view of the lush conservation land and walking trails. The luxurious primary retreat offering a spa-like bath with double vanities .Laundry room and 1/2 bath round out the main level. Upper level boasts 2 additional bedrooms, a full bath and flexible, cozy loft space. Amazing, walk out lower level includes a full gym, patio for grilling, built in cabinets, full bath and spectacular, custom built wine cellar Two car garage. This opportunity is not to be missed!
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 the highly sought-after Pepper Hill Estates, ideally situated on a quiet street near Vinson-Owen Elementary School and within walking distance to Wright-Locke Farm and McClennen Park. This Colonial-style home offers a highly desirable and functional layout. The first floor features an open-concept design with a spacious living room, dining area, and a custom-built kitchen by Schrock Cabinetry, along with a versatile bedroom/home office. The second floor showcases a beautiful primary suite with stunning hardwood flooring, an walk-in closet, and a well-appointed en-suite bath complete with a Jacuzzi tub and separate shower. A well-sized secondary bedroom with its own full bath completes this level. The lower level includes a laundry room and provides direct access to the one-car garage. Enjoy the exclusive-use fenced backyard with a charming patio—great for outdoor entertaining. A fantastic opportunity to move into charming Winchester and enjoy all the town has to offer.
Tucked on a quiet cul-de-sac within an exclusive enclave of homes, this newer residence offers a harmony of refined living and natural beauty. Just moments from the trails and vistas of the Middlesex Fells Reservation, this home is ideally positioned for those who value serenity and effortless access to the outdoors. Thoughtfully designed, it unfolds with an airy, open-concept where a sunlit kitchen, dining area, and family room create an inviting backdrop for everyday living and elegant entertaining. The family room exudes warmth and sophistication, while the chef’s kitchen impresses with an expansive center island and a suite of premium Thermador appliances. A first-floor office or den, paired with a full bath, offers versatility. Upstairs, the primary suite is a true retreat, with soaring ceilings, a spa-inspired bath, and a generous walk-in closet. 3 other roomy bedrooms complete this floor. A full finished basement is a true bonus, with direct walk-out access to the back.
Beautifully updated home offers generous living spaces and a seamless, open flow. Sun-filled living and dining areas feature hardwood floors, elegant detailing, and a fireplace that creates an inviting atmosphere. The kitchen is thoughtfully designed with quartz countertops, custom cabinetry, stainless appliances, wine chiller, and large island that opens to the dining area, which flows into the family room with direct access outdoors - ideal for yard access and entertaining. French doors between the kitchen, dining, and family room help to create a quieter, more private setting for the bedroom and formal living areas. The primary suite provides a private retreat with a full bath, while three additional bedrooms and full bath complete this level. A finished walk-out lower level adds versatility with a fireplace playroom, 5th bedroom, full bath, and laundry. Enjoy professionally landscaped grounds and inviting outdoor areas, complemented by an attached garage and ample parking.
This exceptional Colonial Revival home in a sought-after Winchester neighborhood blends craftsmanship, thoughtful updates and a design layout perfect for entertaining and modern day living. A welcoming front porch introduces a double entry foyer, high ceilings with crown molding and period detail that flow through the formal dining and living room with fireplace to the family room, kitchen and butler’s pantry. Oversized windows drench hardwood floors with sunshine. Keep the French doors open to access the patio and fenced-in back yard, perfect for play. This well-proportioned home includes 2 primary suites, 5 additional bedrooms plus a 2nd floor office with bead board. Enjoy the private, renovated 3rd floor as an owner sanctuary, work space, or kid zone! With abundant storage, partially finished lower level rec room and 2-car garage this home has it all; including, a location close to the town center, schools, and train - all on the south side of Winchester, close to Boston/Cambridge.
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!
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. Desirable Vinson Owen School
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.
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!
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.
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!
Welcome to 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 new flooring and excellent closet space, freshly painted throughout all rooms, 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. Bedroom and livingroom was virtually staged.
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.
