Winchester, MA Homes for Sale

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

Anne Spry Barrett Sotheby's International Realty

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

Nancy McLaughlin Redfin Corp.

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

Philip Vita Compass

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

Kim Covino Compass

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

Nancy Pallotta Gibson Sotheby's International Realty

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

Kim Covino Compass

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

George Sarkis Douglas Elliman Real Estate - The Sarkis Team

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 Boston ONE Team Serhant

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

Wenjun Cao Engel & Volkers 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

Andersen Group Realty Keller Williams Realty Boston Northwest

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

Kim Covino Compass

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

Wei Wenny Fu Phoenix Real Estate

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

Anne Spry Barrett Sotheby's International Realty

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

Nancy Pallotta Gibson Sotheby's International Realty

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,

Jing Chen Peace of Mind Realty

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

Kim Covino Compass

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

Kim Covino Compass

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

Kim Covino Compass

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

Kim Covino Compass

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

Anna Jung K Stadium Realty INC

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

Rose Hall Blue Ocean Realty, LLC

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

Janet Halloran RE/MAX Real Estate Center

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

Kim Covino Compass

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

Kim Covino Compass

EXCEPTIONAL LIVING AWAITS in this renovated / updated grand Contemporary home. Boasting soaring ceilings, oversized windows showcasing scenic private views and hardwood floors throughout; all you need to do is unpack. 4 of the 5 Generous sized bedrooms are located on the main floor - for mostly one-floor-living! The kitchen, complete with granite counter tops, center island seating and stainless,

Amie Pettengill Coldwell Banker Realty - Lexington

In a charming neighborhood with easy access to Peirce Elementary and McClellan Park, this stunning 2017-built Colonial on a corner lot with a massive, fenced-in yard is your new dream home. The main level greets you with gleaming hardwood floors and a thoughtfully designed layout that balances elegant entertaining with everyday comfort and flexibility. A sprawling, sun-filled family room with

Steve McKenna Gibson Sotheby's International Realty

Welcome to The Gates! This sought-after complex is located on the Stoneham/Winchester line in a dream commuter location with easy access to I-93, I-95, and Route 28! Boasting an in-ground pool, meticulously landscaped grounds, and a clubhouse, this is a beautiful place for down-sizers, first-time home buyers, and those alike! Unit 507 offers two bedrooms, including the primary with a walk-in

Philip Vita Compass

New Construction Move- In Ready Townhome at Highland at Vale in Woburn! The Jackson floor plan offers over 2,100 sq. ft. of thoughtfully designed living space with 3 spacious bedrooms and 2.5 baths. The main level features a bright kitchen with stainless steel appliances, abundant cabinetry, and a large center island, flowing into an oversized gathering room and an octagon-shaped dining room with

Erin Sullivan Pulte Homes of New England