Winchester, MA Homes between $1,500,000 and $2,000,000 for Sale

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Newest Winchester, MA Homes between $1,500,000 and $2,000,000 for Sale

$1,699,000

4 Beds ⋅ 3 Baths ⋅ 73596720 MLS

Welcome to 3 Sunset Road, a beautifully updated 4 BR 2.5 bath colonial with rear addition featuring a 1st floor primary option, a fabulous great room w/vaulted ceilings, and a versatile floor plan! This beautiful home is situated on a generous 1/2 acre lot in one of Winchester’s most loved neighborhoods! The large renovated kitchen with custom cabinetry & high end appliances offers plenty of room for storage, cooking and gathering and opens to a lovely dining room w/ easy access to an expansive deck overlooking the gorgeous back yard, perfect for indoor and outdoor entertaining. A warm and inviting living room features a wood-burning fireplace, while the impressive family room with soaring vaulted ceilings provides an incredible space to gather. The luxurious primary suite offers a spacious bath with double vanities, a walk-in closet, and a private sunroom, ideal for a home office, gym, or quiet retreat. Three additional bedrooms and a full updated bath complete the second level. The finished lower-level playroom offers even more flexible living space. Outside, the expansive, private backyard is truly special, offering endless possibilities for kids play, gardening, entertaining, relaxing. A wonderful opportunity to move right in and enjoy spacious living in a fantastic Winchester location, convenient to schools, shops, restaurants, and all that Winchester has to offer!

3 Sunset Road, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.

$1,985,000

4 Beds ⋅ 4 Baths ⋅ 73589478 MLS

Set on over an acre of beautifully landscaped grounds abutting acres of woodland, this extensively renovated Contemporary Cape offers exceptional privacy and a peaceful connection to nature. A thoughtfully designed open floor plan features hardwood floors, a fireplaced living room, elegant dining room, and a beamed-ceiling family room adjoining the remodeled kitchen with stone counters, stainless appliances, and island. A private great room off the foyer, with windows on three walls and a slider to the spacious deck, offers a wonderful retreat. French doors open to the expansive deck overlooking the fenced backyard and wooded surroundings. Upstairs, four bedrooms include a primary suite with custom closets and private bath. The finished walkout lower level offers flexible space for a home office, gym, or guests, with separate entrance and full bath. Stone walls, mature landscaping, a long private driveway, and two-car garage complete this exceptional home.

30 Surrey Rd, Winchester

Listing courtesy of Listing Agent: Anne Spry from Listing Office: Barrett Sotheby's International Realty.

$1,999,000

5 Beds ⋅ 4 Baths ⋅ 73588059 MLS

Welcome to this beautifully appointed and exceptionally spacious home, ideally situated in a quiet, desirable West Side Winchester neighborhood within the sought-after Vinson-Owen School district. Offering an impressive combination of elegant living spaces, flexible accommodations, and thoughtful upgrades, this home provides room for everyone while easily adapting to a variety of lifestyles. At the heart of the home is the expansive granite kitchen, designed for both everyday living and entertaining. Custom cabinetry, Thermador double ovens, a Dacor warming drawer, Sub-Zero refrigerator, wine refrigerator, recessed lighting, and an impressive 50-square-foot center island create a wonderful gathering space with plenty of room for cooking, dining, and entertaining. The kitchen flows into a comfortable family room featuring a custom-built entertainment center and electric fireplace. A gracious formal dining room showcases handcrafted molding and classic wainscoting, while additional first-floor living spaces provide tremendous flexibility for a formal living room, playroom, home office, den, or whatever best suits your needs.One of the home's most appealing features is the first-floor bedroom suite with a full bath, offering exceptional versatility for extended family, guests, an au pair, or anyone seeking the convenience of first-floor living. A dedicated laundry room on this level adds even more functionality. With multiple living areas and flexible rooms throughout the first floor, there are countless ways to create private spaces for additional family members while still enjoying plenty of room to gather together.Upstairs, the generously sized primary suite provides a relaxing retreat with vaulted ceilings, recessed lighting, double closets, and a beautifully tiled private bath with double sinks. Three additional spacious bedrooms, another full bath, and additional office space provide abundant room for family, guests, work-from-home needs, hobbies, or study areas.With its generous proportions, flexible floor plan, multiple bedroom and living configurations, and outstanding West Side location, this is a home designed to grow and change with its owners. Enjoy the peace and privacy of a quiet neighborhood while being part of the wonderful Winchester community. This is more than simply a beautiful house—it is a home offering the space, versatility, and comfort today's buyers are looking for.

21 Amberwood Dr, Winchester

Listing courtesy of Listing Agent: Gayle Winters & Co. Team from Listing Office: Compass.

$1,529,000

4 Beds ⋅ 4 Baths ⋅ 73584817 MLS

An exceptional opportunity in one of Winchester’s most desirable neighborhoods, directly across from the Winchester Country Club. Set on a beautiful .39-acre lot, this distinctive 4-bedroom, 3.5-bath Colonial offers approximately 2,709 sq. ft. of living space, a 2-cargarage, generous room proportions, and a flexible floor plan ready for its next chapter. Offering wonderful possibilities with its generous proportions, flexible floor plan, and impressive setting, the property presents an ideal canvas for buyers looking to renovate and personalize a home to their exact vision. Reimagine the existing spaces with sophisticated modern finishes, create a timeless renovation that complements the home’s character, or explore the possibilities for a more extensive transformation. The spacious lot also provides plenty of room to enhance the outdoor experience with thoughtfully designed landscaping, gardens, patios, entertaining areas, or other outdoor amenities. Beyond the property itself, the location stands out, with the Winchester Country Club just across the street and downtown Winchester conveniently nearby, offering restaurants, cafés, shops, services, and commuter rail access to Boston. Convenient access to Winchester public schools, major routes, and nearby public transportation makes commuting and exploring the Greater Boston area easy. Bring your architect, contractor, and creativity and transform this property into something truly special. With its substantial lot, desirable neighborhood setting, proximity to downtown, and access to everything Winchester has to offer, 25 Arlington Street presents a rare chance to create a home that reflects your own style in an exceptional location.

25 Arlington St, Winchester

Listing courtesy of Listing Agent: Domingo Medina from Listing Office: Coldwell Banker Realty - Lexington.

$1,750,000

4 Beds ⋅ 3 Baths ⋅ 73581571 MLS

NEW Photos! Welcome to One Overlook Way in Winchester. This home is located on a 1/3 acre corner lot on a short cul-de-sac off High Street- a premier location close to Ambrose Elementary School and the Winchester Country Club. Don't miss this spacious 4+ bedroom center-entrance Colonial. with a thoughtfully designed circular flow for everyday living and entertaining. The generously sized eat-in kitchen features stone countertops and stainless steel appliances and connects to the beautiful dining room. The kitchen with room to add an island or large table also opens naturally into the comfortable family room - with gas fireplace, custom built-ins, a new split AC and access to the back and side yard! A larger front-to-back living room with fireplace and box windows is located off the foyer and is complemented by an adjoining oversized library or playroom. Upstairs, the spacious primary suite offers a split AC, private bath with double vanity, full shower and great closet space. Three additional bedrooms feature hardwood floors, generous closets and access to a shared full bath. The third-floor bonus space provides flexible room for guests, a second home office, hangout zone or storage. The finished lower level adds another playroom, with a fireplace and room for exercise, hobbies or relaxation. Enjoy the outdoors in this large, level yard with established plantings, brick patio and plenty of space to entertain. There is a two-car garage plus 300+sf of unfinished storage space above the garage. Please ask the agent for more information. This home truly has it all. This is one home you do not want to miss.

1 Overlook Way, Winchester

Listing courtesy of Listing Agent: Lynne Russo from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.

$1,650,000

5 Beds ⋅ 4 Baths ⋅ 73573887 MLS

Expansive living and unparalleled curb appeal define this exceptional five-bedroom garrison colonial, ideally positioned near the natural beauty and extensive trails of the Fells Reservation. Set in the highly regarded Muraco Elementary School district, this spacious home offers an inviting blend of timeless architecture, thoughtful updates, and remarkable flexibility for today’s lifestyle. The sun-filled first floor features an open, seamless flow designed for both everyday living and effortless entertaining. A thoughtfully appointed eat-in kitchen with premium Sub-Zero and Fisher & Paykel appliances opens to the dining space, creating an ideal setting for gathering. A wood-burning fireplace anchors the living room where you can watch the world go by from the gorgeous picture window. A home office, mudroom, and powder room add functionality to this level. Upstairs, the generous primary suite includes a full bath and convenient laundry, with tree-top views from the Juliet balcony, complemented by four additional bedrooms and a family bath. A finished walk-up attic provides valuable storage and flexible bonus space, while the finished lower level adds a generous family room and several bonus spaces ideal for a second home office, playroom, media space, or additional recreation area, with kitchenette and full bath allowing for ADU possibilities. Outside, enjoy a truly private retreat with a fully fenced yard and pristine in-ground pool, offering exceptional space for outdoor living, entertaining, and relaxation. A two-car attached garage adds everyday convenience. With generous proportions throughout, multiple flexible spaces, an inviting open floor plan, and close proximity to the Fells Reservation, this Winchester Highlands property offers a rare opportunity to enjoy space, privacy, and sophisticated everyday living in one of Winchester’s desirable neighborhoods.

117 Highland, Winchester

Listing courtesy of Listing Agent: Dara Singleton from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.

$1,749,000

5 Beds ⋅ 4 Baths ⋅ 73572890 MLS

A rare offering in one of Winchester's most desirable neighborhoods, this spacious mid-century contemporary spans approximately 3,500 square feet with 5 bedrooms and 3.5 baths on a private 0.24-acre lot. The open main level flows from a light-filled living room with a cathedral ceiling, stained-glass accents, and a fireplace into the dining room, family room, and a renovated kitchen with Silestone quartz countertops, upgraded cabinetry, and direct deck access. Upstairs, two ensuite bedrooms anchor the floor plan, including a generous primary suite with a large jetted soaking tub, vanity, and walk-in closet. Three additional bedrooms and a family bath complete the level. Hardwood floors run throughout, a second fireplace warms the lower-level bonus room, and ductless mini-splits deliver year-round comfort throughout the house. The walk-out lower level offers a versatile bonus room with its own exterior entrance, ideal for a home office, gym, media room, playroom, or guest suite. Three decks extend the living space outdoors for entertaining and dining above the private backyard, and an attached two-car garage adds everyday ease. Set on a quiet street with easy access to commuter rail, downtown Winchester, parks, and bike or jog trails, this is a rare chance to live in your dream home in a community that has it all.

17 Churchill Rd, Winchester

Listing courtesy of Listing Agent: Domingo Medina from Listing Office: Coldwell Banker Realty - Lexington.

$1,599,000

4 Beds ⋅ 2 Baths ⋅ 73572661 MLS

Price Change!! **Open House this weekend or call for private showings** Great offering~ Extensively rebuilt and expanded, this impeccably maintained 4 Bed 2 BA home offers a spacious and versatile floor plan. The impressive 28’ x 20’ great room w/living area and dining area features vaulted ceilings, bay window, and a gas fireplace which flows nicely from the updated kitchen. Step outside to a new oversized Azek deck with plenty of room for grilling, dining, and relaxing. The main level also includes formal living room w/ fplc, plus 2 spacious bedrooms & full bath. offering flexibility for various uses. Upstairs are two additional generously sized bedrooms with hardwood floors and ample closet space, along with a full hall bath featuring a skylight. Additional highlights include a finished lower level, laundry and storage areas, and direct access to a two-car garage. Beautifully landscaped grounds feature perennial gardens, flowering trees, natural stone walls, and exceptional privacy—nestled into one of Winchester’s most desired neighborhoods, all just 7 miles from Boston with convenient access to the town center, Fells trails, major routes and highways. Please see feature/ update list attached.

4 Churchill Road, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.

$1,899,000

4 Beds ⋅ 3 Baths ⋅ 73565817 MLS

Classic Colonial nestled within one of Winchester’s most desirable neighborhoods, offering timeless architecture, exceptional flexibility, and an enviable setting. The first floor features an updated kitchen with slider to the scenic rear yard and oversized brick patio, casual den, half bath, formal dining room, and gracious living room with fireplace and classic built-ins. Double doors lead to a spectacular all-season porch, perfectly positioned for effortless entertaining indoors or out. The second floor offers four corner bedrooms, including a spacious primary suite with double closets, ensuite bath, and convenient laundry. The walk-up third floor invites endless possibilities with an additional bedroom and abundant closet space. Approximately 500 square feet of finished lower-level flex space provides room for a home gym, teen retreat, playroom, or office. Outside, a private, level yard offers ample space for gardens, play, and entertaining, with a generous brick patio for relaxing and gathering. The two-car heated garage features a full walk-up second floor, ideal for storage or future finishing as a studio, office, or home-away-from-home retreat. Simply a beautiful home in an exceptional location—ready to be loved from day one.

85 High St, Winchester

Listing courtesy of Listing Agent: Catherine Albiani from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.

$1,549,000

3 Beds ⋅ 3 Baths ⋅ 73556633 MLS

Private showings available! Resort living just steps from the town center! Completely remodeled with custom finishes throughout, this stunning expanded cape with 3 levels, 3/4 bedrooms, 2.5-baths will exceed your expectations. The first floor features a spacious primary bedroom w/ full bath, an inviting living room w/ beautiful fireplace surrounded & custom built-ins, while the chef's kitchen is designed to impress with high end finishes, a large island and vaulted breakfast nook. The open floor plan flows into the dining room, complete with a custom built-in wine bar, ensuring easy entertaining. The second floor provides two very large bedrooms with great closet space and a tastefully remodeled hall bath. The beautifully finished lower level offers incredible flexibility with a cozy family room, kitchenette, laundry and 1/2 bath, with potential for a 4th BR, making it ideal for entertaining, guests, or extended living space. Step outside to an extraordinary backyard that feels like a resort! Enjoy the professionally landscaped grounds, lush gardens, and an expansive patio creating the ultimate outdoor oasis-featuring a built-in grill, pizza oven, bar seating, a hot tub, greenhouse, and shed. The retractable awnings make for comfortable shaded entertaining. It is truly a backyard that you will use all year round! Ideally located just outside Winchester center, enabling you to enjoy all the benefits of being close to town! This turn-key home is a must see, don't miss this one of a kind, move in ready home with so many recent upgrades!

50 Holland Street, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.

$1,999,000

4 Beds ⋅ 4 Baths ⋅ 73556476 MLS ⋅ ['The Ledges'] BLDG.

Experience elevated living in this exquisitely renovated luxury townhouse at The Ledges! This sought-after condominium community, just minutes from Winchester Center, offers the ease of low-maintenance living w/ the feel of a single-family home, plus exceptional amenities including a private clubhouse, swimming pool, & tennis courts. Featuring the community's most desirable floor plan, this home offers an elegant first-floor primary suite w/ dual walk-in closets and a stunning spa-inspired bath. Meticulously reimagined from top to bottom, every element of this extraordinary renovation was thoughtfully curated using the finest imported designer finishes and bespoke craftsmanship, creating an unparalleled level of luxury. The dramatic open-concept main level is highlighted by soaring vaulted ceilings, a fireplaced living room w/ a custom-designed mantel, & walls of glass that open to a private deck overlooking breathtaking western sunsets & tranquil natural surroundings. The designer kitchen is a true showpiece, featuring premium finishes, a sun-filled breakfast area, & seamless flow into the elegant dining room, ideal for both intimate gatherings & entertaining.The second floor offers 3 rooms including a spacious bedroom, beautifully renovated full bath, loft ideal for a home office, & an additional sitting room/TV room or guest space. The walk-out lower level it’s another suite in itself offering a spacious family room, second kitchenette, dining area, game room, additional bedroom with double closets, a luxurious spa bath, oversized laundry room, and abundant storage. Step outside to a private patio surrounded by peaceful, picturesque grounds, creating the perfect retreat for relaxing or entertaining. Ideally located w/ easy access to Winchester Center, Whole Foods, major highways, restaurants, and shops, this exceptional home offers luxury living just 7 miles from downtown Boston.

7 Wainwright Road Unit 113, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.

$1,749,000

3 Beds ⋅ 4 Baths ⋅ 73555777 MLS

Welcome home to this beautifully renovated gem, perfectly positioned 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 today’s buyers are looking for—featuring a stunning kitchen that flows effortlessly into the dining and living areas, plus a sunken family room ideal for relaxing or entertaining. Step outside to enjoy the beautifully fenced-in yard, offering a private outdoor retreat for play, pets, gardening, or gatherings. Everyday convenience continues with a mudroom located directly off the driveway, multiple off-street parking spaces, and a two-car garage. The finished lower level includes a full bathroom and versatile flex space perfect 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. Thoughtfully renovated from top to bottom, this home features all new systems for peace of mind and effortless modern living. Located just a short walk to Winchester’s vibrant town center and commuter rail.

1 Town Way, Winchester

Listing courtesy of Listing Agent: Vita Realty Group from Listing Office: Compass.

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Winchester, MA Homes between $1,500,000 and $2,000,000 for Sale

Newest Winchester, MA Homes between $1,500,000 and $2,000,000 for Sale

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