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Winchester MA Real Estate

Discover Winchester, MA real estate with the help from expert realtors at The Greene Realty Group. Look through a variety of listings, including commercial spaces, single family homes, apartment, and more.

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6 Vinson Circle Winchester MA 01890

Winchester, MA6 Vinson Circle

Price$4,199,000

Est. Mortgage: $/month

MLS Number 73328916

  • Residential
  • Bedrooms 6
  • Bathroom 8
  • Square Feet 7,500
  • High School Winchester High

Nestled on a cul-de-sac in Winchester's desirable west side, this brand-new construction redefines modern luxury living. Spanning 7,500 sq. ft., this exquisite 6-bedroom, 7.5-bathroom home combines style, comfort, and functionality. Discover an open-concept floor plan bathed in natural light, perfect for entertaining and everyday living. The kitchen features top-of-the-line Wolf appliances, Sub-Zero refrigerator, custom cabinetry, and an oversized island. Adjacent living and dining areas offer ample space for gatherings. The primary suite is a retreat with a spa-like bath, large walk-in closet, and serene atmosphere. Each additional bedroom boasts its own en-suite bathroom for privacy and convenience. The finished lower level offers endless possibilities—a home gym, golf simulator room, or private theater. The walk-out basement leads to a beautifully landscaped backyard, ideal for outdoor activities. A three-car garage completes this exceptional home. Schedule your showing today!

Listed by Peter Kasseris of Coldwell Banker Realty - Lexington

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%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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20 Amberwood Drive Winchester MA 01890

Winchester, MA20 Amberwood Drive

Price$3,898,000

Est. Mortgage: $/month

MLS Number 73322357

  • Residential
  • Bedrooms 6
  • Bathroom 7
  • Square Feet 8,866
  • High School Winchester

Stunning 8800 sq ft brand-new contemporary in one of Winchester's favorite neighborhoods. A gracious foyer w/ high ceiling welcomes you to this elegant home loaded with natural light and architectural detail. Custom features include a gourmet eat-in kitchen w/ granite countertops, high-end appliances, secondary prep area, and fabulous outside dining options from the oversized deck. The fire-placed family room, banquet-size dining room w/ wine-column, private home office and bedroom w/ en-suite bath complete the first floor. Luxurious primary suite w/a large balcony, expansive walk-in closets & spa-like bath w/ dual vanities and a lavish soaking tub on upper level, along w/ 3 additional en-suite bedrooms and an oversized laundry room. Finished lower level features additional entertainment areas, gym&en suite-bedroom. BOSCH A/C units can switch between propane/electric heating. Fantastic location just up the hill from top-rated Vinson Owen School. Enjoy all that Winchester has to offer.

Listed by Sino-US Realty Team and Dan Li of Keller Williams Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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27 Everett Avenue Winchester MA 01890

Winchester, MA27 Everett Avenue

Price$3,799,000

Est. Mortgage: $/month

MLS Number 73324581

  • Residential
  • Bedrooms 6
  • Bathroom 6
  • Square Feet 7,431
  • High School Winchester

This is one of the most notable and distinguished homes on Everett Avenue, with preeminent siting on more than half an acre. This residence combines the magnificence of early 1900s architecture with today's modern amenities. Completely renovated in 2023/2024, this home features hallmark architectural details including Tudor-style balusters and high ceilings. Large rooms, coffered ceilings, original crown moldings, mantels, and decorative trim are enhanced by the beauty of restored hardwood floors. The new kitchen is a chef's dream with a walk-in pantry w/laundry and refrigerator drawers plus a butler's pantry with a wine fridge. A huge family room is flanked by floor to ceiling windows. Upstairs, a magnificent fireplaced primary wing boasts a new spa-like bath with custom walk-in closets plus an adjacent study with extra closets, for relaxing, working or meditation. The huge lawn is one of the biggest you can find, with magnificent old oak trees, beautiful birches & an ample driveway.

Listed by The Pallotta Group and Nancy S. Pallotta of Advisors Living - Winchester

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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4 Norwood Street Winchester MA 01890

Winchester, MA4 Norwood Street

Price$3,675,000

Est. Mortgage: $/month

MLS Number 73333712

  • Residential
  • Bedrooms 5
  • Bathroom 5
  • Square Feet 5,250

Welcome to 4 Norwood St, a stunning custom-built home by Mark Stephen Development. Just a short walk to Winchester town center with easy access to Boston, this home features exquisite millwork, custom built-ins, and premium finishes throughout. The main home offers 4 bedrooms, 3.5 bathrooms, a living room, dining room, sitting room, pantry, and a bar alcove, along with an expansive second-floor office/flex space. A separate but attached wing—perfect for extended family or guests—boasts soaring 13’6” ceilings, a grand entertaining area with chandeliers, a full kitchen, and a private guest primary suite. With every imaginable bell and whistle, this home is truly one of a kind.

Listed by Mark Donnellan of Advisors Living - Winchester

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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2 Chestnut Street Winchester MA 01890

Winchester, MA2 Chestnut Street

Price$3,599,000

Est. Mortgage: $/month

MLS Number 73333668

  • Residential
  • Bedrooms 6
  • Bathroom 5
  • Square Feet 5,500

Welcome to 2 Chestnut Street, an exquisite new construction home in progress by Mark Stephen Development. Situated off coveted Main Street in one of Winchester’s most sought-after neighborhoods, this residence is thoughtfully designed to blend timeless charm with modern conveniences. The home will feature five spacious bedrooms, five full bathrooms, a first-floor office, and a basement offering flexible space for an additional office, playroom, exercise room, or living area. The open-concept kitchen will include premium appliances, a grand nine-foot island, and custom cabinetry, while the primary suite will boast luxurious his-and-her closets and a spa-like bathroom with a soaking tub and marble-tiled shower. A third-floor bonus space adds versatility. With mature landscaping providing privacy and a spacious patio for outdoor living, this property is conveniently located near Winchester town center, top-rated schools, offers easy access to Boston, and promises an unparalleled lifestyle

Listed by Mark Donnellan of Advisors Living - Winchester

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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8 Chestnut Street Winchester MA 01890

Winchester, MA8 Chestnut Street

Price$3,299,000

Est. Mortgage: $/month

MLS Number 73305360

  • Residential
  • Bedrooms 5
  • Bathroom 6
  • Square Feet 5,366
  • High School Winchester

This iconic vintage farmhouse seamlessly blends historic charm with modern luxury. Spanning over 5,366 sq. ft., this home has been completely renovated and thoughtfully expanded for today’s lifestyle. Featuring 5 bedrooms, 4 full and 2 half baths, every inch exudes elegance and comfort. The designer kitchen is a chef’s dream, with high-end appliances, a beverage bar, and a large center island that flows into the open-concept living and dining areas—perfect for entertaining. The spacious primary suite boasts a walk-in closet and a magazine-worthy en-suite bath. Stunning light fixtures throughout add a sophisticated touch. Outside, professional landscaping creates a serene oasis, complete with a cozy fire pit for year-round enjoyment. Nestled in a prime location, this home offers unmatched convenience to Winchester Center, top-rated schools, dining, shopping, The Fells, and more. Don’t miss this rare chance to own a piece of Winchester’s history with all the modern amenities!

Listed by The Marrocco Group of Coldwell Banker Realty - Lexington

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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15 Churchill Road Winchester MA 01890

Winchester, MA15 Churchill Road

Price$2,699,000

Est. Mortgage: $/month

MLS Number 73298854

  • Residential
  • Bedrooms 4
  • Bathroom 5
  • Square Feet 5,501
  • High School Winchester

Indulge in modern luxury with this 2024 masterpiece, set on a double 1/2 acre lot. This 4 bedroom, 4.5-bathroom home seamlessly blends chic style with an abundance of functional space. The architectural design is dramatic, showcasing soaring ceilings, a stunning contemporary fireplace, state of the art kitchen & sun filled living room which opens to a fabulous deck, creating a perfect indoor-outdoor space. The gourmet kitchen features a sleek design w/ a large island, high end appliances, & stylish open shelving. Upstairs, the lavish primary suite features a spa like bath & large custom closet. The 3 additional bedrooms offer ensuite baths. The walk out LL family room w/ wet bar is the perfect space to unwind. This property also features a 2 gar attached garage, mud room, office & laundry room. The double lot offers many possibilities ~ level w/ patio. This home is located near conservation trails, top-rated schools & Boston offering a lifestyle of convenience, luxury & tranquility!

Listed by Kim Covino & Co. Team and Kim Covino of Compass

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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3 Lagrange Street Winchester MA 01890

Winchester, MA3 Lagrange Street

Price$2,699,000

Est. Mortgage: $/month

MLS Number 73324754

  • Residential
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 4,060

Nestled in a sought-after neighborhood, this stunningly reimagined home combines timeless charm and modern comfort, just a short walk to downtown. The inviting foyer welcomes you from a wrap-around porch into an open yet intimate layout connecting the kitchen, dining, and family rooms. A mudroom with marble checkered flooring and a walk-in pantry with a beverage fridge add practical luxury. The second floor offers three spacious bedrooms, including a serene primary suite with a walk-in closet and luxurious en-suite, plus a second bathroom and adjacent laundry room. The third floor features a private retreat with a bedroom, full bath, and flexible space for an office or sitting area. The lower level provides options for a playroom, exercise room, or office. Outdoor living shines with a bluestone patio accessed from the family room, perfect for entertaining. A detached two-car garage completes this exceptional property.

Listed by Mark Donnellan of Advisors Living - Winchester

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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50 Winford Way Winchester MA 01890

Winchester, MA50 Winford Way

Price$2,599,000

Est. Mortgage: $/month

MLS Number 73288818

  • Residential
  • Bedrooms 5
  • Bathroom 5
  • Square Feet 4,270
  • High School Winchester

Stunning new construction! Energy star rated, high efficiency 5 bed 4.5 bath home perfectly situated in a prime East Side location! The first floor welcomes you w/ an open, airy layout, featuring a stylish mudroom, pantry, bath & home office. The gourmet, high-end kitchen flows seamlessly into the living room, complete w/ a cozy fireplace; the dining area extends out to a deck, overlooking a beautifully landscaped yard & patio. The second floor boasts four spacious bedrooms & three full baths, including a lavish primary suite w/ a spa like bathroom. A well-appointed laundry room is also conveniently located on this floor. The third-floor suite is a true retreat, offering two versatile rooms ideal for extended family, office, or lounge, complete w/ a wet bar, an oversized bath & a 5th bedroom with abundant closet space. The expansive lower level adds even more living space, featuring a large family room and an additional full bath, perfect for entertaining. This home truly has it all

Listed by Kim Covino & Co. Team and Kim Covino of Compass

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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6 Ardley Place Winchester MA 01890

Winchester, MA6 Ardley Place

Price$2,300,000

Est. Mortgage: $/month

MLS Number 73331755

  • Residential
  • Bedrooms 5
  • Bathroom 4
  • Square Feet 3,676
  • High School Winchester High

Tucked away on a dead-end street, 6 Ardley Place blends classic character with modern comforts. Beautifully expanded with a complete renovation & redesign in 2013, this home offers a warm & inviting atmosphere w/elegant finishes throughout. The heart of the home is a stunning chef’s kitchen, featuring a 10 foot walnut island, Viking gas stove, beautiful cabinetry, & flows into the family room w/custom built-ins. Plantation shutters & an impressive wet bar. The dining room, anchored by a classic fireplace, is perfect for gatherings. Upstairs, the serene primary suite is complemented by 2 spacious bedrooms & a convenient laundry room. The 3rd floor offers 2 additional bedrooms w/cozy sitting room, & full bath. Set on over half acre, the home boasts incredible curb appeal, a 2-car garage, a sprawling deck overlooks the beautifully landscaped yard w/a bluestone stone patio & fire pit —ideal for outdoor entertaining. Thoughtfully designed w/warmth & sophistication, this home is a true gem!

Listed by McGlynn & Nigro Team, Michele McGlynn and Antonella Nigro of Berkshire Hathaway HomeServices Commonwealth Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. (MLSPIN) from third party sources, including sellers, lessors and public records, and were compiled by MLSPIN. The property listing data and information, and the Images, are for the personal, non-commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLSPIN and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.