Winchester Luxury Homes

Known for its affluence and beauty, Winchester has some truly luxurious homes for sale. All priced over $800,000, you'll find a range of Winchester homes, from new construction mansions to contemporary condos- all with the finest features and amenities. 

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9 Grove Street, Winchester, MA

Price$4,599,000

Est. Mortgage: $/month

MLS Number 72254524

  • Single Family
  • Bathroom 8
  • Full Bath 6
  • Bedrooms 8
  • Year Built 2017

True elegance so rarely experienced, this majestic historic home has been completely renovated and restored to its original grandeur, blending exquisite period details with luxurious modern amenities. Quality throughout with designer touches and high-end finish work, this 8bed/8bath 10,000SF+ home has been tastefully redesigned for today’s lifestyle. This home features gourmet eat-in kitchen with Sub-Zero/Wolf appliances, french doors leading to deck, living room w/ coffered ceilings & FP, mahogany library & DR. Second floor boasts high ceilings, FP Master with spa bath & walk-in closet, en-suite beds and laundry with folding area. 3rd floor great for au-pair w/ 4 beds, full bath & add’l laundry area. Lower level features media room, kitchen/wet bar, game room, wine cellar, mirrored gym equipped w/ rubber flooring and spa bath w/ steam/sauna/rain shower. All new plumbing & heating, "Smarthouse" technology, 400amp electrical, surround sound, intercom system, 3/4 car garage. A must see!

Listed by Kim Covino of RE/MAX Leading Edge

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CENTURY 21 Advance Realty
284 Salem Street
Medford MA, 02115
Office: 781-395-2121

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 2017
* 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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54 Myopia Road, Winchester, MA

Price$2,950,000

Est. Mortgage: $/month

MLS Number 72166793

  • Single Family
  • Bathroom 7
  • Full Bath 5
  • Bedrooms 6
  • Year Built 2000

Decorative wrought iron gates open to a carriage driveway and reveal the spectacular mature gardens that create the estate setting for this Colonial Revival masterpiece. Set upon Myopia Hill, among homes of similar architectural distinction, it is difficult to imagine that such privacy can be available so close to the town of Winchester and within striking distance of the city of Boston. This family-friendly neighborhood provides ease of access to all Winchester offers: fine schools, children’s activities and clubs, boat club, beach, golf course, and the community’s Wright Locke Farm, to name a few. This home is resplendent in architectural detail, both inside and out. The floor plan was designed with a principal goal – to be first and foremost a family home designed around a central core dedicated to a large open plan kitchen and a generously proportioned family room. To the rear a large patio overlooks lawns for children’s activities and a woodland wonderland for exploration.

Listed by Jonathan Radford of Coldwell Banker Residential Brokerage - Boston - Newbury St.

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CENTURY 21 Advance Realty
284 Salem Street
Medford MA, 02115
Office: 781-395-2121

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 2017
* 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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10 Ledgewood Road, Winchester, MA

Price$2,945,000

Est. Mortgage: $/month

Open House

MLS Number 72198378

  • Single Family
  • Next Open House: Sun 22nd 11:30 am - 1:00 pm
  • Bathroom 7
  • Full Bath 4
  • Bedrooms 6

This grand estate is nestled into Winchester's most prestigious neighborhood, Ledgewood Estates, with beautifully wooded surroundings and rolling hills.This private compound has a large wooded backyard with a gunite pool, large outdoor mahogany deck and patio ideal for outdoor entertaining. Seldom does such a magnificent estate come on the market with such privacy and beauty. This estate lies 9 miles from downtown Boston or a short stroll to the commuter rail. This premier property has access to Fells reservation and is minutes away from the charming center of town and highly ranked schools.This exquisite residence features floor to ceiling French pella windows, ten foot ceilings, chunky crown moldings, 3 fireplaces, an enormous state of the art chef's kitchen, oversized island ideal for entertaining, large breakfast nook, custom white cabinets, stadium seating media room,3 car garage, screen porch.Custom designed with a sweeping open floor plan by award winning architect, Frank Olivia

Listed by Denise Petitti of RE/MAX Home Team

{$agent->Name}

CENTURY 21 Advance Realty
284 Salem Street
Medford MA, 02115
Office: 781-395-2121

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 2017
* 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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7 Grove Street, Winchester, MA

Price$2,579,000

Est. Mortgage: $/month

MLS Number 72297573

  • Single Family
  • Bathroom 7
  • Full Bath 5
  • Bedrooms 4
  • Year Built 2017

Spectacular NEW CONSTRUCTION, 6,294 sf home situated on over 20,000+SF lot! Custom built 4+bed, 5F/2H bath oversized colonial with 2 car attached garage in the rear is now ready for Spring Occupancy.The main level features an open floor plan with stunning gourmet kitchen w/10' island equipped with Wolf/Subzero appliances, adjacent Family room w/fireplace & built ins, butler’s pantry/wet bar, breakfast area with french doors leading to outdoor deck & private rear yard, Lavish Master suite offers cathedral ceilings,double walk-in closets, gas FP and luxurious MBath with soaking tub & separate shower. Second floor laundry w/ walk-in storage room, 3 oversized bedrooms and 2 full baths complete the 2nd floor. Perfect in-law/au-pair suite or recreational space with full bath on the third level! The lower level is finished w/ home theater, custom wet bar, exercise area & full bath - perfect for all your entertaining needs! Control 4 Home Automation, built-in speakers, and so much more!!

Listed by Kim Covino of RE/MAX Leading Edge

{$agent->Name}

CENTURY 21 Advance Realty
284 Salem Street
Medford MA, 02115
Office: 781-395-2121

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 2017
* 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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47 WAINWRIGHT Road, Winchester, MA

Price$2,499,900

Est. Mortgage: $/month

MLS Number 72224619

  • Single Family
  • Bathroom 7
  • Full Bath 5
  • Bedrooms 5
  • Year Built 2007

GRACIOUS, CUSTOM RESIDENCE sited on a private lot, in a very desirable location. Quality construction, dramatic architecture, elegant details and lavish appointments. A perfect blend of formal space and comfort. The gourmet kitchen features a breakfast room that leads to an outdoor patio, perfect for entertaining family and friends. The Master Bedroom features a spa- inspired bath and walk in closets. 3 additional bedrooms with en-suite baths and walk in closets complete this lovely home. This is a unique buying opportunity for this type of quality that is only found in custom built homes. Here is your chance to make it yours!

Listed by Dorothea Feffer of Coldwell Banker Residential Brokerage - Winchester

{$agent->Name}

CENTURY 21 Advance Realty
284 Salem Street
Medford MA, 02115
Office: 781-395-2121

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 2017
* 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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35 Central Street, Winchester, MA

Price$2,499,000

Est. Mortgage: $/month

Active With Contract

MLS Number 72304045

  • Single Family
  • Bathroom 5
  • Full Bath 4
  • Bedrooms 4
  • Year Built 1912

Exclusive residence located in one of Winchester's most prominent neighborhoods! This stunning 'California Chic' home offers a high level of architectural detail boasting old world charm with modern high-end amenities. Greeted by a warm spacious foyer, this exquisite home features 12 rooms, 4-5 beds, 4.5 baths, over 5600SF of living space & 5 FPs. Ideal for entertaining, the heart of this home is its gourmet kitchen that opens to an expansive formal LR, DR & coffered ceiling FR equipped w/ sliders leading to the lush outdoor space. Iron staircase leads to the grand 2nd level hallway feat. barrel vaulted ceiling. Master suite with cathedral ceiling, walk-in closets, soaking tub, steam shower & gym; 3 large beds, office & laundry finish this floor. Relax in the tranquil & private backyard featuring in-ground pool, hot tub, outdoor kitchen, stoned patio w/ trellis all surrounded by mature landscaping. A luxurious home close to the center of town, nearby schools & train into Boston!

Listed by Kim Covino of RE/MAX Leading Edge

{$agent->Name}

CENTURY 21 Advance Realty
284 Salem Street
Medford MA, 02115
Office: 781-395-2121

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 2017
* 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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366 Main Street, Winchester, MA

Price$2,399,000

Est. Mortgage: $/month

Active With Contract

MLS Number 72290639

  • Single Family
  • Bathroom 6
  • Full Bath 5
  • Bedrooms 5
  • Village Downtown Winchester

366 Main Street, once described by Boston Magazine as an "Unassuming Palace". Originally built in 1853, this historic Winchester property has been brought back to life by a premier local developer and is anxiously awaiting its next loving owner. Enriched with period detail that cannot be replicated today, this 14 room mansion is located just 7 houses from Winchester Center. With stunning landscaped grounds, stately original exterior detail, and a detached 4 car garage, you can truly live like royalty here. Do you love soaring ceilings, ornate woodwork and adorned mantels? How about an oversized designer kitchen? Or a master suite that would rival any 5-star accommodation? The flawless blend of new and old world design is possible, and this is proof! With 4 levels of finished space this home will wow you at every turn. 5 bedrooms in total including 2 en-suites, and the spectacular master. The lower level is set up for an amazing media room, with full bath and additional recreation room!

Listed by Philip J. Vita of RE/MAX Leading Edge

{$agent->Name}

CENTURY 21 Advance Realty
284 Salem Street
Medford MA, 02115
Office: 781-395-2121

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 2017
* 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 Johnson Road, Winchester, MA

Price$2,249,000

Est. Mortgage: $/month

Open House

MLS Number 72303838

  • Single Family
  • Next Open House: Sun 22nd 12:00 pm - 1:00 pm
  • Bathroom 5
  • Full Bath 4
  • Bedrooms 5

PERCHED HIGH ON A HILL WITH DISTANT VIEWS OF BOSTON! NEW CONSTRUCTION by local master builder! A short drive to downtown where you'll find plentiful boutiques, restaurants, coffee shops and the Commuter Rail to North Station. Within the 3-year old Vinson Owen School district. The first floor features an open floor plan for today's modern lifestyle, with a fireplaced family room, living room, dining room, kitchen and half bath. Enjoy entertaining your guests in the oversized kitchen, boasting a top of the line SS appliance package and granite counters. Experience the great outdoors featuring a large wooden deck and a plentiful back yard for your children to play in. 4 bedrooms are located on the second floor, including the master and an additional en-suite, along with laundry and plentiful closets. The third floor is finished with a 5th bedroom, bathroom and enormous bonus room. Long driveway is heated for your Winter convenience. Easy access to major highways and 7 miles from Boston.

Listed by The Marrocco Group and Monte Marrocco of Coldwell Banker Residential Brokerage - Winchester

{$agent->Name}

CENTURY 21 Advance Realty
284 Salem Street
Medford MA, 02115
Office: 781-395-2121

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 2017
* 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.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

1 Harrington Road, Winchester, MA

Price$2,199,000

Est. Mortgage: $/month

Open House

MLS Number 72256948

  • Single Family
  • Next Open House: Sun 22nd 1:00 pm - 2:30 pm
  • Bathroom 5
  • Full Bath 4
  • Bedrooms 4

1 Harrington Road is now for sale! Don't miss this beautifully designed NEW custom 4 bedroom 4 1/2 bath home located in the FLATS area of Winchester! Close to town, Ambrose elementary, and Wedgemere train station. Wonderful floor plan with dramatic 2-story entry, kitchen/great room combination with floor to ceiling stone fireplace visible from kitchen area, formal living room with french doors to front porch, dining room with wainscoting and beautiful trim work, 3-car garage with direct entry into great mudroom/ half bath area with storage, wide plank wainscoting, and tile floors. Gorgeous staircase with mahogany handrail leads to perfectly designed second floor featuring Master with cathedral ceiling, 2 walk in closets, linen closet, beautiful tile bath with gorgeous windows, high ceilings, glass enclosed shower and & 6ft soaking tub. 3 add'l BR's/3 baths. Finish the basement if you desire, plumbed for add'l full bath, create a media rom, gym, rec room. Located on over 10,000sf lot!

Listed by Kim Covino of RE/MAX Leading Edge

{$agent->Name}

CENTURY 21 Advance Realty
284 Salem Street
Medford MA, 02115
Office: 781-395-2121

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 2017
* 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

7 Ledgewood Road, Winchester, MA
Active With Contract

MLS Number 72216690

  • Single Family
  • Bathroom 4
  • Full Bath 3
  • Bedrooms 4
  • Year Built 1946

Custom Shingle style estate in one of Winchester's most private areas; near town ctr, schools, train, Fells. Beautifully set back on rare acreage ideal for outdoor living Property incl 10% ownership half acre lot with tennis court. Pella Energy Star windows/drs, Wood Mode cherry built-ins, radiant heat wood flrs thru-out Gourmet kitchen w/quartz, 10 foot island, top line SS appliances, gas FP, Butler's pantry w/wine cooler. 1st & 2nd flr master suites & potential for 5th bedroom. Walk-up attic. Perfect family home, also amazing for entertaining for small or large gatherings.

Listed by Peggy Otis of Coldwell Banker Residential Brokerage - Winchester

{$agent->Name}

CENTURY 21 Advance Realty
284 Salem Street
Medford MA, 02115
Office: 781-395-2121

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 2017
* 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.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

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