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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29 Everett Avenue, Winchester, MA

Price$3,299,900

Est. Mortgage: $/month

Active With Contract

MLS Number 72163065

  • Single Family
  • Bathroom 7
  • Bedrooms 6
  • Year Built 2016
  • Parking Spaces 8

Grand New Construction w/ "Smart House" technology! Stylish and sophisticated 12 room 6 bedroom 6 1/2 bath home with 3 car heated garage! Located on prestigious Everett Avenue, this estate like home has been a labor of love for this top local builder and we are now proud to present this home, complete. Custom built and tastefully designed this expansive 5800 sq. ft+ home w/ designer kitchen and baths will exceed your highest expectations! Dramatic entry foyer, with solid mahogany door & wrought iron staircase~ First floor boasts 10 foot ceilings with a spacious open floor plan & large rooms~ A beautiful family room with coffered ceiling and stone/gas fireplace off gourmet kitchen with sunny breakfast room overlooking large rear yard w/ sliders to deck. Formal living room, dining room with wainscoting, butlers pantry, private study or additional bedroom with adjacent full bath on first floor. Fabulous Master suite with fireplace, walk-in closets,and spa-like bath~ Must see this home!

Listed by Kim Covino of RE/MAX Leading Edge

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

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$/month over payments
Federal 30-year interest rate: 3.95% last updated on Jul 13, 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 Aquinas Path, Winchester, MA

Price$2,995,000

Est. Mortgage: $/month

MLS Number 72180972

  • Single Family
  • Bathroom 6
  • Bedrooms 5
  • Year Built 2017
  • Parking Spaces 6

THE ULTIMATE IN LUXURY LIVING LOCATED 7 MILES NORTH OF BOSTON. New construction by local master builder! The design of this spectacular home with the integrated floor plan that every modern, savvy buyer seeks is truly a work of art. 2 floors of finished living with volume control surround sound throughout each room. The master suite with gas fireplace and separate sitting room makes you feel like you're in a boutique hotel, surrounded by elegance. Host your next Summer party outdoors on the exquisite covered Blue Stone patio. Another property by the same builder was featured as the "Home Of The Week" in Sunday's Boston Globe (11/30/2014). Located a short drive to downtown, where you'll find plentiful coffee shops, boutiques, restaurants, taverns, salons and the commuter rail to Boston. Do not miss out on this opportunity to own a true gem. Become a part of the Winchester and desirable Aquinas Path communities and experience all they have to offer!

Listed by Monte Marrocco, Gayle Winters and Philip Massa of RE/MAX Leading Edge

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

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$
$
%
$/month over payments
Federal 30-year interest rate: 3.95% last updated on Jul 13, 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$2,995,000

Est. Mortgage: $/month

Open House

MLS Number 72198378

  • Single Family
  • Next Open House: Sat 29th 1:00 pm - 2:30 pm
  • Bathroom 7
  • Bedrooms 6
  • Year Built 2004

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

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

Do not fill in this field:

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$
$
%
$/month over payments
Federal 30-year interest rate: 3.95% last updated on Jul 13, 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
  • Bedrooms 6
  • Year Built 2000
  • Parking Spaces 6

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.

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: 3.95% last updated on Jul 13, 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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128 Forest Street, Winchester, MA

Price$2,900,000

Est. Mortgage: $/month

MLS Number 72144993

  • Single Family
  • Bathroom 6
  • Bedrooms 5
  • Year Built 2002
  • Parking Spaces 10

The best of both worlds! Find the charm and detail typically only found in a historic home with all the amenities of a contemporary build. Magnificent, shingle-style home built using the finest materials and custom millwork. Stunning archways, custom doors, cabinetry and beautiful mahogany moldings throughout. 1st and 2nd floors include radiant floor heat, gleaming hardwood floors and Sonos system. Chef's kitchen with large mahogany center island and walk-in pantry. Master suite on 1st floor with custom built-in closet has plans for completed bath. Four spacious bedrooms on 2nd floor. Three grand fireplaces, exquisite windows, and partially finished basement. Beautiful screened-in porch and outdoor areas including a 4000 SF Carriage House, with heated, two-car garage with enormous possibilities (architectural plans, included with photos, show carriage house potential). Below is another heated garage with room for 6 cars. Truly a special home for the discerning buyer.

Listed by Donna Addezio and Paula R. Sughrue of Better Homes and Gardens Real Estate - The Shanahan Group

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: 3.95% last updated on Jul 13, 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 Fernway, Winchester, MA

Price$2,900,000

Est. Mortgage: $/month

MLS Number 72133499

  • Single Family
  • Bathroom 5
  • Bedrooms 5
  • Year Built 1941
  • Parking Spaces 6

Grand estate atop Myopia Hill. Steps to Boat & Country Clubs, handsome stone Tudor w/ slate roof features landscaped grounds & large backyard - ideal for families or entertaining. Gracious foyer steps down to formal living room w/ fireplace & adjacent sunroom. Den w/ custom built-ins & steps out to patio w/ Japanese garden. Elegant dining room w/ French doors opens to outdoor dining area underneath wisteria-covered pergola. Chef's kitchen & breakfast room was part of major addition. Family room w/ custom wet bar. Sprawling master suite boasts fireplace, 2 dressing rooms & en-suite bath w/ soaking tub & steam shower. 4 large bedrooms & 2 renovated baths complete upper level. Lower level w/ large media room, custom wet bar, catering kitchen, gym & storage. Customized 2 car garage. Beautiful landscaping w/ patio, custom lighting & irrigation. Newer windows, heating & cooling systems. Incredible light, detail & privacy in this meticulously kept home just a short drive from Boston.

Listed by Carmela Laurella and David Costello of CL Waterfront Properties

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

Do not fill in this field:

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$
$
%
$/month over payments
Federal 30-year interest rate: 3.95% last updated on Jul 13, 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$2,779,000

Est. Mortgage: $/month

Open House

MLS Number 72057411

  • Single Family
  • Next Open House: Sun 30th 1:30 pm - 3:30 pm
  • Bathroom 7
  • 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

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: 3.95% last updated on Jul 13, 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$2,699,000

Est. Mortgage: $/month

MLS Number 72202007

  • Single Family
  • Bathroom 5
  • Bedrooms 5
  • Year Built 1912
  • Parking Spaces 6

Come home to this exclusive residence located in one of Winchester's most prominent neighborhoods! This stunning home offers a high level of architectural detail boasting old world charm with modern high-end amenities. This 12 room, 4-5 bedroom, 4.5 bath home offers over 5600SF of living w/ 5 FPs. Enter through the custom oversized front door where you will be greeted with a warm foyer. Ideal for entertaining, the heart of this home is its gourmet kitchen that opens up to an expansive formal LR, DR and coffered ceiling FR equipped with sliders leading to the lush outdoor space. Iron staircase leads to the grand 2nd floor w/ lit barrel vaulted ceiling the focal point. Master suite with cathedral ceiling, walk-in closets, spa like bath & gym; 3 large beds, office and laundry finish this floor. Relax in the tranquil and private backyard featuring in-ground pool, hot tub, outdoor kitchen, stoned patio w/ trellis all surrounded by mature & natural landscaping. A luxurious home!

Listed by Kim Covino of RE/MAX Leading Edge

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: 3.95% last updated on Jul 13, 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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19 Dix Street, Winchester, MA

Price$2,450,000

Est. Mortgage: $/month

Active With Contract

MLS Number 72193600

  • Single Family
  • Bathroom 4
  • Bedrooms 4
  • Year Built 1860
  • Parking Spaces 8

Rare offering - the award winning Albert Fitch Bellows home was beautifully restored and now is looking for its next steward.Greeted by the carved staircase and oversized windows you feel immediately transported to serene living. This versatile floor plan offers you flexibility - living rm offers front/back FP & Family Rm both with access to wide porches so you can view Wedge Pond. Large dining rm with cove ceilings connecting to the spacious kitchen is perfect for entertaining. 2nd floor has expansive master with window seat, walk-in closet, & en suite bath. Three other ample bedrooms with scenic views & updated family bath complete this floor. LL in this home is spectacular, built in desks, space galore for entertainment center, pool table & kitchenette. Large walk in wine cellar with original door to home & another full bath. All with access to the spacious backyard and direct pond access. Three car garage, with close proximity to town center & privacy make this home the one to see.

Listed by Anne Spry and Stephanie Mcgowan of Waterfield Sotheby's International Realty

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: 3.95% last updated on Jul 13, 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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61 Arlington Street, Winchester, MA

Price$2,400,000

Est. Mortgage: $/month

Open House

MLS Number 72183294

  • Single Family
  • Next Open House: Sun 30th 1:30 pm - 3:30 pm
  • Bathroom 4
  • Bedrooms 5
  • Year Built 1969

Take in the sweeping views of Winchester Country Club from the front porch or enjoy the back yard patio or 3-season porch - wherever you go, you'll enjoy the beautiful surroundings and numerous updates that this home offers. Owners completely gutted and transformed the first floor by expanding the back side of the home to add a large mudroom with bath and laundry, large eat-in chef’s kitchen with every bell and whistle, expanded dining room and a stunning 3 season room; all with beautiful views of the back yard. 5 bedrooms on 2nd floor. Extensive improvements to landscape and hardscape; including irrigation, drainage and drywell, walkways, flower beds and a variety of specimen plantings. New windows throughout the home, new roof, 400 amp service. Less than 10 miles to Boston. Convenient to Rt 2,3,93 and 128. Enjoy all that Winchester offers - great schools, Middlesex Fells, Wright Locke Farm and much more. This is an exceptional home that must be seen.

Listed by Elizabeth Darby of Century 21 Commonwealth

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: 3.95% last updated on Jul 13, 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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