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

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: 4.03% last updated on Apr 27, 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$3,175,000

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:

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$
$
%
$/month over payments
Federal 30-year interest rate: 4.03% last updated on Apr 27, 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$3,100,000

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: 4.03% last updated on Apr 27, 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:

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$
$
%
$/month over payments
Federal 30-year interest rate: 4.03% last updated on Apr 27, 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 28th 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:

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$
$
%
$/month over payments
Federal 30-year interest rate: 4.03% last updated on Apr 27, 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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251 High Street, Winchester, MA

Price$2,659,000

Est. Mortgage: $/month

MLS Number 72142710

  • Single Family
  • Bathroom 6
  • Bedrooms 5
  • Year Built 2017
  • Parking Spaces 10

NEEDLE IN A HAYSTACK! Almost impossible to find in Winchester....but here it is! New construction on a 24,000 square foot lot. Plenty of space to build a custom pool in your backyard. Quiet and serene location across the street from conservation land with a scenic pond. Enjoy all the pizzaz associated with new construction, including a 1st floor master suite which can be used as a home office, a luxurious master suite with walk in closet and marble bathroom, your very own home theatre with wet bar and lastly, the not-to-be-missed home gym with sauna & steam room. Enjoy a chilled beverage on one of the many decks and patios that surround the home, during the warm Summer evenings. Minutes to the 3 year old Vinson Owen school. Easy access to major highways and only 7 miles North of Boston. Downtown you'll be greeted with plentiful boutiques, taverns, spas, coffee shops, restaurants and the wonderful farmer's market on the common. Become a part of the Winchester community today!

Listed by Monte Marrocco and Philip Massa 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: 4.03% last updated on Apr 27, 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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17 Wolcott Road, Winchester, MA

MLS Number 72161062

  • Single Family
  • Bathroom 5
  • Bedrooms 4
  • Year Built 2017
  • Parking Spaces 6

Stately & Unique brand new colonial home built by local premier builder. This 5000+ sqft home w/ 3 car gar has the perfect blend of quality, superior workmanship & location. Features include an interior rich w/ architectural details; hardwood floors, crown moldings, coffered ceilings, wainscoting & chair railings. Foyer opens to spacious living rm and private office w/built-in cabinetry in both beyond the curved staircase you will find the designer gourmet kitchen w/ quartzite counter tops, work/breakfast island, Wolf & Sub Zero SS appliances & built-in seating extends into an entertaining size dining room & large family room w/ wood FP & triple French door to a stone patio. The 2nd fl with luxurious MB suite, spa bth & walk-in closet. There are 3 additional bdrms one with private bth the others share a Jack & Jill bth and laundry room complete this level. Basement offers oversized mud room, full bth & storage! Still under construction, plenty of time to choose your own finishes

Listed by Errico Team, Kelly Errico and Mary Errico 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: 4.03% last updated on Apr 27, 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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238 High Street, Winchester, MA

Price$2,299,000

Est. Mortgage: $/month

MLS Number 72129449

  • Single Family
  • Bathroom 8
  • Bedrooms 5
  • Year Built 2006
  • Parking Spaces 5

Enjoy residential bliss in this classic colonial home on a lot that affords privacy and tranquility, while not being secluded. Purchased by current owners as new construction in 2008, this home is ideally located in the acclaimed Vinson Owen school district with easy access to Rte. 93 and Boston. This impeccably-landscaped home features lush greenery and mature plantings that are appreciated from every room. Boasting expansive living spaces, chef’s kitchen, intricate detailing, distinctive fireplaces and the finest finishes at every turn, this magnificent residence epitomizes class and style whether you wish to relax casually or entertain grandly. Extra features in this home include security system, oversized 3 car garage, wifi enabled thermostat system, wifi controlled lighting, custom closets in 4 bedrooms, surround sound system in living room and family room, central vacuum, completely wired for cable and internet, and gas fireplaces.

Listed by The Andersen Team 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: 4.03% last updated on Apr 27, 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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53 Hutchinson Road, Winchester, MA

Price$2,099,000

Est. Mortgage: $/month

Active With Contract

MLS Number 72113644

  • Single Family
  • Bathroom 5
  • Bedrooms 6
  • Year Built 2015
  • Parking Spaces 5

Meticulously cared for 2-year old home looking for a long term relationship with new owners! Completed in 2015, this large Colonial is beautifully situated across the street from the golf course and within the Vinson Owen School district. Designed for today's modern lifestyle, this home features 6 bedrooms, 5 bathrooms and eye pleasing, neutral colors throughout. Enjoy the integrated floor plan with an oversized kitchen featuring SS appliances and granite counters. The lower level has since been finished into a bonus room with wall to wall carpet. A large stone patio was added to the backyard, equipped with BBQ and firepit, perfect for roasting marshmallows! Energy efficient living and mobile phone controlled smart home. A short distance to downtown where you'll find plentiful boutiques, restaurant, salons, spas, taverns and the commuter rail to Boston. Don't miss out on this opportunity to become a part of the Winchester community and all it has to offer. Only 7 miles North of Boston!

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

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.03% last updated on Apr 27, 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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15 Lincoln Street, Winchester, MA

Price$1,999,999

Est. Mortgage: $/month

MLS Number 72154104

  • Single Family
  • Bathroom 7
  • Bedrooms 6
  • Year Built 1871
  • Parking Spaces 4

The owners of this lovely Mansard have managed to tastefully blend historic charm, character & wonderful architectural details w/new, top of the line, updated features incl: all new electrical, HVAC, wood siding, roof, insulation & more! (See attached for list of all upgrades.) This home has been painstakingly restored & improved upon, boasting 6 bedrooms, & 6.5 baths. Features incl: a beautiful library, private 3rd floor space (perfect for a teen, nanny or guests), & LL fitness room, studio & wine cellar. Frml living room, dining room & kitchen all open out onto a gorgeous landscape. Take in the beautiful rose garden, vegetable garden, & lovely greenery from your wrap-around porch. Thanks to all automated equipment, these gardens are almost maintenance free! With close to 18,000 sf of land, this lot is almost 3X the size of others in the neighborhood. Absolutely a unique home, inside & out. MUST be seen to be appreciated. A rare oasis, hidden from view. Simply a veritable jewel.

Listed by Lynne Lowenstein of Coldwell Banker Residential Brokerage - Arlington

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: 4.03% last updated on Apr 27, 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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