Winchester Real Estate

Winchester is a town located in Middlesex County, Massachusetts, eight miles north of Boston. Despite its steady growth and proximity to a large metropolitan area, Winchester retains the autonomy, the individuality, and the friendliness of a small town. In Winchester, quite apart from the attractiveness of the town and its surroundings, you will find in the community a very unusual civic spirit. The people of that town take an intelligent interest in the management of its affairs and in its continual improvement and beautification. The Center is a unifying force in the life of the town. In a relatively small area are located the Town Hall, Library, physicians' and dentists' offices, most of the churches, and a shopping district.

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Browse all real estate for sale in Winchester, Massachusetts below. Contact us to schedule a showing or if you have any questions. Create an account to save your favorite Winchester listings and to receive email notifications when similar properties become available. 

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 Avon
1675 Massachusetts Ave
Cambridge MA, 02138
Office: 617-497-6555

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$/month over payments
Federal 30-year interest rate: 3.9% last updated on Nov 30, 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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14 St Thomasmore Drive, Winchester, MA

Price$3,199,000

Est. Mortgage: $/month

MLS Number 72262053

  • Single Family
  • Bathroom 7
  • Full Bath 6
  • Bedrooms 5
  • Year Built 2018

NEW CONSTRUCTION BY LOCAL MASTER BUILDER! The design of this spectacular home with the integrated floor plan that every modern, savvy buyer seeks truly is a masterpiece. Featuring 3 floors of finished living with volume control surround sound throughout each room. Within the 3-year old Vinson Owen school district. Located a short drive to downtown, where you'll find plentiful coffee shops, boutiques, restaurants, taverns & salons. The commuter rail with 2 Winchester locations is a short 15-20 ride to Boston's North Station. Do not miss out on this opportunity to own a true gem. Become a part of the Winchester community and experience all it has to offer!

Listed by Monte Marrocco of Coldwell Banker Residential Brokerage - Winchester

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Century 21 Avon
1675 Massachusetts Ave
Cambridge MA, 02138
Office: 617-497-6555

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$
$
%
$/month over payments
Federal 30-year interest rate: 3.9% last updated on Nov 30, 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

MLS Number 72198378

  • Single Family
  • Bathroom 7
  • Full Bath 4
  • 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

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Century 21 | Adams KC
75 Park Avenue
Arlington MA, 02476
Office: 781-648-6900

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$
$
%
$/month over payments
Federal 30-year interest rate: 3.9% last updated on Nov 30, 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 | Adams KC
75 Park Avenue
Arlington MA, 02476
Office: 781-648-6900

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Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.9% last updated on Nov 30, 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$2,879,000

Est. Mortgage: $/month

Open House

MLS Number 72240645

  • Single Family
  • Next Open House: Sun 17th 12:00 pm - 1:30 pm
  • Bathroom 7
  • Full Bath 6
  • Bedrooms 5

WELCOME TO AQUINAS PATH! HOME TO WINCHESTER'S NEWEST LUXURY DEVELOPMENT! ALMOST SOLD OUT! The ultimate in luxury living conveniently 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 savvy buyer seeks is truly a work of art. Three floors of finished living with volume control surround sound in every room. The kitchen-family room open concept, with oversized sliders to a stone patio, is the ultimate space for entertaining large crowds. Not 1, but 2 butler's pantries, and a second Cape Cod style covered Blue Stone patio, the only one in the neighborhood. The elegant master suite feels like a boutique hotel featuring a spacious fire placed sitting room with custom built-ins, a gorgeous Marble bathroom and, ladies...a to-die-for walk in closet! The lower level is home to a state of the art movie theatre and home gym with mirrored walls. THIS HOUSE IS A "10"! COME AND SEE FOR YOURSELF!

Listed by Monte Marrocco of Coldwell Banker Residential Brokerage - Winchester

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Century 21 Avon
1675 Massachusetts Ave
Cambridge MA, 02138
Office: 617-497-6555

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.9% last updated on Nov 30, 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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22 Saint Thomasmore Drive, Winchester, MA

MLS Number 72223149

  • Single Family
  • Bathroom 7
  • Full Bath 6
  • Bedrooms 5
  • Year Built 2017

Architecturally crafted Colonial located in one of Winchester’s premier locations! This magnificent 7,100+ sqft home with 3-car garage Features 10’ ceilings, an elegant formal dining room with built-ins and butler’s pantry, versatile first floor study with full bath, great room with gas fireplace and incredible millwork including expertly sited built-ins and coffered ceilings. Sunfilled kitchen boasts high end cabinet-fronted appliances and stunning cabinetry with quartzite countertops. Second floor offers 9’ ceilings, en-suite bedroom, Jack & Jill bedrooms, and a breathtaking master suite with a gas fireplace, His & Hers walk-in closets featuring a makeup vanity, custom shelving and plenty of storage. The spa-like master bath boasts heated marble floors, free standing jetted tub & large tiled shower. Third floor offers additional bedroom and full bath. Step outside of this cedar shingled home onto the deck overlooking the built-in grill and stone fire pit. Welcome home!

Listed by Marissa Waite of Barrett Sotheby's International Realty

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Century 21 | Adams KC
75 Park Avenue
Arlington MA, 02476
Office: 781-648-6900

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.9% last updated on Nov 30, 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$2,749,000

Est. Mortgage: $/month

MLS Number 72244192

  • Single Family
  • Bathroom 6
  • Full Bath 5
  • Bedrooms 5
  • Year Built 1853

Let us introduce to you 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 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 with custom closets and marble drenched bathroom. Come tour this beauty today!

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

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Century 21 | Adams KC
75 Park Avenue
Arlington MA, 02476
Office: 781-648-6900

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.9% last updated on Nov 30, 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$2,579,000

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

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Century 21 | Adams KC
75 Park Avenue
Arlington MA, 02476
Office: 781-648-6900

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.9% last updated on Nov 30, 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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184 Ridge Street, Winchester, MA

Price$2,499,000

Est. Mortgage: $/month

MLS Number 72263106

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

Perched atop the West Side Hill, on almost 1 acre, this east facing, sprawling new construction 4Beds 4.5Bath home will exceed your expectations! First floor features huge 30' kitchen with Thermador appliances, 10' center island, custom cabinets, dining area, pantry, mudroom, heated attached 3 car garage, year round sunroom overlooking sprawling "football field" sized back yard, family room off kitchen with natural stone fireplace, office, formal living w/ FP, dining room, butlers pantry, and a dramatic stairway to the second floor. Master is unlike anything you've seen..enter into a sitting room with fireplace, ballroom sized bedroom, lavish master bath with radiant heat floor, custom cabinetry, soaking tub and oversized shower with built in seat. 3 Add'l bedrooms with en-suite baths. Lower level w/ full windows & slider can easily be customized with another full bath/media room/gym;you design.. builder will create for you! Don't miss this spectacular home complete w/ HEATED DRIVEWAY!

Listed by Kim Covino of RE/MAX Leading Edge

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Century 21 | Adams KC
75 Park Avenue
Arlington MA, 02476
Office: 781-648-6900

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.9% last updated on Nov 30, 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
Active With Contract

MLS Number 72246664

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

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 some finishes

Listed by Errico Team, Kelly Errico and Mary Errico of Waterfield Sotheby's International Realty

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Century 21 | Adams KC
75 Park Avenue
Arlington MA, 02476
Office: 781-648-6900

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.9% last updated on Nov 30, 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 Ledgewood Road, Winchester, MA

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

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Century 21 | Adams KC
75 Park Avenue
Arlington MA, 02476
Office: 781-648-6900

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.9% last updated on Nov 30, 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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1 Harrington Road, Winchester, MA

Price$2,199,000

Est. Mortgage: $/month

MLS Number 72256948

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

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 | Adams KC
75 Park Avenue
Arlington MA, 02476
Office: 781-648-6900

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.9% last updated on Nov 30, 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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