Winchester Real Estate

Just 15 minutes northwest of Boston is the beautiful town of Winchester, MA. When your kids are on summer vacation from Winchester's top-ranked public school system, have them spend time sailing at the Winchester Boat Club, keeping fit at the Winchester Swim and Tennis Club, or golfing at the Country Club. A quick trip on the Communter Rail's Purple Line will drop you right at the Fleet Center in central Boston, perfect for easy commuting to work or for an evening out. Don't miss out on D'Agostino's Deli, a famous local spot for subs, sandwiches, party trays, and more delicious deli wonders.

And Winchester real estate doesn't disappoint: find many new construction single-family homes, historic estates, luxurious condos, and more.

View currently listed real estate in Winchester below and contact Century 21 Advance Realty with any questions or to schedule a tour. You can also register with our site to save your favorite properties and receive notifications via email when a new listing matches your preferred criteria. 

10 Ledgewood Road, Winchester, MA

Price$2,995,000

Est. Mortgage: $/month

MLS Number 72198378

  • Single Family
  • Full Bath 4
  • 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

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

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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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54 Myopia Road, Winchester, MA

Price$2,950,000

Est. Mortgage: $/month

MLS Number 72166793

  • Single Family
  • Bedrooms 6
  • Full Bath 5
  • 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.

{$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: 3.95% 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$2,879,000

Est. Mortgage: $/month

Open House

MLS Number 72240645

  • Single Family
  • Next Open House: Sun 22nd 12:00 pm - 2:00 pm
  • Full Bath 6
  • Bathroom 7
  • 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 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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22 Saint Thomasmore Drive, Winchester, MA
Open House

MLS Number 72223149

  • Single Family
  • Next Open House: Sun 22nd 1:00 pm - 2:00 pm
  • Full Bath 6
  • Bathroom 7
  • Bedrooms 5

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

{$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: 3.95% 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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366 Main Street, Winchester, MA

Price$2,749,000

Est. Mortgage: $/month

Open House

MLS Number 72244192

  • Single Family
  • Next Open House: Thu 19th 6:00 pm - 9:00 pm
  • Bedrooms 5
  • Full Bath 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

{$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: 3.95% 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$2,579,000

Est. Mortgage: $/month

Open House

MLS Number 72224619

  • Single Family
  • Next Open House: Sun 22nd 1:30 pm - 3:30 pm
  • Full Bath 5
  • Bathroom 7
  • Bedrooms 5

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: 3.95% 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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3 WOOD Lane, Winchester, MA

Price$2,499,000

Est. Mortgage: $/month

MLS Number 72216562

  • Single Family
  • Full Bath 4
  • Bathroom 5
  • Bedrooms 5
  • Year Built 2003

BREATHTAKING, Chic and Sophisticated one owner custom home. Nestled on large, lush 3/4 acre grounds to ensure ultimate Privacy and Serenity. Exudes great energy and aura. Spacious open floor plan and high ceilings with classic flare. 2 story grand foyer with a custom staircase. Wood burning fireplace in the elegant living room. Gas fireplace in family room adjacent to a spectacular kitchen with a sushi style granite island and a breakfast room that overlooks an expansive covered porch, ideal for indoor/outdoor entertaining. Formal dining room easy to be served. Gracious and easy flow for informal and formal parties. Grand master suite with sunrise views. Additional 4 bedrooms/4 baths complete second floor. Front and back staircase insure privacy. TIMELESS, TRADITIONAL, MODERN LUXURY! Lower level is walk out with high ceilings and great light. Gas fireplace in recreation room and sliders to the yard. Plumbing is ready for additional bathroom. Garage parks 4 cars. Walk to Winchester CC.

Listed by Domingo Medina and Leigh Ventura 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: 3.95% 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

7 Ledgewood Road, Winchester, MA

MLS Number 72216690

  • Single Family
  • Bathroom 4
  • Bedrooms 4
  • Full Bath 3
  • 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: 3.95% 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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23 Brooks Street, Winchester, MA

Price$2,290,000

Est. Mortgage: $/month

MLS Number 72227676

  • Single Family
  • Full Bath 3
  • Bathroom 4
  • Bedrooms 5
  • Year Built 1994

As soon as you start up the magnificent cobblestone-lined drive you know you are arriving somewhere special. This modern take on a Queen Anne Victorian was the original carriage house to the Parkhurst home. Top-of-the-line craftsmanship, elegant details, vaulted ceilings and the expansive open layout will capture your heart. Set perched atop this picturesque sought after neighborhood across from the Upper Mystic Lake in Winchester you have the best of both worlds: close proximity to town in a gorgeous private setting with incredible views and an abundance of natural light at every turn. Home highlights include: gorgeous master retreat with roof top deck and spa tub, 2 car heated garage, full home automation, fire place, eat-in chef's grade kitchen opens to multiple living and outdoor areas for relaxing or entertaining, and custom built-ins throughout, finished lower level featuring a home theatre with drop-down projection screen, home gym and direct access to copious yard space.

Listed by The McLaren Team, Andrea D'Agostino Boike, Jelena Djuragic and Susan C. McLaren of Coldwell Banker Residential Brokerage - Boston - Newbury St.

{$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: 3.95% 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

61 Arlington Street, Winchester, MA

Price$2,250,000

Est. Mortgage: $/month

MLS Number 72183294

  • Single Family
  • Bathroom 4
  • Bedrooms 5
  • Full Bath 3
  • Year Built 1969

Better than NEW! Imagine enjoying the front porch view with a cup of coffee or a glass of wine. Beautiful views from porch, patio, 3-season room and every window are only the beginning. 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. 5 bedrooms on 2nd floor. Ample storage throughout the home. Extensive improvements to landscape and hardscape; including irrigation, drywell, walkways, flower beds and a variety of specimen plantings. New windows, new roof, 400 amp service. Less than 10 miles to Boston and Logan Airport. Convenient to Rt 2,3,93 and 128. Enjoy all that Winchester offers - great schools, Middlesex Fells, Wright Locke Farm and much more. Move in and appreciate the quality and thoughtfulness of every aspect of this exceptional home that is beautifully sited on a .69 acres.

Listed by Elizabeth Darby of Century 21 Commonwealth

{$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: 3.95% 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

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. 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. MLS Property Information Network, Inc. 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.