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. 

9 Grove Street, Winchester, MA

Price$4,499,000

Est. Mortgage: $/month

MLS Number 72254524

  • Single Family
  • Parking Spaces 10
  • Year Built 2017
  • Full Bath 6
  • Bathroom 8

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 Leading Edge Real Estate

{$office->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: 4.53% last updated on Jul 12, 2018
* 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 Central Green, Winchester, MA

Price$3,350,000

Est. Mortgage: $/month

MLS Number 72339037

  • Single Family
  • Parking Spaces 4
  • Village Rangeley
  • Year Built 1930
  • Full Bath 4

Georgian Colonial home short stroll to Winchester Center, public transportation, parks and public schools. The home was taken down to the studs and rebuilt in 2008, the home owners moved back to their home in 2009. This home was renovated with the modern family in mind. Enjoy two private patios and gardens perfect for relaxing or entertaining. The gourmet kitchen offers a spacious island, two ovens plus warming oven, five burner gas stove, all top of the line appliances , plus area for casual dining and adjacent family room with a gas fireplace overlooking the pristine back yard. The home offers five spacious corner bedrooms, Master bedroom features a wood burning fireplace, two walk-in closets and master bathroom. In the basement there is a large room that was once a handball court, spacious enough for a media room. This home offers exquisite detail throughout, one of Winchester's Finest location. See the reasonable heating/cooling costs in attch.

Listed by Peggy Otis of Coldwell Banker Residential Brokerage - Winchester

{$office->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: 4.53% last updated on Jul 12, 2018
* 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

6 Robinson Park, Winchester, MA

Price$3,300,000

Est. Mortgage: $/month

MLS Number 72314311

  • Single Family
  • Parking Spaces 2
  • Year Built 1949
  • Full Bath 4
  • Bathroom 6

Waterfront in Winchester! Sail, swim, boat and beach all in your backyard. This rarely available property was thoughtfully renovated and expanded with modern family living in mind. Stunning water views from nearly every room of this meticulous 5 bedroom colonial featuring tall ceilings, crown moldings and gorgeous hardwood floors throughout. Sun drenched living spaces include an open concept kitchen and family room with vaulted ceilings, gas fireplace and French doors leading to an expansive blue stone patio ideal for entertaining. Spacious master suite boasts impressive walk-in closet and luxurious master bath with laundry room on second floor. Finished lower level walks out to a beautifully landscaped rear yard which gently slopes down to water's edge. This one of a kind setting on a coveted street is ideally located for a short commute to Cambridge and Boston.

Listed by Brian Dougherty of Robert Paul Properties

{$office->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: 4.53% last updated on Jul 12, 2018
* 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

10 Ledgewood Road, Winchester, MA

Price$2,945,000

Est. Mortgage: $/month

MLS Number 72337357

  • Single Family
  • Parking Spaces 9
  • Year Built 2004
  • Full Bath 4
  • Bathroom 7

NEW LISTING! This Grand Estate is located in one of Winchester's most prestigious neighborhoods~ This private residence "Dream Home" was custom built with every amenity and will exceed your expectations. Situated on an acre w/ level manicured grounds, gunite pool w/ fence and auto cover for safety. Large mahogany deck and patio ideal for outdoor entertaining. Enormous state of the art chef's kitchen, freshly updated white quartz, custom cabinetry, oversized island, desk & breakfast bar. Sun-drenched breakfast room w/floor to ceiling windows overlooking expansive rear yard. Game room, gym, sports room with padded walls, media theatre room, and so much more! This exquisite residence features floor to ceiling Pella French doors & windows,10FT ceilings w/ double crown moldings, 3 fireplaces, 3 car garage. Seldom does such a magnificent estate come on the market with such privacy & beauty w/ easy access to Fells reservation, Winchester center shops, restaurants, schools & train to Boston

Listed by Kim Covino of Leading Edge Real Estate

{$office->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: 4.53% last updated on Jul 12, 2018
* 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

54 Myopia Road, Winchester, MA

Price$2,850,000

Est. Mortgage: $/month

MLS Number 72323335

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

This Colonial Revival masterpiece is a testament to one of MF Reynolds finest renovation and expansion projects. Offering a quality of construction and materials exceeding that typically found in new builds, 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 childrens activities and a woodland wonderland for exploration. Set upon Myopia Hill, in an estate setting of spectacular mature gardens, the property is surrounded by homes of similar architectural distinction. This family-friendly neighborhood provides ease of access to all Winchester offers: fine schools, childrens activities and clubs, boat club, beach, golf course, and the communitys Wright Locke Farm, to name a few. It is difficult to imagine that such privacy can be available within striking distance of Boston.

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

{$office->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: 4.53% last updated on Jul 12, 2018
* 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

31 Swan Road, Winchester, MA

Price$2,850,000

Est. Mortgage: $/month

MLS Number 72337827

  • Single Family
  • Parking Spaces 8
  • Year Built 1929
  • Full Bath 3
  • Bathroom 5

UNIQUE OPPORTUNITY ON MYOPIA HILL. Nestled in an exclusive setting with Spectacular 40,000 square feet of park-like grounds surround this English Tudor Revival Estate. This home was built of beautifully textured Water-Struck brick, slate roof and expansive leaded glass windows. The 4,500 square foot main residence features 4 bedrooms, 3 full baths, 2 powder rooms, and a 2 car garage tucked behind the house. First level features a handcrafted wood paneled, living room with majestic English Stone fireplace. Walk into the adjacent private sitting room to enjoy the beautiful gardens surrounding this property. An updated kitchen with Butlers Pantry serves the Formal Dining Room and sunny Breakfast Room. Enjoy the Den/Library off the Kitchen or Foyer. A rare find only 8 miles from Boston and easy access to RT 95, 93, and 128.

Listed by Dorothea Feffer of Coldwell Banker Residential Brokerage - Winchester

{$office->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: 4.53% last updated on Jul 12, 2018
* 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 Grove Street, Winchester, MA

Price$2,499,900

Est. Mortgage: $/month

MLS Number 72297573

  • Single Family
  • Parking Spaces 5
  • Year Built 2017
  • Full Bath 5
  • Bathroom 7

Spectacular NEW CONSTRUCTION, 6,294 sf home situated on over 20,000+SF lot! Custom built 5 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, butlers 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 Leading Edge Real Estate

{$office->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: 4.53% last updated on Jul 12, 2018
* 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

4 Ravine Road, Winchester, MA

Price$2,499,000

Est. Mortgage: $/month

MLS Number 72348070

  • Single Family
  • Parking Spaces 6
  • Year Built 2001
  • Full Bath 5
  • Bathroom 7

UNBEATABLE LOCATION, SITUATED IN THE HEART OF DOWNTOWN WINCHESTER!!! Enter into the dramatic 2-story foyer featuring one of three Swarovski Crystal Chandeliers! Host a dinner party in the Chefs kitchen boasting granite counters, a 48"SUBZERO refrigerator, a 60"gas WOLF range & 2 BOSCH dishwashers. Step out into the pristine garden with built in BBQ and outdoor pizza oven! The dining room has built-in china cabinets, a fireplace and is surrounded with beautiful windows. 5 bed suites, each w/private bath. A Master bed fit for a King & Queen! Seamless flow throughout provides unparalleled luxury living on 4 levels. Gorgeous media room on lower level, featuring a home theatre and bar. Newly finished hardwood floors , and many rooms recently painted. Walk to the farmer's market on the common and explore Winchester's boutiques, restaurants & coffee shops or take the commuter rail to North Station for a day in the city. Within the Ambrose school district and 7 miles North of Boston.

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

{$office->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: 4.53% last updated on Jul 12, 2018
* 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

15 Aristotle Drive, Winchester, MA

Price$2,399,000

Est. Mortgage: $/month

MLS Number 72346813

  • Single Family
  • Parking Spaces 6
  • Year Built 2002
  • Full Bath 4
  • Bathroom 6

THE ULTIMATE IN LUXURY LIVING LOCATED 7 MILES NORTH OF BOSTON!!! This meticulously maintained home has an integrated floor plan that every modern buyer seeks. The first floor features a dining room, living room & family room, both with gas fireplaces and a large kitchen with sliders to the exquisite stone patio for your next Summer gathering. Including granite counters, hardwood floors and a top of the line SS appliance package. Many rooms newly painted in today's neutral Benjamin Moore colors. Work from home? Enjoy the fantastic mahogany home office with custom built ins. Three floors of finished living space boasting 5 large bedrooms, 4 bathrooms and a great room with fireplace, the perfect space for "peace & quiet". Lower level features a game room, home gym and sauna!!! A short drive to downtown, where you'll find coffee shops, boutiques, restaurants, and the commuter rail to Boston. Within the desirable Vinson Owen school district. Become a part of the Winchester community today!

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

{$office->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: 4.53% last updated on Jul 12, 2018
* 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

47 Arlington Street, Winchester, MA

Price$2,245,000

Est. Mortgage: $/month

MLS Number 72343357

  • Single Family
  • Parking Spaces 6
  • Year Built 2000
  • Full Bath 5
  • Bathroom 6

Stunning Colonial set in the heart of Myopia hill w/ serene golf course views & an impeccably landscaped yard, which affords privacy & tranquility. From the minute you walk in, your eyes will be drawn to the magnificent bridal staircase. A room for every occasion, this home is perfect for all of your entertaining needs. Featuring an elegant living room w/ double sided gas fireplace which leads into the den, a 1st floor bedroom w/ private bath & an open-floor family room w/ cathedral ceilings & a gorgeous stone fireplace. The chef inspired kitchen has upgraded, high-end appliances, an oversized island w/ granite countertops & dining area. A formal dining room & wet bar complete the 1st floor. The 2nd level boasts 4 spacious bedrooms, inclusive of the master suite w/ soaring ceiling heights, his & her closets & large master bath. The lower level is complete w/ a recreation room, full bath, exercise room & media room. With a 3 car garage & incredible location, make this dream home yours!

Listed by Andersen Group Realty and Sven Andersen of Keller Williams Realty Boston Northwest

{$office->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: 4.53% last updated on Jul 12, 2018
* 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.