Recently Listed Properties

Below are the newest homes for sale offered in Winchester MA. You might also be interested in viewing upcoming open houses in Winchester.

Contact us or call 781.729.9030 for local knowledge and real estate expertise and for a tour of Winchester recent homes for sale. If you would like to save your favorite Winchester real estate and receive email updates when new homes match your search criteria, register with our site.

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 your exclusive Mediterranean villa 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

Better Homes and Gardens | The Shanahan Group
552 Main Street
Winchester MA, 01890
Office: 781-729-9030

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 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

512 SOUTH BORDER Road, Winchester, MA

Price$2,200,000

Est. Mortgage: $/month

MLS Number 72201123

  • Land Residential
  • Acreage 0.76

DEVELOPERS AND BUILDERS: This lot currently has a 7,100+ single family home sited in the middle of three- 11,000+ SQ FT LOTS in a highly desirable area close to I-93, downtown Winchester & Middlesex Fells Reservation. Over 33,500 sq. ft of land. These lot’s are large enough to build 3 spectacular homes. Surrounding new construction abuts this property line where houses are assessed $1.5M-1.8M. Plot plan is attached. Please contact listing broker for further details. PROPERTY SOLD AS IS. *No access inside fenced area without listing broker *

Listed by Nancy Ciampa McLaughlin and Michael Maggio of Redfin Corp.

Better Homes and Gardens | The Shanahan Group
552 Main Street
Winchester MA, 01890
Office: 781-729-9030

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 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

512 SOUTH BORDER Road, Winchester, MA

Price$2,200,000

Est. Mortgage: $/month

MLS Number 72201118

  • Single Family
  • Bathroom 5
  • Bedrooms 4
  • Year Built 1965
  • Parking Spaces 12

DEVELOPERS AND BUILDERS: This lot currently has a 7,100+ single family home sited in the middle of three- 11,000+ SQ FT LOTS in a highly desirable area close to I-93, downtown Winchester & Middlesex Fells Reservation. Over 33,500 sq. ft of land. These lot’s are large enough to build 3 spectacular homes. Surrounding new construction abuts this property line where houses are assessed $1.5M-1.8M. Plot plan is attached. Please contact listing broker for further details. PROPERTY SOLD AS IS. *No access inside fenced area without listing broker *

Listed by Nancy Ciampa McLaughlin and Michael Maggio of Redfin Corp.

Better Homes and Gardens | The Shanahan Group
552 Main Street
Winchester MA, 01890
Office: 781-729-9030

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 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

19 Amberwood Drive, Winchester, MA

Price$1,299,000

Est. Mortgage: $/month

MLS Number 72202752

  • Single Family
  • Bathroom 3
  • Bedrooms 3
  • Year Built 1973
  • Parking Spaces 6

This meticulously cared for Dutch Colonial with its contemporary flair & style with great flow for entertaining. As you walk into the foyer you will be dazzled by this sun splashed home. 1st floor offers private office,1/2 bath, family room (once a master bedroom) w/built-ins, surround sound, custom bar and sliding doors to a deck and gorgeous yard.Full Bathroom in hall was once the master bath w/entrance from bedroom. The kitchen w/ island and custom cabinets looks out through the wall of glass to the exquisite lush and manicured yard with stone walls and perennial beds bursting with colors. Included in this view is a sunroom with built in bar & family/den room with fireplace. Dining room and living room with gleaming hardwood floors. 2nd floor offers three bedrooms and a full bath. The 25x20 master with built-in Armoires has a private porch overlooking the yard. Lower level with kitchen cabinets w/eat-in area, sink and a play/movie room! Stroll to Vinson Owen! Furniture Neg.

Listed by Danielle Devarne of Century 21 Commonwealth

Better Homes and Gardens | The Shanahan Group
552 Main Street
Winchester MA, 01890
Office: 781-729-9030

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 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

224 Cross Street, Winchester, MA

Price$1,100,000

Est. Mortgage: $/month

MLS Number 72202653

  • Single Family
  • Bathroom 4
  • Bedrooms 5
  • Year Built 2017
  • Parking Spaces 1

NEW CONSTRUCTION! HANDSOME ATTACHED SINGLE FAMILY HOME LOOKING FOR A LONG TERM RELATIONSHIP WITH NEW OWNER! Located a short distance to downtown, with plentiful boutiques, restaurants, coffee shops, salons and the commuter rail to Boston. The 1st floor features an integrated floor plan for today's modern lifestyle with an open concept family room and kitchen (perfect for entertaining friends and family). A formal dining room and 1/2 bath complete the first level. Lots of natural light and gleaming hardwood floors throughout. The 2nd floor features a master en suite with walk-in closet and a spa like bathroom. Laundry, 2 additional bedrooms, and a full bath complete the 2nd floor. The 3rd level walk up is home to 2 more bedrooms and a bathroom. The lower level basement can be finished for an additional charge. Nothing to do but move in, decorate, and host your next party in your new home!! Within the Lynch School district, easy access to major highways and only 7 miles from Boston!

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

Better Homes and Gardens | The Shanahan Group
552 Main Street
Winchester MA, 01890
Office: 781-729-9030

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 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

224 Cross Street, Winchester, MA 01890

Price$1,100,000

Est. Mortgage: $/month

MLS Number 72202667

  • Condo or Co-op
  • Bedrooms 5
  • Bathroom 4

NEW CONSTRUCTION! HANDSOME ATTACHED SINGLE FAMILY HOME LOOKING FOR A LONG TERM RELATIONSHIP WITH NEW OWNER! Located a short distance to downtown, with plentiful boutiques, restaurants, coffee shops, salons and the commuter rail to Boston. The 1st floor features an integrated floor plan for today's modern lifestyle with an open concept family room and kitchen (perfect for entertaining friends and family). A formal dining room and 1/2 bath complete the first level. Lots of natural light and gleaming hardwood floors throughout. The 2nd floor features a master en suite with walk-in closet and a spa like bathroom. Laundry, 2 additional bedrooms, and a full bath complete the 2nd floor. The 3rd level walk up is home to 2 more bedrooms and a bathroom. The lower level basement can be finished for an additional charge. Nothing to do but move in, decorate, and host your next party in your new home!! Within the Lynch School district, easy access to major highways and only 7 miles from Boston!

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

Better Homes and Gardens | The Shanahan Group
552 Main Street
Winchester MA, 01890
Office: 781-729-9030

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 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

18 Cambridge Street, Winchester, MA

Price$975,000

Est. Mortgage: $/month

Open House

MLS Number 72202780

  • Single Family
  • Next Open House: Sun 30th 12:00 pm - 1:00 pm
  • Bathroom 4
  • Bedrooms 5
  • Year Built 1970

Come see this stately & spacious 5 BD, 4 full bath home with breathtaking seasonal lake views. Located within Myopia Hill with an incredible heated driveway, this is your chance to have the privacy & space you’ve been looking for! Containing a room for every occasion, this home is perfect for your entertaining needs. The 1st floor has everything you could wish for, with a chef’s inspired kitchen featuring granite countertops & stainless steel appliances, an inviting living room for relaxation by the fireplace, elegant formal dining room which leads out to the deck & 4 spacious bedrooms, inclusive of the master & master bath. Enjoy a grand open concept family room with full bath, office space & gas fireplace on the lower level which leads out to the beautiful patio. Enter into another office, playroom, bedroom, full bath & additional kitchen, perfect for an in-law or au pair suite. With a 2 car garage & a peaceful backyard, this home truly has it all.

Listed by The Andersen Team and Sven Andersen of RE/MAX Leading Edge

Better Homes and Gardens | The Shanahan Group
552 Main Street
Winchester MA, 01890
Office: 781-729-9030

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 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

17 Cedar Street, Winchester, MA 01890
Open House

MLS Number 72202827

  • Condo or Co-op
  • Next Open House: Sat 29th 11:30 am - 1:00 pm
  • Bedrooms 4
  • Bathroom 4

This lovely townhouse, built in 2012, has beautiful details including hi ceilings, gorgeous crown moldings &handsome finishes. The open-plan 1st fl consists of a LR, dining area & a granite kitchen with maple cabinets, stainless steel appliances, a large peninsula and a window overlooking the back yd - a half bath and direct entry to the garage complete this floor. On the 2nd fl, there are 2 lg corner bedrooms, each with double closets and serviced by a bathroom with a double vanity, tiled bath/shower and a big laundry closet. The master bedroom and ensuite bath are also on the 2nd floor; the master features a roomy walk-in closet, and the bathroom, with a double vanity and tiled shower/bath, also has a linen closet. Another en-suite bedroom/bath with 2 closets encompasses the entire 3rd floor. Two finished rms, one set up as a media rm, are on the lower level. Please submit any offers by 3 PM on Tuesday, August 1.

Listed by Martha Hoffmann of Coldwell Banker Residential Brokerage - Cambridge - Huron Ave.

Better Homes and Gardens | The Shanahan Group
552 Main Street
Winchester MA, 01890
Office: 781-729-9030

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 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 Conant Road, Winchester, MA 01890

MLS Number 72202516

  • Condo or Co-op
  • Bedrooms 2
  • Bathroom 3

Feel right at home in this bright, spacious & beautifully maintained end unit townhouse in the sought after Willows! End units don’t come along often, so don’t miss this exciting opportunity! Featuring an open kitchen with new stainless steel appliances, a large pantry that offers plenty of space and storage. Dine in the formal dining room and be able to cozy up to a warm fire in the living room, plus den/office/another bedroom. In the warmer months, relax on either of the 2 balconies this unit has to offer. The 2nd floor showcases 2 good-size bedrooms, 2 full baths, inclusive of the master with master bath and walk-in-closet and in-unit laundry. Bamboo floors throughout and large storage room in the basement & garage. Enjoy all of the amenities at the professionally managed Willows has to offer, including a luxury clubhouse with fitness room, full kitchen, common area and heated pool. Close proximity to the Commuter Line to Boston, restaurants and shops of downtown Winchester.

Listed by Maureen Schlegel of Century 21 Advance Realty

Better Homes and Gardens | The Shanahan Group
552 Main Street
Winchester MA, 01890
Office: 781-729-9030

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 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

259 Swanton Street, Winchester, MA 01890

MLS Number 72200363

  • Commercial Office

PROFESSIONAL OFFICE SPACE FOR LEASE - The perks of Winchester center with easy parking! Formerly a doctors office, this 2500SF space is perfect for a medical practice, law office, specialized healthcare or insurance office. Contains ample parking with dedicated 30+ spaces available. Prominently located right off of major intersection with great visibility from Main Street. Minutes to all major highway routes 128 and 93, as well as MBTA Commuter Rail. In walking distance to Winchester Center restaurants, banks and shops.

Listed by Donna Addezio of Better Homes and Gardens The Shanahan Group

Better Homes and Gardens | The Shanahan Group
552 Main Street
Winchester MA, 01890
Office: 781-729-9030

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 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

141 Ridge Street, Winchester, Ma 01890

MLS Number 72200822

  • Rental
  • Bathroom 1

Spacious 3 bedrooms 1 bathroom in a ranch style house, hardwood floors, open floor concept, living and dining rooms, modern kitchen with granite countertop and stainless steel appliances, parking for 2 cars, large yard with play set. LOCATED WITHIN WALKING DISTANCE TO VINSON OWEN SCHOOL. No basement access.

Listed by Anna Mean of L & A Realty

Better Homes and Gardens | The Shanahan Group
552 Main Street
Winchester MA, 01890
Office: 781-729-9030

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 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

34 Charles, Winchester, Ma 01890

MLS Number 72201597

  • Rental
  • Date Available 08/01/2014
  • Bathroom 2

Spacious 3 bedroom townhouse with 1 1/2 baths. This sunny unit has a large rear yard and many perennial plantings. First floor with hardwood floors, 2nd floor has newer carpet, all in very nice condition. Included with this rental are new high efficiency washer and dryer and 3 window a/c units.

Listed by Kim Covino of RE/MAX Leading Edge

Better Homes and Gardens | The Shanahan Group
552 Main Street
Winchester MA, 01890
Office: 781-729-9030

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 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

200 Swanton Street, Winchester, Ma 01890

MLS Number 72204306

  • Rental
  • Bathroom 1

Come home to serenity with the peaceful view of the duck pond and gardens from your private balcony. Oversized living/dining/kitchen combo. All new kitchen with new appliances and breakfast bar, Brand new bath, king size bedroom with walk in closet. Close to downtown Winchester with all the wonderful shops and restaurants, farmers' market, and the commuter rail to Boston. Half mile to tennis and beach. Pool, clubhouse, coin operated laundry, and extra storage.Plenty of parking in this card entry gated complex. Easy access to all major routes.

Listed by Diane Plunkett and Sheri O'Connor of Plunkett Properties

Better Homes and Gardens | The Shanahan Group
552 Main Street
Winchester MA, 01890
Office: 781-729-9030

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 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

63 Shore Road, Winchester, MA 02190

MLS Number 72201885

  • Commercial Office

Individual office space located in an office suite. Locking office with window. Shared spaces include a kitchen, board/conference room, front entry desk, lobby/reception area. Clean, professional space in an elevator building, steps to Commuter Rail and ample parking. Deeded parking can be rented for $100. LOCATION IS KEY - Winchester Center. Starbucks, Commuter Rail, parking lots, street parking, restaurants. Good signage is available at the street, front entry, office suite door, reception area too!

Listed by Bill Patterson of Craft Realty

Better Homes and Gardens | The Shanahan Group
552 Main Street
Winchester MA, 01890
Office: 781-729-9030

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 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

63 Shore Road, Winchester, MA 02190

MLS Number 72201886

  • Commercial Office

Individual office space located in an office suite. Locking office with window. Shared spaces include a kitchen, board/conference room, front entry desk, lobby/reception area. Clean, professional space in an elevator building, steps to Commuter Rail and ample parking. Deeded parking can be rented for $100. LOCATION IS KEY - Winchester Center. Starbucks, Commuter Rail, parking lots, street parking, restaurants. Good signage is available at the street, front entry, office suite door, reception area too!

Listed by Bill Patterson of Craft Realty

Better Homes and Gardens | The Shanahan Group
552 Main Street
Winchester MA, 01890
Office: 781-729-9030

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 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

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.