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.

86 Church Street, Winchester, MA

Price$1,849,000

Est. Mortgage: $/month

Open House

MLS Number 72364668

  • Single Family
  • Next Open House: Sun 22nd 1:00 pm - 3:00 pm
  • Parking Spaces 7
  • Year Built 1890
  • Full Bath 3

Stunning and timeless, this beautiful Victorian masterfully blends high-end updates with exquisite period details, such as gorgeous leaded windows and a superb original pocket door in the dining room. Newly renovated designer kitchen features Thermador appliances, Perlick beverage fridge, custom cabinetry, gas fireplace, and reclaimed heart pine flooring. Meticulously chosen finishes like grass cloth wallpaper, custom window treatments, antique and modern lighting create spaces that welcome and delight. Generous bedrooms on the 2nd and 3rd levels, including the serene master retreat, have ample closets and are freshly updated; 3 remodeled baths impress. Sizable lower level bonus room is perfect for movie night, working out and entertaining. Brand new modern office is handsomely designed down to the last detail, flooded w/natural light and set away from main house for privacy. Lovely backyard oasis; wonderfully close to Center’s vibrant restaurants, shopping, schools and train stations

Listed by Stephanie Mcgowan of Waterfield Sotheby's International Realty

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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: 4.52% last updated on Jul 19, 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.

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51 Wedgemere Avenue, Winchester, MA

Price$1,799,000

Est. Mortgage: $/month

Open House

MLS Number 72365181

  • Single Family
  • Next Open House: Sat 21st 12:30 pm - 2:30 pm
  • Parking Spaces 4
  • Village The Flats
  • Year Built 1914

Don’t miss this rare opportunity to live on one of the most desirable streets in the “Flats". Seldom do you find homes like this charming English Tudor for sale. This home has everything you could want and more! The grand entrance has an elegant fireplace w/hand carved mantel & leads to a front to back lv rm & 2nd stunning fireplace w/built-in bookcases. Off lv rm is a wonderful & bright Sunroom. An elegant dnrm has plenty of space for small & large gatherings. Hand painted ceiling adds charm to this room. Original butler’s pantry opens to spacious updated kitchen. Washer & dryer on main level & elegant half-bath. Completing this level spacious Family Room. The 2nd level has oversized landing which leads to 4 bdrms including master bedroom.Original claw foot tub & separate shower are delightful. The 3rd level 2 add'l bdrs & bath - lower level has a lg bonus rm & 1/2 ba - private yard w/bluestone patio. Two car garage. Location, character & space describes this gorgeous home

Listed by Janet Halloran of Leading Edge Real Estate

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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: 4.52% last updated on Jul 19, 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.

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15 Cardinal Street, Winchester, MA

Price$924,900

Est. Mortgage: $/month

Open House

MLS Number 72362368

  • Single Family
  • Next Open House: Sat 21st 12:00 pm - 1:30 pm
  • Parking Spaces 4
  • Year Built 2015
  • Full Bath 3

Gorgeous sun filled townhouse located on quiet cul-de-sac will live more like a single family. So much space w/private yard & driveway.Beautiful gourmet kitchen w/ large marble island,countertops, stainless steel appliances. Open floor plan w/ dining area to living room featuring fireplace & custom bookshelves. Office on the main floor features french doors & custom bookcases. Master bedroom has a beautiful master bath & custom walk in closet w/ expansive shelving/drawers.Two more bedrooms, a full bath and laundry closet finish the upstairs. The delightful finished basement features a family room, children's art/play area and another bonus room & bath for guests.Off the first floor mudroom is the back deck & pretty new patio to enjoy the professionally landscaped yard w/ new plants & fruit trees and shed.This neighborhood in the Muraco school district is near the bike path, the Fells, KidStock, ballet school and Russian math to name a few.Don't miss this beauty.

Listed by The Synergy Group and Susan Silkes of Leading Edge Real Estate

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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: 4.52% last updated on Jul 19, 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.

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85 Loring Avenue, Winchester, MA

Price$809,900

Est. Mortgage: $/month

MLS Number 72365545

  • Single Family
  • Parking Spaces 4
  • Year Built 1962
  • Full Bath 2
  • Bathroom 3

This home has been lovingly maintained and updated and is in mint condition Bright sunny granite kitchen and family room overlook private yard.Living room and dining room have gleaming hardwood floors. Three bedrooms on the second floor have spacious closets. Full basement has a large recreation room with fireplace and full bath. Central air,newer windows and gas heat are just a few of the amenities of this wonderful home.Located conveniently to a park, bike path and a short distance to major highways. This is a Lynch School neighborhood . Move right in and enjoy!

Listed by Nan Shanahan of Better Homes and Gardens | The Shanahan Group

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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: 4.52% last updated on Jul 19, 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.

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907 Main Street, Winchester, MA 01890
Open House

MLS Number 72364599

  • Condo or Co-op
  • Next Open House: Sat 21st 1:00 pm - 2:30 pm
  • Half Bath 1
  • Bathroom 3
  • Year Built 2005

A distinctive residence with likeness to a Beacon Hill row house. The multi level townhouse is an urban oasis yet in the heart of thriving Winchester minutes from schools, public transit & 8 miles from Boston city line. This residence offers 3+ bedrooms and over 2700 sq ft on 4 levels. Best features are the open concept kitchen/living room with breakfast bar & fireplace; dining room with private deck; master suite with walk in closet & generous bath; a huge loft perfect for 3rd bedroom/play room/au pair suite & finally the lower level office/4th bedroom option with brick patio. Amenities of this home are wonderful architectural detail; high ceilings; gleaming hard wood floors; gas heating & cooking; central air & garage parking. NO EXPENSE HAS BEEN SPARED!

Listed by Nancy Ciampa McLaughlin of Redfin Corp.

{$office->Name}

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: 4.52% last updated on Jul 19, 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.

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Winchester, MA 01890

Price$799,000

Est. Mortgage: $/month

Open House

MLS Number 72365139

  • Multi-Family 2 Family - 2 Units Side by Side
  • Next Open House: Sun 22nd 2:00 pm - 3:00 pm
  • Year Built 1910
  • Bedrooms 8

Looking to buy an investment property? This is your chance to buy an incredible 2 unit multi-family in Winchester! Located just one mile from downtown Winchester and the commuter rail, this amazing location with a 3 car garage is a must see. Each unit features three levels of spacious living, containing 4 bedrooms and 2.5 baths in each unit, as well as an unfinished basement with ample room for storage. Don't miss out on this exciting opportunity to have that investment property you've always dreamed of!

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

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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: 4.52% last updated on Jul 19, 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.

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3 Brookside Avenue, Winchester, MA

Price$769,900

Est. Mortgage: $/month

Open House

MLS Number 72363094

  • Single Family
  • Next Open House: Sat 21st 1:00 pm - 2:30 pm
  • Parking Spaces 3
  • Year Built 1940
  • Full Bath 1

Classic New England Cape located in the popular Muraco School section of Winchester! This 3 bed, 1½ bath home offers a fantastic opportunity to become part of the Winchester community. This well-maintained home has updated systems, newer windows, hardwood floors & charming details including; crown molding, marble faced fireplace & built in cabinetry. The first level offers an expansive formal living room w/ a stunning fireplace that flows into the dining room, kitchen, half bath & a private sun filled office. You’ll love the convenient side entrance from the kitchen leading you to an enclosed breezeway/mudroom & attached garage. On the second level are 3 spacious bedrooms, full bath & bonus room which would make an excellent playroom, office or guest bedroom. Basement offers additional room for storage or expansion. Enjoy the private fenced in backyard with patio, storage shed & a wonderful location w/ easy access to both Route 93 & 95, restaurants, shops & public transportation.

Listed by Theuer, Pirani & Wile and Julie Wile Fish of Leading Edge Real Estate

{$office->Name}

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: 4.52% last updated on Jul 19, 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.

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200 Cross Street, Winchester, MA

Price$739,900

Est. Mortgage: $/month

MLS Number 72365132

  • Single Family
  • Parking Spaces 3
  • Year Built 1950
  • Full Bath 1
  • Bathroom 2

Muraco School District !! This 3 bedroom, 1 1/2 bath Cape style home is very deceiving from the outside. So much more room than you'd think. Formal living room has wall to wall carpet over the hardwood floors. Cabinet packed kitchen, formal dining room with parquet floors, the first floor bedroom is being used as an office. Full bath. Upstairs finds two large bedroom with large closets and there is a half bath. Hardwood floors in all rooms.The basement area is finished with a laundry room with cabinets, a sink and a refrigerator. There is a family room and another office area. A plus is the storage room and extra storage under the stairs. Walk out the basement to the large back yard which has a patio and a shed. The home is close to everything -train, bus, downtown, schools. Purchase now and be in your new home in time for school. Open House Saturday 12-2 pm and Sunday 12-2 pm.

Listed by Patricia Marsh of Realty Executives Marsh & Associates

{$office->Name}

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: 4.52% last updated on Jul 19, 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.

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36 Chester Street, Winchester, MA

Price$699,900

Est. Mortgage: $/month

Active With Contract

MLS Number 72362451

  • Single Family
  • Parking Spaces 3
  • Year Built 1860
  • Full Bath 1
  • Bathroom 2

New to the market! Solid mid 1800 Colonial style home in need of upgrades and clean up located on a quiet tree lined street within close proximity to all of Winchester's amenities and a short walk to Muraco Elementary School. Location and land make this an opportunity for a contractor to upgrade. Being offered as is. This is a flipper's dream! Perfect opportunity to modernize and restore the property to its original glory. A rare and unique diamond in the rough with unlimited potential to be enjoyed by a new generation. Offering a level fenced in backyard perfect for those summer barbecues with plenty of off street parking. Perfect opportunity to set up roots in one of the most sought after communities minutes from Boston!

Listed by Robin Dunbar Bain and Paula Savard of Aberman Associates, Inc.

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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: 4.52% last updated on Jul 19, 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.

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5 Nelson Street, Winchester, MA

Price$699,900

Est. Mortgage: $/month

Open House

MLS Number 72366040

  • Single Family
  • Next Open House: Sun 22nd 11:30 am - 1:30 pm
  • Parking Spaces 2
  • Year Built 1887
  • Full Bath 2

Picture Perfect Colonial in downtown Winchester neighborhood. This beautiful and bright home has it all! Full of character and charm, this home features 3 bedrooms, 2 full remodeled bathrooms, a stunning kitchen with stainless steel appliances, beadboard ceiling, granite countertops and wide board hardwood floors with first floor laundry. Extra space in the lower level is great for a playroom or office. Close to train, schools and Winchester Center! Showings to begin at Open House 7/22 11:30-1:30.

Listed by Stephanie Mcgowan of Waterfield Sotheby's International Realty

{$office->Name}

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: 4.52% last updated on Jul 19, 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.

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17 Lakeview Road, Winchester, MA 01890

MLS Number 72364106

  • Rental
  • Date Available 07/15/2018
  • Year Built 1901
  • Bedrooms 6
  • Waterfront

WATERFRONT - MYSTIC LAKE - GORGEOUS - picturesque Lake access from rear yard. This beautiful home is located in a very desirable neighborhood of distinctive homes and is situated on a 43,239 sq' lot abutting the Mystic Lakes - having 7 Bedrooms - 4 full Baths and 2 Half Bathrooms, Spacious Lakeview Kitchen and Great Room. The Foyer has a spectacular double staircase leading to the second level featuring a large Master Suite - 4 additional Bedrooms and three full Baths - the third floor has two additional Bonus Rooms/Bedrooms - which could be used for a Nanny Suite or two individual Bedrooms and full Bath. The Lower Level has a large Recreation Room - Exercise Room Bathroom and Laundry. Enjoy all this Home has to offer - stroll or run the trails along the Mystic River - just minutes to Commuter Train - Winchester Center - Middle and High Schools - the Ambrose School District and just 12 miles to Boston.

Listed by Lucille Murray of Leading Edge Real Estate

{$office->Name}

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: 4.52% last updated on Jul 19, 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.

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9 Fletcher Street, Winchester, MA 01890

MLS Number 72362863

  • Rental
  • Date Available 09/01/2018
  • Year Built 1910
  • Bedrooms 4
  • Pets Yes w/ Restrictions

Turn of the Century Charm - located in the "Flats" !!! Walk to downtown & train - close to beach, tennis, shopping. Big and bright - Hdwd fls 1st & 2nd flr, carpet in 3rd flr. Fireplace liv rm, formal din rm w/tray ceiling, family rm or office with slider to private deck, kitchen with double Jenn-Aire stoves in center island for easy entertaining. Sunny breakfast room leading to big porch over looking fish pond. 2nd fl has 3 bdrms including one with private bath (alternative master bedroom), Guest/Nanny suite on 3rd fl w/fireplace & full bath- 2 car garage.

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

{$office->Name}

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: 4.52% last updated on Jul 19, 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.

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44 Spruce Street, Winchester, MA 01890

MLS Number 72362227

  • Rental
  • Date Available 09/01/2018
  • Year Built 2000
  • Bedrooms 4
  • Pets Yes w/ Restrictions

Spacious light filled rooms. Side street neighborhood. Four bedrooms, two and one half baths. Hardwood floors. Master bedroom, guest bedroom and private bath have cathedral ceilings with skylights. Two car garage. Walk to schools. Walk to commuter rail from this in-town location! Washer and dryer in unit. All fenced in side and rear yard. Available September 1, 2018

Listed by Dylan Archambault of Archambault Real Estate

{$office->Name}

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: 4.52% last updated on Jul 19, 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.

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10 Chesterford Road East, Winchester, MA 01890

MLS Number 72362380

  • Rental
  • Bedrooms 3
  • Pets Yes w/ Restrictions

Beautiful home located on dead end street available NOW for rent - Spacious & renovated 3 bedroom single family with 2.5 baths with attached garage. Newly renovated granite and maple kitchen, master suite with 2 rooms and a private bath and jacuzzi tub. Very private setting with rear patio, expansive yard and beautiful plantings. Complete with all appliances including washer and dryer.

Listed by Kim Covino of Leading Edge Real Estate

{$office->Name}

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: 4.52% last updated on Jul 19, 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.

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418 Main Street, Winchester, MA 01890

MLS Number 72364592

  • Rental
  • Date Available 08/01/2018
  • Year Built 1876
  • Bedrooms 2

A meticulously kept Mansard Colonial home offering a spacious townhouse style apartment. A spacious living room and dining room, both with hardwood floors, overlooks the beautiful backyard for quiet enjoyment. The working kitchen with warm cherrywood cabinetry, an electric cooktop, wall oven and refrigerator. Two bedrooms and a nicely updated full bath on the 2nd floor. This unit has exclusive use of a screened in porch overlooking the beautifully landscaped yard. A short walk to downtown Winchester and the Commuter rail stop makes this a must see unit!

Listed by Annette Gregorio of Leading Edge Real Estate

{$office->Name}

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: 4.52% last updated on Jul 19, 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.

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41 Thompson Street, Winchester, MA 01890

MLS Number 72364767

  • Rental
  • Date Available 08/01/2018
  • Bedrooms 2

Located in the heart of downtown Winchester!! This 2 bed 1 bath apartment is situated in desirable location with easy access to the commuter train to Boston, restaurants and shops! Two large bedrooms, high ceilings, great closet space, lots of windows with natural light, updated gas heating system and located in the Lincoln school district.

Listed by Ngoc Anh Goldstein of Leading Edge Real Estate

{$office->Name}

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: 4.52% last updated on Jul 19, 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.

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