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.

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

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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: 4.03% 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.

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35 Rumford Street, Winchester, MA 01890
Open House

MLS Number 72243626

  • Condo or Co-op Condex
  • Next Open House: Sat 21st 1:00 pm - 3:00 pm
  • Bedrooms 4
  • Half Bath 1
  • Year Built 2012

Built in 2012, this gorgeous 4 bedroom 2½ bath energy-efficient townhouse is beautifully appointed inside & out. Upon entering the foyer, you’ll be impressed by the high ceilings, crown moldings, hardwood floors (on all 3 floors), & natural sunlight flooding every room. The much-desired open floor plan includes a living room w/fireplace, dining room, & stunning chef’s kitchen w/granite countertops, a huge island, maple cabinets, 2 pantries, & SS appliances. The 2d floor offers 3 spacious bedrooms including a huge master suite w/walk-in closet & bath. The 3d floor has great versatility w/ 2 additional rooms: a huge 4th bedroom or family room w/ fireplace & an office w/ built in closets & skylight. The exterior of the home features a one car attached garage, a welcoming farmers porch in the front yard, a fenced in side & back yard w/ deck, garden, gazebo & patio areas for relaxation & summer fun. 8/10 mile to downtown Winchester’s commuter rail, fine eateries, & shops.

Listed by Lorrie Parajeckas of Century 21 Commonwealth

{$agent->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: 4.03% 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.

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35 Rumford Street, Winchester, MA

Price$989,800

Est. Mortgage: $/month

Open House

MLS Number 72243628

  • Single Family
  • Next Open House: Sat 21st 1:00 pm - 3:00 pm
  • Bedrooms 4
  • Full Bath 2
  • Year Built 2012

Built in 2012, this gorgeous 4 bedroom 2½ bath energy-efficient attached single family is beautifully appointed inside & out. Upon entering the foyer, you’ll be impressed by the high ceilings, crown moldings, hardwood floors (on all 3 floors), & natural sunlight flooding every room. The much-desired open floor plan includes a living room w/fireplace, dining room, & stunning chef’s kitchen w/granite countertops, a huge island, maple cabinets, 2 pantries, & SS appliances. The 2d floor offers 3 spacious bedrooms including a huge master suite w/walk-in closet & bath. The 3d floor has great versatility w/ 2 additional rooms: a huge 4th bedroom or family room w/ fireplace & an office w/ built in closets & skylight. The exterior of the home features a one car attached garage, a welcoming farmers porch in the front yard, a fenced-in side & back yard w/ deck, garden, gazebo & patio areas for relaxation & summer fun. 8/10 mile to downtown Winchester’s commuter rail, fine eateries, & shops.

Listed by Lorrie Parajeckas of Century 21 Commonwealth

{$agent->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: 4.03% 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.

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7 Wainwright Road, Winchester, MA 01890
Open House

MLS Number 72243410

  • Condo or Co-op
  • Next Open House: Sun 22nd 1:00 pm - 2:00 pm
  • Bedrooms 3
  • Half Bath 1
  • Year Built 1989

Come see this bright & sunny “B” Unit Townhouse in the luxurious Ledges! Perfectly located near the beautiful in-ground pool, allowing for convenience when guests are over for all of your summer BBQs. This 3 bedroom, 3 full, 1 half bath townhouse features a spacious open floor living room with vaulted ceilings, elegant dining room with access to the private deck, spacious eat-in kitchen, cozy den & ½ bath complete the 1st floor. Upstairs you will find the master bedroom with cathedral ceilings, his & her closets & a large master bath, as well as another bedroom & full bath. Just steps down to the lower level, enjoy a 3rd bedroom, full bath, beautiful office, tons of storage space & the inviting family room with surround sound, perfect for watching the big game. This unit has a 2 car attached garage, as well as off-street parking for 2 cars. Onsite pool, clubhouse & tennis court makes it so you never have to leave. Move-in ready, come enjoy all of the amenities the Ledges has to offer.

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

{$agent->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: 4.03% 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.

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11 Middlesex Street, Winchester, MA

Price$949,000

Est. Mortgage: $/month

Active With Contract

MLS Number 72242850

  • Single Family
  • Bedrooms 4
  • Full Bath 2
  • Year Built 1953
  • Parking Spaces 2

COMPLETELY RENOVATED and expanded! Two level ranch with over 2200SF of gorgeous space! This move-in ready 4 bedroom 2 full bath home is equipped with all the modern aesthetics and appeal that today's buyers are looking for. The open concept main floor features an eat-in kitchen with new cabinets, beautiful granite countertops and stainless steel appliances; sunny living room with fireplace, dining area, three spacious bedrooms and one full bathroom. Relax down in your fully finished lower level offering an oversized media room, separate laundry room and large bedroom with full bath/walk-in closet - great for an au-pair suite!! Seller has done a beautiful job renovating and expanding this home! Brand new two zone heating/cooling systems, large level backyard, new landscaping, new siding and so much more!! Located close to center, schools, shops, restaurants and train into Boston. Don't miss the opportunity to move right into this wonderful home !

Listed by Kim Covino of RE/MAX Leading Edge

{$agent->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: 4.03% 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.

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85 Canal Street, Winchester, MA

Price$849,900

Est. Mortgage: $/month

Open House

MLS Number 72243294

  • Single Family
  • Next Open House: Sun 22nd 11:30 am - 1:00 pm
  • Bedrooms 3
  • Full Bath 2
  • Year Built 2017

This new construction townhouse with a large private yard will live more like a single family! The open concept first floor offers a kitchen with granite counters and center island, stainless steel appliances (gas oven), dining area, & living area featuring a handsome gas fireplace with stone surround. A lovely 1/2 bath is also offered on this level. Three bedrooms, laundry & two full baths are found on the second floor. One of those bedrooms being your master suite with walk in closet & full bathroom. The third floor and lower level offer versatility to truly make this home fit whatever needs you have. Perhaps a 4th bedroom and playroom? Maybe an office and media room’? An art studio or man cave? The choice is yours! This unit boasts a private rear deck overlooking a professionally landscaped yard complete with sprinkler system and the serene sounds of a babbling brook just outside your window. ~OPEN HOUSE Sunday Oct 22nd 11:30am-1:00pm~

Listed by The Synergy Group, Paul Cirignano and Philip J. Vita of RE/MAX Leading Edge

{$agent->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: 4.03% 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

163 Main Street, Winchester, MA

Price$659,000

Est. Mortgage: $/month

Open House

MLS Number 72243354

  • Single Family
  • Next Open House: Sun 22nd 12:00 pm - 1:00 pm
  • Bedrooms 4
  • Full Bath 2
  • Year Built 1961

Walking distance to Winchester Center, Public Transportation, Lincoln Elementary & McCall. A great opportunity to own a charming, move-in ready home containing that wonderful open floor plan you’ve been looking for. The main floor features stunning hardwood floors throughout its spacious open floor layout w/ample amounts of natural light streaming through the beautiful bay windows & skylight in the kitchen. Perfect for intimate gatherings, the inviting living room, dining room & eat-in kitchen all open to both the spacious yard & relaxing patio. The top floor contains 3 generously sized bedrooms, 2 baths, inclusive of the master with walk-in closet & master bath. Steps down to the lower level, you will find a cozy family room, additional bedroom/office & mudroom with 1/2 bath. This home offers plenty of storage in the laundry room & basement, which could be finished by its new owners. With plenty of off-street parking & its prime location, you’ll want to call this beautiful home yours!

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

{$agent->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: 4.03% 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

11 Canal Street, Winchester, MA

Price$499,000

Est. Mortgage: $/month

MLS Number 72243670

  • Single Family
  • Bedrooms 2
  • Full Bath 1
  • Year Built 1926
  • Parking Spaces 3

ATTENTION: Investors & Contractors. Great potential for new construction or a remodel. This property is zoned as General Business District 3 which may offer a builder creative options. Home is being sold "as is". Conveniently located near schools, public transportation, restaurants and shops. Don't miss out on this great opportunity!

Listed by Paula Sughrue of Better Homes and Gardens The Shanahan Group

{$agent->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: 4.03% 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
Open House

MLS Number 72244700

  • Condo or Co-op
  • Next Open House: Sun 22nd 12:00 pm - 2:00 pm
  • Bedrooms 1
  • Year Built 1966

Why pay rent when you can own and build equity in beautiful Winchester ? Centrally located condo offers all utilities included in monthly fee. Enjoy the scenic views of the duck pond and manicured grounds from the comfort of your own balcony. Walk to the commuter rail and lovely downtown Winchester. Convenient to highway and public transportation. An inground pool, parking for guests, laundry facilities and security are all included in this complex. Affordable living in a gorgeous town with an excellent school system. Priced to sell as is. Showings begin at OPEN HOUSE ON SUNDAY, OCT 22ND FROM 12:00-2:00PM.

Listed by The Synergy Group and Susan Silkes of RE/MAX Leading Edge

{$agent->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: 4.03% 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

11 Tufts, Winchester, MA 01890

MLS Number 72242883

  • Rental
  • Bathroom 3
  • Date Available 12/01/2017
  • Bedrooms 4

SHORT-TERM POSSIBLE, SMALL DOGS CONSIDERED 5 year-old (so no lead paint), 4-story home in a side-by-side two-family. Available around December 1. Brand new condition with all the bells and whistles. Built by a high-end Winchester builder, located on a cul-de-sac that ends at Muraco Elementary. 3 or 4 beds 2 1/2 baths (1 powder, 1 family with dual sinks, 1 master ensuite with Jacuzzi, shower, dual sinks) 2 zone AC, gas heat, on-demand hot water kitchen with stainless Bosch appliances, Cambria quartz countertops, gas, touch faucet 3 car garage (end over end), with opener, (savings vs. renting a storage locker!) plantation shutters built-ins recessed lighting cable ready low-e, energy efficient windows back porch and big fenced-in yard built-in bar basement storage 2nd fl laundry 3rd floor bonus room Restoration Hardware lighting walk-in master closet approx. 1 mi walk to Winchester station

Listed by Robyn Huschle of Coldwell Banker Residential Brokerage - Winchester

{$agent->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: 4.03% 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

226 Washington Street, Winchester, MA 01890

MLS Number 72241971

  • Rental
  • Bathroom 1
  • Date Available 12/01/2017
  • Bedrooms 2

Available December 1st, this sunny 2 bedroom apartment is walking distance to Winchester Center, Public Schools, T-Station, Commuter Rail, Restaurants, and Shopping. Located on the second floor, this unit features an open floor plan, large kitchen and eating area, 2 bedrooms with closets and one full bath. Also included is central air, an enclosed front porch, a back deck, an in-unit washer and dryer, additional private storage in the basement and a driveway with 2 assigned parking spots. Professional landscaping and snow plowing included. Excellent Location: Easy to access all major routes.

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

{$agent->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: 4.03% 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

10 Loring Avenue, Winchester, MA 01890

MLS Number 72243498

  • Rental
  • Bathroom 2
  • Bedrooms 2

Winchester, MA - Well Maintained Inside And Out 2 Bedrooms, 1.5 Bath Duplex Townhouse With 3 Levels Of Living Space; Just Minutes To Routes 38, 93, 95/128, Burlington Mall, And 30 Minutes Drive To Downtown Boston, Mass General Hospital; MBTA Littleton/495 Train Station Is Just A 35 Minutes Drive. Home Features: Many Updates; Gleaming Hardwood Floors Throughout, Freshly Painted Walks, Eat-In-Kitchen With Gas Stove, Refrigerator, Dishwasher And Lots Of Cabinets; Updated Windows; Nice Attic Space For Office Or Study; Very Clean Basement With Laundry Machines Hook-Up And Storage Space; Beautiful Landscaped Back Yard For Your Family Enjoyment; Off- Street Parking For 2 Cars With Restrictions; Heating And Hot Water Tank Is Operated Via Gas, Paid By Tenant; Owner Pays The Water And Sewer Bills. Pets: Owner Would Consider a Declawed Spaded Cat; Move-In-Costs: First Month, Security Deposit, 1/2 Broker's Fee, Plus $30 Credit/Background Processing Fee.

Listed by Herman Davis of Boston Metro North Realty

{$agent->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: 4.03% 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

2 Winchester Place, Winchester, MA 01890

MLS Number 72243811

  • Rental
  • Bathroom 1
  • Date Available 12/01/2017
  • Bedrooms 1

Apartment rental 2 rooms. Kitchen with skylight and bedroom. Rent includes water and weekly household trash removal. Parking Permits are available through town hall. No smoking in building This is a 7 month rental

Listed by Deborah L. Leavitt of Century 21 Commonwealth

{$agent->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: 4.03% 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.