Winchester Homes for Sale

Winchester, Massachusetts is 8 miles north of Boston. Winchester is child-friendly and home to lakes, parks, and trails. Winchester keeps its public spaces well maintained. Winchester is a family-friendly bedroom community. 

Discover Winchester Real Estate

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10 Hillcrest Parkway, Winchester, MA

Price$1,289,000

Est. Mortgage: $/month

Open House

MLS Number 72245061

  • Single Family
  • Next Open House: Sat 21st 12:00 pm - 1:30 pm
  • Full Bath 3
  • Bathroom 3
  • Bedrooms 4

NESTLED AWAY AMONGST TREES, WITH NOT TOO DISTANT VIEWS OF THE NORTH RESERVOIR, THIS IS NOT YOUR AVERAGE HOME! Fantastic location on a very quiet street, within walking distance to many walking trails in the Fells Reservation. Newly finished hardwood floors, freshly painted kitchen cabinets, new light fixtures and shower doors...this house is move in ready! Host your next Thanksgiving in the vast living room-dining room combination, open floor plan concept with fireplace and wet bar. All bedrooms are located on the lower level with many windows allowing for plenty of natural light. Gorgeous screened in porch with whimsical stone flooring. Newer furnace (2013) and roof (2015). A short drive to downtown Winchester where you'll find many boutiques, salons, taverns, coffee shops and the commuter rail to North Station. Within the Muraco school district and only 7 miles North of Boston. Become a part of the Winchester community today and experience all this town has to offer!!!

Listed by Monte Marrocco of Coldwell Banker Residential Brokerage - Winchester

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Barrett Sotheby's International Realty - Concord
33 Walden Street
Concord MA, 01742
Office: 978-369-6453

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.90% last updated on Aug 10, 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 Ginn Road, Winchester, MA

Price$1,125,000

Est. Mortgage: $/month

Open House

MLS Number 72244913

  • Single Family
  • Next Open House: Sat 21st 12:00 pm - 1:30 pm
  • Full Bath 2
  • Bathroom 3
  • Bedrooms 3

Feel at home in 23 Ginn Rd. Curb appeal abounds in this well maintained home from its welcoming front porches and easy entry - which features large open kitchen, family room with one of the three stoned hearths, access to deck overlooking charming, serene yard. Flanked by spacious, bright dining room with gorgeous sliding french doors perfect for entertaining. Living room is at the front of the home with fireplace, more bright windows and oversized mantle with built-in shelves. Easy living in this home with first floor master with en-suite and two additional bedrooms with ample closets and family bath. Lower level is the perfect space for play. Built in bar for entertaining, the third fireplace in the home with access to flat, treasured back yard. Enjoy your own laundry room, 1/2 bath and additional hang out space all with access to patio. Two car garage and additional storage shed make this home just as practical as it is pretty.

Listed by Anne Spry and Alexis Nardone of Waterfield Sotheby's International Realty

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Barrett Sotheby's International Realty - Concord
33 Walden Street
Concord MA, 01742
Office: 978-369-6453

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.90% last updated on Aug 10, 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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124 Arlington Street, Winchester, MA

Price$1,750,000

Est. Mortgage: $/month

Open House

MLS Number 72245091

  • Single Family
  • Next Open House: Sat 21st 1:00 pm - 2:30 pm
  • Full Bath 5
  • Bathroom 5
  • Bedrooms 6

Recently acquired, this home presents a rare opportunity to own a custom build in one of Winchester's most desirable neighborhoods. From the front farmer's porch enter the elegant foyer with dramatic staircase and picture welcoming guests into your formal living room with stunning wainscoting. The open concept offers perfect flow from here to the dining room with exterior access to the private, professionally landscaped back yard. Next to the dinging room sits the eat-in kitchen offering highest end custom cabinetry and additional access to the rear patio and yard. Fireplaced family room, mud room, and bonus front-facing bedroom or office with connecting 3/4 bath complete this level. Second level master suite features sitting area, dueling walk-in closets, and soaking tub. Three large bedrooms, two of which are connected by marble-floored bathroom, plus additional full bath and separate laundry complete this floor. Third floor features another bedroom plus full bath and family room.

Listed by Kara Spelman of Better Homes and Gardens Real Estate - The Shanahan Group

{$agent->Name}

Barrett Sotheby's International Realty - Concord
33 Walden Street
Concord MA, 01742
Office: 978-369-6453

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.90% last updated on Aug 10, 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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5 Churchill Road, Winchester, MA

Price$1,699,000

Est. Mortgage: $/month

Open House

MLS Number 72245191

  • Single Family
  • Next Open House: Sat 21st 11:00 am - 12:30 pm
  • Full Bath 5
  • Bathroom 5
  • Bedrooms 6

Have you been dreaming of the opportunity to live in a luxury new construction home in Winchester without a $2M+ price tag?? Even better, a neighborhood you can be proud of?? TA-DA, you're dreams can come true! Perfectly situated on the corner of Churchill Circle (a quiet cul-de-sac) is 5 Churchill Road. The best of ALL worlds! Brand new construction by PREMIER local builder in a highly desirable quaint New England town. The open concept first floor kitchen and family room with fireplace, slider out to the rear patio, and large windows will make you fall in love with this airy space. The second floor master exudes elegance with large walk-in closet and spa-like bathroom. On this level you will also discover a junior suite with bath and 2 additional bedrooms with full bath. But wait, there's more! The upper level offers another bedroom, full bathroom, and 2 additional rooms for you to use however your imagination sees fit. A dream location for commuters with easy access to 93 AND 95.

Listed by Philip J. Vita of RE/MAX Leading Edge

{$agent->Name}

Barrett Sotheby's International Realty - Concord
33 Walden Street
Concord MA, 01742
Office: 978-369-6453

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.90% last updated on Aug 10, 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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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}

Barrett Sotheby's International Realty - Concord
33 Walden Street
Concord MA, 01742
Office: 978-369-6453

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.90% last updated on Aug 10, 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

MLS Number 72244192

  • Single Family
  • Bedrooms 5
  • Full Bath 5
  • Bathroom 6
  • 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}

Barrett Sotheby's International Realty - Concord
33 Walden Street
Concord MA, 01742
Office: 978-369-6453

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.90% last updated on Aug 10, 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 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 R. Sughrue of Better Homes and Gardens Real Estate - The Shanahan Group

{$agent->Name}

Barrett Sotheby's International Realty - Concord
33 Walden Street
Concord MA, 01742
Office: 978-369-6453

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.90% last updated on Aug 10, 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 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}

Barrett Sotheby's International Realty - Concord
33 Walden Street
Concord MA, 01742
Office: 978-369-6453

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.90% last updated on Aug 10, 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

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}

Barrett Sotheby's International Realty - Concord
33 Walden Street
Concord MA, 01742
Office: 978-369-6453

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.90% last updated on Aug 10, 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

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
  • Bathroom 3

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}

Barrett Sotheby's International Realty - Concord
33 Walden Street
Concord MA, 01742
Office: 978-369-6453

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.90% last updated on Aug 10, 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

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
  • Bathroom 3

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}

Barrett Sotheby's International Realty - Concord
33 Walden Street
Concord MA, 01742
Office: 978-369-6453

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.90% last updated on Aug 10, 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

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
  • Bathroom 3

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}

Barrett Sotheby's International Realty - Concord
33 Walden Street
Concord MA, 01742
Office: 978-369-6453

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.90% last updated on Aug 10, 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.