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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184 Ridge Street, Winchester, MA

Price$2,499,000

Est. Mortgage: $/month

MLS Number 72263106

  • Single Family
  • Bathroom 5
  • Full Bath 4
  • Bedrooms 4
  • Year Built 2017

Perched atop the West Side Hill, on almost 1 acre, this east facing, sprawling new construction 4Beds 4.5Bath home will exceed your expectations! First floor features huge 30' kitchen with Thermador appliances, 10' center island, custom cabinets, dining area, pantry, mudroom, heated attached 3 car garage, year round sunroom overlooking sprawling "football field" sized back yard, family room off kitchen with natural stone fireplace, office, formal living w/ FP, dining room, butlers pantry, and a dramatic stairway to the second floor. Master is unlike anything you've seen..enter into a sitting room with fireplace, ballroom sized bedroom, lavish master bath with radiant heat floor, custom cabinetry, soaking tub and oversized shower with built in seat. 3 Add'l bedrooms with en-suite baths. Lower level w/ full windows & slider can easily be customized with another full bath/media room/gym;you design.. builder will create for you! Don't miss this spectacular home complete w/ HEATED DRIVEWAY!

Listed by Kim Covino of RE/MAX Leading Edge

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

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$
$
%
$/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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83 Thornberry Road, Winchester, MA

Price$849,000

Est. Mortgage: $/month

MLS Number 72263361

  • Single Family
  • Bathroom 3
  • Full Bath 2
  • Bedrooms 4
  • Year Built 1970

Beautiful Multi-Level home built with traditional Colonial styling throughout in sought after West Side Vinson Owen school district! Interior Colonial details include: crown moldings, wooden muntin windows, oak flooring and traditional fireplace mantels. Millennial+ Granite/Maple kitchen with oak floors, recessed lighting, chair rail/raised moldings and more. Steps away from the kitchen, you'll find a rear area mud room, an oversized half bath and direct access to the generous sized two car garage with ample storage & work area and rear access to the yard & storage shed. A few steps further, finds an oversized picture window fireplaced family rm and a bright and sunny multi-purpose rm w/laundry facilities, a desk area, double hung windows and a full walkout to the rear yard. The upper level wing offers 4 bedrooms, including, an ample sized MBR, both family & master baths and a linen closet. Impeccable grounds and just a very short walk to the Whipple Hill nature preserve trailhead!

Listed by Don Coughlin of RE/MAX Leading Edge

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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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17 Symmes Road, Winchester, MA
Open House

MLS Number 72262296

  • Single Family
  • Next Open House: Sat 16th 1:00 pm - 2:30 pm
  • Bathroom 4
  • Full Bath 3
  • Bedrooms 5

Been looking for that special house with tons of character? Updated? Close to Winchester Center and train stations? Close to schools? Presenting 17 Symmes Road, a quintessential Winchester Center home with glowing woodwork, charming built in cabinetry and a large front porch- perfect for neighborhood get-togethers! First floor features a gorgeous living room with wood paneling, window seat and fireplace, large dining room and eat-in kitchen. The kitchen features stainless steel appliances, granite counters and opens to a den, perfect for playroom or family room. The second floor features three bedrooms, including a newer master bedroom suite and updated bathrooms. The third floor is spacious with two bedrooms and a full bathroom, including laundry room. Lots of updates including central air, electrical and newer windows. Enjoy all that Symmes Rd has to offer with your beautifully manicured, fully-fenced yard with patio. Start 2018 in your dream home!

Listed by Karen S. Garrett of Better Homes and Gardens Real Estate - The Shanahan Group

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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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14 St Thomasmore Drive, Winchester, MA

Price$3,199,000

Est. Mortgage: $/month

MLS Number 72262053

  • Single Family
  • Bathroom 7
  • Full Bath 6
  • Bedrooms 5
  • Year Built 2018

NEW CONSTRUCTION BY LOCAL MASTER BUILDER! The design of this spectacular home with the integrated floor plan that every modern, savvy buyer seeks truly is a masterpiece. Featuring 3 floors of finished living with volume control surround sound throughout each room. Within the 3-year old Vinson Owen school district. Located a short drive to downtown, where you'll find plentiful coffee shops, boutiques, restaurants, taverns & salons. The commuter rail with 2 Winchester locations is a short 15-20 ride to Boston's North Station. Do not miss out on this opportunity to own a true gem. Become a part of the Winchester community and experience all it has to offer!

Listed by Monte Marrocco of Coldwell Banker Residential Brokerage - Winchester

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Barrett Sotheby's International Realty - Lincoln
152 Lincoln Road
Lincoln MA, 01773
Office: 781-259-4040

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$
$
%
$/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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2 Elm Street, Winchester, MA

Price$999,000

Est. Mortgage: $/month

Active With Contract

MLS Number 72261332

  • Single Family
  • Bathroom 3
  • Full Bath 2
  • Bedrooms 4
  • Year Built 1910

This farmhouse has been completely renovated with thoughtful attention to details. The spacious eat-in kitchen is a chef's dream, featuring a large island with hammered copper sink, double Wolf range, granite counters, and custom butternut cabinetry. The sunny family room is off the kitchen and offers built-in bookcases. The living room is a cozy place to entertain, with a fireplace surrounded by built-ins. The first floor offers one bedroom which could be used as an office. The showpiece of the second floor is the master suite, which offers multiple closets, including a walk-in. The spa-like master bath has a double vanity, stand-up shower and champagne tub. The second floor also offers two additional bedrooms, a full bath, and a laundry room.The house features a Beacon Hill-style backyard, a perfect spot for outdoor dining. This house couldn't be closer to downtown Winchester and its amenities, including shopping, the Farmer's Market, library, schools, parks, and train to Boston.

Listed by Theuer - Pirani Team 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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10 Cleveland Road, Winchester, MA 01890
Open House

MLS Number 72261299

  • Condo or Co-op
  • Next Open House: Sat 16th 11:15 am - 12:15 pm
  • Bedrooms 3
  • Bathroom 4
  • Full Bath 3

The feel of a singe family home! Lovely 3 bedroom townhouse just completed with beautiful high end designer finishes & a spacious floor plan! 3 finished levels, Sunny chefs kitchen with island, Kitchen Aid appliances, quartz countertops, dining area off kitchen open to living/family room with gas fireplace. Cathedral ceiling Master with private bath, walk in closet, second floor laundry, finished lower level makes a great family room/media/rec room complete with another full bath! each unit has its own large, level deeded/exclusive use yard! Don't miss out on this great home at this unbeatable price. Call for a private showing!

Listed by Kim Covino 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

8 Cleveland Road, Winchester, MA 01890
Open House

MLS Number 72261300

  • Condo or Co-op
  • Next Open House: Sat 16th 11:15 am - 12:15 pm
  • Bedrooms 3
  • Bathroom 4
  • Full Bath 3

The feel of a singe family home! Lovely 3 bedroom townhouse just completed with beautiful high end designer finishes & a spacious floor plan! 3 finished levels, Sunny chefs kitchen with island, Kitchen Aid appliances, quartz countertops, dining area off kitchen open to living/family room with gas fireplace. Cathedral ceiling Master with private bath, walk in closet, second floor laundry, finished lower level makes a great family room/media/rec room complete with another full bath! each unit has its own large, level deeded/exclusive use yard! Don't miss out on this great home at this unbeatable price. Call for a private showing!

Listed by Kim Covino 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

5 Harvard Street, Winchester, MA

Price$729,000

Est. Mortgage: $/month

MLS Number 72260208

  • Single Family
  • Bedrooms 3
  • Bathroom 2
  • Full Bath 2
  • Year Built 1891

Move right in this well designed, beautiful 3 bed 2 bath colonial near Winchester center. This house offers large living space, smart floor plan, high ceilings, a delightful kitchen, modern bathrooms and brand-new hardwood floor throughout! New roof as well! Entry via front porch to first floor which boasts a sun-splashed living room with bay windows, a formal dining room, a newly added bathroom and a gorgeous kitchen! Second floor presents with three good sized bedrooms and one bath, all well connected with elegant hallway. Third floor offers two large finished rooms good for any purpose. Large basement is great for storage and potential expansion. Detached one car garage converted to shed. Flat backyard with mature grape vines, perfect for garden lovers or fenced in to turn into joyful playground for kids. located in family oriented neighborhood with walking to top rated schools. Convenient to hospital, park, commuter rail, highways, shops and Boston! Sweet home for years to come!

Listed by Yanjie Jiang of DayDay-Up Realty

{$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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49 Jefferson Road, Winchester, MA

Price$1,875,000

Est. Mortgage: $/month

Open House

MLS Number 72259751

  • Single Family
  • Next Open House: Sat 16th 1:00 pm - 2:30 pm
  • Bedrooms 5
  • Bathroom 5
  • Full Bath 3

New England Shingle-style home just completed! Located on a bucolic tree lined cul de sac less than a mile from Winchester center. Picturesque & full of character w/ striking elements such as tall gables trimmed w/ corbels, premium red cedar shingles w/ fieldstone siding & gorgeous landscaping. Upon entry, long sight lines maximize natural light & showcase the flow of the open first floor plan. Custom built-ins, trim, & coffered ceilings frame & punctuate the view, making the high-ceilinged spaces intimate. These impressive open spaces are unified by richly hued 3 ¼” white oak hardwood floors & high-end finishing details, yet are free of excess formality. More than 4,000 beautifully finished square feet over three levels w/ many unique features include 4 custom fieldstone fireplaces w/ circa-1800 reclaimed, hand-hewn wood mantels. The spa-like Master Suite is simply divine. This architecturally distinguished home offers comfortable yet elegant living, & could be yours in the New Year!

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.

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52-54 Swanton ST.,, Winchester, MA

Price$575,000

Est. Mortgage: $/month

Active With Contract

MLS Number 72258957

  • Single Family
  • Bedrooms 2
  • Bathroom 2
  • Full Bath 1
  • Year Built 1867

Conveniently located Winchester property is currently mixed use - residential and commercial - and could be the perfect home for you AND your business!! The first floor housed a photography business and includes 2 offices, a studio and half bath. The upper 2 floors are currently used as a 7 room family home. Level 2 has an open plan kitchen and living room, plus 2 additional rooms that have been used as bedrooms. Level 3 has 2 bedrooms, a den and full bath. Needs work - but great potential and a terrific opportunity to create spaces that will fit your specific needs. Being sold as-is. Buyers to do due diligence regarding the types of businesses that can be operated in the property or regarding the possiblity of returning house to a 2 family. Quigley Court is a town plowed right of way that runs along the side of the house.

Listed by Kimberly A. Redmond of Exit Family First Realty

{$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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16 Robinhood Road, Winchester, MA

Price$899,000

Est. Mortgage: $/month

MLS Number 72258576

  • Single Family
  • Bedrooms 4
  • Bathroom 2
  • Full Bath 2
  • Year Built 1954

Looking to move to Winchester? This beautiful move in ready home, is the perfect fit for you! Come see this charming and spacious 4 bedroom, 2 full bath Ranch just a brief walk to the highly acclaimed Ambrose Elementary School. Located on a corner lot in a popular west side neighborhood with a beautiful backyard. Featuring hardwood floors throughout it’s spacious open concept layout on the main floor. Built for easy entertaining with the living room and dining room both opening up to an incredible family room with soaring cathedral ceilings and french doors which opens up to a peaceful patio and backyard setting. Containing 4 generously sized bedrooms, 2 full baths inclusive of the master bath and an exceptional work area and extra storage with convenient access to the 2 car garage. Additional amenities include, central air, sprinkler system, an attached 2 car garage and off-street parking for 2 cars. Make this incredible home yours!

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

{$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

83 Church Street, Winchester, MA 01890

MLS Number 72258508

  • Condo or Co-op
  • Bedrooms 2
  • Bathroom 2
  • Full Bath 2
  • Year Built 1983

Everything you've been looking for! It's the former "Wyman School" - a short walk to downtown offering fine restaurants, unique shops, commuter rail, and Farmers Market. This is a 1st floor unit with a master bedroom and bath on the 1st fl AND the 2nd floor! Living room has a 17-foot ceiling and round-arched window over French doors to a pretty garden area. A curved balcony overlooks the living room and offers generous additional space for a nice study or library. The first level also has a formal dining room with full-mirrored wall, high ceilings, hardwood floors, and generous closets. Washer & dryer in the unit Additional storage room in the basement. One deeded garage and additional outside parking for second car. Well maintained brick building. New gas heating system. Pets negotiable. OPEN HOUSE SUNDAY, DEC. 10th 12-2 PM.

Listed by Diane Plunkett and Lynn Ricci of Plunkett Properties

{$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

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