Homes for Sale Winchester MA

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

As you search through listings please be sure to contact us with any questions or to schedule a viewing. Register on the site to save your favorite listings and to receive email notifications when similar listings come to market.

You may also be interested in viewing homes for sale in
Arlington | Belmont | Cambridge | Waltham | Woburn

r=1-12
310 Main Street, Winchester, MA

Price$1,139,500

Est. Mortgage: $/month

MLS Number 72436394

  • Single Family
  • Parking Spaces 5
  • Year Built 1890
  • Full Bath 2
  • Bathroom 2

BUILDER/OWNER WILLING TO WORK WITH BUYER ON CUSTOM RENOVATION on this Great in-town location 3200+ sq ft colonial on a 10,000+ sq ft lot. Expansive front porch with gazebo-style roof welcomes you to this home. First floor features charming foyer with curved staircase, office/bedroom that connects to full bath, entertainment-sized living room with fireplace and French doors, formal dining room, cozy den loaded with windows, and kitchen with granite counter tops and stainless steel appliances. Second floor has 3+ bedrooms and full bath. Walk-up third floor has bedroom/office as well as ample storage space. Hardwood floors throughout most of first and second floors. Don't miss your opportunity to raise your family in this great house within walking distance to everything this great town has to offer.

Listed by Tom Doherty of Gibson Sotheby's International Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 4.45% last updated on Jan 17, 2019
* 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

72 Irving Street, Winchester, MA 01890

MLS Number 72435739

  • Condo or Co-op
  • Bathroom 2
  • Year Built 1910
  • Full Bath 2
  • Bedrooms 2

Welcome to Winchester! Calling all first-time home buyers, down-sizers or looking for an alternative to renting. This is a wonderful first floor condo, turn-key newer construction with two-bedroom, two full bathrooms. The open floor plan offers an impressive eat-in kitchen, finished with granite counter tops, gas for cooking and stainless-steel appliances. The lower level is that perfect get away family room / den to watch Sunday afternoon football, or just catch up with that book. Storage room and the washer and dryer are included in the sale. Irving Street is close to the outstanding Winchester center, which offers the commuter rail to Boston, coffee houses, artisan stores and several local restaurants. Easy access to Routes 93 & 95. Taking the back roads through West Medford is a great alternative to commute to Cambridge.

Listed by Peter Rooney of William Raveis R.E. & Home Services

$
$
%
$/month over payments
Federal 30-year interest rate: 4.45% last updated on Jan 17, 2019
* 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 Royalston Avenue, Winchester, MA

Price$1,799,000

Est. Mortgage: $/month

MLS Number 72432766

  • Single Family
  • Parking Spaces 4
  • Year Built 2018
  • Full Bath 4
  • Bathroom 5

When the weather gets cold, the trees are bare, and there's snow falling down around us, don't you just want to hibernate? When New England hits us hard isn't it less important to go out for a night on the town, and more important to whip up a scrumptious dinner in your own home and curl up on the couch with a glass of wine and a movie? What make these pastimes even more desirable is when you can do them in a place like 19 Royalston. This 5 bedroom, 4.5 bathroom property with stunning kitchen featuring top of the line appliances will make you never want to leave home again! The 1st floor boasts a family room with fireplace, kitchen with SubZero refrigeration and Wolf cooking, dining room with wet bar, 1/2 bath, and home office with exterior access. A favorite feature consistently done by this developer is having all 5 bedrooms on the 2nd level! The vast 3rd level may be best of all! This space can easily be used as a playroom, media room, or au-pair quarters as it offers a full bath!

Listed by Philip J. Vita of Leading Edge Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 4.45% last updated on Jan 17, 2019
* 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

512 South Border Road, Winchester, MA

Price$1,589,900

Est. Mortgage: $/month

MLS Number 72430943

  • Single Family
  • Parking Spaces 4
  • Year Built 2018
  • Full Bath 4
  • Bathroom 5

This beautiful new construction, three level Colonial home in Winchester is a must see, with a 60-90 day delivery! Located across the street from Middlesex Fells Reservation, this is the perfect location for everything Winchester has to offer. This home will feature gorgeous finishes including eat-in kitchen with new quartz counters, stainless steel appliances and formal dining room. The spacious rooms through-out the home include a finished basement with full size windows, and finished 3rd floor with a 5th bedroom and bonus room!

Listed by Gary J. Litchfield of Mass. Real Estate Solutions, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 4.45% last updated on Jan 17, 2019
* 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

18 Border Street, Winchester, MA 01890

MLS Number 72430405

  • Condo or Co-op
  • Half Bath 1
  • Bathroom 2
  • Year Built 1890
  • Full Bath 1

NO CONDO FEES!! This charming DELEADED turn-key home is in pristine condition and is full of character and personality. Everything has been beautifully and tastefully updated, including new kitchen appliances, beautiful quartz countertops, and many cosmetic upgrades. Enjoy breakfast in the sun-filled dining area with skylight and sliders out to the deck, which overlooks a STUNNING fenced in back yard that features mature fruit trees, gorgeous landscaping, storage shed, and a SPRINKLER SYSTEM. Enjoy cozy evenings in front of the beautiful gas fireplace. Hardwood floors, high ceilings, ample closet and storage space (including potential expansion in the partially finished basement), and second floor laundry top off the list to make this home perfect. All in Winchester for under $600K!

Listed by Jennifer Hardin of True North Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 4.45% last updated on Jan 17, 2019
* 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

15 Royalston Avenue, Winchester, MA

Price$1,599,999

Est. Mortgage: $/month

MLS Number 72430067

  • Single Family
  • Parking Spaces 4
  • Year Built 2003
  • Full Bath 3
  • Bathroom 4

This distinctive, updated colonial accents today's more casual lifestyle with a spacious, open floor plan, hardwood floors, and a kitchen you'll fall in love with - maple cabinets, granite counters, a huge island to seat 6+, & breakfast counter overlooking the fireplace living room. Immense dining room w/butler's pantry/2nd sink & dishwasher. The amenities continue with a 1/2 bath, 1st floor guest room, & office w/pocket doors to provide solitude from a busy household. The 2nd floor has 3 bedrooms, bath, huge laundry room, & a truly luxurious master suite w/large walk-in closet & cathedral ceilinged bath w/soaking tub, double sinks, make-up table, and large glass shower. The lower level has a huge mudroom off the 2 car garage, & large family room & bath. But wait, there's more - sliders from the kitchen lead out to a mahogany deck & a gorgeous built-in pool. A truly great Winchester home in which to live, to entertain, and to enjoy for many years to come! Muraco School!

Listed by The Lorrie Parajeckas Group and Lorrie Parajeckas of Compass

$
$
%
$/month over payments
Federal 30-year interest rate: 4.45% last updated on Jan 17, 2019
* 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

16 Marshall Road, Winchester, MA

MLS Number 72427239

  • Single Family
  • Parking Spaces 4
  • Year Built 1951
  • Full Bath 3
  • Bathroom 3

Live in one of the most sought after neighborhoods in Winchester and just 10 minutes from Boston. This Mid Century Modern home offers beautiful designer finishes inside and out, with it's lush landscaping, breathtaking deck and water feature. The open and airy living space is flooded with light all day from many skylights thru out. Fully appointed kitchen with marble breakfast bar, sub zero refrigerator and gold accents. The truly enormous master suite includes cathedral ceilings, window seat, it's own fireplace, incredible walk in closet with island, and exquisite master bath. Two additional bedrooms and full bath on main living level, French doors to office/study, a large media room and full bath on lower level is ideal for extended stay guests. Direct access from two car garage, additional storage. Just a quick walk to Wedgemere Station or delightful downtown Winchester and all schools.

Listed by Candice Macoul and Lorelei Ritter of RE/MAX Luxury Living RE

$
$
%
$/month over payments
Federal 30-year interest rate: 4.45% last updated on Jan 17, 2019
* 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

62 Swanton Street, Winchester, MA 01890

MLS Number 72426564

  • Condo or Co-op
  • Bathroom 2
  • Year Built 2018
  • Full Bath 2
  • Bedrooms 3

CONSTRUCTION COMPLETE!! NEW PRICE-- Brand new construction! Three bedroom two bathroom condo with open concept kitchen and family room for easy entertaining. Kitchen boasts beautiful white cabinets with granite counters, stainless steel appliances including 5 burner gas range with exhaust hood fan. Master bedroom has walk in closet and spacious master bathroom with subway tile shower. Two additional bedrooms with spacious double closets. Bonus additional recreation room in lower level and full laundry room. Home features gleaming hardwood floors throughout, central air, 6 panel shaker style doors, private driveway, patio, and farmers porch. Close to charming Winchester Center with great restaurants, coffee shops, boutiques, and commuter rail station for easy commute into the city. Nearby to brand new tri-town bike path and highly sought after schools. Routes 93 and 95 close by! Truly a commuters dream! OFFERS IF ANY ARE DUE BY MONDAY, JANUARY 21ST BY 5:00 PM.

Listed by Kristine Welch of Greater Metropolitan R. E.

$
$
%
$/month over payments
Federal 30-year interest rate: 4.45% last updated on Jan 17, 2019
* 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

47 Arlington Street, Winchester, MA

Price$2,050,000

Est. Mortgage: $/month

MLS Number 72426120

  • Single Family
  • Parking Spaces 4
  • Year Built 2000
  • Full Bath 5
  • Bathroom 6

Gorgeous Colonial in move-in condition. Impeccable Myopia Hill location overlooking the Winchester Country Club with stunning light & serene golf course views, beautiful landscaping. Sweeping open floor plan is perfect for both relaxed daily living & luxurious entertaining. Outstanding craftsmanship include: high ceilings, large windows, oversized doors, exquisite bridal staircase. The sun-drenched front to back kitchen with large island & dining area opens to a covered porch - the perfect spot to enjoy your morning coffee overlooking the 4th hole. The two story foyer leads to the cathedral ceiling fireplace family room, fireplace living room & large dining room. The back entry provides easy access to the 1st floor guest room & fireplace study. The second floor includes the front to back master bedroom suite with three additional bedrooms, 2 baths & large laundry room. Spend your weekends enjoying the media room, exercise room & spacious play room or game room.

Listed by Anne Spry and Jane Byrne of Waterfield Sotheby's International Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 4.45% last updated on Jan 17, 2019
* 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

4 Town Way, Winchester, MA

Price$1,949,000

Est. Mortgage: $/month

MLS Number 72424070

  • Single Family
  • Parking Spaces 6
  • Year Built 2018
  • Full Bath 4
  • Bathroom 5

Currently Under Construction and ready for Spring occupancy!! Amazing 6000sf casual/ open concept colonial offering a great opportunity to customize and create your dream home! This beautiful home offers all of today's amenities with an oversized 2-car garage, direct entry into mudroom, gourmet kitchen w/ island, adjacent family room with fireplace, formal living and dining with crown moldings and wainscoting. Second floor features include Master suite with walk-in closets, luxurious master bath, laundry room with custom cabinetry and wash sink, four oversized corner bedrooms filled with lots of light & hardwood floors. 3rd floor with 2 add'l rooms & full bath~Great rear yard w/deck & sliders from kitchen. This home is located in sought after East side of town, convenient to the center, Lincoln school district, and is truly a great neighborhood! Basement family/media w/fireplace, kitchenette/ full bath &-plenty of space for gym or guest suite~ Call today for private showing!

Listed by Kim Covino of Leading Edge Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 4.45% last updated on Jan 17, 2019
* 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 Meadowcroft Road, Winchester, MA

Price$1,929,000

Est. Mortgage: $/month

MLS Number 72423009

  • Single Family
  • Parking Spaces 4
  • Year Built 1953
  • Full Bath 4
  • Bathroom 6

UNBEATABLE LOCATION, SITUATED IN THE HEART OF WINCHESTER!!! Completely renovated property in The Rangeley Estates. The first floor features an open floor plan for today's modern lifestyle, with a fireplaced living room, dining room and spacious kitchen. Enjoy entertaining your guests in the oversized kitchen, boasting a top of the line SS appliance package, granite counters and a slider with direct access to a large wooden deck. 4 bedrooms are located on the second floor, including the master and an additional en-suite, along with laundry and plentiful closets. The third floor is finished with a 5th bedroom, bathroom and large sitting room. Walk to the common and explore Winchester's boutiques, restaurants & coffee shops or take the commuter rail to North Station for a day in the city. Within the Ambrose school district and 7 miles North of Boston.

Listed by The Marrocco Group and Monte Marrocco of Coldwell Banker Residential Brokerage - Winchester

$
$
%
$/month over payments
Federal 30-year interest rate: 4.45% last updated on Jan 17, 2019
* 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

7 Conant Road, Winchester, MA 01890

MLS Number 72419379

  • Condo or Co-op
  • Half Bath 1
  • Bathroom 3
  • Year Built 1999
  • Full Bath 2

This 2 bed 2.5 bath end/corner unit has great light, with extra windows, and sliders to THREE balconies, off Living Room & each Bedroom. The Foyer opens to the LivRm with gas FP and contemporary mantel, a bright Dining Area, and turning staircase to the sleeping Level. Stove & microwave, oak cabinets, refrigerator. Master Bedroom, with private bath; main bath w/spa-jet tub. Carpeted bedroom floors, professionally painted walls. Plenty of closet space. Large bonus storage area in basement & attic.It is building 3, level 2.

Listed by McDonough & Wang Group, Alina Wang and Richard McDonough of Leading Edge Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 4.45% last updated on Jan 17, 2019
* 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.