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
7 Gardner Place, Winchester, MA

Price$1,450,000

Est. Mortgage: $/month

Open House

MLS Number 72418629

  • Single Family
  • Next Open House: Sat 19th 12:00 pm - 1:30 pm
  • Parking Spaces 2
  • Year Built 1932
  • Full Bath 3

The Gardner-Swan Ell House is a rarity, an intact Pre-Revolutionary structure whose tasteful updates and versatility make it timeless. Dating back to 1764 and originally connected to 89 Cambridge St as a shoe shop, architect Frank Patterson Smith moved the historic Ell to its present location in 1931. The Middlesex Canal ran along the property line and the land was the site of “Gardner Locks”. The present owners lovingly maintained and updated the original home with an addition in 1997 - an expansive family room, entry hall and eat-in kitchen. Beamed ceilings in the living and dining room, a home office with a separate entrance, fireplaces and charming butler's pantry add to its unique character. The second floor includes a master bedroom suite with fireplace plus 3 additional bedrooms and two baths. Spacious front and back yards, front patio and water gardens provide great space for outdoor play and entertaining. This welcoming home will delight and surprise you for years to come!

Listed by Anne Spry and Katie Tully 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

5 Allen Road, Winchester, MA
Open House

MLS Number 72411104

  • Single Family
  • Next Open House: Sat 19th 12:00 pm - 1:30 pm
  • Parking Spaces 4
  • Village East Side
  • Year Built 2018

New construction in Winchesters popular East Side. This 11 room, 5 bedroom home is perfect for today's buyer. Thoughtfully designed with an open yet traditional feel with coffered ceilings & rich millwork. The 1st floor has a formal living room w/fireplace, formal dining room, front to back family room, gorgeous kitchen with high-end appliances, quartz counters & center island, 1/2 bath & mud room. The 2nd floor features 4 bedrms, laundry room & 3 full baths. The master bedroom has two walk-in closets, a luxurious bath & sitting area. The 3rd floor has a bonus room plus a 5th bedroom with full bath perfect for au-pair, in-law or teen suite. The basement is partially finished with a bonus/play room, space for a gym/office and plenty of storage. This home is perfect for the family looking for a quiet neighborhood, with all the benefits of owning a brand new home. Lincoln School District less than a mile from Wedgemere train station and shops & restaurants OPEN HOUSE Sat Jan 12th 12-1:30

Listed by The Synergy Group and Paul Cirignano 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

31 Swan Road, Winchester, MA

Price$2,199,999

Est. Mortgage: $/month

Price Changed

MLS Number 72410499

  • Single Family
  • Parking Spaces 10
  • Year Built 1929
  • Full Bath 3
  • Bathroom 5

What does it mean to have a Swan Road address? It means you've arrived! Give yourself the gift of owning 31 Swan Road. A stately Tudor style home with magnificent grounds, situated on one of the finest roads that Winchester has to offer. The stunning brick exterior, adorned with slate roof, will impress you from moment one. As you enter, the beautiful foyer will leave you breathless. The sunken living room with Bath Stone fireplace and hand crafted wood walls is something straight out of a magazine. Enjoy the opulence and grandeur of a time gone by, seamlessly combined with a sensible layout and amenities of today such as a renovated kitchen with Wolf, Viking, and SubZero appliances. The second level is home to four bedrooms, and 3 full baths, including the master suite drenched with natural light, thanks in part to the homes South facing direction. Should you venture off these park-like grounds you'll find yourself within walking distance to both Winchester Country Club and Boat Club.

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

200 Swanton Street, Winchester, MA 01890

MLS Number 72410101

  • Condo or Co-op
  • Bathroom 1
  • Year Built 1966
  • Full Bath 1
  • Bedrooms 2

Welcome to this Stunning 2 BR unit on Terrace level with amazing view of duck pond and flowering garden area from private outdoor patio at Parkview Condominiums. Spacious open LR/DR with updated kitchen and bath. Kitchen to include stainless steel appliances, glass tile backsplash, Corian countertops and huge peninsula great for parties. 2 huge bedrooms with lots of closet spaces. Private storage space and laundry in the building. In ground pool and beautiful out door spaces. Low condo fee with all utilities included. One off street parking space and huge guest parking lot. Easy access to Rte. I95, Rte. I93, "T" and Boston. Walking distance to shopping, Winchester town center and many more.

Listed by Fariba Rostam of Boston City 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

33 Dunster Lane, Winchester, MA

Price$799,000

Est. Mortgage: $/month

MLS Number 72409440

  • Single Family
  • Parking Spaces 3
  • Year Built 1930
  • Full Bath 2
  • Bathroom 2

1930's side entrance colonial with natural woodwork and hardwood floors. Large living room with fireplace; formal dining room with built-in china closet, recently updated kitchen - and gorgeous "step down" family room with gas fireplace, cathedral ceiling; French doors to patio and in-ground pool, lots of natural light, King size master bedroom plus two additional bedrooms on 2nd floor. Two full baths, partially finished play room in basement, sunny enclosed porch, and almost a half acre of land. All this in a prime neighborhood in the new Vinson Owen school district. Commuter rail to Boston, easy access to all major routes, beautiful downtown area, and excellent restaurants. Perfect home for a young family! Come see all that Winchester has to offer in addition to the fabulous schools!

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

$
$
%
$/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

Price$599,900

Est. Mortgage: $/month

MLS Number 72404962

  • Single Family
  • Parking Spaces 2
  • Year Built 1890
  • Full Bath 1
  • Bathroom 2

NEW PRICE!! Amazing opportunity to own a single family in Winchester! 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

32 Lockeland Road, Winchester, MA

Price$1,679,000

Est. Mortgage: $/month

MLS Number 72403833

  • Single Family
  • Parking Spaces 6
  • Year Built 2018
  • Full Bath 3
  • Bathroom 4

Completely rebuilt from the ground up, this gorgeous 5 bedroom home is loaded with luxury and custom finishes. The open floorplan leaves nothing to be desired and is highlighted by 8' ceilings, crown moldings and gleaming wood flooring. A rear hall with tile flooring allows access to a ½ bath, laundry room, 2 car garage and back patio. Be WOW'd by the custom kitchen which features a center island, gas range, stunning built in buffet and is wide open to the fireplaced family room. An open formal living room/dining room combo overlooks the beautiful grounds through double sliding doors. The main level also features a large bedroom with adjacent full bath with custom tile and a walk in shower. The second level features three corner bedrooms and a massive master suite with ultra-luxurious bath featuring soaking tub, glass shower with custom tile and double vanity sink. Enjoy quality materials inside and out such as mahogany doors, wood siding and meticulous landscape design.

Listed by Joanne Mulkerin of J. Mulkerin 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

44 Edward Drive, Winchester, MA

Price$749,000

Est. Mortgage: $/month

MLS Number 72387298

  • Single Family
  • Parking Spaces 3
  • Year Built 1987
  • Full Bath 3
  • Bathroom 4

BEST PRICE by far PER SQ' in WINCHESTER. Absolutely Gorgeous - "Spacious Townhouse" - Desirable Pepper Hill Estates - 3 Floors of Finished Living Space - 9 Rooms - New Vinson-Owen School District. 1st Floor - Open Floor Plan - Kitchen - Living Room w/Marble Fireplace and Sliders to a large Balcony overlooking Conservation - Dining Room w/views of Whipple Hill - Office /4th BD. 2nd Flr has 2 BD's - lg Master Suite w/BA, Jacuzzi Tub, Shower, Custom Walk-in Closet, a 2nd BD w/Slider Closet, Washer/Dryer and a Family BA. Lower Level has a spacious Recreation Rm w/Sliders to Patio, 3rd Bedrm/Exercise Rm, BA and lg Storage Rm. Exterior has lovely Garden Area - Garage and 3 Off-Street Parking Spaces. Recent UPDATES include - New Heating System - New Roof - New Skylight - Ceramic Tile Lower Level Flr - Corian Countertops and Sinks in Kitchen & BA's. Enjoy all Winchester Amenities - Winchester Center - one of the Top and Finest School Systems in Massachusetts. Just 12 Miles to Boston.

Listed by Lucille Murray 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

44 Edward Drive, Winchester, MA 01890

MLS Number 72386482

  • Condo or Co-op
  • Half Bath 1
  • Bathroom 4
  • Year Built 1987
  • Full Bath 3

BEST VALUE PRICE PER SQ' in WINCHESTER. Absolutely Gorgeous - "Spacious End-Unit Townhouse" - Desirable Pepper Hill Estates - 3 Floors of Finished Living Space - 9 Rooms - New Vinson-Owen School District. 1st Floor - Open Floor Plan - Kitchen - Living Room w/Marble Fireplace and Sliders to a large Balcony overlooking Conservation - Dining Room w/views of Whipple Hill - Office /4th BD. 2nd Flr has 2 BD's - lg Master Suite w/BA, Jacuzzi Tub, Shower, Custom Walk-in Closet, a 2nd BD w/Slider Closet, Washer/Dryer and a Family BA. Lower Level has a spacious Recreation Rm w/Sliders to Patio, 3rd Bedrm/Exercise Rm, BA and lg Storage Rm. Exterior has lovely Garden Area - Garage and 3 Off-Street Parking Spaces. Recent UPDATES include - New Heating System - New Roof - New Skylight - Ceramic Tile Lower Level Flr - Corian Countertops and Sinks in Kitchen & BA's. Enjoy all Winchester Amenities - Winchester Center - one of the Top and Finest School Systems in Massachusetts. Just 12 Miles to Boston.

Listed by Lucille Murray 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

16 Wickham Road, Winchester, MA

Price$1,859,000

Est. Mortgage: $/month

Open House

MLS Number 72376288

  • Single Family
  • Next Open House: Sun 20th 12:00 pm - 1:30 pm
  • Parking Spaces 4
  • Year Built 2018
  • Full Bath 4

New Construction! Located on a popular quite side street , just a short walk to the Wedgmere Train Station. Thoughtfully designed floor plan perfect for today's living with a contemporary open concept layout combined with rich mill working and warm finishes throughout. On the 1st floor, theres a formal living room, large fireplaced family rm, kitchen w/expanded eating area, formal dining rm, 1/2 bath & a 1st floor office/guest bedroom w/full bath. The 2nd flr features 4 bedrms, a spacious laundry room & 3 full baths. The master bedroom runs front to back, has two closets, a luxurious bath & sitting area. The 3rd floor has a bonus/game room and attic storage. The basement is finished with a bonus/play room and separate room for a gym or office plus 1/2 bath. This home is perfect for the family that is looking for a quiet neighborhood, with all the benefits of owning a brand new home. ~OPEN HOUSE Saturday Jan 12th 2:00-3:00pm~

Listed by The Synergy Group and Paul Cirignano 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

1 Central Green, Winchester, MA

Price$2,599,000

Est. Mortgage: $/month

Open House

MLS Number 72339037

  • Single Family
  • Next Open House: Sat 19th 12:00 pm - 2:00 pm
  • Parking Spaces 4
  • Village Rangeley
  • Year Built 1930

Exquisite Georgian Colonial with private setting in one of Winchester's highly desirable location. This home was renovated to the studs in 2008 with modern family living in mind. The home features a gourmet kitchen, and five spacious corner bedrooms plus nursery, including a master Suite with fireplace and two walk in closets/dressing area. Outside there are two private patios and lovely gardens. This home is a short stroll to the center, parks and public school. Come see all of the wonderful amenities this home has to offer.

Listed by Peggy Otis 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

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.