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
12 Prospect Street Winchester MA 01890

Price$2,499,000

Est. Mortgage: $/month

MLS Number 72493394

  • Single Family
  • Garage 2
  • Parking Spaces 6
  • Village near center
  • Year Built 1880

Spectacular NEW RENOVATION! This breathtaking home with gorgeous kitchen featuring state of the art design with Thermador appliances, full wine tower, 42'' fridge, 6 burner gas range, quartzite island with seating for 4/5 and breakfast nook overlooking beautiful 27.000+ sf lot with perennial plantings and unique stone and shingle 3 car garage/ carriage house. Formal dining room with beautiful woodwork; double crown moldings, wainscoting, 2 chandeliers and bay window seating area. Elegant formal LR with lit built ins and fplc. Family room w/ oversized wood burning fplc, and a wall of windows beaming with sunlight. Enjoy summer evenings on the expansive front porch or on the rear terrace/ & patio with 6 person Jacuzzi offering gorgeous sunset views over Winchester center! This Magnificent home features 7 spacious bedrooms each w/ generous closet space & high ceilings. Pella windows, 400amp electric, 3 zone A/C, irrigation well, 3 car garage. Basement media room MUST SEE!

Listed by Kim Covino of Leading Edge Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.84% last updated on Jun 20, 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

25 Thornberry Road Winchester MA 01890

Price$1,400,000

Est. Mortgage: $/month

MLS Number 72491257

  • Single Family
  • Garage 1
  • Parking Spaces 5
  • Year Built 1959
  • Full Bath 4

Fabulous renovation in this large contemporary home with 5 bedrooms and 4 bathrooms with open floor plan and top of the line finishes. Enter through the mudroom from attached garage or from the gracious front porch. Expansive, open kitchen/dining area with over sized, beautiful island, perfect for entertaining and top of the line appliances. This sunny room opens to a first floor family room and attached home office/guest suite. Lower level offers a large family room with deck overlooking landscaped yard and another guest suite along with plenty of storage space. Large, gracious foyer awaits you on the second floor with three bedrooms including a large master suite with walk-in closet and heated bathroom floor. The third floor offers a perfect loft area and some more storage space. All in a serene setting in the highly sought after Vinson Owen school district.

Listed by Lesley Smith of Waterfield Sotheby's International Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.84% last updated on Jun 20, 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

38 Prospect Street Winchester MA 01890

Price$2,349,000

Est. Mortgage: $/month

MLS Number 72490271

  • Single Family
  • Garage 2
  • Parking Spaces 8
  • Year Built 1910
  • Full Bath 3

Nestled amidst the most gorgeous landscape & serene settings you will find, this very special home is like no other! This gorgeous 4/5 bed 3.5 bath home was expanded & renovated inside and out by the current owners. From the moment you enter into the stunning foyer, you will feel the welcoming warmth and see the quality that surrounds with the wide plank Hickory floors, open concept living room/dining room with high coffered ceilings, oversized wood-burning fireplace, custom built-ins, and sun-filled sitting room off to the side with exterior access to private fieldstone patio. Chef's kitchen featuring inset cabinets, breakfast nook w/ bench, built-in desk, butler's pantry w/ wet-bar, coffee bar, wine storage & add'l pantry/mudroom. Cozy family room just off kitchen with custom built in media wall. 2nd level features master suite w/ walk-in closet & spa-like master bath; three additional rooms each w/ gorgeous views and unique characteristics. LL mudroom to garage entry,

Listed by Kim Covino of Leading Edge Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.84% last updated on Jun 20, 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

48 Cabot Street Winchester MA 01890

Price$1,650,000

Est. Mortgage: $/month

MLS Number 72488975

  • Single Family
  • Garage 2
  • Parking Spaces 4
  • Year Built 1922
  • Full Bath 3

Stunning 5 bedroom Colonial in Winchester's desirable Flats neighborhood, First floor features hardwood floors, high ceilings, formal dining room with chair rail, inviting living room with fireplace, adjacent sun-room with built-in cabinets & study/home office with french doors & custom book shelves. Gourmet kitchen with high-end stainless steel appliances, large island & french doors leading to a lovely deck, patio, fenced yard & 2-car garage. Large master suite with full bath, double vanity, soaking tub & tiled shower. Three additional bedrooms with ample closet space, full bath & laundry room on 2nd floor. Bonus third floor bedroom suite with full bath, cathedral ceiling & skylights. Huge lower level playroom,exercise room & half bath. Improvements include high efficiency heating and cooling with 9 zones, new driveway,new carpet in basement and new windows,. Beautiful fenced in back yard. 2008 home updated.

Listed by Richard Brenner of Brenner Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.84% last updated on Jun 20, 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

32 Grove Place Winchester MA 01890

Price$635,000

Est. Mortgage: $/month

Active With Contract

MLS Number 72488380

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

You must step inside to see all the charm of this inviting home located on a dead end street! Surprisingly spacious throughout, this home features many sought after details - high ceilings, crown molding, exposed brick, hardwood floors, recessed lighting, and more! First floor features a gracious floor plan to include an entry foyer, updated kitchen complete with granite counters and SS appliances, lovely dining room, living room with bay window, a fully renovated bath, and a third bedroom option. Retreat upstairs to find two additional bedrooms, each with jack and jill access to a beautifully renovated bathroom w/cathedral ceiling and skylight. The large enclosed front porch offers a great spot to relax in after a long day! Conveniently located just .5 miles to Wedgemere station for commuter rail to Boston. Enjoy living in Winchester with it's top rated schools, vibrant town center, restaurants, shops, farmer's market, and more! Ambrose School district.

Listed by Antonella Nigro of Berkshire Hathaway HomeServices Commonwealth Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.84% last updated on Jun 20, 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

20 St. Thomas More Drive Winchester MA 01890

Price$2,499,000

Est. Mortgage: $/month

MLS Number 72488480

  • Single Family
  • Garage 3
  • Parking Spaces 5
  • Year Built 2000
  • Full Bath 4

Welcome home to this beautiful custom built brick colonial in a neighborhood of several newly built homes. The foyer is two story with curved staircase into the open floor plan. The family room has a cathedral ceiling, floor to ceiling fireplace, beautiful elliptical windows that add plenty of sunshine to this room with spacious built ins. The kitchen has hardwood flooring, Thermador appliances, and wet bar. There is a step down sunroom for dining with a wall of windows, skylights and a patio door that leads to your private backyard. This home has 2 work at home office/homework rooms on the first floor, both with glorious windows to make your workday a pleasure. This home has a 3 car garage with direct access to mudroom/laundry There is a walkup finished 3rd floor and 2 sliders in the walkout LL. 4 floors of finished space. Located in the recently finished Vinson Owen School district & newly completed Winchester High School. There are 2 commuter rail stops & just 10 miles from Boston

Listed by Buono/Lyons Team of Century 21 CELLI

$
$
%
$/month over payments
Federal 30-year interest rate: 3.84% last updated on Jun 20, 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

17 George Road Winchester MA 01890

MLS Number 72487841

  • Condo or Co-op
  • Bedrooms 2
  • Bathroom 1
  • Square Feet 968

Modern and updated townhouse. Amazing opportunity to own at The Residences in Winchester! Quiet and peaceful street. Two bedroom town home flooded with natural light, can be converted to three bedrooms. Three levels of living. Great space for entertaining: tastefully updated kitchen with marble countertops opens to dining area with easy access to private backyard. It feels very private in this backyard. Hardwood floors throughout. Basement offers potential for family room or office and great storage space. More storage in the attic. Two tandem parking spaces. Well-run, pet friendly condo association. Low condo fee. Minutes to top rated Winchester public schools, recreational activities, Whole Foods, Stop & Shop, Winchester Center with its cafes, shops, restaurants, commuter rail to Boston, Farmer's Market on Saturdays. Enjoy convenience of the nearby tennis courts, barbecuing and gardening in the summer in the backyard…. Be a part of this warm, welcoming community!

Listed by Katya Pitts of Leading Edge Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.84% last updated on Jun 20, 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

3 Orient Street Winchester MA 01890

Price$839,000

Est. Mortgage: $/month

MLS Number 72487198

  • Single Family
  • Garage 1
  • Parking Spaces 4
  • Year Built 1925
  • Full Bath 2

Classy, Charming and Comfortable best describes this Lovely Bungalow in a Perfect Location. Living room is Open and Airy with Coffered Ceilings, Dentil Crown Moulding, French Doors, Brick Fireplace, Beautiful Wall Sconces. The Kitchen has an abundance of room with Beautiful Cabinetry, Marble Countertops and Stainless Appliances. Formal Dining Room and Handsome Den giving away to More Enjoyment. Master Bedroom up or Master Bedroom Down. Guest Bedroom for those Extended Stays. Main Bath with Porcelain Walk in Shower, Glass Doors and Marble Flooring. Outside Enjoyment is so very easy whether it is on the Front Porch, Back Deck, or in the Beautiful Fenced in Yard. Whichever Spot you Chose - Tranquility will come! This home is in walking distance to the Muraco Elementary School.

Listed by Mary L. Lawton of Lawton Real Estate, Inc

$
$
%
$/month over payments
Federal 30-year interest rate: 3.84% last updated on Jun 20, 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

7 Conant Road Winchester MA 01890
Active With Contract

MLS Number 72484635

  • Condo or Co-op
  • Bedrooms 2
  • Bathroom 3
  • Square Feet 1,409

Luxury 2br 2.5ba townhouse with a garage at the sought after Willows at Winchester! This top-notch community invites you to enjoy the summer at the heated outdoor pool, new exercise room and the gorgeous clubhouse. This two level end unit townhouse features an open floor plan. The first floor boasts sparking hardwood floors throughout, a spacious fireplaced living room with a sliding door to the deck/balcony, a fully applianced modern kitchen open to the living room & dining room. Half bathroom on the first floor. Both bedrooms on the upper level feature recently replaced carpets and walk-out balconies open to the peaceful neighborhood. Master bedroom has oversized master bath and walk-in closet. Hallway bath with a spa tub. One car garage with one off street parking in the front. Central AC, in-unit laundry on 2nd floor, and extra storage room in the basement, convenient location to downtown Winchester shops, restaurants and commuter rail to Boston.

Listed by Wei Fu of Phoenix Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.84% last updated on Jun 20, 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

23 Yale Street Winchester MA 01890

Price$2,249,000

Est. Mortgage: $/month

MLS Number 72485458

  • Single Family
  • Garage 2
  • Parking Spaces 3
  • Village The Flats
  • Year Built 1901

Stunning colonial in the Flats recognized as the “Nickerson House". Has undergone major renovation to combine meticulously preserved historical features w/latest demands of comfort & functionality. Featuring 6 bedrms, 4.5 baths, exquisite design, soaring ceilings, vast areas w/radiant floors, central AC, night lighting, wireless speakers, stylish fixtures. Elegant kitchen w/granite counters, large island & high-end appliances opens to family room. Sun-lit dining room, sitting & living room anchored by dramatic brick fireplace. Luxurious master suite w/fireplace, rounded bay, walk-in California Closet. En suite bath w/exceptional design: soaking tub, shower, double sink vanity, heated floor, A/C. Three other large bedrms, full bath, closet w/laundry hookup complete 2nd flr. Spacious playroom, 2 bedrms, bath on 3rd flr. Media room, gym & laundry on finished lower level. Flat private yard w/patio, porch, landscape lighting & sprinklers. 2 car garage, walk to Ambrose, center, commuter rail

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.84% last updated on Jun 20, 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

29 Dunster Lane Winchester MA 01890

Price$1,999,000

Est. Mortgage: $/month

MLS Number 72484222

  • Single Family
  • Parking Spaces 7
  • Village Westside
  • Year Built 1945
  • Full Bath 5

MUST BE SEEN. Spacious and elegant don't begin to describe this spectacular 7700+sf. home. Masterful design and modern luxury are uniquely blended into the construction of this exceptional property. It is truly an entertainers dream. The incredible gourmet kitchen will please even the most demanding culinary artist. The newly renovated kitchen flows into the dining area and unsurpassed Great Room, which is the heart of this home. The Great Room features a full wet bar, Brazilian cherry floors, fireplace and coffered ceilings. 5 bedrooms, 5 baths and an abundance of comfortable spots to gather provides everyone their place to "live". Enormous Master Bedroom boasts of a fireplace, walk-in, sitting area, bathroom w/soaking tub, heated floors and sauna. Relax and consider star gazing from the Hot Tub on the 3rd floor roof deck. There's also a steam/shower on this level along with a kitchenette. The lower level home office and play room with wet bar complete this incredible home.

Listed by Steve O Brien of Century 21 Adams KC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.84% last updated on Jun 20, 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

15 Cambridge Street Winchester MA 01890

Price$2,998,000

Est. Mortgage: $/month

MLS Number 72484213

  • Single Family
  • Garage 2
  • Parking Spaces 10
  • Year Built 1941
  • Full Bath 5

Live Waterfront - on Mystic Lake! This totally renovated and expanded Colonial is now a modern classic, designed for comfortable, gracious living. Open First Flr features Lg windows/glass paneled drs across back, providing abundant natural light and stunning views from Kit/Fam Rm, Liv Rm w/FP and Dining Rm. Gorgeous Cook's kitchen w/high-end appliances, Lg island, leathered granite and mahogany counter tops, and wet bar for entertaining. Handsome private, paneled office w/FP, Mud Room and half bath complete floor. Second Flr boasts 4 bedrooms, all w/meticulously finished en suite baths. Retreat-like master w/dressing closet, 2nd double wardrobe, luxurious bath w/soaker tub with lake and Boston Skyline views. All finished LL w/separate entrance incl: Media/Game Rm w/FP; flexible 5th Bdrm suite, in-law, au-pair or workout rm; full bath accessed via bdrm or hall; 2nd ldry area. Sited on prof. landscaped 29K+ sf lot w/new deck, stone patio and steps to 111 ft Lakefront. 8 miles to Boston

Listed by Ann Basmaji of Waterfield Sotheby's International Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.84% last updated on Jun 20, 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.