Winchester Real Estate, Homes and Condos for sale

All Winchester homes currently listed for sale in Winchester as of 09/16/2019 are shown below.  You can change the search criteria at any time by pressing the 'Change Search' button below.

If you have any questions or you would like more information about any Winchester homes for sale or other Winchester real estate, please contact us and one of our knowledgeable Winchester REALTORS® would be pleased to assist you.


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$3,790,000
9 Grove St, Winchester MA 01890
8
BEDS
8
BATHS
10,602
SQFT
$357
$/SQFT
0.77
ACRES
1914
BUILT
"Restored to its former grandeur, and renovated to modern splendor is your new home in highly desirable Winchester, MA - just 7 miles from downtown Boston. Enjoy all the convenience of being close to the city but still far enough away to relax in the serenity of this premium suburb (bonus - Winchester is situated close by to the PRIVATE AIR TRAVEL HUB of Bedford Hanscom Field Airport). Features of the home you will appreciate include a SECOND MASTER, smartly placed across the home from the main m"
* LISTED OVER 120 DAYS  * PRICE LOWERED - $3,990,000 TO $3,790,000 
$2,998,000
15 Cambridge Street, Winchester MA 01890
5
BEDS
6
BATHS
5,305
SQFT
$565
$/SQFT
0.67
ACRES
1941
BUILT
"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 b"
* LISTED OVER 120 DAYS 
$2,995,000
6 Harrison Street, Winchester MA 01890
6
BEDS
8
BATHS
6,765
SQFT
$443
$/SQFT
0.45
ACRES
2019
BUILT
"New construction colonial will take your breath away! Entryway opens up to an open concept layout: Family room w/ gas fireplace, dining room, living room, grand kitchen, office, mudroom w/ built-ins & 1.5 baths. The kitchen features an oversized island w/ White Rhino counters, Wolf double oven w/ grill, griddle, custom hood & pot filler, 54 sub zero fridge/freezer, 2 sinks, 2 dishwashers & pantry. Sliders open up to a patio & expansive lawn. 2nd floor features the grand master suite plus 3 addit"
* LISTED OVER 120 DAYS  * PRICE LOWERED - $3,095,000 TO $2,995,000 
$2,699,000
65 Myopia Road, Winchester MA 01890
4
BEDS
5
BATHS
7,206
SQFT
$375
$/SQFT
0.90
ACRES
1952
BUILT
"IMMACULATE ESTATE WITH STUNNING GROUNDS & HEATED POOL!!! This prestigious Myopia Hill address is an incredible Colonial set on an acre of land, affording privacy & tranquility. The home features a grand foyer, elegant dining room with fireplace, a chef's kitchen, and a vaulted breakfast nook; perfect for all your entertaining needs. The adjoining living & family room boasts soaring ceilings, natural light streaming through oversized windows & an impressive stone fireplace. The 2nd level features"
$2,680,000
5 Wagon Wheel Rd, Winchester MA 01890
5
BEDS
6
BATHS
7,097
SQFT
$378
$/SQFT
1.11
ACRES
2015
BUILT
"This massive home sits on an acre of land of one of Winchester neighborhoods. Recently built (2015) and meticulously maintained, it is turn-key at a very high standard. It includes 7,097 square feet of living space, a huge heated pool, year-round 10 person spa, and professionally landscaping. Extreme privacy like no other. Fourteen rooms, 5 bedrooms, 6 full baths, finished basement, and a 3-car heated garage are the core of this estate. The patio has an extensive yard and room for a tennis cou"
* PRICE LOWERED - $2,780,000 TO $2,680,000 
$2,475,000
29 McCall Rd, Winchester MA 01890
4
BEDS
5
BATHS
5,620
SQFT
$440
$/SQFT
1.50
ACRES
1994
BUILT
"Custom built Myopia Hill Colonial was part of the Schrafft Estate peacock garden. From the moment you traverse the driveway nestled in greenery, this exceptional setting will capture your heart. The magical lot with beautiful mature plantings offers privacy with front porch, patios & lawn space. The spacious kitchen provides ample room for cooking & gathering with dining area & center island which flows into the 2 story, beamed ceiling family room with fireplace, interior balcony & oversized win"
* PRICE LOWERED - $2,600,000 TO $2,475,000 
$2,299,000
60 Wedgemere Avenue, Winchester MA 01890
6
BEDS
6
BATHS
7,526
SQFT
$305
$/SQFT
0.33
ACRES
1929
BUILT
"INCREDIBLE, VINTAGE, HISTORIC, TUDOR LOOKING FOR A FAMILY TO MAKE NEW MEMORIES!!! Are you looking for a home which is both modern & loaded with historic charm & character? Look no further, welcome to 60 Wedgemere Avenue. Located in the exclusive Flats Of Winchester, this meticulously maintained home has it all! Boasting a Chef's kitchen with a top of the line SS appliance package, huge granite island & French doors to a private stone patio, perfect for a firepit during those impending cooler ev"
* NEW LISTING 
$2,299,000
12 Prospect Street, Winchester MA 01890
7
BEDS
5
BATHS
5,461
SQFT
$421
$/SQFT
0.64
ACRES
1880
BUILT
"Breathtaking & completely renovated signature property 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 for"
* LISTED OVER 120 DAYS  * PRICE LOWERED - $2,379,000 TO $2,299,000 
$2,275,000
5 Fox Hunt Ln, Winchester MA 01890
4
BEDS
5
BATHS
7,730
SQFT
$294
$/SQFT
1.23
ACRES
1982
BUILT
"Understated and unique luxury. This traditional brick colonial opens into an interior of simple, contemporary beauty. Situated on 1.2 acres that border the 13th fairway of the Winchester Country Club, the home s 300-foot elevation affords sweeping views across the Mystic Lake and into East Boston, with brilliant sunrises that change hourly with the light and weather. A large deck and patio invite outside entertaining. Inside, the home mixes traditional and contemporary elements: an expansive l"
$1,999,000
3 Summit Ave, Winchester MA 01890
5
BEDS
3
BATHS
3,100
SQFT
$645
$/SQFT
0.23
ACRES
1910
BUILT
"A truly spectacular renovation! Get excited about this one, you won't be disappointed. This is gorgeous, top quality work done to the highest standard by very well known builders. Every room has been transformed to clean, sleek surroundings that will bring you joy to live in. The owners put huge money into this project and it shows, from the custom built cabinetry and counters in the kitchen to gleaming hard wood floors everywhere to the cool, modern baths with fabulous tile, tubs and fixtures. "
$1,995,000
20 St. Thomas More Dr., Winchester MA 01890
6
BEDS
5
BATHS
6,726
SQFT
$297
$/SQFT
0.46
ACRES
2000
BUILT
"Welcome home to this beautiful custom built brick colonial in a neighborhood of several newly built homes. The double door 2-story entry opens into a stunning staircase. The family room has a cathedral ceiling, impressive fireplace, and beautiful elliptical windows. The kitchen has hardwood flooring, Thermador appliances, and wet bar. Built for entertaining and everyday living. There is a step down sunroom for dining with a wall of windows, skylights and a patio door that leads to your private b"
* LISTED OVER 120 DAYS  * PRICE LOWERED - $2,299,000 TO $1,995,000 
$1,980,000
326 Highland Ave, Winchester MA 01890
6
BEDS
5
BATHS
5,190
SQFT
$382
$/SQFT
0.60
ACRES
1903
BUILT
"Amazing price for this Majestic Winchester home with detail and craftsmanship unlike any other~ Situated proudly on a private, oversized lot with lovely level rear yard, patio and 2 car garage, offering some of the most gorgeous custom hand milled woodwork you've ever seen~ breathtaking bridal staircase with 30' ceilings, spectacular stained glass windows, from one room to the next, this home will impress. Formal Mahogany dining room with beamed ceilings and oversized fireplace, living and fami"
* PRICE LOWERED - $2,199,000 TO $1,980,000 
$1,949,000
38 Prospect Street, Winchester MA 01890
4
BEDS
4
BATHS
4,121
SQFT
$473
$/SQFT
0.70
ACRES
1910
BUILT
"Fabulous price for this home! Nestled amidst the most beautiful 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 firepla"
* LISTED OVER 120 DAYS  * PRICE LOWERED - $2,099,000 TO $1,949,000 
$1,899,000
12 Priscilla Lane, Winchester MA 01890
5
BEDS
4
BATHS
5,000
SQFT
$380
$/SQFT
0.23
ACRES
2019
BUILT
"Beautiful NEW CONSTRUCTION Home on the East Side! This exquisite 5 bedroom 3.5 bath colonial features desirable open floor plan for today's family living! Thoughtfully designed with high-end finishes & details, this home offers an oversized 2-car garage, direct entry into mudroom, gourmet kitchen w/ island & Chefs appliances, family room with FP adjacent to kitchen & direct exterior access to patio. sun-drenched formal LR & DR with crown molding ~ Second floor features include master suite w/ "
* NEW LISTING 
$1,899,000
5 Fernway, Winchester MA 01890
5
BEDS
4
BATHS
4,262
SQFT
$446
$/SQFT
0.88
ACRES
1928
BUILT
"Beautifully set within Myopia Hill, this updated Tudor style home, contains magnificent period details while being updated for modern luxury living. This one of a kind home has surprises at every turn; The main level boasts a central family room, hidden library, immaculate chef s eat in kitchen, half bath, hardwood floors throughout, exceptional outdoor space, two stone patios, firepit, and lush conservation land. The second floor contains 5 spacious bedrooms and 3 full baths which includes th"
$1,825,000
8 Black Horse Ter, Winchester MA 01890
5
BEDS
5
BATHS
3,833
SQFT
$476
$/SQFT
0.25
ACRES
1892
BUILT
"This one of a kind, centrally located home awaits its 4th owner since 1892! Beautifully maintained & tastefully updated, 8 Black Horse Terr is both an heirloom masterpiece with intricate period detail as well as an inviting, livable home. Enjoy views of the center from the large farmer's porch. The spacious foyer with spindle woodwork perfectly presents the fireplace beamed ceiling living room, beamed ceiling dining room overlooking a luscious backyard, first floor office & inviting kitchen wit"
* NEW LISTING 
$1,800,000
379 Main St, Winchester MA 01890
5
BEDS
4
BATHS
3,223
SQFT
$558
$/SQFT
0.33
ACRES
1846
BUILT
"Have you been looking and looking for a large updated classic Winchester home with an open floor plan and close to town? Finally it s come on the market! This handsome updated home with an open sunny floor plan is only a 5-10 min walk to town center, train, and schools. The 21 x 15 kitchen flows into the 21 x 21 fireplaced skylit family room. Off the family room is a sky-lit cathedral ceiling sunroom featuring a hot tub and French doors out to the garden. The fully equipped kitchen has every"
$1,780,000
24 Calumet Rd, Winchester MA 01890
5
BEDS
5
BATHS
4,182
SQFT
$426
$/SQFT
0.34
ACRES
1927
BUILT
"This well-designed Dutch Colonial Revival in the Winchester Flats, marked by modern amenities, radiates original warmth & character. Formal & informal rooms on the 1st floor are connected by a pleasing circular flow that feels open & natural. Elegant details include high ceilings, crown moldings, wainscoting, hardwood floors, built-ins & a split formal staircase. Entertaining is a pleasure w/both formal dining & living rooms leading to a large kitchen w/island, breakfast bar, & dining area w/sli"
$1,699,900
58 Salem St, Winchester MA 01890
5
BEDS
4
BATHS
6,040
SQFT
$281
$/SQFT
0.26
ACRES
2015
BUILT
"This impressive builder s home is full of surprises and stellar craftsmanship. Thoughtfully laid out w/ designer finishes, custom cabinetry, rich hardwood flooring, crown mouldings & beautiful lighting fill this home. The chef s grade kitchen features professional-grade Wolf appliances, calcutta marble countertops & island, dual dishwashers & sinks, & stylish pendant lighting. The flexible main living area includes casual living room, formal sitting area, extensive formal dining w/ built-in "
* NEW LISTING 
$1,699,000
5 W Chardon Rd, Winchester MA 01890
6
BEDS
4
BATHS
4,198
SQFT
$405
$/SQFT
0.30
ACRES
1950
BUILT
"Well maintained custom colonial in desirable neighborhood. Corner lot w/mature plantings & great curb appeal. This sun-filled home boasts six bedrooms & three fireplaces, completely renovated approx. 2008. First floor offers two generous sized bedrooms w/versatility; office, au pair or in-law w/full bathroom & shower. Large eat in kitchen flows into family room w/gorgeous stone fireplace. French doors lead to dining room with double sided fireplace shared with living room. Second floor offers "
* PRICE LOWERED - $1,749,900 TO $1,699,000 
$1,699,000
46 Lorena Road, Winchester MA 01890
5
BEDS
4
BATHS
4,756
SQFT
$357
$/SQFT
0.77
ACRES
1957
BUILT
"MUST SEE INSIDE this beautiful East Side contemporary home, set on a large private lot surrounded by homes 2M+ in very desirable area near center. This 5 bedroom, 3.5 bath home is completely renovated~ Close to Winchester Center schools, shops & train to Boston! Plenty of living space on the first floor, boasting a gorgeous high end kitchen w/Sub Zero fridge, double wall oven, walk-in pantry with wine fridge, playroom/ mudroom off the kitchen, dining room w/walls of windows, living room with fpl"
* PRICE LOWERED - $1,749,000 TO $1,699,000 
$1,675,000
272 High St, Winchester MA 01890
4
BEDS
4
BATHS
4,215
SQFT
$397
$/SQFT
0.81
ACRES
1995
BUILT
"Looking for some peace and quiet? You will find it at 272 High Street! This meticulously maintained colonial was custom built for its current owners, in a magnificent setting abutting the Whipple Hill conservation area. Lots of beautiful windows allow tons of natural light and a spectacular view. Large open kitchen, with island and eating area, open to a bright family room. First floor also includes formal dining room, living room and office. Second floor offers four large bedrooms, one with en "
* PRICE LOWERED - $1,725,000 TO $1,675,000 
$1,649,900
508 South Border Road, Winchester MA 01890
5
BEDS
5
BATHS
4,450
SQFT
$371
$/SQFT
0.28
ACRES
2019
BUILT
"This beautiful new construction, three level Colonial home is a must see, with a 60 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 bedr"
* LISTED OVER 120 DAYS 
$1,599,000
22A Grove Street, Winchester MA 01890
4
BEDS
4
BATHS
5,772
SQFT
$277
$/SQFT
0.34
ACRES
1985
BUILT
"EXCEPTIONAL HOME LOOKING FOR IT'S NEW OWNER! The welcoming foyer is equipped with a switch for lowering the chandelier for easy cleaning. The oversized addition (2012) is home to a large living room with gas fireplace, open to a spacious Chef's style kitchen, a quaint breakfast nook & doors to the exterior deck. A tremendous area for entertaining a crowd with an oversized island, granite counters, SS appliances, double ovens & wine cooler. Radiant heated floors throughout much of the house. This"
 
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