Winchester MA Real Estate & Homes for Sale
The median home value in Winchester, MA is $1,015,000.
This is
higher than
the county median home value of $454,300.
The national median home value is $185,800.
The average price of homes sold in Winchester, MA is $1,015,000.
Approximately 80.39% of Winchester homes are owned,
compared to 15.01% rented, while
4.6% are vacant.
Winchester real estate listings include condos, townhomes, and single family homes for sale.
Commercial properties are also available.
If you see a property you’re interested in, contact a Winchester real estate agent to arrange a tour today! $1,749,00071 Myopia Road Winchester, MA 01890
Open House: Friday, 6/22 11:00-12:30PM ADDITIONAL INFORMATIONATTENTION WINCHESTER AFICIONADO'S: Do we have the home for you! Available for the first time in more than 45 years! Nestled in ever so nicely on its wooded and oversized lot is this 4 bed, 4 full bath home located in the highly acclaimed Myopia Hill. Imagine homeownership on one of the finest streets that Winchester has to offer. Within walking distance to the prestigious Winchester Country Club, this property will lure you in from moment one. Enter in to the main level which boasts a new kitchen, beautiful formal dining room with built ins, sunroom beaming with natural light from every angle, a fireplaced family room, a fireplaced library, AND the first of two master suites. Want MORE? The second level provides two beds that share a bathroom and a second master suite. The lower level, walk out, recreation room with bar area and additional fireplace is the icing on the cake to this amazing home. Come see how you can live everyday as if you were in a private retreat here at 71 Myopia. $2,150,00011 Hutchinson Rd Winchester, MA 01890
Open House: Friday, 6/22 12:00-2:00PM ADDITIONAL INFORMATIONGorgeous family home located in Winchester by the Winchester country club and the Vinson Owen School District. This home is meticulously cared for and looking for a large family to call it home. This home features stunning cherry floors throughout the 1st & 2nd floor. The first floor consists of an office/den, dining room, large open concept kitchen that flows to the eating area and family room. The second floor houses a large master suite w/ master bath and two walk-in closets, two large bedrooms, laundry room and bathroom. The Au Paire Suite is quite large with it's own sitting area, work space and full bath. The third floor is fully finished with two more bedrooms and a full bath. The basement is nicely finished with a great work out area, kids game room and classroom/office area with a full bath to finish it off. Don't miss the 3 car heated garaged for those car enthusiasts. The backyard is HUGE! Half acre just ready for an in-ground pool to finish it off...... $1,049,0004 Rangeley Ridge Winchester, MA 01890
Open House: Saturday, 6/23 10:00-11:30AM ADDITIONAL INFORMATIONA superb residence situated in the heart of downtown Winchester that is impeccably decorated & designed to the highest standard on an absolutely exquisite 18,0000 sq ft lot with garage parking! This home offers 3 bedrooms, 1.5 baths & is perfect for todayâs busy lifestyle. Outstanding architectural detail, materials & finishes are displayed inside & outside this absolutely magnificent home. Main level offers a traditional colonial style layout with beautifully appointed eat in kitchen overlooking the spectacular fenced in rear yard including a brick patio with steps down to a terraced garden with mature plantings & seasonal views of town from this esteemed âœRangeleyâ neighborhood; a fireplaced living room; formal dining room; sunny home office & half bath. The 2nd floor is adorned with 3 corner bedrooms, a well appointed full bath & plentiful closets. Walk to town, commuter rail, schools, restaurants & all downtown has to offer. Absolutely turnkey! 
Open House: Sunday, 6/24 11:00-1:00PM ADDITIONAL INFORMATIONWelcome to The Ledges town home community. Winchester's most desirable town home complex surrounded by nature and mature landscape. This unit has been meticulously maintained and has a lovely front yard. Hardwood floors on the first floor with doors leading to the deck from the fireplace living room. Open floor plan for easy living and entertaining. Updated Kitchen with a bright and lovely eat in Area overlooks your garden. Dining room opens to Living room for easy entertaining. 1st floor master bedroom has cathedral ceilings, spacious bath and 2 walk-in closets, additional Bedroom on the 1st floor and a full Bath with Tub and Shower. 2nd floor has a loft ideal for home office or media room. 3rd bedroom with bath allows privacy for your guests or extended family. Lower Level is a walk out, consists of a Family Recreation Room with Sliding glass doors, and a finished Bonus Room with a spacious closet. Large Storage area with built ins. Open House Sunday 11-1. $1,349,0001 Woodside Road Winchester, MA 01890
Open House: Sunday, 6/24 12:00-1:30PM ADDITIONAL INFORMATIONWelcome to the Flats! Beautiful 1895 Colonial on a 12,000sqft lot, just 1mile from the town center. Private and serene back yard with a blue stone patio and new 6ft cedar fence located directly off the kitchen. Sprinkler system and NEW 2-car garage with a 22x14 2nd floor just waiting for your imagination to finish. An inviting front porch opens into the grand foyer with a classic staircase. Bright, sun-drenched double parlor with lovely built-in details. Formal dining room, kitchen with granite counters/island, gas stove, stainless steal appliances and half bath complete the 1st floor. The second floor offers a master bedroom with new wood floor, walk-in closet, beautifully updated master bath, three additional bedrooms and large family bath. Third floor is wonderful space with full bath, 2 bedrooms and ample storage. The partially finished lower level is great flex space with even more storage options. Great home in a fantastic location...come enjoy all Winchester has to offer! 
Open House: Friday, 6/22 10:00-11:00AM ADDITIONAL INFORMATIONWelcome to a move-in ready & low-maintenance, freshly painted 3 bed/2.5 bath newer townhouse! The open concept 1st floor living, dining & kitchen area features hardwood floors, large windows & high ceilings. Wooden staircase leads to the large master bedroom & master bath with double vanities & walk-in closet, a bonus bay window allows for lots of natural light. 2nd floor includes a 2nd bedroom, full bath and balcony access. The 3rd floor has a study area and 3rd bedroom with French doors, two walk-in closets, skylight & additional storage. Benefit from a finished basement with large family room & a mudroom space off the attached garage. Enjoy the comfort of central heat & AC and tankless hot water heater. A private backyard patio is perfect for BBQs and entertaining, and balcony and front porch allow for additional outdoor space. Located less than 1/2 a mile to Lynch Elementary and Horn Pond, approx. 1 mile to Winchester Center, middle & high schools, and train, & near major highways. 
Open House: Friday, 6/22 11:00-12:00PM ADDITIONAL INFORMATIONCharming Farmhouse style home within walking distance of Town Center, Schools, Commuter Rail, Middlesex Fells Reservations, and amenities! This bright and sunny property offers many features that are sure to appeal to today's buyers: beautifully remodeled kitchen with granite countertops & stainless appliances, generous master bedroom suite with a fireplace and ensuite bath, a home office/study on the 2nd floor, 3 full bathrooms, Central AC, tasteful lighting, lovely hardwood floors, 1st floor laundry, ample closets, and much more. The 4th bedroom/Family Room on the 1st floor adds flexibility of living arrangements. The landscaped backyard, front porch, and 1-car attached garage complete the setting for this picturesque property located on a large corner lot. Convenient access to the highways allows for ease of commuting. Open House Saturday & Sunday: 12-1:30 pm. $1,288,00018 Chester St Winchester, MA 01890
Open House: Saturday, 6/23 11:00-12:30PM ADDITIONAL INFORMATIONJust Listed! First Open House this Sunday from 11-12:30. Luxury Colonial Style Home located on a quiet tree lined street just a short distance to Winchester Center, Town Schools, MBTA Commuter Rail & Middlesex Fells Reservation. You'll love the Spacious Open Concept first floor as it features an Amazing Chef's kitchen with lots of Natural Light, Frigidaire SS Appliances and Granite Counters! With 3 levels of living this home does not disappoint as there is room for everyone! $1,429,90077 Irving Street Winchester, MA 01890
ADDITIONAL INFORMATIONCurrently UNDER CONSTRUCTION and almost complete~ Enjoy designer chosen finishes in this new construction home by local premier builder! Located on a lightly traveled dead end street off Washington and behind desirable Muraco Elementary School, this stunning 4 bedroom 3 1/2 bath home features an ideal open floor plan, bright kitchen with quartz island and stainless steel appliances, family room with corner gas FP and high end finishes throughout. High ceilings, large sunny rooms, 4 generous bedrooms, luxurious master suite with huge walk-in closet and master bath featuring custom shower & soaking tub~ Great rear yard and deck! Finish the basement as you desire~ Located only 7 miles from Boston, close to center of town and public transportation...don't miss the opportunity to occupy this home before the end of summer! Schedule your private showing today! (please excuse the on-site unwanted images :) $1,350,00026 York Rd Winchester, MA 01890
Open House: Saturday, 6/23 1:00-2:30PM ADDITIONAL INFORMATIONA spacious Colonial on a cul-de-sac in a sought after neighborhood within the Ambrose school district! This updated/expanded home is perfect for every lifestyle and wonderful for entertaining, especially by the pool in the summertime! The first floor boasts a step down Living Room and Dining Room, a wonderful Kitchen with an island, skylight, fireplace and dining area overlooking a patio and the pool. A bedroom, full bath and a bedroom with en suite and walk in closet complete this floor. Walk upstairs to a Master Bedroom with en suite, walk in closet and office/nursery as well as a dressing room/home office and additional bedroom. The lower level, with garage access, offers tiled playroom/family room space, laundry and a full bath. Enjoy hardwood floors throughout, central air, newer systems and roof in a location 1.3 miles from the shops and restaurants of Winchester Center, close to Wedgemere Commuter Rail Station and Rte 93. Must see! Open Houses Sat 6/23 & Sun 6/24 1-2:30 $2,499,0004 Ravine Road Winchester, MA 01890
Open House: Saturday, 6/23 12:00-1:30PM ADDITIONAL INFORMATIONUNBEATABLE LOCATION, SITUATED IN THE HEART OF DOWNTOWN WINCHESTER!!! Enter into the dramatic 2-story foyer featuring one of three Swarovski Crystal Chandeliers! Host a dinner party in the Chefs kitchen boasting granite counters, a 48"SUBZERO refrigerator, a 60"gas WOLF range & 2 BOSCH dishwashers. Step out into the pristine garden with built in BBQ and outdoor pizza oven! The dining room has built-in china cabinets, a fireplace and is surrounded with beautiful windows. 5 bed suites, each w/private bath. A Master bed fit for a King & Queen! Seamless flow throughout provides unparalleled luxury living on 4 levels. Gorgeous media room on lower level, featuring a home theatre and bar. Newly finished hardwood floors , and many rooms recently painted. Walk to the farmer's market on 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. $1,250,00017 Olde Village Dr Winchester, MA 01890
Open House: Saturday, 6/23 12:00-1:30PM ADDITIONAL INFORMATIONAuthentic Royal Barry Wills Country Cape in Vinson Owen district. This 3,242 sq ft home sits on a large professionally landscaped lot with serene woodland feel. As you enter you are greeted by an inviting foyer leading to a fireplaced living rm, formal dining rm, home office & family rm equipped w/built-in wet bar & separate built-in media cabinets, plus sliders leading to private patio. Make your way to the custom kitchen w/beautiful cherry full over-lay cabinets (which are INDEED back in style).Quality craftsmanship & incredible attention to detail throughout. There is a one of a kind master suite on 1st flr with dressing rm & full master bath. Home office has its own 1/2 bath & could be 4th bdrm. An impressive spiral staircase leads to the 2nd flr where youâll find 2 bedrooms, full bath & a large unfinished area perfect for future expansion.The roof & heating system are brand new! Showings begin June 19. Weekend open houses June 23&24, 12:00-1:30pm. Seller to review offers 2pm 6/25 $1,299,00020 Mason St Winchester, MA 01890
Open House: Saturday, 6/23 12:30-2:00PM ADDITIONAL INFORMATIONWelcome to 20 Mason St, Winchester. This stunning colonial, circa 1928 has been beautifully, meticulously and expertly expanded, updated and renovated. Featuring a new kitchen addition with quartz and walnut counters, black stainless steel appliances and custom cabinetry.From here the new deck, portico and garden are easily accessed.The front to back living room is the perfect gathering space with a wood burning fireplace and original mill work restored to perfection. On the 2nd level the Master bedroom has a beautiful new en suite bath with heated marble floors and dual head tile shower. New custom closets complete this lovely suite. On this level there are 2 other bedrooms and a family bath. Upstairs on the 3rd level there is a home office, another full renovated bath and the 4th bedroom. Perfectly landscaped to embrace the natural woodland setting, this lovely property is close to the town center, commuter rail, Lincoln Elementary and McCall Middle School. $1,250,000104 Hillcrest Parkway Winchester, MA 01890
Open House: Saturday, 6/23 11:30-1:30PM ADDITIONAL INFORMATIONWelcome to 104 Hillcrest Parkway! Located directly across from the breathtaking Middlesex Fells Reservation. This picturesque street truly is one of the most enticing in all of Winchester. Home has been exceptionally maintained and is bursting with character. Main level is ideal for entertaining with it's brilliant open floor plan and stunning hardwood floors. Massive family room with gorgeous built in book cases, eat-in kitchen, mudroom with a slider to the patio. There is also a living room with a gas fireplace, elegant dining room, and an office with it's own half bath. Sprawling master suite has 2 walk-in closets, and a balcony overlooking the backyard. Bonus heated room above the 2 car garage offers a variety of uses. Ecostar Majestic Slate roof is environment-friendly and super efficient. Central A/C, newer hot water heater, main level laundry and more. Winchester has a superior school system, easy access to Boston, and a great downtown area. The perfect town to raise a family! $1,629,000170 Forest Street Winchester, MA 01890
Open House: Saturday, 6/23 11:00-1:00PM ADDITIONAL INFORMATION170 Forest Street will exceed your expectations once inside.Entertaining is made easy with the expansive, open concept dining room, kitchen, & living room and ample parking with the 2 car garage & 6 off street parking spaces. This oversized colonial features a versatile first floor bonus room that could be a study, game room or an extra guest bedroom. Enjoy your morning coffee on the elevated 16' X 22' rear deck that overlooks your private,1/2 acre lot, well suited for that perfect tree house or lazy rope swing.The 2nd floor boasts a spacious, private master suite with his & her closets, a luxurious designer bath with soaking tub & large glass shower. You will be surprised to see the sun drenched, fully finished 3rd floor with the 4th full bathroom and space for yet another bedroom, bonus room or separate living suite. The large walk out basement would be the perfect space to finish for extended family who deserve a full private suite while still being connected to everyone else. 
Open House: Saturday, 6/23 12:00-1:30PM ADDITIONAL INFORMATIONWith its premier downtown location, enjoy all that Winchester has to offer just out your front door! Beautifully situated on a picturesque, tree lined street, the home is just minutes from Winchesterâs Victorian downtownâs shops and restaurants, award-winning schools, and Commuter Rail station. Built in the 1850s, this historic Colonial features high ceilings, wide pine flooring, and newer windows. This is the perfect opportunity for a savvy buyer to modernize and restore the property to its original glory. Enjoy summer barbecues on the secluded backyard patio and near-limitless outdoor activities are yours to explore in the Middlesex Fells Reservation. A unique opportunity to own a special home. $2,399,00015 Aristotle Drive Winchester, MA 01890
Open House: Sunday, 6/24 12:00-1:00PM ADDITIONAL INFORMATIONTHE ULTIMATE IN LUXURY LIVING LOCATED 7 MILES NORTH OF BOSTON!!! This meticulously maintained home has an integrated floor plan that every modern buyer seeks. The first floor features a dining room, living room & family room, both with gas fireplaces and a large kitchen with sliders to the exquisite stone patio for your next Summer gathering. Including granite counters, hardwood floors and a top of the line SS appliance package. Many rooms newly painted in today's neutral Benjamin Moore colors. Work from home? Enjoy the fantastic mahogany home office with custom built ins. Three floors of finished living space boasting 5 large bedrooms, 4 bathrooms and a great room with fireplace, the perfect space for "peace & quiet". Lower level features a game room, home gym and sauna!!! A short drive to downtown, where you'll find coffee shops, boutiques, restaurants, and the commuter rail to Boston. Within the desirable Vinson Owen school district. Become a part of the Winchester community today! $1,800,0006 Central Street Winchester, MA 01890
Open House: Friday, 6/22 11:30-12:30PM ADDITIONAL INFORMATIONThis beautiful property located on one of Winchesterâs most desired streets close to town center is a short distance from both train stations. High ceilings and large windows make the first floor sunny and bright. The unique open floor plan has a great flow and is perfect for entertaining and day to day living. The large lot allows for expansion potential. Enjoy the perennial gardens, patio and lawn. Exceptional architectural details include open staircase, original period moldings, period millwork, recently restored antique stained-glass windows and numerous built-ins. Updates include gut-renovated 3rd floor bathroom, new fixtures in all bathrooms, new windows on 3rd floor, new gutters. Close to all that Winchester has to offer: shops, restaurants, farmers market, Middlesex Fells and much more. This is a home that you must see. 
Open House: Saturday, 6/23 12:00-1:00PM ADDITIONAL INFORMATIONDramatic new construction (2017) residence located in the heart of Winchester close to schools, shopping, Middlesex Fells Reservation, rail station & downtown! An elegant, modern two level condo that boasts the perfect blend of contemporary finishes with fantastic room layouts that all feel very large. Enjoy an open plan with 2000 sq ft including living/dining room; a well-appointed kitchen w/breakfast bar, stainless steel appliances & custom glazed maple cabinets; 3 bedrooms with natural light streaming in & 2 exquisite, luxurious full baths. Bonus loft offers flex space for 4th bedroom/home office/play room area. Amenities include high ceilings; gas fireplace; designer architectural details throughout; hardwood floors; in-unit laundry; energy efficient gas heating & cooking; central air; LED lighting; professionally manicured back & side yards & garage parking (with storage above!) Self-managed 2 unit association with no monthly fee. 
ADDITIONAL INFORMATIONThis spacious condo is just minutes away from downtown Winchester and its amenities including shopping, restaurants, Farmerâs Market, library, award-winning schools, parks, and commuter rail. Renovated kitchen offers custom made maple cabinets. Granite countertops and a breakfast bar. The open concept kitchen and living room make great use of the space and would be perfect for entertaining. The second floor offers a bright full bath, a bedroom, and a spacious bonus room that would be perfect for a home office, playroom, or guest space. The third-floor master suite is a private retreat featuring a skylight, a custom designed bathroom with skylight and make-up table, plenty of storage space. This unit has a full basement family room with spacious closets, a half bath and in-unit laundry station with additional storage and counter space. The 2,600 acre Middlesex Fells reservation is close by, known for walking, running & biking trails. $1,349,0001 Alden Ln Winchester, MA 01890
ADDITIONAL INFORMATIONBeautifully appointed center entry colonial in desirable East Hill neighborhood, features 3 levels of well designed space perfect for busy yet , comfortable living. The kitchen featuring granite counters with a breakfast bar and stainless steel appliances also has a spacious casual dining area and opens directly to the 2 car garage. There is a formal living room and a dining room with gas fireplace as well as a family room adjacent to the kitchen. A lovely staircase leads to the second level with 4 corner bedrooms each of generous proportions , including a master suite with home office and a bath with a Jacuzzi and separate shower. The third floor is perfectly finished for a 5 th bedroom with plenty of storage and a 3/4 bath. This home has CA on all levels, and is sited on a beautiful corner, flat lot in Lincoln School district. Offers due by Tuesday, June 19th by noon $639,00012 James Street Winchester, MA 01890
Open House: Saturday, 6/23 1:00-2:30PM ADDITIONAL INFORMATIONPerfect opportunity to own your own home in one of the best school system towns in the state. This beautifully updated and well maintained ranch is ideal for any family, whether downsizing, first time home buying or making a school system move. This welcoming home boasts newer windows, an updated granite and stainless kitchen, wood floors, three lovely bedrooms, one and half baths and central air! You will love the flexible floor plan with dining area, open to the fire-placed living room and a terrific kitchen, plus garden access. The lower level has a laundry area, half bath, a family room, and easy access to the patio and garage, especially convenient on those rainy or snowy days. The back deck is perfect for summer cook outs, the lot is large, lush and affords privacy combined with terrific play space, great for kids and dogs alike. Enjoy coffee on the charming side patio, close to Wright Locke Farm, great schools, parks, public transportation and all that Winchester has to offer! $949,00053 Ledyard Road Winchester, MA 01890
Open House: Saturday, 6/23 12:00-1:30PM ADDITIONAL INFORMATIONWelcome to 53 Ledyard Road! The high 8' 4" ceilings and oversized rooms of this Expanded Cape will amaze you. You'll immediately feel at home in the fireplaced living room complete with custom built-ins and window seats, all bathed in natural light. The first floor also features a spacious dining room, eat-in kitchen with stainless steel appliances and a family room with easy access to the deck and backyard. The second level boasts a master suite with a cathedral ceiling and walk-in closet, plus 3 additional bedrooms with generous closet space and a family bath. Bonus spaces in the basement could easily serve as play, music or workout rooms. Outside a beautifully landscaped yard complete with irrigation system awaits. Well maintained with newer windows, roof and hot water heater. Much loved Lincoln School neighborhood just a short distance to downtown Winchester Center, Commuter Rail and Middlesex Fells Reservation. $1,925,000239 Ridge Street Winchester, MA 01890
Open House: Saturday, 6/23 12:00-2:00PM ADDITIONAL INFORMATIONWelcome to 239 Ridge St! Not a single detail was overlooked when designing this home. Premium materials were used, like Hardie siding and Andersen windows to ensure quality craftsmanship. When driving up, youâll notice the expansive stone driveway which leads into the grand entrance. The main floor features an open concept with a chefâs kitchen offering top of the line appliances, granite countertops and more! Enjoy entertaining your guests on the deck overlooking the large backyard. Back inside, the staircase leading to the top floor will bring you to 4 bedrooms, including the master suite, 2 full baths, and the laundry room. The master includes cathedral ceilings, a walk in closet, and a luxurious Carrara marble en-suite bathroom. You can continue entertaining in the completely finished bottom floor. This floor includes a library, media room, wet bar, full bath and garage access. This custom home sits on over 20,000 sq ft of land - it is a must see! $1,399,0007 Canterbury Road Winchester, MA 01890
ADDITIONAL INFORMATIONOriginally built in 1941 & fully rehabbed & expanded in 2005, this custom colonial is calling you home! Located in a lovely, crescent-shaped neighborhood & sited on more than 10,000 SF of fenced, private lot, this home offers expansive living for family & guests. Mudroom leads to a cookâs kitchen, with friendly breakfast nook.Open to the kitchen is a FR featuring custom built-ins & an entertainment center. Sliders lead to an oversized deck overlooking the beauty & serenity of your secluded back yard. Completing the first floor is a formal LR & DR & home office all featuring gleaming hardwood floors. Step upstairs into your master suite, boasting dueling closets fitted with custom, California Closet systems, and bath complete with separate soaking tub and shower. Guests will enjoy the privacy of their own en-suite bath and walk in closet, while 2 generous bedrooms share the marble hall bath. Laundry room completes this floor. Finished basement with FP & another half bath. Welcome Home!
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