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    Winchester Homes Under $500k

    Scroll down to view current home under $500k for sale in Winchester, MA. Save your favorite listings when you register with us, and you can get email updates when new properties match your search criteria. Contact us if you have questions or would like to set up a tour of one of the listings below.

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    282 High Street Winchester Ma 01890

    MLS Number 71828971

    • Rental
    • Date Available 07/01/2015

    Executive rental opportunity in new vinson owen school district at it's best! Magnificent home in this younger brick colonial equipped with wonderfully large, bright, and generous rooms throughout. Light filled two story entry and great room with 2 sided fireplace adjacent to kitchen and dinette. Super spacious kitchen with multiple, newer stainless appliances known for its ability to serve large events with ease. Over sized butlers pantry with wine refrigerator lead to expansive dining room. Dark cherry built-ins make up large 1st floor private office. Nearby is a first floor bedroom (1 of 5) and bathroom. Second level equipped with fantastic master suite with fireplace and dressing room. Finished lower level perfect for au pair private area with kitchen or generous family/play room. 3 car garage, with extra storage bay complete this fabulous home at the end of cul de sac, abutting 100 acres of serene conservation land on the winchester lexington border. New vinson owen school.

    Listed by Anthony Marino of Gibson Sotheby's International Realty

    Better Homes and Gardens | The Shanahan Group
    41 Thompson Street
    Winchester MA, 01890
    Office: 781-729-9030

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    6 Dix Terrace Winchester Ma 01890

    MLS Number 71828965

    • Rental
    • Date Available 09/01/2015

    Stunning 3-bedroom 2.5 bathroom 2 level new construction luxury apartment walking distance to winchester center. Pride of craftsmanship is more evident including top of the line fully applianced custom kitchen. Some features include radiant floor heat, meticulously crafted woodwork and modern fixtures. Entertainment system installed including flat screen tvs and sonos music system throughout. Not your typical rental, this home is above and beyond all expectations. A must see!

    Listed by Rachel Ventresca of Greater Metropolitan R. E.

    Better Homes and Gardens | The Shanahan Group
    41 Thompson Street
    Winchester MA, 01890
    Office: 781-729-9030

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    200 Swanton Street Winchester MA 01890
    Active With Contract

    MLS Number 71793915

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

    Move right into this beautifully renovated condo on the 6th floor of the Parkview Condominiums! The gorgeous new kitchen has granite counter tops, breakfast bar,maple cabinets, stainless steal appliances with dishwasher and microwave . The open concept is great for entertainment. Large living room with slider doors to the balcony where you can enjoy the amazing views of the courtyard and the Fells Reservation. Great amenities, low condo fees includes all utilities, lots of closets, plus extra storage in lower level, pool, parking and laundry facilities. Well maintained grounds with bird sanctuary, duck pond and barbeque areas. Just a short stroll to shops, restaurants, town center and public transportation. This is easy living in a great location.

    Listed by Ides Miller of Coldwell Banker Residential Brokerage - Winchester

    Better Homes and Gardens | The Shanahan Group
    41 Thompson Street
    Winchester MA, 01890
    Office: 781-729-9030

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    200 Swanton Street Winchester MA 01890

    MLS Number 71785888

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

    Opportunity knocks to own rather than rent in desirable Winchester. This main level studio condo features new carpet and appliances. Looking over the beautiful Japanese gardens, this unit needs nothing. Just a short distance to shops, town center public transportation and commuter train to Boston. Condo fee includes heat, air conditioning, electricity and a beautiful pool to enjoy on those hot summer days.

    Listed by Kelli Cantillon of Century 21 Commonwealth

    Better Homes and Gardens | The Shanahan Group
    41 Thompson Street
    Winchester MA, 01890
    Office: 781-729-9030

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    560 Main Street Winchester MA 01890

    MLS Number 71826214

    • Commercial

    Prime center of town location! Direct visibility from Main Street and Mount Vernon.

    Listed by Arthur Horiatis of Tory Row Real Estate

    Better Homes and Gardens | The Shanahan Group
    41 Thompson Street
    Winchester MA, 01890
    Office: 781-729-9030

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    99 Swanton Street Winchester MA

    Winchester MA99 Swanton Street

    Price$499,900

    Est. Mortgage:$/month

    Open House

    MLS Number 71818624

    • Single Family
    • Next Open House: Sun, 3rd 12:00 pm
    • Bedrooms 3
    • Bathroom 2
    • Street # 99

    This renovated and deleaded home in the Muraco school district is only 1/2 mile to downtown shops and the train station and even closer than that to the school. Completely remodeled kitchen with cherry cabinets, granite counters, stainless steel appliances, and breakfast bar open to living room. Hardwood flooring, Sun Room and 3 bedrooms also on the main level. Updated bathrooms. New 2 zone gas forced hot water heat and vinyl high efficiency windows & siding. Finished basement Play Room with brand new Berber carpeting and laundry room with washer and dryer included. Vacant, freshly painted, clean and in move-in condition. First open house at the new price on Sunday May 3rd from 12PM to 2PM.

    Listed by John W. Lowenstein of Red Line Real Estate

    Better Homes and Gardens | The Shanahan Group
    41 Thompson Street
    Winchester MA, 01890
    Office: 781-729-9030

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    247 Washington Winchester MA 01890
    Open House

    MLS Number 71827407

    • Condo or Co-op
    • Next Open House: Sun, 3rd 12:00 pm
    • Bedrooms 2
    • Bathroom 1
    • Year Built 1945

    Great opportunity to own and live in Winchester! Popular Washington Green just a short walk to center of town and train, and popular Muraco School district. This 3 story townhouse offers the convenience to use public transportation and leave the car at home! First floor offers efficient kitchen, dining room and living room. Level two has 2 bedrooms and bath. Third floor is multi-functional: use as a home office, exercise room, or large family room. Lower level has storage and laundry room. This area is semi-finished and a great teenage game room. Deeded parking space outside back door.

    Listed by Mary Price of Better Homes and Gardens The Shanahan Group

    Better Homes and Gardens | The Shanahan Group
    41 Thompson Street
    Winchester MA, 01890
    Office: 781-729-9030

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    107 Cross Street Winchester MA 01890
    Open House

    MLS Number 71825481

    • Condo or Co-op
    • Next Open House: Sun, 3rd 12:00 pm
    • Bedrooms 2
    • Bathroom 2
    • Year Built 1910

    This renovated Penthouse unit condo overlooks the Aberjona River, beautiful Davidson Park, and is close to Winchester Hospital, the Muraco School and the commuter rail. The eat-in kitchen is complete with granite counters, pendant lights over the island counter and under cabinet lights along the working counter. Ceiling fans in the living room and both bedrooms. The unit has hardwood floors in the kitchen & the combination living/dining room and wall to wall carpets in both bedrooms. Other features include central air-conditioning and tilt-in insulated windows. Deeded parking for three cars. Also included is an extra 300 square feet of private storage space in the basement. Building is pet friendly with a limit of 2 pets. Access to Route 93 is approximately a mile away. The refrigerator, washer (GE Profile), and dryer is included with the sale as gifts to the new owners.

    Listed by Sal Dipinto of RE/MAX Andrew Realty Services

    Better Homes and Gardens | The Shanahan Group
    41 Thompson Street
    Winchester MA, 01890
    Office: 781-729-9030

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    22 Grove Place Winchester Ma 01890

    MLS Number 71825147

    • Rental
    • Date Available 08/01/2015

    Winchester!!! Fully furnished !!! This is a tastefully furnished 2 bedroom condo less than a 5 minute walk to the commuter train to north station! Just bring your clothes and move into style and luxury. Quiet setting a short walk to downtown and the mystic lakes. Approx 2 miles from tufts and davis square, somerville for the trendy night life and restaurants.Bonus finished lower level. For the roommates that want a little privacy, the finished lower level has separate full bath, murphy bed, office and lounge area.

    Listed by John Heenan, Jaclyn White of Exit Realty Beatrice Associates

    Better Homes and Gardens | The Shanahan Group
    41 Thompson Street
    Winchester MA, 01890
    Office: 781-729-9030

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    23 Shepard Court Winchester MA 01890
    Open House

    MLS Number 71828521

    • Condo or Co-op
    • Next Open House: Sun, 3rd 2:00 pm
    • Bedrooms 3
    • Bathroom 1
    • Year Built 1890

    OH 5/3 SUN 2-3 * Enjoy single family like living when you live in this cozy & updated 5RM, 3BR townhouse on a pretty cul-de-sac. This rear facing unit has a huge exclusive private yard, its own deck, patio area & its own driveway for 2 car parking. Enter through a large mud room/foyer area w/ a large closet leading to a spacious Living Room. Large & recently renovated eat in kitchen w/ granite counters & stainless steel appliances. Tiled bathroom. Hardwood floors. Expansion possibilities in private deeded & walkout basement that has a 1/4 bath with a toilet that can be converted to a half or full bath. Private washer &dryer in the unit. All appliances will stay. High efficiency replacement windows. Pet friendly 2 unit association, with low condo fees of only $50/month! Both units are owner occupied. Few doors away from McDonald Field for basketball, soccer, baseball field & playground. Close to public transportation, commuter rail ¢er. Best single family alternative on the market!

    Listed by Jessica Ye of Keller Williams Realty

    Better Homes and Gardens | The Shanahan Group
    41 Thompson Street
    Winchester MA, 01890
    Office: 781-729-9030

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    39 Westland Avenue Winchester Ma 01890

    MLS Number 71820364

    • Rental
    • Date Available 05/01/2015

    Newly remodeled, beautiful cape style home in a fabulous winchester neighborhood within walking distance to ambrose elementary school and park. This home features a wonderful open floor plan, brand new white kitchen with bosch and jenn-air stainless appliances and granite counters, cathedral family room right off the kitchen and deck, extra large living room with a gas fireplace, newly installed/refinished hardwood floors throughout and freshly painted inside and out. There is also a new high efficiency gas heating system, central air conditioning, partially finished basement and beautiful landscaping maintained by owner. This is not your typical rental property! Available may 1st. Long term lease preferred.

    Listed by Ida M. Bianco of Coldwell Banker Residential Brokerage - Winchester

    Better Homes and Gardens | The Shanahan Group
    41 Thompson Street
    Winchester MA, 01890
    Office: 781-729-9030

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    121 Loring Avenue Winchester Ma 01890

    MLS Number 71824905

    • Rental
    • Date Available 05/16/2015

    Spacious and sunny 1450sf two bedroom, two full bathroom apartment on the first floor of a two-family home. Large foyer leads to the living room and formal dining area which opens to a renovated kitchen with tile backsplash, granite counters, cherry cabinets and updated appliances plus a large dining area and breakfast bar. The master bedroom has a sitting area, 3 closets and bathroom. There is a dedicated washer and dryer and large storage area in the basement plus direct access to the garage. The exterior features private yard, large welcoming porch and additional parking. Wood floors throughout and central air-conditioning. Owners will consider pets.

    Listed by Susan Condrick of Hammond Residential Real Estate

    Better Homes and Gardens | The Shanahan Group
    41 Thompson Street
    Winchester MA, 01890
    Office: 781-729-9030

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    18 Hemingway Street Winchester MA

    Winchester MA18 Hemingway Street

    Price$499,000

    Est. Mortgage:$/month

    Open House

    MLS Number 71827144

    • Single Family
    • Next Open House: Fri, 1st 11:00 am
    • Bedrooms 3
    • Bathroom 1
    • Street # 18

    What a fantastic opportunity to own an adorable house close to Winchester Center. Close to top ranked schools and all this prestigious town has to offer. This fabulous Vintage Colonial has been recently updated with a gorgeous kitchen with stainless steel appliances, over-sized island with granite counter tops and a beautiful tile floor. The living room and dining room, with wainscoting, are bright and open. The full size bathroom has been tastefully updated and is located on the first floor. This home boasts front and back mud rooms, great for muddy little feet and paws! The second floor has two bedrooms both with hardwood. The bonus room is located on the third floor and is a great hideaway space perfect for home office, kids play room or an extra bedroom. The basement provides ample storage space with laundry hook-up. The small back yard, with patio, make this a great condo alternative. There's also two driveways. A real charmer!

    Listed by Stephen McKenna, Anne Marie Kelly of Bowes Real Estate Real Living

    Better Homes and Gardens | The Shanahan Group
    41 Thompson Street
    Winchester MA, 01890
    Office: 781-729-9030

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    30 East Street Winchester MA 01890
    Open House

    MLS Number 71827303

    • Condo or Co-op
    • Next Open House: Sun, 3rd 2:30 pm
    • Bedrooms 3
    • Bathroom 2
    • Year Built 1961

    Welcome home. This 3 bedroom townhouse is in exceptional condition. There are hardwood floors and updated windows throughout first and second level. The living room is bright with multiple windows. Dining area has wall AC unit and is adjacent to galley style kitchen equipped with new refrigerator and hood. Stove, dishwasher, recessed lighting and ceiling lights are additional kitchen amenities. The second floor has 3 generous bedrooms, each with a ceiling fan. The full bath has ceramic tile surround in tub/shower and tiled floor. Full lower level has spacious family room, second full bathroom, laundry and utility areas. All this plus Winchester Schools.

    Listed by Suzanne Winchester Miller of Hammond Residential

    Better Homes and Gardens | The Shanahan Group
    41 Thompson Street
    Winchester MA, 01890
    Office: 781-729-9030

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    846 Main Street Winchester Ma 01890

    MLS Number 71795713

    • Rental

    A single family house with handicap ramp - big, bright family room with sliders to deck and yard. Lots of cabinets and appliances in open kitchen. Living room, dining room, bedroom, full bath and laundry on 1st floor; 2 bedrooms and full bath on 2nd floor. Hardwood and carpet. Walk to shops, easy access to all major routes, on the bus line.

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

    Better Homes and Gardens | The Shanahan Group
    41 Thompson Street
    Winchester MA, 01890
    Office: 781-729-9030

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    156 Mount Vernon Street Winchester Ma 01890

    MLS Number 71797980

    • Rental

    Prime location! Easy walking distance to winchester center, public transportation, restaurants, library middlesex fells and only 20 minutes from downtown boston. This meticulously maintained 3 bedroom, 1.5 bath is one side of a totally renovated turn of the century colonial. Modern kitchen and baths, large rooms with high ceilings, 3 heating zones, heated finished basement. Parking on old oak lane. No pets

    Listed by Theuer - Pirani Team, Joan Theuer, Peter Pirani of RE/MAX Leading Edge

    Better Homes and Gardens | The Shanahan Group
    41 Thompson Street
    Winchester MA, 01890
    Office: 781-729-9030

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    200 swanton Winchester Ma 01890

    MLS Number 71823560

    • Rental
    • Date Available 05/01/2015

    Lobby level . No stairs. Updated kitchen and bath hardwood floors slider to deck and view of duck pond . Rent includes heat and electric, cable is available and additional. Walk to town and commuter train to north station. Swimming pool and additional parking.

    Listed by Theuer - Pirani Team, Joan Theuer of RE/MAX Leading Edge

    Better Homes and Gardens | The Shanahan Group
    41 Thompson Street
    Winchester MA, 01890
    Office: 781-729-9030

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    Wedge Pond Road Winchester Ma 01890

    MLS Number 71812049

    • Rental
    • Date Available 05/01/2015

    Simultaneously in the center of things, yet off the beaten path. Convenient location, ample living space, plenty of character and very good overall condition. Prior tenant has just vacated, so owner is "freshening up" for the next tenant, including paint, cleaning and a new counter top in the kitchen. Target occupancy is may 1st. Three bedrooms on the 2nd floor plus a fourth room that has been used as an office/ computer room / walk-in closet. Third floor has several rooms, one of which is finished and has newly installed electric baseboard heat. A second room with rough finish also now has heat. There is a laundry hook-up in the basement. This home has it's own driveway for two cars. Easy to see if you hurry.

    Listed by Tim Garvey of Century 21 Commonwealth

    Better Homes and Gardens | The Shanahan Group
    41 Thompson Street
    Winchester MA, 01890
    Office: 781-729-9030

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    200 Swanton Street Winchester MA 01890
    Open House

    MLS Number 71822003

    • Condo or Co-op
    • Next Open House: Sun, 3rd 2:00 pm
    • Bedrooms 2
    • Bathroom 1
    • Year Built 1966

    Bright, and freshly painted (April 2015), two bedroom condo at the Parkview. Updated kitchen with white cabinetry, granite counters, and breakfast bar, opens onto the spacious living room with sliders to balcony overlooking lushly landscaped pond. The unit is conveniently situated near the elevator. The comprehensive condo fee includes heat, air conditioning, hot water, and electric, along with the building's additional amenities of laundry facilities, and outdoor swimming pool. Great location close to restaurants, public transportation, and downtown Winchester.

    Listed by Linda Sharpe, Judith Spang of Hammond Residential

    Better Homes and Gardens | The Shanahan Group
    41 Thompson Street
    Winchester MA, 01890
    Office: 781-729-9030

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    7 Conant Road Winchester Ma 01890

    MLS Number 71823818

    • Rental
    • Date Available 06/01/2015

    The willows! Great opportunity for someone wanting one floor living. Beautiful 2 bedroom 2baths and garage parking. Enjoy the open floor layout for casual living and easy entertaining. Hardwood floors and gas fireplace, private patio off living room. The garage with attic for extra storage! Kitchen with d&d. Large master bedroom with walk-in closet. Laundry in unit. This is a corner unit, located at the rear with lots of parking. The willows offers luxury amenities - enjoy the club house, exercise room and swimming pool. You'll have a great living experience in this beautiful and well maintained complex, plus everything winchester has to offer: great schools, walking distance to the middlesex fells reservation, shops, restaurants, the commuter rail and easy acess to boston.

    Listed by Ides Miller of Coldwell Banker Residential Brokerage - Winchester

    Better Homes and Gardens | The Shanahan Group
    41 Thompson Street
    Winchester MA, 01890
    Office: 781-729-9030

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    750 Main Street Winchester MA 01890

    MLS Number 71822500

    • Commercial

    Approximately 500 sf second floor, two room office suite, all utilities included. Plenty of off street parking and walking distance to Winchester center, shopping, restaurants and transportation.

    Listed by Paul Cirignano of RE/MAX Leading Edge

    Better Homes and Gardens | The Shanahan Group
    41 Thompson Street
    Winchester MA, 01890
    Office: 781-729-9030

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    750 Main Street Winchester MA 01890

    MLS Number 71822504

    • Commercial Office

    two room office suite, corner unit with lots of natural light. Large parking lot provides plenty of parking. All utilities included!

    Listed by Paul Cirignano of RE/MAX Leading Edge

    Better Homes and Gardens | The Shanahan Group
    41 Thompson Street
    Winchester MA, 01890
    Office: 781-729-9030

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    8 Winchester Place Winchester MA 01890

    MLS Number 71770863

    • Commercial Office

    Affordable rent. Lease includes: heat, water, electrical. Impressive light open space. Located in Winchester Center. Close to highway and Public Transportation.

    Listed by Deborah L. Leavitt of Century 21 Commonwealth

    Better Homes and Gardens | The Shanahan Group
    41 Thompson Street
    Winchester MA, 01890
    Office: 781-729-9030

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    8 Winchester Place Winchester MA 01890

    MLS Number 71770848

    • Commercial Office

    This FURNISHED(optional) Office space has it all: Affordable Rent Includes: Heat, Water, Electrical. Large Conference Room, Large Full Kitchen! Parking is close by in Town Parking lots. Very attractive Light Open Space with expansive lay out. Located in Winchester Center close to Highway and Public Transportation. "No More Boston Traffic"

    Listed by Deborah L. Leavitt of Century 21 Commonwealth

    Better Homes and Gardens | The Shanahan Group
    41 Thompson Street
    Winchester MA, 01890
    Office: 781-729-9030

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    63 SHORE Road Winchester MA 01890

    MLS Number 71795657

    • Commercial Office

    SELLER to pay YOUR 2015 CONDO FEES!! ....TOP floor, corner office is the CROWN JEWELL of the Judkin Green, offering private bath ( plus 2 additional restrooms). 1,677 sf of space in attractive, BRICK, ELEVATOR BUILDING, just off the rotary in downtown area. Currently set up as doctor's offices with multiple, private exam rooms, each with sink setups, high ceilings, nice light and many with fab water views. Much glass and panoramic views of Aberjona/Judkins waterway and its wildlife. Fabulous WATERVIEW office space on Shore Road in Winchester! Reception area with large waiting area. Includes two deeded parking spaces. Located beside the Arthur Griffin Museum, minutes to rte 93 and 95, 15 minutes north of Boston, and a five minute walk from the train station. Great space with "bird's eye" views of local architecture and surroundings.

    Listed by Judy McCoy of Coldwell Banker Residential Brokerage - Andover

    Better Homes and Gardens | The Shanahan Group
    41 Thompson Street
    Winchester MA, 01890
    Office: 781-729-9030

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