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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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    7 Verplast Winchester Ma 01890

    MLS Number 71938683

    • Rental

    Bright and sunny duplex style home with new kitchen and renovated baths on cul de sac. Newer windows and roof, well maintained, full unfinished basement with washer & dryer, great common yard space. Half bath on first floor. Fresh coat of paint and newly finished hardwood floors throughout. Kitchen and bath tiled. Great condition. New high efficiency forced hot water by oil heating system. Landlord would like lease to end in July or August 2017.

    Listed by Anne Spry of Waterfield 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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    Federal 30-year interest rate: 3.72% last updated on 2016-02-04

    This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

    200 Swanton Winchester Ma 01890

    MLS Number 71954120

    • Rental
    • Date Available 02/01/2016

    New granite countertops, sink, appliances, LED lights below and above cabinets, vanity in bathroom, motion detecting light in shower, carpet, paint and fixtures. Beautiful view from the enclosed porch, best school district and great community, easy access to Rt. 93/95. Walk to town center and community rail station. Rent includes heat, hot water, electric, snow removal, etc.

    Listed by Weidong Li of United Real Estate, LLC

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

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    Federal 30-year interest rate: 3.72% last updated on 2016-02-04

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    1 Irving Street Winchester Ma 01890

    MLS Number 71946937

    • Rental
    • Date Available 08/15/2016

    13 Year young, modern, clean 5 bedroom home. Within walking distance to Winchester center and highly rated Muraco Elementary School. Some of the many features: Hard wood floors,central A/C,central vacuum system,skylights in 3rd floor loft,granite counter tops,new appliances,large mahogany deck,fenced in yard,attached private parking,2 gas fireplaces,carpeted finished basement with full bath,large closets throughout! Best value in a large 5 bedroom, 4 1/2 bath space that Winchester has to offer!

    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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    Federal 30-year interest rate: 3.72% last updated on 2016-02-04

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    266 Highland Avenue Winchester Ma 01890

    MLS Number 71952205

    • Rental

    Great Winchester home . Walking distance to Center and train . 4 BR and 3 Baths . Furnished great value! one year lease , First , last and security . Call for showing

    Listed by William O Shea 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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    Federal 30-year interest rate: 3.72% last updated on 2016-02-04

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    17 Belknap Terrace Winchester Ma 01890

    MLS Number 71940985

    • Rental
    • Date Available 12/14/2015

    Sun filled 3-bedroom townhouse with brook view. Walk to schools, kid-friendly cul-de-sac street. Next to bike path that leads to town center and Horn Pond. Central A/C, deck and garage, Many new replacements.

    Listed by Weidong Li of United Real Estate, LLC

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

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    183 washington Street Winchester Ma 01890

    MLS Number 71945738

    • Rental
    • Date Available 02/01/2016

    Impressive grand entrance foyer with reverse stairway convenient downtown location 3 blocks from boston-lowell train, public and parochial school and shopping. House just refurbished and freshly painted with refinished hardwood floors. New mechanical systems, wood deck off kitchen. New insulated windows to be installed. Washer dryer provided in basement. Gas stove in eat in kitchen w/ stainless steel appliances; 3 walk-in closes provide extra storage in unit. Extra room for office, den or guest bedroom. Apartment is on second and third floor.

    Listed by Caci/ Fitzgerald Team, Bill Caci, Laura Fitzgerald 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 71796912

    • Commercial Office

    Excellent opportunity to own your own office in this 14 unit office condo. Judkin green is located in downtown winchester center overlooking judkins pond. This garden level condo consists off open space with an office and a private lavatory. On site deeded parking with easy street parking for customers and employees ( requires free town sticker). Just a half block walk to train to boston and lowell. New roof on front building in 2012. Parking space # 4

    Listed by Caci/ Fitzgerald Team, Laura Fitzgerald 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 71947614

    • Commercial Office

    Price recently reduced! Seize the opportunity to own this penthouse office suite at Judkin Green in downtown Winchester. Great for an owner-occupant or investor alike. Most desirable unit placement in the building. Sweeping views of Judkins Pond and the Aberjona River with its diverse wildlife. Formally a medical office with ten exam rooms/offices, three bathrooms, and nine sinks. Can be reconfigured and/or repurposed for general office use. Executive suite has its own bathroom. Includes two deeded garage spaces. Elevator. Close to routes 93, 95, 3 and 38. Top-notch amenities abound just outside your door. Steps to the Winchester Center MBTA Commuter Rail station where you can quickly be whisked to Boston’s North Station, Medford, and points northwest. Building upgrades include a new furnace, boiler, and air handlers as well as an energy retrofit. Local and responsive management company.

    Listed by John Campbell, Katy Trivedi of Boston Area Home Search

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

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    360 Cambridge Street Winchester Ma 01890

    MLS Number 71940379

    • Rental

    One of the only single-family homes available in Winchester! COMPLETELY RENOVATED. This sun-filled home includes new hardwood flooring, a large eat-in kitchen with dining room, laundry room with washer/dryer combo included and spacious living room with fireplace! Each bedroom is approximately 15'x17' with ample closet space!! Extra storage in garage along with a well-sized backyard space. Its location allows for easy access to all major highways. Home is available now..Pets are considered on a case-by-case basis. First, security, and broker fee to move in.

    Listed by Daniel Delloiacono of Commonwealth Residential, LLC

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

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    Federal 30-year interest rate: 3.72% last updated on 2016-02-04

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    58 Swanton Street Winchester Ma 01890

    MLS Number 71952142

    • Rental
    • Date Available 02/01/2016

    This lovely apartment has 3 good sized bedrooms on the 2nd floor. Plus an updated full bathroom and 1/2 bathroom.Newly finished hardwood floors through out. The 1st floor has a bright and sunny living room and an large sized dinning room. The eat in kitchen is packed with newly painted cabinets and granite counter tops. The yard is compact, but boasts a deck with attached awning and a patio area. Full basement for storage and extra bonus room.

    Listed by Fintan Doherty of ePlace

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

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    284 High Street Winchester Ma 01890

    MLS Number 71949078

    • Rental

    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. Two car garage, completes 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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    46 Florence Street Winchester Ma 01890

    MLS Number 71916571

    • Rental

    Classic small apartment in a big house. Brand new laminate floor. One bedroom with walk-in closet. large living room, eat-in kitchen and bath. Separate entrance, utilities included. 1 off street parking spot. Convenient location. No smoking or pets -- make a proposal!

    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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    Federal 30-year interest rate: 3.72% last updated on 2016-02-04

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    7 Conant Winchester Ma 01890

    MLS Number 71950812

    • Rental
    • Date Available 03/01/2016

    The Willows in Winchester. Beautiful two bedroom two baths and a private garage parking. Enjoy the open floor plan for casual living and easy entertaining. Hardwood floors throughout 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, first floor, located at the rear with lots of parking. 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 access 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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    Federal 30-year interest rate: 3.72% last updated on 2016-02-04

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    2 Wyman Court Winchester Ma 01890

    MLS Number 71949829

    • Rental
    • Date Available 02/01/2016

    Grand Victorian home in desirable Winchester! Private entrance to this second floor of a 2 family unit boasts a beautiful staircase leading into the spacious two story foyer complete with sitting areas. This newly renovated 7 room, 4 bedroom home features gleaming hardwood floors, high ceilings, oversized windows, crown moldings, custom built-ins & authentic period details. Sitting areas, eat in kitchen, dining room, den/office, and 2 private oversized balconies overlooking the grounds complete this home. 3 car parking including 1 garage included. Near Winchester center, restaurants, shopping, commuter rail, local schools and hospital. Conveniently located to 93 & 95, easy access to Boston & Logan.

    Listed by Karen Simpson of Coldwell Banker Residential Brokerage - Boston - Charlestown

    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 71877257

    • Commercial Office

    Are you searching for a Professional space for your business but don't need a giant office all to yourself? Check out this OPPORTUNITY! There are TWO available offices within this FULLY REMODELED, DESIGNER FURNISHED office suite to be shared with a financial management firm. Rent INCLUDES One Office, Utilities and Internet as well as use of the beautiful conference room, reception area, kitchenette and supply room. This move-in ready space is just waiting for you and your clients. Do not wait to schedule an appointment to view the new home of your business or you will miss out!

    Listed by Matthew Quinlan of Classified Realty Group, LLC

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

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    main Street Winchester Ma

    MLS Number 71947796

    • Business Opportunities Restaurant w/out Liquor

    Great Opportunity to Own a Restaurant in the Center of an Affluent town like Winchester , Ma . and Start Making $$ . Or do you have other Locations and want to make this Fabulous location an addition to Your Portfolio ?

    Listed by Stephen Latzanakis of Stephen Latzanakis

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

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    22 Lebanon Street Winchester Ma 01890

    MLS Number 71947919

    • Rental
    • Date Available 01/12/2016

    Walk to the highly rated Muraco School from this 5 bedroom home in Winchester! This lovely 19th century home has a first floor kitchen, pantry, dining room with built-ins, and sun- drenched living room, all with hardwood, and a tiled half bath. Level two boasts three bedrooms all with hardwood and a full tiled bath. Need additional space? The third level easily provides this with two additional bedrooms and office/ sitting room. Other amenities include: off street parking for 3 cars (tandem), washer/dryer hookup, walk to park, easy access to Rte. 93 and Boston and the Fells Conservation Area with over 2500 acres of walking and biking trails.

    Listed by The Andersen Team 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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    main Street Winchester MA 01890

    MLS Number 71947142

    • Commercial

    Buy this existing Restaurant and start making $$$$ , Or bring your concept to this existing Great downtown location. Open 6 days a week , closed Sundays . add Breakfast or other items or add constant demand for Delivery .

    Listed by Stephen Latzanakis of Stephen Latzanakis

    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 71947020

    • Rental
    • Date Available 02/01/2016

    New granite countertops, sink, appliances, LED lights below and above cabinets, vanity in bathroom, motion detecting light in shower, carpet, paint and fixtures. Beautiful view from the enclosed porch, best school district and great community, easy access to Rt. 93/95. Walk to town center and community rail station. Rent includes heat, hot water, electric, snow removal, etc.

    Listed by Weidong Li of United Real Estate, LLC

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

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    Federal 30-year interest rate: 3.72% last updated on 2016-02-04

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    282 High Street Winchester Ma 01890

    MLS Number 71828971

    • Rental

    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. Two car garage, completes 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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    Federal 30-year interest rate: 3.72% last updated on 2016-02-04

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    65 Harvard Street Winchester Ma 01890

    MLS Number 71935925

    • Rental

    Renovated 2nd floor apt. in quiet residential neighborhood. Apt. has 6 rooms; kitchen, living room, 3-4 bedrooms and 2 baths. Updated kitchen, refinished hardwood floors, and freshly painted. Fully applianced kitchen and W/D included. Close to public transportation and major commuting highways. Students will attend Muraco Elementary School, McCall Middle School and Winchester High School, all scoring very high on MA MCAS tests. Tenant to share in grounds maintenance with 1st fl. tenant and responsible for own snow removal. Tenant to pay own water/sewer bill (separately metered). Owner requires 1 year lease, first month's rent, 1 month's rent as security deposit and good credit history.

    Listed by Albert Earle of Century 21 Crowley - Braese

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

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    Federal 30-year interest rate: 3.72% last updated on 2016-02-04

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    5 Tufts Road Winchester Ma 01890

    MLS Number 71940854

    • Rental
    • Date Available 01/01/2016

    Beautiful single family home available for 3 months or less. Huge, Newly Tiled, finished Family room in basement , 3 large bedrooms, a huge living room with a fireplace, separate dining room, and a very large EIK with tile floors, rest of house is with hardwood floors! There is a sizable yard and a small basketball court in the backyard. Ample parking with one garage spot! Not Deleaded.

    Listed by Carl Kelly of WEICHERT, REALTORS« - Channing Real Estate

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

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    2 Rangeley Road Winchester Ma 01890

    MLS Number 71851843

    • Rental

    A unique opportunity to rent a bit of Beacon Hill in the heart of Winchester! 2nd/3rd floor unit in an 1880's antique. This historic property with a formal LR and DR has just been completely renovated with elegant high-end finishes, 2.5 marble baths, master suite with walk in closet, and a second BR with a cathedral ceiling. The kitchen has a custom made island, SS appliances including a wine refrigerator, Jen-Air gas stove and a pantry with handsome quartzite shelves that match the counter tops. Just a block away from the Commuter Rail Station and all Winchester has to offer. RENT INCLUDES HEAT, landscaping, private courtyard, two off street parking spaces and rubbish removal.

    Listed by Anne Rich of Coldwell Banker Residential Brokerage - Wellesley - Central St.

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

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    Federal 30-year interest rate: 3.72% last updated on 2016-02-04

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    1026 Main Winchester MA 01890

    MLS Number 71930063

    • Commercial

    Landmark free standing building with high visibility, flexible zoning, ample parking and fully updated systems. Currently used as professional office space including conference rooms, full kitchen, 11 private offices, high ceilings, ample storage and private parking. Multiple signage options. Current owner is relocating locally. Building is priced to sell. Potential Re-Development Opportunity with neighboring parcels. Call for details. This is the "office" part of the building, the second condo "warehouse" is not currently for sale or lease.

    Listed by Cheryl Masson of Anseris Group

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

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    Federal 30-year interest rate: 3.72% last updated on 2016-02-04

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    10 MT VERNON Street Winchester MA 01890

    MLS Number 71937195

    • Commercial

    Prime retail space in busy winchester center-perfect for bank, ups store-fedex-learning center-fitness center-walk in office. Lessee responsible for portion of business insurance-taxes and utilities space available october 2015... Additional space available in lower level up to 3,200 square feet! At $20.00 per sq foot

    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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