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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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      35 Vine Winchester Ma 01890

      MLS Number 71995236

      • Rental

      Sunny 2 bedroom, minutes from Winchester center and commuter rail, heat and hot water included, a great deal, new carpets, 2 car parking, one car parking is garage under parking, building has an elevator, coin op laundry, storage, in a well kept brick building, centrally located, easy access to public transportation. *pictures of a similar unit

      Listed by Carleen Leblanc of CJL Management Co., Inc.

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

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      Est. Mortgage: $/month

      Federal 30-year interest rate: 3.66% last updated on 2016-04-28

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

      92 Forest Street Winchester Ma 01890

      MLS Number 71995249

      • Rental

      This Cape has just been delightfully renovated and is waiting for new tenants. Brand new gourmet kitchen with granite, stainless and glass tile, which leads to the new deck outside. 2 full baths are new as well, with marble, washer/dryer, full size showers and oh so pretty. Newly sanded hardwood floors, all new paint, replacement windows, new doors, new roof, and new lawn make this a delight to live in. Bonus extra space in basement that could easily become a playroom or home gym. Close to highways and walk to everything!

      Listed by Nancy S. Pallotta 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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      Federal 30-year interest rate: 3.66% last updated on 2016-04-28

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      24 Lorena Road Winchester Ma 01890

      MLS Number 71995262

      • Rental

      Fabulous portrayal of well-preserved Mid-Century Modern architecture! Nestled into a private natural setting, this home offers easy open living with tons of space, loads of natural light and an address that is much coveted in Winchester. 5 bedrooms, and 3.5 baths offer room for all; take comfort on newly refinished hardwood floors with radiant heat. An expansive living room is highlighted by the field stone-clad wood burning fireplace and the family room offers high ceilings, a wall of glass doors opening to the patio and huge private back yard. Over-sized 2 car garage, original custom teak kitchen cabinets and a bonus very large play room makes this home a special offering in a very exclusive neighborhood.

      Listed by Nancy S. Pallotta 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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      Federal 30-year interest rate: 3.66% last updated on 2016-04-28

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      92 Middlesex Street Winchester Ma 01890

      MLS Number 71996841

      • Rental
      • Date Available 07/01/2016

      Totally renovated townhouse with 4 bedrooms and 2.5 baths in great location. Amenities include: central air, in-unit laundry, fireplace, deck & fenced in yard. Beautiful open floor plan, Brazilian cherry floors and vaulted ceilings. Granite and stainless steel kitchen with breakfast bar. Master suite boasts, walk-in closet, master bath and soaring ceilings. Plenty of storage space n basement and attached garage. Available July 1st.

      Listed by Lesley Smith 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: 3.66% last updated on 2016-04-28

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      44 Grove Street Winchester Ma 01890

      MLS Number 71996762

      • Rental
      • Date Available 08/01/2016

      Charming and Sun Splashed 4BR, 2 1/2 Bath single family home on beautifully landscaped lot to include : Spacious living room with fireplace, Dining room with corner build in and a modern eat in kitchen leads to mudroom and back deck. Handsome hardwood floors throughout. First floor Bedroom/Office and 1/2 bath. Three more bedrooms including master suite with walk in closet and another full bathroom on second floor. Lower level family room with fire place and a playroom. Laundry and lots of storage space. Lovely and flat back yard and a huge back deck. Mins to Wedgemere and Winchester center, Shops and Restaurants and more. Easy access to Rtes 3, 38, 95 and 93.

      Listed by Fariba Rostam of Boston City 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: 3.66% last updated on 2016-04-28

      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

      Winchester MA200 Swanton, Unit 227

      Price$185,000

      Est. Mortgage: $/month

      MLS Number 71995950

      • Condo or Co-op
      • Bedrooms 1
      • Bathroom 1

      Bright and Sunny! Enjoy your morning coffee on the sunny east facing balcony overlooking the Middlesex Fells Reservation on the horizon and the private WILDLIFE SANCTUARY AND Pond in the garden area. Make this well maintained second floor unit your own by sprucing up the kitchen and bath. The condo fee includes (ALL UTILITIES) electricity,heat, water, hot water and Air Conditioning and use of the pool. Close to restaurants and shopping. Pergo wood flooring in the living room. Five minutes to the train and Rts 93 and 95. Gated Parking. Whether HOME or an investment Well worth it!

      Listed by Caci/ Fitzgerald Team, Bill Caci and 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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      Federal 30-year interest rate: 3.66% last updated on 2016-04-28

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

      36 Robinhood Road Winchester Ma 01890

      MLS Number 71996452

      • Rental
      • Date Available 07/01/2016

      Spacious renovated home with 5 bedrooms, 3 1/2 baths on a great West side street. This home offers three full floors of space with generously sized rooms, lots of sunshine and a bright and open floor plan~ potential for a first floor bedroom if needed with adjacent full bath. Fully applianced granite kitchen with dining area, living room with picture window, formal dining room & sunroom. Expansive wrap around deck with 2 access doors makes enjoying the rear yard easy. Master suite on the 2nd floor with updated bath, and plenty of closet space~ finished lower level with large family room, 1/2 bath, laundry, and storage. 2 car attached garage~ Newly installed high efficiency gas furnace, whole house water filtration system, alarm system & newer windows, you will be very comfortable in this great home! *New Vinsen Owen elementary school district*

      Listed by Kim Covino 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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      Federal 30-year interest rate: 3.66% last updated on 2016-04-28

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

      45 Cross Street Winchester MA

      Winchester MA45 Cross Street

      Price$499,900

      Est. Mortgage: $/month

      Open House

      MLS Number 71980174

      • Single Family
      • Next Open House: Sun, 1st 11:30 am
      • Bedrooms 3
      • Bathroom 2
      • Year Built 1916

      Wonderful opportunity to own a sunny updated 3 bedroom colonial full of character and warmth. Walking distance to the Muraco School, about 1 mile to Winchester center, and close to I93 and Winchester Hospital. Kitchen with cherry cabinets, granite and stainless steel appliances. Fantastic large fenced in and level yard with stone patio, swingset and shed. Kitchen, bath, electrical, plumbing and windows (except 2 in kitchen) have all been updated within the last 7 years. 2nd floor laundry.

      Listed by Melinda Johnson of Coldwell Banker Residential Brokerage - Sudbury

      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: 3.66% last updated on 2016-04-28

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

      50 Lake Street Winchester MA 01890

      Winchester MA50 Lake Street, Unit J

      Price$415,000

      Est. Mortgage: $/month

      Active With Contract

      MLS Number 71991989

      • Condo or Co-op
      • Bedrooms 2
      • Bathroom 1

      Water views from the charming condo close to everything from buses and trains to shopping. Great in town feel and ready for a buyer to move right in and enjoy breezes off the water from the patio. Great floor plan and such a pretty and sunny living room. Good size master with closet system. Lower level is great for a media room. Afford to live in Winchester!

      Listed by Nan Shanahan 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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      Federal 30-year interest rate: 3.66% last updated on 2016-04-28

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

      60 Lake Street Winchester MA 01890

      Winchester MA60 Lake Street, Unit B

      Price$429,000

      Est. Mortgage: $/month

      Open House

      MLS Number 71973634

      • Condo or Co-op
      • Next Open House: Sun, 1st 12:00 pm
      • Bedrooms 2
      • Bathroom 1

      Opportunity to live in the popular Wedge Pond Condominiums! Excellent location, near all of the amenities - shopping, grocery store, restaurants, MBTA Commuter Train (Wedgemere & Winchester stations). 2 bedroom, 1 bath unit with pond views and one deeded parking space! Flexible, open floor plan. Good sized Master Bedroom and closet! Pull down attic stairs installed. Don't miss this one!

      Listed by Therese Ryan of Therese Ryan Real Estate

      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: 3.66% last updated on 2016-04-28

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

      7 Conant Road Winchester MA 01890

      Winchester MA7 Conant Road, Unit 51

      Price$495,000

      Est. Mortgage: $/month

      MLS Number 71987299

      • Condo or Co-op
      • Bedrooms 2
      • Bathroom 2

      Amazing move in ready 2 bedroom, 2 bath single level living unit at the Willows! Enjoy the spacious, open living and dining areas with a gas fireplace and private patio. Comes with a modern eat-in granite countertop kitchen with gas cooking and in-unit laundry area. Gleaming teak hardwood floors throughout with brand new carpet in bedrooms. Master bedroom is bright and sunny with a second private patio, and boasts a walk-in closet with a double vanity bathroom. Fantastic second bedroom with additional full bathroom in hallway. The unit features a highly desirable attached garage--a rare find in the complex! Condo association amenities include a clubhouse with a pool, exercise room, and meeting area for resident's use.

      Listed by William Shao of RE/MAX Best Choice

      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: 3.66% last updated on 2016-04-28

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

      48 Mount Vernon Street,2nd FLOOR Winchester MA 01890

      MLS Number 71987415

      • Commercial Office

      Located in downtown Winchester, a beautifully renovated 3-story office building offers one of the highest quality building improvements and tenant fit up in town. The 1,440 s.f. 2nd floor space contains 4 offices, & reception area, with extensive river and streetscape views. Space is in excellent condition, fully air conditioned and shares kitchenette and 2 bathrooms with 1 other tenant. Call for floor plan/lease terms. Opportunity to rent fully furnished at an additional cost.

      Listed by Peter Tedesco of Mount Vernon Advisors

      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: 3.66% last updated on 2016-04-28

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

      44 Spruce Street Winchester Ma 01890

      MLS Number 71983632

      • Rental
      • Date Available 07/01/2016

      Built new in 2000. Bright and Spacious, Light filled rooms. Walk to town location. Nearby commuter rail, schools, shopping. Side street residential family neighborhood. Four bedrooms, two and one half baths. Master bedroom and private bath has cathedral ceilings with skylights, and walk in closet. Two car garage under, bonus room in basement. Laundry machines in unit. Private fenced in yard. Available July 1, 2016

      Listed by Dylan Archambault of Archambault Real Estate

      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: 3.66% last updated on 2016-04-28

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      22 Clematis Street Winchester Ma 01890

      MLS Number 71982199

      • Rental
      • Date Available 09/01/2016

      Winchester single family 9 years new 5 bedroom 4.5 bath Brick front center entrance colonial Gourmet Built in gas cook-top wine rack granite kitchen available 09/01/16 off street parking walking distance to Winchester hospital and 22 minutes by car to downtown Boston. Winchester boasts a commuter rail one mile away to downtown Boston also.Please call for private qualified showing! Long term lease desired 3 years Available September 1st 2016 must be pre qualified no pets a bonus and will consider pets for added consideration.Great credit needed! No lead in child safe house $5.5 k a month with pets an extra charge if accepted , House is modern and short walk to town commuter train rt 93 4 minutes away call today.Please call for pre approvals as owner wants approvals details before showings on final approval based on income and credit and ability to pay the rent . 36 month lease term wanted but will consider a one or two year. Gas fireplaces in living room and master bedroom.

      Listed by Christopher D'Errico of Greater Boston Properties, Inc

      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: 3.66% last updated on 2016-04-28

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      3 Dunham Street Winchester Ma 01890

      MLS Number 71976871

      • Rental
      • Date Available 05/01/2016

      Conveniently located close to downtown Winchester and the train. Two bedroom, 1.5 bath with the feel of a single family. Beautiful hardwood floors. New kitchen cabinets and stainless steel appliances, Bosch gas five burner stove, dishwasher and fridge. Front loading LG washer/dryer. Lots of storage in basement. Third floor ideal for home office. Available May 1st.

      Listed by Mary Kelly of Property Central, Inc.

      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: 3.66% last updated on 2016-04-28

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      183 Washington Winchester Ma 01890

      MLS Number 71976057

      • Rental

      Recently renovated two level condo in a two family property. Walking distance to winchester center. This condo is absolutely beautiful and must be seen to be appreciated. Amazing hardwood floors throughout.The kitchen ,bathroom living room, dining room and bedroom/office located on first level. Three large bedrooms on top level. All new stainless steel appliances in kitchen. Large private deck off the kitchen is perfect . The owner is willing to negotiate lease terms so please contact the listing agent to discuss further. One car off street parking. The owner will be paving the left side of driveway for more parking for the tenants. Great location and pets okay...

      Listed by Danielle J. Felice of New England Properties

      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: 3.66% last updated on 2016-04-28

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

      38 Wedgemere Avenue Winchester Ma 01890

      MLS Number 71975321

      • Rental
      • Date Available 04/15/2016

      Highly desirable Flats location. Gracious 4bed, 2.5bath Colonial located on one of Winchesters prettiest streets. First floor features: Front to back fireplace living room with custom bookshelves and cabinets. Formal dining room with natural light and wainscoting just off the Tuscan style kitchen. Entertaining is easy with the kitchen flowing nicely to a casual eating area, family room with gas fireplace, bar and Cherry built-ins. Second floor has 4bedrooms all with hardwood floors, a full bath and a 3/4 en suite master bath. Additional features include, Finished basement with fireplace, Central Air, Security system, Detached two-car garage and lovely, private backyard patio. Close to Winchester center, Train and VO school district. Pets negotiable.

      Listed by Catherine Albiani 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: 3.66% last updated on 2016-04-28

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

      40 Church Street Winchester Ma 01890
      Open House

      MLS Number 71963694

      • Rental
      • Next Open House: Sun, 1st 12:00 pm

      The feel of a single family home.! This unit has ideal mix of luxury & convenience. A rare find architecturally significant brick, granite, & stone construction & roof deck and private balconies. The 1st fl features open design w/ sun filled gourmet kitchen w/ Viking appliances, leading to dining area/ family rm w/ stone accented fireplace, custom millwork w/ French doors leading to private patio. 2nd fl offers 2 bedrms w/ full bth & wlk-in closets, w/ access to the oversized roof deck. The 3RD fl offers a Master Suite w/ custom millwork, wlk-in closet, stone accented FP & French doors opening to private balcony. The lower level is ideal for oversized family, media, workout or play rm. All baths have radiant heating. Exterior features include extensive lighting, fieldstone walls and heated brick pavers throughout entire driveway.Single car garage and additional parking.2 Townhomes located at 40 Church Street are ready for occupancy and 1 to be built w/ possibility to design & customize

      Listed by Dorothea Feffer 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: 3.66% last updated on 2016-04-28

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      15 Thompson Street Winchester MA 01890

      MLS Number 71974159

      • Commercial

      Retail space in downtown Winchester Directly across from Starbucks

      Listed by David Errico of The Winchester Companies

      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: 3.66% last updated on 2016-04-28

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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 and 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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      Federal 30-year interest rate: 3.66% last updated on 2016-04-28

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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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      Federal 30-year interest rate: 3.66% last updated on 2016-04-28

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      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.

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