Homes for Sale Winchester MA

Winchester, Massachusetts is 8 miles north of Boston. Winchester is child-friendly and home to lakes, parks, and trails. Winchester keeps its public spaces well maintained. Winchester is a family-friendly bedroom community. 

Discover Winchester Real Estate

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38 Prospect Street Winchester MA 01890

Price$2,349,000

Est. Mortgage: $/month

MLS Number 72490271

  • Single Family
  • Garage 2
  • Parking Spaces 8
  • Year Built 1910
  • Full Bath 3

Nestled amidst the most gorgeous landscape and in one of the most serene settings you will find, this very special home is like no other! Formerly a carriage house, this gorgeous 4/5 bed 3.5 bath home was renovated/rebuilt keeping many of the unique carriage house elements in place. From the moment you enter into the stunning foyer, you will feel the welcoming warmth and see the quality that surrounds with the wide plank Hickory floors, open concept living room/dining room with high coffered ceilings, oversized wood-burning fireplace, custom built-ins, and sun-filled sitting room off to the side with exterior access to private fieldstone patio. Chef's kitchen feat. inset cabinets, breakfast nook w/ bench, built-in desk, butler's pantry w/ wet-bar, wine storage & add'l pantry/mudroom; cozy family room off kitchen. 2nd level features master suite w/ walk-in closet & spa-like master bath; three additional rooms each w/ gorgeous views and unique characteristics. LL mudroom to garage entry

Listed by Kim Covino of Leading Edge Real Estate

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$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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19 Hillside Avenue Winchester MA 01890

Price$2,099,000

Est. Mortgage: $/month

MLS Number 72489931

  • Single Family
  • Garage 2
  • Parking Spaces 3
  • Year Built 1888
  • Full Bath 4

Presenting 19 Hillside Avenue! A lovely and updated Robert Coit home, thoughtfully renovated by its current owners. Enjoy a bright kitchen with granite countertops, stainless steel appliances and large island with access to the deck. A formal dining room offers a charming window seat open to the living room with fireplace, both featuring magnificent views of Winchester. The second floor offers large bedrooms and new spacious master bedroom with office, balcony and walk in closet. Additional bedrooms and bathroom on the third floor. The lower level has been fully finished with large family room including custom spiral staircase, gym and in law/au pair suite with its own sitting room, bedroom and full bathroom as well as outdoor access. Outdoor entertaining is a must with expansive yard, sweeping stone patio and deck. Located on a dead end street just steps from Winchester Center, schools and train! A gracious mix of old and new, 19 Hillside Avenue is a special property.

Listed by Karen S. Garrett of Better Homes and Gardens Real Estate - The Shanahan Group

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$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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48 Cabot Street Winchester MA 01890

Price$1,650,000

Est. Mortgage: $/month

Open House

MLS Number 72488975

  • Single Family
  • Next Open House: Sat 25th 12:00 pm - 1:30 pm
  • Garage 2
  • Parking Spaces 4
  • Year Built 1922

Stunning 5 bedroom Colonial in Winchester's desirable Flats neighborhood, thoughtfully modernized for today's living. First floor features hardwood floors, high ceilings, formal dining room with chair rail, inviting living room with fireplace, adjacent sunroom with built-in cabinets & cozy family room with french doors & custom book shelves. Gourmet kitchen with high-end stainless steel appliances, large island & french doors leading to a lovely deck, patio, fenced yard & 2-car garage. Large master suite with full bath, double vanity, soaking tub & tiled shower. Three additional bedrooms with ample closet space, full bath & laundry room on 2nd floor. Bonus third floor bedroom suite with full bath, cathedral ceiling & skylights. Huge lower level playroom, media area & half bath. Improvements include high efficiency heating and cooling with 9 zones, new driveway, bamboo plantings,basement improvements such as new windows,. Excellent location near downtown, schools & train.

Listed by Richard Brenner of Brenner Real Estate

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$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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20 St. Thomas More Drive Winchester MA 01890

Price$2,499,000

Est. Mortgage: $/month

MLS Number 72488480

  • Single Family
  • Garage 3
  • Parking Spaces 5
  • Year Built 2000
  • Full Bath 4

Welcome home to this beautiful custom built brick colonial in a neighborhood of several newly built homes. The foyer is two story with curved staircase into the open floor plan. The family room has a cathedral ceiling, floor to ceiling fireplace, beautiful elliptical windows that add plenty of sunshine to this room with spacious built ins. The kitchen has hardwood flooring, Thermador appliances, and wet bar. There is a step down sunroom for dining with a wall of windows, skylights and a patio door that leads to your private backyard. This home has 2 work at home office/homework rooms on the first floor, both with glorious windows to make your workday a pleasure. This home has a 3 car garage with direct access to mudroom/laundry There is a walkup finished 3rd floor and 2 sliders in the walkout LL. 4 floors of finished space. Located in the recently finished Vinson Owen School district & newly completed Winchester High School. There are 2 commuter rail stops & just 10 miles from Boston

Listed by Buono/Lyons Team of Century 21 CELLI

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$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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32 Grove Place Winchester MA 01890

Price$649,900

Est. Mortgage: $/month

Open House

MLS Number 72488380

  • Single Family
  • Next Open House: Sat 25th 12:30 pm - 2:00 pm
  • Garage 1
  • Parking Spaces 2
  • Year Built 1890

You must step inside to see all the charm of this inviting home located on a dead end street! Surprisingly spacious throughout, this home features many sought after details - high ceilings, crown molding, exposed brick, hardwood floors, recessed lighting, and more! First floor features a gracious floor plan to include an entry foyer, updated kitchen complete with granite counters and SS appliances, lovely dining room, living room with bay window, a fully renovated bath, and a third bedroom option. Retreat upstairs to find two additional bedrooms, each with jack and jill access to a beautifully renovated bathroom w/cathedral ceiling and skylight. The large enclosed front porch offers a great spot to relax in after a long day! Conveniently located just .5 miles to Wedgemere station for commuter rail to Boston. Enjoy living in Winchester with it's top rated schools, vibrant town center, restaurants, shops, farmer's market, and more! Ambrose School district.

Listed by Antonella Nigro of Berkshire Hathaway HomeServices Commonwealth Real Estate

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$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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28 Wainwright Road Winchester MA 01890

Price$899,900

Est. Mortgage: $/month

MLS Number 72487683

  • Single Family
  • Garage 2
  • Parking Spaces 6
  • Year Built 1977
  • Full Bath 3

This Mint Condition home has been meticulously maintained located in Desirable Million dollar neighborhood. 9 foot ceilings, abundant closets & Solid 6 panel doors throughout, Heated garage & driveway. This Spacious sunlit home features Inviting living room with brick fireplace & cathederal ceilings. Large dining room with sliders to wooden deck and private yard. 3 large bedrooms all with ample closets, full tiled bath w/ large linen closet on main level; Master complete with shower stalled bathroom. Lower level features high ceilings and fireplace with Gorgeous Stone Hearth, recessed lighting, 4th Bedroom, Full bath w/ tub & shower, Laundry room & 5 - zone irrigation, security & fire alarm systems. Fantastic location; Minutes to Boston, Shopping, Winchester Hospital, Walking trails, Ponds, Farm, newer Vinson Owen Elementary school and Everything else Winchester has to offer!

Listed by Patti Fitzgerald of Keller Williams Realty

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$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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17 George Road Winchester MA 01890

MLS Number 72487841

  • Condo or Co-op
  • Bedrooms 2
  • Bathroom 1
  • Square Feet 968

Amazing opportunity to own at The Residences in Winchester! Quiet and peaceful street. Two bedroom town home flooded with natural light, can be converted to three bedrooms. Three levels of living. Great space for entertaining: tastefully updated kitchen with marble countertops opens to dining area with easy access to private backyard. Hardwood floors throughout. Basement offers potential for family room or office and great storage space. More storage in the attic. Two tandem parking spaces. Well-run, pet friendly condo association. Low condo fee. Minutes to top rated Winchester public schools, recreational activities, Whole Foods, Stop & Shop, Winchester Center with its cafes, shops, restaurants, commuter rail to Boston, Farmer's Market on Saturdays. Enjoy convenience of the nearby tennis courts, barbecuing and gardening in the summer in the backyard…. Be a part of this warm, welcoming community!

Listed by Katya Pitts of Leading Edge Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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3 Orient Street Winchester MA 01890

Price$839,000

Est. Mortgage: $/month

MLS Number 72487198

  • Single Family
  • Garage 1
  • Parking Spaces 4
  • Year Built 1925
  • Full Bath 2

Classy, Charming and Comfortable best describes this Lovely Bungalow in a Perfect Location. Living room is Open and Airy with Coffered Ceilings, Dentil Crown Moulding, French Doors, Brick Fireplace, Beautiful Wall Sconces. The Kitchen has an abundance of room with Beautiful Cabinetry, Marble Countertops and Stainless Appliances. Formal Dining Room and Handsome Den giving away to More Enjoyment. Master Bedroom up or Master Bedroom Down. Guest Bedroom for those Extended Stays. Main Bath with Porcelain Walk in Shower, Glass Doors and Marble Flooring. Outside Enjoyment is so very easy whether it is on the Front Porch, Back Deck, or in the Beautiful Fenced in Yard. Whichever Spot you Chose - Tranquility will come!

Listed by Mary L. Lawton of Lawton Real Estate, Inc

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$
%
$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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7 Conant Road Winchester MA 01890

MLS Number 72484635

  • Condo or Co-op
  • Bedrooms 2
  • Bathroom 3
  • Square Feet 1409

Luxury 2br 2.5ba townhouse with a garage at the sought after Willows at Winchester! This top-notch community invites you to enjoy the summer at the heated outdoor pool, new exercise room and the gorgeous clubhouse. This two level end unit townhouse features an open floor plan. The first floor boasts sparking hardwood floors throughout, a spacious fireplaced living room with a sliding door to the deck/balcony, a fully applianced modern kitchen open to the living room & dining room. Half bathroom on the first floor. Both bedrooms on the upper level feature recently replaced carpets and walk-out balconies open to the peaceful neighborhood. Master bedroom has oversized master bath and walk-in closet. Hallway bath with a spa tub. One car garage with one off street parking in the front. Central AC, in-unit laundry on 2nd floor, and extra storage room in the basement, convenient location to downtown Winchester shops, restaurants and commuter rail to Boston. Open house Fri 5-6pm; Sat&Sun12-2pm

Listed by Wei Fu of Benoit Real Estate Group,LLC

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$
%
$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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23 Yale Street Winchester MA 01890

Price$2,249,000

Est. Mortgage: $/month

MLS Number 72485458

  • Single Family
  • Garage 2
  • Parking Spaces 3
  • Village The Flats
  • Year Built 1901

Stunning colonial in the Flats recognized as the “Nickerson House". Has undergone major renovation to combine meticulously preserved historical features w/latest demands of comfort & functionality. Featuring 6 bedrms, 4.5 baths, exquisite design, soaring ceilings, vast areas w/radiant floors, central AC, night lighting, wireless speakers, stylish fixtures. Elegant kitchen w/granite counters, large island & high-end appliances opens to family room. Sun-lit dining room, sitting & living room anchored by dramatic brick fireplace. Luxurious master suite w/fireplace, rounded bay, walk-in California Closet. En suite bath w/exceptional design: soaking tub, shower, double sink vanity, heated floor, A/C. Three other large bedrms, full bath, closet w/laundry hookup complete 2nd flr. Spacious playroom, 2 bedrms, bath on 3rd flr. Media room, gym & laundry on finished lower level. Flat private yard w/patio, porch, landscape lighting & sprinklers. 2 car garage, walk to Ambrose, center, commuter rail

Listed by Andersen Group Realty and Sven Andersen of Keller Williams Realty Boston Northwest

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$
%
$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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29 Dunster Lane Winchester MA 01890

Price$1,999,000

Est. Mortgage: $/month

MLS Number 72484222

  • Single Family
  • Parking Spaces 7
  • Village Westside
  • Year Built 1945
  • Full Bath 5

MUST BE SEEN. Spacious and elegant don't begin to describe this spectacular 7700+sf. home. Masterful design and modern luxury are uniquely blended into the construction of this exceptional property. It is truly an entertainers dream. The incredible gourmet kitchen will please even the most demanding culinary artist. The newly renovated kitchen flows into the dining area and unsurpassed Great Room, which is the heart of this home. The Great Room features a full wet bar, Brazilian cherry floors, fireplace and coffered ceilings. 5 bedrooms, 5 baths and an abundance of comfortable spots to gather provides everyone their place to "live". Enormous Master Bedroom boasts of a fireplace, walk-in, sitting area, bathroom w/soaking tub, heated floors and sauna. Relax and consider star gazing from the Hot Tub on the 3rd floor roof deck. There's also a steam/shower on this level along with a kitchenette. The lower level home office and play room with wet bar complete this incredible home.

Listed by Steve O Brien of Century 21 Adams KC

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$
%
$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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15 Cambridge Street Winchester MA 01890

Price$2,998,000

Est. Mortgage: $/month

MLS Number 72484213

  • Single Family
  • Garage 2
  • Parking Spaces 10
  • Year Built 1941
  • Full Bath 5

Live Waterfront - on Mystic Lake! This totally renovated and expanded Colonial is now a modern classic, designed for comfortable, gracious living. Open First Flr features Lg windows/glass paneled drs across back, providing abundant natural light and stunning views from Kit/Fam Rm, Liv Rm w/FP and Dining Rm. Gorgeous Cook's kitchen w/high-end appliances, Lg island, leathered granite and mahogany counter tops, and wet bar for entertaining. Handsome private, paneled office w/FP, Mud Room and half bath complete floor. Second Flr boasts 4 bedrooms, all w/meticulously finished en suite baths. Retreat-like master w/dressing closet, 2nd double wardrobe, luxurious bath w/soaker tub with lake and Boston Skyline views. All finished LL w/separate entrance incl: Media/Game Rm w/FP; flexible 5th Bdrm suite, in-law, au-pair or workout rm; full bath accessed via bdrm or hall; 2nd ldry area. Sited on prof landscaped 29K+ sf lot w/new deck, stone patio and steps to 111 ft Lakefront. 8 miles to Boston.

Listed by Ann Basmaji of Waterfield Sotheby's International Realty

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$
%
$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

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