Winchester Homes for Sale

Winchester, Massachusetts is a quiet, bedroom community conveniently located just 8 miles north of Boston. Winchester is home to several lakes and parks. Winchester is a family-friendly community that is home to several well-maintained parks, several lakes, and lots of trails.

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Browse all homes for sale in Winchester, Massachusetts below. Contact us to schedule a showing or if you have any questions. Create an account to save your favorite Winchester listings and to receive email notifications when similar properties become available. 

5 Cambridge Street Winchester MA 01890

Price$4,499,000

Est. Mortgage: $/month

MLS Number 72476341

  • Single Family
  • Garage 2
  • Parking Spaces 10
  • Year Built 1857
  • Full Bath 4

Majestic WATERFRONT Estate situated on the west bank of the Mystic lake with breathtaking views over the water and onto the Boston Skyline! Over an acre of rolling hills, the most gorgeous and serene setting in all of Winchester; this property is like no other! This home has been completely & lovingly renovated and restored to its original grandeur blending exquisite detail with modern day luxuries.This home boasts 12' ceilings on the first and showcases 13 rich and elegant rooms that you can only appreciate in person. Enter though the grand foyer and your eye is drawn through the living room windows and over the rolling hills of the beautifully manicured lawn to the lake and beyond to the Boston skyline! With Winchester being only 8 miles north of the city and Logan airport, this home is a commuters dream. 5 bedrooms on the second floor with 4 baths,Grand Master overlooking lake with fireplace & gorgeous spa bath. Must see this rare and never before offered home for sale in Winchester

Listed by Kim Covino of Leading Edge Real Estate

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$/month over payments
Federal 30-year interest rate: 3.75% last updated on Jul 11, 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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9 Grove Street Winchester MA 01890

Price$3,990,000

Est. Mortgage: $/month

MLS Number 72461829

  • Single Family
  • Garage 3
  • Parking Spaces 3
  • Year Built 1914
  • Full Bath 6

Restored to its former grandeur, and renovated to modern splendor is your new home in highly desirable Winchester, MA - just 7 miles from downtown Boston. Enjoy all the convenience of being close to the city but still far enough away to relax in the serenity of this premium suburb (bonus - Winchester is situated close by to the PRIVATE AIR TRAVEL HUB of Bedford Hanscom Field Airport). Features of the home you will appreciate include a SECOND MASTER, smartly placed across the home from the main master bedroom; GYM and SAUNA/STEAM/SPA room to keep healthy, whole and mindful; WIRED FOR SMART HOME FEATURES including audio, video, and security. A third floor for extended guests or staff features a SECOND LAUNDRY ROOM, and the finished basement hosts an 1100 BOTTLE WINE CELLAR, MEDIA ROOM, and kitchen area, that will be the space to entertain your guests for movie nights or big games. A 3+ CAR GARAGE completes this magnificent home.

Listed by Michael Carucci and James Raggi of Gibson Sotheby's International Realty

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$/month over payments
Federal 30-year interest rate: 3.75% last updated on Jul 11, 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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6 Harrison Street Winchester MA 01890

Price$3,095,000

Est. Mortgage: $/month

MLS Number 72466644

  • Single Family
  • Garage 3
  • Parking Spaces 4
  • Village The Flats
  • Year Built 2019

New construction colonial will take your breath away! Entryway opens up to an open concept layout: Family room w/ gas fireplace, dining room, living room, grand kitchen, office, mudroom w/ built-ins & 1.5 baths. The kitchen features an oversized island w/ White Rhino counters, Wolf double oven w/ grill, griddle, custom hood & pot filler, 54" sub zero fridge/freezer, 2 sinks, 2 dishwashers & pantry. Sliders open up to a patio & expansive lawn. 2nd floor features the grand master suite plus 3 additional bedrooms, all w/ ensuite bathrooms & walk-in closets. Master includes dramatic vaulted ceilings, cupola, attached sitting room, oversized celebrity style closet & master bathroom w/ soaking tub, rain shower & marble floors. The 3rd floor has 2 bedrooms & 1 full bathroom. Finished lower level w/ sunken media room, cable/internet setup, central vac & sitting room w/ full bathroom. Additional features: oversized laundry room; heated floors in full bathrooms; heated oversized 3-car garage.

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: 3.75% last updated on Jul 11, 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: 3.75% last updated on Jul 11, 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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65 Myopia Road Winchester MA 01890

Price$2,699,000

Est. Mortgage: $/month

MLS Number 72506620

  • Single Family
  • Garage 2
  • Parking Spaces 6
  • Year Built 1952
  • Full Bath 4

IMMACULATE ESTATE WITH STUNNING GROUNDS & HEATED POOL!!! This prestigious Myopia Hill address is an incredible Colonial set on an acre of land, affording privacy & tranquility. The home features a grand foyer, elegant dining room with fireplace, a chef's kitchen, and a vaulted breakfast nook; perfect for all your entertaining needs. The adjoining living & family room boasts soaring ceilings, natural light streaming through oversized windows & an impressive stone fireplace. The 2nd level features 4 spacious bedrooms, including the grand master suite with elegant master bath & dream walk-in closet. 2nd floor mezzanine game room, 3rd floor open office loft, home gym area,

Listed by The Marrocco Group and Monte Marrocco of Coldwell Banker Residential Brokerage - Winchester

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%
$/month over payments
Federal 30-year interest rate: 3.75% last updated on Jul 11, 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 McCall Road Winchester MA 01890

Price$2,600,000

Est. Mortgage: $/month

Open House

MLS Number 72526503

  • Single Family
  • Next Open House: Sun 21st 12:00 pm - 1:30 pm
  • Garage 3
  • Parking Spaces 3
  • Village Myopia Hill

Custom built Myopia Hill Colonial was part of the Schrafft Estate peacock garden. From the moment you traverse the driveway nestled in greenery, this exceptional setting will capture your heart. The magical lot with beautiful mature plantings offers privacy with front porch, patios & lawn space. The spacious kitchen provides ample room for cooking & gathering with dining area & center island which flows into the 2 story, beamed ceiling family room with fireplace, interior balcony & oversized windows on three sides to enjoy all seasons. The elegant foyer opens to fireplace living room & vaulted ceiling dining room - both with access to serene patios for gracious entertaining. Enjoy a treetop view from the 2nd floor which includes a private master suite bedroom, guest room with ensuite bath, 2 additional bedrooms with shared bath & game room. Direct entry from the 3-car garage with access to both the basement & large mudroom, half bath & laundry, offers ease of living. Truly a retreat!

Listed by Anne Spry and Stephanie Mcgowan of Waterfield Sotheby's International Realty

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$
%
$/month over payments
Federal 30-year interest rate: 3.75% last updated on Jul 11, 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: 3.75% last updated on Jul 11, 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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12 Prospect Street Winchester MA 01890

Price$2,499,000

Est. Mortgage: $/month

MLS Number 72493394

  • Single Family
  • Garage 2
  • Parking Spaces 6
  • Village near center
  • Year Built 1880

Spectacular NEW RENOVATION! This breathtaking home with gorgeous kitchen featuring state of the art design with Thermador appliances, full wine tower, 42'' fridge, 6 burner gas range, quartzite island with seating for 4/5 and breakfast nook overlooking beautiful 27.000+ sf lot with perennial plantings and unique stone and shingle 3 car garage/ carriage house. Formal dining room with beautiful woodwork; double crown moldings, wainscoting, 2 chandeliers and bay window seating area. Elegant formal LR with lit built ins and fplc. Family room w/ oversized wood burning fplc, and a wall of windows beaming with sunlight. Enjoy summer evenings on the expansive front porch or on the rear terrace/ & patio with 6 person Jacuzzi offering gorgeous sunset views over Winchester center! This Magnificent home features 7 spacious bedrooms each w/ generous closet space & high ceilings. Pella windows, 400amp electric, 3 zone A/C, irrigation well, 3 car garage. Basement media room MUST SEE!

Listed by Kim Covino of Leading Edge Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 3.75% last updated on Jul 11, 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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16 Calumet Road Winchester MA 01890

Price$2,349,000

Est. Mortgage: $/month

MLS Number 72514667

  • Single Family
  • Garage 2
  • Parking Spaces 5
  • Year Built 1915
  • Full Bath 4

New price! One of the most beautiful homes in the Winchester Flats, this thoughtfully renovated home with gorgeous curb appeal is sure to impress with its 12 rooms, each boasting beautiful craftsmanship, exquisite detail, beautiful sunlight, and a location that cannot be beat! Situated on a manicured 16k level lot with mature trees, perennial gardens, and an abundance of privacy. The farmhouse style kitchen w/dining area features custom inset cabinetry, Viking stove, direct access to mudroom & half bath and offers panoramic views of the oversized level rear yard. 2nd level master suite with fireplace, and inviting spa-like bath. 3 additional spacious bedrooms and 2 full baths complete this floor. 3rd floor offers additional bedroom and full bath. Lower level rec. room/TV room, laundry, and lots of great storage! Enjoy endless summer evenings on the wraparound screened porch located off the cozy den. A/C, 2 car garage, Ambrose school. Call for a private showing anytime.

Listed by Kim Covino of Leading Edge Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 3.75% last updated on Jul 11, 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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5 Fox Hunt Lane Winchester MA 01890

Price$2,275,000

Est. Mortgage: $/month

MLS Number 72506669

  • Single Family
  • Garage 2
  • Parking Spaces 4
  • Year Built 1982
  • Full Bath 4

Understated and unique luxury. This traditional brick colonial opens into an interior of simple, contemporary beauty. Situated on 1.2 acres that border the 13th fairway of the Winchester Country Club, the home's 300-foot elevation affords sweeping views across the Mystic Lake and into East Boston, with brilliant sunrises that change hourly with the light and weather. A large deck and patio invite outside entertaining. Inside, the home mixes traditional and contemporary elements: an expansive living room with custom Butternut woodwork and vaulted ceiling; a kitchen/family room with a gas fireplace; a TV and billiards room; a master bedroom suite with a fireplace and attached office/dressing room. The second floor features two ensuite bedrooms, plus options for additional bedrooms. The walk-out lower level includes an indoor pool, greenhouse, and a fourth bedroom with a separate entrance, bathroom, and sauna.

Listed by Cynthia Houle of Berkshire Hathaway HomeServices Commonwealth Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 3.75% last updated on Jul 11, 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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38 Prospect Street Winchester MA 01890

Price$2,099,000

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 & serene settings you will find, this very special home is like no other! This gorgeous 4/5 bed 3.5 bath home was expanded & renovated inside and out by the current owners. 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 featuring inset cabinets, breakfast nook w/ bench, built-in desk, butler's pantry w/ wet-bar, coffee bar, wine storage & add'l pantry/mudroom. Cozy family room just off kitchen with custom built in media wall. 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: 3.75% last updated on Jul 11, 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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6 Thornton Road Winchester MA 01890

Price$1,999,000

Est. Mortgage: $/month

MLS Number 72425766

  • Single Family
  • Garage 2
  • Parking Spaces 4
  • Year Built 2013
  • Full Bath 3

Prepare to be impressed by this well-crafted 14 room colonial w/an interior rich w/ architectural details; hardwood floors, crown moldings, wainscoting & chair rails.This 5 year old 14 room unique home has 5 bedrooms & 3 1/2 baths. The first floor features an oversized gourmet kitchen w/ 2-tiered island, & SS appliances. The adjoining FR has a gas fireplace, cathedral ceiling and access to a large deck overlooking a flat back yard, an open LR with a 2nd gas fireplace & built-in bookcases, DR w/ bay window, and a private office complete the first floor. The 2nd floor consists of 4 BDRM's including a spacious MBRM w/ walk-in closet & premium en-suite, laundry & sitting area. On the 3rd floor you will find a 5th BDRM w/en-suite, plus airy playroom w/ reading nooks. Finished lower level with high ceilings consists of two+sizable rooms and walk-out access to the rear yard. Convenient location in the desirable VO school district & close to parks, shopping & public transportation.

Listed by Errico Team of Waterfield Sotheby's International Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.75% last updated on Jul 11, 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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