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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57 Lawson Road Winchester MA 01890

Price$1,949,000

Est. Mortgage: $/month

MLS Number 72463191

  • Single Family
  • Garage 2
  • Parking Spaces 2
  • Year Built 1956
  • Full Bath 4

Can you feel the excitement through your screen? Because we can! Not everyday does a property like this become available in one of the most SOUGHT AFTER neighborhoods that our idyllic Winchester has to offer. This 4 bedroom, 4 full bathroom, lovely colonial checks off all the boxes. Neighborhood, check! LINCOLN SCHOOL DISTRICT, check! Sensible layout, check! Oversized family room, check! Formal spaces for entertaining, check! Office, check! Finished basement with fireplace, check! Need we say more? Enter in to a dramatic 2 story foyer that will make you swoon from the moment you enter. Not enough? Let's not forget to tell you about the master suite with TWO full bathrooms (the key to any successful relationship) and TWO walk-in closets! The heart of the home, the kitchen, boasts top of the line appliances, a large center island, and full eat-in area. Situated just over 1/2 mile from Town it makes walking to dinner, to shops, to schools, the commuter rail, or just for coffee a breeze!

Listed by Philip J. Vita of Leading Edge Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 4.31% last updated on Mar 14, 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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2 Gershon Way Winchester MA 01890

Price$1,200,000

Est. Mortgage: $/month

Active With Contract

MLS Number 72462916

  • Condo or Co-op
  • Garage 2
  • Half Bath 1
  • Bathroom 3
  • Year Built 2019

WINCHESTER'S 1ST 55+ COMMUNITY LUXURY DEVELOPMENT ON THE WEST SIDE! This new construction development is the proud winner of The National Association of Home Builders gold award recipient for design (2018). Imagine luxury finishes throughout, including 9' ceilings, hardwood floors and plenty of natural light. The open concept floor plan boasts a 1st floor master suite with oversized walk-in closets and luxurious bathroom. The kitchen is adorned with ceiling height cabinets, granite countertops and a top of the line stainless steel appliance package. Cozy up to the gas fireplace featuring custom built-ins & coffered ceilings. The dining room has sliders to a private, covered deck. The bonus room could be a home office, library or studio for your beloved hobbies. 1st floor also features a powder room and laundry. Upstairs you'll find 2 additional spacious bedrooms, a full bath and an open loft area. 2 Car garage. A short drive to downtown Winchester and only 7 miles from Boston

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

$
$
%
$/month over payments
Federal 30-year interest rate: 4.31% last updated on Mar 14, 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 Gershon Way Winchester MA 01890

Price$1,200,000

Est. Mortgage: $/month

Active With Contract

MLS Number 72462917

  • Condo or Co-op
  • Garage 2
  • Half Bath 1
  • Bathroom 3
  • Year Built 2019

WINCHESTER'S 1ST 55+ COMMUNITY LUXURY DEVELOPMENT ON THE WEST SIDE! This new construction development is the proud winner of The National Association of Home Builders gold award recipient for design (2018). Imagine luxury finishes throughout, including 9' ceilings, hardwood floors and plenty of natural light. The open concept floor plan boasts a 1st floor master suite with oversized walk-in closets and luxurious bathroom. The kitchen is adorned with ceiling height cabinets, granite countertops and a top of the line stainless steel appliance package. Cozy up to the gas fireplace featuring custom built-ins & coffered ceilings. The dining room has sliders to a private, covered deck. The bonus room could be a home office, library or studio for your beloved hobbies. 1st floor also features a powder room and laundry. Upstairs you'll find 2 additional spacious bedrooms, a full bath and an open loft area. 2 Car garage. A short drive to downtown Winchester and only 7 miles from Boston

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

$
$
%
$/month over payments
Federal 30-year interest rate: 4.31% last updated on Mar 14, 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 Gershon Way Winchester MA 01890

Price$1,350,000

Est. Mortgage: $/month

Active With Contract

MLS Number 72462918

  • Condo or Co-op
  • Garage 2
  • Half Bath 1
  • Bathroom 3
  • Year Built 2019

WINCHESTER'S 1ST 55+ COMMUNITY LUXURY DEVELOPMENT ON THE WEST SIDE! This new construction development is the proud winner of The National Association of Home Builders gold award recipient for design (2018). Imagine luxury finishes throughout, including 9' ceilings, hardwood floors and plenty of natural light. The open concept floor plan boasts a 1st floor master suite with oversized walk-in closets and luxurious bathroom. The kitchen is adorned with ceiling height cabinets, granite countertops and a top of the line stainless steel appliance package. Cozy up to the gas fireplace featuring custom built-ins & coffered ceilings. The dining room has sliders to a private, covered deck. The bonus room could be a home office, library or studio for your beloved hobbies. 1st floor also features a powder room and laundry. Upstairs you'll find 2 additional spacious bedrooms, a full bath and an open loft area. 2 Car garage. A short drive to downtown Winchester and only 7 miles from Boston

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

$
$
%
$/month over payments
Federal 30-year interest rate: 4.31% last updated on Mar 14, 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

6 Gershon Way Winchester MA 01890

Price$1,350,000

Est. Mortgage: $/month

Active With Contract

MLS Number 72462368

  • Condo or Co-op
  • Garage 2
  • Half Bath 1
  • Bathroom 3
  • Year Built 2019

WINCHESTER'S 1ST 55+ COMMUNITY LUXURY DEVELOPMENT ON THE WEST SIDE! This new construction development is the proud winner of The National Association of Home Builders gold award recipient for design (2018). Imagine luxury finishes throughout, including 9' ceilings, hardwood floors and plenty of natural light. The open concept floor plan boasts a 1st floor master suite with oversized walk-in closets and luxurious bathroom. The kitchen is adorned with ceiling height cabinets, granite countertops and a top of the line stainless steel appliance package. Cozy up to the gas fireplace featuring custom built-ins & coffered ceilings. The dining room has sliders to a private, covered deck. The bonus room could be a home office, library or studio for your beloved hobbies. 1st floor also features a powder room and laundry. Upstairs you'll find 2 additional spacious bedrooms, a full bath and an open loft area. 2 Car garage. A short drive to downtown Winchester and only 7 miles from Boston

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

$
$
%
$/month over payments
Federal 30-year interest rate: 4.31% last updated on Mar 14, 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

15 Wagon Wheel Road Winchester MA 01890

Price$1,495,000

Est. Mortgage: $/month

MLS Number 72462242

  • Single Family
  • Garage 2
  • Parking Spaces 4
  • Year Built 2011
  • Full Bath 3

Enjoy spectacular views of the Boston skyline from this 2011 built Contemporary Colonial on a desirable cul-de-sac! There's something for everyone with this flexible floor plan. Large formal entry, living room with triple windows, formal dining room, maple kitchen with oversized cherry & granite island that seats 6. This first floor also has a guest bedroom with walk-in closet, bathroom, home office, laundry & mud room. The 2nd level has a "Great" room with Palladian windows has many options for a family/media/game room. The master bedroom has a very large bathroom & there are also 3 additional bedrooms & bathroom, one of which is a huge bonus room with gas burning stove. Sliders from the kitchen to a large deck, to a stone patio & beautiful garden with perennials (almost 1/2 acre) all with amazing views & privacy. Windows galore for great light, tankless hot water, pull down attic with plumbing/electric, alarm & sprinkler systems.***Open House Sun March 17th 12 noon to 1:30pm

Listed by Marjie Fitzpatrick of Coldwell Banker Residential Brokerage - Arlington

$
$
%
$/month over payments
Federal 30-year interest rate: 4.31% last updated on Mar 14, 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$4,299,000

Est. Mortgage: $/month

Open House

MLS Number 72461829

  • Single Family
  • Next Open House: Sat 23rd 1:30 pm - 3:00 pm
  • Garage 3
  • Parking Spaces 3
  • Half Bath 2

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

$
$
%
$/month over payments
Federal 30-year interest rate: 4.31% last updated on Mar 14, 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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14 Berkshire Drive Winchester MA 01890

Price$1,325,000

Est. Mortgage: $/month

MLS Number 72461066

  • Single Family
  • Garage 2
  • Parking Spaces 12
  • Half Bath 1
  • Year Built 1973

Stately custom built colonial on a beautifully landscaped private lot! Enter through the circular driveway to this lovely home featuring a sunny front to back living room, a formal dining room, a spacious kitchen, an oversized family room with a fireplace and a glass slider leading to the deck, and a half bath with the laundry on the first level. Upstairs is the roomy master suite with a convenient 3/4 bath ensuite. Across the hall are three more good sized bedrooms and an adjacent full bathroom. The huge finished lower level offers even more living area with a kitchenette, game room, recreation space, gym/bonus room, and a 3/4 bath. There is ample storage and space throughout the home. Enjoy outdoor living on the large back deck overlooking the sprawling treelined yard. Parking is easy with a two car attached garage and long circular driveway. Very close to the Whipple Hill Conservation center and within the Vinson Owen school district. Come see this gem of a home at the open houses!

Listed by Shane Small and Allister Booth of Redfin Corp.

$
$
%
$/month over payments
Federal 30-year interest rate: 4.31% last updated on Mar 14, 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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98 Cambridge Street Winchester MA 01890

Price$900,000

Est. Mortgage: $/month

Open House

MLS Number 72460884

  • Single Family
  • Next Open House: Sun 24th 11:30 am - 1:00 pm
  • Garage 2
  • Parking Spaces 3
  • Half Bath 1

Located in upscale Winchester on an expansive lot bordered by woodlands, this lovely split entry ranch offers convenience to the town's amenities as well as privacy in the back & side yards. Imagine waking up to bright sunlight pouring in to your meticulously maintained home. Enjoy breakfast in the open concept dining/living room or in the kitchen counter seating. Or, have coffee on your spacious side or rear deck. Use the slate patio for entertaining or to relax. Back inside, easily step downstairs where you'll find an oversized finished room with the 2nd fireplace, suitable for a home office, family rm, or media viewing. Also, on this level you have a laundry area, a half bathroom, and abundant storage space. There is a large two-car garage with additional storage. 2016 updates include a new roof and rebuilt stainless steel lined chimney & maintenance free leaf filter gutters. The gleaming hardwood floors were refinished in 2018 and the interior freshly painted in 2019. Welcome home!

Listed by Michaela Pixie Mahtani of Leading Edge Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 4.31% last updated on Mar 14, 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

3 Gershon Way Winchester MA 01890

Price$1,200,000

Est. Mortgage: $/month

Active With Contract

MLS Number 72459269

  • Condo or Co-op
  • Garage 2
  • Half Bath 1
  • Bathroom 3
  • Year Built 2019

WINCHESTER'S 1ST 55+ COMMUNITY LUXURY DEVELOPMENT ON THE WEST SIDE! This new construction development is the proud winner of The National Association of Home Builders gold award recipient for design (2018). Imagine luxury finishes throughout, including 9' ceilings, hardwood floors and plenty of natural light. The open concept floor plan boasts a 1st floor master suite with oversized walk-in closets and luxurious bathroom. The kitchen is adorned with ceiling height cabinets, granite countertops and a top of the line stainless steel appliance package. Cozy up to the gas fireplace featuring custom built-ins & coffered ceilings. The dining room has sliders to a private, covered deck. The bonus room could be a home office, library or studio for your beloved hobbies. 1st floor also features a powder room and laundry. Upstairs you'll find 2 additional spacious bedrooms, a full bath and an open loft area. 2 Car garage. A short drive to downtown Winchester and only 7 miles from Boston

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

$
$
%
$/month over payments
Federal 30-year interest rate: 4.31% last updated on Mar 14, 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

6 Agawam Road Winchester MA 01890

Price$1,950,000

Est. Mortgage: $/month

Open House

MLS Number 72458378

  • Single Family
  • Next Open House: Sun 24th 12:00 pm - 2:00 pm
  • Garage 2
  • Parking Spaces 8
  • Half Bath 1

A HIDDEN TREASURE! Your private oasis with backyard bordering 350 ft. elevation summit of Mt. Pisgah conservation area, the highest point in Winchester. Amazing views of Boston! Enjoy the delightful breeze off Mystic Lake above the Winchester Country Club golf course. Perched high all by itself, this exceptional meticulously maintained three story eleven room home has totally private, beautifully landscaped grounds. Enjoy all seasons indoors and out. The family room is mahogany paneled with a fireplace & eat-in chef's kitchen. Create the ideal flow for today's lifestyle. On the second floor the master bedroom suite contains a fireplace & sitting area addition. Enjoy your daily private time without traveling to the spa hotel. Gracious and flexible floor plan allows for comfort and privacy. Turn the lower level into a media play area. Truly a rare great find, ample parking in your own, Full Loop - landscaped central island - Driveway. 8 mi to Boston, near 93 95 128 2 3.

Listed by Dorothea Feffer of Coldwell Banker Residential Brokerage - Winchester

$
$
%
$/month over payments
Federal 30-year interest rate: 4.31% last updated on Mar 14, 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

166 Pond Street Winchester MA 01890

Price$979,000

Est. Mortgage: $/month

Active With Contract

MLS Number 72458235

  • Single Family
  • Garage 1
  • Parking Spaces 4
  • Year Built 1942
  • Full Bath 3

Move right in to this pristine 8 room 4 bedroom 3 bath renovated home with space galore! Easy living with direct entry from the heated garage, huge rear yard abutting Horn Pond trails w/oversized patio complete with SunSetter electric awning, heat lamps and surround sound speakers, all completely fenced in! This home has been tastefully updated and has a floor plan that will appeal to all buyers. Great first floor offering expansive living room with a bay of windows overlooking yard, wood burning fireplace with custom mantle, updated kitchen with stainless steel appliances and adjacent dining room. The sun-filled master suite features hardwood floors, picture windows, walk-in closet w/dressing area & full bath. Two additional spacious bedrooms & renovated spa-like full bath w/ oversized shower complete upper floor. Stylish and inviting lower level w/family room, ledge stone FP, built-ins, laundry area, full bath and 4th bedroom all complete with a separate entry -great for in-laws!

Listed by Kim Covino of Leading Edge Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 4.31% last updated on Mar 14, 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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