Winchester MA Homes for Sale

Winchester, Massachusetts is a quiet bedroom community located 8 miles north of Boston. Winchester is a family-friendly community that is perfect for raising a family. There are several well-maintained parks in town as well as several bodies of water. 

Check out single family homes for sale in Winchester, MA. Search through hundreds of listings to find the right real estate for you. Save your favorites when you register with us, and you can get email updates when similar properties that match your criteria are posted. Contact us for more information!

5 Nelson Street, Winchester, MA

Price$699,900

Est. Mortgage: $/month

MLS Number 72366040

  • Single Family
  • Parking Spaces 2
  • Year Built 1887
  • Full Bath 2
  • Bathroom 2

Picture Perfect Colonial in downtown Winchester neighborhood. This beautiful and bright home has it all! Full of character and charm, this home features 3 bedrooms, 2 full remodeled bathrooms, a stunning kitchen with stainless steel appliances, beadboard ceiling, granite countertops and wide board hardwood floors with first floor laundry. Extra space in the lower level is great for a playroom or office. Close to train, schools and Winchester Center! Showings to begin at Open House 7/22 11:30-1:30.

Listed by Stephanie Mcgowan of Waterfield Sotheby's International Realty

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Longwood Residential
1309 Beacon Street | Suite 300
Brookline MA, 02446
Office: 617.396.3100

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$
$
%
$/month over payments
Federal 30-year interest rate: 4.52% last updated on Jul 19, 2018
* 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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85 Loring Avenue, Winchester, MA

Price$809,900

Est. Mortgage: $/month

MLS Number 72365545

  • Single Family
  • Parking Spaces 4
  • Year Built 1962
  • Full Bath 2
  • Bathroom 3

This home has been lovingly maintained and updated and is in mint condition Bright sunny granite kitchen and family room overlook private yard.Living room and dining room have gleaming hardwood floors. Three bedrooms on the second floor have spacious closets. Full basement has a large recreation room with fireplace and full bath. Central air,newer windows and gas heat are just a few of the amenities of this wonderful home.Located conveniently to a park, bike path and a short distance to major highways. This is a Lynch School neighborhood . Move right in and enjoy!

Listed by Nannette Shanahan of Better Homes and Gardens Real Estate - The Shanahan Group

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Longwood Residential
1309 Beacon Street | Suite 300
Brookline MA, 02446
Office: 617.396.3100

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.52% last updated on Jul 19, 2018
* 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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200 Cross Street, Winchester, MA

Price$739,900

Est. Mortgage: $/month

MLS Number 72365132

  • Single Family
  • Parking Spaces 3
  • Year Built 1950
  • Full Bath 1
  • Bathroom 2

Muraco School District !! This 3 bedroom, 1 1/2 bath Cape style home is very deceiving from the outside. So much more room than you'd think. Formal living room has wall to wall carpet over the hardwood floors. Cabinet packed kitchen, formal dining room with parquet floors, the first floor bedroom is being used as an office. Full bath. Upstairs finds two large bedroom with large closets and there is a half bath. Hardwood floors in all rooms.The basement area is finished with a laundry room with cabinets, a sink and a refrigerator. There is a family room and another office area. A plus is the storage room and extra storage under the stairs. Walk out the basement to the large back yard which has a patio and a shed. The home is close to everything -train, bus, downtown, schools. Purchase now and be in your new home in time for school. Open House Saturday 12-2 pm and Sunday 12-2 pm.

Listed by Patricia Marsh of Realty Executives Marsh & Associates

{$office->Name}

Longwood Residential
1309 Beacon Street | Suite 300
Brookline MA, 02446
Office: 617.396.3100

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.52% last updated on Jul 19, 2018
* 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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51 Wedgemere Avenue, Winchester, MA

Price$1,799,000

Est. Mortgage: $/month

MLS Number 72365181

  • Single Family
  • Parking Spaces 4
  • Village The Flats
  • Year Built 1914
  • Full Bath 3

Don’t miss this rare opportunity to live on one of the most desirable streets in the “Flats". Seldom do you find homes like this charming English Tudor for sale. This home has everything you could want and more! The grand entrance has an elegant fireplace w/hand carved mantel & leads to a front to back lv rm & 2nd stunning fireplace w/built-in bookcases. Off lv rm is a wonderful & bright Sunroom. An elegant dnrm has plenty of space for small & large gatherings. Hand painted ceiling adds charm to this room. Original butler’s pantry opens to spacious updated kitchen. Washer & dryer on main level & elegant half-bath. Completing this level spacious Family Room. The 2nd level has oversized landing which leads to 4 bdrms including master bedroom.Original claw foot tub & separate shower are delightful. The 3rd level 2 add'l bdrs & bath - lower level has a lg bonus rm & 1/2 ba - private yard w/bluestone patio. Two car garage. Location, character & space describes this gorgeous home

Listed by Janet Halloran of Leading Edge Real Estate

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Longwood Residential
1309 Beacon Street | Suite 300
Brookline MA, 02446
Office: 617.396.3100

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.52% last updated on Jul 19, 2018
* 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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86 Church Street, Winchester, MA

Price$1,849,000

Est. Mortgage: $/month

Open House

MLS Number 72364668

  • Single Family
  • Next Open House: Sun 22nd 1:00 pm - 3:00 pm
  • Parking Spaces 7
  • Year Built 1890
  • Full Bath 3

Stunning and timeless, this beautiful Victorian masterfully blends high-end updates with exquisite period details, such as gorgeous leaded windows and a superb original pocket door in the dining room. Newly renovated designer kitchen features Thermador appliances, Perlick beverage fridge, custom cabinetry, gas fireplace, and reclaimed heart pine flooring. Meticulously chosen finishes like grass cloth wallpaper, custom window treatments, antique and modern lighting create spaces that welcome and delight. Generous bedrooms on the 2nd and 3rd levels, including the serene master retreat, have ample closets and are freshly updated; 3 remodeled baths impress. Sizable lower level bonus room is perfect for movie night, working out and entertaining. Brand new modern office is handsomely designed down to the last detail, flooded w/natural light and set away from main house for privacy. Lovely backyard oasis; wonderfully close to Center’s vibrant restaurants, shopping, schools and train stations

Listed by Stephanie Mcgowan of Waterfield Sotheby's International Realty

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Longwood Residential
1309 Beacon Street | Suite 300
Brookline MA, 02446
Office: 617.396.3100

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.52% last updated on Jul 19, 2018
* 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 Brookside Avenue, Winchester, MA

Price$769,900

Est. Mortgage: $/month

MLS Number 72363094

  • Single Family
  • Parking Spaces 3
  • Year Built 1940
  • Full Bath 1
  • Bathroom 2

Classic New England Cape located in the popular Muraco School section of Winchester! This 3 bed, 1½ bath home offers a fantastic opportunity to become part of the Winchester community. This well-maintained home has updated systems, newer windows, hardwood floors & charming details including; crown molding, marble faced fireplace & built in cabinetry. The first level offers an expansive formal living room w/ a stunning fireplace that flows into the dining room, kitchen, half bath & a private sun filled office. You’ll love the convenient side entrance from the kitchen leading you to an enclosed breezeway/mudroom & attached garage. On the second level are 3 spacious bedrooms, full bath & bonus room which would make an excellent playroom, office or guest bedroom. Basement offers additional room for storage or expansion. Enjoy the private fenced in backyard with patio, storage shed & a wonderful location w/ easy access to both Route 93 & 95, restaurants, shops & public transportation.

Listed by Theuer, Pirani & Wile and Julie Wile Fish of Leading Edge Real Estate

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Longwood Residential
1309 Beacon Street | Suite 300
Brookline MA, 02446
Office: 617.396.3100

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.52% last updated on Jul 19, 2018
* 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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36 Chester Street, Winchester, MA

Price$699,900

Est. Mortgage: $/month

Active With Contract

MLS Number 72362451

  • Single Family
  • Parking Spaces 3
  • Year Built 1860
  • Full Bath 1
  • Bathroom 2

New to the market! Solid mid 1800 Colonial style home in need of upgrades and clean up located on a quiet tree lined street within close proximity to all of Winchester's amenities and a short walk to Muraco Elementary School. Location and land make this an opportunity for a contractor to upgrade. Being offered as is. This is a flipper's dream! Perfect opportunity to modernize and restore the property to its original glory. A rare and unique diamond in the rough with unlimited potential to be enjoyed by a new generation. Offering a level fenced in backyard perfect for those summer barbecues with plenty of off street parking. Perfect opportunity to set up roots in one of the most sought after communities minutes from Boston!

Listed by Robin Dunbar Bain and Paula Savard of Aberman Associates, Inc.

{$office->Name}

Longwood Residential
1309 Beacon Street | Suite 300
Brookline MA, 02446
Office: 617.396.3100

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.52% last updated on Jul 19, 2018
* 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 Cardinal Street, Winchester, MA

Price$924,900

Est. Mortgage: $/month

Price Changed

MLS Number 72362368

  • Single Family
  • Parking Spaces 4
  • Year Built 2015
  • Full Bath 3
  • Bathroom 4

Gorgeous sun filled townhouse located on quiet cul-de-sac will live more like a single family. So much space w/private yard & driveway.Beautiful gourmet kitchen w/ large marble island,countertops, stainless steel appliances. Open floor plan w/ dining area to living room featuring fireplace & custom bookshelves. Office on the main floor features french doors & custom bookcases. Master bedroom has a beautiful master bath & custom walk in closet w/ expansive shelving/drawers.Two more bedrooms, a full bath and laundry closet finish the upstairs. The delightful finished basement features a family room, children's art/play area and another bonus room & bath for guests.Off the first floor mudroom is the back deck & pretty new patio to enjoy the professionally landscaped yard w/ new plants & fruit trees and shed.This neighborhood in the Muraco school district is near the bike path, the Fells, KidStock, ballet school and Russian math to name a few.Don't miss this beauty.

Listed by The Synergy Group and Susan Silkes of Leading Edge Real Estate

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Longwood Residential
1309 Beacon Street | Suite 300
Brookline MA, 02446
Office: 617.396.3100

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.52% last updated on Jul 19, 2018
* 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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312 Washington Street, Winchester, MA

Price$889,000

Est. Mortgage: $/month

Active With Contract

MLS Number 72360757

  • Single Family
  • Parking Spaces 3
  • Village Muraco
  • Year Built 1880
  • Full Bath 2

Finally! A fabulous, beautifully renovated home that you can afford in the coveted Muraco District! This one is a gem. Open and airy farmhouse sits on a gorgeously landscaped lot highlighted by a stone patio with a fire pit, lovely mature plants and a huge deck off the kitchen. The interior shines with sleek lines in the open, modern kitchen, dining room and family room. Antique wood floors have been perfectly restored, taking the design element of this home to a really beautiful height. There are 4 bedrooms, second floor laundry, sleek bathrooms and full dry basement for storage. There is also a big farmers porch to relax on as you sip your coffee, and lots of driveway space. BONUS: Solar panels (owned, not rented) keep electric bills extremely low (see attached utility bills). Close to town, schools, trains, the Fells and highway. Open Sat & Sun!

Listed by Nancy S. Pallotta of Leading Edge Real Estate

{$office->Name}

Longwood Residential
1309 Beacon Street | Suite 300
Brookline MA, 02446
Office: 617.396.3100

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.52% last updated on Jul 19, 2018
* 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 Bates Road, Winchester, MA

Price$1,199,000

Est. Mortgage: $/month

MLS Number 72358930

  • Single Family
  • Parking Spaces 2
  • Year Built 2017
  • Full Bath 3
  • Bathroom 4

Just Completed!! New construction townhouse with the feel of single family living! Two story foyer welcomes you into the spacious first floor with high-end designer finishes throughout and the ideal open concept floor plan. Bright and sun-filled living room with sliders leading to private exterior deck, separate dining area off the chef's kitchen with island, stainless steel appliances, and quartz countertops. The second floor offers a luxurious Master Suite, oversized walk-in closet and private bath. Two spacious bedrooms and additional full bathroom with double vanity and separate laundry room finish off the second floor. Enjoy the convenience of an attached 2-car garage with additional deeded parking in driveway, exclusive yard rights, just finished walk-out lower level makes a great family room or guest suite with full bath and so much more!

Listed by Kim Covino of Leading Edge Real Estate

{$office->Name}

Longwood Residential
1309 Beacon Street | Suite 300
Brookline MA, 02446
Office: 617.396.3100

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.52% last updated on Jul 19, 2018
* 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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8 Bates Road, Winchester, MA

Price$1,199,000

Est. Mortgage: $/month

MLS Number 72358931

  • Single Family
  • Parking Spaces 2
  • Year Built 2017
  • Full Bath 3
  • Bathroom 4

JUST COMPLETE! Surprisingly spacious 4 level new construction townhouse with the feel of single family living! Two story foyer welcomes you into the spacious first floor with high-end designer finishes throughout and the ideal open concept floor plan. Bright and sun-filled living room with sliders leading to private exterior deck, separate dining area off the chef's kitchen with island, stainless steel appliances, and quartz countertops. The second floor offers a Master Suite with cathedral ceiling, oversized walk-in closet and private bath. Two spacious bedrooms and additional full bathroom with double vanity and separate laundry room finish off the second floor. Enjoy the convenience of an attached 2-car garage with additional parking in driveway, exclusive use yard rights, walk-out lower level just finished~ great for family room or guest suite with full bath!

Listed by Kim Covino of Leading Edge Real Estate

{$office->Name}

Longwood Residential
1309 Beacon Street | Suite 300
Brookline MA, 02446
Office: 617.396.3100

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.52% last updated on Jul 19, 2018
* 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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101 Harvard Street, Winchester, MA

Price$679,000

Est. Mortgage: $/month

Active With Contract

MLS Number 72358216

  • Single Family
  • Parking Spaces 3
  • Year Built 1880
  • Full Bath 1
  • Bathroom 2

Extensively renovated in 2012, this home has all of the amenities you’d wish for. Located at the end of a dead end street w/ proximity to all of Winchester’s amenities & just a brief walk to Muraco Elementary. Greeted by a charming farmers porch, perfect for your morning coffee or to relax on after a long day. The 1st floor has a wonderful open layout containing a living room, adjoining dining room w/ a kitchen pass-through window to the completely renovated kitchen featuring a gas stove, stainless steel appliances, granite countertops & recessed lighting. The ½ bath & laundry room complete the 1st floor. The 2nd floor boasts 3 generously sized bedrooms, a full bath & a 4th room that could serve as an office or nursery. Containing an unfinished lower level, this home has plenty of room for future expansion. Offering a level fenced-in backyard & plenty of off-street parking, take this opportunity to establish your family in one of the most sought after communities in the Boston area.

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

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Longwood Residential
1309 Beacon Street | Suite 300
Brookline MA, 02446
Office: 617.396.3100

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.52% last updated on Jul 19, 2018
* 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 Oak Street, Winchester, MA

Price$1,199,000

Est. Mortgage: $/month

MLS Number 72358421

  • Single Family
  • Parking Spaces 6
  • Year Built 1860
  • Full Bath 3
  • Bathroom 4

The 4th of July may be over, but you'll still be seeing fireworks after touring 29 Oak Street in Winchester! Envision yourself re-living the summer day that we wait for all winter long. Host another memorable BBQ in the lovely yard and grill on the patio. Whip up a flag cake on your center island in your gorgeous designer kitchen with granite counters and stainless appliances. Watch your guests stir up a refreshing cocktail in your dining room, thanks to the thoughtful open concept layout of the first level. Central A/C too cold? Turn on your fireplace in the living room and keep the entertaining going! After a long day of enjoying family and friends head upstairs and take your nights rest in one of the 4 bedrooms. Included in those 4 bedrooms are (2) master suite options! All ideal for kicking back and remembering the laughs and fun of the day you just had. But it doesn't have to be over. Make 29 Oak yours and recreate this lovely day again and again for many years to come ...

Listed by Philip J. Vita and Casey L. Elia of Leading Edge Real Estate

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Longwood Residential
1309 Beacon Street | Suite 300
Brookline MA, 02446
Office: 617.396.3100

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.52% last updated on Jul 19, 2018
* 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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258 Cross Street, Winchester, MA

Price$759,000

Est. Mortgage: $/month

MLS Number 72357284

  • Single Family
  • Parking Spaces 4
  • Year Built 1860
  • Full Bath 2
  • Bathroom 2

This gracious home is just minutes away from downtown Winchester and its charming amenities, including shopping, restaurants, Farmer’s Market, library, award-winning schools, parks, and commuter rail. The 2,600 acre Middlesex Fells reservation is close by, known for walking, running & biking trails. The updated kitchen offers a spacious layout, with gas stove, pantry, mudroom, and pass-through to the dining room. The living room's high ceilings and large windows offer a sunny spot to relax or entertain. The second floor offers two full baths, a linen closet with laundry, and two bedrooms, including an unusually spacious master for a house of this era. The third floor has two more bedrooms, and a large storage space.The basement offers plenty of storage space and a walk-out bulkhead to the fenced backyard. There is also large side yard, perfect for outdoor games. Replacement windows throughout, central air, irrigation system. Great opportunity to enjoy all that Winchester has to offer.

Listed by Theuer, Pirani & Wile and Peter Pirani of Leading Edge Real Estate

{$office->Name}

Longwood Residential
1309 Beacon Street | Suite 300
Brookline MA, 02446
Office: 617.396.3100

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.52% last updated on Jul 19, 2018
* 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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40 Forest Street, Winchester, MA

Price$769,000

Est. Mortgage: $/month

MLS Number 72355219

  • Single Family
  • Parking Spaces 3
  • Year Built 1927
  • Full Bath 1
  • Bathroom 3

A truly immaculately maintained home with lots of love and care. Great opportunity for a family to get into Winchester at a great price. House freshly painted, newer appliances, recently replaced windows. Great location, family oriented town. Muraco elementary school and high school are within the walking distance. Finished basement and enclosed porch add to the living space. A lot of children activities including kids playground, soccer field, tennis courts, gymnastic, ballet, Kidstock Creative Theater, music lessons etc near by. Main improvements: 2008 Roof replacement, 2007 Installed Liners-6 stainless steel furnace flue, 2013 new boiler conversion to gas, 2015 2nd floor windows replacement, 2016 house insulation cellulose, 2017 1st floor windows replacement and full bath on the second floor and haft bath on the first floor renovated. 2018 painted almost all the rooms inside the house and installed new water tank

Listed by Aleksandr Sukennik of Boston Hub Real Estate

{$office->Name}

Longwood Residential
1309 Beacon Street | Suite 300
Brookline MA, 02446
Office: 617.396.3100

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.52% last updated on Jul 19, 2018
* 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 Middlesex Street, Winchester, MA

Price$1,399,900

Est. Mortgage: $/month

MLS Number 72353281

  • Single Family
  • Parking Spaces 4
  • Year Built 2018
  • Full Bath 3
  • Bathroom 4

Welcome home to this beautiful new construction colonial, with 4 bedrooms and 3.5 baths, located just north of the center within walking distance to Lynch School. This architecturally designed home has over 3,500 sq ft of stunning interior living space with hardwood floors, crown molding and wainscoting to enhance the character and charm. Offering all of today’s amenities with a 2-car garage, direct entry into the mudroom, custom kitchen and adjacent family, dining and formal living room. Large sliders and windows fills the family and dining room with an abundance of natural light which overlook a private backyard with your own spacious deck and manicured lawn. The second floor features a master suite with walk-in closet and en-suite bath. A separate laundry room, 3 spacious bedrooms and 2 additional full baths complete this level. The versatile third floor and lower level offer plenty of space for a media room, au-pair suite, gym, office and potential for additional bedroom & bath.

Listed by Theuer, Pirani & Wile and Julie Wile Fish of Leading Edge Real Estate

{$office->Name}

Longwood Residential
1309 Beacon Street | Suite 300
Brookline MA, 02446
Office: 617.396.3100

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.52% last updated on Jul 19, 2018
* 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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26 Pond Street, Winchester, MA

Price$1,149,990

Est. Mortgage: $/month

MLS Number 72351738

  • Single Family
  • Parking Spaces 7
  • Year Built 1841
  • Full Bath 3
  • Bathroom 3

Elegance, style and grandeur! Welcome to The Barstow House, built in 1841, listed as a historic home on the National Registrar. METICULOUSLY cared-for and loaded with character, this picture perfect Greek Revival home seamlessly blends old-world charm with modern comfort and convenience. Energy Efficient home with solar panels, 5-zone heating system and more to reduce your carbon footprint! Front-to-back living room/dining room book-ended by dueling marble fireplaces under soaring 9-foot ceilings sets the perfect scene for family and friendly gatherings. Outside, almost a full half-acre of usable, level land. Separate side entry from driveway grants option of turning the library/sunroom into the Perfect Home Office! Behind the home sits the beautiful 2 car Carriage House w/heated and insulated 2nd floor studio/shop space. After dinner, take the walking trail at the rear of the property right to the top of Horn Pond Mountain for sunset views of Boston! Don't miss this rare opportunity!

Listed by Russell Hulteen and Ida M. Bianco of Coldwell Banker Residential Brokerage - Winchester

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Longwood Residential
1309 Beacon Street | Suite 300
Brookline MA, 02446
Office: 617.396.3100

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.52% last updated on Jul 19, 2018
* 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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42 Cabot Street, Winchester, MA

Price$2,175,000

Est. Mortgage: $/month

MLS Number 72351616

  • Single Family
  • Parking Spaces 6
  • Year Built 1920
  • Full Bath 4
  • Bathroom 5

Stunning Colonial Revival from the 1920's, which was renovated and restored by the popular TV Show and website "This Old House" in 2002. Combining the most modern and exquisite details, this 5 bedroom, 4.5 bath home is sure to amaze you! Complete with an elegant dining room with custom built-in shelves, formal living room w/ fireplace and gorgeous beamed ceiling, an inviting sunroom and immaculate eat-in kitchen featuring stainless steel appliances, gas stove and pantry with wine refrigerator. Steps up to the 2nd floor, you will find 3 generously sized bedrooms and 2 full baths; inclusive of the master suite with dream walk-in closet and renovated master bath. The 3rd floor boasts 2 additional bedrooms, a cedar closet and full bath. The finished lower level contains a media room, full bath, laundry room and ample storage. During the warmer months, escape to the serene fenced in backyard setting. With a 2 car garage and incredible location in the Flats, make this magnificent home yours!

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

{$office->Name}

Longwood Residential
1309 Beacon Street | Suite 300
Brookline MA, 02446
Office: 617.396.3100

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.52% last updated on Jul 19, 2018
* 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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1 Woodside Road, Winchester, MA

Price$1,349,000

Est. Mortgage: $/month

MLS Number 72349385

  • Single Family
  • Parking Spaces 2
  • Village Flats
  • Year Built 1895
  • Full Bath 3

Welcome to the Flats! Beautiful 1895 Colonial on a 12,000sqft lot, just 1mile from the town center. Private and serene back yard with a blue stone patio and new 6ft cedar fence located directly off the kitchen. Sprinkler system and NEW 2-car garage with a 22x14 2nd floor just waiting for your imagination to finish. An inviting front porch opens into the grand foyer with a classic staircase. Bright, sun-drenched double parlor with lovely built-in details. Formal dining room, kitchen with granite counters/island, gas stove, stainless steal appliances and half bath complete the 1st floor. The second floor offers a master bedroom with new wood floor, walk-in closet, beautifully updated master bath, three additional bedrooms and large family bath. Third floor is wonderful space with full bath, 2 bedrooms and ample storage. The partially finished lower level is great flex space with even more storage options. Great home in a fantastic location...come enjoy all Winchester has to offer!

Listed by Catherine Albiani and Carrie Simpson of Century 21 Commonwealth

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Longwood Residential
1309 Beacon Street | Suite 300
Brookline MA, 02446
Office: 617.396.3100

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$
$
%
$/month over payments
Federal 30-year interest rate: 4.52% last updated on Jul 19, 2018
* 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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203 Highland Avenue, Winchester, MA

Price$979,000

Est. Mortgage: $/month

Active With Contract

MLS Number 72349022

  • Single Family
  • Parking Spaces 4
  • Year Built 1869
  • Full Bath 3
  • Bathroom 3

Charming Farmhouse style home within walking distance of Town Center, Schools, Commuter Rail, Middlesex Fells Reservations, and amenities! This bright and sunny property offers many features that are sure to appeal to today's buyers: beautifully remodeled kitchen with granite counter tops & stainless appliances, generous master bedroom suite with a fireplace and ensuite bath, a home office/study on the 2nd floor, 3 full bathrooms, Central AC, tasteful lighting, lovely hardwood floors, 1st floor laundry, ample closets, and much more. The 4th bedroom/Family Room on the 1st floor adds flexibility of living arrangements. The landscaped backyard, front porch, and 1-car attached garage complete the setting for this picturesque property located on a large corner lot. Convenient access to the highways allows for ease of commuting.

Listed by Seeme Moreira of Coldwell Banker Residential Brokerage - Winchester

{$office->Name}

Longwood Residential
1309 Beacon Street | Suite 300
Brookline MA, 02446
Office: 617.396.3100

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.52% last updated on Jul 19, 2018
* 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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18 Chester Street, Winchester, MA

Price$1,288,000

Est. Mortgage: $/month

MLS Number 72348257

  • Single Family
  • Parking Spaces 4
  • Year Built 1870
  • Full Bath 3
  • Bathroom 4

New to market! Luxury Colonial Style Home located on a quiet tree lined street just a short distance to Winchester Center, Town Schools, MBTA Commuter Rail & Middlesex Fells Reservation. You'll love the Spacious Open Concept first floor as it features an Amazing Chef's kitchen with lots of Natural Light, Frigidaire SS Appliances and Granite Counters! With 3 levels of living this home does not disappoint as there is room for everyone! Submit your offer today!

Listed by Miles Plant of Boston Local Properties, LLC

{$office->Name}

Longwood Residential
1309 Beacon Street | Suite 300
Brookline MA, 02446
Office: 617.396.3100

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.52% last updated on Jul 19, 2018
* 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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77 Irving Street, Winchester, MA

Price$1,429,900

Est. Mortgage: $/month

MLS Number 72348251

  • Single Family
  • Parking Spaces 2
  • Year Built 2018
  • Full Bath 3
  • Bathroom 4

Currently UNDER CONSTRUCTION and almost complete~ Enjoy designer chosen finishes in this new construction home by local premier builder! Located on a lightly traveled dead end street off Washington and behind desirable Muraco Elementary School, this stunning 4 bedroom 3 1/2 bath home features an ideal open floor plan, bright kitchen with quartz island and stainless steel appliances, family room with corner gas FP and high end finishes throughout. High ceilings, large sunny rooms, 4 generous bedrooms, luxurious master suite with huge walk-in closet and master bath featuring custom shower & soaking tub~ Great rear yard and deck! Finish the basement as you desire~ Located only 7 miles from Boston, close to center of town and public transportation...don't miss the opportunity to occupy this home before the end of summer! Schedule your private showing today! (please excuse the on-site unwanted images :)

Listed by Kim Covino of Leading Edge Real Estate

{$office->Name}

Longwood Residential
1309 Beacon Street | Suite 300
Brookline MA, 02446
Office: 617.396.3100

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.52% last updated on Jul 19, 2018
* 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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104 Hillcrest Parkway, Winchester, MA

Price$1,250,000

Est. Mortgage: $/month

MLS Number 72347971

  • Single Family
  • Parking Spaces 4
  • Year Built 1926
  • Full Bath 2
  • Bathroom 3

Welcome to 104 Hillcrest Parkway! Located directly across from the breathtaking Middlesex Fells Reservation. This picturesque street truly is one of the most enticing in all of Winchester. Home has been exceptionally maintained and is bursting with character. Main level is ideal for entertaining with it's brilliant open floor plan and stunning hardwood floors. Massive family room with gorgeous built in book cases, eat-in kitchen, mudroom with a slider to the patio. There is also a living room with a gas fireplace, elegant dining room, and an office with it's own half bath. Sprawling master suite has 2 walk-in closets, and a balcony overlooking the backyard. Bonus heated room above the 2 car garage offers a variety of uses. Ecostar Majestic Slate roof is environment-friendly and super efficient. Central A/C, newer hot water heater, main level laundry and more. Winchester has a superior school system, easy access to Boston, and a great downtown area. The perfect town to raise a family!

Listed by Ryan Mirisola of Premier Homes Real Estate

{$office->Name}

Longwood Residential
1309 Beacon Street | Suite 300
Brookline MA, 02446
Office: 617.396.3100

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.52% last updated on Jul 19, 2018
* 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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4 Ravine Road, Winchester, MA

Price$2,499,000

Est. Mortgage: $/month

MLS Number 72348070

  • Single Family
  • Parking Spaces 6
  • Year Built 2001
  • Full Bath 5
  • Bathroom 7

UNBEATABLE LOCATION, SITUATED IN THE HEART OF DOWNTOWN WINCHESTER!!! Enter into the dramatic 2-story foyer featuring one of three Swarovski Crystal Chandeliers! Host a dinner party in the Chefs kitchen boasting granite counters, a 48"SUBZERO refrigerator, a 60"gas WOLF range & 2 BOSCH dishwashers. Step out into the pristine garden with built in BBQ and outdoor pizza oven! The dining room has built-in china cabinets, a fireplace and is surrounded with beautiful windows. 5 bed suites, each w/private bath. A Master bed fit for a King & Queen! Seamless flow throughout provides unparalleled luxury living on 4 levels. Gorgeous media room on lower level, featuring a home theatre and bar. Newly finished hardwood floors , and many rooms recently painted. Walk to the farmer's market on the common and explore Winchester's boutiques, restaurants & coffee shops or take the commuter rail to North Station for a day in the city. Within the Ambrose school district and 7 miles North of Boston.

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

{$office->Name}

Longwood Residential
1309 Beacon Street | Suite 300
Brookline MA, 02446
Office: 617.396.3100

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.52% last updated on Jul 19, 2018
* 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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185 Mystic Valley Parkway, Winchester, MA

MLS Number 72347765

  • Single Family
  • Parking Spaces 3
  • Year Built 1859
  • Full Bath 1
  • Bathroom 2

With its premier downtown location, enjoy all that Winchester has to offer just out your front door! Beautifully situated on a picturesque, tree lined street, the home is just minutes from Winchester’s Victorian downtown’s shops and restaurants, award-winning schools, and Commuter Rail station. Built in the 1850s, this historic Colonial features high ceilings, wide pine flooring, and newer windows. This is the perfect opportunity for a savvy buyer to modernize and restore the property to its original glory. Enjoy summer barbecues on the secluded backyard patio and near-limitless outdoor activities are yours to explore in the Middlesex Fells Reservation. A unique opportunity to own a special home.

Listed by Stephanie Walsh and Monika Kordowska of Better Homes and Gardens Real Estate - The Shanahan Group

{$office->Name}

Longwood Residential
1309 Beacon Street | Suite 300
Brookline MA, 02446
Office: 617.396.3100

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.52% last updated on Jul 19, 2018
* 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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