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Winchester Home Search

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Newest Listings in Winchester, MA

6 Ivy Cir, Winchester image
6 Ivy Cir, Winchester $1,449,000

First time on the market; one owner for 57 years. Enjoy all Winchester has to offer in this Colonial at the end of a cul-de-sac with a near center location. Hardwood fl...

  • 3 Beds
  • 2 Baths
  • 73118070 MLS
  • NEW Status
Courtesy of Leading Edge Real Estate

Listing courtesy of Leading Edge Real Estate.

14 Bonad Rd, Winchester image
14 Bonad Rd, Winchester $1,375,000

Tasteful updates & thoughtful design shine through in this meticulously cared for Cape-Cod style home. Step into the bright and airy dining room adorned w/ elegant French...

  • 3 Beds
  • 3 Baths
  • 73115173 MLS
  • NEW Status
Courtesy of Barrett Sotheby's International Realty

Listing courtesy of Barrett Sotheby's International Realty.

62 Richardson St, Winchester image
62 Richardson St, Winchester $1,060,000

Stunning Two-Family home in idyllic Winchester - Ideal for multi-generational living, investors or buyers looking for a top rated School District. This home is perfectly ...

  • 5 Beds
  • 3 Baths
  • 73117876 MLS
  • NEW Status
Courtesy of Strategy Street

Listing courtesy of Strategy Street.

7 Conant Rd Unit 66, Winchester image
7 Conant Rd Unit 66, Winchester — The Willows $749,000

Exceptional Condo Town House at "The Willows" offers 6 rooms, 2 bedrooms, 2.5 bathrooms and 3 balconies all with beautiful tree top views of the lush landscaping at this ...

  • 2 Beds
  • 3 Baths
  • 73117798 MLS
  • The Willows Bldg.
  • NEW Status
Courtesy of Coldwell Banker Realty - Lexington

Listing courtesy of Coldwell Banker Realty - Lexington .

19 West Chardon Rd, Winchester image
19 West Chardon Rd, Winchester $1,250,000

Preparation meets opportunity! Contemporary multi-level with wonderful space & functionality in sought-after neighborhood. This home offers lifestyle advantages on 3 floo...

  • 4 Beds
  • 2 Baths
  • 73117532 MLS
  • NEW Status
Courtesy of Leading Edge Real Estate

Listing courtesy of Leading Edge Real Estate.

29 Edward Dr Unit 29, Winchester image
29 Edward Dr Unit 29, Winchester — Pepper Hill Estates $899,000

Welcome to luxury and convenience at Pepper Hill Estates. This premier end unit townhouse boasts exquisite hardwood floors, recessed lighting, and a chef's dream kitchen ...

  • 3 Beds
  • 4 Baths
  • 73117165 MLS
  • Pepper Hill Estates Bldg.
  • NEW Status
Courtesy of Keller Williams Realty Boston Northwest

Listing courtesy of Keller Williams Realty Boston Northwest.

30 Florence St, Winchester image
30 Florence St, Winchester $649,800

Looking for affordable real estate in desirable Winchester? Contractors and savvy buyers take notice. Built in 1915, this 3 bedroom, 1 bathroom, 1156 sq.ft. Single Family...

  • 3 Beds
  • 1 Baths
  • 73116698 MLS
  • ACTIVE Status
Courtesy of Stuart St James, Inc.

Listing courtesy of Stuart St James, Inc..

1 Marshall Rd, Winchester image
1 Marshall Rd, Winchester $1,999,000

Extensive renovation and addition of classic center entrance colonial. The first floor offers a kitchen with island, gas fireplaced family room with sliders leading to a...

  • 4 Beds
  • 4 Baths
  • 73116002 MLS
  • ACTIVE Status
Courtesy of Better Homes and Gardens Real Estate - The Shanahan Group

Listing courtesy of Better Homes and Gardens Real Estate - The Shanahan Group.

12 James St, Winchester image
12 James St, Winchester $899,000

Great opportunity to own in Winchester. Lovingly maintained ranch style home in Vinson-Owen district features hardwood floors throughout, a sunny living room with firepla...

  • 3 Beds
  • 2 Baths
  • 73115607 MLS
  • ACTIVE Status
Courtesy of Compass

Listing courtesy of Compass.

11 Wickham Rd, Winchester image
11 Wickham Rd, Winchester $3,100,000

Location is key for this stunning Colonial home situated on a quiet street. Exquisite craftsmanship, opulent finishes, & meticulous upgrades define this must-see property...

  • 4 Beds
  • 5 Baths
  • 73114972 MLS
  • ACTIVE Status
Courtesy of Coldwell Banker Realty - Lexington

Listing courtesy of Coldwell Banker Realty - Lexington .

11 Main St, Winchester image
11 Main St, Winchester $1,045,000 ▼

This stunningly updated ranch features new appliances, new granite countertops and backsplash, gleaming hardwood floors throughout the home, and beautifully updated bathr...

  • 3 Beds
  • 2 Baths
  • 73114160 MLS
  • PRICE CHANGED Status
Courtesy of Compass

Listing courtesy of Compass .

89 Thornberry Road, Winchester image
89 Thornberry Road, Winchester $1,799,000

Inviting family home located in a picture perfect neighborhood, situated among beautifully maintained, high-end homes. This 5 Bedroom 2.5 bath colonial will meet your eve...

  • 5 Beds
  • 3 Baths
  • 73113874 MLS
  • ACTIVE Status
Courtesy of Compass

Listing courtesy of Compass .

22 Fletcher St, Winchester image
22 Fletcher St, Winchester $1,150,000

Great single-family alternative in sought after Winchester Flats. This beautiful previously gut-renovated Townhome lives like a single-family with huge backyard and patio...

  • 3 Beds
  • 3 Baths
  • 73113387 MLS
  • ACTIVE Status
Courtesy of Compass

Listing courtesy of Compass .

22 Fletcher St Unit 22, Winchester image
22 Fletcher St Unit 22, Winchester $1,150,000

Enjoy life in sought after Winchester Flats with this beautiful previously gut-renovated Townhome that lives like a single-family with huge backyard and patio. Close to t...

  • 3 Beds
  • 3 Baths
  • 73111198 MLS
  • ACTIVE Status
Courtesy of Compass

Listing courtesy of Compass .

19 Verplast Ave, Winchester image
19 Verplast Ave, Winchester $1,100,000

Colonial farmhouse on private 4,318 sqft lot at the end of a private cul-de-sac. Needs some cosmetics but most major items done. Recent renovations from 2010 include new...

  • 3 Beds
  • 2 Baths
  • 73113100 MLS
  • ACTIVE Status
Courtesy of The Synergy Group

Listing courtesy of The Synergy Group.

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non commercial use of consumers having a good faith interest in purchasing, leasing or renting listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing, leasing or renting. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.

Search All Winchester Real Estate

The Town of Winchester is approximately 8 miles from Boston and it is the 7th wealthiest community in Massachusetts.  Sought after for it's high ranking schools, whimsical town center, and charming New England neighborhoods, Winchester often makes it's way to the top of the wish list for many home buyers.  It's home to the yummy Gingerbread Construction company, walking trails at Horn Pond, and unique shops and restaurants in the center of town.

Learn More About Winchester:

WINCHESTER SCHOOLS

TOWN HALL

WINCHESTER LIBRARY

HORN POND

WINCHESTER RECREATION PROGRAM

WINCHESTER RESIDENTS FACEBOOK PAGE

Our website features the best Winchester real estate search for homes, condos, land and foreclosure properties available. It is the only site you will ever need! It is easy-to-use and updated every 15 minutes.  You can save searches, and get daily email alerts of new listings, price changes, sold data, and market reports. Our Interactive Map Search allows you to view properties on a map or refine your search by drawing the boundaries around the area you desire. 

Curious about what’s happening in your neighborhood? You can create a custom market report to see what’s active, under contract, and sold in your neighborhood! 

Considering selling or refinancing your home? Get an INSTANT property valuation now!

Contact us today to find out how we can be of assistance to you!

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