Winchester Condos for Sale

Welcome to Winchester, Massachusetts, a charming town nestled in Middlesex County, where historic charm meets modern convenience. Known for its picturesque streets, vibrant community, and top-rated schools, Winchester offers a unique blend of suburban tranquility and urban accessibility. Just a short drive or train ride from downtown Boston, residents enjoy the best of both worlds—an idyllic lifestyle surrounded by nature and the bustle of city life.

As you explore the real estate market in Winchester, you’ll find an array of stunning condos for sale that cater to diverse lifestyles. Whether you’re a young professional seeking a low-maintenance living space, a growing family looking for a community-oriented environment, or a retiree desiring a peaceful retreat, Winchester’s condos offer something for everyone. Many of these properties boast modern amenities, open floor plans, and beautiful views of the surrounding landscape, providing the perfect backdrop for your next chapter.

The town’s rich history is reflected in its architecture, with many condos featuring unique designs that blend classic charm with contemporary flair. Additionally, residents enjoy easy access to local parks, walking trails, and a vibrant downtown area filled with boutique shops, cafes, and restaurants.

Investing in a condo in Winchester means more than just acquiring a property; it’s about embracing a lifestyle. Experience the warmth of a close-knit community, the beauty of nature, and the convenience of city living—all in one remarkable location. Explore the condos for sale in Winchester today and discover your dream home in this enchanting town!

Newest Winchester Condos for Sale

$179,990

2 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24194479 MLS ⋅ Riverwalk BLDG.

Move right into this well-maintained townhouse offering 2 bedrooms, 1.5 baths, and an attached garage in the desirable Riverwalk community. The spacious living room features a vaulted ceiling, fireplace, and abundant natural light, while the kitchen offers ample cabinet and counter space with sliding door access to a private deck overlooking a wooded backdrop. Upstairs you'll find two generously sized bedrooms, including a primary bedroom with a vaulted ceiling and walk-in closet, along with a full bath. Conveniently located near Routes 8 and 44, Highland Lake, the Farmington River, shopping, restaurants, and outdoor recreation, this home offers comfortable, low-maintenance living in a great location. Schedule your private showing today! Association has scheduled deck replacement for later this year.

111 Riverton Road Unit 57, Winchester

Start Your Search

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.