Chester Homes with Cape Cod Style

Welcome to Chester, Connecticut—a charming riverside town nestled in the heart of Middlesex County. Known for its picturesque landscapes and vibrant community, Chester offers a unique blend of small-town charm and modern amenities. With its historic downtown, filled with quaint shops, art galleries, and delightful eateries, you'll find plenty of opportunities to explore and enjoy local culture. The Connecticut River adds to the town's allure, providing scenic views and recreational activities for outdoor enthusiasts.

One of the standout features of Chester is its stunning array of Cape Cod-style homes. These quintessential New England residences boast a timeless appeal, characterized by their steep rooflines, dormer windows, and shingle siding. With their cozy interiors and functional layouts, Cape Cod homes are perfect for families and individuals alike, offering both comfort and style. Many of these homes are set against the backdrop of Chester’s lush greenery and serene landscapes, creating a peaceful retreat from the hustle and bustle of everyday life.

Living in Chester means embracing a community-oriented lifestyle, with seasonal events and activities that bring neighbors together. From farmers' markets to summer concerts in the park, there's always something happening in this vibrant town. Whether you’re looking to buy your first home or searching for a charming getaway, Chester’s Cape Cod-style residences offer the perfect blend of warmth and character. Discover the beauty of Chester and the inviting charm of its Cape Cod homes—your dream home awaits!

Newest Chester Homes with Cape Cod Style

$499,000

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24189125 MLS

NEW PRICE!! Beautiful view from this WATERFRONT home on Chester Cove! Steps to fishing or kayaking just out your door. Enjoy watching the wildlife from the 20x10 deck directly off the kitchen/dining/living rooms. Wonderful light enters through the abundant windows on the first floor with its open floor plan, kitchen with granite, newer appliances and a window over the kitchen sink you won't want to walk away from; there's also sliders to the deck and a full bath. On the second floor there are three spacious bedrooms along with a second full bath. The whole house underwent full renovations between 2012-2013 including new kitchen, baths, gleaming oak flooring, foam insulation, new HVAC, new electrical; the updates continued along with a new roof in 2017, and just recently new carpeting on second floor, new stove and microwave plus a new dryer. Bring your creativity to finish the lower walk-out level with its charming brick architecture along with newer radiant-heated, poured concrete floors and french doors -- this could be an amazing walkout steps to the water! This house would be a perfect vacation rental.... Rent a few weeks/Stay a few weeks!

135 Middlesex Ave, Chester

$900,000

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24172811 MLS

Welcome to 136 Goose Hill Rd. This home has been tastefully redesigned inside and out with no expense spared. Featuring 4 bedroom, 3 full bathroom, over 3,300 sq ft of beautifully finished living space sitting on just over 2 acres. Step inside to discover all-new hardwood flooring throughout the main level and a thoughtfully designed open-concept layout ideal for both everyday living and entertaining. At the heart of the home is a spectacular chef's kitchen featuring an oversized island, quartz counters, stainless steel appliances, custom wet bar area, formal dining space, and inviting sitting area. Just beyond the kitchen, the great room showcases vaulted ceilings, a fireplace, and an abundance of natural light. The first-floor primary suite is a true retreat with a spacious walk-in closet, and a beautifully remodeled spa inspired bathroom. Upstairs, you'll find three additional bedrooms, another full bathroom, and a dedicated laundry room for added convenience. The finished lower level offers flexible space perfect for a media room, home gym, recreation area, or playroom. Step outside onto the oversized two-tier deck overlooking the expansive backyard - an ideal setting for entertaining or relaxing in total privacy. Additional upgrades include a new roof, windows, siding, HVAC system, and brand-new 5-bedroom septic system. Complete with a 2-car garage and set in a picturesque location, this turnkey property offers the perfect blend of luxury, comfort, and functionality.

136 Goose Hill Rd, Chester

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.