Second Hill Real Estate

Welcome to Second Hill, a delightful neighborhood nestled in the heart of New Milford, Connecticut, within the picturesque Litchfield County. This charming community offers a perfect blend of suburban tranquility and vibrant local culture, making it an ideal place for families, professionals, and retirees alike.

Second Hill is characterized by its tree-lined streets and well-maintained homes, creating a warm and inviting atmosphere. Residents enjoy a strong sense of community, with friendly neighbors who take pride in their surroundings. The area boasts a variety of architectural styles, from classic New England colonials to modern designs, providing a diverse selection of homes to suit every taste.

One of the highlights of living in Second Hill is its proximity to nature. The neighborhood is surrounded by beautiful parks and scenic trails, perfect for hiking, biking, or simply enjoying a leisurely stroll. Lake Lillinonah, just a short drive away, offers opportunities for fishing, kayaking, and picnicking, making it a popular spot for outdoor enthusiasts.

Second Hill is conveniently located near the vibrant downtown area of New Milford, where residents can explore charming boutiques, delightful cafes, and a variety of dining options. The community also hosts seasonal events and farmers' markets, fostering a strong sense of local pride and engagement.

With excellent schools, easy access to major highways, and a welcoming atmosphere, Second Hill is not just a place to live—it's a place to thrive. Discover the charm and convenience of this lovely neighborhood and make it your new home today!

Newest Listings in Second Hill

$829,500

3 Beds ⋅ 4 Baths ⋅ 24194207 MLS

This quintessential Connecticut home with over $240K improvements is nestled on a picturesque very private 2-acre lot bordering the scenic 150- acre Second Hill Reservoir and preserve. This beautifully updated Cape featuring handsome stonework warming both the exterior and interior offers the perfect blend of privacy, nature, and convenience. With 3 bedrooms, 3.5 baths, this home features a flexible floor plan ideal for full-time living or a weekend retreat. The spacious living room with 10-foot ceilings showcases hardwood floors and a stunning stone fireplace, while the bright sunroom invites year-round enjoyment of the surrounding landscape. Two main-level bedrooms offer private full baths, including a primary suite with direct access to the sunroom. Upstairs, an additional bedroom and full bath provide excellent guest accommodation and peaceful hillside views. The partially finished walk-out lower level offers abundant space for recreation, hobbies, or a home office. An oversized detached two-car garage and level backyard complete the package. Located just minutes from New Milford's charming town green, shopping, dining, and hospital, this property is a rare opportunity to enjoy country living with modern convenience. Walking trails, kayaking, fishing, and the beauty of the reservoir are right outside your French doors.

142 Second Hill Rd, New Milford

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.