Refine Search
Map
Sort by
$749,000
4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24196454 MLS
Older than America, the historic Chilson Bailey House offers a rare opportunity to own a true circa 1750 center-chimney Colonial while enjoying the comfort of a thoughtfully designed 2008 addition. Offering four bedrooms in total, two bedrooms are located within the original 1750 portion of the home, which is not currently livable and requires renovation. This gives the next owner the opportunity to restore an authentic piece of Connecticut history at their own pace while enjoying comfortable living from day one. Everyday living takes place in the 2,963-square-foot addition, featuring a spacious country kitchen with an oversized island, a soaring great room with a floor-to-ceiling stone fireplace, wide-plank pine floors, a first-floor primary suite, and an expansive second-floor loft ideal for a home office, family room, or creative space. Outside, an impressive barn and detached garage offer exceptional space for car collectors, hobbyists, contractors, woodworking enthusiasts, or anyone needing room for projects, equipment, or recreational vehicles. Significant improvements have already been completed, including the addition, detached garage, septic system, 200-amp electrical service, leased solar, and new windows in the original home. For the buyer who sees possibility where others see a project, this is a chance to live comfortably today while bringing the historic heart of an extraordinary Connecticut property back to life.

19 High St, Middlefield
$729,999
3 Beds ⋅ 3 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 24195983 MLS
Welcome Home to Middlefield! Experience the perfect blend of modern comfort and timeless farmhouse charm in this stunning new construction ranch, thoughtfully designed for effortless one-level living. Situated on a clear, level, and fully usable one-acre lot just up the hill from beautiful Lake Beseck, this home offers the ideal combination of privacy, convenience, and style. Boasting 2,278 square feet, this spacious home features three bedrooms, 2.5 bathrooms, and an attached two-car garage. The open-concept floor plan is designed for both everyday living and entertaining, with a welcoming great room that serves as the heart of the home. Unwind in the bright and inviting sunroom, or enjoy the ease and accessibility that only single-story living can provide. Located in the thriving town of Middlefield, this property offers the best of both worlds-peaceful rural surroundings with exceptional access to major amenities. Commuters will appreciate the convenient highway access, placing New Haven just 20 minutes away and Hartford approximately 25 minutes away. Outdoor enthusiasts will love being just minutes from Lake Beseck, scenic hiking trails, championship golf courses, and nearby ski areas. Excellent schools, shopping, dining, and a variety of cultural attractions are all within easy reach, making this an exceptional place to call home. There's still time to select your finishes so don't wait long! Please note, pictures and drawings may contain optional fini

123 Way Rd, Middlefield
$625,000
3 Beds ⋅ 2 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 24195242 MLS
Cavanaugh & Company is proud to present 46 Powder Hill Road, a beautifully maintained Center Hall Colonial home in one of Middlefield's most desirable neighborhoods. Designed for both everyday living and entertaining, this exceptional home features a bright, open first floor with newly refinished hardwood flooring, spacious living areas, and a beautifully appointed kitchen complete with granite countertops, premium stainless steel appliances, and a center island. The family room offers built-ins, a gas fireplace, and access to a back patio equipped with a Weber grill. This level also includes a living room with a large wood-burning fireplace and custom screen, a fully remodeled bathroom with high-end features, and an inviting sunroom with private views of nature and professionally landscaped gardens. The second floor features three generously sized bedrooms and a fully remodeled, luxury bathroom with heated flooring. For your safety and convenience, the property also comes equipped with a generator. This home is conveniently located just minutes from downtown Middletown, Wesleyan University, shopping, dining, parks, golf courses, and major highways.

46 Powder Hill Rd, Middlefield

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.