5 Maine and Connecticut Listings with Homes, Land, and Lakefront

In the heart of downtown Winthrop along busy Route 133, this commercial building is positioned on a major connector road with high traffic counts—an address designed for visibility and everyday flow. Inside, the first floor offers 3,100 square feet of usable space, organized into a straightforward working layout that supports a range of operations. The floor plan includes four distinct shop areas plus an office, with a bathroom on the first floor for added convenience. Two of the shop areas feature radiant heat in the floor, providing a strong foundation for comfort, while leaving room to add the needed heat source. With its practical footprint and central in-town setting, the space invites an owner to shape it into something tailored, efficient, and deeply connected to Winthrop’s daily rhythm.

On a quiet in-town address in Randolph, this charming, well-maintained home balances comfort, character, and day-to-day convenience. Hardwood floors run throughout both levels, lending continuity and warmth from room to room. Interiors feel generous and inviting, with large spaces and many windows that bring in natural light. A mudroom entry sets an easy, lived-in tone, while the thoughtfully designed first floor is arranged for smooth flow—equally suited to everyday routines and hosting. The kitchen connects naturally to a formal dining room, and the home offers both a spacious living room and a comfortable family room, creating distinct places to gather or unwind. A convenient half bath rounds out the main level. The result is a home that feels welcoming from the moment you step inside and continues to live well through every season.

Set in the bucolic foothills of the Litchfield Hills, 17 Old Homestead Lane offers a rare stretch of park-like land in St. John’s Peak, one of Connecticut’s most tranquil enclaves. The setting invites a slower rhythm—room to roam, reflect, and imagine a future home shaped around the landscape. Old-age rock walls lend a sense of history and texture, while wetlands and conservation at the back of the lot provide a natural buffer and open up options for home placement toward the front. Outdoor life extends beyond the property line, with a nature preserve directly behind and additional preserves throughout St. John’s Peak. When you want a change of pace, the beloved downtown of Kent is close by, along with Lake Waramaug, Warren, and New Preston—an easy orbit for culture and natural beauty.

Size: 12.00 acres

Along the water’s edge on Cobbosseecontee Lake, this waterfront offering invites an easy, on-the-water routine from day one. Bring your boat and settle into the rhythms of lake life, with the added option to buy into the private community dock association for convenient shared docking access on highly sought-after Cobbossee Lake. Set in West Gardiner, Maine, the setting centers daily life around the shoreline—morning departures from the dock, unhurried afternoons on the lake, and evenings defined by the calm that comes with having the water close at hand. With its emphasis on access and simplicity, it’s a place designed to make time on the lake feel less like a weekend plan and more like a natural part of every day.

Size: 2.00 acres

Set on a generous 9.75-acre parcel in the heart of Manchester, this offering is defined by possibility and practicality. With public water and sewer connections available, the land brings rare utility convenience to a setting that still feels expansive and open-ended. The scale invites a wide range of future visions—whether held as a long-term investment or explored as a development opportunity—while keeping everyday access to town close at hand. It’s a straightforward, infrastructure-ready canvas, where the appeal lies in what you can thoughtfully create rather than what’s already built. A property like this supports planning at your own pace, with room to imagine an end result that fits both the site and the rhythms of life in Manchester.

Size: 10.00 acres