5 Charming New England Homes and Waterfront Retreats Under $300K

Originally built in 1910, this Colonial in East Canaan offers the kind of old-house canvas that invites thoughtful restoration. Currently configured as a two-family, it includes a 2-bedroom apartment on the first floor and a 1-bedroom apartment on the second, with the flexibility to convert back into a spacious single-family residence. The main level is anchored by a large country-style eat-in kitchen with a fireplace and pantry, alongside a generous living room and two bedrooms. Upstairs, the second-floor apartment provides its own kitchen and living room, plus a bedroom and full bath—an arrangement that suits multi-generational living or extended stays. A screened porch opens to a nice backyard, rounding out the home’s everyday rhythms. With plenty of potential throughout, it’s ready to be brought back to its full charm and character.

Along the water’s edge in Ashland, this rare Squam offering centers on a hard-to-find, highly desirable large slip—an easy launching point to explore pristine Squam Lake. The everyday rhythm is refreshingly simple: no trailering, no extra logistics. Just hop in and head out, with the lake’s celebrated quiet coves and “nooks and crannies” opening up in every direction. Convenience comes built in, with straightforward access to I-93 for weekends that begin quickly and end late on the water. For those who love a place with a story, Squam’s cinematic legacy adds a subtle layer of charm—this is the lake where *On Golden Pond* was filmed. It’s a small footprint with an expansive horizon, made for unhurried days afloat.

Size: –

Along the water’s edge on Cobbosseecontee Lake, Lot 9 Wentworth Cove sets the scene for an easygoing Maine lake routine. The listing invites you to bring your boat and lean into the rhythms of waterfront living—morning launches, unhurried afternoons on the water, and evenings that naturally drift back to the shoreline. Located in West Gardiner, this offering centers on access to the lake itself, making time outdoors feel like the main event. Whether you’re planning simple weekends by the water or longer stays that revolve around boating, the focus here is clear and refreshingly straightforward: a place to start enjoying lake life, right where Cobbosseecontee Lake meets the cove.

Size: 2.00 acres

Set on 9.75 acres in the heart of Manchester, this parcel offers a rare blend of space and practical infrastructure. With public water and sewer connections available, the land is positioned for a range of future possibilities, whether held as a long-term investment or explored as a development opportunity. The setting invites a quieter, more expansive daily rhythm—room to imagine how roads, homes, or shared green space might take shape over time—while still being tied into municipal services that can simplify next steps. In a town context like Manchester, having acreage of this scale with public utilities on hand can be an increasingly hard combination to find. It’s a straightforward canvas, ready for a vision that fits the landscape and the community around it.

Size: 10.00 acres

Set on Robinson Hill Road in Oxford, Maine, this move-in ready farmhouse offers a straightforward, country-minded lifestyle with space to spread out. The classic farmhouse setting is complemented by a barn and a dedicated workshop—an appealing trio for anyone who values hands-on projects, storage, or room for hobbies that don’t belong indoors. With its move-in ready condition, the day-to-day feels refreshingly simple: settle in first, then take your time shaping the outbuildings to suit your routines, whether that means tinkering in the workshop or organizing gear in the barn. It’s the kind of property that supports quiet productivity and practical comfort, where home life can extend naturally beyond the main house and into the working spaces just steps away.