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3 Sold Connecticut Homes with Poolside, Convenient, and Historic Charm

By Awais Manzoor

1 min read

Across three Connecticut addresses, classic New England homes turn outward, treating the backyard as a true extension of daily life. In Woodbury, a cul-de-sac Colonial pairs privacy with a private inground pool and retreat-like setting. Wallingford adds neighborhood ease and commuter access while keeping outdoor living simple on a level lot. On Tolland Green, a Historic Register Italianate residence offers a more storied kind of escape, where heritage and setting shape the experience as much as the house itself.

20 Stagecoach Road | Contact for pricing

20 Stagecoach Rd, Woodbury, CT 06798
20 Stagecoach Rd, Woodbury, CT 06798
robertleonard
LISTING AGENT:
Robert Leonard

Originally built as a classic Colonial, this spacious 4-bedroom residence sits on a cul-de-sac in a highly sought-after Woodbury neighborhood, offering a sense of privacy and calm. Inside, hardwood floors set a warm foundation, while a fireplace anchors the main living space for easy, everyday comfort. The layout extends to a partially finished walkout lower level—ideal for flexible use—opening the home to the backyard setting beyond. Outdoors, a private inground pool and backyard retreat create a summer-ready backdrop for quiet mornings and long evenings at home. Offered strictly as-is, the property is described as having strong bones and needing very little to shine, making it a compelling opportunity for buyers who appreciate location, setting, and the satisfaction of bringing a well-positioned home to its full potential.

Price: Contact for pricing

Size:
2,157 sq ft
Contact:
Robert Leonard, William Raveis, 914.505.4416

18 Reskin Dr | Contact for pricing

18 Reskin Dr, Wallingford, CT 06492
18 Reskin Dr, Wallingford, CT 06492
carolkleeman
LISTING AGENT:
Carol Kleeman

On a quiet street in Wallingford, this three-bedroom home pairs everyday convenience with a calm, lived-in setting. Hardwood floors run throughout, creating an easy continuity from room to room. The walkout lower level adds welcome flexibility, with a workshop area alongside another large room—ideal for projects, storage, or simply spreading out. Outside, a level lot makes the outdoor space feel open and approachable, while the patio becomes a natural spot to unwind as evening sets in. A babbling stream provides a gentle soundtrack, turning simple moments outdoors into a small ritual. Close to Route 5 and I-91, the location keeps shopping, schools, medical services, and restaurants within easy reach, balancing peaceful privacy with practical access.

Price: Contact for pricing

Size:
1,280 sq ft
Contact:
Carol Kleeman, William Raveis, 860.729.6835

714 Tolland Stage Rd | Contact for pricing

714 Tolland Stage Road, Tolland, CT 06084
714 Tolland Stage Road, Tolland, CT 06084
debburlingame
LISTING AGENT:
Deb Burlingame

With heritage dating to Historic Tolland Green, this Italianate Style colonial—listed in the Historic Register—carries a storied past, once owned by Dr. Gilbert Preston, who rebuilt an earlier Salt Box style home into the residence seen today. The current owners have lovingly renovated, updated, and repaired the property from top to bottom, inside and out, with a detailed list of work available through the listing. A side entrance offers flexibility for a private office space or an in-law space, comfortably separated from the main living areas. Outdoors, perennial plantings, stone steps, and walkways create a Zen-like atmosphere that feels thoughtfully aligned with the home’s grandeur. In the backyard, privacy frames easy evenings around the firepit and patio, with room to tinker in the large barn and a structurally renovated two-car garage—spaces that invite both quiet retreat and purposeful projects.

Price: Contact for pricing

Size:
3,064 sq ft
Contact:
Deb Burlingame, Re/Max Bell Park, 401.430.0134