Connecticut’s high-end residential market delivered a remarkable series of transactions in 2025, showcasing the continued strength and allure of luxury real estate in one of the Northeast’s most desirable states. Despite broader trends of cautious spending and rising interest rates seen across many segments of the national housing market, Connecticut’s ultra-wealthy buyers remained highly active, closing multi-million-dollar deals that set new benchmarks in both pricing and prestige.
The most expensive sale of the year took place in Westport, where the former estate of television icons Phil Donahue and Marlo Thomas sold for an astonishing $54 million. The estate, spread across three parcels, was a defining example of the kind of unique and expansive properties that continue to attract top-tier buyers in Fairfield County. The property’s sale marked not just a financial milestone but also a symbolic one, representing the region’s enduring appeal to celebrities, executives, and investors seeking privacy, space, and proximity to New York City.
Not far behind in value, a Greenwich estate located on Clapboard Ridge Road sold for $43.5 million, making it one of the largest single-parcel residential deals in the state’s history. The property, a sprawling 26,000-square-foot mansion, featured every conceivable amenity—from indoor pools and home theaters to extensive landscaping and custom architectural elements. The sale reaffirmed Greenwich’s role as a cornerstone of Connecticut’s luxury real estate market and a consistent draw for high-net-worth individuals, both domestic and international.
In Branford’s picturesque Thimble Islands, a different type of luxury transaction caught the eye of real estate watchers. A group of three homes located on Wayland Island was sold together for $2.75 million. Though significantly lower in price than the Greenwich and Westport deals, the transaction stood out for its uniqueness. The island property, featuring 14 bedrooms and surrounded by Long Island Sound, captured the imagination of buyers seeking seclusion and charm in a truly distinctive setting.
Westport continued to be a hotspot for luxury real estate beyond just the Donahue estate. A Georgian-style mansion on Langhorne Lane sold for $17.4 million, offering 17 bathrooms, a stately exterior, and interiors that balanced traditional elegance with modern luxury. The property was emblematic of the kind of classic architectural style that has retained enduring appeal among buyers who value historic character blended with contemporary upgrades.
Greenwich saw additional major transactions throughout the year. One notable waterfront property on Mead Point changed hands for $40 million, further illustrating the premium placed on water access and scenic views in the area’s most exclusive enclaves. Meanwhile, the condominium segment also saw significant activity, including a penthouse unit at The Modern selling for $6.2 million. The high-end condo market, once seen as secondary to single-family estates in Connecticut, began to show signs of rising prominence in 2025, especially among buyers seeking a more manageable footprint with upscale finishes and amenities.
The diversity of the luxury market was also reflected in historic home sales. In Essex, a residence dating back to 1647 was the oldest home sold in the state in 2025. These kinds of transactions speak to the strong emotional and historical connection that some buyers have to properties with legacy value. The demand for homes with storybook charm and architectural significance remained solid, often attracting buyers willing to invest in restoration and preservation as part of their purchase goals.
The state government also participated in notable real estate transactions. In Killingly, Connecticut acquired 640 acres of land for the purpose of expanding public parkland and conservation areas. Though not a residential deal, the acquisition was significant for its scale and environmental implications, highlighting the broader role that real estate plays in public planning and sustainability efforts.
In Westport’s Daybreak Commons, a residence in an age-restricted, 55-and-older community sold for $2.1 million, marking the highest price for a home in that demographic category in 2025. The sale reflected growing demand for luxury retirement and active adult housing, where affluent older buyers seek comfortable, well-located homes with access to lifestyle amenities and services tailored to their needs.
Connecticut’s luxury market remained strong even as the overall housing sector saw only modest gains statewide. Buyers at the upper end of the spectrum appeared less deterred by economic concerns or interest rate fluctuations, focusing instead on lifestyle, exclusivity, and location. Waterfront properties, estates with historic relevance, and homes with unique geographic or architectural features remained especially desirable, while developers and brokers noted sustained demand for quality over quantity.
With 2025 drawing to a close, these headline-grabbing transactions reinforced Connecticut’s reputation as one of the premier destinations for luxury residential real estate in the country. As the market moves into 2026, brokers anticipate continued activity in the top-tier segment, supported by stable demand, limited inventory of truly exceptional properties, and the enduring appeal of Connecticut’s blend of elegance, natural beauty, and proximity to urban centers.
These landmark sales served not only as indicators of market strength but also as reflections of a broader narrative: even in a time of shifting economic headwinds, the appetite for distinctive, well-situated luxury homes remains strong among discerning buyers.
