Jace Lamonica
Connecticut’s upscale enclaves promise prestige and comfort, but the cost of living can be staggering. Here, you’ll find historic estates and vibrant downtowns that attract those with substantial means. For anyone willing to spend a lot on a good living, these ten destinations are perfect for you.
Greenwich
In Greenwich, you’ll find some of the most prestigious waterfront properties in New England. With a median income of $128,839, this affluent town draws hedge fund managers and CEOs seeking privacy and status. Gated estates and high-end boutiques underscore its opulent, high-cost lifestyle.
Westport
The town’s average property value of $614,433 stems from its numerous theaters and art centers that reflect its artsy vibe and attract successful professionals and retirees. Expansive waterfront parks and gourmet dining solidify its reputation as a chic yet costly enclave.
Darien
Finance executives flock to Darien, drawn by its proximity to Wall Street and exclusive residential appeal. The town’s meticulously maintained parks and marinas create a picturesque setting, but the cost of living exceeds 60% of the national average, making it a high-stakes address.
New Canaan
Colonial and Tudor-style homes define New Canaan’s architectural character, with some fetching up to $2 million. Boutique shops and bistros line the charming downtown and attract well-heeled residents who seek a seamless blend of historic architecture and contemporary luxury.
Wilton
With expansive green spaces and farm-to-table dining, this town attracts families looking for a rural feel without sacrificing amenities. A top-tier school district drives up home values to nearly $1.2 million. While families find room to roam, the price of entry stretches budgets.
Ridgefield
Ridgefield’s thriving arts scene includes the Aldrich Contemporary Art Museum, drawing affluent creatives. Maintaining this upscale lifestyle comes with high costs for culture lovers because the area’s colonial-era homes are both a selling point and a financial commitment. The average property value is $912,500.
Weston
Filled with large estates that provide ample privacy, the town provides tranquility but at a cost. Home prices average $753,789, and the lack of commercial development is one of many factors that contribute to higher property taxes. The upscale atmosphere here encourages the influx.
Fairfield
A nightlife and university culture lend to the energy of this coastal town. Yet, its $877,666 median home price is a barrier to entry. Beachfront living and trendy downtown eateries attract high-income earners, and affordability takes a back seat to entertainment.
Stamford
Corporate headquarters and international firms anchor this bustling hub and push housing costs up while creating job opportunities for young, affluent professionals willing to pay for convenience. Stamford’s financial district drives demand for upscale apartments, with median rents exceeding $3,000.
Avon
Avon’s idyllic setting features golf courses, creating a suburban paradise. With homes averaging $497,500, the town attracts nature lovers and families. As property values climb, some residents question whether the town’s charm is worth the escalating cost of living.
