66 Beachside Avenue in Westport, CT, is a 12,500-square-foot contemporary home on two gated acres along Beachside Avenue. Designed by PBS Architects, the property offers Long Island Sound views, private beach access, and a range of indoor and outdoor amenities.
The property includes a heated Gunite pool, spa, stone terrace, and a heated pavilion with an automated screen system, fireplace, and TV. The outdoor kitchen, complete with a pizza oven, provides space for cooking and dining outside. A fire pit and bocce court offer additional outdoor recreation. A private footpath leads to 300 feet of sandy beach, where residents can fish, observe wildlife, or launch a kayak or paddleboard.
The house is designed with open-concept living and extensive glass walls to maximize natural light and views. The entry hall leads to a living room with a linear fireplace, a family room with a vaulted ceiling and wood-burning fireplace, and a chef’s kitchen featuring a 17-foot marble waterfall island, high-end appliances, and a glass-enclosed breakfast room. A butler’s pantry, sunroom, and dining room are also part of the main level.
A glass-lined floating staircase leads to the upper floors. The primary suite features a vaulted ceiling, gas fireplace, private balcony, and a bathroom with a soaking tub, glass-enclosed shower, and double vanity. There are three additional en suite bedrooms on the second level. The third level includes a recreation room with a full wet bar and access to a balcony with a hot tub, as well as a fifth bedroom with an adjacent bath.
The lower level includes a 1,500-bottle wine cellar and a glass-enclosed gym. A separate apartment with a full kitchen, bath, and private entrance provides space for guests, extended family, or a home office.
The property last sold for $10,750,000 in 2024.
Cress is an innovative real estate advisory firm representing buyers and sellers of high-end properties throughout Fairfield County, CT and beyond. On the sell side, Cress delivers marketing-driven support designed to expand visibility and maximize outcomes. Through its co-listing model, Cress partners alongside listing agents to provide digital-first distribution, high-quality content creation, and proactive demand generation strategies that extend well beyond traditional MLS exposure.
On the buy side, Cress offers flat-fee representation and commission rebate programs that bring efficiency and transparency to luxury transactions while maintaining a high standard of service. Known for strategic insight, modern marketing execution, and deep local knowledge, Cress provides a smarter, more aligned approach to buying and selling real estate.
For more information, visit www.callcress.com.
Doug Cress
(212) 203-5251
doug@cress.co
License #RES.0832278
Fairfield County, CT
Enterprise Realty Inc.
License #REB.0751297
45 Huntington Plaza
Shelton, CT 06484
