The Rose Hill estate in Southport, CT has topped the list of luxury real estate transactions in Fairfield, CT with a record-breaking $15 million sale. Located at 385 Harbor Road (photos) in the heart of the Southport Historic District, Rose Hill is a property steeped in history, offering a combination of architectural grandeur, modern amenities, and breathtaking waterfront views.
A Legacy of Elegance
Originally constructed in 1854, Rose Hill has long been a landmark in Southport. Its Italianate design is a showcase for 19th-century architecture, with intricate details and commanding proportions. The estate was once home to Dennis Dammerman, a former vice chairman of General Electric. After his passing in 2013, Rose Hill was sold for $9 million to owners who spent $1.3 million to modernize the property.
A Waterfront Haven
The estate spans nearly two acres, making it one of the largest properties in Southport Village. With 265 feet of direct waterfront access and a private dock, Rose Hill offers uninterrupted views of Southport Harbor, the fairways of the Country Club of Fairfield, and the expanse of Long Island Sound.
The 10,000-square-foot main house features expansive public rooms with high ceilings, perfect for hosting elegant gatherings. Large windows frame the picturesque surroundings, filling the interiors with natural light. Adding to its appeal, the estate features a detached guest house above a three-car garage, offering a private one-bedroom apartment with a kitchen and full bath. Other amenities include a pool, a bocce court, and landscaped gardens.
Redefining Fairfield’s Market
This $15 million sale not only set a record for Fairfield this year, but also positioned Rose Hill among the top residential transactions in Connecticut for 2024, highlighting the strength of the state’s high-end real estate market. The transaction underscores Southport’s unique appeal as a destination for buyers seeking historic properties with modern amenities in an idyllic waterfront setting.
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
