32 Oakland Ave

Offered for the first time as a rental, this is truly one of the most beautiful and special homes in Sag Harbor Village-an unparalleled summer escape. Tucked away in the heart of Sag Harbor Village, this exceptionally charming and private retreat offers a rare opportunity to experience waterfront living at its finest. Set on 2/3 of an acre and centered on Otter Pond, the home enjoys serene open water views from almost every room, lush mature landscaping, and a sense of tranquility that feels worlds away-yet situated in the heart of town and moments from village shops, restaurants, and marinas. Designed for both relaxation and entertaining, the property features a large pool, an expansive veranda perfect for al fresco dining, and multiple indoor living spaces including three beautifully appointed living rooms filled with natural light. Additional highlights include a dedicated home office, a gym, and a garage for added convenience. Current Availability: Off Season (9/8/26-4/30/27): $130,000 Year round: $325,000 February 2027: $15,000 March 2027 $15,000 April 2027: $20,000 5/1/2027- 5/23/2027: $25,000 June 2027: $60,000 July 2027: $125,000 August-LD 2027: $135,000 MD-LD 2027: $295,000