Listed on 09/08/2026

Listed by Jeremy Dunham

Days on market: 29

Property Status: Active Experience effortless Sag Harbor Village living in this impeccably designed one-bedroom, one-bath residence at Watchcase. Offering approximately 1,000 square feet of beautifully appointed interior space, the apartment is ideally located just one block from Main Street and two blocks from the harbor. A private garden-level entrance near the pool leads into an inviting open-concept living and dining area with an eat-in kitchen and seamless access to a private patio. Multiple exposures provide abundant natural light, along with views of the Watchcase gardens, Sag Harbor Village, and the surrounding harbor landscape. Residents enjoy access to Watchcase's exceptional amenity package, including concierge and porter services, an on-site building manager and superintendent, a heated saltwater pool, and the Watchcase Pavilion featuring a fitness center, yoga studio, locker rooms, sauna, spa treatment room, and an elegant events lounge with fireplace and catering kitchen. The Grand Lobby Living Room is home to the Vault Bar and a dramatic two-sided fireplace, creating an additional welcoming space for residents and guests. Blending historic architecture, modern luxury, resort-style amenities, and one of Sag Harbor Village's most desirable locations, this residence offers a rare opportunity to experience the very best of Watchcase living. Office Phone: (631) 875-2475 Copyright © 2026 My State MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.

Listed on 07/20/2026

Listed by Jeremy Dunham

Days on market: 79

Property Status: Active An exceptional one-bedroom bungalow at the renowned Watchcase Factory, this impeccably designed 1,097-square-foot residence offers a rare blend of privacy, sophistication, and world-class amenities in the heart of Sag Harbor Village. Tucked along picturesque Church Street, this elegant pied-a-terre delivers effortless luxury just moments from the Village's celebrated restaurants, boutiques, marinas, and beaches. Thoughtfully designed for seamless indoor-outdoor living, the residence features an expansive open-concept kitchen, dining, and living area that flows gracefully to a beautifully landscaped, sun-filled private garden-an idyllic setting for morning coffee, afternoon lounging, or intimate al fresco dining. A second private patio at the front entrance offers an additional outdoor entertaining space overlooking historic Church Street. The serene primary suite overlooks the garden and features a spacious walk-in closet and a luxurious four-fixture bath designed with timeless finishes. Direct access from the secure underground garage allows for effortless arrivals and departures, with designated parking space #5 reserved exclusively for the residence. As a guest of Watchcase, enjoy one of the Hamptons' most coveted luxury lifestyle experiences. Resort-caliber amenities include full concierge services, a live-in resident manager, full-time superintendent, complimentary bicycles, a heated saltwater pool, beautifully landscaped owners' park, and the acclaimed Watchcase Pavilion featuring a state-of-the-art fitness center, yoga and Peloton studio, spa treatment room, sauna, elegant locker rooms, and an owners' lounge with fireplace and catering kitchen. The iconic Grand Lobby welcomes residents and guests with the Vault Bar, soaring ceilings, and a dramatic two-sided fireplace, creating an atmosphere of understated elegance. Perfectly positioned just one block from Sag Harbor's charming Main Street and two blocks from the Hamptons' only deep-water marina, this turnkey luxury residence offers an unparalleled opportunity to experience village living at its finest. A refined sanctuary with timeless design, exceptional privacy, and five-star amenities-this is Watchcase living at its very best. Office Phone: (631) 875-2475 Copyright © 2026 My State MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.

Listed on 09/14/2026

Listed by Jeremy Dunham

Days on market: 23

Property Status: Active Instantly delightful, this two bedroom two bath home with 3rd bedroom flex space is accessed through a private garden off the landscaped Church Street courtyard at Watchcase. Offering a spacious greatroom with open kitchen and large center island, the oversized windows open onto the second larger garden allowing light to fill the residence. The exposed brick walls and old pine beamed 11 ft ceilings add to the architectural heritage and Watchcase spirit. The master bedroom offers a generous walk in closet and luxurious 5 fixture master bath with Watchcase signature wetroom. The second bedroom has an en-suite bat also accessible from the living room and gorgeous garden views. One block from Sag Harbor's charming Main Street and two blocks from the Hamptons only deep-water port, Watchcase is a 63 Loft, Town House, and Bungalow condominium amongst elegant landscaped gardens. Residents benefit from an amenity package, including: Resident Building Manager, Concierge, Heated pool, and The Watchcase Pavilion with fitness room, yoga studio, Peloton room, locker rooms with sauna, spa room, and events lounge with fireplace and catering kitchen. The Grand Lobby Living Room hosts the Vault Bar and a massive two-sided fireplace. Office Phone: (631) 875-2475 Copyright © 2026 My State MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.

Listed on 07/03/2026

Listed by Jeremy Dunham

Days on market: 96

Property Status: Active Watchcase Penthouse PH-402 | Sag Harbor Perched high above Sag Harbor Village within the iconic and historically significant Watchcase Factory, Penthouse PH-402 offers a rare opportunity to experience refined Hamptons living with sweeping water views and exceptional indoor-outdoor entertaining spaces. Spanning approximately 1937 square feet over two living levels, this elegant 3-bedroom residence features 2 full bathrooms, 2 powder rooms, and a spectacular private rooftop terrace designed for effortless luxury. The main entry level opens into a dramatic great room, where the kitchen, dining, and living areas flow together beautifully around a fireplace, all framed by captivating views of Sag Harbor. A powder room completes this level. One flight below, the private bedroom level includes two gracious guest bedrooms sharing a full bath, a waterfront-facing balcony, and a sumptuous ensuite primary suite offering a serene retreat. The crown jewel of the home is the rooftop terrace, set far above the village with stunning water views, lounge and dining areas, a gas fire pit, outdoor kitchen, and its own powder room - making it an unforgettable destination for entertaining or quiet evenings under the Sag Harbor sky. Residents of Watchcase enjoy a world-class amenity package, including concierge service, porters, a full fitness center with locker rooms, a yoga studio, a spa treatment room, a sauna, a heated 64' x 22' saltwater pool, a live-in resident manager, and a full-time superintendent. Two parking spaces are also available. A truly exceptional penthouse in one of Sag Harbor's most coveted addresses - come experience the good life at Watchcase. Office Phone: (631) 875-2475 Copyright © 2026 My State MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.