Known as The Old King Farmhouse and Owl Hollow, this historic 1.05± acre compound is one of Peconic’s most distinctive properties, pairing a beautifully preserved c.1860 Italianate Victorian residence with a remarkably purpose-built artist’s studio in the heart of the North Fork.
Rich in history and thoughtfully stewarded over time, the approximately 3,260-square-foot residence offers four bedrooms and two-and-a-half baths while preserving many of its original architectural details, including period fireplaces, wide-plank wood floors, oversized windows, and graciously proportioned rooms filled with natural light. The interiors strike a rare balance between historic character and understated elegance, allowing the home’s craftsmanship and surrounding landscape to take center stage.
Across the grounds, Owl Hollow serves as an extraordinary extension of the property. The approximately 1,200-square-foot studio is defined by soaring timber trusses, dramatic north-facing windows, a wood-burning fireplace, and its own Certificate of Occupancy, offering exceptional flexibility as an artist’s studio, creative workspace, guest retreat, entertaining pavilion, or wellness space.
Set among mature specimen trees, clipped hedges, perennial gardens, and a fenced vegetable garden, the grounds unfold as a series of outdoor rooms centered around a heated 18′ x 36′ saltwater pool. A rare pre-existing, non-conforming wattle-and-daub stable offers additional storage or future possibilities, while separate driveways, updated utilities, new septic systems, rental permits, and separate Certificates of Occupancy further enhance the property’s versatility. Both the residence and studio have an established history as luxury rentals.
Located in the bucolic hamlet of Peconic, moments from renowned vineyards, farm stands, beaches, and marinas, The Old King Farmhouse and Owl Hollow represent an increasingly rare opportunity to own a historic North Fork compound where architecture, landscape, and creative living exist in perfect harmony.
Welcome to your private coastal escape. Set on 2.75 secluded acres overlooking the Long Island Sound, this sun-filled 3-bedroom, 1-bath retreat offers sweeping water views, mid-century bungalow charm, and a sense of quiet luxury. Enjoy morning coffee on the expansive deck, take in unforgettable sunsets each evening, with private stairs offering direct access to the secluded beach, enhancing an already exceptional waterfront experience.
Clean, open interiors make relaxing effortless, while a full basement and 1-car garage add everyday convenience. This is a true seasonal sanctuary where the North Fork’s natural beauty becomes your daily backdrop.
Ask about available months.
Southold Town Rental Permit #1247
PECONIC TRAILS: An extraordinary opportunity to invest in the future of the North Fork. 45 contiguous acres with all development rights intact, comprising a productive vineyard, open agricultural land and pristine woodland in the heart of Peconic, moments from the Long Island Sound. Approximately 27.7 acres are planted with mature Vitis vinifera vines, including 14 acres of Cabernet Franc, 1.1 acres of Malbec and 12.6 acres of Pinot Meunier. Professionally managed by a preeminent local vintner, the well-tended vineyard currently supplies grapes used in the production of award-winning North Fork wines.
Coming to market as the North Fork’s new-construction sector increasingly favors upscale, luxury residences and sophisticated indoor-outdoor living, this expansive and increasingly rare offering presents compelling potential for continued agricultural production, a landmark vineyard estate, conservation subdivision residential development, a boutique luxury residential enclave, or a retail winery as contemplated under Southold Town Code § 280-13 Use Regulations, all subject to applicable zoning, subdivision and site-plan review, permits and other governmental approvals. A prior site plan for a multi-lot residential development is on file with the Town of Southold Planning Department, providing a valuable foundation from which a buyer may explore the property’s future potential.
Privately framed by woodlands and distinguished by sweeping vineyard, farmland and open-sky vistas, Peconic Trails offers the scale, natural beauty and flexibility required to create something truly exceptional. Located amid celebrated vineyards, farm stands, beaches and historic hamlet centers, this is more than an acquisition—it is an opportunity to steward a remarkable piece of North Fork land while shaping its next chapter. Plant your roots today and establish an enduring North Fork legacy. AC (agricultural conservation 2 acre) zoning.
The Jefferson House, built in 1750, beautifully renovated and brought back to life in 2021.
This historic home is the perfect place to stay this summer and welcome family and friends. Truly the most unique home offered for rent on the North Fork.
Situated on 7 acres of natural and manicured gardens with specimen trees, fruit orchards and an outdoor patio – all nestled between vineyards and town parks on Peconic Lane – this picturesque gem offers everything needed inside and out to make your stay truly memorable.
The house has all the modern amenities including a chef’s kitchen, 3 bedrooms and baths, charming living and sitting rooms, a dining room, a music room, central air and original charm galore.
Conveniently located within walking distance of transit links, pickleball and tennis courts, and athletic fields, and a half-mile from one of the finest Long Island Sound beaches at the end of Mill Lane.
2027 prices: June $9,000, July $16,500, August $16,500, September $9,000. Two week stay considered.
Please inquire for availability.
Southold Town Rental Permit #0669
Charming updated Soundfront beach house! This home is what dreams are made of. Steps away is a plush, powder white sandy path leading to a serene private beach where panoramic vistas and mesmerizing sunsets will sweep you off your feet. Offering approximately 1,600 sq. ft. of living space, the first level boasts an eat-in-kitchen, living room with fireplace to cozy up to during those brisk fall evenings, access to a 110 sq. ft. screened-in porch – perfect for enjoying your morning coffee, a family room/dining area with soaring pitched ceilings, a full bath, laundry room and a bonus room that is currently used as a bedroom. Two additional bedrooms are located on the second floor – both with water views. There is also a new HVAC system in place. A multitude of opportunities await. This property is also offered as a compound. See 3645 Soundview Ave.
Fall is just around the corner!
Don’t miss your chance to own a home in the heart of Wine Country and experience the beauty and fun of farm country right outside your door!
Imagine apple picking, pumpkin picking, fresh pies, local fruit stands, beautiful farms, vineyards, and so much more.
**People drive for miles to visit this beautiful destination—you could have the opportunity to live here! **
Welcome to the Heart of North Fork Wine Country! Experience the perfect blend of peace, comfort, and convenience in one of Eastern Long Island’s most sought-after destinations. Nestled on a quiet street surrounded by picturesque vineyards, this charming ranch features brand-new kitchen with stainless-steel appliances brand new bathroom a garage and full basement, offering plenty of space for everyday living and future possibilities. Enjoy the relaxed North Fork lifestyle with farm stands, local markets, and seasonal farm attractions just minutes away. Spend your summers exploring beautiful beaches on both the Long Island Sound and Peconic Bay, and visiting the area’s renowned wineries, vineyards and dining. Outdoor enthusiasts will appreciate the nearby parks featuring tennis courts, baseball fields, and recreational spaces, all within walking distance. Conveniently located with easy access to the main roads and County Road 48, you’ll enjoy both tranquility and accessibility. Don’t miss this rare opportunity to make this your perfect North Fork living lifestyle and rare opportunity to create your dream retreat in Long Island’s celebrated wine country! Check out Tripadvisor, yelp for the best farms, restaurant and winery. So much to choose from you will always have something to do.
North Fork retreat! A powder white sandy path leads to a gorgeous private beach offering 116 ft. of waterfrontage while incredible sparkling Sound views, sunsets, and lush greenery set this property apart. Enjoy water views from the open concept main level and the expansive 800+ sq. ft. rear deck – perfect for lounging, al fresco dining and taking in the fresh sea air. With over 3,000 sq. ft. of living space and an unfinished basement that offers an additional shy 1,000 sq. ft. without the 2-car attached garage, there is ample space for entertaining and to accommodate large gatherings. The first level includes a living/dining room and kitchen that flow seamlessly into one another while walls of glass allow natural light to saturate the space and provide access to the deck. There is also a bonus room conveniently located on the first floor. The second level boasts an oversized 800+ sq. ft. primary suite – also with gleaming water views, which can be divided into two ensuites. Two additional bedrooms and a full bath complete this level. All baths are updated and there are new HVAC and water filtrations systems in place. There is oil heat with the oil tank located in the basement. This property is also offered as a compound. See 3651 Soundview Ave.
