luxury real estate for rent Orient, United States

2026 Seasonal Rates: July $35,000; August 1-LD $37,500: Step into stylish comfort with this beautifully designed modern farmhouse, offered fully furnished and move-in ready. This stunning 4-bedroom, 3.5-bath home combines rustic charm with contemporary elegance, perfect for comfortable family living or entertaining in style. Inside, you’ll find rich hardwood floors throughout and an open-concept living space that flows seamlessly into a chef’s kitchen, equipped with high-end appliances, custom cabinetry, and an oversized island—ideal for gatherings or gourmet cooking. The spacious bedrooms are tastefully furnished, with the primary suite featuring a luxurious en-suite bath. The remaining 2.5 bathrooms are equally refined with modern fixtures and thoughtful finishes. Outside, enjoy your own private oasis with an in-ground pool, perfect for relaxing or hosting on warm Summer days. Make this stylish offering your for the Summer season of 2026!

2026 Rates: June $8,500/week; July and August $10,000/week (Two Week Minimum For All Rentals). Spend your summer in style at this exquisite brand-new modern farmhouse, offering the perfect blend of luxury, comfort, and North Fork charm. Located just minutes from Greenport Village, local farmstands, renowned wineries, and pristine beaches, this home is the ideal summer retreat. Set on a full 1-acre lot, this spacious and sun-filled residence features an open-concept layout with elegant hardwood floors throughout. The heart of the home is a high-end chef’s kitchen, fully equipped for entertaining and flowing seamlessly into a stylish living area complete with a gas fireplace—perfect for unwinding after a day on the Sound. The first-floor primary ensuite bedroom offers a serene private escape, while the second floor includes a junior ensuite and two additional guest bedrooms with a shared full bath—providing ample space and comfort for family and friends. Step outside to your own private oasis featuring a 20x40 heated in-ground pool, surrounded by lush landscaping and plenty of space for outdoor dining and lounging. Whether you’re sipping wine under the stars, enjoying a day at the beach, or exploring nearby Greenport’s vibrant shops and restaurants, this stunning farmhouse offers the ultimate summer experience.

Available Seasonally June 20K, August 16th-Labor Day15K, Available September 15K and October 15K TIMELESS TRANQUALITY ON GARDINERS BAY - An inviting seasonal beachfront retreat on Gardiners Bay, thoughtfully designed as a peaceful escape from the demands of everyday living. Begin your mornings with beautiful sunrises over the water and settle into the quiet rhythm of bayfront living throughout the day. The home offers an open airy layout with three full sized water-facing bedrooms, updated fully equipped kitchen and baths and comfortable modern amenities throughout. A generous enclosed porch provides a versatile space for dining, working remotely or simply slowing down. Outdoors, a charming portico invites alfresco meals with a gas grill while an outdoor shower completes the experience– an effortless calming setting for refined yet relaxed bayfront living. Fully furnished and equipped with necessary linens and towels. Close to fine dining, golf and a versatile selection of wineries for additional enjoyment and entertainment.

Bright and spacious Contemporary summer rental on the North Fork. Featuring floor to ceiling windows, great room, 6 bedrooms, 3.5 bathrooms, eat-in kitchen, recreation room. Private back yard with 40x20 salt water heated pool. Offered June $25,000; July 1-23 $27,000 (RENTED); Aug 1-15 $20,000; Sept 9-30 $18,000. Permit #1230.

Not available for year round rent at this time. Newly renovated three bedroom, two bath bungalow just outside of popular Greenport Village. This house provides a sense of privacy and relaxation close to the beach. Located less than one mile away, the captivating Rocky Point Beach is a picturesque retreat for everyone to enjoy. Additionally, there is the exquisite Truman's Beach nearby, which provides a stunning view of Connecticut. Lavender Bay and Sep's Farm are conveniently located only 0.4 miles away. The exterior of the property is designed for entertainment, featuring a spacious patio, barbecue area, fire pit, and even an outdoor shower to refresh after a dip in the nearby beaches. Seasonal Rates: June $6,000 , July $8,000 , Aug-LD $10,000

Offered July $35,000; Aug $35,000; Sept $25,000; Oct $20,000. Elegantly renovated and exceptionally spacious, this contemporary retreat is nestled within a parklike setting of sweeping lawns, lush gardens, and mature landscaping that affords remarkable privacy. Refined outdoor amenities include a heated gunite pool, outdoor shower, firepit, and walking path to abutting Island’s End Golf & Country Club. The main house and annex are filled with natural light, featuring soaring ceilings, oversized windows, and glass doors that open seamlessly to two expansive decks for effortless indoor-outdoor living. A generous poolside patio offers additional space for lounging and entertaining, while the decks provide inviting areas for alfresco dining, grilling, and relaxation. Bedrooms are thoughtfully positioned to ensure comfort and privacy for guests. Peaceful and secluded, yet just moments from Greenport Village, Seps Farm Stand, and sound and bay beaches, this home is impeccably suited for gracious North Fork entertaining.

2026 Rates: $45,000 for Memorial Day Weekend-Labor Day: Welcome to 619 Bailey Avenue, a fully restored and turnkey farmhouse ideally located on the fringe of Greenport Village. Once part of a historic North Fork farm and estate, this circa 1900 residence has been thoughtfully reimagined to offer the perfect blend of classic charm and modern comfort for a summer escape. Original details—including hardwood floors, custom millwork, and timeless architectural elements—have been beautifully preserved, while stylish updates throughout create a relaxed and functional living environment. The custom chef’s kitchen is a true centerpiece, featuring a 48” range, oversized island, bespoke cabinetry, and an 8-foot bi-fold glass door that opens to the backyard for effortless indoor-outdoor living. The first floor offers a spacious living room with wood-burning fireplace, formal dining room, dedicated home office, powder room, and a flexible bedroom or bonus space. Upstairs, you’ll find two guest bedrooms and a full bath, along with a sun-filled primary suite featuring vaulted ceilings, a large walk-in closet, and a spa-like en-suite bath with double vanity and dual-head walk-in shower. Set on a generous and private lot, the backyard provides ample space to relax and entertain, complemented by a detached one-car garage. Enjoy close proximity to Greenport Village, Kontokosta Winery, nearby bay and Sound beaches, and local favorites like Sep’s Farm Stand—making this an exceptional North Fork summer retreat.

2026 Rates: May $26,000; June $29,000; July $36,000; September $27,000; October $24,000. Experience North Fork summer living in this newly constructed gem! Nestled in the sought-after Stirling Eastern Shores community, this impeccably designed modern farmhouse offers exclusive access to a private Long Island Sound beach, just a five minute walk from the property. Step inside to discover a light-filled and meticulously styled interior adorned with contemporary finishes and furnishings. The heart of the home is the chef's kitchen seamlessly integrated into the Great Room and anchored by a cozy gas fireplace. On the first floor, you'll find a convenient half bath, a junior en-suite bedroom, a spacious mudroom, and a sizeable 2-car garage. Ascend to the second level to encounter two additional guest bedrooms sharing a full bathroom, along with a stunning primary en-suite bedroom. The primary bath boasts a luxurious double vanity, a walk-in shower, a soaking tub, and an expansive walk-in closet for added convenience and indulgence. Outside, the property showcases a captivating landscape featuring a sprawling stone patio enveloping a 20x40 heated salt-water pool, complemented by an outdoor shower - an ideal setting for hosting gatherings and enjoying the summer sun.

2026 NO LONGER AVAILABLE; 2027 RATES COMING SOON This substantial post-modern residence offers the perfect North Fork retreat for those seeking space, comfort, and effortless entertaining. From the moment you enter, the home’s expansive layout welcomes you with bright, open living areas designed for relaxing and hosting with ease. With five generously sized bedrooms and three well-appointed bathrooms, there is plenty of room to accommodate guests throughout your stay. Inside, the home features beautiful hardwood floors, detailed custom moldings, and two inviting fireplaces that create a warm and refined atmosphere. Multiple living spaces allow guests to gather comfortably or enjoy quiet moments throughout the home. Step outside and experience a truly exceptional outdoor setting designed for summer living. The backyard is centered around a heated 20' x 44' saltwater pool w/ electric cover and surrounded by multiple outdoor dining and lounging areas perfect for entertaining, relaxing, and enjoying long summer evenings. Whether hosting a casual poolside barbecue or an elegant outdoor dinner, the setting provides the perfect backdrop for memorable gatherings. This property offers the ideal combination of space, comfort, and resort-style outdoor living—perfect for enjoying the very best of the North Fork.

In our beloved 2,350 acres of Mashomack Nature Preserve, there are a handful of residences. At the end of this long private road through this preserve, one can find this breathtaking newly constructed modern home with no details left behind. This expertly crafted home is loaded with premium amenities, top-of-the-line appliances, and walls of windows overlooking Coecles Harbor, this home has no comparisons. With 3,800 sq. ft., the home features an open floor plan with sweeping water views from every vantage point, whether dining, cooking, or lounging. Continue entertaining outside on the large outdoor waterfront deck where you become one with nature. The master and one of the guest bedrooms are en-suite, and the 2 additional bedrooms share a bath. All the bedrooms have abundant closet storage. Enjoy this newly constructed private waterfront property this summer!, Additional information: Cooling:SEER Rating 12+

2026 Rates: April $7,500; May $12K; June $15K; July $25K; A1-LD $27,500; Sept $12,500; October $10K: This beautifully curated home away from home, blends modern design with warmth and style. Experience elegant comfort in your private retreat with natural light, modern decor and thoughtful touches throughout. Nestled on a quiet, tree lined street, this special haven features a front porch, fully equipped open kitchen, and spacious backyard with a pool and fire pit. Enjoy all season living in this home away from home just a 10 minute walk to The LIRR station, Hampton Jitney, and The North Ferry.

2026 Rates: August 1-15 $25,000: Escape to this exceptional seasonal rental, perfectly situated on the shores of the Long Island Sound. This beautifully appointed waterfront home offers the ultimate coastal living experience, featuring private stairs leading directly to the beach, an in-ground heated gunite pool, and panoramic water views from nearly every room. With 4 spacious bedrooms—including a luxurious primary en-suite—and 3 full bathrooms, there’s plenty of room for family and guests to unwind in comfort. The heart of the home is a dramatic post and beam Great Room, designed for both relaxing and entertaining, with soaring ceilings and expansive windows that flood the space with natural light. Step out onto the large balcony to take in sweeping views of the Sound, enjoy morning coffee as the sun rises over the water, or end the day with a spectacular sunset. Additional amenities include a 1-car garage, central air, and thoughtfully landscaped grounds that ensure privacy and tranquility. Whether you’re lounging poolside, walking along the shoreline, or enjoying evening breezes from the balcony, this home offers an unforgettable seasonal escape.

Ground floor one bedroom apartment in Driftwood Cove, steps outside of Greenport Village. Newly renovated with new floors throughout, refreshed kitchen with new stove & refrigerator, freshly painted. Living/dining room with coat closet, bedroom with walk-in closet, full bath, AC. Community laundry with new washing machines & dryers, parking lot. Close to Greenport Village shops, restaurants, groceries, Mitchell Park, waterfront wharf, high school, Jitney, LIRR, and bay beaches. Maximum occupancy 2, no pets, minimum FICA score 650. Driftwood Cove rental application required including background and financial checks. Subject to Board of Director’s approval.