Greenport West, NY Homes for Rent

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  $4,500 Per Month

  • 4 Beds
  • 2 Baths
  • 1,800 Sq Ft
  • House for Rent

  336 2nd St, Greenport, NY 11944

  * low-maintenance North Fork lifestyle,* weekend retreat,* turnkey without renovation headaches,* walkability,* lock-and-leave second home,* income potential,* simpler ownership vs larger estatesWEEKLY RENTAL 3500, monthly 12,000 “Freshly repositioned for the spring market, this beautifully renovated Village home offers exceptional value and immediate enjoyment.

  Ron Moschetta Keller Williams Realty Greater

  336 2nd St, Greenport, NY 11944
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  $75,000 Per Month

  • 4 Beds
  • 3.5 Baths
  • 3,800 Sq Ft
  • House for Rent

  47L S Ferry Rd, Shelter Island, NY 11964

  Rental is Available in 2026: August $75,000. Located 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

  Tina Marika Kaasik Daniel Gale Sothebys Intl Rlty

  47L S Ferry Rd, Shelter Island, NY 11964
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  $15,000 Per Month

  • 3 Beds
  • 2 Baths
  • 2,556 Sq Ft
  • House for Rent

  1855 Village Ln, Orient, NY 11957

  Available April $6,000; May $6,000; June $15,000; Aug 2-16 $12,500 (RENTED); Sept $12,000.Impeccably restored 19th Century gem located in the heart of Orient Village with bay views. Close to bay and sound beaches, and a stroll to all village amenities. Featuring 2 parlors, 3 bedrooms, library, office, eat-in kitchen, updated baths, charming garden, out-door dining, and grill, out-door shower.

  Janet Markarian Daniel Gale Sothebys Intl Rlty

  1855 Village Ln, Orient, NY 11957
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  $10,000 Per Month

  • 4 Beds
  • 2.5 Baths
  • 2,000 Sq Ft
  • House for Rent

  405 the Short Ln, East Marion, NY 11939

  Ideally Located in Desirable Pebble Beach Farms on a Quiet Street and Surrounded on Two Sides by Preserved Land, This Comfortable 4-Bedroom, 2.5-Bath Home Offers Privacy and Plenty of Space to Relax and Enjoy. A Wraparound Rocking-Chair Front Porch Welcomes You, While the Spacious Furnished Rear Deck Overlooks a Beautifully Landscaped Yard and Large Heated 24' x 52' Inground Pool with Water Slide

  Paul Loeb Douglas Elliman Real Estate

  405 the Short Ln, East Marion, NY 11939
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  $20,000 Per Month

  • 5 Beds
  • 3 Baths
  • 3,700 Sq Ft
  • House for Rent

  2700 Sound Dr, Greenport, NY 11944

  2026 Rates: August 1-15 $20,000, September $25,000, October $20,000: 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

  William Walters Daniel Gale Sothebys Intl Rlty

  2700 Sound Dr, Greenport, NY 11944
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  $3,750 Per Month

  • 3 Beds
  • 1 Bath
  • House for Rent

  220 Fiddler Ln, Greenport, NY 11944

  Charming, beach-inspired Greenport home offering easy single-level living just blocks from a beautiful Bay beach and a marina with two waterfront restaurants. Recently painted with warm, inviting décor, hardwood floors throughout, and a clean, functional kitchen. A screened-in porch adds extra hangout space, and a simple outdoor shower brings classic North Fork summer charm. The primary bedroom

  Rita Rooney Douglas Elliman Real Estate

  220 Fiddler Ln, Greenport, NY 11944
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  $11,200 Per Month

  • 4 Beds
  • 4 Baths
  • 3,200 Sq Ft
  • House for Rent

  750 Kerwin Blvd, Greenport, NY 11944

  Greenport-Immaculate and spacious home. A welcoming front porch leads to the sunny Living room and dining room. A fully equipped gourmet kitchen with Thermador appliances with sliding doors to back deck, family room with vaulted ceilings also has access to large back deck, there is another den/office, a full bathroom with shower and laundry all on the first floor. The second floor there are two

  Amy Kirincic The Agency Northshore NY

  750 Kerwin Blvd, Greenport, NY 11944
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  $3,000 Per Month

  • 3 Beds
  • 2 Baths
  • 1,300 Sq Ft
  • House for Rent

  3670 Rocky Point Rd, East Marion, NY 11939

  Beautifully Renovated. 3 Bedrooms/2 Bathroom. One Floor Living with Deck and Nice Yard. Fully Furnished. Beach at the End of the Road. Year-Round $4,000. FALL 2026 - Labor Day thru September $8,000; October $8,000. OFF SEASON - November 2026 to April 2027- $3,000 (for single or multiple months). SUMMER 2027 - Memorial Day to Labor Day $34,000; Memorial Day thru June $8,000; July $12,000, August

  Paul Loeb Douglas Elliman Real Estate

  3670 Rocky Point Rd, East Marion, NY 11939
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  /19

  $20,000 Per Month

  • 3 Beds
  • 2.5 Baths
  • 2,000 Sq Ft
  • House for Rent

  580 South Ln, East Marion, NY 11939

  Available Seasonally June 20K, August 16th-Labor Day15KTIMELESS 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

  Phyllis Caldwell Daniel Gale Sothebys Intl Rlty

  580 South Ln, East Marion, NY 11939
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  $49,000 Per Month

  • 6 Beds
  • 5.5 Baths
  • 6,600 Sq Ft
  • House for Rent

  57305 Route 48, Greenport, NY 11944

  Spectacular, contemporary seasonal rental home with pool and Jacuzzi on the Long Island Sound front. 150 feet of direct waterfront and beach, with incredible view. Meticulously renovated and professionally designed. 6 bedrooms, 5.5 bathrooms. Hamptons luxury in North Fork. Home situated on 1 acre, 6,600 square feet. One master bedroom has jacuzzi and steam room and two extra bedrooms with full

  Zepur Diktas Compass Greater NY LLC

  57305 Route 48, Greenport, NY 11944
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  $19,000 Per Month

  • 3 Beds
  • 2 Baths
  • 1,750 Sq Ft
  • House for Rent

  300 Marion Place, East Marion, NY 11939

  Private, peaceful home on a serene acre of property with mature plantings and wonderful landscaped greenery. Just renovated, featuring open modern Kitchen/Dining combo for modern entertaining. Separate family room across open foyer with fireplace and loads of puzzles & games. Charming covered front porch looks out onto expansive front yard. Back deck with grill overlooks pool and backyard. (Pool

  Laura Wanamaker Howard Hanna Coach

  300 Marion Place, East Marion, NY 11939
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  /20

  $8,000 Per Month

  • 3 Beds
  • 2 Baths
  • 1,000 Sq Ft
  • House for Rent

  1050 Pine Ave, Southold, NY 11971

  North Fork summers are defined by sun-soaked beach days, vineyard hopping, and slow evenings spent cooking under the open sky—and this charming 3-bedroom, 2-bath cottage captures it all. Tucked away in Southold, this inviting rental places you right in the heart of the North Fork, perfectly positioned to experience everything the area has to offer. Spend your mornings browsing Southold’s curated

  Kieran Collings Douglas Elliman Real Estate

  1050 Pine Ave, Southold, NY 11971
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  $7,000 Per Month

  • 4 Beds
  • 2 Baths
  • 1,500 Sq Ft
  • Property for Rent

  1110 Gillette Dr, East Marion, NY 11939

  Perfect summer rental, Short Stroll to beautiful Bay Beach, Charming 4 br, 2ba Cape, Family room, views to the West over preserved land, totally upgraded and recently renovated, flexible rental times, 14 days minimum. Rental Permit # 1269. June $7,000.00July $9,000.00 or $2,500.00 weekly 14 day minimum, August till LD, $12,000.00 or $3,500.00 weekly 14 day minimum

  Tom Uhlinger Douglas Elliman Real Estate

  1110 Gillette Dr, East Marion, NY 11939
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  $6,300 Per Month

  • 4 Beds
  • 4.5 Baths
  • 3,500 Sq Ft
  • House for Rent

  63615 North Rd, Greenport, NY 11944

  Available for $450 per night two week minimum, utility reimbursement. Private Soundfront Wooded Classic post and beam chalet. You will be delighted to see how close you are from your back door to the bluff on the sound!" Walk down a path to your stairs to your beach. If you stay the entire season you may see one other person. Everything is private. Inside you are surrounded by warmth and light.

  Kenneth Zahler Richmond Realty Corp

  63615 North Rd, Greenport, NY 11944
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  $20,000 Per Month

  • 4 Beds
  • 4 Baths
  • 3,200 Sq Ft
  • House for Rent

  950 Blue Marlin Dr, Southold, NY 11971

  Beachfront, located in Southold Shores, this architect's own home is built with all the beautiful appointments you can imagine. Embracing the purity of architectural detail, together with a refined simplicity, this waterfront home offers a timeless elegance. Sweeping sunsets eye-catching angles and thoughtful details provide constant visual interest. A large 4 bedrooms with 4 baths ensuite,

  Lori Feilen William Raveis New York LLC

  950 Blue Marlin Dr, Southold, NY 11971
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  $45,000 Per Month

  • 3 Beds
  • 3 Baths
  • 1,528 Sq Ft
  • Condo for Rent

  123 Sterling Ave Unit 2, Greenport, NY 11944

  SUMMER RENTAL! BOAT SLIP: Perched above the water with expansive views of Greenport Harbor and Stirling Basin, this unit offers modern luxury on one of Greenport Village's most beautiful streets. This unit includes a private boat slip, dedicated indoor and outdoor parking spaces, in-unit laundry. Four blocks from the center of the village commercial district with shops, restaurants, and

  Lisa Gillooly Compass Greater NY LLC

  123 Sterling Ave Unit 2, Greenport, NY 11944
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  $25,000 Per Month

  • 4 Beds
  • 3.5 Baths
  • House for Rent

  910 Glenn Rd, Southold, NY 11971

  Introducing your perfect retreat! This stunning 4-bed, 3.5-bath waterfront oasis nestled on West Creek in Southold. Enjoy access to Peconic Bay via your private dock. Spanning approx 3500 sq ft, revel in the elegance of oak floors, a luxurious soaking tub, and high ceilings throughout. The 1st floor has 2 primary ensuites, a spacious Great Room with cozy fireplace, laundry, and 2.5 baths +2-car

  Andrea Parks Douglas Elliman Real Estate

  910 Glenn Rd, Southold, NY 11971
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  $8,700 Per Month

  • 4 Beds
  • 3 Baths
  • 2,018 Sq Ft
  • House for Rent

  59 Peconic Ave, Shelter Island, NY 11964

  Classic Cape Cod Retreat Near Shell BeachEnjoy summer on Shelter Island in this charming Cape Cod–style home with tranquil water views just across the street and easy access to one of the island’s most popular beaches. Located less than half a mile from Shell Beach, this 4-bedroom, 3-bath home is set in a friendly, sought-after summer community.The bright, open living and dining area

  Debra Von Brook Binder Daniel Gale Sothebys Intl Rlty

  59 Peconic Ave, Shelter Island, NY 11964
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  $8,000 Per Month

  • 6 Beds
  • 2.5 Baths
  • 2,460 Sq Ft
  • House for Rent

  100 Maple Ln, Orient, NY 11957

  Offered Sept $8,000. Enjoy the ease of summer on the North Fork in this classic 1910 hilltop home overlooking Orient Bay and Long Island Sound. A three-sided wraparound porch extends the main living spaces outdoors through multiple glass doors, creating a seamless indoor-outdoor flow filled with light and salt breezes. Inside, the home offers inviting spaces for gathering, including a spacious

  Janet Markarian Daniel Gale Sothebys Intl Rlty

  100 Maple Ln, Orient, NY 11957
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  $30,000 Per Month

  • 8 Beds
  • 7 Baths
  • 5,400 Sq Ft
  • House for Rent

  650 Pine Ave, Southold, NY 11971

  Masterfully crafted resort style property, where coastal luxury meets effortless living. Tucked within a coveted private beach community with beach access, this resort-style property was designed for gathering, entertaining, and unwinding in total privacy. The home features a show-stopping 20’ x 40’ heated saltwater pool, framed by lush, manicured grounds that feel both serene and indulgent.

  Colin McCarthy Thomas J McCarthy Real Estate

  650 Pine Ave, Southold, NY 11971
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  $7,000 Per Month

  • 1 Bed
  • 1 Bath
  • 750 Sq Ft
  • House for Rent

  Unlisted Address

  Experience the charm of this delightful rental cottage nestled in Southold, North Fork, just a stone’s throw from Founder's Landing Park and Wharf House, with one of the most amazing sugar sand beaches in our community. This unique, fully furnished one-bedroom retreat features flexible rental periods and competitive rates throughout the year.Imagine waking up to the serene views of a

  Nicholas Planamento William Raveis New York LLC

  Unlisted Address
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  $10,000 Per Month

  • 3 Beds
  • 1.5 Baths
  • 1,578 Sq Ft
  • House for Rent

  425 Old Shipyard Ln, Southold, NY 11971

  Southold-Enjoy the North Fork in this adorable cottage. Located in Founder's Landing Southold beach community. Three bedrooms, living room, kitchen with dining area and sunroom overlooking yard and pool. This charming home has everything you need for a great summer getaway. Close to community beach and Park. Close to town, restaurants, shopping, The giving room yoga and juice bar, Southold fish

  Amy Kirincic The Agency Northshore NY

  425 Old Shipyard Ln, Southold, NY 11971
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  $8,000 Per Month

  • 4 Beds
  • 3 Baths
  • 2,600 Sq Ft
  • House for Rent

  60 Water Terrace, Southold, NY 11971

  Settle into summer on the North Fork in this beautifully maintained and updated 4 bedroom, 3 full bath home located in the Angel Shores community of Southold. The layout is ideal for entertaining or just enjoying the lazy days of summer. This special home offers a 1st floor bedroom and full bath, along with a 2nd story spacious primary en-suite and 2 additional bedrooms to comfortably accommodate

  Natalie Hough Daniel Gale Sothebys Intl Rlty

  60 Water Terrace, Southold, NY 11971
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  /5

  $4,000 Per Month

  • 3 Beds
  • 1 Bath
  • 1,100 Sq Ft
  • House for Rent

  310 Old Shipyard Ln, Southold, NY 11971

  Southold Village Rental Charming and well-located, this 3-bedroom, 1-bath residence offers easy North Fork living just moments from the heart of Southold. A short distance to Southold Town, local shops, dining, and the waterfront, as well as close proximity to Founders Beach for swimming, sunsets, and seaside relaxation. The home features a comfortable layout with light-filled living spaces,

  Eric Frend Corcoran

  310 Old Shipyard Ln, Southold, NY 11971
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  $5,000 Per Month

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft
  • House for Rent

  8415 Soundview Ave, Southold, NY 11971

  Step inside this charming 2 bedroom, 1 bath bungalow nestled on the serene shores of Great Pond in Southold. This cozy waterfront retreat offers tranquil water views and is just around the corner from Kenny's Beach and the popular Little Fish restaurant. Enjoy kayaking, paddle boarding, and fishing right from your backyard. Centrally located in the heart of the North Fork, you're perfectly

  Nicole Fitzgerald Signature Premier Properties

  8415 Soundview Ave, Southold, NY 11971
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  $27,000 Per Month

  • 4 Beds
  • 4.5 Baths
  • 3,100 Sq Ft
  • House for Rent

  590 Soundview Ave, Southold, NY 11971

  This Spacious Open Floor Plan Home Features Two Separate Living Areas, a Treetop Waterview Deck, A Chef's Kitchen with Pantry and a Large Stylish Dining Table. This Inviting Home's Layout Offers Comfortable Gathering Spaces. The Resort-Style Outdoor Living Area is Highlighted by an Inground Pool with a Built-In Hot Tub and Elegant Bluestone Pool Surround. Generous Seating Area Including Hammock,

  Paul Loeb Douglas Elliman Real Estate

  590 Soundview Ave, Southold, NY 11971
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  $12,000 Per Month

  • 4 Beds
  • 3 Baths
  • 2,900 Sq Ft
  • House for Rent

  110 Sleepy Hollow Ln, Southold, NY 11971

  Discover this stunningly renovated 4-bedroom, 3-bath home, offering an expansive open floor plan, a cozy den, and a versatile bonus room. Designed for both comfort and style, the chef’s kitchen includes a massive eat-in-quartz island and boasts top-of-the-line Fisher & Paykel appliances, including a double-drawer dishwasher, induction cooktop, and convection oven.Perfect for entertaining

  Paul Loeb Douglas Elliman Real Estate

  110 Sleepy Hollow Ln, Southold, NY 11971
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  $7,000 Per Month

  • 2 Beds
  • 2 Baths
  • 1,825 Sq Ft
  • House for Rent

  130 Village Ln, Orient, NY 11957

  Available July 13-27 (14 nights) $7,000; Aug 3-Sept 7 (5 weeks) $13,000. Beautiful renovated 2-bedroom, 2 full bath home in Orient Village.Open concept – living/dining/gourmet kitchen. Lower level with screening room, office, full bath. Walk from Jitney. Enjoy all village amenities, bay & sound beaches. Close to Orient Beach State Park & Cross Sound Ferry. Permit# 1364.

  Janet Markarian Daniel Gale Sothebys Intl Rlty

  130 Village Ln, Orient, NY 11957
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  $7,500 Per Month

  • 3 Beds
  • 2.5 Baths
  • 2,000 Sq Ft
  • House for Rent

  485 Pine Rd, Southold, NY 11971

  2026 Rates: September $7500; October $10,000: Discover your perfect getaway in this expansive and meticulously updated ranch home, designed for relaxation and rejuvenation. Experience a resort-like atmosphere with the stunning gunite, heated saltwater pool, complemented by a beautiful stone surround and convenient outdoor shower. Step inside to find high vaulted ceilings that create an airy

  William Walters Daniel Gale Sothebys Intl Rlty

  485 Pine Rd, Southold, NY 11971
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  $50,000 Per Month

  • 4 Beds
  • 4.5 Baths
  • 3,300 Sq Ft
  • House for Rent

  400 Youngs Rd, Orient, NY 11957

  Stunning Orient retreat with a private heated gunite pool; enjoy an ideal location with a beach and village just down the block. This tranquil home features soaring ceilings, two fireplaces, four ensuite guest rooms, a private office, an enormous eat-in kitchen, a light-filled dining room, a hotel-like master suite with a second-floor balcony, charming front porch, two living rooms, and beautiful

  Bridget Elkin Compass Greater NY LLC

  400 Youngs Rd, Orient, NY 11957
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  $10,000 Per Month

  • 5 Beds
  • 7 Baths
  • 3,500 Sq Ft
  • House for Rent

  495 N Parish Dr, Southold, NY 11971

  Southold, North Fork.Experience the beauty of seasonal living on Southold Bay. This newly renovated contemporary bayfront estate home invites you to bask in its light and bright ambiance, perfect for relaxation and rejuvenation. With its Zen-inspired organic design, you’ll find comfort and privacy combined with the conveniences of modern life.Nestled near the Southold Yacht Club, just

  Nicholas Planamento William Raveis New York LLC

  495 N Parish Dr, Southold, NY 11971
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  $30,000 Per Month

  • 4 Beds
  • 3 Baths
  • 2,350 Sq Ft
  • House for Rent

  485 Hickory Ave, Southold, NY 11971

  Impressive Goose Creek home with water views and large heated in-ground pool! This four bedroom, three bath house features a first floor primary bedroom with en-suite, a gourmet kitchen and open living space. The newly designed landscape with outdoor kitchen (not pictured) is ideal for entertaining or relaxing. Enjoy its large fire pit and BBQ grill after an afternoon of Kayaking. Close to

  Mackenzie Needham Daniel Gale Sothebys Intl Rlty

  485 Hickory Ave, Southold, NY 11971
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  $10,000 Per Month

  • 3 Beds
  • 2 Baths
  • 2,000 Sq Ft
  • House for Rent

  275 Maier Place, Southold, NY 11971

  Seasonal Rental in Scenic Southold, NY – 3 Bed, 3 Bath RetreatEscape to the heart of the North Fork with this beautifully appointed 3-bedroom, 2-bath seasonal rental in picturesque Southold, NY. Nestled among the region's famed vineyards, farm stands, and white sand beaches, this home offers the perfect blend of charm, comfort, and convenience.Inside, you'll find a spacious and

  Mary Terry MCKENNASHEA LLC

  275 Maier Place, Southold, NY 11971
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  $10,000 Per Month

  • 4 Beds
  • 2.5 Baths
  • 2,440 Sq Ft
  • House for Rent

  2905 Private Rd, East Marion, NY 11939

  4 Bedroom, 2.5-Bath Expanded Ranch with Large Deck and a 20' x 45' Heated Inground Gunite Pool. All Set on 3+ Wooded Acres with Mini Vineyard Adjacent to Preserved Land for Privacy. Central Airconditioning, Updated Baths, Hardwood Floors and Attached 2-Car Garage. Parks District Beach Rights to Beautiful Truman's Beach on the Long Island Sound. Farmstands, Islands End Golf, a Waterfront Tasting

  Paul Loeb Douglas Elliman Real Estate

  2905 Private Rd, East Marion, NY 11939
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  /19

  $35,000 Per Month

  • 3 Beds
  • 3 Baths
  • 3,400 Sq Ft
  • House for Rent

  745 Golfview Ct, East Marion, NY 11939

  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

  Janet Markarian Daniel Gale Sothebys Intl Rlty

  745 Golfview Ct, East Marion, NY 11939

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