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luxury houses for rent Old Saybrook, United States

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23

House Old Saybrook (United States)

Embrace the Quintessence of Summer Living at the Historic Fenwick Cottage ~ Nestled in the heart of the Borough of Fenwick, this iconic Victorian waterfront cottage presents a rare opportunity to experience summer as it was meant to be. With its shingled exterior and timeless charm, the Fenwick Cottage is an idyllic retreat for the discerning summer resident. This shingled historic cottage boasts an open floor plan complemented by high ceilings and original architectural elements, creating an atmosphere of elegance and comfort. Each room in this storied residence has panoramic vistas, ensuring that the serene beauty of the shoreline is always within sight. Fenwick Cottage is a haven for everyone, with access to golf, tennis, pristine beach and boating - all the ingredients for an unforgettable summer. Available for a one or two-month rental during the peak of summer - July and/or August

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$75,000 IC / month
9bedrooms
6bathrooms
land  2,064

By William Pitt Sotheby's International Realty

33

House Old Saybrook (United States)

Summer 2025! -- Enjoy June, July, August, and/or September at 8 Belaire Manor. This beautiful property is a water-front, 4 bedroom, one-level home situated on a sandy beach in a private association. Wake up every morning to ocean waves, and watch the panoramic sunrises and sunsets which are magical here. Upon pulling into the driveway, you'll be greeted by breathtaking water views. The expansive patio right on the beach is perfect for entertaining or relaxing, and is just a few steps to the water. Enjoy spending days taking long walks, running, seashell collecting, swimming, grilling, entertaining, and making priceless memories. Inside, this beach home offers: stunning ocean views, high ceilings with fans, a wall of windows with sliding door, central air, recessed lighting, New England style light and bright design, open concept one-level living, ample closet space, laundry, 4 bedrooms, and 2 full baths. The kitchen is complete with granite, stainless steel appliances, and a large island with breakfast bar. Recent home upgrades include new furniture, new guest mattresses, and custom window treatments. Outside, there is a full bath, driveway parking for 4 cars, and grassy front yard. Saybrook marina, Fenwick golf course, The Kate theater, restaurants, and shopping are all close by. Only 2 hours from NYC.

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$18,000 IC / month
4bedrooms
3bathrooms
land  688

By William Pitt Sotheby's International Realty

24 listings near Old Saybrook

Nearby
22

Property Old Lyme (United States)

Academic furnished rental in White Sands Beach. Large living room with fireplace, dining room with table for eight, fully applianced kitchen, sunroom/office, laundry and full bath all on the first floor.The four bedrooms and newly updated hall bath are upstairs. Cable and wi-fi installed. Across the road are a tot lot, basketball court and large open space for other games. A short walk to the Association beach. New hardwood floors installed upstairs . Rental start date is September 1.

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$2,200 IC / month
4bedrooms
2bathrooms
land  1,295

By William Pitt Sotheby's International Realty

Nearby
36

Property Clinton (United States)

SPECTACULAR 5 BEDROOM DIRECT WATERFRONT HOME WITH PRIVATE BEACH AVAILABLE FOR THE ACADEMIC YEAR. Built in 1912 but completely remodeled within past 20 years, this open concept home offers unparalleled water views of Long Island Sound and Duck Island. The home is 3 stories (bedrooms on 2nd and 3rd floors) and rises above the water via a stone staircase from the beach and patio area. This home offers TONS of natural privacy from neighbors, upscale decor, kitchen island that seats 8 with a Dining Room close by, working stone fireplace, Sun Room, multiple decks (in front to the home and off the Primary), Rec Room / TV on 3rd floor...the perfect living and entertaining home. This home will serve as a retreat from your hectic life!

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$9,000 IC / month
5bedrooms
5bathrooms
land  2,064

By William Pitt Sotheby's International Realty

Nearby
31

House Clinton (United States)

Fabulous opportunity for a furnished academic rental available starting September 1st. This beautifully appointed direct waterfront home with private beach in Clinton Ct is a perfect home for to make lasting memories. Large living room / dining room combo opens to the covered deck with beautiful views of Long Island Sound. Large family / media room with wet bar also with views offers a more casual living space. A few steps up to private bedroom suite with Queen size bed offers private living for guests or in-laws. Second level offers Primary bedroom suite with King size bed and full bath and laundry access, 2nd bedroom with queen size bed and 3rd bedroom with 2 twins and additional shared bath. This home sleeps 8 extremely comfortably. Two car garage complete with EV charger. Come spend your summer in luxury at this beautiful direct waterfront home. This home is perfectly situated between New York City and Boston two hours either direction and easily accessible by train.

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$12,500 IC / month
4bedrooms
5bathrooms
land  1,862

By William Pitt Sotheby's International Realty

Nearby
19

House Clinton (United States)

Academic rental available Sept through June 2025. Three bedroom ranch in coveted Harbor View Beach Association. Steps from the Association Beach. This home offers three nice sized bedrooms, updated kitchen and a comfortable living room.

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$1,800 IC / month
3bedrooms
1bathroom
land  931

By William Pitt Sotheby's International Realty

Nearby
20

Property Clinton (United States)

Discover timeless elegance in this beautifully refreshed antique colonial home, perfectly situated in the heart of downtown Clinton. With 3-4 spacious bedrooms, an enclosed front porch, a barn for storage, this inviting residence has both comfort and character, making it an ideal retreat for families or those seeking a serene lifestyle. Enjoy fresh paint throughout, highlighting the home's classic architectural details while providing a bright and airy atmosphere. The property is just a short stroll to the marina and docks, where you can indulge in waterfront activities, restaurants, and picturesque views. Step outside and explore the charming sidewalks of the neighborhood, leading you to delightful shops, cafes, and local amenities-all within walking distance. Don't miss your chance to enjoy this setting in a prime water community. Schedule your private tour today and experience the unique charm of this downtown classic.

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$3,400 IC / month
4bedrooms
2bathrooms
land  1,942

By William Pitt Sotheby's International Realty

Nearby
29

House Madison (United States)

ANNUAL RENTAL. This charming 4-bedroom home, close to downtown Madison, Hammonasset State Park and commuting, was built in 1920 and has all the modern conveniences. The first floor is open with living and dining areas, updated kitchen, bedroom or office, full bath, laundry room, family room and screened-in porch overlooking a beautiful backyard. On the second floor there are three bedrooms - one large enough to be a bonus room - all with great closet space. Tenants are responsible for all utilities, trash and snowplowing. Landlord is responsible for lawn maintenance. Pets possible (dog or cat less than 30lbs), no smoking. Credit check and renter's insurance required.

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$3,200 IC / month
4bedrooms
2bathrooms
land  3,359

By William Pitt Sotheby's International Realty

Nearby
22

Property Madison (United States)

An EXECUTIVE RENTAL near Madison's town center, available now for the ACADEMIC period to May 01. This is one of the very best ACADEMIC Rentals in town AND if needed, it may be POSSIBLE TO EXTEND for an increased amount. This gracious yet big Colonial is light and bright with numerous touches that you would expect in a home like this including: a Gedney designed kitchen with Bosch appliances, over-sized bedroom closets, a Master Suite, first floor Laundry ROOM, 2 fireplaces, central AC, family & living rooms designed for entertaining. A very nice feature: the NUMEROUS rooms & spaces for working at home, online learning or just a place to get away. All of this and what a location with a view of private gardens, a brick patio and an inground pool with an outside bathroom and changing room with shower.

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$6,500 IC / month
4bedrooms
3bathrooms
land  5,625

By William Pitt Sotheby's International Realty

Nearby
9

Property Orient (United States)

Magical 1840's Cottage in Browns Hills with endless views across Orient Bay. Beautiful south facing garden abutting farm fields. Three bedrooms 1.5 baths, outdoor shower, deeded sound beach. A private, tranquil natural sanctuary in bucolic Orient. Offered July $15,000; Aug $15,000; Sept $8,000; year-round, furnished starting Sept $32,000/mo. Permit #0308.

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$15,000 IC / month
3bedrooms
2bathrooms
land  2,388

By Daniel Gale Sotheby's International Realty

Nearby
20

Property Waterford (United States)

Live in a wonderful quiet neighborhood surrounded by water. Sit on the wrap around porch and enjoy views of the Niantic River. Great community for walking and enjoy the private beach only for this neighborhood. This home has a lot of character and space. Large living room with wood burning fireplace, large dining room, spacious kitchen with a lovely sunroom attached. Laundry and a powder room on the first floor. The second floor includes 4 bedrooms and 2 full baths. Many windows throughout this antique home create a light and airy property. There is a detached two car garage with a guest house. A large flat lot with plenty of parking.

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$3,200 IC / month
4bedrooms
3bathrooms
land  4,856

By William Pitt Sotheby's International Realty

Nearby
28

House Orient (United States)

Amazing North Fork home with heated salt water gunite pool located in Grandview Estates featuring 4 bedrooms (1st floor bedroom with ensuite, 2 ensuite guest bedroom on the second floor with 1 additional guest bedroom and guest bathroom) office/den also located on the second floor with a large sitting area and balcony at the landing of the second floor, large, finished basement with projection TV. Available October, November, and December for 2-week minimum period for $3,000 per week. Permit #0441.

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$110,000 IC / month
4bedrooms
5bathrooms
land  4,452

By Daniel Gale Sotheby's International Realty

Nearby
20

House East Marion (United States)

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.

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$4,600 IC / month
3bedrooms
2bathrooms
land  1,012

By Daniel Gale Sotheby's International Realty

Nearby
17

House Orient (United States)

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. Offered May $7,000; Aug 12-26 $10,000; Sept $10,000; Oct $7,000; Nov $6,000. Permit #0483.

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$10,000 IC / month
3bedrooms
2bathrooms
land  1,335

By Daniel Gale Sotheby's International Realty

Nearby
15

House Orient (United States)

Experience breathtaking views of Long Island Sound and Orient Point County Park from this spacious open-concept home. This beautifully updated 4-bedroom, 4-bathroom residence offers a private 20x40 heated saltwater in-ground pool and serene backyard. Host memorable gatherings in the spacious kitchen, perfect for indoor and outdoor dining. The expansive master suite boasts breathtaking views, a king-size bed, an office nook, dressing area, a full bathroom, and a private balcony. The lower level features a cozy sitting and entertainment room, an exercise room, a full bathroom, laundry facilities, a 2-car garage, and direct access to the pool and backyard. Enjoy easy access to the pristine sound beach, hiking trails, Orient State Park, and Duryeas restaurant. Located at the tip of Long Island, this exceptional home is perfect for anyone seeking coastal living with ample entertainment and relaxation space. Permit# 0234. Offered Apr $11,000; May $20,000; June $25,000; Sept 5-30 $25,000; Oct $20,000; Nov $15,000.

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$20,000 IC / month
4bedrooms
4bathrooms
land  3,885

By Daniel Gale Sotheby's International Realty

Nearby
14

House Orient (United States)

Enjoy a beautiful airy and bright mint condition Bay Front Orient Contemporary home, perfect for relaxing and entertaining. This 4-bedroom 4.5 bath home has gourmet kitchen, fireplace, open common space for easy entertaining. First floor has access to bay side screened porch from living room and den (or 4th bedroom with full bath). Second floor master bedroom and a guest bedroom open onto upper bay side deck, a third bedroom with full bath completes the layout. Private stairs to the beach and deeded beach rights to association Bay beach just a short walk from the house. Property is close to all village amenities: Country Store, Post Office, Marinas, Bay and Sound beaches. Offered Apr $10,000; May $12,000; June $15,000; July $35,000; Aug $35,000; Sept $20,000; Oct $15,000; Nov $10,000. Permit# 1020.

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$10,000 IC / month
4bedrooms
5bathrooms
land  1,942

By Daniel Gale Sotheby's International Realty

Nearby
18

House East Marion (United States)

Relax and enjoy this beautifully appointed bay front house w/ private beach and stunning views of Orient Harbor, Bug Light and Shelter Island. Moor your boat in the bay; kayak, swim, fish or chill on the decks and porches. Basement game room w/ Ping-Pong, TV and games. Conveniently located near shopping, restaurants, ferries, farm stands, vineyards.

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$12,000 IC / month
4bedrooms
4bathrooms
land  1,578

By Daniel Gale Sotheby's International Realty

Nearby
10

House Greenport (United States)

Situated in a charming and serene neighborhood in Greenport and located just minutes from both Greenport Village and Southold Town Beach, this recently updated Cape offers 1,500 sq. ft. with 4-bedrooms, 2-baths and a spacious living area that flows seamlessly into a bright and airy eat-in kitchen. A full, unfinished basement leads out to an expansive, fenced backyard, and the attached 1-car garage and driveway capable of accommodating 2 additional vehicles ensures sufficient parking for tenants. Don't overlook the opportunity to rent this gem! Please note that the reported square footage is an approximation as the Town of Southold does not have records of the square footage for the second half story.

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$3,800 IC / month
4bedrooms
2bathrooms

By Daniel Gale Sotheby's International Realty

Nearby
30

Farmhouse Greenport (United States)

Summer 2024 Rates: May24-June30 $20K, July2-Aug1 $30K, Aug2-Sept3 $35K, Sept4-Oct4 $15K: Rare new construction on a quiet side street in Greenport Village, this modern luxury home is the perfect base to explore the beaches, wineries, and farm-to-table dining of the North Fork. Walking distance to downtown Greenport and a short drive from all the major North Fork sights. Or just whittle away your days enjoying the amenities of your luxurious home retreat. Lounge in your heated saltwater pool while sipping a cold drink. Curl up with a book in front of your gas fireplace. Catch up on sleep surrounded by plush bedding on your memory foam mattress. Immerse yourself in the low-key North Fork lifestyle at your private Greenport Getaway.

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$13,500 IC / month
5bedrooms
4bathrooms
land  526

By Daniel Gale Sotheby's International Realty

Nearby
23

House Greenport (United States)

Classic contemporary style New Construction in the heart of Greenport Village. This 2900+ sqft offering features 4 wide white oak hardwood floors throughout w/ inviting Great Room, eat-in Kitchen and Junior Suite bedroom on Main Level. The second floor features an cozy additional den/media room with two generously sized guest bedrooms sharing a full bathroom, laundry, ample storage, a primary ensuite bedroom with walk-in closet and large walk-in shower. In addition to the 1st and 2nd floors is a partially finished basement with separate outdoor access already in place or as lower level gym or media room. For those looking for tremendous value and as central Greenport Village location, this is an absolute must see.

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$3,950 IC / month
4bedrooms
4bathrooms
land  607

By Daniel Gale Sotheby's International Realty

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