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AVAILABLE THIS SEPTEMBER 1 TO JUNE 30, 2027. PARTIALLY FURNISHED. PAINTED ALL WHITE. NEWER REFINISHED HARDWOOD FLOORS! NEWER BATHROOM! This open concept 2 bedroom home, hardwood floors, and located in one of the best beach Associations off Neck Road, is perfect for 1-2 people. Fabulous deck off the back of the home provides a perfect place to enjoy a book or glass of wine. Absolutely NO pets, no smoking. Owners retain use of the garage. Come enjoy the academic term by the shore!
…By William Pitt Sotheby's International Realty
AVAILABLE FROM EARLY SEPTEMBER 2026 TO END OF MAY 2027! Welcome to this enchanting 4 bedroom, 2 full bath home, where the beach is just a half-block stroll away! Located off Neck Road, 1 mile from the heart of Madison, CT, this residence offers the perfect blend of coastal charm and convenience. As you enter, the first floor greets you with a Family Room, through to a Kitchen, then onto the Living Room. The sunroom is a tranquil space to unwind, offering views of the outdoors and filling the home with warmth year-round. The 1st is rounded out with 2 well appointed bedrooms. The second floor is a private retreat featuring the oversized Primary Bedroom and an additional bedroom, each designed to provide a peaceful escape with ample space and comfort. Step outside to the expansive outdoor deck, where you can soak up the sun or entertain guests in the sea breeze. The fenced yard ensures privacy, while the patio with an awning offers a shaded sanctuary for those long summer days.This home's prime location near the beach allows for endless days of sand and surf, while the close proximity to downtown Madison ensures all the conveniences of town living are just moments away. If you are seeking an academic rental, this home offers a lifestyle of comfort and relaxation. NO PETS.
…By William Pitt Sotheby's International Realty
AVAILABLE FOR THE MONTH OF AUGUST. Live the ultimate shoreline lifestyle on Middle Beach Road, Madison's most prestigious and sought-after coastal street. This delightful 2-bedroom, 1-bathroom garage apartment (on the 2nd floor) offers a rare opportunity to enjoy stunning dual views, capturing the sparkling waters of the Long Island Sound from one side and the serene, ever-changing landscape of the salt marsh from the other. The interior features a functional layout with a welcoming Living Room and an efficient galley kitchen. Step out onto your private back deck-the perfect spot for morning coffee or evening relaxation while taking in the peaceful marsh views and coastal wildlife. Best of all, you are just a short, scenic walk away from East Wharf Beach or The Surf Club and Madison's charming downtown, filled with local shops, dining, and the iconic RJ Julia Booksellers. Don't miss this chance to experience the perfect blend of natural beauty and unbeatable convenience on the shoreline.
…By William Pitt Sotheby's International Realty
Fabulous academic rental available Sept 1st through May 31st 2027. This direct waterfront four bedroom home set on a one of kind property with access to a private beach. Enjoy fabulous views from your deck, large yard and tidal pool. Plenty of space for everyone with a bedroom with full bath on the main level, Primary en suite on the second floor with private balcony and two additional bedrooms with full bath; this home will sleep 8/9 guests comfortably. Central Air in the main house and every convenience you could possibly want.
…By William Pitt Sotheby's International Realty
Available from September 15, 2026, through May 15, 2027, this stunning direct-waterfront academic rental offers an unparalleled coastal lifestyle with breathtaking, panoramic views from almost every room. The bright, sunny interior features an open-concept main level, highlighting a gourmet kitchen with quartz countertops and stainless steel appliances, alongside a generous living and dining area complete with a gas fireplace and walls of glass that frame the ever-changing coastal vistas. Sliders open to an expansive wrap-around deck perfect for relaxing, while the direct-access beach with its natural tidal pools awaits just steps away. The home's flexible layout includes a convenient main-floor bedroom with a full bath and laundry, while the upper level boasts a second bedroom, a full bath, and a one-of-a-kind primary suite featuring soaring ceilings, dramatic walls of glass, and a private balcony for your morning coffee. Please note that this is a strict no pets, no exceptions property.
…By William Pitt Sotheby's International Realty
Renovated 2-bedroom, 2-bathroom cottage for rent at 98 Union Street in Guilford, Connecticut - walking distance to Guilford Green, the town center, restaurants, and shops. This shingle-style home, named Seascent, pairs a classic Shoreline exterior - white siding, picket fence, and blue front door - with a fully updated interior. The open-concept main level features vaulted ceilings, hardwood floors, and a chef's kitchen with a navy blue island, quartz countertops, stainless steel French-door refrigerator, gas range, and stainless range hood. Globe pendant lighting hangs above the island, and a built-in banquette dining nook and living area with sectional seating complete the main floor. A built-in ladder leads to a loft space, adding flexible square footage above the living room. The primary bedroom offers a vaulted ceiling, shiplap accent walls, and a walk-in closet-ready dresser wall. A second bedroom provides comfortable guest or home-office space. Both full bathrooms have been updated, including a double-vanity bath with stone countertops, black matte fixtures, and tree-print wallpaper. Outside, a private paver patio in the fenced backyard offers space for outdoor seating and entertaining, and a personal driveway provides off-street parking - a rare find this close to downtown Guilford. Available August 15 on a 12-month lease. Tenant responsible for all utilities. No pets. Located within walking distance of Guilford Green.
…By William Pitt Sotheby's International Realty
Rare find in the Town of Essex, Village of Ivoryton! This absolutely immaculate 3 bedroom, 1 1/2 bath ranch style home is situated on a beautiful lot in a wonderful neighborhood. The home has undergone a major renovation from top to bottom including hardwood floors, windows, stainless kitchen appliances, washer, dryer and central air. Relax or entertain on a spacious deck. There is a full basement and separate outbuilding for storage. The lovely half acre lot has been professionally landscaped. The driveway and parking area are paved. No smoking. No pets. No short term leases. Credit & Background Check, Security Deposit required. Make this gem your new home!
…By William Pitt Sotheby's International Realty
Live the Good Life in Historic Essex Village! This beautifully renovated 3 level apartment in an 1880 duplex home blends timeless charm with modern design in the heart of the Connecticut River Valley. Thoughtfully reimagined with an architecturally designed open floor plan, the light-filled first floor features soaring 9+ foot ceilings and generous spaces for living, dining, and entertaining. The stylish kitchen boasts stainless steel appliances, granite countertops, and crisp white cabinetry. A full bath completes the main level. Upstairs, the private primary suite offers a serene retreat with its own full bath, dressing area, and a wall of closets. The third floor provides flexible space-ideal for a home office or storage. Comfort is ensured with split-unit AC/heat on all levels and efficient oil-fired hot water heat on the first and second floors. Laundry is conveniently located in the basement. Relax on your private backyard patio. Just steps from your front door, enjoy Essex's unique shops, fine dining, scenic marinas, and the beautiful Connecticut River. Perfectly situated midway between New York and Boston, this is Village living at its very best!
…By William Pitt Sotheby's International Realty
Rarely available! This historic 1860 Essex Village waterfront home is nestled on a quiet lane with direct waterfront on Middle Cove. Step back in time and experience the charm of this Vintage home, complete with many original features, while still enjoying modern amenities and updated appliances. The home boasts original wood floors, a stunning floor-to-ceiling bay window in the living room, and a built-in hutch with a Butler's Pantry in the dining room. Upstairs, the primary bedroom is a spacious two-room suite, accompanied by an additional bedroom and bath. The semi-finished lower level, reminiscent of a cozy tavern room, provides walkout access to the patio, backyard, and waterfront. View stunning sunsets over Middle Cove! Relax on the inviting front porch or take a short stroll to the Griswold Inn, Noah's, the Black Seal, and an array of charming shops, yacht clubs, and marinas. The barn outbuilding is not included in the rental. No pets, no smoking. Minimum 1-year lease. Conveniently located halfway between New York and Boston. You will love living in one of the Historic Homes of Essex Village!
…By William Pitt Sotheby's International Realty
Escape to the serene shores of Long Island Sound with this exquisite summer rental in the coveted Fenwick area of Old Saybrook, Connecticut. This traditional Fenwick Cottage has a harmonious blend of classic charm and modern luxury, making it the perfect waterfront getaway for relaxation and entertainment. Spacious waterside family room featuring a magnificent fieldstone fireplace, creating a warm and inviting atmosphere for family time or quiet contemplation. A large, beautifully designed chef's kitchen with top-of-the-line appliances, an inviting eating area, and a wet bar, catering to culinary enthusiasts and effortless hosting. Expansive covered wrap-around porch with a cozy outdoor fireplace and a luxurious hot tub, perfect for evening relaxation or social gatherings. There is an elevator off the kitchen. This Fenwick summer rental is not just a home; it's a retreat that promises unforgettable moments and tranquility amidst the natural beauty of the shoreline. Whether you're basking in the sun, enjoying the hot tub under the stars, or preparing gourmet meals in the chef's kitchen, this property will be an unparalleled summer experience. Discover the magic of Fenwick and create memories that will last a lifetime.
…By William Pitt Sotheby's International Realty
Charming Farmhouse Rental in the Hamburg Cove section of Lyme available for lease. This spacious home has an updated kitchen with walk in pantry, newly refinished flooring on the first floor, charming stone fireplace and views of the cove from your patio. A dining room with built in china cabinet and door to the back yard, bookcases & french doors to enjoy in the living room, two front porches, one enclosed for 3 season enjoyment. There is an antique garage perfect for storage. All bedrooms are on the 2nd floor and the home features 1 1/2 baths. New siding and windows add to this well maintained home. Yearly lease, credit check, security deposit required, immediate occupancy.
…By William Pitt Sotheby's International Realty
Academic Rental in White Sand Beach. Four Bedrooms and two full baths. Large front to back living room with wood burning fireplace. The dining room table can seat eight comfortably and the kitchen is fully applianced. The first floor laundry is just off the kitchen. There is an office/den just off the dining room leading to and outdoor patio. A short walk brings you to the beach and across the road are tennis courts, basketball court and play area.
…By William Pitt Sotheby's International Realty
Offered June $10,000 ($2,500/wk); July $20,000 ($5,000/wk); Aug $25,000 ($6,250/wk); Sept $12,000 ($3,000/wk); Oct $10,000 ($2,500/wk). Two-week minimum. This contemporary waterfront home on Great Pond enjoys sunrise over the water and spectacular sunsets over Long Island Sound from its hilltop setting in one of the North Fork’s most distinctive beach communities. Surrounded by native plantings and filled with natural light and cooling breezes, the home is designed for effortless indoor-outdoor living. Spanning three floors and 2,600 square feet, it features 3 bedrooms, 4 full baths, and multiple spaces for gathering, entertaining, or quiet retreat. Enter from the spacious front deck, with seating for four and views of lush natural landscape and Sound. The main level comprises an open-plan living room with a wood-burning fireplace, dining area, eat-in kitchen, TV room, full bath, and a rear deck with dining table for six overlooking Great Pond. The ever-changing landscape of water, sky, and birdlife makes this a haven for nature lovers. Upstairs are two ensuite bedrooms, both enjoying beautiful water views and brand-new bathrooms, the one in the master suite benefiting as well from a long bathtub. The garden level offers a third bedroom, full bath, laundry area, movie and screening room, and an office/den with glass doors opening onto a rear deck with lounge chair, sauna, and outdoor shower. A private path leads directly to Great Pond, where kayaks and a canoe await exploration. Additional amenities include bicycles, a massage chair, piano, binoculars, telescope, and EV charger. Kenney’s Beach and the beloved Little Fish restaurant are just a short bike ride away, creating an exceptional blend of comfort, privacy, and outdoor adventure in the heart of the North Fork.
…By Daniel Gale Sotheby's International Realty
Life is Better by the Beach! Welcome to 34 Corsino Avenue, a cozy 3 bedroom, 1 bath unfurnished ranch available as a year-round rental in the desirable Miami Beach Association. Just a short stroll to the association's beautiful private beach on Long Island Sound, this charming home offers the relaxed coastal lifestyle you've been looking for. Ideally suited for one or two occupants, the home features tile flooring throughout, an updated kitchen with a new stainless steel electric range, range hood, and refrigerator, plus three bedrooms that offer flexibility for guests, a home office, or hobbies. A bright three-season room provides additional living space, while the oversized deck and private backyard create the perfect setting to relax, entertain, or enjoy the sea breeze. If you've been dreaming of year round beach living, don't miss this opportunity to enjoy one of Old Lyme's shoreline community. Pets will be considered with owner approval. Tenants will be responsible for Electric, cable/ internet and snow removal.
…By William Pitt Sotheby's International Realty
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
…By Daniel Gale Sotheby's International Realty
Rental Available August 25, 2026- June 15, 2027 An incredible East Rock opportunity. This magnificent 5 BR furnished home is available for academic rent. An elevator takes you to all 3 floors of this amazing home as well as down to the full dry basement perfect for storage. Main floor boasts a Living room, dining room, a huge kitchen that opens to a family room as well as a big deck that leads to a fully fenced in private yard. The second floor has 4 BR's, one with built-ins doubles as a great home office.2 full beautiful new baths. The third floor is fabulous! A private family room, loft, huge bonus room, a bedroom and new beautiful bathroom. Tons of built in bookshelves throughout. Gas heat, central air. Located in the private corner of Everit street across from the park with off street parking. Minutes to Foote school and a short walk to Yale and Downtown New Haven. No smoking. No pets. 700 Minimum credit score. LISTING AGENT MUST BE AT ALL SHOWINGS AND TIMES ARE LIMITED SO PLEASE GIVE PLENTY OF NOTICE Rentspree Application Accepted
…By William Pitt Sotheby's International Realty
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.
…By Daniel Gale Sotheby's International Realty
Available June $15,000; July $35,000 (RENTED); Aug 17-31 $18,000; Sept $20,000. Sound Front Contemporary Octagonal Home with Private Beach. Contemporary and chic, mint condition 1970's modular octagonal home located on a breath-taking sound front walk-out private beach in Orient. Three bedrooms, each with a full bath and an additional powder room. Updated kitchen and bathrooms. Every room is furnished with period mid-C style furniture. Living room has original Malm wood burning fireplace. Many spacious common areas, including glazed porch connecting the two octagonal wings. Relax on the large water-side deck with hot tub while enjoy panoramic water views from every room. Permit #0465.
…By Daniel Gale Sotheby's International Realty
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 living room with a wood-burning fireplace, a formal dining room, and a generous eat-in kitchen with a butler’s pantry. A TV room/bedroom and full bath complete the ground floor. Upstairs are five bedrooms, including a primary bedroom with a private balcony and half bath, along with a full bath for the four additional bedrooms. The private grounds include an in-ground pool. Latham’s Farm Stand and Orient Village are just a short walk away. September is an ideal time to enjoy this peaceful, timeless retreat.
…By Daniel Gale Sotheby's International Realty
Stunning waterfront shingle style home overlooking Long Island Sound with private beach access. Waterview, heated pool. Wrap-around porch. Original beach stone fireplace, vintage beadboard walls, large, updated gourmet kitchen, open common area, 5 bedrooms, 3 bathrooms, large master ensuite with private screen water view balcony. Beautiful interior furnishings, with teak rocking chairs, chaise lounges and picnic table on porch and pool area for entertaining. Close to Orient Village amenities, marinas, Country store, Yacht Club, and bay beaches. Offered June 3-27 $28,000; Sept 2-16 $14,000. Permit# 1108.
…By Daniel Gale Sotheby's International Realty
2026 Rates: NO AVAILABILITY New Modern Farmhouse Completed in 2021 and located in the heart Hog's Neck in Southold Hamlet. This home features an impressive 20 x 50 heated pool with electric cover, out door shower and sprawling paver patio. The interior is open and airy with Chef's Kitchen outfitted with Thermador appliances, large living room with built in shelving, gas fireplace and formal dining room. All four bedrooms are located on the second level: 1 Primary En-suite, 1 Junior Suite, 2 Guest Bedrooms and Full Hallway Bathroom. You will enjoy being within close proximity to Goose Creek, South Harbor Park Beach and Southold's vibrant business district!
…By Daniel Gale Sotheby's International Realty
Authentic 1770 Cottage in the heart of Orient Village. Lovingly restored & maintained Village home on beautifully landscaped lot, offering private grounds & distant views of sunsets over the bay. Furnished in period antiques, screened-in porch off kitchen, first floor bedroom. Walk to amenities, bay beach, Yacht Club, marina, farm stand & Jitney. Offered Sept 3-Oct 3 for $8,000. Permit #0091.
…By Daniel Gale Sotheby's International Realty
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. Available Apr $10,000; May $12,000; Sept $20,000; Oct $15,000; Nov $10,000; Dec $10,000. Permit# 1020.
…By Daniel Gale Sotheby's International Realty
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