Deep River CT Real Estate & Homes for Rent

Mid-Century Contemporary with views of Long Island Sound in a private community with association beach across the road. Cathedral ceilings & large windows add to the bright & open feeling of the communal area. Water view deck for relaxing and entertaining. 1000 sf of living area plus 800 sf walk-out basement converted to a fully renovated recreation room/office with recessed lighting, new furniture, renovated bathroom, and laundry. Offered Sept 5-30 $6,500; year $4,000/mo. Permit# 0368

Down a private driveway with breathtaking views of the sea, privacy and luxury collide! This impressive beach estate rests on 12.3 acres and 460' of waterfront beach tucked away in a protected cove on the Long Island Sound. 6 bedrooms include their own ensuite bathroom, plus two half baths, a gourmet eat-in kitchen that is truly a chef's domain with multiple seating areas, and views of the inner courtyard. Huge living room with a roaring fireplace, additional living rooms, pool house, TV room and incredible outdoor vignettes. You'll never want to leave! Near all the North Fork has to offer - award winning vineyards, renowned restaurants, boating and great shopping! $65K July 13-Aug 3. Permit #0792

This beautifully furnished private deeded beach home is available to rent year-round or seasonal. The home is super clean and move in ready! There are three large bedrooms, three full bathrooms, a living room on each floor, updated kitchen, hardwood floors and central air conditioning. Amazing location just a few homes away from the sound beach to enjoy swimming, fishing and sunsets! Southold Town Rental Permit #1040

HILLCREST ESTATES RESORT-STYLE ENTERTAINING! This stunning home boasts 4 oversized Bedrooms (Sleeps 13+), 2.5 Baths, 1st floor Office, LR, DR, Den with Fireplace, Designer EIK, Rec Room with ping-pong and air-hockey tables. Magnificent, resort-style, landscaped private yard with expansive patios, multiple outdoor seating areas, heated inground pool, outdoor shower, fire pit, sports court, tree swing, front porch and more. Freshly painted, beautifully decorated open spaces to accommodate large gatherings. Private resident beach, a stones throw to Orient ferry, village, boating, Greenport, fine restaurants, golf courses and vineyards.

Contemporary private, secluded home in bucolic Browns Hill, Orient. 12 x 25 heated/saltwater/gunite pool with deck & patio overlooking farm fields with distant bay view. A welcoming space from the foyer to the living room with wood burning fireplace, updated gourmet kitchen and dining room with panoramic farm and bay views. Three levels of living space with one bedroom & full bath on each floor: lower-level bedroom with deck, ground floor master ensuite bedroom with full bath and deck, second floor loft/bedroom. Wrap around deck and outdoor shower. Association Sound beach, just a short walk. Offered July $30,000; Aug $30,000. All inclusive. Permit # 0174.

Spacious & immaculate Sound front Contemporary home sitting on a hilltop in Orient, overlooking Long Island Sound to the north & farm fields to the south. Meticulously renovated & professionally designed 4 bedrooms, 5.5 baths with 128 ft of private beach. The ground floor has a large family room with glass doors to a blue stone patio, lawn, & stairs to the beach. This level includes an ensuite bedroom, additional full bath, Malm fire drum, & infra-red sauna. The main floor offers an open floor plan with living/dining/den/kitchen, a 2-sided fireplace, new kitchen, new baths, waterside & farm view decks. A professional ping-pong table, CAC, & outdoor shower are additional amenities. The panoramic Sound and farm views on 1.84 acres offer unique privacy. Offered July 65,000; Aug 75,000. Permit# 1059.

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 $3,200/mo. Permit #0308.

Stunning Waterfront shingle style home overlooking Long Island Sound. 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 Aug-LD $55,000; Sept 5-30 $25,000. Permit# 1108.

Beautifully converted 19th C Barn - three story residence with 4 bedrooms, 3 full baths, Eat-in kitchen, deck off living room with sound views, and private beach access. Apr $5,000; May $5,000; June $8,000; July $15,000; Aug $15,000; Sept $10,000; Oct - Mar $4,000/mo; yearly $6,500/mo. Permit# 0774.

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. June $25,000, July $35,000 Permit #0441.

Orient Village- Located in Orient at 944 Youngs Avenue, on a private country lane sits this perfect country cottage, oh so close to Orient's favorite Youngs Road Beachfront. 3 bedrooms and 2 full baths, lovely outdoor deck, yard and overlooking a flower farm and just down the street from Village lane, the Orient Country Store and the Jitney. August $14K RP# 907

Available 2024: MD-LD 40K, June 10K, July 15K, Aug-LD 18K. Experience the ultimate North Fork summer with the perfect combination of comfort and privacy in this spacious 4 bedroom home with heated pool on 3.5 acres. Explore the pristine beaches, beautiful vineyards and breweries or check out one of the many chef renowned restaurants the area has to offer. This property is the ideal retreat for a memorable summer getaway on the North Fork.

Come to the beautiful North Fork and spend your summer in this outstanding, stylish home in private sound front community at 560 Grandview Drive, Orient. Large bright home with 4 bedrooms and 3 baths, great room with fireplace, primary bedroom en-suite with fireplace, super floor plan and chic furnishings, set on 1 acre, heated pool with Jaccuzzi; ready for your off season or summer vacation and beyond. Close to beautiful beaches, Orient village, and the Jitney. Available June $14K, July $30K, August-LD $35K. Year Round $8,500/monthly. Rental Permit# 0473

SUMMER 2024 - 3 Bedroom/2 Bath Home. Open Floor Plan and Vaulted Ceilings. Back Deck and Pool to Enjoy the Days of Summer. Several Nearby Beaches Too! Memorial Day to Labor Day $55,000; June $15,000; July $20,000; August to Labor Day $25,000; $5,000 Weekly with Two Week Minimum. Permit #0586.

Spacious and grand, historic Terry Mulford House C. 1716, set on 5.8 private acres, fully renovated, with 5 bedrooms and 4 new full baths. New eat-in kitchen, living room with piano and flat screen TV. Relax on the wrap-around porch or rear courtyard. A short trip to Orient and Greenport Village, Orient State Park, marinas, sound, and bay beaches. Price includes all utilities, mid-term, and departure housekeeping. Offered May $9,000; June $13,000; July $15,000; Aug $15,000; Sept $10,000; Oct $4,000; yearly $3,500/mo. Permit #0667.

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 $7,000. Permit #0091.

Rental Permit # 1102 Welcome to 1405 Terry Lane, Orient, a fully renovated waterfront residence with a private beach that extends for miles in each direction and a new, heated 20 x 40 in-ground pool with views overlooking the Long Island Sound. Situated on 1.63 acres at the end of a private road, a remote gated entrance opens to a white stone driveway that passes by a private half acre vineyard and consummates at the 3 bedrooms, 2.5 bathroom home with the master bedroom with en-suite bathroom on the first floor. The home has hardwood floors throughout, a modern kitchen with expansive views of the Long Island Sound, a four seasons room that lead to an spacious deck with awnings and all of the amenities one could ask for when entertaining guests. The sprawling lawns and have manicured landscaping and plantings private both room to play, privacy, incredible sunsets and a serene environment. This is truly both a remarkable and unique getaway to spend your summer months. August 1 - 31 $32,500 & August 1 - September 3 $35,500

House is at the end of Ketcham Lane. Introducing a Sequestered Post Modern custom designed home. The property backs up to Cove Beach Estates and NYS Ruth Oliva Preserve. This 3 + bedroom home offers high ceilings and sun-filled rooms with high-end hardwood floors throughout. The well maintained property features an inground backyard pool and patio entertainment area, all just a stones throw from the Long Island Sound and the Peconic Bay.

Village Lane summer house - full season rental - historic charm seamlessly blended with modern amenities. Water views. Hardwood floors, lots of light, unique architectural interest with sophisticated decor for the discerning traveler. Rent reflects MD-LD.

Beautifully updated & fully renovated traditional Arts & Crafts home in the heart of Orient Village and one block from Orient Harbor. Gourmet kitchen with Thermador 6 burner/griddle stove, Subzero refrigerator, Bosch dishwasher. Enclosed front porch. Fenced yard, outdoor shower, backyard deck for relaxing, grilling & dining. Professionally landscaped with vegetable garden and outdoor shower. Offered April $9,000; Sept $16,000. Permit #0827.

Year Round ONLY $4500 Per Month!! Welcome To Plum Island Lane In The Much Sought After Community Of 'Orient By The Sea' - Which Is A Stones Throw From The Private Beach! This Perfect Get Away Home Consists Of 3 Large Bedrooms, 1.5 Bathrooms, A Spacious EIK, Bright Open-Plan Living Room, Laundry And Recently Installed In-Ground 20 x 40 Saltwater Swimming Pool! This Gem Of A Home Was Completely Renovated To A Premium Standard In 2021. It Is Fully Furnished And Contains All New Modern Appliances. Close To The Cross Sound Ferry, Orient State Park And Public Marina. Reserve A Viewing Right Away And Avoid Missing Out On This Beauty! May: $6,000 - June: $10,000 - July: $18,000 - August to LD: $18,000 - September: $9,000 & MD to LD: $32,000. Rental Permit #: 0812

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; Nov $6,000. Permit #0483.

Lovely, sunlight filled ranch in 'Orient by the Sea' community. Stellar vacation location just 4 houses from the community's gorgeous, private LI Sound beach. Eat in Kitchen, Dining & Living rooms, Ensuite primary, 2 add'l bedrooms & 2nd full bath. Front & back porches and spacious yard. Nearby Orient State Park offers miles of hiking, cycling trails, birding, wildlife viewing and a miles-long, sandy Bay beach. Rental permit # 1100 exp. 3/25/2026.

Summer rental in Orient. Beautifully renovated inside and out featuring 4 bedrooms, 2.5 baths, plus a spacious backyard with pool. Available for August-LD. RP# 0930

Step into summer in Orient this year. Relax and rejuvenate in the quiet soundfront beach community of Orient by the Sea. Sunny open concept floor plan incudes glass doors that lead out to the covered backyard deck and invites indoor and outdoor entertaining. Just a short drive away to Greenport's many restaurants, the area's popular wineries for a tasting. Or enjoy a bike ride to Orient Beach State Park for a peaceful day on the bay. MD-LD $20,000 June $5,000, July $8,000 Aug $10,000 Permit #0863