Old Saybrook CT Real Estate & Homes for Rent

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.

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

Impeccably restored and updated 1850's Farmhouse in the heart of Orient Village. Featuring a great room with open floor plan - gourmet kitchen/dining/living room, a second-floor master bedroom with sitting room, full bath, and walk-in closet for a total of 3-bedrooms 2.5 baths in the main house. There is a separate Cottage with kitchenette, bedroom, and full bath, perfect for guests. Lovely private grounds with gardens, grand lawn, and heated salt water gunite pool. Walking distance to all village amenities, beaches, and marinas. Offered June $20,000; July $45,000; Aug $45,000; Sept $25,000. Permit # 1019.

Private, recently renovated, arts and crafts style ranch located in the heart of Orient Village. Three bedrooms, 2 full baths, open kitchen/ living room/ dining room, library, front porch, rear deck with screened outdoor dining area & grilling station. Close to beaches, marinas & village amenities. Offered Aug $15,000. Permit #0505.

Very spacious, sunlight filled beauty just 3 minutes to gorgeous LI Sound beach. 44' x 24' gunite, heated, saltwater pool. Open concept LR/DR/KI with sliders to expansive deck overlooking sprawling & private yard and pool area. Upstairs has a large, 2nd living room with billiards, foosball, tv area & sliders to another deck. 2 primary bedrooms - one on each level. 2nd floor primary has living room area and a wet bar. Home & grounds impeccably maintained and tastefully furnished throughout. Fine dining & state park just down the road. A scenic 9 mile drive to bustling downtown Greenport. Rental Permit #1117. Exp. 5.6.26.

Vineyard Views. Modern Farmhouse on private 1 acre located on the only private, working vineyard in Orient Village. 16 x 32 heated pool, newly renovated chef's kitchen and baths. The home features 3 bedrooms, 3 full baths. Ground floor designed with open common space and designer furnishings for luxurious entertaining, featuring living room with cathedral ceiling with sliders to pool and deck, eat-in kitchen and dining room with sliders to vineyard deck. Den with pull out queen bed, bedroom with queen bed, 2 full baths, laundry and screened porch complete the ground floor plan. Second floor has 2 additional bedrooms; master with king bed, and 3rd bedroom with 2 full beds, and full bath. Amenities include central air, fully stocked kitchen with Aga stove, high speed internet, TVs with streaming video, gas grill. Walk to Village, Yacht Club & steps to association Willow Terrace bay beach. Embrace the North Fork lifestyle. Offered June $25,000; July $45,000; Aug-LD $55,000. Two-week options available. Permit #0516

Available for 2024! Newly constructed modern farmhouse with 4 bedrooms, all with ensuite baths. Get away from it all in this hotel-like Orient home. Open concept kitchen, dining, living with beautiful light filled bedrooms. Enormous blue stone patio leads to in-ground pool and beautifully landscaped yard beyond. Minutes from the private association beach, Orient State Park and Duryeas Restaurant & Bar. Past tenants all loved their stay at this home!! June 40k, July 45k, Aug 50k

Relax, rejuvenate and recharge in this updated North Fork gem! This charming home boasts a new kitchen, large living room with fireplace and separate dining room. Unwind on the screened-in porch, listening to the sounds of nature, or host BBQs in the large fenced-in yard, ideal for games and activities. Three bedrooms and a full bath on the 2nd floor provide comfortable sleeping for up to 6 guests. Located on a quiet road, you're still close to beaches, farm stands, and local vineyards! June $6,500 for 2 weeks. July $8,500 for 2 weeks. 2 week minimum. Permit# 0494.

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.

BOOK '24 NOW: Various Rates All Year Long: East Marion, North Fork - Coveted and rare rental (Rates: Season 2023 $87k; June $20k, Aug-LD $40k; Bal of Sept OR Oct $20k; off Season Winter $7000 per mo etc) on the bay in private setting overlooking Bug Light and Long Beach. Spectacular setting with heated, waterside pool. One floor living with many access points to southeast facing deck/terrace. Incredible sunrises - and sunsets reflected on the lighthouse and bay. Living room w/fireplace, sunroom/office, EIK with upscale appliances; DR w/sliders to terrace for outdoor dining. Waterside master suite w/full bath, 3 additional bedrooms w/guest bath. Large 3+ car garage for cars and summer toys. Private yard space for playing and pique-nique'ng. The ultimate North Fork beach house rental for you and your guests. Home sleeps up to 12 people comfortably. Life doesn't get better than at Tara-by-the-Bay. Close proximity to area farmstands, lavender fields, wineries and destination restaurants in Greenport. Permit #0248.

Charming and chic 3 bedroom, 1.5 bath Cottage on Lake Marion with many charming original features. Open, sunny floor plan with common area that opens onto spacious lakefront deck perfect for relaxing, grilling & dining. Wood burning fireplace, fully equipped cook's kitchen, private dock, outdoor shower, & easy stroll to association bay beach. Offered June $8,000; Aug $16,000. Permit# 0692.

A light, bright and mint condition Orient Village 4 bedroom, 4 bath bayfront home, featuring beautiful classic lines and architectural details throughout. Walls of windows and high ceilings showcase stunning sunsets over Orient Harbor and beyond. Gourmet kitchen, open floor plan with glass doors to outdoor dining area, waterside lawn, two decks and stairs to the water makes this a perfect opportunity for entertaining and family relaxation. Rental includes a gas grill, 2 boat moorings and nearby association sandy beach. This very well appointed home includes an open fireplace, perfect for an extended stay throughout the fall and beyond in an idyllic location that beckons peace and relaxation surrounded by nature and luxury. Permit# 0595.

Private, peaceful home on a serene acre of property. Just renovated, featuring open modern Kitchen/Dining combo for casual entertaining. Separate family room across open foyer with fireplace and loads of puzzles & games. Charming covered front porch looks out onto front yard. Back deck with grill overlooks pool and backyard. Three bedrooms: 1 Queen, 2 full beds and primary with king bed and en-suite bathroom with large shower. Hall bathroom with tub. Laundry in basement. Tasteful furnishings, all the basics & wifi together make this an easy place to settle in and retreat to for a great vacation & workplace away from the everyday home office. Treadmill for workouts. Beach rights at the end of the Bay Avenue. The surrounding area has it all: vineyards, farm stands, restaurants, beaches, downtown Greenport and more. Avail for use: Fire Pit - Solo Stove, 3 bikes.

Cape-Cod-Style Cedar-Shingle House situated on edge of low bluff. Wooded lot with 2nd-story master bedroom suite/deck. Fantastic 180-degree views of Gardiner's Bay, Bug Lighthouse, Shelter Island, Orient Village and East Hampton with 150-feet of private sandy beach and boat mooring. Permit #0049.

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.

Live the waterfront dream! Imagine having the choice to wake up overlooking Gardiner's Bay or tranquil Marion Lake. This immaculate 3 bedroom, 3 bathroom home offers unparalleled views and much more. Your own Right of Way to the Bay, a mooring for your boat and lakefront access in the backyard! Meticulously appointed and ready for the season! Cozy up by one of the 3 gas fireplaces, indulge in a luxurious soak in one of 2 tubs or have coffee on one of the four waterside balconies. You will not want to leave! Ren permit # 1075

Unwind on Marion Lake and recharge on the Bay! This 2-bedroom, 1 bathroom lakefront cottage is the perfect escape! Just steps away from the Bay allows you to play the day away! Rinse off in the outdoor shower, dine outside on the large deck overlooking Marion Lake and then chill out by the fire pit, making s'mores and creating memories! June:$10K, July:$15K, Aug:$17.5K, Sept:$12K, Oct:$10K, Mem Day-Oct:$60K Permit # 1060

Imagine waking up to breathtaking sunrises over the bay and the sound of gentle waves lapping at your doorstep. This Bay front cottage offers the perfect atmosphere to unplug, relax and connect on your own terms. 3 bedrooms, 1 full & 2 half baths, sunroom, outdoor shower and waterside firepit. Book now to create your unforgettable memories! June:$15K, July: $20K, Aug:$25K, Sep:$15K, Oct:$15K, Mem-Oct:$80K Permit # 0449

Cute as a button cottage located in Gardiners Bay Estates. Tucked away in a private sandy beach community w/ mooring and bulkhead space to tie up to for boaters and a swim platform for summertime fun! Back patio to chill, grill & dine al fresco or screened in porch to kick back & relax, rain or shine. Just 3 miles to Greenport Village, 1/2 mile to Sep's Farm Stand & Lavender By the Bay & only 7 miles to the Orient Ferry. (Southold Town Rental Permit #0775)

Immaculate shingle-style home perched above the Long Island Sound. Enjoy endless water views and breathtaking sunsets from the heated pool and private beach. Open floor plan with EIK and fireplace, bedrooms across three floors, including first and second-floor primary suites with private waterside balconies. The large finished basement features a media/game room. The private office is ideal for remote work and has a third private waterside balcony-prime indoor/outdoor summer living just a mile from Greenport Village's shops and restaurants. Personal property manager to address any tenant needs. Hamptons luxury with North Fork vibes. Two-week minimum.

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. Available May- $10,000,October - $10,000. Permit# 0026.

Enjoy these breath taking views of Spring Pond out to Gardiner's Bay and Bug Light House. Pass by the renown Lavender Farm on your way to this open concept sun filled home in Gardiners Bay. Offering all the luxuries and amenities within a short distance to a private sandy bay beach. Enjoy August on the North Fork and simply relax. bug

2024 Rates: June $5,000/week or $20K/month; July $6,750/week or $27,000/month; A1-LD $7,125/week or $28,500/month. 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.

Wonderful North Fork summer rental with in ground pool located on a quiet block with a private community sandy beach at the end of Gillette Drive. This spacious home features 3 bedrooms and 2 bathrooms with a fenced in back yard with beautiful views of a lavender farm. Vineyard, Farm stand and golf course less than a mile away and approximately only 2 miles from the town of Greenport where you can enjoy great activities and fine dining.

2025 Rates: MDW-LD $142,500; June $30K; July $52,500; A1-LD $55K. This Modern Hamptons style home offers everything you could ask for from a Summer retreat to the East End. Featuring over 3500sqft of living space, the impressive Great Room is the centerpiece of the house and flows seamlessly to the rear yard which features a 20x40 heated gunite pool with sun deck, large architectural stone patio w/ fire-pit and large gas fired grill. In addition, you will enjoy lazy summer walks to the Rock Cove Estate community private Sound side beach and peak-a-boo water-views from the second floor. All bedrooms are generously proportioned but the Primary En-Suite is truly spectacular with high vaulted ceilings, private waterside balcony, walk in closet and En-suite full bathroom. Bonus feature, the second floor offers a game/media-room w/ full-size pool table, shuffle board table and waterside balcony. Don't let this amazing offering slip away!