Westbrook 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

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

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! $20,000 per month through April. Open to 2 week rentals at $6K/week- 2 week minimums. Permit #0792

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.

Available 2024: MD-LD 44K, June 12K, July 18K, Aug-LD 20K. 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.

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.

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.

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.

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!

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.

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.

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.

Pleasantly Updated Open Floor Plan Ranch with Vaulted Ceiling and Separate Den with Fireplace and TV. 3 Bedrooms, 2 Baths. Central Airconditioning. A Nice Deck, Heated Inground Pool, Outdoor Kitchen (with fridge and grill) and a Memorable Community Long Island Sound Beach Nearby to Enjoy. Summer 2024 - $4,900 Weekly with Two Week Minimum; June $18,000; Off Season (January to Mid-May) $3,500 Per Month. Permit # 0796.

2024 Rates: June $20K, July $35K Luxurious living in Greenport's private Rock Cove Estates. A stone's throw away to the deed private beach on the Long Island Sound. Highly desirable area where you can enjoy summer walks, lazy days at the beach or gorgeous sunsets. Create memories to last a lifetime in this beautifully decorated home. Close to Greenport Village, restaurants, shopping, wineries, and recreational activities.

2024 Rates: June $17,500, July $23,500, A1-LD $25,000 Welcome to 155 Caiola Ct, located in the desirable seaside community of Rock Cove Estates. This beautifully appointed home offers ideal amenities, beach access and location that one would desire from a Summer retreat. The interior features an inviting foyer leading into an formal dining room, open living room and eat-in-chef's kitchen. Additionally the main level offers a laundry off of the mud-room, sprawling first floor primary en-suite bedroom and home office. The second level features two guest bedrooms that share a full bathroom and a junior en-suite with private bathroom. The grounds are lush, full of mature plantings and showcases a large wood deck overlooking an impressive free-form in-ground swimming pool that basks all day in the summer sun. Additionally, you will enjoy private beach access just a short walk from the house, easy access into Greenport Village and a centralized launching point to enjoy world class vineyard, farm stands, fishing, hiking and so much more that the North Fork has to offer. Book your summer retreat now before this gem slips away!

Welcome to the stunning & newly renovated 485 Sutton Place in Greenport. This magnificent home seamlessly blends comfort, style and luxury living. The home provides a bright & airy feel throughout amongst its two levels of living. The first floor provides two spacious bedrooms and a full bathroom along with a bonus room with kitchenette that leads directly out to the backyard. Make your way to the second floor where you are welcomed by high ceilings and open concept living. A stylish living room with fireplace opens to the eat-in-kitchen and dining room with direct access to the balcony for alfresco dining. Completing the second level is a modern full bathroom, sizable bedroom, and an en-suite bedroom with a half bath. Kick back, relax and unwind in the private and spacious backyard that flaunts a new in-ground heated 18x36 saltwater pool with bluestone coping. The adjacent patio offers ample space for dining and provides shade to escape the summer heat. A dedicated fire pit area is the perfect space to cozy up on summer nights, toast to memories and treat yourself to delicious s'mores. Located on the North Fork of Long Island, this home's prime location provides convenient access to all the magnificent amenities the coveted town of Greenport has to offer and is less than a mile away to Greenport Village. For the wine aficionados, spend your day at the nearby Kontokosta Winery, a waterfront winery perched atop bluff that overlooks the Long Island Sound. Looking for a beach day? You have the option to spend your summer days at two nearby beaches, one private and one public. Experience the ultimate summer getaway on the North Fork.

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.

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.

Relax, rejuvenate and recharge in this updated North Fork gem with new kitchen, outdoor deck, screened in porch and large fenced in yard. Three bedrooms and full bath on the 2nd floor. Located on a quiet road but 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.

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

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.

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.

This unique home has a style all its own. Stylish & chic, an impeccably restored historic Saltbox. It boasts an updated kitchen and bathrooms that a queen would admire. Enjoy its warm & open floor plan, calming fireplaces in common room/bedroom and kitchen. Walk on original wide floorboards from the 19th century & enjoy the lush decor and comfortable furniture from 20th century. Short distance to Greenport amenities, walking distance to beach. House Incl. Prius/smart car charger. Rental Permit #0722

Gorgeous turn key fully furnished 1 bedroom 1 bath apartment with close proximity to local restaurants, shops and wineries. Separate Entrance with all utilities included: heat, ac, water, and wifi.

Square footage is approximate as Town of Southold does not have square footage of second half story recorded.