Westport CT Real Estate & Homes for Rent

Bring your Boat! DIRECT WATERFRONT LIVING at Channel Marker 16 W/ DEEP WATER DOCK and Stunning 24/7 views of Saugatuck harbor activity. Fully rebuilt home w/ sweeping water views, an open floor plan, 4700 SF total, with 4 bedrooms, 4.5 baths (3400+/- SF of living space on 2 floors and a bonus 1400 SF of large lower level consisting of mudroom, 2 garage bays and a spacious recreation FLEX-space w/ water views). Located on Saugatuck Island, a truly unique Utopia, offering beaches for residents, quiet streets, exceptional sunrises and sunsets and an over-abundance of outdoor waterfront activity! Fish off your dock, Kayak, paddle board or just sit back, relax and take in the sights of the vast assortment of wildlife, rowers and sailing regattas. The home has a coastal and casual aesthetic throughout. The Living/ Dining/Great Room and Gourmet Kitchen w/ 13' Island, all look out to the Harbor. In addition to a stellar location, the home offers: Wolf and Subzero Appliances, a Family room w/ fireplace, Master suite w/ private deck, Master bath w/ soaking tub, Separate home office, Dual Tv/Entertainment areas, outdoor shower and a very large Rec area. Enjoy all Westport has to offer in way of fine dining, boutique browsing, Arts, Music and Cultural Events. A quick and easy NYC commute. Please note: Agent is an owner.

This incredible cottage is located on the most private and serene multi-acre estate in central-most Westport. located just minutes from the beach, town center and i95.Enjoy the best of Westport from this prestigious address.

NEWLY RENOVATED!!!!! Welcome to your dream summer rental. Gorgeous spacious home situated at the end of a long private driveway in a fully fenced professionally exquisite landscaped property on 2.14 level acres. This beautiful colonial with a dramatic two story foyer, new light natural hardwood floors, high ceilings, custom millwork & beautiful details is finished on 4 levels. 2 Home Offices with extensive built-ins is perfect to work remotely. Formal Living Room with fireplace flows into the banquet style formal Dining Room. Entertain with ease in the fully equipped modern Eat-in Kitchen complete with high end appliances including a wolf range, subzero refrigerator, 2 dishwashers and a huge marble island. Family Room with fireplace and french doors leading out to the patio. The Game Room is the perfect place to host with its stunning bar and pool table. Bluestone patio provides relaxed living and easy entertaining. Elegant Primary Bedroom with dual walk in closets and 2 luxe spa Bathrooms and a steam shower. Second floor has 3 more ensuite Bedrooms. The 3rd floor has a media room , work out area including free weights and an elliptical as well as a full bath. The massive patio features a built in grill, seating and eating areas, great for outdoor entertaining. Heated Pool House with Kitchenette, full bath and an extra Bedroom. Full house generator. Your own putting green. Fabulous opportunity to enjoy summer in Westport at its best!!!

Welcome to an exquisite rental located at 398 Greens Farms Road in the prestigious town of Westport, CT. This elegant residence offers a seamless blend of sophistication and comfort, promising an unparalleled living experience. Spanning over 7000 square feet, this home features 6 spacious bedrooms, including a luxurious primary suite complete with two walk-in closets and dressing room. The residence boasts five full, two half bathrooms and a gourmet kitchen equipped with state of the art appliances, an envious pantry, a butler's pantry and a built-in coffee machine. The property is situated on an expansive 1.25 acres with waterfront views of a serene lake. Enjoy the gunite heated in-ground pool with safety cover, outdoor fireplace or drive a short distance to the beach, while participating in the vibrant amenities of Westport. This residence offers ample storage and flexibility with a 3-car garage, third-floor flex space suitable for a playroom, office, or additional storage. Additional conveniences include two laundry rooms. Experience refined living near shopping and the charm of Westport

Single family home on dead end road for rent in convenient commuter location. This peaceful home is within walking distance to Westport Saugatuck Train Station and a two-minute drive to interstate i-95. Home features living room, eat-in kitchen, 4 bedrooms, two full baths, lower level laundry and finished room, large deck, spacious level backyard and garage.

Tucked away at the end of a peaceful private cul-de-sac, this delightful Cape Cod-style home offers both charm and convenience. Ideally located in the heart of Westport, it's perfect for commuters with quick access to the train, as well as nearby restaurants, shops, beaches, and top-rated schools. Inside, you're welcomed by a spacious living room featuring cathedral ceilings, a cozy fireplace, and a ceiling fan. The large eat-in kitchen is outfitted with granite countertops, modern appliances, a ceiling fan, wall unit A/C, and beautiful wood floors. From the kitchen, step out onto the patio and enjoy a serene, expansive backyard-ideal for outdoor relaxation or entertaining. Additional highlights include a lovely enclosed porch, perfect for gatherings, and hardwood floors throughout much of the home. The main level offers two generous bedrooms with plush carpeting and ceiling fans. Upstairs, the primary suite features a private bath and a charming reading nook. The unfinished lower level includes a washer/dryer, a dedicated home office, ample storage space, and a game room with sliders that open to the backyard. While the basement is not heated, it remains comfortably warm thanks to the furnace located in the area. Tenants in residence, no lockbox - 24 hour confirmed appointments required.

Spend your summer pools side on direct Long Island Sound, for the month of July! Simply sit back and enjoy stunning sunsets and sensational water-wildlife from every living room. Located just 3 doors from the beach and within 1 +/- miles to Metro North train station. One would be hard-pressed to find a more delightful refuge to host family and friends and reap the benefits of living on Saugatuck Island. Wake-up overlooking the Sound and enjoy your morning cup of coffee, or head out on an early coastline paddle or kayak from your personal dock. This is your chance to experience one of Fairfield County's most unique waterfront settings in one of Fairfield County's most unique towns! Within easy accessibility to Westport's 5-star rated restaurants and shopping, along with Westport's town-owned 18 hole Golf Club, offering; Tennis, Sailing, Swimming pools, pickle-ball and Paddleball facilities. An amazing opportunity to make lasting memories! Not one to miss!

Experience the perfect summer retreat in the heart of Westport. This beautifully furnished home offers a blend of comfort and convenience, just minutes from downtown, the Levitt Pavilion, restaurants, beaches and Longshore Country Club. The spacious layout features a light-filled interior with colorful, tasteful decor, ideal for families or friends. Enjoy outdoor living on the expansive slate patio, complete with dining and seating areas, plus a fireplace and BBQ. Inside, central AC ensures comfort, while the eat-in kitchen and family room provide communal spaces and private sleeping arrangements offer restful retreats. Available from May 23 through September 30th, with flexible lease terms-monthly rate is $20,000. Make the most of your summer in this exceptional Westport retreat.

Furnished Yearly Rental with dramatic views of the Long Island Sound and pool at one of the areas premier addresses- Steps To Compo Beach and Longshore Country Club. Located on prestigious Bluewater Hill, this home is part of association with deeded Beach rights and Tennis courts. This home offers 4 bedrooms, 3 full baths, flexible floor plan with great entertaining areas, outdoor patios and property. Available 9/1/25. Shorter Term Rental option possible @15,000/mo

Furnished Short Term Rental with dramatic views of the Long Island Sound and pool at one of the areas premier addresses- Steps To Compo Beach and Longshore Country Club. Located on prestigious Bluewater Hill, this home is part of association with deeded Beach rights and Tennis courts. This home offers 4 bedrooms, 3 full baths, flexible floor plan with great entertaining areas, outdoor patios and property. Available after 9/1/25

Summer rental starting May 15. Nama-stay at a sweet pink cottage by the shore reminiscent of childhood days at the beach. Located at the end of a cul-de-sac four houses in from the water on Saugatuck Shores, this private home has an extra spacious, fully fenced, level yard giving you the best of both worlds - a lawn within a water community and quick access to the water. Home has three bedrooms and two baths on the main level. One bathroom has a shower and the other has a tub. Both have Waterworks and Restoration Hardware fixtures and tiles. Kitchen is petite yet gourmet with white Italian carrera marble counters, Viking gas stove, Bosch dishwasher, farm house sink and stainless steel refrigerator. Also on the main level is a large entry vestibule and a Florida lanai room in the back overlooking the yard. Upstairs is a one room loft space. Home has hardwood floors throughout. Plenty of parking. Dream location minutes from everything. Price is per month through October 15, 2025.

Nestled behind privacy gates in the heart of Westport's coveted Long Lots neighborhood, 101 Roseville Road presents a grand center hall Colonial that seamlessly blends timeless elegance with modern luxury. Built in 2007, this stately residence spans 5,955 square feet across four finished levels, offering ample space for both intimate gatherings and grand entertaining. Upon entering, you're greeted by a sun-drenched interior filled with natural light, accentuating the home's open floor plan. The updated kitchen serves as the heart of the home, featuring top-of-the-line appliances and finishes that cater to culinary enthusiasts. Adjacent to the kitchen, multiple living areas provide versatile spaces for relaxation and socializing. This exquisite property boasts five generously sized bedrooms and seven bathrooms (five full and two partial), ensuring comfort and privacy for family and guests alike. The primary suite is a sanctuary, complete with a lavish en-suite bathroom and an expansive walk-in closet designed to accommodate even the most extensive wardrobe.

Find a place where I can be ME! The perfect In-Town location with winter views of the Saugatuck River and convenience to Main Street with numerous restaurants, shopping, and festivals. Ride your bike to the Farmer's Market or Library. You'll be greeted by a warm and inviting porch when you drive up to the home. Once inside, you'll love the charm of yesteryear. The gourmet kitchen has a new refrigerator, beams, tile floor, and a half bath. The primary bedroom has a separate walk-in closet just outside the door, and two additional bedrooms with a renovated bath. The lower level has a new washer and dryer. It's freshly painted and ready for you to enjoy the best of summer ever! Please ask about pets. Sorry, NO SMOKING.

Nestled in a picturesque neighborhood just minutes from Compo Beach, Longshore Golf Club and downtown Westport, this charming summer home is the perfect escape for those seeking a luxurious yet relaxed retreat. With stunning landscaping, expansive living spaces, and a sparkling heated salt-water pool, this property offers the best of coastal living. Enjoy entertaining in the fenced in backyard complete with a patio, grill and outdoor TV. Across the street there are public pickleball courts, tennis courts and baseball fields. Your summer playground is ready for you! Rental available for the month of July only.

Discover a fully renovated 5-bedroom, 4-bath home in Westport,CT, offering the perfect blend of upscale elegance and family-friendly comfort. On the main level, you'll find a sophisticated dining room with a gas fireplace beneath a starlit chandelier, a cozy living room with an electric fireplace, and an adjacent family room with a 60" smart TV and a built-in coffee/tea bar. Spacious kitchen with 10' island is perfect for family gatherings. Downstairs, a finished basement playroom keeps the little ones entertained meanwhile a private home gym with a treadmill, Peloton, and Pilates reformer keeps everyone active. The spa-inspired primary suite pampers with a deep soaking tub, rain shower and a steam room. A main-floor guest suite offers a king bed and ensuite bath, ideal for guests. Upstairs, two rooms come with twin beds, desks, and plenty of toys. Another nursery/bedroom offers a full bed with a twin trundle, plus a crib and changing table. Family-friendly touches include a high chair, booster seat, and a convenient washer/dryer. Outside, a resort-like yard invites you to relax. Dive into the new heated in-ground saltwater pool with spa, or lounge on the Restoration Hardware seating by the gas fire pit, surrounded by lush hydrangeas and lavender. An enchanting side garden with white pebbles, string lights, a waterfall feature, and an herb garden adds to the outdoor magic. Best of all, downtown Westport is just minutes away, making this home the perfect summer escape.

FABULOUS ON THE WATER RENTAL~YEARLY RENTAl but Flexible. Completely RENOVATED MOD CHiC !! Phenomenal WIDE WATER VIEWS. BIG covered front porch with outdoor fire pit in front yard and outdoor shower. Best Compo Beach views~Sunrise and Moonrise each day. Plenty of parking(6 cars, very rare) at this 4BD 3.1 Bath Compo Beach Bungalow. Won Westports prestigious "Preservation Award". Fabulous home !

Welcome home! Pristine and fully updated yearly, unfurnished rental in the Greens Farms neighborhood of Westport. 1940's charm with 2300 square feet over 3 floors, 3 bedroom, 2.5 bathroom cape- desirable layout with option for primary bedroom on main or second level. Beautiful & bright kitchen with granite countertops and stainless steel appliances, with a wall of built-in cabinetry/pantry in the adjacent breakfast room. Sliding glass doors lead to the deck with grill, access to the storage shed and one car garage. The private & picturesque yard is lined with stone walls, fencing, pretty landscaping and bluestone walkways-a nice place to relax or play. The lower level has flexible rooms, office and playroom, along with a half bath, laundry and plenty of storage. Bright and sunny den/sunroom, living room with fireplace, and dining room round out the first floor. This is truly a charming home close to everything, including the Greens Farms Metro North train station. Photos were taken before Tenants were in place. Available June, 2025

Beautiful one-bedroom home with abundant windows and outdoor patio space. This newly renovated home boasts an open floor plan with a brand-new kitchen and bathroom. Nestled on two gorgeous acres in the Coleytown neighborhood of Westport, yet just minutes from downtown.

This beautifully renovated 1 bedroom, 1 bath apartment offers a perfect blend of modern style and natural elegance. Vaulted ceilings, add a sense of openness to the space. The combination of modern stainless steel appliances, butcher block counters and classic hardwood floors create a sophisticated living space, while large windows bring in an abundance of natural light. 1 hour from New York. Close proximity to I95, Merritt Parkway and Train. 1.5 miles to downtown Westport.

Discover luxurious living at Bradley Commons, a gated community of upscale townhomes. This stunning two-bedroom, 2.5-bath residence is just minutes away from all the best Westport/Saugatuck; shopping, beaches, top-rated schools, and within walking distance to the Metro-North train station for easy commuting. The townhome features a brand-new, beautifully designed kitchen that brings a boutique hotel feel to the home with an abundance of natural light throughout. The open living room and dining area lead to a private deck with sliders, offering serene views of the professionally landscaped grounds. Wood floors span all two levels of this spacious home, enhancing its elegance. Key Features: Two spacious bedrooms 2.5 modern bathrooms, brand-new kitchen with luxury finishes Open concept living and dining area with access to a private deck. Hardwood floors throughout Beautifully landscaped grounds Gated, private community with a secure, upscale feel. Enjoy the perfect blend of style, comfort, and convenience in this prime Westport location. Please note: Marble kitchen table and chairs, desk/shelves remain in residence. 24 hour notice required.

CHARMING CORNER TOWNHOUSE IN A QUIET BLOCK AND CLOSE TO ALL!

Wonderful two bedroom home in Greens Farms area of Westport. Home features two bedrooms, small home office and tastefully updated kitchen with beautiful cabinetry, granite counter tops and center island/peninsula. Kitchen opens into living/dining area. Great backyard to host bbq's. Minutes to Compo Beach, Longshore, and downtown Westport. Easy access to I-95 and Merritt Parkway.

Escape to a private island retreat that you didnt now existed in Westport, where luxury meets coastal charm. This newly renovated, designer-furnished home spans over 4,000 sq. ft. and sits directly on the beach in Compo Mill Cove.With four/five beautifully appointed bedrooms, a bonus bedroom/au pair suite, 5.1 bathrooms, and a dedicated office or artist's space, this home offers both comfort and inspiration. The gourmet kitchen features a separate Sub-Zero fridge and freezer.Step off the back deck onto the sandy beach, where kayaks, paddleboards, a ping-pong table, and the ocean await. The lush front yard adds to the serene setting. A deeded deep-water boat slip at Compo Beach completes this exclusive offering.Available for August at $60K/month-don't miss this rare beachfront escape. No vehicles or cars are allowed on the island. Complete and Exclusive Private Island with only 19 single family homes on the island. A once in a lifetime experience with no worries in the world once you walk across the foot bridge. Come & relax & enjoy. Most pets are allowed-inquire.

A short walk to Compo Beach from a beautiful, luxurious, colonial home. Stunning interior design, chic furnishings. Double lot with patio feeds onto an open green lawn ideal for outdoor enjoyment and entertaining. Around the corner from Longshore for golf, tennis, swimming and boating. A perfect summer escape available for 6 weeks from June 20 to August 1. This is a six week rental, for a total of $40,000.

Charming Downtown Westport 2-Bedroom Apartment Live in the heart of Westport! This spacious two-bedroom apartment was fully renovated in 2019 and offers the perfect blend of convenience and comfort. Located off Myrtle Avenue, you'll be just steps away from the renowned Levitt Pavilion for the Performing Arts, the Westport Library, Bedford Square, The Westport Country Playhouse, and the town's award-winning restaurants. Inside, enjoy a bright and open living area, perfect for relaxing or entertaining. Both bedrooms provide ample space, ensuring comfort and privacy. Whether you're looking for a vibrant downtown lifestyle or a cozy retreat, this apartment delivers. Don't miss this opportunity to be in Westport and all it has to offer!