Westport CT Real Estate & Homes for Rent

One of a kind vacation spot with private beach and truly panoramic water views of close by Islands. Light & bright contemporary Ranch with cathedral ceilings in the Great Rm with 3 glass sliders to deck. Additional deck on the beach to continue the good life with morning coffee and memorable dinners watching glorious sunsets. Oysters, clams & campfires on your own beach. FLEXIBILITY OF DATES. PREFER 1 MONTH: JULY OR AUGUST. Price is per month starting July 1. A true vacation spot with private beach!

Welcome to this beautiful 4-bedroom, 3.5-bathroom home that blends timeless elegance with modern comfort. Designed for effortless everyday living and exceptional entertaining, the spacious eat-in kitchen flows seamlessly into the living room, dining room, and a charming parlor-perfect for enjoying an evening beverage over a game or good conversation. Relax and watch a movie or read a good book in the family room. Start your mornings in the serene sunroom, bathed in natural light and warmth, offering a peaceful retreat with your coffee. The home features generously sized bedrooms, including an expansive primary suite that serves as a luxurious private escape. Step outside to a beautifully landscaped yard complete with a sparkling pool-ideal for relaxing or hosting gatherings on warm summer days. Located just moments from picturesque beaches and offering easy access to town, major highways, and the train, this exceptional property delivers both convenience and a lifestyle of comfort and coastal charm.

Only rental in Westport under $2k. A two bedroom at that. Or one bedroom plus office if you're working from home. Newly refinished Hardwood floors throughout. Updated Bathroom. While a very convenient location, the backyard is very quiet and serene. Walking Distance To Westport Train Station, Easy Access To 95. Walking distance to Coveted Waterfront Restaurants, to the waterfront in general, to a park.

Discover this 4 bedroom home, tucked away on a quiet cul-de-sac close to train, beach and all Westport amenities. Welcoming and well maintained, the flexible floor plan offers an array of possibilities to work from home, entertain and have play space inside and out. The well proportioned rooms flow from the living room, through the dining room, the updated kitchen with stainless appliances. into a grand family room with vaulted ceilings and sliders accessing the deck. A new master bedroom with lux bath and walk in closets will not disappoint! There are 3 additional bedrooms and 2 more full baths plus an office with a fireplace on this level. The walk-out lower level features an additional family/play room that opens to a second deck. 2 car garage. Available in July for yearly rent. Must have good credit.

Annual unfurnished rental. Cloud 9 is 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.

Charming In-Town Single Family Home for Rent - (1-3 Years term avaiaable). Enjoy this sun-filled single-family home ideally located in the heart of town. A warm and inviting living room with a fireplace provides the perfect space to gather and unwind. The bright and open kitchen with granite countertops is conveniently located next to the dining room and opens to a private patio-perfect for relaxing or entertaining at any time of day. The main level also features a spacious primary bedroom with an en-suite bath, plus two additional bedrooms. The versatile lower level includes extended living space with two additional bedrooms and a shared full bathroom. Alternatively, it can function as a town-approved home occupation/professional space, complete with a separate, exterior entrance-ideal for a business setup with two offices and a waiting room. Located just minutes from shopping, the train station, Levitt Pavilion, the Westport Library, and a variety of restaurants, this home offers both comfort and convenience.

Rent for the Summer Options available. The most private and serene of the remaining multi-acre estates in central-most Westport is available for rent! Two minutes from the beach, town, 95, and the Saugatuck Hamlet & rail station. Top public schools in CT. Near Yale and Wesleyan Universities. A grand family home and estate property - for leisure, recreation and entertaining. A stone-gated and walled circular driveway, at the terminus of a private road cul-de-sac. Abuts three 8-figure residences properties and the 22-acre Aspetuck Land Trust /Haskins Preserve. The best of Westport lifestyle: Walk the dog on your own 4-acre property or the Haskins Preserve, with entrance steps away. Stroll your stunning rose-filled garden maze, groomed lawns and ornate flower beds. Swim and entertain at one the largest heated pools in CT (60' x 30'), pool cabana with bar, full and half bath / changing rooms. Share family memories in the ~8,000 sq. ft. main residence, where historic charm meets modern luxury . Four grand fireplaces, large formal living / converted ballroom, antique stone and beamed family room, gourmet kitchen w/professional appliances and baking island. This property is available for rent or purchase.

Escape to timeless elegence at this grand 1929 estate in Westport CT. Set gracefully on over six acres of meticulously landscaped grounds, this 1929 stone Tudor offers an extraordinary blend of historic elegance and modern luxury. With 8,831 square feet of refined living space, the main residence features six bedrooms, four full and two half bathrooms, and a seamless flow between grand interiors and stunning outdoor spaces. From the moment you arrive, the manicured lawns and magnificent gardens create a breathtaking first impression. Inside, 9-foot ceilings, rich hardwood floors, and exquisite craftsmanship are showcased throughout. A gracious garden room and an inviting sunroom provide panoramic views of the property's verdant vistas, while the expansive country kitchen-complete with a butler's pantry-makes entertaining effortless. Luxury and comfort abound, with four-zone air conditioning, beautifully proportioned rooms, and an abundance of natural light. The estate's centerpiece is a gorgeous pool, surrounded by lush greenery, offering a serene retreat just minutes from downtown Westport and the beaches. A rare opportunity to rent a truly remarkable property where beauty, sophistication, and timeless design come together.

Step into timeless charm at this perfect summer getaway! Welcome to 35 Dogwood Lane, Westport, CT Be surrounded by a timeless Stone Tudor Estate on 6+ Pristine Acres, located on the most private and serene of the remaining multi-acre estates in Westport. Set gracefully on over six acres of meticulously landscaped grounds, this 1929 stone Carriage house offers 1,200 square feet, creating an extraordinary blend of historic elegance and modern luxury. The Carriage house is a large two-bedroom with an expansive living space. A rare opportunity to rent a truly remarkable property where beauty, sophistication, and timeless design come together.

Comfortable Cape with 2 fireplaces and great location short walk to Old Mill Beach and Compo Beach. Nice back yard and convenient to new Deli/Resturant.

Rent for the Summer or Full Year: Options available. The most private and serene of the remaining multi-acre estates in central-most Westport is available for rent! Two minutes from the beach, town, 95, and the Saugatuck Hamlet & rail station. Top public schools in CT. Near Yale and Wesleyan Universities. A grand family home and estate property - for leisure, recreation and entertaining. A stone-gated and walled circular driveway, at the terminus of a private road cul-de-sac. Abuts three 8-figure residences properties and the 22-acre Aspetuck Land Trust /Haskins Preserve. The best of Westport lifestyle: Walk the dog on your own 4-acre property or the Haskins Preserve, with entrance steps away. Stroll your stunning rose-filled garden maze, groomed lawns and ornate flower beds. Swim and entertain at one the largest heated pools in CT (60' x 30'), pool cabana with bar, full and half bath / changing rooms. Share family memories in the ~8,000 sq. ft. main residence, where historic charm meets modern luxury . Four grand fireplaces, large formal living / converted ballroom, antique stone and beamed family room, gourmet kitchen w/professional appliances and baking island. This property is available for rent or purchase.

NEWLY RENOVATED! Gorgeous spacious fully furnished home situated at the end of a long private driveway in a fully fenced professionally exquisite landscaped park like property on 2.14 level acres. This beautiful colonial with a dramatic two story foyer, high ceilings, custom millwork & beautiful details is finished on 4 levels. New light natural hardwood floors. 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 E-I-K complete with high end appliances including a wolf range, subzero refrigerator, 2 dishwashers & an oversized marble island. Family Room with fireplace & french doors leading out to the patio. The Game Room is the perfect place to host with its stunning bar & pool table. Bluestone patio provides relaxed living & easy entertaining. Elegant Primary Bedroom with dual walk in closets & 2 luxe spa Bathrooms & a steam shower. Second floor has 3 more ensuite Bedrooms. The 3rd floor has a media rm, work out area incl free weights & an elliptical as well as a full bath. The massive patio features a built in grill, seating and eating areas, great for entertaining. Heated Pool House with Kitchenette, full bath and an extra Bedroom. In the LL, a recreational space offers additional option for play. Tons of storage space. Full house generator. Your own putting green. Fabulous opportunity to take advantage of Westport.

Welcome to your dream summer rental! This incredible property offers gorgeous landscaping, a private pool, a pool house, a fire pit, an outdoor kitchen, and an amazing fully furnished patio, with new oversized Tucci umbrellas. With 7 bedrooms and 2 half baths, there's plenty of space for you and your guests. The modern kitchen comes equipped with a brand new high-end pizza hearth oven, perfect for entertaining your family and friends. And if you're looking to stay active during your stay the property boasts a full-size, fully equipped gym with high end equipment and AV system. After a long day of outdoor activities, settle into the media room with its 100" screen for a movie night or relax in the full office and guest room located on the first floor. Enjoy the full basement with video games, ping pong and air hockey, plus a closet full of games and toys. This summer rental truly has it all - from the luxurious amenities to the incredible array of outdoor entertainment space. Whether you're looking to host the ultimate summer BBQ or simply unwind with your loved ones, this property is the perfect summer getaway for you. Don't miss out on this amazing opportunity and enjoy all that Westport has to offer this summer!!!!

Great opportunity if you want to get to know Westport before purchasing your new home. This rental is available for 7.5 months, mid September through end of April. Perhaps you are planning a construction project this fall and need to get out of the house during renovation. This updated, professionally decorated, fully furnished townhouse could be your solution. It's a bright end unit with lots of light and an open living/dining room area. A lovely patio is accessible through both the living room and dining room areas. The eat-in Beverly Ellsley custom kitchen has exquisite built-ins, rich wood counters, new double ovens and new dishwasher. Upstairs both the primary and secondary bedroom are en-suite. The lower level offers a movie viewing room with a full bath and wet bar. Regents Park is a well-known gated townhome community in the Greens Farms area of Westport giving you easy access to downtown shopping, the train to NYC, and the beaches. It offers a security guard, Har tru tennis court with lights for evening play, and pickleball. Give Westport a try, you won't regret it!

This captivating haven at Saugatuck Shores, nestled along the pristine shores of Bermuda Lagoon, 100 feet of private beach and a deepwater dock-your perfect launchpad for unforgettable summer adventures or a warm winter escape. With soaring ceilings framing breathtaking water views, this open and airy oasis is ideal for year-round relaxation. Enjoy sunsets on the expansive wrap-around deck or cozy up inside by the fire as snow falls. Indulge your inner chef in the gourmet kitchen, featuring an industrial stove, then gather around the marble table for meals with stunning views as your backdrop. The master suite is a true retreat with its own waterside deck, walk-in closets, and a luxurious bath complete with a Jacuzzi tub, shower, and double vanity. The main level includes three additional bedrooms, two with charming lofts perfect for younger guests. On chillier days, head to the lower level family room with a cozy fireplace, or enjoy the 85-degree indoor 42ft pool, sauna, steam room, and gym-perfect for wellness and relaxation. Step outside to your private beach, where you can watch buffleheads dive, or swans and herons glide through the wetlands, a tranquil sight during snowy winter days. Fully furnished and ready for you to customize, this waterfront gem offers the ultimate balance of nature, wellness, and beauty, whether it's summer or winter in Connecticut.

Turnkey two-bedroom, two-bath townhouse in Riverside Walk puts you in the heart of Westport. Walk to Starbucks, Bedford Square dining, Main Street shops, and summer concerts at the Levitt Pavilion. A private elevator brings you from your reserved garage space to bright single-level living with ceilings over nine feet high on both floors and hardwood throughout. The white kitchen offers granite counters, stainless appliances, a large walk-in pantry, and a dining area that opens to an oversized bluestone patio for easy indoor-outdoor entertaining. The generous primary suite includes a walk-in closet. The second bedroom enjoys calming Saugatuck River views, perfect for guests or a home office. Recent upgrades include a brand-new water heater plus a new full-size washer and dryer, giving you worry-free comfort. Minutes to Metro-North, Compo Beach, and all Westport amenities. Garage elevator exits at the same level as the front doors, allowing step-free access.

YEARLY RENTAL IN LONG LOTS SCHOOL DISTRICT: Welcome to a private and spacious 4-5 bedroom, 3.1 bath Colonial, offered as an unfurnished, yearly rental. The main level has an inviting foyer open to the living room, and down the hall is the gourmet kitchen with a peninsula that seats 2-3 plus an adjoining family room with wood burning fireplace. The family room has sliding glass doors that open to a large deck overlooking the private backyard. The sun-lit dining room with gleaming hard wood floors, plus half bath, complete the main level. The second floor has a spacious primary suite with a large walk-in cedar closet and full bath with soaking tub and shower. Just down the hall are 3 additional bedrooms with 2 full baths, along with an office (or 5th bedroom). One of the guest bedrooms is ensuite. Off the kitchen is the daylight walk-out lower level which has been smartly finished with engineered wood flooring, sound proof walls/ceiling, a laundry room plus storage. The 2 car garage is on-level with the main floor, rounding out this impressive property. Walk to Long Lots Elementary, 3 min to the Greens Farms Metro North station and 5 minutes to the beach and Main Street, Westport. At the end of a cul de sac, quiet and private. Available August 1st.

Experience resort-style living at "The Park", an exceptional gated estate on 3 private acres in the heart of Westport. This meticulously renovated home offers 8 bedrooms-including a private 2-bedroom apartment with full kitchen and living space-perfect for guests, staff or extended family. At the heart of the home is a stunning, designer chef's kitchen w/ island, gorgeous built-ins, walls of windows and folding glass doors that seamlessly bring the outdoors in through the expansive patio, overlooking breathtaking grounds, specimen trees, and lush raised-bed gardens. Perfect for entertaining or quiet enjoyment, the outdoor amenities include a natural pool w/waterfall, spa, pool house, sauna, sportcourt & magical play areas. Inside, you'll find a first-floor bedroom suite, state-of-the-art home theater, private gym, Living room w/ fireplace, sitting room, Dining Room w/ butlers pantry, office or playroom. Upstairs find 4 additional guestrooms, a spacious playroom/office w/ balcony, spacious Laundry Room & a luxurious Primary Suite w/2 custom walk-in closets, a spa-like bath & a private balcony to take in the serene surroundings. Every inch of this home is crafted for comfort and elegance, blending modern luxury with timeless sophistication. Ideally located just minutes from top schools, beaches, shops & restaurants, train station, country clubs, hiking trails, highways & only 20 minutes to an airport, -The Park is truly a one-of-a-kind luxury lifestyle beyond compare.

Set gracefully on over six acres of meticulously landscaped grounds, this 1929 stone Tudor offers an extraordinary blend of historic elegance and modern luxury. With 8,831 square feet of refined living space, the main residence features six bedrooms, four full and two half bathrooms, and a seamless flow between grand interiors and stunning outdoor spaces. From the moment you arrive, the manicured lawns and magnificent gardens create a breathtaking first impression. Inside, 9-foot ceilings, rich hardwood floors, and exquisite craftsmanship are showcased throughout. A gracious garden room and an inviting sunroom provide panoramic views of the property's verdant vistas, while the expansive country kitchen-complete with a butler's pantry-makes entertaining effortless. Luxury and comfort abound, with four-zone air conditioning, beautifully proportioned rooms, and an abundance of natural light. The estate's centerpiece is a gorgeous pool, surrounded by lush greenery, offering a serene retreat just minutes from downtown Westport and the beaches. A rare opportunity to rent a truly remarkable property where beauty, sophistication, and timeless design come together.

The chic and stylish summer rental you've been waiting for! 3 bedroom / 2 bath newly renovated and tastefully designed beach house in a quiet and private location near Westport's Compo Beach and Old Mill Beach. This home includes all the amenities you would expect: a chef's kitchen with breakfast bar, a full dining table for eight, a relaxing and zen-like living room, and even a den that can double as a guest and/or office space. Relax in a newly designed main bedroom with queen-sized bed and en-suite bathroom. Two additional well-appointed bedrooms each have a full-sized bed, ample closet space and share the other updated bath. Grab the beach chairs and towels (included) and take a stroll to the beach, or just stay home to enjoy your book in the fully furnished backyard, with beautiful flowering plants, manicured lawn and an inviting patio and hammock. The converted shed in the backyard, dubbed the Little Casa, is furnished with a desk and daybed, with space to enjoy your morning yoga or use as an inspiring workspace. Experience the amazing beach town of Westport with its bustling downtown and restaurants, its beaches, sailing, kayaking. Enjoy the multiple free summer concerts at the Levitt Pavilion, weekend farmers markets, Wakeman town farm, hiking trails, art shows, and more to make enjoyment of beach, pools, golf and tennis easy! June: (RENTED), July 10-31: $10,500, August: $15,000. Potential to extend monthly beyond summer. Weekly rate is $5,000 including utilities.

35 Dogwood Lane, Westport, CT Be surrounded by a timeless Stone Tudor Estate on 6+ Pristine Acres, located on the most private and serene of the remaining multi-acre estates in Westport. Set gracefully on over six acres of meticulously landscaped grounds, this 1929 stone Carriage house offers 1,200 square feet, creating an extraordinary blend of historic elegance and modern luxury. The Carriage house is a large two-bedroom with an expansive living space. A rare opportunity to rent a truly remarkable property where beauty, sophistication, and timeless design come together.

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!!!

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 available 6/1 -6/30 and August 15th - 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