Westport CT Real Estate & Homes for Rent

Enjoy a convenient lifestyle at this centrally located well maintained Custom Colonial with a gorgeous pool, expansive covered patio, fabulous yard in the heart of Westport. Featuring an open spacious floor plan, gourmet kitchen with large center island leading to the dining room, family room with a dramatic two-sided floor to ceiling stone fireplace. Walls of glass open to the stone patio overlooking a private, fenced acre, in-ground pool, green house/barn. The 2nd floor includes a large primary suite plus 3 generously sized bedrooms all en-suite. Minutes to all town amenities, train, shopping, beaches, schools. Rental options include summer and short term (different pricing, min 3 months)

Enjoy the summer at this well maintained Custom Colonial with a gorgeous pool, expansive covered patio, fabulous yard in the heart of Westport. Featuring an open spacious floor plan, gourmet kitchen with large center island leading to the dining room, family room with a dramatic two sided floor to ceiling stone fireplace. Walls of glass open to the stone patio overlooking a private, fenced acre, in-ground pool, green house/barn. The 2nd floor includes a large primary suite plus 3 generously sized bedrooms all en-suite. Minutes to all town amenities, train, shopping, beaches, schools. Rental options include May, June (20K per month), July, August (25K), September (20K), min 3 month term

Newer custom colonial offered for rent - preferably partially furnished - for a period of one to two years, beginning this summer. Completely rebuilt in 2011 by its current owners, this home sits on a manicured .70 acre parcel at the end of a quiet cul-de-sac, walking to Westport town center. The home features high ceilings and an open floor plan, with 4 large bedrooms & 3 updated bathrooms (all on same level); a large laundry room on the second floor; and an open kitchen to family rm; cozy living rm, dining rm; and large butler's pantry on the first floor. The master bedroom suite features vaulted ceilings, a large walk in closet, and a spa bathroom with double sinks. The backyard is quiet and serene, and mostly fenced, and features a patio and pergola with fireplace and lovely plantings. The walk out lower level offers a cozy, hidden home office & gym/guest room w/ half bath. The owners paid close attention to the quality of the construction and green design/energy efficiency when building this home. A heat recovery ventilator pipes clean air into the house 24/7. OFFERED AS AN ANNUAL RENTAL ONLY; NOT FOR SALE. No short term leases will be considered.

Charming one bedroom, one bath cottage yearly furnished rental in the Old Hill neighborhood of Westport. This stand alone cottage has lovely natural light with hardwood floors, high ceilings & a full kitchen with a breakfast bar. The primary bedroom has a walk in closet & hardwood floors. There is a stackable washer/dryer laundry in the full bath. The deck & additional patio offer lovely outdoor space. The tenant has access to one bay of the garage. The landscaping, snow removal & trash collection are included in the rent. Move right in & enjoy all that Westport has to offer. Available May 1st.

This charming Cape Cod Colonial sits on a beautiful, level acre+ lot with a semi-circular driveway. The home features four bedrooms and two full baths, with two bedrooms on the main floor and the primary plus an additional bedroom upstairs. The living room boasts a wood-burning fireplace and an oversized window overlooking the front yard. The updated kitchen, equipped with stainless steel appliances, offers plenty of counter space and has a door leading to the side yard. The spacious dining room is perfect for entertaining. On the main level, the two additional bedrooms are generously sized, with one ideal as a home office featuring a picturesque bow window overlooking the backyard. Upstairs, you'll find the large primary bedroom and a fourth bedroom, both sharing an updated full bath. The expansive, level backyard includes a large stone patio, perfect for outdoor gatherings. An oversized two-car garage provides ample storage. Conveniently located near town shopping, the train, and the Merritt Parkway, this home is a must-see!

Designed by renowned architect Nancy Thiel, this pristine farm-style residence, featured in "Cottages & Gardens", sits on a prime location directly opposite of the Hunt Club. It boasts high ceilings, an open floor plan, and an abundance of natural light. The main floor encompasses a fabulous kitchen, complete with a large center island, top-of-the-line appliances, and ample storage. In addition, the main floor features a formal living room, an elegant dining room, a cheerful family room, and a private office. All of these rooms feature 9' ceilings and beautiful hardwood floors. The second floor has four generously sized bedrooms, each with its own en-suite bathroom and walk-in closet. The luxurious primary suite stands out with its two massive walk-in closets, custom built-in drawers, a dressing area, and a spa-like bathroom that offers a serene retreat. Ascending to the third floor, you'll discover a versatile space that can serve as a second office, or a private getaway. The lower level presents a fifth bedroom with a full bathroom, ideal for accommodating guests or creating a private space for an au-pair or in-law. Additionally, the lower level features a spacious playroom with a fireplace. The finished walk-out lower level provides seamless access to the outdoors and adds to the home's overall living space. The architect's past-meets-present approach when designing this house is topped off by the state of the art geothermal heating and cooling system.

SPEND YOUR SUMMER IN WESTPORT - WELCOME! Stylish and sophisticated condominium located in a quiet garden setting. Park in you garage, take the elevator up one floor to enter this beautiful end unit, open floor plan with 9 foot ceilings and views of the property and river. A cook's delight.... the kitchen boasts white cabinetry, granite countertops, and stainless appliances. Beautiful hardwood floors throughout the unit, detailed millwork to include built-ins and crown molding. The spacious bedroom has a French door that leads to a private bluestone patio. Conveniently located to downtown Westport .... it's just a short stroll to fabulous main street, restaurants, the library, Levitt Pavilion - and many more attractions. Come soak up the sun, enjoy this beautiful condo and all the amenities Westport has to offer.

LARGE LOG HUNTING LODGE ON THE RIVER WITH INGROUND POOL BEUTIFUL GROUNDS VERY PRIVATE ONE FLOOR LIVING. 4 BEDROOMS 3.5 BATHS SLEEPS 8 TOTAL. 1 HOUR TO NYC BEACH ACCESS. WONDERFUL RARE OPPORTUNITY TO RENT THE HOME YOU ALL ALWAYS WONDERED ABOUT. THE BEAUTIFUL TRANQUIL RIVER VIEW LODGE LOG HOME THAT SITS ON THE MAJESTIC SAUGATUCK RIVER. WITH OVER 575+ FEET OF DIRECT WATER FRONTAGE VIEWS THAT WRAP AROUND THIS WONDERFUL HOME. THIS HOME HAS BEEN ENJOYED BY NUMEROUS THEATRICAL PEOPLE BEFORE THEN BECAME A PRIVATE RESIDENCE THAT HAS BEEEN PHOTOGRAPHED IN NUMEROUS MAGAZINES AND MULTIPLE HOUSE TOURS. COME ENJOY IT FOR THE SUMMER AND FALL IN LOVE AND WE COULD CONSIDER SELLING. MAY 25,000 / JUNE 30,000 / JULY AND AUGUST 40,000/ MONTH SEPTEMBER 30,000. A WONDERFUL VACATION CLOSE TO NYC PLEASE NO DRIVE BY PRIVATE ESTATE. Renter responsible for electricity and gas for the pool If less than 90 days, 15% tax required

Wonderful private legal two bedroom carriage house on the Saugatuck River private estate. Freshly painted with wall to wall carpet in bedrooms and loft area. Wood floors in the living room with vaulted ceiling. washer / dryer in unit. Bonus loft for storage. This charming home is available for long term rental. Very private please no pets or smoking. Owner takes care of lawn and snow removal. This property is very private. This is the cottage only. Home could be furnished for additional cost Photos of prior renters furniture .PRIVATE PROPERTY PLEASE MAKE APPOINTMENT NOT APPROPRIATE TO DRIVE DOWN WITHOUT APPOINTMENT. Sorry No Short Term

Located on a quiet neighborhood street, this 5-bedroom home spans a full acre, offering a tranquil setting for your summer retreat. It's ideally positioned near all town amenities, perfect for enjoying Westport's lively summer scene. The home welcomes you with a spacious living room, large windows highlighting scenic views, and a dining area leading to a sunlit deck-great for relaxing summer evenings. The kitchen features custom cabinetry, stone countertops, a center island, and high-end Thermador appliances, complemented by a bay window that brings in abundant natural light. Next to the kitchen, the family room provides extra space for relaxation and entertainment. The lower level includes a versatile bedroom or office, a full bathroom, large pantry and substantial storage. This floor also has a large living room and playroom leading to a large stone patio, perfect for outdoor dining and activities. Upstairs boasts 3 additional bedrooms, including one with an en-suite. The primary suite is on a separate upper level, providing privacy and luxury with a vaulted ceiling, sitting area, large walk-in closet, and a deluxe bathroom featuring a hydro tub. Choose this home for your summer stay in Westport, where convenience meets quiet comfort!

AVAILABLE from 6/26/25-8/24/25. Enjoy your summer at this wonderful Greens Farms Colonial. What a perfect spot to come home to, after a day at the beach! Spend your evenings on the screened porch & in the festive, private back yard with a great patio featuring multiple seating areas, fire pit, hot tub (with outdoor smart TV) and swing set. The main level offers a living room complete with a comfortable TV area, a spacious country Eat-in Kitchen plus a Home Office -no need to travel to work from here! 3 sweet Bedrooms upstairs share a bath. The Primary has a king sized bed. One Bedroom has a twin with a trundle bed that opens to a king. The other has two twins and one twin has a trundle. The lower level offers a Home Theater, complete with recliners, plus the laundry. Detached Garage has been converted to an Entertainment/Lounge/Game Room with smart TV, piano and more! Owners reserve walk-up attic for their belongings. Just over an hour by train service from NYC. Enjoy all that Westport has to offer including great dining, Compo Beach, Longshore Country Club, Westport Country Playhouse and concerts under the stars all summer long at the Levitt Pavillion

***Attention -additional living space available*** in-law-suite in the lower unit****This beautifully renovated colonial home is situated in a highly desirable and convenient location. It combines modern updates with a spacious layout, making it an exceptional choice for your next home. The property features five well-appointed bedrooms, an impressive 2x large eat-in kitchens, a cozy living room complete with a 2x fireplaces, an office space for productivity, and a stunning dining room that opens into a sunroom. Three fully renovated bathrooms and hardwood floors throughout add to the appeal. You'll also benefit from in-unit 2x laundry facilities. Enjoy the privacy of a yard set back from the road, providing a peaceful retreat. Don't miss your chance to make this remarkable home yours!

Direct Waterfront Home With Private Dock And Beach Across a one-lane bridge to coveted Saugatuck Island in vibrant Westport, CT stands this authentic mid-century modern pied-a-terre directly on Westport Harbor. Architect designed for renowned songwriter Hy Zaret ("Unchained Melody") to exude both charm and sophistication. It offers spectacular views of the water, sailboats and seabirds from its walls of windows, multiple decks, private dock and sandy beach. Take a swim, look for oysters and rinse off in the outdoor hot and cold shower. This home will invite you to slow down, relax and enjoy the gentle, fresh breezes of summer. Some features that make this home special are: *Open floor plan for large living room/dining room area with sliding glass doors to . *A master, en-suite bedroom that opens to a deck, two walk-in closets, a sitting room and bath. *A skylighted kitchen, with tons of storage, high end appliances, a built-in desk, breakfast bar for two and a pass-through to the dining area. *A dining area with a fireplace and a sliding glass door to a deck. *A fireplace and a queen size sleep sofa in the family room that has its own bathroom and single bed alcove. *A two-car attached garage with generous, additional parking in the driveway. *A bedroom on the ground floor with a water view, another full bathroom and a fully equipped laundry room. *To be furnished, by the owner's interior decorator, to their exacting specifications.

Cute 1-bedroom convenient location to beach, longshore shopping and train. Comes with a 1 car garage and utilities included.

30 Hitchcock is truly a summer vacation retreat. The property features a recently built 40 foot saltwater, gunite heated pool and spa. The expansive outdoor patio and deck is perfect for summer gatherings. An upper deck off the main level with BBQ grill, dining and seating, covered lower deck with outdoor TV and seating, expansive bluestone patio, pergola, and poolside dining and seating complete with a firepit table and heat lamp. The lower level features a family/recreation room and gym with a separate refrigerator and full bathroom that opens up to the patio/pool. The front porch is perfect to view the sunset over cocktails. The expansive square footage is well utilized with 9+ high ceilings and a great room living space, separate den, 2 home offices, a downstairs guest bedroom suite/full bath, and 5 additional bedrooms upstairs. Beach pass available. NYC an hour to 1 hour 15 min away by train. Availability: flexible dates Jun 14th- Labor Day.

Light, bright Contemporary/Ranch with incredible water views of the LI Sound. Enjoy Compo Beach life and take in the spectacular sunrises and sunsets from the warmth of the sunroom or the sundrenched deck. Open floor plan, bathed in natural light, where you can gaze out at the LI Sound from the expanse of windows. A modern Poggenpohl kitchen with stainless appliances opens to a rear terrace with grill and outdoor dining space with a secret garden feeling. Tranquil Master Suite with sitting area, spa like bath, and private deck. Three more spacious bedrooms with hardwood floors, built-ins for work at home space, and full bath complete the bedroom wing. Beautiful private property with outdoor shower. Close to Compo beach and the premier Longshore Park with dining, golf, pool, boating, tennis, marina. Only minutes to the train station, and town center with all of Westport's amenities. Live, work, play at the beach and make memories that will last a lifetime! The monthly rent of $20,000 is for a 12 month lease. Shorter term rents are Seasonally adjusted. Summer rent for June, July and August is $33,000 per month.

2nd floor unit in free standing building. Open floor plan, soaring ceilings + a loft. Conveniently located ...walk to town and Westport's fantastic shops & restaurants.

This bright and spacious contemporary home is nestled at the end of a sought-after cul-de-sac, offering both privacy and convenience. Featuring 5 bedrooms, 3 full and 1 half baths, and a flexible three-level floor plan, this home is designed for modern living. Ideally located within walking distance to top-rated Bedford Middle School and Staples High School renowned for academic excellence and exceptional extracurricular programs. Beyond its prime location, the neighborhood offers a wealth of amenities, including Wakeman Town Farm, a vibrant community space with educational workshops, gardening and programs for kids and adults, and opportunities to connect with farm animals. The expansive 1.18-acre flat, dry lot provides ample outdoor space, while a multi-tiered deck and newly upgraded patio create the perfect setting for entertaining. Residents can also enjoy easy access to Compo Beach, Longshore Golf, swimming, and tennis, experiencing the best of Westport's renowned coastal lifestyle.

Looking for a year-round rental that feels like a permanent vacation? Nestled in sought-after Saugatuck Shores, on a secluded cul-de-sac, this charming home boasts 3 bedrooms and 2.5 baths. Its airy design with expansive windows bathes the space in natural light, creating a serene atmosphere for unwinding. Revel in stunning vistas of both Long Island Sound and Bermuda Lagoon, accessible through French doors leading to a balcony-ideal for sipping your morning beverage and witnessing breathtaking sunrises. Steps away lies the harbor, offering opportunities for kayaking, paddleboarding, or a refreshing swim in calm waters. Take leisurely walks to the Cedar Point Yacht Club, immersing yourself in the charm of this beachside community. Plus, enjoy proximity to Westport's downtown, featuring upscale shops and dining, Longshore's golf and tennis amenities, and Compo Beach. Please note: availability begins in October.

What a great location for a summer rental! Walk to Coffee An (best donuts around!), walk to Hudson Malone Restaurant. Walk to town! Easy bike ride to beach and or Longshore. This is a great house, oozing with the charm of bygone years. There is even a "sleeping porch" off of the Primary bedroom! Enjoy all that Westport has to offer!!! Available for rent July and August for a two month term but flexible on either end. Note: Addtl fee of $350 due at lease signing for exit cleaning. Also available for Short Term furnished rental.

Location Location Location... Large studio apartment on 2nd floor. Enjoy the comfort and convenience of central air conditioning and laundry in the unit. Take full advantage of all that the neighborhood and Westport has to offer in this prime location, a short distance to train station, I95, Riverside Ave with plenty of shops and restaurants. Off street parking.

Welcome to 45 Washington Avenue and prepared to be wowed! This vintage colonial has been renovated with superb taste and style creating a home that is idyllic for today's lifestyle. Marvelous open floor plan with custom kitchen and baths. Private office with separate entrance. Spacious walk out lower level with playroom, gym, bedroom and full bath. Deck and patio overlook large yard. Dream location minutes away from everything! Walk to town, shops, library, restaurants, and the Levitt Pavilion from one of Westport's best locations. Pets considered. Monthly rental price to increase July 1st to $13,500 for the remainder of the rental term.

Bright, spacious apartment with cathedral ceiling, open kitchen, bedroom, bath. Laundry in unit. Great central location. Walk to town.

Secluded Mediterranean inspired estate located on prestigious Bluewater Hill South with tennis courts and private beach rights to Compo Beach located steps away. Magnificent historical gardens designed by F.L. Olmstead of Central Park fame in the early 1900's. A crescent shaped pool and pergola over patio crown the front lawn and gardens. The upper living level open floor plan boasts water and garden views from the over sized windows throughout the rooms. The living and dining rooms feature a gas fireplace. A balcony off the living room has seating for many guests. Renovated kitchen with custom Maple cabinets and flooring, built in cabinets, stainless steel appliances and dining area. The den located off the kitchen with the laundry can function as an additional bedroom if needed. Master Suite has large renovated bath with custom built in cabinets. Enter on the garden level through the front door and see a sweeping staircase with mahogany railing or take the convenient elevator if needed. This level features three additional bedrooms, two full baths, family room and sun room. The attached two car garage entrance is through the sun room. This home is truly turn key, decorated and furnished with all the comforts needed to enjoy living this resort lifestyle! The upper garden is shared with the owners. SUMMER term begins May 16th, June, July and August.

Enjoy the Summer in Westport!! Beautiful home located in the Greens Farms section of Westport. Spacious living room, hardwood floors throughout, deck overlooking stream, waterfall, and stainless steel appliances. House available from June 20th to Sept 2nd. Enjoy everything Westport has to offer.