Westport CT Real Estate & Homes for Rent

Discover the charm of this 2-bedroom, 1-bathroom apartment located on the second floor of a Saugatuck neighborhood two-family home. This ideally situated apartment is only minutes from the train and Saugatuck restaurants. It boasts a flexible floor plan with large, bright rooms, high ceilings, and a finished walk-up attic space perfect for a home office, exercise room, art studio, or storage. The updated kitchen features granite counters, while additional highlights include central A/C, hardwood floors, and a whole-house generator powered by solar energy. Enjoy the convenience of a one-car detached garage bay and your own washer and dryer in the basement. The tenant is responsible for oil/heat, cable/internet, water, and liability insurance, while the landlord covers electricity (within an estimated usage), sewer, grounds maintenance, taxes, and trash service. This prime location is just minutes from downtown, Longshore, and Compo Beach, making it a true Westport gem! No pets please.

Remarkable Westport Estate: The "John Morehouse Jennings" House. Stunning 1832 home, awarded by the Westport Historic District Commission for its exceptional restoration, is nestled within nearly 40 acres of Audubon-protected land. It ensures ultimate privacy on its own 2-acre lot, complete with a pool, tennis court, and a separate historic guest house. The main house, spanning 7,444 square feet, is a masterpiece that blends historic grace with modern living standards. It features generous room layouts, high ceilings, five fireplaces, and a kitchen wine cellar, making it a perfect home for entertaining with a charm and elegance seldom found. The updated guest house, with 790 square feet, is archived in the Historic Barns of Connecticut. It includes two bedrooms, one bath, an eat-in kitchen, and a garage, making it ideal for a nanny, grandparent, or caretaker. The property is an oasis framed by mature plantings along the Audubon preserve. Outdoor living is enhanced by a large bluestone patio with a fireplace and pergola, a beautifully landscaped pool with a diving board, a 12-person spa, and a separate gazebo. The expansive yard includes a HarTru tennis court, a large garden, an outdoor shower, and plenty of space for sports, a trampoline, or a swing set. Located just 1/2 mile from Southport Beach and within walking distance from the train, this magnificent Greens Farms estate offers an opportunity to own a piece of Westport history with unparalleled beauty and sophistication.

Rare rental opportunity in Saugatuck Shores! Experience the charm of one of Westport's premier waterfront communities, perfect for leisurely walks, biking, and access to three private beaches equipped with adirondack chairs, picnic tables, kayak storage and grills. Enjoy the best of coastal living, just minutes away from Saugatuck's great restaurants, train station and shopping on Main Street. Access is available to golf, tennis, the sailing school, and a waterfront restaurant at Longshore Country Club. Island Way's bright and airy living spaces are tastefully furnished and feature woodburning fireplaces to cozy up to on chilly nights, high ceilings and custom finishes. The chef's kitchen is a highlight with professional-grade appliances and a spacious marble island. Upstairs, four bedrooms, including a primary suite with a spa bath, provide serene spaces for relaxation after an active day. Available August 1. Available month of August. Also available at yearly rate of $15,000PM starting September 1

Rare rental opportunity in Saugatuck Shores! Experience the charm of one of Westport's premier waterfront communities, perfect for leisurely walks, biking, and access to three private beaches equipped with adirondack chairs, picnic tables, kayak storage and grills. Enjoy the best of coastal living, just minutes away from Saugatuck's great restaurants, train station and shopping on Main Street. Access is available to golf, tennis, the sailing school, and a waterfront restaurant at Longshore Country Club. Island Way's bright and airy living spaces are tastefully furnished and feature woodburning fireplaces to cozy up to on chilly nights, high ceilings and custom finishes. The chef's kitchen is a highlight with professional-grade appliances and a spacious marble island. Upstairs, four bedrooms, including a primary suite with a spa bath, provide serene spaces for relaxation after an active day. Available September 1 (August available at summer rate). August available at summer rate of $25,000PM

Available immediately for yearly unfurnished rental or (6 month minimum) winter/academic year rental furnished or unfurnished. This totally refreshed 4 Bedroom, 3.5 Bath 2007 Colonial, is nestled on the banks of the Saugatuck River on a quiet cul-de-sac, a 10 minute stroll to Westport's Main Street with a wonderful river deck for kayak launch or quiet contemplation. New Primary Bath and Powder Room, extensively renovated Kitchen, freshly painted throughout, newly refinished hardwood floors, new lighting and so much more.Also available for sale. MLS # 24022717. Owner will entertain rental purchase and also financing for qualified buyers.

This modern residence is located in the center of downtown Westport. Ideally situated in the heart of it all, this location is conveniently situated near dining, shopping, and entertainment. This inviting one-bedroom home feature upscale amenities and spectacular views, making it the perfect alternative to New York City living, in a suburban setting. The Residences at 33 Elm offer a lifestyle of luxury furnished (additional fee) or unfurnished. Lease terms can be arranged for one-year, two-years, or more. A video walk through is available upon request. Developed by David Adam Realty, designed by Architect Frederick W. Hoag.

Located on a private street, this brand new beautifully renovated shore colonial offers luxurious living on a quiet and quaint cul-de-sac by a stream. A short walk to town, fine dining, art galleries, high end shopping and all Westport has to offer, with top rated schools around the corner. This unique location is only minutes from Compo beach. This multi-level apartment is set among beautiful trees and a charming neighborhood. Find comfort in living at the in-demand location rich with history, where the mill workers and artists once made Westport what it is today. This wonderful home features vaulted ceilings upstairs with 14 feet ceilings in the bedrooms. The large family room leads into the elegant dining room with a coastal cathedral ceiling. The gourmet kitchen boasts marble countertops and your very own wine cooler. The fresh basement allows for bonus storage/office/workshop with an extra fridge and a new laundry unit. The French door flows out to the cozy covered porch just steps away from your private patio retreat underneath the mature Japanese maple. The front and back yard give ample room for enjoyment. Just minutes to metro north station to Manhattan this is the perfect place to enjoy as your home. Owner pays for landscaping and snow removal. Renters pay for all utilities, pet fee, and trash pickup. No smoking. Private driveway. Monthly Pet Fee

Beautiful one-bedroom apartment 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. All utilities included!

Playhouse Square is adjoining the Westport Country Playhouse and conveniently located in downtown. The first floor, except for the bathroom, was resurfaced with an engineering hardwood flooring instead of carpet. Tenant is the process of packing and I couldn't take pictures. Living room has a cathedral ceiling and a fireplace. The Kitchen has newer stainless steel appliances and adjoins the dining area. A bedroom on the first floor maybe used as an office. Second floor master bedroom has sliders to a private deck, a walk -in closet and a regular closet as well and well sized master bath. Two dedicated parking space in the parking garage. Walking distance to restaurants, shopping, library and post office. Short drive to Metro North train station. During the visit you will see the unit as furnished by the present tenant. Agent is part owner.

Spectacular Waterfront Living in Westport! This Nantucket Style home is indeed a "jewel". Panoramic views from every floor and a sophisticated open floor plan for entertaining. Relax and enjoy all the serenity of living on the water yet just 3 minutes to Westport Center and railway station. Meticulously maintained. A private patio offers an oasis for outdoor living and watching the sunset. Do not forget to stroll over the bridge on a hot summer night for ice cream and enjoy the many restaurants just 3 minutes away. Absolutely no pets!

Enjoy the Island Lifestyle at this beautiful, mint-condition home available for Lease on spectacular Saugatuck Island. Scenic splendor surrounds you, and every day becomes a vacation when you reside in this sought-after water community where private beaches, marinas, sea breezes and a friendly atmosphere enhance the quality of life. Beautifully landscaped and set on a picturesque property with some water views, this Modern home is sparkling and ready for immediate enjoyment. Available either furnished OR unfurnished, this is the ideal home to spend up to one year in. The cathedral ceiling living room and dining room both have views of the attractive surroundings and are filled with light. The remodeled kitchen is immaculate, with granite counters and stainless steel appliances. Step out onto the wraparound deck and enjoy a view of Long Island Sound, sunshine and fresh air. The family room has a fireplace and access to the patio and level backyard. Four bedrooms each have good closet space and there are two meticulous, updated full baths. Additional spaces include the full laundry room with sink, one car garage and a storage shed. There is an automatic generator. The owner will cover the costs of landscaping through the season. ADT security system. This home is available with OR without the tasteful furnishings shown in the photos, and is available for immediate occupancy through July 15, 2025.

2022 Preservation Award Winner HIDDEN GEM PRIVATE BACKYARD. This convenient and walkable-to-town home is an award-winning makeover of an early 1900's barn in-the-heart of Westport's sought-after Kings Highway Historic District. Its privacy will surprise you, nestled in one of the most picturesque, in-town, quintessential-Connecticut settings you could wish for. In this quiet and private residence, wake up to a view of the red barn next door that was a speakeasy during Prohibition. Sip cool refreshment on your quiet back porch under a breeze from the ceiling fan, while contemplating the tranquil view of an old-style fieldstone drywall. When it gets buggy out, you can drop automated screens at the press of a button and continue your meal without missing a beat. Sonos-connected speakers pipe your favorite music indoors and outdoors --wherever "you" and your entertainment merge. The Barn is accented inside and out with authentic beams that were part of its origin as shelter to farm animals. New life is breathed into every square inch of this home to carry it into its next 100 years. Artifacts have been salvaged and reused such as the barn doors rails and horseshoes re-attaching the original rustic door to the front facade. The fireplace installed in the early 1900s during the barn's conversion to a residence is prominent and newly-operational with its original swinging black wrought iron screens, andirons and brick from the now-defunct North Haven Stiles Family Found

Fabulous three/four-bedroom home with lovely eat-in kitchen, dining room/family room, living room, two full baths. 2000 square feet-very spacious. Extra-large deck overlooking huge back yard lined with beautiful trees and decorative rocks. Nice garage and stone storage shed. Across the street from the Saugatuck River. Enjoy kayaking, swimming, and all water activities. Walk to train, shops, restaurants, Compo Beach, Long Shore Park and golf. Top rated school system. Great location!

Great Westport location walkable to train, beach, longshore. Amazing house with extra large front yard set far off Compo Rd South. This beauty offers privacy in a coveted Westport location. The long private tree-lined driveway offers a dramatic entrance to the home with a front yard large enough for a soccer game! The house has 4 bedrooms and 5 bathrooms with tremendous natural light. The master suite is on the 1st floor, with 3 additional bedrooms on the upper level. There is a great home office. Gorgeous hardwood floors throughout the home. A finished basement with a full bath that offers convenient guest space. Plus, a great sunroom in the back that allows for relaxation to sit and enjoy the mature landscaping. Open concept living with high ceilings. Location! Location! Location! This house is an A+ location near the beach. Move-in ready so you can be in Westport for the summer and be ready for the great schools in the fall. A must see for renting.

This spacious 3 bedroom cape is only a block from Post Road activity and easily accessible to train and highway, sited in a pleasant Greens Farms neighborhood. Here you are an easy walk to Starbucks, Carvel or the landmark Sherwood Diner for refreshment or meeting.The home has been rented for more than 10 years by the same tenant, and is ready for occupancy just in time for the school year. Many features make it worthy of such a happy and lengthy residency. Multiple windows invite the outdoors and light into the rooms, creating gracious entertainment and peace-filled spaces. A welcoming fireplace, bay windows and charming built-ins mark the home as thoughtfully designed, vintage 1930s construction. The SUN ROOM/DEN can multi-purpose as tv room and office. The KITCHEN is next to an oversized parking pad behind the house that is a great staging area for visitors or major packing/unpacking of cars. The kitchen bay window and dining room overlook the fenced backyard lawn and play area. A SUN ROOM might be your favorite home office because of its own exterior door for direct access by clients.The 1st floor PRIMARY BEDROOM has full bath ensuite and can flex as a cozy FAMILY ROOM. Central to the house, this bedroom is convenient to all social activity in kitchen, living room and dining room -- and across from stairs to the 2nd floor where 2 more bedrooms and full bath offer a quieter existence. Both upstairs bedrooms are substantially larger(see square footage on floor plan).

Newly renovated 1-bedroom apartment for lease in downtown Westport! Amazing location in the center of Main Street and walking distance to all the popular shops and restaurants. All new appliances, high end finishes, washer/dryer in suite, and private balcony overlooking Main Street!

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 $18,500 is for a 12 month lease. Shorter term rental rates are Seasonally adjusted.

Furnished rental with water views and access. Forget your cares and your car! Artist's restored farmhouse with oodles of charm, sophistication and amenities (central air, porch, two swings, two patios, BBQ grill, grassy yards, outdoor Ping Pong, chef's kitchen and hydro tub for relaxing) in Westport's 'happening' restaurant village of Saugatuck. A 5-minute walk to everything: the train to NYC (one hour), kayak and paddle board rentals, ice cream, wine shops, dining. Across from a lovely riverside park with footpaths and nearby boardwalk. Stroll to library, Levitt Pavilion and bike to the beach and town golf, tennis, and sailing. What a location!

Convenient in town location. Walk to downtown, restaurants, library, Levitt pavilion. Charming home with beautiful private yard.

Classic colonial centrally located within Westport. Convenient to schools, Post Rd, shopping and beach. Large and bright bedrooms with Harwood floors. Natural gas and connected to town sewer. Finished walk-out lower

Direct Waterfront...Special & Wonderful Summer rental! Available July and August. Spend a secluded Summer overlooking the Mill Pond in Westport, CT, steps away from Compo Beach and all Westport offers, Sherwood Island State Park. Antique home with manicured lawn, landscaped beds, and stone walls. This 3 bedroom, 2 bathroom home is tastefully decorated, eclectic, and versatile for every occasion. Luxury hotel living in a Summer Paradise! Hardwood floors, large kitchen with pantry, Island, and 2 ovens. Waterviews from virtually everywhere, inside and outside. Expansive Living and Dining Rooms, a sunroom off the kitchen that's perfect for reading, napping, or entertaining. Library on the first floor and an office to work from(if you have to). Great place to enjoy a quiet book-filled Summer and just a quick train ride into NYC. Outdoor kitchen with pizza oven, outdoor shower, fire pit, hot tub, and sauna. Kayaks and Canoes included. Available July 1 Westport has great beaches, parks, shopping, and restaurants. Unique and beautiful property. Easy to show!

Well maintained charming 3-4 Bedroom, 2 Full Bath rental available for August 2024. The location is ideal for both convenience and access to Westport amenities some of which includes: downtown Westport shopping, Compo Beach, Longshore Club Park, Metro North Train Station, top rated schools and I-95. Highly desirable neighborhood. The open floor plan and abundance of natural light are definite highlights, creating a welcoming atmosphere throughout the home. White Kitchen has new stainless steel appliances that opens up into the Dining area and the Living Room. There are 3 Bedrooms on the second floor and on the upper floor there is an additional room that can serve as a Bedroom or a private Office based on the tenants needs. The lower level Family Room is large and sunny with a full bath and new shower. Recently painted inside and outside. Hardwood floors in all rooms except for the lower level. The screened-in porch and deck offer great spaces for relaxation and entertainment, while the flat spacious backyard adds even more versatility for outdoor activities. Central Air. Lease term is one year or longer.

Cute as a button. You will find so much more than expected both inside & out of this wonderful home. Privacy and nature surround you in this 3 bedroom 2.5 bath raised ranch in Old Hill. This home is spotless. The main floor has a living room, dining room and eat-in kitchen. A master bedroom with ensuite bath and 2 additional bedrooms complete the main level. The lower level has a spacious playroom/den with sliding doors, an office nook or studio space and a laundry room, plus an attached 2 Car Garage. An amazing bi-level, 50+/- foot deck overlooks a babbling brook. Convenient to the Westport Family YMCA, Merritt Pkwy, I-95, Metro-North and downtown. This is the rental you have been looking for! The owner prefers a multiyear lease. Road to be resurfaced in the next few weeks.

Flexible terms The Month of August is $16,000/mo.

Spend the academic year in this charming, turnkey furnished home. Fabulous open plan sited in a most convenient Westport location. Walk to the river, the library and Levitt, restaurants and downtown. Less than 1 minute by car to the grocery store & 3 minutes to the Saugatuck train station. Fully fenced property with a secret entrance to adjacent ballfields & public rec facilities. Easy living with every modern convenience. If you are in need of a wonderful and welcoming place - look no further.