Westport CT Real Estate & Homes for Rent

Charming Cape house situated on one acres of beautifully landscaped and maintained grounds. Prime location across from the Hunt Club with unencumbered views of serene horse stables. Enter the home through an inviting sun porch and convenient mudroom area before stepping into the newly renovated kitchen. The spacious living room has an easy flow that is ideal for entertaining friends and spending quality time with family. The office/den area is ideal for those working from home or seeking a quiet space to focus. Off the kitchen, access a large back patio overlooking a heated gunite pool and sweeping backyard. Upstairs the home features 3 large bedrooms, ample closet space and 2 full bathrooms. You'll love the tranquility this private oasis provides.

11 Bellaire Drive in Westport, CT is a warm and welcoming one-year or school-year rental home, furnished and ready to move into on a quiet and convenient Westport cul-de-sac. Whether you are in transition, testing the suburbs, renovating a house or just haven't found the right home to buy yet, this is your opportunity to enjoy convenience and comfort with access to all Westport has to offer. A commuter's dream, this 4 bedroom home has a great yard, updated kitchen, plenty of space without feeling cavernous, and an open floor plan. Landlord somewhat flexible on fully or partially furnished.

Set well back from the road at the end of a long, tree-lined drive, this private Contemporary residence offers a rare pairing of seclusion and central Westport convenience. A short stroll from the Metro-North station, Compo Beach, and Longshore Club Park, the home rests on a level, professionally landscaped 1.05-acre lot in the coveted Compo Beach neighborhood - and, notably, sits comfortably outside the flood zone. Inside, natural light pours across 4,449 square feet of light-filled living space. The main level opens through a gracious foyer to a beamed-ceiling living room with fireplace, a warm family room anchored by a second fireplace, and a well-appointed kitchen with a dedicated home office just off it. A first-floor primary suite makes single-level living effortless, complete with skylight, walk-in closet, and en-suite full bath. Upstairs, three additional bedrooms - including a second suite with its own full bath and walk-in closet - surround a versatile loft, with laundry conveniently placed on the same level. Rich hardwood floors run throughout. A rear sunroom invites easy indoor-outdoor living, opening to the deck, porch, and private grounds, while the finished lower level adds flexible space and a further full bath. Move-in ready and ideally positioned for summer at the beach - an A+ location, out of the flood zone, and ready to welcome its next residents.

Tucked behind a tall fence flanked by stone pillars. Less than 5 minutes to town, schools, beach and train. Easy one floor living. Sun-filled main level open floor plan featuring a Living Room with fireplace, a large well-equipped Kitchen with a spacious Dining Area and Breakfast Bar, and a Family Room with walls of windows inviting nature in. There is also a private office next to the first floor Primary Bedroom with a full Bath. Several French doors are strategically placed to access the oversized deck that spans the length of the rear of the house, and there is a staircase leading to the picturesque backyard. Upstairs you will find the 2nd Bedroom with vaulted ceiling, skylights and a full Bath which can easily be used as a Studio or Office. The finished walk-out lower level offers the 3rd Bedroom and full Bath plus a large flex space for a Playroom, Recreation. Lower level would make for a fabulous au-pair or in-law suite. The Mudroom connects the house to the 2 car Garage, and above the Garage is a large unfinished space that is approximately 22X24. House has a generator. So much to love about this wonderful property.

Location, location, location! Located at the center of Saugatuck. Walking distance to train, restaurants, rowing club, gym, close to Compo Beach, Longshore, Golf, and tennis! Historic Landmark Queen Anne Victorian House c. 1899 with beautiful architectural detail. Well maintained and updated. Grand windows surround the house with light, featuring 9-foot ceilings on the main floor and a wonderfully spaced layout. There are 3 bedrooms, 3 baths, and a den that could be a 4th bedroom. Additionally, there is a large attic and 2-story detached garage with lots of storage. Don't miss this opportunity to call Westport your home and take advantage of the top-rated schools and many fabulous amenities.

Live the Westport lifestyle you've been dreaming of! Perfectly situated in one of Westport's most convenient neighborhoods, this charming renovated apartment places you just minutes from Compo Beach, the train, Saugatuck's renowned restaurants, Longshore Club Park, and downtown Westport. Filled with warmth and natural light, this inviting two-bedroom home features beautiful hardwood floors throughout, an open-concept living space with a skylight and decorative fireplace, and a well-appointed kitchen with granite countertops, a gas range featuring Air Fry mode, and a lighted ceiling fan. Efficient central air conditioning and heating, along with a newer roof, provide year-round comfort and peace of mind. Additional highlights include a private entrance, private attic storage with direct access from the unit, designated storage space in the shared basement, and a shared laundry area. Relax on your private front patio or enjoy the shared backyard, complete with additional storage beneath the deck. As an added benefit, the owner will retain the Compo Beach kayak rack membership; details are available upon request. Whether you're grabbing your morning coffee downtown, dining along the Saugatuck River, spending the day at Compo Beach, or catching the train into the city, you'll appreciate how effortlessly everything is within reach. Fixed utilities make life effortless. Welcome to 19 Hale Street...where convenience, charm, and the best of Westport come together.

Nestled near the beach, this inviting apartment offers a relaxed lifestyle with easy access to local amenities and coastal attractions. Move right into this furnished haven. Newer maple floors in the kitchen, thoughtful storage space, and mini-spilt unit installed in 2022. Modern, thoughtful touches throughout. The kitchen showcases a propane stove, granite counters and ceiling fan. Private entrance through an external staircase. Designated storage space in the home's shared basement, where the shared washer & dryer are located. Enjoy private use of the deck along with a shared backyard and additional storage beneath the deck. Owner will keep Compo Beach Kayak rack membership, inquire for further details! Fixed utilities make life effortless. Very-walkable location: just over a mile to the Westport train station, the vibrant restaurants of Saugatuck and Longshore. Meet friends for an Americano at the amazing Old Mill Market. Enjoy a delicious dinner at the club overlooking the river. The perfect place awaits at 19 Hale Street!

Step into the timeless charm of this 1920s Classic Colonial, perfectly situated on nearly an acre of lush, manicured grounds. With 2,570 square feet of refined living space, this home effortlessly blends vintage character with modern convenience. The interior features four spacious bedrooms and two-and-a-half baths, offering a thoughtful layout that feels both grand and inviting. The heart of the home opens up to a beautiful, spacious deck and yard, providing a serene backdrop for morning coffee or afternoon relaxation. For those who need extra space, the 1,269-square-foot unfinished basement offers incredible storage potential, complemented by the convenience of a two-car attached garage. The location is truly unbeatable, placing you just moments away from local favorites like The Little Barn, Big Y, and an array of popular shops and restaurants. This is a rare opportunity to enjoy a quintessential New England lifestyle in a premier setting. PLEASE SEE ADDITIONAL REMARKS RE: UTILITIES AND LAWN CARE.

Is this Westport or Provence? Sited high above Greens Farms is this charming and spacious renovated cottage on a prime, flat and open estate property. A water lover and swimmer's dream, with stunning, large heated pool (with kick pads) and spa (seats 8+). All-new gourmet kitchen, newly finished pickled wood floors, fresh paint throughout. Decorated for stylish and comfortable living, it's the perfect place to call home. Sunny living room, spacious family room with fireplace and wet bar. Private setting, away from main house. Walk to Greens Farms train station, quick bike ride to Burying Hill beach. Organic garden onsite with fresh herbs and occasionally vegetables available too! Full pool and spa privileges. See floor plans in attachments.

Imagine starting your day with a walk to a private beach, an afternoon on the water, and dinner just minutes away in vibrant Saugatuck. This beautifully furnished home offers the lifestyle that makes Westport one of Connecticut's most coveted coastal communities. Walk or bike to three private association beaches with Adirondack chairs, picnic areas, kayak racks, and grills, then enjoy the nearby amenities of Longshore Club Park, including golf, tennis, sailing, swimming, and waterfront dining. Just minutes from the train, Main Street boutiques, and acclaimed restaurants, the location offers the perfect blend of seaside tranquility and everyday convenience. Inside, sun-filled living spaces feature soaring ceilings, custom millwork, rich hardwood floors, and wood-burning fireplaces that create a warm yet sophisticated atmosphere. The chef's kitchen is appointed with professional-grade appliances, an oversized marble island, and generous space for entertaining. Upstairs, four spacious bedrooms, including a serene primary suite with a spa-inspired bath, provide a peaceful retreat after a day by the water. Thoughtfully designed indoor and outdoor living spaces complete this exceptional opportunity to experience the very best of Westport living. Available September 10, 2026 to June 30, 2027

Available rental in greens farms!!! Come sample living in Westport and enjoy everything the town has to offer. Overlooking Signal Lake this antique home has all the charm of a house from the 1800s with the conveniences of today. A beautiful screened porch gives perfect 3 season enjoyment of the outside. Upstairs find the primary suite, another ensuite bedroom and 2 additional bedrooms. Flexible floor plan with room for home work space (office) with separate entrance. Tesla charger. Very convenient to both Westport train stations, and Compo beach. Set back off the road on a neighborhood cul-de-sac on a beautiful landscaped acre.

Welcome to 108 Harbor Road, a beautifully updated 4-bedroom, 2.5-bath home on desirable Saugatuck Island in Westport. Enjoy an open floor plan, recently renovated, and stylish finishes in every room. Just a short stroll to the water, this inviting home offers the best of coastal living and easy access to all that Westport has to offer. Available for up to 10 months starting September 8.

Move right into this completely renovated, like-new first-floor 2-bedroom rental in one of Westport's most convenient locations. Every detail has been thoughtfully updated, offering modern finishes, stylish design, and the comfort of an all-new living space. Ideally situated directly across from the picturesque Saugatuck River and just minutes from vibrant Westport Center, shopping, dining, train stations, and major commuting routes, this home combines exceptional convenience with a desirable neighborhood setting. Unit 1 features easy one-level living with a bright and inviting living room, two spacious bedrooms, a beautifully renovated full bath, and the convenience of an in-unit washer and dryer. Enjoy relaxing on the screened porch overlooking the level backyard-perfect for outdoor enjoyment. Ample off-street parking completes this exceptional rental. Experience the best of Westport living in a fully renovated, move-in-ready home that feels brand new.

Lovely sunny cottage with recent updates--separate and private, attached to main house, on a beautiful cul de sac in the heart of Westport. Private entry and large entry foyer suitable for study/office, large eat-in kitchen with stone countertops, stainless steel appliances, stairs to living room and separate bedroom with ample closet space, new bath and washer/dryer. Private garage, 1 spot only, guest parking is on street. Tenant pays credit check. Utilities are paid as additional flat fee of $150/month. Please note: This is a single occupancy unit.

Prominently situated at the end of a private enclave surrounded by nature is where you will find 4 Nappa Lane. This beautifully renovated home offers a serene escape while being perfectly positioned just minutes from everything Westport has to offer. Step inside to discover a bright, open interior where modern updates meet effortless style. The heart of the home features a fully renovated kitchen that flows seamlessly into spacious living areas, all framed by large windows and sliders to the outdoor deck that bring the lush greenery of the outdoors in. Each room has been thoughtfully refreshed with refinished hard wood floors, beautifully tiled kitchen and baths and a neutral palette, creating a sophisticated backdrop for any lifestyle. The primary suite serves as a tranquil retreat, complemented by an additional en-suite, and 2 other well-appointed bedrooms that offer versatility and flexibility. A partially finished walkout lower level offers a flexible space for work or play. The back garden provides a private oasis for relaxing or entertaining. With its blend of modern luxury and a secluded, natural setting, this home is a rare rental opportunity in a prime location.

** JULY / AUGUST SUMMER RENTAL ** Tucked away on a quiet cul-de-sac in Westport's prestigious Red Coat neighborhood, this beautiful contemporary home offers exceptional privacy on 2+ serene acres with direct access and views of the Saugatuck River. Designed with a timeless mid-century modern aesthetic, the open floor plan is centered around a dramatic vaulted living room featuring a circular fireplace, wet bar, and walls of glass that fill the home with natural light. The main level lives like a ranch, offering a spacious primary suite and two additional bedrooms, all conveniently located on one floor. Large windows throughout frame picturesque views of the pool, spa, and surrounding landscape, creating a seamless connection between indoor and outdoor living. The walkout lower level features a generous family room, den, 3 additional bedrooms, a convenient kitchenette, and a pool changing room with shower. Walls of glass overlook the pool and bring abundant natural light into the space. A private pathway leads to the Saugatuck River, where you can wade, fish, or launch a kayak right from the property's riverfront access. Ideally located just minutes from the YMCA, Merritt Parkway, downtown Westport, and the town's award-winning schools, this rare rental opportunity combines architectural character, resort-style amenities, and an exceptional Westport setting. ** LANDLORD COVERS POOL AND LANDSCAPING. ALSO AVAIL. YEARLY

Fully Furnished & All Utilities Included: Prime Turnkey Living in Downtown Westport Experience the ultimate in convenience and coastal charm with this bright and cozy 2-bedroom, 1-bathroom apartment located right in the heart of Westport. Situated in a historic charm-filled brick building, this unit offers an unbeatable lifestyle for commuters or anyone looking to enjoy the very best and convenience of Fairfield County living. Step out your front door and you are immediately immersed in the vibrant energy of the Saugatuck and Downtown Westport areas. Access to the prestigious Westport School District (Saugatuck Elementary, Staples High School). Fully furnished, all-inclusive in this highly sought-after, walk-to-town location rarely stay on the market long.

Embrace the rhythm of coastal living in this stunning, fully furnished retreat on Saugatuck Island. Spanning 4,200 square feet across three thoughtfully designed levels, this residence is more than just a home-it's a sanctuary defined by light, salt air, and sophisticated design. The experience begins in the striking foyer, where an open lighthouse cupola soars overhead, bathing the interior in a warm, natural glow. Every corner of this 5-bedroom home reflects an eye for detail, featuring exquisite finishes and curated decor that blend luxury with a relaxed, beachside soul. Outdoor living is a cornerstone of the lifestyle here. Step out onto the screened deck to catch the sea breeze or retreat to the private, fenced backyard. Whether you're hosting a summer cookout at the built-in grill on the stone patio or enjoying the lush green space, the grounds are designed for effortless enjoyment. Best of all, two private beaches are just moments away, offering easy access to swimming, boating, or simply lounging by the shore. While it feels worlds away from the daily grind, this island gem is incredibly convenient. You are just minutes from the Metro-North, major highways, local yacht clubs, and the vibrant dining and shopping scene that makes Westport so desirable. Whether you're looking to spend your days biking quiet roads or watching the sunset over the sound, this property offers a rare opportunity to live the ultimate beach retreat lifestyle.

It is the luxury rental you have been waiting for... Perfectly positioned at the edge of Mill Pond, this exceptional home offers breathtaking views and fabulous sunrises from every room. Whether you are looking for a summer vacation or considering making Westport your home, this is a rare opportunity to experience the very best of coastal living. Featuring a first floor bedroom and 4 additional bedrooms on the 2nd floor, the thoughtfully designed layout provides flexibility for guests and family. There is a gourmet kitchen perfect for entertaining while endless outdoor living areas create the ultimate setting for relaxation. This home showcases high end designer furnishings- every space feels like an elegant and comfortable retreat. Just a stroll to Compo beach your private oasis includes a heated pool, putting green, pickleball court, in-home gym and kayak.

*Charming Compo Beach Rental. Experience the best of Westport living in this beautifully renovated 3-bedroom, 3-bathroom home located just steps from Compo Beach and the Longshore Club. Available as a winter/school year rental starting January 2026 for $9500/month. Walk to Compo Beach or enjoy nearby amenities at the Longshore Club, including golf, tennis, and pools. Open-concept living spaces with hardwood floors throughout. The first-floor den with an adjacent full bath can serve as a 4th bedroom or guest room. Fully updated eat-in kitchen perfect for entertaining. Relax by the gas fireplace or unwind in the screened-in porch. The primary suite includes an updated ensuite bath, while two additional bedrooms feature vaulted ceilings and skylights. Outdoor Living: Enjoy the private backyard deck with a BBQ, string lights, and a cozy seating area. Dogs considered on a case-by-case basis (no cats). Non-smoking home.

Beach Town Living at Its Finest! Experience the pinnacle of Westport living in this stunning new architectural gem. Situated in the prestigious Hunt Club neighborhood, this classic Colonial is set on a private rear lot offering privacy and serenity. Built to the highest standards by a local craftsman, the home spans four expansive levels of living space with 6 bedrooms, 5.1 baths, and seamless transitional design. The light-filled, open-concept floor plan is outfitted with every modern amenity, anchored by a true chef's kitchen featuring a commercial-grade 8-burner Wolf range, a full suite of stainless steel appliances, a classic subway tile backsplash, and a center island built for both cooking and entertaining. The adjoining family room invites you in with a stone fireplace & custom built-ins. The second level offers a thoughtfully designed layout for guests alike: a luxurious primary suite with a spa-like bath featuring a soaking tub and double vanity, two bedrooms connected by a Jack-and-Jill bath, and two additional bedrooms sharing a full hall bath & second-floor laundry room. The fourth level delivers exceptional flex space and a sixth bedroom with its own private en-suite bath, ideal for guests, an au pair, or a private home office retreat.

Renovated 5-bedrooms, 3 bathrooms home in a great Westport location! Updated : kitchens, bathrooms, Harwood flooring, New AC, New navien boiler. Stainless steel appliances, 2 car garage, new laundry machines. The 1.55 acre property has room to walk and bike on a flat, 1/2 mile cul de sac. You won't find a better home and property that has great living spaces and sunshine peaking through ever window. Close to the award-winning Staples High School. Excelent credit a must, application through RentSpree.

15 Timber Lane, Westport, CT | School Year Furnished Rental Experience luxury living in the coveted Roseville neighborhood of Westport. Situated on 1.45 private acres at the end of a quiet cul-de-sac, this beautifully furnished 4-bedroom, 5-bath home offers the perfect school year retreat. Designed for comfortable living and entertaining, the home features two spacious primary suites with vaulted ceilings, a cathedral ceiling family room with fireplace, formal living room, private home office, screened porch, and multiple gathering spaces. The gourmet eat-in kitchen is appointed with limestone countertops and premium Sub-Zero, Viking, and Bosch appliances. Step outside to your own private oasis featuring a heated gunite pool, hot tub, expansive patio, pergola-covered deck, and beautifully landscaped grounds. Ideally located just minutes from Westport's award-winning schools, downtown shops and restaurants, Compo Beach, Longshore Club Park, Metro-North train station, and major commuter routes. Features: Fully furnished * 4 Bedrooms * 5 Full Baths * Two primary suites * Heated gunite pool * Hot tub * Gourmet kitchen * Multiple fireplaces * Home office * Screened porch * Three-car garage * Private cul-de-sac setting. Available for a 9-10 month school year lease. An exceptional opportunity to enjoy one of Westport's most desirable neighborhoods in a private, turnkey home.

Wake up just steps from the Saugatuck River, grab a coffee from your favorite local cafe, and enjoy the convenience of having Westport's best restaurants, boutiques, and the Metro-North train station all within walking distance. This beautifully renovated 2-bedroom, 1-bath apartment combines timeless charm with fresh, modern finishes in one of Westport's most sought-after neighborhoods. Spend mornings sipping coffee in your private backyard, afternoons strolling along the river or with your paddleboard, and evenings enjoying everything downtown Westport has to offer-all just minutes from your front door. Compo Beach also a short drive away! Features you'll love: Newly renovated throughout 2 spacious bedrooms | 1 full bath Bright, modern kitchen and stylish finishes throughout Private backyard space perfect for relaxing Steps to the Saugatuck River Walk to restaurants, coffee shops, shopping & Metro-North Easy access to I-95 for a seamless NYC or Stamford commute Whether you're commuting to the city or embracing the coastal Westport lifestyle, this home offers the perfect balance of location, comfort, and convenience.

Enjoy this sun-drenched renovated contemporary split-level home with open floor plan. Featuring a private, fenced in yard, this inviting renovated property offers the perfect blend of style, comfort and convenience, just minutes from town, beaches, shopping, dining, schools, train and all that Westport has to offer.