Westport CT Real Estate & Homes for Rent

Stunning 4-Bedroom Historic Gem in the Heart of Downtown Westport Step into a rare piece of Westport history with this beautifully restored and fully renovated apartment, perched on the 3rd floor of a charming 1892 walk-up commercial building. This expansive 4-bedroom, 2-bath residence seamlessly blends timeless character with modern updates, offering a truly unique and inviting layout. With generous proportions throughout, this home features plush carpeting in the living areas and bedrooms, and sleek finishes in the kitchen and bathrooms. The open floor plan provides excellent flow for entertaining or simply enjoying the spaciousness of this one-of-a-kind property. You'll love the unbeatable location - just steps from vibrant downtown Westport and moments from the Levitt Pavilion, where music and community events are always on the calendar. This is a rare opportunity to live in a distinctive, historic space that's move-in ready and available for immediate occupancy. Don't miss your chance to experience this special property - schedule your showing today!

Tenant in residence. Experience the perfect blend of charm, sophistication, and convenience in this beautifully updated Colonial home, nestled in the vibrant Saugatuck Enclave. Just a short stroll away from the Metro North train station, popular restaurants, and the scenic river, this residence offers both tranquility and accessibility. Boasting four spacious bedrooms, two full bathrooms, and a half bath, this home is designed for modern living. Enter through the inviting front door into a gracious foyer, flanked by a home office on the left and an expansive formal living room on the right, featuring a cozy wood-burning fireplace. The heart of the home is the open-concept kitchen and family room, bathed in natural light from numerous windows. A formal dining room seamlessly connects to the living room, creating an ideal space for entertaining. Upstairs, the primary suite occupies the entire rear side of the home, providing a private retreat away from the other three bedrooms. The lower level offers a versatile playroom or movie room, along with convenient laundry and ample storage space. Outside, enjoy informal gatherings on the patio, surrounded by a generous, well-maintained yard. This home is a delightful haven with close proximity to all the amenities that make Saugatuck a sought-after community.

Charming Greens Farms Gem - Newly Renovated From Top to Bottom! Welcome to this stylishly furnished rental in the sought-after neighborhood. This 3-bedroom/3-bath residence has been thoughtfully updated, blending timeless charm with modern comforts. Situated in a prime Westport location, this home offers easy access to everything that makes life here so special. You're just minutes from beautiful beaches, local shops, and award-winning restaurants, as well as Longshore Club Park, where you can enjoy golf, tennis, swimming, sailing, and so much more. Only 5 minutes from the train station and 95. The convenience and lifestyle can't be beat. Upon entering, you're greeted by a light-filled living room, a cozy den, and a full formal dining room-ideal for gatherings and everyday living. The eat-in kitchen offers a welcoming space to cook and dine, featuring stylish finishes and plenty of room to enjoy morning coffee or casual meals. Upstairs, you'll find 2 generously sized BRs w/ample closet space & natural light. The fully finished lower level adds wonderful flexibility with a 3rd bedroom, full bath, & spacious rec room that opens directly onto the brand-new deck. Step outside to enjoy a fully fenced backyard, perfect for outdoor entertaining, summer BBQs, or simply relaxing in your private oasis.

BRAND NEW ROOF. BRAND NEW BOILER. Even though the house is not new, it sure will seem like it is! But that isn't the best part about this house...this lovely home is in a catbird seat location! Walking distance to the best Westport has to offer...Main Street shops & restaurants, the library, the Levitt Pavilion, the farmers' market or the Playhouse. A quick bike ride to Longshore Park or Compo beach, this home sits in the heart of Westport. Newly painted and refreshed, this home is so easy to enjoy. A lovely, sunlit living room with a wood-burning fireplace is wonderful for entertaining. A roomy, eat-in kitchen is adjacent to the dining room with sliding doors that leads out to a deck. Having dinner on the deck is like dining among the treetops! Two ample-sized bedrooms and a hall bath, along with the Primary bedroom with ensuite bath, complete the upper floor of this home. The downstairs has an office or workout space (you decide how to use it!) and a large family room with a fireplace and sliders that lead out to the newly landscaped backyard. To complete the package, this house has a very convenient attached two-car garage. The only thing better than the location, is the wonderful home itself!

This light filled home is set on 2 acres finished on both levels with over 2300 sq ft of living space. Beautiful flat back yard for fun summer games. Just 3 minutes from the Metro North, and convenient to all the Westport amenities.

Just a 3-minute walk to Compo Beach waterfront! Short-term summer unfurnished rental in the center of Compo Beach. Ideal location! 4 bedroom with office, 3 full, 1 half bath. Eat-in kitchen, family room with large deck, finished basement with door to back yard, private laundry room. Lots of space in this 3,129sf home. All bedrooms with new window AC units. BBQ on the deck, play in the yard, walk to the beach. Enjoy the summer at Compo Beach! Wont last! Pet friendly. Available July 8th - Aug 31st

This beautifully maintained Westport 1-bedroom apartment provides the perfect blend of convenience and charm. Ideally situated within walking distance of trains, buses, restaurants, bars, and coffee shops, it's also just a short drive to Compo Beach, Longshore, and Main Street. Flooded with natural light, this bright and airy second-floor unit features gleaming hardwood floors and an updated kitchen equipped with a refrigerator, electric range, dishwasher, microwave, and sink. River views and landscaped grounds make this location perfect. The landlord provides heat, hot water, snow removal, and trash collection. Tenants are responsible for electricity and cable/internet. Additional perks include one assigned parking space and access to a coin-operated laundry in the basement. Must have excellent credit, strong references, and proof of income. No pets, smoking, or vaping allowed. Don't miss this fantastic opportunity to live in the heart of Westport!

Charming Summer Retreat in the Heart of Westport! Blend timeless New England charm with today's modern comforts in this beautifully appointed 5-bedroom, 4.5-bath home, perfectly located on a quiet cul-de-sac just steps from Winslow Park, The Westport Country Playhouse, and downtown. This spacious home sleeps 10 comfortably and is finished on three levels, offering plenty of room for family and guests. The main level features elegant living spaces filled with natural light, while the lower level includes a casual hangout area, a second kitchen, a bedroom, and a full bath - ideal for entertaining or providing extra privacy for guests. Outside, enjoy a beautiful back deck and a lush yard perfect for summer barbecues or relaxing with a book. Bike to Compo Beach, stroll into town for evening dinners, or spend the day at nearby Longshore - all just minutes away, including the train for easy NYC access. Rental dates are flexible during the summer months. This is your perfect summer escape in Westport - luxurious, private and convenient!

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. Tenant does credit check. Utilities are paid as additional flat fee of $150/month.

Charming beach cottage nestled in a serene Compo Beach cul-de-sac, this delightful home offers a perfect blend of comfort and coastal living. Featuring vaulted ceilings throughout that enhance its spacious feel, a cozy stone fireplace, and elegant wood floors, the open floor plan creates an inviting atmosphere. The sunroom leads to a stone patio, ideal for gatherings, overlooking a fenced, meticulously manicured backyard, providing both privacy and a picturesque outdoor retreat. Enjoy the convenience of walking or biking to Compo Beach, just moments away, and the proximity to town amenities adds to the appeal of this idyllic seaside retreat. Perfect for those seeking a relaxed lifestyle in a sought-after beach community, bring your paddle board, kayak and bike!

Enjoy all that Westport has to offer at this multi-level colonial on cul-de-sac in bucolic neighborhood. There's room for all with the flexible floor plan featuring 4-5 bedrooms including main and upper level primary suites, multiple home office options and terrific storage. On the main level you will find inviting living and dining room spaces with vaulted ceilings which open to the kitchen providing great flow for entertaining. The updated kitchen features granite counters, stainless appliances and breakfast bar. A few steps below are the laundry/mud room and a cozy family room with fireplace and sliders to the screened porch overlooking a deck and wooded property. Also located on this level are the spacious primary or in-law suite featuring double closets and full bath with shower and double sinks. Completing this level are a half bath and flex room, which can be used as an office or 5th bedroom. The upper level, accessed by a short flight of stairs, provides three additional bedrooms; one en-suite, and a renovated full bath. Storage galore can be found in the unfinished basement with cedar closet, extra fridge and access to the two car garage. This lovingly cared for home has been freshly painted inside, has HW floors throughout & numerous new appliances. Centrally located minutes from town, Levitt Pavilion, shopping & restaurants.

Back on the Market - Freshly Updated and Ready for You! Available August 1st, this beautifully maintained 4-bedroom, 2-bathroom ranch offers flexible one-level living in a prime Westport location. With brand new carpeting in the bedrooms, a brand new washer and dryer, and a newly finished sunroom perfect for a home office, gym, or playroom, this rental checks every box. Located on a private street in a quiet neighborhood, this home also offers ample off-street parking and outdoor space ideal for entertaining-just in time for summer! The versatile layout provides options for a fourth bedroom, guest suite, or work-from-home setup. Enjoy the convenience of being within walking distance to Compo Beach and just minutes from downtown Westport and the train. A large attic and shed provide excellent storage, and all appliances have been updated. Don't miss this fantastic opportunity to rent a move-in ready home in one of Westport's most desirable areas. Available August 1st. Security deposit and credit check required.

Nestled on a tranquil lane, this updated 4 bed, 2.5 bath home boasts a modern kitchen with new appliances, cabinets, and a center island. Fresh paint, lighting, and flooring enhance the entire space. Relax in the large private yard or on the new stone patio. Spacious bedrooms with ample closet space add to the appeal. Conveniently located near the Merritt Parkway, YMCA, transportation, and shopping. Don't miss this charming and convenient property. Interior of home has been painted since picture were taken.

Nestled on the coveted Turkey Hill Road S. in the heart of Greens Farms, this impeccably maintained 5BR Colonial offers the perfect blend of classic elegance and modern comfort. Set on professionally landscaped grounds, this home is a true retreat, complete with a Glengate-designed Gunite saltwater pool, spa, and stunning stonework. Inside, the thoughtfully designed layout creates an inviting and sophisticated atmosphere. The gourmet kitchen is a chef's dream, featuring high-end appliances, quartz countertops, a spacious island, a butler's pantry, and ample storage. The sun-drenched living spaces offer seamless flow for both relaxing and entertaining, with refined architectural details throughout. The private primary suite is a sanctuary, boasting two walk-in closets, a dressing area, and a spa-like bath with a soaking tub. Two additional BRs are en-suite, while the other two share a Jack-and-Jill bath, ensuring comfort and privacy for all. The third floor bonus room is a versatile space-ideal for a playroom, media room, or home office. Enjoy summer days by the resort-style pool and outdoor entertaining area, featuring a built-in BBQ, fire pit, and lush surroundings. Located within walking distance of the Greens Farms train station and just minutes from beaches, shopping, and dining, this home offers the best of both privacy and convenience. This exceptional property is available for annual rentals and will also consider summer and short-term options.

Live in style in the Heart of Saugatuck - A Gem of a Westport neighborhood. This may be the perfect blend of comfort and convenience. Meticulously maintained unit, nestled mere minutes from Westport train, shops and restaurants. The freshly painted and deep-cleaned interior space is bathed in natural light, and boasts ample room to entertain or just chill. Also well-positioned to access Westport's vibrant Downtown, famous beaches/tranquil Long Island Sound, Y, public golf course, 95 and the Merritt-this residence is a commuter's dream. The Kitchen is well appointed; LR, BR and Bath are all spacious. And complemented by energy-efficient HVAC systems, including a programmable thermostat, quality dishwasher and conveniently located washer and dryer. All poised to ensure your comfort year-round. Easy to clean and healthy elegance of hardwood and tile flooring creates a timeless appeal. As a resident, you'll benefit from included trash removal and snowplowing, as well as one space in the off-street parking lot, steps from the building front door. Embrace the wonderful cultural amenities the Fairfield County lifestyle has to offer!! Don't miss this exceptional opportunity to make this coastal gem in Mid Fairfield County your new home. The previous tenant stayed for 9 years! Please Note: There is ONE off street parking space with this rental. And the landlord seeks a 2 year lease. Landlord requires applications using RentSpree. Link available in Listing or ask agent.

~HIGH END LIVING~ This home is located in the "Golden Triangle" of downtown Westport. Bedford Square is a unique multi-purpose destination that includes premier residences, beautiful public areas, high-end retail and dining. It is the culmination of the renovation and restoration of the stately 1923 Bedford Mansion and historic Firehouse. Bedford Square is ideally situated in the heart of this vibrant and prosperous community at the foot of Main Street and Church Lane. This luxury rental consists of a one bedroom floor plan and all feature upscale amenities and amazing views. Whether you are looking for an alternative to New York City living or want to downsize, Bedford Square offers a lifestyle of convenience to its residents.

~HIGH END LIVING~ This home is located in the "Golden Triangle" of downtown Westport. Bedford Square is a unique multi-purpose destination that includes premier residences, beautiful public areas, high-end retail and dining. Bedford Square is the culmination of the renovation and restoration of the stately 1923 Bedford Mansion and historic Firehouse. Bedford Square is ideally situated in the heart of this vibrant and prosperous community at the foot of Main Street and Church Lane. This luxury rental consists of a one-bedroom floor plan in the main building/pavilion and four distinct townhomes. It features upscale amenities and amazing views. Whether you are looking for an alternative to New York City living or want to downsize, Bedford Square offers a lifestyle of convenience to its residents.

Rent for a year OR rent for the summer! Come and see this centrally located property, (5 minutes to the beach, 5 minutes to town). Enjoy all that our town has to offer in this spacious home and kick back and have some fun this summer. Flat, fenced in backyard, great for bbq's.Expansive lower level wit TWO separate entrances. Available immediately, furnished or unfurnished Available on a monthly basis for $7000 a month, or grab all 3 summer months for $20,000! Also yearly lease available, for $5900 a month.

***LEASE TERM AUGUST 10, 2025 TO JUNE 20, 2026. FURNISHED*** Enjoy an array of seasonal delights at this wonderful, well-appointed home, beginning with the conclusion of summer when you can enjoy the sparkling pool, pool house, gracious patio w/outdoor fireplace & built-in grill, gorgeous lawns, gardens & more. When autumn's splendor arrives, enjoy the timeless grace of the beautiful interiors - beginning w/casually elegant living & dining rms, a quiet office/library, gourmet kitchen w/Sub Zero & Thermador appliances opening into a stunning breakfast rm which is completely surrounded by tall windows & French doors overlooking the grounds, and a wonderful family rm w/cathedral ceiling, built-ins, French doors to the patio. The BRs include a vltd ceil primary suite w/walk-in clst, balcony, classic marble bath w/dual vanities, glass shower & soaking tub. The remaining BRs are well-proportioned and have accompanying designer baths. The guest/pool house is a delightful surprise w/LR w/fpl, sleeping loft, full bath. Additional comforts include a two car attached garage w/EV charger, generator, and more. The lifestyle extends to the amenities of adjacent Staples High School, where tennis courts and the outdoor track & athletic fields are available after-hours. This is an ideal opportunity to utilize Westport's award-winning education or experience this celebrated community while home shopping in the area. 2.1+/- miles to train.

Dive into the extraordinary at The RiverHouse! Immerse yourself in a world of casual luxury living in this breathtaking boutique home right on the water, where vibrant in-town living comes alive like never before. Imagine yourself aboard a boat, basking in the tranquility of your massive private covered porch-your personal sanctuary! Meet the charming swans, Romeo and Juliet, who nest just below and just welcomed their adorable cygnets. Connect with the beauty of nature and recharge your spirit in this picturesque setting. Picture calling this stunning, pet-friendly, fully renovated cape your home, where every detail has been crafted with your comfort and enjoyment in mind. This luxury apartment is overflowing with features: generous closet space, custom cabinetry, high-end appliances, and the ultimate convenience of an in-unit washer and dryer! Every window offers breathtaking water views that will inspire and delight you. Step outside and find yourself just moments away from captivating restaurants, trendy shops, and exciting entertainment options-all at your fingertips. Ditch the car and dive into the vibrant community that surrounds you. And let's not forget the added perk of garage parking! This beautifully renovated historic building beckons you to indulge in a lifestyle filled with luxury, inspiration, and endless possibilities. Don't let this incredible opportunity slip away!

Set at the end of a peaceful cul-de-sac just off Hogan Trail, this welcoming home offers rare privacy with easy access to everything Westport has to offer. The 0.45-acre property includes a gently flowing backyard stream and a storybook footbridge perfect for quiet moTucked at the end of a quiet cul-de-sac off Hogan Trail, this inviting Westport home offers rare privacy with close access to town amenities. The 0.45-acre property features a gently flowing backyard stream and a charming footbridge perfect for peaceful mornings, outdoor play, or simply enjoying the soothing sound of moving water. Upstairs, the main level includes a bright living room that flows into the dining area, kitchen, and a deck ideal for everyday use or entertaining. Three bedrooms and two full bathrooms complete this floor. The lower level adds flexibility with two more bedrooms, a full bath, a spacious laundry room, and a second kitchen. A large family room with fireplace opens to a private deck. Lower level accessory apartment is now part of the whole-house rental, offering a great setup for guests, extended family, remote work, or recreation. The location combines the comfort of a quiet neighborhood with the convenience of being close to I-95, the train, downtown shops, Saugatuck dining, and Westport's top-rated public schools and beaches. Recent improvements include a new boiler, newer AC/heat pump, and new flooring throughout the lower level.

~HIGH END LIVING~ This home is located in the "Golden Triangle" of downtown Westport. Bedford Square is a unique multi-purpose destination that includes premier residences, beautiful public areas, high-end retail and dining. Bedford Square is the culmination of the renovation and restoration of the stately 1923 Bedford Mansion and historic Firehouse. It is ideally situated in the heart of this vibrant and prosperous community at the foot of Main Street and Church Lane. This luxury one-bedroom duplex home is in the main building/pavilion. It features upscale amenities and amazing views. Whether you are looking for an alternative to New York City living or want to downsize, Bedford Square offers a lifestyle of convenience to its residents. Rental lengths of yearly, two years or more.

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 OR SEPTEMBER. Price is per month starting July 1. A true vacation spot with private beach!

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.