Westport CT Real Estate & Homes for Rent

Looking for the perfect summer getaway? Look right here! Nestled in sought-after Saugatuck Shores, on a secluded cul-de-sac, this charming home boasts 3 bedrooms and 2 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. As a bonus, all utilities and outdoor maintenance are included. ***Leases under 90 days incur a 15% occupancy CT tax on first 30 days***

AVAIL FOR MAY 2024 or SEPT 3, 2024 - JUN 26, 2025 for $15,950/mo. ANNUAL LEASE for SEPT 3, 2024 - SEPT 3, 2025 available for $18,950/mo. Like-new, tastefully furnished Compo Beach gem with private seasonal pool and unobstructed water/park views. Steps to sand/water, ample parking, glass roof deck, 9' ceilings. In the center of all yet private due to its unique configuration & UV floor-to-ceiling windows. Enjoy panoramic 180-degree views of LI Sound from 722 SF glass deck as you lounge. Stroll to Compo Beach & its many amenities. Sunlit views from top level great room with dining and chef's kitchen & spacious MBR suite (comb. twins) which are all steps from the deck. Main level has 3 more ensuite BRS (King as 2nd MSTR, Queen & Twin), laundry room & office/bedroom with kitchenette & stairs to pool. Large Subzero fridge plus fridge drawers, dual-fuel Wolf range, Miele dishwasher, 2nd dishwasher, Legacy solid painted maple Shaker cabinets & quartz counters. All-Clad & Le Creuset etc. cookware. FEMA compliant home has 2 garages, 5 guest parking places, great REC/cabana area (596SF) w/fully retractable glass-paneled door to pool & fenced backyard. Spectacular, pristine home has a versatile floor plan, energy-efficient, low maintenance for carefree seaside living. IMPORTANT. *Leases under 90 days incur 15% CT tax on first 30 days.

Move into Westport and enjoy everything it offers, including Compo Beach this summer! This updated home near Aspetuck Land Trust can be yours. Renovated 4 bedroom 3 bath home allows flexibility of spaces. Enter into a bright space- open floor-plan with a kitchen, family room space (with fireplace) and a dining area. Through the hall find a full bathroom, living room (with fireplace) and bedroom. Upstairs find a primary bedroom which includes a balcony, full bath, bedroom, laundry and homework area. The lower level could function for guests, live in help, playroom, or an office. Convenient to train, town and the beach! EV charger. This is a YEARLY UNFURNISHED LISTING!

Come spend August in the famous Historic District of Westport! Walk to all of Main Street's wonderful shops, cafes and restaurants... hang out at our award-winning library... or take in a play at the Westport Country Playhouse. All of the town's greatest amenities are just a stroll away! This furnished summer rental has 4 bedrooms, 3 full bathrooms, an updated kitchen, and lots of space for everyone. A screened porch is perfect for balmy evenings, while the fully fenced yard is equipped with play equipment and an outdoor dining area. Enjoy Westport's beaches with access to the owners' SUV w/beach sticker, plus bikes, stand-up paddle board, beach chairs, Peloton bike and tread. Rental is for the month of August, but dates are slightly flexible. Dogs accepted on a case-by-case basis. All adult applicants to come through RentSpree.

Westport summer rental. Fabulous location with downtown right outside your door! Walking distance to town, and five minutes to the beach, this home is loaded with charm. This truly unique, artistic in-town home is the perfect summer rental. Plenty of room for the family and guests (sleeps 9), great cook's kitchen with two dishwashers, beautiful master suite, front porch, stone patio terrace with full outdoor seating, zoned central air and walking distance to town! In addition to the garage, there is plenty of paved parking in back of house. Five minutes to beach and Longshore, walking distance to Levitt Pavilion. Flexible lease terms - 1 month minimum, check with agent. King, Queen and Full size beds in bedrooms, and Queen size sleeper sofa in family room. Attic bedroom has twin sleeper sofa and double bed. Dining room seats 8-10, kitchen table and island seats 5-8. Owner reserves one closet in master, exercise room (4th bedroom) and office room will be locked. Available June through Sept. - 1 month minimum with 4 month maximum.

Welcome home! Pristine and fully updated yearly, unfurnished rental in the Greens Farms neighborhood of Westport. Charming 3 bedroom, 2.5 bathroom cape- desirable layout with option for primary bedroom on main or second level. Beautiful & bright kitchen with granite countertops and stainless steel appliances, with a wall of built-in cabinetry/pantry in the adjacent breakfast room. Sliding glass doors lead to the deck with grill, access to the storage shed and one car garage. The private & picturesque yard is lined with stone walls, fencing, pretty landscaping and bluestone walkways-a nice place to relax or play. The lower level has flexible rooms, office and playroom, along with a half bath, laundry and plenty of storage. Bright and sunny den/sunroom, living room with fireplace, and dining room round out the first floor. This is truly a charming home close to everything, including the Greens Farms Metro North train station.

Sophisticated Lifestyle at Sought-after In Town location! Popular restaurants, spectacular shopping and riverside park all nearby. Remodeled from top to bottom! Flexible open floor plan with walls of windows overlooking bucolic brook and level lot. Stylish rooms feature curved window wall and wood burning fireplace in living room. Dining area with French doors overlooks lawn. Newly remodeled kitchen includes breakfast bar and access to private rear patio by the brook - an ideal spot for your morning coffee! Spacious first floor primary suite includes new full bath. Upper level features 2 Bedrooms, remodeled full bathroom, laundry area and access to private balcony deck. Yearly unfurnished rental available for multiple years. No Smoking. References required.

This sundrenched end unit is located in Whitney Glen condominiums, a complex for ages 62 and older. This 2nd floor unit has vaulted ceilings in LR, DR & MBR with Clerestory windows for spacious feeling and lots of natural light. The eat-in kitchen has stainless appliances and newer granite counters. The master bedroom has a full bath and walk-in closet. The spacious second bedroom has the second full bath adjacent to it. This unit has a covered porch overlooking the scenic private property, with room for table and chairs - perfect for dining alfresco. Additionally, there is an in-ground salt water pool and pool house in the complex. The assigned parking spot is directly in front of the unit, plus there is visitor parking close by. Private storage room in basement plus pull down attic in the unit. Walk to downtown, the Senior Center, the library plus CVS and Trader Joes. Enjoy all Westport amenities: beach, golf, tennis, etc. At least one occupant must be 62 yrs. or older. Available for yearly rental, beginning June 1. Owner prefers 2 year lease. Good credit a must. New carpet is scheduled to be installed prior to occupacy. Owner is a licensed real estate agent. Photos taken prior to this tenant

18k for 4 weeks; 20k for 5 weeks.

~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. The luxury rentals consist of one and two-bedroom floor plans in the main building and four distinct townhomes. 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. We can arrange terms of yearly, two years or more.

Let's extend SUMMER! Step into your ultimate rental oasis tucked away in a serene cul-de-sac, boasting over 3100sf of luxury living. This meticulously cared-for property boasts 4 bdrms/3 full bths, ensuring every inch is dedicated to relaxation & enjoyment. Be swept away by the majestic views of Signal Lake from your sprawling multi-level deck, setting the scene for endless adventures in kayaking, canoeing, paddleboarding. Lose yourself in the tranquility of the surroundings, all while being just a stone's throw away from the sandy shores of Compo Beach & a mere 3-minutes to Westport Train. There's more! The heart of this haven lies in its extraordinary chef's kitchen. Entertain guests in style as the open layout seamlessly connects the kitchen to the living spaces. As the temp. drops, cozy up by the newly appointed fireplace, a perfect spot to watch the vibrant autumn hues unfold. Explore all that Westport has to offer-from the sun-kissed shores of Compo Beach to the vibrant pulse of Main Street's charming shops & delectable dining options. Easy access to Longshore Club, Levitt Pavilion, Sherwood Island & Burying Hill beaches, the adventures are endless. Don't let this opportunity slip away! Experience the ultimate autumn escape, where nature's beauty harmonizes w/ the comforts of home. Whether it's lounging on the dock w/ a good book, savoring sunsets at Compo Beach or embarking on a paddle boarding expedition down the river, this home is your ticket to retreat and relax!

Welcome to The Sherwood Cottage! DIRECT WATERFRONT rental with breathtaking views over Sherwood Mill Pond and just steps to the golden sandy beach at Old Mill. Featured in Connecticut Cottages and Gardens, the current owners worked with noted architect Robert Dean in 2018 to raise the home and superbly redesign, and reimagine, this darling 1900s oyster shack - creating an idyllic beach oasis. As you enter the home you will be wowed by the gorgeous open-plan living space, comprising styllishly renovated kitchen, dining room and living room where contemporary design blends seamlessly with charming coastal cottage! Amazing, folding glass NanaWall at the back of the house opens completely to the balcony, creating an incredible feeling of being at one with water and nature. Let the sea breezes embrace you! And at the end of a long day of fun in the sun, head upstairs to find all three bedrooms, 2 full baths and laundry. Primary bedroom is ensuite with balcony overlooking the pond and the other two bedrooms have a balcony with views over the beach and LI Sound. Launch your kayaks and paddleboards right off the back of the house and rinse off in the outdoor shower when you're done! Also enjoy all the nearby amentities of Longshore Club Park - golf, tennis, sailing, outdoor pools, pickleball and dining at La Plage. Available as a yearly furnished rental from May 1st at $12k/mth Also available as Summer rental July/August at $19,500/mth (min 2 months).

This luxurious Antique Colonial is available for lease during the academic year/as a winter furnished rental. 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.

Walk to train, located in Stoney Point Association, Open Floor Plan, Hardwood Floors, Viking Appliances, Center Island, Kitchen opens to Family Room, Large Deck overlooks Private one acre partially fenced in yard. Mature plantings on lovely grounds with Napoleon Outdoor pizza oven. Beautiful condition. New Driveway. Refinished hardwood floors. Walk to Shops, Restaurants, Park and Train Station. Enjoy private one acre yard and center of town living. Near Beach, Golf, Tennis and walkable to water. Dog will be considered on case by case basis and must meet owner's agent. This home is a real pleasure to Show. See article on area schools in addendum.

This stunning custom 6-bedroom home, located on one of the most prestigious cul-de-sacs in Westport, embodies the best of casual elegance and masterful design. This exceptional residence, sited on magnificent property, is available for annual rent, and also for summer enjoyment with a 3+ month summer term preferred. Designed by the acclaimed Pagliaro Bartels Sajda Architects, the home boasts an open floor plan that incorporates luxury and beauty into every room, creating a versatile modern home that's perfect for informal entertainment and cosmopolitan sophistication. The backdrop of nature in an unbelievable setting enhances the ambiance of this home, and gorgeous fireplaces, built-ins, glass walls, and spectacular light through multiple huge windows create a seamless flow for true indoor/outdoor living. Almost every room offers stunning views of the beautifully landscaped property, gunite pool & spa. The remarkable architectural and custom details throughout the home, the full home generator, the security system, the home entertainment system, and many other features make this home truly unique. Walk to schools, as well as Wakeman Town Farm and a local market/coffee shop/restaurant. Close to beautiful Westport beaches, golf, horseback riding, the town center, fabulous restaurants, and only a 1-hour express train ride to NYC! Furnished year rental $35k, unfurnished year rental $30k, summer months $55k/month.

This stunning custom 6-bedroom home, located on one of the most prestigious cul-de-sacs in Westport, embodies the best of casual elegance and masterful design. This exceptional residence, sited on magnificent property, is available for annual rent, and also for summer enjoyment with a 3+ month summer term preferred. Designed by the acclaimed Pagliaro Bartels Sajda Architects, the home boasts an open floor plan that incorporates luxury and beauty into every room, creating a versatile modern home that's perfect for informal entertainment and cosmopolitan sophistication. The backdrop of nature in an unbelievable setting enhances the ambiance of this home, and gorgeous fireplaces, built-ins, glass walls, and spectacular light through multiple huge windows create a seamless flow for true indoor/outdoor living. Almost every room offers stunning views of the beautifully landscaped property, gunite pool & spa. The remarkable architectural and custom details throughout the home, the full home generator, the security system, the home entertainment system, and many other features make this home truly unique. Walk to schools, as well as Wakeman Town Farm and a local market/coffee shop/restaurant. Close to beautiful Westport beaches, golf, horseback riding, the town center, fabulous restaurants, and only a 1-hour express train ride to NYC! Furnished year rental $35k, unfurnished year rental $30k, summer months $55k/month.

This stunning custom 6-bedroom home, located on one of the most prestigious cul-de-sacs in Westport, embodies the best of casual elegance and masterful design. This exceptional residence, sited on magnificent property, is available for annual rent, and also for summer enjoyment with a 3+ month summer term preferred. Designed by the acclaimed Pagliaro Bartels Sajda Architects, the home boasts an open floor plan that incorporates luxury and beauty into every room, creating a versatile modern home that's perfect for informal entertainment and cosmopolitan sophistication. The backdrop of nature in an unbelievable setting enhances the ambiance of this home, and gorgeous fireplaces, built-ins, glass walls, and spectacular light through multiple huge windows create a seamless flow for true indoor/outdoor living. Almost every room offers stunning views of the beautifully landscaped property, gunite pool & spa. The remarkable architectural and custom details throughout the home, the full home generator, the security system, the home entertainment system, and many other features make this home truly unique. Walk to schools, as well as Wakeman Town Farm and a local market/coffee shop/restaurant. Close to beautiful Westport beaches, golf, horseback riding, the town center, fabulous restaurants, and only a 1-hour express train ride to NYC! Furnished year rental $35k, unfurnished year rental $30k, summer months $55k/month.

Enjoying tranquil views of the river and waterfall, this exquisite home offers a private retreat, minutes from town. Open and airy living spaces include a great room with soaring ceilings and a stone fireplace, a brilliant sunroom and a well-appointed home office with river views. The chef's kitchen is home to a spacious island, professional appliances and a butler's pantry. Relax on the sun-drenched terrace or by the swimming pool and spa. Upstairs, unwind in the primary suite with a private balcony and spa bath with a steam shower and soaking tub. A finished third level offers space for a game room or playroom, as well as a home gym, and the main level guest suite is perfect for an in-law or au pair. Available for rent June 22, 2024 - July 14, 2024 ONLY.

~HIGH END LIVING~ This Two Floor Duplex 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 duplex rental consists of a two-bedroom, two floor plan in the main building. All feature upscale amenities and amazing views. There is an elevator just for this unit, to access the main and upper floors of the apartment (ADA compliant). 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. Terms of yearly, two years or more. A walk through video is available upon request.

Welcome home to Sue Terrace. This completely renovated colonial boasts 4BR/3FB and is being offered as a yearly, furnished (or unfurnished) rental. The term includes 4 summer months (July/August 2024 and May/June 2025) to enjoy at Compo Beach Park or Longshore pool, golf and tennis. This family home is centrally located in Westport and walking distance to shopping (Fresh Market, CVS, Trader Joes) Winslow Park and restaurants such as Terrain and Sakura. Prefer to entertain at home? 16 Sue Terrace has an open floor plan, high cathedral ceilings, a sunroom, and a private backyard with patio, outdoor kitchen and shared basketball hoop. Sue Terrace is a private cul-de-sac where everyone is welcome and many come to stay.

Spectacular, sundrenched home overlooking the beautiful Aspetuck River with a heated gunite swimming pool. Home was totally renovated and upgraded in 2015 and is available for immediate occupancy. Privately situated on 8 acres, yet conveniently close to all that Westport has to offer. The home has over 8000 sq ft on just two floors with 5 bedrooms, 6 full and one-half baths. The layout also offers the option for multi-generational living with bedrooms both on the first and second floors, multiple rooms for offices, 3-car garage, plentiful parking, and so much more. Main floor is 4900 +/- sq ft all on one level with an additional 2400 +/- on the second floor, and a large recreation/media room space of 870 +/- sq ft over the 3-car garage. Features include: Great room with floor to ceiling stone fireplace, vaulted ceiling and French doors leading to large blue stone patio plus deck, large gourmet kitchen with two islands, huge recreation/media room over the garage, sumptuous primary suite with 2 bathrooms, walk-in closets and private balcony with a view of the river, hardwood floors throughout, heated swimming pool, sauna, central air conditioning, whole house generator ...and so much more. Natural gas for heating, cooking, generator, and pool heater. Landlord pays for swimming pool and generator maintenance.

Come enjoy JULY in your very own Country Club with pool and tennis court! Experience one of Westport's most coveted neighborhoods tucked away with a sense of privacy near a 16 acre park/nature preserve, yet centrally located to town, train and Compo Beach. This light filled open floor plan contemporary home has been renovated with all new upgrades and a sleek modern design with soaring ceilings and walls of windows. The downstairs primary bedroom has a luxurious bath and the three additional bedrooms upstairs all have their own baths and a playroom/office that could function as a fifth bedroom. All you need to pack is a bathing suit and sneakers! Available July 1 - July 31

TOO GOOD TO BE TRUE! Once you turn the bend on Harbor Road it is like a retreat in the fabulous town of Westport! This gorgeous 3 bedroom, 2.1 bath with a sleeping loft is relaxing in a gorgeous beach community. If you always wanted to try beach living this is the place for you. The entire house is sun-drenched and has water views from almost every room! This home also boasts a stone patio and outdoor fireplace for family and friends to gather. Saugatuck Shores beach community is a fun and friendly neighborhood. -- The property is close to Saugatuck Rowing Club which has a beautiful fitness facility and restaurant. It is super easy to commute from the train station away from the traffic. Close proximity to other fabulous restaurants like Tarantino's, Gabriele's and The Whelk to name a few. Best of all is this home has front row seating on an amazing deck overlooking the water to the 4th of July fireworks celebration. - Imagine waking up to a full view of the sunrise every morning! Come and take a walk along the sound with a beautiful view of the lighthouse and relax and the beach. A moment of zen in the heart of Westport Connecticut!

Life's a beach! Dive into coastal living with this completely renovated 3-bedroom, 1-bath beach bungalow at Comp Beach. Beautifully finished wood floors throughout, complemented by an inviting open floor plan featuring a cozy fireplace and gourmet kitchen perfect for entertaining. The kitchen opens to a private oversized backyard with a charming bluestone terrace and refreshing outdoor shower"ideal for rinsing off after a day of sun and sand. Enjoy year-round relaxation in the screened-in porch, and with a 1-car garage and 2 driveways. Ready to make waves? Grab your towel, sunscreen, and make this your home sweet home!

Fully Furnished, Summer Rental. WATERFRONT PARADISE! Tranquil location offers unrivaled access to Panoramic Ocean views of Long Island Sound. A short walk across the Wooden Footbridge w/ Sherwood Mill Pond on your left and LI Sound on your right leads to the gated private Island of Compo Mill Cove & a handful of unique waterfront homes. The property itself has been customized from top to bottom w/ exceptional thought & detail. Only house on the Cove w/ a secure, storm surge concrete wall. Featuring over 3950 sq ft of living space, 5 beds, 5.2 baths, an open floor plan w/ wall to wall windows that offer 180 degree views of the ocean from every room. First fl features a living room w/ fireplace, family room, beautifully appointed wet bar, dining area, & gourmet kitchen w/ exclusive granite, Viking appliances, modern design, & a first fl bedroom w/ ensuite bath. Upstairs offers 3 additional bedrooms including a primary w/ a fireplace, private balcony w/ outdoor fireplace, & bathroom w/ sauna shower, tub, & double vanity. The highest quality materials were used in every corner of the home, from beautiful marble to custom imported Italian sici tiles, to state of the art electronic & digital components that can be used from within the home or remotely no detail was overlooked. Outdoors is equally as impressive w/ an infinity pool, outdoor kitchen, shower, terrace w/ fireplace, lush gardens, & impeccable landscaping that sit behind a gated, secure stone wall border. 1 hr from NYC