111 houses for rent in Cannondale, Wilton town Fairfield County Connecticut

Welcome to Bronson House, Greenfield Hill's premier luxury rental, where elegance meets modern comfort in a serene, private setting. This highly efficient two-bedroom, 2.5-bath home offers exquisite living designed for discerning tenants who crave sophistication and convenience. Featuring cutting-edge SMART home technology, experience seamless, maintenance-free living at its finest. Nestled on the 2nd and 3rd floors with easy elevator access, this sun-drenched, expansive residence boasts a thoughtfully crafted open floor plan and in-unit laundry for ultimate convenience. The stunning primary suite on the main level invites you to enjoy the ease of one-level living, while the upper floor reveals a spacious second bedroom, a luxurious full bath, a walk-in closet, plus a versatile sitting room or office space perfect for remote work or relaxation. Immerse yourself in the charming lifestyle of Greenfield Hill with desirable local amenities just steps away, Greenfield Hill Cleaners, Greenfi

Imagine being able to view one of the town's loveliest Formal Gardens, from huge windows, throughout this stunning Mid-Century Modern home. Nestled tranquilly on a park-like private cul de sac, in Westport's highly-sought Coleytown neighborhood. 8 Bayberry Ridge is minutes from the Merritt and multiple Train stations. Become a resident of the Westport, CT community! Enjoy its pristine Beaches, superb public Golf course, upscale shopping, and thriving cultural life. This home offers 3,300 SF of Open, High-Ceilinged and Light-Filled space. The Kitchen/Living Room, with its charming timber beams, is one of several distinct and unique interior environments-all seamlessly connecting with the spectacular, Four Season Garden views, creating a colorful and ever-changing visual display from inside the home. Indulge in the Great Room with soaring Cathedral ceilings. Unwind in the Solarium, or take a refreshing dip in the Indoor Pool-ideal for year-round relaxation, fitness, and entertaining. The

Welcome to an exceptional opportunity in The Cove! This rare four-bedroom, three-and-a-half bathroom townhouse offers over 2,500 square feet of beautifully designed living space in desirable neighborhoods. Enjoy the luxury of a custom white kitchen with quartz countertops, stainless steel appliances, and natural gas cooking. The open-concept layout is perfect for entertaining, with a private outdoor area ideal for barbecuing and gatherings. Additional features include a one-car attached garage, visitor parking, and modern comforts like natural gas heat and air conditioning. Located just a short walk to the water, scenic parks, and convenient public transportation, this home truly combines lifestyle and location. Opportunities like this don't come often

Lovely, freshly updated second-floor studio apartment in a prime Bethel location. This bright and charming unit features fresh paint, brand-new flooring, a brand-new range, and an included window AC unit. Enjoy the ultimate convenience of having a newer washer and dryer right inside the unit. Situated upstairs from the landlord, this property is a commuter's dream, located close to the Bethel Train Station and close to everything downtown Bethel has to offer. Tenant is responsible for credit report, background check, electric, renter's insurance, and snow removal. Move-in ready and waiting for you!

A quiet country lane near the Lake Club (pool lake and tennis club) introduces this lovely Colonial set back on a beautiful, level property. The desirable open floor plan encompassing a warm and inviting kitchen and family room w/ a stone fireplace encourages lingering and relaxation. The gracious living room also with a fireplace and an expansive dining room are perfect for more formal entertaining. A large bonus room, 1st floor office, laundry and mudroom complete this level. The master suite enjoys a full bath and walk-in closet. Down the hall are three additional bedrooms and large hall bath. Finished walk-out lower level. Convenient location

8 Sherwood Drive, Westport. Enjoy the best of the Westport lifestyle in this charming rental, ideally located in one of the town's most sought-after neighborhoods. Just a short stroll to picturesque Old Mill Beach and moments from vibrant downtown Westport, this home offers the perfect blend of coastal living and everyday convenience. A welcoming sunroom greets you as you enter, filling the home with natural light and creating the perfect space to relax or entertain. Sun-drenched rooms, hardwood floors throughout, and a thoughtfully designed layout make this home warm and inviting. The main level also features a bedroom and a full bath, offering flexibility for guests, a home office, or convenient one-level living. The finished lower level provides additional living space ideal for a family room, recreation area, gym, or playroom. Step outside to a private backyard with a charming deck and pergola, perfect for outdoor dining or relaxing. Enjoy easy access to all of Westport's amenities

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, sleep

Yearly rental in long lots school district: welcome to a private and spacious 4-5 bedroom, 3.1 bath Colonial, offered as an unfurnished, yearly rental. The main level has an inviting foyer open to the living room, and down the hall is the gourmet kitchen with a peninsula that seats 2-3 plus an adjoining family room with wood burning fireplace. The family room has sliding glass doors that open to a large deck overlooking the private backyard. The sun-lit dining room with gleaming hard wood floors, plus half bath, complete the main level. The second floor has a spacious primary suite with a large walk-in cedar closet and full bath with soaking tub and shower. Just down the hall are 3 additional bedrooms with 2 full baths, along with an office (or 5th bedroom). One of the guest bedrooms is ensuite. Off the kitchen is the daylight walk-out lower level which has been smartly finished with engineered wood flooring, sound proof walls/ceiling, a laundry room plus storage. The 2 car garage is o

Furnished Short Term Rental with dramatic views of the Long Island Sound and pool at one of the areas premier addresses. Steps To Compo Beach and Longshore Country Club. Located on prestigious Bluewater Hill, this home is part of association with deeded Beach rights and Tennis courts. This home offers 4 bedrooms, 3 full baths, flexible floor plan with great entertaining areas, outdoor patios and property. Available after 10/15/26

Come live your best Summer at the Beach. Just steps from a private deeded beach that you share with 12 houses at the end of a quiet dead end street. You can soak up Summer everyday by paddle boarding to a sandy beach island off the coast (2 paddle boards included). This gorgeous updated five bedroom property is an entertainer's dream and a retreat for those who want to get away to relax, while only being 1 hour away from NYC. Inside you can enjoy beautiful water views from almost every room in the house. The heart of the home is an open concept space with a chef's kitchen, casual living area with a wood burning fireplace and a dining area to provide the perfect place to gather. Sliding doors lead to the expansive deck that provides an area to sip morning coffee, watch tv, grill out for dinner and dry off after a dip in the jacuzzi. Corn hole, volleyball net, Giant Jenga, bikes, fire pit, numerous lounging options, outdoor TV, grill and dining table provide amble ways to enjoy the backy

Wake up to breathtaking sunrises over the Westcot Beach water views. This beautifully renovated 3 bedroom 2 1/2 baths apartment, is perfectly positioned in a quiet Shippan Point's neighborhood. The light filled living area is enhanced by fireplace and dining area. The modern kitchen features quality appliances (new refrigerator and water filter) ample storage and generous counter space. A sliding door leads to private terrace creating a calm and inviting atmosphere for family BBQs and entertainment. Heat, and hot water is included in the rent. Located few minutes from shops, restaurants, marinas, parks and public transportation. 35 miles from NYC, 7 minutes to RR station and less to I95 entrance. Enjoy morning walks along the water front and easy access to what the neighborhood has to offer

Available from 8/9/26. 9/9/26 with possibility of extending through September and into October. Enjoy your summer at this wonderful Greens Farms Colonial. What a perfect spot to come home to, after a day at the beach! Spend your evenings on the screened porch & in the festive, private back yard with a great patio featuring multiple seating areas, fire pit, hot tub (with outdoor smart TV) and swing set. The main level offers a living room complete with a comfortable TV area, a spacious country Eat-in Kitchen plus a Home Office. No need to travel to work from here! 3 sweet Bedrooms upstairs share a bath. The Primary has a king sized bed. One Bedroom has a twin with a trundle bed that opens to a king. The other has two twins and one twin has a trundle. The lower level offers a Home Theater, complete with recliners, plus the laundry. Detached Garage has been converted to an Entertainment/Lounge/Game Room with smart TV, piano and more! Owners reserve walk-up attic for their belongings. Just

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

Welcome to 63 Kings Hwy North in Westport! A yearly furnished rental with an inviting front porch welcomes you home to this light-filled historic four bedroom cape within walking distance to the wonderful town of Westport. The front to back living room boasts a wood burning fireplace for cozy evenings and a large dining room is great for entertaining family and guests. The renovated kitchen will delight the cook in the family. Spend time on the back patio overlooking a large open garden area. Enjoy all that Westport has to offer its' residents, to include exceptional public and private schools. Enjoy the Longshore Golf Course, the Longshore Club Park with three pools and tennis courts. Compo Beach for summer fun. The Westport Playhouse. And a walking riverfront downtown featuring gourmet restaurants and boutique shops. All this within one hour to NYC. Owner prefers to rent the home furnished yearly, but could be available unfurnished for $6,500 per year, or ask about for six months

Beautifully designed for effortless living, this light-filled and airy home at 20 Grassy Plains blends luxury, comfort, and convenience in one exceptional offering. Featuring a highly sought-after first-floor primary suite, this residence is ideal for both everyday living and long-term flexibility. An elevator connects multiple levels, providing ease and accessibility throughout the home, along with a finished basement offering approximately 1,500 square feet of additional living space. The open-concept floor plan is enhanced by abundant natural light, soaring ceilings, and seamless indoor-outdoor flow. The chef's kitchen is equipped with top-of-the-line appliances, custom cabinetry, and premium finishes, opening beautifully to the main living and entertaining spaces. Step outside to a spacious deck perfect for outdoor dining, relaxing, and entertaining guests. Thoughtfully designed with both elegance and practicality in mind, this home offers modern luxury, low-maintenance living, and

Summer furnished rental! Come out to the country and enjoy this beautifully updated, spotless and spacious colonial style home, fully furnished for all your needs. Plenty of room to work remotely (upstairs or on the first floor) and a large level backyard to enjoy the outdoors. Enclosed porch and large patio overlooking gorgeous and private back yard. Convenient to Wilton center, take a train to NYC, enjoy Merwin meadows lake and playground with the little ones, 15 minutes to Westport beaches or walk the Norwalk valley river trail. Room for four people to relax and enjoy the summer months. First floor has living room with fireplace, office with beautiful windows to view the outdoors, stunning new eat in chefs kitchen as well as formal dining room. Large family room is bright with cathedral ceiling and two desks for remote learning. Finished lower level recreation/play room has ping pong table and play area. Term is flexible!

This modern farmhouse was recently completed 2019 with highest level of craftsmanship, stunning interior and exceptional modern design. Covered front porch with seating area welcomes you and leads to grand front door entry with two-story foyer. Sun-filled open floor concept 9ft+ ceilings, white oak flooring and contemporary vibe. Fully furnished with essentials and many extras(bikes, scooters, and more). Custom kitchen/family room with marble counters, shiplap ceilings, a center island with breakfast bar, dining area, and a gas fireplace. Large barn doors from the family area lead to a formal living room that can be closed for quite time or opened for entertaining. The formal dining room, office, mudroom, and two half-baths are located on the first floor. A beautiful master suite with sitting area, x-large walk-in closet, and a luxurious marble bath is located on the second level. There are four additional bedrooms, one with en-suite bathroom and the other two sharing a Jack and Jill b

Available from 8/9/26. 9/9/26 with possibility of extending through September and into October. Enjoy your summer at this wonderful Greens Farms Colonial. What a perfect spot to come home to, after a day at the beach! Spend your evenings on the screened porch & in the festive, private back yard with a great patio featuring multiple seating areas, fire pit, hot tub (with outdoor smart TV) and swing set. The main level offers a living room complete with a comfortable TV area, a spacious country Eat-in Kitchen plus a Home Office. No need to travel to work from here! 3 sweet Bedrooms upstairs share a bath. The Primary has a king sized bed. One Bedroom has a twin with a trundle bed that opens to a king. The other has two twins and one twin has a trundle. The lower level offers a Home Theater, complete with recliners, plus the laundry. Detached Garage has been converted to an Entertainment/Lounge/Game Room with smart TV, piano and more! Owners reserve walk-up attic for their belongings. Just

Call this property home and enjoy year long views overlooking the private pond and panoramic back yard. This home comes complete with everything you need to enjoy the peace and quiet, or entertain with this open floor plan offering great space on the main level and lower level finished basement, complete with walkout to the back yard, fireplace, and full bath. My favorite part of the house is the 3 seasons room off the kitchen and the living room, which has great energy as a place to enjoy meals, or have your morning coffee and the look out over the peaceful surroundings of the home. House was fully updated with new kitchen and baths in recent years and offers a great living space. Current tenant in process of moving out. Will be fully out by the end of the month

This beautiful & modern country home has it all! Privately situated down a country lane, you'll enjoy newer construction featuring a sunny open flow of rooms with hardwood flooring, vaulted ceilings, sliding French doors and patio! An open kitchen with breakfast bar looks on to the living/dining space, lined with windows and enhanced with a stunning stone fireplace & vaulted ceilings. Upstairs you'll find a surprisingly large primary bedroom with room for your home office/exercise equipment, second bedroom & large spa-inspired full bath with separate tub and shower. There are so many places to enjoy the bucolic scenery of trees, rolling hills & birds, come see this very special home. Must have confirmed appointment. Tenant is responsible for lawn maintenance, landlord will manage snow removal

Fully Furnished Seasonal Rental in Westport. Fall 2026 through Spring 2027 Fully furnished contemporary home located on a quiet cul-de-sac, minutes from downtown Westport, beaches, and restaurants. Offering 4 bedrooms, 3 full bathrooms, and 4,711 sq ft of living space, this home features an open floor plan with high ceilings, oversized windows, and a double-sided brick fireplace. The property includes a fully equipped kitchen with stainless steel appliances, gas range, and heated wood floors, a formal dining room, two living areas, and a welcoming foyer with a piano. The lower level offers a recreation room with ping pong, toys, books, and fitness equipment, while the primary suite features a soaking tub, heated floors, and a walk-in closet. Additional amenities include central air, an attached two-car garage, public utilities, a porch, deck, gas grill, outdoor seating, and a full-house automatic backup generator. Close to Sherwood Island State Park, golf courses, tennis courts, and to

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

Escape to your own private sanctuary in this sun-filled, flexible layout home located in the highly desirable In-Town neighborhood, close to all of Westport's amenities. Offering a rare blend of dramatic natural beauty and everyday convenience, this property features breathtaking, unobstructed views of a waterfall on Lee's Pond, which flows directly into the historic Saugatuck River. This is a 5-bedroom house (3 bedrooms have the waterfall view) with an upstairs playroom. 2 of the 5 bedrooms have their own den area and a full bathroom-including a back staircase providing a separate living area with great privacy and independence for guests, an au pair, or in-laws. Launch your kayak right from your backyard and enjoy a scenic paddle directly into vibrant downtown Westport. Enjoy shopping, dining, and community events just minutes away. Host unforgettable summer cookouts on the patio while relaxing to the serene, soothing sounds of the waterfall

An exceptional opportunity to rent the main private residence of a spectacular waterfront home in Westport. Set along the Saugatuck River and including a pool, this tastefully renovated home in a prime location invites you to experience the very best of Westport living. Offering 4 bedrooms and 3.5 baths, the home provides generous space for comfortable everyday living. Thoughtfully designed work-from-home options allow for privacy and productivity, while a loft flex space and fully finished lower-level offer options for a playroom, gym, additional office and more. The home is beautifully appointed with a gourmet kitchen, luxurious baths, welcoming balconies, hardwood floors, and designer fixtures and finishes throughout. Available fully furnished, every space feels curated, comfortable, and effortlessly elegant. Outside, the waterfront living unfolds in every season allowing you to enjoy panoramic views of the river flowing through downtown and out to Long Island Sound. Quiet and priva

Recently updated! Well maintained charming 3-4 Bedroom, 2 Full Bath rental available for October 1, 2026. 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 newish stainless steel appliances, new countertops and hardware that opens up into the Dining area and the Living Room. There are 3 Bedrooms on the second floor. On the third 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, newish vanity and shower. Hardwood floors in all rooms except for the lower level. The screened-in porch has a new tiled floor. The porch and deck of