luxury properties for rent Connecticut, United States

Discover the perfect blend of antique charm and modern convenience at 50 Ledge Hill Road. This delightfully updated and maintained antique colonial is available for annual rental, offering a truly peaceful and picturesque retreat on six and a half acres of serene land. Despite the feeling of total privacy and seclusion, you'll remain conveniently located within a fifteen-minute drive of all local amenities. The home features three bedrooms and one and a half baths along with ample living space: a dedicated living room, a comfortable family room, an office, and a den, providing flexibility for working from home or hosting guests. The charming, eat-in kitchen is pleasantly sized, perfect for casual, everyday dining or holiday gatherings. Step outside and enjoy the expansive, sprawling backyard, featuring an inground pool for fun all summer long. The home also features brand-new central air conditioning and landlord-maintained solar energy and professional landscaping. With its blend of historic character, abundant space -inside and out, wonderful amenities and prime location, 50 Ledge Hill Road is a renter's dream. Don't miss this unique opportunity-schedule your private tour today.

DIRECT WATERFRONT with unobstructed views of Long Island Sound. LIFE IS BETTER AT THE BEACH. Available for the month of June. Amazing home to gather with friends and family offering large open floor plan, 5 bedrooms, large 3rd floor rec room, porch for al fresco dining...Don't feel like cooking? Head over to the Madison Beach Hotel & treat yourself to cocktails, lunch, dinner with amazing views. Life is Short...Enjoy Madison at its finest.

Instantly inviting this circa 1940 's classic Connecticut cottage also known as Little Fox Farm is brimming with character and jewel like qualities on nearly 3 acres a wonderful mixture of meadows, light woods, and mature trees as well as stunning perennial flower gardens developed over 30 years by its owner a designer. Set back on the property the house is in mint condition with beautiful wood floors really celebrates the natural light in every room and enjoys woodland and meadow views with peeks at gardens right outside the windows. The Living room is open to both the formal dining room with a gas fireplace and the recently updated the kitchen. Two stone patios one in the front of the house and another in the rear of the house create private places to relax or entertain or just soak up the lovely scenery at different times of day. The primary bedroom is a quiet private suite at the back of the house There is a small bedroom also used as an office. There is a mudroom with laundry. The property features a very detailed designed horse barn that stuns in it beauty yet is also completely functional for a very happy horse or used as an art studio, office, guest quarters. The two car detached garage a quick walk from the house is actually pretty and has a large finished storage space. There is room for a pool or expansion of the house. Only once in a blue moon does such a dreamlike romantic property come to the market!

Enjoy direct waterfront living in desirable Stony Creek with sweeping views of the Thimble Islands and Long Island Sound. This fully furnished, renovated home features an open floor plan with a spacious kitchen, dining area, and great room, all designed to capture the water views. The main level includes a sitting room and half bath. The second floor offers a primary suite with full bath and water views, a guest bedroom with en-suite bath, two additional bedrooms, and a third full bath. Hardwood and tile flooring throughout. Outdoor features include a front porch and patio overlooking the water. A gently rolling lawn transitions to a natural stone shoreline, complete with a private dock ideal for small watercraft. Located in Stony Creek Village near shops, restaurants, hiking trails, and the Legacy Theatre. Just minutes to downtown Branford, 10 minutes to New Haven, and approximately 75 miles to NYC. Spend the month of August in this beautifully appointed home, ideally located to enjoy all that the shoreline has to offer. Available for August rental at $20,000. Also available for academic rental.

Direct Waterfront Academic Rental in Stony Creek Available 9/1/26 - 5/31/27 Enjoy direct waterfront living in desirable Stony Creek with sweeping views of the Thimble Islands and Long Island Sound. This fully furnished, renovated home features an open floor plan with a spacious kitchen, dining area, and great room, all designed to capture the water views. The main level includes a sitting room and half bath. The second floor offers a primary suite with full bath and water views, a guest bedroom with en-suite bath, two additional bedrooms, and a third full bath. Hardwood and tile flooring throughout. Outdoor features include a front porch and patio overlooking the water. A gently rolling lawn transitions to a natural stone shoreline, complete with a private dock ideal for small watercraft. Located in Stony Creek Village near shops, restaurants, hiking trails, and the Legacy Theatre. Just minutes to downtown Branford, 10 minutes to New Haven, and approximately 75 miles to NYC. Utilities not included. Spend the month of August in this beautifully appointed home, ideally located to enjoy all that the shoreline has to offer. Available for August rental at $20,000.

WATERVIEW SUMMER RENTAL AVAILABLE FOR JULY ONLY as August is now rented. This quintessential Seasonal Beach Cottage with WATER VIEWS is special The views out over Long Island Sound AND a wonderful wraparound South facing Open Porch to catch the summer breezes are both part of this charming Cottage, located directly across from the very desirable private Overshore (SANDY) Beach Association with it's large grass play area, boardwalk, gazebo & even a raft!, Besides the water views from every room, a light & bright open floor plan, high ceilings, a small but cool sleeping porch/room, new ceiling fans, updated Bathrooms, full size washer & dryer and an outside hot/cold shower, the Kitchen has granite counters, stainless appliances including a dishwasher & a butler's pantry. Also OFF SEASON in May & June or September & October possible too at a lesser rate. One time $350 cleaning fee. Sleeps 9.

Embrace the serene beauty of Middle Beach with this exquisite academic rental, available from September 15th through May 15th, 2027. This direct waterfront property offers a tranquil retreat with open-concept living and breathtaking views of the water. The main level is designed for comfort and elegance, featuring a cozy gas fireplace, an updated kitchen with modern amenities, a convenient dry bar, and the first of three full bathrooms. As you ascend to the second level, you'll find four well-appointed bedrooms and two additional full baths, ensuring ample space to comfortably accommodate six guests. Wake up to the soothing sights of the shoreline in the primary bedroom, which boasts panoramic water views, a spacious walk-in closet, and an en-suite bathroom equipped with a stall shower and double sinks. The third floor unveils a hidden gem: a deck and office nook that present the ideal vantage point for witnessing the captivating sunsets that Middle Beach is known for. This space provides a peaceful haven for work or relaxation, enveloped by the natural splendor of the coast. While some pets may be considered, please note that cats are not permitted. This property is a rare opportunity to experience coastal living at its finest during the fall, winter, and spring months. Don't miss the chance to call this waterfront haven your temporary home.

Enjoy the best weeks of summer in Madison in this exceptional, academic rental! Available August 10th, this beautifully-crafted residence offers the ideal blend of comfort and tranquility, just minutes from the shoreline and town center. The thoughtfully designed interior features a welcoming living room with gas fireplace, creating an inviting atmosphere for evening reading or entertaining family and friends. The well-appointed kitchen with custom cabinetry and granite countertops flows seamlessly into a charming dining area -perfect for hosting gatherings or quiet meals.The dedicated den/office provides an ideal space for working from home. A convenient half bath with laundry room completes the main level. Upstairs, the primary suite is a peaceful retreat with a full bath, complemented by two additional bedrooms and another full bath. The basement is partially finished providing the possibility for an in-home gym, recreation room, secluded office, additional storage space or all of the above! The private, fully-fenced backyard sanctuary features a stunning bluestone patio and custom wood-burning fireplace, offering a serene environment for outdoor relaxation, and the two-car, detached garage adds practical convenience. This property is the perfect setting for professional pursuits while maintaining access to coastal amenities and a plethora of commuting options. With so much to offer, make sure to view 41 Liberty Street today!

Welcome to 28-A Jefferson Avenue in the charming city of Danbury, CT. This beautiful single-family rental property is a true gem, offering a blend of modern comfort and serene surroundings. Built in 2021, this stunning home is situated on the desirable west side of Danbury, in a peaceful neighborhood with a private, wooded backdrop. The thoughtful design of this home provides a perfect balance of functionality and contemporary living, making it an ideal place to call home. Step inside this inviting residence and discover a well-appointed interior with a spacious open-concept layout. The main level features a modern kitchen equipped with like-new appliances, creating a perfect space for both everyday living and entertaining. The seamless flow from the kitchen into the main living areas allows for gatherings of any size,while the deck offers a peaceful retreat overlooking the woods, providing privacy and a tranquil natural setting. With five bedrooms, including a generously sized primary suite, and additional finished space in the basement, this home offers ample room for comfortable living and hosting guests. Embrace the convenience of this location with easy access to Danbury, Bethel, and major highways, making it a commuter's dream. Additional highlights of this property include a two-car garage, ample driveway parking, and extra street parking for your guests. Whether you're relaxing in the backyard, enjoying the modern amenities, or exploring the local community, 28-A Jefferson Avenue offers a perfect blend of comfort, style, and convenience. Don't miss the opportunity to make this beautiful rental property your new home sweet home in Danbury, CT.

Now available for rent, this quintessential, fully renovated, New England Gambrel Colonial is nestled on a half-acre and located on a quiet cul-de-sac in the scenic shoreline town of Old Lyme. This four-bedroom home with gleaming refinished hardwood floors, has been fully updated and offers the best of coastal living, situated just minutes from Old Lyme Village, Long Island Sound, Black Hall River Marina, and White Sands Town Beach. This property offers the best of coastal living where breathtaking sunsets, sandy beaches, and endless water activities are right at your doorstep. Whether it's kayaking, paddle boarding, fishing, boating, or simply enjoying nature, this location is perfect for creating lasting memories. Fully repainted and designed for both comfortable entertaining and everyday living, the new spacious eat-in kitchen flows seamlessly into the inviting dining room. Sliders lead to a private deck overlooking the expansive backyard, which is ideal for summer barbecues, relaxing, or recreation. The main level also offers a living room, a new full bathroom, and a bedroom, providing flexibility for guests, multi-generational living, or a home office. Three bedrooms and a new full bath complete the second level. Experience the beauty, comfort, and lifestyle of Old Lyme's shoreline.

Discover the perfect blend of colonial charm and modern convenience in this sophisticated annual rental, located in the highly sought-after **Westleigh** condominium complex. This unfurnished residence stands out with its unique and versatile dual-entry design, offering convenient access from both the main and lower levels. The main level welcomes you into a bright, airy living space ideal for everyday comfort, while the secondary lower-level entrance provides excellent flexibility for a private home office, a functional mudroom, or streamlined gear storage for the active enthusiast. Life at Westleigh offers a peaceful, maintenance-free retreat set across beautifully manicured grounds, allowing you to enjoy the changing Connecticut seasons without the hassle of upkeep. You'll be perfectly positioned just minutes from the historic Litchfield Green, where world-class dining, curated boutiques, and vibrant community events await. For the outdoor lover, the nearby White Memorial Conservation Center offers miles of pristine trails for hiking and biking. This unit is an exceptional find for those seeking a quiet, professional environment within one of Litchfield County's most prestigious communities. Schedule your private tour today and see why Westleigh is the standard for luxury rental living in Litchfield.

Fantastic rental opportunity in one of Greenwich's most popular neighborhoods. Located on a quiet cul-de-sac street, this sunny three-bedroom, two-full-bath ranch features a private backyard and is ready for occupancy on June 1st, 2026. Key features include: An open floor plan-family room and eat-in kitchen, updating with new quartz countertops. Large primary bedroom with an en-suite full bath, plus an additional den/office ideal for working from home. Nicely proportioned secondary bedrooms-full bath. Laundry Room. A detached two-car garage with walk-up storage. Situated right around the corner from the Cos Cob Train Station for an easy city commute. The home is central to everythingGreenwich has to offer, including Cos Cob Park, Mill Pond shopping, Bruce Park, Todds Point Beach and local schools both private and public.

Academic rental located in the charming town of Chester Connecticut. Ideally located for access to nearby colleges including Wesleyan and Connecticut College. This adorable, well maintained home is located just over a mile from the inviting downtown center of Chester with its bustling restaurants and interesting shops. The home has a lovely open floor plan on the main level which includes an updated kitchen with a new induction cooktop range. While preparing a meal you can be engaged with those in the living or dining room through the window like pass through that opens into these spaces. Sliders from the living and dining room open onto the rear yard and patio. Enjoy relaxing outside or fire up the grill and prepare dinner. Also on the main floor is a half bath and plenty of storage. Access the second floor by climbing the coolest oak spiral staircase. Enjoy a large primary bedroom with ensuite bath and ceiling fan. The second bedroom is just down the hall past the hallway bath. The laundry room is conveniently located in this bathroom. The yard is generous and private. The dates of occupancy are September 1- May 31(possibly through June 30). The use of the wood stove will be considered by the landlord.

TIME TO PLAN YOUR SUMMER VACATION! OR RENT YEARLY! Enjoy country living in this stunning location with spectacular views and total privacy. Only 90 minutes from NYC. Swim in the heated gunfire pool. Explore the homes 142 acres. Plenty of room for family and friends who want to experience the beauty of Litchfield County. There is a 6 Bedroom main house with a 2 bedroom plus loft guest house. Total 8 Bedrooms and 4 Full baths. Can sleep 19 with every bed filled. Explore 142 acres of open fields and forest. The house has a chic modern interior that is tastefully decorated. There is easy access to Litchfield County's many private schools. Enjoy the hiking trails at local land trust, canoeing or kayaking on the Housatonic river or Lake Waramaug. There are country fairs, art shows, local theatre, great restaurants and many fine shops to explore. Rental available starting Available mid May through mid September for $25K per month plus expenses. Also available September $12k per month for yearly lease. Minimum 24 hour notice to view.

Available for the Sept 2026 through June 2027. This sun- filled colonial has been lovingly restored for easy comfortable living. Open views of the Long Island Sound throughout this home offers room for all. Screened in wrap around porch to enjoy the warm days and nights. Updated kitchen with stainless appliances and large dining nook, mud room, office and dedicated laundry room and half bath all found on the main level. Four levels of living make this the perfect home for multi generations: with a main level bedroom with Queen bed, Primary Suite on the second level with en-suite bath and office nook with a private balcony, second bedroom with bunks -on the third level is the fourth bedroom with twin beds, shared full bath on the second level. Lower level has a rec/play room. Access to the Soundview Association beach.

Annual furnished rental available April 2026. Tranquil country cottage on Lake Lillinonah. Rare opportunity to rent with direct lake frontage, lovely grassy area by the lake and dock. This well appointed 2 bedroom home is the perfect writer's or artist's retreat, nestled on a lightly wooded hillside overlooking CT's best kept secret lake. 90 minutes to Manhattan. Enjoy the 2 patios and deck areas among the lovely perennials and stone walls with calming lake views. Relax in the quiet country life on the lake. Great for bass fishing, too. Interior is scheduled for painting mid March.

AVAILABLE FOR THE MONTH OF JULY. Classic Madison charm meets modern family living in this inviting 4 bedroom Colonial on Wildcat Road. Step through the front door to discover hardwood floors that flow throughout, two fireplaces that add warmth and character, and an extra-large (front to back) Living Room perfect for gatherings large and small. Gardeners will love the Greenhouse, right off the Dining Room! Just off the Living Room leads to a delightful screened porch-ideal for morning coffee or summer dinners-and a spacious patio for outdoor entertaining. The walk-out lower level is completely finished and currently serves as a generous family room, offering a wood burning stove, spacious laundry area, flexible space for play, relaxation, or entertaining. Located close to Madison's charming town center and the Town Campus, this home delivers both convenience and community. As a special bonus, enjoy access to the inground pool next door-a rare perk that makes summer living effortless. Whether you're hosting friends, enjoying quiet evenings by the fire, or exploring all that Madison has to offer, this home provides the perfect backdrop for everyday life and lasting memories.

AVAILABLE FOR THE MONTH OF JUNE. Classic Madison charm meets modern family living in this inviting 4 bedroom Colonial on Wildcat Road. Step through the front door to discover hardwood floors that flow throughout, two fireplaces that add warmth and character, and an extra-large (front to back) Living Room perfect for gatherings large and small. Gardeners will love the Greenhouse, right off the Dining Room! Just off the Living Room leads to a delightful screened porch-ideal for morning coffee or summer dinners-and a spacious patio for outdoor entertaining. The walk-out lower level is completely finished and currently serves as a generous family room, offering a wood burning stove, spacious laundry area, flexible space for play, relaxation, or entertaining. Located close to Madison's charming town center and the Town Campus, this home delivers both convenience and community. As a special bonus, enjoy access to the inground pool next door-a rare perk that makes summer living effortless. Whether you're hosting friends, enjoying quiet evenings by the fire, or exploring all that Madison has to offer, this home provides the perfect backdrop for everyday life and lasting memories.

AVAILABLE FOR THE MONTH OF AUGUST. Classic Madison charm meets modern family living in this inviting 4 bedroom Colonial on Wildcat Road. Step through the front door to discover hardwood floors that flow throughout, two fireplaces that add warmth and character, and an extra-large (front to back) Living Room perfect for gatherings large and small. Gardeners will love the Greenhouse, right off the Dining Room! Just off the Living Room leads to a delightful screened porch-ideal for morning coffee or summer dinners-and a spacious patio for outdoor entertaining. The walk-out lower level is completely finished and currently serves as a generous family room, offering a wood burning stove, spacious laundry area, flexible space for play, relaxation, or entertaining. Located close to Madison's charming town center and the Town Campus, this home delivers both convenience and community. As a special bonus, enjoy access to the inground pool next door-a rare perk that makes summer living effortless. Whether you're hosting friends, enjoying quiet evenings by the fire, or exploring all that Madison has to offer, this home provides the perfect backdrop for everyday life and lasting memories.

A Timeless Summer Tradition: Renovated Victorian Shingled beach house in the Borough of Fenwick Experience the quintessential New England summer in the historic Borough of Fenwick. This stunning, shingle-style Victorian beach house seamlessly blends old-world coastal charm with modern, high-end luxury. Featuring 8 spacious bedrooms and 4.5 baths, this expansive residence is the perfect sanctuary for large families or those who love to entertain against the backdrop of the Long Island Sound. The heart of the home is a totally renovated gourmet eat-in kitchen, designed for the culinary enthusiast and large-scale hosting. Beyond the kitchen, life slows down on the magnificent wrap-around screened porch-the perfect vantage point to enjoy your morning coffee or an evening cocktail while overlooking the water and catching the sea breeze. Retreat to the third floor, where a dedicated playroom offers a private escape or a quiet workspace away from the main living areas. From its cedar-shingled exterior to its thoughtfully updated interior, every inch of this home invites you to relax, recharge, and rediscover the magic of a Fenwick summer.

6 WEEKS OF BLISS!! THINKING OF RENTING A CHARMING HOUSE IN MADISON FOR THE SUMMER? Available from July 19, 2026 to August 30, 2026. The Landlords are seeking a renter to take the entire term (no weekly or 2 week rentals available). Called The Wendell Farm, this 3 bedroom home has a chef's kitchen, hardwood floors, open floor plan, and newly added Master Suite in 2008. Spectacular Madison Beaches are a 5 minute drive away. Downtown Madison is 3 minutes away. The public middle school across the street, Polson Middle School, has tennis courts and playing fields. The property is complete with the quintessential red barn. Come experience the easy summer lifestyle in Madison. Landlords and house are pet friendly. Tenant pays for electricity.

AVAILABLE EARLY SEPTEMBER TO THE END OF MAY, 2027. Classic Madison charm meets modern family living in this inviting 4 bedroom Colonial on Wildcat Road. Step through the front door to discover hardwood floors that flow throughout, two fireplaces that add warmth and character, and an extra-large (front to back) Living Room perfect for gatherings large and small. Gardeners will love the Greenhouse, right off the Dining Room! Just off the Living Room leads to a delightful screened porch-ideal for morning coffee or summer dinners-and a spacious patio for outdoor entertaining. The walk-out lower level is completely finished and currently serves as a generous family room, offering a wood burning stove, spacious laundry area, flexible space for play, relaxation, or entertaining. Located close to Madison's charming town center and the Town Campus, this home delivers both convenience and community. As a special bonus, enjoy access to the inground pool next door-a rare perk that makes summer living effortless. Whether you're hosting friends, enjoying quiet evenings by the fire, or exploring all that Madison has to offer, this home provides the perfect backdrop for everyday life and lasting memories.

Experience the quintessential summer lifestyle in this light-filled 2-bedroom, 2-bathroom modern beach cottage, designed for those who value sunshine and salt air. Perfectly situated just steps away from private beach access, this home is the ultimate retreat for relaxation and coastal adventure. A private oasis for summer BBQ's on the beautiful deck, central air, Newly renovated. Outdoor shower for when you return from the sandy beach. AVAILABLE JUNE - $7,000, JULY - $10,000, AUGUST - $10,000

RESERVE YOUR MONTH AT THE BEACH IN MADISON ! RELAX IN THIS VINTAGE 3-BEDROOM DORMERED CAPE W/ STUNNING SCREENED PORCH ~ SET IN PRIVATE SANDY BEACH COMMUNITY A SHORT WALK TO THE BEAUTIFUL WAVES OF LONG ISLAND SOUND ~ HOME IS PRESENTLY AVAILABLE FOR THE FULL MONTH OF JULY