luxury properties for rent Connecticut, United States

Just off South Avenue, with much quieter surroundings, sits a modern farmhouse Colonial almost new construction with innovative design, high-style and unparalleled building quality. The exterior blends classic colonial style with contemporary flair. The interior space is thoughtfully created to provide open concept living with transitional finishing elements that will satisfy the needs of today's sophisticated families. The home offers over 7,800SF of finished space including 5 en-suite designer inspired bedrooms and 5.5 baths. The third floor offers additional recreational space and the lower level is finished with gym, office and rec room.

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.

ANNUAL UNFURNISHED (OR PARTIALLY FURNISHED) RENTAL), AVAILABLE AUGUST 1. Located between downtown Madison and the Hammonasset State Park Beach, this 3 bedroom renovated ranch offers a comfortable life style. The house offers a deck to enjoy the outdoors, large yard, easy access to the Shoreline Greenway Trail and beach access at the end of Webster Point Road. The primary bedroom has a full bath, the other two bedrooms share a full bath. AC is via window units and heat is electric. This house is cute and comfortable. Some pets considered.

Academic Year Rental. Nestled in the wooded canopy of the Litchfield Hills, this cozy 3 bedroom cottage offers the perfect blend of charm and serenity. Inside, the kitchen welcomes you with a cheerful atmosphere, while an inviting living room features a large picture window and stone fireplace - perfect for chilly evenings. The home also includes a generously sized lower level that provides excellent extra living space for a media room, home office, or guest retreat. Step outside onto the deck to enjoy an ideal spot for summer grilling, or unwind in the screened-in porch to take in the lovely, elevated views toward the Housatonic River and experience spectacular evening sunsets. The property features softly rolling lawns with perfectly situated Adirondack chairs, inviting you to relax in your own quiet, private sanctuary. Listen to the tranquil chorus of native birdlife and the soothing sounds of the surrounding forest. Just minutes from the historic Cornwall Covered Bridge, this captivating property delivers the ultimate New England country escape.

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.

Rental Available August 25, 2026- June 15, 2027 An incredible East Rock opportunity. This magnificent 5 BR furnished home is available for academic rent. An elevator takes you to all 3 floors of this amazing home as well as down to the full dry basement perfect for storage. Main floor boasts a Living room, dining room, a huge kitchen that opens to a family room as well as a big deck that leads to a fully fenced in private yard. The second floor has 4 BR's, one with built-ins doubles as a great home office.2 full beautiful new baths. The third floor is fabulous! A private family room, loft, huge bonus room, a bedroom and new beautiful bathroom. Tons of built in bookshelves throughout. Gas heat, central air. Located in the private corner of Everit street across from the park with off street parking. Minutes to Foote school and a short walk to Yale and Downtown New Haven. No smoking. No pets. 700 Minimum credit score. LISTING AGENT MUST BE AT ALL SHOWINGS AND TIMES ARE LIMITED SO PLEASE GIVE PLENTY OF NOTICE Rentspree Application Accepted

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.

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.

AVAILABLE FOR ANNUAL RENT. FURNISHED OR UNFURNISHED. 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.

Beautifully updated and impeccably maintained, this 4-bedroom, 2.5-bath Colonial offers three finished levels of thoughtfully designed living space in a desirable New Canaan neighborhood. Designed for both everyday living and entertaining, the home features hardwood floors throughout, a stunning renovated kitchen, updated bathrooms, and a finished lower level that provides flexible space for a home office, fitness area, media room, recreation room, or additional living space. Step outside and enjoy the best of indoor-outdoor living with a covered porch, spacious patio, fire pit, and fully fenced backyard, creating multiple areas for relaxation, entertaining, and enjoying the property's peaceful surroundings. Nestled on a beautifully landscaped property in a quiet neighborhood setting, yet just minutes from town, parks, dining, shopping, and commuter routes, this move-in-ready home offers an exceptional combination of comfort, convenience, and privacy. Available July 1. Photos are from a previous listing.

Beautifully renovated and furnished home with direct water views!! Located directly across from the Pardee Seawall Park on the Long Island Sound, don't miss this 2 bedroom colonial cottage that has it all. New hardwood floors in the living room and bedrooms, along with beautiful tiles in both bathrooms and kitchen. Kitchen fully renovated with quartz counter tops and brand new stainless steel appliances. Laundry room right off of the kitchen with a new stackable washer and dryer unit. Detached garage and plenty of off street parking spaces. Cathedral ceilings in the master bedroom with direct water views off a large balcony. Close to many restaurants, shopping, parks, and I-95. Available August 31st to May.

The Connecticut coastal lifestyle awaits you - an incredible opportunity to live in Darien on the Five Mile River Road across the street from the water! This charming New England colonial has been completely renovated featuring 4 bedrooms, and 3 full baths, situated on a private hilltop with views, and a large flat backyard. Located in a highly sought after neighborhood with top rated schools, this home features a gorgeous new kitchen with new appliances and flooring, new bathrooms, new central air, new windows, lighting and a new roof! The primary suite is dreamy and offers a fireplace, full bath, and an adjacent dressing room (or office), and water views. Plenty of natural light throughout the house. A formal dining room off of the living room, a breakfast room with wood beams off of the kitchen, and a sunroom/family room that opens onto a lovely stone terrace for outdoor dining. Updated back entrance mudroom area with storage. Two working fireplaces, a wood paneled library/music room/den complete with built in bookshelves and built in bar-perfect for entertaining! The house is ready to move in with immediate occupancy available. Pets upon approval. Convenient to both Darien and Rowayton train stations, with shopping and restaurants and all amenities close by.

Step into this delightful and charming fisherman's cottage in the heart of downtown Old Saybrook. Built in 1800, 43 Pennywise Lane blends warm and cozy character with surprising spaciousness. The owner has preserved this home's historical integrity while adding in modern comforts. The first floor features an oversized primary suite with full bath, office space and reading nook. The eat-in kitchen is highlighted by gleaming wood counters and a beautiful decorative fireplace. Rounding out the first floor, you'll find the sun filled napping corner, a tucked away charming TV area and a second full bath. You'll also appreciate the mini-mudroom drop zone perfect for your bags, boots and hats! Upstairs you'll find an additional bedroom and a second media or lounge area. This space is ideal for guests or a quiet place to unwind. Enjoy the convenience of an outdoor shower, grill, fire pit and the nicely sized, partially fenced in yard. Fancy a stroll to town? It's just down the block with terrific shopping and dining. Enjoy all the amenities that make this shoreline town so popular and accessible, including access to Amtrak and the Shoreline East Train. Tenant: renters insurance, heat, electric, water and a one time end of lease cleaning. Landlord: all other utilities. No pets or smoking. A truly special place to hang your hat. Available September 15, 2026 - May 31, 2027. Also July and August at 6K per month.

STUNNING MEMORIAL DAY - LABOR DAY RENTAL with POOL and TENNIS COURT (with lights). Enjoy a month or all summer at this resort-style escape with newly renovated interior and incredible entertaining space indoors and out. Extraordinary cook's kitchen with breakfast nook opens into an expansive sun-filled room overlooking lawns, tennis court and pool. Updated bedrooms and bathrooms provide a comfortable and chic look. Long distant views and rolling, verdant lawns add to the magic of this property. Close to top restaurants, art galleries, shopping and outdoor recreation. Only 90 minutes to NYC. Note: Field card indicates that there are 3 bedrooms but the house has 4 bedrooms and a 1250 tank.

Charming 3-4 Bedroom Rental in Desirable Darien Water Community - $5,800/month Welcome to this inviting 3-4 bedroom, 2 full bathroom home in a sought-after Darien water community. Perfect for families or anyone seeking a blend of comfort and coastal living, this well-maintained residence offers flexible space to suit your lifestyle. The private, fenced-in backyard provides a safe haven for the family and pets to play, while also creating the perfect setting for outdoor dining and relaxation. Enjoy easy access to Holly Pond-just a short walk from your door-where you can embrace the waterfront lifestyle that makes Darien so special. This home combines practical living spaces with the lifestyle you've been dreaming of, all in one of Fairfield County's most desirable communities

All-inclusive furnished rental. Available: Winter- 3 month min. $8000/month. Summer Season- Memorial Day thru Labor Day $65,000/season. Summer monthly- $25,000/month. Escape to the serene countryside and experience the authentic charm of this beautifully renovated antique home with a refreshing, heated pool. This rental is fully equipped and all-inclusive with bi-weekly housekeeping. Step inside and discover the beauty of a historical Colonial home, thoughtfully updated with modern comforts. The rooms offer plenty of space and showcase exposed beams and vaulted ceilings. You'll appreciate the natural touch of hardwood floors and the convenience of five fireplaces for those cooler evenings. Stay comfortable all year long with central air conditioning ensuring a pleasant stay in any season. The heart of the home is a charming country kitchen, providing an ideal space for cooking up delightful meals. It opens onto a stone patio, inviting you to enjoy the outdoors with relaxed gatherings. Take in the tranquil views of the countryside as the property sits on level open land adjacent to a land trust. You'll find all the local amenities you need nearby, including a variety of recreation and cultural venues, shopping and fine dining options. 60 minutes to lower Fairfield County, NYC is 90 minutes.

Rarely available! This historic 1860 Essex Village waterfront home is nestled on a quiet lane with direct waterfront on Middle Cove. Step back in time and experience the charm of this Vintage home, complete with many original features, while still enjoying modern amenities and updated appliances. The home boasts original wood floors, a stunning floor-to-ceiling bay window in the living room, and a built-in hutch with a Butler's Pantry in the dining room. Upstairs, the primary bedroom is a spacious two-room suite, accompanied by an additional bedroom and bath. The semi-finished lower level, reminiscent of a cozy tavern room, provides walkout access to the patio, backyard, and waterfront. View stunning sunsets over Middle Cove! Relax on the inviting front porch or take a short stroll to the Griswold Inn, Noah's, the Black Seal, and an array of charming shops, yacht clubs, and marinas. The barn outbuilding is not included in the rental. No pets, no smoking. Minimum 1-year lease. Conveniently located halfway between New York and Boston. You will love living in one of the Historic Homes of Essex Village!

Incredible country home with heated gunite swimming pool skillfully blended into the natural stone landscape. The perfect place for relaxing and entertaining, whilst enjoying open, sunshine views over the golf course. Views from every room! Located within the River Oaks Country Club with resort quality amenities, this large and tastefully furnished 4 bedroom (each with walk-in closets), 3 & 1/2 bath home is offered fully furnished and in mint condition. Laundry room is located on the bedroom level. Enter the master bedroom suite through double doors, featuring two walk-in closets and spacious en-suite bathroom with cast iron tub, double vanity and dressing area. Large walk-in shower with rain fall, wall jets and sitting bench. Additional windowed room off the bathroom which could be used as an office / gym / huge closet! This well equipped home includes central air-conditioning and a superbly appointed kitchen with Viking appliances, wet bar, breakfast dining area and a large island with bar seating. The formal dining room and outside deck area with BBQ grill are accessible from the kitchen. A feature fireplace in the spacious living room and attached 3 car garage complete this home. The fenced in rear yard with expansive patio area, waterfall and custom-built infinity pool designed and constructed by premier area designer, Dobson Pool Company. Available academic term September 2026-2027 $7500/mth plus utilities. Also available summer term 2027, $20,000/mth plus utilities.

Welcome to 14 Island View Ave-a masterfully redesigned coastal retreat nestled in the heart of highly desirable Pine Orchard. Spanning 2,100 square feet, this thoughtfully renovated home seamlessly blends modern luxury with relaxed shoreline living. Boasting 5 spacious bedrooms and 2.5 beautifully appointed baths, the residence features a bright, open floor plan optimized to capture gorgeous, unobstructed water views. Every detail has been meticulously curated during its full remodel, offering an unparalleled turn-key experience in one of the area's most coveted neighborhoods.

The views from this charming Sachems Head waterfront home are exceptional. Located next to the Sachems Head Yacht Club this fully furnished academic rental is a dream come true. Four bedrooms and two full baths, with an additional bedroom and full bath on the ground level in the warmer months. Additional rooms offer an excellent option for home offices. The main level features a wood-burning fireplace and an open floor plan with views from nearly every window. Available September 1, 2026 through June 1, 2027. Flexibility in early June extension. Pets are considered with owner approval. Excellent credit required. Showings by appointment only.

TIME TO PLAN YOUR SUMMER VACATION! OR RENT YEARLY! Available June and July. Call for Summer Pricing! 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. Available starting September $12k per month for yearly lease. Call for Summer Rental pricing. Minimum 24 hour notice to view.

A charming light-filled 4 bedrooms/ 4baths rental jewel in MINT condition with new baths, gourmet kitchen, freshly painted inside and out, new floors, and beautifully landscaped with pool. Take your pick for your Primary bedroom either on the first floor or upstairs! A relaxing and entertaining retreat with spacious rooms including the first floor family room as well as a great finished Lower Level walk out recreation room with a full kitchen, study, full bath. Could be a separate in-law or out-of-town guest quarters! And enjoy the outdoors in your wonderful screened-in porch overlooking a woodland stream. Convenient to the village, shopping, schools, train and the Merritt.

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.