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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 modernized Kitchen is equipped with high-end appliances. Lounge on the comfortable Screened Porch, surrounded by lush Nature. Retreat to one of the three Bedrooms, each with its Full Bath. The Finished Lower Level features a sauna, and a mirrored wall for dance or exercise. Garage has an EV charger. Multiple Patios + a Screened Porch beckon as perfect Outdoor Living and Entertaining venues. This rental provides a peaceful sanctuary, with its blend of indoor and outdoor spaces.
…By William Pitt Sotheby's International Realty
Welcome home to this freestanding ranch home in Pond Place, where tranquility and convenience abound! Bright and sunny, this single-level home has an open floor plan with surrounding outdoor views and vaulted ceilings with a center tower of light. Updates throughout, a stunning brick fireplace, wood posts and beams, bamboo floors, large deck with arbor, cul de sac location and private storage shed make this home special. Pond Place offers the best of both worlds in wonderful Avon - a tranquil environment of tree lined streets, walking trails, pond, tennis courts, dog-friendly community plus a convenient location to recreation, restaurants, shops, schools and major routes.
…By William Pitt Sotheby's International Realty
Magical antique on a country lane, just minutes from Lake Waramaug, New Preston for great shopping and dining! Available June, July or August at $4500 per month. Large open kitchen and family room, inviting everyone to be together with windows overlooking the private gardens and patio, which brings nature in. Dining room with wood floors and oversized windows. Enjoy exposed beams and fireplace in the living room and adjoining music area and library. There are 2 bedrooms and a full bath on the main level. The Laundry area is off the kitchen. Master bedroom, with wood floors, full bath, sitting/dressing area and ample closets, on the upper level. Hiking to nearby neighboring farm on the quiet lane. Nearby are New Milford, Washington, Kent and Litchfield which offer lakes, rivers, trails with hiking, fishing, water sports and more.
…By William Pitt Sotheby's International Realty
The ideal country House for your unforgettable Summer/Fall In Greenwich. Available from June 21st - September 13th. This amazing shingle style home was custom built in 2010 and offers 8482 square feet of beautifully detailed interior spaces with high ceilings Throughout. Offering graciously scaled public rooms, a private study, gorgeous formal dining room, a gourmet kitchen with breakfast room, access to a deck as well as a terrace for alfresco dining, fun filled third floor game room, 6 wonderful family bedroom suites, a walkout lower level with exercise room and a gorgeous brand new pool with spa! Rental Terms: Annual: $39,500 Per Month
…By Sotheby's International Realty - Greenwich Brokerage
HISTORIC DOWNTOWN MYSTIC - TWO BEDROOM APARTMENT WITH 1 FULL BATH. 1,475 SQUARE FEET. ONE COVERED GARAGE BAY AND ONE UNCOVERED PARKING SPACE INCLUDED. WASHER & DRYER IN UNIT. Well loved and cared for property! Excellent Location near great restaurants, resort shopping, deep water marinas and amazing scenery. Live a Dream in Historic Downtown Mystic! Tenant pays electric, heat, A/C, Liability Insurance. No Smoking, no vaping and no pets.
…By William Pitt Sotheby's International Realty
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.
…By William Pitt Sotheby's International Realty
Sneak away from the hustle and bustle and spend the month of August at Captain Eber Judd House (circa 1740). This historical gem, reminiscent of Nantucket and Essex Whaling Captain's homes, oozes charm with its stunning wide plank floors, beams, and original fireplaces. Located in the heart of downtown Madison, it's just steps from the gorgeous beach, the quintessential downtown, and the Friday Farmer's Market. This home shines with historical moments, yet it is appointed with modern amenities, making time spent here a delight. Enjoy coffee in the morning in the three season sunroom, a glass of wine and views of the Long Island Sound by the firepit (s'mores anyone?), afternoon snoozes on the back terrace or cozy up with a book in the library or family room. The 1st floor features the cook's kitchen, elegant dining room, family room, library, sunroom, study, laundry room, and a full bath. You'll find 3 bedrooms and 2 full baths on the second floor. Tucked away, yet close to everything, this home is a wonderful place to hang your hat for the month of August. Truly one of a kind! Simply drop your bags and exhale. No pets or smoking, excellent credit is required.
…By William Pitt Sotheby's International Realty
Experience the ultimate coastal lifestyle in this sun-drenched, TOP FLOOR condo at 185 Melba Street, Unit #305 located in the sought-after Breaker Beach community of Milford. This 823-square-foot home perfectly balances modern interior updates with the serene atmosphere of waterfront living. The Updated Kitchen features sleek granite countertops, custom cabinetry, and updated appliances. Your own private screened-in Balcony is located off the living area, for year-round enjoyment, offering peaceful water views and refreshing sea breezes. Enjoy the peace and quiet of a top-floor unit with no neighbors living above you! Living at Breaker Beach feels like a permanent vacation with direct access to Long Island Sound. Step out of the building and onto the private association beach which offers a dedicated barbecue and picnic area overlook the water, and the calm local waters - perfect for kayaking, swimming, or paddleboarding. Convenience features include secure building with elevator access, a laundry room and dedicated storage space in the basement and plenty of parking for residents and guests. Located in the charming Point Beach/Woodmont area, you are just a short drive from Milford Town Center, known for its historic green, boutique shopping, and vibrant dining scene. Convenient access to the Milford Train Station and major highways, blending a tranquil beach retreat with easy accessibility.
…By William Pitt Sotheby's International Realty
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.
…By William Pitt Sotheby's International Realty
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.
…By William Pitt Sotheby's International Realty
DIRECT WATERFRONT in OLD GREENWICH Enjoy western facing views and gorgeous sunsets on this expansive 1 ACRE property close to Greenwich Point, schools, train, and Village of OG. Enjoy year round carefree living at this updated 4 bedroom home. Open floor plan with spectacular natural light throughout. Spacious gourmet kitchen w/adjoining family room w/fireplace and French doors opening to the oversized soccer field size back yard directly to the water. A large Living room w/fireplace, lovely dining room and office on first floor complete this ideal family retreat. A perfect home and location! Owner pays for Landscaping. Updated dock pending approval. Rental Terms: Annual: $25,000 Per Month
…By Sotheby's International Realty - Greenwich Brokerage
This classic circa 1800 antique farmhouse sits on a private 3-acre lot and is perfectly situated just minutes from the famed Litchfield Green, but worlds away. Featuring 2 bedrooms and 2 bathrooms with an additional flexible den space, this charming residence overlooks Butternut Brook and offers 1,608 square feet of comfortable living space. The property is surrounded by 200 acres of protected land, with 150 acres of immediately accessible walking trails right at your doorstep. Enjoy the serenity of private woodland exploration, seasonal wildlife viewing, and peaceful morning outings without ever leaving your neighborhood. This rare combination of pastoral privacy and trail access creates an unparalleled retreat setting while maintaining convenient access to Litchfield's historic town center, renowned dining, shopping, and cultural attractions.
…By William Pitt Sotheby's International Realty
New flooring and fresh paint throughout. Updated kitchen cabinets and countertops, new bathroom vanities and light fixtures. Adorable three bedroom, two full bath ranch style home with walk up attic for unlimited storage on a beautifully landscaped corner property in a convenient location minutes to everything. Cozy living room with oversized window and built in shelving. Large dining room plus a den with sliders to patio and a terrific rear yard. City water/sewer and all landscaping included. Strong credit is an absolute must. A cozy gem completely refreshed and ready for immediate occupancy.
…By William Pitt Sotheby's International Realty
Beautifully renovated half duplex, townhouse style unit located in Morris Cove, just steps from the Pardee Seawall Park! Newer vinyl laminate flooring throughout the main floor, upper level, and finished third floor. Updated kitchen with quartz counter tops, stainless steel appliances, and cabinets. Both bathrooms with quartz top vanities, and a full wall of a marble backsplash in the upper level full bathroom. Finished third floor flex space with skylights, and a basement with laundry and plenty of room for storage. Enclosed three season porch and a fenced in back yard. Close to Fort Hale Park, Lighthouse Point Beach, major highways, Yale, downtown, and so much more!
…By William Pitt Sotheby's International Realty
AVAILABLE FROM EARLY SEPTEMBER 2026 TO END OF MAY 2027! Welcome to this enchanting 4 bedroom, 2 full bath home, where the beach is just a half-block stroll away! Located off Neck Road, 1 mile from the heart of Madison, CT, this residence offers the perfect blend of coastal charm and convenience. As you enter, the first floor greets you with a Family Room, through to a Kitchen, then onto the Living Room. The sunroom is a tranquil space to unwind, offering views of the outdoors and filling the home with warmth year-round. The 1st is rounded out with 2 well appointed bedrooms. The second floor is a private retreat featuring the oversized Primary Bedroom and an additional bedroom, each designed to provide a peaceful escape with ample space and comfort. Step outside to the expansive outdoor deck, where you can soak up the sun or entertain guests in the sea breeze. The fenced yard ensures privacy, while the patio with an awning offers a shaded sanctuary for those long summer days.This home's prime location near the beach allows for endless days of sand and surf, while the close proximity to downtown Madison ensures all the conveniences of town living are just moments away. If you are seeking an academic rental, this home offers a lifestyle of comfort and relaxation. NO PETS.
…By William Pitt Sotheby's International Realty
Furnished Studio Apartment- Available May 15th- Sept 15th. The studio is graced with stunning views of Fence Creek, providing a picturesque backdrop to your daily living. Just steps away from the sandy shores of East Wharf Beach and the vibrant Madison town center, you'll have the best of coastal living right at your fingertips. Designed with efficiency in mind, the space features a queen bed that effortlessly converts into a couch, allowing you to maximize the living area during the day. The apartment is equipped with a modern split system to ensure your comfort in all temperatures, and the convenience of an in-unit washer and dryer adds to the ease of your stay. Whether you're seeking a tranquil spot to unwind or a base to explore the local attractions, this studio apartment is the ideal choice for a memorable summer getaway. Embrace the laid-back lifestyle of Madison and let the gentle sea breeze and calming creek views soothe your soul.
…By William Pitt Sotheby's International Realty
JULY &/OR AUGUST ~ Enjoy One or Two Months in Madison for 2026 at a Price you can't beat !! Summers in Madison are what they're cracked up to be !! Spend your Days one of 3 Local Manicured Sandy Beaches (East Wharf, West Wharf or the Surf Club) all located Directly on Long Island Sound. When the day is done, head Back Home for the Tranquility of this Country Cape on a Private and Secluded Hillside ~ Chill & Grill on the Outside Patio as the Sunsets over the Rear of the House. Take advantage of Sundays Free Concerts on the Green, Thursdays music events at Madison Beach Hotels The Grassy Strip and don't forget to pick up something Fresh on Fridays from The Farmers Market on the Green.
…By William Pitt Sotheby's International Realty
Over forty private wooded acres, a mountain stream, and hiking trails that lead to your own waterfall. This three-bedroom rustic stone cottage in the heart of the Litchfield Hills is the kind of country rental that's hard to find and harder to leave. A screen porch overlooks the running water, the living room has handsome exposed beams and opens to a covered porch, and wood-burning fireplaces make evenings in the formal dining room feel exactly right. One bedroom on the main level; the primary and third bedrooms up a level. The setting is quintessential Connecticut, located off a scenic country roads lined with antique homes. Macedonia Brook State Park at your doorstep, the village of Kent just minutes away, Metro-North is close by, and New York City just two hours away.
…By William Pitt Sotheby's International Realty
Great South Wilton location and award winning Wilton schools! Move right into this bright 3 bedroom ranch style unit with 2 full baths; sun filled eat-in-kitchen with vaulted ceiling, skylight, and dining area; large living room; plus den/office with laundry - all conveniently on one level. This rental includes the use of the one car garage and pull-down attic storage; plus includes electric, water, hot water, trash, landscape, mowing, plowing, and maintenance of the furnace. Tenant to pay for oil and cable only. Pets considered on case by case basis. Tenant has use of the front and side yard (backyard for the other unit). Available immediately!
…By William Pitt Sotheby's International Realty
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
…By William Pitt Sotheby's International Realty
Lovely Furnished Summer Rental available in the Ferry Landing District of Hadlyme. The perfect spot to escape and enjoy the Lower Connecticut River Valley and everything it has to offer. Take the Hadlyme Historic Ferry over to Chester Village to enjoy great restaurants, art galleries, and ice cream! The Gillette's Castle with extensive walking paths is a stones throw away. Kayaking, and boating is available to you at the Ferry Landing boat launch. Lyme is home to miles of hiking trails throughout the town and connecting to open space and traveling beyond it's borders. Golf & Tennis is available in the area. This property requires a 2 month minimum with the ability to lease May-September. (with premium during July & August) Charming, thoughtfully renovated colonial furnished with family antiques yet has all of today's amenities and is on the National Historic Register. Open-plan chefs kitchen with family room, casual dining and gas fireplace. Fabulous pantry/laundry room, Formal Dining, Living room with piano, front sitting room with half bath. Upstairs are 3 generous bedrooms with ensuite baths. Handsome wide board floors with tile bathrooms.This home is exquisite and filled with warmth, you will feel at home. Many more details to share. Landlords live in proximity of this gatehouse, on private estate.
…By William Pitt Sotheby's International Realty
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
…By William Pitt Sotheby's International Realty
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.
…By William Pitt Sotheby's International Realty
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
…By William Pitt Sotheby's International Realty
Located on one of the most picturesque streets in Riverside and part of the Willowmere Waterfront Association. This classic center hall colonial offers over 3200 square feet with generous living spaces including a formal dining and living room, sunroom and family room adjacent to the well-appointed galley kitchen. 4 bedrooms and 3 full bath. An oversized bluestone terrace overlooks a beautiful level half acre with western exposure. You'll love going home to this special neighborhood. Rental Terms: Annual: $16,000 Per Month
…By Sotheby's International Realty - Greenwich Brokerage
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