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AVAILABLE FOR MONTH OF AUGUST. Relax and unwind for a summer at the beach. This well maintained, 3 bedroom home with vintage beach house charm, has easy access to a private association sandy beach just steps away. The open Living Room and Dining Room with the original wood floors are adjacent to a well equipped and modestly updated kitchen for all of your food preparation needs. There is also a mudroom off the kitchen which includes a shower with hot and cold water, making it easy to rinse off when returning from the beach. A Ductless AC system cools off the whole house. The 2nd floor has three bedrooms- one king (master), one full and one with 2 twin beds plus a full bath with shower. A wonderful, expansive front porch, with screens, is a great place to entertain or read. The spacious back and side yards are perfect for all types of summer games and provide a clear view down to the water! The 2 car garage is perfect for storing lawn chairs and beach gear (provided), as well as bikes. The neighborhood is great for taking walks and bike riding. Easy access to downtown Madison by bike or car. Some pets considered.
…By William Pitt Sotheby's International Realty
Rare opportunity to lease on a short-term basis a fully furnished townhouse in the beautiful Heritage Village 55+ community. This beautifully remodeled Franklin model overlooks the 13th hole and a picturesque pond, offering tranquil golf course views from the private rear patio. The updated white kitchen features granite countertops, tiled backsplash, stainless steel appliances, and comes fully equipped. The sun-filled living and dining rooms boast cathedral ceilings, a wood-burning fireplace, and sliding doors leading to two private patios, creating an inviting space for relaxing or entertaining. Upstairs, you'll find two spacious bedrooms, a tastefully remodeled full bath with a walk-in shower, and a conveniently located laundry area. Energy-efficient mini-split heat pumps provide year-round heating and cooling. Additional features include a detached one-car garage just steps away, abundant nearby guest parking, and access to the community's exceptional amenities, including pools, tennis, pickleball, fitness, and an extensive selection of clubs and activities. Applications accepted through Rent Spree.
…By William Pitt Sotheby's International Realty
Academic rental available Sept through June! Stunning,spacious 4BR, 3BA Colonial perfectly situated close to town, schools,vibrant shopping,and local beaches. This inviting home features a light-filled living room with fireplace, formal ding room, functional eat in kitchen, separate family room, a private main level office, and a charming porch. Enjoy comfort, premium convenience, and a prime coastal-town lifestyle for the academic term.
…By William Pitt Sotheby's International Realty
Available from September 15, 2026, through May 15, 2027, this stunning direct-waterfront academic rental offers an unparalleled coastal lifestyle with breathtaking, panoramic views from almost every room. The bright, sunny interior features an open-concept main level, highlighting a gourmet kitchen with quartz countertops and stainless steel appliances, alongside a generous living and dining area complete with a gas fireplace and walls of glass that frame the ever-changing coastal vistas. Sliders open to an expansive wrap-around deck perfect for relaxing, while the direct-access beach with its natural tidal pools awaits just steps away. The home's flexible layout includes a convenient main-floor bedroom with a full bath and laundry, while the upper level boasts a second bedroom, a full bath, and a one-of-a-kind primary suite featuring soaring ceilings, dramatic walls of glass, and a private balcony for your morning coffee. Please note that this is a strict no pets, no exceptions property.
…By William Pitt Sotheby's International Realty
ACADEMIC RENTAL. Welcome to 32 Sheep Pasture Road - a three bedroom, two bath ranch conveniently located close to everything and offering privacy in a wooded setting. Recently renovated, the open floor plan flows nicely from the foyer into the living room, dining area and kitchen. The sun room leads to the patio and private backyard. The bedrooms are nicely sized and share a hall bath with tub/shower. The primary bedroom has two closets and a full bath with a walk-in shower. Access the two-car garage from the mudroom/laundry area. Dogs will be considered on a case-by-case basis. No smoking, credit check and two months security required. Lease available as of 8/1.
…By William Pitt Sotheby's International Realty
This charming Cape Cod sits on a desirable corner lot, blending timeless character with thoughtful modern updates. Featuring two bedrooms and one full bath, the home offers a warm and inviting living space that highlights its classic 1940s charm. The updated kitchen, features granite countertops, stainless steel appliances, and beautiful wood flooring. The bathroom offers a spa-like feel with elegant marble flooring and marble-tiled walls. Abundant storage throughout the home provides plenty of space to stay organized. Conveniently located and full of character, this home is ready for its next tenant. Background and credit check required.
…By William Pitt Sotheby's International Realty
AVAILABLE FOR THE MONTH OF AUGUST. Live the ultimate shoreline lifestyle on Middle Beach Road, Madison's most prestigious and sought-after coastal street. This delightful 2-bedroom, 1-bathroom garage apartment (on the 2nd floor) offers a rare opportunity to enjoy stunning dual views, capturing the sparkling waters of the Long Island Sound from one side and the serene, ever-changing landscape of the salt marsh from the other. The interior features a functional layout with a welcoming Living Room and an efficient galley kitchen. Step out onto your private back deck-the perfect spot for morning coffee or evening relaxation while taking in the peaceful marsh views and coastal wildlife. Best of all, you are just a short, scenic walk away from East Wharf Beach or The Surf Club and Madison's charming downtown, filled with local shops, dining, and the iconic RJ Julia Booksellers. Don't miss this chance to experience the perfect blend of natural beauty and unbeatable convenience on the shoreline.
…By William Pitt Sotheby's International Realty
AVAILABLE THIS SEPTEMBER 1 TO JUNE 30, 2027. PARTIALLY FURNISHED. PAINTED ALL WHITE. NEWER REFINISHED HARDWOOD FLOORS! NEWER BATHROOM! This open concept 2 bedroom home, hardwood floors, and located in one of the best beach Associations off Neck Road, is perfect for 1-2 people. Fabulous deck off the back of the home provides a perfect place to enjoy a book or glass of wine. Absolutely NO pets, no smoking. Owners retain use of the garage. Come enjoy the academic term by the shore!
…By William Pitt Sotheby's International Realty
Enjoy the beach this summer! A rare year-round rental in the coveted Hartford Avenue beach community. This charming home offers a first-floor primary bedroom and a brand-new main-level full bath. Also found on the first level are a kitchen, dining room, living room, family room, 2 fireplaces, a washer and dryer, and an additional brand-new half-bath. Two bedrooms and a brand new full bath are found on the second floor. Enjoy a wonderful enclosed porch, an outside patio, and a large level yard. A private sandy beach is just a short stroll away. Whether it's the energy of the summer or the peaceful solitude of winter, this location is ideal for enjoyment throughout all four seasons. Convenient to town, restaurants, shopping, the town green, and schools. Don't miss your chance to secure a year-round piece of paradise on the CT shoreline.
…By William Pitt Sotheby's International Realty
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.
…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
Experience New York-style sophistication in this stunning townhouse apartment located in the vibrant center of downtown Milford. This residence masterfully blends modern urban aesthetics with coastal charm, offering a refined and peaceful living environment just steps from the energetic Milford Green. Spacious open-concept layouts with high-end finishes that evoke a true Manhattan loft feel, perfect for both daily living and effortless entertaining. Retreat to your own outdoor sanctuary, ideal for morning coffee or evening relaxation under the stars. Benefit from easy access to the train station, I-95, and the Merritt Parkway for a seamless regional commute. Easy access to top-tier restaurants, cozy coffee shops, tennis courts, and local parks. Enjoy immediate proximity to seasonal events, boutiques, and the vibrant culture of the Milford Green. No Smoking
…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
Annual Furnished Rental. Nestled in the heart of one of Madison's most sought-after beach communities, this charming and meticulously maintained home offers an effortless coastal lifestyle just moments from Overshores Beach. Thoughtfully furnished and move-in ready, the home features a welcoming floor plan with a sunny kitchen, comfortable family room, classic living room, home office, powder room, and delightful three-season porch perfect for enjoying summer breezes. Upstairs are two generously sized bedrooms and a full bath. The kitchen blends vintage character with modern convenience, featuring stainless steel appliances and timeless appeal. Whether you're working remotely from the dedicated office, relaxing with a book on the porch, or taking a short walk to the beach, this home is designed for easy living. Fully furnished and equipped with linens, kitchen essentials, beach towels, and chairs, this turnkey rental offers everything needed to enjoy life on the Connecticut shoreline. Hardwood floors throughout. Security deposit, credit/background check, and excellent credit (750+) required. $250 end-of-lease cleaning. No pets. No smoking.
…By William Pitt Sotheby's International Realty
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.
…By William Pitt Sotheby's International Realty
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.
…By William Pitt Sotheby's International Realty
SEPT '26 - MAY '27 ACADEMIC WATERFRONT RENT Plan ahead. With amazing views out over Long Island Sound & beyond this light & bright Beach Colonial was built in 2006 plus has a recent 3 BR addition! Featuring an open floor plan, all in excellent condition with lots of glass & a wrap around deck to take full advantage of it's setting. Located at the very end of a private street this special home is in a nice quiet setting especially in the off season. Hardwood floors both up & down, central vac, a first floor den with sleeper couch that is perfect for that unexpected guests with a full bath right around the corner, newer propane heat and fully air conditioned. Set up high on piers, you'll feel like you are on a boat! Enjoy awesome sunrises AND sunsets from a single location! August might be available too. Exact dates to be determined. Unique opportunity.
…By William Pitt Sotheby's International Realty
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.
…By William Pitt Sotheby's International Realty
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.
…By William Pitt Sotheby's International Realty
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.
…By William Pitt Sotheby's International Realty
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.
…By William Pitt Sotheby's International Realty
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.
…By William Pitt Sotheby's International Realty
This in-town house will make you feel right at home with its abundance of charm, comfortable furnishings and bright open floor plan. First floor bedroom and full bath. Eat in kitchen with granite counters and stainless appliances also offers a combination washer/dryer. Sun drenched living room with vaulted ceiling makes cottage space very special. A second bedroom or office space upstairs with an additional half bath. Parking for one car included. Walk to everything Madison has to offer: shops, restaurants, beaches, farmer's market. Can be rented furnished or unfurnished.
…By William Pitt Sotheby's International Realty
**FIRST FLOOR** unit located on well- known Townsend Avenue. This unit has a combination of tile and hard wood floors throughout, with a spacious kitchen and seperate formal dining area. Full bathroom off of kitchen with a titled stall shower. Large walk-in storage closet off of dining area along with spacious closets in both bedrooms providing plenty of storage. Fully fenced backyard shared with other tenant as well as a private driveway with one parking spot, followed by plenty of on street parking. Close to the highways, train station, shopping, restaurants and so much more!
…By William Pitt Sotheby's International Realty
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.
…By William Pitt Sotheby's International Realty
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.
…By William Pitt Sotheby's International Realty
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