The agencies at Killingworth
These agencies offer a selection of luxury properties location at Killingworth. Feel free to contact them for personalized assistance.
Welcome to your ultimate winter retreat! Available for rent for the very first time, this meticulously remodeled 3-bedroom Colonial offers an unparalleled blend of modern luxury, cozy comfort, and complete privacy. Every inch of this home has been thoughtfully designed and comes fully furnished with exceptional, high-end decor throughout. Step inside to find a bright and spacious family room featuring a generous dining area-the absolute perfect setup for hosting holiday dinners and warm family gatherings. The flexible floor plan is designed for convenience, offering comfortable first-floor bedrooms and an additional private bedroom suite on the second level. Outside, embrace the beauty of the season on your private side deck, complete with a cozy gas fire pit. Whether you're sipping morning coffee or stargazing on a crisp winter night, this space is designed for all-season enjoyment. Situated on 6.5 acres of serene, wooded land, you will enjoy ultimate peace and privacy while still being close to local winter attractions. This is not your average rental-it is a pristine, loved home waiting to host your perfect winter season. Just bring your toothbrush and move right in!
…By William Pitt Sotheby's International Realty
ANNUAL RENTAL! 1 BEDROOM PARTIALLY FURNISHED HOME IN CLINTON. Welcome home to 80 River Road, a charming rental opportunity located in the vibrant community of Clinton, CT. Offering 1 bedroom, 1 full bath, this close to 1000SF rental is perfect for 1 person or a couple. Perfectly positioned for those seeking convenience and coastal living, this property offers a comfortable retreat with easy access to all that the Connecticut shoreline has to offer. Meticulously maintained and freshly prepared for its next resident. Enjoy an open, light-filled layout with ample living space. Relax in the private backyard and enjoy the beautifully landscaped grounds. Tenant pays all utilities, Landlords handles lawn care and snow plowing. NO PETS.
…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
This meticulously cared for ranch offers the ideal blend of comfort, style, and convenience-all just moments from town. Set on a stunning private property, the home's setting, condition, and location make it a rare rental opportunity. Step inside to a one level layout filled with charm and thoughtful updates. The newly refreshed kitchen features brand-new appliances, updated countertops and backsplash, and gleaming hardwood floors. A dedicated laundry room adds everyday convenience. The sunroom, equipped with a new ductless split system, opens to a wraparound deck where you can relax and take in the peaceful surroundings. The family room is warm and inviting with its fireplace, while the dining room flows seamlessly into a bright, natural light filled living room-also with a fireplace. The bedroom wing includes a spacious primary suite with a newly renovated bath and walk in closet. Three additional bedrooms and a gorgeous brand-new full bath complete this private area. The large basement provides partial storage space, and the attached two car garage adds even more practicality. One of the best features of this property is its unbeatable location-just a short walk, bike ride, or drive to downtown Madison, East Wharf Beach, the train station, and I95. A rare chance to enjoy privacy, convenience, and quality living in one exceptional home.
…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
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
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 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
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
Term is 9/1/2026-6/31/2027. Price is per month. 24 hour notice to show. Beautifully furnished 3 bed, 2.1 baths house a short walk from East Wharf Beach. Rebuilt from top to bottom in 2018-19 with an open floor plan. A fenced back yard has a bluestone terrace. The living room features a gas fireplace, a well equipped kitchen has a large pantry and a vaulted ceiling family room provides ample room for all. First floor en-suite primary bedroom. Two spacious bedrooms and a full bath are on the second floor. Central AC/heat. This charming house on a quiet cul de sac is close to all Madison has to offer.
…By William Pitt Sotheby's International Realty
Coastal Meets Retro in this adorable Cottage Style Home Near East Wharf Beach in Madison, CT !! Furnished 2 bedroom, 1.5-bathroom cottage rental in Madison, Connecticut - an academic-year lease a short distance from East Wharf Beach on the Connecticut Shoreline. This fully furnished Madison cottage blends a relaxed beach-house feel with mid-century character, including a vintage-style blue refrigerator in the kitchen. The layout offers two bedrooms, one and a half bathrooms, and a dedicated smaller room ideal for a home office or study. Recent updates include new windows (2026)- on order and will be installed in August, updated flooring throughout, making this a turnkey, move-in ready rental. Available fully furnished for the academic year, [September] through [May]. Minutes to East Wharf Beach, Madison town center, Boston Post Road shopping and dining, and Long Island Sound. One dog or small pet considered; no cats. . A rare furnished seasonal rental on the Connecticut Shoreline in Madison, CT 06443.
…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
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
Daydreaming about waking up to the sounds of waves and walking to your very own private beach? Make your dreams come true at 118 Middle Beach Road! With 7 bedrooms, 5 full baths, and 2 half baths, this iconic property comfortably accommodates up to 14 guests. The main level is an entertainer's paradise featuring an oversized kitchen, formal dining area, living room with views from every angle, and generously-sized screened-in porch! In addition to six of the seven bedrooms, the second floor features a family room perfect for kicking back and soaking in the expansive views! The third floor is a private retreat with the seventh bedroom and enormous recreation room. Let's also remember the large, water-facing screened-in porch perfect for soaking in the sunrise and sunset each day. Just outside, sun, sand, and saltwater air await you! This is the perfect place to be this summer - schedule your private viewing today and enjoy your own private beach in a few short months! One month for $45,000, two weeks for $22,500 or one week for $12,500. Please reach out to listing agent for most up-to-date availability.
…By William Pitt Sotheby's International Realty
EXCITING NEWS! This absolutely darling academic rental is unexpectedly available as Tenant had a change in plans. Fully furnished 1 bedroom 1 bath carriage house apartment available for rent SEPTEMBER 2025 - JUNE 2026. This 2nd floor unit overlooks a beautifully manicured backyard and features a private entrance and ample off street parking. Enjoy the walk to beach and downtown as this rental is prime location here in Madison! Completely renovated with modern fixtures, the Upper Deck is one of the prettiest and well kept rentals. Kitchen is updated with modern finishes and opens to the living / family room area. The bedroom is nicely sized with a queen bed and ample closet space. The full bath has been renovated and features a stackable washer dryer. This rental does not last! Landlord covers snow removal, lawn care, trash, WIFI and Cable. Tenant covers for electricity and water. No smoking. EXCELLENT credit required. Ideal only for single person or couple based on septic size. Two months security required.
…By William Pitt Sotheby's International Realty
Relocating to the area? House hunting and yet to find the perfect home? Perhaps looking to spend the academic year along the gorgeous CT shoreline? Look no further as you've found the perfect spot to hang your hat for the academic year here at 32 Tuxis Road. This home is a beautifully restored, quintessential Madison beach house available for rent from September 8, 2026 - June 30, 2027. Originally built in 1915, and maintaining much of the original architecture, this renovated home offers a blend of old world charm and modern luxuries. Desirable open floor plan, chef's kitchen, 5 well sized bedrooms, 4.5 bathrooms and walkable to 3 beaches this house offers all you could desire from a rental. Immaculate condition and desirable location! Dogs considered. Landlord to cover cable, wifi, landscaping, snow plowing and trash removal. Tenant to cover electricity, water, propane and all other utilities. No garage bays and large primary walk-in closet available. Two month's security required.
…By William Pitt Sotheby's International Realty
Located on a private lot in a quiet neighborhood, this three bedroom home is available for rent on a yearly basis. An expansive primary suite is located on the first floor, including a large walk-in closet and private bathroom. Two large bedrooms and an updated bathroom are located on the second floor. Fresh paint, updated bathrooms, recently re-finished hardwood floors, mature plantings, screened-in patio, first floor office, beautiful front porch, and attached 1-car garage are just a few of the standout features. Tenant is responsible for all utilities, lawn maintenance, and snow removal. The home is equipped with solar panels, making the electric bill very affordable.
…By William Pitt Sotheby's International Realty
Excellent Location near town and beaches. 2 Bedroom 1st floor unit with hardwood throughout. Open layout between the kitchen and family room with a butcher block counter top separating the two. Both bedrooms are nicely sized and the unit comes with an updated central full bathroom. Additional storage space in the basement with easy access from the hall. Available immediately.
…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
FURNISHED RENTAL AVAILABLE - September 1, 2026 to May 31, 2027. Comfortable and nicely decorated, this home has 2 bedrooms upstairs that share a newer renovated full bath. This home is located in a private association with access to the Overshores Beach, one of the nicest association beaches on Neck Road. Recently renovated kitchen, newer mud room, newer first floor full bath, laundry room on 1st floor, sunny year round office on the south side of the home, and outdoor shower. Walk / bike to downtown Madison. No smoking permitted. NO PETS. Credit check and security deposit required.
…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
July is available at $20,000/mo. August has been rented. Also available for April, May and June at $12,000/mo. Academic available at $6500/mo. Discover coveted Madison living on a private beach lane complete with an in-ground pool. Embrace coastal luxury in this stunning 4-bedroom, 5.1-bathroom shoreline retreat. 52 Kelsey Place features a chef-inspired kitchen, central air, 2-car garage, large patio with fire pit and BBQ, inviting fireplace, luxurious steam shower in primary bathroom, outdoor shower, and more. Perfect for entertaining, with room for everyone!
…By William Pitt Sotheby's International Realty
Year-round at $7500/mo or Academic at $6500/mo. Discover coveted Madison living on a private beach lane complete with an in-ground pool. Embrace coastal luxury in this stunning 4-bedroom, 5.1-bathroom shoreline retreat. 52 Kelsey Place features a chef-inspired kitchen, central air, 2-car garage, large patio with fire pit and BBQ, inviting fireplace, luxurious steam shower in primary bathroom, outdoor shower, and more. Perfect for entertaining, with room for everyone! Also available for April, May and June at $12,000/mo and or July and August for $20,000.
…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
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
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These agencies offer a selection of luxury properties location at Killingworth. Feel free to contact them for personalized assistance.