The agencies at Madison
These agencies offer a selection of luxury properties location at Madison. Feel free to contact them for personalized assistance.
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
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
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
4 bedroom Cape with huge fully-fenced back yard. Less than 1/2 mile to middle school, high school, school activities, playing fields and so much more. Enormous great room with tons of natural light and seating options. Close proximity to beaches, town, commuter routes. Available September 1, 2025 or end of August.
…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
This bright and airy home features a stunning great room with vaulted ceilings and beautiful views of the West River. The open-concept space flows seamlessly into a modern kitchen equipped with granite countertops, stainless steel appliances, and a large island perfect for entertaining. Just down the hall, you'll find three generously sized bedrooms and a full bath with a tiled shower/tub. Hardwood floors run throughout the home, and laundry is conveniently located just off the kitchen. Step outside to enjoy a private backyard with a deck, a detached one-car garage, and an extra storage shed. Best of all, the association beach is right at the end of the street, offering vacation-like living year-round. Don't miss this fabulous opportunity for shoreline living at its finest!
…By William Pitt Sotheby's International Realty
Historic Charm Meets Modern Luxury: Carriage House Living in Downtown Guilford Experience the quintessential Shoreline lifestyle in this stunning, light-filled carriage house at 200 Whitfield Street. Tucked privately away in heart of downtown Guilford, this unique residence seamlessly blends historic architectural character with high-end, contemporary updates. Step inside to breathtaking open-concept living defined by soaring post-and-beam vaulted ceilings, exposed timber trusses, and rich wide-plank hardwood floors. The sun-drenched main space features skylights, expansive windows, and a chef's kitchen complete with white shaker cabinetry, sleek dark countertops, a gas cooktop island with breakfast bar, and stainless steel appliances. The living space flows effortlessly to a pristine, updated full bath featuring a custom tile and glass walk-in shower, alongside a convenient dedicated laundry and storage room. Every corner of this property radiates historic warmth, style, and total comfort. Best of all, your location is unmatched. Leave your car behind and take a short stroll to the historic Guilford Green, boutique shopping, local cafes, fine dining, the Guilford Free Library, and the shoreline train station. Jacobs Beach and Guilford Harbor/Marina are just down the road. An extraordinary rental opportunity in an unbeatable downtown location.
…By William Pitt Sotheby's International Realty
Renovated 2-bedroom, 2-bathroom cottage for rent at 98 Union Street in Guilford, Connecticut - walking distance to Guilford Green, the town center, restaurants, and shops. This shingle-style home, named Seascent, pairs a classic Shoreline exterior - white siding, picket fence, and blue front door - with a fully updated interior. The open-concept main level features vaulted ceilings, hardwood floors, and a chef's kitchen with a navy blue island, quartz countertops, stainless steel French-door refrigerator, gas range, and stainless range hood. Globe pendant lighting hangs above the island, and a built-in banquette dining nook and living area with sectional seating complete the main floor. A built-in ladder leads to a loft space, adding flexible square footage above the living room. The primary bedroom offers a vaulted ceiling, shiplap accent walls, and a walk-in closet-ready dresser wall. A second bedroom provides comfortable guest or home-office space. Both full bathrooms have been updated, including a double-vanity bath with stone countertops, black matte fixtures, and tree-print wallpaper. Outside, a private paver patio in the fenced backyard offers space for outdoor seating and entertaining, and a personal driveway provides off-street parking - a rare find this close to downtown Guilford. Available August 15 on a 12-month lease. Tenant responsible for all utilities. No pets. Located within walking distance of Guilford Green.
…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
Academic Rental October 1, 2026 -May 31, 2027. Charming 3-bedroom, ranch-style home in the Harbor View Beach Association. Large living room, 3 generous bedrooms, updated kitchen and bath just steps to the association beach.
…By William Pitt Sotheby's International Realty
Fabulous opportunity for an ACADEMIC furnished rental in Guilford's coveted Mulberry Point. Freshly painted throughout in July 2026- This furnished home is located in one of Guilford's best Association Beach neighborhoods. Water views from most rooms in this flexible, fully furnished, two level home, steps from the Long Island Sound. Enjoy the best kept secret in Guilford with beach rights to Mulberry Point's private beach. Only three miles to the Guilford Green and only 25 minutes into downtown New Haven or take the train straight from Guilford. Basic TV, Internet & Garbage Removal included. Available Sept 1, 2026 -May 31st 2027
…By William Pitt Sotheby's International Realty
Experience the splendor of coastal living with this academic rental, available from October 1st, 2026, through April 2027. Situated in the prestigious Mulberry Point area, this home is a haven of tranquility, offering panoramic views of the Long Island Sound from every room.This residence has been completely renovated in 2022, showcasing an open layout that maximizes the natural light and scenic vistas. The heart of the home is the large kitchen, featuring new stainless appliances that cater to both the culinary enthusiast and the entertainer. Step outside onto the beautiful stone patio, an idyllic setting for both relaxation and social gatherings, with the Long Island Sound as your backdrop. The first floor is thoughtfully designed with convenience in mind, housing a bedroom with a queen-sized bed and an updated full bath. Additionally, the inclusion of a washer and dryer on this level adds to the practicality of the home. Ascend to the second floor to find two more bedrooms: one with a queen bed and the other with three twin beds, each offering updated accommodations and awe-inspiring views of the Sound. This property is not just a house; it's a retreat that promises a unique blend of comfort and natural beauty. Whether you're savoring the quiet mornings with the sound of the waves or stargazing on the patio, this Mulberry Point gem is the perfect academic rental for those looking to immerse themselves in the coastal lifestyle.
…By William Pitt Sotheby's International Realty
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
AVAILABLE FOR THE MONTH OF AUGUST. Embrace Coastal Serenity in a Fully Renovated 5 bedroom, direct waterfront Estate WITH ITS OWN PRIVATE BEACH! Discover the epitome of waterfront luxury in this exquisite Clinton, CT residence, where historic charm meets modern elegance. Nestled on a generous .51-acre lot, this multi-level home boasts of a direct waterfront access with plenty of privacy. Built in 1912 and meticulously renovated along the way. Experience the perfect blend of timeless architecture and contemporary updates. A spacious primary suite (with private balcony!) and two additional bedrooms on the second floor, plus two bedrooms and a rec room on the third floor, provide ample space for family and guests. Step outside to enjoy multiple decks with a panoramic view of Long Island Sound and private beach access for tranquil waterfront living. A spacious Living Room with a fireplace, formal Dining Room, light filled Great Room, and a Sunroom offer diverse areas for relaxation and entertainment. This property is a rare gem, offering a waterfront lifestyle coveted by many but enjoyed by few. Whether basking in the warmth of your fireplace or soaking up the sun on your private beach or deck, this home is a sanctuary for those who seek a blend of luxury and tranquility. It's the perfect home for a month retreat!
…By William Pitt Sotheby's International Realty
Where New England architecture meets timeless elegance! Experience the pinnacle of shoreline living in this spectacular waterfront estate, perfectly positioned on a private, peninsula-like setting in Sachem's Head community. Boasting breathtaking, panoramic views of Long Island Sound, this 1930s residence is a masterwork of historic character and unique architectural artistry. The home's rich heritage is reflected in its exquisite details, from the enduring beauty of Stony Creek Granite and warm Pecky Cypress woodwork, to the original porthole windows in the grand family room. In the formal dining room, a distinctive ribbed ceiling, designed to evoke the overhead of a classic ship's cabin, creates an unforgettable atmosphere for entertaining. The heart of the home features a generous galley kitchen that balances functionality with style, offering abundant cabinetry, expansive counter space, and dining area with plenty of windows making sure no view is missed. Retreat to the second floor to find six spacious bedrooms, each offering its own unique perspective of the water, while the finished third-floor flex space serves as an ideal game room or private sanctuary. Spread across two manicured acres, enjoy relaxed seaside living with multiple sun porches and expansive patio for gatherings. Take advantage of the Vineyard Place Association amenities, all while being just a short drive from charming downtown Guilford!
…By William Pitt Sotheby's International Realty
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.
…By William Pitt Sotheby's International Realty
Academic year RENTAL, AVAILABLE 9/8/2026 - 5/1/2027 Only steps to Grove Beach in this charming Cape style 3 bedroom, 1 & half bath home with one bedroom, the full bath and study on the main floor for easy living. The eat-in kitchen is open to the living room and looks out to the beautifully landscaped large back yard. The generously sized primary bedroom and third bedroom are on the second floor. Central air on the main floor, Enjoy the beach community and the off season. Close to restaurants, shopping, beaches! NO Pets, NO Smoking, Tenant responsible for all utilities, use of fireplace is not allowed per insurance, items not allowed to be stored in basement, Credit check required. Cleaning $200.
…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
Charming Four Bedroom New England Contemporary Colonial with Beach Rights. Discover the perfect balance of relaxation and accessibility in this vibrant academic rental. Nestled in a picturesque New England setting, this home is designed for those who love to get out and explore. Start your morning with a stroll to Julie's Cup of Joe for coffee or enjoy your weekends utilizing your private beach rights. The home features 4 spacious bedrooms, 2.5 bathrooms and a layout that is perfect for entertaining indoors or outdoors. Whether you are hosting friends or settling in for a quiet evening, this property offers the ultimate convenience. Don't miss your chance to live in one of the town's most desirable locations!
…By William Pitt Sotheby's International Realty
Discover the perfect blend of antique charm and modern convenience at 50 Ledge Hill Road. This delightfully updated and maintained antique colonial is available for annual rental, offering a truly peaceful and picturesque retreat on six and a half acres of serene land. Despite the feeling of total privacy and seclusion, you'll remain conveniently located within a fifteen-minute drive of all local amenities. The home features three bedrooms and one and a half baths along with ample living space: a dedicated living room, a comfortable family room, an office, and a den, providing flexibility for working from home or hosting guests. The charming, eat-in kitchen is pleasantly sized, perfect for casual, everyday dining or holiday gatherings. Step outside and enjoy the expansive, sprawling backyard, featuring an inground pool for fun all summer long. The home also features brand-new central air conditioning and landlord-maintained solar energy and professional landscaping. With its blend of historic character, abundant space -inside and out, wonderful amenities and prime location, 50 Ledge Hill Road is a renter's dream. Don't miss this unique opportunity-schedule your private tour today.
…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
Summer 2026 -- Available: June 15-30 for $9,000 -- Rented: July/Aug/Sept. This beautiful property is a direct waterfront, 4 bedroom, one-level home situated on a sandy beach in a private association. Wake up every morning to ocean waves, and enjoy the panoramic sunrises/sunsets which are magical here. Upon pulling into the driveway, you'll be greeted by breathtaking water views. The expansive patio right on the beach is perfect for entertaining or relaxing, and is just a few steps to the water. Enjoy spending days lounging on the beach, taking long walks, running, seashell collecting, swimming, entertaining, and making priceless memories. Inside, this beach home offers: stunning ocean views, high ceilings with fans, a wall of windows with sliding door, central air, recessed lighting, New England style light and bright design, open concept one-level living, ample closet space, laundry, 4 bedrooms (king bed in master), and 2 full baths. The kitchen is complete with granite, stainless steel appliances, and a large island with breakfast bar. Recent home upgrades include new furniture, new mattresses, and custom window treatments. Outside, there is a full bath, driveway parking for 4 cars, and grassy front yard. Saybrook marina, Fenwick golf course, The Kate theater, restaurants, and shopping are all close by. Only 2 hours from NYC and Boston.
…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
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.
…By William Pitt Sotheby's International Realty
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. July and August 2026. Also available September 15, 2026 - May 31, 2027 for 3K per month.
…By William Pitt Sotheby's International Realty
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These agencies offer a selection of luxury properties location at Madison. Feel free to contact them for personalized assistance.