$2,000 Per Month
- 1 Bed
- 1 Bath
- 594 Sq Ft
- House for Rent
43 Boston Post Rd, Madison, CT 06443
43 Boston Post Rd, Madison, CT 06443$2,000 Per Month
43 Boston Post Rd, Madison, CT 06443
43 Boston Post Rd, Madison, CT 06443$6,000
Total Monthly Price
1023 Boston Post Rd, Madison, CT 06443
Lease required. Minimum rental term is one week at $1,500 per week. SUMMER/FALL VACATION RENTAL IS CLOSE TO EVERYTHING: One mile to downtown and beaches! FULLY RENOVATED in 2021, this furnished, open concept cottage combines the living room, kitchen and dining area and has a separate bedroom and full bath. WALK/BIKE TO DOWNTOWN AND BEACHES; driving takes under 5 minutes. Amenities include 2 split
$3,600 Per Month
82 Wall St Unit 200, Madison, CT 06443
82 Wall St Unit 200, Madison, CT 06443$2,975 Per Month
82 Wall St Unit 300, Madison, CT 06443
82 Wall St Unit 300, Madison, CT 06443$18,000 Per Month
153 Middle Beach Rd, Madison, CT 06443
Spend your summer by the shore at 153 Middle Beach Road in Madison, a classic coastal retreat available for July and/or August 2026. Perfectly positioned in one of Madison's most sought-after beach neighborhoods, this charming home offers the relaxed lifestyle that makes summer on the Connecticut shoreline so special. Wake up to salty sea breezes, enjoy your morning coffee on the spacious front
Sheila Tinn-Murphy Berkshire Hathaway NE Prop.
$1,600
Total Monthly Price
37 Dudley Ln, Madison, CT 06443
ENJOY THE CONVENIENCE OF A LOCATION THAT PROVIDES ACCESS TO HAMMONASSET STATE PARK, DONAHUE'S, DUNKIN DOUGHNUTS, LENNY & JOE'S WITHOUT EVER GETTING IN THE CAR !! COMPLETELY REMODELED ~ EVERYTHING IS NEW !! KITCHENS AND BATH / ECONOMICAL PROPANE HEAT WITH NEWER WALL UNIT, STORM DOOR & DOUBLE PANE THERMAL WINDOWS / FREESTANDING UNIT WITH ITS OWN DRIVEWAY FOR OFF STREET PARKING / CITY WATER AND
$3,000 Per Month
33 Copse Rd Unit B, Madison, CT 06443
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
Julie Ovian William Pitt Sotheby's Int'l
$3,750
Total Monthly Price
1281 Durham Rd, Madison, CT 06443
For Rent or PurchaseCharming Large Madison Mother/Daughter Home!This delightful 4-bedroom Home features a large modern chef's kitchen, a cozy living room with a fireplace, 2 bedrooms on the first floor, a spacious bathroom, laundry area, and a bonus room that adds extra width to the house.Upstairs, you'll find a brand-new large living room, kitchen, bathroom, and 2
$6,000 Per Month
72 Cherry Ln, Madison, CT 06443
AVALIABLE SEPTEMPER FIRST 2026. Relax and enjoy this summer in a beautiful property situated just 200 yards from West Wharf Beach and 3/10th of a mile from Surf Club Beach. This newly renovated 2500 Sqft house is surrounded by golfing fairways of Madison Country Club and is located on a private lane. The property boasts a fully remodeled and newly decorated family room, dining room, large eat-in
Bob Yostos Coldwell Banker Realty
$3,400
Total Monthly Price
32 Bassett Ln, Madison, CT 06443
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
$4,500 Per Month
38 Tuxis Rd, Madison, CT 06443
Move right in on September 8th. Designed for both relaxation and productivity, this thoughtfully maintained one-floor residence offers generous living spaces and high-end finishes throughout. The home features three spacious bedrooms, including beautifully updated bathrooms that provide a luxurious retreat. A versatile overflow room offers additional flexibility with a dedicated desk/workspace
Meig Walz Newcomb Coldwell Banker Realty
$20,000
Total Monthly Price
52 Kelsey Place, Madison, CT 06443
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
$8,000 Per Month
187 Wildcat Rd, Madison, CT 06443
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
Kirsten Adams William Pitt Sotheby's Int'l
$4,200
Total Monthly Price
33 Hartford Ave, Madison, CT 06443
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
$2,350 Per Month
65 Old Route 79 Unit 5, Madison, CT 06443
Enjoy easy living in the charming Railside Place community, a small and well-maintained townhouse complex ideally located within walking distance of downtown Madison. Stroll to local shops, restaurants, the impressive town library, and all the conveniences that make Madison one of Connecticut's most desirable shoreline towns. This pristine townhouse offers a bright, open floor plan with a
Sheila Tinn-Murphy Berkshire Hathaway NE Prop.
$4,200
Total Monthly Price
33 Ridgewood Ave, Madison, CT 06443
Available for the Sept 2026 through June 2027. This sun- filled colonial has been lovingly restored for easy comfortable living. Open views of the Long Island Sound throughout this home offers room for all. Screened in wrap around porch to enjoy the warm days and nights. Updated kitchen with stainless appliances and large dining nook, mud room, office and dedicated laundry room and half bath all
$7,500 Per Month
2 Race Hill Rd, Madison, CT 06443
Rare opportunity to lease a truly one-of-a-kind furnished Academic Rental set on over 12 idyllic acres in the heart of Madison's picturesque countryside. Surrounded by nature at its finest, this private "Gentleman's Farm" offers an extraordinary setting with rolling pastures, tranquil ponds, wooded trails, and sweeping views. The antique Cape, originally built in 1740 with a thoughtfully designed
Rose Ciardiello William Raveis Real Estate
$5,000
Total Monthly Price
146 Middle Beach Rd, Madison, CT 06443
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
$11,000 Per Month
122 Taylor Ave, Madison, CT 06443
AVAILABLE FOR MONTH OF JULY. 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
Kirsten Adams William Pitt Sotheby's Int'l
$5,000
Total Monthly Price
2203 Durham Rd, Madison, CT 06443
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
$6,000 Per Month
187 Wildcat Rd, Madison, CT 06443
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
Kirsten Adams William Pitt Sotheby's Int'l
$4,000
Total Monthly Price
141 Middle Beach Rd, Madison, CT 06443
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
$3,000 Per Month
43 Neck Rd, Madison, CT 06443
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
Phoebe Schreiner William Pitt Sotheby's Int'l
$3,300
Total Monthly Price
27 Ridgewood Ave, Madison, CT 06443
SEEKING A 3 BEDROOM FULLY FURNISHED ACADEMIC RENTAL IN A MADISON BEACH COMMUNITY? This lovely home, located in the Neck Road area of Madison, with beach rights, is filled with old world charm but with modern conveniences - large Living Room is the entire front of the home, over looking a screened in porch. There is a dedicated Dining Room, 1st floor Den (office) with pull out couch and access to
$10,000 Per Month
71 Beach Ave, Madison, CT 06443
Summer furnished rental is available August 1-30th at $10,000 per month. It is also available from July 25-August 30 for $12,500. This is a wonderful opportunity for a summer vacation rental just 1 home away from a sandy, private beach on Long Island Sound in Madison. A well-built ranch located on a sweet beach lane; it offers 3 bedrooms, 2 full baths, a well-equipped modern kitchen, a large
Carol Farmer William Raveis Real Estate
$12,000
Total Monthly Price
147 Overshore Dr W, Madison, CT 06443
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
$5,600 Per Month
41 Liberty St, Madison, CT 06443
Enjoy the best weeks of summer in Madison in this exceptional, academic rental! Available August 10th, this beautifully-crafted residence offers the ideal blend of comfort and tranquility, just minutes from the shoreline and town center. The thoughtfully designed interior features a welcoming living room with gas fireplace, creating an inviting atmosphere for evening reading or entertaining
Melanie Abbott William Pitt Sotheby's Int'l
$5,250 Per Month
16 Shorelands Dr, Madison, CT 06443
Year-round rental in desirable beach community. This spacious, sunny 4+ bedroom, 3 full bath home has been entirely repainted inside, has had some updates, and kitchen has been upgraded. Large, oversized rooms both upstairs and down. Hardwood floors thoughout the first floor. Basement has new laminate floors. This property has deeded beach rights to one of Madison's loviest sandy beaches, huge
Alison Gould Gould Group LLC
$35,000 Per Month
19 Middle Beach Rd, Madison, CT 06443
This beautiful waterfront home has unobstructed views of Long Island Sound.This gorgeous home was built in 2012 with all the bells and whistles. Available for academic rent September 7th 2026 through mid June 2027 at 7K per month. JULY and AUGUST of 2027 is $35,000 PER MONTH. Ask about pets. 5 bedrooms/4 baths, City Water, Natural Gas and Central Air. Lots of parking.
Sheila Tinn-Murphy Berkshire Hathaway NE Prop.
$3,700 Per Month
31 Highland Terrace, Madison, CT 06443
Enjoy coastal living in this charming year-round rental just a short walk to private Fountain Beach in Madison. Rent also includes a spot to store a kayak, paddle board or row boat at the private beach. This 2-bedroom, 1-bath home features an inviting open floor plan with beautiful hardwood floors and an updated kitchen. The spacious living room includes a decorative fireplace, while the large 3
Janelle Maffeo Realty ONE Group Connect
$9,000 Per Month
118 Middle Beach Rd, Madison, CT 06443
ACADEMIC RENTAL! The iconic, water-front 118 Middle Beach Road is available for rent for the academic year beginning October 1, 2026. This sensational property offers comfortable occupancy for up to fourteen people with 7 bedrooms, 5 full baths, and 2 half baths. The main level is an entertainer's dream featuring an oversized, eat-in kitchen, formal dining area, living room with water views from
Melanie Abbott William Pitt Sotheby's Int'l
$2,900 Per Month
52 Overshores E, Madison, CT 06443
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
Kirsten Adams William Pitt Sotheby's Int'l
$2,400 Per Month
68 Kelsey Place, Madison, CT 06443
BEACH ! Adorable beach association ranch home available for Academic rental starting first week of Sept through May. Pets considered with additional rent. Large 3 season front porch extends living space. 2 BR plus an additional fold down futon in den. Eat in kitchen. Full shower bath was totally renovated 3 years ago. Stackable washer and dryer is 3 years old. Paved driveway can accommodate 3
Deborah Rowe William Raveis Real Estate
$7,000 Per Month
165 Middle Beach Rd, Madison, CT 06443
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
Kirsten Adams William Pitt Sotheby's Int'l
$12,000 Per Month
509 Boston Post Rd, Madison, CT 06443
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
Phoebe Schreiner William Pitt Sotheby's Int'l
$5,700 Per Month
146 Chittenden Field Ln, Madison, CT 06443
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
Sue Knapp William Pitt Sotheby's Int'l
$2,400 Per Month
55 Overshores W, Madison, CT 06443
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
Kirsten Adams William Pitt Sotheby's Int'l
$6,000 Per Month
156 Kelsey Place, Madison, CT 06443
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
Todd Gould William Pitt Sotheby's Int'l
$45,000 Per Month
118 Middle Beach Rd, Madison, CT 06443
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,
Melanie Abbott William Pitt Sotheby's Int'l