32

Homes for Rent near Walter C. Polson Upper Middle School

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  • /16

    $3,700 per month

    • 2 Beds
    • 1.5 Baths
    • 1,590 Sq Ft
    • House for Rent

    3 Highland Terrace, Madison, CT 06443

    Beach cottage rental. Private beach one block away plus access to more. 3 options to rent: 1. Full year @ $3900/month (includes summer re price) 2. For the summer July/August @ $9000 3. Academic September 1-June 31 @$3400 The house is a 1920's converted bungalow. Yellow with a white picket fence. We call it the enchanted cottage not only because of how it looks and feels but because it is

    3 Highland Terrace, Madison, CT 06443
  • /30

    $9,000 per month

    • 7 Beds
    • 7 Baths
    • 5,075 Sq Ft
    • House for Rent

    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, 2025. 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

    118 Middle Beach Rd, Madison, CT 06443
  • /14

    $2,200 per month

    • 2 Beds
    • 1 Bath
    • 1,210 Sq Ft
    • Apartment for Rent

    710 Boston Post Rd Unit 714 2nd floor apt, Madison, CT 06443

    TWO BEDROOM APARTMENT IN DOWNTOWN MADISON. Enjoy he convenience of being downtown, close to Madison shops, library and beaches. Recently refreshed, this apartment is ready for immediate occupancy. shared laundry in the building Excellent credit, two months security, credit check and references required. No smoking or pets.

    Sue Woods William Pitt Sotheby's Int'l

    710 Boston Post Rd Unit 714 2nd floor apt, Madison, CT 06443
  • /21

    $3,500 per month

    • 3 Beds
    • 2 Baths
    • 1,568 Sq Ft
    • House for Rent

    116 Overshores E, Madison, CT 06443

    RELAX IN THIS VINTAGE 3-BEDROOM COLONIAL W/ STUNNING SCREENED PORCH ~ SET IN PRIVATE SANDY BEACH COMMUNITY A SHORT WALK TO THE BEAUTIFUL WAVES OF LONG ISLAND SOUND ~ HOME WILL BE AVAILABLE EARLY SEPTEMBER FOR THE ACADEMIC YEAR AT $3,500/MONTH

    Tom Clancy William Pitt Sotheby's Int'l

    116 Overshores E, Madison, CT 06443
  • /39

    $3,300 per month

    • 4 Beds
    • 2 Baths
    • 1,530 Sq Ft
    • House for Rent

    32 Bassett Ln, Madison, CT 06443

    AVAILABLE FROM SEPTEMBER 8, 2025 TO JUNE 15, 2026! 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

    Kirsten Adams William Pitt Sotheby's Int'l

    32 Bassett Ln, Madison, CT 06443
  • /20

    $5,000 per month

    • 3 Beds
    • 1.5 Baths
    • 1,398 Sq Ft
    • House for Rent

    75 Circle Beach Rd, Madison, CT 06443

    Secure your academic rental now!! Available Sept 15, 2025- May 15, 2026. Fully Furnished, all utilities included.

    Cindy Breckheimer Forever Homes Real Estate LLC

    75 Circle Beach Rd, Madison, CT 06443
  • /33

    $6,250 per month

    • 4 Beds
    • 3 Baths
    • 3,495 Sq Ft
    • House for Rent

    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 updateds, 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

    16 Shorelands Dr, Madison, CT 06443
  • /34

    $5,000 per month

    • 3 Beds
    • 2.5 Baths
    • 1,861 Sq Ft
    • House for Rent

    8 Lawson Dr, Madison, CT 06443

    Pristine cape right around the corner from East Wharf beach. Walk or ride bikes to the beach, and along the Long Island Sound coastline. Enjoy evenings outside on the spacious patio with stone fire pit, outdoor furniture, dining table, and built-in grilling station. Ride bikes or walk to town and nearby restaurants. Entertain family and guests in the beautifully designed kitchen, and comfortable

    Meig Walz Newcomb Coldwell Banker Realty

    8 Lawson Dr, Madison, CT 06443
  • /29

    $3,100 per month

    • 3 Beds
    • 2 Baths
    • 1,529 Sq Ft
    • House for Rent

    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

    Kirsten Adams William Pitt Sotheby's Int'l

    27 Ridgewood Ave, Madison, CT 06443
  • /30

    $8,000 per month

    • 4 Beds
    • 2.5 Baths
    • 3,127 Sq Ft
    • House for Rent

    144 Middle Beach Rd, Madison, CT 06443

    Your beach sanctuary awaits!!! This direct waterfront beauty will be available as an academic year rental from Labor Day through Memorial Day. Enjoy your own private sandy beach at low tide. With 4 bedrooms and 2.5 baths, you'll have plenty of space for friends and family. Upon entry, you are welcomed by an open floor plan, with a tastefully remodeled kitchen, living room and dining room combo,

    Agota Perry-Hill William Raveis Real Estate

    144 Middle Beach Rd, Madison, CT 06443
  • /31

    $13,000 per month

    • 3 Beds
    • 1.5 Baths
    • 1,518 Sq Ft
    • House for Rent

    22 Fairview Ave, Madison, CT 06443

    What a fantastic location! Enjoy the month of August this charming, mint condition, furnished cape located in the very desirable Seaview beach area. Perfect retreat for a relaxing escape by the sea. Your very own beach association is just steps away. All you need is a beach chair and a good book and feel any stress you may have simply dissipate! The sunrises and sunsets are spectacular. You will

    Anne-Marie Pagli William Raveis Real Estate

    22 Fairview Ave, Madison, CT 06443
  • /29

    $3,300 per month

    • 3 Beds
    • 1.5 Baths
    • 1,518 Sq Ft
    • House for Rent

    22 Fairview Ave, Madison, CT 06443

    This charming three bedroom beautifully furnished cape is located in one of the most desirable areas in Madison-Seaview Beach. It is available Oct. 1, 2025-May 31, 2026. The house has several updates including the appliances. One of the bedrooms is located on the first floor and two very spacious bedrooms are on the second floor. There is a sun filled familyroom, a cozy livingroom with a

    Anne-Marie Pagli William Raveis Real Estate

    22 Fairview Ave, Madison, CT 06443
  • /29

    $5,750 per month

    • 3 Beds
    • 3 Baths
    • 2,467 Sq Ft
    • House for Rent

    29 Parker Ln, Madison, CT 06443

    ACADEMIC FURNISHED RENTAL - Available Sept 15th through May 15th 2026. Fabulous direct waterfront home offers a gracious open layout on the first level. Newly updated kitchen with a back deck for grilling opens to the dining room and first floor living area with gas fireplace. Step out onto the deck and enjoy the water views all year long. A mud room that leads to a recently remodeled full bath

    Sue Knapp William Pitt Sotheby's Int'l

    29 Parker Ln, Madison, CT 06443
  • /31

    $15,000 per month

    • 4 Beds
    • 2 Baths
    • 2,016 Sq Ft
    • House for Rent

    121 Overshores W, Madison, CT 06443

    WONDERFUL 4 BEDROOM VINTAGE SUMMER HOME, AVAILABLE FOR THE MONTH OF AUGUST 2025. Renovated but with old world charm - plenty of gathering areas for family and friends in Living Room, Dining Room, Sun Room and outdoor patio. Kitchen was renovated, along with 1st floor bath, house has new exterior shingles, new outdoor shower (for the post beach days), new septic. Located in the coveted (and

    Kirsten Adams William Pitt Sotheby's Int'l

    121 Overshores W, Madison, CT 06443
  • /10

    $2,450 per month

    • 2 Beds
    • 1 Bath
    • 692 Sq Ft
    • House for Rent

    24 Gull Rock Rd, Madison, CT 06443

    ACADEMIC RENTAL. 9/15/2025 - 5/15/2026. ALL UTILITIES INCLUDED! Charming Guest House Retreat off Middle Beach Road. Welcome to this delightful guest house, called "The Nest", an escape nestled just 1/2 block from Long Island Sound in the town of Madison. Offering a cosey amount of living space, this property is the perfect blend of convenience and coastal charm. There is an inviting Family Room,

    Kirsten Adams William Pitt Sotheby's Int'l

    24 Gull Rock Rd, Madison, CT 06443
  • /23

    $2,800 per month

    • 2 Beds
    • 2 Baths
    • 1,684 Sq Ft
    • House for Rent

    52 Overshores E, Madison, CT 06443

    ACADEMIC RENTAL AVAILABLE - September 8, 2025 to May 31, 2026. 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

    52 Overshores E, Madison, CT 06443
  • /39

    $16,000 per month

    • 4 Beds
    • 2 Baths
    • 1,530 Sq Ft
    • House for Rent

    32 Bassett Ln, Madison, CT 06443

    AVAILABLE FROM JULY 11 TO AUGUST 23! RENT THE ENTIRE TIME OR FOR ANY PORTION OF! 3 WEEKS = $8,000, 6 WEEKS = $16,000. 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

    Kirsten Adams William Pitt Sotheby's Int'l

    32 Bassett Ln, Madison, CT 06443
  • /39

    $3,000 per month

    • 4 Beds
    • 2 Baths
    • 1,530 Sq Ft
    • House for Rent

    32 Bassett Ln, Madison, CT 06443

    AVAILABLE FROM MAY 7 TO JUNE 25! 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

    Kirsten Adams William Pitt Sotheby's Int'l

    32 Bassett Ln, Madison, CT 06443
  • /17

    $4,500 per month

    • 3 Beds
    • 2.5 Baths
    • 3,516 Sq Ft
    • House for Rent

    30 Beaver Pond Rd, Madison, CT 06443

    Spacious and stylish academic rental available September 2025 to May 2026. Beautifully appointed three bedroom, 2 1/2 bath single story home with modern updates, generous living space, and a thoughtfully designed layout. Updated kitchen, expansive living areas with plenty of natural light, and a lovely finished basement with storage. Brand new propane fired heating system and central air.

    Dana Weinstein Coldwell Banker Realty

    30 Beaver Pond Rd, Madison, CT 06443
  • /8

    $4,000 per month

    • 1 Bath
    • 490 Sq Ft
    • House for Rent

    141 Middle Beach Rd, Madison, CT 06443

    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

    Sue Knapp William Pitt Sotheby's Int'l

    141 Middle Beach Rd, Madison, CT 06443
  • /26

    $6,000 per month

    • 4 Beds
    • 2.5 Baths
    • 2,100 Sq Ft
    • House for Rent

    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, 2026. 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

    Sue Knapp William Pitt Sotheby's Int'l

    146 Middle Beach Rd, Madison, CT 06443
  • /31

    $14,000 per month

    • 4 Beds
    • 2 Baths
    • 1,886 Sq Ft
    • House for Rent

    71 Beach Ave, Madison, CT 06443

    71 Beach Avenue is available July 19th with the following options: 7/19-8/31/25 for $20,000. Or rent for the month of August for $14,000. A rambling one-level home, it is fully furnished. One home away from its own private beach, it is a truly special property. This beautifully maintained home has three bedrooms and two full bathrooms. You can feel the breeze off the Sound throughout the house,

    Carol Farmer William Raveis Real Estate

    71 Beach Ave, Madison, CT 06443
  • /24

    $2,000 per month

    • 1 Bed
    • 1 Bath
    • 792 Sq Ft
    • Townhouse for Rent

    65 Old Route 79 Unit 13, Madison, CT 06443

    Great location close to town, train, shopping and beaches. Large kitchen with lots of cabinetry and counter space with a convenient eat-in area too! The bedroom is large and bright with a walk-in closet plus an additional closet. The unit comes with a stackable washer/dryer. The pull down stairs attic has some additional storage space. Central air and radiant heat. This small complex offers

    Sheila Tinn-Murphy Berkshire Hathaway NE Prop.

    65 Old Route 79 Unit 13, Madison, CT 06443
  • /28

    $11,000 per month

    • 3 Beds
    • 1.5 Baths
    • 1,418 Sq Ft
    • House for Rent

    122 Taylor Ave, Madison, CT 06443

    AVAILABLE FOR MONTH OF AUGUST. Relax and unwind for a summer at the beach. This well maintained, freshly painted 3 bedroom home with vintage beach house charm, has easy access to a private Association beach just steps away. Three carpeted bedrooms are: one king (master), one full and one with 2 twin beds. This home has an "L" shaped Living Room and Dining Room. The kitchen is well equipped for

    Kirsten Adams William Pitt Sotheby's Int'l

    122 Taylor Ave, Madison, CT 06443
  • /31

    $11,000 per month

    • 3 Beds
    • 1.5 Baths
    • 1,418 Sq Ft
    • House for Rent

    122 Taylor Ave, Madison, CT 06443

    AVAILABLE FOR MONTH OF JULY. Relax and unwind for a summer at the beach. This well maintained, freshly painted 3 bedroom home with vintage beach house charm, has easy access to a private Association beach just steps away. Three carpeted bedrooms are: one king (master), one full and one with 2 twin beds. This home has an "L" shaped Living Room and Dining Room. The kitchen is well equipped for all

    Kirsten Adams William Pitt Sotheby's Int'l

    122 Taylor Ave, Madison, CT 06443
  • /31

    $12,000 per month

    • 3 Beds
    • 2 Baths
    • 1,529 Sq Ft
    • House for Rent

    27 Ridgewood Ave, Madison, CT 06443

    AVAILABLE FOR THE MONTH OF JULY 2025. SEEKING A 3 BEDROOM FULLY FURNISHED SUMMER 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

    Kirsten Adams William Pitt Sotheby's Int'l

    27 Ridgewood Ave, Madison, CT 06443
  • /30

    $6,500 per month

    • 3 Beds
    • 3 Baths
    • 1,713 Sq Ft
    • House for Rent

    23 Linden Ln, Madison, CT 06443

    You truly can't find a better location to rent a water area home for the summer months. This sweet, 3 bedroom cape is meticulously maintained w/ spectacular marsh views and only a 3 minute stroll to one of Madison's premier beaches, East Wharf Beach. Linden Lane is well known by those who live there as a perfect, quite lane enhanced by pride of ownership homes and marsh views that are

    Amy Kirst William Pitt Sotheby's Int'l

    23 Linden Ln, Madison, CT 06443
  • /20

    $5,500 per month

    • 3 Beds
    • 1.5 Baths
    • 1,398 Sq Ft
    • House for Rent

    75 Circle Beach Rd, Madison, CT 06443

    Available Jan 15- May 1st only or by Full Month (January can be pro-rated). Fully Furnished, all utilities included.

    Cindy Breckheimer Forever Homes Real Estate LLC

    75 Circle Beach Rd, Madison, CT 06443
  • /16

    $7,500 per month

    • 2 Beds
    • 2 Baths
    • 1,204 Sq Ft
    • House for Rent

    57 Harbor Ave, Madison, CT 06443

    MONTH OF AUGUST!... You don't want to miss this one... A short walk to a nice sandy beach on Long Island Sound. Cozy and efficient Bungalow in Beach Community. Open Floor Plan. Kitchen with granite counters, hardwood floors throughout, central air conditioning. First Floor Master Bedroom with full bath and king bed, and second bedroom is on the upper floor with 2 single beds and its own

    Alison Gould Gould Group LLC

    57 Harbor Ave, Madison, CT 06443
  • /40

    $5,500 per month

    • 4 Beds
    • 2.5 Baths
    • 2,511 Sq Ft
    • House for Rent

    72 Cherry Ln, Madison, CT 06443

    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 kitchen, four bright bedrooms, 2

    Bob Yostos Coldwell Banker Realty

    72 Cherry Ln, Madison, CT 06443
  • /31

    $8,949 per month

    • 4 Beds
    • 3 Baths
    • 1,869 Sq Ft
    • House for Rent

    43 Soundview Ave, Madison, CT 06443

    Fabulous academic rental available 10/1 through May 31st 2025. This direct waterfront four bedroom home set on a one of kind property with access to a private beach. Enjoy fabulous views from your deck, large yard and tidal pool. Plenty of space for everyone with a bedroom with full bath on the main level, Primary en suite on the second floor with private balcony and two additional bedrooms with

    Sue Knapp William Pitt Sotheby's Int'l

    43 Soundview Ave, Madison, CT 06443
  • /30

    $4,000 per month

    • 6 Beds
    • 3 Baths
    • 3,593 Sq Ft
    • House for Rent

    106 Buffalo Bay, Madison, CT 06443

    Six bedroom home situated on one acre in the private beach association of Buffalo Bay, with access to the Association's beach and tennis court, steps from the house. Tranquil private waterfront setting, close to town center..Fully furnished, including all linens, sheets, tableware, etc. Available Sep.1, 2025 thru May 31,2026 at $4,000/month, plus CT mandated rental tax of $600. Security deposit

    Steve Adkins Berkshire Hathaway NE Prop.

    106 Buffalo Bay, Madison, CT 06443
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