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First Time Offered In 25 Years. This contemporary raised ranch, set on 2.36 secluded acres, is located in a quiet cul-de-sac neighborhood just minutes to town. The living room with hardwood floors features a cathedral ceiling with beams, a wood burning fireplace, floor to ceiling windows with double sliders to a deck with built in bench, perfect for morning coffee or evening enjoyment. The adjacent dining room also has sliders to a patio. The kitchen with breakfast bar is waiting for your personal touches. Down the hall you will find 2 spacious guest bedrooms with large closets that share a hall bath. The primary bedroom with walk-in closet has its own full bath. Downstairs is a large family room with a wood stove to keep things cozy and sliders to an additional patio. The laundry is also located on this level. Though located in a private wooded setting, this home is conveniently located to town, beaches, parks and all that Madison has to offer.

3 Beds ⋅ 2 Baths ⋅ 24199405 MLS

First Time Offered In 25 Years. This contemporary raised ranch, set on 2.36 secluded acres, is located in a quiet cul-de-sac neighborhood just minutes to town. The living room with hardwood floors features a cathedral ceiling with beams, a wood burning fireplace, floor to ceiling windows with double sliders to a deck with built in bench, perfect for morning coffee or evening enjoyment. The adjacent dining room also has sliders to a patio. The kitchen with breakfast bar is waiting for your personal touches. Down the hall you will find 2 spacious guest bedrooms with large closets that share a hall bath. The primary bedroom with walk-in closet has its own full bath. Downstairs is a large family room with a wood stove to keep things cozy and sliders to an additional patio. The laundry is also located on this level. Though located in a private wooded setting, this home is conveniently located to town, beaches, parks and all that Madison has to offer.

35 Aileen Dr, Madison

$880,000

Turn down a long, picturesque driveway to a stunning mid-century cape, unseen from the roadway. Note, the spectacular fieldstone chimney on the large addition of the gable-end plus the closed in screened porch to the west. Ahead you'll find a large, detached 2-car garage and off to the south a small barn with great potential for an equestrian opportunity. From the screened in porch, enter the house thru its French doors. The field stone fireplace is a match to the exterior chimney. The semi-circular staircase rises to an upstairs reading room with its own fireplace and just off the primary bedroom. Both the reading room and bedroom enjoy the added light of angle-mounted skylights. Walking to the south, you'll pass the upstairs full bath, a second staircase, another full bedroom, and a study at the end of the hall. Take the traditional staircase back to the first floor and step into the foyer by the front door. Turn either left into a large, fully-equipped eat-in kitchen or turn right into a magnificent full-width dining room with a large, central fireplace with multiple windows on 3 sides over-looking the estate's grounds. Walk outside the house and turn to the west to see the well-maintained rolling acres before you. This is a lovely, well cared for private home on a very beautiful 7+ acre lot.

2 Beds ⋅ 2 Baths ⋅ 24183654 MLS

Turn down a long, picturesque driveway to a stunning mid-century cape, unseen from the roadway. Note, the spectacular fieldstone chimney on the large addition of the gable-end plus the closed in screened porch to the west. Ahead you'll find a large, detached 2-car garage and off to the south a small barn with great potential for an equestrian opportunity. From the screened in porch, enter the house thru its French doors. The field stone fireplace is a match to the exterior chimney. The semi-circular staircase rises to an upstairs reading room with its own fireplace and just off the primary bedroom. Both the reading room and bedroom enjoy the added light of angle-mounted skylights. Walking to the south, you'll pass the upstairs full bath, a second staircase, another full bedroom, and a study at the end of the hall. Take the traditional staircase back to the first floor and step into the foyer by the front door. Turn either left into a large, fully-equipped eat-in kitchen or turn right into a magnificent full-width dining room with a large, central fireplace with multiple windows on 3 sides over-looking the estate's grounds. Walk outside the house and turn to the west to see the well-maintained rolling acres before you. This is a lovely, well cared for private home on a very beautiful 7+ acre lot.

2415 Durham Rd, Madison

$210,000

Enjoy the best the shoreline has to offer in this charming seasonal summer cottage. Bring your swimsuits, sunscreen, and a book... and move right into this furnished, turnkey summer house. One of the largest cottages, this home has central air, 2-3 parking spaces, and a lovely lot. Sun-filled, airy, and spacious, with a large kitchen and dining room, a generous living room, and 2 additional rooms. Listed as a 1-bedroom, but could easily be used as 2 bedrooms, or 1 bedroom and a flex room. The half bath even has an all-in-one washer/dryer unit. You'll love the outdoor shower, fresh air, under the stars, no sand in the house. Outside is a large storage shed and a screened gazebo, perfect for al fresco dining! Finish out the summer enjoying sunsets and relaxation. A quick bike ride to Hammonasset Beach State Park, restaurants, downtown Madison, the movie theater and shops.

1 Beds ⋅ 1 Baths ⋅ 24197701 MLS

Enjoy the best the shoreline has to offer in this charming seasonal summer cottage. Bring your swimsuits, sunscreen, and a book... and move right into this furnished, turnkey summer house. One of the largest cottages, this home has central air, 2-3 parking spaces, and a lovely lot. Sun-filled, airy, and spacious, with a large kitchen and dining room, a generous living room, and 2 additional rooms. Listed as a 1-bedroom, but could easily be used as 2 bedrooms, or 1 bedroom and a flex room. The half bath even has an all-in-one washer/dryer unit. You'll love the outdoor shower, fresh air, under the stars, no sand in the house. Outside is a large storage shed and a screened gazebo, perfect for al fresco dining! Finish out the summer enjoying sunsets and relaxation. A quick bike ride to Hammonasset Beach State Park, restaurants, downtown Madison, the movie theater and shops.

40 East St, Madison

$529,000

Nicely maintained 3-bedroom, 3-full-bath home nestled in a quaint cul-de-sac setting. The home is in very good condition and offers comfortable living space both inside and out. The spacious kitchen features granite countertops, plenty of cabinet space, and a center island-perfect for everyday living and entertaining. Primary Bedroom has its own private full bath. Living Room-Dining combination offers a slider to a deck overlooking the peaceful backyard and small pond, creating a relaxing setting to enjoy the outdoors. Lower level offers a large family room with a walk-out to a patio, providing additional living and entertaining space. With its peaceful setting, versatile living spaces, and inviting outdoor areas, this home is ready to welcome its next owners.

3 Beds ⋅ 3 Baths ⋅ 24198297 MLS

Nicely maintained 3-bedroom, 3-full-bath home nestled in a quaint cul-de-sac setting. The home is in very good condition and offers comfortable living space both inside and out. The spacious kitchen features granite countertops, plenty of cabinet space, and a center island-perfect for everyday living and entertaining. Primary Bedroom has its own private full bath. Living Room-Dining combination offers a slider to a deck overlooking the peaceful backyard and small pond, creating a relaxing setting to enjoy the outdoors. Lower level offers a large family room with a walk-out to a patio, providing additional living and entertaining space. With its peaceful setting, versatile living spaces, and inviting outdoor areas, this home is ready to welcome its next owners.

25 Samantha Ln, Madison

$749,900

Tucked away on a sweet cul-de-sac at the end of a private road, well off of Route 79, this spacious 4-bedroom Colonial welcomes you with a wonderful sense of privacy and tranquility. Enjoy plenty of room to gather, relax, and make yourself at home, including a full finished walk out basement with endless possibilities. This low maintenance home features a new roof, hardwood floors throughout, a new kitchen island & new granite countertops. The inviting first floor features a bright family room with a wood burning fireplace and French doors to a freshly painted deck. There are only a few steps to the 2-car attached garage. It also features a comfortable living room and dining room. The second floor has 4 large bedrooms with newly installed hardwood floors. The primary bedroom with vaulted ceilings and skylight has an en-suite bathroom with soaking tub & walk in shower. There is a walk-up attic off of the second bedroom, currently being used as an office. Laundry is on the second floor opposite the family bathroom. Two more large bedrooms complete the second floor. The walk-out basement is partially finished with a game room, office area, bedroom and full bathroom. Ideally located near hiking & biking trails for the nature enthusiast. Enjoy all that the charming town of Madison has to offer; award winning high school, 3 beautiful town beaches, plus Hammonasset State Park, shops, restaurants, state of the art library plus a wonderful community.

4 Beds ⋅ 4 Baths ⋅ 24195345 MLS

Tucked away on a sweet cul-de-sac at the end of a private road, well off of Route 79, this spacious 4-bedroom Colonial welcomes you with a wonderful sense of privacy and tranquility. Enjoy plenty of room to gather, relax, and make yourself at home, including a full finished walk out basement with endless possibilities. This low maintenance home features a new roof, hardwood floors throughout, a new kitchen island & new granite countertops. The inviting first floor features a bright family room with a wood burning fireplace and French doors to a freshly painted deck. There are only a few steps to the 2-car attached garage. It also features a comfortable living room and dining room. The second floor has 4 large bedrooms with newly installed hardwood floors. The primary bedroom with vaulted ceilings and skylight has an en-suite bathroom with soaking tub & walk in shower. There is a walk-up attic off of the second bedroom, currently being used as an office. Laundry is on the second floor opposite the family bathroom. Two more large bedrooms complete the second floor. The walk-out basement is partially finished with a game room, office area, bedroom and full bathroom. Ideally located near hiking & biking trails for the nature enthusiast. Enjoy all that the charming town of Madison has to offer; award winning high school, 3 beautiful town beaches, plus Hammonasset State Park, shops, restaurants, state of the art library plus a wonderful community.

2125 Durham Rd, Madison

$899,000

Give away the leaf blower and the yard tools (or sell, whichever you prefer) and get ready to enjoy life on a peaceful cul-de-sac in Madison's highly desirable Strathmore Farms community with natural gas and city water, 3 Longview Terrace is an exceptional stand-alone condominium home that captures the essence of luxurious coastal living. Recent updates to this home include the furnace and roof, both new in 2025. This thoughtful 3-bedroom Colonial seamlessly blends elegance and comfort, offering a flowing first-floor layout that includes a formal dining room, a living room, an eat-in kitchen that opens to a family room with a fireplace as a focal point, and rounded out with a dedicated home office/flex space. The beautiful eat-in kitchen is the heart of the home with sliding doors that open to a large deck overlooking the meadow. Beyond the elegant interior, this property is a dream for nature enthusiasts, offering access to the community gazebo as well as kayaking, paddle boarding, and birdwatching. Enjoy the marsh-view setting, the quick two-mile drive to the stunning shoreline of Hammonasset Beach State Park, and convenience to Madison village. This home combines the space and privacy of a detached home with a premier, carefree lifestyle.

3 Beds ⋅ 4 Baths ⋅ 24193091 MLS

Give away the leaf blower and the yard tools (or sell, whichever you prefer) and get ready to enjoy life on a peaceful cul-de-sac in Madison's highly desirable Strathmore Farms community with natural gas and city water, 3 Longview Terrace is an exceptional stand-alone condominium home that captures the essence of luxurious coastal living. Recent updates to this home include the furnace and roof, both new in 2025. This thoughtful 3-bedroom Colonial seamlessly blends elegance and comfort, offering a flowing first-floor layout that includes a formal dining room, a living room, an eat-in kitchen that opens to a family room with a fireplace as a focal point, and rounded out with a dedicated home office/flex space. The beautiful eat-in kitchen is the heart of the home with sliding doors that open to a large deck overlooking the meadow. Beyond the elegant interior, this property is a dream for nature enthusiasts, offering access to the community gazebo as well as kayaking, paddle boarding, and birdwatching. Enjoy the marsh-view setting, the quick two-mile drive to the stunning shoreline of Hammonasset Beach State Park, and convenience to Madison village. This home combines the space and privacy of a detached home with a premier, carefree lifestyle.

3 Longview Ter Unit 3, Madison

$899,000

Set on a peaceful cul-de-sac in Madison's highly desirable Strathmore Farms community, 3 Longview Terrace is an exceptional stand-alone condominium home that captures the essence of luxurious coastal living. This thoughtful 3-bedroom Colonial seamlessly blends elegance and comfort, offering a flowing first-floor layout that includes a formal dining room, a living room, an eat-in kitchen that opens to a family room with a fireplace as a focal point, and rounded out with a dedicated home office/flex space. The beautiful eat-in kitchen is the heart of the home with sliding doors that open to a large deck overlooking the meadow. Beyond the elegant interior, this property is a dream for nature enthusiasts, offering access to the community gazebo as well as kayaking, paddle boarding, and birdwatching. Enjoy the marsh-view setting, the quick two-mile drive to the stunning shoreline of Hammonasset Beach State Park, and convenience to Madison village. This home combines the space and privacy of a detached home with a premier, carefree lifestyle.

3 Beds ⋅ 4 Baths ⋅ 24192261 MLS ⋅ Strathmore Farms BLDG.

Set on a peaceful cul-de-sac in Madison's highly desirable Strathmore Farms community, 3 Longview Terrace is an exceptional stand-alone condominium home that captures the essence of luxurious coastal living. This thoughtful 3-bedroom Colonial seamlessly blends elegance and comfort, offering a flowing first-floor layout that includes a formal dining room, a living room, an eat-in kitchen that opens to a family room with a fireplace as a focal point, and rounded out with a dedicated home office/flex space. The beautiful eat-in kitchen is the heart of the home with sliding doors that open to a large deck overlooking the meadow. Beyond the elegant interior, this property is a dream for nature enthusiasts, offering access to the community gazebo as well as kayaking, paddle boarding, and birdwatching. Enjoy the marsh-view setting, the quick two-mile drive to the stunning shoreline of Hammonasset Beach State Park, and convenience to Madison village. This home combines the space and privacy of a detached home with a premier, carefree lifestyle.

3 Longview Ter Unit 3, Madison

$999,000

Live the Connecticut Shoreline Life on 4 Private Acres. Picture mornings on your sun-filled balcony overlooking open fields, afternoon walks along Madison's public beaches, and evenings on the covered patio as the light fades over the tree line and old stone walls. Pastoral. Private. Purposeful. The main house, 3-bedroom and 2.5-bathroom, has wide wood flooring throughout. The primary ensuite has a private balcony accessed through private double sliding glass door. Two separate staircases. One staircase gives private access to primary bedroom. Livingroom, dining room, eat-in-kitchen, open floor plan, and enclosed porches provide flexible living space. Enclosed potting room off of the kitchen offers easy access to garden beds for wholesome farm to table dinners.

5 Beds ⋅ 6 Baths ⋅ 24187090 MLS

Live the Connecticut Shoreline Life on 4 Private Acres. Picture mornings on your sun-filled balcony overlooking open fields, afternoon walks along Madison's public beaches, and evenings on the covered patio as the light fades over the tree line and old stone walls. Pastoral. Private. Purposeful. The main house, 3-bedroom and 2.5-bathroom, has wide wood flooring throughout. The primary ensuite has a private balcony accessed through private double sliding glass door. Two separate staircases. One staircase gives private access to primary bedroom. Livingroom, dining room, eat-in-kitchen, open floor plan, and enclosed porches provide flexible living space. Enclosed potting room off of the kitchen offers easy access to garden beds for wholesome farm to table dinners.

1209 Durham Rd, Madison

$139,900

New roof, new windows, new deck! 32 North Street is ready for you and calling you home! Set on one of the largest lots in Dud's Village, this lovely cottage is the idyllic seasonal abode. Equipped with 2 bedrooms, 1 full bath, and an outdoor shower, you will surely enjoy your summers along the Madison shoreline here. The recently refreshed kitchen and fresh coat of paint throughout will undoubtedly delight. And let's not forget the new floors in the kitchen and living room. The enclosed front porch is simply charming offering additional living space and featuring daybeds for cool summer sleepovers. Outside is an entertainer's paradise - a desirable corner lot with the oversized deck and enough yard space to host all your family and friends. Just a short distance to Salt Meadow Park, Hammonasset Beach State Park and downtown Madison, you'll always have something to do! And with summer right around the corner, you'll want to move quickly! Schedule your tour today and fully embrace coastal living at its finest! The village is seasonal - April 1st through October 31st. Land is leased by cottage owners, and the land lease is currently $5,400 per year. New windows and deck to be completed as soon as possible.

2 Beds ⋅ 1 Baths ⋅ 24170543 MLS

New roof, new windows, new deck! 32 North Street is ready for you and calling you home! Set on one of the largest lots in Dud's Village, this lovely cottage is the idyllic seasonal abode. Equipped with 2 bedrooms, 1 full bath, and an outdoor shower, you will surely enjoy your summers along the Madison shoreline here. The recently refreshed kitchen and fresh coat of paint throughout will undoubtedly delight. And let's not forget the new floors in the kitchen and living room. The enclosed front porch is simply charming offering additional living space and featuring daybeds for cool summer sleepovers. Outside is an entertainer's paradise - a desirable corner lot with the oversized deck and enough yard space to host all your family and friends. Just a short distance to Salt Meadow Park, Hammonasset Beach State Park and downtown Madison, you'll always have something to do! And with summer right around the corner, you'll want to move quickly! Schedule your tour today and fully embrace coastal living at its finest! The village is seasonal - April 1st through October 31st. Land is leased by cottage owners, and the land lease is currently $5,400 per year. New windows and deck to be completed as soon as possible.

32 North St, Madison

$125,000

Escape to the Connecticut shoreline with this beautifully maintained seasonal cottage in Dud's Village in Madison-the perfect summer retreat just minutes from the beach. Located less than one mile from Hammonasset Beach State Park, Connecticut's largest shoreline park, this charming getaway offers effortless access to two miles of sandy beaches, scenic walking and biking trails, and endless summer activities. Residents of Dud's Village also enjoy a private path that leads directly to the beach, making spontaneous sunset walks and beach days part of everyday life. This fully furnished, move-in-ready cottage has been thoughtfully maintained and cared for, allowing you to start enjoying the season immediately. The cozy interior includes one bedroom with built-in storage, a nicely stocked kitchen, a sleeper sofa for additional guests, a remodeled bathroom with a fresh modern feel, and the added convenience of an in-unit washer and dryer. Step outside to your spacious wrap-around deck, designed for relaxed coastal living and easy entertaining. The outdoor space comes complete with a grill, tabletop firepit, and patio seating, creating the perfect setting for summer evenings, morning coffee, or gathering with friends after a day at the beach.

1 Beds ⋅ 1 Baths ⋅ 24160104 MLS

Escape to the Connecticut shoreline with this beautifully maintained seasonal cottage in Dud's Village in Madison-the perfect summer retreat just minutes from the beach. Located less than one mile from Hammonasset Beach State Park, Connecticut's largest shoreline park, this charming getaway offers effortless access to two miles of sandy beaches, scenic walking and biking trails, and endless summer activities. Residents of Dud's Village also enjoy a private path that leads directly to the beach, making spontaneous sunset walks and beach days part of everyday life. This fully furnished, move-in-ready cottage has been thoughtfully maintained and cared for, allowing you to start enjoying the season immediately. The cozy interior includes one bedroom with built-in storage, a nicely stocked kitchen, a sleeper sofa for additional guests, a remodeled bathroom with a fresh modern feel, and the added convenience of an in-unit washer and dryer. Step outside to your spacious wrap-around deck, designed for relaxed coastal living and easy entertaining. The outdoor space comes complete with a grill, tabletop firepit, and patio seating, creating the perfect setting for summer evenings, morning coffee, or gathering with friends after a day at the beach.

16 North St, Madison

$595,000

Nestled in the highly sought-after Windermere East community, this rare free-standing condo offers the perfect blend of privacy, comfort, and coastal charm in beautiful Madison. Enjoy serene river views and a peaceful setting just moments from the shoreline. This well-maintained home features 2 bedrooms and 2 full baths, a spacious fireplaced living room, and a bright kitchen ideal for everyday living. The new HVAC system with gas heat and central air ensures year-round comfort and efficiency. A lovely 3-season sunroom that offers additional living space and opens to a private patio-perfect for relaxing, entertaining and enjoying the view of the river. Ideal for kayaking right from your backyard, with space to conveniently store your kayak onsite. A standout feature of this unit is the full basement-an uncommon find in the complex-offering abundant storage, a cedar closet, and partially finished space with endless possibilities. Ideally located within walking distance to Hammonasset Beach State Park and scenic walking trails, and just minutes to marina's and downtown Madison where you'll find fine dining, a charming movie theater, shops and the beloved RJ Julia Booksellers. Enjoy the best of shoreline living in one of Madison's most desirable communities-an ideal choice for those looking to downsize or create the perfect coastal escape.

2 Beds ⋅ 2 Baths ⋅ 24160683 MLS ⋅ Windermere East BLDG.

Nestled in the highly sought-after Windermere East community, this rare free-standing condo offers the perfect blend of privacy, comfort, and coastal charm in beautiful Madison. Enjoy serene river views and a peaceful setting just moments from the shoreline. This well-maintained home features 2 bedrooms and 2 full baths, a spacious fireplaced living room, and a bright kitchen ideal for everyday living. The new HVAC system with gas heat and central air ensures year-round comfort and efficiency. A lovely 3-season sunroom that offers additional living space and opens to a private patio-perfect for relaxing, entertaining and enjoying the view of the river. Ideal for kayaking right from your backyard, with space to conveniently store your kayak onsite. A standout feature of this unit is the full basement-an uncommon find in the complex-offering abundant storage, a cedar closet, and partially finished space with endless possibilities. Ideally located within walking distance to Hammonasset Beach State Park and scenic walking trails, and just minutes to marina's and downtown Madison where you'll find fine dining, a charming movie theater, shops and the beloved RJ Julia Booksellers. Enjoy the best of shoreline living in one of Madison's most desirable communities-an ideal choice for those looking to downsize or create the perfect coastal escape.

10 Runnymede Ln Unit 10, Madison

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