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$1,950,000

Completely rebuilt and expanded in 2026, this custom coastal home with deeded beach rights is located in Madison's charming Seafields Association. Thoughtfully designed with designer details throughout, the home provides elevated shoreline living with glimpses of Long Island Sound, state-of-the-art appliances, high-end finishes, a bright, open layout, mudroom, butler's pantry with laundry, and a warm family room with fireplace and wine bar. The private primary suite features a balcony with distant water views, a spa-inspired marble wet room bath, and custom walk-in closet. Outdoor living includes a patio, fenced in yard, outdoor shower - an ideal setting for entertaining and coastal living.

3 Beds ⋅ 4 Baths ⋅ 24177522 MLS

Completely rebuilt and expanded in 2026, this custom coastal home with deeded beach rights is located in Madison's charming Seafields Association. Thoughtfully designed with designer details throughout, the home provides elevated shoreline living with glimpses of Long Island Sound, state-of-the-art appliances, high-end finishes, a bright, open layout, mudroom, butler's pantry with laundry, and a warm family room with fireplace and wine bar. The private primary suite features a balcony with distant water views, a spa-inspired marble wet room bath, and custom walk-in closet. Outdoor living includes a patio, fenced in yard, outdoor shower - an ideal setting for entertaining and coastal living.

26 Bassett Ln, Madison

$1,695,000

Historic gem on the Madison Village Green. Once known as "Hartsbourne," this storied Madison residence is celebrated for its premier location overlooking the town green and its timeless architectural presence. A true local landmark, the home is distinguished by its striking curved eaved roofline, reminiscent of a pagoda with a unique flat seamed copper roof center. Beautifully aligned with the neighboring Congregational Church, the home shares architectural harmony through its grand columns and elegant two-story shutters. The architect, Mr. Volney Pierce, was commissioned to design this exceptional residence and later the Congregational Church. Inside, the home offers more than 3,900 square feet of living space with soaring 9+ foot ceilings on the main level, 2nd floor with five generously sized bedrooms, five working fireplaces, and the 3rd floor a uniquely large attic with unlimited possibilities. At the back of the property are the outbuildings, a 3 car garage and small coop/shed. "Hartsbourne", has abundant historic character throughout. Set on 1.5+ acres in the heart of Madison's charming village, this is a rare opportunity to own a true piece of local history.

5 Beds ⋅ 4 Baths ⋅ 24173597 MLS

Historic gem on the Madison Village Green. Once known as "Hartsbourne," this storied Madison residence is celebrated for its premier location overlooking the town green and its timeless architectural presence. A true local landmark, the home is distinguished by its striking curved eaved roofline, reminiscent of a pagoda with a unique flat seamed copper roof center. Beautifully aligned with the neighboring Congregational Church, the home shares architectural harmony through its grand columns and elegant two-story shutters. The architect, Mr. Volney Pierce, was commissioned to design this exceptional residence and later the Congregational Church. Inside, the home offers more than 3,900 square feet of living space with soaring 9+ foot ceilings on the main level, 2nd floor with five generously sized bedrooms, five working fireplaces, and the 3rd floor a uniquely large attic with unlimited possibilities. At the back of the property are the outbuildings, a 3 car garage and small coop/shed. "Hartsbourne", has abundant historic character throughout. Set on 1.5+ acres in the heart of Madison's charming village, this is a rare opportunity to own a true piece of local history.

30 Meeting House Ln, Madison

$149,900

With a new roof in process, 32 North Street is 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 roof to be completed as quickly as possible.

2 Beds ⋅ 1 Baths ⋅ 24170543 MLS

With a new roof in process, 32 North Street is 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 roof to be completed as quickly as possible.

32 North St, Madison

$142,900

Nestled in the heart of picturesque Madison, this charming 2-bedroom, 1-bathroom seasonal cottage offers a serene sanctuary for enjoying summers along the shoreline. With a cozy living space, this quaint abode is perfectly designed for those seeking a peaceful beachside getaway. As you step inside, you're greeted by a warm and inviting atmosphere that captures the essence of coastal living. The open-plan living area maximizes the cottage's compact footprint, providing a comfortable space for relaxation and intimate gatherings. The kitchen is well-equipped for preparing light bites and beach picnics, while the two snug bedrooms offer a restful night's sleep after a day of fun in the sun. The loft space above the bedrooms awaits your imagination and offers an abundance of possibilities - pre-wired and ready to be finished to your heart's content! The cottage's prime location means you're just a short walk from the expansive sandy shores of Hammonasset Beach State Park. Madison's vibrant community is also at your doorstep, with its quaint downtown area, boutique shops, excellent restaurants, and attractions like the Madison Art Cinema and the historic E.C. Scranton Library. Whether you're looking for outdoor adventure or small-town charm, this cottage is the perfect seasonal home. Embrace the simplicity of cottage living and the beauty of coastal Connecticut with this delightful property, where endless summer memories await. Land lease - currently $5,400 per year.

2 Beds ⋅ 1 Baths ⋅ 24168727 MLS

Nestled in the heart of picturesque Madison, this charming 2-bedroom, 1-bathroom seasonal cottage offers a serene sanctuary for enjoying summers along the shoreline. With a cozy living space, this quaint abode is perfectly designed for those seeking a peaceful beachside getaway. As you step inside, you're greeted by a warm and inviting atmosphere that captures the essence of coastal living. The open-plan living area maximizes the cottage's compact footprint, providing a comfortable space for relaxation and intimate gatherings. The kitchen is well-equipped for preparing light bites and beach picnics, while the two snug bedrooms offer a restful night's sleep after a day of fun in the sun. The loft space above the bedrooms awaits your imagination and offers an abundance of possibilities - pre-wired and ready to be finished to your heart's content! The cottage's prime location means you're just a short walk from the expansive sandy shores of Hammonasset Beach State Park. Madison's vibrant community is also at your doorstep, with its quaint downtown area, boutique shops, excellent restaurants, and attractions like the Madison Art Cinema and the historic E.C. Scranton Library. Whether you're looking for outdoor adventure or small-town charm, this cottage is the perfect seasonal home. Embrace the simplicity of cottage living and the beauty of coastal Connecticut with this delightful property, where endless summer memories await. Land lease - currently $5,400 per year.

92 Fourth Ave, Madison

$3,495,000

Exceptionally located less than a tenth of a mile from both the town green and beaches - with your own private beach access - this stunning residence sits on 1.57 secluded acres and has been completely re-imagined with uncompromising attention to detail and the finest materials. The home offers 16 thoughtfully designed rooms. Sun filled interiors feature over sized windows and expansive sight lines, anchored by a massive family room and a top of the line chef's kitchen. The lower level is a true walkout guest suite with additional living space plus a separate garage apartment for overnight guests. Outside amenities evoke a private resort: a gunite pool, extensive stone patios, two fully equipped outdoor kitchens, and a charming grassy area framed by mature landscaping for complete privacy. This is a rare coastal estate that blends modern, high end finishes with relaxed, year round seaside living. Practical luxury continues with a three car garage, circular driveway, and generous storage. This is truly a must see, and all reasonable offers will be entertained.

5 Beds ⋅ 6 Baths ⋅ 24166497 MLS

Exceptionally located less than a tenth of a mile from both the town green and beaches - with your own private beach access - this stunning residence sits on 1.57 secluded acres and has been completely re-imagined with uncompromising attention to detail and the finest materials. The home offers 16 thoughtfully designed rooms. Sun filled interiors feature over sized windows and expansive sight lines, anchored by a massive family room and a top of the line chef's kitchen. The lower level is a true walkout guest suite with additional living space plus a separate garage apartment for overnight guests. Outside amenities evoke a private resort: a gunite pool, extensive stone patios, two fully equipped outdoor kitchens, and a charming grassy area framed by mature landscaping for complete privacy. This is a rare coastal estate that blends modern, high end finishes with relaxed, year round seaside living. Practical luxury continues with a three car garage, circular driveway, and generous storage. This is truly a must see, and all reasonable offers will be entertained.

45 Island Ave, Madison

$1,975,000

Updated 4 bedroom 2 Full bath Cape on 15+ Acres of rolling Meadows and woods bordering State Forest and over 800 feet of frontage on Opening Hill. Extensive updating includes new windows and doors, original wide-board refinishing in the original building. A new kitchen in the cathedral ceilinged family room addition with deck that commands beautiful views of two spring fed, stocked ponds below the home. Just updated with New Doors and Windows and 2 full baths. A traditional paneled downstairs family room with wood burning fireplace offers direct access to the basement and under house double length garage.

4 Beds ⋅ 2 Baths ⋅ 24163897 MLS

Updated 4 bedroom 2 Full bath Cape on 15+ Acres of rolling Meadows and woods bordering State Forest and over 800 feet of frontage on Opening Hill. Extensive updating includes new windows and doors, original wide-board refinishing in the original building. A new kitchen in the cathedral ceilinged family room addition with deck that commands beautiful views of two spring fed, stocked ponds below the home. Just updated with New Doors and Windows and 2 full baths. A traditional paneled downstairs family room with wood burning fireplace offers direct access to the basement and under house double length garage.

441 Opening Hill Rd, 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

$1,975,000

Modern luxury meets sustainable living in a premier location. Set on more than two private acres in one of the area's most sought-after neighborhoods, this brand-new contemporary home offers a bright, open-concept design that blends sophisticated style with everyday comfort. At the heart of the home, the chef's kitchen impresses with a Sub-Zero refrigerator, Wolf appliances, custom cabinetry, and stunning quartzite countertops. The space flows effortlessly into the expansive great room, where a dramatic floor-to-ceiling fireplace creates a striking focal point for gathering and entertaining. The main-level primary suite serves as a private retreat, featuring its own stone fireplace, spacious walk-in closet, and luxurious ensuite bath. The walkout lower level adds exceptional flexibility with two additional bedrooms, a shared full bath, two generous flex spaces ideal for a home office, gym, media room, or recreation area, plus an additional half bath. Designed with both efficiency and longevity in mind, the home is equipped with an energy-efficient geothermal heating and cooling system, providing year-round comfort while helping reduce utility costs. A premium metal roof offers outstanding durability, low maintenance, and lasting protection for decades to come. Additional features include a two-car garage and exceptional privacy, all just minutes from Madison's charming village center, beautiful beaches, and convenient access to I-95.

4 Beds ⋅ 4 Baths ⋅ 24155109 MLS

Modern luxury meets sustainable living in a premier location. Set on more than two private acres in one of the area's most sought-after neighborhoods, this brand-new contemporary home offers a bright, open-concept design that blends sophisticated style with everyday comfort. At the heart of the home, the chef's kitchen impresses with a Sub-Zero refrigerator, Wolf appliances, custom cabinetry, and stunning quartzite countertops. The space flows effortlessly into the expansive great room, where a dramatic floor-to-ceiling fireplace creates a striking focal point for gathering and entertaining. The main-level primary suite serves as a private retreat, featuring its own stone fireplace, spacious walk-in closet, and luxurious ensuite bath. The walkout lower level adds exceptional flexibility with two additional bedrooms, a shared full bath, two generous flex spaces ideal for a home office, gym, media room, or recreation area, plus an additional half bath. Designed with both efficiency and longevity in mind, the home is equipped with an energy-efficient geothermal heating and cooling system, providing year-round comfort while helping reduce utility costs. A premium metal roof offers outstanding durability, low maintenance, and lasting protection for decades to come. Additional features include a two-car garage and exceptional privacy, all just minutes from Madison's charming village center, beautiful beaches, and convenient access to I-95.

81 Strawberry Hill Rd, Madison

$2,290,000

Less than one mile from downtown Madison, this new construction home offers refined living with white oak floors, custom millwork, coffered ceilings, and abundant natural light throughout. The main level features 9-foot ceilings, a dramatic floor-to-ceiling gas stone fireplace with built-ins, a chef's kitchen with Sub-Zero and Wolf appliances, double ovens, pot filler, wet bar with wine chiller, walk-in pantry, first-floor laundry, private office, and a luxurious primary suite with soaking tub, oversized rain shower, double vanity, custom walk-in closet, and floor-to-ceiling tile. Upstairs includes four bedrooms and three full baths, walk-in closets, and a bonus room with floor-to-ceiling nickel gap and oversized French doors leading to your new home gym. Additional highlights include central vacuum system, elevated covered patio, and a high-ceiling basement (9 ft) ready for finishing.

5 Beds ⋅ 5 Baths ⋅ 24145947 MLS

Less than one mile from downtown Madison, this new construction home offers refined living with white oak floors, custom millwork, coffered ceilings, and abundant natural light throughout. The main level features 9-foot ceilings, a dramatic floor-to-ceiling gas stone fireplace with built-ins, a chef's kitchen with Sub-Zero and Wolf appliances, double ovens, pot filler, wet bar with wine chiller, walk-in pantry, first-floor laundry, private office, and a luxurious primary suite with soaking tub, oversized rain shower, double vanity, custom walk-in closet, and floor-to-ceiling tile. Upstairs includes four bedrooms and three full baths, walk-in closets, and a bonus room with floor-to-ceiling nickel gap and oversized French doors leading to your new home gym. Additional highlights include central vacuum system, elevated covered patio, and a high-ceiling basement (9 ft) ready for finishing.

92 Scotland Ave, Madison

$2,295,000

Built by a highly regarded shoreline builder known for uncompromising attention to detail, this residence is designed for buyers who appreciate elevated finishes, enduring quality, and effortless livability. The home features an open floor plan with white oak hardwood floors, 9-foot ceilings, custom millwork, and oversized Pella windows throughout. A stunning bluestone entry leads to an elegant interior anchored by an eat-in kitchen with a 5' x 7.5' quartz island, Sub-Zero refrigeration, a six-burner Wolf gas range, double wall ovens, farmhouse sink, and wet bar with wine chiller and refrigerator drawers. The living room offers coffered ceilings, a stone-surround gas fireplace, and sliding doors to a partially covered bluestone patio, creating seamless indoor-outdoor living. The primary suite is a private retreat with a spa-inspired bath featuring a soaking tub, oversized rain shower, dual vanities, and a walk-in closet. Three additional bedrooms each include en-suite baths, complemented by a bonus room with cathedral ceilings and full bath. Additional highlights include a private office, formal dining room, custom pantry and mudroom, set up for a generator, and a well-appointed laundry room.

4 Beds ⋅ 6 Baths ⋅ 24147939 MLS

Built by a highly regarded shoreline builder known for uncompromising attention to detail, this residence is designed for buyers who appreciate elevated finishes, enduring quality, and effortless livability. The home features an open floor plan with white oak hardwood floors, 9-foot ceilings, custom millwork, and oversized Pella windows throughout. A stunning bluestone entry leads to an elegant interior anchored by an eat-in kitchen with a 5' x 7.5' quartz island, Sub-Zero refrigeration, a six-burner Wolf gas range, double wall ovens, farmhouse sink, and wet bar with wine chiller and refrigerator drawers. The living room offers coffered ceilings, a stone-surround gas fireplace, and sliding doors to a partially covered bluestone patio, creating seamless indoor-outdoor living. The primary suite is a private retreat with a spa-inspired bath featuring a soaking tub, oversized rain shower, dual vanities, and a walk-in closet. Three additional bedrooms each include en-suite baths, complemented by a bonus room with cathedral ceilings and full bath. Additional highlights include a private office, formal dining room, custom pantry and mudroom, set up for a generator, and a well-appointed laundry room.

23 Sheep Pasture Rd, Madison