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343 Horse Pond Rd, Madison
$675,000
3 Beds ⋅ 3 Baths ⋅ 24207706 MLS
***Seller financing available - below market rate! Ask agent for details*** This sun-drenched and beautifully updated Cape offers a rare blend of charm, versatility, and an exceptional shoreline location. With two distinct living spaces, the property presents an outstanding opportunity for multigenerational living or a compelling investment property. The main residence features a stylishly renovated kitchen opening to a spacious dining area, two bedrooms-including an impressively spacious primary bedroom-two full baths, and a fabulous rear deck perfect for outdoor dining and entertaining. The attached in-law suite offers privacy and independence with its own updated kitchenette, full bath, washer and dryer, and beautiful open loft-style bedroom-ideal for extended family, guests, a private home office, or potential rental income. Outside, enjoy a large detached garage, hot tub, and storage shed. Located across from Cole's Farm, with a fishing pond just a short walk away and Hammonasset Beach State Park within an easy bike ride. Convenient to scenic trails, downtown, shopping, and dining, this unique property offers extraordinary flexibility and coastal living at its best!

343 Horse Pond Rd, Madison
39 Mill Rd, Madison
$550,000
5 Beds ⋅ 2 Baths ⋅ 24206863 MLS
The Perfect Location on picturesque 3/4 of an Acre. Walk to Hammonasset State Park and enjoy the Trails and 2-Miles of Pristine Sandy Beach ~ This Antique Saltbox boasts a total of 2,262 square feet of heated living space. Windows have been upgraded with Pella Double Pane Insulated Windows throughout. Included in the floor plan is a legal 1-Bedroom Apartment on the first floor. You'll need to Roll up your sleeves and do some work, but the results should pay dividends.

39 Mill Rd, Madison
3 Little Hollow Rd, Madison
$795,000
4 Beds ⋅ 3 Baths ⋅ 24205125 MLS
Welcome home to this classic four-bedroom Colonial offering timeless charm, modern updates, and an ideal layout for everyday living, complete with gorgeous wide plank flooring throughout. Freshly updated, the home features stylish new light fixtures and major mechanical upgrades, including a new roof (2022) and a new Carrier HVAC system for the second floor (2026). At the heart of the main level is an eat-in kitchen with cabinets painted in 2022, a new dishwasher (2024), and a spacious dining area set in front of a cozy fireplace. Sunlight pours into the breathtaking family room featuring soaring vaulted ceilings and a warm gas fireplace. Glass French doors open from the welcoming foyer into the living room, which boasts its own fireplace and connects seamlessly to the formal dining room. A dedicated mudroom off the kitchen includes a new washer and dryer (2024), alongside a convenient first-floor half bath. Upstairs, the primary suite serves as a peaceful retreat with vaulted ceilings, an expansive walk-in closet, and a private full bath. Three additional generous bedrooms share a renovated full bath with double sinks. Step outside to an impressive deck overlooking a lush yard-perfect for outdoor dining, playing, or relaxing. Ideally located just minutes from top-rated schools, vibrant town amenities, and picturesque local beaches, this move-in-ready property offers the ultimate combination of space, style, and peace of mind.

3 Little Hollow Rd, Madison
420 Summer Hill Rd, Madison
$1,295,000
4 Beds ⋅ 3 Baths ⋅ 24200477 MLS
Set on nearly two private acres in a quiet, peaceful setting, this beautifully maintained home offers more than 4,000 square feet of spacious, light-filled living. Built in 1999 and presented in excellent condition, the home features an inviting open floor plan, generously sized rooms, four large bedrooms, and two fireplaces that add warmth and character. Abundant natural light highlights the home's beautiful architectural details and creates a bright, welcoming atmosphere throughout. The expansive living spaces offer wonderful flexibility for both everyday living and entertaining, while a peaceful deck provides the perfect place to relax and enjoy the privacy and natural surroundings. A full walk-out basement offers exceptional potential for additional finished living space-ideal for a home gym, recreation room, playroom, office, or media room. Completing the property is a spacious three-car garage. Offering impressive scale, privacy, natural light, and a serene setting, this exceptional home combines comfort and versatility with timeless appeal.

420 Summer Hill Rd, Madison
148 Mungertown Rd, Madison
$1,149,000
4 Beds ⋅ 4 Baths ⋅ 24205471 MLS
A Rare Madison Historic Homestead - Built with Purpose, Rich in History Discover a truly distinctive property at the former Helen Foster Snow homestead. The home was owner-built for his own family, reflecting a personal vision of home and a place to put down roots, not a property created simply for resale. Its history and individuality set it apart from the ordinary. This special offering includes two separate parcels totaling approximately 3.02 acres. The approximately 1.5-acre homesite features the main residence, a separate one-bedroom guest house, two barns, and a picturesque pond, offering a unique combination of historic character, flexible living space, and room to pursue your interests. An additional approximately 1.52-acre parcel is included, providing extra land and future possibilities. Buildability has not been confirmed, and buyers are encouraged to conduct their own due diligence regarding zoning, approvals, and potential uses. Whether you envision multigenerational living, space for hobbies and creative pursuits, a workshop, or simply a property with character and room to spread out, this distinctive Madison homestead offers a rare opportunity to make a special place your own. More than a house, this is a property with a story, built for family and ready for its next chapter conveniently located just minutes from Hammonasset Beach State Park, The Surf Club, and all that the Connecticut shoreline has to offer.

148 Mungertown Rd, Madison
23 Esterly Farms Rd Unit 23, Madison
$489,000
2 Beds ⋅ 3 Baths ⋅ 24203806 MLS ⋅ Esterly Farms BLDG.
Welcome to 23 Esterly Farms, an exceptional end-unit townhouse offering the perfect blend of style, comfort, and turnkey convenience in one of Madison's most sought-after condominium communities. This meticulously maintained 2-bedroom, 2.5-bath home has been thoughtfully updated throughout, allowing you to move right in and enjoy worry-free living. The sun-filled interior showcases fresh paint, all-new Harvey replacement windows, updated lighting, new window treatments, and a beautifully remodeled primary bath. The refreshed kitchen features brand-new stainless steel appliances, while the inviting living area is highlighted by a fireplace with elegant new glass doors. Additional upgrades include a new washer and dryer, delivering everyday convenience and modern functionality. Significant mechanical improvements provide added peace of mind, including a new furnace, central air condenser, and hot water heater. Nearly every major system has been updated, making this home truly move-in ready.

23 Esterly Farms Rd Unit 23, Madison
6 Bower Rd, Madison
$559,900
3 Beds ⋅ 1 Baths ⋅ 24203485 MLS
Escape to the Connecticut shoreline with this beautifully styled Cape, ideally situated in desirable Madison. Offering 3 bedrooms and 1 full bath, this charming home features inviting indoor and outdoor living spaces designed for comfortable everyday living and relaxed coastal living. Set on a private, lightly wooded corner lot, the property offers a peaceful sense of privacy while remaining close to everything Madison has to offer. Recent improvements include new cedar siding, windows throughout with custom window treatments, propane fireplace installation, and professional interior painting, all completed in 2025. The roof and septic system were both replaced in 2022. Just a 5-minute drive to vibrant downtown Madison, enjoy easy access to charming boutiques, restaurants, and cafes, as well as Hammonasset Beach State Park, with miles of sandy shoreline and scenic coastal walks. Convenient access to I-95 puts downtown New Haven approximately 25 minutes away. Turnkey and thoughtfully updated, this inviting Cape offers the perfect blend of classic New England charm, modern improvements, and an exceptional shoreline location. A wonderful opportunity to enjoy the best of Madison living in a peaceful coastal setting.

6 Bower Rd, Madison
22 Stone Rd, Madison
$3,200,000
5 Beds ⋅ 4 Baths ⋅ 24203132 MLS
Experience coastal Madison living with beach rights in this to be built 5-bedroom, 3.5-bathroom home featuring 4,937 square feet of high-end craftsmanship. Designed with an airy, open layout, the main level boasts 9'+ ceilings, Red Oak hardwood floors, and a chef's kitchen equipped with white Shaker cabinetry, quartz countertops, a butler's pantry, and premium Sub-Zero, Wolf, and Bosch appliances. Modern efficiency meets high design with 4-zone HVAC and tankless hot water. Upstairs, unwind in luxurious porcelain-tiled baths complete with Kohler fixtures, custom glass-door showers, and a soaking tub. Outside, enjoy a large main deck, covered front entry, landscaped grounds, and a spacious 3-car garage all just minutes from the shoreline, local schools, and downtown Madison.

22 Stone Rd, Madison
67 Blakeman Rd, Madison
$650,000
3 Beds ⋅ 3 Baths ⋅ 24172475 MLS
BEACH HOME! BEACH RIGHTS! NEEDS WORK! It is not everyday that an opportunity to own a double lot in such a shoreline area. This charming English Cottage-style Cape, situated on a generous footprint for the area, is ready for it's next chapter-whether that involves a thoughtful renovation or the construction of a brand-new coastal home perhaps. Residents enjoy deeded rights to a private association sandy beach located just at the end of the street! The main residence of which there are no photos for obvious reasons once you see it (NEEDS WORK) currently features three bedrooms and 1.5 baths but adding to the property's versatility is a delightful in good condition accessory apartment, which offers a full kitchen, full bath, a private bedroom and a cozy living area anchored by a stone fireplace and two separate exterior entrances. This setup is ideal for multi-generational living, a great guest suite or potential rental income. Maybe live in this while redoing the other portion. The property is a double lot that accommodates four dedicated parking spaces - a true luxury for beachside living. Best of all, the property is located where no flood insurance is required, offering peace of mind alongside the salt air. Whether you choose to polish this unique gem or start fresh with a custom build, this is the perfect canvas for your seaside lifestyle.

67 Blakeman Rd, Madison
118 River Rd, Madison
$5,000,000
3 Beds ⋅ 3 Baths ⋅ 24192754 MLS
Some properties are defined by the house that sits on them. Others are defined by the land itself...by history, landscape and a sense of beauty that simply cannot be created. This is such a place. Owned and farmed by the same family for 200 years, this remarkable 16 Acre piece sitting on the Hammonassett River is the last piece of the original farm to be sold. With over 1500 ft. bordering the river, the property unfolds across open hay fields, tidal marshes and expansive river views. The landscape changes with the seasons and the light, grasses moving with the wind and water reflecting the ever changing sky...a landscape that is both bucolic and breathtaking. This is an exceptional setting for a distinctive country residence, a private retreat or a place to enjoy a quieter chapter of life. An existing, well appointed, three bedroom ranch home sits on the property and enjoys the same remarkable views. Comfortable as it stands, the home could ultimately serve as a guest house, artist's studio or private office. The property offers the potential for more than one lot, but with generations of family ownership, the sellers have hopes to see the land remain intact, so no soil testing has been undertaken for subdivision. A survey is available and buyers considering additional development should conduct their own due diligence. After two centuries in the same family, this is a rare opportunity to become the next steward of an extraordinary Connecticut landscape.

118 River Rd, Madison
35 Aileen Dr, Madison
$499,900
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
78 Lantern Hill Rd, Madison
$900,000
24200319 MLS
Build Your Dream Home on Prestigious Lantern Hill Road Discover an exceptional opportunity to own a 1.2acre parcel tucked away on one of Madison's most coveted and private culdesacs. Located at 78 Lantern Hill Road, this hidden gem offers the perfect balance of tranquility and convenience-less than a mile from Madison's beautiful beaches, vibrant town center, boutique shopping, dining, golf, and quick access to I95 for effortless commuting. Surrounded by impeccably maintained, luxury homes-many valued around the $3 million mark-this premier lot provides an ideal canvas for an elegant coastal residence. Mature trees, serene natural surroundings, and underground utilities enhance the setting, making it ready for a highend build that complements the neighborhood's sophistication. Experience the best of shoreline living in Madison, celebrated for its charming village atmosphere, thriving arts and culture, abundant recreation, and pristine coastline. Whether you envision a yearround sanctuary or a summer retreat, this location offers a rare blend of privacy, luxury, and accessibility. Don't miss the chance to build in one of Connecticut's most soughtafter seaside communities.

78 Lantern Hill Rd, Madison
2415 Durham Rd, Madison
$880,000
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
17 Barberry Ln, Madison
$2,700,000
4 Beds ⋅ 6 Baths ⋅ 24197827 MLS
RARE OPPORTUNITY in the highly sought-after Barberry Farms Association! With only 2 MLS sales since 2021, homes in this premier beach community seldom become available. Enjoy private access to a wonderfully wide & deep sandy beach that has storage bins & an area for kayaks & small sailboats to make life easier. BIG home, BIG rooms. Spanning 4,833 sq ft, this 10 room Colonial features hardwood floors throughout. Off the formal entry foyer sits a den/library w/ built-ins, ideal for a home office, & a formal living room centered by a wood-burning fireplace. The main level also boasts a formal dining room w/ a bow window, & a center island chef's kitchen w/ granite counters, double ovens & a real walk-in pantry. Adjacent to the kitchen, a natural light filled family room offers a gas fireplace, a bow window & sliders out to a broad bluestone patio for outdoor entertaining. Upstairs features cathedral ceilings, a vaulted game room, a large laundry room w/ utility sink that is super convenient, & 4 bedrooms, 3 w/ walk-in closets. Highlights include 2 ensuites! The primary retreat has a spacious bathroom with deluxe spa tub, oversized glass shower, long double vanity, even an English heated towel rack. Set on professionally landscaped grounds, the flat open backyard is ready for lawn games or a future pool. Features include 4 full/2 half baths, a full basement, 8-zone (!) natural gas heat, city water & a 3 car garage. Exceptional coastal living. Don't wait another 5 years!

17 Barberry Ln, Madison
40 East St, Madison
$210,000
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
6 Woodland Rd Unit 4A & 4B, Madison
$265,000
24198543 MLS
INCREDIBLY CONVENIENT LOCATION just off Exit 60 of I-95 & Route 79...East Shore Medical Center, A 2,000 Sq Ft medical office condominium on the second floor in an elevatored building. Reception area, treatment rooms, offices & consulting rooms. Everything perfectly laid out for a medical practice. Across the street from Madison Ambulance. Lots of parkng. Easy access to Route 79, I-95 & Route 1. HVAC units are 1 year old. Building recently painted and re-roofed.

6 Woodland Rd Unit 4A & 4B, Madison
25 Samantha Ln, Madison
$529,000
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. Rockland Preserve is just across the street with hiking/biking trails. Chatfield Hollow State Park just few minutes away.

25 Samantha Ln, Madison
2125 Durham Rd, Madison
$749,900
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
262 Mungertown Rd, Madison
$1,750,000
4 Beds ⋅ 4 Baths ⋅ 24191892 MLS
Welcome to an incredible opportunity to build your custom dream home in South Madison! Tucked off the main road for optimal peace and quiet, this interior 2.32-acre level, treed lot is situated on the hidden, secluded end of Mungertown Road. Accessed via a private, shared residential driveway, it offers the perfect balance of PRIVACY and GREAT CONVENIENCE. Just THREE MILES to town and beaches, ONE MILE to Hand and Polson schools, and .25 MILES to the state-of-the-art Neck River Elementary, opened in 2025. Enjoy quick access to I-95 and the train. Work with an ELITE CONNECTICUT BUILDER with 35-PLUS YEARS EXPERIENCE to customize one of his flexible floor plans or BRING YOUR OWN! This property offers tremendous potential and versatility. Optional high-end features can be tailored to the buyer's taste, such as hardwood floors, crown molding, coffered or tray ceilings, and raised paneling. Personalize your home with your choice of cabinets, countertops, lighting, and tile fixtures, all built for LOW MAINTENANCE with multiple heating options available. Conveniently located near local shopping, dining, parks, and major commuter routes. A rare opportunity in an ideal Madison location-contact us today to start planning your dream build!

262 Mungertown Rd, Madison
15 Highland Ter, Madison
$2,190,000
5 Beds ⋅ 3 Baths ⋅ 24191331 MLS
COME EXPERIENCE THIS ONE-OF-A-KIND, FULLY RENOVATED MADISON HOME ON A RARE DOUBLE LOT WITH PRIVATE BEACH RIGHTS! Just 300 feet from the sandy shoreline, this exceptional home has been completely reimagined from a traditional raised ranch into a stunning elevated ranch with a bright, open-concept floor plan designed for modern living and effortless entertaining. Every detail has been thoughtfully curated to blend contemporary elegance with coastal charm. The main level features a spectacular chef's kitchen anchored by a nearly 10-foot white quartz island, premium appliances, and exceptional finishes. Two driveways provide ample parking, while two sets of washers and dryers offer added convenience. Multiple living spaces are bathed in natural light, including a breathtaking sunroom with brand-new oversized Marvin picture windows framing serene views toward Long Island Sound. A spacious hallway leads to a beautifully renovated full bath, a conveniently located laundry area, and the luxurious primary suite. Originally two bedrooms, this private retreat now offers a remarkable 9' x 12' walk-in closet and a spa-inspired ensuite featuring a double vanity, dual rain showers, and built-in shower benches. The finished lower level includes three generously sized bedrooms, a beautifully renovated full bath with a double vanity, a second brand-new washer and dryer, and an expansive family room, providing flexible space for guests, recreation, or relaxing after a day at the beach!

15 Highland Ter, Madison
3 Longview Ter Unit 3, Madison
$899,000
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
3 Longview Ter Unit 3, Madison
$899,000
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
1209 Durham Rd, Madison
$999,000
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
32 Liberty St, Madison
$1,299,000
3 Beds ⋅ 3 Baths ⋅ 24181259 MLS
Rare coastal compound opportunity in Madison's highly desirable Seaview Beach area. Situated on approximately one-half acre just moments from the shoreline, this unique property features a main residence and a newer detached accessory dwelling unit, offering flexibility rarely found in one of Connecticut's premier shoreline communities. The main home is clean, functional, and ready for a new owner's vision, while the newer detached dwelling provides additional living space ideal for guests, multigenerational living, rental income, a private home office, or extended family. Separate utilities further enhance the property's versatility. Located within Madison's top-rated school district and surrounded by higher-end homes, this property offers a unique combination of location, flexibility, and long-term potential. Enjoy convenient access to beaches, downtown Madison, restaurants, shopping, marinas, parks, and commuter routes. Whether you're seeking a private coastal retreat, family compound, investment opportunity, or future expansion potential, opportunities like this are increasingly rare. Seller financing available for qualified buyers. Buyer to perform all due diligence regarding future use, expansion, and development opportunities.

32 Liberty St, Madison
77 Silo Hill, Madison
$1,300,000
5 Beds ⋅ 4 Baths ⋅ 24183446 MLS
Welcome to this fabulous one-owner custom home in sought-after Neck River Farms. A gracious, spacious foyer warmly welcomes you inside, setting the tone for the beautifully maintained interior filled with abundant natural light. A dedicated home office with elegant French doors offers the perfect space for working remotely or quiet study. The inviting living room is ideal for entertaining, featuring oversized windows, soaring ceilings, and detailed crown molding. The heart of the home is the well-appointed kitchen with a vaulted ceiling, complete with a large center island, generous pantry storage, and granite countertops. It flows seamlessly into the cozy family room, where a wood-burning fireplace creates a perfect gathering space. Upstairs, you'll find 4 bedrooms plus a versatile guest suite above the garage, complete with a full bath and private back staircase-ideal for extended stays or multigenerational living. The primary bedroom is spacious with a luxurious bath and walk-in closet. The finished basement provides additional flexible space for a playroom, fitness area, or media room. Situated at the end of a cul-de-sac, this home offers privacy on 4.12 acres of beautifully landscaped grounds. The level backyard features a lovely stone patio and plenty of room for a pool. Additional highlights include a newer 3-year-old asphalt shingle roof, new furnace and air handler. A rare opportunity to own a spacious and thoughtfully designed home in a desirable location

77 Silo Hill, Madison
26 Bassett Ln, Madison
$1,850,000
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
30 Meeting House Ln, Madison
$1,695,000
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
32 North St, Madison
$139,900
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
508 Old Toll Rd, Madison
$550,000
24170118 MLS
Overview Turnkey opportunity to acquire a well-established restaurant business in the desirable shoreline town of Madison, Connecticut. The James Madison House Restaurant benefits from strong local recognition, consistent year-round traffic, and proximity to the town center and coastal attractions. This is an ideal opportunity for an owner-operator or experienced restaurateur to step into an existing operation with immediate income potential and upside. Key Highlights Established restaurant with loyal customer base Prime shoreline location in high-income demographic Turnkey operation with existing kitchen and infrastructure Consistent year-round business with seasonal upside Located within an active commercial setting Opportunity to rebrand or enhance concept Facility Fully built-out restaurant space Equipped commercial kitchen Dining area with established layout Lease in place Growth & Expansion Opportunities Extend operating hours / add service days Introduce new menu concepts or bar program Increase marketing and digital presence Expand catering / private events

508 Old Toll Rd, Madison
885 Boston Post Rd, Madison
$599,900
24168048 MLS
Fully approved and ready to go, this exceptional commercial lot is situated in the heart of vibrant downtown Madison. Boasting approvals for a 5,000 square foot building the property includes a brand-new septic system, 13 designated parking spaces with additional parking options, and unbeatable proximity to restaurants, shopping, the train station, and I-95. Imagine welcoming clients or customers just a short stroll from Madison's beautiful beaches in this high-visibility location. Whether you're looking to create a professional office, boutique retail space, or explore endless other possibilities, this is a rare chance to establish your business in one of the shoreline's most desirable communities. The potential here is truly unlimited!

885 Boston Post Rd, Madison

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