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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

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

45 Island Ave, Madison
$3,000,000
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

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

24 Indigo Trl, Madison
$2,550,000
4 Beds ⋅ 5 Baths ⋅ 24159028 MLS
Set on 5.65 secluded acres in the heart of Madison, this exceptional English Georgian custom home offers a rare blend of timeless architecture, refined craftsmanship, and natural beauty. Surrounded by mature woodlands, the property is a private retreat, complete with a gently winding stream and the preserved stone remnants of a historic mill-an evocative nod to the land's rich past. Inside, the home is thoughtfully designed for both elegant living and everyday comfort, featuring expansive, light-filled spaces and exquisite millwork throughout. The custom chef's kitchen is a true centerpiece, appointed with premium appliances, striking imported granite countertops, and impeccable detailing. A grand entryway welcomes you with a sweeping staircase and a beautifully crafted coffered ceiling, setting the tone for the quality and sophistication found in every room. Layout designed for first floor primary suite. This is a home for those who appreciate enduring design, superior construction, and a setting that feels worlds away-yet remains close to everything Madison has to offer.

24 Indigo Trl, Madison

31 Neptune Ave, Madison
$2,495,000
3 Beds ⋅ 3 Baths ⋅ 24212438 MLS
This charming 1920 coastal home, rich in character and timeless appeal, must not be missed. Seamlessly blending architectural details with breezy seaside style, it embodies classic coastal living. Designed around a distinctive gable-front-and-wing architectural footprint, the home extends deeply from front to back, creating abundant interior space while maximizing outdoor living. An open floor plan, hardwood floors, plentiful windows, beadboard detailing, and a mix of cathedral and tray ceilings fill the home with natural light and offer glimpses of the Long Island Sound. The lush, fenced private gardens provide a serene setting for entertaining, relaxing, and recreation. Three separate entrances from the house lead to a step-down slate patio, creating an effortless connection between indoor and outdoor living. The kitchen, three bathrooms, and glass enclosed porch have been thoughtfully updated, featuring stainless steel appliances and beautiful bluestone flooring. Two staircases and double sitting rooms provide flexibility for everyday living and entertaining. Two fireplaces add warmth and character, while two laundry rooms and dual-zone heating and air conditioning provide convenience. Just minutes from downtown Madison and the train station, the property offers access to two beaches- including one just three houses away, plus deeded rights to the coveted Barberry Farms Association beach, making this home a truly special seaside retreat.

31 Neptune Ave, Madison

23 Sheep Pasture Rd, Madison
$2,215,000
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

92 Scotland Ave, Madison
$2,195,000
5 Beds ⋅ 5 Baths ⋅ 24145947 MLS
THIS NEW CONSTRUCTION HOME with a first flow primary bedroom suite 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. Less than a mile from downtown.

92 Scotland Ave, 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

81 Strawberry Hill Rd, Madison
$1,975,000
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

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

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

87 Wildcat Springs Dr, Madison
$1,600,000
4 Beds ⋅ 4 Baths ⋅ 24208958 MLS
Set on one of Madison's most coveted streets, this distinguished 3665-square-foot Colonial offers a rare combination of refined living space and a private resort-style setting, all just minutes from downtown Madison. A gracious two-story foyer with classic wainscoting sets the tone, leading to an elegant formal dining room and a private main-level office. At the heart of the home, the chef's kitchen is finished with crisp white cabinetry, granite counters, a gas cooktop, double wall ovens, a walk-in pantry, and an oversized island with seating. It flows into a sunlit breakfast room and a welcoming family room with a gas fireplace. Gleaming hardwood floors run throughout. The second floor offers four generous bedrooms, including a serene primary suite with a spa-inspired bath and two walk-in closets. A second-floor laundry and a versatile bonus room above the garage, ideal as a home gym, playroom, or media retreat, add everyday ease and room to grow. Outdoors, the property is a true private escape. A spacious deck off the main living area offers room for alfresco dining and lounging, with stairs leading down to a beautifully landscaped, fully fenced yard framed by mature evergreens. The centerpiece is a stunning free-form in-ground pool surrounded by an expansive stamped concrete terrace, where a raised stone spa spills into the pool over a cascading waterfall.

87 Wildcat Springs Dr, 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

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

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

22 Kingsbridge Way Unit 22, Madison
$1,225,000
4 Beds ⋅ 3 Baths ⋅ 24213580 MLS
Welcome to a truly special waterfront residence where sophisticated updates, thoughtful design, and an extraordinary setting come together. A completely rebuilt and expanded deck, beautifully appointed with cable rail, takes full advantage of the year-round Hammonasset River views. Inside the kitchen is truly a dream come true, featuring tasteful, sophisticated finishes and an impressive 10' island. The first floor has been extensively remodeled to create an open, effortless flow throughout the living spaces. Included in this remodel is exquisite white oak flooring. One of the home's most captivating features is the stunning sunroom, transformed from what was once a porch and rebuilt from the studs out into a wonderful year-round space overlooking the river. The upper floor has been completely repainted and offers a spacious, versatile layout. The private primary ensuite with a walk-in closet is complemented by 3 good-sized bedrooms. At the heart of the bedroom level is a wonderful expansive loft overlooking the family room below. Filled with possibilities, this peaceful retreat is ideal for a home office, hobby space, library, or a cozy den - providing a quiet escape while remaining connected to the main living area. Enjoy the convenience of this location which is within walking distance to Hammonasset Beach State Park, while downtown Madison is just minutes away.

22 Kingsbridge Way Unit 22, Madison

7 Sunset Rd, Madison
$1,215,000
4 Beds ⋅ 2 Baths ⋅ 24216954 MLS
Welcome to this beautifully updated, bright and inviting ranch offering the perfect blend of classic charm and coastal living. Featuring 4 bedrooms and 2 full baths, this home boasts beautiful hardwood floors, a sun-filled living room with a cozy stone fireplace, and a fresh, clean feel that makes you feel right at home. The open kitchen features stainless steel appliances, a center island, and an easy flow into the dining area, creating a wonderful space for everyday living and entertaining. The spacious primary suite offers a private retreat, while three additional bedrooms provide flexibility for guests, a home office, or other needs. Ideally located approximately 1,000 feet from the water, across from the Madison Beach Club tennis courts and south of the Post Road, this delightful home is a short stroll to The Surf Club, East Wharf Beach, and the shops, restaurants, and charm of downtown Madison. A wonderful opportunity to enjoy the relaxed lifestyle and timeless appeal of this sought-after shoreline community!

7 Sunset 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

24 Buck Hill Rd, Madison
$1,125,000
4 Beds ⋅ 3 Baths ⋅ 24200335 MLS
Set on a prime corner lot, this classic New England colonial is perfectly sited to welcome you home. The professional landscaping and stunning hardscaping accent this spectacular property. Step inside to a sun-drenched two-story foyer where detailed wainscoting and warm hardwood floors greet you. Elegant crown molding and custom paneling seamlessly frame the light-filled main spaces. At the center of daily life sits a custom chef's kitchen with an oversized island made for large or small gatherings. It flows into a family room anchored by a cozy fireplace, offering endless room for all - perfect for holidays or everyday! Access the deck and patio from either the family room or the kitchen and appreciate the added space for overflow when entertaining. Upstairs, the primary suite is surrounded by recessed panel wainscoting and crowned with an elegant tray ceiling, features a walk-in closet and expansive bathroom. Three spacious bedrooms complete the second floor as well as a hall bath, laundry and abundant storage. Expanding your options, a massive bonus room stretches over the entire three-car garage, ideal for a media room, play area, or home office.

24 Buck Hill Rd, Madison

148 Mungertown Rd, Madison
$1,070,000
4 Beds ⋅ 4 Baths ⋅ 24217499 MLS
A Rare Historic Madison Homestead - Timeless Character, Thoughtful Updates & Move-In Ready! Discover the history and distinctive character of this circa-1752 Madison homestead, once home to Helen Foster Snow, the pioneering American journalist, author, and humanitarian known for her groundbreaking reporting from China in the 1930s. Lovingly renovated and thoughtfully updated by the owner of East Guilford Construction, a builder specializing in historic homes, this property was undertaken as a personal project for his own family, reflecting his appreciation for historic architecture, traditional craftsmanship, and the comforts of modern living. The result is a unique historic property that blends old-world charm with thoughtful updates, offering the next owner the opportunity to simply move in and enjoy. The main residence offers 4 bedrooms and 4 full baths, with distinctive architectural details and individual character throughout. A separate one-bedroom guest house provides additional living flexibility, while two barns offer versatile space for hobbies, workshops, storage, or creative pursuits. A picturesque pond adds to the property's special charm. The property at 148 Mungertown Road, together with the adjacent 1.52-acre parcel at 140 Mungertown Road, is being sold together, bringing the combined acreage to approximately 3 acres. The additional land offers further possibilities, subject to applicable zoning and town approvals.

148 Mungertown Rd, 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

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

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

69 Bradley Corners Rd, Madison
$850,000
7 Beds ⋅ 4 Baths ⋅ 24214953 MLS
Welcome to 69 Bradley Corners Road, a truly unique property nestled on over 6 acres in beautiful Madison! Offering an incredible combination of privacy, space, and resort-style amenities, this home is anything but ordinary. Enjoy your own private retreat complete with a picturesque pond, tennis court, and in-ground pool, perfect for entertaining or simply enjoying everything this property has to offer. Inside, you'll find a stunning primary suite and a spacious layout featuring a full in-law apartment for guests or multigenerational living. Looking for even more space? The lower level offers additional potential to expand your living area and make it your own. With over 6 acres to enjoy, endless possibilities, and amenities rarely found together in one property, this is truly a one-of-a-kind opportunity. Properties like this don't come along often. Don't miss your chance to see everything this incredible Madison home has to offer!

69 Bradley Corners Rd, Madison

150 Race Hill Rd, Madison
$799,999
4 Beds ⋅ 3 Baths ⋅ 24208079 MLS
A rare and remarkably charming Antique in one of Madison's most picturesque settings. Set on 7+ acres along quiet Race Hill Rd, this beautifully preserved circa-1764 Cape blends centuries of character with thoughtful updates and the ease of modern living. Originally restored to the studs in 1996, the 2,091 sq.ft. main house retains an extraordinary amount of its original character, including chestnut flooring, period hardware, exposed beams and other details that give the home a wonderful sense of history. The floor plan is warm and inviting. The dining area opens to a family room with rustic beams, one of the original fireplaces and windows overlooking the private grounds. The family room, which could also work as a 1st floor bedroom, is highlighted by a 2nd original fireplace, built-ins and a full bath. The formal living room is distinguished with a 3rd fireplace, loads of windows and original cabinetry. A charming kitchen with cathedral ceilings and exposed beams, and a terrific sun room with a stone floor and private entrance complete the main living spaces. Upstairs you'll find three bedrooms and a full bath. And then there is the guest cottage! A beautifully renovated, year-round 701 sq.ft. legal one-bedroom cottage, that is an exceptional addition to the property-ideal for guests, extended family, a private office or rental use. Thoughtfully refinished and entirely independent, the cottage adds a level of flexibility rarely found.

150 Race Hill Rd, Madison

42 Concord Dr, Madison
$799,900
4 Beds ⋅ 3 Baths ⋅ 24206829 MLS
Perched on a scenic knoll in a highly desirable neighborhood, this classic colonial exudes curb appeal. A newly laid, meandering brick walkway leads to two inviting front entrances. Inside, the welcoming foyer opens to a sun-drenched living room that flows seamlessly into a beautifully renovated kitchen. A chef's dream, the kitchen boasts crisp white cabinetry, a contrasting grey-washed center island with waterfall "Carrara-style" quartz countertops, and a spacious dining area perfect for hosting large gatherings. French doors open to a serene four-season porch and a sizable deck, making indoor-outdoor entertaining effortless. The main level also features a generous family room with a cozy gas fireplace. With its own private entrance, this versatile space is ideal for an in-law suite, au-pair quarters, or a quiet home office. Upstairs, the primary suite is a true sanctuary, complete with a walk-in closet and a tastefully renovated, spa-like bath featuring heated floors. Three additional spacious bedrooms, all customized with California Closets, share a second beautifully updated full bath. Freshly painted throughout, the home also features a finished lower level with brand-new composite flooring and a highly functional mudroom just off the garage. This is a lovely home in a sought after private neighborhood and the community of Heatherwood is special within itself- come and experience all that it has to offer.

42 Concord Dr, Madison

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