321 houses for sale in North Madison, Madison town New Haven County Connecticut

Tucked away on 4.5 beautiful acres in Killingworth, 79 Chestnut Hill Road offers exceptional privacy, peaceful pond views, and a welcoming sense of home from the moment you arrive. This distinctive 3-bedroom, 3-bath antique residence is filled with warmth and character, thoughtfully updated to provide the comfort and convenience of modern living. Extensive improvements completed between 2008 and 2026 include fresh interior paint, beautifully refinished natural hardwood floors, and a new elevated bluestone patio. Additional updates include the roof, windows, exterior paint, gutters, and water heater, along with updated electrical and plumbing, three-zone heating, central air, and a whole-house automatic generator. The kitchen and bathrooms have also been tastefully updated while preserving the home's timeless charm. Outside, mature trees, protected rear privacy, and an expansive, usable lawn create a serene backdrop with plenty of room to garden, entertain, explore, or simply enjoy the

Tucked away on 4.5 beautiful acres in Killingworth, 79 Chestnut Hill Road offers exceptional privacy, peaceful pond views, and a welcoming sense of home from the moment you arrive. This distinctive 3-bedroom, 3-bath antique residence is filled with warmth and character, thoughtfully updated to provide the comfort and convenience of modern living. Extensive improvements completed between 2008 and 2026 include fresh interior paint, beautifully refinished natural hardwood floors, and a new elevated bluestone patio. Additional updates include the roof, windows, exterior paint, gutters, and water heater, along with updated electrical and plumbing, three-zone heating, central air, and a whole-house automatic generator. The kitchen and bathrooms have also been tastefully updated while preserving the home's timeless charm. Outside, mature trees, protected rear privacy, and an expansive, usable lawn create a serene backdrop with plenty of room to garden, entertain, explore, or simply enjoy the

Terrific 3Br and 2Bth Embankment Ranch w/ Vaulted Ceilings, Fireplace and a Fabulous fully fenced back yard! Check out those Pics and our Virtual Reality Tour. New Roof. New Septic Tank. Open Floor Plan. Oil Hot Water Heat. Two Car Garage. Thermopane Windows. Front Porch. Great Rear Decking overlooking a Private Rear Yard. Welcome FHA and VA Buyers. We are always here to help!

Tucked onto a quiet cul-de-sac in a wonderful section of North Branford close to Lake Gaillard and scenic hiking trails, this 3-bedroom raised ranch is full of character and ready for its next chapter. Built in 1974 and lovingly maintained, the home offers gleaming hardwood floors throughout the main level and a warm, easy flow from room to room. A standout feature is the graceful curved wall that gently separates the living and dining rooms from the kitchen-an unusual architectural touch you won't find in the average raised ranch. The living room centers around a cozy wood-burning fireplace, perfect for taking the chill off a Connecticut evening. Off the dining room, sliders open to a sunporch overlooking a private, beautifully framed backyard and generous side yard. The main level features three bedrooms and a convenient Jack-and-Jill full bath accessible from both the hallway and the primary bedroom. A second full bath in the lower level adds flexibility, and the two-car attached ga

Welcome to this stunning 4-bedroom, 2.1-bath Colonial, perfectly situated on a quiet cul-de-sac and nestled on a picturesque, lightly wooded 4-acre lot. Surrounded by gorgeous landscaping and offering exceptional privacy, this beautiful home combines timeless elegance with modern comfort. Step inside to an inviting open floor plan designed for today's lifestyle. The spacious family room features a cozy wood-burning fireplace and sliding glass doors that lead to an incredible outdoor living space, making it ideal for entertaining family and friends. Enjoy evenings around the newly installed patio with a built-in fire pit, all overlooking the peaceful, fenced backyard. The gourmet kitchen is sure to impress with granite countertops, new stainless steel appliances, abundant cabinetry, and generous workspace for preparing meals and entertaining with ease. Upstairs, you'll find four spacious bedrooms, including a relaxing primary suite, along with a large bonus room that offers endless poss

A MAGNIFICENT REVIVAL and TIMELESS BLEND OF SOMETHING OLD and SOMETHING NEW. One of the finest restorations in New England, the Pitkin mansion is a true historical treasure. Carefully dismantled and moved to its current site in 1955, the property is nestled within nearly 4 acres of mature trees, manicured lawns, and magical gardens. This classic revival will be celebrated by the most discerning antique home enthusiasts and home lovers alike. Modern flair has been discreetly integrated to enhance function and enjoyment. Contemporary comforts include a poured concrete foundation, geothermal system, full house generator, humidifier, CENTRAL A/C, propane gas, Pella windows, security system, CITY WATER, underground utilities, NEW SEPTIC SYSTEMS, and much more. Significant additions include attached 2-car garage, detached 2-car garage w/half bath and upper bonus room, pool and pool house w/half bath and kitchenette, tennis court, garage barn w/FULL APARTMENT, all exemplifying a harmonious fu

A MAGNIFICENT REVIVAL and TIMELESS BLEND OF SOMETHING OLD and SOMETHING NEW. One of the finest restorations in New England, the Pitkin mansion is a true historical treasure. Carefully dismantled and moved to its current site in 1955, the property is nestled within nearly 4 acres of mature trees, manicured lawns, and magical gardens. This classic revival will be celebrated by the most discerning antique home enthusiasts and home lovers alike. Modern flair has been discreetly integrated to enhance function and enjoyment. Contemporary comforts include a poured concrete foundation, geothermal system, full house generator, humidifier, CENTRAL A/C, propane gas, Pella windows, security system, CITY WATER, underground utilities, NEW SEPTIC SYSTEMS, and much more. Significant additions include attached 2-car garage, detached 2-car garage w/half bath and upper bonus room, pool and pool house w/half bath and kitchenette, tennis court, garage barn w/FULL APARTMENT, all exemplifying a harmonious fu

Beautifully maintained and spacious, this oversized 3-bedroom, 2.5-bath raised ranch offers over 2,500 sq ft of living space and rests on a level Guilford property. Light and bright throughout, the main level features an open floor plan with a fireplaced living room flowing into the dining room with crown molding, a bay window and beautiful new hardwood floors in the living spaces. The kitchen offers abundant cabinetry and granite countertops. A true highlight is the stunning four-season sunroom, filled with natural light and showcasing a soaring cathedral wood ceiling, exposed beams and skylight. Sliders open to the deck and beautiful backyard-perfect for relaxing or entertaining. This level also includes a full bath with double vanity and ceramic tile plus a generously sized primary bedroom with its own full bath. The finished lower level adds approximately 728 sq ft of versatile living space with a large family room, three-season screened porch and access to the two-car garage. Majo

Welcome to 81 Briarwood Drive, a beautifully maintained 3-bedroom, 3 full-bath home offering the perfect blend of comfort, versatility, and homestead living in one of Guilford's most peaceful neighborhoods. The permitted, mostly finished walk-out basement adds exceptional living space with luxury vinyl flooring, a full bath, laundry hookups, and plumbing already in place for a future kitchenette, making it ideal for a recreation room, guest suite, home office, or potential in-law setup. An unfinished area remains for ample dry storage and mechanicals. A second laundry hookup has also been added on the main level for convenience. Nature lovers will appreciate the raised garden beds, greenhouse, chicken coop, mature fruit trees, grapevines, berry bushes, and established landscaping. The private backyard is surrounded by mature trees and features a screened porch, rustic brick patio, and firepit for relaxing or entertaining. The eat-in kitchen offers granite countertops and newer stainles

Situated on 1.62 acres, this 4-bedroom, 2-bath ranch offers endless potential for investors, contractors, or buyers looking to create their dream home. The expansive backyard, once used as a sports field, provides an incredible amount of usable outdoor space that's rarely found. Inside, you'll find hardwood floors in many rooms, a spacious living room with a fireplace, a 2-car attached garage, and a bright sunroom/family room just off the kitchen featuring walls of windows overlooking the backyard. The home does require significant updating and repairs, but the layout, lot, and location provide an exceptional opportunity to add value. Conveniently located close to downtown shops, restaurants, and commuter routes

SO CLOSE TO TOWN! Rare opportunity to own NEW CONSTRUCTION south of Boston Post Road and close to the Guilford Center. This quality built Colonial offers a stylish from porch and is set back from the street for privacy. Professionally landscaped with dramatic hardscape features, it borders the Westwood Trails. Light and bright with large windows and high ceilings. The kitchen is a Chef's delight with Wolf stove, under counter microwave, huge center island with granite counters and open to the family room. Storage galore! including a large pantry for all your needs. Open to the family room with gas Fireplace and French doors to the stone patio and private area for entertainment. Spacious front room can be used as a private office. Enormous great room offers tremendous flexibility. Formal Dining room for gracious dining. The spacious bedrooms and the spa like primary bath will soothe and delight you. A walkup attic and full basement will accommodate all your storage needs. This home has

SO CLOSE TO TOWN! Rare opportunity to own NEW CONSTRUCTION south of Boston Post Road and close to the Guilford Center. This quality built Colonial offers a stylish from porch and is set back from the street for privacy. Professionally landscaped with dramatic hardscape features, it borders the Westwood Trails. Light and bright with large windows and high ceilings. The kitchen is a Chef's delight with Wolf stove, under counter microwave, huge center island with granite counters and open to the family room. Storage galore! including a large pantry for all your needs. Open to the family room with gas Fireplace and French doors to the stone patio and private area for entertainment. Spacious front room can be used as a private office. Enormous great room offers tremendous flexibility. Formal Dining room for gracious dining. The spacious bedrooms and the spa like primary bath will soothe and delight you. A walkup attic and full basement will accommodate all your storage needs. This home has

Nestled on more than 1.4 private acres, this sprawling ranch offers 3 bedrooms, 2 full bathrooms, an oversized two-car garage, two storage sheds, and so much more. The spacious eat-in kitchen features a propane gas stove, stainless steel appliances, and ample space for everyday living and entertaining. The light filled living room is highlighted by a stunning three unit picture window and a beautiful oversized stone fireplace, creating a warm and inviting atmosphere. The heated basement offers endless possibilities for additional living space, a recreation room, home office, or workshop. Conveniently located just minutes from Chamard Vineyards, award-winning beaches, shopping, dining, and all the shoreline has to offer. Sold AS IS

A Fantastic Opportunity in an Adorable Neighborhood Welcome to a home that offers incredible potential, a great location, and peace of mind with many of the major systems already updated. While this property needs work and updating, the big-ticket items have been taken care of, making this an exciting opportunity for someone looking to build equity and create a home that truly reflects their style. Recent improvements include a 2024 roof, 2024 central air conditioning, 2024 furnace, 2025 oil tank, 2025 garage doors, a 2023 hot water heater, and a brand-new septic system installed in 2026. With so many important mechanical and structural components recently addressed, you can focus your energy on transforming the interior and making the home your own. Nestled in an adorable, established neighborhood surrounded by homes that are significantly more expensive, this property presents a rare opportunity. Whether you're looking for a renovation project or an investment opportunity, the possib

Gracefully blending timeless architecture with exceptional everyday living, this beautifully appointed Colonial offers thoughtfully designed open spaces both inside and out. A welcoming wraparound porch creates an elegant first impression, while the interior unfolds into an open floor plan ideal for entertaining. The chef-inspired kitchen features a generous center island, double ovens, and a sunny breakfast area that opens seamlessly to the expansive family room. Anchored by a cozy fireplace, this space extends effortlessly through sliding doors to an expansive deck overlooking the private backyard. The outdoor setting is a true retreat. Highlighted by a sparkling inground pool and a built-in fire pit nestled on an upper terrace-creating the perfect setting for summer gatherings, relaxing evenings, and outdoor entertaining. The primary suite offers a peaceful sanctuary with abundant natural light, a spacious walk-in closet, and an ensuite bath featuring a whirlpool soaking tub, separa

A Fantastic Opportunity in an Adorable Neighborhood Welcome to a home that offers incredible potential, a great location, and peace of mind with many of the major systems already updated. While this property needs work and updating, the big-ticket items have been taken care of, making this an exciting opportunity for someone looking to build equity and create a home that truly reflects their style. Recent improvements include a 2024 roof, 2024 central air conditioning, 2024 furnace, 2025 oil tank, 2025 garage doors, a 2023 hot water heater, and a brand-new septic system installed in 2026. With so many important mechanical and structural components recently addressed, you can focus your energy on transforming the interior and making the home your own. Nestled in an adorable, established neighborhood surrounded by homes that are significantly more expensive, this property presents a rare opportunity. Whether you're looking for a renovation project or an investment opportunity, the possib

LIVE. WORK. PLAY! Opportunity to own a property offering an in-home business location. Your business occupies the ground level while your residence is nestled on the luxurious second and third floors, offering comfortable distance between your home and professional workspace to meet with clients. Custom built with high quality appointments and thoughtfully constructed with your personal and professional needs in mind. Designed to offer a comfortable, low maintenance lifestyle. The main level offers a conference room, two offices, kitchenette and half bath. The residence above embraces an amazing kitchen with heated floors and high end appliances a guest bedroom and impressive full bath. The Primary Suite occupies the entire third level with large walk in closet and luxuriously appointed full bath, Garage is heated and offers an electric car charging station. A unique opportunity to LIVE, WORK, and PLAY at Home!

Bring your vision to this charming 3-bedroom, 1.5-bath home set on almost an acre in desirable Guilford. Featuring a 2-car garage, hardwood flooring underneath the existing carpet, dining room, eat in kitchen and a spacious living room with a fireplace, this home offers a great foundation for your personal touches. The lower level provides additional living space with a half bath and walk-out access-perfect for a man cave, den, home office, or recreation room. While the home needs updating, the canvas is here to create something truly your own! Enjoy the privacy of nearly an acre while being part of the sought-after Guilford shoreline community. A great opportunity for someone looking to add value and make a home their own. *SOLD AS IS

Move-in ready and located in a desirable Madison neighborhood near schools and Bauer Park, this expanded Cape offers space, flexibility, and modern updates throughout. Recent improvements include updated kitchens, all 3.5 renovated bathrooms, and new flooring, creating a fresh and welcoming feel. The main level features an eat-in kitchen, formal dining room, and a family room with vaulted ceilings, exposed beams, a wood-burning fireplace, and French doors leading to a covered deck overlooking the private backyard. Upstairs are the primary suite, two additional bedrooms, and a versatile fourth bedroom with its own private entrance. The heated walkout lower level includes a kitchenette, full bath, and separate entrance, providing an ideal in-law suite, guest space, or multigenerational living arrangement. Offering 2,128 square feet of above-grade living area plus approximately 1,240 square feet of finished lower-level space, this home combines move-in-ready comfort with exceptional versa

Private Pet friendly End unit newly refreshed! Ranch style offers Cathedral Ceiling Living Room with Fireplace and Dining area; Kitchen with new Stove; Refrigerator; and Dishwasher and sink. Primary Bedroom with attached Full Bath and Laundry room with Washer and Dryer. There is a Spiral staircase to Loft area featuring its own Balcony and a Large storage room or possible walk in closet. Can be a guest room, office or exercise area. Close to Hiking trails; Lake Quonnipaug offering a public boat launch for Kayaks or small fishing boats. Beach is a short drive away. Move in condition / ask listing agent for list of updates. Just unpack and settle in!

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, a

CLASSIC KILLINGWORTH SALTBOX! This is a beautifully maintained home on 5+ acres, that has had many upgrades. The central air conditioning system is new in 2026, and the inviting kidney shaped, inground pool has a new liner. The kitchen was remodeled a few years ago, and features granite counters, island seating, as well as a separate dining area. Sliders from the kitchen open to the deck (with new awning), and patio area. There are hardwood floors throughout, two fireplaces, solid, six panel doors, updated baths, and a walk-in closet in the primary bedroom. All of the windows have been replaced with Andersen thermopane windows. The walk-up attic provides great space for storage, and there is a full basement as well. Beyond the pool is 14 x 26 barn/shed, with a loft. This building could be used as a workshop, studio, playhouse, gym space, or' The grounds have been professionally landscaped, and feature a full irrigation system and many blossoming perennials. Don't miss this well maintai

CLASSIC KILLINGWORTH SALTBOX! This is a beautifully maintained home on 5+ acres, that has had many upgrades. The central air conditioning system is new in 2026, and the inviting kidney shaped, inground pool has a new liner. The kitchen was remodeled a few years ago, and features granite counters, island seating, as well as a separate dining area. Sliders from the kitchen open to the deck (with new awning), and patio area. There are hardwood floors throughout, two fireplaces, solid, six panel doors, updated baths, and a walk-in closet in the primary bedroom. All of the windows have been replaced with Andersen thermopane windows. The walk-up attic provides great space for storage, and there is a full basement as well. Beyond the pool is 14 x 26 barn/shed, with a loft. This building could be used as a workshop, studio, playhouse, gym space, or' The grounds have been professionally landscaped, and feature a full irrigation system and many blossoming perennials. Don't miss this well maintai

Step into nearly three centuries of Connecticut history, beautifully reimagined for modern living. Privately set on 1.5 beautifully established acres, this exceptional circa-1752 former Helen Foster Snow homestead is a rare convergence of architectural authenticity, exceptional craftsmanship, modern comfort, and effortless shoreline living. Just minutes from Hammonasset Beach State Park (~5 miles) and The Surf Club (~4 miles), the property offers an extraordinary sense of privacy and tranquility while remaining close to the beauty and amenities of the Connecticut shoreline. Once home to renowned journalist, author, and humanitarian Helen Foster Snow, the residence possesses a sense of history that cannot be recreated. Wide-plank floors, hand-hewn beams, period details, and beautifully proportioned, light-filled rooms preserve the soul of the original home, while extensive improvements have made the property exceptionally comfortable for contemporary living. What makes this estate parti

Looking for a home with heart and soul' One that has been lovingly maintained and thoughtfully updated' This gracious 3,800 sqft Colonial sits proudly on a beautiful lot in one of Killingworth's most desirable neighborhoods. At the heart of the home is a beautifully appointed cook's kitchen that opens seamlessly to a sun-drenched family room, where expansive windows frame views of the private backyard and surrounding natural beauty. A first-floor office provides the perfect work-from-home space, while a well-designed mudroom keeps everyday life organized. An inviting living room and charming powder room complete the main level. Upstairs, you'll find 4 generously sized bedrooms, including a spacious primary suite featuring a large walk-in closet and an elegantly updated bath. A standout feature is the exceptional play and recreation room - ideal for movie nights, sleepovers, a home gym, game room, or whatever suits your lifestyle. With access from both the 1st and 2nd floors, it offers

Set on an expansive, private parcel, this impressive home offers an abundance of space, privacy, and potential. Built by the original owner, this property has remained in the same family and is now being offered as part of an estate. Inside, you'll find five spacious bedrooms, two full and two half baths, hardwood floors, three fireplaces, and multiple living spaces. The expansive walkout basement adds even more versatility with a dedicated recreation area and bar, creating a great space for entertaining, game nights, or relaxing. A lofted garage and generous basement provide an abundance of storage and flexible space for hobbies, projects, and future possibilities. Outside, a deck and patio overlook the private grounds, while the driveway is beautifully lined with mature Rose of Sharon plantings. The property abuts Town of Clinton property, offering the added benefit of knowing you won't have to worry about future development behind you. This property is truly a diamond in the rough,

Back on the market through no fault of the home the previous buyers' financing fell through. A full inspection was completed with no requests made. Their loss is your second chance.Tucked at the end of a quiet cul-de-sac on 1.4 private acres, this one-owner Guilford Colonial has been waiting 38 years for its second chapter and it's ready to tell a new story. Start your mornings on the covered back porch, coffee in hand, ceiling fans turning, watching the yard wake up and end summer nights out there too, because this porch is where this house does its living. Inside, the open-concept kitchen anchors it all: granite island, stainless appliances, and a sightline that runs straight to the brick fireplace in the family room, so whoever's cooking never misses a moment. When the weather turns, this is a cozy-nights-by-the-fire kind of home. The flexible main level keeps up with real life a bonus room off the dining area ready to become a walk-in pantry or office, and a den with half bath that

The Well Maiden Estate is a rare architecturally significant waterfront estate where cascading waterfalls, winding streams, and Kroopa Pond converge across 3.5 private acres to create one of Connecticut's most extraordinary residential settings. Just minutes from the Connecticut shoreline, marinas, beaches, and fine dining, and ideally positioned between New York City and Boston, this private luxury retreat offers a rare opportunity to own a legacy estate equally suited for year-round living or a distinguished second-home escape. Originally a historic fishing shack, the restored wing blends seamlessly with a striking architectural residence designed to embrace its natural surroundings. Soaring vaulted and barreled wood ceilings, walls of glass, rich hardwood and slate floors, and 2 grand living rooms with magnificent fieldstone fireplaces create warm, sophisticated spaces with captivating water views. Chef's kitchen with Garland 6-burner range, double ovens, flat-top grill, Sub-Zero re

Whether you're coming from work or working from home, 48 Russett Drive offers an oasis in your busy lives. Situated on 3/4 of an acre of lush, professionally landscaped lawns bordered by mature perennials and featuring a captivating view of Bishop's Farm Apple Orchards, this home will make you feel that you've entered another world, but you're only minutes from I-95, Boston Post Road and Guilford Center. This contemporary house exudes comfort, modern convenience and privacy, removed from the noise of modern life. The first floor living/dining/kitchen/sun room and backyard decks are drenched with sun most of the day and are adjoined by a family room with a cozy gas fireplace, a full wall entertainment center and a 1/2 bath. New appliances in the updated kitchen complement its sleek and practical design, with a walk-in pantry for additional storage. The airy and light second floor features a primary bedroom with cathedral ceiling, a walk-in closet and en suite bath. An additional full ba

Opportunity to make sweat equity, this home needs work. Kitchen, living room, dining room, 4 bedrooms, 2 baths, 2 car garage make up this expanded ranch on a lovely level lot on cul-de-sac. The dining room could be a second family room. Open flow for entertaining. Just minutes to downtown Madison and beaches. Top schools. Owner is not in position to make repairs. Perfect home to update to your style and build equity!