luxury properties for sale New Haven County, United States

Highly sought after and rarely available-until now! 89-2 Cottage Road is the seasonal Madison cottage you'll want to run toward. Proudly part of the historic Little Colony community settled by veterans just after World War II, this lovely abode offers two bedrooms and a thoughtfully renovated full bath. The heart of the home is a generous, open-concept living space featuring a beautifully updated kitchen with granite countertops and a center island with a waterfall edge. Outfitted with newer appliances, new flooring throughout, and professional landscaping outside, each upgrade was carefully chosen to cultivate a beautiful yet serene space-easy to maintain, even easier to enjoy! Plus, the fully screened-in porch means there is plenty of space for gathering family and friends at the shoreline. Unlike many original cottages in the area, 89-2 was constructed with the integrity of a small home, featuring a full basement and crawl space for storage, insulation, and an oil heating system. Its larger size allows for conveniences uncommon in seasonal living, including a dishwasher and an in-home washer and dryer. Located within a short distance to Hammonasset, Madison town beaches, and town center, this is more than just a home-it is a gateway to a vibrant shoreline lifestyle. Seize this rare opportunity to own a piece of Madison history in a highly sought after community and come see for yourself why 89-2 Cottage Road is the ideal haven for making lifelong summer memories

Discover sophisticated elegance and masterful craftsmanship in this conveniently located residence. The heart of the home is a breathtaking great room, defined by soaring 10 foot ceilings, warm cherry floors and a commanding granite fireplace. Designed for the discerning entertainer, this space features mahogany crown molding, custom glass front cabinetry and a convenient wet bar, all bathed in natural light through the stately Palladian window and 2 glass doors providing access to the patio and beautiful gardens. Off to the side is the dramatic staircase to the second floor and 2 secret closets which provide additional storage. The primary bedroom suite is a true retreat, highlighted by a dramatic Roman arched ceiling and an indulgent ensuite bath finished in exquisite black marble with striking white veining. The suite includes a private sitting room featuring custom oak floors with elegant cherry inlay, complete with a refrigerator and sink for ultimate convenience. 4 additional bedrooms including one on the first floor provide plenty of space for all, including those who prefer not to climb the stairs. Outside, is a large private yard with plush green grass made possible by the irrigation system. There is a sizable 2 car garage with a fully finished room above suitable for an office or home gym. With thoughtful details throughout, beautiful woodwork and massive custom arched mahogany doors, this home offers a seamless blend of grand scale living and private luxury.

Tucked away on a peaceful cul-de-sac within Southbury's award-winning Region 15 school district, this thoughtfully designed Colonial offers timeless appeal, exceptional privacy, and everyday comfort. The spacious kitchen is appointed with granite countertops, Viking double wall ovens, a Viking gas cooktop with warming drawer, oversized pantry and a Bosch dishwasher, perfectly suited for daily living and entertaining. Rich hardwood floors extend throughout the main level, where the sun-filled family room features soaring vaulted ceilings, a ceiling fan, and a charming wood-burning stove. Upstairs, the spacious primary suite offers a walk-in closet and spa-like bath with jetted tub and separate shower, accompanied by three additional bedrooms and a convenient second-floor laundry room. The unfinished lower level with epoxy-coated floor and additional electrical service provides outstanding workshop or future finishing potential. Outside, enjoy a private deck, flourishing vegetable garden, peach and pear trees, and a beautifully private setting. Conveniently located just minutes from I-84, Route 67, shopping, dining, and everyday amenities.

**7/26/26 Open House Cancelled** Updated, 4-bedroom, 2-bathroom New England gem boasting 2,348 square feet of thoughtfully designed living space. Pride of ownership shines through with improvements already completed for you, including a new roof (2026), freshly painted exterior (2026), a replaced septic system (2021), and a new well (2020). Interior features include a gorgeous remodeled kitchen with quartzite counters and stainless steel appliances that flows into a family room featuring dramatic cathedral ceilings and easy access to the rear yard entertaining space. The exterior is a true staycation paradise. The level backyard hosts a pristine in-ground pool paired with a dedicated pool shed equipped with electricity-ideal for pool storage. Peace of mind thanks to an upgraded 200-amp electrical service complete with a generator transfer switch. Perfectly situated just north of Route 1, this home offers the ultimate shoreline lifestyle. Enjoy being just a 5-minute drive to Madison's quintessential town center and a quick 8-minute drive to the beach. Move right in and start enjoying summer by the pool!

Charming 3-bedroom home offering multiple flexible spaces to fit your needs. This well-maintained home features refinished original hardwood floors, central air, a spacious mudroom/laundry room, a walk-in pantry, and a walk-up attic providing excellent storage or future potential. Enjoy outdoor living with a covered front porch and side yard patio while taking in the privacy of the wooded rear portion of the 1.3-acre property. The detached barn is ready for its next owner's vision, while ample parking adds to the property's convenience. Located in a quiet area near the Watertown line with convenient access to everyday amenities and nearby outdoor recreation.

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

Set gracefully on a beautifully landscaped property framed by classic New England stone walls, this timeless Colonial has been thoughtfully refreshed and offers the perfect balance of warmth, charm, and modern comfort. A welcoming covered front porch opens an inviting interior with a classic, smart floor plan. At the heart of the home is the Kitchen featuring honed granite, GE Monogram stainless steel appliances, and a center island with a gas cooktop. This space opens to the Family Room highlighted by a wood fireplace and windows overlooking the front yard. The Sunroom with sliders to the large deck presents additional space for work, life and play. The 1st floor is rounded out with a gracious Dining Room, Living Room with a gas fireplace and a sweet Powder Room. Upstairs you'll find four bedrooms. The Primary will impress with a walk-in closet, full bath, elegant wainscoting, and an adjoining flex space. Three bedrooms and a full bath complete the floor. The unfinished lower level, creatively reimagined as a play space, offers expansion possibilities as does the unfinished walk up attic. Enjoy evenings on the patio beneath the pergola, dine with a view, unwind in the enclosed hot tub, rinse off in the outdoor shower, or simply take in the beauty of the grounds. Additional highlights include a shed and woodshed. Offering timeless appeal, exceptional outdoor living, and a coveted Madison location, this is a home where memories are waiting to be made.

This magical light-filled New England 7,945 s.f. cottage takes full advantage of its private waterfront location overlooking LIS and a wildlife estuary. Sited in a private community on 1.27 acres with 300' of water frontage provides panoramic water views of sunrises and sunsets from most rooms. A heated swimming pool, two beaches and mooring rights guarantee outdoor pleasures. There is also room for a tennis court. The house was expanded from its original 1912 footprint and fully renovated over 3 years (1987-1990) with the best curated materials including Tischler high impact windows throughout. French doors in the 18' ceilinged living room, dining room and family room all open to a flagstone terrace. The 6+ bedrooms, all but one with ensuite bathrooms, can be accessed by elevator or front and back stairs. There is also a separate handicapped accessible apartment. The impressive, newly renovated kitchen with table sitting up to eight is equipped with top of the line appliances. Privacy, gracious living space and endless recreation possibilities make this special property an ideal retreat. Check floor plans for more details.

If you like the idea of a tiny house but can't figure out how to downsize that much, here is your solution! This adorable one room cottage in the woods has space for you and the basics, a nice usable kitchen and a full bathroom with a shower. The owners have poured a ton of love into it in the form of a brand new roof, new well, new windows, new range, refrigerator, washer & dryer, cleared the property of many trees, and put in a new well pressure tank. The furnace is on the newer side, as is the hot water heater. They put in a new bathroom sink and repaired the septic. It's cozy and comfortable, cute and ready for you! There is a total of 596 liveable square feet when the kitchen is included in the number. Explore the nearby Larkin Trail, or just relax by the stream that runs along the side of the property. The house is not connected to the sewer line in the street, but a new owner can look into that if expansion is your plan. Being sold as-is.

For this private Wolcott estate property, the experience begins well before you arrive at the front door and makes a lasting impression. Ornamental iron gates framed by stone pillars and walls open to nearly 4 private acres, where a long, winding drive leads past vineyards, fruit trees and mature plantings, to a circular courtyard with a three-tiered cascading fountain. Designed as the builder's personal home, the property reflects exceptional attention to design, materials, and craftsmanship. The stucco exterior is accented by substantial stonework and a towering cedar-lined entry leading to the front door. Inside, the home offers four bedrooms, four full baths, and one half bath, with generous spaces designed for family living, gathering, and entertaining. Magnificent Schonbek crystal chandeliers bring brilliance and drama to the double story foyer. Brazilian cherry inlaid floors, elegant yet understated molding, and rich architectural details create a warm, refined interior that feels impressive without losing its sense of comfort. The home was thoughtfully positioned to capture natural light throughout the day, with interior and exterior spaces that remain closely connected to the land.

This turnkey, sun-filled Colonial situated south of Route 80 in Madison perfectly blends meticulous maintenance with smart, modern updates. The gracious main level features elegant French doors opening to a bright living room, a generous formal dining room- a perfect place for family gatherings and a cozy family room centered around a classic wood-burning fireplace. The heart of the home is the handsome eat-in kitchen-complete with cherry cabinetry, granite counters, and stainless appliances. Family room flows seamlessly into a stunning four-season sunroom wrapped in walls of windows and skylight's that stream natural light. A classic, updated half bath completes the first level. Upstairs, pristine hardwood floors run through four comfortable bedrooms, including a primary suite with double closets and a private, full bath. All four bedrooms are generous in size and there is a lovely common bathroom that services the three additional bedrooms. Outside, a maintenance-free Azek deck overlooks a private backyard framed by perennial gardens and mature trees. Major capital improvements - a new roof, gutters, skylights, new exterior paint, and updated windows ensure total peace of mind. Just minutes from Madison's beautiful beaches and quaint town center, this home will certainly fit all your needs and so much more.

This 4-bedroom Colonial offers the perfect combination of space, comfort & location. Ideally situated in a subdivision close to shopping, restaurants and major highways. The main level welcomes you with a spacious eat-in kitchen featuring abundant cabinetry, perfect for cooking & gathering. Sliders from the kitchen lead out to an oversized deck, creating a seamless indoor-outdoor flow for hosting. The kitchen opens directly to a large family room with built-ins & fireplace, making it the perfect spot to unwind. A formal dining room for special occasions and a bright living room that offers additional flexible living space. The second floor features four generously sized bedrooms and two full bathrooms. The spacious primary suite includes its own private full bath and an impressive walk-in closet. The additional bedrooms are well-proportioned and ideal for family members, guests, or home office space. The finished walk-out lower level adds over 1,100 square feet of additional living space & includes another full bathroom. This versatile area is perfect for a guest suite, gym, office, media room, or playroom. With sliders to the private backyard, you have easy access to the above ground pool. Additional highlights include a two-car garage, central air, & a beautifully landscaped lot. Plus...City water & sewers and economical solar panels to keep your electric bill way down. With its generous layout and excellent location, this home truly offers the best of comfortable living.

Welcome to 238 Scotland Road, a rare 5-bedroom home with private in-law accommodations, pool, situated on nearly an acre of privacy. A lovingly cared-for home offering exceptional space, comfort, and versatility. Features include hardwood floors throughout, central air conditioning, and a beautiful new primary suite designed for relaxation and convenience. The heart of the home is the updated kitchen, thoughtfully renovated and perfect for everyday living or entertaining. Just beyond, a bright and inviting three season sunroom provides the ideal place to unwind year-round and opens onto a Trex deck to the backyard and pool. Cozy up on cooler evenings beside the charming wood-burning stove, creating the perfect setting for relaxing nights at home. Step outside to enjoy the private inground vinyl-lined pool with a newer liner, offering endless opportunities for summer fun, entertaining, and making lasting memories with family and friends. Adding incredible flexibility, the property includes an attached in-law apartment with its own separate entrance and full bath, making it ideal for extended family, guests, or multi-generational living. Additional highlights include a newer roof, public water, generous living spaces, and a peaceful setting that feels secluded while remaining just minutes from town, beaches, shopping and dining. This well-loved home offers the perfect combination of privacy, thoughtful updates, and room to grow-ready for its next chapter.

The historic c. 1904 Scranton Homestead, described as a Colonial Revival gem, has come to the market! This much admired 3700 sf in town landmark offers an estate feel on a large, beautifully landscaped lot providing both privacy and convenience, moments from the village center and East Wharf Beach. With four bedrooms, this residence borrows from classic forms, with window styles, columns and porches found only in the most important homes of the era. Hand-worked trim, coffered ceilings, and detailed fireplaces speak to the craftsmanship available at the turn of the last century. Assets include a fully private primary suite with fireplace and custom dressing room, a third floor multi use space ready for special guests or activities. A well balanced blend of preserved history and modern comfort, the centerpiece of the home is an expansive fully updated chef's kitchen open to a great room with a cathedral, beamed ceiling and a wall of oversized glass bringing in light and showcasing the gardens, stone walls and patio features.

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

Well-maintained traditional Colonial located in the highly sought-after Lighthouse Point neighborhood. The main level features a bright and inviting living room and dining area with beautifully maintained hardwood floors, along with a spacious kitchen offering newer vinyl flooring and a convenient half bath. Upstairs, you'll find three comfortable bedrooms, all with hardwood flooring, and a full bathroom. The partially finished lower level adds extra living space and includes an additional convenient full bathroom. This home also offers valuable updates and features, including a tankless water heater, waterproofed basement, newer windows, and a whole-house filtration system. Enjoy outdoor living in the spacious multi-level yard complete with a deck, detached garage, and water views of Long Island Sound! Just a short walk to the park, beach, restaurants and so much more!

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.

Tucked into one of the shoreline's most sought-after neighborhoods, this 3-bed, 2-bath beach house feels like the setting of your own coastal retreat. Wake up and slip out for morning walks with deeded beach rights, coffee in hand, the salt air greeting you first thing. With its move-in-ready design, this home works beautifully as a full-time residence or a seasonal getaway-low-maintenance enough to lock and leave, yet comfortable and spacious enough for year-round living. Inside, the light-filled layout invites easy gatherings, while outside, the lifestyle is unmatched. Spend summer afternoons on the sand, weekends out on the water, and evenings dining at nearby restaurants that make this area so loved. Just beyond your doorstep, you'll find country clubs, parks, and golf courses, all part of the rhythm of this vibrant shoreline community. Whether it's morning beach access, a boat ride from your own mooring, weekend tee times, or simple strolls through the charming streets, life here is designed to be enjoyed. This isn't just a house by the beach-it's a lifestyle where the best of the coast meets the comforts of home. Bring your offers!

Embrace the enchantment of Shoreline Living at its finest with this sun-drenched haven at 3 Arrowhead, a jewel nestled in a quaint community with the river at your doorstep. As you step into this radiant abode, you're welcomed by a symphony of natural light and the serene melodies of local birdsong. The home's design harmoniously blends the outdoors with the indoors, creating a tranquil retreat. The heart of the home is the designer kitchen, which seamlessly transitions into an elegant dining room and a spacious living room, crafting an ideal setting for memorable gatherings. Journey upstairs to discover the luxurious Primary Bedroom, a sanctuary featuring a stone-adorned en-suite bathroom and a private deck that beckons you to unwind and soak in the picturesque views. Two additional generously-sized bedrooms, a well-appointed bath, and a convenient laundry area complete the upper level. Ascend to the versatile spacious living area offering a half bath, additional sleeping quarters, a dedicated office space, and a cozy reading nook, all complemented by the comfort of central air. Outside, the property is framed by verdant lawns, meticulously curated shrubbery, and an expansive patio that's perfect for alfresco entertainment or quiet reflection. This home is not just a residence; it's a lifestyle awaiting your arrival. We eagerly anticipate welcoming you to your new coastal sanctuary.