Listings by Tom Scott

DIRECT WATERFRONT – Rare Opportunity in Gulf Beach Neighborhood Situated on over an acre of beautifully manicured lawn with lush gardens and natural seagrass, this direct waterfront property overlooks the picturesque Gulf Pond. Tucked away on a quiet cul-de-sac in the sought-after Gulf Beach neighborhood, this updated classic Cape offers the perfect blend of charm, comfort, and location. The four-bedroom home with two full baths has hardwood floors and water views from nearly every room. It features a sun-filled living room with fireplace, a formal dining room and a remodeled kitchen with granite countertops and stainless steel appliances. The adjacent family room opens onto a spacious, two-tiered waterside deck—ideal for entertaining or simply enjoying the peaceful waterfront setting. The partially finished lower level includes a workshop and recreation room with entry to a three-car garage. A private driveway and ample on-street parking make hosting gatherings easy. Perfect for nature lovers and bird watchers, 8 Captains Walk is just a short stroll to Gulf Beach and offers kayaking right from your front yard. You'll also enjoy easy access to Milford’s charming historic downtown, harbor, restaurants, boutiques, and marinas. Conveniently located near I-95, the Merritt Parkway, and the Milford train station, New York City and New Haven are in easy reach. Whether you're looking for a year-round residence or a weekend retreat, this home offers timeless style, quality construction, and the potential to expand—all in a stunning waterfront setting. Schedule your private showing today.

183 FEET OF LONG ISLAND SOUND FRONTAGE. Experience rare privacy and panoramic views from this exceptional Point Lookout residence in Milford. Perfectly positioned on one of the largest waterfront lots in the area, the property offers unobstructed vistas of Long Island Sound, Charles Island, and the entrance to Milford Harbor. A sweeping waterside lawn sets the stage for summer gatherings, while the heated inground pool—with its own pool/storage shed—is an amenity seldom found on Milford’s waterfront. Just steps away, Point Lookout residents also enjoy access to the Point Lookout Association’s private sandy beach, complete with kayak racks for coastal adventures. Inside, floor-to-ceiling windows in the living room frame yacht-like water views and create a bright, airy ambiance, complemented by a cozy fireplace. The remodeled kitchen boasts premium cabinetry and appliances, seamlessly opening to the dining and living areas for effortless entertaining. The spacious primary suite is a retreat of its own, featuring breathtaking water views, direct access to the pool and patio, and a luxurious bath that flows into an open-air atrium and private garden. Hardwood floors and original wood paneling throughout much of the home add warmth and timeless character. Additional highlights include a two-car garage, abundant storage, driveway parking for at least five vehicles, and beautifully landscaped garden and patio. With ample room to expand, this property offers many possibilities—alongside daily picture-perfect sunrises and sunsets. Just minutes from Milford’s historic downtown, restaurants, boutiques, and marinas, as well as the Milford Yacht Club, parks, and tennis courts, the location combines convenience with tranquility. Easy access to I-95, the Merritt Parkway, and the Milford train station makes travel to New Haven and New York City a breeze. This mid-century coastal gem offers the perfect balance of natural beauty, privacy, and prime location—whether you’re searching for a full-time residence or a waterfront escape. Relax, watch the boats sail by, and embrace the lifestyle this home offers. Schedule your private showing today.

Located right on Merwin Point with sweeping, unobstructed views of Long Island Sound to the east, south, and west, this majestic 4,700 sq. ft. waterfront home offers a once-in-a-lifetime opportunity. Built circa 1910 and originally known as the Blakeslee Cottage, named after the original owner/builder, this stately residence sits in the heart of the historic Borough of Woodmont—just steps from the water and a short drive to New Haven and Yale University. This rare offering includes a private half-acre with a lawn, rock and seagrass peninsula across the street. Inside, the main level features a gracious living room with a grand fireplace opening to a spacious waterside porch. A second fireplace warms the adjacent family room, located next to a first-floor bedroom and full bath. The main level also includes a second bedroom with bath, a formal dining room, family room and kitchen. Upstairs, you'll find four additional bedrooms, two full baths, and a waterside deck with panoramic views. The finished lower level adds versatile bonus space, complete with a rec room, built-in bar, belly stove, and ample storage. Outdoors, entertaining is effortless with parking for up to 11 cars: a stamped concrete driveway, a three-car garage (center bay wide enough for a boat) with driveway, semicircular front drive, and a third private driveway on the east side of the home. Enjoy beach walks, morning runs, and endless water activities—boating, fishing, swimming, and sunbathing—right outside your front door. Public parks, tennis and basketball courts, and Milford Harbor’s marinas and yacht club are all nearby. The Borough of Woodmont is a short drive to New Haven and Yale University, and Milford offers several well-established marinas in addition to the Milford Yacht Club. Easy access to the Milford train station, I-95, and the Merritt Parkway makes this location ideal for both year-round living and weekend getaways. A truly exceptional waterfront lifestyle awaits. Call today for your private showing.

Welcome to an exceptional opportunity to live by the water in comfort, style, and tranquility. Built in 2004 and impeccably maintained with numerous upgrades, this 2,500+ sq ft coastal residence offers sweeping views of Long Island Sound and the Housatonic River from nearly every room. The flexible floor plan features three spacious bedrooms, each with a full bath, plus a dedicated home office and 3.5 bathrooms finished with marble and natural stone. Designed for both elegance and ease of living, the main level showcases unobstructed water views from the kitchen with imported Poggenpohl cabinetry and high-end appliances. The light-filled dining area and a living room with waterside deck is perfect for entertaining or quiet evenings overlooking the water. Upstairs, the primary suite is a private retreat with generous closets, a luxurious spa bath, a private waterside deck, and breathtaking water views. The lower level offers a private waterside suite with its own entrance and deck, ideal for guests or an in-law setup. Quality craftsmanship is evident throughout, with hardwood and tile flooring, fine millwork, and high-end finishes. Additional highlights include a two-car garage with ample storage, paver drive and courtyard, an EV charging station, indoor backup generator, and professionally landscaped grounds with mature plantings. From your own backyard, launch a kayak or small boat and enjoy direct access to the water. As a unique bonus, a rooftop widow’s walk provides panoramic views of Long Island Sound, Charles Island, and the Housatonic River—an inspiring setting for a home office or private sanctuary. Located in Milford’s sought-after Cedar Beach neighborhood, this home is just steps from a sandy beach and the Connecticut Audubon Society Coastal Center, known for birdwatching, nature trails, and peaceful walks. Milford’s historic downtown, restaurants, boutiques, harbor marinas, the Yacht Club, and public parks are all nearby. Easy access to I-95, the Merritt Parkway, and the Milford train station makes New Haven and New York City within easy reach. This home combines modern convenience with timeless coastal charm. Whether you seek a full-time residence or a waterfront getaway, this property offers a rare blend of natural beauty, quality construction, and prime location. Swim, fish, boat, and relax—right outside your door. Schedule your private showing today.