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$2,995,000 (USD)
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Chester Area Single Family Home

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288 Middlesex Avenue Chester, CT 06412

4 Bed
6 Baths
4626 sqft
MLS# 24201816
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Set along a coveted and historic stretch of the Connecticut River, East View is a rare waterfront compound where extraordinary frontage, architectural integrity and Connecticut River Valley charm converge. Just over one mile from the village, this turnkey 2.65-acre estate offers 285 feet of direct river frontage, protected views and deep-water access. The river is the focal point framed by manicured grounds and a broad terrace leading gently to the water. A six-pile, deep water dock with two slips and a 16-ton lift is designed for serious boaters, while paddling is enjoyed from the floating dock and a small beach. Rooted in historic design and masterfully renovated in 2010, the residence blends timeless New England architecture with modern livability. Equally suited to weekends on the water, extended family gatherings, or multi-generational living, the property offers flexible spaces designed to entertain and live comfortably. Find a total of six garage bays for auto collections, boats, or a workshop. Minutes away discover Chester Village restaurants and artisans. Just across the river, the Goodspeed Opera House adds celebrated cultural dimension, and the neighboring seasonal Connecticut Valley Railroad evokes the region's rich history. The quiet elegance of East View offers a rare opportunity to experience the Connecticut River at its most extraordinary-where boating, history, culture, village life, and natural beauty converge.
Listing Courtesy of SMART MLS / Listed By: Nancy Mesham, Coldwell Banker Realty
$2,950,000 (USD)
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Beach Area Single Family Home

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297 Lalley Boulevard Fairfield, CT 06824

4 Bed
5 Baths
3243 sqft
There are few places in Fairfield where life feels this easy. At 297 Lalley, the beach, train, town, schools, restaurants, and farmers market are all within easy reach, yet home feels remarkably private, spacious, and peaceful. Custom built with exceptional attention to how people actually live, the home is open, bright, and filled with natural light. At its center is a dramatic kitchen anchored by a single slab of Danby marble, creating an island that naturally becomes the gathering place. Thoughtful details are everywhere, from two dishwashers and generous storage to carefully planned circulation that makes entertaining effortless. The connection to the outdoors is equally compelling. The kitchen and family room open toward an indoor/outdoor fireplace, creating an inviting setting from spring through fall, with the pool and patio just beyond. Beneath the home is a tremendous amount of additional storage, with the flexibility to create a future garage if desired. Upstairs, the third-floor "crow's nest" rises above the neighboring homes, offering a fifth-bedroom option with a full bath. It's a quiet retreat with views toward Long Island Sound. Morning brings sunrise over the water; evening brings sunset from the front porch. Walk to the beach, bike to the farmers market, head into town for dinner, or catch the train to New York without adding another commute to your day. Spacious, comfortable, and beautifully designed, this home captures the best of Fairfield Beach living.
Listing Courtesy of SMART MLS / Listed By: Cindy Raney, Coldwell Banker Realty
$2,850,000 (USD)
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N/A Area Single Family Home

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775 South Street Middlebury, CT 06762

8 Bed
8 Baths
9619 sqft
MLS# 24151632
Broadview Estate - A masterpiece in colonial revival design -Perched gracefully on the gentle hilltops of Middlebury! The Cameron Clark design is well preserved and displays a high quality of workmanship and materials, as well as the gracious proportions and classically inspired details inherent of the colonial revival. This residence is one of the finest examples of this style. Together the house and related garden cottages, grounds and surrounding landscapes of fields and woodlands, drape across the gentle hilltops of Middlebury with magnificent vistas east, west and north. It constitutes one of the most beautiful and historically significant properties in the area. The estate encompasses the seventeen room main house and three guest cottages: converted stables with unique industrial accents, classic cape, and pool side studio. The main home features magnificently scaled formal and informal settings, exquisite millwork, hardwood floors. Chefs' quality kitchen with sensational marble, large butler's pantry, breakfast nook, informal dining room, 800 bottle temperature controlled wine room complete this area. This opens to the library and raised paneled great room with vaulted ceilings and stone fireplace. Pass by the sweeping free-standing staircase which leads to the second level and enter the formal dining room and living room both with fireplaces adjacent to a mahogany paneled office. The wonderful conservatory overlooking the beautiful gardens, sauna room, two half baths
Listing Courtesy of SMART MLS / Listed By: Kary Apanovitch, Coldwell Banker Realty
$2,750,000 (USD)
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Red Coat Area Single Family Home

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25 Hermit Lane Westport, CT 06880

6 Bed
7 Baths
7054 sqft
MLS# 24204051
Privately nestled in Red Coat, this distinctive classically designed Colonial offers just over 7,000 sq. ft. of above-grade living space, with 6 bedrooms, 5 full and 2 half baths, and an attached 3-car garage. Set on 1.59 beautifully landscaped acres, this home pairs timeless architecture with sophisticated finishes, and an effortless flow designed for entertaining, working, and everyday living. The welcoming front entrance is framed by a spacious covered porch. Inside, the gracious foyer features herringbone hardwood floors and detailed wainscoting, setting an elegant tone throughout. The living room features a fireplace and double French doors opening to the expansive patio. Two archways lead to a versatile bonus room with a dry bar, an ideal setting for a pool table or casual gathering space. The formal dining room, accessed through French doors from the foyer, features built-in hutch cabinetry. It connects seamlessly to the kitchen, which is exceptionally equipped with custom cabinetry and hutches, two sinks, center island, a separate pantry, and Wolf appliances. The kitchen opens to the expansive family room, where 3 sets of French doors bring in abundant natural light and lead to the rear patio and built-in grill. A convenient mudroom with a private half bath connects the main living spaces to the attached three-car garage, with access to the au pair quarters above. A private office tucked quietly off the family room and an additional half bath complete the main lev
Listing Courtesy of SMART MLS / Listed By: Nicholas "Nick" Mastrangelo, Coldwell Banker Realty