These five unique properties showcase a blend of historic architecture, waterfront locations, and expansive grounds across Connecticut. Caritas Island offers a private 3.5-acre waterfront retreat with a historic main house, deep-water dock, and guest accommodations. A Greenwich Colonial features a tennis court, putting green, and a separate guest apartment, while another historic estate features two 18th- and 19th-century homes on nearly six acres. A 2.98-acre Colonial balances historic charm with modern updates, featuring beautifully landscaped grounds and outdoor entertainment spaces. Lastly, a waterfront estate with multiple residences, a tennis court, and a scenic riverfront setting provides a rare opportunity to own a historic and expansive property.
1. Waterfront Estate on 3+ Acres
Listed for $7,495,000, Caritas Island is a 3.5-acre private estate on Long Island Sound, accessed by a gated causeway and featuring a c.1909 stone main house with 12 bedrooms and 10 bathrooms. The property includes a c.1870 three-bedroom guest cottage, a six-car garage with two staff apartments, a lap pool, a greenhouse, a pond, a sandy beach, and a natural swimming cove. With a 200-foot pier capable of accommodating a 75- to 150-foot boat and zoning for subdivision or nonprofit use, the estate offers opportunities for renovation or redevelopment.
Where is Stamford?
Stamford, CT, is a coastal city in Fairfield County, located in southwestern Connecticut along Long Island Sound. It is approximately 35 miles northeast of New York City, making it a major business and commuter hub with a direct Metro-North train line to Grand Central Terminal. Stamford is known for its thriving downtown, corporate headquarters, waterfront parks, and a mix of urban and suburban living, offering a blend of modern amenities and scenic coastal views.
Living Room
A white coffered vaulted ceiling, parquet wood flooring, and large French doors leading to an outdoor view. Plush seating in warm tones, a red velvet sofa, and an ornate area rug add elegance and comfort. Expansive windows provide natural light and frame a scenic waterfront setting.
Dining Room
White octagonal table with woven-back chairs, set against a backdrop of floor-to-ceiling windows. Terracotta tile flooring, sheer drapery, and a crystal chandelier add warmth and sophistication. French doors open to an outdoor patio with stunning water views.
Bedroom
Bright and airy bedroom features a white bed with pastel blue bedding, matching nightstands, and a classic writing desk. A built-in window seat with flowing drapes offers a relaxing nook with natural light. A modern egg chair and glass coffee table add a contemporary touch to the serene space.
Poolside
Long, narrow pool surrounded by stone decking and green cushioned lounge chairs under white umbrellas. A glass-enclosed sunroom and stone patio with a dining area enhance the charm of the classic home. Stunning waterfront views provide a tranquil and private setting for relaxation.
Source: Coldwell Banker
2. Updated 19th Century Colonial Home
Listed for $3,100,000, this 4,420-square-foot Colonial home, built in 1850, is set on a well-maintained property featuring a putting green, tennis court, and a detached one-car garage with a one-bedroom apartment above. The main house includes four bedrooms, six bathrooms (three full, three half), an open kitchen/family room, a sunroom, formal living and dining rooms, an office, and three wood-burning fireplaces. Additional features include a breakfast room with terrace views, a mudroom leading to an attached three-car garage, and a finished lower level with a second family room/game room, all located in the North Mianus school district with convenient access to the train, dining, and shopping.
Where is Cos Cob?
Cos Cob, CT, is a neighborhood in the town of Greenwich, located in Fairfield County along the Long Island Sound. It is approximately 3 miles east of downtown Greenwich and about 35 miles northeast of New York City, offering a mix of suburban charm and waterfront living. Known for its marinas, parks, and historic sites, Cos Cob provides a quieter, residential alternative to downtown Greenwich while still offering convenient access to shopping, dining, and Metro-North train service.
Porch
Front porch with a gray shingled exterior, white columns, and a rich wooden door. A wicker sectional with cushions and a coffee table creates a comfortable outdoor seating area. Lush greenery, including potted ferns and a manicured lawn, enhances the inviting atmosphere.
Kitchen
White cabinetry, black countertops, and a marble-topped island with seating for four. Stainless steel appliances and a farmhouse sink add modern functionality to the classic design. French doors lead to an adjacent sitting area, enhancing the open and inviting atmosphere.
Bedroom
A plush upholstered bed with patterned bedding, flanked by classic wooden nightstands and table lamps. Warm hardwood flooring and soft beige walls create a cozy and inviting atmosphere. An en-suite bathroom with white cabinetry is visible through an open doorway.
Bathroom
Bathroom with bold blue walls, a white vanity with a solid surface countertop, and chrome fixtures. A large mirror and multiple windows provide ample natural light, complemented by sheer white curtains. A tiled shower with a built-in niche adds functionality to the fresh and airy space.
Source: Coldwell Banker
3. Two 18th & 19th Century Homes on 6 Acres
Listed for $1,800,000, this 5,730-square-foot home blends two historic properties, the Dawson House (built in 1856) and the Ring Family Homestead (built in 1750 and relocated from Maine in 1985). The five-bedroom, seven-bathroom home features nine fireplaces, wide board floors, hand-blown glass windows, exposed beams, and period details preserving its historic authenticity. Set on nearly six acres across two lots, the property includes three post-and-beam outbuildings, a garage, wooded trails, a stream, and carefully restored architectural elements.
Where is Fairfield?
Fairfield, CT, is a coastal town in Fairfield County, located in southwestern Connecticut along Long Island Sound. It is approximately 50 miles northeast of New York City and 20 miles southwest of New Haven, offering a mix of suburban and waterfront living with direct Metro-North train access to Manhattan. Known for its top-rated schools, historic districts, and scenic beaches, Fairfield also features a vibrant downtown, parks, and cultural attractions, making it a desirable place to live.
Living Room
A large wooden fireplace with built-in cabinetry and a roaring fire. Classic furnishings, including a beige sofa, a wingback chair, and a rocking chair, sit atop a traditional patterned area rug. Natural wood flooring and wainscoting add rustic character to the room.
Dining Room
Inviting dining space has beamed wood ceiling, wide-plank flooring, and a traditional chandelier. A dark wooden table with upholstered chairs sits near large windows framed with rich wood trim. Adjacent kitchen with brick flooring is visible through a doorway, enhancing the home’s historic charm.
Kitchen
Kitchen with exposed wooden beams, brick flooring, and a farmhouse-style aesthetic. A large black range sits between custom cabinetry with natural wood and red-painted finishes. A built-in wooden dining table and antique-inspired fixtures add to the cozy, old-world ambiance.
Bedroom
Bedroom exudes historic charm with its beautifully carved twin beds, wide-plank hardwood floors, and soft neutral tones. Large windows allow natural light to fill the space, complementing the antique wall sconces and vintage standing mirror. A timeless and serene retreat with a touch of classic elegance.
Exterior
This breathtaking colonial-style home is set on a sprawling green landscape, framed by lush woodlands. The symmetrical façade, classic wooden siding, and elegant blue entryway exude historical elegance. The property features a grand stone staircase leading to the entrance, accentuated by charming period details. A picturesque retreat that perfectly blends tradition and modern luxury.
Source: Coldwell Banker
4. The Wedding Cottage
Listed for $2,050,000, “The Wedding Cottage” is a 3,316-square-foot Colonial built in 1930, set on a 2.98-acre lot in the heart of town. The home features four bedrooms, four bathrooms, a large kitchen with gourmet appliances, a paneled living room with a stone fireplace, a sun-filled family room, and a first-floor office/bedroom with a bar area. Outdoor spaces include a flagstone terrace, a stone fire pit, landscaped gardens, and a large shed for storage or additional use.
Where is Darien?
Darien, CT, is a coastal town in Fairfield County, located along Long Island Sound in southwestern Connecticut. It is approximately 40 miles northeast of New York City and 10 miles southwest of Stamford, offering a convenient commute via Metro-North Railroad. Known for its affluent neighborhoods, top-rated schools, and scenic beaches, Darien features a charming downtown, waterfront parks, and a strong sense of community.
Living Room
Beige paneled walls and large windows allow natural light into the space. A glass coffee table sits atop layered rugs, surrounded by a neutral-colored sofa and blue velvet armchairs. Built-in shelving, a bay window with a cushioned bench, and a set of French doors lead to an adjacent area.
Dining Area
Wide-plank hardwood floors and a large wooden dining table with Windsor chairs define the dining area. Cream-colored cabinetry, a black countertop, and a small island with barstools are present in the open kitchen. A metal drum pendant light hangs above the table, and a built-in hutch with black hardware is against the wall.
Kitchen
Cream-colored cabinetry contrasts with black countertops and a farmhouse-style sink under a double window. A marble-topped island with seating serves as a central gathering spot. A built-in fireplace with glass display cabinets and a circular mirror adds warmth to the space.
Bedroom
A tufted upholstered bed with white linens is positioned against a soft green wall. Warm wooden doors and flooring contrast with the neutral tones of the furniture. A vintage-style dresser and matching nightstand complement the space, with natural light streaming in.
Patio
Stone patio with a dining table and chairs is surrounded by lush greenery. Flowering plants, including pink peonies, are arranged in landscaped garden beds. Adirondack chairs are positioned on the well-manicured lawn, providing additional seating.
Source: Coldwell Banker
5. The Marsh House
Listed for $3,100,000, “The Marsh House” is a 14.6-acre waterfront estate in Old Lyme, featuring a 6,742-square-foot main residence originally built as a stone sheep barn in 1912 and later renovated with large arched windows and slate roofing. The property includes a separate Boathouse with a full kitchen, Great Room, and guest quarters, as well as the Gate House, a two-bedroom home on a separate 0.96-acre parcel. Additional features include a tennis court, pool, professionally landscaped gardens, and direct frontage on the Lieutenant River, with potential for a separate building lot.
Where is Old Lyme?
Old Lyme, CT, is a coastal town in New London County, located along Long Island Sound at the mouth of the Connecticut River. It is approximately 30 miles southeast of Hartford and 100 miles northeast of New York City, offering a mix of historic charm, waterfront living, and rural landscapes. Known as the birthplace of American Impressionism, Old Lyme has a rich artistic heritage, home to the Florence Griswold Museum and a vibrant arts community, along with beaches, marinas, and nature preserves.
Living Room
High-ceiling living room has exposed wooden beams and a stone fireplace. Neutral-colored sofas and leather chairs surround a glass coffee table on a striped area rug. Framed artwork and decorative accents complement the traditional architectural details.
Dining Room
Large arched window overlooking lush greenery. Terracotta tile flooring complements the wooden ceiling beams and furniture. Pendant lighting and wall sconces provide warm illumination around the modern and rustic seating arrangement.
Kitchen
Cream-colored cabinetry, a central island with storage, and a brown countertop. Terracotta tile flooring complements the stainless steel refrigerator and glass-fronted upper cabinets. Multiple pendant lights and recessed lighting illuminate the space, while a breakfast nook sits near a window.
Bedroom
Bedroom has a large arched window overlooking a swimming pool and landscaped greenery. Neutral-colored walls and a patterned area rug complement the simple furnishings. A doorway leads to an adjoining space with additional glass doors.
Pool
Stone-clad home has a symmetrical facade with dormer windows and a central balcony. A rectangular swimming pool sits in the landscaped backyard, surrounded by a stone patio and lush greenery. French doors on the lower level provide access to the outdoor space.
Source: Coldwell Banker
