Connecticut’s real estate landscape is a graceful fusion of historic mansions, coastal retreats, and grand countryside estates. With its close proximity to New York City, the state attracts buyers seeking both luxury and a serene, timeless atmosphere. Now, let’s explore the five most expensive houses that showcase Connecticut’s finest living.
5. New Canaan, CT – $13,900,000
Located in New Canaan, Connecticut, this estate is listed for $13,900,000 and spans 18,000 square feet. It includes 12 bedrooms, 16 bathrooms, a 2,000 square feet guest house, a 5,000 square feet wellness center, and a custom pool with spa, with the original home built in 1929 and major renovations completed between 2014 and 2017.
Where is New Canaan?
New Canaan, Connecticut, is a town known for its mid-century modern architecture and vibrant village center. It offers a blend of boutique shopping, restaurants, and cultural attractions like the Glass House and Carriage Barn Arts Center. The town has extensive parks and nature preserves, including Waveny Park and Irwin Park. Its residential areas feature a mix of historic homes and contemporary designs.
Living Room
Coffered ceiling panels with intricate relief designs draw the eye upward in the formal living room, where carved wood paneling surrounds a central fireplace. Velvet seating, a piano in the bay window area, and an antique chandelier all contribute to the room’s classical grandeur. Hardwood floors and a large patterned rug anchor the furnishings in a warm, symmetrical layout.
Kitchen
Under exposed ceiling beams and a large skylight, the kitchen features two islands, glass-front cabinets, and a wood-framed dining area. A massive range hood and a stone-tiled floor add rustic charm, while pendant lights hang across the room. Multiple prep zones and storage units make the layout both functional and visually balanced.
Dining Room
Encased in hand-painted floral walls and trimmed in gold, the dining room hosts a long formal table beneath an ornate crystal chandelier. A marble fireplace with a carved mantle lines one end, while arched French doors open to the garden. Delicate sconce lighting and polished furniture enhance the old-world aesthetic.
Bedroom
Just past the fireplace and built-in media cabinet, the bedroom leads into an adjoining space with its own chandelier and furniture suite. Upholstered headboards and footboards pair with a tufted bench, all aligned with large multi-pane windows. Neutral walls and wide-plank flooring give the space a calm and open feel.
Bathroom
Along one wall, a marble-topped bathtub sits below iron-grid windows, while dual vanities with arched mirrors stretch across the opposite side. A fireplace at the far end adds comfort to the spa-like design, complemented by a soft mural above. White cabinetry and floor tiles create a crisp and elegant finish.
Source: Danielle Malloy, Jess Lane Alsina @ Serhant Connecticut, LLC. via Coldwell Banker Realty
4. Greenwich, CT – $33,000,000
Set behind stone walls and a gated Cherry tree-lined drive in Greenwich, Connecticut, this $33,000,000 estate offers 18,954 square feet of living space. It features 8 bedrooms, 13 bathrooms, and spans 8.23 acres, including a 75-foot heated pool, pool house, tennis court, wine cellar, gym, and a separate apartment above the garage.
Where is Greenwich?
Where colonial settlers first laid roots in 1640, Greenwich, Connecticut, now thrives as a town of distinct neighborhoods. It is divided into sections like Cos Cob, Riverside, and Old Greenwich. The town features a strong boating community, with marinas and yacht clubs along the coastline. Greenwich also hosts Audubon centers and expansive nature preserves for outdoor exploration.
Kitchen
Centered around a long island with marble countertops and chrome barstools, the kitchen features high-end appliances and a sleek stainless steel range hood. Tall windows bring in natural light across white cabinetry, integrated refrigeration, and reflective backsplash panels. Pendant lights hang overhead, breaking up the otherwise streamlined ceiling.
Office / Library
Bookshelves reach up two stories in the library, wrapping around tall windows and a central desk setup beneath a decorative metal balcony. Lighting within the shelves casts a soft glow on the dark wood paneling and green accent rug. A rolling ladder, gold ceiling trim, and traditional desk create an elegant workspace.
Game Lounge
In the entertainment level, a pool table with a blue felt top sits in the foreground beside a gray sectional and flat-screen TV. The space also includes a bar area and small tables, with mirrored columns dividing zones without closing them off. Light walls and recessed lighting balance the darker floors and furniture accents.
Home Theater
Lined in acoustic paneling and illuminated by soft wall sconces, the theater features three rows of plush mauve recliners. A large projection screen dominates the front wall, flanked by floor speakers and topped by a recessed ceiling. Folded throws and side tables add comfort to the viewing setup.
Pool Area
At the heart of a U-shaped brick estate, the pool is framed by manicured hedges, modern lounge furniture, and symmetrical architecture. A central lap pool runs between two wings of the home, with stone pavers and umbrellas lining both sides. Surrounding buildings feature dormers, arched doorways, and balustrades for a stately composition.
Source: Leslie Mcelwreath, Joseph Barbieri @ Sotheby’S International Realty via Coldwell Banker Realty
3. Greenwich, CT – $35,000,000
This historic estate in Greenwich, Connecticut, is listed for $35,000,000 and offers 9,300 square feet of living space. It features 8 bedrooms, 9 bathrooms, and is set on 66 acres with amenities including a pool and pool house, tennis court, two carriage houses with apartments, greenhouses, a caretaker’s cottage, and paddocks.
Where is Greenwich?
Greenwich, Connecticut, is a coastal town that combines suburban living with a strong financial industry presence. It offers public beaches, golf courses, and a vibrant downtown centered around Greenwich Avenue. The town is home to the Bruce Museum, historic sites, and several annual cultural events. Its neighborhoods range from waterfront properties to sprawling inland estates.
Entry Hall
Just beyond the front door, the entry hall is lined with crown molding, traditional paneling, and antique furnishings arranged along both sides. A piano, a settee, and decorative vases sit among framed artwork and vintage rugs that define the space. Sunlight enters through a half-moon transom window, highlighting the polished wood floors and classic staircase.
Living Room
Soft light filters through tall windows in the living room, where cushioned floral seating faces a large central rug and round tables. Arched alcoves display collections of fish sculptures and nautical-themed items, with pastel blue backings adding contrast. Double doors open to an adjacent room, enhancing the flow and openness.
Library
Along the back wall of the library, built-in shelves stretch from floor to ceiling and surround a ladder, portrait paintings, and a central display gable. Patterned armchairs and a round table create a reading area beside a carved fireplace, while curtains and upholstery feature botanical motifs. Wood paneling and gold sconces add to the room’s old-world character.
Lounge
Surrounded by carved wood paneling, the lounge includes vintage armchairs and a small settee arranged around a central rug. A grand piano sits along one side, while display shelving and a tall grandfather clock add character to the corners. Floral curtains and framed artwork complete the softly lit, formal setting.
Bedroom
Situated along two walls of windows, the bedroom holds a patterned bed facing a marble fireplace surrounded by traditional trim. Beside the fireplace, built-in shelving with mint-green interiors showcases porcelain and books. Matching floral fabrics appear on the curtains, chairs, and headboard, maintaining a unified and elegant palette.
Source: Peter Janis @ Bhhs New England Properties via Coldwell Banker Realty
2. Darien, CT – $35,000,000
Perched on Hay Island in Darien, Connecticut, this $35,000,000 estate offers 8,684 square feet of living space surrounded by panoramic waterfront views. It includes 6 bedrooms, 8 bathrooms, a two-bedroom guest house, a pool house, and spans 18.15 acres featuring an infinity-edge pool, sandy beaches, a spa, and a dock. The main house was built in 2010.
Where is Darien?
Darien, Connecticut, is a coastal town located along the Long Island Sound between Stamford and Norwalk. It is known for its top-rated schools, small-town atmosphere, and waterfront parks. The town features two public beaches, a bustling downtown, and easy access to New York City by train. Its residential areas blend historic homes with modern developments.
Living Room
Anchored by a tufted ottoman, the living room blends neutral velvet seating with floral accent chairs beneath a coffered ceiling. Tall windows line the wall facing the water, while columned arches define the room’s layout. Soft gold drapes and red-patterned pillows add warmth to the cool-toned space.
Dining Room
Across from the main living area, the dining room features a polished wood table with high-back cream chairs and a crystal chandelier. Carved moldings and columned arches frame the views out to the water, visible through large divided-light windows. A pale blue patterned rug extends beneath the table, echoing the coastal palette.
Breakfast Nook
In a turret-style corner of the home, the breakfast room holds a round table surrounded by an eclectic mix of tufted and wooden seating. A metal lantern chandelier hangs from the vaulted ceiling, and a fireplace anchors one wall between two large windows. Houseplants and coastal views surround the space with natural texture and light.
Infinity Pool
Near the main residence, a sleek infinity pool is edged by a wide stone patio with multiple loungers and shaded seating. Built into a raised platform with a stone facade, the pool aligns with the tree line and views beyond. Landscaping includes flowering shrubs and planters that soften the modern lines.
Aerial View
Set on a wooded peninsula, the estate includes a main house, pool, and guest structures all positioned beside a secluded sandy cove. Mature trees surround the manicured lawn, with a small fleet of kayaks stored near the shoreline. The pool area sits elevated above the waterline, bordered by stone walls and lounge terraces.
Source: Leslie Mcelwreath @ Sotheby’S International Realty via Coldwell Banker Realty
1. Greenwich, CT – $43,000,000
Located in Mead Point, this waterfront property is listed for $43,000,000 and spans 11,500 square feet. The home includes 6 bedrooms, 11 bathrooms, and sits on 2.72 acres, offering features such as a new pool and spa, greenhouse, orchard, floating dock, and multiple entertaining areas across several levels.
Where is Greenwich?
Greenwich, Connecticut, sits along the Long Island Sound and serves as a gateway between New York City and New England. It is known for its historic homes, upscale shopping, and extensive parks and beaches. The town hosts several cultural institutions, including the Bruce Museum and the Greenwich International Film Festival. Its neighborhoods range from coastal communities to country estates.
Living Room
Framed by French doors and coastal views, the formal living room includes a white sofa flanked by patterned chairs, arranged around a fireplace. Built-in shelves, arched niches, and classic molding add architectural detail, while soft blues and yellows accent the furniture. A chandelier and sconces provide layered lighting throughout the room.
Kitchen
Anchoring the kitchen, a blue island with bar seating contrasts with white cabinetry and marble countertops set against glossy hardwood floors. Twin lantern-style pendant lights hang above the workspace, and a farmhouse sink sits under a window with diamond mullions. An open archway frames the view toward a blue-accented dining alcove and staircase.
Dining Room
Positioned beside a fireplace and beneath a ring chandelier, the dining area centers around a circular table with ten upholstered chairs. Hand-painted floral wallpaper and arched openings lead into a sunlit sitting room, while French doors open to a terrace with water views. Blue and cream tones unify the palette from ceiling molding to chair upholstery.
Rec Room
Inside the lower level, the game room features a ping-pong table, bar seating, dining booth, and multiple lounging areas beneath a paneled ceiling. Green accents appear in the bar, chairs, and light fixtures, creating a coastal palette. Nautical-themed art and a fireplace add a casual, family-friendly feel to the open-plan layout.
Pool Area
Behind the home, a rectangular pool with integrated spa overlooks manicured lawns and a curved waterfront beyond the stone terrace. Multiple loungers with umbrellas are placed near the pool, while a small bistro set sits at the edge of the property. The landscape flows outward to meet inlets and islands visible in the distance.
Source: Heather Platt @ Sotheby’S International Realty via Coldwell Banker Realty
