Tour 5 of the Most Expensive Sprawling Mansions in Connecticut on the Market

Grand waterfront estates, historic mansions, and secluded countryside retreats make Connecticut’s real estate a haven of luxury and timeless elegance. The Gold Coast, stretching through Greenwich and Darien, is home to some of the most expensive properties, featuring sprawling lawns, private docks, and breathtaking Long Island Sound views. Beyond the coast, lavish estates in Litchfield County offer rolling hills, equestrian facilities, and timeless colonial architecture. Whether nestled along the shoreline or tucked into the countryside, these properties exude sophistication and exclusivity.

Let’s explore the five most expensive houses in the Constitution State.

5. Greenwich, CT – $5,995,000

Situated on an isolated lane, this 8,818 sq. ft. Elizabethan-style manor is an exquisite recreation of an English estate from the 17th century, constructed with original beams brought over from England. Listed for $5,995,000, the home sits on over four acres of landscaped grounds and features 5 bedrooms, 6 bathrooms, gracious formal rooms, and a chef’s kitchen. The property includes 8 garage bays for car enthusiasts and extensive outdoor amenities, including an infinity pool, an outdoor kitchen, a pool house with a guest suite, a lighted Har-Tru tennis court, and a putting green.

Where is Greenwich?

Greenwich, Connecticut, is a coastal town on Long Island Sound, known for its affluent neighborhoods and proximity to New York City. It has a strong financial sector, with many hedge funds and investment firms based in town. The downtown area features upscale shopping, fine dining, and cultural attractions like the Bruce Museum. Outdoor spaces, including Greenwich Point Park and the Audubon Center, offer scenic waterfront views and nature trails. With a mix of urban sophistication and suburban tranquility, Greenwich remains a sought-after place to live and visit.

Living Room

Exposed wooden beams and a vaulted ceiling define the living room’s structure. A floor-to-ceiling stone fireplace serves as the focal point, flanked by seating arrangements in rich patterns. Large windows and glass doors line the walls, letting in natural light and leading to an outdoor space. A mix of sofas, armchairs, and tables provides multiple areas for conversation and relaxation.

Kitchen

Wood cabinetry and stainless steel appliances fill the kitchen. A central island with a gas cooktop and marble countertop provides additional workspace. Double ovens, a large refrigerator, and a tiled backsplash create a professional-grade cooking environment. Glass-front cabinets display dishware, while a mix of recessed and natural lighting brightens the room.

Dining Room

A long wooden dining table sits beneath a crystal chandelier, surrounded by high-backed chairs. Large windows and glass doors bring in views of the outdoor landscape. The space is accented with a fireplace, a wooden sideboard, and soft drapery. Natural wood beams contrast with striped walls, adding to the room’s character.

Entertainment Room

This entertainment room is a combination of home theater and gaming space, which features a projector screen, pool table, and plush recliner seating. Framed movie posters line the walls, reinforcing the cinematic theme. Rows of chairs provide extra seating for guests. The carpeted floor and dimmable lighting enhance the entertainment experience.

Bedroom

An open loft and exposed wooden beams give the bedroom a sense of depth. A large bed with a carved wooden frame sits opposite a seating area with a leather sofa. Built-in bookshelves frame the windows, offering storage and display space. French doors lead to an adjacent room, while warm tones and classic furnishings complete the space.

Source: Yashmin Lloyds @ Compass Connecticut, LLC. via Coldwell Banker Realty

4. Washington, CT – $6,250,000

Designed in 1885 as a summer retreat for the Gilded Age by renowned architect Ehrick Rossiter, Rock Gate is a 9,165 sq. ft. Queen Anne shingle-style estate situated among the landscapes of Washington, CT. Listed for $6,250,000, the home features 5-6 bedrooms, 5 full bathrooms, and 1 half bathroom, with restored butternut wood panels, walnut and fir floors, arched windows, porches, and turreted roofs. Modern updates include a remodeled primary bath with a dressing room, fresh paint, stylish wallpaper, new carpeting, and upgraded systems such as boilers, hot water tanks, plumbing, lighting controls, and a well pump. Ten fireplaces, a wine cave, and wide staircases add to its character. The property includes a heated gunite saltwater pool, a new 1-bay detached garage, a 3-bay garage with a walk-up loft, stone pathways, and a private rear terrace surrounded by trees.

Where is Washington?

Tucked into the hills of Litchfield County, Washington, Connecticut, is a town where history, nature, and small-town charm come together. It served as the inspiration for the fictional town of Stars Hollow in the television series Gilmore Girls. The town is home to The Gunnery, a private boarding school, and the Gunn Memorial Library, which reflects its rich literary culture. Outdoor activities are popular, with hiking trails in Steep Rock Preserve and scenic views along the Shepaug River. Washington’s blend of history, nature, and culture makes it a quiet but vibrant community.

Foyer

Intricate wood paneling and carved details define the foyer. A curved archway frames the entrance to the steps, which are covered in a patterned carpet. The coffered ceiling and warm wood tones create a rich, traditional atmosphere. Decorative wall sconces add soft lighting to the space.

Dining Room

Bookshelves filled with leather-bound volumes line the walls of the dining room. A white fireplace contrasts with the blue paneling, adding a focal point. A chandelier hangs above the polished wood table, surrounded by upholstered chairs. Large windows bring in natural light, highlighting the elegant details.

Wine Cellar

A wine cellar with floor-to-ceiling racks holds an extensive collection of bottles. Dark wood shelving and a richly patterned rug add warmth to the space. A framed vintage print and soft lighting create a refined atmosphere. Wooden blinds filter natural light, maintaining the ideal environment for storage.

Home Office

The home office features a curved wall with multiple windows. Patterned wallpaper and a Persian rug add depth to the space. Dark wood furnishings, including display cabinets and a grand desk, reinforce the traditional aesthetic. A white fireplace provides a cozy element to the room.

Bedroom

Built-in window seats and lattice windows bring charm to the bedroom. A crystal chandelier hangs above, adding an elegant touch. Blue and white patterned wallpaper complements the upholstered seating and bedding. Bookshelves integrated into the walls provide both storage and decoration. The soft color palette and natural light create a peaceful retreat.

Source: Maria Taylor @ Klemm Real Estate Inc via Coldwell Banker Realty

3. Stamford, CT – $7,495,000

Listed for $7,495,000, Caritas Island is a private 3.5-acre waterfront estate in Stamford with 300-degree views of Long Island Sound. Accessed by a gated causeway, the property includes a 14,149 sq. ft. main house built in 1909 with 12 bedrooms and 10 bathrooms, a 3-bedroom guest cottage from 1870, and a 6-car garage with two staff apartments above. Outdoor features include waterside terraces, a lap pool, a greenhouse, a pond, a sandy beach, and a natural swimming cove. A 200-foot pier with a 13-foot draft can accommodate boats between 75 and 150 feet, protected by a stone breakwater. The estate, which totals over 4 acres per the property deed, offers opportunities for renovation, new construction, or subdivision into two lots and is also zoned for nonprofit use.

Where is Stamford?

Stamford, Connecticut, is a coastal city on Long Island Sound and part of the New York metropolitan area. It has a major business district with corporate headquarters, financial firms, and a growing tech sector. The city’s downtown offers restaurants, shopping, and cultural venues like The Palace Theatre. Parks and waterfront areas, including Cove Island Park and Harbor Point, provide outdoor recreation. With a mix of urban development and green spaces, Stamford balances city life with access to nature.

Living Room

Curved ceilings and detailed molding frame the bright living room. A large chandelier hangs overhead, casting light over a mix of plush seating. Expansive windows and glass doors open to views of the water and surrounding landscape. A patterned rug anchors the space, adding contrast to the white walls.

Kitchen and Dining Area

Terracotta flooring and exposed beams add warmth to the open kitchen and dining area. A large wooden dining table sits under a crystal chandelier, positioned near floor-to-ceiling windows. White cabinetry and stone accents contrast with the rustic elements. A second level overlooks the space, adding depth to the design.

Library

Deep green bookshelves line the walls of the library, filled with an extensive collection of books. Gilded mirrors and gold-trimmed columns add decorative elements. A fireplace with an ornate frame sits between tall windows, bringing in natural light. Comfortable seating and a central coffee table create a cozy reading space.

Bedroom

Four-poster beds and classic furniture define the airy bedroom. Large windows frame views of the water, bringing in natural light. A mix of upholstered seating and wooden pieces create a balance of comfort and elegance. Neutral tones and soft patterns enhance the timeless feel of the room.

Lap Pool

A long, narrow pool stretches alongside the stone patio, lined with lounge chairs and umbrellas. Greenery and potted plants soften the edges of the space. Glass doors lead into the home, connecting the indoor and outdoor areas. Water views complete the setting, making it a relaxing retreat.

Source: Joseph Barbieri @ Sotheby’S International Realty via Coldwell Banker Realty

2. Newtown, CT – $11,000,000

Perched atop a hill with sweeping views of the Aspetuck River, Red Gate Farm is a 54-acre equestrian estate in Fairfield County, listed for $11,000,000. The 10,800 sq. ft. stone manor home features 4 bedrooms, 5 full bathrooms, and 3 half bathrooms. Inside, an 18-foot grand entry leads to a formal living and dining room, a kitchen/family room, a bar, six fireplaces, a walk-in wine cellar, and an elevator serving all three floors. The equestrian facility includes three barns with 69 stalls, wash stalls, tack rooms, laundry, rubber flooring, full haylofts, a Grand Prix/derby field, indoor and outdoor riding rings, a round pen, staff apartments, an office with a viewing room, a gym, paddocks, fenced pastures, and equipment garages. A long private driveway provides access to this exceptional property.

Where is Newtown?

Newtown, Connecticut, is a historic town in Fairfield County, founded in 1705. Its town center features the iconic Newtown flagpole and a mix of colonial and Victorian architecture. Ferris Acres Creamery, a popular local spot, draws visitors for homemade ice cream. The town offers outdoor recreation at places like Collis P. Huntington State Park, with trails for hiking and horseback riding. With a blend of history, small-town charm, and natural beauty, Newtown remains a vibrant community.

Living Room

Exposed wooden beams line the ceiling, adding warmth to the living room. A stone fireplace with a carved wooden mantel serves as the focal point. Large windows framed by patterned drapes bring in natural light and offer views of lush greenery. Plush seating and antique-style furniture create an inviting space for conversation or reading.

Dining Room

Golden chandeliers hang from the beamed ceiling, casting a glow over the dining table. Tall windows draped with dark curtains provide a view of the garden. A polished wood china cabinet and decorative sculptures line the walls. The long table, surrounded by high-backed chairs, serves as the heart of the space.

Office

Floor-to-ceiling bookshelves filled with leather-bound volumes surround the home office. An intricately carved wooden arch frames the central bookcase, drawing attention to the rich details. A large wooden desk sits near a window, offering a workspace with a scenic view. Leather armchairs and a vintage globe add character to the room.

Bedroom

Exposed brick surrounds the fireplace, giving the bedroom a rustic charm. Ornate seating pieces with tufted upholstery create a cozy lounge area. A large bed with a quilted cover sits beneath a window framed by draped valances. Soft lighting from sconces and lamps enhances the room’s inviting atmosphere.

Bathroom

Sky-blue painted clouds stretch across the bathroom ceiling, framed by wooden beams. A glass-enclosed shower sits between two round windows, bringing in natural light. Dual vanities with marble countertops offer storage and convenience. A freestanding clawfoot tub completes the elegant design.

Source: Krissy Blake @ Sotheby’S International Realty via Coldwell Banker Realty

1. Salisbury, CT – $11,950,000

Valued at $11,950,000, Linden Hill Farm is a 72-acre estate in Litchfield County featuring an 8,334 sq. ft. Georgian Revival home built in 1929 with 6 bedrooms, 5 full bathrooms, and 3 half bathrooms. The property includes original oakwood floors, six antique fireplaces, and multiple outbuildings. A double-height entrance hall leads to a stone terrace overlooking 40 acres of fields and meadows. Reception rooms feature antique French doors opening to gardens, while a sunroom connects to a formal garden. The eat-in kitchen has a center island, commercial-grade appliances, a butler’s pantry, and a dining area with French doors to the terrace. A paneled library adjoins. The primary suite includes a fireplace, two baths, two dressing rooms, a sitting room, and a private terrace. Two additional ensuite guest rooms have fireplaces, while a separate wing offers three more bedrooms and a game room. Outdoor amenities include a pool with a summer kitchen, a pool house, and a tennis court.

Where is Salisbury?

Nestled in Connecticut’s northwest corner, Salisbury sits near the borders of New York and Massachusetts, surrounded by rolling hills and scenic lakes. It is known for its scenic countryside, historic homes, and proximity to the Appalachian Trail. The town hosts the annual Salisbury Winter Sports Association ski jump competition, a long-standing local tradition. Lakeville, a village within Salisbury, offers access to lakes and outdoor recreation. With a blend of rural charm and cultural attractions, Salisbury attracts both residents and visitors year-round.

Kitchen

Copper cookware lines open shelves, bringing warmth to the bright kitchen. A large island with a marble top offers seating and workspace. Stainless steel appliances, including a professional-grade range, blend with white cabinetry. A window above the sink frames a garden view, adding to the room’s welcoming feel.

Dining Room

Hand-painted floral wallpaper wraps around the dining room, adding charm to the space. A chandelier with multiple candle-like lights hangs from the ceiling, illuminating the polished wooden table. French doors let natural light in, leading to a garden view. A fireplace with an ornate mantel sits against the wall, framed by classic decor.

Wine Cellar

Rows of wine bottles fill custom wooden racks in the wine cellar. A brick floor and arched ceiling create an old-world atmosphere. A sturdy wooden table sits at the center, providing space for tasting and selection. Soft lighting enhances the warmth of the space, making it ideal for storage and display.

Bedroom

Four-poster bed with twisted wooden columns stands as the centerpiece of the bedroom. Blue and white toile fabric covers the canopy and accents the windows. A fireplace with a carved mantel adds elegance, while a cozy seating area provides a spot to unwind. Large windows brighten the room, offering views of the surrounding landscape.

Pool

Neatly trimmed hedges and a row of umbrellas frame the poolside retreat. Lounge chairs with striped cushions line the stone patio, inviting relaxation. A gazebo at the far end offers shade and a quiet escape. Clear blue water reflects the sky, creating a serene outdoor setting.

Source: Peter Klemm @ Klemm Real Estate Inc via Coldwell Banker Realty