With $5 million, Connecticut’s real estate market offers a captivating glimpse into luxury living in the heart of New England. These properties range from historic estates with timeless charm to modern retreats boasting cutting-edge design, all set against the state’s picturesque landscapes. Imagine sprawling grounds with lush gardens, waterfront homes overlooking serene rivers or Long Island Sound, and grand interiors designed for comfort and elegance. Whether nestled in quaint towns or within easy reach of bustling cities, these homes showcase the best of upscale living. In this post, we’ll uncover ten stunning properties that define high-end real estate in Connecticut.
10. Greenwich, CT – $4,900,000

For $4,900,000, here’s your chance in Greenwich. This 5-bed, 5-bath, 6,753 sq ft single-family home, built in 1936, is situated on a 1.1-acre lot. The property includes two fireplaces and spacious living areas designed for both comfort and entertaining. The layout features five bedrooms and 4.1 baths, offering ample space for relaxation. Outdoor areas provide serene lake views and a private setting. The home combines thoughtful design with a picturesque location.
Where is Greenwich, CT?

Greenwich, Connecticut, is located in the southwestern corner of the state, in Fairfield County, along Long Island Sound. It lies approximately 35 miles northeast of New York City, 15 miles southwest of Stamford, and about 85 miles southwest of Hartford, the state capital. Positioned near Interstate 95 and the Merritt Parkway (Route 15), Greenwich is known for its affluent neighborhoods, historic charm, and vibrant downtown areas. The town offers scenic coastal views, beautiful parks, and a blend of cultural and recreational amenities, while providing convenient access to the New York metropolitan area.
Living Room

This elegant living room, part of a 6,753 sq ft residence with 5 beds and 5 baths, features high vaulted ceilings and a statement marble fireplace as its focal point. Large windows allow natural light to illuminate the modern and sophisticated space, creating an inviting atmosphere.
Dining Room

Adjacent to the living room, the dining space is designed for formal gatherings, with ample room to accommodate a large dining table. Its tall windows and clean aesthetic seamlessly integrate with the home’s expansive 6,753 sq ft layout.
Kitchen

The chef’s kitchen boasts sleek cabinetry, high-end stainless-steel appliances, and a functional design that highlights the scale of this 6,753 sq ft property. The flow from the kitchen to surrounding areas emphasizes the home’s thoughtful design.
Primary Bedroom

This spacious primary suite, part of the 5-bedroom, 5-bathroom layout, features high ceilings and abundant natural light from multiple large windows. Its serene atmosphere perfectly complements the home’s luxurious scale.
Home Office

The circular office space is a standout feature in this 6,753 sq ft property, offering custom built-ins and a panoramic view through its surrounding windows. It serves as a bright and functional workspace within the residence.
Source: Stephen M Archino @ Sotheby’S International Realty Via Coldwell Banker Realty
9. New Canaan, CT – $4,985,000

This is what $4,985,000 gets you in New Canaan. This 6-bed, 8-bath, 6,000 sq ft single-family home features en suite bathrooms for all bedrooms and three finished floors. The interior includes 9’+ ceilings and high-quality materials with detailed craftsmanship. The lower level offers additional finishing potential to suit specific needs. Outdoor spaces include broad stone terraces overlooking a large back lawn. The layout is designed to combine functionality with elegant living.
Where is New Canaan, CT?

New Canaan, Connecticut, is located in the southwestern part of the state, in Fairfield County, about 8 miles north of Stamford and 10 miles northeast of Greenwich. It lies approximately 40 miles northeast of New York City and 50 miles southwest of Hartford. Positioned near the Merritt Parkway (Route 15) and U.S. Route 123, New Canaan is known for its charming downtown, historic homes, and renowned modernist architecture, including works by the Harvard Five. The town offers a blend of cultural attractions, beautiful parks, and a suburban atmosphere with convenient access to nearby urban centers.
Living Room

This living room features coffered ceilings and built-in shelves, creating a refined yet functional space within this 5-bedroom, 5-bath, 6,753 sq. ft. home. The layout offers seamless integration with adjacent areas, perfect for relaxation and hosting.
Kitchen

The kitchen highlights a large island, detailed cabinetry, and gold accents, complementing the upscale charm of the residence. With ample space, it connects effortlessly to other areas, emphasizing practicality within its expansive layout.
Dining Room

This dining area, surrounded by large windows, provides a bright, airy setting ideal for gatherings. The design balances elegance with comfort, reflecting the sophistication of this spacious property.
Source: Christine Saxe & Amanda Bryan @ Compass Connecticut, LLC. Via Coldwell Banker Realty
8. Westport, CT – $4,995,000

For $4,995,000, here’s what’s waiting in Westport. This 8-bed, 11-bath, 10,556 sq ft single-family home spans three living floors with 16 rooms and ceilings between 12 and 13 feet. The layout includes a grand central hall connecting the salon, grand room, library, dining room, and a modern kitchen with an attached family room and deck. The primary suite offers separate closets and bathrooms, including a new showpiece bath with a balcony and a large water feature. Outdoor spaces feature balconies, decks, sunrooms, and porches with water views in multiple directions. Additional amenities include a 6-car garage, roof deck, and access to the association pool, beach, and deep-water dock.
Where is Westport, CT?

Westport, Connecticut, is located in the southwestern part of the state, in Fairfield County, along Long Island Sound. It lies approximately 47 miles northeast of New York City, 25 miles southwest of New Haven, and about 70 miles southwest of Hartford. Positioned near Interstate 95 and the Merritt Parkway (Route 15), Westport is known for its upscale neighborhoods, vibrant arts community, and charming downtown area. The town features scenic waterfront parks, beaches, and cultural attractions such as the Westport Country Playhouse and offers a blend of suburban living and easy access to nearby urban centers.
Entry

This entryway features intricate wainscoting, a coffered ceiling, and classic chandeliers. Large windows allow natural light to flood the 10,556 sq ft home, complementing the room’s detailed architectural elements.
Living Room

The formal sitting room is adorned with rich red walls, intricate crown molding, and expansive windows. Detailed curtains frame views of the landscaped grounds, reflecting the elegance of this 10,556 sq ft home. This 8-bedroom, 11-bath property balances ornate details with functional luxury.
Primary Bedroom

The primary bedroom offers an expansive layout with large windows overlooking the estate. It is part of the home’s 8 bedrooms and features connections to the elegant design theme seen throughout the 10,556 sq ft property. This private space ensures both comfort and style.
Home Office

This wood-paneled library provides a cozy retreat with built-in shelves and large windows. The space harmonizes with the rest of the 10,556 sq ft home, offering a private area within its 8 bedrooms and 11 bathrooms. The room is designed for functionality and elegance.
Pool Area

The landscaped backyard features a large pool surrounded by lush greenery. As part of this 10,556 sq ft home, the outdoor space complements the interior’s refined design. The estate offers privacy and leisure, seamlessly integrating with the 8-bedroom, 11-bath layout.
Source: Mark Gilrain @ Brown Harris Stevens Via Coldwell Banker Realty
7. Branford, CT – $4,950,000

Check out what $4,950,000 can buy in Branford. This 4-bed, 4-bath, 3,871 sq ft single-family home features multiple French doors, balconies, and custom windows designed to capture natural light and scenic views. The main level includes a well-equipped kitchen and a spacious dining area suitable for large gatherings. The living room opens to a wraparound porch offering expansive and picturesque views. The upper level contains four bedrooms, including a primary ensuite with vaulted ceilings, two balconies, and 180-degree water views. The layout emphasizes seamless indoor-outdoor living and thoughtful design throughout.
Where is Branford, CT?

Branford, Connecticut, is located in the southern part of the state, along the Long Island Sound coastline, in New Haven County. It lies approximately 10 miles east of downtown New Haven, 40 miles south of Hartford, and about 80 miles northeast of New York City. Positioned near Interstate 95 and U.S. Route 1, Branford is known for its scenic shoreline, historic town center, and natural attractions like the Thimble Islands. The town offers a mix of residential charm, cultural heritage, and outdoor recreational opportunities, with easy access to nearby urban and coastal amenities.
Dining Room

The dining area, set in a bay window configuration, offers water views through multiple surrounding windows. This area is designed to connect seamlessly with the rest of the home’s 4-bedroom, 4-bath layout.
Kitchen

The kitchen includes stainless steel appliances, a center island, and expansive windows facing the waterfront. Its design integrates with the 4-bedroom, 4-bathroom structure for functional living.
Primary Bedroom

The primary bedroom features panoramic water views through large windows and provides direct access to other parts of the 4-bedroom, 4-bathroom home. Its layout optimizes natural light and space.
Sunroom

This windowed sunroom offers a tranquil spot to enjoy the waterfront scenery. It’s a well-planned space within the 4-bedroom, 4-bathroom home.
Pool Area

The outdoor pool is set within a landscaped yard, with the home’s 4 bedrooms and 4 bathrooms designed to accommodate both indoor and outdoor living seamlessly.
Source: Vicky Welch @ William Raveis Real Estate Via Coldwell Banker Realty
6. Darien, CT – $5,299,000

Here’s what $5,299,000 can offer you in Darien. This 6-bed, 10-bath, 9,203 sq ft single-family home features landscaped grounds with an oversized saltwater pool, spa, flagstone terrace, outdoor kitchen, fire pit, and a pool house with a full bath. The interior includes a two-story foyer, living room with views of the grounds, dining room, library, gaming room, and screened porch. The chef’s kitchen offers a walk-in pantry, butler’s pantry, abundant storage, and a windowed breakfast room adjacent to the family room. The primary suite includes a spa-like bath with a soaking tub, separate shower, double sinks, and an oversized walk-in closet. Additional amenities include a finished third floor with a bedroom and bath, a lower level with a recreation room, gym, and a 500+ bottle wine cellar.
Where is Darien, CT?

Darien, Connecticut, is located in the southwestern part of the state, in Fairfield County, along Long Island Sound. It lies approximately 40 miles northeast of New York City, 10 miles southwest of Stamford, and about 70 miles southwest of Hartford. Positioned near Interstate 95 and the Merritt Parkway (Route 15), Darien is known for its affluent residential neighborhoods, charming downtown, and beautiful coastal parks. The town offers a blend of suburban tranquility and convenient access to nearby urban centers and shoreline attractions.
Entryway

The entryway showcases a wooden front door framed by frosted glass panels and sidelights. A staircase with elegant wooden railings and white wainscoting leads to the upper floor. Large windows above the door provide abundant natural light, highlighting the hardwood floors and detailed wall paneling.
Living Room

The living room features a central fireplace with a decorative mantel, complemented by navy blue walls and crown molding. Built-in shelving and a large window add functionality and brightness. A wide entryway connects the room to adjacent spaces, creating a seamless flow.
Formal Dining Room

The dining room includes a large rectangular table with seating for eight and is anchored by a chandelier. Dual windows dressed with patterned curtains bring in natural light. Neutral walls, wainscoting, and a mirrored sideboard add elegance and symmetry to the space.
Kitchen

The kitchen centers around a large island with stone countertops and built-in storage, offering seating for three. Custom white cabinetry lines the walls, while dual ovens, a six-burner gas stove, and a farmhouse sink provide a chef-friendly layout. Recessed lighting and hanging pendant fixtures brighten the space.
Family Room

The family room boasts a vaulted ceiling with exposed beams and a central circular window. A stone fireplace creates a warm focal point, complemented by oversized windows framing garden views. Comfortable seating surrounds a central coffee table, providing a cozy yet open feel.
Source: Pamela Huber @ Compass Connecticut, LLC. Via Coldwell Banker Realty
5. Stamford, CT – $4,995,000

At $4,995,000, this is what’s available in Stamford. This 5-bed, 7-bath, 7,353 sq ft single-family colonial home features a meticulously updated chef’s kitchen and multiple entertaining spaces, including a formal dining room, family room, oversized living room, and home office with coffered ceilings. The primary suite on the upper level includes a private balcony with LI Sound views, a dressing room/office, two walk-in closets, and a bathroom with a jacuzzi tub overlooking the water. The second level offers three additional bedrooms, each designed for comfort and style. The top level includes a versatile sitting/game room, a home office, and a bedroom with an en suite bathroom. Panoramic views of the LI Sound enhance nearly every corner of the home.
Where is Stamford, CT?

Stamford, Connecticut, is located in the southwestern part of the state, in Fairfield County, along Long Island Sound. It lies approximately 35 miles northeast of New York City, 15 miles southwest of Norwalk, and about 80 miles southwest of Hartford. Positioned along Interstate 95 and the Merritt Parkway (Route 15), Stamford serves as a major business hub and cultural center for the region. The city is known for its vibrant downtown, corporate offices, diverse neighborhoods, and scenic waterfront areas. Stamford offers a blend of urban amenities, suburban neighborhoods, and convenient access to both New York City and the Connecticut shoreline.
Living Room

This expansive living room with vaulted ceilings and tall French doors highlights the elegance of this 5-bed, 7-bath home. Ocean views fill the space with natural light, emphasizing the hardwood floors and detailed trim work.
Dining Room

The dining room, part of this 5-bed, 7-bath property, features a coffered ceiling and hardwood floors. A central chandelier adds refinement, while its seamless layout connects it to adjoining spaces.
Kitchen

The kitchen in this 5-bedroom, 7-bath home showcases white cabinetry, a central island, and marble countertops. Large windows offer scenic water views, complementing the functional and open design.
Home Office

This home’s 5 bedrooms and 7 baths include a paneled office with built-in bookshelves. Expansive windows with water views enhance the space’s practicality and architectural charm.
Primary Bedroom

The primary bedroom of this 5-bedroom, 7-bath home features French doors leading to a private balcony. Ocean views, hardwood floors, and neutral tones create a tranquil retreat.
Patio

The 5-bed, 7-bath home includes a backyard with a paved seating area overlooking the coastline. A manicured lawn and lush landscaping complete the serene outdoor setting.
Source: Jodi Boxer & Jessica Buckley @ Keller Williams Prestige Prop. Via Coldwell Banker Realty
4. Ridgefield, CT – $4,995,000

With $4,995,000, this could be your next home in Ridgefield. This 8-bed, 9-bath, 11,480 sq ft single-family home features a chef’s kitchen with a large Aga stove, custom cabinetry, commercial-grade appliances, a walk-in pantry, and a fully equipped butler’s pantry. The main level includes a family room, eat-in area, formal dining room with access to a covered porch and fireplace, a living room, and a library. The upper level offers a primary suite with a fireplace, dressing room, and luxury bath, along with three en suite bedrooms, an Au Pair/In-Law suite with a full kitchen and living area, and a private office/library. The finished third floor includes a media/rec room, one en suite bedroom, two additional bedrooms, and a retro-style bathroom. Additional amenities include an elevator accessing all floors and a wellness level with an indoor pool, radiant heated floors, a full bathroom, and an exercise room.
Where is Ridgefield, CT?

Ridgefield, Connecticut, is located in the southwestern part of the state, in Fairfield County. It lies approximately 50 miles northeast of New York City, 25 miles southwest of Danbury, and about 60 miles southwest of Hartford. Positioned near U.S. Route 7 and State Route 35, Ridgefield is known for its historic town center, preserved colonial architecture, and vibrant arts community. The town offers a blend of small-town charm, cultural attractions, and access to outdoor recreation in nearby parks and trails, providing a peaceful yet well-connected suburban environment.
Dining Room

This elegant dining room accommodates 8 guests and opens to the landscaped gardens through French doors. It is part of an 8-bedroom, 9-bathroom home, blending formal design with functional space for entertaining.
Kitchen

The expansive gourmet kitchen, featuring two islands and custom cabinetry, is a centerpiece of this 8-bedroom, 9-bathroom home. Large windows flood the space with natural light, enhancing the polished wood flooring and modern appliances.
Primary Bedroom

This primary bedroom, situated in an 8-bedroom, 9-bathroom home, includes a fireplace and built-in bookshelves. Its generous layout is complemented by views of the surrounding greenery, offering a peaceful retreat.
Library

The classic library in this 8-bedroom, 9-bathroom estate features floor-to-ceiling bookshelves, a fireplace, and large windows. The elegant wood paneling and tranquil atmosphere create a perfect reading sanctuary.
Indoor Pool

The indoor pool area, part of this 8-bedroom, 9-bathroom residence, includes stone finishes and wood accents for a luxurious feel. Floor-to-ceiling windows connect the space to the outdoors, providing natural light year-round.
Backyard

The landscaped gardens include a central courtyard, manicured hedges, and flowering plants, adding charm to this 8-bedroom, 9-bathroom estate. French doors lead directly to this serene outdoor space, perfect for relaxation or gatherings.
Source: Peggy Marconi & Karla Murtaugh @ Compass Connecticut, LLC. Via Coldwell Banker Realty
3. Salisbury, CT – $4,750,000

Take a look at what $4,750,000 brings you in Salisbury. This 4-bed, 4-bath, 4,548 sq ft single-family home features an L-shaped porch leading to a light-filled entrance hall and a bluestone patio with expansive views. The main level includes a living room with oak floors and a fireplace, a dining room with a built-in breakfront and patio access, and a chef’s kitchen with antique brick floors, a large island, stone countertops, and high-end appliances. A den with a fireplace, a custom mudroom, and a powder room complete the first floor. The second level offers a primary suite with panoramic views, an oversized walk-in closet, and a custom bathroom, along with three additional bedrooms and two full baths. A detached garage with radiant floor heating includes a second-floor space ready for conversion into a studio or office.
Where is Salisbury, CT?

Salisbury, Connecticut, is located in the northwestern corner of the state, in Litchfield County, near the borders of New York and Massachusetts. It lies approximately 45 miles northwest of Hartford, 25 miles northeast of Poughkeepsie, New York, and about 50 miles southeast of Pittsfield, Massachusetts. Positioned along U.S. Route 44 and near State Route 41, Salisbury is known for its rural beauty, historic charm, and proximity to the Appalachian Trail and the Taconic Range. The town offers a peaceful, scenic setting with cultural attractions such as the historic Salisbury Congregational Church and outdoor recreation opportunities like hiking, fishing, and exploring nearby lakes and nature reserves.
Living Room

The living room highlights built-in shelving and a classic brick fireplace, framed by wide windows that bring in natural light. This space complements the balance of style and comfort in this 4-bedroom, 4-bath residence.
Kitchen

The kitchen offers a central island, brick flooring, and glass-paneled cabinets, blending traditional charm with modern functionality. Its design supports the versatile layout of the 4-bedroom, 4-bath home.
Patio

The outdoor patio features a pergola and a dining area overlooking scenic views, creating a serene spot for entertaining. This inviting addition enhances the appeal of the 4-bedroom, 4-bath property.
Source: William Melnick & Elyse Harney Morris Elyse Harney Real Estate Via Coldwell Banker Realty
2. Sharon, CT – $4,850,000

For $4,850,000, this is what’s on the market in Sharon. This 8-bed, 9-bath, 8,072 sq ft single-family home includes a main level primary suite and multiple sitting rooms with wood-burning fireplaces, all opening to a three-story atrium. The second floor features seven ensuite bedrooms, one serving as a gym and another as an office. The property is part of an association managing 50 acres with a heated Gunite pool, pool house, and tennis and pickleball courts. Originally built in 1812 and expanded in 1923, the home retains historic details, including art deco bathrooms and William Morris wallpaper. The layout blends historic charm with modern amenities and community features.
Where is Sharon, CT?

Sharon, Connecticut, is located in the northwestern corner of the state, in Litchfield County, near the New York state border. It lies approximately 35 miles west of Torrington, 45 miles northwest of Hartford, and about 20 miles southeast of Millerton, New York. Positioned near State Route 4 and U.S. Route 7, Sharon is known for its rolling hills, pastoral landscapes, and historic town center. The town offers a tranquil, rural atmosphere with cultural and natural attractions such as the Sharon Audubon Center, the Appalachian Trail, and a range of historic homes and buildings.
Living Room

The living room in this 8-bedroom, 9-bath home showcases a traditional design with detailed crown molding, a grand piano, and a fireplace, offering a comfortable yet elegant setting for gatherings.
Formal Dining Room

This formal dining room, part of the 8-bedroom, 9-bath residence, features ornate drapery, an antique sideboard, and a chandelier, providing a refined atmosphere for hosting memorable meals.
Primary Bedroom

The master bedroom in this 8-bedroom, 9-bath home includes a marble fireplace, custom built-ins, and a seating area, creating a luxurious and functional retreat within the estate.
Pool Area

The outdoor pool, part of this 8-bedroom, 9-bath property, is complemented by a stone patio and nearby tennis courts, offering both relaxation and activity options in a private setting.
Source: Diana Bisselle & Laurie Dunham @ William Pitt Sotheby’S Int’L Via Coldwell Banker Realty
1. Norfolk, CT – $4,995,000

This is what’s up for $4,995,000 in Norfolk. This 6-bed, 8-bath, 5,671 sq ft home features wide red pine floors, high ceilings, two wet bars, and nine wood-burning fireplaces. The gourmet kitchen includes custom cabinetry, a fireplace, and a fish sink on the back porch. The main bedroom offers a private sitting area, a fireplace, and a steam shower, while three additional ensuite bedrooms with fireplaces are located on the upper floor alongside a playroom and laundry. Outdoor amenities include a custom oval heated gunite pool, a poolhouse with a kitchenette, a half bath, dressing rooms, and an outdoor shower, surrounded by stone-walled perennial gardens. An ensuite studio is located above the heated garage, adding versatility to the property.
Where is Norfolk, CT?

Norfolk, Connecticut, is located in the northwestern part of the state, in Litchfield County. It lies approximately 20 miles north of Torrington, 40 miles northwest of Hartford, and about 50 miles southeast of Pittsfield, Massachusetts. Positioned near U.S. Route 44 and Connecticut Route 272, Norfolk is known for its scenic countryside, historic charm, and vibrant arts community. The town features attractions such as the Norfolk Chamber Music Festival at the Yale Summer School of Music, Haystack Mountain State Park, and a picturesque village green surrounded by 19th-century architecture. Norfolk offers a peaceful rural atmosphere and is a popular destination for nature enthusiasts, artists, and history lovers.
Living Room

This spacious living room, part of a 6-bedroom, 8-bathroom estate, features expansive glass doors and windows framing serene garden views. The layout offers ample space for relaxation and gatherings, accentuated by the natural light streaming in. Elegant wood accents and neutral tones complete the tranquil ambiance.
Dining Room

The dining room, within this 6-bedroom, 8-bathroom home, boasts large windows that brighten the space with natural light. A central fireplace anchors the room, creating a warm setting for meals and entertaining. The room seamlessly connects to adjacent areas, enhancing flow and accessibility.
Bedroom

One of six bedrooms in this 8-bathroom property, this bedroom exudes charm with its large windows and plush carpeting. The space offers a private retreat, complemented by access to an en-suite bathroom. A seating nook adds functionality and comfort to this inviting space.
Pool Area

This estate’s circular pool is surrounded by lush greenery, offering privacy and a picturesque setting. Adjacent to the pool, a covered cabana adds a perfect space for outdoor relaxation or hosting gatherings. The stone patio enhances the aesthetic and functionality of the outdoor area.
Source: Martha Mullins @ William Pitt Sotheby’S Int’L Via Coldwell Banker Realty