5 Bedroom homes for sale & real estate in Westport, CT

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ABOUT THIS HOME
5 Bedroom Homes for Sale in Westport, CT
Modern coastal living on a quiet cul-de-sac in Westport's Saugatuck Shores. Completed in 2021, this five-bedroom, four-bath home spans more than 2,944 sq ft of finished space with a thoughtful open layout and timeless design. The main level features 9-ft ceilings, a sunlit living room with gas fireplace, and large windows framing serene water views. The kitchen offers custom cabinetry, quartz waterfall island, and premium stainless appliances, connecting seamlessly to the dining area for easy entertaining. A first-floor bedroom with full bath provides flexible use as a guest suite or home office. Upstairs, the primary suite includes a gas fireplace, walk-in closet, and spa-style bath with s

$2,995,000

5 beds4 baths3,486 sq ft

3 Nassau Rd, Westport, CT 06880

Quiet cul-de-sac • Finished roof deck • Stone terrace

ABOUT THIS HOME
5 Bedroom Homes for Sale in Westport, CT
Tucked away on a picturesque property with a peaceful pond and complete privacy, this custom-built home is truly exceptional. From the moment you step onto the welcoming front porch, you'll feel the warmth and quality throughout. The sunlit kitchen is beautifully appointed with top-of-the-line appliances and a built-in banquette by the cozy fireplace, opening seamlessly to the inviting family room with a stunning fireplace & French doors to the patio. Entertain effortlessly in the elegant dining room w/ butler's pantry & spacious living room. A first-floor office w/ pocket doors offers a quiet retreat for work or study. Upstairs, the primary suite is a sanctuary w/ vaulted ceili

$3,950,000

5 beds6 baths5,771 sq ft

116 Roseville Rd, Westport, CT 06880

Custom-built home • Inviting family room • Sunlit kitchen

NEW CONSTRUCTION

ABOUT THIS HOME
5 Bedroom Homes for Sale in Westport, CT
Bluewater Home Owenoke Opportunity Knocks Again! Another beach masterpiece is underway and this 6050 sqft 5BR/3Car garage designed home with private yard, pool with spa, pond views and walking distance to Compo Beach will be ready Spring 2026. Enjoy this new beach construction living in the heart of Westport while peacefully tucked away on a private cul-de-sac. Bluewater Home Owenoke Opportunity Knocks Again! Another beach masterpiece is underway and this 6050 sqft 5BR/3Car garage designed home with private yard, pool with spa, pond views and walking distance to Compo Beach will be ready Spring 2026. Enjoy this new beach construction living in the heart of Westport while peacefully tucked a

$11,795,000

5 beds6 baths6,050 sq ft

14 Owenoke Park, Westport, CT 06880

Private yard • Pond views • Pool with spa

NEW CONSTRUCTION

ABOUT THIS HOME
5 Bedroom Homes for Sale in Westport, CT
Nestled in one of Westport's most desirable walk-to-town neighborhoods, this exceptional new construction home combines timeless charm with modern luxury. Designed by acclaimed architect Judith Larson and crafted by trusted builder Redcoat Homes, this residence offers the perfect balance of style and functionality. Located on a level third-acre on a quiet cul-de-sac, the property is beautifully landscaped with a gunite pool. With 5 bedrooms, 6 full bathrooms, and four finished levels, the home is ideal for both family living and entertaining. An expansive, open floor plan is accentuated by Redcoat Homes' signature oversized windows and doors, flooding the space with natural light. The high-

$4,299,000

5 beds6 baths4,879 sq ft

5 Franklin Ave, Westport, CT 06880

Open floor plan • Spacious home office • Chef's kitchen

ABOUT THIS HOME
5 Bedroom Homes for Sale in Westport, CT
THE BEDFORD HOUSE - Architecturally and historically significant estate in coveted Greens Farms. This exceptional property offers a rare opportunity to own one of Westport's most superb homes. Set on 2.33 acres with a gunite pool/spa, court and a 2400 sq ft barn featuring a 3-car garage, loft & more, the estate blends timeless elegance with modern comfort. Originally built in 1904 and designed by noted architects Visscher and Burley, this Colonial Revival home has undergone thoughtful renovations over the years to preserve and enhance its character. The main residence features 5 Bedrooms and 6.5 Baths with a well-planned layout for today's lifestyle. High ceilings, oversized windows,

$3,500,000

5 beds6.5 baths5,789 sq ft

221 Greens Farms Rd, Westport, CT 06880

2.33 acre lot • 3 garage spots • Pool

Property at 111 Sturges Hwy, Westport, CT 06880, 5 beds, 7 baths

$3,550,000

5 beds7 baths7,359 sq ft

111 Sturges Hwy, Westport, CT 06880

Property at 26 Treadwell Ave, Westport, CT 06880, 5 beds, 4.5 baths

$3,295,000

5 beds4.5 baths3,200 sq ft

26 Treadwell Ave, Westport, CT 06880

Property at 16 Burr School Rd, Westport, CT 06880, 5 beds, 4.5 baths

$3,395,000

5 beds4.5 baths5,056 sq ft

16 Burr School Rd, Westport, CT 06880

Property at 17 Clover Ln, Westport, CT 06880, 5 beds, 3.5 baths

$2,195,000

5 beds3.5 baths3,000 sq ft

17 Clover Ln, Westport, CT 06880

Property at 26 Hitchcock Rd, Westport, CT 06880, 5 beds, 4 baths

$2,639,000

5 beds4 baths4,549 sq ft

26 Hitchcock Rd, Westport, CT 06880

Property at 40 Hermit Ln, Westport, CT 06880, 5 beds, 5 baths

$2,849,000

5 beds5 baths4,142 sq ft

40 Hermit Ln, Westport, CT 06880

Property at 489 Main St, Westport, CT 06880, 5 beds, 4 baths

$900,000

5 beds4 baths2,192 sq ft

489 Main St, Westport, CT 06880

Property at 1 Coastal Ct, Westport, CT 06880, 5 beds, 6 baths

$4,995,000

5 beds6 baths5,550 sq ft

1 Coastal Ct, Westport, CT 06880

Property at 13 Terhune Dr, Westport, CT 06880, 5 beds, 5.5 baths

$3,999,000

5 beds5.5 baths5,710 sq ft

13 Terhune Dr, Westport, CT 06880

Property at 10 Tierney Ln, Westport, CT 06880, 5 beds, 6 baths

$4,899,000

5 beds6 baths7,400 sq ft

10 Tierney Ln, Westport, CT 06880

Property at 36 Maple Ave S, Westport, CT 06880, 5 beds, 6.5 baths

$5,499,000

5 beds6.5 baths7,000 sq ft

36 Maple Ave S, Westport, CT 06880

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ABOUT THIS HOME
5 Bedroom Homes for Sale in Westport, CT
Welcome to 38 Gregory Boulevard, an impeccably maintained two-family home in one of East Norwalk's most desirable coastal neighborhoods. Ideally situated just a short walk to the beach, restaurants, local markets, and the water, this property perfectly combines coastal charm with everyday convenience. The first unit features a nicely sized 2-bedroom, 1-bath layout, filled with natural light and well-kept interiors. The second unit is a spacious 3-bedroom, 3-full-bath across two levels, offering abundant living space - perfect for an owner-occupant or extended family. Both units have been meticulously cared for and show true pride of ownership throughout. A beautifully landscaped yard and in

$1,050,000

5 beds4 baths3,315 sq ft

38 Gregory Blvd, Norwalk, CT 06855

7,405 sq ft lot • Built 1904 • Listed 10 days

ABOUT THIS HOME
5 Bedroom Homes for Sale in Westport, CT
Looking for a stunning beach home with a private dock? Welcome to this exceptional waterfront retreat on coveted Gregory Point, overlooking Norwalk Harbor. Perfectly positioned with west-facing views, this residence captures dazzling sunsets and a dynamic harbor scene from nearly every room. Beautifully renovated, this modern coastal farmhouse is the epitome of move-in-ready luxury. The sunlit chef's kitchen-with wood-burning fireplace-opens to a casual family room wrapped in water views. Entertain effortlessly in the formal dining room or spacious living room designed for gatherings. Host unforgettable dinners in the formal dining room and entertain friends in the relaxed and spacious livi

$4,250,000

5 beds4 baths4,241 sq ft

9 Sylvester Ct, Norwalk, CT 06855

West-facing views • Formal dining room • Private dock

ABOUT THIS HOME
5 Bedroom Homes for Sale in Westport, CT
Built by renowned master builder John Heggland, this exceptional 7,811 sq ft Georgian Colonial estate is gracefully sited on 2.45 private acres in one of Wilton's most sought-after, nature-rich locations. Known for his uncompromising craftsmanship and timeless architectural integrity, Heggland delivers a residence that blends classic elegance with the finest in modern luxury and energy-efficient design. Inside, a double-height foyer with a sweeping staircase introduces rich hardwood floors, intricate moldings, and finely paneled walls. Formal living and dining rooms open to an inviting family room centered around a fireplace. The chef's kitchen features custom cabinetry, a butler's pantry,

$3,495,000

5 beds8 baths6,990 sq ft

76 Sturges Ridge Rd, Wilton, CT 06897

Ensuite bedrooms • Spa-inspired bath • Butler's pantry

Keller Williams Prestige Prop

3D WALKTHROUGH

ABOUT THIS HOME
5 Bedroom Homes for Sale in Westport, CT
Welcome to an unrivaled sanctuary of sophistication at 342 Midlock Road, gracefully situated in the prestigious enclave of Greenfield Hill. This stately residence, perched on a coveted cul-de-sac off Burr Street, unfurls over two lush acres of meticulously manicured, fully fenced grounds. Upon entry, be enveloped in luxury as you traverse through spaces adorned with custom millwork, nine ft ceilings, abundant natural light and more. The heart of this home is an eat-in chef's kitchen, replete with top-tier stainless steel appliances, which connects you to multiple other spaces for enjoyment or repose. Entertain with panache in the formal dining room, garden room, library, living room or grea

$2,799,999

5 beds6.5 baths7,269 sq ft

342 Midlock Rd, Fairfield, CT 06824

2.03 acre lot • 3 garage spots • Pool

ABOUT THIS HOME
5 Bedroom Homes for Sale in Westport, CT
Modern elegance meets estate living at 88 Merry Meet Circle, set on 3+ manicured acres in Fairfield's premier gated community, The Ridge. Perfectly positioned where Fairfield meets Westport, this gracious colonial manor offers 5+ bedrooms, 6 full and 2 half baths, and 4 beautifully finished levels-just minutes from vibrant downtowns, beaches, dining, and trains. A grand two-story foyer with a custom staircase and Swarovski chandelier sets a stunning first impression. Sunlit interiors flow effortlessly with French doors opening to expansive terraces and lush landscaping. The chef's kitchen is a true centerpiece, featuring Wolf appliances and two large islands-perfect for both casual gatherin

$2,498,000

5 beds7 baths8,136 sq ft

88 Merry Meet Cir, Fairfield, CT 06824

Gated community • Custom staircase • Swarovski chandelier

NEW CONSTRUCTION

ABOUT THIS HOME
5 Bedroom Homes for Sale in Westport, CT
Greenfield Hill proposed new construction on a 2.65-acre lot along a Town-designated Scenic Road, to be built by award-winning design-builder Bonnie Paige in collaboration with Vicente Burin Architects. The proposed residence is based on a design sold in Southport Village; interested buyers may tour similar homes and meet the team to tailor plans, finishes, and timeline. The property sits among notable estate properties and near Brett Woods Conservation Area (186 acres) and the Roy and Margot Larsen Wildlife Sanctuary (155 acres), with convenient access to the centers of Fairfield, Southport, and Westport and approximately 55 miles to Manhattan. Construction will begin after purchase and ex

$3,750,000

5 beds5.5 baths5,000 sq ft

22 Brett Rd, Fairfield, CT 06824

New construction • Approved for a pool • 2.65 acre lot

Property at 54 Cove Ave, Norwalk, CT 06855, 5 beds, 4 baths

$1,895,000

5 beds4 baths2,662 sq ft

54 Cove Ave, Norwalk, CT 06855

Property at 2281 Redding Rd, Fairfield, CT 06824, 5 beds, 4.5 baths

$4,995,000

5 beds4.5 baths4,191 sq ft

2281 Redding Rd, Fairfield, CT 06824

Property at 101 Brambley Hedge Cir, Fairfield, CT 06824, 5 beds, 5 baths

$1,695,000

5 beds5 baths5,136 sq ft

101 Brambley Hedge Cir, Fairfield, CT 06824

Property at 29 Saddle Rd, Norwalk, CT 06851, 5 beds, 2 baths

$750,000

5 beds2 baths1,980 sq ft

29 Saddle Rd, Norwalk, CT 06851

Property at 2683 Bronson Rd, Fairfield, CT 06824, 5 beds, 4.5 baths

$3,649,000

5 beds4.5 baths4,771 sq ft

2683 Bronson Rd, Fairfield, CT 06824

Property at 145 Lyons Plain Rd, Weston, CT 06883, 5 beds, 5.5 baths

$1,569,000

5 beds5.5 baths3,579 sq ft

145 Lyons Plain Rd, Weston, CT 06883

Property at 2015 Redding Rd, Fairfield, CT 06824, 5 beds, 5.5 baths

$2,995,000

5 beds5.5 baths5,965 sq ft

2015 Redding Rd, Fairfield, CT 06824

5 Bedroom Homes for Sale in Westport

There are currently 16 5 bedroom homes in Westport. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Westport stay on the market for 57 days and receive 1 offers. Popular neighborhoods include Cranbury, Seven Coves, Fairfield Beach, East Norwalk, and Long Island. This map is refreshed with the newest listings in Westport every 15 minutes.

In the past month, 33 homes have been sold in Westport. In addition to houses in Westport, there were also 16 condos, 0 townhouses, and 1 multi-family unit for sale in Westport last month. Westport is a not walkable city in Fairfield County with a Walk Score of 21. Westport is home to approximately 26,374 people and 16,962 jobs. Find your dream home in Westport using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Westport are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Westport. Our Westport real estate stats and trends will give you more information about home buying and selling trends in Westport. If you're looking to sell your home in the Westport area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Westport with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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