Homes for Sale in Westport, CT with 5-Bedrooms

NEW PRICE!! Discover the epitome of luxury in this beautifully furnished Colonial estate located in Westport's prestigious Red Coat neighborhood. Offering over 7,000 square feet of elegant living space plus an additional 2,400 square feet in the finished lower level, this 6-bedroom, 5.2-bath home is designed for both everyday comfort and grand entertaining. The gourmet kitchen is outfitted with

Jolanta Rojek eXp Realty

Located on a quiet private lane just two blocks from Compo Beach, this newly built coastal residence at 22 Appletree Trail offers a rare combination of modern craftsmanship, thoughtful design, and effortless beach living in the heart of Westport. Spanning approximately 4,791 sq ft of living space, the home blends timeless architectural elements with refined contemporary finishes. White oak

Deborah Aulfinger Gold & Home Realty

Tucked away in the heart of Westport, Hillspoint offers the perfect blend of luxury, lifestyle and location. Minutes to Longshore Club Park, Compo Beach, town and train, it delivers rare privacy with exceptional convenience. Inside, soaring ceilings and sun-filled spaces create a light, airy flow enhanced by high-end finishes throughout. Designed for everyday living and effortless entertaining,

Michelle Genovesi William Raveis Real Estate

Ready for SUMMER 2026! Bluewater Home's newest luxury creation is close to completion. This 6050 sqft 5BR/3Car garage designed home with private yard, pool with spa, pond & LI sound views and walking distance to Compo Beach offers privacy and multiple balconies and indoor/outdoor spaces. Oversized rooms and expansive kitchen with double islands, scullery kitchen, elevator and private primary

Deirdre Andreoli Compass Connecticut, LLC

Set in Westport's sought-after Hunt Club neighborhood, this European-inspired Colonial offers over 6,300 square feet across three finished levels, including expansive recreation spaces and a dedicated home theater. A dramatic two-story entry introduces refined formal and informal rooms, including a fireplaced living room, formal dining room, private office, and an expansive eat-in kitchen with

Zach Wright William Pitt Sotheby's Int'l

Set in a serene natural setting, this custom Colonial offers a comfortable layout with a balance of privacy and convenient access to top-rated schools, shopping, and dining. The main living spaces are bright and inviting, with generous windows that frame views of the surrounding greenery and create an easy flow for everyday living and entertaining. Upstairs, four bedrooms are located on one

Lynne Nolan Compass Connecticut, LLC

Set on over 3 private acres with sweeping water views, 2 Judy Point Lane is a remarkable Westport waterfront estate offering approximately 14,000 square feet of living space and a rare compound-style layout. The property consists of two substantial residences connected by a breezeway, creating exceptional flexibility for multi-generational living, extended guests, or a private guest house.

Daniel Kramp Christie's International Real Estate

Introducing 1 Coastal Court, a rare opportunity to own in Westport's only gated community, an exclusive four-lot enclave envisioned and built by Joe Feinleib, founder of Coastal Luxury Homes and one of Fairfield County's most respected builders.This private neighborhood blends timeless architecture with modern luxury. Each custom residence, ranging from 5,000 to 7,500 square feet, plus generous

Julie Vanderblue Higgins Group Real Estate

Imagine a residence where every element has been considered for gracious living in stylish surroundings. This newly completed home by awardwinning Able Construction is set on a peaceful Coleytown estatearea street, framed by scenic land that enhances its sense of calm. A dramatic foyer with a woodaccented ceiling and millwork feature wall introduces interiors defined by creative decor, walls of

Doug Bross Coldwell Banker Realty

Like-new custom modern home with open-concept living designed for comfort and entertaining. The main level connects the family room, dining room, office, and chef's kitchen featuring Sub-Zero and Wolf appliances, invisible speakers, quartzite countertops, custom cabinetry, two large islands and multiple sliding glass doors leading to an outdoor oasis. The spacious pantry includes custom shelving,

Gina Hackett Compass Connecticut, LLC

Timeless elegance in Westport's renowned Old Hill. Set on 2.22 bucolic acres w/a heated Gunite pool & picturesque pond, this expansive 5-6 bedroom,4.5 bath farmhouse blends classic charm w/thoughtful recent enhancements that delivers a renewed sense of style & energy to the home. A renovated kitchen remains the heart of the home, featuring a generous center island & a stunning, glass-walled

Mary Kate Klemish-Boehm Brown Harris Stevens

Set in one of Westport's most sought-after central neighborhoods, this gracious 5+ bedroom custom Colonial with a stunning gunite pool and spa offers the perfect balance of timeless elegance and modern comfort. Sun-filled interiors and thoughtful design create seamless flow for both entertaining and everyday living. The main level features a private office, elegant dining room with butler's

Christine Oleynick Keller Williams Realty

New construction by renowned Red Coat Homes, ideally set on a quiet cul-de-sac in a premier Westport neighborhood. Designed by architect Judith Larson, this exceptional home offers over 7,000 sq ft of refined living space on more than one acre, complete with a resort-style pool. Timeless architecture and sophisticated finishes create spaces ideal for entertaining, work, and everyday living, with

Danna Rogers Higgins Group Bedford Square

Set in a coveted estate enclave prized by CEOs and captains of industry, this exceptional, shingle-style residence embodies timeless architecture, extraordinary craftsmanship, and meticulous attention to detail. Built custom for a CEO, the home showcases uncompromising quality and gracious curb appeal that leave a lasting impression. Designed for seamless indoor-outdoor living and grand-scale

Cyd Hamer William Pitt Sotheby's Int'l

Direct Waterfront | Greens Farms An extraordinary new waterfront estate by award-winning Coastal Luxury Homes is coming to one of the most coveted stretches of the Connecticut shoreline. Set in the heart of Greens Farms, this spectacular 12,948 square foot modern residence will span four levels and capture sweeping, unobstructed views across Sherwood Island, Burying Hill Beach, and Long Island

Andrew Whiteley Brown Harris Stevens

Absolutely exquisite colonial is located on one of the most sought after neighborhoods. This home will greet you w/a mahogany front porch that leads inside to a grand foyer. This timeless residence boasts a custom kitchen w/high-end appliances, a Butler's pantry, large island & the convenience of a desk station. The elegant formal living room features a cozy fireplace, while the family room

Heather Fitzgerald Coldwell Banker Realty

Introducing an exceptional new build from Simple Plan Home Builders, multiple HOBI Award winners known for iconic Westport homes. Just a short stroll to Compo Beach, this striking modern coastal retreat is privately set on a coveted cul-de-sac, blending luxury, light, and effortless living. Spanning three and a half levels, this six-bedroom home features an airy layout with refined finishes

Lianne Owen Coldwell Banker Realty

Hidden along a private lane in Westport's Greens Farms neighborhood, this extraordinary 20-acre waterfront estate unfolds as one of the most remarkable shoreline settings ever offered. For more than 65 years, it has been held and enjoyed by the same family as a place to gather, unwind, and take in the ever-changing views across Sherwood Island Park and Long Island Sound. Surrounded by protected

Andrew Whiteley Brown Harris Stevens

RARE OPPORTUNITY TO CUSTOMIZE NEW CONSTRUCTION BY COASTAL LUXURY HOMES. PLANS APPROVED & PERMITS IN PLACE. CONSTRUCTION CAN BEGIN IMMEDIATELY, SAVE 6+ MOS ON NEW BUILD TIMELINE. This ultra luxury modern cul-de-sac residence features stucco exterior, DaVinci Boral roof, and expansive windows up to 10ft high. Main level includes luxe chef's kitchen w/ breakfast room opening to the great room with

Jennifer Tanner The Riverside Realty Group

Now under construction with summer completion, this exceptional new construction 6-bedroom SIGNATURE home by SIR Development offers a rare opportunity to work with the builder's in-house Design Team to place your own SIGNATURE on this new home. With over 30 years of experience and more than 300 completed homes, SIR Development has earned a stellar reputation for exceptional craftsmanship &

Julie Haroun Westport Residential, LLC.

Discover luxury living in the heart of Westport at 32 Webb Road, a newly built 2026 Colonial offering 8,412 square feet of open-concept living on a private 0.64-acre cul-de-sac lot just minutes from Compo Beach. This exceptional new construction features 8 ensuite bedrooms and 9 bathrooms, including a stunning primary suite with a private balcony, walk-in closet, and spa-like bath. Multiple

Judy Michaelis Coldwell Banker Realty

Better than new! This beautifully appointed 4-level home blends contemporary design with warmth, comfort, and thoughtful upgrades throughout. The heart of the home is a cook's dream kitchen with gourmet appliances, a full pantry, and a massive center island showcasing stunning finishes. Designed for both beauty and function, it opens seamlessly to the bright, welcoming family room. Together,

Jennifer Twombly Compass Connecticut, LLC

Welcome to 282 North Avenue, a timeless Westport residence set on a beautifully landscaped parcel in one of the town's most desirable locations. This inviting home blends classic New England charm with modern comfort, offering bright, well-proportioned living spaces designed for both everyday living and entertaining. Sun-filled interiors feature hardwood floors, oversized windows, and a flowing

Thomas Mele Dorrance Realty

This pristine Colonial offers timeless Westport elegance and effortless living, set on 1.12 flat, manicured acres framed by classic stone walls in a coveted, quiet neighborhood just one hour from NYC. The five-bedroom home features five full and two half baths, two dedicated offices, two versatile bonus spaces, custom millwork throughout, and abundant storage-perfect for today's work-from-home,

Danna Rogers Higgins Group Bedford Square

Design Your Dream Home with an Award-Winning Builder. Step into a world of elegance and sophistication with a soon-to-be-built 6,660 sq. ft. masterpiece by Coastal Luxury Homes. Known for their innovative designs, sleek modern lines, and unparalleled craftsmanship, Coastal Luxury Homes has earned a reputation for creating some of the most sought-after residences. With a focus on prime location,

Annie Klyver Higgins Group Real Estate

This is the second of 2 custom homes, beautifully sited at the end of a private lane in the heart of Greens Farms. Combining classic design with modern detailing by an established local builder of premier residences, this masterfully crafted home is sure to delight even the most discerning buyer. The main level showcases expert millwork and warm white oak accents throughout, flowing from the

Laurie Crouse Coldwell Banker Realty

Beautiful Georgian Colonial style home in desired Greens Farms neighborhood design by renowned architect Judith Larson. A fabulous Redcoat design team make this home a must, perfect for todays's lifestyle with a classic feel. This 6 bedroom residence is set on a flat, level.70 acre property embodying a perfect synergy of architectural excellence and an enviable location. Crafted for modern living

Kelly Loucas Compass Connecticut, LLC

Single Family with legal accessory apartment. New 5 bedroom septic system- just installed and new furnace and hot water heater in apartment. Let your imagination soar in creating your ideal situation. The main house and the accessory apartment each has a fireplace, The main house has 3 bedrooms and the apartment 2 bedrooms and each has 2 full baths. Hardwood Floors, laminate floor, vinyl floor,

Gabrielle DiBianco Higgins Group Bedford Square

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

James Lanzaro Compass Connecticut, LLC

Stunning modern transitional home built by Compo Luxury Homes in 2024 and ideally located just minutes to downtown Westport, Compo Beach, and the train. Set on .65 acres with city water, sewer, and natural gas, this beautifully designed residence offers over 8,000 square feet across four finished levels with 6 bedrooms, 6 full and 2 half baths. The open floor plan features a chef's kitchen with

Danna Rogers Higgins Group Bedford Square

NEW CONSTRUCTION TO BE BUILT IN THE COVETED HUNT CLUB NEIGHBORHOOD - Renowned, luxury builder Mattera Construction is well-known for architecturally significant & stunning modern homes filled with elegance, timeless beauty, custom interiors with state-of-the-art amenities. Now offering a perfectly designed 6 bedroom home finished on 4 levels filled with elegant finishes, well sited on a quiet

Patricia Shea Coldwell Banker Realty

NEW CONSTRUCTION BY RENOWNED LUXURY BUILDER MATTERA CONSTRUCTION - STEPS TO COMPO BEACH! A rare opportunity to own a brand-new, architecturally refined home in one of Westport's most coveted coastal locations-just steps to Compo Beach, Longshore Club, downtown Westport, the train, and schools. Currently under construction, this impeccably designed 6-bedroom residence spans four finished levels

Judy Michaelis Coldwell Banker Realty

Welcome to 27 Owenoke Park, a timeless direct waterfront retreat, offering sweeping views where history, nature and Long Island Sound converge. Tucked away from NYC's hustle, yet close enough to commute, Owenoke Park has always been one of Westport's most coveted neighborhoods. Set directly on the Long Island Sound shoreline with over 80' of water frontage, including private access to the tidal

Karen Scott Compass Connecticut, LLC

True Beauty In The Making! Construction of this 8,417SF dream residence with pool and spa on 1 private acre in coveted Greens Farms, Westport, is in full swing. 24 Edgemarth Hill was designed and will be crafted and appointed with the finest materials - see rendering photos of what's to come. Flaunting walls of windows, sexy floor-to-ceiling stone and textured accents, vaulted ceilings, and

Jaclyn Picarillo Higgins Group Bedford Square

Another extraordinary masterpiece by Coastal Luxury Homes, ideally situated in one of Westport's premier neighborhoods. Spanning over 9000 square feet of living space this 6 bedroom estate is defined by bold architectural lines, chic designer interiors, expansive balconies and seamless indoor-outdoor living. A resort caliber pool, fully equipped outdoor kitchen, and lush manicured grounds

Jen Kass Higgins Group Bedford Square

Now fully complete, this newly built residence in Greens Farms offers a rare blend of architectural presence, modern comfort, and understated luxury. Crafted by a seasoned Westport builder with a fresh perspective, the home delivers a level of finish and warmth that distinguishes it from typical new construction. The outdoor experience is now fully realized with a custom gunite pool and over

John Schiaroli Coldwell Banker Realty