Westport Homes with Colonial Style

Welcome to Westport, Connecticut—a picturesque coastal town nestled in the heart of Fairfield County. Known for its stunning landscapes, vibrant arts scene, and rich history, Westport offers a unique blend of suburban charm and sophisticated living. With its proximity to Long Island Sound, residents enjoy a plethora of outdoor activities, from sailing and fishing to leisurely strolls along the scenic beaches. The town's downtown area is bustling with boutique shops, gourmet restaurants, and cultural venues, making it a perfect place for both relaxation and entertainment.

One of the standout features of Westport’s real estate market is its collection of stunning Colonial-style homes. These timeless residences exude elegance and charm, showcasing classic architectural details such as symmetrical facades, large windows, and inviting front porches. Many of these homes are set on beautifully landscaped lots, offering plenty of space for outdoor gatherings and family activities. Inside, you'll find spacious layouts, hardwood floors, and traditional fireplaces that create a warm and welcoming atmosphere.

Living in a Colonial-style home in Westport not only provides a sense of history and character but also places you in a community that values quality of life. With top-rated schools, thriving local businesses, and a strong sense of community, Westport is more than just a place to live; it's a lifestyle. Whether you're raising a family or looking for a tranquil retreat, Westport's Colonial homes offer the perfect backdrop for your next chapter. Come and experience the charm of Westport for yourself!

Newest Westport Homes with Colonial Style

$1,629,000

4 Beds ⋅ 3 Baths ⋅ COMING SOON Status ⋅ 24203692 MLS

Coming Soon! This classic colonial sits on a level, 1.08-acre, lot on a quiet side street with no wetlands and is serviced by natural gas. The interior features an open floor plan, whole house generator, and a dedicated main-level office. Outdoor amenities include a front porch, a large screened-in porch, a deck, and an in-ground pool. Additional information and professional photos will be available on Tuesday, September 15.

35 Bonnie Brook Rd, Westport

$7,985,000

6 Beds ⋅ 6 Baths ⋅ COMING SOON Status ⋅ 24205532 MLS

Introducing 12 Beltas Farm Lane, an extraordinary new construction estate in Westport, Connecticut, set within Beltas Farm-one of Westport's newest and most distinctive luxury enclaves. Once part of a 23-acre working family farm, this special setting has been thoughtfully transformed into an intimate collection of exceptional residences, with nearly five acres preserved as open space. The result is something increasingly rare in Westport: beautiful open views, a sense of space and privacy, and an enclave of significant luxury homes. Offered at $7,895,000 and built by Fairfield County Contractors, known for exceptional quality and craftsmanship, this remarkable new Westport home encompasses more than 9,000 square feet of sophisticated living space. A handsome wood roof introduces timeless architecture and the exceptional level of finish found throughout. Designed for today's luxury lifestyle, the residence features six ensuite bedrooms and beautifully proportioned living and entertaining spaces filled with natural light and oriented to capture the property's open views. A wine cellar adds another layer to the home's exceptional entertaining spaces, while the thoughtful floor plan balances impressive scale with comfortable everyday living. Outside, a stunning pool and spa create a private resort experience surrounded by the beauty and openness of the Beltas Farm setting. What distinguishes 12 Beltas Farm Lane is not simply the caliber of the new construction, but the rarity

12 Beltas Farm Ln, Westport

$1,500,000

4 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24206148 MLS

This is the land and location Westport buyers are chasing hardest right now, and finding least. It won't last more than a moment. Bring your architect or builder or we can share ours. The acre is flat, easily buildable, screened on every side. The house could be reimagined however the value is in the land. Its a private blank canvas on a cul-de-sac. Long Lots, on the cusp of Hunt Club - the neighborhood and the country club. Close to town but not too close. A quick drive to Greens Farms station, Burying Hill Beach, and the many Post Road amenities - dangerously close to Fatto a Mano, though proximity to Equinox balances that right out. Zone Specifics: AA Zone, 30 ft from the street and 25 ft from the side setbacks, max 3 stories height of 40 ft, 25% lot coverage. No wetlands. Public water, septic. Access to both Gregg Lane and Grist Mill. Existing solar will be removed and settled by the trust. Buyers are responsible for their own due diligence; neither the trust nor the seller's agent can make any representations. The address is 4 Grist Mill Lane, the driveway is actually at the end of Gregg Lane. Not subject to probate. AS-IS. Ideal for a 6,000 sq foot plus new home in the $5-6+M value range. The deadline for submitting offers is 9/18 by 5pm.

4 Grist Mill Ln, Westport

$4,750,000

5 Beds ⋅ 7 Baths ⋅ ACTIVE Status ⋅ 24204438 MLS

A fresh take on Modern Luxury awaits at this new construction home set on stunning property in the Old Hill area of Westport. Now complete and ready for immediate enjoyment, this dynamic residence is perfectly located for convenience to commuting, the train station, schools, shopping and more. Exhilarating architecture will awaken your senses as you approach this customquality home. Walls of glass blend the natural setting with stunning interiors, and bring sunlight deep into the spectacular rooms. The chef's kitchen is a showpiece, featuring bespoke oak cabinetry, premium finishes, and a substantial walkin pantry. Dual mainlevel offices support today's lifestyle. 5 spacious bedrooms and 7 refined baths create a harmonious balance of comfort and sophistication. The primary suite is a serene retreat with three fitted closets and a spalevel ambiance. Additional bedrooms offer generous scale and thoughtful design. A sunlit upstairs lounge and a finished thirdfloor space provide flexible areas for work, play, or creativity. The finished lower level offers exceptional spaces for fitness, media, or entertaining. Outside, an expansive patio overlooks 1.68 acres of private grounds, ideal for gatherings or quiet reflection. A 3car garage (with a separate bay for a trophy vehicle or storage) and sleek modern detailing complete this remarkable offering. An inspired blend of architecture, setting, and convenience await in a prime location. Pool permit in place.

1 Twin Oaks Ln, Westport

$2,650,000

3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24203635 MLS

Impeccable, effortlessly sophisticated house with lovely water views nestled on private road in idyllic Saugatuck Shores steps to Long Island Sound and Bermuda Lagoon. Designed by top architect VITA Design, the house combines relaxed coastal luxury with an elevated contemporary aesthetic for easy living, enjoyable year round. Features warm beach-inspired woods, high-end finishes, high ceilings, light wood floors, oversized windows and abundant natural light. On the main level the sleek chefs kitchen w/ center island flows seamlessly into the dining area and great room w/ wood-burning fireplace framed by floor-to-ceiling windows. Office/bedroom and full bath complete the main level. Second floor features serene primary suite with water view, custom built-ins and luxurious bath. Two additional bedrooms, full bath, laundry, and stylish reading nook complete this level. The front to back top floor bonus room with water views on both sides, leads out to spectacular roof deck terrace with view of Long Island Sound --a wonderful outdoor living space perfect for entertaining or quiet enjoyment to take in glorious sunsets, sunrises and Fourth of July fireworks over the Sound. The lower level offers additional versatile rec room, mudroom, attached garage. Private back yard. House is FEMA compliant. Lovely neighborhood for walking, biking, boating, kayaking. Close golf/tennis. Quick drive to the train station, Saugatuck shops and dining, and all Westport has to offer.

14 Promised Rd, Westport

$9,860,000

6 Beds ⋅ 9 Baths ⋅ ACTIVE Status ⋅ 24205443 MLS

Newly completed, this exceptional modern estate offers approximately 9,200 square feet on 2.1 private acres just minutes from downtown Westport, Compo Beach, and Metro-North. Thoughtfully designed with European craftsmanship, premium finishes, and sophisticated smart-home technology, the home blends timeless design with exceptional functionality. A dramatic floating staircase anchors four finished levels featuring soaring ceilings, custom millwork, and engineered white oak flooring. The chef's kitchen showcases dual quartzite waterfall islands, custom rift white oak cabinetry, a walk-in pantry, and a professional appliance suite. The primary suite offers cathedral ceilings, a fireplace, private balcony, dual dressing rooms, and a spa-inspired bath with heated floors and a soaking tub. Designed for seamless indoor-outdoor living, the nearly 950-square-foot covered terrace features granite flooring, a wood-burning fireplace, outdoor kitchen, heated 20' 40' saltwater pool, 10-person spa, and room for a future tennis or pickleball court. The walk-out lower level includes a family room, wet bar, fitness studio, guest suite, and flexible space for a theater, golf simulator, or media lounge. Prepare to fall in love.

9 Over Rock Ln, Westport

$899,000

2 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24204656 MLS

Welcome to 1 Maplewood Avenue-Your Opportunity to Call Westport Home! Charming, stylish, and filled with possibilities, this inviting **2-3 bedroom Westport home** offers an exceptional opportunity to enjoy one of Fairfield County's most desirable communities and its **highly regarded school system**. Step inside to discover **beautifully refinished hardwood floors** and a bright, comfortable floor plan designed for today's lifestyle. The **updated kitchen features stainless steel appliances**, while refreshed **tile bathrooms** add a clean, modern touch. Need more room? You'll love the versatility of the **finished walk-up attic**, perfect for a home office, creative studio, guest space, or additional retreat. A separate **playroom** provides even more flexibility for recreation, entertaining, or everyday living. Situated on a corner lot with generous parking, the property offers space, convenience, and plenty of potential to make it your own. Whether you're purchasing your **first home, downsizing, or looking for an exciting opportunity to enter the Westport market**, 1 Maplewood Avenue delivers the perfect combination of charm, updates, flexible living space, and location. Westport living may be more attainable than you think-come discover the possibilities at 1 Maplewood Avenue!

1 Maplewood Ave, Westport

$4,600,000

6 Beds ⋅ 8 Baths ⋅ ACTIVE Status ⋅ 24204809 MLS

Resort-style living meets modern luxury at 2 Windy Hill Road. Set on a private landscaped acre, this newly completed 8,100+ SF estate by HOBI Award-winning builder Cypress Development was thoughtfully designed for the way today's luxury buyer lives, entertains, and unwinds. A dramatic two-story foyer introduces light-filled interiors highlighted by soaring ceilings, white oak flooring, natural stone finishes, and walls of European windows and doors. At the heart of the home, the chef's kitchen features marble countertops and backsplash, Sub-Zero and Wolf appliances, custom oak cabinetry, dual dishwashers, and a stunning waterfall island that seamlessly connects to the home's gathering spaces. The primary suite serves as a private retreat with vaulted oak-beamed ceilings, fireplace, sitting area, private balcony overlooking the pool, custom dressing room, and spa-like bath with heated floors and dual showers. Designed for both entertaining and wellness, the lower level includes a glass-enclosed gym, custom marble-topped bar, recreation space, guest suite, and a dedicated area ready for a golf simulator or theater. Outside, enjoy a gunite pool with automatic cover, covered outdoor living area, expansive granite patios, outdoor kitchen provisions, and a large flat lawn surrounded by mature landscaping, stone walls, and privacy plantings. A rare offering that delivers the comfort of everyday living with the amenities of a private resort.

2 Windy Hill Rd, Westport

$3,400,000

5 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 24204780 MLS

This beautifully renovated Ward French custom home offers elegant formal spaces, a chef's kitchen, flexible guest and office accommodations, a luxury primary suite, fitness studio and sitting room with balcony. The home's 2,442 square foot lower level offers tremendous untapped potential, providing an opportunity to create customized luxury amenities such as a home theater, golf simulator, wine cellar, wellness spa, or guest retreat. Outdoors a spectacular 20' x 40' pool and spa, multiple entertaining patios, and lush private landscaping create a true retreat. Moments from schools and town amenities, this exceptional Westport residence perfectly balances luxury and everyday living.

27 Woody Ln, Westport

$7,015,000

6 Beds ⋅ 10 Baths ⋅ ACTIVE Status ⋅ 24204343 MLS

Move right in THIS October! Just weeks away from completion, come see this 8,417SF dream residence w/sauna, pool & spa on 1 private acre in coveted Greens Farms as the finishing touches are being made. 24 Edgemarth Hill was designed, crafted, and appointed with the finest materials - see rendering photos. Flaunting sexy floor-to-ceiling walls of windows, stone and textured accents, vaulted ceilings, and romantic balconies, this is a spec build with all the custom features the most discerning buyer desires. Finished on 4 floors - be ready to be "WOWED": enviable public rooms; 2 indoor fireplaces and 1 outside on the covered porch; 6+ bedrooms (guest bedroom on the main level) including the most sumptuous Primary Bedroom with fireplace, balcony, wet bar/coffee bar, 2 walk-in closets, and gorgeous bath; 8 full and 2 half baths. LL includes a Media room w/ultra luxe wet bar, Gym & sauna, & 6th Bdrm. Above the 3 car garage, you'll find addt'l finished space w/full bath. This cul de sac neighborhood is just minutes to shops, restaurants, beach, Longshore, and train, but once you've arrived you'll never want to leave your own private paradise. The resort style grounds include: 20x40 pool & spa, sleek built-in grill w/custom stone countertop, glorious entertaining patios & covered porch, outdoor shower, & professional landscaping. Expect nothing less than SENSATIONAL. Built by Coastal Luxury Homes.

24 Edgemarth Hill Rd, Westport

$2,350,000

5 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 24203971 MLS

Beautifully renovated 1799 antique Colonial offering timeless charm, modern luxury, flat pool-worthy property, and exceptional convenience, just one light to the Greens Farms train. This special home captures the soul of historic Westport while delivering the comfort of today's lifestyle. Thoughtfully renovated, it blends original character, architectural detail, warmth, and six fireplaces with the amenities today's buyers expect. Set on a flat property with room for a potential pool, the home offers inviting indoor and outdoor spaces ideal for entertaining and everyday living. At the center is a chef's kitchen with a Sub-Zero refrigerator, a Wolf range, custom cabinetry, and generous prep space, opening to a sun-filled family room. Formal rooms, antique details, and multiple fireplaces create a space that feels both elegant and welcoming. The primary suite offers an oversized dressing room with abundant closet space, and a spa-like bath with a soaking tub and steam shower. The finished lower level includes a game room, wine cellar, and flexible recreation space. Outside, the expansive lawn offers space for sports, gatherings, gardens, or a future pool. Ideally located with one light to Greens Farms train, and minutes to Long Lots Elementary, Post Road shopping, and Main Street dining. A rare blend of antique charm and modern living.

28 Bulkley Ave N, Westport

$6,999,999

6 Beds ⋅ 9 Baths ⋅ ACTIVE Status ⋅ 24196804 MLS

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 and blends timeless elegance with modern living. The main level offers light-filled, open living spaces ideal for both everyday living and entertaining, featuring a custom chef's kitchen with breakfast area, expansive family room, formal living and dining rooms, private office, mudroom, and thoughtfully placed powder rooms. The second level showcases a luxurious primary suite with two generous walk-in closets and a spa-inspired bath, along with four additional ensuite bedrooms and a dedicated laundry room. The walk-out lower level includes a spacious recreation room, gym, guest bedroom with full bath, and flexible space for today's lifestyles. A finished third floor provides additional living space-perfect for a playroom, media room, or home office-with a half bath. Designed with Mattera Construction's signature attention to detail, craftsmanship, and integrity, this home offers the ultimate Westport lifestyle-coastal, convenient, and effortlessly elegant. New construction. Premier beach-area location. A home that rarely comes to market.

32 Narrow Rocks Rd, Westport

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