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11 Edgewater Hillside, Westport
$3,899,000
4 Beds ⋅ 5 Baths ⋅ 24160000 MLS
COMPO BEACH WATER VIEWS at this picture-perfect beach house. Edgewater Hillside is the best-kept secret at Compo Beach, a private Hamptons-style cul de sac where each home is prettier than the next and water views abound. This exceptional residence combines timeless design with high-end amenities and so much space to live and entertain, walking distance to Compo Beach and Old Mill Beach, and moments to Longshore Club Park's golf, tennis, swimming and boating, and downtown. The four beautifully-finished levels are highlighted by so much attention to detail: soaring coffered ceilings, built-ins, and oversized windows taking in the views of the Sound, the Mill Pond and walls of blooming hydrangea. A chef's dream kitchen is equipped with Viking and Subzero appliances, and a fully-equipped outdoor kitchen and stunning stone fireplace make entertaining a breeze in all seasons. The generously-sized primary suite offers a sumptuous bath with soaking tub, walk-in closet and gas fireplace. The versatile floor plan includes a third floor retreat also with jaw-dropping views, balcony and full bath. The fully finished lower level also includes a full bath. The home and road access are not in a flood zone, and city water, sewer and natural gas plus a whole-house generator make life easy. Enjoy privacy, water views and the lifestyle only Compo Beach offers. Even room for a small pool! Also available fully furnished for a turnkey beach residence!

11 Edgewater Hillside, Westport
17 Vineyard Ln, Westport
$3,895,000
5 Beds ⋅ 6 Baths ⋅ 24170642 MLS
Stunning custom-built residence, newly completed in 2024, set within one of Westport's most coveted enclaves. Impeccably designed, this home offers soaring ceilings, refined finishes, and exceptional craftsmanship throughout. At the heart of the home, a chef's kitchen features an oversized center island, Thermador appliance package, seamlessly opening to the dining room adorned with Thibaut wallpaper. The family room showcases vaulted ceilings, a Carrara marble gas fireplace, and French doors leading to the backyard and patio for effortless indoor-outdoor living. The main level also includes a formal living room, office, powder room, mudroom, and access to a three-car garage. Upstairs, the primary suite features vaulted ceilings, two oversized walk-in closets, and a spa-like bath with double vanities, soaking tub, and glass-enclosed shower. Three additional bedrooms, two full baths, and a spacious laundry room complete the second level. A finished third floor provides a versatile bonus room with full bath. The lower level features a media room, fitness space, second office, and ensuite guest suite. Professionally landscaped and fenced, the grounds offer privacy and a beautiful setting for outdoor living. Just minutes to Westport's beaches, shopping, dining and metro north for seamless access to NYC.

17 Vineyard Ln, Westport
4 Buena Vista Dr, Westport
$3,875,000
5 Beds ⋅ 5 Baths ⋅ 24126601 MLS
Want to enjoy everything there is to love about the beach area, without the hassle of a flood zone? This home has everything you need. Perched at the top of Compo Hill, 4 Buena Vista Drive is a picture perfect colonial with water views and modern upgrades.This beautifully maintained home offers a traditional layout with high ceilings, arched doorways, and abundant natural light from the oversized windows. Thoughtful details include custom millwork, a butler's pantry, and spacious living/dining room great for entertaining. An open kitchen with high end appliances overlooks the family room with lots of custom built ins and a wood burning fireplace. Upstairs, the primary suite includes dual closets, wonderful water views, and a private deck creating a serene retreat. Primary bath has radiant heat. Three other upstairs bedrooms are spacious and flexible, including one with a Murphy bed for multipurpose use. In the lower level, there is a versatile hangout space and an additional bedroom which has access to a full bath. A generous mudroom for all your belongings, and 2 car tandem garage with lots of storage space rounds out this level. Enjoy the outdoors with a stone patio for dining, and admire the professional landscaping throughout the property. A whole-house generator and countless upgrades ensure comfort and peace of mind.

4 Buena Vista Dr, Westport
42 Easton Rd, Westport
$3,870,000
6 Beds ⋅ 7 Baths ⋅ 24164674 MLS
Majestically sited behind a classic stone wall and fence on 1.16 dry flat acres, this exceptional 6-bedroom, 5.2-bath residence offers the perfect blend of elegance, comfort, and modern living. Designed by noted local architect William A. Achilles, the home showcases a dramatic open floor plan filled with natural light and refined architectural detail across three beautifully finished levels. At the heart of the home is a stunning chef's kitchen featuring state-of-the-art appliances, custom cabinetry, and generous gathering spaces ideal for entertaining and everyday living. A private study provides the perfect work-from-home retreat, while the luxurious primary suite offers a serene escape with a spa-like bath and abundant closet space. There are 4 additional Bedrooms on the 2nd floor. The Lower level boasts a legal 6th bedroom and bath, a gym and a perfect spot for an in-home theatre. Thoughtful craftsmanship and high-end finishes are evident throughout, complemented by a 20kw generator for peace of mind. Outdoors, enjoy your own private resort with a gunite pool, spa, and automatic cover, surrounded by expansive lawn, gorgeous patio and mature landscaping with an in-ground irrigation system-perfect for play, relaxation, and entertaining. This is a rare opportunity to enjoy timeless design, modern amenities, and exceptional space both inside and out.

42 Easton Rd, Westport
116 Roseville Rd, Westport
$3,860,000
5 Beds ⋅ 7 Baths ⋅ 24138367 MLS
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 ceilings, a private sitting room, balcony overlooking the pond, and a luxurious spa-like bath. Three additional bedrooms, two full baths, & a bright laundry room complete the second floor. A private three-room suite off a separate entrance - including a family area, bedroom, full bath, and loft - provides perfect flexibility for guests, in-laws, or family members. The lower level offers a gym, full bath & sauna for healthy living. Outside, enjoy a resort-like lifestyle with a stunning 50-foot pool w/auto cover, mature landscaping, and breathtaking gardens. Set on 2.69 beautifully landscaped acres in a premier multi-million-dollar neighborhood convenient to everything beautiful Westport offers. This special home presents the perfect blend of elegance, comfort, quality & natural beauty - a true masterpiece.

116 Roseville Rd, Westport
365 Greens Farms Rd, Westport
$3,850,000
6 Beds ⋅ 5 Baths ⋅ 24124482 MLS
Generously sited on 2.15 stunning acres in Greens Farms, the Joseph H. Wakeman House is a perfect example of New England ingenuity and warmth. Built in 1840, this distinguished Federal-style residence was thoughtfully reimagined in the 1930s by an owner intent on showcasing its craftsmanship and enduring quality. The current residents were similarly captivated by its character and history. Located in the heart of one of Westport's most coveted and convenient neighborhoods, the park-like grounds, with sweeping lawns and meandering stone walls, are enchanting in every season. Inside, the home is warm and inviting-walls painted in pristine white provide a clean backdrop that highlights architectural details and period millwork. Wideboard flooring and 9-foot ceilings extend throughout, underscoring the timeless proportions and charm. Welcomed through double front doors, guests are immediately drawn to the gracious front hall or library, lined with bookshelves and anchored by the home's original staircase - a space so inviting, it is hard to leave. The elegant LR, with its rare double fireplaces, easily accommodates a grand piano, while the intimate formal DR-also with a fireplace, encourages evenings when friends linger. A butler's pantry connects seamlessly to the gourmet kitchen, which opens to the terrace and is bathed in natural light.The spacious FR features wide French doors to the yard, while a charming mudroom offers a practical yet welcoming entry.

365 Greens Farms Rd, Westport
18 Woodhill Rd, Westport
$3,800,000
6 Beds ⋅ 7 Baths ⋅ 24144655 MLS
Nestled near the end of an upscale cul-de-sac in prime Greens Farms, the newest SIR SIGNATURE Home blends timeless design with modern luxury on beautifully flat, private grounds. A heated gunite pool with auto cover anchors the expansive backyard w/ two connecting raised patios creates a true indooroutdoor retreat. Inside, sunfilled spaces showcase the craftsmanship SIR is known for. High ceilings, custom millwork, wide-plank oak floors, and a stunning chef's kitchen opens to a spacious family room w/ a distinctive beamed ceiling & walls of glass overlooking the property are just some of the highlights which place this fine home in a class of its own. The purposeful layout offer effortless flow for everyday living and entertaining. Six bedrooms include a serene primary suite w/ spa inspired bath incl floating white oak vanity and generous dressing room. The finished third floor provides flexible bonus space w/ bath for work or play, while the fully finished walk-out lower level offers recreation, fitness, and media options. The private office with custom cabinetry provides an ideal place to work in serene surroundings. Thoughtful amenities like designer lighting, a terrific mudroom, pantry, and attached garage complete this exceptional home. Close to Greens Farms school, beaches, walk to Westport Tennis Club and only 1.6 mi to train. A rare opportunity to buy from Westport's most trusted builder with over 300+ completed homes in one of the town's most coveted neighborhoods.

18 Woodhill Rd, Westport
312 Compo Rd S, Westport
$3,750,000
4 Beds ⋅ 4 Baths ⋅ 24173977 MLS
Coastal Living at Its Finest - Compo Beach, Westport, CT Some homes are simply houses - others are a lifestyle, and this exceptional Compo Beach Colonial is unmistakably the latter. Built in 2012 and maintained in pristine condition, this 4-bedroom, 3.5-bath residence offers the rare combination of newer construction quality and effortless coastal elegance, nestled just minutes from the sparkling shores of one of Westport's most coveted neighborhoods. Step inside to an open, airy floor plan bathed in natural light, where a spectacular great room and chef's kitchen flow seamlessly together - crisp whites, soothing blues, and natural textures creating a relaxed yet decidedly high-end atmosphere that simply lives beautifully. When the weather calls, the oversized porch becomes the true soul of the home - the perfect setting for morning coffee, evening gatherings, and the unhurried moments that define summer on the Connecticut shore. Upstairs, the primary suite redefines comfort with a private sitting room, home office, and a spa-inspired bath featuring heated floors, a heated towel rack, and a deep soaking tub - thoughtful luxuries that make every day feel like a getaway. With generous secondary bedrooms, meticulous finishes throughout, and a location that puts Compo Beach, Westport's beloved amenities, and Metro-North all within easy reach, this is coastal Connecticut living at its absolute finest.

312 Compo Rd S, Westport
24 Spriteview Ave, Westport
$3,650,000
4 Beds ⋅ 4 Baths ⋅ 24156059 MLS
FEMA-COMPLIANT and masterfully built in 2018, this extraordinary coastal residence at 24 Spriteview Avenue on Saugatuck Island offers an unrivaled waterfront lifestyle in one of Westport's most coveted enclaves. 4 bedrooms include 2 sumptuous primary en-suites and 3.5 impeccably appointed baths. All rooms are drenched in natural light and showcase captivating water views, creating a seamless connection to the shoreline. Custom stained hardwood floors, solar panels, and a full-house Tesla generator combine refined elegance with modern efficiency and peace of mind. The chef's eat-in kitchen is drenched in sunlight, appointed with premium appliances and an oversized island, flowing effortlessly into the family room where walls of glass open to expansive waterfront terraces designed for sophisticated entertaining. A built-in bar with kegerator elevates every gathering. A private office, bespoke built-ins, and three gas fireplaces add warmth and distinction throughout. Multiple decks and a breathtaking rooftop terrace frame panoramic sunrise and sunset vistas, along with front-row views of July 4th fireworks over the water. Residents enjoy access to three private beaches, a private backyard dock, and proximity to Cedar Point Yacht Club. Just minutes to town, train, and schools-yet a world away-the ultimate turnkey waterfront sanctuary.

24 Spriteview Ave, Westport
10 Winding Ln, Westport
$3,600,000
5 Beds ⋅ 5 Baths ⋅ 24163168 MLS
Experience the pinnacle of luxury living in this exceptional 4,600 sq ft, 5-bedroom home, ideally located in highly sought-after Old Hill. Perfectly positioned on a pristine 1-acre lot, this stunning home offers a rare "walk-to-everything" lifestyle-just steps from shopping, top-rated restaurants, and Earthplace. Designed for both elegant entertaining and everyday comfort, the home features an open-concept floor plan enhanced by timeless architectural details and modern upgrades. Sun-drenched living spaces on the main level include a gourmet kitchen, formal living room, dining area, family room, office, and a versatile pool cabana or fitness room-all seamlessly opening to an expansive patio for effortless indoor-outdoor living. Two first-floor ensuite bedrooms provide flexible accommodations. Upstairs, the luxurious primary offers a private retreat, complemented by a large playroom, laundry room, and two additional bedrooms with a shared bath-creating a versatile layout. The resort-style outdoor setting is equally impressive, featuring a gunite pool with spa, pergola, fire pit, outdoor grill area, vegetable garden, and a fully integrated lighting and sound system. Mature, century-old trees, curated specimen plantings, and extensive stonework create a private, park-like oasis. For the buyer seeking privacy while being near all the amenities that Westport has to offer, this extraordinary property combines classic elegance, modern amenities, and an unbeatable location.

10 Winding Ln, Westport
22 Burritts Lndg S, Westport
$3,550,000
5 Beds ⋅ 5 Baths ⋅ 24130961 MLS
Live the dream in this 4,800+ sq. ft. 5BR, 5BA home on 1 acre in one of Westport's most desirable private beach neighborhoods - just a 5-minute walk to the train! Fully remodeled in 2024, this home features a stunning covered stone porch, gourmet kitchen, formal dining room, multiple fireplaces, home office, and spacious family rooms. The luxurious primary suite offers dual walk-in closets, a spa-like bath, and a sleek electric fireplace. A finished lower level includes a media room, guest suite, and full bath. Bedroom above the garage with private bath, dual closets, and separate HVAC. Enjoy association amenities: private beach, pool, and dock with boat slips. Not in flood zone. Whole-house generator included.

22 Burritts Lndg S, Westport
123 Cross Hwy, Westport
$3,500,000
5 Beds ⋅ 6 Baths ⋅ 24166688 MLS
A sophisticated blend of past & present, this private sanctuary offers the ultimate in modern design in the heart of Westport. Designed for effortless indoor-outdoor living, the property features 5 BRs, 4.5 BAs, a separate guest house, expansive decking & a gunite pool set on private 1.35 acres. The home retains its massive original central chimney now the striking centerpiece of the open main level. The rooms flow seamlessly to the exterior gardens, while expansive walls of glass create a natural connection to the outdoors throughout the seasons. The spectacular 14' limestone kitchen island anchors the space alongside a limestone accent wall & a dramatic portrait window overlooking the patio, dining pavilion & pool. Each impeccably curated room showcases a refined juxtaposition of old & new, creating a cohesive, timeless aesthetic. The luxurious primary suite includes a stunning marble bath, dressing room & scenic views of the grounds. The finished walk-out lower level offers space for yoga, fitness, recreation, plus a walk-in natural stone wine cellar & pool changing room. Tiered steps lead to the pool terrace, ideal for lounging amid magnificent specimen trees and lush gardens. A separate guest house mirrors the organic warmth & texture of the main residence. Mature landscaping screens the fully fenced private level property in a prime Westport location within walking distance to Wakeman Farm, minutes to the train, beaches, shops, restaurants, schools, and other amenities.

123 Cross Hwy, Westport
150 Hillspoint Rd, Westport
$3,500,000
4 Beds ⋅ 4 Baths ⋅ 24154934 MLS
Just steps from the sand, this captivating Compo Beach retreat delivers the coastal lifestyle buyers dream about-effortless, elegant, and designed to be lived in year-round. Set above the flood zone on .52 acres of exquisitely landscaped grounds, this lovingly maintained 4-bedroom, 4-full-bath home feels both refined and relaxed, with outdoor living woven into every experience. Sunlight streams through expansive windows and doors, creating a seamless flow between indoors and out. The open main level invites connection, anchored by a welcoming living room with stone fireplace, a sunlit dining area, and well-designed kitchen that opens to an expansive Azek deck-ideal for summer dinners and sunset gatherings. A casual family room and coveted screened-in porch overlook the grounds, offering peaceful spaces to unwind. A main floor bedroom with access to a renovated hall bath provides flexibility, while a mudroom and direct access to the two-car garage add everyday ease. Upstairs, the primary suite is a private escape with vaulted beamed ceilings, a spa-like renovated bath with oversized shower, and a large walk-in closet. Two additional bedrooms, a light-filled study area, laundry room, and a dramatic bonus/rec room with soaring ceilings complete the second floor. The lower level gym provides walk out to patio with cozy firepit and outdoor shower. Full House Generator. Room for pool. Natural Gas, City Water and Sewer. Easy for commuters - located minutes to train and I-95

150 Hillspoint Rd, Westport
13 Terhune Dr, Westport
$3,499,999
6 Beds ⋅ 6 Baths ⋅ 24114691 MLS
Welcome to this beautifully crafted new construction home in the heart of Westport, where timeless design and thoughtful details come together to create a luxurious space. From the moment you step inside, you're welcomed by a bright and open floor plan with high ceilings and wide-plank flooring that runs throughout the main living space. Natural light fills every room, highlighting the custom finishes and high-end craftsmanship that define this exceptional home. The kitchen is a true showpiece, designed for both everyday living and entertaining. Full custom inset cabinetry and professional appliances, sleek quartz countertops and double oversized center islands provide plenty of prep space and seating. On the exterior, the home is clad in classic hardy board, an expansive outdoor kitchen, and elaborate stone detail with plenty of room for a pool, spa, or however you wish to complete your outdoor oasis. At the end of a quiet cup-de-sac, yet situated in a prime Westport location close to schools, beaches, shopping, and commuting options, this new construction offers everything you need in a forever home-modern comfort, classic style, and room to grow. Pool/spa included for $4,399,000

13 Terhune Dr, Westport
42 Spriteview Ave, Westport
$3,499,000
3 Beds ⋅ 4 Baths ⋅ 24167502 MLS
A rare convergence of water, light and privacy, this extraordinary waterfront home offers a lifestyle few ever experience.Perfectly positioned between the open expanse of the Long Island Sound and the quiet rhythm of a private canal, the home is set on a private island just one hour from New York City, yet feels worlds away. Sweeping, unobstructed views stretch endlessly in every direction, with sunsets that transform the sky into a daily work of art. Defined by its clean, modern lines and expansive walls of glass, the home is designed to fully embrace its surroundings.Three spacious decks extend the living experience outdoors, each offering a distinct vantage point from morning light over the water to the stillness of evening reflections along the canal. Inside, newly installed wide-board white oak floors bring warmth and understated sophistication to a home that is entirely move-in ready. Every space is oriented toward water, creating a seamless connection between interior living and the natural beauty beyond. With direct water frontage, a private beach and an ever-changing coastal backdrop, this is more than a home, it is a singular waterfront retreat defined by light, scale and the quiet luxury of complete privacy.

42 Spriteview Ave, Westport
249 Greens Farms Rd, Westport
$3,480,000
7 Beds ⋅ 9 Baths ⋅ 24132302 MLS
Storied and superbly restored, 'The Lookout' at 249 Greens Farms Rd blends the grandeur of a 1907 Victorian with todays modern luxury. Privately set among perennial gardens and antique copper beeches, this iconic 16-room residence offers a gracious floor plan with elegant formal spaces, a chefs eat-in kitchen, media room, wine cellar, and inviting family areas. Original architectural details shine alongside impeccable updates. The primary suite features a spa bath and custom closets; three additional bedrooms offer flexible space. Outside, relax by a sparkling pool or host gatherings on the lush, landscaped lawn. An adjacent lot for added privacy or future expansion is also available. A true Westport landmark, steps from town, schools, and rail, this is a rare opportunity to own an estate rich in character and comfort. Shown by appointment

249 Greens Farms Rd, Westport
3 Bolton Ln, Westport
$3,470,000
6 Beds ⋅ 7 Baths ⋅ 24126676 MLS
This beautiful home with undeniable curb appeal crafted by Andy Frank, sits on a flat, centrally located acre in the heart of Westport. Designed with light-filled spaces and an open, eat in kitchen, the home is finished across 4 levels, offering versatile living for today's lifestyle. The primary suite flows into a large sitting area with a lovely deck overlooking the pristine backyard. Enjoy 5 additional bedrooms, sun drenched interiors, private home office with patio, and a walk-out lower level perfect for recreation or guest space. Outside, in the fully-fenced backyard, there is an 18x42 pool by RI pools with safety cover and spa, fire-pit, outdoor shower, kitchen and a huge play area which creates a private retreat, ideal for all seasons. A whole house generator ensures comfort and peace of mind year-round. Blending timeless design, functionality and location this Westport gem truly checks every box.

3 Bolton Ln, Westport
1 Flower Farm Ln, Westport
$3,450,000
5 Beds ⋅ 8 Baths ⋅ 24148553 MLS
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 offers a stone fireplace, coffered ceilings with French doors leading to a bluestone terrace, overlooking the gorgeous landscaped property. Gather in the sophisticated formal dining room w/yet another fireplace. The main level graciously accommodates a guest bedroom suite with a full bath, walk-in closet, as well as a study adorned w/Cherrywood & built-ins, leading to a serene blue stone screened-in porch. The main level also has the convenience of 2 powder rooms & a mudroom, as you enter from the 3 car garage. Upstairs, discover the luxurious primary bedroom w/a sitting room, 2 walk-in closets, changing room, & spa-like bathroom w/a claw hydro tub, shower & private balcony access. Additionally, there are 3 more bedrooms each w/a custom full bathroom, along w/a generous bonus room. The fully finished 3rd floor offers versatility with a half bath. Entertain on the lower level, featuring a theater room, gym w/sauna, family room, wine room & powder room. Outside, the meticulously landscaped grounds showcase an inground gunite pool, hot tub, pool house w/a full bathroom overlooking 2 acres.

1 Flower Farm Ln, Westport
2 Half Mile Cmn, Westport
$3,400,000
4 Beds ⋅ 5 Baths ⋅ 24190832 MLS
Meticulously maintained and move-in ready, 2 Half Mile Common offers comforts, flexibility, and convenience. With 4 generously sized bedroom this light-filled home features a finished lower level with a full bath, gym, and recreation space, plus a separate playroom over the garage that's ideal as a second home office, studio, or playroom. Enjoy a fenced backyard with beautifully landscaped grounds, hot tub and outdoor kitchen, perfect for entertaining or play. Need more space? There is a 3rd floor just waiting to be finished! Ideally located on a quiet cul-de-sac, this home is within walking distance to Staples High School and Wakeman Town Farm, and just minutes from downtown Westport, beaches, shopping, dining, and Metro-North for an easy NYC commute. A rare opportunity to enjoy turnkey living in one of Westport's most convenient locations.

2 Half Mile Cmn, Westport
3 Bowling Ln, Westport
$3,400,000
6 Beds ⋅ 6 Baths ⋅ 24169947 MLS
Now under construction with a summer move-in, this exceptional 6-BDRM SIGNATURE Home is set on a quiet cul-de-sac in Westport's sought-after Long Lots school district. Built by SIR Development-renowned for over 30 years and 300+ homes of exceptional craftsmanship-this residence seamlessly blends timeless design with modern luxury. A welcoming interior showcases 10-foot ceilings on the main level, highlighted by custom oak beam detailing and expansive windows that fill the home with natural light. The thoughtfully designed open floor plan is ideal for both everyday living and effortless entertaining. The chef's kitchen features custom SIR cabinetry, premium Thermador appliances, and a fully appointed larder with wet bar, wine cooler, and floor-to-ceiling storage-perfectly tailored for both function and style. The living room opens through sliding glass doors to a granite patio and spacious, level backyard, creating a seamless indoor-outdoor connection. Add'l main-level highlights include a private office with custom built-ins, formal LR, and a well-designed mudroom for everyday convenience. Upstairs, 5 generously sized BDRMs include a luxurious primary suite w/ a vaulted, beamed ceiling, fireplace, dual walk-in closets, and a spa-inspired bath designed for relaxation. The finished walk-out lower level offers exceptional versatility, complete w/ 6th BDRM, full bath, media room, gym, and custom built-ins w/ref drawers-ideal for guests,recreation, or extended living.

3 Bowling Ln, Westport
5 Michele Ln, Westport
$3,400,000
6 Beds ⋅ 9 Baths ⋅ 24170058 MLS
Set at the end of a private cul-de-sac in Westport's coveted Coleytown neighborhood, 5 Michele Lane is a statement of craftsmanship, scale, and resort-style living. Surrounded by mature plantings for exceptional privacy and just steps from the Saugatuck River, this custom Colonial blends timeless architecture with elevated design throughout. A classic wood shingle exterior and wood roof set the tone, while the interior showcases 9'+ ceilings, marble tile, extensive millwork, and refined trim details. A dramatic Venetian plaster foyer introduces the home's elegant yet inviting aesthetic. Spanning three expansive levels plus a walk-up attic, the residence offers 6 bedrooms, 7 full baths, and 2 powder rooms-designed to accommodate both grand entertaining and comfortable everyday living. Seven fireplaces add warmth and architectural character across the home's generous living spaces. The outdoor setting is truly exceptional, featuring a resort-caliber gunite pool with integrated spa, expansive bluestone patio, outdoor kitchen, and a beautifully designed pergola-creating a private retreat ideal for entertaining or relaxation. Inside, the home continues to impress with well-proportioned rooms, a luxurious primary suite, and en-suite bedrooms throughout. The finished lower level offers additional space for recreation, wellness, or guests, complemented by a private sauna, wine cellar, additional laundry, guest suite, rec room, gym and lounge.

5 Michele Ln, Westport
2 Webb Rd, Westport
$3,400,000
6 Beds ⋅ 7 Baths ⋅ 24146001 MLS
Winner of the 2025 HOBI Award for "Best In Town Spec Home" in CT! Exceptional new construction, on a quiet cul-de-sac, in one of Westport's most desirable neighborhoods. Walk to Post Road shops, restaurants, Winslow Dog Park, Main Street, Library & Levitt Pavilion. Only 3 miles to train! This stunning home offers 6 bedrooms, 5 full and 2 half baths across 4 finished floors. Features include a Gunite pool with automatic safety cover, a large, flat, fenced in, private yard with walk-out lower level, full house generator, EV charging outlet, and city water, sewer, and natural gas. Traditional layout with modern, high-end finishes and an abundance of natural light. Built by multi-award-winning Westport Family Homes.

2 Webb Rd, Westport
1 Boxwood Ln, Westport
$3,400,000
5 Beds ⋅ 8 Baths ⋅ 24146662 MLS
Welcome to 1 Boxwood Lane, a private estate where timeless design meets a lifestyle centered on wellness, balance, &renewal. Set on a coveted quiet lane, the circular drive & stone walls introduce a sense of calm while sweeping lawns & specimen plantings create a serene, park-like environment worlds away from daily stress. Inside, sun-drenched interiors open seamlessly through French doors & expansive windows. The open layout encourages effortless living, anchored by a recently renovated custom Chef's Kitchen-perfect for nourishing gatherings & everyday enjoyment. Architectural details, intricate millwork, & graceful transitions between living & dining areas reflect craftsmanship rarely seen today. Designed as a true personal retreat, the home offers spaces that support both mind & body. The Primary Suite w/ fireplace & spa-inspired bath provides restorative comfort, complemented by 3 additional en-suite bedrooms & a second-floor Family Room offering options. A private Office w/fireplace creates a peaceful work-from-home sanctuary. At the heart of the home's wellness experience is a heated indoor Pool & Spa, visible from the private Home Gym-offering year-round opportunities for fitness, relaxation & stress relief in a resort-like setting. Whether swimming, training, or unwinding poolside, this space elevates daily living into a holistic lifestyle.1 Boxwood Lane offers a rare year-round country club atmosphere-designed for wellness, connection, and effortless luxury.

1 Boxwood Ln, Westport
119 Long Lots Rd, Westport
$3,352,000
5 Beds ⋅ 5 Baths ⋅ 24166818 MLS
In Westport's coveted Long Lots neighborhood, this residence makes a striking first impression, set back in quiet privacy behind mature trees and landscaped grounds. Reimagined and expanded in 2010, the home offers sunlit rooms of impressive scale ideal for both memorable entertaining and everyday luxury, with high-end updates and amenities at every turn. An inviting first-floor lounge with pool table provides room to gather, while the gourmet chef's kitchen showcases premium appliances, an oversized island and countertops of statuary marble, and generous prep and entertaining areas. A private suite above a 3-car garage includes gathering room with fireplace, bedroom and full bath with room for guests and home office. The park-like property unfolds as a resort-style retreat featuring a sparkling pool, patio with pizza oven, expansive sunny lawn, outdoor fireplace and beautifully terraced gardens. A no-maintenance koi pond and a greenhouse add to the rare, estate setting, and a hot tub offers year-round enjoyment. 5 bedrooms include a sumptuous primary suite with fireplace, spa bath with heated floors, steam shower, and luxe statuary marble and nickel vanity, offering a private sanctuary. Enjoy property views from the 2nd floor deck. Walk to the ALL NEW Long Lots Elementary School that's underway and 2 min to middle and high schools. It's privacy, elevated living spaces and curated outdoor living at this exceptional residence 5 minutes to train and Westport's lively downtown

119 Long Lots Rd, Westport
1 Wheeler Gate, Westport
$3,300,000
4 Beds ⋅ 5 Baths ⋅ 24198512 MLS
Compo Commons classic! Impeccably maintained, and recently renovated, this wonderful home seamlessly pairs Connecticut charm with a contemporary edge, and a nod to what is current. The dramatic foyer welcomes you to a gracious and tailored living room with a fireplace or the intimate dining room with a built-in dry bar and beautiful bay window. The gorgeous gourmet kitchen offers enviable counter space, a huge center island, high-end appliances and custom cabinetry; it opens to a soaring great room with cathedral ceiling, Shaker-inspired paneling, a striking wood burning fireplace, and 2-story windows. The abundant natural light and spaciousness is captivating. Upstairs, the luxurious primary bedroom suite includes separate lounge/seating areas, a stunning bathroom, dressing area and walk in closet. There are three additional bedrooms and two full bathrooms completing the second floor. A portion of the full basement has been finished to offer maximum flexibility for end use. The professionally landscaped half acre property, boasts a stone patio with retractable striped awning for those lingering, late afternoon golden hour conversations. After 29 years and a full roster of meaningful Westport memories, the current owners are looking for the next stewards to take the reins. This is an amazing opportunity to be close to all that makes this coastal town tick and become a part of a coveted neighborhood near restaurants, shopping, train and beach.

1 Wheeler Gate, Westport
4 Wild Rose Rd, Westport
$3,300,000
5 Beds ⋅ 5 Baths ⋅ 24167522 MLS
Wonderful reimagining of this circa 1880 antique home on a quiet in-town cul-de-sac. Set on a level half acre and beautifully rebuilt and expanded by Further Afield, the home now features 3 levels of brand new living space. An English inspired kitchen features inset cabinetry, marble countertops, Bertazzoni appliances and an 11' island with storage and seating. A separate larder/pantry with oak countertops hides small appliances and includes food storage, microwave, wine fridge and a second sink for functionality. Family Rm with built-ins and wood-burning FPL features a wall of glass doors to the patio and gorgeous private property with room for a pool. 5 BRS on one level include a stunning primary suite with 10' ceilings, two walk-in closets and a marble bath. A well-outfitted mudroom, laundry rm and finished lower level flexible space complete this new home. Amazing in-town location with sidewalk access to Westport's main shopping district, restaurants and the Saugatuck River. Another beautiful restoration from Westport's Further Afield!

4 Wild Rose Rd, Westport
10 Sprucewood Ln, Westport
$3,276,000
5 Beds ⋅ 5 Baths ⋅ 24171000 MLS
Tucked at the end of a coveted Hunt Club lane, 10 Sprucewood Lane offers exceptional privacy, architectural refinement, & an enviable setting within one of Westport's most sought-after neighborhoods. Thoughtfully renovated in 2017, this sophisticated Colonial showcases a gracious & versatile floor plan that seamlessly balances classic elegance with modern living. Sun-filled interiors & a curated neutral palette create a refined atmosphere throughout more than 5,000 square feet of beautifully appointed living space. At the center of the home is a stunning chef's kitchen, featuring Carrera marble, stainless steel appliances, & a walk-in pantry - expertly designed for both effortless daily living and elevated entertaining. Formal living spaces & the expansive great room connect seamlessly to an entertainer's backyard, highlighted by a spacious mahogany deck, sweeping lawn, & charming stone walls. A screened-in porch off the living room offers an inviting space for relaxation, casual dining, or gathering with guests. Distinctive highlights include two primary ensuite bedrooms - one featuring a luxurious steam shower, four fireplaces, two mudrooms, an oversized garage, & a dramatic great room anchored by a striking see-through fireplace. The fully finished lower level provides exceptional flexibility with an ensuite bedroom, home office, recreation room with fireplace, and an additional mudroom with abundant storage and direct exterior access. Room for a pool. Welcome Home!

10 Sprucewood Ln, Westport
27 Woody Ln, Westport
$3,250,000
5 Beds ⋅ 5 Baths ⋅ 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
16 Burr School Rd, Westport
$3,250,000
5 Beds ⋅ 5 Baths ⋅ 24118985 MLS
A masterful full renovation by acclaimed Coastal Luxury Homes, this extraordinary modern residence redefines sophistication in the heart of Westport. Set on a pristine, private acre on a coveted cul-de-sac, the home dazzles with soaring ceilings, dramatic walls of glass, and exquisite luxury finishes throughout. Designed for the way you live today, it offers two primary suite options, an architecturally striking double-sided floor-to-ceiling fireplace, and a show-stopping gourmet kitchen outfitted with premier appliances and custom millwork. A finished lower level extends the living space, perfect for media, fitness, and leisure. With an expansive patio for entertaining and room for a pool, this rare offering delivers the ultimate lifestyle - minutes to town, train, beaches, and top-rated schools.

16 Burr School Rd, Westport
3 Hickory Hill Rd, Westport
$3,250,000
5 Beds ⋅ 5 Baths ⋅ 24123838 MLS
3 Hickory Hill Rd, an exceptional new construction sits on a quiet cut-de-sac close to Westport's Town Tennis courts & ball fields & 3 mins to Main St. With over 5000SF on 4 finished levels, this home blends modern design, luxury finishes, & thoughtful functionality. The main level features 9' ceilings, wide-plank white oak floors & a dramatic oak & glass staircase with white oak wall paneling.The chef's kitchen offers custom cabinetry, quartzite countertops & backsplash, a luxury Thermador appliance package & center island with seating for four. The breakfast area flows into a spacious FR with sliders to a bluestone patio. A gas-ready fireplace with stunning Sahara Noir marble surround & oak paneling is the focal point. Elegant tray-ceiling DR, walk-in pantry & mudroom with side & garage entry, large -format porcelain tile floors, custom oak -paneled cabinetry & benches complete the main level. Upstairs, the primary suite boasts a cathedral ceiling, dual walk-ins & spa- like bath with heated floors, Victoria & Albert soaking tub, large frameless shower with LED niches, custom cabinetry, marble counters & wall-mounted California Faucets. 2 BRS share a Jack & Jill bath, while the 4th has its own ensuite. The 3rd floor offers a private office & recreation/playroom & and the finished lower level includes the 5th BR, full bath & gym/media room. Professionally landscaped 0.34 acre lot with stone walls, sprinklers & room for a small pool. Home is EV charger & generator ready.

3 Hickory Hill Rd, Westport

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