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19 E Horseshoe Ln, Westport
$3,200,000
5 Beds ⋅ 5 Baths ⋅ 24169575 MLS
Located on a quiet cul de sac only one mile from Metro North Train Station/I95 and two miles from Compo Beach, Longshore Country Club and downtown Westport - could your new home be any more convenient? Multiple HOBI award winning builder, CCO Habitats, presents its latest new construction project - a 5 bedroom, 4.5 bath home finished on 4 levels with room for a smaller pool. As always, there are some new features to discover, making this home unique from anything previously built. There's a warm, welcoming vibe, with oversized European tilting windows allowing the natural light to blend seamlessly with the white oak and glass interiors. Cozy modern. Sophisticated and stylish. An open floor plan presents a variety of lifestyle options. You can have either one or two offices and still have four multipurpose rooms to enjoy in different ways. Perhaps a living room, a family room, a media room and a great room? And that's not even including the gym! Maybe you'd prefer a library or a studio - go for it! There's an EV outlet waiting for you and yes, it's generator ready as well. It's just so easy. Functionality meets beauty and combines to create a truly livable home. Come discover. Come enjoy. Come home.

19 E Horseshoe Ln, Westport

91 Turkey Hill Rd S, Westport
$3,200,000
5 Beds ⋅ 6 Baths ⋅ 24166415 MLS
Beautifully sited in prestigious Greens Farms this timeless 5 BR, 6BA clapboard-and-stone Colonial offers stunning architecture & resort like privacy just moments from train, town & beaches. A gracious front porch & exquisite landscaping create an immediate sense of presence; classic, composed & quietly impressive. Inside, a soaring entry filled w/natural light introduces interiors defined by beautiful scale, 9-ft ceilings & gracious flow. Formal living room w/gas fireplace & dining room w/wet bar lend elegance to entertaining while a handsome office/den w/custom built-ins offers warmth & intimacy. The kitchen is refined & inviting w/quartz countertops, Sub-Zero appliances, walk-in pantry & breakfast/dining area opening to bluestone terrace. The expansive family room anchored by a substantial stone fireplace creates a natural gathering place & French doors open seamlessly to the outdoor living space. The main level also includes a secondary entry w/back staircase, laundry room, additional office & 2nd powder room. Upstairs the primary suite is a true retreat w/oversized walk-in closets, dressing area & spa-like marble bath. 4 additional generously proportioned bedrooms including two en-suite offer flexibility for family & guests. Finished 3rd fl ideal for playroom, gym, media room, 6th BR. Outside sprawling grounds, expansive bluestone terraces, exceptional masonry & stunning saltwater gunite pool & spa create a private oasis w/serene resort-like feel. Impeccably presented.

91 Turkey Hill Rd S, Westport

10 Side Hill, Westport
$3,175,000
6 Beds ⋅ 6 Baths ⋅ 24178615 MLS
Now more than ever, home is a haven - a place to live, work, relax, and entertain. Privately sited on 1 beautifully landscaped acre in highly sought-after Old Hill, this sophisticated 6,000+ SF home with a brand-new pool offers 6 bedrooms, exceptional living spaces, and breathtaking western sunsets overlooking Earthplace's 62-acre nature sanctuary. A rare blend of privacy, style, and convenience, all within walking distance to town. Designed for both elegant entertaining and comfortable everyday living, the main level features a stunning chef's kitchen with custom cabinetry, pantry, and sun-filled dining area flowing seamlessly into the spacious family room with fireplace - all overlooking the expansive lawns, sparkling pool, and serene natural setting. Formal living and dining rooms provide elegant gathering spaces, while a private office/playroom and guest bedroom with full bath complete the first floor. The luxurious primary serves as a private retreat with sitting area or office, walk-in closet, and spa-inspired bath. Four additional bedrooms, two full baths, and a conveniently located laundry room complete the second level. The top floor offers exceptional bonus space, including a vaulted-ceiling playroom, additional room, and half bath. The lower level provides versatile space featuring a gym, mudroom, and extensive storage. Chic yet welcoming interiors, contemporary amenities, and extraordinary natural surroundings combine to create the ultimate Westport retreat.

10 Side Hill, Westport

16 Gault Park Dr, Westport
$3,151,600
5 Beds ⋅ 5 Baths ⋅ 24150527 MLS
Built in 2014, this modern farmhouse offers timeless design and an easy flow on a flat, private, fully fenced 1-acre with possible pool site. A welcoming front porch opens to a front-to-back living room with impressive stone fireplace. The sun-filled dining room features a coffered ceiling, paneling & Serena & Lily chandelier. The chef's kitchen is beautifully appointed with high-end appliances, quartz countertops and center island, plus abundant storage, incl. walk-in pantry. Just off the kitchen, a vaulted family room with oak beams and a gas fireplace includes space for everyday dining and flows seamlessly to a stone patio, ideal for outdoor dining and summer grilling. A ground-floor bedroom with full bath provides flexibility, while a custom office with work space and built-ins could serve as a den, creating the option for a main-level suite ideal for in-laws, guests, or an au pair. A shiplap-lined mudroom with cubbies includes a chic powder room and leads directly to the 2-car garage, prewired for EV. Upstairs, a 2nd family room offers separate hangout or study space. The primary suite features a vaulted ceiling, 2 walk-in closets, and a spa-like marble bath with soaking tub and steam shower. Additional bedrooms include one en-suite and two with a Jack-and-Jill bath. Finished lower-level is ready for gym equipment or toys, and a walk-up attic offers expansion possibilities. Set in a biking & dog walker's neighborhood close to town, train, beach, and award-winning schools

16 Gault Park Dr, Westport

55 Center St, Westport
$3,150,000
5 Beds ⋅ 5 Baths ⋅ 24163297 MLS
Located in Westport's coveted Greens Farms neighborhood, this light-filled home is perfectly sited high and dry on a private park-like acre with room for a pool and pool house. A renovated kitchen with top-of-the-line appliances and sunny breakfast nook opens to a spacious great room with stone fireplace and expansive deck overlooking the property, ideal for indoor-outdoor living. The flexible floor plan includes a rare first-floor bedroom with full bath, ideal for guests, au pair, or multi-generational living, along with a finished walk-out lower level offering additional space for recreation, media, or work-from-home needs. The primary suite features two walk-in closets and a new spa-like bath. With 5 bedrooms and 5 baths, the home offers ample space for living, working, and entertaining. Modern conveniences include city water, city sewer, natural gas, and an EV charger. Exceptional location just minutes to Greens Farms Elementary, the Greens Farms train station, Burying Hill Beach, and downtown Westport shopping and dining.

55 Center St, Westport

26 Treadwell Ave, Westport
$3,150,000
5 Beds ⋅ 5 Baths ⋅ 24132802 MLS
26 Treadwell Avenue is where historic charm meets a modern edgy vibe. Reimagined from the ground up in 2025 by Michael Greenberg, this 1894 Victorian Farmhouse has been transformed into a statement of refined design and craftsmanship. Notable features include exposed beams, white oak floors that ground the space, and curated architectural finishes that make every room feel intentional. Set on a beautifully landscaped half-acre in the heart of Westport's Saugatuck neighborhood, the home blends relaxed charm with elevated living. The classic wraparound porch leads to airy, light-filled interiors where natural textures and clean lines mix seamlessly. A separate guest apartment above the detached garage adds flexibility-perfect for visitors, a studio, or a private office. It's a rare find: timeless character with a fresh, modern perspective.

26 Treadwell Ave, Westport

6 Over Rock Ln, Westport
$3,150,000
5 Beds ⋅ 5 Baths ⋅ 24100975 MLS
Timeless New England Colonial on 1.3 acres blending historic architecture with modern updates. Built in 1860 and reimagined by designer Dan Barsanti with curated interiors by Rena Levine, this five-bedroom, five-bath residence features refined millwork, wide-plank floors, and bespoke lighting. The open main level includes a bright kitchen with premium appliances, dining area, and living room with French doors to a bluestone patio and heated pool. A first-floor suite provides flexible guest or office space; the upper level hosts a spacious primary suite, marble bath, and dressing area. Systems include upgraded HVAC, EV-ready garage, and smart-home controls. Set on 1.3 acres with mature landscaping and a fenced backyard. Just 1 mi to Compo Beach, 0.9 mi to Longshore Golf Club, 1.0 mi to Levitt Pavilion, and 1.1 mi to Downtown Westport shops and dining. Offered furnished with curated designer pieces for a move-in experience rarely available in Westport.

6 Over Rock Ln, Westport

34 Sasco Creek Rd, Westport
$3,135,000
3 Beds ⋅ 5 Baths ⋅ 24133270 MLS
Walk to the beach! Rare opportunity to own 2 flat acres encompassing a renovated beach house and a remarkable modern barn designed with walls of glass. All uniquely located in the Greens Farm community of Westport, boasting LI Sound beach access and abutting the Connecticut Audubon trails. An updated 3-bedroom Cape offers one level living with a primary suite on the main floor and two bedrooms on the upper level. A glass enclosed sunroom with French doors opens to a private patio overlooking the expansive fenced yard. The beautifully renovated two story barn with skylights and oversized windows capture an abundance of the surrounding light from the rear Western exposure. Two half baths and an upper-level space for work or relaxation complete the barn. This seaside beach residence with glorious grounds features specimen trees, wildflowers and more. The main home offers 1882 square feet. The barn provides an additional 2,098 square feet. This seaside beach residence uses solar panels and has a generator. Vacation living can be embraced everyday!

34 Sasco Creek Rd, Westport

24 Washington Ave, Westport
$3,126,000
4 Beds ⋅ 4 Baths ⋅ 24175092 MLS
There is a moment just inside the front door, when the house introduces itself. The entrance hall-original, unhurried, exactly as gracious as 1919 intended-tells you everything. This is a home that was built when details mattered and time was taken. A century later, nothing essential has been lost. The living room and formal dining room carry that same quiet elegance, their proportions generous, their light beautiful through Anderson architectural-grade windows. Then comes the turn- into the 2013 addition, where a stunning chef's kitchen anchors a family room that opens through French doors onto a covered deck. Beyond it, a private landscaped backyard unfolds like a secret: lush, park-like, deeply planted and utterly your own. An outdoor shower with hot and cold water, a detached two-car garage, gravel driveway and an automated irrigation system make it as effortless as it is beautiful. Upstairs, the primary suite earns its name- spacious bedroom, sitting room, a spa bath, place to exhale. Three additional bedrooms, each with the soul of the original house, share a handsome hall bath.A finished third-floor now features two versatile offices and a full bath, offering flexible space ready for your next chapter. New roof, siding insulation, 4-zone A/C, sewer and water mains from 2013. 4300 SF set on .39 acres of one of Westport's most sought-after residential streets -walking distance to town.This home exudes charm and is completely, confidently, move -in ready.

24 Washington Ave, Westport

28 Pin Oak Ct, Westport
$3,100,000
6 Beds ⋅ 7 Baths ⋅ 24109321 MLS
Stunning brand new construction just minutes from downtown!! - Fantastic 6 bedroom, 6.1 bath colonial boasts 6,500+ sq/ft of living space! - Open floor plan with 9' ceilings and tons of natural light! - Gorgeous kitchen features Thermador appliances, white shaker-style cabinetry, quartz counters, tile backsplash, custom step-in wine locker, and large walk-in pantry! - Great flow for entertaining on the main level between the open kitchen, living room with gas fireplace, and spacious dining room! - Spectacular primary suite with vaulted ceiling, attached sitting / dressing room, 2 walk-in closets, and impressive en-suite bath featuring heated tile floor, rainfall shower head + soaker tub! - 3 additional bedrooms on the 2nd floor - Great 3rd floor offers huge family room + another bedroom with private en-suite bath - Bedroom on the main floor doubles as a great home-office option - Huge walk-out lower level with lots of natural light offers tons of options as additional family / play room, home gym, etc. - Lower level also features a custom wine cellar room + full bath + storage room - Fantastic location offers lots of privacy as the last house on a dead-end street! - Large & private back yard & site plan approved with a pool permitted, ready to go (additional cost) - Hardwood floors and LED lighting throughout - Generac Generator - Another quality home by Andy Frank, a builder with 30+ years of experience!

28 Pin Oak Ct, Westport

4 Jennings Ct, Westport
$3,100,000
5 Beds ⋅ 7 Baths ⋅ 24116296 MLS
Tucked away on a sought-after Westport cul-de-sac, this elegant 5-bedroom home offers the perfect blend of luxury, comfort, and convenience. Set on over an acre of beautifully landscaped property, enjoy resort-style living with a stunning gunite pool, private patio, and lush lawn-ideal for summer entertaining or peaceful relaxation. The spacious first-floor primary suite is a true retreat, complete with his and her separate bathrooms and a private sauna. The heart of the home is the chef's kitchen featuring a Wolfe cooktop, Sub-Zero refrigerator, and generous workspace, opening to a sun drenched eating areas. With two dedicated offices, working from home is effortless. Located just minutes from schools, shopping, beaches, and transportation, this centrally located gem offers the best of Westport living-privacy, space, and style-all in one of town's most desirable neighborhoods. A rare find that checks every box!

4 Jennings Ct, Westport

36 Bauer Pl Ext, Westport
$3,025,000
6 Beds ⋅ 6 Baths ⋅ 24161889 MLS
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, these spaces flow onto the patio for easy indoor-outdoor living. A living room and dining room complete the inviting main level. Upstairs, the fabulous primary suite features custom closets and a spa-like bath. Two bedrooms share a chic Jack & Jill bath, while a 4th bedroom is ensuite. A laundry room is conveniently located on this level. The 3rd floor offers a bedroom, full bath, and a spacious flexible living area-perfect for guests, an office, playroom, or recreation space. The lower level is a true wellness retreat with a fully customized gym, sauna, and full bath. Perfectly set in a sought-after neighborhood, it's just a short walk to Long Lots Elementary and minutes to shopping, dining, and the Greens Farms train. With more than $100K in next-level enhancements, this residence has evolved into a truly spectacular home. Beautifully decorated, warm, and welcoming, this home is ready to enjoy from day one. Modern conveniences include city water, city sewer, natural gas, and generator readiness.

36 Bauer Pl Ext, Westport

35 Woody Ln, Westport
$3,015,000
5 Beds ⋅ 4 Baths ⋅ 24158858 MLS
Enjoy the resort lifestyle in this beautiful home! Discover unparalleled luxury and privacy at 35 Woody Lane, a meticulously renovated 5-bedroom, 3.5-bath sanctuary on 2.18 acres. Nestled at the end of a serene cul-de-sac in the acclaimed Long Lots neighborhood, this turnkey residence blends timeless elegance with modern sophistication. Step into a chef's dream kitchen featuring a massive island, custom cabinetry, high-end stainless appliances, vaulted ceilings with skylights, and seamless flow to the living areas, ideal for effortless entertaining. The exquisite primary suite offers a spa-like bath, custom built-ins, and peaceful treetop views. Generous secondary bedrooms and baths provide comfort for family and guests. The crown jewel: a resort-style backyard oasis with a sparkling gunite pool, full tennis court, hot tub, fire pit, expansive deck, and lush, private landscaping, your own secluded escape for year-round enjoyment, al fresco dining, and play. Experience the perfect fusion of luxury living and Westport lifestyle, minutes to top schools, Compo Beach, and commuter rail.

35 Woody Ln, Westport

240 North Ave, Westport
$3,000,000
5 Beds ⋅ 5 Baths ⋅ 24181944 MLS
"MEADOW WOOD" - Nearly two acres of Westport's most spectacular land is the setting for this storied estate, which has been completely remodeled, expanded and transformed for modern living. Totally fenced & screened w/privacy trees, this unique property offers rare sophistication with a stunning main residence, gunite pool, and a 2,447+/- sqft barn. Gated driveways lead to both the main house & the barn, and the stunning setting makes an enduring impression. The glamorous echoes of a Hollywood-style estate combine w/incredible updates throughout the transformed interiors. The front-to-back LR has a distinctive bay window & dual doors to a serene porch that gazes across the expansive grounds. The incredible great room is the focal point of this expertly-designed floorplan, combining a Chef's kitchen w/expansive island, endless storage, Thermador appliances, breakfast/casual dining area, all leading to the incredible DR & fam rm which has a wall of folding glass doors creating an effortless flow between the gorgeous interior & exterior spaces while preserving open views across the property. A BR suite w/private access, large laundry rm, mudrm, garage & powder rm complete this level. Upstairs, well-appointed BRs w/designer baths await. The primary suite is an exquisite space w/tray ceiling, fpl, plush bth, walk-in dressing rm & an amazing balcony that spans much of the rear of the home. An elegant patio lines the heated pool. The barn is a dream for auto enthusiasts.

240 North Ave, Westport

22 Sturges Commons, Westport
$3,000,000
5 Beds ⋅ 8 Baths ⋅ 24178328 MLS
22 Sturges Commons offers the rare combination of timeless elegance, true neighborhood living, and unmatched convenience in one of Westport's most sought-after locations near the Hunt Club. Just one traffic light to the Greens Farms Station train station, this home makes commuting to New York City effortless while allowing you to return home to a peaceful walking neighborhood where charming streets converge, creating the classic community feel that is increasingly rare in Westport, CT real estate. Set on beautifully landscaped property, the home is designed for both relaxed everyday living and exceptional entertaining. The fully fenced backyard features a sparkling pool and spa, expansive outdoor spaces for dining and gatherings, and plenty of room for sports and play. Inside, warmth and sophistication define every space. The gourmet chef's kitchen opens seamlessly to a spacious step-down family room with soaring ceilings and abundant natural light, creating the perfect heart of the home. Formal living and dining rooms provide elegant entertaining spaces, while multiple options for home offices and flexible living make this property ideal for today's lifestyle. Offering 5 ensuite bedrooms, 8 baths, a third-floor office or yoga retreat, and a finished lower level complete with gym, media room, and playroom, this exceptional Westport home blends luxury, comfort, and functionality in one of the best commuter locations in Fairfield County.

22 Sturges Commons, Westport

2 Mortar Rock Rd, Westport
$3,000,000
4 Beds ⋅ 6 Baths ⋅ 24173081 MLS
Better than new, this pristine 2016 custom-built residence offers a rare standard of refinement and sophisticated excellence. With 4,000+sqft and an elevator accessing all four finished levels, the home blends modern architecture with beautifully executed transitional design. The open-concept main level features a magnificent chef's kitchen, spacious dining area, and expansive living room with gas fireplace, custom built-ins, beams, and tray ceiling. Four-inch white oak flooring runs throughout. A wall of glass doors opens to a breathtaking private setting with a remote-controlled awning, ideal for effortless indoor/outdoor living. Four bedrooms include the luxurious primary suite with tray ceiling, built-ins, and serene garden views, plus a spa-like bath with heated floors, soaking tub, double vanity, and walk-in closets. Two additional en-suite BRs and an exceptional home office with dual built-in desks, double-height bookcases, library ladder, and automated shade complete the level. The third floor offers a skylit fourth bedroom with full bath and cedar closet. The finished lower level includes a playroom/gym, office, and half bath. A 2car garage, elevator to all levels, full-house generator, security and sound systems elevate the offering. Ideally set on a desirable cul-de-sac minutes to the beach, train, town, library, and farmers market, making this an incredible location from which to enjoy all of Westport's most coveted amenities. Move-in ready and truly exceptional.

2 Mortar Rock Rd, Westport

36 E Main St, Westport
$2,999,000
6 Beds ⋅ 6 Baths ⋅ 24192039 MLS
Nestled in the heart of Westport, Connecticut, this stunning new construction residence redefines elegant suburban living with unparalleled sophistication, timeless grace and is complete and ready for immediate occupancy. Boasting six generous bedrooms and six luxurious bathrooms, the home features soaring nine-foot ceilings that bathe its expansive interiors in natural light and create an atmosphere of airy grandeur. Thoughtfully designed with premium finishes, custom millwork, and state-of-the-art systems. From the chef's kitchen with Thermador Appliances and a commanding kitchen island to the serene primary suite with a warming fireplace and a walk in closet fit for royalty; every detail invites effortless entertaining and refined daily living. Spanning three floors, this home offers exceptional versatility with a peaceful third floor sanctuary housing a private office and media room for entertainment or productivity. The finished lower lever further elevates the lifestyle with a spacious additional family room and an exercise studio, creating inviting spaces for relaxation, recreation, and personal wellness. Set against Westport's coveted landscape, located across from Winslow Park and upscale shopping, this exceptional property offers a rare opportunity to embrace modern luxury within one of Fairfield County's most distinguished communities.

36 E Main St, Westport

221 Greens Farms Rd, Westport
$2,995,000
5 Beds ⋅ 6 Baths ⋅ 24171950 MLS
The Bedford House: Architecturally and historically significant estate in Greens Farms. This exceptional property offers a rare opportunity to own one of Westport's true gems with a remarkable provenance. Set on 2.33 acres with a gunite pool & spa, court and a 2400 SF barn w/ 3 car garage, loft and more, this estate blends timeless elegance with modern comfort. Originally built in 1904 and designed by noted architects Visscher and Burley, this Colonial Revival style home has undergone thoughtful renovations over the years to preserve and enhance its original character. High ceilings, oversized windows, detailed millwork and sun-filled rooms create a sense of warmth and sophistication. Recent renovations include a new cedar roof on both house and barn, a like-new pool, spa & mechanicals, refinished hardwood floors, updated HVAC and new appliances. A unique highlight of this estate is its location across from Nyala Farms, offering scenic views of 50 acres of open meadows and fields with a deed restriction preventing any further development. Enjoy the ultimate lifestyle, minutes to the train, beaches, schools, shops and fine dining.

221 Greens Farms Rd, Westport

216 Hillspoint Rd, Westport
$2,995,000
5 Beds ⋅ 5 Baths ⋅ 24133642 MLS
A rare opportunity in the heart of Compo Beach! This beautifully rebuilt updated 5BR, 4.5BA home offers over 4,600 sq ft of living space on a spacious and private .33-acres-uncommon scale for the neighborhood. Just steps from Old Mill and Compo Beaches, enjoy the privacy of a tucked-away residence with the convenience of in-town living and coastal beach access right across the street. Built with character by ship captain William Sherwood in the early 1800s, the home retains its historic charm and has been thoughtfully rebuilt, structurally reinforced, and expanded-preserving its architectural essence while introducing high-end finishes and craftsmanship. Timeless character blends with modern comfort featuring wide-plank floors, exposed beams, and custom millwork warmth, while natural light fills every room. From the inviting family rooms to the formal living and dining rooms, each centered around beautiful fireplaces that add depth and atmosphere. The chef's kitchen with cherry cabinetry and high-end appliances opens to stone patios and lush gardens-perfect for entertaining. Ideal as a spacious year-round family residence or weekend guest retreat, the flexible layout includes a serene primary suite with spa bath and dressing room, three additional bedrooms, and a finished open-plan third floor with water views and full bath-perfect for guests, office, or studio. The lower level showcases steel beam construction and meticulous care.

216 Hillspoint Rd, Westport

30 Saint Johns Pl, Westport
$2,925,000
5 Beds ⋅ 4 Baths ⋅ 24182424 MLS
Saint John Place is the street people who know Westport quietly hope opens up. It almost never does. Reimagined in 2007 by Renato Gasparian Associates and refreshed in 2022, this house has all the right moves. Inside, the main level opens up the way you hope it will. The great room stretches nearly thirty-four feet and flows into the dining area and a kitchen built around a center island, with a custom walk-in pantry right behind it. A sun room pulls in the morning light. There's a separate family room, plus a real office with a door that closes. Upstairs, five bedrooms give everyone somewhere to land. The primary suite has a spa bath with a soaking tub, a separate shower, and two walk-in closets (because who likes to share?). The laundry is up here too, in its own room. The outdoor spaces close the deal. A bluestone patio wraps around a good portion of the house with a stone fireplace. The deep flat lot is screened by mature plantings and gives you the privacy people leave town to find. You're in the heart of Westport's in-town neighborhood, which means the car can stay in the driveway. Walk to a different cuisine every night, the shops, the Library, the Westport Country Playhouse, summer nights at the Levitt Pavilion. The Saugatuck River is right there, and a celebrated omakase counter is a few minutes on foot. When you do want the car, the beach is a short drive away. Beautiful house, easy life, almost everything a walk from the door. Tour online @ 30saintjohn.com

30 Saint Johns Pl, Westport

299 Saugatuck Ave, Westport
$2,900,000
4 Beds ⋅ 6 Baths ⋅ 24169465 MLS
*THANK YOU FOR YOUR INTEREST, SELLER REQUESTS HIGHEST/BEST OFFERS BY 3PM MONDAY 6/1/26*Set on over an acre of park-like, usable property, this stunning Modern home with an oversized gunite pool is a showcase of exhilarating design. In an area known for major watefront properties as well as immediate convenience to the railroad station and all commuting routes, this home blends sophisticated elegance with an easy lifestyle. A gracious, landscaped approach brings you to the grand double-door entrance lined with windows and into a vaulted ceiling foyer. The interior captures gorgeous light all day through walls of glass & numerous skylights. The floor plan is an entertainer's dream, accommodating groups large or small in refined surroundings. The living and family rooms each have floor-to-ceiling stone fireplaces and glass doors to the rear deck. The DR has a picture-perfect view across the property. Gourmet E-I-K w/Wolf gas cooktop, Sub Zero ref/frz, Viking double ovens, pantry, center island w/seating & a breakfast area enhanced by scenic views. An adjacent sunroom transitions the space out to the deck. Two half baths complete this level. The airy atmosphere continues up front & rear stairs to the 2nd level, beginning w/a grand primary suite w/priv sitting rm, king-size BR w/pool view balcony, vast dressing rm & two lux baths. Three addl' BRs have double clsts & two full baths. Fin LL w/rec rm, office, storage. Enjoy a porch that leads to the pool/spa. 3 car garage, generator.

299 Saugatuck Ave, Westport

3 Nassau Rd, Westport
$2,875,000
5 Beds ⋅ 4 Baths ⋅ 24136334 MLS
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 soaking tub and glass shower. Three additional bedrooms and two full baths complete the second floor. The third-level loft opens directly to a finished roof deck with sweeping water views-ideal for relaxing or gatherings. The property's outdoor spaces include a heated gunite saltwater pool, stone terrace, and level yard surrounded by low-maintenance landscaping. Additional features include white-oak flooring, energy-efficient systems, and an attached two-car garage. Conveniently located near Saugatuck Shores, just 4 minutes to the Metro-North train station and about 13 minutes to Compo Beach, with quick access to Longshore Club Park, Ned Dimes Marina, and downtown Westport restaurants. A refined coastal retreat blending design, comfort, and proximity.

3 Nassau Rd, Westport

3 Hubbels Ln, Westport
$2,875,000
6 Beds ⋅ 7 Baths ⋅ 24131692 MLS
Come see the latest CCO Habitats new construction home - located at the end of a private road - 3 Hubbel's Lane - and buffered by non developable land for privacy. Only one mile to downtown/Main Street (.6 mile to Coffee An' for the best donuts in town!!) with sidewalks to make the stroll even easier! Go the other way, and you're 1.5 miles from the newly renovated Coleytown school district. Close enough for super convenience without being so close that you have to deal with traffic. Easy peasy lemon squeezy! This home is finished on 4 levels with over 6300 finished square feet of living space, and as always, has some new design elements to make it unique from any other CCO Habitats creation. Oversized European doors and tilting windows plus an amazing wall of windows give incredible natural light. Warm and soft with the coastal boho design that is so chic as well as comfortable to live in. A first floor office. A gym. EV outlet and generator ready. Move in and enjoy life in Westport!

3 Hubbels Ln, Westport

5 Northside Ln, Westport
$2,865,000
6 Beds ⋅ 5 Baths ⋅ 24089498 MLS
A true Westport landmark, Staffordshire Hall is an extraordinary gated stone estate blending timeless grandeur with modern luxury. Privately nestled on manicured grounds, this bespoke manor spans three levels of meticulously crafted living space. A sweeping circular drive leads to the columned entrance. The Great Hall stuns with a stone hearth, coffered ceilings, and French doors opening to the grounds. Rich architectural details, soaring ceilings, French doors and oversized windows define the main level's expansive rooms. The family room with fireplace leads to a terrace, lush lawn, and custom pool/spa with dramatic fountains. A grand library with French doors, built-ins and a wet bar has beautiful sunlight and views. Entertain in the elegant formal dining room with butler's pantry or cook in the sunlit gourmet kitchen with its own terrace and a comfortable seating area. Upstairs, find 5 spacious and distinguished bedrooms, and 3 beautifully updated baths, including a tranquil primary suite with spa bath, walk-in closet, sitting room/nursery, and private balcony. The walk-out lower level is a luxe separate living space with full kitchen incl AGA stove, Porcelanosa bath, 6th BR (5 BRs per town), and private entry, making it ideal for guests, staff, multi-generational living or home office space. Three car garage, two laundry rooms & plentiful storage. The interior was rebuilt and is in excellent, move-in condition; the home is suited to classic or modern style choices.

5 Northside Ln, Westport

27 Bauer Pl Ext, Westport
$2,850,000
5 Beds ⋅ 6 Baths ⋅ 24195597 MLS
Still hoping to move before school starts? This exceptional new construction home is ready for immediate occupancy! Built by SIR Development, Westport's premier luxury builder with 30+ years of experience and 300+ homes built, this hidden gem sits at the end of a cul-de-sac in a welcoming neighborhood within walking distance to Long Lots Elementary School. The open layout spans 4 beautifully finished levels and showcases SIR Signature Home craftsmanship and designer finishes throughout. The custom eat-in kitchen with butler's pantry features sleek white cabinetry with warm oak accents, quartz countertops, handmade ceramic tile backsplash and premium Thermador appliances, opening seamlessly to the inviting family room with fireplace. The main level also offers a private study with custom oak shelving, formal dining room, mudroom and powder room. The luxurious primary suite features vaulted ceilings, a spa-inspired bath and two walk-in closets. The finished 3rd floor includes a 5th bedroom and full bath. The walk-out lower level offers custom built-ins, recreation room, gym and half bath. Outside, enjoy a level backyard, spacious granite patio with room for a pool, professionally landscaped grounds and fencing for privacy. Connected to city water and sewer with propane gas, this move-in-ready home offers the perfect blend of luxury, comfort and style.

27 Bauer Pl Ext, Westport

8 Washington Ave, Westport
$2,850,000
5 Beds ⋅ 6 Baths ⋅ 24173805 MLS
Award-winning builder proudly presents a rare, beautifully restored high Victorian Gothic home chronicled for its grace and splendor. Original architectural details artfully remain, including the only known local example of clustered colonette posts adorning the veranda. The interior showcases curved archways, carved mahogany stair banister and newel post, and detailed window trim. White oak Smallbone kitchen with La CornuFe range and mosaic marble tile opens to a dining/great room. Light fixtures and appliances were individually selected with an artist's eye. Sun-filled, the home offers six-inch white oak flooring throughout, stunning renovated baths, and all-new mechanicals with an electric heat pump and Smart home technology. The flexible layout includes a first-floor guest suite with full bath, powder room, and living room with fireplace. The second level boasts three bedrooms, one en-suite, plus a hall bath. The finished third level works as a primary suite, guest suite, or office with full bath and laundry. The detached two-car barn and garage conceal a legal one-bedroom cottage with a private garden. New kitchen, appliances, flooring, heat pump, and renovated bath; ideal for extended family or income. Both structures feature Smart eco-systems controlling security, sound, light, and climate via voice or phone. While away the hours on one of the two porches overlooking the private garden and stone wall. This coveted walk-to-town gem is an investment in loving life here.

8 Washington Ave, Westport

33 Burnham Hl, Westport
$2,825,000
4 Beds ⋅ 2 Baths ⋅ 24130770 MLS
Beach Living Awaits at 33 Burnham Hill Road, Westport. Build or reimagine the home of your dreams on this generous .61-acre lot (approximately 100' x 266'), perfectly positioned on a peaceful cul-de-sac in Compo Beach. The property features a beautiful stone wall, an expansive yard, and is surrounded by homes of substantial size. With ample room for a pool, it presents endless opportunities for outdoor enjoyment and design flexibility. This rare offering combines privacy, community, and coastal charm - all just moments from Westport's sandy shoreline, Longshore Club Park, and the vibrant downtown scene. Imagine mornings with ocean breezes, afternoon walks to the beach, and evenings watching the sunset over Long Island Sound. From a modern beach retreat to a charming New England escape, the possibilities here are as inspiring as the setting itself. Enjoy all that Westport has to offer - schools, fine dining, shopping, recreation, and an easy commute to NYC - from one of the town's most beautiful neighborhoods. 33 Burnham Hill: Where your coastal dream begins.

33 Burnham Hl, Westport

21 Dover Rd, Westport
$2,800,000
5 Beds ⋅ 5 Baths ⋅ 24167866 MLS
Spacious and impeccably maintained Colonial tucked away on a quiet cul-de-sac in one of Westport's most desirable locations, just moments to town, schools, trains, beaches, and everyday conveniences. Offering four finished levels, this beautifully updated home features 5 bedrooms, 4 full baths, and a powder room. Designed for both comfortable daily living and effortless entertaining, the home showcases sun filled interiors, hardwood floors throughout, and timeless architectural details. The updated kitchen opens seamlessly to the inviting family room with fireplace, while formal living and dining rooms offer additional space for gathering and entertaining. A spacious mudroom with first floor laundry adds everyday convenience. Additional highlights include two fireplaces, a brand new roof, whole house generator, and irrigation system. Set on professionally landscaped grounds with inviting outdoor living spaces and a private level backyard with room for a pool. Exceptional opportunity in a sought after Westport location. Additional professional photography will be added closer to the live date.

21 Dover Rd, Westport

20 Old Hill Rd, Westport
$2,795,000
5 Beds ⋅ 6 Baths ⋅ 24115085 MLS
Welcome to this beautifully maintained 1945 stone-front Cape in the heart of Old Hill. Loved by the same family for 22 years, it radiates warmth and character. With 5 bedrooms, 5.5 baths, and two flexible spaces for home offices, it offers comfort and versatility, including a first-floor suite ideal for guests or in-laws. The light-filled kitchen flows into an inviting dining area and cozy sunken family room with a stunning river-rock fireplace-perfect for gatherings or quiet evenings. French doors open to a level backyard with a bluestone terrace, outdoor fireplace, and grilling area, creating an ideal setting for entertaining. A 3-car tandem heated garage, mudroom, pantry, and laundry room add practicality, while a gracious dining room and front-to-back living room with built-ins and a second fireplace set the stage for special occasions. Upstairs, the serene primary suite offers a balcony, spa-inspired bath, and dressing room. Three additional bedroom, 2 additional full baths and a loft provide space for everyone. The finished lower level features a playroom, gym area, full bath, and ample storage with walk-out access to the Garage . Move-in ready with room to personalize, this special home invites you to start your next chapter in one of Westport's most desirable neighborhoods. Don't miss the chance to make it yours!

20 Old Hill Rd, Westport

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