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$1,150,000
24187682 MLS
Don't miss this great opportunity close to town. The .87Acre lot is elevated ,rolling and ideally positioned off Kings Highway. There are distance views of the river and town through the trees. There is an older small 1400 sq ft. single family home that has been a rental for many years. The previous owners in the 30's made each floor into apartments. Each level with its own entrance features a living room , one bedroom, kitchen and full bath. This small house offers a unique opportunity to be a ADU or separate office as part of a new home that can be built.There is a sewer hook up for the new house has been paid in full. Please refer to town hall for required building regulations. This is a rare opportunity for the next owner to create something special close to town. Need permission to walk property and see house.

119 Kings Highway North Road, Westport

$3,499,000
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

$5,999,999
7 Beds 8 Baths 24183173 MLS
Set on 1.70 private acres in the heart of Greens Farms, this distinctive new construction by Dwell offers a rare combination of timeless design, exceptional privacy, and resort-caliber outdoor living. Offering 8,700+/- sq ft, this exceptional residence features 7 bedrooms, 8 bathrooms, and thoughtfully designed living spaces crafted with an emphasis on enduring design rather than passing trends. The chef's kitchen serves as the heart of the home with an 11-foot waterfall island, Wolf and Sub-Zero appliances, custom cabinetry and millwork, and full scullery kitchen. Designed with both functionality and flexibility in mind, the home features a first-floor guest suite, expansive bonus room over the three-car garage, dual laundry stations, two wet bars, secondary staircase, 4 fireplaces, walkout basement, and ensuite bedroom accommodations on all four finished levels. Outdoor amenities include a heated 20' x 40' pool, covered outdoor living room with vaulted ceiling and wood-burning fireplace, sunken fire pit, expansive lawn areas, and professional landscaping with mature trees and multiple activity zones. Approximately one mile from Old Mill Beach and minutes to both train stations and town.

13 Edgemarth Hill Rd, Westport

$2,795,000
6 Beds 7 Baths 24183141 MLS
Experience timeless elegance in this extraordinary Colonial estate nestled in Westport's coveted Red Coat neighborhood. Offering more than 7,000sf of beautiful living space, plus an additional 2,400sf in the finished lower level, this exceptional residence combines luxury, comfort, and functionality. Featuring 6 spacious bedrooms and 5.2 baths, the home is thoughtfully designed for both everyday living and sophisticated entertaining. The chef's kitchen is equipped with premium Wolf appliances and opens to expansive gathering spaces, while a formal dining room, private office, and game room with a dry bar provide endless opportunities to entertain. The spectacular lower level is a destination of its own, complete with a home theater, recreation room, and an impressive wine cellar for the discerning collector. The luxurious primary suite serves as a private retreat with its own fireplace, spa inspired bath with jacuzzi, private balcony, and elegant finishes. 3 additional en suite bedrooms, separate nanny quarters, and a flexible bonus room offer exceptional versatility. Recently refreshed with new interior and exterior paint, all new heating and cooling systems, and stunning hardwood floors throughout, this home is truly move in ready. A welcoming covered front porch adds classic New England charm, while the private backyard is designed for outdoor enjoyment with a built in grill, spacious patio, and integrated sound system. 3 car garage and an unbeatable location.

25 Hermit Ln, Westport

$9,860,000
6 Beds 9 Baths 24181904 MLS
Newly completed by Compo Luxury Homes, 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, year-round 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. Additional highlights include a DaVinci slate roof, premium European windows and lift-and-slide doors, Lutron lighting, whole-home networking, seven-zone HVAC, security system, and a 32kW Generac generator.

9 Over Rock Ln, Westport

$3,685,000
4 Beds 6 Baths 24180388 MLS
Welcome to 3 Laurel Lane, a stunning new construction nestled in the heart of Westport, Connecticut. Discover the epitome of elegance & sophistication. This modern masterpiece is set on a .21 acre lot. The stunning new luxury construction is designed by renowned Coastal Luxury Homes. Known for their architectural brilliance & unparalleled craftsmanship, Coastal Luxury Homes are a testament to innovative design & meticulous attention to detail. The rich architecture features flowing lines, glass elements, & harmonious blend of natural materials, create a stunning visual impact. The interior showcases an open-concept layout that is as functional as it is beautiful. Every corner will showcase high-end finishes, from cabinetry to the designer fixtures. The rich hardwood floors guide you into the Living Room. Adjacent to the living area, the gourmet Kitchen awaits, boasting ample storage & a generous island that invites culinary creativity. The Kitchen is a chef's paradise, equipped with top-of-the-line appliances & designed for both entertaining & everyday living. The four Bedrooms with en-suite Bathrooms provide both privacy and comfort for family and guests. Ascend to the third level, where you'll find a versatile Rec-Room equipped with full bath. The finished LL features a large Family Room. This home, offers not only luxury but also the convenience of nearby beaches, dining, and shopping. Come experience the perfect blend of refinement & comfort in this exceptional property!

3 Laurel Ln, Westport

$6,795,000
7 Beds 7 Baths 24180715 MLS
A rare offering in Westport's coveted Compo Beach neighborhood, this extraordinary estate sits on a prized double lot just moments from Compo Beach, Longshore Club, train & vibrant downtown. Featured in Westport Magazine, the property masterfully blends the charm of a beautifully preserved historic residence from 1928 w/ a remarkable 6,000 sq ft addition completed in 2008. The result is a seamless fusion of timeless New England architecture, modern luxury and exceptional craftsmanship. Spanning 9,000 square feet across 4 finished levels, the home offers 7 bedrooms, 6 full & one half baths, 6 fireplaces, soaring 10-foot ceilings, plus a 1st floor in-law/au pair suite. Sunlight pours through an abundance of windows, enhancing the home's gracious proportions & creating a bright, welcoming atmosphere throughout. A dramatic limestone & marble foyer w/ spiral staircase introduces elegant and inviting living spaces enhanced by custom hand-carved moldings and millwork, including a gracious living room with floor-to-ceiling arched windows, library, music room & private offices. The spectacular 900-square-foot chef's kitchen and great room, anchored by a reclaimed limestone fireplace from Burgundy, France, is the heart of the home-an extraordinary gathering place where family & friends come together effortlessly for intimate evenings & grand-scale entertaining.

21 Compo Pkwy, Westport

$1,495,000
24181616 MLS
**Plans submitted and waiting on final approvals likely completed July/August.** Rare opportunity to build new in one of Westport's most sought-after neighborhoods. Set on approximately one acre on a quiet Coleytown side street, this property offers the ideal combination of privacy, natural surroundings, and convenience. Surrounded by established homes and just minutes from top-rated schools, downtown Westport, shopping, dining, beaches, and commuter routes, the location speaks for itself. The sellers have nearly completed the permitting process, and the property can be purchased with fully approved plans, allowing the next owner to move directly into the construction phase and avoid the time and uncertainty of approvals. The existing home is being sold as-is. A premier opportunity to create a custom home in an exceptional Westport setting. Rendering of home to be built.

9 Berkeley Rd, Westport

$14,900,000
5 Beds 9 Baths 24179641 MLS
Panoramic views of Long Island Sound extend from this gated, resort-like estate. Designed to maximize its spectacular waterfront setting, the east-facing main house takes in the coastal views from walls of windows, glass French doors, and private balconies. Effortless indoor-outdoor flow defines the main level, where a charming screened-in porch and awning-covered veranda overlook a Gunite pool with spa. First floor rooms facing the water include the living room and office, both with fireplaces, the formal dining room and the open kitchen/family room. This floor also has a billiard/media room, full bar, refrigerated wine room, two powder rooms and laundry. Idyllic second floor primary suite features waterfront balcony and sitting room, 3 walk-in closets and marble bathroom. Three additional en-suite bedrooms, each with balconies, complete this level. Perched on the third floor is a home gym with waterfront balcony, full bath and sauna. Newly added wing above attached two-car garage with one-bedroom guest suite. Perfect for summer entertaining, the backyard terrace offers a bar with built-in barbecue and a sitting area with firepit by the pool. Beyond the manicured lawns, the 168-ft seawall leads to an 80-ft pier and 20-ft private dock. Side yard with secluded outdoor shower, exterior-access powder room and kayak storage rack. Spacious two-bedroom guest cottage with 1.5 baths, kitchen, laundry and attached one-car garage. Commercial-sized generator powers main house & cottage.

279 Saugatuck Ave, Westport

$7,926,000
6 Beds 7 Baths 24177287 MLS
Set within Westport's most prestigious private estate enclave, surrounded by grand coastal estates and quintessential antique treasures, this exceptional Greens Farms 2+ acre* new construction offering is poised to become one of Fairfield County's most coveted addresses. Perfectly positioned, moments from beaches, downtown boutiques, vibrant dining scene, and just an express train to Manhattan, the property offers a rare blend of privacy, convenience, and timeless sophistication. Fully customizable and designed to fit your lifestyle and desired scale, this masterfully built residence will feature bespoke craftsmanship, rich stone, curated designer finishes, advanced smart home technology, and world-class amenities tailored entirely to your vision. Expansive grounds offer tranquil space for a private resort-style setting with endless possibilities for outdoor living and recreation. Walk the property with us and the Coastal Luxury Homes team and begin designing your dream estate.

Clapboard Hill Rd Unit (New Build), Westport

$4,850,000
5 Beds 5 Baths 24172211 MLS
Introducing The Winslow Manor, one of Westport's most exceptional estates, is a secluded retreat defined by beauty, privacy, and grace, now available for the first time in decades, inviting its next residents to experience the privilege of living within this storied and extraordinary sanctuary. Just steps from downtown & completely remodeled in 2002, welcome home to a rare and timeless estate where classic Arts & Crafts architecture meets the tranquility of a private countryside retreat. Set on over 2.5+ sprawling acres of pristine grounds, this exceptional 5 Bed, 5 Bath residence offers more than 5,100 sqft of refined living, surrounded by natural beauty & complete privacy. From the moment you arrive down the private, meandering drive framed by mature landscaping; The Winslow Manor evokes a sense of warmth, character, and enduring craftsmanship. Rich architectural details, beamed ceilings, inviting living spaces, & thoughtfully designed interiors create a home that feels both grand and deeply welcoming- as if stepping into a piece of cozy history, carefully preserved and elevated for modern living. Designed for both relaxation & recreation, the estate unfolds into an extraordinary outdoor experience. A sparkling Gunite pool, multiple terraces, Pergolas, & dedicated home gym create the ultimate summer retreat, while the surrounding pond and protected wetlands attract an abundance of wildlife, offering peaceful views and a connection to nature rarely found so close town.

22 Evergreen Ave, Westport

$1,899,000
4 Beds 4 Baths 24177591 MLS
Rarely does an opportunity like this become available in Westport. Set on 2.36 private acres with approximately 300 feet along the scenic Aspetuck River, this exceptional property offers a remarkable setting to renovate, expand, or create the custom estate you've always envisioned. The existing four-bedroom residence features a spacious primary suite with fireplace, an expansive kitchen, and a great room with fireplace opening to a deck overlooking the river. Whether you choose to preserve and enhance the current home or design an entirely new legacy property, the possibilities are extraordinary. Just minutes to downtown Westport, beaches, shopping, dining, and top-rated schools, this is a rare offering in one of Fairfield County's most desirable communities.

36 Lyons Plain Rd, Westport

$10,500,000
4 Beds 6 Baths 24177056 MLS
Designed by renowned architect and builder Frazier Forman Peters, this stone estate is set on nearly 3.5 private, meticulously landscaped acres in Westport. Crafted over more than two decades, the residence reflects exceptional artistry, scale, and craftsmanship. A gated entry and winding stone drive arrive at a stately porte-cochere and attached two-car garage, establishing a grand sense of arrival. Spanning over 10,500 square feet, the home offers four bedrooms, five full baths, one half bath, and living spaces defined by soaring ceilings, natural light, and timeless materials. The formal living room serves as a centerpiece with oak herringbone floors, Venetian plaster walls and ceilings, oversized windows, and a fireplace. Nearby, a double-height dining room with vaulted ceilings and imported Jerusalem stone creates a striking setting for entertaining. The chef's kitchen features professional-grade appliances, custom cabinetry, a large center island, and adjoining sitting area. A lofted library and study wrapped in handcrafted Honduran mahogany sits beneath skylights, while additional gathering spaces include a den, sunroom, wet bar, billiards lounge, and media room. A dedicated wellness wing offers an indoor lap pool, fitness center, sauna, and primary suite with dressing gallery, spa bath, studio, and private retreat. Grounds include an outdoor pool, tennis court, greenhouse, gazebo, pool house, and separate groundskeeper's residence.

47 Charcoal Hill Rd, Westport

$4,450,000
6 Beds 8 Baths 24145772 MLS
Are you dreaming of an estate property? Something a bit more than the generic flat acre on a cul de sac? How do two acres on the Aspetuck River sound to you? With views from your bedroom? The sounds of a waterfall next door lulling you to sleep? Having sunnies tickle your toes in the summertime? Maybe a bit of fly fishing for trout? Or perhaps some paddleboarding? Yes, of course, there's a 20x40 salt water pool, but . . the river - wow! Welcome to the latest offering from CCO Habitats - a new construction home with over 8300 sf of finished space on 3 floors. A floorplan you will love, with not only 2 designated offices, but a private first floor bedroom as well. Organic, modern, warm and inviting, with a calming palette sure to blend with and enhance your personal taste. An open starfish floorplan for togetherness as well as privacy. 10 foot ceilings on the first floor. Luxurious European oversized doors and windows provide amazing natural light. Custom cabinetry throughout. 6 bedrooms, 6/2 bathrooms. All of the bedrooms are ensuite with walk in closets. The wine room - where it belongs - in the dining room. An amazing gym that will tempt even the people least prone to exercise into movement. A walk-out lower level that doubles as a pool house, complete with a second laundry, full bath, wet bar and entertaining space. It's all here; only a mile from the award-winning Coleytown schools. This is the one you've been waiting for. Unique. Special. Just like you. :)

159 Easton Rd, Westport

$5,650,000
7 Beds 9 Baths 24172635 MLS
Experience modern luxury in this new SIR SIGNATURE Home by SIR Development, Westport's premier builder. Set on 1.02 private acres on a coveted cul de sac, this home offers a striking approach, 3car garage, and rare backyard privacy, all within walking distance to Bedford Middle, Staples High, Wakeman Fields, and Town Farm. A fresh contemporary aesthetic features a dramatic two story foyer, 10ft ceilings, custom paneling, character grade oak floors, refined millwork, and expansive windows. Sun-filled living and dining rooms complement the great room with a sleek 60inch fireplace and reclaimed beams. The chef's kitchen includes full size SubZero refrigerator and freezer, Wolf cooktop and double ovens, quartzite waterfall island, custom cabinetry, and walk-in pantry. A private office with built ins enhances work from home convenience. Outdoor living shines with a covered porch, granite patio, outdoor kitchen, and direct access to the 20x40 saltwater pool. The luxurious primary suite offers vaulted ceilings with antique beams, oversized walk ins, and a spa bath with custom vanities and textured tile. All five second floor bedrooms are ensuite. The finished third floor adds a full bath, office/craft room, and playroom. The walkout lower level includes a bedroom and bath, gym, wet bar, media room with raised platform, and large recreation area.

8 Pleasant Valley Ln, Westport

$3,795,000
4 Beds 4 Baths 24171986 MLS
Located in prestigious Greens Farms, this European-inspired Colonial offers a rare opportunity to enjoy immediate charm while planning for the future. Set behind private gates on expansive, picturesque grounds, the property is surrounded by multimillion-dollar estates-making it an exceptional canvas for new construction or a significant estate expansion. The existing home is beautifully renovated, offering flexibility with gracious living and dining rooms, a sun-filled sunroom, cozy family room, and a curated Chef's kitchen with Calacatta marble, bespoke cabinetry, and top-tier appliances. A serene Primary Suite and additional bedrooms upstairs, the home functions perfectly as-is-or as a future guest house or accessory residence with thoughtful modifications. The sweeping land provides ample room for a new main residence set further back on the property, while maintaining the current home for extended family, guests, staff, or as a pool house. Outdoor living is equally compelling, with an expansive covered stone terrace, fire pit, and open meadow-like grounds offering endless possibilities for a pool, tennis court, barn, or gardens. Whether you choose to embrace the home's timeless appeal or create a legacy estate tailored to your vision, this is a unique chance to live comfortably now while building for tomorrow-all in one of Westport's most coveted locations, just minutes to Westport's vibrant downtown with award winning restaurants, premium shopping, beaches, and train.

61 Clapboard Hill Rd, Westport

$4,250,000
6 Beds 9 Baths 24165540 MLS
Exceptional new construction by AR Luxury Homes with 7,500+/- square feet of thoughtfully designed living space across four finished levels in a prime Westport location. This 6-bedroom, 6 full and 3 half bath residence blends refined craftsmanship with modern functionality, featuring an open-concept layout ideal for both everyday living and entertaining. The heart of the home is a custom-designed kitchen equipped with premium appliances including Wolf and Sub-Zero, expansive island, and seamless flow to the family room with fireplace. Three fireplaces throughout the home add warmth and architectural interest. White oak flooring, custom millwork, and high-end finishes elevate every space. The upper levels offer a luxurious primary suite with spa-like bath and custom closet, along with well-appointed secondary bedrooms. A fully finished lower level with walkout access provides flexible space for recreation, fitness, or additional living. Set on a level .50-acre property, the outdoor experience is complete with a 15' x 30' heated gunite pool, bluestone patio, and professionally planned landscaping-perfect for enjoyment and relaxation. Additional features include city water and sewer, propane gas, 400-amp electrical service, 24 KW generator, and wiring for audio, security, and smart home systems. A rare opportunity to own a new construction home with exceptional scale, quality, and amenities. Still time to customize finishes.

6 Janson Dr, Westport

$3,450,000
5 Beds 5 Baths 24169922 MLS
A rare offering indeed! Welcome to 4 Charcoal Lane, an unrivaled multi-generational estate mere minutes from top-rated schools, shopping, restaurants and all that Westport has to offer. Sited on 2 private acres, this extraordinary property offers panoramic views of a 7-acre nature preserve, affording permanent tranquility. The meticulous renovations center around a gracious farmhouse-style Colonial with stunning features and superior craftsmanship, plus a spectacular post-and-beam Party Barn. A gourmet chef's Kitchen is the heart of the main residence, featuring a 14-foot Calacatta marble island and a suite of professional-grade appliances with dual Family Room fireplaces nearby. The Living Room's unique tray ceiling was specially designed for a superior piano experience. Upstairs, the Primary Suite is highlighted by a gorgeous spa bath. The property's exceptional appeal is anchored by the Country Carpenters barn, connected by a breezeway w/barn doors that create an inviting welcome to backyard entertaining. This luxury 1BR barn features 20-foot ceilings, heated floors, a full kitchen, and hinge-free retractable doors to seamlessly blend indoor/outdoor living. Resort-style amenities await outdoors with a Pebble Tec pool, waterfall hot tub & blue granite patio that remains cool underfoot on hot summer days. The entertainment porch features built-in heaters, see-thru fireplace and outdoor television. This is more than just a home, it's a legacy waiting to be claimed!

4 Charcoal Ln, Westport

$2,670,000
5 Beds 3 Baths 24161256 MLS
A rare opportunity to own one of Charcoal Hill's signature properties, this exceptional Frazier Peters stone home pairs historic craftsmanship with a level of care and refinement that is increasingly hard to find. Set atop 2.3 +/- gated acres and introduced through a stunning circular drive, the residence showcases Peters' hallmark use of native stone, warm wood tones, and artisan detail, creating a home that feels both enduring and deeply inviting. More recent expansion and remodeling have sensitively enhanced the home. Sunfilled rooms with vaulted ceilings and handhewn finishes offer a balance of scale, with multiple living spaces that transition seamlessly to the outdoors. The grounds unfold in a series of thoughtfully designed moments including lush perennial gardens, winding paths, quiet terraces, and vibrant seasonal color. At the center is a sparkling, oversized pool with a waterfall spa and a fully outfitted stone pool house, which is an ideal retreat for summer living. A heated 4car stone garage with a finished upper level provides flexible space for a studio, office, or possible guest space. Every corner of the property reveals another place to gather, from sunny patios to shaded areas beneath large awnings, all wrapped in exceptional privacy yet minutes to the energy and amenities of downtown Westport. A home where history, beauty, and modern comfort come together with uncommon harmony.

56 Charcoal Hill Rd, Westport

$5,895,000
4 Beds 6 Baths 24166955 MLS
Everything stays on the other side. That is what people here say about the footbridge. You cross it, and whatever you were carrying does not come with you. Compo Mill Cove is a gated private peninsula of nineteen homes on Long Island Sound, and no car has come out here since 1903. It is the reason the loudest thing you hear most mornings is the tide turning under the bridge. Everyone in this town is trying to buy quiet. Out here it is structural. This is the one with the water in every room: 5,567 SF of Brooke Girty-designed shingle style, built in 2008 and laid out so the Sound is never more than a glance away. Century-old reclaimed French oak floors. A three-story Nautilus stair through the center of the house. Five fireplaces. A Viking and SubZero kitchen. A primary suite with its own fireplace, dual walk-ins and a balcony above the water. Four bedrooms, generously scaled, plus a full third floor for guests, a studio or an office. Then the part you actually live in. A screened porch for the mornings. A Brazilian hardwood deck and hot tub for the evenings. Your own sandy beach with a kayak pulled up on it, held by a Race Coastal-engineered bulkhead. A private gate opening into the protected shoreline and woodland of Sherwood Island State Park. Green's Farms station minutes away, Manhattan about an hour. Nineteen homes. There will not be a twentieth. Your car is 150 feet away. You will not want it.

46 Compo Mill Cv, Westport

$6,375,000
4 Beds 5 Baths 24165538 MLS
Boater's Paradise-Live the Ultimate Saugatuck Shores Waterfront Lifestyle. Experience unparalleled, direct waterfront access from this striking contemporary perched directly on the shores of Long Island Sound. Featuring its own rare private dock, this property is a true boater's/water lover's paradise. Enjoy all that Saugatuck Shores has to offer-boating, jet-skiing, paddle boarding, or kayaking from your own backyard. Dramatic walls of glass bathe the interior with natural light throughout effortlessly blending modern architectural lines with unparalleled, panoramic views of Bermuda Lagoon, Peck Ledge Lighthouse and boating channels which can be seen from almost every room. The open-concept main level transitions seamlessly to a massive sundeck, setting the ultimate stage for indoor-outdoor entertaining. Spend summers relaxing by your private waterfront gunite pool and spa, rinse off in your outdoor shower or unwind in the custom indoor sauna. Positioned within the coveted, private Covlee Beach Association, residents enjoy access to a private sandy beach with additional dock slips, kayak and paddleboard storage, a playground, picnic area, and fire pit just steps away, blending complete privacy with an active coastal community. From the Great Room with its dramatic fireplace and vaulted ceiling, to the custom Kitchen with fireplace, to the cozy Family Room and Study, there are so many spaces to delight. All bedrooms, including primary suite, have decks overlooking the Sound.

21 Covlee Dr, Westport

$7,350,000
6 Beds 7 Baths 24152219 MLS
Set behind gates on over four exquisitely landscaped acres in Westport's coveted Beachside enclave, 69 Beachside Avenue is a private coastal estate offering a rare blend of scale, privacy, and resort-style living just moments from the shoreline. A long, gracious approach leads to a timeless residence defined by exceptional craftsmanship and sun-filled interiors. Expansive living spaces feature soaring ceilings, seamless flow, and walls of glass that frame the estate's serene, park-like setting-ideal for both grand entertaining and everyday living. At the center of the home, a chef's kitchen opens to elegant formal and informal spaces, creating an effortless environment for hosting. Each room is thoughtfully appointed with high-end finishes, bespoke details, and a refined sense of understated luxury, now fully realized with a newly completed primary bath designed as a private, spa-like retreat. Outdoors, the property transforms into a true resort experience, with a stunning pool and spa, spacious terraces, and a full Har-Tru tennis court set amid rolling lawns and mature plantings, offering exceptional privacy and tranquility. Perfectly positioned near Westport's beaches, Longshore Club, and vibrant downtown, this property also offers the rare advantage of direct access to Greens Farms Academy, a feature shared by only a select few homes. This property is where luxury, land, and lifestyle come together in one of Westport's most prestigious addresses.

69 Beachside Ave, Westport

$5,925,000
6 Beds 9 Baths 24163899 MLS
Located within the highly desirable Stony Point association, this exceptional home offers a rare combination of privacy, water views, and convenience just moments from the train, local restaurants, and everyday amenities. This particular home enjoys private dock membership, providing summer boat access just steps from your door. Completely transformed and expanded in 2016, the home features over 6,500sf of thoughtfully designed living space, including 6 bedrooms and 9 baths. Expansive panoramic windows capture serene water views and fill the home with natural light. A dramatic two-story entry foyer and soaring ceilings create an impressive sense of space. The open-concept kitchen/living room is a true centerpiece, featuring a massive 12-foot island with seating for 6, high-end appliances, dual dishwashers, a wine fridge, an ice maker - ideal for both everyday living and entertaining. Designed for effortless indoor-outdoor living, the home seamlessly connects its interior to exceptional outdoor entertaining areas. The spacious family room features sliders that open directly to the expansive covered patio with retractable screens, an outdoor kitchen, and a relaxing pool and spa. The 3rd floor great room has amazing water views, and features a 1/2 bath and wet bar. Additional highlights include a private office, whole house generator, 2 laundry rooms, sauna, a mudroom, and a charming 'hidden' playroom. A truly turnkey offering, this home embodies the very best of the Stony Point

3 Stony Point W, Westport

$1,329,000
3 Beds 3 Baths 24158630 MLS
Spacious sophistication in the heart of Downtown Westport. Perfectly positioned just moments from shopping, dining & recreation, this lovely in-town home offers a rare blend of comfort, flexibility, and location. The inviting living room with wood-burning fireplace sets the tone for relaxed gatherings and quiet evenings alike. The open-concept kitchen features granite countertops and flows seamlessly into the dining area, with French doors leading to a private stone patio - ideal for morning coffee or alfresco entertaining. The main level includes a spacious primary suite with en-suite bath, along with two additional BRs. Downstairs, the finished lower level offers additional space with two more bedrooms and a full bath, offering flexible space for guests, rec/playroom, or multi-generational living. For those seeking a professional setup, the town-approved home occupation designation allows for a separate entrance, two offices, and a waiting room - a turnkey solution for small business owners or remote professionals. With quick access to the Westport Library, Levitt Pavilion, and the town's vibrant dining & shopping scene, this property delivers both lifestyle and convenience. Nearby commuting options include the Metro North Railroad to NYC, Merritt Parkway, I-95. A rare opportunity to live and work in one of Fairfield County's most sought-after communities, or to find a home that offers private space for visitors or extended family. AVAILABLE FOR RENT AT $6,700/mo.

310 Main St, Westport

$10,500,000
7 Beds 7 Baths 24160355 MLS
Hidden along a private lane in Westport's Greens Farms neighborhood, this extraordinary 20-acre waterfront estate unfolds as one of the most remarkable shoreline settings ever offered. For more than 65 years, it has been held and enjoyed by the same family as a place to gather, unwind, and take in the ever-changing views across Sherwood Island Park and Long Island Sound. Surrounded by protected open space with no immediate neighbors, the property offers a rare sense of peace and privacy-reminiscent of the Lowcountry, the Hamptons, or Nantucket, a scale and atmosphere seldom found in Westport. Beautiful in every season, the setting also offers extraordinary birdlife and nature watching. Yet it remains moments to the Post Road, train, and town centers, and just one hour from Manhattan. A collection of residences and outbuildings is thoughtfully positioned across the land, including two circa 1940s three-bedroom guesthouses with sweeping water views, creating a true family compound where generations can come together while maintaining a sense of independence. Other structures offer flexibility for staff or future use. The grounds invite a lifestyle centered around the outdoors, with a tennis court, indoor pool, pool house, and formal gardens set within expansive lawns that stretch toward the water. Whether preserved, enhanced, or reimagined, this is a once-in-a-generation opportunity to shape a legacy estate-one that will be experienced and remembered for years to come.

4 Sherwood Island Ln, Westport

$4,495,000
6 Beds 7 Baths 24158946 MLS
Imagine a residence where every element has been considered for gracious living in stylish surroundings. This newly completed home by awardwinning Able Construction is set on a peaceful Coleytown estatearea street, framed by scenic land that enhances its sense of calm. A dramatic foyer with a woodaccented ceiling and millwork feature wall introduces interiors defined by creative decor, walls of glass, and exquisite lighting. The great room, anchored by a marble fireplace and French doors to the pool and patio, flows into the designer kitchen with a striking island, stone counters, custom cabinetry, Thermador appliances, and a beautiful and functional pantry. The dining room is a jewel, offering an elegant setting with illuminated shelving and views of the grounds. A quiet office and superb mudroom add daily convenience. A glasslined stair tower leads to sunfilled bedroom suites, beginning with the sublime primary suite set beyond double doors. An arched entry reveals a kingsized bedroom with balcony, two custom walkin closets, and a spalike bath with glass shower and distinctive vanity. The upper level also offers a laundry room with double washer and dryers and access to the finished thirdfloor bonus space. The lower level includes a fifth bedroom suite, recreation room, gym and media areas, and generous storage. Outside, the pool becomes the centerpiece for entertaining and relaxing at this designcentric showplace of style.

21 Lockwood Cir, Westport

$6,895,000
6 Beds 9 Baths 24156057 MLS
Introducing an exceptional new build from Simple Plan Home Builders, multiple HOBI Award winners known for iconic Westport homes. Just a short stroll to Compo Beach, this striking modern coastal retreat is privately set on a coveted cul-de-sac, blending luxury, light, and effortless living. Spanning four levels, this six-bedroom home features an airy layout with refined finishes throughout. The open-concept kitchen flows seamlessly into the main living spaces, highlighted by a statement fireplace. A glass-enclosed office offers privacy, while additional living and dining areas, a stylish scullery, and an oversized mudroom add everyday functionality. A dramatic pivot door opens to a gallery-style entry. Upstairs, the primary suite is a serene retreat with its own fireplace, dual walk-in closets, a dressing area, and a spa-like bath. Four en-suite bedrooms and a laundry room complete the second floor, while the top level offers a private sixth suite, office, and flexible open spaces. The walk-out lower level expands the home with walls of glass, a terrace, gym, bar, wine cellar, media/playroom, and additional office. Outside, a 16'x32' pool, multiple terraces, and a grilling area create effortless summer living, complemented by a three-car garage with EV charging.

8 Loretta Ct, Westport

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