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2 Judy Point Ln, Westport
$8,700,000
8 Beds ⋅ 10 Baths ⋅ 24159043 MLS
Set on over 3 private acres with sweeping water views, 2 Judy Point Lane is a remarkable Westport waterfront estate offering approximately 14,000 square feet of living space and a rare compound-style layout. The property consists of two substantial residences connected by a breezeway, creating exceptional flexibility for multi-generational living, extended guests, or a private guest house. Dramatic interiors feature soaring ceilings, expansive windows, and multiple stone fireplaces that frame the natural beauty of the surrounding landscape. Generous living and entertaining spaces flow effortlessly to outdoor terraces and landscaped grounds designed for both relaxation and gathering. The property includes a waterside pool overlooking the water, a private dock for boating, and a gated driveway set among mature plantings that enhance the estate's sense of privacy. Additional amenities include the potential for an indoor pool and spa, offering an opportunity to further elevate the home's resort-like experience. A rare offering combining scale, versatility, and waterfront living in one of Westport's most sought-after coastal settings.

2 Judy Point Ln, Westport

7 Mortar Rock Rd, Westport
$4,000,000
6 Beds ⋅ 8 Baths ⋅ 24178067 MLS
Welcome to 7 Mortar Rock, a thoughtfully designed living space. This stunning 6 bedroom transitional modern farmhouse showcases the exceptional craftsmanship and attention to detail that have made the Thomas Brothers Builders highly sought after. Perfectly blending beauty and functionality, this home is tailored to today's lifestyle while delivering timeless appeal. At the heart of the home is a spectacular chefs kitchen featuring quartz countertops and a large island with seating for four and an expansive dining area ideal for everyday living and entertaining. Sun filled spaces with nearly 10 foot ceilings on the main level creates and airy welcoming atmosphere throughout the home. Patio doors off the kitchen open seamlessly to a beautifully landscaped backyard with stone patio and built in gas fire pit. Ideally situated on a quiet cul-de-sac in one of Westport's most desirable locations this property offers the rare convenience of being just minutes from downtown shopping, dining, commuting options and Compo Beach.

7 Mortar Rock Rd, 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

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

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

2 Ledgemoor Ln, Westport
$2,700,000
5 Beds ⋅ 6 Baths ⋅ 24159517 MLS
Set on a quiet, private cul-de-sac very close to town and Winslow Park, this custom five-bedroom Colonial offers an exceptional opportunity for a new owner to leave their mark and add significant value. Designed with best-in-class materials and a thoughtfully planned layout, the home retains its gracious scale, natural flow, and exceptional character. Deferred maintenance has created the chance to elevate a well-loved property and return it to the signature splendor that defined it. The main level features a gourmet kitchen with Sub Zero & Viking appliances, stone counters, custom cabinetry and an adjacent breakfast room leading to a large family room, living room with fireplace, formal dining room, and two private offices with built-ins. French doors from most main floor rooms open to a balcony overlooking a heated Gunite pool and a large, level play area. The walkout lower level has a wall of French doors and is an exquisite poolside space that includes a fully-equipped wet bar, rec/game rm, gym and a full guest suite. Upstairs, the spacious bedroom layout provides comfort and flexibility for a variety of needs. Set on 1.16 +/- acres moments from shopping and recreation, the home is being offered as-is. ***Listing photos include a mix of current 2026 images and select photos from 2009 to illustrate the full potential of the property. Please note that showings are welcomed and booked by appointment, and no open houses are planned.***

2 Ledgemoor Ln, Westport

6 Imperial Lndg, Westport
$2,400,000
4 Beds ⋅ 4 Baths ⋅ 24156649 MLS
Tucked at the end of a quiet cul-de-sac in one of Westport's most convenient locations, 6 Imperial Landing offers the perfect blend of privacy, light-filled living, and effortless luxury. Thoughtfully designed and finished across three levels, this 4-bedroom, 3 full and 1 half bath home features well-proportioned rooms, an open layout, and an abundance of natural light throughout. Expansive windows bring the outdoors in, creating a bright and welcoming atmosphere in every space. The heart of the home is a chef's kitchen that flows seamlessly into the main living areas - ideal for both everyday living and entertaining. The primary suite is a true retreat, complete with dream walk-in closets and a newly renovated, spa-like bath designed for comfort and relaxation. The finished lower level adds exceptional versatility, offering a playroom, gym, kitchenette, and an additional bedroom or private office - perfect for today's flexible lifestyle. Set on beautifully landscaped grounds, the property features a waterfall, multiple patios, and a fully fenced backyard, creating a private oasis for relaxing and entertaining. A 3-car garage adds both convenience and functionality. With many recent upgrades throughout, this home is truly move-in ready - simply unpack and enjoy. A rare and special opportunity to experience the full Westport lifestyle, just minutes from the train, restaurants, Longshore, Compo Beach, Saugatuck Center, and downtown.

6 Imperial Lndg, Westport

4 Raymond Pl, Westport
$2,275,000
4 Beds ⋅ 5 Baths ⋅ 24180382 MLS
A beautifully refined Colonial offering 2,695 square feet of thoughtfully designed living space, plus an additional 485 square feet in the finished lower level. Privately sited on a .21-acre property bordering Birchwood Country Club, this home is located on a quiet street just moments from Saugatuck and downtown Westport. A charming front porch welcomes you into a home that was thoughtfully renovated and expanded in 2013, blending timeless design with modern comfort. Sun-filled interiors, quality craftsmanship, & an effortless floor plan create an ideal setting for both everyday living & entertaining. The heart of the home is the bright chef's kitchen, which opens seamlessly to the family room & overlooks the patio & fully fenced backyard, perfect for indoor-outdoor living. The residence features four bedrooms, four full baths, & one half bath, including a spacious primary suite with walk-in closets & a spa-inspired bath. Three additional bedrooms & two full baths complete the second floor. A generous mudroom adds convenience, while the finished lower level offers exceptional flexibility with a recreation room, full bath, & dedicated home office.Surrounded by mature landscaping & set in a peaceful, private setting, this property is just minutes from Saugatuck Center, Metro-North, & the shopping & dining of downtown Westport. A polished & sophisticated offering, it seamlessly combines classic architecture, modern livability, & an exceptional location. Welcome home!

4 Raymond Pl, Westport

50 Kings Hwy S, Westport
$1,890,000
3 Beds ⋅ 3 Baths ⋅ 24151092 MLS
Elegance, style, and thoughtful design converge in this stunning Westport residence, perfectly situated on a full acre of park-like grounds. Set back from the road, the property offers both privacy and convenience, just minutes from Saugatuck Center and downtown Westport. Inside, recent updates and tasteful renovations are showcased at every turn. The living room features a marble fireplace and serene views of the front and rear grounds, while a private office provides a tranquil retreat. The gourmet kitchen is a chef's dream, with a center island and seating, quartz countertops and backsplash, stainless steel appliances, a gas cooktop, pantry, and direct access to the patio. An open layout seamlessly connects the kitchen to a cozy sitting/breakfast area and a spacious dining and family room, complete with an accent fireplace and sliding doors overlooking the backyard. Upstairs, the primary suite is elegantly appointed with custom built-ins and a luxurious designer bath, complemented by two additional bedrooms and a beautifully finished second bath. The walk-out lower level offers versatile space for a recreation room, gym, or additional living area. Designed for both entertaining and everyday living, the home effortlessly blends indoor and outdoor spaces. Step outside to an exquisite patio with a sitting wall, pergola, and fire pit, opening onto an expansive backyard. This exceptional residence presents a rare opportunity to experience luxurious, comfortable living in one

50 Kings Hwy S, Westport

422 Riverside Ave, Westport
$1,800,000
5 Beds ⋅ 4 Baths ⋅ 24176205 MLS
A rare opportunity in the heart of Westport's coveted Saugatuck section. Set on 1.10 dry acres w/ beautiful views overlooking the Saugatuck River, this property known historically as Twin Hickory's offers a unique blend of history, charm, & future potential. Rich in character & dating back more than a century, the property traces its roots to the Franklin M. Raymond estate. Orig constructed as a barn in the late 1800s & thoughtfully converted into a residence in the 1930s, the home & accompanying barn remain a fascinating piece of Westport's architectural history. The existing residence offers approximately 3,345 sq ft of living space w/ 5 bdrms, 3.5 ba. Filled w/ warmth & character, the home presents endless possibilities for restoration, renovation, or reimagining. Set back from the road & accessed from both Riverside Ave & Cherry Ln, the property enjoys an exceptional setting just minutes from downtown Westport, the train station, award winning schools, parks, restaurants, shopping, & major highways. Builders & developers take notice. With half acre zoning, no wetlands, dual street frontage, beautiful river views, & a prime location, this property offers exceptional redevelopment potential & a rare opportunity to create something truly special. Whether your vision is to preserve a piece of Westport history, renovate an architecturally significant home, or build a custom dream residence, opportunities of this caliber & flexibility are increasingly rare.

422 Riverside Ave, Westport

12 Harbor Rd, Westport
$1,699,000
3 Beds ⋅ 2 Baths ⋅ 24099855 MLS
Nestled in the tranquil waterfront community of Saugatuck Shores, this home offers a private escape like no other. The open kitchen features a custom stone fireplace, sleek granite countertops and spacious island with abundant storage. The adjacent dining room has a charming bay window and seamlessly flows out to one of the 2 decks, perfect for al fresco dining and entertaining. The home includes a separate wing with two bedrooms and full bath, while the primary boasts a marble bath and sliding doors that open to the second deck. A private office and discreetly tucked away laundry complete this first level. The living room perched on its own level impresses with soaring ceilings, exposed wood beams and a cozy wood stove. The room is bathed in natural light and offers stunning views of the yacht club and the beautifully landscaped grounds . Enjoy membership at the Covlee Association granting access to a private marina, community beach and boat launch-ideal for paddle boarding and kayaking or simply enjoying the outdoors. All this is just minutes from the train, shopping, dining and schools. Plus the property is FEMA compliant. Perfectly positioned to embrace the best of Saugatuck, this home is a true sanctuary.

12 Harbor Rd, Westport

42 Kings Hwy S, Westport
$1,600,000
4 Beds ⋅ 3 Baths ⋅ 24138795 MLS
Step into this beautifully renovated modern home, where refined craftsmanship meets contemporary elegance. The grand foyer opens to a stunning living room with soaring double-height ceilings and a dramatic floor-to-ceiling stone fireplace. The gourmet chef's kitchen impresses with custom cabinetry, Viking appliances, quartz countertops, and a spacious eat-in area. Designed for effortless entertaining, the layout connects the kitchen, dining, and family rooms seamlessly. Upstairs, the luxurious primary suite features a large walk-in closet and a spa-like bath with a soaking tub and oversized shower. Three additional bedrooms offer generous storage, plus a versatile open workspace on the second floor. Enjoy year-round relaxation in the sunroom leading to a spacious deck and professionally landscaped backyard-perfect for outdoor gatherings. Conveniently located across from Birchwood Country Club and just 1 mile from the Westport Train Station.

42 Kings Hwy S, Westport

4 Davenport Ave, Westport
$1,351,175
3 Beds ⋅ 3 Baths ⋅ 24166299 MLS
Built in 1892, this designer-owned Victorian has been thoughtfully reimagined for modern living while preserving its original character and architectural integrity. Rooted in Westport's early history, the home reflects a seamless balance between timeless craftsmanship and refined contemporary design. Influenced by Scandinavian simplicity with subtle Japanese sensibility, the interiors are light-filled, calm, and intentionally curated. A south-facing orientation and skylights fill the home with natural light throughout the day. The main level offers effortless flow between living, dining, and kitchen spaces, along with a dedicated first-floor office. Three bedrooms and 2.5 baths include a serene primary suite with walk-in closet and ensuite bath featuring understated luxury details. A walk-up attic offers future expansion potential for a studio, guest suite, or additional bedroom, while the full basement provides generous storage and utility space. Covered front and rear porches, a private patio, and landscaped grounds extend the living experience outdoors. Extensive updates include a new roof, updated windows, central air, upgraded mechanicals, and enhanced insulation. Ideally located within walking distance to town, train, and river, this home offers a rare blend of convenience, history, and quiet modern luxury.

4 Davenport Ave, Westport

170 Imperial Ave, Westport
$1,350,000
3 Beds ⋅ 2 Baths ⋅ 24170051 MLS
Classic 3 Bedroom Colonial in the heart of Westport set on a picturesque level .21-acre. Full of potential, this home awaits your creative vision. Good flow and hardwood floors throughout. Flat, pretty property with city water and sewer available nearby. Detached one car garage. Ideally located just a short walk to the Saugatuck River, train, restaurants, shops, the Rowing Club, and coveted Saugatuck Center. Bike to Compo Beach, Longshore Park and golf course, Ned Dimes Marina, the Westport Farmers' Market, Salmon Park, The Levitt Pavilion, Westport Library, The Westport Country Playhouse, and downtown Westport. Home is being sold "as-is". Amazing opportunity for a buyer, designer, investor or builder who understands the great potential in this most sought-after neighborhood.

170 Imperial Ave, Westport

23 Bridge St, Westport
$1,058,500
4 Beds ⋅ 3 Baths ⋅ 24151653 MLS
Set in the heart of Westport, 23 Bridge Street offers a rare opportunity to own a character-rich home at a price point that is increasingly hard to find in town. Ideally located just minutes from the Metro-North Railroad train station, this property delivers exceptional everyday convenience for commuters and weekend explorers alike. The home borders over 1.5 acres of town-owned open space, a truly rare feature in this part of Westport so close to the center of town. An in-ground pool adds to the lifestyle appeal (pool photo is digitally rendered). Inside, the home is rich with antique barn-style character dating back to the early 1900s. Signature rooms include a dramatic great room with cathedral ceilings and a striking cobblestone fireplace wall, which flows seamlessly into an enclosed sunroom. At ground level, a walk-out offers exceptional versatility, featuring an additional bedroom, full bath, and partial kitchen. This property presents multiple paths forward: remodel in place, expand, or add an additional level. Plans are available for review, offering buyers a head start on unlocking the home's full potential. Surrounded by luxury shopping, renowned dining, and Westport's elevated lifestyle, this is a compelling opportunity to create long-term value in a premier location. Perfectly positioned minutes from Saugatuck Center, Compo Beach, Longshore Club Park, and downtown Westport-this is historical charm paired with modern convenience, 50 miles from NYC, Welcome Home!

23 Bridge St, Westport

201 Bradley Ln Unit 201, Westport
$1,015,000
2 Beds ⋅ 3 Baths ⋅ 24168481 MLS ⋅ Bradley Commons BLDG.
Welcome to Bradley Commons, a private gated enclave in the heart of Westport's vibrant Saugatuck neighborhood-just minutes to the train, Compo Beach, top-rated schools, and premier dining and shopping. This exceptional end-unit townhome features a bright open floor plan with hardwood floors, high ceilings, and abundant natural light. The chef's kitchen offers granite countertops, gas range, French door refrigerator, large pantry, and breakfast bar, flowing seamlessly into the dining area with sliders to a private deck-ideal for entertaining. The sun-filled living room with eastern exposure includes a gas fireplace, powder room, and generous closet space. Upstairs, the spacious primary suite boasts walk-in closets and a luxurious ensuite bath with double vanity and oversized shower. A second en-suite bedroom and upper-level laundry provide comfort and convenience. The versatile lower level is perfect for a guest suite, office, gym, or den, with direct access to a private patio and yard, plus ample storage and entry to the attached one-car garage. Beautifully maintained with professional landscaping and abundant guest parking, Bradley Commons offers turnkey living in an unbeatable location.

201 Bradley Ln Unit 201, Westport

503 Bradley Ln Unit 503, Westport
$999,000
2 Beds ⋅ 3 Baths ⋅ 24157132 MLS ⋅ Bradley Commons BLDG.
Welcome to Bradley Commons - a private, gated enclave in the heart of Westport's coveted Saugatuck neighborhood. Originally presented as the model home for the community, this distinguished end-unit residence showcases elevated finishes, thoughtful architectural detail, and a premier setting within the complex. Just a five-minute walk to the Metro-North station, the home offers effortless access to Manhattan while embracing Westport's coastal lifestyle - ideal as a full-time residence or refined weekend retreat. A gracious, light-filled entry framed by windows on two sides introduces a grand, beautifully designed staircase that serves as an elegant focal point. The main level features 9+ foot ceilings, rich hardwood floors, and an open-concept layout designed for modern living. The family room with gas fireplace flows seamlessly to the dining area and private deck - perfect for entertaining or quiet evenings at home. The chef's kitchen is both refined and functional, offering a generous peninsula with seating, stainless steel appliances, custom cabinetry, and a separate pantry - all overlooking a private, manicured green backyard that provides a serene natural backdrop.

503 Bradley Ln Unit 503, Westport

202 Bradley Ln Unit 202, Westport
$880,000
2 Beds ⋅ 3 Baths ⋅ 24136555 MLS ⋅ Bradley Commons BLDG.
Nestled in a private gated enclave, this sophisticated Westport townhouse blends timeless elegance with modern comfort. Enjoy a coveted lifestyle with walkable access to Metro-North and Saugatuck's vibrant dining scene. Bradley Commons is a beautifully maintained, gated condominium complex offering an effortless lifestyle. Rich millwork, gleaming hardwood floors, large windows and an attached garage elevate this pristine home's appeal. The custom granite kitchen boasts premium stainless steel appliances and flows seamlessly into open-concept living and dining rooms, anchored by a cozy fireplace and glass doors leading to a sun-kissed deck. Two luxurious en-suite bedrooms. The first is the sun-filled primary suite, which has dramatic double doors, a tray ceiling with gorgeous mouldings, two fitted closets and a large spa-like bath with double vanity and glass shower. 2nd bedroom w/cathedral ceiling & full bath. Convenient bedroom-level laundry. The walk-out lower level offers a spacious family room perfect for entertaining or relaxing, and there is a space used as a convenient home office. Recent upgrades include new central air, heating, and hot water systems that are all less than 1.5 years old. Minutes from Compo Beach's scenic shoreline and Longshore Club Park's golf, tennis, sailing and marina amenities, the Saugatuck Rowing Club and beautiful river access, this residence offers the best of Westport living. A rare opportunity for refined coastal charm and convenience.

202 Bradley Ln Unit 202, Westport

230 Saugatuck Ave Unit U-6, Westport
$740,000
2 Beds ⋅ 3 Baths ⋅ 24120074 MLS ⋅ Indian River Green BLDG.
Welcome to Indian River Green! Located in a private community of 20 Townhouse Style Units in the desirable Saugatuck neighborhood with walk to train convenience. Beautiful Open Concept design with custom kitchen which features skylights, vaulted ceiling, corian countertops and tile backsplash. The dining room has built -in bookcases and opens to the spacious Living Room which boasts a fireplace, built-ins, vaulted ceiling and sliders that access your private patio. Private half bath with laundry along with sunlit entry foyer complete the main level. As you walk up the light and bright staircase you are greeted to the Primary Bedroom Suite which showcases a high ceiling, sliders to a wonderful upper balcony/deck and beautiful full bath. The second Bedroom has a vaulted ceiling with an ensuite full bathroom. A wrap around entry porch and private 1 car garage complete this attractive home. Just minutes to the heart of downtown shopping and beaches with easy access to the train and I-95. Enjoy all that the Westport lifestyle has to offer. The perfect place to call home!

230 Saugatuck Ave Unit U-6, Westport

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.

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