Refine Search
Sort by
24 Blue Ribbon Dr, Westport
$2,400,000
4 Beds ⋅ 4 Baths ⋅ 24168290 MLS
**PLEASE SUBMIT ALL OFFERS BY TUESDAY MAY 5TH AT NOON** Classic charm meets modern comfort in this beautifully updated 4-bedroom, 3 full and 1 half bath home, set in one of Westport's most loved walking neighborhoods-just minutes to top schools, vibrant downtown, and an easy hour to NYC. A bright, spacious eat-in kitchen is the heart of the home, opening to a back deck for effortless indoor-outdoor living and flowing into a sun-filled family room with vaulted ceilings and custom built-ins-perfect for gathering or unwinding. Upstairs, the primary suite is a true retreat, featuring a luxe bath with soaking tub, heated floors, heated towel bars, and generous walk-in closets. All baths are beautifully updated, and the home offers incredible flexibility with a first-floor office, elegant living room, and a bonus sunroom ideal as a playroom, lounge, or creative space. Step outside and you'll find your own private resort-a gorgeous heated pool with a chic cabana, made for summer entertaining, long weekends, and effortless staycations. A finished lower level adds even more space to spread out, making this home as functional as it is inviting.

24 Blue Ribbon Dr, Westport

13 River Ln, Westport
$2,400,000
4 Beds ⋅ 4 Baths ⋅ 24150512 MLS
Set within one of the area's most coveted neighborhoods, this exceptional colonial residence embodies timeless elegance & gracious Southern charm. Beautifully maintained & thoughtfully designed, the home offers an inviting sense of warmth & refinement that is felt from the moment you arrive. Manicured grounds frame the property in privacy and tranquility, creating a serene backdrop for daily living. The pool, perfectly scaled & quietly elegant, enhances the setting-ideal for peaceful afternoons, relaxed gatherings, & unhurried summer evenings. Inside, generously proportioned rooms & a flowing layout create a home that lives as beautifully as it entertains. A private home office provides a quiet retreat for work or reflection, while a dedicated guest suite offers visitors comfort and privacy, allowing them to feel truly at home. The heart of the residence is the chef's kitchen, thoughtfully appointed with premium appliances & refined finishes, where everyday moments & special occasions unfold with ease. Throughout the home, classic craftsmanship & attention to detail create a sense of enduring quality & understated luxury. Outdoors, the bluestone patio offers a private & inviting extension of the living space-perfect for alfresco dining, evening conversation, or simply enjoying the peaceful surroundings. Balancing tranquility with convenience, this distinguished property is more than a home-it is a lifestyle defined by grace, comfort, & timeless appeal! Welcome Home!

13 River Ln, Westport

30 Cavalry Rd, Westport
$2,375,000
4 Beds ⋅ 5 Baths ⋅ 24154690 MLS
Stunningly re-imagined & rebuilt, designed for flexibility & privacy Westport residence offers TWO distinct living levels w/bdrm suites on both floors. Ideal for today's evolving lifestyles. Main-level living is complimented by a private lower-level retreat, perfect for guests, home offices, or extended living needs, all set on beautiful, serene property.Prepare to be wowed by this 4-bedroom, 3 full and 2 half bath masterpiece, set on over 2 acres of private, picturesque grounds with plenty of room for a pool.This home is fully equipped with the latest in smart home technology. The open-concept floor plan centers around a to die for chef's kitchen w/top-of-the-line appliances & designer finishes-that flows seamlessly into the living room w/a cozy fireplace, stylish bar, & show-stopping wine display. Expansive sliders open to a sun-soaked deck w/panoramic views of your sprawling backyard extending all the way to the Saugatuck River!.The luxurious primary suite is a private retreat, featuring a spa-inspired bath w/radiant heated floors, fireplace,& generous walk-in closet.A dramatic spiral staircase leads to an intimate office loft, while sliding doors open to a deck w/breathtaking vistas. Second ensuite bedroom, half bath, & welcoming foyer complete the first floor.On the lower 2 add'l bdrms share a jack & jill bath. You'll also find a laundry room, powder room, and a spacious family room with frplc.Finished 3rd level w/endless possibilities for a gym, office or rec room

30 Cavalry Rd, Westport

5 Farnham Ct, Westport
$2,351,009
5 Beds ⋅ 5 Baths ⋅ 24171058 MLS
Timeless elegance meets modern comfort in this stunning 1936 brick Colonial, beautifully updated while preserving the warmth, character, and craftsmanship of its vintage roots. Set in one of Westport's most desirable coastal locations, this 5-bedroom, 4.5-bath antique home is filled with architectural detail and storybook charm at every turn. Graceful arched doorways, a curved staircase, detailed moldings, leaded decorative windows, cozy window seats, original crystal and brass hardware, and three fireplaces create an atmosphere that feels both refined and deeply welcoming. Each room has been thoughtfully refreshed with an eye toward comfort, function, and timeless style, while honoring the home's original soul. Outdoor living is equally inviting, with lovely gardens, a spacious patio, a built-in grill, and a firepit perfect for relaxed evenings under the stars. Enjoy an exceptional Westport lifestyle just moments from Compo Beach, Longshore Club, the train, and Saugatuck's beloved restaurants and shops. The result is a rare blend of old-world beauty and updated livability - a home that feels elegant yet warm, sophisticated yet inviting. 5 Farnham Court is a truly special Westport residence for those who appreciate character, quality, location, and enduring design.

5 Farnham Ct, Westport

41 Richmondville Ave Unit Duplex 2, Westport
$2,350,000
2 Beds ⋅ 3 Baths ⋅ 24090155 MLS ⋅ The Mill Westport BLDG.
Welcome to Residence Duplex 2 at The Mill Westport, a spectacular unit with spacious rooftop deck which offers high-end luxury living with all the amenities of a fine custom home in the heart of downtown Westport. With a concierge on-site and approximately 10,000 square feet of spectacular interior and exterior amenity spaces such as The Great Room & Cafe, Pool, Health & Wellness Center, Patio & Rooftop Deck, residents will enjoy carefree, 5-star living. The 31 residences feature large windows, open floor plans, and light wood floors. Their refined details include a large waterfall-edged kitchen island, linear gas fireplaces, Sub Zero and Wolf appliances, full-size washer/dryers, and up-to-date bathrooms with radiant heated master bath floors. A variety of floor plans are available to meet the unique needs of discerning buyers seeking a bespoke lifestyle, with some offering spectacular terraces. All homeowners have access to heated or covered parking. Set in a tranquil, residential neighborhood within walking distance of downtown Westport's many shops, restaurants, activities and close to beaches and commuting options to New York City. The redevelopment and adaptation of The Mill Westport into a luxurious residential property is being undertaken by Coastal Luxury Homes and Gault Family Companies, two Westport-based firms with a proven track record of surpassing the highest expectations.

41 Richmondville Ave Unit Duplex 2, Westport

86 Maple Ave S, Westport
$2,345,000
4 Beds ⋅ 4 Baths ⋅ 24148769 MLS
Renovated, refreshed, and move-in ready, this sunfilled Greens Farms gem offers the perfect blend of charm, style, and modern comfort. Set on a beautifully landscaped, level acre with gunite pool and expansive patio, the outdoor living experience is exceptional. Fresh paint inside and out, a new pergola, and thoughtful landscaping create irresistible curb appeal. Step inside and feel instantly at home. The inviting Dining Room and elegant Living Room with fireplace flow seamlessly toward a private office. The updated eat-in kitchen features gleaming new countertops and opens directly to the dramatic Great Room, where soaring ceilings and French doors frame views of the tiered patio, lush grounds, and pool. Upstairs, you'll find four bright bedrooms and two full baths. The spacious Primary Suite is a true retreat, complete with a sitting room, two walk-in closets, a well appointed bath, and striking vaulted ceilings. The heated lower level offers flexible bonus space, ideal for a playroom, gym, or creative studio. Two car garage with new mudroom. A home that feels as good as it looks. You're going to love it.

86 Maple Ave S, Westport

11 Dogwood Ln, Westport
$2,337,500
4 Beds ⋅ 3 Baths ⋅ 24098937 MLS
Experience the best of Westport living in this stunning Mid Century Modern residence set on 1.87 prime acres in the heart of town. This is all about the property! Tucked away on a beautifully landscaped property, this 4-bedroom home offers the perfect blend of privacy, modern design, and everyday convenience. Inside, expansive windows bathe the open living spaces in natural light, with soaring ceilings and a seamless indoor-outdoor flow. The spacious kitchen, elegant dining area, and inviting living room create an ideal setting for entertaining. Retreat to a serene primary suite with views of the picturesque grounds. Step outside to your own private oasis featuring a sparkling in-ground pool, lush lawns, and mature plantings- fully fenced and perfect for relaxation or play. Enjoy the combination of public water, and town sewer. Located minutes from downtown shopping, restaurants, beaches, top-rated schools, and the train. A truly exceptional offering in one of Westport's most sought-after locations.

11 Dogwood Ln, Westport

24 Burr School Rd, Westport
$2,325,000
5 Beds ⋅ 5 Baths ⋅ 24172330 MLS
Tucked away towards the end of a quiet cul-de-sac in a prime central Westport location, this beautifully updated home offers the perfect blend of privacy, convenience, and lifestyle. Set on 1.05 acres and just moments from town, close to schools, shopping, and commuting options, this five-bedroom residence is designed for both everyday living and effortless entertaining. The heart of the home is the open kitchen featuring a large sunny dining area, center island, breakfast bar and exceptional flow into the family room-ideal for gatherings and modern living. A charming living room with a warm and inviting fireplace seamlessly flows into the private formal dining room, creating elegant spaces for more intimate gatherings. This residence includes 4.5 baths and a thoughtfully designed layout throughout. The luxurious primary suite is a true retreat, complete with an adjacent office/dressing/make-up area or baby's room-exceptional custom closets-including a spacious walk-in with built-ins-and a spa-inspired bath with jetted tub. The finished lower level, with private room with large closet, open space and full bath, provides ideal flexible space for storage, playroom, or gym. Outdoors, enjoy a private oasis with an in-ground pool framed by beautiful stone walls and mature plantings. Set back from the road, the property offers both tranquility and seclusion while remaining close to all that Westport has to offer.

24 Burr School Rd, Westport

9 Marsh Rd, Westport
$2,325,000
4 Beds ⋅ 3 Baths ⋅ 24162314 MLS
Don't miss this rare opportunity to wake up every day to the serenity of breathtaking water views & the charm of coastal living at 9 Marsh Rd, nestled in the coveted Saugatuck Shores of Westport. Perfectly positioned on a private 0.23-acre lot within a tranquil waterfront community, this FEMA-compliant home has been meticulously remodeled to offer modern elegance & everyday comfort. Step inside to find an open-concept layout featuring 2 cozy fireplaces, gleaming hardwood floors, a bright, updated eat-in kitchen complete w/ a spacious island, walk-in pantry & top-of-the-line appliances. With 4 bedrms & 3 full bths, this home provides plenty of room for family & guests. The primary suite is a true retreat, w/ an oversized walk-in closet & a spa-like bathroom w/a soaking tub, stall shower & double sinks. The heart of the home is the sunlit family room, where soaring ceilings & walls of windows frame sweeping water views. Step out onto the expansive Ipe deck w/sleek marine railings, the perfect spot for al fresco dining, birdwatching, or admiring stunning sunsets. The private, fenced yard features an outdoor shower, a whole-house generator, a 2-car garage, & enclosed storage. Embrace the coastal lifestyle w/ ease: stroll to nearby Canal Beach, launch your kayak or paddleboard, or set sail from the Cedar Point Yacht Club, a short walk from the home. And, when you're ready for a change of pace, Westport's vibrant downtown, gourmet dining, & boutique shopping are just minutes away.

9 Marsh Rd, Westport

368b Wilton Rd, Westport
$2,310,000
4 Beds ⋅ 3 Baths ⋅ 24130527 MLS
*THANK YOU FOR YOUR INTEREST: Seller has requested highest and best offers by Monday 3/9/26 at 3pm* Set on a tranquil acre on a three home spur back and off the road, this meticulous, move-in ready Colonial with a sparkling gunite pool & spa is the home you have been waiting for. The prime Westport location offers convenience to commuting options, town centers, schools, beaches & more. The professionally-landscaped property w/specimen plantings & artisanal stonework is the perfect backdrop for this classic Colonial. The home's interior was freshly painted in a neutral palate and the hardwood floors were just refinished. The front-to-back LR w/ the 1st fireplace has three exposures, filling it with light. The DR is ready to host memorable occasions. The custom gourmet kitchen has fresh white cabinetry, stone counters, Sub Zero & Wolf appliances including double wall ovens & gas cooktop, walk-in pantry and an effortless flow to the captivating brkfst rm w/French doors to both a deck & exquisite sun rm. The family rm is a signature highlight w/ skylit cathedral ceil, 2nd fpl, wet bar & French doors. Upstairs, the expanded primary suite has a king-sized BR, two large walk-in clsts & a unique, luxurious octagonal bth w/htd flr, glass shower & hydro tub. The spacious BRs access an updated full bath. Finished LL rec/play/gym space w/office plus lrg storage rm in addition to very spacious attic. The resort-style pool area has a waterfall spa, built-in grill/bar. Generator, 2c gar.

368b Wilton Rd, Westport

117 Weston Rd, Westport
$2,300,000
5 Beds ⋅ 4 Baths ⋅ 24155788 MLS
Set in a serene natural setting, this custom Colonial offers a comfortable layout with a balance of privacy and convenient access to top-rated schools, shopping, and dining. The main living spaces are bright and inviting, with generous windows that frame views of the surrounding greenery and create an easy flow for everyday living and entertaining. Upstairs, four bedrooms are located on one floor, offering a practical and cohesive bedroom arrangement. The top level features an extra room that can serve as a bedroom, home office, playroom, or media room-flexible to suit a variety of needs. Outdoors, enjoy a private yard retreat with a heated gunite pool and spa, surrounded by mature landscaping for a peaceful setting ideal for relaxing or hosting. This property delivers a tucked-away feel while remaining close to modern conveniences.

117 Weston Rd, Westport

5 Minard Dr, Westport
$2,300,000
5 Beds ⋅ 4 Baths ⋅ 24129810 MLS
Set in the coveted Saugatuck Shores enclave, this 5BR/4BA Colonial offers timeless design & modern amenities for today's living. The open floor plan includes a sun-filled living room with gas fireplace & dining area, highlighted by the heart of the home-a chef's dream kitchen with abundant storage, granite countertops, Sub-Zero refrigerator & 2 refrigerator drawers, Wolf six-burner double oven, microwave/convection, Miele espresso machine & kitchen island. The well-planned first floor also features a fifth bedroom with convenient access to a full bath w/radiant heated flrs, perfect for use as a den, study, guest room, or for one-level living. French doors open to a serene patio & private yard, ideal for dining, entertaining, or quiet evenings surrounded by nature. On the second level, the private quarters are anchored by a tranquil primary suite with fireplace, walk-in closet, & spa-bath w/radiant heated flrs. Three additional bedrooms with generous closets are complemented by two full baths, including one en-suite. A laundry room & pull-down attic with generous storage round out this level. Brazilian Chestnut hardwood floors extend throughout, adding warmth & elegance. Energy-efficient systems enhance comfort. Just minutes to town, train, and I-95, this is the ultimate Westport coastal retreat, blending everyday comfort with refined sophistication for today's modern lifestyle.

5 Minard Dr, Westport

18 River Ln, Westport
$2,275,000
5 Beds ⋅ 6 Baths ⋅ 24120643 MLS
Update: Offers are due at 6pm on Monday June 15th. Set along one of Westport's most coveted stretches of the Saugatuck River, 18 River Lane is a timeless 1939 English Manor offering a rare blend of architectural character, waterfront serenity, and exceptional potential. Privately sited on 1.38 picturesque acres with sweeping river views and mature landscaping, this six-bedroom residence embodies the elegance and craftsmanship of a bygone era. Rich in period details, the home features graciously scaled rooms, distinctive architectural elements, and an inviting floor plan designed for both comfortable living and entertaining. The versatile layout includes a full walk-out lower-level apartment/studio, ideal for guests, extended family, a home office, creative workspace, or au pair accommodations. The spectacular riverfront setting provides a sense of tranquility and privacy while remaining just minutes from downtown Westport, the train, beaches, and top-rated schools. An extraordinary opportunity exists to further expand the estate, as the adjacent 1.13-acre building lot is also available for purchase, creating the potential for a remarkable compound or future development opportunity. A truly rare offering where historic charm, waterfront living, and limitless possibilities converge.

18 River Ln, 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

21 Woods Grove Rd, Westport
$2,250,000
4 Beds ⋅ 4 Baths ⋅ 24146391 MLS
Nestled on the freshwater banks of the Saugatuck River, this extensively renovated/refreshed custom-built riverfront beauty sits high and dry with assumable flood insurance of approx. $1400 a year. Experience the river deck complete with swim ladder, perfect for a kayak launch or swim, memorable entertaining or simply enjoy the quietude of this picturesque & peaceful escape. Tall ceilings & light-filled rooms, accented by wide doorways & beautiful hardwood floors, welcome you into the sunny Living and Dining Rooms, & the newly updated Chef's Kitchen. The Family Room opens to the large stone terrace with pergola which overlooks the River just beyond the good sized, flat backyard. Upstairs you will find 9' ceilings through-out, beginning in the open common area that accesses the Primary Bedroom with 2 walk-in closets & brand new lux Bath, plus 3 additional Bedrooms- one with private Bath & two sharing a Jack & Jill Bath. The finished 3rd floor has flexible space for an office, playroom or gym, plus an attic for storage. Improvements include the total freshly painted interior, new Primary Bath & Powder Room, extensive Kitchen updates, new fireplace, new lighting, new AC, all floors refinished, garage with Tesla charger & so much more. On a quiet in-town cul-de-sac with a private association "swimming hole" at the end of street and a short walk to the center of downtown Westport.

21 Woods Grove Rd, Westport

55 Compo Rd N, Westport
$2,236,055
2 Beds ⋅ 3 Baths ⋅ 24173921 MLS
There is a quality of light that artists seek-the kind that pours through the soaring atelier window of the great room in this updated vintage home. Once the studio of Norman Mason, each aspect of its design was in service to his art. Set on 1.26 acres overlooking Winslow Park, this charming home carries its history lightly and beautifully. The dramatic great room is anchored by an oversized fireplace, newly refinished hardwood floors and a special light that imbues the space with a certain atmosphere whether holding a dinner party for 20 or relaxing alone with a good book. The kitchen has been thoughtfully updated for how we live now-new appliances, clean lines, proper workspace, a walk-in pantry. The library offers a quiet place to work from home. The first floor primary suite is its own private world, serene and removed, with a generous walk-in closet and full bath that feels both practical and indulgent. Guests have a separate wing with room to settle in, while additional space throughout the property invites expansion, reinvention or room to grow. Step outside and the story continues. The grounds are lush and unhurried. The perennial gardens and flat sweep of lawn provide a living landscape that changes with the seasons. Moments from the center of town, theater, shops and restaurants, the particular rhythm of a place that is sophisticated and yet part of a neighborhood.

55 Compo Rd N, Westport

4 Burr Farms Rd, Westport
$2,200,000
4 Beds ⋅ 3 Baths ⋅ 24129625 MLS
Welcome to this captivating expanded cape retreat in the heart of Westport on a sought after, centrally located, walk to school street. Every aspect speaks the language of artistry and elevated attention to detail. This custom built sanctuary is an artist's haven nestled admist nature's finest tapestry. The residence boasts a thoughtfully designed living space harmoniously arranged on a picturesque one acre canvas. The husband and wife team has effortlessly married the timeless interior elegance of French-inspired craftsmanship with the serene exterior beauty reminiscent of Monet's gardens. Each room is designed with a commitment to detail, offering a beautiful blend of classic design and modern comfort. The bespoke interiors are crafted to evoke a sense of refined sophistication with artisan touches and quality finishes throughout. The piece de resistance is the magnificent primary suite. Not just offering breathtaking views from the balcony of the owner's own realization of Monet's garden, but an alice in wonderland entrance to a sitting room, bedroom with soaring ceilings, gas fireplace and double walk in boutique style closets. Two artistically accented bedrooms sharing a vintage hall bath rounds out the second level living accenting the Parisian inspired, effortlessly chic and timeless primary ensuite. The fourth bedroom resides on the first level boasting two beds hidden in custom cabinetry that currently serves as an office. Wander your way into this wonderland!

4 Burr Farms Rd, Westport

234 Wilton Rd, Westport
$2,199,120
4 Beds ⋅ 4 Baths ⋅ 24157114 MLS
Wilton Road places you minutes from town and the shoreline. At 234, convenience and privacy coexist. A turn onto a side lane and a set-back approach behind mature trees create a setting that feels distinctly separate from the street. Originally built in 1884, the home has been fully renovated and thoughtfully expanded. A 2024 addition reshaped the main level, enlarging the kitchen and introducing a newly constructed family room anchoring the home. Tall ceilings, open sight lines, and abundant natural light create a sense of volume rarely found in homes of this era. It lives larger than its footprint. The kitchen centers around an oversized island, with a cozy banquette tucked into the corner. A beverage bar and architectural wine display are seamlessly integrated. The flow from kitchen to family room to dining is open and intuitive. Sliders extend to an expansive stone patio with a built-in grill station and fireplace, creating an easy transition between indoors and out. An expansive lawn invites play, set within the safety of the private backyard. Upstairs, the primary suite features a private sitting room, boutique-style dressing room, and a light-filled bath with a soaking tub and glass-enclosed shower. Additional bedrooms are carefully arranged, including a private suite, offering flexibility for guests. Historic at its core and thoughtfully expanded for today. Set where Westport unfolds at your doorstep, and designed with the scale to fully enjoy it.

234 Wilton Rd, Westport

60 Sylvan Rd N, Westport
$2,199,000
4 Beds ⋅ 4 Baths ⋅ 24126100 MLS
This 4-bedroom, 3-full, 1-half bath Colonial offers 3,430 sq ft of thoughtfully designed living on a 1.01-acre lot in Westport's Old Hill neighborhood. The main-level primary suite features a spa-inspired bathroom, walk-in closet, and abundant natural light. A chef's kitchen with custom cabinetry opens to spacious living and dining areas, creating an open flow for entertaining or daily living. Additional living spaces include a home office, family room, and flex room adaptable for media, gym, or recreation. Outdoor amenities include a private yard, patio, and mature landscaping. Features include a security system, ample storage, premium finishes, and high ceilings throughout. Located 0.5 miles from Longshore Club Park, 0.6 miles from Kings Highway Elementary School, 1.2 miles from Staples High School, and 1.0 miles from Westport Center and Compo Acres Shopping. Nearby restaurants, cafes, and local shops within 0.5-1.0 miles, with easy access to I-95. Includes flexible floor plan, vaulted ceilings,and multiple living spaces. Ideal for varied living arrangements, work-from-home setups, and entertaining.

60 Sylvan Rd N, Westport

4 Cardinal Ln, Westport
$2,150,000
4 Beds ⋅ 4 Baths ⋅ 24172650 MLS
Welcome to 4 Cardinal Lane ~ a beautifully expanded and thoughtfully updated home set on two private, level acres in one of Westport's most desirable cul-de-sac neighborhoods. Originally built in 1964 and enhanced with a significant 2015 addition, this 4-bedroom, 3.5 bath residence offers over 4,100 square feet of versatile living space designed for both everyday comfort and effortless entertaining. The layout blends classic charm with modern functionality, featuring sun-filled living spaces, a wood-burning fireplace, an office and seamless flow throughout. The standout "bungalow" addition creates a one-of-a-kind experience, complete with a bar and direct access to the patio, perfect for hosting gatherings year-round. Upstairs, the primary suite offers a peaceful retreat with a walk-in closet and well-appointed bath, while three additional bedrooms provide flexibility for family and guests. A partially finished basement adds more usable space, including a dedicated gym area. Outside, the expansive backyard is a rare find offering endless potential for outdoor living, play, or future enhancements. The patio extends the home's entertaining footprint, creating an ideal setting for dining and relaxing. Just minutes from Westport's top-rated schools, beaches, golf course, tennis and pickle courts, town center, and train this is a unique opportunity to own a spacious, move-in ready home with exceptional indoor-outdoor living and standout entertaining spaces in a coveted setting.

4 Cardinal Ln, Westport

17 Clover Ln, Westport
$2,150,000
5 Beds ⋅ 4 Baths ⋅ 24148164 MLS
SOPHISTICATED CONTEMPORARY RETREAT - CLOVER LANE Exciting opportunity to own a beautifully reimagined Contemporary home on an expansive 1.27 acres at the end of a peaceful Westport cul-de-sac. This thoughtfully renovated 3000 square-foot residence features open concept living areas with streaming natural light and captivating views of mature lush greenery. A sleek, designer kitchen serves as the heart of the home with contemporary cabinetry, premium countertops, and curated finishes. Seamless indoor-outdoor flow creates an ideal environment for both intimate gatherings and group entertaining. Highlights include: * Dramatic floor-to-ceiling windows framing natural beauty * Soaring ceilings enhancing spaciousness * Thoughtfully renovated bathrooms with modern fixtures * Multiple access points to outdoor terraces and patios * Clean architectural lines celebrating mid-century heritage with contemporary sophistication * The generous, private grounds offer endless possibilities while recent updates ensure modern comfort and efficiency. City water, Natural Gas and City Sewer complete this unique residence. Enjoy tranquil living surrounded by nature's beauty with ultimate privacy, plus prime location minutes from Westport's beaches, top schools, vibrant downtown, and Metro North train service. A rare opportunity to embrace sophisticated contemporary living on substantial acreage in coveted Westport.

17 Clover Ln, Westport

10 Reimer Rd, Westport
$2,125,000
4 Beds ⋅ 4 Baths ⋅ 24152179 MLS
Thank you for your interest , sellers are respectfully requesting highest and best offers by 3/22 @5pm . stunning 5-bedroom, 3.5-bath home offers beautifully updated living space on a level 1-acre lot at the end of a sought-after cul-de-sac, just minutes to top-rated schools, beaches, & the many amenities of Westport. Flooded w/ natural light from vaulted ceilings & skylights, the chef's kitchen features a Wolf range & an oversized island ideal for gathering and opens seamlessly to a comfortable living area w/ a fireplace & a wet bar. French doors lead to a TimberTech deck overlooking the private, level backyard, creating effortless indoor-outdoor living. Freshly finished hardwood floors run throughout the home, complementing the bright interiors. The dining room showcases a wall of windows. The family room includes built-in bookshelves/entertainment center, a second fireplace, half-bath and offers access to a bluestone patio, another inviting space to relax or entertain. The primary suite is exceptionally spacious w/ a vaulted ceiling, dual walk-in closets, and a luxurious bath, along with an adjacent bedroom w/ Belvedere balcony, currently used as an office, which could also function as a nursery. 3 additional well-appointed bedrooms, including one ensuite, provide comfort and privacy for family or guests. The basement includes a wine cellar & full-height unfinished space, offering exceptional storage & potential for future expansion. Freshly painted on the exterior

10 Reimer Rd, Westport

5 Willow Walk, Westport
$2,121,000
4 Beds ⋅ 3 Baths ⋅ 24140916 MLS
SELLER IS REQUESTING HIGHEST AND BEST OFFERS BE SUBMITTED BY SUNDAY, NOVEMBER 23RD AT 8PM. Nestled on a quiet, picturesque cul-de-sac, this beautifully maintained home enjoys a prime Westport location-just steps from Staples High School and Bedford Middle School, with direct gated access for ultimate convenience. A short drive brings you to all the amenities Westport has to offer, from shopping and dining to beaches and vibrant town life. Set on a private, level acre, the outdoor spaces are truly exceptional. An expansive deck, dedicated fire-pit area, and fully fenced backyard create the perfect setting for entertaining, play, and year-round enjoyment. Inside, the classic and highly desirable layout features a welcoming two-story foyer, a dramatic great room with exposed beams, vaulted ceilings, and a wood-burning fireplace, an eat-in kitchen with a cozy sitting area, and an oversized dining room ideal for gatherings. The second floor includes all four bedrooms, highlighted by a spacious primary suite with vaulted ceilings, a walk-in closet, and a serene spa bath. The finished lower level offers flexible space for a playroom, gym, office, or all of the above-plus abundant storage. A rare combination of location, layout, and lifestyle-this one won't last.

5 Willow Walk, Westport

342 Greens Farms Rd, Westport
$2,100,000
4 Beds ⋅ 5 Baths ⋅ 24122231 MLS
From city politics to select suburb - this home offers you the desired change with NYC still within reach. Nestled in Westport's prestigious Greens Farms enclave, this Victorian estate blends timeless character with modern sophistication. Originally built in 1861 and expanded in 2008, it offers over 6,600 sq ft of refined living space on 2.02 serene acres. Enjoy lush lawns, a private pool, outdoor kitchen, and hot tub-perfect for relaxing, entertaining, or quiet reflection. Inside, historic charm meets modern comfort with original fireplaces, soaring ceilings, and exquisite millwork. The gourmet kitchen, anchored by a large island, opens to an expansive great room and includes a butler's pantry with a walk-in commercial refrigerator. The lower level features arched doorways, natural light, and flexible space for a gym, playroom, office, or guest suite. A luxurious bar and theater-style entertainment area with mahogany tray ceilings adds sophistication, while a rooftop balcony makes every evening special. A six-car garage plus rear access for two more vehicles ensures convenience. Just minutes to Metro-North, I-95, beaches, and Westport's amazing restaurants and shops, this home offers the perfect blend of New England charm and modern luxury-all with NYC within easy reach.

342 Greens Farms Rd, Westport

33 Pequot Trl, Westport
$2,100,000
5 Beds ⋅ 5 Baths ⋅ 24120910 MLS
Set on a 1-acre lot in Old Hill, this 5-bedroom, 4.1-bath Colonial offers 4,035 sq ft of open, light-filled living space. The main level features a welcoming foyer, formal living and dining rooms, and a family room with large windows overlooking the landscaped backyard. The kitchen includes a gas cooktop, wall oven, microwave, refrigerator, freezer, ice maker, and dishwasher, opening seamlessly to the deck with scenic views. The primary suite provides a spacious bedroom and modern en-suite bath. Hardwood floors extend throughout the main living areas. Three fireplaces add warmth and charm. Finished lower level with walk-out access provides living space. The attic and basement offer ample storage. Attached 3-car garage. Includes 3D walkthrough and video tour. Conveniently located near King's Highway Elementary (1.0 mi), Coleytown Middle (1.5 mi), Staples High School (2.0 mi), shops, restaurants, and commuter routes. Exceptional opportunity to combine classic Colonial style with modern functionality.

33 Pequot Trl, Westport

2 Fairport Rd, Westport
$2,068,000
5 Beds ⋅ 5 Baths ⋅ 24144977 MLS
Experience a new standard of modern elegance in this brand new luxury home in the heart of Westport. Spanning over 4,200 square feet of finished living space across four beautifully appointed levels, this residence features stunning white oak floors and premium finishes throughout. The main level features a bright open floor plan that seamlessly integrates a gourmet kitchen with large center island into a spacious dining area and family room anchored by a warm gas fireplace. A dedicated first-floor office offers a quiet, sophisticated workspace, with the convenience of a nearby mudroom and powder room. In the back, the transition to the outdoors is seamless, as the family room opens to a covered patio and a sparkling in-ground gunite pool with bluestone surround. To ensure absolute tranquility, the yard will be professionally completed with fencing, trees, and shrubs. The second level of the home has four bedrooms, including a primary suite with a generous walk-in closet and a spa-like bathroom featuring a double sink, large shower, and soaking tub. An additional en-suite bedroom includes a walk-in closet, while two more bedrooms share a well-appointed bath. A laundry room with a dedicated sink is also located on this level. The third floor offers a bright flex space, while the fully finished basement provides a fifth bedroom, full bathroom, and a spacious playroom. Enjoy the convenience of city water, sewer, and natural gas in a quiet neighborhood close to premier shopping.

2 Fairport Rd, Westport

4 Joann Cir, Westport
$2,050,000
4 Beds ⋅ 3 Baths ⋅ 24179836 MLS
HIGHEST AND BEST DEADLINE: SUNDAY, 6/7 BY 5PM -- Beautifully renovated and perfectly positioned in one of Westport's most coveted and centrally located neighborhoods, this 4-bedroom home offers the turnkey lifestyle today's buyers are seeking, with modern updates, flexible living spaces, and easy access to everything that makes Westport so special. Just minutes from top-ranked schools, downtown shopping and dining, Compo Beach, and transportation -- the location is simply exceptional. The sun-filled main level features a welcoming living room with vaulted ceiling, fireplace, and seamless flow into the dining room. The renovated kitchen showcases crisp white cabinetry, quartz countertops, marble backsplash, chic lighting, and sweeping views of the private backyard. The primary suite has been thoughtfully transformed with a tray ceiling, large walk-in closet, and luxurious marble bath with double vanity, soaking tub, and shower. Two additional bedrooms and a renovated full bath complete the upper level. The lower level offers outstanding flexibility with a fourth bedroom, renovated full bath, convenient home office, and spacious family room featuring custom built-ins, a wood-burning fireplace, and sliders to the patio and backyard. An additional lower level provides a large recreation room, dedicated laundry room, cedar closet, and abundant storage. Move right in and enjoy a turnkey lifestyle in one of Westport's most desirable neighborhoods.

4 Joann Cir, Westport

34 Pequot Trl, Westport
$2,050,000
5 Beds ⋅ 4 Baths ⋅ 24178738 MLS
Discover this serene setting in a sought after Old Hill neighborhood. Two thoughtful and beautifully executed additions have made this sprawling 12 room home flow with the versatility to fit today's varied lifestyles. Comfortable open living spaces have been designed with the flexibility to offer multi-generational spaces, a home office or simply to allow for room to grow in the way that pleases you best. The welcoming living room with its broad bay window and formal fireplace provides ample room for your guests and the Baby Grand piano! The custom country kitchen is both practical and beautiful with wide plank wood floors, cherry and glass cabinetry, granite counters and a walk-in pantry. The adjoining family room with it's cathedral ceiling is filled with natural light and includes a fireplace, wet bar and French doors that open to a wraparound deck. The most recent addition is an impressive library with long, tall windows set amid tailored built-ins. An additional exterior entry makes it ideal for home office use while the adjacent full bathroom and closet offers the possibility of a first floor bedroom suite. The informal rear foyer includes access to a laundry area, powder room and extra closets. Just beyond is a 2nd private office or den. Upstairs you'll discover the primary suite with full bathroom and walk-in closet, as well as 4 very spacious additional bedrooms. Unseen value found in the new roof, updated mechanicals and whole house generator!

34 Pequot Trl, Westport

Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

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.

How much is your home worth?

Get instant property value now!