Westport CT Real Estate & Homes for Sale

The most private and serene of the remaining multi-acre estates in central-most Westport... Just two minutes from the beach, town center, I-95, and the Saugatuck Hamlet rail station. Located Near several well-regarded school systems in Connecticut. This grand estate offers space for recreation, relaxation, and entertaining. A stone-gated, walled circular driveway marks the end of a private road cul-de-sac, abutting three luxury residences and the 22-acre Aspetuck Land Trust / Haskins Preserve. Enjoy the best of the Westport lifestyle: walk your dog across your own 4-acre property or through the Preserve with its entrance just steps away. Stroll among rose gardens, groomed lawns, and ornate flower beds. Host guests at one of Connecticut's largest heated pools (60' x 30'), with a cabana including bar, full and half baths, and changing rooms. The ~8,000 sq. ft. main residence blends historic charm and modern luxury: four grand fireplaces, a former ballroom, an antique stone-and-beamed family room, and a gourmet kitchen with professional appliances and baking island. A detached 1-bedroom guest cottage / legal rental with a 4-car garage completes this rare offering to own a historic estate property in central Westport.

Nestled along Westport's prestigious 'Gold Coast,' this architecturally magnificent estate on 4+ acres of park-like grounds with a breathtaking pool and professional-grade Har-Tru tennis court is a haven for luxury living and distinguished entertaining. Surrounded by major estates in one of the most sought-after coastal regions in the Northeast, it boasts access to pristine beaches, sophisticated amenities, and renowned schools, all within an easy commute to NYC. A gated driveway winds through lush, specimen plantings, arriving at an impressive parking court and the home's awe-inspiring foyer with double staircases, custom ironwork, and panoramic windows. Highlights include a sun-drenched great room with limestone fireplace, cathedral-ceiling library, and gourmet kitchen with top appliances, marble finishes, and custom cabinetry. The second-floor bedrooms feature breathtaking views, including a five-star primary suite, while additional third-floor bedrooms enhance flexibility. A gym overlooks the tennis court, and a wine cellar/tasting room elevates entertaining. Stone terraces surround the pool, featuring a pergola with an outdoor kitchen and retractable cover. One of only four deeded gates to directly access the grounds of Greens Farms Academy. This exceptional property offers unparalleled luxury, privacy, and lifestyle opportunities.

Location, location, location! Make Westport your new home. First time on the market in 30 plus years! Adorable 1930's Cape and separate cottage. Live in one and rent the other, rent both, or build your dream home. The charming, sun filled home (#22) offers 1128 sq ft of living space with 2 bedrooms, one full bath, living room, dining area, sunroom and updated kitchen, with beams, hardwood floors and spacious deck off the sunroom. The cottage (#24) at 904 sq ft has 2 bedrooms, one full bath, living/dining area, updated kitchen, stone floors on main level, and inviting back patio. Close to beaches, shopping and restaurants.

Tucked away at the end of a peaceful cul-de-sac, this custom-built home offers comfortable living, an abundance of natural light throughout, & unmatched convenience, being 5 minutes from schools & Green's Farms train station. With 4 bedrooms, 4.5 bathrooms, & flexible living spaces, this home is designed for entertaining & everyday family living. A double-height foyer welcomes you with a feature turning staircase & double ceiling windows.The formal living room features a marble fireplace, while the private office w/pocket doors offers the ideal work-from-home retreat. The expansive & light filled family room includes a second fireplace & French doors that open to the lush yard w/ gunite pool & spa. The adjoining kitchen, with breakfast area, radiates with sleek quartz countertops and modern cabinets. Upstairs, the primary suite features a partial cathedral ceiling, dual walk-in closets, & a spa-inspired bathroom, complete with modern soaking tub & separate shower. The 2nd level includes an additional three generously sized bedrooms, 2 w/walk-in closets. The walk-out lower level offers incredible flexibility, perfect for an in-law or guest suite w/ a full bathroom & separate entrance. Step outside to a level, fully fenced backyard for privacy where the pool, spa & patios are ideal for al fresco dining, relaxation, and entertaining. Utilities include city water, sewer & natural gas. A rare opportunity to own a home in one of Westport's most sought-after locations.

Set on a picturesque cul-de-sac, this elegant Colonial offers timeless charm and modern amenities. Nestled on a level two-acre lot, the home boasts lovely curb appeal and a private, fully fenced backyard perfect for entertaining, play, and recreation. Inside, you'll find four spacious bedrooms with the option for a fifth bedroom or private home office on the main level, complete with a full bath. The front-to-back living room features custom built-ins, while the generous formal dining room is ideal for hosting gatherings. The heart of the home is the oversized eat-in kitchen with granite countertops, stainless steel appliances, a large island, and a convenient mudroom entry. The kitchen flows seamlessly into the welcoming family room with a cozy fireplace and sliders that open to a serene screened porch that overlooks the stunning heated gunite pool and spa, complete with soothing waterfall feature. Enjoy outdoor living on the stone patio, surrounded by beautifully landscaped grounds. The finished lower-level great room offers endless possibilities-whether for a playroom, media center, gym, or additional living space. Additional features include a two-car garage, central air, a pull-down attic for extra storage, and a portable generator. Located just minutes from shopping, top-rated schools, town amenities, and train access, this beautifully maintained home offers tranquility and convenience - just in time for summer!

Nestled behind a classic fieldstone fence on a serene, level acre, this impeccably restored 1879 Colonial masterfully blends timeless elegance with modern comfort. With 4 bedrooms, 4 full baths, every corner of this home tells a story-inviting you to step into another era. The elegant formal dining room, anchored by an original Dutch door, speaks to the home's storied past and provides an ideal setting for memorable gatherings. The living room features rich built-ins and a classic wood-burning fireplace, offering a cozy yet sophisticated ambiance. Just beyond, a light-filled sunroom opens to serene views of the manicured grounds-an idyllic spot to relax and reflect. The eat-in kitchen connects to a sunken family room where sunlight streams through french doors that lead to a breathtaking stone patio with a cozy outdoor fireplace. The exterior is as carefully considered as the interior. The professionally landscaped grounds, are a living masterpiece-lush with perennial gardens that bloom through the seasons and surround a tranquil pond with a gentle fountain. Upstairs, the primary suite is a private sanctuary complete with a sun-drenched sitting room that offers views of the garden below. Located within close walking distance to Long Lots Elementary, this home is more than just a residence-it's a rare opportunity to live in a piece of history, beautifully reimagined for today.

With a concierge on-site and 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. Closings have commenced and the residences at The Mill are ready for immediate occupancy.

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.

Idyllically set on 600 feet of the West Branch of the Saugatuck River, this 4 acre property is the ideal setting to create your dream lifestyle. The homeowner/developer of the original 111 acre subdivision chose this site, above all others, to build his legacy compound comprised of two acres in Westport and two in Weston. Enjoy, expand or recreate the well cared for 3,800 square foot Colonial which is sited primarily in Westport and finished on three floors with river views from many rooms. The two bedroom guest house/barn, built over a large garage, is primarily located in Weston and provides the potential for a variety of options. This is a rare opportunity to create an extraordinary waterfront estate on one of Westport/Weston's premier properties.

Welcome to this sun-filled Colonial in the heart of Westport! This beautifully updated 4-bedroom home offers the perfect blend of classic charm and modern convenience. Enjoy peace of mind with city water, city sewer, a generator, and an outdoor sprinkler system. Inside, an expanded Kitchen and Family Room create a bright, open-concept, ideal for everyday living and entertaining. A spacious Screened Porch invites indoor-outdoor enjoyment, while the Mudroom adds functionality and ease of entry from the garage. Upstairs, the freshly added Jack & Jill bath offers smart convenience for busy mornings. A flexible main-level office with an adjacent full Bath can easily convert to a first-floor Bedroom-perfect for guests or multi-generational living. There is even additional open finished space in the lower level for a playroom. Located in a sought-after Westport neighborhood close to town, schools, and commuting options, this home checks every box for comfort, space, and style.

Prepare to fall in love with this extraordinary home, crafted with love by a talented architect for his own family. The charming shingle-style residence at 9 Bobwhite Drive is nestled on a picturesque, level acre amidst other fine homes in a peaceful cul-de-sac setting, offering plenty of space for fun and entertainment. You'll find joy around every corner with its custom woodwork, innovative cabinetry, and impressive 7-foot solid cherry doors. The living room boasts a stunning double-height ceiling, oversized windows, coffered details, and a grand fireplace. Select a book from the peaceful balcony library overlooking the living room and settle in! At the heart of this home is the "Cooks' Kitchen," featuring custom cabinetry, marble countertops, a limestone floor, dining space and another cozy fireplace. Just off the kitchen, a sun-drenched sunroom with a slate floor invites you to unwind. The first floor also offers a formal dining room and two bedrooms plus a full bath for your convenience. Upstairs, you'll discover three additional bedrooms (one ensuite) and the delightful primary suite, complete with beautiful built-ins in the dressing room and two spacious walk-in closets. The third floor is a canvas ready for your imagination, already prepped for a bathroom and future heating. Dream up your ideal space-perhaps a golf simulator? This home is truly a gem waiting to be cherished!

Welcome to this exceptional custom-built Colonial nestled on one of the most tranquil and conveniently located cul de sacs Westport has to offer. Thoughtfully designed and meticulously maintained, 5 Elwil defines the epitome of a "Forever Home". The Main floor features a welcoming Living Room with fireplace and multiple built-ins, a Great Room with fireplace and lofted cathedral ceilings, an Informal Dining room open to a Gourmet Kitchen and a splendid Formal Dining room with coffered ceilings. All main floor living spaces are beautifully proportioned, flooded with magnificent light and offer a unified cohesive circular flow. Upstairs you will find a spacious Primary Bedroom and bath along with 3 large, sunlit en-suite bedrooms and a sizable Recreation Room above the 3 car garage. For those searching for main floor living, there is a (5th) ensuite bedroom perfect for guests or multigenerational living. Outside you will find several bluestone patios that promise to call guests outdoors in the warmer months while offering remarkable privacy and views of nature year-round. Notable features & conveniences include: establishes garden beds with irrigation, a hardwired Generator, underground service lines, an updated survey offering pool feasibility & potential future development, a reverse osmosis water filtration system, a spacious attic for storage and a full

Charming curb appeal is your introduction to this sweetly updated classic neighborhood colonial. A third of an acre parcel is beautiful with flower beds and outdoor features. To drive up feels like coming home. Inside, the first level offers a chic yet homey open plan living space. The large living room includes a fireplace. The dining room is bright. The kitchen has white cabinets, stone counters, stainless appliances, and open shelves. The mudroom connects the garage. It includes a stackable laundry and a powder room. Upstairs are three good-sized family bedrooms, a hall bath, and a good-sized primary bedroom with three closets (one very large walk-in) and en suite bath. The finished walkout lower level is perfect for play, tv, exercise or other activities. Public water and sewer. Centrally located such that everything is CLOSE - shopping, westport center, train and transportation, the beach. Come Enjoy this charming and pleasant Westport home!

A Truly Exceptional Home That Has It All! Every so often, a home comes along that checks every box. This beautifully updated, move-in-ready house offers everything you could want: city sewer and water, natural gas for heating and cooling, a whole-house generator-all in a prime location on a quiet cul-de-sac. The property boasts underground electrical lines, a fenced-in yard with mature plantings, and is conveniently located close to schools, shopping, and restaurants. Inside, this home has been meticulously maintained and thoughtfully updated, featuring a renovated kitchen and baths, central air, refinished hardwood floors throughout, and fresh interior and exterior paint. The spacious primary bedroom suite includes a luxurious bath with both a shower and a tub. With three additional generously-sized bedrooms, excellent storage space, and a finished basement, this home truly has room for everything. Step outside to enjoy a massive new Trex deck with a pergola, two bluestone patios, and a cozy firepit area. There's also potential for further expansion, making this a home that can grow with you.

Discover the ease of living at 15 Lone Pine Lane, a home located in one of Westport's most coveted in-town neighborhoods. This property's central location ensures convenience, while the quiet streets provide a peaceful retreat. The interior has been refreshed over the years showcasing noticeable upgrades like a modern kitchen, updated bathrooms and lighting. Hidden upgrades include the recent connection to sewer, a new roof in Dec 2019 and new wood flooring which further enhance this move-in-ready home. The interior is light & cheerful and was recently painted neutral finishes that create a welcoming ambiance. The eat-in kitchen seamlessly flows into the family room and playroom (which could also be a DR), perfect for gatherings and entertainment. Outside, enjoy a private, fenced-in level yard featuring a bluestone patio and a handcrafted stone wall, ideal for outdoor relaxation and entertainment. The property includes an oversized two-car garage with expansion potential above, adding to its versatile appeal. This home is meticulously maintained and recently painted inside & out. Enjoy the vibrant community life with a short walk to local coffee shops, a scenic stroll along the Saugatuck River to the library or a free concert at Levitt Pavilion. Nearby, discover a variety of shops and restaurants, the Westport Country Playhouse and fresh produce at the Farmers Market, all within walking distance from your new home on Lone Pine Lane.

This spectacular architect designed 5 Bedroom, 4 full Bath Contemporary is beautifully sited on an extraordinary and private 1.3 acre property with Pond, and just minutes to all of Westport's fabulous amenities and train Service to NYC. Tasteful renovations throughout 3700 square feet of living space offer dramatic, sun-filled interiors, Dining Room overlooking step-down Living Room with soaring ceiling, Fireplace, and access to expansive Deck, Office opening onto Screened Porch, Chef's Kitchen with Dining Area, private Primary Suite, Walk-out Lower Level with very versatile Great Room with Fireplace, Bedroom and Bath, an immaculate attached over-size Two-Car Garage with generous storage, and a Whole House Generator. First Floor: Foyer with random-width oak flooring, Guest Closet and access to Over-size attached Two-Car Garage. Dining Room with random-width oak flooring overlooking Step-down Living Room with random-width oak flooring, gas-log Fireplace, 2-story ceiling with Fan and Track Lighting, and twin Sliding Doors to expansive Deck. Chef's Kitchen with 12' ceilings and Skylight, oak flooring, Center Island Cook-top, timeless laminate Cabinetry, semi-circular Dining Area with wainscoting, and Built-in Desk. Wonderful Office/Bedroom with oak flooring, built-in Bookcases and Cabinetry, and sliding door to delightful Screened Porch. Full Hall Bath with oak flooring. Second Floor: Laundry Room with tile flooring. Bedroom with oak flooring. PLEASE OPEN ADDENDUM.

Discover Westport's Premier Coastal Gem. Immerse yourself in modern elegance with this stunning new beach house, located in the highly sought-after Saugatuck Shores neighborhood. Constructed in 2022, this five-bedroom, four-and-a-half-bathroom residence spans over 3,700 square feet of finished living space. Tucked away on a peaceful cul-de-sac, the home offers easy access to the vibrant energy and amenities of Saugatuck. The first floor features an open layout with soaring 9-foot ceilings, a sunlit living room with serene water views, and a sleek gas fireplace. The space effortlessly flows into a gourmet kitchen and formal dining area. A flexible first-floor bedroom, paired with a full bath, is perfect for guests or a home office. The second floor boasts a luxurious primary suite with its own gas fireplace, breathtaking water vistas, and a spa-like bath for the ultimate retreat. Three additional bedrooms, paired with two beautifully designed bathrooms, provide comfort and privacy. On the third floor, a versatile space awaits-ideal for a studio, lounge, or recreational area, with direct access to a rooftop deck overlooking the water. Outside, this expansive 0.25-acre property is a private oasis. Enjoy a heated gunite saltwater pool, a spacious terrace, and a large yard-perfect for outdoor fun, relaxation, and entertaining. This home masterfully blends contemporary design, comfort, and functionality in one of Westport's most desirable locations. SF Incl Fin LL

Prepare to experience the extraordinary and discover the future at this new residence by Skyview Builders. Now complete and ready for immediate enjoyment, this world-class estate elevates the standard against which all others are measured. Set on two spectacular, level acres in the heart of Westport's premier estate section, long considered a haven for celebrities & influential figures. The gated approach leads to an unrivaled custom home characterized by innovative materials & finishes incl a mirror-effect glass partial facade, glass entry canopy, KLAR windows/doors w/triple pane glass & quality construction practices that represent the future of building technology. Enter a refined environment where every intuitively designed space flows harmoniously. As you explore the interior, you will encounter customized built-ins, porcelain accents, linear fireplaces, LED-lit curtain channels, fine fixtures & much more. The hub of this home is the awe-inspiring gourmet kitchen/Great room w/sliding glass wall to the rear, hidden prep kitchens, enclosed outdoor entertaining space w/sep summer kitchen all leading to the pool terrace w/spa, swim-up bar, sunken seating area w/fire table. Each of the 6 lux BR suites has a priv bath. The primary suite has spectacular dressing rms & a spa bath unlike any other. The 3rd flr bonus rm opens to a roof deck w/hot tub. The fin LL dazzles w/media rm, spa, wine cellar, full wellness suite. Ask about Skyview's luxury homes in Greenwich & Westport.

Welcome to your dream retreat in the heart of Westport, Connecticut! Nestled on over 2 acres of serene and private land, this quaint cottage offers the perfect blend of rustic charm and modern convenience. Ideally located, you'll find yourself just moments away from the train station, vibrant downtown Westport, and the scenic Compo Beach. The property's expansive grounds provide ample opportunity for customization and growth, boasting enough space to expand the existing cottage footprint and even build a 2,000 square foot Accessory Dwelling Unit (ADU). This flexibility makes it an ideal choice for those looking to create a multi-generational living space or a guest retreat. Step inside to discover a warm and welcoming interior with cozy living spaces, featuring charming details that reflect the character of this delightful cottage. Large windows allow natural light to pour in, creating a bright and airy atmosphere. The surrounding landscape offers lush greenery and a sense of tranquility, providing a private oasis to relax and unwind. Whether you're looking to enjoy the convenience of nearby amenities, explore the beautiful beaches, or simply savor the peace and privacy of your own estate, this property offers the perfect canvas for your vision. Don't miss the chance to make this Westport gem your own!

Sited perfectly on a gorgeous one-acre property in the heart of wonderful Westport, this light and bright 3-4-bedroom, 3 full bath mid century modern ranch home has enough space to breathe, play and work. There are Large rooms, open spaces, two fireplaces, central air, hardwood floors throughout, and so many closets that one would have to work at being disorganized. Everything flows beautifully here. An enormous open concept space includes granite kitchen with island, and large walk-in pantry, a sunny family dining area and enormous family room with vaulted ceiling. A huge, lavish primary suite which opens to a deck, has vaulted ceilings, a very large walk-in closet, 6-piece bath with jetted tub and double walk-in shower, a large vanity with sink and great built-ins plus water closet with a second sink. Decks, patios, cabana and large shed enhance the outdoors. Decorated in a neutral palette, this great home is now looking forward to its next owners to move in and make updates along the way.

Nestled on a rare double lot in Westport's coveted Compo Beach, this custom-built sanctuary blends timeless elegance with modern coastal luxury. Embracing the essence of beachside living, this 4,532 sq. ft. home boasts exquisite millwork, a gourmet kitchen with custom cabinetry, and sun-drenched living spaces. French doors lead to a private terrace featuring an outdoor kitchen, shower, and fireplace, while a stunning heated rooftop deck offers panoramic Long Island Sound views, a gas fireplace, and built-in sound system-perfect for sunset entertaining. The primary suite is a serene retreat with a fireplace, office nook, spa bath, and dual walk-in closets. Four additional en-suite bedrooms ensure privacy and comfort. A radiant-heated mudroom, two-car heated garage with EV charging, and professionally landscaped grounds complete this unique coastal offering-just minutes from downtown Westport, Metro-North, and 50 miles from Midtown Manhattan.

Please submit "Highest and Best" by noon on Monday 4/21/25 Gorgeous renovation from top to bottom of this 5-bedroom Colonial, perfectly nestled on a private cul-de-sac in a prime Westport location. Boasting a bright and airy open floor plan, this home offers sophisticated style and modern comfort at every turn. Step into a gracious entry foyer that sets the tone for the beautifully updated interior. The spacious front-to-back formal living room features a classic wood-burning fireplace, while the fully reimagined eat-in kitchen will delight any chef with its brand new cabinetry, sleek Quartz countertops, and top-of-the-line stainless steel appliances. The kitchen flows effortlessly into the dining room, ideal for entertaining and continues into the inviting family room, highlighted by a surround of windows and abundant natural light. French doors lead to a stunning four season sunroom, the perfect place to relax year round. Step outside to a newly finished deck overlooking a fenced, level backyard, offering privacy and space for play and gatherings. Upstairs, you'll find five generously sized bedrooms, including a luxurious primary suite complete with a renovated bath and a large walk-in closet. Add'l highlights include beautifully refinished hardwood floors throughout, all-new bathrooms, updated electrical, and fresh interior and exterior painting. No detail has been overlooked in this extensive renovation-please see the complete list of improvements for more.

Freshly-updated, meticulously-kept contemporary set down a quiet, pretty lane off of a central multi-million dollar street in desirable Hunt Club area. Bright, stylishly-renovated spaces, soaring ceilings and a host of high-quality details. Two story front to back entry and floor to ceiling double fireplace in sun-drenched living and dining room. Gleaming top of the line quartzite kitchen w/stainless equipment, spacious breakfast banquette, Subzero wine fridge, Juliska lighting & center island. Expansive deck overlooks the level, manicured yard and provides the perfect complement for entertaining, relaxation and sport. Upstairs, the airy primary suite boasts a glamorous, spa-like luxury bath, fireplace, and dual custom designed closets. Three ample family bedrooms, also with custom closets, a separate office, and spacious walk-in cedar closet. Several modern enhancements and cool features such as smart thermostats, extra insulation, EV garage outlet, docking drawer in kitchen and electrified hairdryer drawer & heated towel bars in primary bath. Superb commuter location, just moments to schools, shopping/dining amenities, beach and Metro North. Sewer, city water and natural gas complete this beautiful, move-in ready picture.

Here is the moment you have been waiting for! Your chance to get into Westport and all it has to offer at a very rare price point! The location is sublime, 5 minutes from the train, 5 minutes to Compo Beach! This ranch style home has so much to offer. 3 BR's on the main floor with a 4th in the fully finished, walk-out lower level. Lower level has a kitchen, bath, separate entrance, newer flooring. Perfect for in-law, au pair, visitors, office, whatever you can imagine! On the main floor, the bath has been completely remodeled. Replete with Kohler finishes, new tiling, faux wood waterproof flooring, heated bidet, and a beautiful cobalt blue, glass vessel sink! Granite countertops in the kitchen, with a newer LG refrigerator. 14 ft. vaulted ceilings in the family room, with sliders leading to deck, as well as the fully fenced and flat backyard. This home is not to be missed and certainly will not last. Come make this your home!

Welcome to 27 Blue Ribbon Road - A Serene Retreat in the Heart of Westport. Tucked away on a quiet, tree-lined street where neighbors still greet each other by name, this expanded split-level home offers the perfect blend of comfort, style, and community. With 4 spacious bedrooms, a dedicated home office, and a thoughtfully updated layout, this property is ideal for both everyday living and entertaining. Step inside to discover updated kitchen, opening into an expanded family room with a vaulted ceiling. The home's classic shingle siding exudes timeless charm, while large windows fill the interior with natural light. Finished basement playroom area with bathroom and sliding doors to the pool. Outdoors, enjoy a private backyard oasis featuring a beautiful in ground pool-perfect and fenced garden area for relaxing summer days or hosting friends and family. Whether you're walking the dog, chatting with neighbors at the bus stop, or enjoying the peaceful surroundings, this neighborhood offers a rare sense of connection and tranquility. Don't miss the opportunity to make this warm, welcoming home your own.