Smithtown NY Real Estate & Homes for Sale

Welcome to Mellow Street - a peaceful little cul-de-sac in Fairfield's coveted beach area with an ideal location. Close to the train, vibrant downtown, restaurants, theater, and endless fun activities. There is room for everyone in this wonderful remodeled (2008-2011) home. Just under 2500 square feet of comfortable space. Enjoy 5 bedrooms, 3 full baths, and lots of special features. The chef's kitchen offers cherry wood cabinets, double ovens, custom tile backsplash, under-counter lighting, and a generous center island with granite countertops. The spacious family room, perfect for gatherings with vaulted ceiling & gas fireplace, opens to a private fenced-in yard with a generous stone patio. There's a butler's pantry / laundry room with a second refrigerator, sink, and lots of additional cabinetry - perfect for party food prep. The primary bedroom suite has a full bath, dressing room / office or nursery, lots of closets and additional accessible attic storage space through the walk-in closet. Central air, recessed lighting, crown moldings, one car garage, tankless hot water heater, plenty of storage and a full unfinished basement. All of this and just minutes to the beach!

Coveted Southport waterfront. Builder's own 11,000+ sq. foot custom home on private Rock Point Road off Pequot Avenue and walking distance to Southport Beach and Village. Magnificent 1.9-acre lot with 200 feet directly on Long Island Sound with views towards Westport's Gold Coast of Beachside Avenue and the Manhattan skyline in the distance. A beautiful pool and pool house pull you outside to enjoy every changing tide and sky. Outstanding value when compared to neighboring sales and tremendous potential upside awaits the prudent purchaser. A similar sized lot on the street recently sold for $7m and the house directly next door sold in 2020 for $16.5m. Come and see for yourself. Don't miss out as all of our best local waterfront properties are being snatched up. Close to the town centers of Westport, Southport and Fairfield and just 50 miles to NYC.

Custom design your dream beach house on the shores of the Long Island Sound and Westport's Gold Coast. This modern masterpiece, proposed by award-winning Coastal Luxury Homes, offers an open floor plan that seamlessly blends the chef's kitchen, great room, and dining areas. Floor-to-ceiling windows provide expansive views of the LI Sound, while glass and metal walls create a contemporary ambiance. With 4 bedrooms and 3 bathrooms, including a luxurious master suite with a walk-in closet, this home is perfect for coastal living. Enjoy your morning coffee while taking in the sunrise, take a morning dip or stroll along the coastline. The prime location offers easy access to sandy beaches, nearby shops, restaurants, entertainment venues, and Westport Metro North Station. Additional features include high ceilings throughout, hardwood floors on multiple levels, a cozy fireplace in the main living area, French doors leading to outdoor spaces, and smart home technology.Don't miss out on this opportunity to own your slice of heaven! Schedule a meeting today to make this dream beach home yours. PLEASE ABSOLUTELY NO WALKING PROPERTY WITHOUT A CONFIRMED APPOINTMENT. RECENT TOWN APPROVALS ON NEARBY PROPERTIES SUGGEST THAT A LARGER HOME OF APPROX. 3000 SQFT MAYBE APPROVED. PLEASE ASK FOR DETAILS.

Welcome to this charming extended ranch on a picturesque acre in Rowayton! This spacious home features an inviting inground pool and a beautiful level yard perfect for outdoor entertaining, fun and games. A rarity in Rowayton! One floor living featuring a large eat-in kitchen, oversized dining room with sliders to deck, music room, living room with raised hearth wood-burning fireplace overlooking pool and back yard. Additional spacious family room with beamed vaulted ceiling, providing a inviting atmosphere for gatherings and watching the game. All 4 bedrooms are good sized, perfect for accommodating your family's needs, along with private office space in the upper level. Oversized two-car garage and with plenty of parking in circular driveway. The property offers potential for renovation, expansion and adding value on a rare open arce of land. 60 min. to NYC on Metro North. Walk to Bayley Beach, Library, dog park, village shops and great restaurants, train station, pickleball courts, paddle tennis, tennis, community dock to launch your kayak or paddleboard and so much more! Property also listed as land MLS 24004543

This magnificent estate was designed by renowned architect Roger Ferris and boasts 5 levels of living with spectacular water vistas of Southport Harbor. Entry to the main level is through an imposing 2 story limestone portico into the embrace of a soaring space that is the Gallery with its mesmerizing marmalade marble floor and stunning floating wrought iron circular staircase. From this point, all major rooms on the floor emanate in a logical clockwise progression: Living Room, Library, Family Room, Eat in Kitchen and Dining Room. Fabulous floor to ceiling windows and French doors open to take full advantage of Southport Village & Harbor, Country Club of Fairfield, Long Island Sound and the Manhattan skyline. The gracious Master Bedroom Suite has a sitting room with fireplace, his & hers full baths, dressing areas and private studies. Below the Master Suite are 6 en-suite bathrooms and media/playroom area. Below the main level is a Cabana Room with kitchenette, elaborate bath complex, sauna, exercise room, office and wine cellar which leads to an outdoor pool and limestone patio. Progressing down, the next level brings you to the indoor sports facility including a squash/basketball court and dance studio. The lowest level of this home has a 75 foot long Italian marble lined indoor pool with a glass skylight roof. Included on this stunning property is an outdoor heated gunite pool with spa. The Guest House has a Living Room, Kitchen, 2 Bedrooms, 2 Full Baths & 2 Bay Garage.

Welcome to Waters Edge, a luxury new construction condominium direct waterfront destination with a modern coastal aesthetic designed by award-winning architect Bruce Beinfield offering an unparalleled lifestyle with breathtaking views, owners' deep water dock and direct access to Long Island Sound. Expansive modern-edge balconies and sophisticated details reflect the vision and quality embodied in this magnificent structure. Each room is designed to capture the ever-changing water views. This private enclave is indeed a seaside sanctuary situated in the heart of the coastal village of Rowayton. Features: Largest unit, 2 story, 9' ceilings with seamless wall of windows offering panoramic water views from the living room to the kitchen, 2 FP's and expansive balcony on each floor. Shared owner's features include: Built in gas grill, fire pit, several seating areas, green space, direct dock access and visitor parking.

Welcome to Waters Edge, a luxury new construction condominium direct waterfront destination with a modern coastal aesthetic designed by award-winning architect Bruce Beinfield offering an unparalleled lifestyle with breathtaking views, owners' deep water dock and direct access to Long Island Sound. Expansive modern-edge balconies and sophisticated details reflect the vision and quality embodied in this magnificent structure. Each room is designed to capture the ever-changing water views. This private enclave is indeed a seaside sanctuary situated in the heart of the coastal village of Rowayton. Features: 2 story home, additional private entrance to green space, living room w/ fireplace, expansive balcony on each floor. Shared owner's features include: Built in gas grill, fire pit, several seating areas, green space, direct dock access and visitor parking.

Embrace the quintessential beach lifestyle in this exquisitely designed home, nestled on one of Fairfield's most vibrant & sought-after streets. Perfectly located within walking distance to beaches, eateries, shops, and lively entertainment, with the convenience of nearby train access and top-rated schools, embodying everything the Fairfield lifestyle has to offer. As you step inside, you're greeted by a soaring staircase & 3 levels of meticulously updated living space. The home features new hardwood floors & a chef's kitchen w/ quartz countertops, an expansive island, & stainless appliances. The floor plan flows effortlessly from a versatile home office to a stylish dining room that balances formal and casual settings with a uniquely crafted bar wall feat. a wine rack and liquor cabinet shelving. The living room, designed for relaxation & entertaining, blends beautifully w/ the kitchen & overlooks the manicured yard. The 1st floor also boasts a mudroom w/ cubbies, powder room, & laundry room. Ascend to the 2nd floor where you'll find 3 spacious bedrooms & 2 baths, incl. a primary suite w/ a spa-like bath, feat. a soaking tub, glass shower, dual vanities & a walk-in closet. The top floor offers flex space for a bonus or media room. Additional luxuries incl.a private suite above the 2-car garage-perfect for an au-pair, in-law or office, & the fenced yard & patio area are ideal for hosting gatherings & BBQs. At 93 Howard St, you don't just find a home-you discover a lifestyle!

Wonderful opportunity on coveted Sasco Hill neighborhood cul-De-Sac. Ideally situated on expansive 1/3 acre property. 1st floor bedroom and full bath offers the opportunity for 1st for primary bedroom. Spacious living room with fireplace, updated kitchen with granite counters & stainless steel appliances flows to large sunroom. Finished lower level family room, playroom or office offers versatility. Incredibly convient location close to everthing. Less than a mile to Sasco & Pine Creek beaches. Minutes to train, golf, tennis, Southport village & harbor and vibrant Fairfield town center. No flood insurance required. Pictures from home's previous listing. Tenant in place until 10/1/2014.

Imagine a lifestyle where the urban pulse meets tranquil beach vibes-welcome to your dream turnkey home at Harbor Shores! This meticulously maintained home welcomes you w/a bright and inviting floor plan that flows seamlessly, accentuated by sun-filled rooms and hardwood floors. Front to back living room, centered around a beautifully appointed gas fireplace w/an elegant mantle, offers a warm and inviting atmosphere that is a versatile space perfect for relaxing or entertaining. The beautiful oversized updated kitchen leads you to exceptional outdoor living space. An expansive deck with a sunken hot tub complements the charming patio area and gardens beyond. The Wisteria-covered arbor creates a magical space perfect for relaxing in a saltwater breeze. On a cul-de-sac in a blissful near-water setting, this home stands historically resilient against nature's whims and storms. Experience the enchantment of summer listening to live music echoing across the harbor, visible 4th of July fireworks from your private deck, and the serenity of soaking in your hot tub under a starlit sky. Outdoor enthusiasts will revel in the proximity to pickleball courts and marinas- launch your paddleboard/kayak within a block from your doorstep to explore the scenic waters anytime. Top-tier dining options, and SONO train station all just moments away. Upgrades include new roof, beautiful bathrooms, and kitchen. This delightful home positioned within a vibrant waterfront community is not to be missed!

SOUTHPORT CHIC -Attention Investors... this home is rented until June 2025. Just steps to the beach, Harbor and quaint Southport Village, this French inspired beauty will make you feel like you've been whisked away to the European countryside although you're just 50 minutes from Manhattan. In the neighborhood of multi-million dollar seaside estates, restored antique homes, and newer builds with that Je ne sais quoi quintessential New England charm, this French Provincial prize is perfectly private, buffered from the road on a picturesque 2.79 acres with magnificent heated pool. Timeless and sophisticated, boasting 5200sf, the large and inviting public rooms with French doors unite the indoors with outside patios and entertaining spaces. You'll adore the high ceilings, elegance, and easy lifestyle in the comfortable sun-drenched spaces: living room with fireplace; oversized dining room; kitchen with large island and breakfast area opening to the family room with fireplace; library with fireplace and bar; office; laundry, and mudroom. There is a luxurious guest suite on the main floor along with a smaller bedroom with full bath. Come upstairs to the gracious primary suite with fireplace, balcony overlooking the pool, walk-in closet and marble bath. Three additional bedrooms and two full baths complete the 2nd and 3rd floor. C'est Magnifique!

Wonderful combination of two fully subdivided lots in the historic waterfront village of Rowayton! Front lot is 0.61 acres with a charming, expanded 1938 cape home of 2,780 sqft. The adjoining rear lot is a wooded .75 acre parcel providing total privacy & an opportunity for development or build your dream home! Ample room for a pool on each lot! First time on the market in more than 50 years. The home is in great condition with freshly refinished hardwood floors throughout, most rooms have been painted with a newly installed oil tank; the home is move-in ready for summer fun! Come make this lovely Rowayton home your own!

Move in ready this modern colonial is located in the sought after waterfront community of Rowayton. Step inside from the covered front entry where an open floor plan greets you featuring a beautifully crafted staircase that traverses all 4 levels. The 9' ceilings, 8' high doors strike a dramatic styling and there are custom millwork accents throughout. The oversized windows flood the interior with natural light, creating a bright and airy atmosphere with serene property views that can be enjoyed from within and from the wrap-around elevated deck. With 12 rooms on 4 levels there is plenty of room to live in comfort. The layout is ideal and provides for using rooms the way that fit your lifestyle needs that includes 4 bedrooms on the 2nd floor w/3 full baths, optional 4th bedroom on the lower lever w/full bath and guest suite on the 4th floor w/full bath. This is "right sizing" and designed for low maintenance & high energy efficiency utilizing quality materials & skilled craftsmanship, Marvin Windows, ERV (Energy Recovery Ventilation unit) and Bosch Heat Pumps your indoor air comfort is assured. This location offers easy access to the vibrant amenities of Rowayton and surrounding communities including Bailey Beach & LIS, marinas, the village shops, dining venues, Pinkney Park concerts, farmers market, RR and much more all just 38 miles to NYC.

Completed in 2024 this quality-built home is new from the ground up. Whether you are "Upsizing" "Downsizing" or "Rightsizing" this 5 bedroom, 5-1/2 bath modern colonial is ready to adapt to your lifestyle. Step inside the main level where an open floor plan welcomes you with features that include a beautifully crafted four level staircase that traverses the two-story window wall, the 9' ceilings and 8' high doors all strike a dramatic styling with custom millwork throughout. Oversized windows flood the interior with morning light and bring the outside in. The open floor plan has a great flow for day-to-day living with easy access to the elevated deck. Designed for low maintenance and high efficiency utilizing quality material & skilled craftsmanship, Marvin Windows and Bosch Heat Pumps your year-round comfort is assured. Additional features include a walk-in pantry, pre-wired for an EVC, abundant closet & storage space. This location offers easy access to the vibrant amenities of Rowayton including Bayley Beach and Long Island Sound. Close to the Village, train station, shops, restaurants, Pinkney Park, Community Center, dog park and more. If you are new to the area checkout the RCA Rowayton Civic Association.

Welcome to 61 Witch Lane, an enchanting farm house on a gracious flat lot in the center of Rowayton. With 6 beds and over 4,200 SF, this home is a rare find in the quaint seaside village of Rowayton. Upon entering, one is met by an inviting foyer with soaring ceilings, an enclosed mudroom and a spacious living room that enters into the dining room and kitchen. The first floor is complete with a home office along with a full bath and bedroom, perfect for a nanny, in-law suite, or guest room. A front and back staircase lead to the second floor with a cozy den featuring floor to ceiling built-ins, a primary suite, 3 additional bedrooms, a bathroom and laundry room. The third floor offers the perfect bonus space for a playroom/family room, gym and anything in-between along with an additional bedroom and office. A front flagstone patio with a porch swing adds charm while the backyard patio is perfect for summer evening bbqs. The sprawling front yard is complemented by the always desirable corner lot. Walk to town, beach, schools, train and everything that Rowayton has to offer.

Nestled in the heart of Fairfield, this meticulously maintained two-family home is a rare find. Boasting a generous 1,900 square feet of living space, it offers a total of 5 bedrooms and 2 full baths across both units. Convenience is key with this property, as it's just minutes away from the town center and train station, offering easy access to great restaurants and shopping. Additionally, the property sits on a spacious .16-acre lot, providing ample room for expansion or outdoor enjoyment. Nature enthusiasts will appreciate the short drive to the town's beautiful beaches, perfect for soaking up the sun and enjoying water activities. Updates throughout the home ensure modern comfort, while the inclusion of city sewers, water, and natural gas adds further convenience. Whether you're looking for a new place to call home or seeking an investment opportunity, this property has it all. Don't miss out-schedule a viewing today and make this gem yours!

This inviting, turn-key home sits on a lovely corner lot within the coveted Fairfield Beach Community. Built in 2014, it offers beautiful living spaces and an open floor plan. Custom window seats, hardwood floors, a sunny breakfast nook, 2 balconies and traditional millwork add to its warm and welcoming atmosphere. The hub of this home features a chef's kitchen which opens to a sun-filled family room with built-ins and a fireplace-ideal for entertaining family and friends. A quiet work space can be found in the 1st floor office by closing its French doors. The primary suite offers a private oasis with a balcony, an ensuite spa bathroom and two custom walk-in closets. This home also features three additional light filled bedrooms on the 2nd floor. The fully finished 3rd floor offers additional space with a 2nd office and a playroom, or could be used as a 5th bedroom with its full bath. The covered 3rd floor balcony is the perfect spot to watch the July 4th fireworks! There are 2 additional spaces off the main level used for the family's hobbies: a wood shop and a gym. The home at 126 Carlynn represents a wonderful opportunity, just a block from Fairfield Beach Club or Penfield Beaches! Enjoy the coastal lifestyle of walking on the beach, easy bike riding or jogging through this close knit neighborhood. Beach life year-round along Long Island Sound.

Opportunity to create your own new dream home or work with the current home and renovate on a beautiful property on a quiet neighborhood street, close to all Rowayton amenities. Nature-lover's dream spot with mature perennials and trees, just waiting for a new owner to bring it back to life. House is sold 'as is'. Centrally located, Rowayton address- walk to train, town, schools, etc. Sale is subject to probate court approval.

Step into the epitome of luxury coastal living in this architecturally stunning, sun-flooded California contemporary home set on oversized 1/4 acre dry lot in the heart of FFLD Beach--steps from town & Penfield Beach. This 5/6 BR beach haven boasts unmatched quality w/sensational glass railing staircase & hallways, 9-ft ceilings, 5" white oak floors throughout 3 floors & an abundance of oversized windows, glass doors & decks that bring the outdoors in. Central to this breathtaking home is the chef's dream kitchen, equipped w/a spectacular 10 ft waterfall quartz island, 48" paneled SUB-ZERO refrigerator, 48" Wolf double oven stove, walk-in pantry & custom wet bar w/sink & beverage fridge. Front porch, gorgeous formal living room, large dining room, casual breakfast area & family room w/gas fireplace & back deck create a seamless, airy 1st fl. flow. Upstairs, 5 BR including primary suite w/soaring vaulted ceilings, huge deck & sublime, spa-like bath w/enormous marble shower & radiant heated floors. 4 add'l generously sized BR, 2 BA & laundry room w/cabinetry complete the 2nd level. 3rd level w/full bath & deck w/soaring views offers endless possibilities for playroom, 6th BR, gym, office or combination. Lower level loggia overlooks huge lot w/endless possibilities & pool permit in place. Oversized garage, GENERAC FULL home generator, outdoor shower, gas/sewer. This is your chance to live your best life at the BEACH!

Dramatic and spacious Saugatuck Shores contemporary is bathed in sunlight. Owners have updated throughout and added beautiful additional interior living spaces and a private rooftop deck. Flexible floor plan with 4-5 bedrooms and 4 full updated baths with a clean, European sensibility. The main living area enjoys vaulted ceilings and a welcoming open floor plan with double sliders to another oversized deck. The main living room is enhanced by a floor to ceiling fieldstone fireplace and a unique bar. The bright and polished kitchen features a wonderful oversized island plus generous space for dining. The newer upper level family room addition with gorgeous full bath and closet can easily function as an additional bedroom suite if desired. The bedroom wing on the main level includes a remodeled primary suite with full bath, walk in closet and fireplace, plus sliders to the private patio. An oversized additional family bedroom is also improved by an en suite bath. Two additional family bedrooms share the updated hall bath. The main level is anchored by a striking vaulted foyer that opens to both the front and rear of this one of a kind home. The property is fully fenced for privacy and enhanced by specimen plantings and mature landscaping plus plenty of room to enjoy outdoor activities. Most desirable location for commuters, outdoor enthusiasts and anyone who desires to live every day like they are on vacation!

Impeccably built 5 bedroom Colonial beauty in the heart of the Fairfield Beach area. Enjoy captivating water views from fabulous rooftop deck complete with retractable awning, at 120 Rhoda Avenue, built by renowned local builder, Mcdillon in 2014. Sited on .23 acres on a quiet side street, this home is just steps to sandy beaches & a quick walk to Sherman Elementary School. The home's tremendous curb appeal & first quality luxury finishes will please the most discerning tastes. The open 1st floor plan includes complete chefs kitchen & family room with gas fireplace, butlers pantry leading to coffered dining room & open sitting room. Up mid-flight over pristine 2 car garage, is a private en suite bedroom perfect for guest, in-law, au pair or home office. On 2nd floor, find primary bedroom with double walk in closets & balcony overlooking backyard. Luxurious primary spa bath incl huge double vanity, soaking tub and generous walk in shower. Next is laundry room w/ sink and 2 more large jack & jill bedrooms connected by lovely full bath w/ double sinks. The 3rd floor is a perfect 5th en suite bedroom, family room, or office. Step out onto the top floor balcony, or relax on the private covered rooftop deck and take in tempting water views. Lovely fenced backyard incl large bluestone patio and covered loggia gathering area, playspace & new generator. Come see all this lovely home offers in comfort, style & convenience- steps to the beach & just a mile to town & train.

This beautiful Sasco Hill estate includes four buildings on a beautifully landscaped 4.42 acre private lot. The main house, a farmhouse colonial is 6934 SF with 5 bedrooms and 4.5 bathrooms. The guest house has a full apartment on the 1st floor with a 2nd level private office. There is a fully finished lower level gym with a full bath, steam shower and large work out area. Each level has a separate entrance. In addition, there is a 863 SF heated and air conditioned pool house with full kitchen, full bathroom, family room with fireplace, laundry room and changing area. The fourth building is a 1800 sf 6 car garage with a heated and air conditioned commercial chef kitchen. There is a walk up 2nd level above the garage for additional storage. On the opposite side of the arched breezeway, is a large climate controlled white oak wine room with 10' ceilings which is attached to a wine tasting area and sunroom. In addition to the four buildings on the property, there is tennis court and a large covered patio with a stone fireplace and outdoor kitchen located in the pool area. Please see photos and be sure to watch the virtual tour for more details on this one of a kind ,beautiful Southport 4.42 acre estate.

A Luxury Townhouse with 3500 square feet offers an exceptional living experience in every detail. With its spacious layout and carefully crafted design, this townhouse boasts a perfect blend of elegance and comfort. Upon entering, you'll immediately notice the thoughtfully designed interior that exudes sophistication. The townhouse features 4-5 generously sized bedrooms. Each bedroom is featuring high-end fixtures and luxurious finishes. The townhouse offers the convenience of a 2-car garage, And for those seeking ease of movement between floors, an elevator is seamlessly integrated. The heart of the home is the gourmet kitchen, a culinary haven equipped with top-of-the-line appliances. Natural light and fresh air abound with the inclusion of balconies, These balconies provide a perfect vantage point to take in views of the surroundings while maintaining an intimate connection to the outdoors. Attention to detail and craftsmanship is evident throughout the entire townhouse, with high-quality materials and finishes enhancing the overall aesthetic. From the rich hardwood flooring to the intricately designed lighting fixtures, every element contributes to an ambiance of opulence and refinement. Images are of builder's recent work and examples of what's to be built. There's still time to customize and make this your own. WALK TO TOWN, BEACH, TENNIS, RESTAURANTS AND SHOPS.

Welcome to Fairfield! Fabulous in-town location minutes to the beach!! Newly renovated kitchen with new appliances and bathrooms....freshly painted for the new owners! Four bedrooms, 3-1/2 bath, sun-filled public room, inviting sunporch, mudroom, deck off the 3rd floor overlooking the back garden and 2-car garage make this a perfect choice! Move right in and make this your new home......new windows, new roof, new HVAC with 3 zones for heating/ac. 4th Bedroom with deck access on 3rd floor could be family room/office! Perfect!

Experience the epitome of modern living in this stunning property nestled within the private Shorefront Park association. From the moment you step inside, natural light floods the space, accentuating the impeccable finishes that adorn every corner. With seamless transitions between indoor and outdoor areas, the expansive living spaces cater to both intimate gatherings and large entertaining. The heart of this home lies in the sleek German kitchen, equipped with top-of-the-line Miele and Sub-Zero appliances, custom cabinetry, and a spacious island for culinary creations. Immerse yourself in unparalleled sound quality with the built-in Sonos sound system spanning all three stories. Step outside and discover your own private oasis, perfectly landscaped and complimented with a glistening pool, and inviting lounge and dining areas. Take a moment to relax on the front porch and soak in the breathtaking views of the Harbor, including front-row seats to the mesmerizing 4th of July fireworks display. Beyond the confines of this property, Shorefront Park offers unique amenities including two private beach areas ideal for launching kayaks and paddle boards. With proximity to SONO's vibrant dining, shopping, and entertainment scene, as well as easy access to the train station just a stroll away, this property offers the perfect blend of tranquility and convenience, all just 60 minutes from the bustling metropolis of NYC. Agent/Owner FEMA compliant.