Lewisboro NY Real Estate & Homes for Sale

BETTER THAN NEW WAITING JUST FOR YOU! Welcome to 10 Tommys Lane, South Salem! This charming & completely updated 1 level 3-bed, 2 bath home is ready to welcome a new owner. The bright and open kitchen with an island, stainless appliances & quartz countertops is a perfect spot to whip up a new recipe. The cozy wood-burning fireplace is the focal point of the spacious Living Room. Fresh new bright Bath Rooms. You'll love the hardwood floors throughout the house Enjoy a sunny day on the deck over looking the private back yard. Additionally there's an 2 car attached garage It's the real deal!

NEW Listing in a prime location! This farmhouse-style home boasts a completely refreshed kitchen with brand new countertops and flooring, as well as freshly painted interiors. Conveniently situated near the New Canaan train station, shopping centers, and restaurants, this property offers easy access to amenities. Step into a welcoming foyer leading to a spacious living room with a cozy fireplace and an adjoining dining area. The eat-in kitchen, which opens onto a deck, is perfect for entertaining guests. Additionally, the main level features an office and a guest room. Upstairs, the master suite awaits with a recently renovated bathroom, vaulted ceilings, ample windows, and a walk-in closet. Three more generously sized bedrooms provide plenty of space for family or guests. The walk-out lower level includes a mudroom, den, laundry facilities, and ample storage space. Outside, a separate three-bay barn/garage offers parking for five or more vehicles, along with a workshop area suitable for motorcycles and heavy equipment. Surrounded by lush foundation plantings, lawns, woodlands, and a tranquil pond, this property offers a serene landscape for relaxation and enjoyment.

Step into a world of enchantment with this captivating 2-bedroom, 1.5-bathroom cape-cod style cottage nestled amidst serene nature in the heart of South Salem. Surrounded by absolute serenity and beautiful scenery, this property exudes charm reminiscent of a magical fairytale. Meticulously maintained, the all-original house retains its timeless allure while offering modern comfort and convenience. Recently upgraded with a brand-new boiler, warmth and comfort are ensured throughout the seasons. The spacious bedrooms provide a cozy retreat, inviting relaxation after a long day. Perfectly situated, this cottage offers the ideal blend of rural tranquility and urban convenience. It's not just a haven for nature lovers; it's also a commuter's dream retreat, being within an hour's reach of NYC. Whether you're seeking a peaceful escape or a charming residence to call home, don't miss the opportunity to own this slice of paradise in South Salem. Schedule a viewing today and immerse yourself in the enchanting ambiance of this captivating cottage.

Elegant Estate Living in Tranquil Splendor. Welcome to this stunning retreat nestled on 1.94 acres of lush, manicured grounds. As you approach the grand entrance, you'll be greeted by the stately main home, with 10-foot coffered ceilings, 9,656 square feet of living space spanning across 4 finished floors, chef's kitchen equipped with top-of-the-line appliances, a breakfast room, and a convenient coffee bar, 6 bedrooms and 6.5 baths, a third floor play room or theater, and a lower level featuring an additional rec room, wet bar, exercise room, and workshop. Step outside to a private, flat backyard and discover the sparkling over- sized pool, surrounded by lush gardens and a charming pool house. Imagine lazy summer afternoons lounging by the water, sipping cool drinks, and entertaining friends and family in your outdoor paradise.

Fabulous contemporary privately set on two acres in a convenient locale. Designed for easy living, entertaining and working from home year-round or as a weekend retreat. Welcoming two-story entry with abundant natural light through clerestory windows and skylights provides an instant wow factor. Enjoy views of the open yard through generously sized living and dining room windows. The sleek kitchen with large center island flows into a cozy den, mudroom, powder room and out to a lovely deck, rolling lawn and stone walls. A separate office flexes as a studio or gym. The upper level features a large primary bedroom with spa bathroom; two bedrooms, bathroom, laundry room, and a mezzanine area - perfect as office/den/guest space. This special property is approximately one mile from Scotts Corners. Ideally located close to nature preserves, the elementary school, town park, award-winning golf, The Inn by Jean-Georges, New Canaan shops, restaurants, and train.

Completely refreshed in 2024! This beautiful, classic colonial is situated on a quiet cul-de-sac, providing a sense of peace and tranquility. As you approach the gated entrance, down an allee of flowering pear trees, you're greeted with an estate-like feeling that sets the tone for what's to come, and you'll be delighted to discover a beautiful and level 2.1-acre lot, creating a private setting for you to call home. Step into the backyard oasis, and you'll be amazed by the spectacular in-ground heated pool with spa and waterfall, all perfect for those warm summer days. The deck, gazebo and summer kitchen offer an ideal space for outdoor entertaining, while the lush greenery imparts a sense of serenity that's hard to find. Inside, the sun-filled great room is the perfect place to relax and unwind, while the custom kitchen with center island offers plenty of space to prepare your favorite meals. The luxurious primary suite provides the perfect place to rest and rejuvenate after a long day. For the artist in you, the art studio (or 5th Bedroom/Home Office) with vaulted ceilings and fireplace provides a peaceful space to unleash your creativity. This property offers the perfect blend of luxury, privacy, convenience, making it the perfect place to call home. Just down the road are recreation facilities at the Onatru Farm Park with fields for baseball, soccer and lacrosse, tennis courts and a play area. Easy commute to NYC, just 54 miles to Grand Central Terminal.

Sophisticated and spacious 4 bedroom home set on 3 acres close to town and the border of New Canaan. Quiet and private street, lovely setting with mature plantings. Well cared for home with tasteful upgrades and a convenient floorpan. Bright and open with high ceilings throughout. Many windows and natural light with beautiful attention to detail. Home office with French doors off the entrance, bonus room on second floor with many possibilities. Large lower level area perfect for the home gym and walkout to the outdoors. Potential pool site. Peaceful and quiet setting yet all the conveniences nearby, 5 minutes to Scott's Corners and 10 minutes to downtown New Canaan and the train.

Stunning proposed new transitional home nestled on 2.78 acres in private nature setting with reservoir views. This exquisite home will be stylishly designed with high end finishes and gracious open living spacious. Additional 2000+sqft can be finished in lower level. Plans and specifications can be customized to your specific needs. Pool site available.

Welcome to 25 Lukes Wood Road (aka Father's Folly), one of the most unique homes and desirable neighborhoods in New Canaan. A straight shot along beautiful Oenoke Ridge from the vibrant downtown, you will be immediately captivated by its covered front porch and sunny upper deck. You will not be disappointed when you walk in the front door and see all the light! The heart of this home lies in the inviting living spaces, especially a gracious living room with a fireplace, picture window overlooking the private yard and access to the terrace with a stone fireplace. The eat-in gourmet kitchen is a chef's dream. A butler's pantry leads to the formal dining room and light filled family room, a favorite gathering spot. The designated office, first floor guest suite, and expansive mudroom complete the first floor. Upstairs you'll find an incredible great room with a cathedral ceiling, rustic beams and balcony. The two story primary suite, with dressing room and spa like bath, opens to a large western facing balcony. The four additional bedrooms have en-suite baths. The finished 3rd floor provides endless possibilities, from a gym, art studio, playroom ... The expansive flat yard is perfect for outdoor recreation and entertaining, from soccer games to garden parties and a potential pool site. There is even a sugar shack for continuing the tradition of making your own syrup. LOCATION is key! Nearby Scotts Corner, Bedford and Vista provide even more options for dining and shopping.

The owners have spared absolutely no expense on this 11,000+SF masterpiece, which is a testament to luxury, comfort, and elegant living with abundant dining & entertaining spaces. This 6-bed, 11-bath estate rests on nearly 2.5 perfectly manicured acres in a prime westside location. Expansive windows allow sunlight to flood into every room boasting a seamless open layout & fabulous views of the 30 x 50 outdoor lagoon pool and flat yard. Quartz countertops in the newly finished Chef's kitchen with 60'' Wolf and Sub Zero refrigerator/freezer, double dishwashers, built in banquette that can seat up to 14 guests. Other luxuries include: 3 car heated garage, full house automatic generator, 1500 SF finished walkout LL, primary suite w baths/closets in separate wings for privacy, radiant floor and fireplace- you'll feel like you've escaped to the most amazing vacation retreat! Don't miss this one! Spa-like primary suite bathrooms- including one of which offering radiant flooring, a steam shower, soaking tub, beverage fridge. The entire home has custom insulation for effective heating/cooling. Resort-Style Amenities: 30 x 50 Lagoon pool, brand new two story guest/pool house w kitchen/full bath/W/D, lush landscaping provide tranquility, walk out lower level w extra bonus room, bath, media/theater, temp controlled wine cellar. 3 Car Heated Garage: Ideal for car enthusiasts. Plus, a mudroom just inside of pool/patio area, with radiant flooring/full bath.

Also, just listed as FURNISHED MLS #170608924. Drive through the electronic iron gates to a breathtaking 18,000+ SF, 3-story residence of handcrafted brick and imported French slate capped roof conveying a sense of permanence, substance & Old World quality reminiscent of grand country homes of Europe. On 6+ acres, tailored for an American lifestyle this European style home is met inside w/a balanced mix of classic luxury and relaxed modern-day conveniences & furnishings accentuated by contemporary art. Designed with two wings, this home hosts business associates & entertains guests without having to sacrifice the on-going family activities. North wing w/2-Story Library, Conference/Reading rm, Main Office, Bar, Living & Music rms. Accessed through a separate courtyard entrance, the South wing includes Dining rm, Parlor/Reception rm, 2nd Office, Valcucine ergonomic Kitchen, Breakfast area, Family rm, Back Staircase, Service/Mudroom, Fitness Center w/Sauna. 2 Laundry rms. Primary suite w/Sitting rm, 2 Fireplaces, 2 Baths, WIC, Dressing rm & Terrace. 6 add. en-suites w/Porcelanosa baths. Bespoke Millwork, Chandeliers, Floor-to-Ceiling Paneled Walls & French Doors w/Transom Windows. 8 Chesney fireplaces. A family-wellness focused estate w/enticing, extensive indoor & outdoor features & activities. Private fresh water pond. Pool. Tennis Court. 2,000SF Cottage. Heated Garage w/auto exhaust. 10-12 family cars or 25 collectible cars. Details Beds, Baths, More on 266MichiganRoad.com

FURNISHED. Move In For Holidays! On 6+ acres, tailored for an American lifestyle this 18,000 SF European Style home is met inside w/a balanced mix of classic luxury and relaxed modern-day conveniences and furnishings accentuated by contemporary art. Curated by DDC-NYC from a global selection, the furniture was chosen in ways that maximize elegance, style, sophistication & functionality. Designed to host business associates and entertaining without sacrificing the on-going family activities, the home has two distinctive wings. North, with 2-Story Library, Conference/Reading rm, Main Office, Bar, Living and Music rms. Accessed via a separate courtyard, the South wing includes a Dining rm, Reception rm, 2nd Office, Valcucine ergonomic Kitchen, Breakfast area, Family rm, Back Staircase, Service/Mudroom. 2 Laundry rms. Primary Suite with Sitting rm, 2 Fireplaces, 2 Baths, WIC, Dressing rm and Terrace. 6 addit. En-Suites w/Porcelanosa Baths. Bespoke Millwork, Italian Chandeliers, Floor-to-Ceiling Paneled Walls, French Doors with Transom Windows. 8 Chesney Fireplaces. A family-wellness focused estate with enticing, extensive indoor and outdoor features & activities. Fitness Center w/Sauna. Viewing Anteroom leads to Game rm. Home Theater and Wine Cellar. Private fresh water Pond. Pool. Tennis Court. 2,000SF Cottage. Heated Garage with auto exhaust for 10 family cars or up to 25 collectible cars. Details incl. beds & baths on 266MichiganRoad.com. Unfurnished listing #170591063

What a compound this is! A classic colonial transformed into a modern chic estate with over 6,200sqft. Gorgeous updated kitchen and tons of amazing entertaining space inside and out. The brand NEW primary suite is awesome with two fireplaces, sitting area, dual walk-in closets and bonus office suite with deck overlooking the stunning grounds. Four acres of privacy with custom pool, jacuzzi and waterfall. Fantastic guest house with over 2,400sqft of living space, full kitchen, fireplace, putting green and room for six cars. Simply spectacular in a magical setting!

Welcome to 277 South Bald Hill Road, a stunning center hall Colonial nestled in the picturesque town of New Canaan, CT. This spacious 4-bedroom, 2.5-bathroom home offers over 4128 square feet of beautifully designed living space, making it the perfect retreat for first home buyers, growing families, or those looking to escape the hustle and bustle of NYC.Situated on a sprawling 4.31-acre lot with tranquil pond views and lush landscaping, this property offers an idyllic setting for both relaxation and entertainment. The home's generous size rooms boast a seamless circular flow, and two cozy fireplaces in the living room and family room create inviting spaces to unwind.The renovated, expansive kitchen is a chef's dream, featuring stunning granite countertops, a large island, and a charming eat-in area. Elegant paneling in the dining room adds a touch of sophistication, perfect for hosting family dinners and gatherings. A private office off the kitchen provides the ideal workspace for those working from home.The family room's vaulted ceiling adds to the home's spacious atmosphere, while large windows throughout the home allow for an abundance of natural light to fill each room. Enjoy the peace and privacy that this beautiful home offer.Don't miss this incredible opportunity to own a piece of New Canaan's private landscape and open space. Schedule a viewing today to experience the beauty and charm of this stunning property for yourself.

Welcome to 34 Louises Lane, where sophistication meets practicality in this beautifully appointed home. Recently repainted on the outside and in move-in condition, this residence boasts a double-height entry gallery leading to 5900 sq ft of light-filled living space. From an elegant living room and dining room to a chef's kitchen that opens to an expansive family room with cathedral ceiling, every detail exudes luxury and comfort. The home features a tremendous bonus room, exercise room, and a 1500-bottle wine cellar, perfect for entertaining or relaxation. The serene first-floor master suite and four additional bedrooms, two with hidden playrooms attached, offer ample space for family and guests. Outdoor entertaining is effortless with two terraces and a heated saltwater pool with a kitchen area, creating a haven for enjoyment and relaxation. This meticulously maintained property is ready to welcome you home.

Nestled on one of the highest points on Kitchawan Road, this fabulous light-filled 3-bedroom, 2.5 bathroom home offers 2256 square feet of spacious living space. With the added bonus of a 4 bedroom septic, this home offers great flexibility for expansion. Set on a half acre level lot with mature landscaping, the main level welcomes you with a spacious foyer leading into a bright and airy living area complete with fireplace and adjacent dining room. The eat-in kitchen is equipped with new appliances leading out to a covered patio perfect for entertaining. Additionally, the main level includes a den offering the perfect space for a home office, complemented by a convenient powder room. Also on the main level is one large bedroom featuring an ensuite bath and an additional room with patio access. On the second floor, you'll find a generously sized second bedroom with versatile possibilities, a full bath and a third bedroom with two spacious closets. The property is located in a serene outdoor environment. In addition to its many upgrades, also featured is a new well pump installed in 2024. A prime location just 10-15 minutes to Ridgefield, Bedford, Pound Ridge, New Canaan, and Katonah. Outdoor enthusiasts will appreciate the proximity to Ward Pound Ridge, Leon Levy Preserve, Onatru Park and all the amenities of Lewisboro Town Park, including a playground, and a state-of-the-art town pool and tennis courts. With its convenient proximity to various recreational and lifestyle amenities including world class dining and shopping, this home provides an idyllic retreat while still being in proximity to NYC.

Real North Country feel the moment you turn onto this unique, private road in Pound Ridge - like stepping onto the wooded lane to the lake in New Hampshire or Maine. Cute cottage with lot's of potential/needs lot's of work/sold strictly as is. Cash offers only. Short hike to large, clear lake. A worthy project and a special place.

Welcome to this exquisite stone and shingle home, an extraordinary masterpiece built in the timeless English Cotswold tradition. Updated in 1999 and again in the early 2000's, this impeccably designed home showcases unparalleled craftsmanship, and captivates with its attention to every detail, offering a truly custom living experience. As you step inside, you'll be greeted by the allure of Palladian windows, arched doorways, and meticulously crafted custom moldings that adorn the interiors. The ambiance of this home is one of elegance and charm, with a seamless blend of classic antiques and modern comforts, creating a harmonious living space. The heart of this enchanting estate is its stone pool, where you can bask in the sunlight and enjoy refreshing swims on warm summer days. A gated entrance leads to the meticulously landscaped gardens surrounding the fenced-in property, which boasts a myriad of vibrant flora and whimsical sculptures. This stone and shingle manor house offers a rare opportunity to reside in a truly unique and captivating residence. Embrace the charm of the English Cotswold tradition, paired with modern luxury and convenience, in this exceptional home.

Welcome Home! This pride of ownership, classic Colonial-style residence in sought-after South Ridgefield is perfectly sited on an acre of pristine, level property and boasts everything you need for modern living incl a great floorplan, multi-use spaces, hardwood floors and plenty of natural light from an abundance of large windows. The heart of the home is the impressive eat-in kitchen with beautiful Corian counters, stainless appliances and crisp white cabinetry. The adjoining family room features a wood-burning fireplace as well as French doors to the patio and yard beyond. The perfect floorplan continues with a spacious dining room for easy entertaining, a living room which can also function as a library or music room and a half bath. A practical mudroom with access to the 3-car garage creates a seamless flow for the deposition of groceries, sports equipment and winter boots! Upstairs, the primary suite does not disappoint with a large walk-in closet and an updated full bath including a vanity with double sinks, a relaxing stand-alone tub and separate shower. 2 spacious bedrooms share a Jack and Jill bath with 2 additional bedrooms accessing a hall bath. The finished lower level includes a large rec room which can be repurposed as an office, playroom or media room, as well as a dedicated gym. The park-like, level backyard has a relaxing patio and is surrounded by mature trees. Great location close to major routes south for an easy commute to NYC and lower Fairfield County.

Welcome to a truly exceptional New Canaan architectural masterpiece built in 2004, nestled on a majestic private lane occupied by only 6 estates, enveloped by serene forests and 48 acres of reservoir conservancy. This picturesque estate offers a tranquil escape and sense of openness with intricate millwork and wainscoting adorning every corner, 9 to 12-foot ceilings on every level and sun-drenched spaces throughout. Spanning over 11,000 square feet, with an additional 4,000SF+ lower level, with 6 bedrooms, 7.2 baths on 4.7 acres with room to add a custom pool, step inside to discover a seamless blend of ultimate privacy and modern luxuries throughout 4 finished levels. Immerse yourself in the serenity just 5 minutes to downtown New Canaan and an hour to NYC, where luxury and tranquility converge in perfect harmony.

This modern, light-filled home on 4 private acres is located in an estate area at the end of a cul-de-sac with an easy drive to town. Custom-built to maximize natural light, the European windows and glass doors showcase the property's beautiful natural surroundings. The thoughtful open design offers options for gathering with an elegantly informal floor plan. A stunning two-story entrance opens to the great room with fireplace, adjacent formal dining room and a front-to-back view of the glass enclosed all season sunroom with stone fireplace.The great room opens to a custom finished kitchen made for entertaining with butler's pantry and a dedicated prep kitchen/pantry space. A breakfast room with vaulted ceiling connects to an outdoor patio and grilling area. On the second floor, the primary suite has a fireplace, balcony, a custom walk-in closet and spa-like bath. The comfortable guest suite has a sitting room with fireplace & kitchenette.The second floor has two additional ensuite bedrooms.The upper floor features a 2 br. suite with custom closets, vanities, a tiled shower room, a living room and reading nook. The lower level has game room,media area, kitchenette, gym, bedroom, and full bath. Set in a quiet neighborhood with wide streets, this is a walker and cyclist's paradise. Peaceful privacy, abundant flat land, and relaxed livability make this a unique offering.

THE HOUSE THAT HAS IT ALL- Sophisticated yet totally livable 5 bedroom Contemporary home designed by noted architect Vuko Tashkovich (trained under I.M. Pei & Eliot Noyes) and sited on 3.27 acres of spectacularly landscaped property with a pool, pool house with a changing room, bath and outdoor shower, a 1/2 basketball court, sports field and lake with a dock- perfect for kayaking, fishing, etc. Minutes to the charming town of Pound Ridge, Scotts Corners, with farmers markets and an array of eclectic shops and restaurants. The public spaces flow beautifully with walls of glass showcasing the verdant views of the outdoors. All of the rooms that a buyer could desire are here: renovated eat-in kitchen, screened/glassed in porch, work-out room, home offices, family room, guest suite and more. The outdoors have mature specimen plantings including Japanese Maples, Dogwoods, Weeping Beech, Lilacs, Weeping Cherry- mesmerizing views from every room.

Exquisite Contemporary Colonial nestled on 3+ acres of bucolic woodlands with flowering perennials, specimen plantings, and stunning outcroppings. This modern farmhouse is offered in pristine, move-in condition with sought-after amenities, quality detailing, and superb craftsmanship. Includes custom millwork, wide-plank wood floors, soaring ceilings with hand-notched wood beams and 3 fireplaces. Effortless flow enhanced by oversized windows and glass doors providing abundant natural light. Main level encompasses formal Living & Dining Room that open to two large decks, eat-in chef's Kitchen w/dutch door, all-season Sunroom, & Powder Room. Three Bedrooms on 2nd level including Primary Suite w/fireplace, loft & luxurious en-suite bath w/heated floors. Lower level features spacious Family Room w/walk out slider to stone patio. New whole house generator, Lutron lighting, Sonos sound system, bluestone walkways, & fresh paint inside and out. Quiet cul-de-sac just minutes to Scott's Corners.

Introducing this newly constructed masterpiece by Nordic Builders, a beacon of modern elegance and sophistication. Located amongst other prestigious estates, this modern farmhouse boasts a stunning three-story entrance, complete with elegant lighting and a striking glass-enclosed staircase. And that's just the beginning! Designed with meticulous attention to detail, the property showcases 10-foot ceilings, custom oversized European windows and doors, intricate moldings, three fireplaces and more. A showstopping custom kitchen, ideal for culinary enthusiasts, leads into the inviting family room, the heart of the home. Additional features include a grand glass sunroom with accordion doors opening to a landscaped backyard, an outdoor kitchen, pool, and fire pit. spacious library, a mudroom, a four-floor elevator, and an attached heated three-car garage. The home features 6 spacious en-suite bedrooms, 7 full baths and 2 half baths. The highlight of the home is the expansive custom primary suite with a private deck, and luxurious bathroom with radiant heated floors, touch-activated mirrors, elegant eggshell bathtub and an advanced shower system. Everywhere you look, the magnificent home embodies "Best in Class," redefining luxurious living for today's discerning buyers!

ONE OF NEW CANAAN'S FINEST ESTATE PROPERTIES. A peaceful, private refuge sited high on Oenoke Ridge offering panoramic distant views. Over 5 park-like acres overlooking the New Canaan Reservoir and surrounded by some of New Canaan's finest estates and country properties. Spectacular grounds featured in multiple magazines & garden tours, and recipient of several landscape design awards. A tranquil, bucolic backdrop combining a natural stone hardscape with an array of specimen plantings and a wildflower meadow with trail. Pool with spa flanked by a pergola-covered dining terrace & an outdoor stone fpl. Mature, producing apple orchard&peaceful perennial garden w/terrace &water feature. Intriguing&dramatic renovated 19th Century barn converted by the Hobbs family retaining original antique hand hewn beams&details while incorporating more recent updates from architects Lousie Brooks and Joeb Moore. Nearly 6400 square feet of impeccably finished living space with high ceilings, exposed posts and beams, random-width floors and walls of windows to capture light & views. Stunning 2-story LR w/massive floor-to-ceiling stone fpl & whimsical catwalk w/shelving creating a 2nd flr library. Sun-filled DR. Fabulous Louise Brooks Kit connects to outdr dining space & Fam Rm. 6 BRS inc. 1stFlr Primary Suite/Bat designed by Joeb Moore. Gym &RecRms. Lg deck&expansive lawns for outdr entertaining. Det 3-car Garage w/2nd Flr Office/Great rm plus Guest Suite. Sep drive provides addl parking.Rare!