Lewisboro NY Real Estate & Homes for Rent

Looking for space, privacy, and a home that feels like a retreat? This classic 4-bedroom, 3.5-bath colonial sits on over 8 acres of peaceful land and is available for annual or extended rental. The home has tons of character with modern updates throughout - updated kitchen with newer appliances, refreshed hardwood floors, renovated bathrooms, and a light-filled family room with a beautiful solarium. There's also a partially finished lower level and laundry room with newer washer and dryer. The home has two two-zone central air/heating system and a full-house generator for peace of mind. The best part? The landlord takes care of the lawn maintenance, so you get all the beauty of the outdoors without the hassle. Whether you're relaxing at home or entertaining guests, the property offers tons of space to spread out and enjoy. It's a unique and welcoming home you won't want to miss!

Discover the perfect blend of elegance and modern comfort in this newly renovated home nestled on two serene acres in New Canaan. Boasting five spacious bedrooms and three and a half baths, this home offers ample space for relaxation and entertaining. The heart of the home is an open floorplan kitchen and dining area, featuring a large kitchen island perfect for culinary creations and gatherings. The formal living room and the family room each have a working fireplace, creating warm and inviting spaces. Upstairs, a fully finished third floor provides a dedicated office space, ideal for those who work from home. The property also includes a large bonus room above the two-car garage, which can serve as an entertainment area or exercise space. With an additional room on the main floor available for home office use, this property accommodates today's need for versatile work and living spaces. Every corner of this home has been thoughtfully updated with modern finishes, ensuring a luxurious and comfortable lifestyle. Experience the best of New Canaan living in this exceptional rental property, where every detail has been designed for your comfort and convenience.

SUMMER SEASONAL RENTAL - (6 weeks preferred) available July 12 - August 23rd. Looking to escape the city for a countryside retreat in a private setting that provides plenty of room for entertainment, an in-ground heated pool, tennis court, golf chipping area, trampoline & opportunities to explore the mature gardens? Look no further...Experience all that summer has to offer at your own private summer camp. Sprawling 5 bedroom, 5.5 bath country ranch on 4+ private acres. Spend warm summer days by the pool, host your own tennis tournament or play games on the rolling lawn. Enjoy relaxing summer nights dining al fresco by the pool or watching shooting stars sitting by the firepit - life doesn't get better than this. Many recent updates to this home give it a chic modern vibe. This rental is $36K a month. For each additional week over a month there is a $9K per week.

Welcome to this stunning modern farmhouse, a perfect blend of timeless charm and contemporary comfort. Nestled on a peaceful cul-de-sac in Wilton, this 4-bedroom, 3-full-bath home offers an ideal retreat surrounded by serene natural beauty. Step inside to discover soaring ceilings and an open floor plan that seamlessly connects the living, dining, and kitchen spaces-perfect for everyday living and effortless entertaining. Oversized windows flood the home with incredible natural sunlight, enhancing the warm, inviting ambiance throughout. The thoughtfully designed layout features a luxurious primary suite complete with a walk-in closet and spa-like bath, plus three spacious additional bedrooms and beautifully appointed full baths. A versatile bonus room on the second floor offers space for indoor play for those rainy summer days. Set on a level property, the home includes a covered patio with outdoor TV and an exceptionally private, flat backyard-ideal for entertaining, gardening or play. Located just minutes from both Wilton Center and Main Street Ridgefield, you'll enjoy the best of both towns with boutique shopping, dining, top-rated schools, and easy commuter access. Experience exceptional modern farmhouse living in a truly picturesque and peaceful setting. Available from mid June through Mid August.

THIS MAGNIFICENT ESTATE HAS BEEN FEATURED IN THE N.Y. TIMES MAGAZINE FOR ITS EXTRAORDINARY ENTRY AND CONSTRUCTION. BE IT THE OVERSIZED POOL, ELEVATOR ON ALL 3 FLOORS, SPORTS & TENNIS COURT, MEDIA ROOM, HIS & HER BATHS WITH SEVERAL ADDITIONAL PRACTICAL AND FUN AMENITIES LIKE A CUSTOM BUILT BAR, TWO STEAM SHOWERS, UPSTAIRS AND DOWNSTAIRS LAUNDRY ROOMS, AN EXERCISE ROOM WITH EQUIPMENT, POOL TABLE, SAUNA, WINE ROOM, ETC. ETC. IT CAN BE RENTED PARTIALLY FURNISHED. TV'S, STEREO SYSTEM INSIDE AND OUTSIDE GRACE THIS ONE OF A KIND BEAUTIFUL BRICK HOME WITH PRIVACY ON ALL SIDES BUT CLOSE TO THE MAIN ROAD THIS HOME BOASTS ONE OF THE TOP SCHOOL SYSTEMS AND SPECIAL ED. PROGRAMS IN CT. STONE WALLS & SPECIMEN PLANTINGS ABOUND. NEW CANAAN IS ONE OF THE SAFEST COMMUNITIES IN THE TRI STATE AREA, A MUST CONSIDER IN THESE TIMES. IT IS A MUST SEE. YOU WILL NOT BE DISAPPOINTED. AN ENTERTAINERS DELIGHT FOR GATHERINGS OR JUST CONDUCTING BUSINESS FROM HOME. THE BEAUTY OF ITS LANDSCAPING, MOLDINGS, VERANDA AND CLASSIC DESIGNS ARE RARE IN TODAY'S BUILDING COMMUNITY. WITH THE HIGHEST QUALITY CONSTRUCTION IT WAS BUILT BY A MASTER BUILDER WITH ITS CURRENT OWNERS AND IT IS IN TURN KEY CONDITION.

ONE MONTH SUMMER RENTAL - Available July 20 - The perfect summer retreat! This beautifully elegant and relaxing 5 bed, 4.5 bath country home is set on 2 acres with sweeping lawns front and rear in a sought-after neighborhood, less than 3 miles from downtown New Canaan's must-try restaurants, shops and train. Gourmet eat-in kitchen, light-filled rooms throughout and game room with pool table and dart board make this the perfect home-from-home with outdoor dining and living areas including a sparkling, heated, gunite pool, patio and stone fire pit. 5th bedroom with full bath on main floor currently being used as office but owners can move twin bed from lower level, if desired. Sleeps 10 comfortably. Discover all that New Canaan has to enjoy, including walking trails, nature center, parks, spectacular new library and only 45 miles from NYC

Welcome to 60 Squires Lane, an exceptional rental opportunity nestled at the top of a peaceful cul-de-sac on the west side of town. This beautifully maintained 5-bedroom, 3.5-bath home offers space, style, and serenity on over 5 acres of lush, private grounds. Step inside to find sun-drenched rooms, gleaming hardwood floors, and a gracious flow ideal for both everyday living and entertaining. The elegant living and dining rooms provide a classic backdrop for hosting, while the beautiful kitchen and lofty family room with vaulted ceilings and a cozy fireplace invite joy, relaxation and connection. The spacious layout offers five generously sized bedrooms, including a serene primary suite, and multiple flexible spaces perfect for a home office, playroom, or guest quarters. Enjoy outdoor living surrounded by nature, with plenty of room to explore, play, or simply unwind in total privacy. All just minutes from New Canaan's charming village center, top-rated schools, shops, dining, and train to NYC.

Spend the summer in beautiful Connecticut by the pool, or enjoy beaches and boating on the Long Island Sound, just 6 miles away from this elegant and stately 7-bedroom New Canaan estate with a refined elegance for sophisticated yet comfortable living. The versatile spaces, unique design elements and thoughtful layout are perfect for casual gatherings or elegant, formal entertaining. The property boasts a brand new pool and gazebo, sweeping lawns and gardens, gracious covered porches, and expansive blue stone terraces. Designed by premier builder Alex Kaali-Nagy and decorated by Lynn Morgan, this exceptional West Road residence has unparalleled attention to detail. Luxurious amenities include a full house generator, three-floor elevator access, seven en- suite bedrooms, large chefs eat-in kitchen, wet bar, main and upper floor family rooms, and a lower-level gym, This impeccable beauty should not be missed.

Welcome to the former residence of Ace Frehley of the iconic band KISS. Cross through iron gates, over a stone bridge and up a circular driveway with garden pond and waterfall and arrive at this 6400 sf 5 bedroom 6 1/2 Bathroom home. Situated across from a 70 acre private farm w/ accessible hiking trails, makes this a perfect escape. Akin to something out of a magazine, this breathtaking home has wide open spaces, lots of glass & light. Come record in the restored studio, if you'd like :)

An incredibly rare opportunity to reside in a mid-century modern home designed by world renowned Harvard Five Architect, Eliot Noyes. In The Lee Ault House, originally built in 1951 and recently renovated with the utmost care and consideration for maintaining the brilliant mid-century modern design, the indoors and outdoors blend seamlessly to create a stunning, light filled home. You will delight in expansive views of nature, mature trees and level property with patios & courtyards and floor to ceiling glass walls throughout. This truly spectacular home is both minimalist yet inviting with new white oak floors throughout. The newly installed, state-of-the-art spacious kitchen/breakfast room which features Miele appliances, John Pawson stainless steel fixtures, a large island with Carrera marble countertops, and custom cabinetry. Bathrooms feature Carrera marble sinks and custom white oak cabinetry along with John Pawson fixtures and sink in the primary bath. The private and tranquil 4+ acre property was originally designed by Landscape Designer Thomas Church, and the home's original pool has been opened and heated. Available Furnished with flexible lease term. The furnished option includes Fritz Hansen furniture (interior), Carl Hansen patio furniture, and Francis Mallman grill. How wonderful to have the good fortune to live in a work of art. Offered as a flexible term furnished summer rental starting May 2025 through September 2025.

Beautiful 3 Bedroom 3 Bath Ranch Style Home set on 1.6 acre lot, Meticulous Maintained with trees and flower gardens, 1 car garage entering into lower level family room with cast iron fire fireplace, 1 bedroom on lower level with private bath and walk out to patio area, New Washer & Dryer, 2nd level 3 Bedrooms with 2 bath, Large Living Room with Fireplace and Bay Window, Dining Area with Slider Door to Wooden Deck, New Kitchen with Stainless Steel Appliances, Propane cooking gas, Quartz Counter-top and Back splash, Freshly Painted Rooms, All season Room with Heat, Covered Car Port, New Trane C/A System , Forced Air Oil Heat System, New Furnace, New Energy Efficient Windows, Well & Septic. Close to New Canaan Train Station, Easy Access to Merritt Parkway. Good Credit & References a Must (All offers to be considered must be submitted by Sunday 4/20/25 @ 12:00 pm)

Welcome to Gramercy Park! Exquisite, boutique enclave of eight luxury residences nestled in the heart of sought-after New Canaan, CT. Private and pristine, Unit 302 offers turn-key living, complete with elevator access & in-unit washer/dryer. This 3 bedroom, 3.1 bath residence features 2,417 sq. ft. of carefully crafted living space centered around a chef's kitchen with top-of-the-line SubZero/Wolf appliances, custom cabinetry & marble countertops, with seamless flow into an elegant main living/dining area. Light & bright primary bedroom with spa-like full bath w/marble finishes & generously-sized walk-in closet; 2nd Main Floor Bedroom and Den. Upstairs, 3rd bedroom & Family Room, open to below. A stunning, oversized covered balcony overlooking the serene & tastefully landscaped community garden for year-round outdoor enjoyment, 2 dedicated parking spaces (one covered - #302), ample guest parking and complimentary use of the community clubhouse with outdoor kitchen, seating area and fitness center w/TV & Internet access complete the package. Offering secure entry and 24-hour package room for added peace of mind, Gramercy Park is a modern sanctuary brimming with charm, steps from exceptional dining, bespoke retail shops, parks, and vibrant local events -- all one hour from Manhattan.

Timeless New Canaan gem! This renovated upper unit has 3 bedrooms, 2 full baths, 2 fireplaces and one attached garage space. Enjoy cozy evenings by the fireplace in one of two living rooms, original woodwork and soaring vaulted ceilings. The updated eat-in kitchen, complete with custom cabinetry, stainless steel appliances, and granite counters is perfect for hosting gathering. Step outside to a large, private patio, ideal for relaxing or entertaining. Steps from your door you'll find top-rated restaurants, boutiques, the farmers market, library, schools, and Waveny Park. Also nearby is Metro North and a quick hop to the Merritt Parkway. Fully separated utilities (electric, hot water) ensure flexibility. Don't miss this in-town treasure!

Timeless New Canaan gem! Single floor living, one bedroom, one bath lower unit with updated kitchen and washer and dryer in unit. Ample parking included. Steps from your door you'll find top-rated restaurants, boutiques, the farmers market, library, schools, and Waveny Park. Also nearby is Metro North and a quick hop to the Merritt Parkway. Fully separated utilities (electric, hot water) ensure flexibility. Don't miss this in-town treasure!

This bright and airy two-bedroom duplex spans two floors, and offers postcard views of Main Street. Completely reimagined in a 2023 gut renovation, this residence blends modern design, comfort and energy efficiency at the highest standards. The contemporary open-concept layout features glistening white oak floors, sun-drenched windows, quartz countertops, a sleek Bosch stainless steel appliance suite, ensuite bedrooms with stylish, spa-like bathrooms, a home office and a charming porch. Recessed lighting throughout enhances the home's sophisticated ambiance. Nestled in a prime heart-of-town location, this exceptional home is just moments from renowned restaurants, boutique shopping, the commuter express train, and all the best in-town amenities.

Nestled in the charming town of Wilton, Hayworth Wilton offers a beautifully renovated two bedroom two bath apartment home. Designed with modern living in mind, this home boasts spacious interiors that blend comfort and functionality. In-unit laundry, central air conditioning, off-street parking. Residents can unwind by the pool, stay active in the fully equipped fitness center, and enjoy the convenience of nearby parks, shopping, and dining. Combining serene surroundings with easy access to local amenities, Hayworth provides the perfect place to call home. Pets welcome. The nearby Metro North is less than a mile away and closely located to major highways. Minutes to shops, nightlife, and restaurants.

Just steps away from everything! This charming unit is minutes from town, shops, restaurants, and the train station. Freshly painted and move-in ready, it features a spacious eat-in kitchen with granite countertops, a brand-new dishwasher, and a refrigerator. Step out onto a generously sized deck directly from the kitchen. Elegant molding details add character throughout. Enjoy the convenience of an in-unit washer and dryer. A lower-level basement provides extra storage if needed. Private parking is available at the rear of the home, along with a designated garden area for those who love to plant. Area rugs are required to protect the flooring. No pets allowed.

This newly constructed apartment has the flexibility of a one-bedroom with a extra space that can be used as a second bedroom, office, or den. Located on a private lot along Route 7 in Wilton, the home provides a serene setting with a picturesque brook and expansive grassy field, all while being conveniently close to local amenities. Apartment Highlights: Custom Kitchen - Granite countertops & brand-new stainless steel appliances Luxury Bathroom - Elegant granite walls Highly Efficient Heating & Cooling - Keeps utility costs low Ample Parking - Plenty of space for tenants & guests Fenced-In Play Area Shared Picnic Tables - Enjoy meals outdoors Blue Stone Pathway - A charming entrance to your home Scenic Brook View - A peaceful, natural setting Massive Apartment - Spacious layout with flexible living options Additional Amenities: Mini split heating & cooling Private deck & yard space Dishwasher & in-unit washer/dryer Pet-friendly Water included A perfect blend of modern living and nature-don't miss out!

Welcome to this newly constructed, energy-efficient first floor 3 bedroom apartment located on a private lot along Route 7 in Wilton. Custom Kitchen with granite countertops and brand new stainless steel appliances refrigerator, range, microwave, dishwasher and washer dryer in the unit. Luxury Bathrooms featuring granite walls, Energy-Efficient Heating and Cooling. Amply parking for tenants and guests. Convenient location close to everything.

Welcome to this beautifully appointed 4-bedroom, 3-bath Colonial, just steps from Ridgefield's charming Main Street. Enjoy the ultimate in convenience with shopping, restaurants, library, Ballard Park, a movie theater, and more all within walking distance. This better-than-new home boasts a fully finished walk-out basement featuring radiant heated floors, a pool table, ping pong, and a full entertainment center-perfect for relaxing or entertaining guests. The main level showcases a gourmet chef's eat-in kitchen, a spacious open-concept living and dining area with gleaming hardwood floors, and abundant natural light. Upstairs, retreat to the luxurious primary suite with a spa-inspired bath and walk-in closet. Two additional spacious bedrooms, a full hall bath, and a convenient laundry area complete the upper level. The third-floor finished space offers flexible space ideal for a fifth bedroom, home office, gym, or playroom-whatever suits your lifestyle. Don't miss the opportunity to rent in this exceptional home that combines comfort, style, and an unbeatable location.

This beautiful, pristine studio apartment is located on a peaceful, private property in bucolic North Stamford. Enjoy the tranquility of this lovely setting, while still having easy access to stores, restaurants highways, and trains. This sweet studio apartment is the perfect retreat and is absolutely turnkey! There are fabulous, new light hardwood floors throughout. The kitchenette is fabulous and boasts lovely white cabinets and white/grey countertops. There is a new refrigerator and a dishwasher (no stove). This space opens into a small family room space, with some built in storage nooks. The adorable bedroom has a closet and is a cozy space. The Bathroom is pristine, has a shower and is in the same color palate as the kitchen. Heat, hot water and utilities included. No smokers, NO PETS. Studio is attached to main house but not accessible from main house. It has it's own separate entrance, private driveway parking and laundry room. A perfect retreat!

In the heart of downtown New Canaan, this 6,000+ sq. ft. residence offers 5 bedrooms, 4 full baths, and 3 half baths, blending elegance and comfort. The main level features a gourmet chef's kitchen with Wolf appliances, an expansive family room, and two dedicated offices. Soaring 9+ ft. ceilings enhance the light-filled interiors.Upstairs, the primary suite is a true retreat, boasting two-story windows, a spa-inspired bath, and a custom dressing room. Three additional bedrooms, two full baths, and a large second-floor laundry complete the level. The lower level is an entertainer's dream, with a home theater, wine cellar, and wet bar. Outside, expert landscaping, stone walkways, and a full outdoor kitchen set the stage for luxurious al fresco living. A private in-law/au pair suite above the garage offers a living room, bedroom, bath, and kitchenette-ideal for guests or extended family. This extraordinary home combines luxury and location-a must-see! Schedule your private tour today.

Fabulous 2 bedroom unit in the heart of Wilton! Kitchen and baths remodeled and updated! Fresh paint everywhere - Beautiful new hardwood flooring! Close to the pool and tennis court! Walk to everything Wilton has to offer - walk also to the train! Come see as it will rent quickly!

Inviting and spacious 1920 colonial convenient to Branchville Train Station. Walk to Tusk & Cup for coffee plus other vibrant shops/restaurants in the charming Branchville enclave. Total 1,400 sf with 3 bedrooms and 2 full baths including newly remodeled bath on the first floor. Freshly painted interior, hardwood floors, and new wall to wall carpet on the second floor. Expansive kitchen with dining area featuring gas range, open to large living room, plus additional den/office on the main level. The second floor features three spacious bedrooms and second full bath. Convenient laundry in the first floor sun room. Spacious backyard with .72 level acres; plus front porch and side patio. Mowing, plowing, and exterior maintenance is included. Shed & garage are excluded. Available for immediate occupancy. Move right in!

BRAND NEW Construction by Cypress Development in Prime New Canaan Location offering a new detached townhouse. Experience luxury living in this beautifully designed 3-bedroom townhouse, just a short stroll from downtown New Canaan. This new construction showcases an impressive open floor plan, with 9' ceilings and a seamless flow throughout the main living spaces. The gourmet kitchen, equipped with custom cabinets, granite countertops, and high-end appliances is perfectly integrated with the dining area, making it ideal for both casual meals and formal gatherings. The open living room offers a cozy retreat, featuring a modern fireplace that adds warmth and ambiance to the space. On the upper level, the Primary Suite offers a large walk-in closet and a luxurious spa-like bath with soaking tub, providing a serene space to unwind. Two additional bedrooms, two full baths, and a laundry room complete this floor. The fully finished third floor offers a versatile space, perfect for a media room or home office, while the fully finished lower level provides even more living options, with a recreation room and glassed-in gym. Expansive sliding doors lead to a private patio and green space, offering a peaceful outdoor area. Additional features include an attached 2-car garage. This townhouse is a perfect blend of luxury and functionality, offering spacious living in an unbeatable location.