Homes for Sale in New Canaan, CT with 5-Bedrooms

The "Legacy Estate" An Oenoke Ridge Masterpiece: The main brick residence captures the essence of Gilded Age elegance with 10-12 ft ceilings, eight fireplaces, a classic wrap-around-porch, and a porte-cochere. Spanning four finished levels, the main residence seamlessly blends original character with a significant three-story addition completed in 2012. The newer wing features a spacious

Hannelore Kaplan William Raveis Real Estate

Beyond a private gated entrance and sweeping circular drive lies a 2.5-acre sanctuary that redefines New Canaan luxury. Originally envisioned by Douglas Carter Architects and recently reimagined by its designer-owner, this estate seamlessly merges architectural pedigree with contemporary soul. The residence spans four finished levels, where soaring ceilings and walls of glass invite the lush

Jaime Sneddon William Pitt Sotheby's Int'l

Located in the desirable Lake Wind / Ponus Ridge corridor, this custom Colonial estate offers over 9,000 square feet of living space, thoughtfully rebuilt in 2010 and designed for both scale and comfort. The home features 5 bedrooms, 7 full and 3 half baths, six fireplaces (including one outdoor), and multiple porches, with select rooms showcasing cathedral ceilings. Set on 2.74 acres, the

Gene Shklover AG Prime Realty

A storybook entrance framed by classic stone walls opens to four flat, park-like acres leads you to this thoughtfully updated five-bedroom Colonial layered with warmth, character, and the kind of detail that make a house feel instantly welcoming. The light filled chef's kitchen flowing seamlessly into a family room with fireplace and French doors open to the terrace, heated pool, spa, and paddle

Melissa Jones Houlihan Lawrence

119 Proprietors Crossing is an entertainer's dream, featuring stunning architecture by James E. Gearity. Nestled on four private acres, this six-bedroom estate blends timeless elegance with modern luxury. A private drive leads to an elegant fountain, setting an unforgettable tone. Inside, a soaring foyer showcases a dramatic Baccarat chandelier and seven fireplaces, enhancing the warm atmosphere.

Molly Rubins NestSeekers International

Welcome to the iconic Evans House - a striking work of mid-century modern architecture. Designed in 1961 by renowned architect James Evans, this one-of-a-kind residence showcases a striking hyperbolic paraboloid roof that allows for a completely open main level filled with soaring floor-to-ceiling windows. Every room is immersed in natural light and surrounded by serene wooded views, offering

John-Michael Rachinsky-Wood Harbor Bridge Realty

Clark House, a legacy property with extraordinary provenance, was re-imagined by design legends Delphine and Reed Krakoff, adding their imprimatur of spare modern elegance. Reminiscent of a French hunting lodge and built like a fortress from steel and concrete in 1937, the property was purchased as a country residence by copper heiress Huguette Clark, and remained unoccupied and untouched until a

Leslie Razook William Pitt Sotheby's Int'l

Newly completed, gorgeous and with every luxury feature imaginable, 729 Smith Ridge Rd is a sun-drenched modern colonial, convenient to New Canaan town center, yet privately located in the estate section of Smith Ridge. A gated, dramatic approach sets the stage for the epitome of modern luxury inside: oversized windows, 10 foot ceilings, a show-stopping chef's kitchen, an elevator to all four

Amanda Bryan Compass Connecticut, LLC

Discover the epitome of modern living with this stunning brand new construction, perfectly nestled in the vibrant heart of New Canaan. Enjoy unparalleled convenience as you stroll to the charming downtown, catch a train for an effortless commute, or explore the scenic beauty of Waveny Park. With shopping, the newly constructed library, exquisite dining options, and a plethora of amenities just

Maggie Marchesi Compass Connecticut, LLC

Also known as 161 Forest St. which is the front entrance. Official address is 55 New Norwalk Rd which is the back entrance. Current rents are under market value and tenants have been in place long term. Great investment opportunity to own close to town. Each unit also has an attached one car garage, storage and side patio space. New windows and some paint.

Melodye Colucci Keller Williams Prestige Prop.

Set on 7 acres, this exceptional estate offers a private, sophisticated retreat at the end of a Bradford pear-lined gravel drive. The property includes a 10,000-square-foot main residence with pool and pool house, and a remarkable field house designed by architect Louise Brooks. The main house blends timeless elegance with modern design, while the field house delivers a one-of-a-kind recreational

Ashley Dineen Compass Connecticut, LLC

Set on 9.4 acres, this exceptional estate offers a private, sophisticated retreat at the end of a Bradford pear-lined gravel drive. The property includes a 10,000-square-foot main residence with pool and pool house, a two-bedroom guest cottage, and a remarkable field house designed by architect Louise Brooks. The main house blends timeless elegance with modern design, while the field house

Ashley Dineen Compass Connecticut, LLC

Welcome to 137 Linden Tree, a masterpiece of modern luxury and thoughtful upgrades in the heart of Wilton. This meticulously maintained home blends elegance, functionality, and high-end amenities for an extraordinary living experience. The property's curb appeal is striking, with a circular driveway, manicured lawns, curated plantings, and a full-property irrigation system. In the backyard, a

Marion Filley Compass Connecticut, LLC