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256 Country Club Rd, New Canaan
$6,838,000
5 Beds ⋅ 9 Baths ⋅ 24178654 MLS
Set just four minutes from town on nearly three acres adjacent to protected Land Trust property, this exceptional residence offers the privacy, scale, and tranquility of a country estate without sacrificing convenience. Sprawling lawns, stone walls, and a fully finished pool house with pool accessed through a dramatic hornbeam archway, underscore the property's exceptional outdoor living experience. The entry foyer establishes the home's architectural character, unfolding into a generous front to back gallery anchored by mahogany doors that open directly to the 33 foot covered porch and outdoor terrace. Detailed millwork, oak floors, and beautifully proportioned rooms create a sense of continuity throughout, while French doors across the principal living spaces provide a seamless connection between indoor and outdoor living. The kitchen, family room, and informal dining area are thoughtfully arranged in an open, flowing layout oriented toward the grounds, balancing everyday comfort with effortless entertaining. A well appointed mudroom serves the practical demands of daily life with equal attention to detail. The primary suite is distinguished by soaring 12 foot ceilings and dual walk in closets. Four additional en suite bedrooms, a substantial bonus room, and a third floor guest suite/lounge complete the upper levels. The lower level is finished with a generous recreation space, half bath, media room, and a gaming room that walks out to a private terrace.

256 Country Club Rd, New Canaan

211 Oenoke Rdg, New Canaan
$6,250,000
5 Beds ⋅ 7 Baths ⋅ 24174226 MLS
Located on prestigious Oenoke Ridge in the heart of New Canaan, this spectacular modern farmhouse represents the pinnacle of luxury living, offering exceptional craftsmanship, designer finishes, and every high-end amenity imaginable. Perfectly positioned just moments from the New Canaan Nature Center, scenic walking trails, and a short stroll via sidewalks to the Village's renowned restaurants, boutiques, and theater, the location is truly unparalleled. Meticulously maintained and beautifully appointed, the home is defined by airy, light-filled interiors and an exceptional open-concept floor plan designed for both sophisticated entertaining and comfortable everyday living. A gracious wraparound porch welcomes you into elegant interiors featuring a stunning foyer, expansive living room with gas fireplace, and a state-of-the-art chef's kitchen with oversized center island, premium appliances, butler's pantry, and custom bar area. The adjoining family room, anchored by a second fireplace, opens through French doors to the resort-style grounds beyond. Designed for seamless indoor-outdoor living, the private backyard is a true sanctuary, featuring a spectacular Gunite pool and spa surrounded by lush professional landscaping. A spacious stone terrace offers multiple seating and lounging areas, while the fully equipped outdoor kitchen creates the ideal setting for alfresco dining and entertaining. The luxurious primary suite is a serene retreat with vaulted ceilings, a spa-inspired

211 Oenoke Rdg, New Canaan

757 Oenoke Rdg, New Canaan
$5,700,000
7 Beds ⋅ 8 Baths ⋅ 24147831 MLS
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 Smallbone gourmet kitchen, sun-drenched breakfast room, large working pantry, 2-sided fireplace, large center island fit for a master chef and an adjacent family room all designed for casual living and effortless entertaining. The main residence includes a luxurious owner suite with fireplace, balcony, marble bath and 2 walk-in-closets. There are six additional bedrooms on the upper levels. The home is rich with architectural character throughout. The property also includes: - Three Historic Barns: Versatile spaces for collectors, animal lovers, gardeners or car enthusiasts. Grounds: Set high on the ridge, 4 pastoral acres with an identified pool site, multiple gardens, and rolling lawns. Own a piece of New Canaan history on Oenoke Ridge.

757 Oenoke Rdg, New Canaan

108 Logan Rd, New Canaan
$3,325,000
6 Beds ⋅ 8 Baths ⋅ 24184790 MLS
Set on six spectacular acres in one of New Canaan's most picturesque settings, this exceptional estate offers timeless elegance, expansive living spaces, and breathtaking natural beauty. Surrounded by rolling lawns, mature trees, and serene water views, the property is a private retreat less than 10 minutes from town. Designed for both grand entertaining and comfortable everyday living, the residence features five/six bedrooms, six full baths. The gracious main level includes a formal living room, elegant dining room, soaring vaulted-ceiling family room, private office, and a stunning open-concept eat-in kitchen that serves as the heart of the home. A sun-filled four season room provides year-round enjoyment of the spectacular grounds. Two powder rooms and two laundry rooms add exceptional convenience. The second level is highlighted by a luxurious primary suite featuring dual bathrooms and abundant dressing and closet space. Four additional bedrooms and three baths provide ample accommodations, while a dramatic coffered-ceiling great room offers flexibility as a sixth upstairs bedroom, media room, or private guest suite. The finished lower level includes a spacious recreation/playroom and full bath, creating additional living and entertaining space. Outdoor living is equally impressive with multiple stone terraces overlooking a tranquil pond fed by the Mill River, providing a magical setting for relaxing, entertaining, and enjoying nature.

108 Logan Rd, New Canaan

1541 Oenoke Rdg, New Canaan
$3,200,000
5 Beds ⋅ 6 Baths ⋅ 24166609 MLS
Welcome to 1541 Oenoke Ridge, a spectacular country retreat with unparalleled privacy and natural beauty. Beyond the stately stone pillars, you are greeted by 4.5 beautifully landscaped acres including manicured gardens, a lighted tennis/sports court, a swimming pool, a 1-bedroom guest/pool house and a cozy stone fire pit. The main house blends elegance with everyday comfort. Highlights: spacious custom chef's kitchen with dining area, magnificent great room with cathedral ceiling and a paneled wood-burning fireplace, dining room with bay window and a family room with its own fireplace and French doors opening to the wrap around deck overlooking a serene and bucolic backdrop. A perfect setting for entertaining. Ideal for everyday living. Upstairs, the sun-filled primary suite offers a vaulted ceiling, dressing room and luxurious marble bath. Three more bedrooms, one en-suite, and a hall bath complete the second floor. The walk-out lower level is equipped with a kitchenette and full bath, providing flexible space for recreation, work or extended living. Overlooking the heated pool, the charming guest house is perfect for weekend guests, in-laws, a private office or a fitness studio. Whether hosting gatherings or enjoying quiet moments at home, this remarkable property offers endless possibilities. A rare opportunity not to be missed.

1541 Oenoke Rdg, New Canaan

148 W Hills Rd, New Canaan
$3,060,000
5 Beds ⋅ 5 Baths ⋅ 24187724 MLS
Set on 2.18 picturesque acres just six minutes from downtown New Canaan, this exquisitely renovated 5,731-square-foot residence offers the perfect blend of classic New England charm and contemporary sophistication. Thoughtfully reimagined in 2024, the home showcases exceptional craftsmanship, refined finishes, and a layout designed for today's lifestyle. Featuring five spacious bedrooms and four-and-a-half beautifully appointed baths, the home is filled with sunlit living spaces that flow effortlessly for both everyday living and elegant entertaining. From the stunning designer finishes to the generous proportions throughout, every detail has been carefully curated to create a warm yet luxurious atmosphere. The expansive property provides exceptional privacy while offering ample room for outdoor entertaining, recreation, or the addition of a pool. Ideally located just minutes from New Canaan's vibrant village, residents enjoy convenient access to boutique shopping, acclaimed restaurants, parks, and commuter transportation-all while returning home to a peaceful country setting. A rare opportunity to own a turnkey estate where timeless style, modern comfort, and an exceptional location come together in one of Connecticut's most sought-after communities.

148 W Hills Rd, New Canaan

197 Bowery Rd, New Canaan
$2,702,500
6 Beds ⋅ 6 Baths ⋅ 24166472 MLS
Privately set at the end of a long drive and elevated to capture tranquil reservoir views, this more than 5,500 square foot Colonial offers a rare sense of serenity and scale. Designed to embrace its natural surroundings, the home features beautifully proportioned interiors and oversized windows that bathe each space in light. The grand living room with fireplace opens seamlessly to a screened porch, creating an effortless indoor-outdoor experience ideal for quiet mornings or relaxed entertaining. A spacious eat-in kitchen with SubZero, Wolf and Miele appliances, huge center island, and skylight connects to the inviting family room with fireplace. The second level offers a refined primary suite along with five additional bedrooms, including ensuite and Jack-and-Jill configurations. Surrounded by professionally landscaped grounds, with a tennis court and charming gazebo, the property offers a peaceful retreat just minutes from town.

197 Bowery Rd, New Canaan

3 Holmewood Ln, New Canaan
$2,413,250
4 Beds ⋅ 5 Baths ⋅ 24169658 MLS
Set on nearly two acres of beautifully landscaped, park-like grounds, this enchanting 1930s Colonial is tucked away on a private lane just moments from the village and train. Classic architectural details grace the formal living room with fireplace and the elegant dining room, accented by custom built-ins. A richly paneled library with window seat offers an inviting retreat - equally suited as a sophisticated home office. The country kitchen flows effortlessly into a warm and welcoming family room centered around its own fireplace, perfect for both everyday living and effortless entertaining. A generous stone terrace extends the living space outdoors, framing sweeping eastern views across the expansive lawn, flowering trees, and mature plantings. Upstairs, a spacious primary suite is complemented by three additional bedrooms - completing a home that is as timeless in its charm as it is serene in its privacy.

3 Holmewood Ln, New Canaan

23 Jonathan Rd, New Canaan
$2,100,000
5 Beds ⋅ 4 Baths ⋅ 24204185 MLS
Classic Connecticut! Welcome to this spacious 5 bedroom Connecticut home in New Canaan. Stunning pastoral and romantic scenery, stone walls, and stunning heritage trees throughout your private 2 acre property on Cul-de-sac Street. The beautiful and historic Selleck's Chapel is right around the corner. Enjoy your very own post-and-beam detached barn which offers a two-car garage additional flex space, and a loft inside. Inground gunite pool with cabana and patio receive direct sunlight, allowing for fantastic entertaining flow. It's a 7 minute picturesque drive to town on Oenoke Ridge. Brought up to today's standards with new solar panels paid in full, EV charger and a house generator. Guests approach through a circular driveway, with an additional driveway leading to the gorgeous barn for everyday living and mudroom access. This center hall colonial features a gourmet kitchen adjacent to a family room with a fireplace, vaulted ceilings and natural light. Large dining room and living room with wood burning fireplace, lead into an office or bonus room featuring exquisite antique barn floors and vaulted ceilings. 500 ADDITIONAL square feet in lower level! That has a private guest suite with full bath, large laundry room, and playroom or gym. Primary bedroom with ensuite bath on the second floor has balcony overlooking the property grounds perfect for sunsets or morning coffee. 3 additional bedrooms round out the second floor with a shared, renovated bath. Welcome to New Canaan!

23 Jonathan Rd, New Canaan

84 Heritage Hill Rd Unit 84, New Canaan
$840,000
3 Beds ⋅ 2 Baths ⋅ 24184944 MLS ⋅ Oenoke BLDG.
Welcome to this fabulous, completely updated corner-unit townhome, perfectly situated in the heart of New Canaan, steps from downtown. Bathed in natural light from multiple exposures, this exceptional 3-bedroom, 2-full bath residence seamlessly blends timeless style with modern comfort, offering a turnkey lifestyle in one of Fairfield County's most sought-after communities. The thoughtfully designed open floor plan creates an inviting atmosphere for both everyday living and entertaining. Beautifully updated interiors flow effortlessly from room to room, including a flex-space bedroom with a Murphy Bed that converts into a desk for office use. A highlight and one-of-a-kind feature is the recently renovated screened-in porch. This charming outdoor retreat extends your living space and offers the ideal setting for morning coffee, alfresco dining or simply unwinding while enjoying nature. Rarely available in these townhomes, #84 features an in-unit washer and dryer which adds to the home's exceptional functionality. In addition to the assigned parking space, a detached garage is included, which provides valuable parking and additional storage. Residents enjoy a resort-like lifestyle with access to 2 community pools and beautifully maintained grounds. A quick walk to New Canaan's vibrant village center provides access to acclaimed restaurants, boutique shopping, and the train station. With access to the town's award-winning schools, its prime location, sophisticated updates,

84 Heritage Hill Rd Unit 84, New Canaan

125 Heritage Hill Rd Unit A, New Canaan
$730,000
2 Beds ⋅ 2 Baths ⋅ 24173058 MLS ⋅ Oenoke BLDG.
Experience the best of New Canaan living in this impeccable first-floor corner-unit condominium in one of Fairfield's County's most sought-after communities. This beautifully updated 2-bedroom, 2 bath home offers the perfect blend of comfort, style and convenience just walking distant to restaurants, cafes, shopping parks, and the Metro-North Railroad for and easy NYC commute. Filled with both morning and afternoon sunlight, the home features custom floor-to- ceiling built-ins surrounding a marble electric fireplace, crown molding throughout, refreshed hardwood floors (2024) newer windows, and stylish new lighting. The refreshed kitchen (20024) includes a new refrigerator, microwave all stainless-steel appliances, while both full baths were beautifully renovated in 2024. Rare conveniences include a detached one-car garage and a deeded parking space just outside the rear entrance. Additional private basement storage. Enjoy beautifully landscaped grounds, two community pools and low-maintenance living with heat, A/C, hot water, snow and garbage removal, professionally managed included in the HOA. Located near top-rated public schools, new library and beloved town parks, this is the turnkey living in the heart of New Canaan. 125 Heritage Hill Road Unit A is a special place to call home.

125 Heritage Hill Rd Unit A, New Canaan

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