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$1,369,000
2 Beds ⋅ 3 Baths ⋅ COMING SOON Status ⋅ 24194602 MLS ⋅ Orchard Hills BLDG.
Experience the perfect blend of townhouse convenience and single-family privacy in this beautifully updated home at Orchard Hills. Boasting an open-concept main floor, the residence features a gourmet kitchen complete with granite countertops, rich hardwood floors, and premium stainless steel appliances. The inviting living room, anchored by a classic marble fireplace, flows seamlessly into the dining area-creating an ideal space for hosting family and friends. Upstairs, you will find two spacious en-suite bedrooms, including a luxurious Primary Suite featuring a brand-new, spa-like bath and custom closet. The bright, walk-out lower level is a versatile haven, offering a family room with custom built-ins, ample space for a quiet home office, and a dedicated laundry room with abundant storage. Swing open the French doors to your private bluestone terrace, perfect for al fresco dining overlooking the manicured grounds. With the complex recently undergoing extensive renovations-including all-new siding, roofs, drainage, and landscaping-this home offers total peace of mind. Enjoy lazy afternoons by the community pool, or take a short, scenic stroll to Mead Park and the world-class dining and shopping in the Village of New Canaan.

123 Richmond Hill Rd Unit 21, New Canaan
$12,000
4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24191732 MLS
State of the Art construction from the ground up, this exceptional home has been thoughtfully transformed with a complete first-floor gut renovation taken down to the studs, the addition of a second story, and a beautifully finished lower level-all completed in 2025-2026. Offering three finished levels of modern living, this 4-bedroom, 3-full-bath residence is set on a lovely .53-acre property just minutes from downtown New Canaan, award-winning schools, Waveny Park, and the Metro-North train. The main level showcases a stunning new kitchen featuring quartz countertops, quality finishes, and an open-concept design that flows seamlessly into the living and dining areas-ideal for both everyday living and entertaining. Also on the first floor are a full bathroom, a spacious bedroom, a separate room perfect for a home office, and additional flexible bonus space to accommodate a variety of lifestyles. Upstairs, the beautiful primary suite offers a generous walk-in closet and a luxurious ensuite bath. Two additional bedrooms share a well-appointed full bathroom, and a convenient second-floor laundry room completes this level. The finished lower level is filled with natural light and provides two additional rooms ideal for a home office, fitness area, playroom, or media space, along with ample storage. Additional highlights include beautiful hardwood oak flooring, recessed lighting, contemporary finishes throughout, and abundant storage.

133 Jelliff Mill Rd, New Canaan
$950,000
2 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24186026 MLS
Set on a desirable 1-acre lot in a quiet neighborhood setting on the west side of town, this property offers exceptional potential to renovate, expand or reimagine the existing home to fit your lifestyle. Ideally located with easy access to town, the Merritt Parkway, shopping, dining, and top-rated schools, the property combines convenience, privacy, and enduring neighborhood appeal. A rare opportunity to create your dream home in one of New Canaan's most desirable locations. Please do not walk property without confirmed appointment.

158 Spring Water Ln, New Canaan
$950,000
ACTIVE Status ⋅ 24186029 MLS
A rare opportunity to own a beautiful 1-acre property on the sought-after west side of town in one of New Canaan's most desirable neighborhoods. The existing residence offers renovation potential, while the exceptional lot provides the ideal setting to build a custom home. Enjoy the perfect balance of privacy and convenience with easy access to downtown New Canaan, the Merritt Parkway, shopping, dining, parks, and top-rated schools. Please do not walk the property without a confirmed appointment.

158 Spring Water Ln, New Canaan
$2,995,000
5 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 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
$2,495,000
3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24181415 MLS ⋅ Oenoke BLDG.
Rarely offered and just moments from the heart of New Canaan, this beautifully renovated three-bedroom residence offers exceptional comfort, convenience, and timeless style. Set in the intimate Oenoke Lane community, the home has been extensively renovated and thoughtfully improved over the years, creating spaces that feel both elegant and effortless. A desirable end unit with an east-west orientation, the home is filled with natural light and enjoys exceptional privacy, enhanced by protected Land Trust property directly across the street. Sunlight fills the gracious living and dining rooms, while the beautifully reimagined kitchen serves as the heart of the home, featuring quartzite countertops, custom cabinetry, banquette seating, Wolf, Bosch and Sub-Zero appliances, and radiant heated floor. Sliders from the living room, dining room, and kitchen open to a private terrace, creating a seamless connection between indoor and outdoor living. A private elevator provides access to all three levels. Upstairs, the primary suite features a custom dressing area, built-in workspace, and beautifully renovated bath with radiant heated floor. An additional bedroom offers flexibility for guests, family, or office space, while the lower-level bedroom includes built-ins and an en-suite bath with radiant heated floor, ideal for guests or a private retreat. PLEASE NOTE TAXES LISTED ABOVE ($26,201) ARE FOR 145 AND 147 OENOKE LANE COMBINED. QUARTERLY ASSOCIATION FEE INCLUDES TAXES.

145 Oenoke Ln, New Canaan
$8,250,000
6 Beds ⋅ 8 Baths ⋅ ACTIVE Status ⋅ 24184237 MLS
190 Brookwood Lane is set in one of New Canaan's most unique and desirable residential settings - a bucolic landscape of rolling meadows, mature woodlands, and gently flowing streams set on just over 3 acres of quintessential New England beauty. Situated in the heart of New Canaan, the property offers a peaceful and established neighborhood setting where quiet roads, mature trees, and estate-scale properties create an atmosphere increasingly difficult to replicate. This extraordinary proposed residence blends timeless New England architecture with refined modern living. Designed by Tanner White Architects as the quintessential New Canaan colonial with gracious proportions and exceptional scale, the home is envisioned with approximately 7,500 square feet across the first and second floors, including expansive entertaining spaces, dramatic 10-foot ceilings on the main level, generously scaled bedrooms, and seamless indoor-outdoor living throughout. The proposed floor plan includes 6 bedrooms, 8 bathrooms, 3-car garage, and pool with the opportunity to finish attic and lower-level spaces for more than 10,000 total square feet. The oversized homesite provides exceptional flexibility for estate level outdoor amenities while maintaining tremendous privacy and natural beauty.

190 Brookwood Ln, New Canaan
$4,295,000
5 Beds ⋅ 6 Baths ⋅ ACTIVE Status ⋅ 24183490 MLS
This elegant New Canaan home is distinguished by its timeless Federal-inspired architecture and gracious symmetry. The five bedroom five and a half bath residence was thoughtfully redesigned and expanded in 2007 to the highest standard. Set on two beautifully landscaped and very private acres in one of New Canaan's most coveted cul-de-sac settings, this light-filled residence offers over 7,200 square feet of refined living space that effortlessly balances elegance with warmth. The home features a generous first-floor primary suite with luxurious marble bath and walk-in closets, an inviting library with fireplace, and private office also with fireplace. A spectacular kitchen with upscale appliances and marble countertops opens to a family room which flows seamlessly for both intimate living and entertaining on a grand scale. A rear staircase opens to a spacious second floor recreation room, three oversized bedroom suites, and a cozy sitting area. Outside, a heated pool, flagstone terraces, sweeping lawns, and mature gardens create a private outdoor sanctuary worthy of the home itself. Perfectly positioned just moments from the beloved Irwin Park, commuter train, charming New Canaan village, the GreenLink Nature Trail, and highly acclaimed New Canaan public schools and library. This is a rare opportunity to own a truly special property where classic New England beauty, exceptional craftsmanship, and unparalleled location converge.

34 Bayberry Rd, New Canaan
$1,650,000
4 Beds ⋅ 4 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 24073041 MLS
This 4 bedroom,3.5 bath tastefully renovated vintage home has an open floor plan,walls and windows with divided light and high ceilings, creating an instant sense of peace and well being. A stone hearth at the entry is surrounded by walls of bookshelves and a reading corner. The beamed living room and adjacent sun room overlook a romantic tiered garden and flat lawn. The fireplace's stone wall frames the dining space, and French doors open onto the garden patio and pergola. The warm polished wood island featuring a copper bar sink is the centerpiece of a perfect chef's kitchen. Down a private hall is the walk out first floor bedroom with full bath, walk in closet and adjacent laundry room. Upstairs an exercise/ gym space is conveniently located outside the primary suite with it's private office, high ceilings, walk in closet, and elegantly kitted bath (soaking tub, double sinks, walk in shower) Two additional generously proportioned bedrooms share a large hall bath. Convenient to charming Scott's Corners and just a few minutes to New Canaan town center, this is a special spot. Swing on the front porch, have morning coffee on the patio, wander the charming garden features, plant the enclosed garden with vegetables, flowers and herbs. Breathe. Zen living behind a stone wall on a rural street.This one is just right.

496 Trinity Pass Rd, New Canaan
$25,000
5 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 24170927 MLS
Sophisticated Center Hall Colonial totally renovated and expanded in 2008. Arched detailed interior doorways, enormous gourmet kitchen with several chef stations, sinks, 2 dishwashers, calacatta gold marble counters and high end appliances provides the hub where friends & family enjoy gathering. The welcoming great room with coffered ceiling, French doors & fireplace leads to flagstone terrace with outdoor fireplace for indoor/outdoor entertaining. A 2-story solarium offers picturesque seasonal views and overlooks spectacular private property with heated pool, cabana & stream beyond. Luxurious master suite with dressing room & marble bath, rear staircase, finished walk-out lower level, generator, garages for 4 cars and so much more. Located close to restaurants, shopping and commuting. Additional 1,800 sq ft in finished lower level with full bath. Tenant to use landlord's service providers.

490 Lost District Dr, New Canaan
$599,000
2 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24174165 MLS ⋅ St. John Place BLDG.
In-town location. Ideally situated just one block from the Metro North train station to NYC, village center, parks and library and all the plethora of amenities New Canaan has to offer. A circular drive and lush front lawn greet you at this brick 1910 mansion, which has been thoughtfully converted into nine charming residences. The property features park-like estate grounds perfect for picnics on the sweeping level back lawn. Sitting benches and lovely gardens abound. St. John Place is a highly sought-after location on "the Acre". This two-bedroom condo with living room, dining room, kitchen and roof top views is the perfect place to call home. HOA fee includes-heat, hot water, water, snow removal & trash pick up.

24 Saint Johns Pl Unit 4, New Canaan
$4,950,000
5 Beds ⋅ 7 Baths ⋅ ACTIVE Status ⋅ 24161583 MLS
Set on over four and a half acres of private, level grounds in one of New Canaan's most sought after locations, this exceptional estate offers a rare combination of scale, privacy, and close to town convenience. Originally built in 1962 and thoughtfully expanded, the property unfolds as a true compound. The main residence features five bedrooms, seven baths, and beautifully proportioned living spaces anchored by three fireplaces. A seamless connection between the chef's kitchen and family room creates the heart of the home, designed for both everyday living and effortless entertaining. The kitchen is fully equipped with a six burner Wolf gas range, second Wolf oven, Miele dishwasher, Sub Zero refrigerator and freezer, wine cooler, beverage drawers, marble island, and double sinks. Beyond the main residence, the estate continues to impress. A separate antique guest house with full kitchen, 3 bedroom and 1-1/2 bath provides ideal accommodations for extended family or guests. The heated gunite pool and pool house, added in 1991, offer a true retreat setting, complete with a party room, kitchen, bedroom, bath, and sauna for a resort like experience. A rare opportunity to own a private New Canaan estate with exceptional grounds, flexibility of living, and proximity to town.

537 Oenoke Rdg, New Canaan
$2,495,000
5 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24169441 MLS
Updated to perfection, this classic 5-bedroom Connecticut Colonial offers over 5,500 square feet of curated living space, harmoniously positioned on a private, sought-after cul-de-sac within an enclave of 4+ acre estates. The residence unfolds with a sun-drenched brand new chef's kitchen featuring custom cabinetry, premium quartz countertops, and high-end appliances, all flowing through floor-to-ceiling glass sliders to an expansive deck and a grand family room anchored by a stately fireplace. A sophisticated main level offers a formal dining room, elegant living room, and a bespoke private office with picturesque views of the park-like grounds. Upstairs, the primary suite serves as a sanctuary with a dedicated sitting room and new spa-inspired bath, while a separate private-entry in-law suite provides a secluded fifth bedroom and sitting area for ultimate versatility. The newly finished 1,700-square-foot walk-out lower level elevates entertaining with a massive media/playroom, an additional family room, and potential for a custom wine cellar-all just minutes from the vibrant New Canaan town center, top-tier schools, and the Metro-North train.

171 Proprietors Xing, New Canaan
$8,747,000
7 Beds ⋅ 10 Baths ⋅ ACTIVE Status ⋅ 24165330 MLS
FrogPond Estate is a modern Scandinavian masterpiece unlike anything New Canaan has ever seen - an architecturally rare achievement set on 2.25 pristine, private acres, moments from the train and village. Spanning 11,836 plus square feet of sleek, sun-drenched living space, this 7-bedroom, nine-and-a-half-bath residence is defined by its 12-foot ceilings, bespoke millwork, and designer lighting - details that elevate every room into something memorable. Four thoughtfully placed laundry rooms, multiple fireplaces, and a fully custom build throughout speak to a level of intentionality rarely found at any price point. At the heart of the main level, a gourmet kitchen with double islands anchors an open floor plan crafted for both quiet daily living and effortless large-scale entertaining. Walls of glass dissolve the boundary between inside and out, opening to covered porches and private balconies that complete the estate's serene, Scandinavian sensibility. A separate 1,190 sq. ft. guest cottage - complete with its own island and laundry - offers the perfect complement to the main residence, ideal for extended family, guests, or a private retreat. Secluded yet connected, grand yet warm - FrogPond Estate is a singular home that must be experienced to be understood.

259 Frogtown Rd, New Canaan
$7,250,000
6 Beds ⋅ 10 Baths ⋅ ACTIVE Status ⋅ 24156735 MLS
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. Spacious entertaining areas flow seamlessly to a tranquil terrace. The heart of the home includes a chef's kitchen that opens to a Great Room with a remarkable 35.5 foot vaulted ceiling, centered around a large quartz island with integrated audio. A formal dining room beneath another Baccarat chandelier sets the stage for memorable gatherings. The West wing hosts the primary suite, featuring a cozy retreat and a study with a hidden staircase leading to a gym and an 800-square-foot dressing room. An adjacent Junior Primary Suite has its own entrance and living area. Upstairs, four additional bedrooms include two ensuite and two with a jack-and-jill bath. The finished lower level boasts a media room, fitness center, and wine cellar. Outdoors, curated grounds offer a dining pavilion, outdoor kitchen, and a newly constructed pool and spa, with space for a tennis/pickle-ball court. Engineered for efficiency, the estate features commercial-grade systems, radiant heat, and a rare Welsh slate roof. A four-car garage and an elevator service complete this exceptional offering.

119 Proprietors Xing, New Canaan
$2,495,000
3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24136291 MLS
Behind the gates of the once star-studded estate lies a rare opportunity to create a legacy property in one of New Canaan's most peaceful and desirable settings. Part of the former storied estate once associated with famous actors, musicians, and industrialists, the property carries a sense of history and character rarely found in today's land offerings. Set on over four flat acres with mature trees, this unique property offers an increasingly rare combination of privacy and beauty minutes from downtown New Canaan, NYC train service, and walkable to nearby Clubs. The land itself is the true standout: level, framed by large mature trees, creating an ideal canvas for a homesite that has been approved for a six-bedroom septic system. Electric utility infrastructure has been installed, significantly shortening the path toward development. An added perk is a Nature walking trail through recently restored acre of improved wetlands Unlike a typical land offering, buyers have the opportunity to collaborate with an experienced builder/design team to help streamline the process. Options may include building a fully custom residence or working from thoughtfully developed architectural concepts tailored specifically for the property and setting. Part of a limited collection of estate homesites that will ultimately define one of New Canaan's most compelling settings.

48 Brookwood Ln, New Canaan
$2,495,000
ACTIVE Status ⋅ 24136296 MLS
Build your home in one of New Canaan's most desirable and picturesque settings. Set on over two acres of gently rolling land with mature trees and exceptional privacy, this special homesite is just minutes from town, train to NYC, and walkable to the Country Club of New Canaan. Part of the former star-studded estate on Brookwood Lane, the property is located along a bucolic and quiet dead-end lane that epitomizes tranquility and convenience. Unlike a typical land offering, buyers have the opportunity to collaborate with an experienced builder/design team to help streamline the process. Options may include building a fully custom residence or working from thoughtfully developed architectural concepts tailored specifically for the property and setting. Part of a limited collection of estate homesites that will ultimately define one of New Canaan's most compelling settings. Select homes and additional offerings within this Brookwood Lane development will be introduced over time, creating a cohesive and highly curated residential setting. The homesite has already been approved for a six-bedroom septic system, and electric utility infrastructure has been installed, providing an increasingly rare level of readiness and reducing uncertainty for future development. An open canvas in a rarely available ultimate location.

122 Brookwood Ln, New Canaan
$1,625,000
ACTIVE Status ⋅ 170006083 MLS
Beautiful 2 acre lot with meadow and gently flowing stream. Close to town on West Side location. Access to property from Welles Lane.

470 Frogtown Rd Unit Lot 2, New Canaan
$1,625,000
ACTIVE Status ⋅ 170006077 MLS
Beautiful 2 acre lot with meadow and gently flowing stream. Close to town on West Side location.

470 Frogtown Rd Unit Lot 1, New Canaan
$6,595,000
6 Beds ⋅ 9 Baths ⋅ ACTIVE Status ⋅ 24124919 MLS
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.

62 Summersweet Ln, New Canaan
$25,500,000
9 Beds ⋅ 14 Baths ⋅ ACTIVE Status ⋅ 24103956 MLS
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 2014 transformation. The volume of the rooms, soaring ceilings, proportion of the windows and quality of light create a sense of serenity and openness. Stately yet modern, this is a house that can be lived in with comfort and ease. Adjacent to the dining room gallery is a walled garden with a custom pavilion for entertaining. The 52 acres were transformed in collaboration with noted landscape architect Perry Guillot into a private park with a dramatic meandering approach, a great lawn, and woodland trails amongst streams and waterfalls. A 60 x 22 pool and tennis court were also added. At the discrete entrance to the property are twin cottages; a caretaker residence and a gym. Privacy and proximity to NYC and airports along with this caliber of property make this a world class offering and a rarity by any standards.

104 Dans Hwy, New Canaan

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