Featured Properties

Some or all of the listings below are provided by the Madison office.
$4,700,000
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In-Town Area Single Family Home

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32 Webb Road Westport, CT 06880

8 Bed
9 Baths
6863 sqft
MLS# 24125036
Welcome to 32 Webb Road, a stunning new home nestled on a quiet cul-de-sac in one of Westport's most desirable neighborhoods. Thoughtfully designed and masterfully built, this home blends timeless New England architecture with high-end modern finishes and exceptional attention to detail. Step inside to discover a sun-filled open floor plan, custom millwork, and beautifully scaled living spaces. At the heart of the home is the gourmet kitchen, equipped with top-of-the-line appliances, and a large center island-ideal for both everyday living and entertaining. Adjacent to the kitchen, the spacious family room with a large fireplace opens to a private, landscaped property with a large stone patio-perfect for outdoor dining, relaxing, or hosting family gatherings. On the second level, you'll find five spacious en suite bedrooms, including a primary suite featuring a spa-inspired bath, a generously sized closet, a makeup room, and a serene retreat at the end of the day. The finished lower level provides incredible flexibility, including a playroom, private bedroom, entertainment/media room, and a dedicated exercise space-ideal for today's lifestyle. Located just minutes from Compo Beach, downtown, and the train station, 32 Webb Road presents the perfect combination of modern luxury, comfort, and location.
Listing Courtesy of SMART MLS / Coldwell Banker Realty / Judy Michaelis
$4,350,000
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Compo South Area Single Family Home

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102 Compo Road South Westport, CT 06880

7 Bed
8 Baths
5179 sqft
MLS# 24122256
Virtual Tour
THE ESTATES AT COMPO SOUTH - SIR Development presents the last of two luxury residences set back on beautiful property, each with their own distinct Modern style and pool. Officially designated by the State of CT as a Scenic Roadway, this location offers ultimate convenience to every amenity that makes Westport one of the most highly desired towns in the nation. This elevator-ready home begins with a spectacular glass-lined foyer, filling the entire layout with sun. The private office/library with extensive built-ins provides a wonderful place to work. The dining room is accented by steel-framed glass panels and a crisp tray ceiling detail, while the butler's pantry has a fluted backsplash. The incredible gourmet kitchen features a pale oak-accented ceiling, generous island, Thermador appls incl double dishwashers and massive ref/frz. The open flow continues into the fam rm w/bold coffered ceil detail, linear gas fpl and glass doors to the deck. The oversized mudrm links the hub of the home to the garage and casual entry. Upstairs, the first 5 BRs incl the primary suite, which is an awe-inspiring sanctuary of refined design and ultimate comfort, beginning w/the cath ceil BR w/fpl, massive dbl clsts, a designer bath & more. Each BR has unique appeal. 3rd flr bonus space & the 6th BR. The finished, walk-out LL has the 7th BR, rec/gym/media, cabana bar for poolside entertaining, all stepping out to a patio. Just moments to Compo Beach, Longshore Club Park, train and town.
Listing Courtesy of SMART MLS / Coldwell Banker Realty / Douglas "Doug" Bross
$4,249,000
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Compo South Area Single Family Home

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179 Compo Road South Westport, CT 06880

5 Bed
5 Baths
3390 sqft
MLS# 24109550
Welcome to 179 Compo Road South, in the heart of Westport-super close to Longshore, Compo Beach, downtown, the train station-everything Westport has to offer. This Tudor-style gem, originally built in the 1920s, has been thoroughly renovated to honor its heritage while offering every contemporary comfort. Situated high on the hillside, sweeping property views enchant. The classic slate roof is not only elegant but also a lasting testament to the home's quality craftsmanship. As you step inside, you'll be captivated by the hundred-year-old hardwood floors, rich in character, lovingly preserved and flowing onto the main floor. The newly renovated modern kitchen is the centerpiece of the main floor, featuring sleek finishes, premium appliances, and a smart design perfect for both everyday living and entertaining. Inside, every room is comfortable year-round thanks to the updated heating and air conditioning systems-efficiency meets timeless style. A majority of the property is deer-fenced, creating a sanctuary for the beautifully landscaped gardens and allowing you to enjoy the outdoors undisturbed. Step outside to your ultimate retreat: a beautiful pool and pool house with a guest bedroom, full bath, and a luxurious sauna-perfect for relaxing or hosting. Outdoor spa-like retreat featuring a stunning free-form pool with a cascading waterfall from the elevated hot tub above. The outdoor kitchen and built-in grill make alfresco dining effortless in your private oasis.
Listing Courtesy of SMART MLS / Coldwell Banker Realty / Judy Michaelis
$4,000,000
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Greens Farms Area Single Family Home

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221 Greens Farms Road Westport, CT 06880

5 Bed
7 Baths
5789 sqft
MLS# 24123287
THE BEDFORD HOUSE - Architecturally and historically significant estate in coveted Greens Farms. This exceptional property offers a rare opportunity to own one of Westport's most superb antique homes. Set on 2.33 acres with a gunite pool/spa, court and a 2400 sq ft barn featuring a 3-car garage, loft & more, the estate blends timeless elegance with modern comfort. Originally built in 1904 and designed by noted architects Visscher and Burley, this Colonial Revival home has undergone thoughtful renovations over the years to preserve and enhance its character. The main residence features 5 Bedrooms and 6.5 Baths with a well-planned layout for today's lifestyle. High ceilings, oversized windows, finely detailed millwork and sun-filled rooms create a sense of warmth and sophistication. Recent improvements include a new cedar wood roof on both the house & barn, a like-new pool, spa & mechanicals, refinished hardwood floors, updated HVAC and new appliances. A unique highlight of this estate is its location across from Nyala Farms, offering scenic views of over 50 acres of protected meadows and fields with a deed that prevents further development. A rare opportunity awaits the discerning buyer to continue the legacy of this historic property. Enjoy the ultimate lifestyle, minutes to the train, beaches, schools, shops and fine dining.
Listing Courtesy of SMART MLS / Coldwell Banker Realty / Leslie Riback
$3,995,000
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Compo Beach Area Single Family Home

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4 Buena Vista Drive Westport, CT 06880

5 Bed
5 Baths
3129 sqft
MLS# 24126601
Want to enjoy everything there is to love about the beach area, without the hassle of a flood zone? This home has everything you need. Perched at the top of Compo Hill, 4 Buena Vista Drive is a picture perfect colonial with water views and modern upgrades.This beautifully maintained home offers a traditional layout with high ceilings, arched doorways, and abundant natural light from the oversized windows. Thoughtful details include custom millwork, a butler's pantry, and spacious living/dining room great for entertaining. An open kitchen with high end appliances overlooks the family room with lots of custom built ins and a wood burning fireplace. Upstairs, the primary suite includes dual closets, wonderful water views, and a private deck creating a serene retreat. Primary bath has radiant heat. Three other upstairs bedrooms are spacious and flexible, including one with a Murphy bed for multipurpose use. In the lower level, there is a versatile hangout space and an additional bedroom which has access to a full bath. A generous mudroom for all your belongings, and 2 car tandem garage with lots of storage space rounds out this level. Enjoy the outdoors with a stone patio for dining, and admire the professional landscaping throughout the property. A whole-house generator and countless upgrades ensure comfort and peace of mind.
Listing Courtesy of SMART MLS / Coldwell Banker Realty / Debra Shaughnessy
$3,900,000
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Danbury Area Single Family Home

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151-155 Long Ridge Road Danbury, CT 06810

4 Bed
7 Baths
6824 sqft
MLS# 888972
Virtual Tour
ROADSIDE – A Storied 53-Acre Private Estate in Fairfield County, CT

Escape to your own private nature retreat at ROADSIDE, an extraordinary 53.44-acre country estate blending historic charm and modern luxury, just 90 minutes from Manhattan and 1.5 miles from the Redding train station. This rare legacy property offers unparalleled privacy, provenance, and polish—ideal for equestrians, creatives, collectors, and those seeking an exceptional lifestyle sanctuary where inner peace meets outer glow.

Originally built in 1710 and masterfully reimagined in the early 1900s, the meticulously maintained 5,200+ sq ft Colonial farmhouse features 4 bedrooms, 4 full bathrooms, and 3 half baths across three levels of living space. Period details including wide plank floors, six fireplaces, and custom millwork pair beautifully with modern comforts.

The heart of the home is the expansive chef’s kitchen with a dramatic double-sided fireplace that flows into sun-drenched gathering rooms and a glass-wrapped solarium. The luxurious primary suite offers dual spa-like bathrooms, a dressing room, and a private sitting area overlooking the grounds.

One of the most striking spaces is the dream library, complete with a cozy fireplace, intricate built-ins, and a stunning mezzanine loft above—perfect for book lovers, creatives, or remote professionals seeking a peaceful and inspiring work-from-home haven.

The partially finished walk-out lower level includes a media/game room, fitness space, and an impressive 500-bottle wine room. Every corner of the home is designed for comfort, sophistication, and timeless entertaining.

Surrounded by fencing, gated entries, and professional landscaping, the estate is a fully self-contained world. Wander through 2+ miles of groomed trails with electricity throughout—ideal for future equestrian lighting or nature-inspired enhancements. A scenic aerated lily pond, stone bridge, and gentle brook accentuate the estate’s park-like setting.

Outdoor living is elevated with a heated Gunite pool, pergola, gazebo, and a fully equipped outdoor kitchen. Enjoy vibrant fruit orchards, cutting gardens, vegetable beds, and expansive lawns—ideal for recreation, events, or simply reconnecting with nature.

A detached 3-car garage, 3-stall barn with electric and water, and open land provide exceptional lifestyle flexibility: add a tennis court, solar field, guest house, or equestrian amenities. Zoned RA40 and buffered by woodlands, this is a canvas for self-sustaining living or visionary development.

Located on Long Ridge Road, a designated scenic country road with a rich cultural history, this peaceful haven is moments from Candlewood Lake, Waubeeka Lake, Moses Mountain, Tarrywile Park, downtown Danbury, and I-84.

Whether you're a New Yorker seeking a weekend escape, a West Coast buyer craving Northeast charm, or a collector of legacy estates, ROADSIDE is a one-of-a-kind opportunity to own a premier estate in Fairfield County.
Listing by: ONEKEY / Coldwell Banker Realty / Chelsea Stinson
$3,900,000
Active

Starr'S Plain Area Single Family Home

Active

155 Long Ridge Road Danbury, CT 06810

4 Bed
7 Baths
5824 sqft
MLS# 24083893
Virtual Tour
ROADSIDE - A Storied 53-Acre Private Estate in Fairfield County CT Escape to your own private nature retreat at ROADSIDE, a rare 53-acre country estate just 90 minutes from Manhattan. This legacy property blends historic charm with modern luxury in a setting that feels worlds away-yet is 1.5M from the Redding train station and the cultural vibrancy of Fairfield County. Set within a fully fenced, surveillance and professionally manicured landscape, this estate offers: A Private Natural Sanctuary: Meandering trails, a stone bridge, an aerated lily pond, a stream wind through your own personal private woodland reserve plus 2 M of groomed trails. Electricity is available throughout the trail system-ideal for future enhancements such as equestrian trail lighting. A Modernized Historic Home: Originally built in 1710 and reimagined in the early 1900s, the farmhouse-colonial has been meticulously updated with six fireplaces, a double-sided chef's kitchen, and a luxurious primary suite with dual baths and a sunroom. 500 bottle Wine Room. Outdoor Living at Its Finest: A heated gunite pool, outdoor kitchen, pergola & gazebo overlook sweeping vistas. The four-season landscape includes fruit orchards, cutting gardens, and vegetable beds. Flexible Lifestyle Potential: With a detached barn, three-car garage, and ample space for a guest house, tennis court, or livestock, this is a dream property for equestrians, hobby farmers, or those seeking a self-sustaining lifestyle.
Listing Courtesy of SMART MLS / Coldwell Banker Realty / Kathleen "Katie" Harrison