My Active Listings

Some or all of the listings below are provided by the Westport office.
$3,250,000 (USD)
Pending

Beach Area Single Family Home

Pending

274 Pine Creek Avenue Fairfield, CT 06824

2 Bed
3 Baths
2812 sqft
MLS# 24147983
Virtual Tour
Waterfront summer living! This slice of heaven features 2-3 bedrooms, 2.5 bathrooms, and a detached studio apartment with a full bath. This modern architectural masterpiece, designed by award winning architect, Roger Ferris, has breathtaking views and an abundance of natural light, courtesy of the expansive floor to ceiling windows in every room. The dreamy primary bedroom has panoramic water views with the Manhattan skyline in the distance. The second bedroom contains a loft which provides two separate, private sleeping nooks and a lounge area with two-story, floor to ceiling windows. The detached studio apartment makes an ideal option for guests or extra recreational space with a wet bar and loft. The spacious exterior offers ample yard and deck space directly on the water for abundant outdoor living opportunities. Walk to the sandy beach from your yard at low tide or stroll down your sleepy street to the beach access path. This unique home's private, tranquil, waterfront setting makes it hard to believe it is so close to town, Metro North, and 95 for easy commuting, shopping, and dining in beautiful Fairfield.
Listing Courtesy of SMART MLS / Coldwell Banker Realty / Jennifer Rosen
$3,165,000 (USD)
Sold

Long Lots Area Single Family Home

Sold

19 Old Orchard Road Westport, CT 06880

6 Bed
6 Baths
4775 sqft
Virtual Tour
Stunning new construction DREAM HOME in prime location at the end of a cul-de-sac, convenient to all things Westport! Walk to Long Lots Elementary School (0.3 miles), Post Road restaurants/shopping (0.4 miles) and close to train (1.7 miles)! 6 bedrooms, 4 full and 2 half bathrooms. First floor office with many other WFH spaces. Modern design with clean lines, traditional layout. Open floor plan with bright, sunny rooms. Flat, dry, half acre with ROOM FOR POOL and Southern exposure. Large backyard with outdoor living spaces. Full house generator. Natural gas and city water. Completion date: Spring 2022. Still time to work with design team to customize. Westport Family Homes has been a premier builder in Westport for more than a decade.
Listing Courtesy of SMART MLS / Coldwell Banker Realty / Lori Popkin
$2,995,000 (USD)
Sold

In-Town Area Single Family Home

Sold

9 Fernwood Road Westport, CT 06880

5 Bed
5 Baths
4216 sqft
COMPLETELY RENOVATED 5 bedroom Colonial, with tennis court, on 1.47 private acres in the heart of Westport! Filled with natural light, modern design, open floor plan, peaceful setting. Picture being on a country lane, sitting on your porch, looking into woods and feeling like you're away from it all...yet you're in the center of town! Quiet cul de sac, instant neighborhood. Walk to Trader Joes, dog park, restaurants/and close to every Westport amenity/train/schools! Spectacular property w/flat backyard, PLUS an open ball field that is perfect for many activities, PLUS your own Har-Tru tennis court! Room for pool. Main level: 2 Story Entryway, White Kitchen (Quartz countertops, /2 dishwashers/walk in pantry/desk area) that opens to Great Room, Large Dining Room, Screened In Porch, Powder Room, Play Room, Mudroom, Laundry Room, Office/Guest Bedroom w/full bath, Primary Bedroom Suite w/walk in closet and white bathroom). Second floor: 3 bedrooms (1 ensuite, 2 w/shared bathroom, Bonus Room for Gym/2nd Office/2nd Playroom. Tons of storage. Full house generator, electric car charger, windows/siding/appliances/all systems replaced in 2017. Public water, propane, and sewer coming to Fernwood Road. This home has it all and the street and location can't be beat!
Listing Courtesy of SMART MLS / Coldwell Banker Realty / Lori Popkin
$2,825,000 (USD)
Sold

Lower Weston Area Single Family Home

Sold

41 Rogues Ridge Weston, CT 06883

5 Bed
6 Baths
6460 sqft
Virtual Tour
Unique country house with Five-Star amenities. Tastefully designed home boasting 5 BDs & 5.5 BAs of opulence in over 6,460 sqft main home in upscale lower Weston neighborhood. Separate 1400 sq barn w/state-of-the-art gym inclusive of Infrared sauna/steam room w/sitting bench,reclaimed wood, full BA & pvt yoga room. Find yourself in the glamorous great room enamored w/beam exposed high-ceilings, trendy brick flooring w/FPL. Custom built-in wet bar w/ice maker & beverage center perfect for entertaining. Home office w/ built-ins, French doors to pvt grounds, patio overlooking pond, in-ground pool, hot tub. First floor MBR suite w/2nd study, exposed brick walls, Full BA & BR. Back staircase leads to MBR suite featuring gas FPL, WIC, planked floors, pvt deck overlooking landscaped grounds. MBA w/soaking tub. Enjoy a culinary experience in this Gourmet EIK w/newly glazed cabinetry, Wolfe 6 burner range, Double Subzero, built-in Miele coffee bar, warming draw w/sink in new custom center island. Enjoy the ultimate luxury retreat, equipped w/outdoor stone Forno Bravo wood burning pizza oven. Recreation bonus room w/new wide plank floors, high reclaimed wood ceiling w/exposed beams, loft w/rolling staircase, full BA, pvt entrance. Professionally designed landscaping, firepit, outdoor lighting, golf putting green/sand pit, resurfaced heated pool, hot tub, outdoor shower & bocce. Organically irrigated grounds enclosed vegetable/flower garden. Just 20 minutes to Westport train station
Listing Courtesy of SMART MLS / Keller Williams Ny Realty / Christine Ricci
$2,700,000 (USD)
Active

Long Lots Area Single Family Home

Active

114 Cross Highway Westport, CT 06880

5 Bed
5 Baths
4179 sqft
MLS# 24165047
Welcome to a one-of-a-kind home in the heart of Westport - where timeless Colonial charm meets the elegance of a Parisian Estate. Set on an acre+ this home offers sophistication, space, and serenity throughout. The light-filled LR stuns with vaulted ceilings, HW floors, a wood-burning fireplace, and French doors opening directly to the deck and pool - the perfect setting for everyday living or entertaining. The formal DR offers its own fireplace, blending classic character with warmth and style. The chef's kitchen features two iconic AGA stoves, a walk-in pantry, skylights and a large center island. A charming covered porch offers peaceful morning coffee or evening outdoor dining. Upstairs, the primary suite, is a private sanctuary with vaulted ceilings, sunny sitting room, HW floors, walk-in closet, and spa-like bath incl cast iron soaking tub, oversized shower and elegant finishes. Add'l bedrooms 1 en suite the other w hall bath on the 2nd floor and 2 more Bedrooms on the 3rd floor w Hall Bath are bright and spacious, each w/ HW floors and serene views of the pool and gardens. The LL offers gym area, work space, storage and access to 2 car garage. The fully fenced backyard is a private paradise. Stone walls, mature English gardens and spectacular In-ground pool with auto cover add to the magic of this private oasis. Whole House Generator. Minutes to schools, shopping and town offering the rare combination of luxury, charm, privacy and convenience.
Listing Courtesy of SMART MLS / Coldwell Banker Realty / Robert Appell
$2,595,000 (USD)
Active

Greenfield Hill Area Single Family Home

Active

3808 Redding Road Fairfield, CT 06824

4 Bed
5 Baths
5376 sqft
MLS# 24160945
3808 Redding Road is the kind of property that feels discovered rather than found. A place where time has softened the edges, and the landscape tells its own story. Dating to 1769 and set on nearly eighteen acres of open fields and mature trees, this is one of Fairfield's earliest homes, thoughtfully rebuilt in 2008 to preserve its character with modern ease. Inside, the home unfolds with warmth and authenticity. Original beams and centuries-old wood floors ground each space, while natural light moves through refreshed interiors. At the center is a rare three-fireplace hearth - not just an architectural feature, but where the home gathers and winter evenings settle in. Four bedrooms and four and a half baths offer comfort and retreat, with a private balcony off the primary overlooking the property. Outdoors, the experience is equally compelling. Open land gives way to orchard rows planted with heirloom apple varieties, woodland edges, and a landscape long suited to small-scale farming. A historic barn, carriage house, and chicken coop continue the story, offering flexibility for guests, creative pursuits, or a return to its agricultural roots. It's a setting defined not only by its history, but by the space it provides - for gardens, horses, or simply privacy. Close to town yet entirely its own world, 3808 Redding Road is more than a home. It's a place to gather, slow down, and settle into something everlasting.
Listing Courtesy of SMART MLS / Coldwell Banker Realty / Cindy Raney
$2,535,000 (USD)
Sold

Greenfield Hill Area Single Family Home

Sold

1760 Hillside Road Fairfield, CT 06824

4 Bed
6 Baths
6753 sqft
Virtual Tour
Privately sited in the heart of Greenfield Hill, charm and comfort abound at this sprawling country home. Evoking the feeling of an Old World European estate, elegant living spaces create an inviting backdrop for entertaining and every day. Beneath soaring ceilings with exposed wood beams and skylights, the family room centers on a majestic stone fireplace and features an adjacent office and wet bar. An eat-in chef’s kitchen is poised beneath a large skylight. Wide-plank hardwood floors, custom built-ins, handsome fireplaces with antique mantels and repurposed antique doors add to the home’s distinctive beauty. The main level primary suite is home to a full bath and sun-drenched atrium with a private entrance. Up the side staircase, a large home office is outfitted with a built-in desk and bookcases. The main staircase unfolds to a tranquil second-level primary suite with an en-suite bathroom, fireplace, dressing room and a private balcony made for relaxing in the evening with a glass of wine. The attached one bedroom apartment is home to a family room, well-appointed kitchen, bathroom, washer/dryer and private entrance. Enjoy outdoor living and dining on the terrace overlooking the spectacular, sylvan acreage dotted with mature trees and perennial gardens. Minutes from town, shops, restaurants, and schools, including Fairfield Country Day.
Listing Courtesy of SMART MLS / William Raveis Real Estate / Michelle&Team
$2,495,000 (USD)
Coming Soon

Southport Area Single Family Home

Coming Soon

790 Cedar Brook Lane Fairfield, CT 06890

5 Bed
5 Baths
4730 sqft
Set along a storybook private drive, where a gently winding brook passes beneath charming stone bridges, this is a home defined as much by its setting as by the way it lives. There's a quiet magic here-a sense of privacy and calm that feels rare, yet a warmth that makes it easy to imagine putting down roots and staying awhile. Inside, the home unfolds with an easy, natural flow. The spaces are generous without excess, designed for real living and the moments that shape it. The kitchen and great room come together as the heart of the home-open, inviting, and filled with light-where everyday routines and gatherings blend seamlessly. Cathedral ceilings and a wood-burning fireplace add both scale and comfort, creating a place that feels equally suited for slow mornings and full evenings. Thoughtful flexibility is woven throughout, with spaces to work, create, and grow, along with a finished lower level that adapts as life evolves. Upstairs, the primary suite offers a sense of retreat, set apart for quiet and privacy, while several additional bedrooms provide room to expand, host, and settle in. Outdoors, the property invites a slower pace. Dining on the deck, tending to a garden, or simply enjoying the open yard feels effortless, with the soft sound of the brook never far away. Here, privacy and connection coexist-tucked away in a setting that feels like its own small world, yet just minutes from town, train, and shoreline. A place to grow into, and a place to stay.
Listing Courtesy of SMART MLS / Coldwell Banker Realty / Cindy Raney
$2,399,000 (USD)
Active

Saugatuck Area Single Family Home

Active

2 Ledgemoor Lane Westport, CT 06880

5 Bed
6 Baths
4600 sqft
MLS# 24159517
Set on a quiet, private cul-de-sac very close to town and Winslow Park, this custom five-bedroom Colonial offers an exceptional opportunity for a new owner to leave their mark and add significant value. Designed with best-in-class materials and a thoughtfully planned layout, the home retains its gracious scale, natural flow, and exceptional character. Deferred maintenance has created the chance to elevate a well-loved property and return it to the signature splendor that defined it. The main level features a gourmet kitchen with Sub Zero & Viking appliances, stone counters, custom cabinetry and an adjacent breakfast room leading to a large family room, living room with fireplace, formal dining room, and two private offices with built-ins. French doors from most main floor rooms open to a balcony overlooking a heated Gunite pool and a large, level play area. The walkout lower level has a wall of French doors and is an exquisite poolside space that includes a fully-equipped wet bar, rec/game rm, gym and a full guest suite. Upstairs, the spacious bedroom layout provides comfort and flexibility for a variety of needs. Set on 1.16 +/- acres moments from shopping and recreation, the home is being offered as-is. ***Listing photos include a mix of current 2026 images and select photos from 2009 to illustrate the full potential of the property. Please note that showings are welcomed and booked by appointment, and no open houses are planned.***
Listing Courtesy of SMART MLS / Coldwell Banker Realty / Alexander Chingas
$2,360,000 (USD)
Sold

Saugatuck Area Single Family Home

Sold

14 Sandy Hill Terrace Westport, CT 06880

5 Bed
5 Baths
5084 sqft
Virtual Tour
Welcome to this fabulous 5 BR, 4.5 BA colonial nestled in the heart of Westport. Bathed in natural light, the home welcomes you with a two-story foyer, setting the tone for the elegance within. The chef's kitchen boasts high-end Subzero & Wolf appliances including 2 wall ovens, gas cooktop, & Bosch dishwasher, complemented by granite counters, white cabinetry, & a generous island for both prep & casual dining. Entertain effortlessly as the kitchen flows into a spectacular great room w/vaulted ceiling & a fireplace ensconced in stone. Step through French doors to the serene bluestone patio, overlooking a private fenced yard adorned with mature landscaping that blooms in every season. The main level also features a formal dining room, a gracious living room, an office, & a convenient laundry room. Upstairs, retreat to the primary suite w/2 walk-in closets, a vaulted ceiling, sitting area, & ensuite bathroom w/jetted tub & 2 sinks. Four additional bedrooms & two full bathrooms ensure space for all. The lower level offers a gym w/mirrored wall, a full bathroom, & a spacious family room w/fireplace, wet bar w/wine chiller & refrigerator/freezer drawers. French doors open to a patio - potential for an in-law or au-pair suite. Major mechanicals, including a 22KW generator, recently replaced (ask for full list). Situated at the end of a cul-de-sac, this home combines peaceful seclusion & walking distance to school, the river, many restaurants & just 1 mile to the train. Welcome home!
Listing Courtesy of SMART MLS / Coldwell Banker Realty / Kathleen O'Connell

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