Active Listings

$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
$2,495,000 (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
$2,350,000 (USD)
Pending

Lower Weston Area Single Family Home

Pending

6 Winthrop Hills Weston, CT 06883

5 Bed
6 Baths
6684 sqft
MLS# 24159217
Virtual Tour
Welcome to this Modern Colonial, a sanctuary where luxury, comfort & tranquility converge on a premier cul-de-sac, conveniently located to the Merritt Parkway, Weston Center & the campus of award-winning schools and downtown Westport plus beaches. With 5 BRs plus a potential 6th BR/au-pair or in-law suite, this refined retreat offers elegant living & impressive entertaining. The newly reimagined kitchen is a showpiece of style & substance: a spacious island anchors the room, surrounded by premier appliances & abundant storage, all beautifully designed, expertly equipped, and ready for every occasion. Host unforgettable dinners in the formal DR w/gas fireplace, then relax in the warm, inviting fam rm w/custom stone fireplace, French doors & surround sound for movie nights. Multiple home office options include a private library/homework room with built-ins. The luxe primary suite features excellent closet space, a fireplace, spa bath w/hydro tub, shower & dual sinks. The full finished lower level offers all of the room needed so that everyone can have their space, including a game/rec rm, media rm, gym & more, plus storage rooms. Outside, enjoy vast, usable, level lawns, heated pool, sports area, basketball, climbing swing & treehouse. Wraparound porch & screened-in porch offer stunning views of both the picturesque acreage as well as the tranquil hilltop scenery. 4-car garage for the auto enthusiast.
Listing Courtesy of SMART MLS / Coldwell Banker Realty / Alexander Chingas
$2,295,000 (USD)
Pending

Roseville/North Ave Area Single Family Home

Pending

140 Roseville Road Westport, CT 06880

4 Bed
3 Baths
3099 sqft
MLS# 24132813
Perfectly sited on 1.59 acres, this 4-bedroom, 3-bath antique home invites a lifestyle defined by warmth, ease, and understated elegance. Original wideboard floors, an impressive hearth fireplace, and beautifully preserved details create a sense of history, while the open, light-filled layout supports a modern way of living-whether hosting gatherings or enjoying quiet moments at home. The main level is designed for flexibility and comfort, with a first-floor bedroom or office that easily adapts to guests or work-from-home needs. Upstairs, the primary suite offers a calming retreat with a walk-in closet and full bath. Two additional bedrooms, a hall bath and small study provide space for family, creativity or focus. Thoughtful updates, including newer mechanicals and roof ensure a turnkey experience without compromising the home's character. Outdoors, life naturally extends into a private, resort-like setting. A gunite pool and spa invites long summer afternoons, while the expansive, sun-filled lawn sets the stage for entertaining, play or simply unwinding. The detached 2-car garage with heated loft offers a versatile escape-ideal for home gym, studio or relaxed gathering. Moments from town, dining, and all transportation, this is a delightful retreat where every day living feels both effortless and elevated.
Listing Courtesy of SMART MLS / Coldwell Banker Realty / Emily Gordon