Featured Properties

Some or all of the listings below are provided by the Westport office.
$3,275,000 (USD)
Coming Soon

Greenfield Hill Area Single Family Home

Coming Soon

111 Golden Pond Lane Fairfield, CT 06824

5 Bed
8 Baths
8279 sqft
Completely transformed over the past six years by its current owner and designer, this extraordinary residence blends grand-scale architecture with warmth, comfort, and beautifully curated interiors. Tucked at the end of a tree-lined cul-de-sac, the home makes an unforgettable first impression with a dramatic two-story entry, soaring 19-foot ceilings, a statement chandelier, and sweeping dual staircases. Thoughtfully reimagined for both elegant entertaining and everyday living, the home is filled with natural light and inviting spaces throughout. The vaulted family room with stone fireplace and whitewashed beams serves as the heart of the home, while the sun-filled south-facing kitchen showcases exceptional custom design. Rarely found, the property offers luxurious primary suite options on both the main and second levels, creating flexibility for guests, multigenerational living, or evolving lifestyle needs. Outside, the oversized patio overlooks mature trees and offers the perfect setting for entertaining, quiet mornings, or evenings under the stars. The property also provides ample room for a future pool and sport court. Peaceful and private, yet just a 7-minute drive to Metro-North for an easy NYC commute, this is a home that feels both inspiring and deeply livable.
Listing Courtesy of SMART MLS / Listed By: Cindy Raney, Coldwell Banker Realty
$3,149,000 (USD)
Active

Lower Weston Area Single Family Home

Active

214 Good Hill Road Weston, CT 06883

7 Bed
8 Baths
11075 sqft
MLS# 24168594
Rock Ledge, a private estate in Weston, is set on nearly five acres surrounded by protected land at the end of a cherry-tree-lined private drive. A reimagined Tudor Revival that blends historic character with modern living. Originally built in 1918, the property was once the residence of Godspell author John-Michael Tebelak. It has evolved into a compound of a brick mansion, pool house with apartment, and converted barn, largely by architect Jack Franzen. The main residence offers over 11,000 square feet with 7 bedrooms, 6 full and 2 half baths. The two-story media wing includes a home theater, library, office, and billiard room. The conservatory overlooks stone terraces, a waterfall and pond, and gardens. The primary suite and office have private balconies. The estate is further distinguished by multiple auxiliary structures: a carriage house with guest accommodations, a separate guest residence, and a heated party barn dating to circa 1850. A pool with spa, pergola, and outdoor kitchen complete the grounds. Original architectural details such as leaded glass windows, rich hardwood paneling and window seats and doors, five stone and brick fireplaces, and other features have been preserved. Modern additions introduce light-filled living spaces. New appliances and updated mechanicals service the buildings. Rock Ledge offers luxury and privacy rare in this area, and promises a lifetime of enjoyment for a buyer who appreciates its beauty.
Listing Courtesy of SMART MLS / Listed By: John Schiaroli, Coldwell Banker Realty
$2,999,000 (USD)
Active

Compo South Area Single Family Home

Active

2 Mortar Rock Road Westport, CT 06880

4 Bed
6 Baths
3312 sqft
MLS# 24173081
Virtual Tour
Better than new, this pristine 2016 custom-built residence offers a rare standard of refinement and sophisticated excellence. With 4,000+sqft and an elevator accessing all four finished levels, the home blends modern architecture with beautifully executed transitional design. The open-concept main level features a magnificent chef's kitchen, spacious dining area, and expansive living room with gas fireplace, custom built-ins, beams, and tray ceiling. Four-inch white oak flooring runs throughout. A wall of glass doors opens to a breathtaking private setting with a remote-controlled awning, ideal for effortless indoor/outdoor living. Four bedrooms include the luxurious primary suite with tray ceiling, built-ins, and serene garden views, plus a spa-like bath with heated floors, soaking tub, double vanity, and walk-in closets. Two additional en-suite BRs and an exceptional home office with dual built-in desks, double-height bookcases, library ladder, and automated shade complete the level. The third floor offers a skylit fourth bedroom with full bath and cedar closet. The finished lower level includes a playroom/gym, office, and half bath. A 2car garage, elevator to all levels, full-house generator, security and sound systems elevate the offering. Ideally set on a desirable cul-de-sac minutes to the beach, train, town, library, and farmers market, making this an incredible location from which to enjoy all of Westport's most coveted amenities. Move-in ready and truly exceptional.
Listing Courtesy of SMART MLS / Listed By: Alexander Chingas, Coldwell Banker Realty
$2,850,000 (USD)
Active

In-Town Area Single Family Home

Active

24 Washington Avenue Westport, CT 06880

4 Bed
4 Baths
3430 sqft
MLS# 24175092
Virtual Tour
There is a moment just inside the front door, when the house introduces itself. The entrance hall-original, unhurried, exactly as gracious as 1919 intended-tells you everything. This is a home that was built when details mattered and time was taken. A century later, nothing essential has been lost. The living room and formal dining room carry that same quiet elegance, their proportions generous, their light beautiful through Anderson architectural-grade windows. Then comes the turn- into the 2013 addition, where a stunning chef's kitchen anchors a family room that opens through French doors onto a covered deck. Beyond it, a private landscaped backyard unfolds like a secret: lush, park-like, deeply planted and utterly your own. An outdoor shower with hot and cold water, a detached two-car garage, gravel driveway and an automated irrigation system make it as effortless as it is beautiful. Upstairs, the primary suite earns its name- spacious bedroom, sitting room, a spa bath, place to exhale. Three additional bedrooms, each with the soul of the original house, share a handsome hall bath.A finished third-floor now features two versatile offices and a full bath, offering flexible space ready for your next chapter. New roof, siding insulation, 4-zone A/C, sewer and water mains from 2013. 4300 SF set on .39 acres of one of Westport's most sought-after residential streets -walking distance to town.This home exudes charm and is completely, confidently, move -in ready.
Listing Courtesy of SMART MLS / Listed By: Jillian Klaff, Coldwell Banker Realty
$2,790,000 (USD)
Active

Coleytown Area Single Family Home

Active

56 Charcoal Hill Road Westport, CT 06880

5 Bed
3 Baths
2552 sqft
MLS# 24161256
A rare opportunity to own one of Charcoal Hill's signature properties, this exceptional Frazier Peters stone home pairs historic craftsmanship with a level of care and refinement that is increasingly hard to find. Set atop 2.3 +/- gated acres and introduced through a stunning circular drive, the residence showcases Peters' hallmark use of native stone, warm wood tones, and artisan detail, creating a home that feels both enduring and deeply inviting. More recent expansion and remodeling have sensitively enhanced the home. Sunfilled rooms with vaulted ceilings and handhewn finishes offer a balance of scale, with multiple living spaces that transition seamlessly to the outdoors. The grounds unfold in a series of thoughtfully designed moments including lush perennial gardens, winding paths, quiet terraces, and vibrant seasonal color. At the center is a sparkling, oversized pool with a waterfall spa and a fully outfitted stone pool house, which is an ideal retreat for summer living. A heated 4car stone garage with a finished upper level provides flexible space for a studio, office, or possible guest space. Every corner of the property reveals another place to gather, from sunny patios to shaded areas beneath large awnings, all wrapped in exceptional privacy yet minutes to the energy and amenities of downtown Westport. A home where history, beauty, and modern comfort come together with uncommon harmony.
Listing Courtesy of SMART MLS / Listed By: Douglas "Doug" Bross, Coldwell Banker Realty
$2,695,000 (USD)
Active

Valley Forge Area Single Family Home

Active

52 Valley Forge Road Weston, CT 06883

2 Bed
3 Baths
2254 sqft
MLS# 24167448
Set on three private acres of serene woodland along the banks of the Saugatuck River, this extraordinary Riverfront Retreat offers a rare opportunity to live immersed in nature in a modern masterpiece. Creating a seamless connection between the stunning interiors and the tranquil beauty of the surrounding landscape, experience breathtaking river views from the rooftop deck with succulent gardens, from the heated gunite pool surrounded by an oversized terrace and through the walls of glass throughout the home. From the moment you enter, prepared to be wowed by this concrete, glass and bamboo structure, as you flow through the stunning open living spaces into the private first floor Primary Bedroom, then up to the well thought out second floor. Rare and remarkable, this noteworthy home was designed by Specht Harpman and artfully built in 2010 by Michael Greenberg in the bucolic setting of Weston, CT. Enjoy best of both worlds- living in secluded waterfront serenity with effortless access to the areas shopping, restaurants and beaches in Westport and neighboring communities.
Listing Courtesy of SMART MLS / Listed By: Laurie Crouse, Coldwell Banker Realty
$2,500,000 (USD)
Active

Long Lots Area Single Family Home

Active

28 Bulkley Avenue North Westport, CT 06880

5 Bed
5 Baths
3917 sqft
MLS# 24168651
Beautifully renovated 1799 antique Colonial offering timeless charm, modern luxury, flat pool-worthy property, and exceptional convenience, just one light to the Greens Farms train. This special home captures the soul of historic Westport while delivering the comfort of today's lifestyle. Thoughtfully renovated, it blends original character, architectural detail, warmth, and six fireplaces with the amenities today's buyers expect. Set on a flat property with room for a potential pool, the home offers inviting indoor and outdoor spaces ideal for entertaining and everyday living. At the center is a chef's kitchen with a Sub-Zero refrigerator, a Wolf range, custom cabinetry, and generous prep space, opening to a sun-filled family room. Formal rooms, antique details, and multiple fireplaces create a space that feels both elegant and welcoming. The primary suite offers an oversized dressing room with abundant closet space, and a spa-like bath with a soaking tub and steam shower. The finished lower level includes a game room, wine cellar, and flexible recreation space. Outside, the expansive lawn offers space for sports, gatherings, gardens, or a future pool. Ideally located with one light to Greens Farms train, and minutes to Long Lots Elementary, Post Road shopping, and Main Street dining. A rare blend of antique charm and modern living.
Listing Courtesy of SMART MLS / Listed By: Judy Michaelis, Coldwell Banker Realty
$2,450,000 (USD)
Active

Greenfield Hill Area Single Family Home

Active

3808 Redding Road Fairfield, CT 06824

4 Bed
5 Baths
5376 sqft
MLS# 24171406
3808 Redding Road presents a rare opportunity to step into one of Fairfield's most distinctive properties; where early American history and modern living come together. Originally dating to 1769 and fully rebuilt in 2008, the home was reimagined to preserve its architectural integrity while delivering an ease making it livable for today. Inside the tone is warm, grounded, and refined. Original beams and centuries-old floors remain at the core, while refreshed interiors and natural light bring a sense of clarity and renewal throughout. A rare three-fireplace hearth anchors the main living spaces, creating a natural center point for gathering. Four bedrooms and four and a half baths offer both comfort and flexibility, including a primary suite with a private balcony overlooking the property as it comes alive in the spring. The land is expansive, yet entirely manageable. Nearly eighteen acres unfold into open fields, budding orchards, and wooded edges - offering the option to embrace the full scale of the property or maintain a more modest footprint. Whether for gardening, recreation, or quiet enjoyment, the setting adapts easily. A historic barn, carriage house, and chicken coop add character and versatility. Privately set yet just minutes from town, this is a property that delivers both space and convenience. 3808 Redding Road offers a sense of history, a renewed perspective, and the flexibility to live as you choose.
Listing Courtesy of SMART MLS / Listed By: Cindy Raney, Coldwell Banker Realty
$2,450,000 (USD)
Pending

Compo South Area Single Family Home

Pending

171 Compo Road South Westport, CT 06880

4 Bed
5 Baths
3800 sqft
MLS# 24168078
Virtual Tour
Tucked away in a peaceful, private setting, Hidden Ledge offers the best of Westport living in an ideal Saugatuck/Compo location. This stunning brand-new 4-5 bedroom home combines thoughtful design, quality craftmanship, and effortless access to the area's most loved destinations. Walk along sidewalks or bike the designated bike routes to Compo Beach, Longshore, Saugatuck, downtown shops, acclaimed restaurants, the train, library and Westport's coveted Levitt pavilion. Designed and built by local HOME Design Build, this 3800 SF residence features a clean, timeless aesthetic with an abundance of light thanks to its southern and western exposures. Every detail has been carefully curated, from vertical channel accents, Visual Comfort Lighting and Thermador appliances to the wide-plank white oak floors, custom closets and over-sized Marvin windows. A must-see home in the heart of one of Westport's most desirable locations. #171 Compo Rd. S is one of two NEW Constructions currently being built on a private rear parcel set back from Compo Rd. S. offering city water, sewer and buried power lines. ** The driveway will be maintained jointly by both 171 & 169 Compo Rd. S. As permitted, the property has been organized as a land condominium to allow for the 2 New Constructions to be sold separately.
Listing Courtesy of SMART MLS / Listed By: Jacqueline Tanya "Tanya" Sprague, Coldwell Banker Realty
$2,199,000 (USD)
Pending

Long Lots Area Single Family Home

Pending

24 Burr School Road Westport, CT 06880

5 Bed
5 Baths
3380 sqft
MLS# 24172330
Virtual Tour
***SUBMIT ALL OFFERS BY 3PM MONDAY MAY 11***Tucked away towards the end of a quiet cul-de-sac in a prime central Westport location, this beautifully updated home offers the perfect blend of privacy, convenience, and lifestyle. Set on 1.05 acres and just moments from town, close to schools, shopping, and commuting options, this five-bedroom residence is designed for both everyday living and effortless entertaining. The heart of the home is the open kitchen featuring a large sunny dining area, center island, breakfast bar and exceptional flow into the family room-ideal for gatherings and modern living. A charming living room with a warm and inviting fireplace seamlessly flows into the private formal dining room, creating elegant spaces for more intimate gatherings. This residence includes 4.5 baths and a thoughtfully designed layout throughout. The luxurious primary suite is a true retreat, complete with an adjacent office/dressing/make-up area or baby's room-exceptional custom closets-including a spacious walk-in with built-ins-and a spa-inspired bath with jetted tub. The finished lower level, with private room with large closet, open space and full bath, provides ideal flexible space for storage, playroom, or gym. Outdoors, enjoy a private oasis with an in-ground pool framed by beautiful stone walls and mature plantings. Set back from the road, the property offers both tranquility and seclusion while remaining close to all that Westport has to offer.
Listing Courtesy of SMART MLS / Listed By: Julia Broder, Coldwell Banker Realty

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