Featured Properties

Some or all of the listings below are provided by the Westport office.
$1,975,000 (USD)
Active

Old Hill Area Single Family Home

Active

5 Tanglewood Lane Westport, CT 06880

4 Bed
3 Baths
1953 sqft
MLS# 24120677
Set on a quiet, convenient street in Westport's coveted Old Hill, this charming home captures the essence of Fairfield County living. A picturesque acre with level lawns, a sparkling pool, and expansive patios creates an exceptional outdoor retreat ideal for relaxing or entertaining. A welcoming front porch leads into a thoughtfully renovated interior with beautifully proportioned spaces and distinctive architectural details. The dramatic living room features a soaring beamed cathedral ceiling, fireplace, and oversized windows, while a central butler's pantry connects seamlessly to the dining room with its own fireplace and adjacent wine area. The sunlit gourmet kitchen offers customized cabinetry, a professional gas range, and a banquette dining area. The comfortable family room has a third fireplace. The flexible 4-bedroom layout includes a serene primary suite with a luxurious bath, soaking tub, separate shower, and walk-in closet. Additional bedrooms are spacious, including one with a private sitting area. Outdoor living is enhanced by multiple patios, including a covered space perfect for dining beside the pool. Enjoy close proximity to Earthplace, town, schools, train, and shopping.
Listing Courtesy of SMART MLS / Listed By: Douglas "Doug" Bross, Coldwell Banker Realty
$1,779,000 (USD)
Active

N/A Area Single Family Home

Active

28 Old Orchard Drive Weston, CT 06883

5 Bed
6 Baths
4079 sqft
MLS# 24079433
Experience dramatic, modern living in this grand home with a glorious gunite pool & exceptional architectural appeal. Custom-designed, the quality of this residence is readily apparent as you approach from the centrally-located, multi-million dollar neighborhood of fine homes. The stone front, Belgium block-lined drive and specimen landscaping greet you, leading to the soaring two-story foyer. Large windows that fill the rooms w/sunlight are a defining characteristic of the home, including the cathedral-ceil LR w/stone fpl & wide plank floors, holiday-sized DR w/bay window, fam rm w/wet bar and wall of glass to deck. The dine-in kitchen w/ center island, updated stainless steel appls incl gas cooktop & Sub Zero, also opens out to the large deck. A main flr office & 1.5 bths complete the main lvl. Front & rear staircases lead up to the spacious 2nd level where you will find a grand primary suite w/lrg walk-in clst & en-suite bth plus 3 addl BRs & 2 full baths. The incredible finished, walk-out lower level is a highlight, with sun-drenched spaces that add spacious comfort, flexibility and can meet any need - while still offering great storage. The rec rm w/fpl and a pair of offices or bonus rms each have doors to the rear property. The gym has an adjacent full bth, making it an ideal cabana for swimming guests using the pool when entertaining in these splendid surroundings. Enjoy gorgeous views & tranquil privacy, just minutes to the town Center & school campus plus commuting.
Listing Courtesy of SMART MLS / Listed By: Barbara Bross, Coldwell Banker Realty
$1,775,000 (USD)
Active

Lower Weston Area Single Family Home

Active

129 Davis Hill Road Weston, CT 06883

4 Bed
4 Baths
2512 sqft
MLS# 24171415
Set privately in Weston, this extraordinary home is an early masterpiece by Michael Greenberg, featuring a meticulously relocated Vermont barn, rebuilt with exceptional care and craftsmanship. Rich in character, the residence blends rustic authenticity with refined, modern updates. The stunning great room is anchored by a dramatic three-story fieldstone fireplace, while the first-floor primary suite offers its own stone fireplace and a luxurious bath with radiant heated floors. The kitchen is equipped with Wolf, Bosch, and Liebherr appliances. The dining room features a hidden dry bar and a glassware cabinet, with sliders to the top deck for outdoor dining if desired. Upstairs, there are three additional bedroom suites with updated baths, plus a smaller third-floor bedroom ideal for an office or flex space. The finished walk-out lower level includes radiant heat, a bedroom, a full bath, an office, a gym, laundry, and a kitchenette. Outdoors, enjoy a heated Gunite pool and spa with a bluestone patio, surrounded by serene woodland views. Additional features include the Sonos system, whole-house generator, and air purification. Minutes to town and top-rated schools, this move-in-ready retreat is ideal for weekend or year-round living.
Listing Courtesy of SMART MLS / Listed By: Georgia Wasserman, Coldwell Banker Realty
$1,749,000 (USD)
Pending

In-Town Area Single Family Home

Pending

55 Compo Road North Westport, CT 06880

2 Bed
3 Baths
2998 sqft
MLS# 24173921
There is a quality of light that artists seek-the kind that pours through the soaring atelier window of the great room in this updated vintage home. Once the studio of Norman Mason, each aspect of its design was in service to his art. Set on 1.26 acres overlooking Winslow Park, this charming home carries its history lightly and beautifully. The dramatic great room is anchored by an oversized fireplace, newly refinished hardwood floors and a special light that imbues the space with a certain atmosphere whether holding a dinner party for 20 or relaxing alone with a good book. The kitchen has been thoughtfully updated for how we live now-new appliances, clean lines, proper workspace, a walk-in pantry. The library offers a quiet place to work from home. The first floor primary suite is its own private world, serene and removed, with a generous walk-in closet and full bath that feels both practical and indulgent. Guests have a separate wing with room to settle in, while additional space throughout the property invites expansion, reinvention or room to grow. Step outside and the story continues. The grounds are lush and unhurried. The perennial gardens and flat sweep of lawn provide a living landscape that changes with the seasons. Moments from the center of town, theater, shops and restaurants, the particular rhythm of a place that is sophisticated and yet part of a neighborhood.
Listing Courtesy of SMART MLS / Listed By: Emily Gordon, Coldwell Banker Realty
$1,697,000 (USD)
Active

Weston Area Single Family Home

Active

166 Godfrey Road East Weston, CT 06883

4 Bed
5 Baths
4448 sqft
MLS# 24176595
Set back on 3.6 landscaped acres along a quiet country road, this exceptional contemporary offers rare privacy, sun-drenched interiors and easy access to Weston Center and top-rated schools. Designed for entertaining and everyday living, this home features soaring ceilings, dramatic walls of glass, an open floor plan and serene views of a tranquil pond and manicured grounds. A gracious entry opens to an expansive living room w/ fireplace and oversized windows, flowing into the dining room w/ sliders to multiple decks ideal for outdoor dining and relaxation. The kitchen offers s/s appliances, granite countertops, an informal dining area w/ access to an oversized deck overlooking the level yard. The adjoining family room, wrapped in glass and anchored by a fireplace, provides a warm gathering space w/ a seamless indoor-outdoor flow. The MAIN LEVEL PRIMARY SUITE is a private retreat w/ deck access, peaceful views and spa-like bath w/ soaking tub and separate shower. A dedicated office w/ custom built-ins and private entrance offers the ideal work-from-home setting. The upper level has a versatile loft which leads to 3 spacious bedrooms, 2 full baths and a charming hidden loft w/ built-ins. The full footprint lower level features a finished gym, full bath, family room and a guest area, plus substantial unfinished space for storage or future customization. The flexible living spaces, resort-like grounds and recent updates, makes this distinguished Weston residence move-in ready!
Listing Courtesy of SMART MLS / Listed By: Marilyn Heffers, Coldwell Banker Realty
$1,599,000 (USD)
Active

North Madison Area Single Family Home

Active

420 Summer Hill Road Madison, CT 06443

4 Bed
3 Baths
4022 sqft
MLS# 24172058
Privately positioned on nearly two acres in one of Madison's most desirable areas, this expansive Colonial offers a rare combination of privacy, scale, and convenience. Surrounded by natural beauty, the property feels secluded while remaining just minutes from the shoreline and Madison's charming town center, known for its dining, boutique shops, and coastal New England character. A true highlight of the location is its close proximity to Chatfield Hollow State Park-just minutes away-offering scenic trails, a picturesque pond, and year-round outdoor enjoyment. Inside, the home features over 4,000 square feet of living space with generous room sizes, a functional layout, and abundant natural light. Multiple living and entertaining areas provide flexibility for today's lifestyle. The unfinished walk-out basement with high ceilings presents an exceptional opportunity to expand-ideal for a home gym, media room, or additional living space tailored to your needs. The expansive grounds offer endless potential for outdoor living, creating the opportunity for a true private retreat in a sought-after shoreline community. Experience the scale, light, and setting for yourself -schedule your private showing today!
Listing Courtesy of SMART MLS / Listed By: Adriana Radu, Coldwell Banker Realty
$1,550,000 (USD)
Active

Greenfield Hill Area Single Family Home

Active

4041 Redding Road Fairfield, CT 06824

5 Bed
4 Baths
4202 sqft
MLS# 24169234
Virtual Tour
Set on 3.23 acres in the Greenfield Hill area of Fairfield, this 5BR, 4BA home offers privacy, natural surroundings, & a layout designed for the way we live today. Rustic stone walls welcome you to a property overlooking a deep wooded backdrop, with a landscaped lawn defined by a classic stone retaining wall. The main level features a home office, full bath, & an open living and family room with wood-burning fireplace. Access to the covered porch & open deck extends the living space outdoors. The kitchen is functional & welcoming, with a center island, gas range, wall oven, microwave, warming drawer, ample storage, & a dining area for everyday meals. The dining room sits between the kitchen & living spaces, with a bay window overlooking the rear yard. Upstairs, the primary suite offers a private balcony, spa-like bath, large walk-in closet plus two additional closets, & a spiral staircase connection to the main level. Four additional bedrooms include a Jack & Jill bath and hall bath, along with second-floor laundry. Finished lower level with flexible space and unfinished storage. Attached 3-car garage and detached 2-car garage. Enjoy the space and privacy that define Greenfield Hill, with convenient access to Fairfield's town center, Westport, Weston, and Easton, all within approximately a 15-minute drive.This location offers a balance of quiet surroundings and everyday accessibility.
Listing Courtesy of SMART MLS / Listed By: Lori Auerbach, Coldwell Banker Realty
$1,475,000 (USD)
Active

Old Hill Area Land

Active

50 Sylvan Road North Westport, CT 06880

Bed
0 Baths
0 sqft
MLS# 24151295
DREAM YOUR TOMORROW This 1.05 acre of dry, level land that is available for sale, is beautifully sited in the middle of Westport's Old Hill and awaits your imagination. Enter through the original gates of the 1928 Arthur Whiteside Estate at 50 Sylvan North --- the park-like entry to the 25-acre estate built for Whiteside, who founded and headed the commercial credit rating firm of Dun & Bradstreet. There in the 1930's, he perfected a system whereby a client could receive an accurate credit rating on a business within 2 minutes of a request. Whiteside's original Tudor home is visible in the distance where the Sellers of Lot #1 will remain in residence on Lot #2. LOT 1 FOR SALE is flat, pristine, dry and park-like, and enclosed by 1920's fieldstone drywalls which run a full 450' along Sylvan Road North frontage. The Town-Approved Site Plan (FOR DESIGN DEVELOPMENT NOT CONSTRUCTION) is being "simplified" by LandTech to clarify: (1)House site can be moved (2)Sewer and City Water available at street for connection. (3)Natural Gas is available across street, so is being explored as a possibility. Seller has requested feedback from Southern CT Gas about possible hookup to an existing natural gas line across street at 43 Sylvan North/Marion Rd. Still awaiting response from the SCG field manager. (4) utility lines to Lot #2 will logically be moved from the middle of Lot #1 to run alongside the Lot#2 driveway. (5) an optional private and separate Lot#1 entry farther
Listing Courtesy of SMART MLS / Listed By: Martha Eidman, Coldwell Banker Realty
$1,375,000 (USD)
Pending

Downtown North Area Single Family Home

Pending

17 Loren Lane Westport, CT 06880

4 Bed
3 Baths
1560 sqft
MLS# 24168495
Move right into this beautifully updated 4-bedroom, 2.5-bath home ideally set on a fabulous flat property in one of Westport, CT's most desirable walk-to-town neighborhoods. Located on sought-after Loren Lane, this inviting residence offers the perfect blend of comfort, function, and everyday lifestyle just minutes from Main Street, top-rated schools, Metro North train, Compo Beach, and Longshore Club Park. Inside, sun-filled living spaces are anchored by a charming wood-burning fireplace, while the updated kitchen opens seamlessly for daily living and entertaining. A fabulous oversized den provides exceptional living space for relaxing, gathering, or play, and the mudroom with direct garage access adds the practical convenience today's buyers love. The finished lower level delivers outstanding flexibility with dedicated gym space, private home office, and additional room for recreation, media, or storage. Upstairs, four spacious bedrooms offer comfortable accommodations, while the thoughtful floor plan creates an easy flow for modern living. Outside, the level yard is ideal for entertaining, play, and outdoor enjoyment. Rarely does a move-in ready home offer this combination of updated interiors, flexible living space, flat property, and true walk-to-town convenience close to Westport's vibrant downtown shopping, dining, library, parks, beaches, and all this exceptional coastal town has to offer.
Listing Courtesy of SMART MLS / Listed By: Judy Michaelis, Coldwell Banker Realty
$1,329,000 (USD)
Active

In-Town Area Single Family Home

Active

310 Main Street Westport, CT 06880

3 Bed
3 Baths
1437 sqft
MLS# 24158630
Spacious sophistication in the heart of Downtown Westport. Perfectly positioned just moments from vibrant shopping, dining and recreation, this lovely in-town residence offers a rare blend of comfort, flexibility, and location. Bathed in natural light, the inviting living room with wood-burning fireplace sets the tone for relaxed gatherings and quiet evenings alike. The open-concept kitchen features granite countertops and flows seamlessly into the dining area, with French doors leading to a private stone patio - ideal for morning coffee or alfresco entertaining. The main level includes a spacious primary suite with en-suite bath, along with two additional BRs. Downstairs, the finished lower level offers additional space with two more bedrooms and a full bath, offering flexible space for guests, rec/playroom, or multi-generational living. For those seeking a professional setup, the town-approved home occupation designation allows for a separate entrance, two offices, and a waiting room - a turnkey solution for small business owners or remote professionals. With quick access to the Westport Library, Levitt Pavilion, and the town's vibrant dining & shopping scene, this property delivers both lifestyle and convenience. Nearby commuting options include the Metro North Railroad to NYC, Merritt Parkway, I-95. A rare opportunity to live and work in one of Fairfield County's most sought-after communities, or to find a home that offers private space for visitors or extended family.
Listing Courtesy of SMART MLS / Listed By: Barbara Bross, Coldwell Banker Realty

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