Southport, CT Homes for Sale

/8
$3,995,000
- Land
- 2.02 Acres
- $1,977,723 per Acre
817 Sasco Hill Rd, Fairfield, CT 06824

BUILDING OPPORTUNITY ATOP SASCO HILL - This stunning 2-acre parcel atop Sasco Hill, the pinnacle, presents a unique opportunity to build a sensational estate while enjoying captivating views of Southport Harbor and the Norwalk Islands. The exceptional Sasco Hill Road location provides not only privacy but also an extraordinary canvas for a luxurious custom residence, characterized by expansive

Victoria Fingelly Higgins Group Real Estate

817 Sasco Hill Rd, Fairfield, CT 06824
/16
$399,900
- 3 Beds
- 1 Bath
- 1,402 Sq Ft
25 Essex St, Fairfield, CT 06825

Classic 1932 Colonial brimming with charm and strong bones, located in a wonderful Fairfield neighborhood. Centrally situated near shops, schools, and transportation, this home offers an exceptional opportunity to restore and customize to your own taste and style. Featuring 7 spacious rooms, 3 bedrooms, and a walk-up third floor providing abundant storage space, the possibilities are endless. A

Christi McEldowney William Raveis Real Estate

25 Essex St, Fairfield, CT 06825
/40
$4,850,000

Coming Soon
- 5 Beds
- 5 Baths
- 5,103 Sq Ft
22 Evergreen Ave, Westport, CT 06880

Introducing The Winslow Manor, one of Westport's most exceptional estates, is a secluded retreat defined by beauty, privacy, and grace, now available for the first time in decades, inviting its next residents to experience the privilege of living within this storied and extraordinary sanctuary. Just steps from downtown & completely remodeled in 2002, welcome home to a rare and timeless estate

Valerie Alvarez Serhant Connecticut, LLC

22 Evergreen Ave, Westport, CT 06880
/39
$5,950,000
- 3 Beds
- 4.5 Baths
- 2,528 Sq Ft
1681 Fairfield Beach Rd, Fairfield, CT 06824

Some locations on Fairfield Beach simply feel different the moment you arrive. This is one of them. Set along a beautiful stretch of shoreline, the property enjoys a naturally elevated position framed by protective dunes, allowing for an expansive sandy beach experience at both high and low tide. Established seagrass enhances the shoreline's natural beauty, while the manicured lawn creates a

Stephanie Barnes William Raveis Real Estate

1681 Fairfield Beach Rd, Fairfield, CT 06824
/38
$3,190,000

New Construction Open Sun 1PM - 3PM $110K PRICE DROP
- 5 Beds
- 4.5 Baths
- 5,476 Sq Ft
19 Horseshoe Ln, Westport, CT 06880

Located on a quiet cul de sac only one mile from Metro North Train Station/I95 and two miles from Compo Beach, Longshore Country Club and downtown Westport - could your new home be any more convenient? Multiple HOBI award winning builder, CCO Habitats, presents its latest new construction project - a 5 bedroom, 4.5 bath home finished on 4 levels with room for a smaller pool. As always, there are

Maryann Levanti Higgins Group Bedford Square

19 Horseshoe Ln, Westport, CT 06880
/14
$8,696,000

New Construction
- 7 Beds
- 8 Baths
- 9,422 Sq Ft
688 Hulls Farm Rd, Southport, CT 06890

Set within artisan stone walls with curated flowering landscapes, this magnificent stone and stucco residence is a masterful tribute to Southport's enduring architectural legacy. Designed to blend seamlessly among the grand neighboring estates of this coveted enclave, 688 Hulls Farm strikes a rare balance: modern in execution, timeless in presence. Construction begins in April with Coastal Luxury

Jaclyn Picarillo Higgins Group Bedford Square

688 Hulls Farm Rd, Southport, CT 06890
/39
$1,950,000
- 5 Beds
- 3 Baths
- 3,709 Sq Ft
215 Old Post Rd, Fairfield, CT 06824

Incredible opportunity to live in the Fairfield Beach neighborhood, within easy walking distance to beach & marina. Under 1 mile to train & town center. Beautifully renovated vintage home with so many improvements/amenities, including gorgeous expanded kitchen, renovated bathrooms, plantation shutters, new windows, new roof, fresh exterior paint, fencing and more. The inviting foyer welcomes you

Katie O'Grady Compass Connecticut, LLC

215 Old Post Rd, Fairfield, CT 06824
/18
$769,000
- 3 Beds
- 3 Baths
- 2,027 Sq Ft
282 Marlborough Terrace, Fairfield, CT 06825

A unique opportunity to own this side-by-side two-family home in a sought-after neighborhood. Offering exceptional value and versatility, this property is ideal for investors, owner-occupants, or multigenerational living. Unit One features a bright and inviting living room, Bedroom, an eat-in kitchen, and a full bath. Filled with natural light, the space offers a warm, comfortable atmosphere with

Kathleen Blackall William Raveis Real Estate

282 Marlborough Terrace, Fairfield, CT 06825
/2
$143,000

$17K PRICE DROP
- Land
- 9,583 Sq Ft
- $650,000 per Acre
860 Briarwood Ave, Bridgeport, CT 06604

"Prime development opportunity in Bridgeport! This vacant lot offers flexible possibilities for new construction in a growing area. Close to downtown, parks, local universities, and commuter routes. Ideal for investors seeking strong rental or resale demand. Sold as-is , buyer responsible for verifying zoning and permitting."

Rosania Melo Rosania Melo Broker

860 Briarwood Ave, Bridgeport, CT 06604
/39
$2,198,000

Open Thu 1PM - 4PM
- 3 Beds
- 3 Baths
- 3,810 Sq Ft
2 Charcoal Ln, Westport, CT 06880

Located in the highly sought-after Charcoal Hill neighborhood, this move-in ready home on 2+ private acres features 3 bedrooms, 3 full baths, PLUS TWO ADDITIONAL VERSATILE ROOMS that significantly expand the home's livable space. Bordering a 7-acre Aspetuck Land Trust preserve on a quiet cul-de-sac, it offers serene privacy with easy access to town, the Merritt Parkway, and Coleytown schools.

Alexey Gavrilov William Pitt Sotheby's Int'l

2 Charcoal Ln, Westport, CT 06880
/34
$4,700,000

Open Sun 12PM - 2PM
- 6 Beds
- 6.5 Baths
- 7,575 Sq Ft
21 Daniel Ct, Westport, CT 06880

Nestled at the end of an exceptionally wide, tree-lined cul-de-sac on one of Westport's most picturesque streets, this timeless brick estate offers both elegance and privacy while remaining moments from town, beaches, and commuting conveniences. Set with a paver circular driveway and surrounded by mature landscaping, the property exudes warmth, scale, and classic sophistication at every turn.

Meredith Cohen Serhant Connecticut, LLC

21 Daniel Ct, Westport, CT 06880
/38
$900,000

Open Sun 12PM - 1PM $25K PRICE DROP
- 6 Beds
- 4 Baths
- 2,319 Sq Ft
352 Marlborough Terrace, Fairfield, CT 06825

Opportunity knocks! Large, meticulously maintained two-family duplex in prime, high-appreciation Fairfield location. Ideal for investors or owner-occupants seeking strong income potential & long-term value. Rent both units or live in one while offsetting costs with the other. Fully renovated in 2023, this 2,319SF property offers exceptional flexibility with 6BRs and 2 full & 2 half baths split

Kathleen Gibbon Brown Harris Stevens

352 Marlborough Terrace, Fairfield, CT 06825
/33
$1,325,000
- 6 Beds
- 2.5 Baths
- 3,071 Sq Ft
7 Keller Ln, Westport, CT 06880

Pristine Classic Westport Colonial thoughtfully updated to accommodate today's lifestyle. Home offers a gracious Living Room/Fpl/dining area, Six spacious Bedrooms plus 22x 28 Bonus room. Two bedrooms plus full bath on main Level. 16 x 23 Primary Bedroom plus 3 generous bedrooms on upper level. This level serviced by luxurious updated Full Bath. Kitchen is appointed with upscale appliances

Louise Bromberger The Riverside Realty Group

7 Keller Ln, Westport, CT 06880
/14
$4,375,000

New Construction
- 4 Beds
- 4.5 Baths
- 4,100 Sq Ft
143 Roseville Rd, Westport, CT 06880

Nestled in peaceful seclusion yet just moments to town's shops, restaurants and amenities, an extraordinary residence crafted to the highest standards is being imagined to live in harmonious dialogue with the surrounding natural landscape. The proposed new construction masterpiece by Coastal Luxury Homes is thoughtfully designed to honor the property's pristine natural beauty, where a babbling

Jaclyn Picarillo Higgins Group Bedford Square

143 Roseville Rd, Westport, CT 06880
/35
$1,799,000

Open Thu 12PM - 3PM
- 3 Beds
- 3 Baths
- 2,078 Sq Ft
787 Rowland Rd, Fairfield, CT 06824

Wonderful opportunity to live in the desirable Fairfield Beach neighborhood, just two houses from the shoreline and offering private gated beach access through the Fair Acres Association. This inviting coastal retreat captures the very best of Fairfield Beach living. Thoughtfully designed across three levels, the home blends relaxed seaside charm with flexible living spaces. The sun-filled

Katie O'Grady Compass Connecticut, LLC

787 Rowland Rd, Fairfield, CT 06824
/40
$699,000

Open Sat 1PM - 3PM
- 3 Beds
- 1 Bath
- 1,772 Sq Ft
36 Romanock Place, Fairfield, CT 06825

Incredible opportunity in the sought-after Lake Hills neighborhood! Set on a quiet cul-de-sac surrounded by million-dollar-plus new construction, this 3/4-bedroom, 1-bath home offers endless potential. Ready for updates, it's the perfect opportunity to build equity, renovate, or create the home of your dreams. The first floor features a spacious eat-in kitchen, living room, full bath, primary

Kim Vartuli Keller Williams Realty

36 Romanock Place, Fairfield, CT 06825
/39
$2,000,000

Coming Soon
- 6 Beds
- 7.5 Baths
- 8,750 Sq Ft
475 Springer Rd, Fairfield, CT 06824

Set on 284 feet of direct waterfront in Fairfield's beautiful Lake Hills Association, this is the place your grandchildren will tell their grandchildren about. An extraordinary 6-bedroom home offering a true year-round resort lifestyle with a private beach, dock, and panoramic lake views. Designed for entertaining and multi-generational living, the home features 4 finished levels of beautifully

Alan Hamilton William Raveis Real Estate

475 Springer Rd, Fairfield, CT 06824
/40
$2,500,000

Open Sat 2PM - 4PM $200K PRICE DROP
- 5 Beds
- 5 Baths
- 5,793 Sq Ft
28 Bulkley Ave N, Westport, CT 06880

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

Judy Michaelis Coldwell Banker Realty

28 Bulkley Ave N, Westport, CT 06880
/2
$4,300,000
- 6 Beds
- 6 Baths
- 6,000 Sq Ft
378 Penfield Rd, Fairfield, CT 06824

IMAGES FROM BUILDER'S PORTFOLIO.Remarkable CUSTOMIZABLE approx 6,000 Sqft New Beach Construction Home on a very RARE OVERSIZED 0.31 acre lot with a non-pareil luxurious Open floor plan on the Premier street in beach area ! Situated just two blocks away from Penfield Beach. Created by Master Local Builder; NEW GENERATION HEALTHY HOMES. Custom designed to offer state of the art amenities, 7

Helene Salerno Ogents, LLC

378 Penfield Rd, Fairfield, CT 06824
/40
$1,975,000

Open Sun 12PM - 2PM
- 4 Beds
- 3 Baths
- 3,253 Sq Ft
5 Tanglewood Ln, Westport, CT 06880

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

Doug Bross Coldwell Banker Realty

5 Tanglewood Ln, Westport, CT 06880
/39
$3,350,000
- 5 Beds
- 5.5 Baths
- 5,789 Sq Ft
221 Greens Farms Rd, Westport, CT 06880

The Bedford House: Architecturally and historically significant estate in Greens Farms. This exceptional property offers a rare opportunity to own one of Westport's true gems with a remarkable provenance. Set on 2.33 acres with a gunite pool & spa, court and a 2400 SF barn w/ 3 car garage, loft and more, this estate blends timeless elegance with modern comfort. Originally built in 1904 and

Patricia Shea Coldwell Banker Realty

221 Greens Farms Rd, Westport, CT 06880
/39
$800,000

$99K PRICE DROP
- 3 Beds
- 2.5 Baths
- 1,614 Sq Ft
81 Old Stratfield Rd, Fairfield, CT 06825

Located in the heart of Tunxis Hill-one of Fairfield's most convenient neighborhoods-this beautifully maintained Colonial blends classic design with modern living. Featuring 3 bedrooms and 2.1 bathrooms, the home has been freshly painted throughout and is truly move-in ready. Just minutes from shopping, dining, and everyday essentials, 81 Old Stratfield Road offers the perfect balance of comfort

Young Lee Houlihan Lawrence WD

81 Old Stratfield Rd, Fairfield, CT 06825
/2
$5,980,000

New Construction
- 6 Beds
- 9 Baths
- 10,521 Sq Ft
21 Sturges Commons, Westport, CT 06880

NEW CONSTRUCTION TO BE BUILT IN THE COVETED HUNT CLUB NEIGHBORHOOD - Renowned, luxury builder Mattera Construction is well-known for architecturally significant & stunning modern homes filled with elegance, timeless beauty, custom interiors with state-of-the-art amenities. Now offering a perfectly designed 6 bedroom home finished on 4 levels filled with elegant finishes, well sited on a quiet

Patricia Shea Coldwell Banker Realty

21 Sturges Commons, Westport, CT 06880
/2
$6,999,999

New Construction
- 6 Beds
- 9 Baths
- 10,521 Sq Ft
32 Narrow Rocks Rd, Westport, CT 06880

NEW CONSTRUCTION BY RENOWNED LUXURY BUILDER MATTERA CONSTRUCTION - STEPS TO COMPO BEACH! A rare opportunity to own a brand-new, architecturally refined home in one of Westport's most coveted coastal locations-just steps to Compo Beach, Longshore Club, downtown Westport, the train, and schools. Currently under construction, this impeccably designed 6-bedroom residence spans four finished levels

Judy Michaelis Coldwell Banker Realty

32 Narrow Rocks Rd, Westport, CT 06880
/2
$5,650,000

New Construction Open Sun 1PM - 3PM
- 7 Beds
- 9 Baths
- 8,762 Sq Ft
8 Pleasant Valley Ln, Westport, CT 06880

Experience modern luxury in this new SIR SIGNATURE Home by SIR Development, Westport's premier builder. Set on 1.02 private acres on a coveted culdesac, this home offers a striking approach, 3car garage, and rare backyard privacy, all within walking distance to Bedford Middle, Staples High, Wakeman Fields, and Town Farm. A fresh contemporary aesthetic features a dramatic twostory foyer, 10ft

Doug Bross Coldwell Banker Realty

8 Pleasant Valley Ln, Westport, CT 06880
/16
$230,000

$20K PRICE DROP
- 2 Beds
- 2 Baths
- 1,648 Sq Ft
80 Cartright St Unit PHA, Bridgeport, CT 06604

Very Rare Penthouse Unit on Top Floor with Large Balcony. Largest Unit in Complex, Over 1,600 Sq Ft. Two Large Bedrooms. Two Large Full Bathrooms. Picture Frame Molding Throughout unit. Crown Molding in Many Rooms. Hardwood and Parquet floors Throughout. Large Dining Room which opens up to Cozy Living Room with Sliders to the Balcony Providing Nice Vistas of the Surrounding Area. Storage Area and

Christopher Ziko Higgins Group Real Estate

80 Cartright St Unit PHA, Bridgeport, CT 06604
/15
$6,995,826

New Construction
- 6 Beds
- 10 Baths
- 8,417 Sq Ft
24 Edgemarth Hill Rd, Westport, CT 06880

This Beauty will be ready Summer 2026! Construction of this 8,417SF dream residence with pool and spa on 1 private acre in coveted Greens Farms, Westport, is in full swing. 24 Edgemarth Hill was designed and will be crafted and appointed with the finest materials - see rendering photos of what's to come. Flaunting sexy floor-to-ceiling walls of windows, stone and textured accents, vaulted

Jaclyn Picarillo Higgins Group Bedford Square

24 Edgemarth Hill Rd, Westport, CT 06880
/7
$10,650,000

New Construction
- 6 Beds
- 8 Baths
- 9,100 Sq Ft
11 Dogwood Ln, Westport, CT 06880

Another extraordinary masterpiece by Coastal Luxury Homes, ideally situated in one of Westport's premier neighborhoods. Spanning over 9000 square feet of living space this 6 bedroom estate is defined by bold architectural lines, chic designer interiors, expansive balconies and seamless indoor-outdoor living. A resort caliber pool, fully equipped outdoor kitchen, and lush manicured grounds

Jen Kass Higgins Group Bedford Square

11 Dogwood Ln, Westport, CT 06880
/40
$1,700,000

Coming Soon
- 5 Beds
- 4.5 Baths
- 4,676 Sq Ft
282 Glen Ridge Rd, Fairfield, CT 06825

Beautiful Center Hall Colonial in Fairfield's sought after Lake Mohegan neighborhood. This lovingly maintained 5 bedroom, 4 full & 1 half bath home offers the perfect combination of space, functionality & location. A dramatic vaulted entry welcomes you inside where hardwood floors flow throughout the home. The spacious layout includes a home office, formal dining room, expansive family room with

Amie Belile William Raveis Real Estate

282 Glen Ridge Rd, Fairfield, CT 06825
/2
$4,999,999
- Land
- 17 Acres
- $294,118 per Acre
2 A Owenoke Park, Westport, CT 06880

The property consists of 17 waterfront acres including a 7 acre upland section.

Ralph Harvey ListWithFreedom.com

2 A Owenoke Park, Westport, CT 06880
/32
$598,000

Open Sat 1PM - 3PM
- 4 Beds
- 2 Baths
- 2,015 Sq Ft
845 Knapps Hwy, Fairfield, CT 06825

Welcome to 845 Knapps Highway, a move-in ready 4 Bedroom Cape located in Fairfield's desirable Tunxis Hill neighborhood. Filled with natural light and thoughtfully updated throughout, this home offers a flexible floor plan ideal for both everyday living and entertaining. The oversized eat-in kitchen features granite countertops, stainless steel appliances, large center island, vaulted ceilings

Bryan Morris William Pitt Sotheby's Int'l

845 Knapps Hwy, Fairfield, CT 06825
/40
$1,460,000

New Construction
- 2 Beds
- 2.5 Baths
- 1,416 Sq Ft
781 Post Rd E Unit 102, Westport, CT 06880

AMAZING NEW CONSTRUCTION! Located in the heart of Westport, The Gables of Westport presents a collection of eight townhomes and five flats, blending sophisticated design with the ease of in-town living. Enjoy close proximity to Metro-North, major highways, Longshore Club & Park, Compo Beach, Levitt Pavilion, Westport Country Playhouse, fine dining, shopping, and entertainment. Crafted by local

Todd Gibbons Boost Real Estate Group

781 Post Rd E Unit 102, Westport, CT 06880
/2
$4,700,000
- 6 Beds
- 6 Baths
- 6,000 Sq Ft
394 Penfield Rd, Fairfield, CT 06824

IMAGES FROM BUILDER'S PORTFOLIO.Remarkable CUSTOMIZABLE approx 6,000 Sqft New Beach Construction Home on a very RARE OVERSIZED 0.31 acre lot with a non-pareil luxurious Open floor plan on the Premier street in beach area ! Situated just two blocks away from Penfield Beach. Created by Master Local Builder; NEW GENERATION HEALTHY HOMES. Custom designed to offer state of the art amenities, 7

Helene Salerno Ogents, LLC

394 Penfield Rd, Fairfield, CT 06824
/19
$525,000

Open Sat 12PM - 3PM
- 3 Beds
- 2 Baths
- 1,288 Sq Ft
198 Grasmere Ave, Fairfield, CT 06824

Warm, inviting, and full of charm, this brick 3-bedroom, 2-bath townhouse is a rare find in a wonderful location. Originally built as the model home per owner, it offers slightly larger proportions than neighboring units. Features include hardwood floors, original trim details, abundant windows that fill the home with natural light, new roof installed in 2025, and Bosch heating/cooling system

Monica Flanagan William Raveis Real Estate

198 Grasmere Ave, Fairfield, CT 06824
/40
$1,050,000

$25K PRICE DROP
- 4 Beds
- 2 Baths
- 1,919 Sq Ft
464 Round Hill Rd, Fairfield, CT 06824

Welcome to this storybook cape in a prime location! Charming and inviting with a classic layout, yet versatile for today's lifestyle. You'll love the updated Kitchen with quartz countertops and beautiful views of the backyard where tulips, hydrangea, and cherry trees are in bloom. Enjoy breakfast at the kitchen table, or open the sliders and savor your morning coffee on the stone patio. The

Lorelei Atwood Higgins Group Real Estate

464 Round Hill Rd, Fairfield, CT 06824
/32
$355,000
- 2 Beds
- 2.5 Baths
- 1,490 Sq Ft
2612 North Ave Unit F9, Bridgeport, CT 06604

Desirable Brooklawn gated community of well-maintained tri-level townhouses. 1490 sqft luxury townhouse with 2 large bedrooms and 2.5 bathrooms. Open floor plan, hardwood floors on the main level, white kitchen cabinets, and white appliances. Primary king-size bedroom suite with full bathroom and large walk-in closet. 2nd floor laundry. 2nd floor has wall-to-wall carpet. Finished lower level

Mikhail Faifman William Raveis Real Estate

2612 North Ave Unit F9, Bridgeport, CT 06604
/12
$630,000

$69K PRICE DROP
- 6 Beds
- 3 Baths
- 3,069 Sq Ft
195 Lenox Ave Unit 197, Bridgeport, CT 06605

Welcome to 195 Lenox Avenue - a modern and versatile 3-family home perfect for both investors and first-time buyers. With 6 bedrooms, 3 full bathrooms, and a full basement, this property offers plenty of space and excellent rental potential. The first and second floors each allow for an extra bedroom conversion, maximizing cash flow. Inside, the units are updated and well-maintained, providing

Shafran Salim Guy Bocicaut Real Estate

195 Lenox Ave Unit 197, Bridgeport, CT 06605
/40
$1,349,000

Open Thu 11AM - 2PM
- 3 Beds
- 3.5 Baths
- 2,047 Sq Ft
186 Compo Rd S, Westport, CT 06880

Tucked behind a tall fence flanked by stone pillars, this customized contemporary home feels like a private hideaway, but less than 5 minutes to town, schools, beach and train. Looking for one level living? That can be easily accommodated here with a sun-filled main level open floor plan featuring a Living Room with fireplace, a large well-equipped Kitchen with a spacious Dining Area and

Laurie Crouse Coldwell Banker Realty

186 Compo Rd S, Westport, CT 06880

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