Southport, CT Homes for Sale

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  /38

  $925,000

  • 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
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• 

  

  

  /40

  $1,495,000

  • 2 Beds
  • 2.5 Baths
  • 1,764 Sq Ft

  494 Pequot Ave, Southport, CT 06890

  Charming Pied-a-terre in Connecticut's alluring Southport Village! Whether you're looking for a permanent residence or your home away from home, this is a perfect vacation home or condo alternative. Leave without a care or immerse yourself in this historic maritime enclave. A rare find in the heart of the Village, this home is steps from the neighborhood eateries, shops, metro, pub, bakery, post

  Linda Raymond William Raveis Real Estate

  494 Pequot Ave, Southport, CT 06890
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  /17

  $950,000

  • 6 Beds
  • 3 Baths
  • 2,822 Sq Ft

  252 Villa Ave, Fairfield, CT 06825

  Well-maintained rare find - large 3-family home in Fairfield! This property is ideally located in a highly convenient area with easy access to shopping, dining, and major highways. All three units have been completely renovated and are in excellent condition. Each unit features its own laundry hookup. Long-term, reliable tenants are already in place, making this an excellent investment

  Shan Guan Coraland Realty

  252 Villa Ave, Fairfield, CT 06825
• 

  

  

  /27

  $599,000

  • 3 Beds
  • 2 Baths
  • 1,386 Sq Ft

  3 Hills Ln, Westport, CT 06880

  A wonderful lifestyle awaits at Birchwood Condominiums, where low-maintenance living meets exceptional convenience. Ideally located on the Westport-Norwalk border, this sun-filled 3-bedroom, 2-bath residence offers a rare combination of privacy, natural beauty, and walkable access to everyday essentials, including Whole Foods just across the street. Set at the top of Hills Lane in a peaceful,

  Mary Ann Lindwall The Riverside Realty Group

  3 Hills Ln, Westport, CT 06880
• 

  

  

  /39

  $2,699,000

  • 5 Beds
  • 4.5 Baths
  • 4,628 Sq Ft

  1 Angora Rd, Westport, CT 06880

  One of Westport's premiere CUL-DE-SACS, WALKING DISTANCE TO ALL 3 SCHOOLS (Long Lots, Bedford, Staples), and 2.3 MILES TO GREENS FARMS TRAIN STATION, this beautifully renovated (2016/2017) 5-bedroom, 4.5-bath home perfectly blends modern luxury with timeless charm. Set on a full acre of manicured grounds, this property offers a serene retreat just minutes from every essential. The open floor plan

  Gina Hackett Compass Connecticut, LLC

  1 Angora Rd, Westport, CT 06880
• 

  

  /40

  $5,549,000

  • 4 Beds
  • 5 Baths
  • 7,105 Sq Ft

  80 Compo Rd N, Westport, CT 06880

  Timeless design meets modern sustainability in this stunning shingle-style home, set on 1.5 private in-town acres. Sunlight fills every room through oversized Kolbe windows, showcasing park-like grounds and mature plantings. The kitchen impresses with custom cabinetry, a handcrafted zinc island, and top-tier Wolf and Sub-Zero appliances. Step outside to a spectacular bluestone patio with an

  Adrienne Durkin Compass Connecticut, LLC

  80 Compo Rd N, Westport, CT 06880
• 

  

  /3

  $450,000

  • Land
  • 0.16 Acre
  • $2,812,500 per Acre

  37 Bartram Ave, Bridgeport, CT 06605

  St Mary's by the Sea flat and cleared building lot. Single family and multifamily possible at this location. Beautiful tree lined street close to the water.

  David Krasnoff Compass Connecticut, LLC

  37 Bartram Ave, Bridgeport, CT 06605
• 

  

  /40

  $4,990,000

  • 5 Beds
  • 4 Baths
  • 5,779 Sq Ft

  1149 & 1148 Fairfield Beach Rd, Fairfield, CT 06824

  Toes in the sand! Welcome to 1149 & 1148 Fairfield Beach Rd where the best beach memories are made&every day feels like summer....2 wonderful homes:Main Home ~1149 w/direct waterfront & private sandy beach AND 1148 ~ A fun updated guest home just steps across the street. Enjoy true beachfront living w/no steps from your main level family room to an expansive patio where you can enjoy friends and

  Christine Magliocco Higgins Group Real Estate

  1149 & 1148 Fairfield Beach Rd, Fairfield, CT 06824
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  /38

  $2,399,000

  • 5 Beds
  • 6 Baths
  • 5,739 Sq Ft

  2 Ledgemoor Ln, Westport, CT 06880

  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

  Alex Chingas Coldwell Banker Realty

  2 Ledgemoor Ln, Westport, CT 06880
• 

  

  /25

  $1,500,000

  • 2 Beds
  • 2.5 Baths
  • 2,161 Sq Ft

  104 Harvest Commons Unit 104, Westport, CT 06880

  Tasteful turn-key townhome with main level primary suite, open plan and two private outdoor areas to enjoy. Fully renovated with quality materials and a neutral palette that will appeal to all. One of the largest 2 bedroom models with bonus loft/office and vaulted ceilings throughout, plus a finished lower level for your home theater or gym. Every detail has been considered for comfort and peace

  Patricia Prenderville Higgins Group Real Estate

  104 Harvest Commons Unit 104, Westport, CT 06880
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  /38

  $5,925,000

  • 6 Beds
  • 9 Baths
  • 6,561 Sq Ft

  3 Stony Point Rd, Westport, CT 06880

  Located within the highly desirable Stony Point association, this exceptional home offers a rare combination of privacy, water views, and convenience just moments from the train, local restaurants, and everyday amenities. This particular home enjoys private dock membership, providing summer boat access just steps from your door. Completely transformed and expanded in 2016, the home features over

  Debra Shaughnessy Coldwell Banker Realty

  3 Stony Point Rd, Westport, CT 06880
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  /15

  $1,625,000

  • 4 Beds
  • 3.5 Baths
  • 3,360 Sq Ft

  190 North Ave, Westport, CT 06880

  First time on the market in over 50 years, this meticulously maintained 1910 Colonial is a rare and timeless offering in one of Westport's most cherished settings. Set on 2.66 private acres and abutting an additional 7 acres of protected Land Trust, the property offers exceptional privacy, pastoral views, and enduring tranquility. Rich in character and architectural detail, the home features four

  Kim Harizman Compass Connecticut, LLC

  190 North Ave, Westport, CT 06880
• 

  

  /31

  $1,299,000

  • 4 Beds
  • 3.5 Baths
  • 2,340 Sq Ft

  19 Half Mile Common, Westport, CT 06880

  Beautifully renovated split level situated on a centrally located cul-de-sac. This sun-filled residence offers an open floor plan with a bright living room featuring a cozy fireplace, an updated kitchen, and an adjoining dining area. The property includes 4 bedrooms and 3 1/2 renovated baths, highlighted by an oversized primary suite with a spa-like bathroom. The finished lower level provides

  Mary Kate Klemish-Boehm Brown Harris Stevens

  19 Half Mile Common, Westport, CT 06880
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  /32

  $1,329,000

  • 3 Beds
  • 2.5 Baths
  • 2,029 Sq Ft

  310 Main St, Westport, CT 06880

  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

  Barbara Bross Coldwell Banker Realty

  310 Main St, Westport, CT 06880
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  /40

  $899,000

  • 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
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  /25

  $500,000

  • 7 Beds
  • 3 Baths
  • 2,784 Sq Ft

  36 Lee Ave Unit 38, Bridgeport, CT 06605

  This well-maintained two-family home features two spacious units, each with three bedrooms, offering ample living space and comfortable layouts. In excellent condition, the property presents a versatile opportunity for owner-occupants seeking rental income or investors pursuing a strong, income-producing asset. Located in a highly desirable area with solid appreciation and future growth

  Angel Mora eXp Realty

  36 Lee Ave Unit 38, Bridgeport, CT 06605
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  /27

  $680,000

  • 6 Beds
  • 4 Baths
  • 2,860 Sq Ft

  5 Durando Place, Bridgeport, CT 06605

  Exceptional Black Rock Two-Family | Bridgeport, CT A rare opportunity in one of Bridgeport's most sought-after neighborhoods Welcome to this beautifully expanded two-family home nestled in the heart of Black Rock - a charming 1936 residence that masterfully blends timeless period character with thoughtful modern updates. First Floor Unit offers 2 spacious bedrooms and 2 full baths, plus a

  Shelly Olivadoti Berkshire Hathaway NE Prop.

  5 Durando Place, Bridgeport, CT 06605
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  /34

  $550,000

  • 5 Beds
  • 2.5 Baths
  • 2,580 Sq Ft

  839 Laurel Ave, Bridgeport, CT 06604

  Must see this big unique home in person to really appreciate it. First floor consists of Formal dining room, kitchen and living room. Also has a sunroom/mudroom leading to a huge backyard. Upstairs you will find 4 large bedrooms and nook in hallway. Walk upstairs to attic for more recreational space. Full basement.

  Ishwar Rameshar Besmatch Real Estate

  839 Laurel Ave, Bridgeport, CT 06604
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  /40

  $1,269,000

  • 4 Beds
  • 3.5 Baths
  • 2,959 Sq Ft

  185 Windsor Rd, Fairfield, CT 06824

  Tucked away on a quiet cul-de-sac in the desirable University area of Fairfield, this move-in-ready Colonial combines thoughtful updates, flexible living space, and an impressive, detached studio. Offering nearly 3,000 square feet of finished living space across three levels, this 4-bedroom, 3.5-bath home features a remodeled eat-in kitchen with new appliances, quartz countertops, farmhouse sink,

  Carrie Sakey Coldwell Banker Realty

  185 Windsor Rd, Fairfield, CT 06824
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  /40

  $15,000,000

  • 7 Beds
  • 6.5 Baths
  • 6,215 Sq Ft

  4 Sherwood Island Ln, Westport, CT 06880

  Hidden along a private lane in Westport's Greens Farms neighborhood, this extraordinary 20-acre waterfront estate unfolds as one of the most remarkable shoreline settings ever offered. For more than 65 years, it has been held and enjoyed by the same family as a place to gather, unwind, and take in the ever-changing views across Sherwood Island Park and Long Island Sound. Surrounded by protected

  Andrew Whiteley Brown Harris Stevens

  4 Sherwood Island Ln, Westport, CT 06880
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  /38

  $1,599,000

  • 3 Beds
  • 3.5 Baths
  • 3,012 Sq Ft

  71 Aberdeen Way Unit 71, Southport, CT 06890

  Perfectly situated in Southport, this beautifully appointed 3-bedroom, 3.5-bath Colonial townhouse end unit offers an exceptional lifestyle just moments from village shops, restaurants, Southport Harbor, and the Metro-North train. Thoughtfully updated, the remodeled kitchen features quartz countertops, a sleek backsplash, and premium Bosch appliances, centered around a generous island-opening

  Michael Ferraro Compass Connecticut, LLC

  71 Aberdeen Way Unit 71, Southport, CT 06890
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  /40

  $699,000

  • 4 Beds
  • 2 Baths
  • 2,502 Sq Ft

  1335 Black Rock Turnpike, Fairfield, CT 06825

  Best Buy in Fairfield - Nicely Remodeled Spacious 4 Bedrooms & 2 Full bath Home on a convenient location - Close to shopping, Restaurant, Highways and New Train Station. A beautifully designed 4-bedroom, 2 Full bathroom home offering nearly 2500 square feet of living space. This home has a Private beautifully landscaped Back yard. Inside, you'll find a light-filled layout designed for modern

  Aziz Seyal William Raveis Real Estate

  1335 Black Rock Turnpike, Fairfield, CT 06825
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  /38

  $985,000

  • 4 Beds
  • 2 Baths
  • 1,735 Sq Ft

  52 Robin Ln, Fairfield, CT 06824

  Immaculate University area split level home on beautiful lot which is just over one third of an acre. Perfect opportunity to rebuild completely on one of the most generously-sized parcels on this street. Or, to renovate, expand, and reimagine your own dream, simply enjoying its comfort as it was built. Tremendous backyard with classic stone wall. Top-rated schools, close to shopping, and less

  Janet Warren William Raveis Real Estate

  52 Robin Ln, Fairfield, CT 06824
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  /13

  $142,900

  • 2 Beds
  • 1 Bath
  • 850 Sq Ft

  78 Haddon St Unit 1, Bridgeport, CT 06605

  Vibrant Black Rock community convenient to all. Unusually large square footage. Convenient 1st floor end unit. In need of updates but generally in good condition. Great opportunity to refresh to your taste.

  Todd Debek Debek Real Estate Services LLC

  78 Haddon St Unit 1, Bridgeport, CT 06605
• 

  

  /22

  $1,400,000

  • 6 Beds
  • 4 Baths
  • 4,485 Sq Ft

  135 Grace St, Fairfield, CT 06825

  Tucked away at the end of a quiet dead-end street, this beautifully maintained property consists of two half duplex units, offering in each approximately 1,950 square feet of thoughtfully designed, open-concept living space - perfect for both everyday living and entertaining. The property features a spacious, private fenced-in yard, ideal for outdoor gatherings, or simply relaxing in your own

  Matt Lahey Higgins Group Real Estate

  135 Grace St, Fairfield, CT 06825
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  /40

  $2,950,000

  • 6 Beds
  • 5.5 Baths
  • 5,938 Sq Ft

  36 Bauer Place, Westport, CT 06880

  Better than new! This beautifully appointed 4-level home blends contemporary design with warmth, comfort, and thoughtful upgrades throughout. The heart of the home is a cook's dream kitchen with gourmet appliances, a full pantry, and a massive center island showcasing stunning finishes. Designed for both beauty and function, it opens seamlessly to the bright, welcoming family room. Together,

  Jennifer Twombly Compass Connecticut, LLC

  36 Bauer Place, Westport, CT 06880
• 

  

  /26

  $8,995,000

  • 8 Beds
  • 10 Baths
  • 15,172 Sq Ft

  2 Judy Point Ln, Westport, CT 06880

  Set on over 3 private acres with sweeping water views, 2 Judy Point Lane is a remarkable Westport waterfront estate offering approximately 14,000 square feet of living space and a rare compound-style layout. The property consists of two substantial residences connected by a breezeway, creating exceptional flexibility for multi-generational living, extended guests, or a private guest house.

  Daniel Kramp Christie's International Real Estate

  2 Judy Point Ln, Westport, CT 06880
• 

  

  /6

  $22,825,000

  • 8 Beds
  • 10 Baths
  • 12,946 Sq Ft

  11 Beachside Common, Westport, CT 06880

  Direct Waterfront | Greens Farms An extraordinary new waterfront estate by award-winning Coastal Luxury Homes is coming to one of the most coveted stretches of the Connecticut shoreline. Set in the heart of Greens Farms, this spectacular 12,948 square foot modern residence will span four levels and capture sweeping, unobstructed views across Sherwood Island, Burying Hill Beach, and Long Island

  Andrew Whiteley Brown Harris Stevens

  11 Beachside Common, Westport, CT 06880
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  /37

  $3,990,000

  • 5 Beds
  • 7 Baths
  • 7,409 Sq Ft

  13 Rockyfield Rd, Westport, CT 06880

  This pristine Colonial offers timeless Westport elegance and effortless living, set on 1.12 flat, manicured acres framed by classic stone walls in a coveted, quiet neighborhood just one hour from NYC. The five-bedroom home features five full and two half baths, two dedicated offices, two versatile bonus spaces, custom millwork throughout, and abundant storage-perfect for today's work-from-home,

  Danna Rogers Higgins Group Bedford Square

  13 Rockyfield Rd, Westport, CT 06880
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  /32

  $4,899,000

  • 6 Beds
  • 8 Baths
  • 8,190 Sq Ft

  19 Mortar Rock Rd, Westport, CT 06880

  Stunning modern transitional home built by Compo Luxury Homes in 2024 and ideally located just minutes to downtown Westport, Compo Beach, and the train. Set on .65 acres with city water, sewer, and natural gas, this beautifully designed residence offers over 8,000 square feet across four finished levels with 6 bedrooms, 6 full and 2 half baths. The open floor plan features a chef's kitchen with

  Danna Rogers Higgins Group Bedford Square

  19 Mortar Rock Rd, Westport, CT 06880
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  /35

  $1,885,000

  • 3 Beds
  • 3.5 Baths
  • 3,805 Sq Ft

  491 Westway Rd Unit 491, Fairfield, CT 06890

  Located within the only gated enclave in the heart of Southport Village, this exceptional townhome offers a rare blend of privacy, convenience, and refined design. ELEVATOR READY! Just steps from Southport's charming shops, restaurants, train station, and beach, the setting is as desirable as it is walkable. This home spans three thoughtfully designed levels, each showcasing sophisticated,

  Denise Walsh William Raveis Real Estate

  491 Westway Rd Unit 491, Fairfield, CT 06890
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  /6

  $1,250,000

  • Land
  • 0.15 Acre
  • $8,333,333 per Acre

  15 Gorham Ave, Westport, CT 06880

  Nestled on a charming historic street in one of Westport's most desirable neighborhoods, 15 Gorham Avenue offers a rare opportunity to build your dream home just moments from the heart of town. This exceptional property allows for the construction of a approximately 2,500+/- square foot residence, perfectly suited for today's lifestyle while blending beautifully with the character of the

  Peter Lane Ogents, LLC

  15 Gorham Ave, Westport, CT 06880
• 

  

  /38

  $2,095,000

  • 4 Beds
  • 5 Baths
  • 3,921 Sq Ft

  2177 Cross Hwy, Fairfield, CT 06824

  A special property with pool & tennis court, on the Westport border, minutes to shops, restaurants and train. Experience refined luxury in this picturesque setting, situated back from the road down a long, lighted driveway, winding past a serene pond. Nearly 4000 sq ft with 4 bedrooms & 4.5 baths, this open floor plan home features city water, sewer, natural gas, oil heat and central A/C for

  Mary Ellen Gallagher Compass Connecticut, LLC

  2177 Cross Hwy, Fairfield, CT 06824
• 

  

  /25

  $770,000

  • 2 Beds
  • 2 Baths
  • 1,733 Sq Ft

  206 Sterling St, Fairfield, CT 06825

  This charming cape has been beautifully maintained and thoughtfully updated, providing peace of mind and comfort throughout. Ideally located near all of the great amenities that Fairfield has to offer, with easy access to the Merritt and 95. The cozy dining area opens into a bright modern kitchen featuring marble countertops, updated appliances and a dry bar which is perfect for everyday living

  Sarah Callands Coldwell Banker Realty

  206 Sterling St, Fairfield, CT 06825
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  /36

  $559,900

  • 5 Beds
  • 2.5 Baths
  • 2,403 Sq Ft

  1036-1038 Maplewood Ave, Bridgeport, CT 06605

  Back on the market as of 04/14/2026. Renovated in 2025 this 2 family home features 11 Rooms, 5 Bedrooms, 2 Full & 1 Half Bathrooms. Apartment 1 features 5 Rooms, 2 Bedrooms, 1 Bathroom. Apartment 2 features 2 floors of living with 6 Rooms, 3 Bedrooms, 1 Full & 1 Half Bathroom. You are within a few minutes drive to everything including | 0.45 miles to I-95 | 0.5 miles to all major shopping | 1.1

  Paul Ferreira RE/MAX Right Choice

  1036-1038 Maplewood Ave, Bridgeport, CT 06605
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  /40

  $3,000,000

  • 6 Beds
  • 5.5 Baths
  • 5,952 Sq Ft

  70 Meadow Ridge Rd, Fairfield, CT 06824

  Nestled on a picturesque cul-de-sac street in the heart of Southport, 70 Meadow Ridge Rd offers the perfect blend of classic charm and modern convenience. This custom home boasts 6 bedrooms and 5, Bathrooms providing ample space for comfortable living and entertaining. Step inside to discover sun-drenched living spaces featuring gleaming hardwood floors, a cozy fireplace, and an open-concept

  David Krasnoff Compass Connecticut, LLC

  70 Meadow Ridge Rd, Fairfield, CT 06824
• 

  

  /32

  $609,000

  • 5 Beds
  • 3 Baths
  • 2,328 Sq Ft

  8-10 Jetland Place, Bridge Port, CT 06605

  Located in the heart of Black Rock, this home is a fully rented multi-family opportunity in one of Bridgeport's most walkable and desirable neighborhoods. Two units are at or near market rent, with one unit currently below market offering immediate upside potential. Recent improvements include a new kitchen, bathroom, and flooring in the second-floor unit, a finished third-floor living area with

  Eric Garces BHGRE Gaetano Marra Homes

  8-10 Jetland Place, Bridge Port, CT 06605
• 

  /2

  $4,300,000

  • 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
• 

  /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

  $2,800,000

  • 4 Beds
  • 2.5 Baths
  • 4,243 Sq Ft

  118 Roseville Rd, Westport, CT 06880

  This Westport residence is a meticulously executed Passive House retrofit of a modernist concrete home originally built in 1938. Few properties achieve this level of energy efficiency while also prioritizing non-toxic, health-conscious building materials. As you pass through the home's front entry gate and hear the gentle rhythm of tires over gravel, a striking and handsome facade comes into

  Tyler Della Valle Dow Della Valle

  118 Roseville Rd, Westport, CT 06880

Showing Results 41 - 80, Page 2 of 4