Southport, CT Homes for Sale with Pool

• 

  

  

  /39

  $5,925,000

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

  3 Stony Point W, 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 W, Westport, CT 06880
• 

  

  

  /20

  $6,495,000

  New Construction

  • 6 Beds
  • 8 Baths
  • 9,062 Sq Ft

  5 Baldwin Place, Westport, CT 06880

  Rarely does a new construction home and property like this come on the market in Westport. Set at the end of a cul-de-sac, in the coveted Long Lots neighborhood, this 2.3-acre, flat property offers a rare combination of privacy and convenience to town. The property features a resort-style, saltwater pool w/spa and automatic safety cover, expansive covered and open-air patios, and a fully equipped

  Lori Popkin Coldwell Banker Realty

  5 Baldwin Place, Westport, CT 06880
• 

  

  

  /40

  $2,790,000

  • 5 Beds
  • 3 Baths
  • 3,072 Sq Ft

  56 Charcoal Hill Rd, Westport, CT 06880

  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,

  Doug Bross Coldwell Banker Realty

  56 Charcoal Hill Rd, Westport, CT 06880
• 

  

  

  /19

  $3,900,000

  New Construction

  • 5 Beds
  • 4.5 Baths
  • 4,100 Sq Ft

  1008 Fairfield Beach Rd, Fairfield, CT 06824

  1008 Fairfield Beach Road- A Masterpiece on Fairfield's Iconic Coastline. Where modern luxury meets coastal elegance. Presented by one of Fairfield County's premier celebrity developers, this extraordinary new construction beach home offers an unparalleled lifestyle with panoramic, unobstructed views of the Long Island Sound with jaw-dropping sunsets. Stand out in the neighborhood with one of the

  Valerie Alvarez Serhant Connecticut, LLC

  1008 Fairfield Beach Rd, Fairfield, CT 06824
• 

  

  

  /36

  $5,750,000

  • 5 Beds
  • 8 Baths
  • 6,503 Sq Ft

  31 Stonybrook Rd, Westport, CT 06880

  Tucked behind a gated entry in Old Hill, this stunning 5 bedroom, 6.2 bath home offers a rare blend of elegance, privacy and natural beauty. The property has multiple serene water features-a heated saltwater gunite pool with hot tub, a tranquil private pond with fountain and picturesque Stony Brook. The stately stone and wood exterior blends seamlessly with the lush surroundings, while inside, an

  Kristi Law William Pitt Sotheby's Int'l

  31 Stonybrook Rd, Westport, CT 06880
• 

  

  /40

  $3,499,000

  • 5 Beds
  • 4.5 Baths
  • 3,778 Sq Ft

  240 North Ave, Westport, CT 06880

  "MEADOW WOOD" - Nearly two acres of Westport's most spectacular land is the setting for this storied estate, which has been completely remodeled, expanded and transformed for modern living. Totally fenced & screened w/privacy trees, this unique property offers rare sophistication with a stunning main residence, gunite pool, and a 2,447+/- sqft barn. Gated driveways lead to both the main house &

  Doug Bross Coldwell Banker Realty

  240 North Ave, Westport, CT 06880
• 

  

  /40

  $2,950,000

  Open Sat 1PM - 3PM

  • 4 Beds
  • 3.5 Baths
  • 3,660 Sq Ft

  679 Rowland Rd, Fairfield, CT 06824

  Ideally located in one of Fairfield's most desirable beach neighborhoods, this beautiful custom-built FEMA compliant home combines premium construction and efficiency with high-end finishes throughout. Unique features include 2x6 framing, steel beam support, energy efficient foam insulation, dual HVAC and tankless hot water systems, a gorgeous custom kitchen with Thermador appliances and honed

  Amie Belile William Raveis Real Estate

  679 Rowland Rd, Fairfield, CT 06824
• 

  

  /40

  $5,750,000

  • 4 Beds
  • 4.5 Baths
  • 3,800 Sq Ft

  69 Birch Rd, Fairfield, CT 06824

  Your new fully custom near beach luxury residence is ready for you now... Introducing "White Birch", a masterfully executed collaboration between Fairfield County's premier Architect, Builder, & Designer, sets a new benchmark for bespoke coastal living and the effortless estate lifestyle. Every detail has been thoughtfully curated, every finish intentionally elevated, every inch built with

  Jaclyn Picarillo Higgins Group Bedford Square

  69 Birch Rd, Fairfield, CT 06824
• 

  /2

  $2,650,000

  • Land
  • 1.23 Acres
  • $2,154,472 per Acre

  4 Lantern Hill Rd, Westport, CT 06880

  Rare opportunity to build a custom residence on 1.2 acres in Westport. The previous home has been demolished, and the property is offered with approved architectural plans. Bring your preferred builder and collaborate with the project architect to tailor the design to your vision. Also listed as a to-be-built single-family residence.

  Garvey Fox Serhant Connecticut LLC

  4 Lantern Hill Rd, Westport, CT 06880
• 

  

  /40

  $4,850,000

  • 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
• 

  

  /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
• 

  

  /40

  $2,200,000

  • 5 Beds
  • 6 Baths
  • 6,136 Sq Ft

  203 Wildflower Ln, Fairfield, CT 06824

  Nestled at the end of a cul-de-sac in the beautiful Greenfield Hill neighborhood, this fully updated and renovated home sits on a private 2.4-acre lot and offers Fairfield living at its finest. This 5-bedroom home, with four full and two half bathrooms, boasts spacious interiors, an open floor plan, all-new finishes, and a brand-new primary bedroom suite addition above a three-car garage. The

  Danielle Baleeiro Realty ONE Group Connect

  203 Wildflower Ln, Fairfield, CT 06824
• 

  

  /38

  $1,875,000

  $24K PRICE DROP

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

  2177 Cross Hwy, Fairfield, CT 06824

  2177 Cross Hwy welcomes you home. This extensively renovated iconic contemporary awaits your personal touches. The blending of dramatic architecture with everyday comfort, offering nearly 4,000 sq ft of functional living space designed for gathering, relaxing and entertaining. Soaring 22' ceilings, oversized windows and park-like views fill the main living area with light, while a striking

  JaKeith Action Jackson ASJ Realty Partners

  2177 Cross Hwy, Fairfield, CT 06824
• 

  

  /40

  $5,650,000

  New Construction Open Thu 12PM - 2PM

  • 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 cul de sac, 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 two story foyer, 10ft

  Doug Bross Coldwell Banker Realty

  8 Pleasant Valley Ln, Westport, CT 06880
• 

  

  /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
• 

  

  /36

  $1,498,000

  $100K PRICE DROP

  • 6 Beds
  • 3.5 Baths
  • 3,264 Sq Ft

  91 Lockwood Rd, Fairfield, CT 06825

  Welcome to 91 Lockwood Road, where modern farmhouse charm meets timeless comfort in one of Stratfield's most sought-after neighborhoods. Beautifully renovated, this exceptional home offers the perfect blend of style, functionality, and everyday living. Designed for today's lifestyle, the home features 5-6 bedrooms, 3 full baths, and 1 half bath, with bright, versatile living spaces that offer

  Susan Bento Distinct Realty

  91 Lockwood Rd, Fairfield, CT 06825
• 

  

  /40

  $5,199,000

  New Construction Open Sun 12PM - 4PM

  • 6 Beds
  • 8 Baths
  • 8,935 Sq Ft

  4 Sycamore Dr, Westport, CT 06880

  Tucked away on a quiet cul de sac in the desirable Hunt Club area of Long Lots in Westport is a new construction lux home from CCO Habitats. 3 levels of finished living space with 10 foot ceilings on the 1st floor give an amazing sense of openness, as well as better functionality than 4 level homes. Think about it. Who really wants to walk up to the third floor every day? That's right; no one.

  Maryann Levanti Higgins Group Bedford Square

  4 Sycamore Dr, Westport, CT 06880
• 

  

  /22

  $915,000

  • 3 Beds
  • 1.5 Baths
  • 1,680 Sq Ft

  2196 N Benson Rd, Fairfield, CT 06824

  Welcome to 2196 North Benson Road! This unique property is situated on a private drive in the sought after University Area. The spacious, fenced back yard with inground pool serves as an oasis for pets and guests alike. The property boasts a generous first floor MBR and half bath. There are also two gabled bedrooms and a full bath on the second floor. The kitchen extends the entire rear of the

  John Swaim Realty ONE Group Connect

  2196 N Benson Rd, Fairfield, CT 06824

Showing Results 41 - 59, Page 2 of 2