Southport, CT Homes for Sale with Acreage

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  $2,799,000

  • 5 Beds
  • 6.5 Baths
  • 7,269 Sq Ft

  342 Midlock Rd, Fairfield, CT 06824

  Welcome to Summer Tree Gardens, an extraordinary stately home nestled on over 2 acres of meticulously maintained grounds in the prestigious Greenfield Hill neighborhood of Fairfield, CT. This expansive 7,269 sq. ft. home boasts 5 en-suite bedrooms, 8.5 baths, and an array of luxurious features that blend timeless elegance with modern updates. The home was built by builder Christer Krook. Step

  Ken Osborn Higgins Group Bedford Square

  342 Midlock Rd, Fairfield, CT 06824
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  $4,900,000 Open Sun 1PM - 3PM

  • 7 Beds
  • 5.5 Baths
  • 7,995 Sq Ft

  37 Green Acre Ln, Westport, CT 06880

  Enjoy the best of Westport lifestyle at this elegant 4.4-acre private estate. The property is two minutes from the beach, town center, I-95, and the Saugatuck Hamlet rail station. This classic 1936 gracious ~8,000 Sq/Ft residence includes 7 bedrooms and 5.1 baths, four grand fireplaces, a former ballroom, an antique stone-and-beamed family room, and a gourmet kitchen with professional appliances

  Lisa Bortz William Pitt Sotheby's Int'l

  37 Green Acre Ln, Westport, CT 06880
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  $6,500,000

  • 6 Beds
  • 6.5 Baths
  • 6,585 Sq Ft

  69 Beachside Ave, Westport, CT 06880

  Nestled along Westport's prestigious 'Gold Coast,' this architecturally magnificent estate on 4+ acres of park-like grounds with a breathtaking pool and professional-grade Har-Tru tennis court is a haven for luxury living and distinguished entertaining. Surrounded by major estates in one of the most sought-after coastal regions in the Northeast, it boasts access to pristine beaches, sophisticated

  Doug Bross Coldwell Banker Realty

  69 Beachside Ave, Westport, CT 06880
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  $2,400,000

  • 4 Beds
  • 6 Baths
  • 5,540 Sq Ft

  230 Winton Rd, Fairfield, CT 06824

  Located in highly sought-after WINTON PARK, this property features an in-ground POOL, fenced rear yard, stone walls and stone drive flanked by flowering pear trees, culminating in a front courtyard. Winton Park is a private assoc with one-plus acre zoning within walking distance of charming downtown Fairfield. Just a short walk to the train, schools, shopping and dining. Bike to the beach! Built

  Denise Walsh William Raveis Real Estate

  230 Winton Rd, Fairfield, CT 06824
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  $10,950,000

  • 6 Beds
  • 10 Baths
  • 12,440 Sq Ft

  5 Fraser Rd, Westport, CT 06880

  Prepare to experience the extraordinary and discover the future at this new residence by Skyview Builders. Now complete and ready for immediate enjoyment, this world-class estate elevates the standard against which all others are measured. Set on two spectacular, level acres in the heart of Westport's premier estate section, long considered a haven for celebrities & influential figures. The gated

  Doug Bross Coldwell Banker Realty

  5 Fraser Rd, Westport, CT 06880
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  /40

  $25,000,000

  • 6 Beds
  • 11 Baths
  • 19,569 Sq Ft

  1131 Sasco Hill Rd, Fairfield, CT 06824

  Sasco Point- A Rare Waterfront Estate. Perched on over 11 acres with 450 feet directly on Long Island Sound, Sasco Point is an extraordinary coastal retreat. Nestled at the end of prestigious Sasco Hill Road, this architecturally stunning estate blends Swedish, Dutch, and Moorish influences, creating a residence that is as elegant as it is timeless. A discreet gated entrance leads to a winding

  Andrew Whiteley Brown Harris Stevens

  1131 Sasco Hill Rd, Fairfield, CT 06824
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  $2,050,000

  • 4 Beds
  • 5 Baths
  • 3,707 Sq Ft

  27 Blue Ribbon Dr, Westport, CT 06880

  Welcome to 27 Blue Ribbon Road - A serene retreat in the heart of Westport. Tucked away on a quiet, tree-lined street where neighbors still greet each other by name, this expanded split-level home offers the perfect blend of comfort, style, and community. With 4 spacious bedrooms, a dedicated home office, and a thoughtfully updated layout, this property is ideal for both everyday living and

  Meredith Cohen Serhant Connecticut, LLC

  27 Blue Ribbon Dr, Westport, CT 06880
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  /40

  $5,995,000

  • 6 Beds
  • 7.5 Baths
  • 8,812 Sq Ft

  9 Sturges Commons, Westport, CT 06880

  Stunning Custom Built Colonial by Chris Montanaro of Redcoat Homes. Designed by Renowned Architect, Judith Larson. This Home Exudes Sophistication, every detail has been meticulously crafted to offer extraordinary living experience on a 1.10 flat manicured acre. Over 8,000 SQ FT w 8-inch wide plank wht oak floors throughout. 1st FL features a Chef's dream kitchen, generous Dining & Family room

  Kelly Loucas Compass Connecticut, LLC

  9 Sturges Commons, Westport, CT 06880
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  $1,549,000

  • 6 Beds
  • 5 Baths
  • 5,261 Sq Ft

  285 Greens Farms Rd, Westport, CT 06880

  Endless Potential in Prime Location! Bring your vision and transform this Westport gem into the home of your dreams! In the sought-after Greens Farms neighborhood, this property offers a rare opportunity to renovate and customize to your taste. The main residence is brimming with potential, while a beautifully finished attached legal rental unit provides immediate income or flexible living space.

  Danna Rogers Higgins Group Bedford Square

  285 Greens Farms Rd, Westport, CT 06880
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  $5,200,000

  • 6 Beds
  • 7.5 Baths
  • 9,630 Sq Ft

  355 Greens Farms Rd, Westport, CT 06880

  Exceptional Gated Estate in Greens Farms! Welcome to 355 Greens Farms Rd, a spectacular 2.25 acres estate designed for luxurious living and ultimate entertaining. This stunning home is a dream for car enthusiasts, featuring a four-car garage with room for lifts, making it perfect for showcasing and maintaining your collection. Step inside to find a brand-new kitchen and a newly designed primary

  Meredith Cohen Serhant Connecticut, LLC

  355 Greens Farms Rd, Westport, CT 06880
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  $2,599,000

  • 11 Beds
  • 10 Baths
  • 15,118 Sq Ft

  124 Old Battery Rd, Bridgeport, CT 06605

  A very special Fairfield County Connecticut Gold Coast mansion at St. Mary's-by-the-Sea and Long Island Sound. Experience The Chimneys, an architectural gem designed by Charles Wellington Walker in 1928. This Georgian Revival home won America's Finest Home Award in 2015. The 54-foot Grand Hall features a sweeping staircase with hand-wrought iron balustrades. Eleven artful fireplaces add warmth

  Gail Robinson William Raveis Real Estate

  124 Old Battery Rd, Bridgeport, CT 06605
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  $1,999,991

  • 4 Beds
  • 4.5 Baths
  • 5,737 Sq Ft

  215 Paddock Hill Ln, Fairfield, CT 06824

  Paddock Hill Manor is a stunning French Colonial home on 2.03 lush-green acres in the area's pre-eminent gated community, The Ridge. Majestically located on a quiet cul-de-sac steps from Patterson Country Club Golf C. The home blends grandeur and sophistication for entertaining and daily living. Natural light floods the newly painted interiors and refinished hardwood flrs. The grand two-story

  Sholeh Janati Weinbaum Higgins Group Bedford Square

  215 Paddock Hill Ln, Fairfield, CT 06824
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  $10,250,000

  • 6 Beds
  • 9 Baths
  • 5,920 Sq Ft

  828 Sasco Hill Rd, Fairfield, CT 06824

  "Pebbles" | Iconic Sasco Hill Estate Timeless Design. Storied Past. Unrivaled Views. A distinguished Georgian Revival estate set on nearly 3 acres, the largest lot along this coveted stretch of Sasco Hill. With sweeping, unobstructed views of the Country Club of Fairfield, Southport Harbor, Long Island Sound, and the Manhattan skyline, this iconic property offers an extraordinary blend of

  Wendy Ryan Brown Harris Stevens

  828 Sasco Hill Rd, Fairfield, CT 06824
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  $5,850,000

  • 6 Beds
  • 5.5 Baths
  • 6,588 Sq Ft

  17 River Ln, Westport, CT 06880

  This remarkable stone mansion, built in 1929, stands as one of the most historically and culturally significant residences in Westport and Fairfield County, celebrated as an exceptional trophy property. Meticulously restored and in impeccable, move-in ready condition, this home is poised for immediate enjoyment. Crafted in the esteemed tradition of Europe's grand Manor Houses, it boasts

  Alex Chingas Coldwell Banker Realty

  17 River Ln, Westport, CT 06880
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  $2,649,000

  • 4 Beds
  • 4.5 Baths
  • 6,600 Sq Ft

  342 Greens Farms Rd, Westport, CT 06880

  Calling all renovators, designers, and discerning buyers seeking an extraordinary Westport estate. Opportunity awaits at 342 Greens Farms Road, set on 2.02 lush acres just steps from Connecticut's Gold Coast. This 1861 Victorian home, complemented by a thoughtful, high-quality 2008 rear addition, features over 6600 square feet of living space with Audubon Society land bordering the rear and side.

  Adrienne Durkin Compass Connecticut, LLC

  342 Greens Farms Rd, Westport, CT 06880
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  $390,000

  • Land
  • 2.00 Acres
  • $195,000 per Acre

  6 Fox Run Ln, Westport, CT 06880

  This secluded property in Westport, CT at 6 Fox Run Lane offers an opportunity to submit your desired dream home plans to Westport on this picturesque 2 acres of rare undeveloped land. The lot is nestled in a prestigious upscale neighborhood and offers a tranquil bucolic setting, and is surrounded by nature. The new owner may design a custom home to suit your family's needs and preferences

  Derek Greene Derek Greene

  6 Fox Run Ln, Westport, CT 06880
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  $25,000,000

  • 5 Beds
  • 5.5 Baths
  • 11,450 Sq Ft

  122 Beachside Ave, Westport, CT 06880

  A GOLD COAST opportunity: 6.6 acres of pristine estate living culminating at 400 ft of direct Long Island Sound waterfront.A winding drive from the famed Beachside Ave enclave leads past the tennis pavilion, through the shaded trees and into a cobblestone courtyard with fountain and perfectly manicured garden entry.Stepping through the front door, the striking view of blue water tops the lush

  Leslie Clarke Compass Connecticut, LLC

  122 Beachside Ave, Westport, CT 06880
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  $5,500,000

  • 4 Beds
  • 3.5 Baths
  • 4,636 Sq Ft

  87 Red Coat Rd, Westport, CT 06880

  MOST UNIQUE HOUSE IN WESTPORT LARGE LOG HOME ON THE RIVER THAT IS STOCKED WITH TROUT. INGROUND GUNITE POOL BEAUTIFUL GROUNDS VERY PRIVATE ONE FLOOR LIVING. 4 BEDROOMS 3.5 BATHS. 1 HOUR TO NYC BEACH ACCESS. WONDERFUL RARE OPPORTUNITY TO OWN THE HOME YOU HAVE ALWAYS WONDERED ABOUT. THE BEAUTIFUL TRANQUIL RIVERVIEW LODGE LOG HOME THAT SITS ON THE MAJESTIC SAUGATUCK RIVER. WITH OVER 500+ FEET OF

  Rebecca Ellsley Higgins Group Bedford Square

  87 Red Coat Rd, Westport, CT 06880
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  $2,595,000

  • 6 Beds
  • 9 Baths
  • 7,843 Sq Ft

  125 Brett Ln, Fairfield, CT 06824

  Discover your private sanctuary at the end of a serene cul-de-sac in Greenfield Hill. This country compound spans 4.5 picturesque acres, enveloping a French-inspired main house with 6 BRs, 4.2 baths, and an enchanting English garden. Step into the elegant formal living and dining rooms, both warmed by inviting FPs, setting the stage for memorable moments. The custom gourmet kitchen, designed for

  Linna Yuen Coldwell Banker Realty

  125 Brett Ln, Fairfield, CT 06824
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  $9,995,000

  • Land
  • 3.30 Acres
  • $3,028,788 per Acre

  26 Beachside Ave, Westport, CT 06880

  NEWLY PRICED! Oversized 3.30 Private Waterfront Acres with 254 feet of Long Island Sound frontage located on the Premier Gold Coast of Connecticut is ready to be molded into your PERFECT Home... 26 Beachside Avenue is both a most sought after Westport address and NOW has over 254 feet of Direct Long Island Sound frontage. This southern facing, cleared, and elevated land is direct water front with

  Deirdre Andreoli Compass Connecticut, LLC

  26 Beachside Ave, Westport, CT 06880
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  $6,649,000 New Construction

  • 6 Beds
  • 7.5 Baths
  • 8,035 Sq Ft

  7 Roshab Ln, Westport, CT 06880

  Set on over 2 acres in one of Westport's most prestigious neighborhoods, this stunning new construction by HOBI award winner Rick Benson, blends modern luxury with timeless design. Surrounded by mature trees, the home offers privacy & serenity minutes from trains, shopping, & beaches. Inside, discover 6 spacious bedrooms, 7 full/1 half baths, sun-filled interiors with a seamless flow between

  Totney Benson Coldwell Banker Realty

  7 Roshab Ln, Westport, CT 06880
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  $5,485,686 New Construction

  • 7 Beds
  • 9 Baths
  • 7,243 Sq Ft

  25 Ellery Ln, Westport, CT 06880

  Coming Spring 2026 - Have you been quietly creating a wishlist of EVERYTHING you want in your next home? This new mini-estate on a preferred Greens Farms cul-de-sac is YOUR EVERYTHING! There will be no reason to leave home - 25 Ellery offers it all including a pool site. The flow of this house is divine. Rooms are spacious, comfortable, and well-thought out for today's lifestyle. Windows are

  Jaclyn Picarillo Higgins Group Bedford Square

  25 Ellery Ln, Westport, CT 06880
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  $5,499,000 New Construction

  • 6 Beds
  • 9 Baths
  • 9,550 Sq Ft

  11 Tierney Ln, Westport, CT 06880

  Impressively positioned at the end of a private lane in the heart of the Greens Farms, this is the first of 2 custom homes in final stages of construction. Combining classic design with modern detailing, this masterfully crafted home by an established local builder of premier residences is sure to delight even the most discerning buyer. The main level exudes luxury, showcasing the expert millwork

  Laurie Crouse Coldwell Banker Realty

  11 Tierney Ln, Westport, CT 06880
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  $7,299,000 New Construction

  • 7 Beds
  • 9 Baths
  • 8,700 Sq Ft

  7 Brookside Dr, Westport, CT 06880

  Extraordinary new construction opportunity on a flat acre on one of Westport's most coveted cul-de-sacs-walking distance to downtown and close to schools, shopping, beaches, and all the best of Westport living. This over 9,000 sq ft residence will be built by renowned Redcoat Homes, and designed by acclaimed architect Judith Larson. The home will feature a pool, 3-car garage, and exceptional

  Danna Rogers Higgins Group Bedford Square

  7 Brookside Dr, Westport, CT 06880
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  $5,400,700 New Construction

  • 6 Beds
  • 7 Baths
  • 5,800 Sq Ft

  1 Sturges Hwy Unit Lot 1, Westport, CT 06880

  Design Your Dream Home with an Award-Winning Builder. Step into a world of elegance and sophistication with a soon-to-be-built 6,600 sq. ft. masterpiece by Coastal Luxury Homes. Known for their innovative designs and unparalleled craftsmanship, Coastal Luxury Homes has earned a reputation for creating some of the most sought-after residences. With a focus on prime location, architectural

  Annie Klyver Higgins Group Real Estate

  1 Sturges Hwy Unit Lot 1, Westport, CT 06880
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  $5,995,880 New Construction

  • 5 Beds
  • 8 Baths
  • 7,020 Sq Ft

  86 Maple Ave S, Westport, CT 06880

  EARLY opportunity! Coastal Luxury Homes has secured this choice 1 acre lot in Greens Farms to build your future dream home! Currently in the design phase, this 7,020SF irresistible residence will blend seamlessly with the charming aesthetic of this top Westport neighborhood. The home will embody classic New England elegance with a fresh California-inspired interior and expansive open-air

  Jaclyn Picarillo Higgins Group Bedford Square

  86 Maple Ave S, Westport, CT 06880
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  $6,205,176 New Construction

  • 5 Beds
  • 8 Baths
  • 6,302 Sq Ft

  24 Edgemarth Hill Rd, Westport, CT 06880

  Construction is underway atop this quiet cul de sac in coveted Greens Farms, Westport. 24 Edgemarth Hill was designed and will be crafted and appointed with the finest materials - see rendering photos of what's to come. Flaunting walls of windows, sexy floor-to-ceiling stone and textured accents, vaulted ceilings, and romantic balconies, this is a spec build with all the custom features the most

  Jaclyn Picarillo Higgins Group Bedford Square

  24 Edgemarth Hill Rd, Westport, CT 06880
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  /15

  $6,875,480 New Construction

  • 7 Beds
  • 8 Baths
  • 8,800 Sq Ft

  1 Sturges Hwy Unit Lot 2, Westport, CT 06880

  Design Your Dream Home with an Award-Winning Builder Step into a world of elegance and sophistication with a soon-to-be-built 6,600 sq. ft. masterpiece by Coastal Luxury Homes. Known for their innovative designs, sleek modern lines, and unparalleled craftsmanship, Coastal Luxury Homes has earned a reputation for creating some of the most sought-after residences. With a focus on prime location,

  Annie Klyver Higgins Group Real Estate

  1 Sturges Hwy Unit Lot 2, Westport, CT 06880
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  $4,995,000 New Construction

  • 6 Beds
  • 7 Baths
  • 7,500 Sq Ft

  107 Old Rd, Westport, CT 06880

  Welcome to 107 Old Road, an exceptional new development by Joe Feinleib founder of Coastal Luxury Homes. Soon to be the only gated community development in Westport, CT, this uniqiue four-lot enclave presents unparalleled luxury and privacy. Each custom home, to be designed in collaboration with your client, boasts approximately 6,500 to 7,500 square feet of living space, with an additional 1,100

  Nickolaos Andronikidis Shelby's Realty Services

  107 Old Rd, Westport, CT 06880
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  $6,999,999 New Construction

  • 6 Beds
  • 6.5 Baths
  • 8,400 Sq Ft

  3 Tanglewood Ln, Westport, CT 06880

  Introducing an exceptional new construction home by Redcoat Homes. Spanning over 8,000 square feet, this stunning property is situated on a flat, one-plus acre lot in the desirable Old Hill neighborhood of Westport. The location is private yet conveniently close to I-95 and the Merritt Parkway, just minutes from the beach and town. It also borders Earth Place, one of the top family-friendly

  James Lanzaro Compass Connecticut, LLC

  3 Tanglewood Ln, Westport, CT 06880
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  $5,100,000 New Construction

  • 6 Beds
  • 8 Baths
  • 8,185 Sq Ft

  2 Windy Hill Rd, Westport, CT 06880

  Introducing an exceptional new construction by Cypress Development, this luxurious home on a private acre in one of Westport's most sought-after locations seamlessly merges timeless design with modern luxury. Step into an impressive two-story foyer showcasing sun-soaked interiors, hardwood floors, tall ceilings, and meticulous custom millwork. A formal living room and formal dining room set the

  Jacob Bivona Keller Williams Prestige Prop.

  2 Windy Hill Rd, Westport, CT 06880
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  $7,850,000 New Construction

  • 6 Beds
  • 7.5 Baths
  • 9,032 Sq Ft

  9 Grays Farm Rd, Westport, CT 06880

  Skyview Builders presents a unique opportunity - unmatched for both the modern expression of luxurious living it embodies, as well as the captivating private setting over which the residence presides. Two acres of your own private park-like property, nestled against the Paul Newman-Poses Preserve, will create an unforgettable backdrop for this European-inspired home for all seasons. The long,

  Doug Bross Coldwell Banker Realty

  9 Grays Farm Rd, Westport, CT 06880
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  /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

Showing Results 41 - 73, Page 2 of 2