Colonial Homes for Sale in Southport, CT

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  /7

  $4,100,000

  New Construction

  • 6 Beds
  • 5.5 Baths
  • 6,244 Sq Ft

  48 Woodside Ave, Westport, CT 06880

  A rare opportunity to own new construction in Westport's coveted Old Hill neighborhood, offering refined design, a swimming pool, and a walkable lifestyle near Post Road and downtown. Tucked within one of Westport's most sought-after enclaves, this newly constructed 6-bedroom, 5.5-bath home blends architectural sophistication with modern livability. Natural light, clean lines, and

  Judy Michaelis Coldwell Banker Realty

  48 Woodside Ave, Westport, CT 06880
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  /8

  $2,850,000

  Coming Soon

  • 5 Beds
  • 6 Baths
  • 4,529 Sq Ft

  27 Bauer Place, Westport, CT 06880

  Still hoping to move before school starts? This exceptional new construction home is ready for immediate occupancy! Built by SIR Development, Westport's premier luxury builder with 30+ years of experience and 300+ homes built, this hidden gem sits at the end of a cul-de-sac in a welcoming neighborhood within walking distance to Long Lots Elementary School. The open layout spans 4 beautifully

  Julie Haroun Westport Residential, LLC.

  27 Bauer Place, Westport, CT 06880
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  /40

  $5,895,000

  $100K PRICE DROP

  • 4 Beds
  • 6 Baths
  • 5,567 Sq Ft

  46 Compo Mill Cove, Westport, CT 06880

  Set within Compo Mill Cove, a rare private association where homes are accessed only by footbridge and no cars are permitted, this Brooke Girty-designed shingle-style residence offers 5,567 SF of true coastal sanctuary. The footbridge approach immediately separates the home from daily life, delivering a level of seclusion few coastal properties can match. Interiors are warm, considered, and

  Evangela Brock Douglas Elliman of Connecticut

  46 Compo Mill Cove, Westport, CT 06880
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  /40

  $10,500,000

  $5M PRICE DROP

  • 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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  /13

  $7,990,000

  New Construction

  • 6 Beds
  • 8 Baths
  • 6,000 Sq Ft

  4 Compo Pkwy, Westport, CT 06880

  Build your coastal dream home on a rare, full acre* property along one of Compo Beach's most coveted cul-de-sacs, where opportunities of this caliber seldom become available. Ideally positioned just across from Longshore and moments from the shoreline, this extraordinary setting places Westport's most treasured amenities at your fingertips: golf, tennis, swimming, boating, beaches, playgrounds,

  Jaclyn Picarillo Higgins Group Bedford Square

  4 Compo Pkwy, Westport, CT 06880
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  /10

  $2,675,000

  New Construction

  • 5 Beds
  • 5.5 Baths
  • 5,252 Sq Ft

  476 Mill Hill Terrace, Southport, CT 06890

  Beautifully crafted new construction in coveted Southport by a three-time HOBI Award-winning builder, with anticipated completion in Spring 2027. Set on a serene .43-acre property, this thoughtfully designed home will offer over 5,200 square feet of finished living space across four levels, including third-floor bonus space and a walk-out lower level. Featuring 5 bedrooms and 5.5 baths, the home

  Jennifer Peters William Raveis Real Estate

  476 Mill Hill Terrace, Southport, CT 06890
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  /5

  $2,050,000

  • 5 Beds
  • 3.5 Baths
  • 2,509 Sq Ft

  79 Fairfield Place, Fairfield, CT 06824

  Set on a level and flat .24-acre lot in the highly sought-after Sasco Hill area of Fairfield, this charming home offers endless opportunities to customize and create your dream living space. Boasting 2,500 square feet of versatile living area, plus 3 full unfinished basements (could easily be finished), a deck, and an outdoor shed, this property perfectly balances comfort and potential. Enjoy a

  Phyllis Doonan William Raveis Real Estate

  79 Fairfield Place, Fairfield, CT 06824
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  /40

  $4,795,000

  New Construction

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

  2 Windy Hill Rd, Westport, CT 06880

  Resort-style living meets modern luxury at 2 Windy Hill Road. Set on a private landscaped acre, this newly completed 8,100+ SF estate by HOBI Award-winning builder Cypress Development was thoughtfully designed for the way today's luxury buyer lives, entertains, and unwinds. A dramatic two-story foyer introduces light-filled interiors highlighted by soaring ceilings, white oak flooring, natural

  Jacob Bivona Keller Williams Prestige Prop.

  2 Windy Hill Rd, Westport, CT 06880
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  /35

  $1,425,000

  • 5 Beds
  • 2.5 Baths
  • 3,246 Sq Ft

  19 Vineyard Ln, Westport, CT 06880

  Get ready to make 19 Vineyard Lane home! This wonderful family home is ideally situated in the heart of Westport, offering 5 bedrooms and 2.5 baths designed for comfortable, everyday living and effortless entertaining alike. Lovingly cared for by its current owner for 50 years, this home features a first-floor office, while the partially finished basement offers space for a gym or playroom. Set

  Polly Sykes Compass Connecticut, LLC

  19 Vineyard Ln, Westport, CT 06880
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  /21

  $9,860,000

  New Construction

  • 6 Beds
  • 9 Baths
  • 9,200 Sq Ft

  9 Over Rock Ln, Westport, CT 06880

  Newly completed by Compo Luxury Homes, this exceptional modern estate offers approximately 9,200 square feet on 2.1 private acres just minutes from downtown Westport, Compo Beach, and Metro-North. Thoughtfully designed with European craftsmanship, premium finishes, and sophisticated smart-home technology, the home blends timeless design with exceptional functionality. A dramatic floating

  Danna Rogers Higgins Group Bedford Square

  9 Over Rock Ln, Westport, CT 06880
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  /38

  $5,999,999

  New Construction

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

  13 Edgemarth Hill Rd, Westport, CT 06880

  Set on 1.70 private acres in the heart of Greens Farms, this distinctive new construction by Dwell offers a rare combination of timeless design, exceptional privacy, and resort-caliber outdoor living. Offering 8,700+/- sq ft, this exceptional residence features 7 bedrooms, 8 bathrooms, and thoughtfully designed living spaces crafted with an emphasis on enduring design rather than passing trends.

  Doug Bross Coldwell Banker Realty

  13 Edgemarth Hill Rd, Westport, CT 06880
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  /40

  $4,500,000

  $490K PRICE DROP

  • 5 Beds
  • 4 Baths
  • 4,144 Sq Ft

  1149 & 1148 Fairfield Beach Rd, Fairfield, CT 06824

  A rare opportunity to own a premier BEACHFRONT residence offering compelling value in today's luxury market with updated guest home....All BEAUTIFULLY appointed & MOVE IN READY! 60 MINS to NYC! WATERFRONT Home~1149 Walk-Out-To-Sand Waterfront AND Guest Home ~1148 fun & updated (2022) just steps to your Private BEACH. Enjoy true beachfront living w/no steps from your main level family room to an

  Christine Magliocco Higgins Group Real Estate

  1149 & 1148 Fairfield Beach Rd, Fairfield, CT 06824
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  /40

  $3,795,000

  $55K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 3,418 Sq Ft

  61 Clapboard Hill Rd, Westport, CT 06880

  Located in prestigious Greens Farms, this European-inspired Colonial offers a rare opportunity to enjoy immediate charm while planning for the future. Set behind private gates on expansive, picturesque grounds, the property is surrounded by multimillion-dollar estates-making it an exceptional canvas for new construction or a significant estate expansion. The existing home is beautifully

  Lorelei Atwood Higgins Group Real Estate

  61 Clapboard Hill Rd, Westport, CT 06880
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  /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
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  /16

  $1,899,000

  • 4 Beds
  • 3.5 Baths
  • 3,514 Sq Ft

  36 Lyons Plain Rd, Westport, CT 06880

  Rarely does an opportunity like this become available in Westport. Set on 2.36 private acres with approximately 300 feet along the scenic Aspetuck River, this exceptional property offers a remarkable setting to renovate, expand, or create the custom estate you've always envisioned. The existing four-bedroom residence features a spacious primary suite with fireplace, an expansive kitchen, and a

  Charlotte Cotton William Raveis Real Estate

  36 Lyons Plain Rd, Westport, CT 06880
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  /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
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  /40

  $5,499,000

  • 5 Beds
  • 5.5 Baths
  • 4,000 Sq Ft

  2268 Fairfield Beach Rd, Fairfield, CT 06824

  Experience the pinnacle of coastal luxury at this extraordinary waterfront builder's own residence on prestigious Fairfield Beach Road. Designed with uncompromising craftsmanship and impeccable attention to detail, this one-of-a-kind modern masterpiece offers the ultimate waterfront lifestyle with a private sandy beach and your own private dock. Showcasing over-the-top custom finishes throughout,

  Sara Santos Coldwell Banker Realty

  2268 Fairfield Beach Rd, Fairfield, CT 06824
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  /27

  $2,100,000

  $100K PRICE DROP

  • 5 Beds
  • 4.5 Baths
  • 6,330 Sq Ft

  25 Old Rd, Westport, CT 06880

  Set in Westport's sought-after Hunt Club neighborhood, this European-inspired Colonial offers over 6,300 square feet across three finished levels, including expansive recreation spaces and a dedicated home theater. A dramatic two-story entry introduces refined formal and informal rooms, including a fireplaced living room, formal dining room, private office, and an expansive eat-in kitchen with

  Zach Wright William Pitt Sotheby's Int'l

  25 Old Rd, Westport, CT 06880
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  /39

  $2,699,000

  Coming Soon

  • 5 Beds
  • 5.5 Baths
  • 5,014 Sq Ft

  1123 Round Hill Rd, Fairfield, CT 06824

  There's a certain kind of iconic home that settles over you the moment you step inside, because the craftsmanship was never meant to be temporary. Nine-foot ceilings in the living & dining rooms, 3 wood-burning fireplaces, solid proportions & large windows & glass doors that still frame the light the way they were designed to nearly a century ago. The kind of quiet authority that newer

  Veronica Monahan Compass Connecticut, LLC

  1123 Round Hill Rd, Fairfield, CT 06824
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  /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
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  /39

  $2,225,000

  $25K PRICE INCREASE

  • 6 Beds
  • 2 Baths
  • 2,180 Sq Ft

  2142 Fairfield Beach Rd, Fairfield, CT 06824

  OPPORTUNITY KNOCKS TWICE - A unique investment awaits with the only two-family home on the Fairfield Beach Road Peninsula featuring private beach access. This fully furnished property offers excellent rental income during the academic season and serves as a relaxing summer retreat for owners-or an additional rental opportunity. Unit 2142 is a spacious four-bedroom residence, each room furnished

  Michael Menillo Collage Realty

  2142 Fairfield Beach Rd, Fairfield, CT 06824
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  /29

  $1,899,000

  • 3 Beds
  • 2.5 Baths
  • 3,338 Sq Ft

  23 Old Dam Rd, Fairfield, CT 06824

  Wonderful waterfront oasis offers direct access to Long Island Sound via a private dock and includes deeded Fairfield beach access. The home features a bright, open floor plan, creating an inviting coastal atmosphere. The primary bedroom boasts a sitting room, a walk-in closet, and a balcony overlooking the waterfront, providing stunning views of LI Sound & Pine Creek. The property promises

  Katie O'Grady Compass Connecticut, LLC

  23 Old Dam Rd, Fairfield, CT 06824
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  /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
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  /40

  $2,950,000

  • 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
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  /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
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  /34

  $1,399,000

  New Construction

  • 4 Beds
  • 3.5 Baths
  • 3,300 Sq Ft

  30 Country Rd, Fairfield, CT 06824

  This brand-new construction masterpiece showcases an elite architectural design that prioritizes complete autonomy. The two separate units share absolutely no living space walls-the only common point of contact is the garage structure, ensuring the noise control and privacy of a fully detached single-family home. Each residence features its own distinct, privately sectioned, and fully fenced

  Denise Daniels-biagi Coldwell Banker Realty

  30 Country Rd, Fairfield, CT 06824
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  /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
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  /34

  $925,000

  $24K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,166 Sq Ft

  7 Lincoln St, Westport, CT 06880

  A wonderful opportunity to make this home your own. The property offers the potential to be converted back into a single-family residence and is ideally located just moments from vibrant Main Street, Saugatuck Village, the train station, and local schools. Two washers Two dryers Three dishwashers

  Georgia Wasserman Coldwell Banker Realty

  7 Lincoln St, Westport, CT 06880
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  /36

  $3,999,500

  $2M PRICE DROP

  • 3 Beds
  • 4.5 Baths
  • 2,528 Sq Ft

  1681 Fairfield Beach Rd, Fairfield, CT 06824

  Rarely does a property offer frontage on both Long Island Sound and South Pine Creek. Positioned along a naturally elevated stretch of Fairfield Beach framed by protective dunes, the property enjoys a broad sandy beach at both high and low tide. Located within a residential section of Fairfield Beach away from many public beach access points, the setting offers a unique combination of beach,

  Stephanie Barnes William Raveis Real Estate

  1681 Fairfield Beach Rd, Fairfield, CT 06824
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  /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
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  /40

  $1,949,000

  • 4 Beds
  • 3.5 Baths
  • 4,492 Sq Ft

  125 Coleman Rd, Fairfield, CT 06825

  Inspired by today's most sought-after Organic Modern homes, this custom residence blends clean architectural lines, warm natural materials, and highly functional living spaces to create a home that is as beautiful as it is livable. This newly constructed 4-bedroom, 3.5-bath custom home offers approximately 4,500 square feet of refined living on a private, level lot, showcasing exceptional

  Amanda Foss Keller Williams Prestige Prop.

  125 Coleman Rd, Fairfield, CT 06825
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  /40

  $5,650,000

  New Construction

  • 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
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  /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
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  /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
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  /40

  $1,650,000

  $50K PRICE DROP

  • 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
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  /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
• 

  /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
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  /40

  $5,199,000

  New Construction

  • 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

Showing Results 41 - 78, Page 2 of 2