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South Norwalk, CT Homes for Sale with Acreage

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  • /40

    $5,495,000

    • 5 Beds
    • 8 Baths
    • 8,502 Sq Ft

    7 Buttonwood Ln, Darien, CT 06820

    Spectacular quintessential New England home in Darien has it all! Step into a world of refined elegance with this stately 8,000+SF Colonial masterpiece. Set back on nearly two acres of manicured grounds, boasting a custom 2021 Gunite pool, outdoor kitchen, new patio, huge backyard and firepit, this treasured residence is the ultimate venue for indoor & outdoor living and entertaining. The main

    Gaynor Brennan BHHS Darien/New Canaan

    7 Buttonwood Ln, Darien, CT 06820
  • /40

    $4,650,000

    • 5 Beds
    • 7 Baths
    • 8,550 Sq Ft

    49 Hillspoint Rd, Westport, CT 06880

    Tucked away in the heart of Westport, Hillspoint offers the perfect blend of luxury, lifestyle and location. Minutes to Longshore Club Park, Compo Beach, town and train, it delivers rare privacy with exceptional convenience. Inside, soaring ceilings and sun-filled spaces create a light, airy flow enhanced by high-end finishes throughout. Designed for everyday living and effortless entertaining,

    Michelle Genovesi William Raveis Real Estate

    49 Hillspoint Rd, Westport, CT 06880
  • /33

    $13,000,000

    • 5 Beds
    • 10 Baths
    • 9,564 Sq Ft

    10 Shorehaven Rd, Norwalk, CT 06855

    Rarely does an opportunity arise to own a home in the coastal enclave of Shorehaven, and 10 Shorehaven Road is a true masterpiece. This Nantucket-inspired estate blends timeless elegance with relaxed coastal charm, offering unmatched luxury and tranquility. Set along the serene waterfront, the lush, landscaped grounds feature a sparkling pool, spa, and private dock-perfect for boating adventures

    Laurie Morris Compass Connecticut, LLC

    10 Shorehaven Rd, Norwalk, CT 06855
  • /38

    $4,495,000 New Construction

    • 5 Beds
    • 8 Baths
    • 6,535 Sq Ft

    20 Marianne Rd, Darien, CT 06820

    New construction and ready for 2026! On a coveted Darien cul-de-sac, this modern colonial boasts 6500sf of elegance and comfort. Step through the welcoming foyer, complete with a coat room and powder room, and into a spacious, light-flooded living room, perfect for gatherings that stretch into the evening. The custom kitchen is a true centerpiece, with a grand stone island, Thermador appliances,

    Serena Richards Brown Harris Stevens

    20 Marianne Rd, Darien, CT 06820
  • /40

    $1,350,000

    • 5 Beds
    • 4.5 Baths
    • 6,774 Sq Ft

    205 E Rocks Rd, Norwalk, CT 06851

    Welcome to this classical yet modern Victorian/Colonial custom built in 2006 located in the sought after Cranbury area. A must see, this timeless treasure is a blend of beauty & modern comfort. Situated within an expansive, beautifully landscaped 1.42 acre setting adjacent to a 2 acre natural preserve.This 5 bdrm 4.5 bath home was freshly updated with modern interior colors making every room

    Antoinette Antenucci Coldwell Banker Realty

    205 E Rocks Rd, Norwalk, CT 06851
  • /6

    $3,500,000

    • 3 Beds
    • 3.5 Baths
    • 1,299 Sq Ft

    0 Calf Pasture Island Unit 24147619, Norwalk, CT 06854

    Opportunities like this are rare. Calf Pasture Island is one of just 10 private islands off the coast of Norwalk, offering a uniquely private coastal setting and a blank canvas for imagination. Properties like this remain in the same hands for many decades and do not come up for sale often. Located approximately a half mile offshore, it is among the closest islands to the mainland and takes its

    Andrew Whiteley Brown Harris Stevens

    0 Calf Pasture Island Unit 24147619, Norwalk, CT 06854
  • /40

    $2,575,000

    • 6 Beds
    • 4.5 Baths
    • 5,083 Sq Ft

    4 the Fenway, Westport, CT 06880

    Timeless elegance in Westport's renowned Old Hill. Set on 2.22 bucolic acres w/a heated Gunite pool & picturesque pond, this expansive 5-6 bedroom,4.5 bath farmhouse blends classic charm w/thoughtful recent enhancements that delivers a renewed sense of style & energy to the home. A renovated kitchen remains the heart of the home, featuring a generous center island & a stunning, glass-walled

    Mary Kate Klemish-Boehm Brown Harris Stevens

    4 the Fenway, Westport, CT 06880
  • /15

    $1,200,000

    • 4 Beds
    • 2.5 Baths
    • 2,084 Sq Ft

    5 Inwood Ln, Westport, CT 06880

    Walk to beach, Compo Beach neighborhood. Inwood Lane is off of Hale Road, off of Hillspoint Road. The backyard of this home views lovely homes on Loretta Court. Charming, with four bedrooms and a large family room. Lovely deck overlooking the backyard with flowers and fauna. The master suite has it's own wing, with fireplace, walk in closet, and full bath, and is accessible to the large deck

    Charlotte Cotton William Raveis Real Estate

    5 Inwood Ln, Westport, CT 06880
  • /40

    $2,698,000

    • 4 Beds
    • 3.5 Baths
    • 4,186 Sq Ft

    135 Comstock Hill Rd, New Canaan, CT 06840

    Introducing The Sun House with a blend of history and modernity. Enveloped in the charm of 1845 architecture, this Silvermine estate is a treasure trove for the discerning homeowner. Spanning over 4,000 square feet, the fully updated main house boasts four bedrooms and three and a half bathrooms. Step into the chef's kitchen, a culinary haven for the home gourmet, where modern amenities meet

    Marion Filley Compass Connecticut, LLC

    135 Comstock Hill Rd, New Canaan, CT 06840
  • /8

    $925,515

    • 3 Beds
    • 3 Baths
    • 1,762 Sq Ft

    58 Old Rock Ln, Norwalk, CT 06850

    Builder's Opportunity - Solid Foundation, Premium Materials Included Rare 1.2-acre riverfront parcel in desirable West Norwalk, offering stone walkways, mature landscaping, and exceptional natural privacy. The existing structure is ready for rebuild from the deck up on a solid, existing foundation, providing a meaningful head start for builders seeking a high-end custom project in a sought-after

    Chris Buswell DBA Options Real Estate

    58 Old Rock Ln, Norwalk, CT 06850
  • /35

    $4,495,000

    • 5 Beds
    • 6 Baths
    • 6,325 Sq Ft

    15 Marianne Rd, Darien, CT 06820

    Ideally situated between the coveted town centers of Darien and New Canaan, this exceptionally and recently completely redesigned colonial rests on 2.4 acres of pristine, park-like grounds. Enveloped by a perimeter of mature trees, a rare sense of serenity is felt upon arrival. Finished with an uncompromising attention to detail, a sophisticated design aesthetic and superior craftsmanship

    Nellie Snell William Raveis Real Estate

    15 Marianne Rd, Darien, CT 06820
  • /38

    $4,750,000 Coming Soon

    • 6 Beds
    • 8 Baths
    • 6,762 Sq Ft

    66 Stanton Rd, Darien, CT 06820

    Welcome to 66 Stanton Road. Set on 1.34 landscaped acres, this classic 1938 clapboard colonial blends architectural charm with thoughtful updates, including a full renovation and expansion completed in 2009. Designed for effortless living and entertaining, the home offers refined formal rooms and relaxed gathering spaces. A gracious foyer with sweeping curved staircase is flanked by sunlit living

    Amanda Spatola Houlihan Lawrence

    66 Stanton Rd, Darien, CT 06820
  • /15

    $2,200,000

    • Land
    • 2.14 Acres
    • $1,028,037 per Acre

    140L Carter St, New Canaan, CT 06840

    Beautiful level property with approved seven bedroom septic. Buy as land or build custom home. All septic, engineering and drainage plans complete. Ready to build!

    Mitchell Moore Brown Harris Stevens

    140L Carter St, New Canaan, CT 06840
  • /7

    $3,500,000

    • 2 Beds
    • 1 Bath
    • 915 Sq Ft

    0 E Betts Island Unit 24148140, Norwalk, CT 06854

    Opportunities like this are exceedingly rare. Betts Island is one of just 10 private islands off the coast of Norwalk, offering a uniquely private coastal setting and a canvas for imagination. Located approximately one mile offshore, the island is distinguished by its natural land bridge, which connects its two halves and creates a protected cove long favored by boaters. A small bungalow

    Andrew Whiteley Brown Harris Stevens

    0 E Betts Island Unit 24148140, Norwalk, CT 06854
  • /36

    $9,350,000

    • 7 Beds
    • 10 Baths
    • 9,649 Sq Ft

    18 Tokeneke Trail, Darien, CT 06820

    This magnificent Round Meadows estate with a fantastic 9700 sf house on 5.346 acres of private property is now on the market for the first time in more than 54 years. Located in the private Tokeneke Association with protected land trust property to the East and West of it, Round Meadows is the ultimate in privacy and natural beauty. The owners had the vision to preserve, restore and ultimately

    Robin Stineman William Pitt Sotheby's Int'l

    18 Tokeneke Trail, Darien, CT 06820
  • /37

    $13,000,000

    • 5 Beds
    • 10 Baths
    • 10,197 Sq Ft

    865 Hollow Tree Ridge Rd, Darien, CT 06820

    Set on 7 acres, this exceptional estate offers a private, sophisticated retreat at the end of a Bradford pear-lined gravel drive. The property includes a 10,000-square-foot main residence with pool and pool house, and a remarkable field house designed by architect Louise Brooks. The main house blends timeless elegance with modern design, while the field house delivers a one-of-a-kind recreational

    Ashley Dineen Compass Connecticut, LLC

    865 Hollow Tree Ridge Rd, Darien, CT 06820
  • /39

    $15,000,000

    • 5 Beds
    • 10 Baths
    • 10,197 Sq Ft

    865 Hollow Tree Ridge Rd, Darien, CT 06820

    Set on 9.4 acres, this exceptional estate offers a private, sophisticated retreat at the end of a Bradford pear-lined gravel drive. The property includes a 10,000-square-foot main residence with pool and pool house, a two-bedroom guest cottage, and a remarkable field house designed by architect Louise Brooks. The main house blends timeless elegance with modern design, while the field house

    Ashley Dineen Compass Connecticut, LLC

    865 Hollow Tree Ridge Rd, Darien, CT 06820
  • /16

    $1,475,000

    • Land
    • 1.05 Acres
    • $1,404,762 per Acre

    50 Sylvan Rd N, Westport, CT 06880

    DREAM YOUR TOMORROW This 1.05 acre of dry, level land that is available for sale, is beautifully sited in the middle of Westport's Old Hill and awaits your imagination. Enter through the original gates of the 1928 Arthur Whiteside Estate at 50 Sylvan North --- the park-like entry to the 25-acre estate built for Whiteside, who founded and headed the commercial credit rating firm of Dun &

    Martha Eidman Coldwell Banker Realty

    50 Sylvan Rd N, Westport, CT 06880
  • /40

    $2,995,000

    • 4 Beds
    • 3.5 Baths
    • 3,744 Sq Ft

    105 White Oak Shade Rd, New Canaan, CT 06840

    Totally transformed - English countryside meets classic CT! Prominently sited on ~1.3 private acres in the highly coveted South of the YMCA neighborhood, this stunning colonial estate offers an unparalleled lifestyle. Located just minutes from the heart of downtown New Canaan, Waveny Park, and top-rated schools, this extraordinary home is a rare gem. Thoughtfully transformed by its current

    Daniel McCamblau Brown Harris Stevens

    105 White Oak Shade Rd, New Canaan, CT 06840
  • /40

    $2,150,000 Open Thu 11AM - 2PM

    • 4 Beds
    • 3.5 Baths
    • 3,023 Sq Ft

    234 Wilton Rd, Westport, CT 06880

    Wilton Road places you minutes from town and the shoreline. At 234, convenience and privacy coexist. A turn onto a side lane and a set-back approach behind mature trees create a setting that feels distinctly separate from the street. Originally built in 1884, the home has been fully renovated and thoughtfully expanded. A 2024 addition reshaped the main level, enlarging the kitchen and introducing

    Cindy Raney Coldwell Banker Realty

    234 Wilton Rd, Westport, CT 06880
  • /40

    $2,695,000

    • 4 Beds
    • 5 Baths
    • 5,207 Sq Ft

    123 Greens Farms Rd, Westport, CT 06880

    Classic Greens Farms Colonial - Timeless Elegance Meets Modern Comfort ~ Nestled in one of Westport's most desirable neighborhoods, this beautifully updated Center Hall Colonial offers the perfect blend of timeless charm and modern luxury. Ideally located just minutes from Sherwood Island State Park-with its miles of golden sand beaches, scenic picnic areas, and sweeping views-this home provides

    Shalini Madaras Silver Pine Real Estate

    123 Greens Farms Rd, Westport, CT 06880
  • /5

    $2,100,000

    • Land
    • 2 Acres
    • $1,050,000 per Acre

    136L Carter St, New Canaan, CT 06840

    Beautiful level property with approved seven bedroom septic. Buy as land or build custom home. All septic, engineering and drainage plans complete. Ready to Build!

    Mitchell Moore Brown Harris Stevens

    136L Carter St, New Canaan, CT 06840
  • /15

    $1,995,000

    • Land
    • 2.31 Acres
    • $863,636 per Acre

    158L Carter St, New Canaan, CT 06840

    Beautiful level property with approved five bedroom septic. Buy as land or build custom home. All engineering and drainage plans complete. Ready To Build! Flat land with stone walls.

    Mitchell Moore Brown Harris Stevens

    158L Carter St, New Canaan, CT 06840
  • /10

    $1,895,000

    • Land
    • 2.49 Acres
    • $761,044 per Acre

    152L Carter St, New Canaan, CT 06840

    Beautiful level property with appoved five bedroom septic. Buy as land or build custom home. All engineering and drainage plans complete. Ready To Build!

    Mitchell Moore Brown Harris Stevens

    152L Carter St, New Canaan, CT 06840
  • /40

    $999,500

    • 4 Beds
    • 2.5 Baths
    • 2,409 Sq Ft

    153 Fillow St, Norwalk, CT 06850

    Recently renovated and ideally set on a full acre in sought after West Norwalk, this exceptional home borders Oak Hills Golf Course and offers a rare blend of privacy, open space, and sweeping views. A gracious foyer leads to sun-filled living and dining rooms with oversized bay windows overlooking the expansive backyard. The sparkling eat-in kitchen w/new countertops and st/st appliances flows

    Max Dober Keller Williams Prestige Prop.

    153 Fillow St, Norwalk, CT 06850
  • /29

    $2,750,000

    • 5 Beds
    • 6 Baths
    • 4,672 Sq Ft

    12 Dellwood Rd, Darien, CT 06820

    This beautifully designed residence seamlessly blends timeless charm with modern sophistication, showcasing sun-drenched interiors, inviting fireplaces, and refined architectural details throughout. A secluded stone patio overlooks the sparkling in-ground gunite pool and pool house, all set within a serene, park-like landscape - an idyllic backdrop for both intimate gatherings and grand

    Lori Printz Coldwell Banker Realty

    12 Dellwood Rd, Darien, CT 06820
  • /37

    $5,350,000

    • 5 Beds
    • 8 Baths
    • 8,035 Sq Ft

    473 Hollow Tree Ridge Rd, Darien, CT 06820

    Welcome to 473 Hollow Tree Ridge Road in Darien - a custom built, stone and shingle Colonial set on 1.3 professionally landscaped acres offering exceptional indoor and outdoor living. This 5-bedroom smart home blends timeless architecture with extensive upgrades and modern technology throughout. The resort-style backyard features a pool with spa, pool house with nano doors, outdoor shower, custom

    Ellen Mccue Houlihan Lawrence

    473 Hollow Tree Ridge Rd, Darien, CT 06820
  • /7

    $2,695,000 Coming Soon

    • 4 Beds
    • 3.5 Baths
    • 4,260 Sq Ft

    26 Holly Ln, Darien, CT 06820

    Classic Ranch on Expansive Park-Like Acre+ in one of Darien's Most Sought-after Neighborhoods. Nestled on a prime 1.08-acre property, this home offers the perfect backdrop for your dream lifestyle. The light-filled formal living room, highlighted by a wood-burning fireplace and custom built-ins, flows seamlessly into the inviting family room with rich wood paneling and a second wood-burning

    Sara Littlefield BHHS Darien/New Canaan

    26 Holly Ln, Darien, CT 06820
  • /10

    $1,350,000

    • Land
    • 2 Acres
    • $675,000 per Acre

    3 Hilltop Rd, Norwalk, CT 06854

    Set on a quiet 1.99-acre knoll just steps from the water, 3 Hilltop offers a rare opportunity to build in one of the area's most desirable private communities. The elevated setting provides privacy and strong potential for a custom home, with the natural landscape and topography already doing the work. Wilson Point is known for its close-knit community and coastal lifestyle, with access to a

    Zoe Hamann Compass Connecticut, LLC

    3 Hilltop Rd, Norwalk, CT 06854
  • /39

    $2,995,000

    • 6 Beds
    • 6 Baths
    • 4,848 Sq Ft

    9 Point o Woods Rd S, Darien, CT 06820

    Located on a quiet cul-de-sac in Darien's sought-after Ox Ridge School district, this inviting 4 bedroom Cape offers timeless character, privacy, and versatile living. Sun-filled living spaces and a well-designed floor plan enhance everyday comfort while maintaining the home's character. The primary bedroom features a fireplace, creating a warm and inviting retreat, complemented by three

    Ashley Dineen Compass Connecticut, LLC

    9 Point o Woods Rd S, Darien, CT 06820
  • /17

    $6,995,826 New Construction

    • 6 Beds
    • 10 Baths
    • 8,417 Sq Ft

    24 Edgemarth Hill Rd, Westport, CT 06880

    True Beauty In The Making! 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 walls of windows, sexy floor-to-ceiling stone and textured accents, vaulted ceilings, and

    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

    $2,995,000

    • 5 Beds
    • 4.5 Baths
    • 4,454 Sq Ft

    48 Green Meadow Ln, New Canaan, CT 06840

    Experience the pinnacle of New Canaan modernism at 48 Green Meadow, a 4,400+ sq ft architectural masterpiece designed by the acclaimed Austin Patterson Disston Architects. Tucked away at the end of a scenic, ultra-private cul-de-sac, this estate seamlessly fuses eco-conscious Geo-thermal technology with high-end luxury. The open-concept interior is a light-drenched sanctuary featuring five

    Jaime Sneddon William Pitt Sotheby's Int'l

    48 Green Meadow Ln, New Canaan, CT 06840
  • /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
  • /34

    $2,999,000

    • 4 Beds
    • 3.5 Baths
    • 3,411 Sq Ft

    561 Middlesex Rd, Darien, CT 06820

    In the heart of Darien, where history lingers and owls whisper through the trees, stands a timeless 1800s home at 561 Middlesex Road - a place where memory breathes and dreams take root. Set upon 2.6 serene and level acres, yet close to all amenities, this enchanting farmhouse rests within a world of quiet beauty, where a secret garden path winds softly beneath the shade, inviting you to wander,

    Serena Richards Brown Harris Stevens

    561 Middlesex Rd, Darien, CT 06820
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