Old Greenwich, CT Homes for Sale with Acreage

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  /40

  $4,750,000

  • 5 Beds
  • 3.5 Baths
  • 3,443 Sq Ft

  215 Ocean Dr W, Stamford, CT 06902

  Set on 150 feet of private sandy beach along Stamford Harbor, this exceptional Shippan Point waterfront offers a rare combination of direct sandy beachfront, striking views, and an exceptional position along the waterfront. With a western-facing orientation, the property enjoys beautiful sunsets and sweeping water views across the harbor and out toward the New York City skyline. Approached by a

  Joshua Weisman William Raveis Real Estate

  215 Ocean Dr W, Stamford, CT 06902
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  /25

  $19,000,000

  • 5 Beds
  • 8.5 Baths
  • 8,248 Sq Ft

  207 Long Neck Point Rd, Darien, CT 06820

  This dramatic property offers 200 feet of waterfront frontage with your own private beach in the premier Long Neck Point area of Darien. Offering two separately deeded parcels ( that create this magical estate to ensure the peace and tranquility of your own private oasis. East facing views are enjoyed from most rooms in this spectacular home offering natural light throughout the day. Once owned

  Shelly Tretter Lynch Compass Connecticut, LLC

  207 Long Neck Point Rd, Darien, CT 06820
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  /31

  $2,350,000

  $149K PRICE DROP

  • 5 Beds
  • 5 Baths
  • 3,598 Sq Ft

  201 Shore Rd, Greenwich, CT 06830

  On sought-after Belle Haven peninsula near town, this 2008 expanded 5 bed, 3.2 bath home boasts breathtaking Greenwich Harbor views. Perfectly designed for harborside living & entertaining, the sunlit gourmet chef's kitchen & great room boast an expansive island, custom cabinetry and a wall of windows overlooking harbor & park. The spacious living room, complete with wood burning fireplace &

  Meg McAuley Kaicher Coldwell Banker Realty

  201 Shore Rd, Greenwich, CT 06830
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  /23

  $10,350,000

  • 5 Beds
  • 4 Baths
  • 8,223 Sq Ft

  111 Byram Shore Rd, Greenwich, CT 06830

  Dramatic views of Long Island Sound extend from this spectacular 1.50-acre property with 185 ft of direct water frontage, an 80-ft dock, a sandy boat launch and a 528 sq.ft. antique cottage. Walls of glass in the current 5-bedroom residence open to a spectacular deck with pool and panoramic views. Once part of the 43-acre Edgar Marston estate, the property includes c.1885 Queen Anne-style cottage

  Joseph Barbieri Sotheby's International Realty

  111 Byram Shore Rd, Greenwich, CT 06830
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  /16

  $28,500,000

  New Construction

  • 7 Beds
  • 12 Baths
  • 18,370 Sq Ft

  39 Brookridge Dr, Greenwich, CT 06830

  Set along a quiet street 3 mins from town, this exceptional 2027 new construction blends timeless architecture w modern livability. A striking white brick façade, steep gables, and dark-framed windows create a refined yet welcoming presence. Warm interior light highlights expansive living spaces, including a dramatic kitchen and family room designed for both everyday living and elevated

  Amanda Bates Houlihan Lawrence

  39 Brookridge Dr, Greenwich, CT 06830
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  /7

  $5,450,000

  • Land
  • 2.47 Acres
  • $2,206,478 per Acre

  1 Pecksland Rd, Greenwich, CT 06831

  A nearly two-and-a-half-acre parcel occupying the former gardens of the original Round Hill estate -- elevated, set back from the street, with a gently moving creek along the back and a generous flat building envelope. Pecksland is a distinguished Greenwich address, and the parcel's history as the estate's former gardens gives the site a cultivated character before a new home is even built.

  Leslie McElwreath Sotheby's International Realty

  1 Pecksland Rd, Greenwich, CT 06831
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  /28

  $2,149,000

  • 3 Beds
  • 2.5 Baths
  • 2,496 Sq Ft

  12 Sawmill Terrace, Greenwich, CT 06830

  Tucked away down a quiet mid-country lane, surrounded by pretty woodlands, is this modern styled one level home. Large open reception hall, large living room with fireplace, high ceilings, and a wall of sliders. Study/office area, and large formal south-facing dining room with oversized windows that overlook the front yard and lovely mature trees. A step down from the dining room through French

  Edward Mortimer Sotheby's International Realty

  12 Sawmill Terrace, Greenwich, CT 06830
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  /39

  $42,995,000

  • 6 Beds
  • 9 Baths
  • 12,492 Sq Ft

  545 Indian Field Rd, Greenwich, CT 06830

  A rare waterfront estate of true scale and presence, this reimagined coastal masterpiece commands 1.6 acres on the Long Island Sound with sweeping, unobstructed horizon views. Rebuilt from the foundation up, the home delivers level beachfront living with powerful architectural lines, floor-to-ceiling glass, and a seamless connection to the water at every turn. The approach opens to a 19-foot

  Jesse Marinak Serhant Connecticut LLC

  545 Indian Field Rd, Greenwich, CT 06830
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  /40

  $14,995,000

  • 11 Beds
  • 17 Baths
  • 15,479 Sq Ft

  326 Stanwich Rd, Greenwich, CT 06830

  Welcome to An Extraordinary Lakeside Retreat in GreenwichEncompassing an incredible assemblage of 9.4 lakeside acres ideally situated within the Greenwich mid country, Frye Lake Compound is the ultimate sanctuary for those seeking a world of elevated privacy, scenery and architecture. Nestled around the serene 11-acre Frye Lake, this incomparable park-like estate represents an idyllic

  Kevin Sneddon Compass Connecticut, LLC

  326 Stanwich Rd, Greenwich, CT 06830
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  /37

  $4,995,000

  • 6 Beds
  • 4.5 Baths
  • 4,775 Sq Ft

  17 Brookside Park, Greenwich, CT 06831

  Beautifully renovated six-bedroom English country estate blending classic stone and shingle architecture with modern luxury, ideally set on a private, level acre in a coveted in-town location. Tucked down a quiet private lane, this exceptional property offers privacy, and timeless charm. The heart of the home is a fully updated, state-of-the-art eat-in kitchen, seamlessly connected to a gracious

  Alexandra Friedman Compass Connecticut, LLC

  17 Brookside Park, Greenwich, CT 06831
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  /28

  $999,999

  • 4 Beds
  • 2.5 Baths
  • 2,893 Sq Ft

  45 Carriage Dr S, Stamford, CT 06902

  Nestled in a peaceful Cul de sac in Stamford's sought after Westover neighborhood, this classic 4-bedroom Center Hall Colonial offers a rare opportunity to create your dream home on a beautifully landscaped one acre property. Surrounded by mature trees and lush plantings, the setting provides exceptional privacy and timeless curb appeal. Inside, generously sized rooms and a traditional layout

  Timothy Williamson William Raveis Real Estate

  45 Carriage Dr S, Stamford, CT 06902
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  /40

  $2,395,000

  New Construction $100K PRICE DROP

  • 7 Beds
  • 5.5 Baths
  • 6,268 Sq Ft

  31 Gray Farms Rd, Stamford, CT 06905

  31 Gray Farms Rd nails the wish list for today's buyer: new construction, high-end finishes, space to entertain, and a location that can't be beat. Over an acre in Stamford's Newfield area, the home is surrounded by other new builds and minutes to trains MetroNorth (NYC)/Amtrak, I-95, the Merritt Parkway, JCC, Sterling Farms, and houses of worship. Inside, a bright two-story foyer opens to an

  Jonathan Makovsky Compass Connecticut, LLC

  31 Gray Farms Rd, Stamford, CT 06905
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  /38

  $12,100,000

  • 6 Beds
  • 13 Baths
  • 11,668 Sq Ft

  524 Lake Ave, Greenwich, CT 06830

  A gated drive opens to this elegant six-bedroom Mid-Country Manor overlooking tranquil views of Horseneck Brook. A stone courtyard introduces the dramatic four-story residence with elegant foyer, where sweeping butterfly staircases and limestone floors create a striking architectural welcome. From the gracious gallery hall, beautifully proportioned formal and informal rooms unfold-including

  Leslie McElwreath Sotheby's International Realty

  524 Lake Ave, Greenwich, CT 06830
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  /10

  $14,750,000

  New Construction $900K PRICE INCREASE

  • 7 Beds
  • 9 Baths
  • 10,496 Sq Ft

  133 Doubling Rd, Greenwich, CT 06830

  Stunning 6-bedroom Colonial in Mid-Country currently underway (Summer '26 completion). Designed to impress by the renowned Alex Kaali-Nagy Architect AIA with a traditional exterior look, quintessential Greenwich, but a transitional interior with 4 finished levels and thoughtful design touches throughout, including extensive millwork. Exceptional primary suite with walk-in dressing rooms, plus 5

  Amanda Miller Houlihan Lawrence

  133 Doubling Rd, Greenwich, CT 06830
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  /8

  $4,895,000

  $395K PRICE INCREASE

  • Land
  • 2.3 Acres
  • $2,128,261 per Acre

  Unlisted Address

  LAND W/ APPROVALS in Greenwich's ''Golden Triangle''. Build your 10,000SF dream custom-designed home and pool, and get started right away with in-place (!!!) Wetland (IWWA) Permit, Septic Approval, ZBA Approvals. While a carefully designed architectural plan was developed by the award-winning firm, Saniee Architects, customize the interiors and exterior within the approved footprint. There are no

  Sabine Schoenberg PrimeSites, Inc.

  Unlisted Address
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  /49

  $100,000,000

  • 8 Beds
  • 14 Baths
  • 13,163 Sq Ft

  108 Cedar Cliff Rd, Riverside, CT 06878

  Perched in timeless elegance atop an expansive 2.91-acre gated peninsula, with best-in-class views of the Manhattan skyline and the shimmering Long Island Sound, Cedar Cliff is a Mediterranean villa of unrivaled pedigree and commanding presence. Privately situated along a secluded road within Riverside's prestigious Indian Head Association, this storied property occupies the historic grounds of

  Leslie McElwreath Sotheby's International Realty

  108 Cedar Cliff Rd, Riverside, CT 06878
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  /7

  $10,350,000

  $500K PRICE DROP

  • 6 Beds
  • 8 Baths
  • 7,072 Sq Ft

  12 Woodside Rd, Greenwich, CT 06830

  DEER PARK WOODSIDE: This distinguished 1930's brick Georgian is set on a serene, oversized lot within Deer Park Association, embodying the timeless architectural presence of a classic pre-war brick manor. Originally designed as an elegant six-bedroom, six-bath residence, the home offers an exciting opportunity to be reimagined for its next chapter. The exceptional grounds unfold across expansive,

  Leslie McElwreath Sotheby's International Realty

  12 Woodside Rd, Greenwich, CT 06830
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  /28

  $2,195,000

  $200K PRICE DROP

  • 6 Beds
  • 4.5 Baths
  • 10,746 Sq Ft

  677 W Hill Rd, Stamford, CT 06902

  Rare 3.75-Acre Builder Opportunity on W Hill Road Exceptional opportunity to own 3.75 private acres in one of the area's most prestigious and sought-after locations-W Hill Road. This unique property features an existing 4,400 sq ft main residence plus a separate 900 sq ft cottage, offering endless possibilities for builders, investors, or end-users seeking a private estate setting. The current

  Antonio LaRocca The LaRocca Group

  677 W Hill Rd, Stamford, CT 06902
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  /39

  $13,100,000

  • 6 Beds
  • 8 Baths
  • 10,286 Sq Ft

  7 Parsonage Rd, Greenwich, CT 06830

  SUMMER FUN BEGINS HERE! An extraordinary newly constructed residence in the heart of Greenwich,7 Parsonage Road is a masterfully crafted white brick manor on 1.12 acres, defined by timeless elegance and modern sophistication. Spanning four expansive light filled levels served by an elevator, this six-bedroom, six full and two half-bathroom home offers over 10,200+/- square feet of meticulously

  Leslie McElwreath Sotheby's International Realty

  7 Parsonage Rd, Greenwich, CT 06830
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  /43

  $2,299,000

  • 5 Beds
  • 3.5 Baths
  • 2,956 Sq Ft

  42 Stone Brook Ln, Cos Cob, CT 06807

  Tucked at the end of a peaceful cul-de-sac in Cos Cob, within the coveted North Street School district, this serene 5-bedroom home (featuring a main-level en-suite) offers a tranquil escape. Contemporary design shines through vaulted ceilings, skylights, and sun-drenched interiors that flow seamlessly to a large screened-in porch and an expansive 900 sq ft wraparound deck with private wooded

  Cora Lynch-O'Meara Brown Harris Stevens CT, LLC

  42 Stone Brook Ln, Cos Cob, CT 06807
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  /29

  $1,995,000

  • 4 Beds
  • 3.5 Baths
  • 3,546 Sq Ft

  86 Dandy Dr, Cos Cob, CT 06807

  Discover charming, single-level living with incredible space! This classic ranch offers over 2,100 sq. ft. on the main floor, featuring a gracious living room with fireplace, formal dining, and a sunny, open-concept kitchen and family room, plus 4 nicely sized bedrooms. The large screened-in porch offers seamless indoor-outdoor living. Convenience is key with a dedicated laundry/powder room off

  Charles Magyar William Raveis Real Estate

  86 Dandy Dr, Cos Cob, CT 06807

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