Old Greenwich, CT Homes for Sale with Acreage

• 

  

  

  /21

  $1,995,000

  • 4 Beds
  • 3 Baths
  • 3,284 Sq Ft

  297 Cognewaugh Rd, Cos Cob, CT 06807

  Welcome to your dream home at 297 Cognewaugh Road! Nestled in the picturesque landscape on two wooded acres, this delightful 4-bedroom, 3-bathroom residence offers a sprawling 3,284 square feet of living space. From the moment you step inside, you'll be captivated by the warmth of the hardwood floors and the sun-drenched rooms. The spacious formal dining room is perfect for hosting gatherings,

  Russell Pruner Compass Connecticut, LLC

  297 Cognewaugh Rd, Cos Cob, CT 06807
• 

  

  

  /31

  $8,950,000

  • 6 Beds
  • 6 Baths
  • 5,040 Sq Ft

  33 Meadow Wood Dr, Greenwich, CT 06830

  In the gated Quarry Farm neighborhood of the enchanting Belle Haven Association with 24hr security, this property offers a unique opportunity to renovate or build new, 16,000+ sq ft waterfront home. Overlooking Byram Harbor and Long Island Sound, the current 6-bedroom house sits on 2.78 acres with a pool, adjacent to a 1.09-acre protected lot. Once a quarry and later acquired as part of the

  Joseph Barbieri Sotheby's International Realty

  33 Meadow Wood Dr, Greenwich, CT 06830
• 

  

  

  /69

  $2,985,000

  • 4 Beds
  • 5 Baths
  • 3,826 Sq Ft

  681 River Rd, Cos Cob, CT 06807

  Timeless , this architecturally designed contemporary home blends soaring vaulted ceilings with panoramic views, creating a seamless connection to the outdoors. Thoughtfully sited on 2.32 peaceful, private acres, the home embraces natural light as the seasons change, all while remaining minutes from every convenience possible.The open-concept floor plan is ideal for both grand entertaining and

  Paula Waldman BHHS New England Properties

  681 River Rd, Cos Cob, CT 06807
• 

  

  

  /23

  $33,000,000

  • 8 Beds
  • 14 Baths
  • 18,954 Sq Ft

  555 Lake Ave, Greenwich, CT 06830

  Overlooking 8+park-like acres, this majestic brick Georgian was transformed to blend top of the line appointments with a rich array of custom detailing. Crowned by a 3-story chandelier, the impressive reception hall with Wenge walnut parquetry floor opens to a formal Dining Room with fireplace and elegant Living Room with fireplace and custom bar. Distinguished two-story English mahogany library

  Leslie McElwreath Sotheby's International Realty

  555 Lake Ave, Greenwich, CT 06830
• 

  

  

  /23

  $4,350,000

  • 6 Beds
  • 5 Baths
  • 4,958 Sq Ft

  121 Round Hill Rd, Greenwich, CT 06831

  Premier Round Hill Rd location! Fabulous property, pool, stable, the perfect blend of tranquil manicured and natural landscapes. Move right into this 5 bedroom 4 1/2 bath home, also featuring upgrades like generator, irrigation system, and largely new windows. Given this top location, capture much value ''runway'' and create your perfect kitchen and living improvements. Limitedless upside. See

  Sabine Schoenberg PrimeSites, Inc.

  121 Round Hill Rd, Greenwich, CT 06831
• 

  

  /17

  $7,995,000

  • Land
  • 1.90 Acres
  • $4,207,895 per Acre

  2 Vista Dr, Greenwich, CT 06830

  Stunning waterfront building lot in the private downtown Indian Harbor Association with 24-hour security. This gated community has many luxury waterfront homes in the district. The expansive lot has 1.9 acres in a 1/2 zone, allowing for a substantial home to be built. This lot is not subdividable. There is 290 feet of waterfront on Long Island Sound with its own pier and dock. The owners had

  Barbara Wells Houlihan Lawrence

  2 Vista Dr, Greenwich, CT 06830
• 

  

  /17

  $7,995,000

  • Land
  • 1.90 Acres
  • $4,207,895 per Acre

  2 Vista Dr, Greenwich, CT 06830

  Stunning waterfront building lot in the private downtown Indian Harbor Association with 24-hour security. This gated community has many luxury waterfront homes in the district. The expansive lot has 1.9 acres in a 1/2 zone, allowing for a substantial home to be built. This lot is not subdividable. There is 290 feet of waterfront on Long Island Sound with its own pier and dock. The owners had

  Barbara Wells Houlihan Lawrence

  2 Vista Dr, Greenwich, CT 06830
• 

  

  /19

  $2,799,000

  • 5 Beds
  • 5.5 Baths
  • 4,525 Sq Ft

  32 Jeffrey Rd, Greenwich, CT 06830

  A hidden gem close to town, updated and at the end of a cul-de-sac on a great quiet street, this beautiful 4,525-square-ft home on 1 acre offers a perfect blend of tranquility and convenience, located just minutes from town, the property boasts offices, 5 bedrooms, 5.5 baths, creating flexible layout, a perfect lifestyle for today's owner. Perfect for working from home or pursuing your passions.

  Lin Lavery Coldwell Banker Realty

  32 Jeffrey Rd, Greenwich, CT 06830
• 

  

  /39

  $2,200,000 Open Sat 1PM - 3PM

  • 5 Beds
  • 7.5 Baths
  • 6,354 Sq Ft

  25 Cogswell Ln, Stamford, CT 06902

  This stunning 5-bedroom, 7.5 bath brick contemporary blends timeless elegance with modern sophistication. From the grand foyer, showcasing skylights and a limestone feature wall, to the living room with a quartzite fireplace and cathedral ceiling, every space in this home is designed for both beauty and function. The formal dining room, features a large bay window, offering picturesque views. The

  Jim Caldarone William Pitt Sotheby's Int'l

  25 Cogswell Ln, Stamford, CT 06902
• 

  

  /37

  $4,275,000 Open Sun 11AM - 1PM

  • 5 Beds
  • 8 Baths
  • 6,725 Sq Ft

  490 North St, Greenwich, CT 06830

  Rare opportunity to own a 200 year old Barn on one mid-country acre, designed in the 70's by renowned architect Charles Gwathmey. Owners updated it to add additional bedrooms and seamlessly connect indoor and outdoor spaces offering year-round entertainment. Main entrance opens to an expansive 30 X 35' Great room filled with natural light, original beams, and impressive fireplace. A generous

  Spencer Sodokoff Houlihan Lawrence

  490 North St, Greenwich, CT 06830
• 

  

  /11

  $4,350,000

  • Land
  • 2.30 Acres
  • $1,891,304 per Acre

  121 Round Hill Rd, Greenwich, CT 06831

  This property is one of the premier addresses in Greenwich, CT. This oversized, 2.3-acre property is located only minutes to town, public and private schools, and convenient to NYC. Land can't be appreciated from the street. 121 RHR offers a unique blend of privacy and open, magnificent backyard. Manicured lawns, plantings, and old stonewalls bordered by Nature provide the ultimate in

  Sabine Schoenberg PrimeSites, Inc.

  121 Round Hill Rd, Greenwich, CT 06831
• 

  

  /41

  $10,950,000

  • 6 Beds
  • 8 Baths
  • 9,258 Sq Ft

  142 Cedar Cliff Rd, Riverside, CT 06878

  Exquisite 2016 French Normandy manor designed by premier architect, Douglas VanderHorn blends classic elegance with 3 levels of stunning modern aesthetics in coveted Riverside association with Shoreline pool and neighborhood private beach. Sophisticated, custom crafted interior with Italian marble mantels framing four fireplaces, quarter-sawn white oak flooring, 10 ft. ceilings, French doors to

  Alison Farn-Leigh BHHS New England Properties

  142 Cedar Cliff Rd, Riverside, CT 06878
• 

  

  /39

  $24,950,000

  • 10 Beds
  • 19 Baths
  • 17,878 Sq Ft

  97 Pecksland Rd, Greenwich, CT 06831

  Truly unique 19 Acre estate in the heart of mid country! Prepared to be captivated by this custom built masterpiece of design and craftsmanship. Completed in 2009, and offered to the market for the first time since completion, 97 Pecksland has an unrivaled combination of lot size, quality and privacy. Enter through the grand gated entrance and dramatic driveway to the elevated main house on the

  Robert Johnson Brown Harris Stevens CT, LLC

  97 Pecksland Rd, Greenwich, CT 06831
• 

  

  /42

  $8,950,000

  • 10 Beds
  • 9 Baths
  • 9,483 Sq Ft

  14 Meadow Dr, Greenwich, CT 06831

  DISCOVER BREEZEMORE Experience the rare opportunity to own a piece of history with the stunning Breezemore estate located in Greenwich, Connecticut. Built in 1909, this magnificent property offers 10,000 square feet of architectural splendor, old-world charm, and modern conveniences. Set high on 3.2 private, park-like acres within close distance of downtown Greenwich, this property stands

  Ryan Hoffman Houlihan Lawrence

  14 Meadow Dr, Greenwich, CT 06831
• 

  

  /35

  $1,450,000

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft

  630 Steamboat Rd Unit 2B, Greenwich, CT 06830

  Indian Harbor House. Direct waterfront on Greenwich Harbor. Western Exposure with wonderful sunsets. The perfect Pied-a-Terre. Walking distance to the Indian Harbor Yacht Club, Bruce Museum, Bruce Park, Delmar Hotel, Island Beach Ferry, train station and Greenwich Avenue's stores and restaurants. Stunning water views. Magnificent sunlit rooms overlooking the water. Primary bedroom connects via

  Curtis Wood William Raveis Real Estate

  630 Steamboat Rd Unit 2B, Greenwich, CT 06830
• 

  

  /12

  $4,700,000

  • Land
  • 1.00 Acre
  • $4,700,000 per Acre

  1 Pratt Island, Darien, CT 06820

  Are you looking for a private, waterfront haven to build your dream home? Look no further than 1 Pratt Island. This 1 acre property is at the end of a private association with sunrise and sunset views. The lot comes with easements to a deep water dock and an incredible sandy beach steps away. With gorgeous mature trees, this property overlooks Darien Harbor in one direction and Stamford's Shippan

  Keiley Fuller Compass Connecticut, LLC

  1 Pratt Island, Darien, CT 06820
• 

  

  /34

  $44,600,000

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

  545 Indian Field Rd, Greenwich, CT 06830

  An idyllic coastal resort, this regal stone Georgian features 450 feet of direct waterfront acreage with expansive water views of the Long Island Sound to the NYC skyline, inside the exclusive Mead Point Association with 24hr guard-gated security. Masterfully designed and meticulously constructed in 2014 with inspiration from the original 1928 stone manor, this sophisticated residence offers

  Leslie McElwreath Sotheby's International Realty

  545 Indian Field Rd, Greenwich, CT 06830
• 

  

  /23

  $14,900,000

  • 6 Beds
  • 12 Baths
  • 15,171 Sq Ft

  537 North St, Greenwich, CT 06830

  Exquisite six bedroom, 8.4 bathroom stone manor executed to the highest standards sited on 2.97 picturesque acres. Chic and sophisticated interiors by Amy Hirsch throughout three levels of living space with extra high ceilings, oversized custom windows and all modern amenities. Elegant entry hall with a sweeping staircase and 3 stop elevator opens to a floor plan ideal for both formal and casual

  Leslie McElwreath Sotheby's International Realty

  537 North St, Greenwich, CT 06830
• 

  

  /34

  $22,000,000

  • 7 Beds
  • 6 Baths
  • 6,166 Sq Ft

  36, 38, 0 Game Cock Rd, Greenwich, CT 06830

  36, 38 and 0 Game Cock Road make up this 1.1+ acre island property that has been enjoyed as a multi generational family compound. One of only a few Island properties in Greenwich, let alone the Connecticut shoreline, to have it's own private bridge for access. The property boasts a 7 bedroom, 5 bath 6166 SQ FT main house, 3 en-suite bedroom 3238 SQ FT guest house, boathouse for entertaining,

  Brett Smith Brown Harris Stevens CT, LLC

  36, 38, 0 Game Cock Rd, Greenwich, CT 06830
• 

  

  /36

  $13,995,000

  • 7 Beds
  • 11 Baths
  • 9,416 Sq Ft

  88 Cedar Cliff Rd, Riverside, CT 06878

  Magnificent one of a kind Riverside Estate designed by award winning architect Douglas Vanderhorn showcases sweeping waterviews and stunning interior brimming with classical elements and luxurious finishes. This thoughtfully 2008 custom built home boasts impeccable details, high ceilings with walls of windows facing the Sound and fabulous covered porches, ideal for indoor / outdoor living, pool

  Joanne Mancuso Houlihan Lawrence

  88 Cedar Cliff Rd, Riverside, CT 06878
• 

  

  /3

  $4,000,000

  • Land
  • 1.00 Acre
  • $4,000,000 per Acre

  74 Long Neck Point Rd, Darien, CT 06820

  This is a rare opportunity to build the home of your dreams on Long Neck Point - one of the most sought after and picturesque communities on the Eastern Seaboard! As part of a 4 unit subdivision, you will have shared use of two boat docks and Long Island Sound access! Your newly constructed home will enjoy amazing views to Gorham's Pond and Long Island Sound. Walk or bike to Pear Tree Point or

  Jon Magnotta Outlook Realty

  74 Long Neck Point Rd, Darien, CT 06820
• 

  

  /11

  $4,500,000

  • Land
  • 1.24 Acres
  • $3,629,032 per Acre

  92 Pear Tree Point Rd, Darien, CT 06820

  This is a rare opportunity to build the home of your dreams on Long Neck Point - one of the most sought after and picturesque communities on the Eastern Seaboard! As part of a 4 unit subdivision, you will have shared use of two boat docks and Long Island Sound access! Your newly constructed home will enjoy amazing views to Gorham's Pond and Long Island Sound. Walk or bike to Pear Tree Point or

  Jon Magnotta Outlook Realty

  92 Pear Tree Point Rd, Darien, CT 06820
• 

  

  /11

  $4,500,000

  • Land
  • 1.14 Acres
  • $3,947,368 per Acre

  88 Pear Tree Point Rd, Darien, CT 06820

  This is a rare opportunity to build the home of your dreams on Long Neck Point - one of the most sought after and picturesque communities on the Eastern Seaboard! As part of a 4 unit subdivision, you will have shared use of two boat docks and Long Island Sound access! Your newly constructed home will enjoy amazing views to Gorham's Pond and Long Island Sound. Walk or bike to Pear Tree Point or

  Jon Magnotta Outlook Realty

  88 Pear Tree Point Rd, Darien, CT 06820
• 

  

  /20

  $22,000,000 New Construction

  • 8 Beds
  • 12 Baths
  • 14,071 Sq Ft

  8 Fox Run Ln, Greenwich, CT 06831

  Ultra-stylish 2024 custom-built Contemporary from visionary developer SBP Homes graces nearly 5.5 private, gated acres very close to town with pool, spa, two-bedroom pool house, porches, outdoor kitchen, fireplace and tennis court designed for optimum indoor/outdoor entertaining and relaxed living. Luxurious details elevate the 11,000+ sq. Interior with Bulthaup kitchen, living room bar; walls

  James Hoffman Houlihan Lawrence

  8 Fox Run Ln, Greenwich, CT 06831
• 

  

  /20

  $29,750,000 New Construction

  • 9 Beds
  • 15 Baths
  • 17,100 Sq Ft

  26 Meadowcroft Ln, Greenwich, CT 06830

  Build your legacy in one of Greenwich, CT's most sought-after mid-country estate locations. Fully approved by P&Z, Bldg Dept, Conservation and Wetlands. This stone Georgian Colonial blends timeless elegance with modern luxury. Set on 3 level acres at the end of a cul-de-sac, featuring a main residence with over 15,000 sq ft, 7 bdrms across 4 levels and a 2 bdrm, 2,137 sq ft guest house. Crafted

  Brian Milton Compass Connecticut, LLC

  26 Meadowcroft Ln, Greenwich, CT 06830
• 

  

  /12

  $13,850,000 New Construction

  • 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 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 additional

  Amanda Miller Houlihan Lawrence

  133 Doubling Rd, Greenwich, CT 06830
• 

  

  /16

  $4,700,000 New Construction

  • 6 Beds
  • 7 Baths
  • 8,500 Sq Ft

  1 Pratt Island, Darien, CT 06820

  Proposed site plan and new construction drawings by Hatley Homes Design. Are you looking for a private, waterfront haven to build your dream home? Look no further than 1 Pratt Island. This 1 acre property is at the end of a private association with sunrise and sunset views. The lot comes with easements to a deep water dock and an incredible sandy beach steps away. With gorgeous mature trees, this

  Keiley Fuller Compass Connecticut, LLC

  1 Pratt Island, Darien, CT 06820
• 

  

  /16

  $1,700,000 Pre-Foreclosure

  • 6 Beds
  • 4.5 Baths
  • 7,600 Sq Ft

  12 Old Mill Ln, Stamford, CT 06902

  Amazing Home waiting for your touch at Westover Villa, close to New York City. A huge Master Bedroom with a bathroom with jacuzzi, walk-in closets, and an extra room to relax in. This beautiful home offers a Living Room, Dining room, eat-in kitchen, family room, and 5 more bedrooms. Subject to bank approval.

  Jennifer Ramirez Smart Realty

  12 Old Mill Ln, Stamford, CT 06902

Showing Results 41 - 68, Page 2 of 2