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All Old Greenwich Houses For Sale

58 Shore Rd, Greenwich image
58 Shore Rd, Greenwich $19,995,000

You don't look at your home...you look out from it. Set directly on the waterfront in Old Greenwich, this newly constructed residence is a masterclass in design, engineer...

  • 5 Beds
  • 7 Baths
  • 24164225 MLS
58 Shore Road, Old Greenwich image
58 Shore Road, Old Greenwich $19,995,000

You don't look at your home...you look out from it. Set directly on the waterfront in Old Greenwich, this newly constructed residence is a masterclass in design, engineer...

  • 5 Beds
  • 7 Baths
  • 125810 MLS
4 Little Cove Ln, Greenwich image
4 Little Cove Ln, Greenwich $12,900,000 ▼

Exceptional new construction waterfront home set on a private cul-de-sac in one of Old Greenwich's most desirable enclaves. This custom-built residence offers 180-degree ...

  • 5 Beds
  • 7 Baths
  • 24172344 MLS
4 Little Cove Lane, Old Greenwich image
4 Little Cove Lane, Old Greenwich $12,900,000 ▼

Exceptional new construction waterfront home set on a private cul-de-sac in one of Old Greenwich's most desirable enclaves. This custom-built residence offers 180-degree ...

  • 5 Beds
  • 7 Baths
  • 124890 MLS
203 Shore Rd, Greenwich image
203 Shore Rd, Greenwich $9,875,000

Hamptons-Inspired Elegance in Waterfront Lucas Point Experience the ease of coastal living just one hour from New York City in the coveted private waterfront association ...

  • 5 Beds
  • 6 Baths
  • 24196984 MLS
24 Hendrie Drive Extension, Old Greenwich image
24 Hendrie Drive Extension, Old Greenwich $9,500,000

Set on a private, gated 1.6-acre waterfront point in Old Greenwich, this charming Shore Colonial captures beautiful water views and spectacular sunsets. Freshly painted a...

  • 5 Beds
  • 6 Baths
  • 126087 MLS
11 Ledge Road, Old Greenwich image
11 Ledge Road, Old Greenwich $8,750,000

TO BE BUILT estimated Sept 2027. Exceptional new construction in the private Ledge Rd Association with deeded beach access. Elegant floor plan, white oak floors, 4 firepl...

  • 6 Beds
  • 7 Baths
  • 126062 MLS
58 Halsey Dr, Greenwich image
58 Halsey Dr, Greenwich $4,395,000 ▼

Experience exceptional new construction by Build Casa Tua on Halsey Drive. Spanning four finished levels, this home blends timeless architecture with modern luxury. A dra...

  • 5 Beds
  • 7 Baths
  • 24206524 MLS
58 Halsey Drive, Old Greenwich image
58 Halsey Drive, Old Greenwich $4,395,000 ▼

Experience exceptional new construction by Build Casa Tua on Halsey Drive. Spanning four finished levels, this home blends timeless architecture with modern luxury. A dra...

  • 5 Beds
  • 7 Baths
  • 125848 MLS
5 Hunter St, Greenwich image
5 Hunter St, Greenwich $4,195,000

Introducing a newly constructed Contemporary Colonial, by Alfieri Enterprises, that captures the essence of Old Greenwich living offering a seamless blend of classic arch...

  • 6 Beds
  • 7 Baths
  • 24207811 MLS
5 Hunter Street, Old Greenwich image
5 Hunter Street, Old Greenwich $4,195,000

Introducing a newly constructed Contemporary Colonial, by Alfieri Enterprises, that captures the essence of Old Greenwich living offering a seamless blend of classic arch...

  • 6 Beds
  • 7 Baths
  • 125886 MLS
14 Shoreham Club Rd, Greenwich image
14 Shoreham Club Rd, Greenwich $4,000,000

A rare Shorehame Association lot with unobstructed Long Island Sound sight lines offered as an amazing opportunity to build new or reimagine the existing residence in one...

  • 4 Beds
  • 3 Baths
  • 24205297 MLS
681 River Road, Cos Cob image
681 River Road, Cos Cob $3,995,000

Experience modern luxury in this meticulously renovated retreat set on 2.3 private acres, moments from Greenwich amenities. This architectural home offers a brand new gou...

  • 4 Beds
  • 5 Baths
  • 126050 MLS
15 Shorelands Place, Old Greenwich image
15 Shorelands Place, Old Greenwich $3,795,000

Classic Old Greenwich character meets modern living in this beautifully renovated 1907 Shore Colonial. A covered wraparound porch welcomes you to light-filled interiors, ...

  • 4 Beds
  • 4 Baths
  • 125816 MLS
1 Deepwoods Lane, Old Greenwich image
1 Deepwoods Lane, Old Greenwich $3,695,000 ▼

Embrace the Old Greenwich lifestyle in this beautifully updated 4500 sf home. Set back on a quiet street in a desirable neighborhood, the house was thoroughly remodeled ...

  • 5 Beds
  • 4 Baths
  • 125755 MLS
19 Old Club House Road, Old Greenwich image
19 Old Club House Road, Old Greenwich $3,600,000 ▲

Idyllic south of the village location in coveted Shorelands Association offers deeded private beach and dock rights, perfect for kayaking/boating, and a sprawling five-be...

  • 5 Beds
  • 5 Baths
  • 125832 MLS
14 Highview Avenue, Old Greenwich image
14 Highview Avenue, Old Greenwich $3,495,000

LOCATION & CHARM! This 1918 Colonial sits on a coveted street in Old Greenwich. A quintessential wraparound porch opens to a spacious entry, living room with high ceiling...

  • 5 Beds
  • 3 Baths
  • 125771 MLS
14 Highview Ave, Greenwich image
14 Highview Ave, Greenwich $3,495,000

Rich with classic character this 1918 Colonial sits on one of the most coveted streets in Old Greenwich. With an expansive 3,670 square feet, this charm filled home pairs...

  • 4 Beds
  • 3 Baths
  • 24203497 MLS
1 Hendrie Dr Extension, Greenwich image
1 Hendrie Dr Extension, Greenwich $3,300,000

A once-in-a-generation waterfront opportunity in Old Greenwich, perched above Greenwich Cove with breathtaking sunsets, expansive water views, and direct access to "The C...

  • 5 Beds
  • 3 Baths
  • 24194050 MLS
1 Hendrie Drive Extension, Old Greenwich image
1 Hendrie Drive Extension, Old Greenwich $3,300,000

A once-in-a-generation waterfront opportunity in Old Greenwich, perched above Greenwich Cove with breathtaking sunsets, expansive water views, and direct access to ''The ...

  • 5 Beds
  • 3 Baths
  • 125607 MLS
7 Tait Rd, Greenwich image
7 Tait Rd, Greenwich $3,110,000

Welcome to 7 Tait Road, an exquisite Colonial home offering superior quality construction and thoughtful modern design in coveted Old Greenwich. Step onto the welcoming f...

  • 4 Beds
  • 5 Baths
  • 24215682 MLS
7 Tait Road, Old Greenwich image
7 Tait Road, Old Greenwich $3,110,000

Welcome to 7 Tait Road, an exquisite Colonial home offering superior quality construction and thoughtful modern design in coveted Old Greenwich. Step onto the welcoming ...

  • 4 Beds
  • 5 Baths
  • 125895 MLS
6 Meadowbank Rd, Greenwich image
6 Meadowbank Rd, Greenwich $2,895,000 ▼

Updated with a Modern flair this four-bedroom home is near the water, Tod's Point & located on a quiet cul-de-sac in Old Greenwich. Spacious & bright, there is an open de...

  • 4 Beds
  • 4 Baths
  • 24177489 MLS
6 Meadowbank Road, Old Greenwich image
6 Meadowbank Road, Old Greenwich $2,895,000 ▼

Updated with a Modern flair this four-bedroom home is near the water, Tod's Point & located on a quiet cul-de-sac in Old Greenwich. Spacious & bright, there is an open de...

  • 4 Beds
  • 4 Baths
  • 125067 MLS
37 Midbrook Ln, Greenwich image
37 Midbrook Ln, Greenwich $2,795,000

Walk to town, train, Binney Park and bike to beach and come home to a private gated setting. Located on a quiet lane in Old Greenwich, this recently renovated 5 bedroom r...

  • 5 Beds
  • 4 Baths
  • 24216790 MLS
37 Midbrook Lane, Old Greenwich image
37 Midbrook Lane, Old Greenwich $2,795,000 ▼

Walk to town, the train, Binney Park and the beach. Come home to a private gated yard. The major work is already done. Located on a quiet lane in Old Greenwich, this r...

  • 5 Beds
  • 4 Baths
  • 125917 MLS
38 Amherst Road, Riverside image
38 Amherst Road, Riverside $2,425,000

Turnkey, light-filled and thoughtfully renovated, 38 Amherst Road pairs considered design with the kind of space that reveals itself as you move through the home. Open wh...

  • 4 Beds
  • 3 Baths
  • 125980 MLS
14A W End Avenue, Old Greenwich image
14A W End Avenue, Old Greenwich $2,135,000

Discover the timeless appeal of Old Greenwich in this beautifully restored 1910 barn, tucked away off West End Ave in this incredibly convenient and private location. Soa...

  • 3 Beds
  • 2 Baths
  • 126135 MLS
16 Webb Avenue, Old Greenwich image
16 Webb Avenue, Old Greenwich $2,000,000

Unique opportunity to own a charming multi-unit property with a separate cottage. The main house features a welcoming wraparound porch and is currently configured as a tw...

  • 6 Beds
  • 5 Baths
  • 126073 MLS
16 Webb Avenue, Old Greenwich image
16 Webb Avenue, Old Greenwich $2,000,000

Unique opportunity to own a charming main residence paired with a separate cottage. The main house features a welcoming wraparound porch and a second-story deck; currentl...

  • 6 Beds
  • 5 Baths
  • 126072 MLS
61 Center Dr, Greenwich image
61 Center Dr, Greenwich $1,575,000 ▲

Welcome to 61 Center Drive, a move-in-ready Old Greenwich home at the end of a cul de sac. Thoughtfully updated across two levels, this 5-bedroom, 3-full bath home offers...

  • 5 Beds
  • 3 Baths
  • 24200241 MLS
61 Center Drive, Old Greenwich image
61 Center Drive, Old Greenwich $1,575,000 ▲

Welcome to 61 Center Drive, a move-in-ready Old Greenwich home at the end of a cul de sac. Thoughtfully updated across two levels, this 5-bedroom, 3-full bath home offers...

  • 5 Beds
  • 3 Baths
  • 125787 MLS
4 Hassake Road, Old Greenwich image
4 Hassake Road, Old Greenwich $1,495,000

Move right in and enjoy this charming 3-bedroom home, available for immediate occupancy and a quick closing. Whether you're looking to settle in before the school year b...

  • 3 Beds
  • 2 Baths
  • 125506 MLS
66 Mary Lane, Riverside image
66 Mary Lane, Riverside $1,225,000

Classic 1960 split-level home offering comfortable living spaces and a versatile floor plan. The sun-filled living room features a charming bay window, while the generous...

  • 4 Beds
  • 2 Baths
  • 126036 MLS
22 Northway, Old Greenwich image
22 Northway, Old Greenwich $30,000 ▼

Move into this furnished rental in Old Greenwich with spectacular 200 feet of waterfront views of Manhattan and Long Island sound. Amazing vistas from every room of this ...

  • 5 Beds
  • 5 Baths
  • 125617 MLS
24 Hendrie  Drive Extension, Old Greenwich image
24 Hendrie Drive Extension, Old Greenwich $25,000 ▼

Set on a private, gated 1.6-acre waterfront point, this classic Shore Colonial has been freshly painted and thoughtfully refreshed. Offering 5 bedrooms, 5 full and 1 half...

  • 5 Beds
  • 6 Baths
  • 125955 MLS
5 Grimes Road, Old Greenwich image
5 Grimes Road, Old Greenwich $22,500

Rare waterfront rental in private Shorelands Association, recently refreshed with refinished hardwood floors, new carpeting, interior paint, refreshed landscaping, and po...

  • 5 Beds
  • 4 Baths
  • 125468 MLS
32 Highview Avenue, Old Greenwich image
32 Highview Avenue, Old Greenwich $20,000

Old Greenwich - Renovated Victorian South of the VillageThis beautifully renovated and spacious Victorian home (approx. 5,500 SF) is ideally situated south of the village...

  • 6 Beds
  • 5 Baths
  • 125751 MLS
7 W Crossway, Old Greenwich image
7 W Crossway, Old Greenwich $19,500

Set along the shoreline, this furnished waterfront residence offers a rare way to live inside one of Greenwich's most coveted beach communities. Water views greet you fro...

  • 4 Beds
  • 3 Baths
  • 126115 MLS
15 Shorelands Place, Old Greenwich image
15 Shorelands Place, Old Greenwich $19,000

Old Greenwich living doesn't get better than this. 15 Shorelands Place puts you at the heart of a close-knit community within the Town of Greenwich. Minutes from Tod's Po...

  • 4 Beds
  • 4 Baths
  • 125117 MLS
39 Edgewater Drive, Old Greenwich image
39 Edgewater Drive, Old Greenwich $17,000

SHORT TERM RENTAL-12/1 start* This beautifully appointed, fully furnished Craftsman home is full of character and sits in one of Old Greenwich's most desirable locations,...

  • 4 Beds
  • 3 Baths
  • 125867 MLS
6 Meadowbank Road, Old Greenwich image
6 Meadowbank Road, Old Greenwich $15,200

Updated with a Modern flair this four-bedroom home is near the water, Tod's Point & located on a quiet cul-de-sac in Old Greenwich. Spacious & bright, there is an open de...

  • 4 Beds
  • 4 Baths
  • 125768 MLS
1 Cherry Lane, Old Greenwich image
1 Cherry Lane, Old Greenwich $15,000

Location, Location, Location! Wonderful long term OG rental, south of the village on Cherry Lane. 5 Bed Rooms, 3.5 renovated bath rooms. mudroom, home office, formal livi...

  • 5 Beds
  • 4 Baths
  • 125478 MLS
17 Center Road, Old Greenwich image
17 Center Road, Old Greenwich $13,500

Available immediately. Charming and sun-filled, this thoughtfully renovated Old Greenwich home is ideally located just moments from village shops, the train station, libr...

  • 4 Beds
  • 4 Baths
  • 125713 MLS
12 Norton Lane, Old Greenwich image
12 Norton Lane, Old Greenwich $13,500 ▼

THIS HANDSOME WHITEWASHED BRICK AND SHINGLE COLONIAL IS BEAUTIFULLY SITED ON A LEVEL, ONE ACRE PARK-LIKE CUL-DE-SAC SETTING. BOASTING A TRADITIONAL LAYOUT WITH FRONT TO B...

  • 4 Beds
  • 4 Baths
  • 125099 MLS
11 Maple Drive, Old Greenwich image
11 Maple Drive, Old Greenwich $13,000

Built in 2012 and ideally located in the heart of Old Greenwich, this beautifully designed home offers modern comfort across approximately 4,750 sq. ft. on three finished...

  • 5 Beds
  • 4 Baths
  • 125020 MLS
67 Benjamin Street, Old Greenwich image
67 Benjamin Street, Old Greenwich $11,500

Close to beach: Light, bright colonial on exceedingly convenient Benjamin Street, very near school, village, and train. House has large rooms, eat-in kitchen, and looks o...

  • 4 Beds
  • 3 Baths
  • 126006 MLS
3 Old Wagon Road, Old Greenwich image
3 Old Wagon Road, Old Greenwich $10,950

Spacious colonial zoned for North Mianus Elementary and Eastern Middle School. The versatile, open floor plan boasts high ceilings on the 1st and 2nd floors, with options...

  • 5 Beds
  • 7 Baths
  • 125673 MLS
58 Sound Beach Avenue, Old Greenwich image
58 Sound Beach Avenue, Old Greenwich $8,000 ▼

Central AC Just Installed and freshly painted exterior! NOTE: Additional 900 sq ft Carriage/Guest House with 1 bedroom, 1 full bath and living area, perfect for home offi...

  • 3 Beds
  • 3 Baths
  • 125729 MLS
31 Hassake Road, Old Greenwich image
31 Hassake Road, Old Greenwich $7,500 ▼

Spacious, immaculate and bright 4 bedroom home in an ideal location close to schools, train, the village of Old Greenwich with its shops and restaurants, the picturesque ...

  • 4 Beds
  • 2 Baths
  • 125382 MLS
17 Arnold Street, Old Greenwich image
17 Arnold Street, Old Greenwich $5,750 ▼

Welcome to 17 Arnold Street, a charming 4-bedroom, 2-bath home offering approximately 2,156 square feet of comfortable living in a desirable Old Greenwich neighborhood. B...

  • 4 Beds
  • 2 Baths
  • 125887 MLS
530 River Road Unit 1, Cos Cob image
530 River Road Unit 1, Cos Cob $5,250 ▼

HEAT, HOT WATER, LAWN, TRASH, all included. Property on almost 1/2 acre of park-like land. Large patio, great for entertaining. Heating: Oversized one-car attached garage...

  • 3 Beds
  • 2 Baths
  • 125843 MLS

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.

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