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Looking for Greenwich CT Homes for Sale?

Scroll Down to View All Greenwich CT Real Estate From $2MM - $4MM

If you are interested in any piece of Greenwich CT Real Estate, Old Greenwich CT Real Estate, Cos Cob CT Real Estate, or Riverside CT Real Estate, click here to access Charlie's contact information.

If you are just browsing for now, be sure to visit our YouTube channel where we have a Greenwich CT Neighborhood Tour, town comparisons, quarterly market updates, and so much more! 

In our Greenwich Neighborhood Tour you will be able to get a glimpse of the Riverside CT Homes for Sale, Cos Cob CT Homes for Sale, and Old Greenwich CT Homes for Sale.

If you are trying to decide which town (or neighborhood) is right for you, you will find our YouTube channel invaluable. 

Greenwich CT Homes for Sale ($2MM - $4MM)

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
34 Thunder Mountain Road, Greenwich image
34 Thunder Mountain Road, Greenwich $3,990,000 ▼

Welcome to 34 Thunder Mountain Rd - Set on a quiet cul-de-sac with easy access to Glenville, Central Greenwich and Westchester. Substantially re-built in 2024/2025 this m...

  • 5 Beds
  • 6 Baths
  • 125270 MLS
35 Turner Drive, Greenwich image
35 Turner Drive, Greenwich $3,950,000

Set on a beautiful, private property, 35 Turner Drive offers a wonderful combination of open lawn, mature trees, natural rock formations, and established landscaping. The...

  • 4 Beds
  • 3 Baths
  • 125641 MLS
46 S Stonehedge  Drive South, Greenwich image
46 S Stonehedge Drive South, Greenwich $3,895,000

King Merritt Country Retreat on the Lake -New architecturally designed modern lakefront home offers effortless one-level living with a seamless open floor plan, soaring v...

  • 3 Beds
  • 4 Baths
  • 125576 MLS
4 Sachem Ln, Greenwich image
4 Sachem Ln, Greenwich $3,875,000 ▼

Beautifully reimagined modern farmhouse on a quiet Greenwich cul-de-sac, offering 4 bedrooms, 4 full & 1 half baths across four finished levels. Renovated with a timeless...

  • 4 Beds
  • 5 Baths
  • 24187684 MLS
4 Sachem Lane, Greenwich image
4 Sachem Lane, Greenwich $3,875,000 ▼

Beautifully reimagined modern farmhouse on a quiet Greenwich cul-de-sac, offering 4 bedrooms, 4 full & 1 half baths across four finished levels. Renovated with a timeless...

  • 4 Beds
  • 5 Baths
  • 125400 MLS
2 Taconic Road, Greenwich image
2 Taconic Road, Greenwich $3,850,000

Build your dream home on 2.4 picturesque acres ideally located south of the Merritt Parkway and just a short distance from town. Surrounded by exceptional homes this is a...

  • 3 Beds
  • 2 Baths
  • 125731 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
37 Arch St, Greenwich image
37 Arch St, Greenwich $3,600,000

Potential for residential conversion in the heart of downtown Greenwich. Located just two doors from Greenwich Avenue and moments from the Metro-North train station, 37 A...

  • 8 Beds
  • 3 Baths
  • 24174202 MLS
37 Arch Street, Greenwich image
37 Arch Street, Greenwich $3,600,000

37 Arch Street presents a rare opportunity to own a boutique commercial building in the heart of downtown Greenwich, just two doors from Greenwich Avenue and moments from...

  • 124949 MLS
37 Arch St, Greenwich image
37 Arch St, Greenwich $3,600,000

37 Arch Street presents a rare opportunity to own a boutique commercial building in the heart of downtown Greenwich, just two doors from Greenwich Avenue and moments from...

  • 3 Baths
  • 24174195 MLS
89 Indian Field Rd, Greenwich image
89 Indian Field Rd, Greenwich $3,495,000

Beautifully designed and thoughtfully finished, this exceptional New home blends sophisticated style with modern comfort and effortless everyday living. From the moment y...

  • 5 Beds
  • 5 Baths
  • 24201665 MLS
89 Indian Field Road, Greenwich image
89 Indian Field Road, Greenwich $3,495,000

Beautifully designed and thoughtfully finished, this exceptional New home blends sophisticated style with modern comfort and effortless everyday living. From the moment y...

  • 5 Beds
  • 5 Baths
  • 125793 MLS
14 Highview Avenue, Greenwich image
14 Highview Avenue, Greenwich $3,495,000

Rich with classic character, this 1918 Colonial sits on a coveted street in Old Greenwich. A quintessential wraparound porch opens to a spacious entry, living room with h...

  • 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
11 Butternut Hollow Rd, Greenwich image
11 Butternut Hollow Rd, Greenwich $3,495,000

Sun-filled Colonial set on 2 private acres with desirable east/west exposures, offering exceptional privacy and natural beauty. Thoughtfully updated throughout, the home ...

  • 5 Beds
  • 6 Baths
  • 24185738 MLS
11 Butternut Hollow Road, Greenwich image
11 Butternut Hollow Road, Greenwich $3,495,000 ▲

Private 2 acres in fabulous location! Discover this beautifully updated Colonial nestled on two private acres, offering exceptional privacy, picturesque grounds, and a p...

  • 5 Beds
  • 6 Baths
  • 125316 MLS
18 Shady Brook Ln, Greenwich image
18 Shady Brook Ln, Greenwich $3,450,000

Beautifully renovated by the current owners, this 5 bedroom, 5 bath home features refinished hardwood floors throughout, a modern open floor plan with eat-in kitchen/dini...

  • 5 Beds
  • 5 Baths
  • 24202309 MLS
18 Shady Brook Lane, Old Greenwich image
18 Shady Brook Lane, Old Greenwich $3,450,000

Beautifully renovated by the current owners, this 5 bedroom, 5 bath home features refinished hardwood floors throughout, a modern open floor plan with eat-in kitchen/dini...

  • 5 Beds
  • 5 Baths
  • 125791 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...

  • 24196451 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
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
  • 125606 MLS
34 Wescott Street, Riverside image
34 Wescott Street, Riverside $3,295,000

Welcome home to this lovely modern farmhouse in desirable Riverside, recently completed from the ground up with great attention to detail both inside and out. Board & Bat...

  • 4 Beds
  • 5 Baths
  • 125746 MLS
9 Old Forge Rd, Greenwich image
9 Old Forge Rd, Greenwich $3,250,000

Privately set on two magnificent acres at the end of a quiet Mid-Country cul-de-sac, this beautifully updated four-bedroom residence offers an exceptional blend of unders...

  • 4 Beds
  • 3 Baths
  • 24198837 MLS
9 Old Forge Road, Greenwich image
9 Old Forge Road, Greenwich $3,250,000

Privately set on two magnificent acres at the end of a quiet Mid-Country cul-de-sac, this beautifully updated four-bedroom residence offers an exceptional blend of unders...

  • 4 Beds
  • 3 Baths
  • 125797 MLS
13 Lia Fail Way, Greenwich image
13 Lia Fail Way, Greenwich $3,250,000

Set on over an acre at the end of a quiet cul-de-sac within the private Lia Fail Association in Greenwich, CT (Cos Cob), this exceptional stone and clapboard Colonial mas...

  • 4 Beds
  • 7 Baths
  • 24194524 MLS
13 Lia Fail Way, Cos Cob image
13 Lia Fail Way, Cos Cob $3,250,000

Set on over an acre at the end of a quiet cul-de-sac within the private Lia Fail Association in Greenwich, CT (Cos Cob), this exceptional stone and clapboard Colonial mas...

  • 4 Beds
  • 7 Baths
  • 125574 MLS
Doverton Drive, Lot 2, Greenwich image
Doverton Drive, Lot 2, Greenwich $3,250,000 ▼

Within the private Sabine Farm Association, this 5.13-acre parcel offers a rare opportunity to create an exceptional estate in one of Greenwich's most desirable mid-count...

  • 125474 MLS
5 Willow Run Rd, Greenwich image
5 Willow Run Rd, Greenwich $3,250,000 ▼

Impeccably maintained, stunning classic colonial, tucked away on a private road in one of Greenwich's most sought-after enclaves. A combination of traditional New England...

  • 4 Beds
  • 5 Baths
  • 24177801 MLS
5 Willow Run Road, Greenwich image
5 Willow Run Road, Greenwich $3,250,000 ▼

Impeccably maintained, stunning classic colonial, tucked away on a private road in one of Greenwich's most sought-after enclaves. Traditional New England architecture wit...

  • 4 Beds
  • 5 Baths
  • 125330 MLS
20 Sound Beach Avenue, Old Greenwich image
20 Sound Beach Avenue, Old Greenwich $2,999,999

Remarks: Brand New Luxury Home in Old Greenwich Experience luxury living in this stunning New Construction, minutes away from Old Greenwich train station, Tod's Point and...

  • 6 Beds
  • 6 Baths
  • 125824 MLS
37 Mary Ln, Greenwich image
37 Mary Ln, Greenwich $2,999,000

Completely reimagined and expanded to nearly twice its original footprint, this exceptional Riverside residence is the result of a meticulous gut renovation by Abode Inte...

  • 5 Beds
  • 4 Baths
  • 24201047 MLS
37 Mary Lane, Riverside image
37 Mary Lane, Riverside $2,999,000

Completely reimagined and expanded to nearly twice its original footprint, this exceptional Riverside residence is the result of a meticulous gut renovation by Abode Inte...

  • 5 Beds
  • 4 Baths
  • 125774 MLS
2 Choctaw Lane, Greenwich image
2 Choctaw Lane, Greenwich $2,995,000 ▼

Wonderfully updated family Colonial in private King Merritt, set on 1.39 acres in Greenwich. Offering nearly 5,300 square feet of living space, this 4-bedroom, 4-full-bat...

  • 4 Beds
  • 4 Baths
  • 125615 MLS
6 Meadowbank Rd, Greenwich image
6 Meadowbank Rd, Greenwich $2,995,000

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 $2,995,000

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
25 Woodland Drive Unit B, Greenwich image
25 Woodland Drive Unit B, Greenwich $2,900,000

AVENUE TERRACE -- Sophisticated downtown Greenwich living in a private six-home enclave just minutes from Greenwich Avenue and Metro-North. 25B Woodland Drive blends mode...

  • 3 Beds
  • 4 Baths
  • 125789 MLS
67 Bedford Rd, Greenwich image
67 Bedford Rd, Greenwich $2,895,000

Build your dream estate on 4+ private, level acres in the heart of backcountry Greenwich, surrounded by multi-million-dollar homes and just minutes from top transportatio...

  • 24182945 MLS
47 Ridge St, Greenwich image
47 Ridge St, Greenwich $2,895,000 ▲

Tucked at the end of a private road in Cos Cob, this newly built (2025) Louis Contadino-designed home offers a layout rarely available in central Greenwich at this price ...

  • 4 Beds
  • 5 Baths
  • 24168793 MLS
47 Ridge Street, Cos Cob image
47 Ridge Street, Cos Cob $2,895,000 ▲

Tucked at the end of a private road in Cos Cob, this newly built (2025) Louis Contadino-designed home offers a layout rarely available in central Greenwich at this price ...

  • 4 Beds
  • 5 Baths
  • 124781 MLS
154 Valley Road, Cos Cob image
154 Valley Road, Cos Cob $2,850,000

Gently tucked away off Valley Road at the base of one of the many hills along the Mianus River, you will find this distinguished classic center hall colonial, glowing wit...

  • 3 Beds
  • 4 Baths
  • 125745 MLS
71 Orchard Place Unit 2, Greenwich image
71 Orchard Place Unit 2, Greenwich $2,850,000

Bruce Park -- Close to town, restaurants, museum, park, Island Beach/Captain's Island ferries, and the train from this beautiful 3-bedroom single-style townhouse. Located...

  • 3 Beds
  • 3 Baths
  • 124898 MLS
340 Valley Rd Unit 2, Greenwich image
340 Valley Rd Unit 2, Greenwich — Valley Ridge $2,795,000

Rare opportunity to own this turnkey home in the coveted gated community of Valley Ridge. Beautifully updated and meticulously maintained, it offers over 4,000 square fee...

  • 4 Beds
  • 4 Baths
  • 24205426 MLS
  • Valley Ridge Bldg.
340 Valley Road Unit UNIT 2, Cos Cob image
340 Valley Road Unit UNIT 2, Cos Cob $2,795,000

Rare opportunity to own this turnkey home in the coveted gated community of Valley Ridge. Beautifully updated and meticulously maintained, it offers over 4,000 square fee...

  • 4 Beds
  • 4 Baths
  • 125819 MLS
93 Summit Road, Riverside image
93 Summit Road, Riverside $2,795,000

Classic four bedroom Colonial in a convenient Riverside location has been thoughtfully renovated and expanded over the years. Entertain in the spacious living room with f...

  • 4 Beds
  • 5 Baths
  • 124721 MLS
316 Valley Rd, Greenwich image
316 Valley Rd, Greenwich $2,750,000

Some homes are built. This one was sculpted. Elevated above the Mianus River with year-round water views, this four-bedroom Greenwich home feels like a private European ...

  • 4 Beds
  • 5 Baths
  • 24197532 MLS
316 Valley Road, Cos Cob image
316 Valley Road, Cos Cob $2,750,000

Some homes are built. This one was sculpted. Elevated above the Mianus River with year-round water views, this four-bedroom Greenwich home feels like a private Europe...

  • 4 Beds
  • 5 Baths
  • 125638 MLS
9 Maple St, Greenwich image
9 Maple St, Greenwich $2,695,000

Brand new construction in Cos Cob features four finished levels and an abundance of natural light. The main level offers an inviting open-concept kitchen, breakfast area,...

  • 4 Beds
  • 4 Baths
  • 24204244 MLS
9 Maple Street, Cos Cob image
9 Maple Street, Cos Cob $2,695,000

Brand new construction in Cos Cob features four finished levels and an abundance of natural light. The main level offers an inviting open-concept kitchen, breakfast area,...

  • 4 Beds
  • 5 Baths
  • 125766 MLS
73 Thunder Mountain Road, Greenwich image
73 Thunder Mountain Road, Greenwich $2,650,000

Charming center hall colonial at the end of a quiet mid country cul-de-sac. The location is convenient yet offers wonderful seclusion. Set on a park-like, level 2.3 acres...

  • 4 Beds
  • 4 Baths
  • 125114 MLS
165 Shore Rd Unit D, Greenwich image
165 Shore Rd Unit D, Greenwich — Harbor House Association $2,500,000

Moments from the beach in one of Old Greenwich's most distinctive concierge residences. Sun-filled and sophisticated, this beautifully appointed three-bedroom blends time...

  • 3 Beds
  • 4 Baths
  • 24198810 MLS
  • Harbor House Association Bldg.
165 Shore Road Unit D, Old Greenwich image
165 Shore Road Unit D, Old Greenwich $2,500,000

Moments from the beach in one of Old Greenwich's most distinctive concierge residences. Sun-filled and sophisticated, this beautifully appointed three-bedroom blends time...

  • 3 Beds
  • 4 Baths
  • 125734 MLS
51 Glen Road, Greenwich image
51 Glen Road, Greenwich $2,499,999 ▼

Close to town from this rare in-town Greenwich gem -- a corner lot home on a quiet cul-de-sac, just steps from Greenwich Avenue's shops, restaurants, and cafés, the Green...

  • 5 Beds
  • 4 Baths
  • 124257 MLS
7 Sundance Dr, Greenwich image
7 Sundance Dr, Greenwich $2,499,000

A rare opportunity to own an authentic Mid-Century Modern home set on 2 picturesque, private acres in a quiet sought-after neighborhood of Cos Cob. This contemporary resi...

  • 4 Beds
  • 4 Baths
  • 24205550 MLS
7 Sundance Drive, Cos Cob image
7 Sundance Drive, Cos Cob $2,499,000

A rare opportunity to own an authentic Mid-Century Modern home set on 2 picturesque, private acres in a quiet sought-after neighborhood of Cos Cob. This contemporary resi...

  • 4 Beds
  • 4 Baths
  • 125790 MLS
65 Sherwood Pl Unit 65, Greenwich image
65 Sherwood Pl Unit 65, Greenwich $2,490,000

Exquisite individual custom built 2014 condominium unit it a two unit complex. Prime In Town location, walk to Greenwich Avenue. Unit has four levels with four bedrooms a...

  • 5 Beds
  • 6 Baths
  • 24188704 MLS
65 Sherwood Place, Greenwich image
65 Sherwood Place, Greenwich $2,490,000

None

  • 5 Beds
  • 6 Baths
  • 125417 MLS
20 Rustic View Road, Greenwich image
20 Rustic View Road, Greenwich $2,395,000

Set on over an acre in Mid-Country Greenwich, this classic four-bedroom Colonial offers generous living space and a versatile, well-designed floor plan. The main level fe...

  • 4 Beds
  • 3 Baths
  • 125827 MLS
128 Weaver Street, Greenwich image
128 Weaver Street, Greenwich $2,395,000

A Connecticut Classic: Julia & Elijah Lyon Jr. House (circa 1848). Pairing pedigree with possibilities, this quintessential New England home marries historic charm with c...

  • 4 Beds
  • 4 Baths
  • 125404 MLS
12 Sawmill Terrace, Greenwich image
12 Sawmill Terrace, Greenwich $2,149,000 ▼

Serene & Private Escape. With a trending modern sensibility, this light-filled residence showcases oversized windows and doors, and soaring ceilings throughout the home. ...

  • 3 Beds
  • 3 Baths
  • 124059 MLS
241 Pemberwick Road, Greenwich image
241 Pemberwick Road, Greenwich $2,100,000 ▼

Completely reimagined and move-in ready, this spacious 6-bedroom, 4 full and 1 half bath home offers nearly 3,000 square feet of versatile living on a peaceful, private 0...

  • 6 Beds
  • 5 Baths
  • 125665 MLS
241 Pemberwick Rd, Greenwich image
241 Pemberwick Rd, Greenwich $2,100,000 ▼

Completely reimagined and move-in ready, this spacious 6-bedroom, 4 full and 1 half bath home offers nearly 3,000 square feet of versatile living on a peaceful, private 0...

  • 6 Beds
  • 5 Baths
  • 24197775 MLS
1 Midbrook Lane, Old Greenwich image
1 Midbrook Lane, Old Greenwich $2,095,000

Great value and opportunity in this spacious five-bedroom Old Greenwich home! Set South of the Post Road with a flat fenced-in backyard in a wonderful neighborhood. Expa...

  • 5 Beds
  • 3 Baths
  • 125739 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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