Realty.com
Buy

Start here

  • Homes for sale by state
  • Home buying tips
  • Before you start looking
  • The buying timeline

Afford it

  • Today's mortgage rates
  • Mortgage calculator
  • How much can I afford?
  • Get pre-approved

Make the deal

  • Writing a winning offer
  • Inspections & appraisals
  • Closing costs, itemized
  • Find a buyer's agent
Sell

Selling Options

  • What's my home worth?
  • Compare selling options
  • Get an instant cash offer
  • Buy before you sell

Resources

  • How selling works
  • When should I sell?
  • Home selling tips
  • Pricing your home
  • What's worth fixing first
  • Find a seller's agent
Home Loans
Find an Agent
Save searchAdvertiseSign In
Saved homesSaved searchesYour toursYour inquiriesRecently viewedAccount settings

Save search

Map layers

Safety

Safety & registry resources

Review official public-safety information for any area from these government sources:

  • U.S. Dept. of Justice National Sex Offender Public Website (NSOPW)
  • FBI: state sex-offender registry directory
Luxury Homes in Greenwich, CT
Realty.com
Buy

Start here

  • Homes for sale by state
  • Home buying tips
  • Before you start looking
  • The buying timeline

Afford it

  • Today's mortgage rates
  • Mortgage calculator
  • How much can I afford?
  • Get pre-approved

Make the deal

  • Writing a winning offer
  • Inspections & appraisals
  • Closing costs, itemized
  • Find a buyer's agent
Save searchAdvertiseSign In
Saved homesSaved searchesYour toursYour inquiriesRecently viewedAccount settings
  • Rentals
  • Commercial

18 listings
Sell

Selling Options

  • What's my home worth?
  • Compare selling options
  • Get an instant cash offer
  • Buy before you sell

Resources

  • How selling works
  • When should I sell?
  • Home selling tips
  • Pricing your home
  • What's worth fixing first
  • Find a seller's agent
Home Loans
Find an Agent
Save search

Luxury Homes in Greenwich, CT

Luxury Homes in Greenwich, CT

Hide Map
18 Listings
Map

Luxury Homes in Greenwich, CT

18 Listings

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #REB.0790925

Call Thomas
  1. 633 Steamboat Road Apt 4 — photo20Active

    $4,550,000

    2 bd · 3 ba · 2,157 sqft

    633 Steamboat Road Apt 4, Greenwich, CT

    Sally Maloney · Houlihan Lawrence

  2. 59 Le Grande Avenue 11 — photoNew25Active

    $1,850,000

    3 bd · 4 ba · 2,482 sqft

    59 Le Grande Avenue 11, Greenwich, CT

    Leslie McElwreath · Sotheby's International Realty

  3. 25 Indian Harbor Drive 3 — photo20Active

    $1,095,000

    3 bd · 3 ba · — sqft

    25 Indian Harbor Drive 3, Greenwich, CT

    Samantha Behringer · Douglas Elliman of Connecticut

  4. 206 Milbank Avenue 1 — photo20Active

    $5,995,000

    6 bd · 7 ba · 4,000 sqft

    206 Milbank Avenue 1, Greenwich, CT

    Nina Frandson · BHHS New England Properties

  5. 206 Milbank Avenue 2 — photo20Active

    $5,995,000

    6 bd · 7 ba · 4,000 sqft

    206 Milbank Avenue 2, Greenwich, CT

    Nina Frandson · BHHS New England Properties

  6. 340 Valley Road 2 — photo20Active

    $2,795,000

    4 bd · 4 ba · 4,088 sqft

    340 Valley Road 2, Greenwich, CT

    Jennifer Leahy · Compass Connecticut, LLC

  7. 20 Church Street B66 — photo20Active

    $1,499,000

    1 bd · 1 ba · 1,038 sqft

    20 Church Street B66, Greenwich, CT

    Elsa Case · Houlihan Lawrence

  8. 25 Woodland Drive B — photo26Active

    $2,900,000

    3 bd · 4 ba · 2,526 sqft

    25 Woodland Drive B, Greenwich, CT

    Michele Tesei · Houlihan Lawrence

  9. listing photo20Active

    $1,499,000

    1 bd · 1 ba · — sqft

    Address withheld · Greenwich, CT

    Elsa Case · Houlihan Lawrence

  10. 8 Greenwich Hills Drive 8 — photo24Active

    $1,150,000

    2 bd · 3 ba · 1,750 sqft

    8 Greenwich Hills Drive 8, Greenwich, CT

    Leslie McElwreath · Sotheby's International Realty

  11. 165 Shore Road D — photo19Active

    $2,600,000

    3 bd · 4 ba · 1,784 sqft

    165 Shore Road D, Greenwich, CT

    Joy Kim Metalios · Houlihan Lawrence

  12. 275 Mason Street 3D — photo11Active

    $5,695,000

    2 bd · 3 ba · 2,121 sqft

    275 Mason Street 3D, Greenwich, CT

    Angela Ferrara · The Marketing Directors CT LLC

  13. 290 Mason Street 2D — photo11Active

    $4,250,000

    2 bd · 3 ba · 2,053 sqft

    290 Mason Street 2D, Greenwich, CT

    Angela Ferrara · The Marketing Directors CT LLC

  14. 25 West Elm Street 37 — photoPrice Reduced24Active

    $1,350,000

    2 bd · 2 ba · 1,373 sqft

    25 West Elm Street 37, Greenwich, CT

    Julie Hancock · Houlihan Lawrence

  15. 282 Bruce Park Avenue 2 — photo13Active

    $1,958,000

    4 bd · 5 ba · 3,263 sqft

    282 Bruce Park Avenue 2, Greenwich, CT

    Glenn Marr · Marr and Caruso Realty Group

  16. 8 View Street 7 — photo28Active

    $1,495,000

    3 bd · 3 ba · 2,172 sqft

    8 View Street 7, Greenwich, CT

    Jill Barile · BHHS New England Properties

  17. listing photoPrice Reduced21Active

    $2,600,000

    3 bd · 3 ba · — sqft

    Address withheld · Greenwich, CT

    Ted Hildner · Coldwell Banker Realty

  18. 71 Orchard Place 2 — photoPrice Reduced25Active

    $2,600,000

    3 bd · 3 ba · 2,182 sqft

    71 Orchard Place 2, Greenwich, CT

    Theodore Hildner · Coldwell Banker Realty

Realty.com

L. Custen Realty, Inc. d/b/a Realty.com/L. Custen Realty CT, LLC d/b/a Realty.com (Tom O’Leary-Broker)(CT properties only), 8323 Southwest Freeway, Suite 900, Houston, Texas 77074

Equal Housing OpportunityEqual Housing Lender

The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Listing data is derived from various Multiple Listing Services; each source MLS and its required disclaimer are shown with the listings on the applicable page. Realty.com is an independently owned and operated brokerage.

© 2026 Realty.com. All rights reserved.·Privacy·Terms·California Privacy Rights·Accessibility·Licensing

Listing data & MLS disclosures

Greenwich MLS (GMLS)
Listing data courtesy of Greenwich MLS. IDX information is provided exclusively for consumers’ personal, non-commercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data is deemed reliable but is not guaranteed accurate by the MLS.
Listing information ©2026 Greenwich MLS, Inc®. All Rights Reserved. Last Updated: 2026-10-07 06:30:24 UTC
SmartMLS
IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. The listing broker’s offer of compensation is made only to participants of the MLS where the listing is filed.
  • Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #REB.0790925

    Call Thomas

    Greenwich, CT community profile

    Area
    46.2 sq. mi.

    Source: HJN community data

    Greenwich housing market

    September 2026 · This period is still settling

    Greenwich 12-month median sale price trend

    Selling at 100.0% of asking price

    Sales here are closing essentially at asking. MLS · 30 sales · as of Sep 30, 2026

    Homes that sold · County records, as of Sep 18, 2026

    Median sale price
    $2,500,000$1,600,000–$3,753,752 typical range
    Price per sq. ft.
    $790
    Sales
    21
    Paid in cash
    42.9%

    Homes on the market · MLS, as of Sep 27, 2026–Sep 30, 2026

    Median list price
    $4,972,500
    Homes for sale
    104
    Median days on market
    29 days

    Price trend · Assessor repeat sales, as of Sep 30, 2026

    Year-over-year
    -5.0%

    Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 2, 2026

    Median home size
    3,279 sq. ft.