For sale

$29,900,000

Est. $181,376/mo —

•

6,910

sq ft

500 Round Hill Rd, Greenwich, CT 06831

About this home

An extraordinary opportunity to create a new landmark estate on Round Hill Rd's premier building site: a nearly 20-acre offering at a 560 ft elevation - one of the highest points on Round Hill with a spectacular 7,000+ sq. ft. guest house for immediate liveability during the construction phase. Potential to build notable 22,000+ sq. ft. main house with optimal south-facing orientation and Long Island Sound views from second floor on 8-acre lot and additional 12,000+ sq. ft. on 4.2 acre lot for a total of 35,000+/- sq. ft. The existing stone guest house built in 2015 was designed by acclaimed architect Christopher Pagliaro with interior design by Arthur Dunnam of Dunnam Zerbini Design and offers south-facing pool with spa, separate studio apartment for visitors, and attached 3-car garage. Additional buffer lot of 2.3 conservation acres. DISCLAIMER: Photos labeled CONCEPTUAL RENDERING are for illustrative purposes only. Home design shown is not an approved or proposed architectural plan and is intended solely to illustrate the potential use of the property. Buyer to verify all zoning, building, and site requirements.

Single-familyProperty Type

2015Year Built

19.69 acresLot Size

$4,327Price/Sq.Ft.

3 car garageParking

Listed by Joseph Barbieri • Sotheby's International Realty

Listing updated: Oct 7, 2026 at 12:54pm

Redfin checked: a few seconds ago

•Source:GMLS #125964

Payment calculator

$181,376 per month

Principal and interest$163,177

Property taxes

$8,731

HOA dues

Home insurance

$9,468

Utilities

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Open houses

No upcoming open houses.

Nearby open houses (10)

OPEN TODAY, 4PM TO 6PM
$699,900
3 beds1 bath1,866 sq ft
180 Concord Ave, Hartsdale, NY 10530
9,857 sq ft lot • Built 1951 • Listed 6 days
Listing by Xcel Realty Service LLC
OPEN NOV 2, 12PM TO 4PM
$1,599,000
5 beds3 baths3,184 sq ft
114 Pequot Ln, New Canaan, CT 06840
4.01 acre lot • 2 garage spots • Built 1971
OPEN NOV 3, 12PM TO 2PM
$8,740,000
7 beds9.5 baths14,216 sq ft
259 Frogtown Rd, New Canaan, CT 06840
2.25 acre lot • 3 garage spots • Pool
OPEN NOV 7, 1PM TO 3PM
$380,000
2 beds1 bath960 sq ft
151 Courtland Ave Unit 4D, Stamford, CT 06902
$762 HOA • 2 parking spots • Built 1970
OPEN NOV 7, 1PM TO 3PM
$1,159,000
5 beds3.5 baths3,627 sq ft
1148 Rock Rimmon Rd, Stamford, CT 06903
3.26 acre lot • 3 garage spots • Built 1955
OPEN NOV 7, 1PM TO 5PM
$899,000
3 beds1.5 baths1,600 sq ft
15 Beacon Hill Rd, Ardsley, NY 10502
6,098 sq ft lot • Garage • Built 1931
Listing by Coldwell Banker Signature Prop
OPEN NOV 8, 11:30AM TO 1:30PM
$1,375,000
4 beds3 baths2,400 sq ft
27 Meadowlark Rd, Rye Brook, NY 10573
0.48 acre lot • 2 garage spots • Built 1960
Listing by King Merritt Realty
OPEN NOV 8, 12PM TO 4PM
$2,399,000
4 beds4.5 baths5,523 sq ft
38 Lincoln Ave, Rye Brook, NY 10573
0.62 acre lot • 3 parking spots • Built 2006
Listing by Howard Hanna Rand Realty
OPEN NOV 8, 12PM TO 2PM
$2,350,000
3 beds2.5 baths4,250 sq ft
259 Westchester Ave, Pound Ridge, NY 10576
0.27 acre lot • Built 1860 • Listed 96 days
Listing by Compass Greater NY, LLC
OPEN NOV 8, 2PM TO 4PM
$1,575,000
5 beds3 baths2,700 sq ft
32 Dogwood Dr, Scarsdale, NY 10583
9,116 sq ft lot • Garage • Built 1954
Listing by King Merritt Realty

Around this home

Schools

K - 12
Preschool & daycare

Parkway School

Public K-5 • Assigned • 0.8mi

9/10

Western Middle School

Public 6-8 • Assigned • 6.8mi

9/10

Greenwich High School

Public 9-12 • Assigned • 5.5mi

10/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Market insights

500 Round Hill Rd · $29,900,000

DAYS ON MARKET

The average home goes pending in 43 days.

SALE-TO-LIST

Most homes are selling 2% above list price.

LIST PRICE

Median list price in this area is $849,500. (97% lower than this home)

PRICE DROP

17% of homes in this area have had a price drop in the past month.

Property details

Interior
Exterior
Finance

Kitchen

Bathroom

Bedroom

Living

Dining

Interior features
Kitchen island
Partially finished basement
Three fireplaces

Bathrooms
6 full bathrooms
1 half bathroom (7 total)

Heating & cooling
Central air conditioning
Hydro-air heating
Propane heating

Sale and tax history for 500 Round Hill Rd

Sale History
Tax History

Date

Event

Price

GMLS #125964

Oct 1, 2026

Listed

$29,900,000

$4,327/sq ft

GMLS #82213

May 7, 2012

Listed

$22,500,000

$3,256/sq ft

GMLS #77677

Oct 6, 2010

Listed

$29,000,000

$4,197/sq ft

GMLS #59032

Jan 26, 2006

Sold

$8,600,000

$1,245/sq ft

Feb 28, 2005

Listed

$8,850,000

$1,281/sq ft

GMLS #59433

Apr 8, 2005

Listed

$8,150,000

$1,179/sq ft

GMLS #59033

Feb 28, 2005

Listed

$8,850,000

$1,281/sq ft

GMLS #55800

Jan 14, 2005

Sold

$11,000,000

$1,592/sq ft

Mar 16, 2004

Listed

$16,900,000

$2,446/sq ft

GMLS #57213

Oct 13, 2004

Sold

—

Jul 19, 2004

Listed

$16,900,000

$2,446/sq ft

Smart MLS #98194735

Jun 19, 2004

Listing Removed

—

Apr 20, 2004

Listed

$16,900,000

$2,446/sq ft

GMLS #51262

Oct 5, 2003

Sold

—

Sep 6, 2002

Listed

$18,000,000

$2,605/sq ft

GMLS #46575

Aug 12, 2003

Sold

—

Jan 8, 2001

Listed

$13,950,000

$2,019/sq ft

GMLS #46583

Jul 11, 2002

Sold

$13,500,000

$1,954/sq ft

Jan 8, 2001

Listed

$17,000,000

$2,460/sq ft

GMLS #44193

Jan 12, 2001

Sold

—

Jan 12, 2000

Listed

$20,000,000

$2,894/sq ft

Year

Property tax

Land + Additions

Assessment*

2023

$53,553 (+1.0%)

$1,576,120 + $3,125,640

$4,701,760

2022

$53,036 (−2.1%)

$1,576,120 + $3,125,640

$4,701,760

2021

$54,167

$1,370,530 + $3,303,090

$4,673,620

2020

$54,167 (−0.8%)

$1,370,530 + $3,303,090

$4,673,620

2019

$54,588 (+2.7%)

$1,370,530 + $3,303,090

$4,673,620

2018

$53,139

$1,370,530 + $3,303,090

$4,673,620

2017

$53,139 (+50.2%)

$1,370,530 + $3,303,090

$4,673,620

2016

$35,368 (+101.5%)

$1,370,530 + $1,787,310

$3,157,840

2014

$17,550

$1,561,910 + $37,940

$1,599,850

Public record

Beds

—

Baths

—

Stories

—

Lot width

—

Lot depth

—

Lot size

5.04 Acres

Year renovated

—

Finished Sq. Ft.

—

Unfinished Sq. Ft.

—

Total Sq. Ft.

—

Year built

—

Style

Other

County

Fairfield County

APN

2405486

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Dec 11, 2023.

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

3/10 Fire Factor

0.31% chance of being in a wildfire in next 30 years

5/10 Heat Factor

7 days above 98° expected this year, 15 days in 30 years

6/10 Wind Factor

27% chance of strong winds in next 30 years

4/10 Air Factor

5 unhealthy days expected this year, 7 days in 30 years

Provided by First Street

Historical weather

Greenwich, CT • 06831

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

Try the sun simulator tool to see how light moves across the property at different times of day and year.

Provided by Shadowmap

Redfin Estimate for 500 Round Hill Rd

$27,773,878

$2.1M under list price of $29.9M

Nearby comparable homes

The Redfin Estimate uses 6 recent nearby sales, priced between $4.7M to $8.4M.

SOLD AUG 6, 2026
$6,900,000 Last sold price
6 beds6.5 baths6,216 sq ft
530 Round Hill Rd, Greenwich, CT 06831
$3217/sq ft
smaller lot
78 years older
SOLD MAY 20, 2026
$4,685,000 Last sold price
7 beds6 baths5,842 sq ft
379 Round Hill Rd, Greenwich, CT 06831
$3525/sq ft
smaller lot
175 years older
SOLD SEP 1, 2026
$4,950,000 Last sold price
5 beds3.5 baths4,564 sq ft
456 Round Hill Rd, Greenwich, CT 06831
$3242/sq ft
smaller lot
165 years older
SOLD MAR 30, 2026
$5,700,000 Last sold price
5 beds5.5 baths8,208 sq ft
20 Cutler Rd, Greenwich, CT 06831
$3633/sq ft
smaller lot
46 years older
SOLD JUL 8, 2026
$5,600,000 Last sold price
Land6,669 sq ft
960 Lake Ave, Greenwich, CT 06831
$3487/sq ft
smaller lot
37 years older
SOLD MAY 1, 2026
$8,372,500 Last sold price
6 beds7.5 baths9,113 sq ft
13 Wyckham Hill Ln, Greenwich, CT 06831
$3408/sq ft
smaller lot
18 years older

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Early Access listings

EARLY ACCESSCOLDWELL BANKER REALTY COMING SOON

$379,900

2 beds2 baths1,864 sq ft

155 Dockerel Rd, Vernon, CT 06066

Nearby similar homes

$7,500,000

5 beds6 baths8,766 sq ft

603 Round Hill Rd, Greenwich, CT 06831

Private lane • Secluded acres • Glass walls

NEW CONSTRUCTION

$14,495,000

7 beds10 baths14,000 sq ft

532 Round Hill Rd, Greenwich, CT 06831

Private library • Expansive kitchen • 4.01 acre lot

$1,449,000

3 beds2 baths1,713 sq ft

105 Glenville St, Greenwich, CT 06831

Renovated • Level lot • Split-level

$4,100,000

5 beds4.5 baths5,044 sq ft

54 Old Mill Rd, Greenwich, CT 06831

Major renovation • Stone walls • Private acres

NEW CONSTRUCTION

$11,995,000

7 beds9.5 baths15,896 sq ft

86 Howard Rd, Greenwich, CT 06831

5.35 acres • Open-plan kitchen • Heated pool

$3,850,000

Land1,746 sq ft

2 Taconic Rd, Greenwich, CT 06830

Built 1949 • Listed 66 days

New listings for sale in 06831

$3,195,000

4 beds4.5 baths4,422 sq ft

90 W Lyon Farm Dr #90, Greenwich, CT 06831

Secluded stone patio • Manicured lot • Sundrenched interior

$7,500,000

5 beds6 baths8,766 sq ft

603 Round Hill Rd, Greenwich, CT 06831

Private lane • Secluded acres • Glass walls

$3,750,000

6 beds6.5 baths5,131 sq ft

25 Will Merry Ln, Greenwich, CT 06831

Stone terrace • Fenced backyard • Year-round sunporch

$2,399,000

4 beds2.5 baths2,750 sq ft

3 Huntzinger Dr, Greenwich, CT 06831

Pond views • Minutes from town • 1.5 acre lot

$4,500,000

5 beds4.5 baths6,406 sq ft

18 Dwight Ln, Greenwich, CT 06831

Modernist residence • Original brick home • Elegant kitchen

$999,999

4 beds3 baths1,536 sq ft

32 Hollow Wood Ln, Greenwich, CT 06831

Main level laundry • Spacious deck • 4,791 sq ft lot

$1,195,000

4 beds3 baths3,096 sq ft

246 Pemberwick Rd, Greenwich, CT 06831

7,840 sq ft lot • Garage • Built 1980

Details provided by GMLS and may not match the public record. Learn more.

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