For sale

$29,900,000

Est. $183,409/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: 2 minutes ago

•Source:GMLS #125964

Payment calculator

$183,409 per month

Principal and interest$165,209

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 WED, 4PM TO 6PM
$979,000
3 beds2 baths1,980 sq ft
43 Bainbridge Ave, Thornwood, NY 10594
0.29 acre lot • 2 garage spots • Built 1963
Listing by Howard Hanna Rand Realty
OPEN WED, 5PM TO 7PM
180 Concord Ave, Hartsdale, NY 10530
$699,900
3 beds1 bath1,866 sq ft
180 Concord Ave, Hartsdale, NY 10530
9,857 sq ft lot • Built 1951
Listing by Xcel Realty Service LLC
OPEN SAT, 11AM TO 1PM
$1,250,000
6 beds4 baths2,542 sq ft
94 Washington Ave N, White Plains, NY 10603
7,065 sq ft lot • Garage • Built 1966
Listing by Real Broker NY LLC
OPEN SAT, 11AM TO 2PM
$2,895,000
4 beds4.5 baths6,222 sq ft
7 Park Ln, New Canaan, CT 06840
0.31 acre lot • 2 garage spots • Built 2003
OPEN SAT, 11AM TO 1PM
$2,399,000
4 beds2.5 baths2,750 sq ft
3 Huntzinger Dr, Greenwich, CT 06831
1.5 acre lot • 2 garage spots • Built 1967
OPEN SAT, 12PM TO 1:30PM
$1,495,000
6 beds4.5 baths4,000 sq ft
36 Crosshill Rd, Hartsdale, NY 10530
1.57 acre lot • 2 garage spots • Pool
Listing by Keller Williams NY Realty
OPEN SAT, 12PM TO 2PM
$205,000
1 bed1 bath800 sq ft
23 Old Mamaroneck Rd Unit 2C, White Plains, NY 10605
Built 1928
Listing by Keller Williams NY Realty
OPEN SUN, 11AM TO 1PM
$899,000
7 beds3 baths2,360 sq ft
128 Touraine Ave, Port Chester, NY 10573
4,970 sq ft lot • Garage • Built 1930
Listing by The Bridge Realty Group NY LLC
REDFIN OPEN SUN, 1PM TO 3PM3D & VIDEO TOUR
$849,000
4 beds2.5 baths2,298 sq ft
11 Island Heights Cir, Stamford, CT 06902
7,840 sq ft lot • 2 garage spots • Built 1962
OPEN SUN, 1PM TO 3PM
$799,000
5 beds3 baths3,103 sq ft
63 Prospect St, White Plains, NY 10606
0.24 acre lot • Garage • Built 1924
Listing by Julia B Fee Sothebys Int. Rlty

Around this home

Schools

K - 12
Preschool & daycare

Parkway School

Public K-5 • Assigned • 0.8mi

10/10

Western Middle School

Public 6-8 • Assigned • 6.8mi

8/10

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 $841,254. (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

$28,109,458

$1.8M under list price of $29.9M

Nearby comparable homes

The Redfin Estimate uses 6 recent nearby sales, priced between $4.7M to $7.2M.

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 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 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 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 FEB 27, 2026
$7,150,000 Last sold price
5 beds5.5 baths7,916 sq ft
35 Sterling Rd, Greenwich, CT 06831
$3424/sq ft
smaller lot
27 years older

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Early Access listings

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

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