Off market dec 2024 for $15M

$14,403,267

Est. refi paymentEst. refi $4,081/mo

•

8,472

sq ft

385 Harbor Rd, Southport, CT 06890

About this home

For 170 years, "Rose Hill" has graced the crest of Harbor Road, offering breathtaking views considered among the best on the East Coast. This magnificent Italianate landmark boasts 265 feet of direct waterfront access, complete with a private dock. Situated on nearly 2 acres, it stands as one of the largest and most commanding properties in Southport Village, offering unparalleled vistas of the Harbor, the Country Club of Fairfield golf course, and Long Island Sound. The meticulously restored Main House exudes charm and sophistication, featuring large public rooms with high ceilings that provide elegant spaces for entertaining. The spacious bedrooms and bathrooms offer stunning views, ensuring comfort and luxury. Additionally, a delightful guest apartment and wine cellar are located above the detached garage. Experience the epitome of refined living by dining al fresco, lounging by the pool, playing a game of bocce, tending to the garden, or relaxing on one of the many inviting porches. At "Rose Hill," every moment feels like a step back in time to an era when life was lived to its fullest.

Sale also includes 331 Harbor Road (.55 acres). Seperate one bedroom guest house over the garage with kitchen and full bath (1,214 sq. feet) is not included in Main House square footage.

Single-familyProperty Type

1854Year Built

1.86 acresLot Size

$1,700Est. Price/Sq.Ft.

3 car garageParking

Listed by Andrew Whiteley • William Raveis Real Estate

Bought with Jordan Dolger • Higgins Group Real Estate

Source:Smart MLS #24032329

Redfin Estimate

$14,403,267

$597K since sold in December 2024$115K since September

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 306.2% higher than the average sale price ($3.55M) of 6 comparable homes.

SOLD AUG 13, 2026
$4,000,000
A
7 beds8 baths7,105 sq ft
20 Fresenius Rd, Westport, CT 06880
SOLD AUG 26, 2026
$4,500,000
B
6 beds5 baths5,607 sq ft
6 Clapboard Hill Rd, Westport, CT 06880
SOLD SEP 4, 2026
$3,450,000
C
5 beds6.5 baths9,819 sq ft
1 Flower Farm Ln, Westport, CT 06880
SOLD APR 16, 2026
$3,480,000
D
7 beds7.5 baths10,104 sq ft
249 Greens Farms Rd, Westport, CT 06880
SOLD AUG 5, 2026
$2,995,000
E
5 beds5.5 baths5,789 sq ft
221 Greens Farms Rd, Westport, CT 06880
SOLD AUG 3, 2026
$2,850,000
F
6 beds7 baths6,214 sq ft
750 Burr St, Fairfield, CT 06824

Claim this home to receive a free report every month with insights on the changing estimate.

Earn from this home

Sell

$1,957,435

Est. take-home

List your home with Redfin and save $144,033

Refinance

Est. cash available

Get cash now or lower your monthly rate

Market trends in 06890, CT

Last updated September 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

105.5%

+0.0% MoM

Median sale price

$1.7M

$26K MoM

Avg. days on market

33d

3 days MoM

Recently sold homes

2 MoM

New listings for sale

OPEN SUN, 1:30PM TO 3:30PM
$1,180,000
3 beds2 baths2,253 sq ft
228 Woodrow Ave, Southport, CT 06890
$1,350,000
3 beds3.5 baths3,288 sq ft
50 Southport Pl #50, Southport, CT 06890
See all

Provided by Redfin

Sale history for 385 Harbor Rd

Date

Event

Price

Smart MLS #24032329

Dec 6, 2024

Sold

$15,000,000

$1,771/sq ft

Oct 11, 2024

Pending

—

Jul 17, 2024

Listed

$16,000,000

$1,889/sq ft

Jul 15, 2024

Coming Soon

$16,000,000

$1,889/sq ft

Public Records

Oct 4, 2013

Sold

$590,400

$70/sq ft

Public Records

Oct 4, 2013

Sold

$5,313,500

$627/sq ft

Smart MLS #99013871

Oct 4, 2013

Sold

$8,688,000

$1,025/sq ft

Jan 14, 2013

Listed

$10,900,000

$1,287/sq ft

HARBOR BLUFF Landmark 1854 Italianate Mansion - From an extraordinary vantage at the crest of Harbor Road, this historic home commands unparalleled views of idyllic Southport Harbor, the impeccable grounds of the Country Club of Fairfield and Long Island Sound beyond. Offering every imaginable, luxurious amenity from each of 12 exquisite, beautifully proportioned rooms, this magnificent residence is well suited for an intimate lifestyle or grand scale entertaining. This offering consists of the main residence on a 1.21 acre parcel with 120' of direct water-frontage, Pool, Garage/Carriage House and Dock and the adjacent .55 acre parcel with 145' of direct water-frontage. Carriage House features LR, Full Kit. Full Bth, BR (approx.950SF)

Smart MLS #98525177

Dec 31, 2012

Listing Removed

—

Jan 16, 2012

Listed

$10,900,000

$1,287/sq ft

Smart MLS #98525178

Sep 13, 2012

Listing Removed

—

Jan 16, 2012

Listed

$10,500,000

$1,239/sq ft

Smart MLS #98487660

Dec 31, 2011

Listing Removed

—

Jan 17, 2011

Listed

$10,500,000

$1,239/sq ft

Smart MLS #98487661

Dec 31, 2011

Listing Removed

—

Jan 17, 2011

Listed

$12,500,000

$1,475/sq ft

Smart MLS #98454124

Dec 31, 2010

Listing Removed

—

Mar 9, 2010

Listed

$10,500,000

$1,239/sq ft

Smart MLS #98449748

Dec 31, 2010

Listing Removed

—

Feb 1, 2010

Listed

$12,500,000

$1,475/sq ft

Smart MLS #98408143

Dec 31, 2009

Listing Removed

—

Feb 2, 2009

Listed

$15,500,000

$1,830/sq ft

Smart MLS #98340737

Dec 31, 2008

Listing Removed

—

Jul 9, 2007

Listed

$17,500,000

$2,066/sq ft

Public Records

Mar 6, 1992

Sold

$1,700,000

$201/sq ft

Public Records

Jul 1, 1987

Sold

$2,400,000

$283/sq ft

Year

Property tax

Land + Additions

Assessment*

2023

$80,879 (+1.0%)

$2,265,550 + $674,450

$2,940,000

2022

$80,086 (+1.0%)

$2,265,550 + $674,450

$2,940,000

2021

$79,321 (−35.2%)

$2,265,550 + $674,450

$2,940,000

2020

$122,331

$2,980,950 + $1,585,360

$4,566,310

2019

$122,331 (+1.6%)

$2,980,950 + $1,585,360

$4,566,310

2018

$120,368 (+2.1%)

$2,980,950 + $1,585,360

$4,566,310

2017

$117,902 (+1.9%)

$2,980,950 + $1,585,360

$4,566,310

2016

$115,701 (+10.8%)

$2,980,950 + $1,565,270

$4,546,220

2014

$104,417

$2,818,060 + $1,461,320

$4,279,380

Tax history for 385 Harbor Rd

Year

Property tax

Land + Additions

Assessment*

2023

$80,879 (+1.0%)

$2,265,550 + $674,450

$2,940,000

2022

$80,086 (+1.0%)

$2,265,550 + $674,450

$2,940,000

2021

$79,321 (−35.2%)

$2,265,550 + $674,450

$2,940,000

2020

$122,331

$2,980,950 + $1,585,360

$4,566,310

2019

$122,331 (+1.6%)

$2,980,950 + $1,585,360

$4,566,310

2018

$120,368 (+2.1%)

$2,980,950 + $1,585,360

$4,566,310

2017

$117,902 (+1.9%)

$2,980,950 + $1,585,360

$4,566,310

2016

$115,701 (+10.8%)

$2,980,950 + $1,565,270

$4,546,220

2014

$104,417

$2,818,060 + $1,461,320

$4,279,380

*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.

Public record

Beds

—

Baths

—

Stories

—

Lot width

—

Lot depth

—

Lot size

1.21 Acres

Year renovated

—

Sq. Ft.

—

Year built

—

Style

Other

County

Fairfield County

APN

135073

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 13, 2023.

Property details

Parking

Garage Information
Garage & Parking: Detached Garage
Garages Number: 3

Interior

Interior Information
Total Rooms: 12
Laundry Room Location: Second Floor and Garage
Laundry Room Info: Upper Level
Interior Features: Auto Garage Door Opener, Sauna
In-Law Apartment: Yes
In-Law Access: Detached
Fireplaces Total: 2
Cooling System: Central Air, Zoned
Appliances Included: Gas Cooktop, Oven/Range, Range Hood, Refrigerator, Freezer, Icemaker, Dishwasher, Washer, Dryer

Bathroom Information
# of Baths (Full): 6
# of Baths (Half): 2

Bedroom Information
Beds Total: 6

Room Information
Rooms Additional: Foyer, Laundry Room, Sauna, Sitting Room, Wine Cellar
Basement Description: Full, Unfinished

Exterior

Exterior Features
Exterior Siding: Wood
Exterior Features: Cabana, Gutters, Lighting, Guest House, French Doors, Porch, Garden Area, Covered Deck, Underground Sprinkler

Lot Information
Lot Description: Sloping Lot, Golf Course View, Professionally Landscaped, Historic District, Water View

Land Information
Encumbrances Restrictions: Regulated Historic District, Lot Restriction(s)

Pool Information
Swimming Pool
Pool Description: In Ground Pool

Building Information
Foundation Type: Masonry
Construction Description: Frame
Color: Gray

Property Information
Waterfront Description: L. I. Sound Frontage, Walk to Water, Dock or Mooring, Water Community, View
Property Type: Single Family For Sale

Financial

Assessments Information
Assessed Value: $2,940,000

Utilities

Utility Information
Water Source: Public Water Connected
Sewage System: Public Sewer Connected
Hot Water Description: Natural Gas
Heat Type: Hot Air, Zoned
Heat Fuel Type: Natural Gas
Energy Features: Generator, Thermopane Windows

Location

School Information
Middle Jr High School: Roger Ludlowe
High School: Fairfield Ludlowe
Elementary School: Mill Hill

Location Information
State: Connecticut
Nearby Amenities: Bocci Court, Golf Course, Health Club, Library, Private School(s), Shopping/Mall
Directions: Main Street or Sasco Hill Road to Harbor Road
Direct Waterfront
County: Fairfield

Public facts

Beds: —
Baths: —
Sq. Ft.: —
Stories: —
Lot Size: 1.21 acres
Style: Other
Year Built: —
Year Renovated: —
County: Fairfield County
APN: 135073

Home facts updated by county records on Jul 13, 2023

Other

Documents & Disclosures
Supplement Count Public: 2

Around this home

Schools

Mill Hill School

Public K-5 • Assigned • 0.7mi

8/10

Roger Ludlowe Middle School

Public 6-8 • Assigned • 1.2mi

8/10

Fairfield Ludlowe High School

Public 9-12 • Assigned • 1.3mi

9/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Climate risks

1/10 Flood Factor

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

1/10 Fire Factor

Unlikely to be 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

71% chance of strong winds in next 30 years

8/10 Air Factor

13 unhealthy days expected this year, 18 days in 30 years

Provided by First Street

Historical weather

Southport, CT • 06890

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

Estimated sale price

$13.68M – $16.56M

Reach more buyers when you sell with Redfin. Save up to $144,033 in fees. 3 minutes to get started.

Get a free, detailed breakdown of how we calculated your estimate.

Nearby similar homes

OPEN SUN, 1:30PM TO 3:30PM

$1,180,000

3 beds2 baths2,253 sq ft

228 Woodrow Ave, Southport, CT 06890

$950,000

3 beds1.5 baths2,100 sq ft

102 Geneva Ter, Fairfield, CT 06824

$4,700,000

6 beds6 baths6,000 sq ft

394 Penfield Rd, Fairfield, CT 06824

$4,100,000

5 beds4.5 baths4,512 sq ft

42 Puritan Rd, Fairfield, CT 06824

NEW CONSTRUCTION

$2,399,000

4 beds3.5 baths2,950 sq ft

96 Clinton St, Fairfield, CT 06824

NEW CONSTRUCTION

$1,749,000

4 beds3.5 baths3,200 sq ft

54 Timothy St, Fairfield, CT 06824

New listings for sale in 06890

OPEN SUN, 1:30PM TO 3:30PM

$1,180,000

3 beds2 baths2,253 sq ft

228 Woodrow Ave, Southport, CT 06890

$1,350,000

3 beds3.5 baths3,288 sq ft

50 Southport Pl #50, Southport, CT 06890

Home values near 385 Harbor Rd

Data from public records.

Address	Redfin Estimate
406 Harbor Rd, Southport, CT 5 Beds \| 4.5 Baths \| 3921 Sq. Ft.	$3,566,926
241 Harbor Rd, Southport, CT 5 Beds \| 6.5 Baths \| 6523 Sq. Ft.	$8,392,547

Address	Redfin Estimate
260 Harbor Rd, Southport, CT 3 Beds \| 2.5 Baths \| 2207 Sq. Ft.	$3,254,653
273 Harbor Rd, Southport, CT 4 Beds \| 5 Baths \| 4700 Sq. Ft.	$5,395,513

Address	Redfin Estimate
297 Harbor Rd, Southport, CT 4 Beds \| 5 Baths \| 7255 Sq. Ft.	$6,353,051
418 Harbor Rd, Southport, CT 7 Beds \| 6.5 Baths \| 6532 Sq. Ft.	$4,248,580

Property information provided by Smart MLS when last listed in 2024. This data may not match . Learn more.

More real estate resources

Neighborhoods
Minor Civil Divisions
Cities
Zip Codes
Popular Searches

Sasco Hill homes for sale
Fairfield Beach homes for sale
Long Island homes for sale

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Find us

Subsidiaries

Affiliated Business

Countries

United States

Canada

Updated September 2025: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.

GreatSchools Ratings provided by GreatSchools.org.

Wilton homes for sale
Weston homes for sale
Monroe homes for sale
Fairfield homes for sale
New Canaan homes for sale

Houses for rent in Southport	Agents near me	Westport, CT homes for sale	Southport Housing Market
Houses for sale near me	Greenwich, CT homes for sale	New Haven, CT homes for sale
Land for sale near me	Stamford, CT homes for sale	Milford, CT homes for sale
Open Houses near me	West Hartford, CT homes for sale	Southport Property Records
Condos for sale near me	Norwalk, CT homes for sale	CT New Listings

Greenwich homes for sale
Stamford homes for sale
Norwalk homes for sale

06880 homes for sale
06824 homes for sale
06890 homes for sale