239 Jessica Lane

The Ultimate Showstopper 

239 JESSICA LANE, SOUTHPORT 

ON THE HARBOR 

LIBBY TRITSCHLER • 203.913.9454 

ANDREW WHITELEY • 203.258.1595 

WENDY RYAN • 203.964.7450 

ONTHEHARBORREALESTATE.COM 

TEAM AFA / WILLIAM RAVEIS REAL ESTATE

Listing Details 

At A Glance 

2.12 Acres 

5,081 Sq/Ft 

4 Bedrooms 

4 Full, 

2 Partial Bath 

3 Car Attached Garage 

Central Air 

Hot Air Heat - Natural Gas 

Private Well & Septic 

239 JESSICA LANE, SOUTHPORT, CT 

ON THE HARBOR | LIBBY TRITSCHLER • ANDREW WHITELEY • WENDY RYAN 

TEAM AFA AT WILLIAM RAVEIS REAL ESTATE

SITUATED ON A QUIET, COVETED SOUTHPORT CUL-DE-SAC, 

239 JESSICA LANE IS A HOME OF UNPARALLELED DISTINCTION. 

SINCE BEING CUSTOM BUILT BY THE CURRENT OWNERS, THIS RESIDENCE HAS BEEN 

METICULOUSLY MAINTAINED THROUGHOUT THEIR OWNERSHIP. ONE OF THE MOST 

SIGNIFICANT ENHANCEMENTS IS THE MAGNIFICENT TWO-STORY TREE HOUSE, 

THOUGHTFULLY DESIGNED BY THE RENOWNED LOCAL ARCHITECT, MARK FINLEY. THIS 

EXTRAORDINARY SPACE OFFERS AN OASIS OF PRIVACY AMIDST BEAUTIFULLY 

LANDSCAPED GROUND, DESIGNED AND MAINTAINED BY ACCLAIMED OLIVER’S NURSERY. 

THE TREE HOUSE IS THE IDEAL SETTING FOR HOSTING SUMMER DINNER PARTIES OR 

ENJOYING COCKTAILS. IT TRULY DEFIES DESCRIPTION AND MUST BE SEEN TO BE 

BELIEVED. OUTDOOR ENJOYMENT CONTINUES WITH A CUSTOM GUNITE POOL 

SURROUNDED BY AN EXPANSIVE PATIO, PROVIDING A SERENE RETREAT FOR 

RELAXATION AND RECREATION. 

THE LIVING AREAS ACHIEVE A SEAMLESS BLEND OF BOTH 

FORMAL AND INFORMAL SPACES. 

THE EXPANSIVE AND WELL-THOUGHT-OUT DESIGN GUARANTEES COMFORT WHILE 

MAINTAINING A HIGH LEVEL OF STYLE AND SOPHISTICATION. ONE OF THE HOME'S MOST 

DELIGHTFUL SURPRISES AWAITS IN THE WALKOUT LOWER LEVEL – AN AUTHENTIC IRISH 

PUB. THIS WHIMSICAL AND ENTERTAINING SPACE ADDS A TOUCH OF UNIQUE 

CHARACTER AND IS SURE TO BE A FAVORITE GATHERING SPOT. 

TO FULLY APPRECIATE THE EXCEPTIONAL OFFERINGS OF 239 JESSICA LANE, 

A PERSONAL VISIT IS A MUST. 


























































Listing 

1099 Pequot Avenue, Fairfield, CT 06890 List Price: $7,500,000 

MLS#: 170621454 DOM: 32 Tax Parcel#: 136679 Orig. List Price: $7,500,000 

Status: Active Last Update: 01/29/24 

Single Family For Sale 

Neighborhood: Southport 

School Information 

Elem: Mill Hill Interm: Middle: Roger Ludlowe High: Fairfield Ludlowe 

Year Built: 1996 New Construction: No/Resale Acres: 1.90 

Estimated HEATED Sq.Ft. above grade is 11,078; total 11,078 

Property Tax: $199,246 Assessed Value: $7,242,690 Mil Rate: 27.51 

Style: Mediterranean Rooms: 17 Bedrms: 5 Bathrms: 7 Full & 2 Half Fireplaces: 4 

Potential Short Sale: No 

Room Descriptions 

Room Level Apx. Size Features 

Primary BR Suite Upper Fireplace, Full Bath 

Bedroom Upper Full Bath, Walk-In Closet 

Bedroom 

Upper 

Bedroom Upper Full Bath, Walk-In Closet 

Rec/Play Room Upper 

Office 

Upper 

Library Main Fireplace 

Living Room Main Fireplace 

Dining Room Main Fireplace 

Sun Room 

Main 

Family Room Main Fireplace 

Bedroom 

Upper 

Additional Rooms: Foyer, Wine Cellar 

Laundry Location: Main Level Has In-Law Apart: Possible 

Features 

Appliances Incl.: Gas Cooktop, Gas Range, Oven/Range, Range Hood, Refrigerator, Freezer, Subzero, Dishwasher, Washer, Dryer 

Interior Features: Audio System, Auto Garage Door Opener, Cable - Pre-wired, Humidifier, Intercom, Security System 

Handicap Feat.: 32" Minimum Door Widths, 60" Turning Radius, Hallways 36+ Inches Wide 

Energy Features: Generator, Programmable Thermostat 

Attic: Has Attic - Access Via Hatch, Crawl Space Basement Desc.: Full, Crawl Space, Unfinished, Concrete Floor, Garage Access 

Exterior Features: Balcony, French Doors, Gutters, Lighting, Patio, Stone Wall, Terrace, Underground Sprinkler, Underground Utilities 

Garage Spaces: 4 Car Parking Spaces: Driveway Type: Private, Circular, Asphalt, Crushed Stone 

Garage/Parking Type: 4 Car, Attached Garage 

Lot Description: On Cul-De-Sac, Water View In Flood Zone: Yes 

Waterfront Feat.: Direct Waterfront - Direct Waterfront, L. I. Sound Frontage, View, Walk to W Swimming Pool: Has Pool 

Nearby Amenities: Golf Course, Health Club, Library, Park, Private School(s), Stables/Riding 

Home Owners Association Information 

Home Owner's Association: No Association Fee: Fee Payable: 

Association Fee Provides: 

Special Assoc. 

Assessments: 

No 

Utility Information 

Hot Water System Natural Gas Est. Annual Heating Cost 

Heat Type: Hot Air, Fueled By: Natural Gas Fuel Tank Location: Non Applicable 

Cooling: Central Air, Zoned Radon Mitigation: Air Unknown, Water Unknown 

Water & Sewer Service: Public Water Connected, Sewage System: Septic 

Public Remarks 

Coveted Southport waterfront. Builder's own 11,000+ sq. foot custom home on private Rock Point Road off Pequot Avenue and walking 

distance to Southport Beach and Village. Magnificent 1.9-acre lot with 200 feet directly on Long Island Sound with views towards Westport's 

Gold Coast of Beachside Avenue and the Manhattan skyline in the distance. A beautiful pool and pool house pull you outside to enjoy every 

changing tide and sky. Outstanding value when compared to neighboring sales and tremendous potential upside awaits the prudent purchaser. 

A similar sized lot on the street recently sold for $7m and the house directly next door sold in 2020 for $16.5m. Come and see for yourself. 

Don't miss out as all of our best local waterfront properties are being snatched up. Close to the town centers of Westport, Southport and 

Fairfield and just 50 miles to NYC. 

Listing Contract, Showing $ Compensation Information 

Listing Date: 01/29/24 Closed Date: Expiration Date: Date Available: Negotiable 

Listing Contract Type: Exclusive Right to Sell/Lease 

Buyer's Agent Comp.: 2% of sale price 

Showing Inst: Call or Text Andrew Whiteley for all showings 203.258.1595. 24 Hr Notice Required. 

Directions: Harbor Rd or Beachside Ave to Pequot Ave. On private, gated Rock Point Rd Lockbox: None 

Listing & Selling Agent/Broker Information 

List Team: On the Harbor Team AFA at William Raveis Real Estate 

(203) 913-9454 

(TM100218) Leader's Lic.#: RES.0774354 

List Agent: Elizabeth Tritschler (9269) Lic.#: (203) 913-9454 Libbyt@afahomes.com 

List Office: William Raveis Real Estate (RAVE80) (203) 255-6841 

Co List Team: Team AFA at William Raveis Real Estate (TM100177) 

(203) 256-3264 

Leader's Lic.#: REB.0750197 

Co List Agent: Andrew S. Whiteley (8005) Lic.#: (203) 258-1595 andreww@afahomes.com 

Co List Office: William Raveis Real Estate (RAVE80) (203) 255-6841 

Information contained in this Smart MLS listing has been compiled from various sources, all of which may not be completely accurate. Smart 

MLS makes no warranty or representation as to the accuracy of listing information. All information that influences a decision to purchase a 

listed property should be independently verified by the purchaser. Report Generated on 03/01/2024 6:11:19 PM, Copyright 2024 Smart MLS, 

Inc. All rights reserved.

TEAM OVERVIEW 

ON THE HARBOR OFFERS OVER 30 YEARS OF COLLECTIVE REAL ESTATE EXPERIENCE MARKETING 

AND SELLING ACROSS ALL PRICE POINTS AND IN VARIOUS MARKET CONDITIONS. OTH FEATURES THE 

COMBINED TALENTS AND EXTENSIVE SPHERES OF INFLUENCE OF AFA’S TOP PRODUCING 

INDIVIDUAL AGENTS OVER THE PAST SEVERAL YEARS. THIS IS A FORMIDABLE ALLIANCE WHEN YOU 

CONSIDER THAT AFA AS A GROUP HAS BEEN CONSISTENTLY RANKED BY THE WALL STREET 

JOURNAL AS THE #1 REAL ESTATE TEAM IN ALL OF NEW ENGLAND BY CLOSED SALES VOLUME. LET 

US SHOW YOU HOW WE MAY BE OF SERVICE IN HELPING YOU ACHIEVE YOUR INDIVIDUAL REAL 

ESTATE GOALS. 

LIBBY MCKINNEY-TRITSCHLER - EXECUTIVE VICE PRESIDENT OF SALES 

LIBBY MCKINNEY-TRITSCHLER IS A FIFTH GENERATION FAIRFIELD RESIDENT, AND SHE CURRENTLY 

LIVES IN SOUTHPORT VILLAGE. IN HER 15+ YEARS AT AFA, LIBBY HAS CONSISTENTLY BEEN A TOP 

PRODUCING AGENT AND SHE HAS BEEN INVOLVED WITH ALL OF THE TEAM'S HIGHEST RECORDED 

SALES. LIBBY’S INSIDER KNOWLEDGE OF THE SOUTHPORT MARKET AND HER UNEQUALLED WORK 

ETHIC ARE TREMENDOUS ASSETS TO HER CLIENTS. LIBBY'S ABILITY TO WORK SUCCESSFULLY WITH A 

WIDE VARIETY OF BUYER AND SELLER CLIENTS ACROSS VARIOUS PRICE POINTS IS REFLECTIVE IN 

HER CONSISTENTLY OUTSTANDING SALES PRODUCTION. LIBBY CONTINUES HER FAMILY’S LONG- 

STANDING COMMITMENT TO PUBLIC SERVICE, AND SHE SERVES ON THE BOARDS OF THE STEWART 

B. MCKINNEY FOUNDATION AND THE WESTPORT/WESTON YMCA 

ANDREW WHITELEY - PRESIDENT OF PREMIER HOME COLLECTION 

A MANHATTAN NATIVE, ANDREW HAS CONSISTENTLY BEEN RANKED AMONG THE TOP-PRODUCING 

BROKERS IN THE COUNTRY. SINCE MOVING TO CT OVER 25 YEARS AGO – HE HAS LIVED IN 

SOUTHPORT, GREENFIELD HILL, GREENWICH AND EASTON. THROUGH HIS PROFESSIONAL AND 

SOCIAL NETWORKS, ANDREW HAS DEVELOPED UNPARALLELED INSIDER KNOWLEDGE OF THE 

PREMIER PROPERTY MARKET, AND AS SUCH HE IS PRIVY TO MANY OF THE UNLISTED AND 

UNADVERTISED RESIDENTIAL PROPERTIES POTENTIALLY FOR SALE, THE SO-CALLED “POCKET 

LISTINGS”. THIS UNIQUE POSITION PROVIDES HIS CLIENTS WITH OTHERWISE UNAVAILABLE ACCESS 

TO THE MOST COVETED PROPERTIES. ANDREW IS A REGULAR CONTRIBUTOR TO BOTH NATIONAL 

AND LOCAL MEDIA ON REAL ESTATE TRENDS AND THE LUXURY MARKET OVERALL AND HE SERVES 

ON THE FORBES REAL ESTATE COUNCIL. FOR THE PAST SEVERAL YEARS, ANDREW HAS BEEN THE 

TEAM’S TOP PRODUCER AND ONE OF THE MOST SUCCESSFUL AGENTS WITHIN THE ENTIRE WILLIAM 

RAVEIS NETWORK OF 4,500+ AGENTS AND 135+ OFFICES. HE EMBRACES HIS POSITION AT AFA AS 

PRESIDENT OF THE GROUP’S PREMIER HOMES DIVISION AND ENJOYS SELLING THE UNIQUE 

LIFESTYLE AND CHARACTER OF LIVING ON THE HARBOR TO THE WORLD. 

WENDY HINMAN RYAN – EXECUTIVE VICE PRESIDENT OF SALES 

BORN AND BRED IN FAIRFIELD COUNTY, WENDY HAS LIVED HERE ALL HER LIFE AND EMBRACES THE 

SPIRIT THAT THE COMMUNITY HAS TO OFFER. HER LOVE FOR OUTDOOR ACTIVITIES, CLOSE 

COMMUNITY AND LOCAL CHARM IS WHAT HAS ENCOURAGED HER TO REMAIN WORKING AND 

LIVING LOCALLY. WENDY GREW UP ATTENDING BOTH PRIVATE AND PUBLIC SCHOOL IN 

GREENWICH. SHE MOVED ON TO RECEIVE HER BA FROM BOSTON COLLEGE MAJORING IN 

MARKETING AND COMMUNICATIONS WHILE COMPETING AS A DIVISION I ATHLETE IN SAILING. PRIOR 

TO ENTERING THE REAL ESTATE FIELD, WENDY HELD A SUCCESSFUL CAREER IN MARKETING AND 

PROMOTIONS. SHE CONSULTED VARIOUS FORTUNE 500 CLIENTS IN BUILDING, LAUNCHING AND 

PROMOTING THEIR BRANDS. HER KNOWLEDGE AND EXPERTISE IN MARKETING STRATEGY WILL GIVE 

HER CLIENTS A DISTINCT ADVANTAGE IN REACHING THEIR SPECIFIC GOALS. CLIENT SERVICE HAS 

ALWAYS BEEN PARAMOUNT IN WENDY’S PROFESSIONAL CAREER AND CONTINUES TO BE IN REAL 

ESTATE. WENDY SERVICES A WIDE VARIETY OF CLIENTS WITH A SPECIALTY IN RELOCATION, NEW 

CONSTRUCTION AND INVESTMENT PROPERTIES. SHE UNDERSTANDS THE DIFFICULTY IN NAVIGATING 

THE COMPLICATED REAL ESTATE MARKET AND THRIVES TO MAKE THE EXPERIENCE AS SEAMLESS AS 

POSSIBLE FOR ALL HER CLIENTS. 




SALES HISTORY 

1143 SASCO HILL ROAD - $17,500,000 * 

340 WILLOW STREET - $16,350,000 

66 BEACHSIDE AVENUE - $16,000,000 

1093 PEQUOT AVENUE - $10,900,000 

1143 SASCO HILL ROAD - $9,375,000 


1147 SASCO HILL ROAD -$8,000,000 





1376 PEQUOT AVE - $6,050,000 



825 HARBOR ROAD - $5,995,000 

935 HARBOR ROAD - $5,900,000 

750 HARBOR ROAD - $5,900,000 * 




1110 HARBOR ROAD - $5,200,000 


104 OLD SOUTH ROAD - $4,900,000 * 

780 HARBOR ROAD - $4,725,000 




564 HARBOR ROAD - $4,300,000 * 

1093 PEQUOT AVENUE - $4,200,000 


222 WILLOW STREET - $3,995,000* 


1100 HARBOR ROAD - $3,875,000 

225 OLD SOUTH ROAD- $3,700,000 


319 HARBOR ROAD - $3,625,000 * 

916 PEQUOT AVENUE - $3,625,000 

789 HARBOR ROAD - $3,300,000 * 

225 OLD SOUTH - $3,300,000 

89 HARBOR ROAD - $3,300,000 

971 HULLS FARM ROAD - $3,250,000 

72 ROSE HILL ROAD - $3,250,000 

807 PEQUOT AVENUE - $3,200,000 * 


807 PEQUOT AVENUE - $3,200,000 * 

390 HARBOR ROAD - $3,000,000 


390 HARBOR ROAD - $3,000,000 

1100 HARBOR ROAD - $2,950,000 

753 ROWLAND ROAD - $2,950,000 

683 PEQUOT AVE - $2,900,000 



14 WILLOW STREET - $2,760,000 

73 CHRISTMAS TREE LN - $2,765,000 

1070 PEQUOT AVENUE - $2,700,000 

1011 PEQUOT AVENUE - $2,650,000 

608 HARBOR ROAD - $2,640,000 

321 TAINTOR DRIVE - $2,600,000 



240 HARBOR ROAD - $2,570,000 


1003 PEQUOT AVENUE - $2,550,000 


932 MILL HILL ROAD - $2,500,000 

191 MAIN STREET - $2,500,000 


221 HARBOR ROAD - $2,395,000 

50 WARNER HILL - $2,375,000 * 

1450 HILLSIDE ROAD - $2,350,000 

52 ROWAYTON AVE - $2,325,000 

319 HARBOR ROAD - $2,280,000 


1133 CEDAR ROAD - $2,250,000 


154 MILL HILL TERRACE - $2,200,000 * 

1088 HARBOR ROAD - $2,100,000 * 

285 REDDING ROAD - $2,100,000 

26 LONG LOTS LANE - $2,100,000 

865 PEQUOT AVENUE - $1,900,000 

226 MAIN STREET - $1,875,000 

441 PEQUOT AVENUE - $1,865,000 

1051 CEDAR ROAD - $1,816,000 

93 BEACHSIDE AVE - $1,800,000 

999 MERWINS LANE - $1,780,000 


191 MAIN STREET - $1,700,000 




SALES HISTORY 

223 MICHIGAN AVE - $1,735,000 

809 CEDAR ROAD - $1,690,000 

49 SOUTHPORT GREEN - $1,650,000 * 


776 PEQUOT AVENUE - $1,570,000 

1337 FAIRFIELD BEACH - $1,560,250 

1123 SASCO HILL - $1,515,000 

81 MAIN STREET - $1,511,000 

23 LARBERT ROAD - $1,500,000 

82 SOUTH GATE LANE - $1,485,000 

100 JESSICA LANE - $1,465,000 

448 PEQUOT AVENUE - $1,437,500 

207 MAIN STREET - $1,400,00 

301 FULLING MILL SOUTH - $1,375,000 

471 WESTWAY ROAD - $1,325,000 

70 BURRWOOD COMMON - $1,284,000 

1233 S. PINE CREEK - $1,283,000 

1 RIVER LANE - $1,281,500 

64 ARBOR TERRACE - $1,280,000 * 

171 PADDOCK HILL LANE - $1,275,000 

2 ELMWOOD DRIVE - $1,262,500 

1400 MILL HILL ROAD - $1,245,000 


17 ROSE HILL ROAD - $1,235,000 

55 DAYBREAK LANE - $1,210,000 

300 SOUTH GATE LANE - $1,202,000 

300 CHESTNUT HILL - $1,200,000 

165 BUTTERNUT LANE - $1,175,000 

75 SOUTHPORT GREEN - $1,155,000 

21 DAYBREAK LANE - $1,137,500 

1 IMPERIAL LANDING - $1,125,000 

63 SOUTHPORT GREEN - $1,124,500 

91 CATALPA ROAD - $1,100,000 

99 LYONS PLAIN ROAD - $1,100,000 

83 GRIST MILL LANE - $1,095,000 

46 STATION STREET - $1,074,600 

66 SUNNY RIDGE ROAD - $1,050,000 


5 EVELYN STREET - $1,050,000 

141 BEERS ROAD - $1,049,000 


701 OLD ACADEMY RD - $1,002,500 

50 SOUTHPORT PLACE - $1,001,500 

430 MILL HILL TERRACE - $980,000 

107 TAYLOR PLACE - $980,000 

561 PEQUOT AVENUE - $970,000 

55 SHERMAN STREET W - $960,000 * 

160 MOREHOUSE LANE - $950,000 

45 SOUTHPORT GREEN - $949,000 * 

30 DAYBREAK LANE - $949,000 

156 PEQUOT AVENUE - $925,000 

191 S. GATE LANE - $860,000 * 

240 VILLAGE LANE - $840,000 

4250 CONGRESS STREET - $830,000 


50 SOUTHPORT PLACE - $825,000 

100 TAYLOR PLACE - $825,000 

170 WOODROW AVE - $825,000* 

155 WOODROW AVE - $800,000 


300 FULLING MILL LANE - $787,000 

20 REDDING ROAD - $775,000 * 

470 PEQUOT AVE - $752,500 

62 SPRUCE STREET - $725,000 

15 OLD DAIRY LANE – $725,000 

40 ABERDEEN WAY - $710,000 * 

1146 VALLEY ROAD - $700,000 

306 STURBRIDGE LANE - $670,000 

136 ARBOR DRIVE - $655,000 

450 CENTER STREET - $650,000 * 

200 WESTFORD DRIVE - $649,000 

500 PEQUOT COURT - $640,000 

510 MILL HILL ROAD - $635,000 * 

605 CENTER STREET - $625,000 

61 VILLAGE LANE - $585,000 

133 ARBOR DRIVE - $582,000 

240 MAIN STREET - $565,000 

83 SPRUCE STREET - $545,000 

208 SOUTHPORT WOODS - $499,000 * 

98 KINGS DRIVE - $490,000 

140 SHERWOOD DRIVE - $425,000 

147 WESTFORD DRIVE - $420,000 

592 CENTER STREET - $400,000 

18 MILL HILL ROAD - $400,000 

PENDING 


319 HARBOR ROAD - $3,625,000 

240 HARBOR ROAD - $3,250,000 

*DENOTES OTH REPRESENTING BOTH BUYER & SELLER 

239 JESICA LANE, SOUTHPORT, CT 



SOUTHPORT, CONNECTICUT 

IN THE 1700S, MILL RIVER VILLAGE WAS A SMALL HAMLET OF A FEW 

HOUSES AND A WHARF AT THE MOUTH OF FAIRFIELD’S MILL RIVER. BY 

1831 THE VILLAGE HAD CHANGED ITS NAME TO SOUTHPORT AND WAS A 

BUSTLING COMMERCIAL AREA WITH WAREHOUSES, CHURCHES, 

SCHOOLS, STORES, AND ELEGANT HOUSES. 

SOUTHPORT BECAME A LEADING COASTAL PORT ON LONG ISLAND 

SOUND, ITS SHIPS CARRYING PRODUCE AND GOODS BACK AND FORTH TO 

NEW YORK CITY. A MEASURE OF ITS SUCCESS IS THE FACT THAT 

THROUGHOUT THE 1800S IT POSSESSED THE ONLY TWO BANKS IN TOWN. 

HOWEVER, COMPETITION FROM STEAMBOATS AND THE RAILROAD TOOK 

ITS TOLL ON PROSPERITY. RESOURCEFUL SHIPPERS TEAMED WITH LOCAL 

FARMERS AND BUSINESSMEN TO KEEP THE PORT GOING; THE 

SOUTHPORT ONION, A HIGH-QUALITY ONION WAS DEVELOPED AND 

GROWN ON FAIRFIELD’S HILLS AND SHIPPED IN SOUTHPORT MARKET 

BOATS, KEEPING THE HARBOR PROFITABLE UNTIL THE END OF THE 

CENTURY. 

TODAY, MUCH OF THE OLD VILLAGE AREA IS PART OF AN HISTORIC 

DISTRICT, WHERE BUILDINGS FROM THREE CENTURIES ARE PROTECTED 

FOR FUTURE GENERATIONS.

239 Jessica Lane

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