Maine's Oldest Running Business

F.O. Bailey History

F.O. Bailey History

The F.O. Bailey Story

In a place known for L.L. Bean and lobsters, F.O. Bailey has become synonymous with Maine’s most coveted real estate markets.  What began as a general merchandise store on Portland’s Ingham Wharf in 1819 has transformed into Maine’s go-to partner for commercial and residential real estate.

The pivot didn't happen overnight, but we are thrilled to be here.

F.O. Bailey Company has managed to stay relevant for over 200 years thanks to our dynamic way of thinking, highly qualified team, and elite customer service. Regularly out-performing the brokers at national firms, our reputation, partnerships, and referrals serve as the foundation for our continued growth.

Employing the most up-to-date strategies and technologies, our agents specialize in everything from the purchases and sales of luxury single-family homes to multi-family investments and industrial properties.

The Jones Era:

In 2014, the F.O. Bailey Company changed hands when real estate broker, David Jones, and his wife, Nancy McInnis-Jones, purchased the company from Joy Piscopo. According to Piscopo, the F.O. Bailey name is synonymous with “integrity, expertise, and experience,”. For that reason, she was careful to select new owners that would live up to that standard. 

“It’s a Maine tradition!” said David Jones. “The name F.O. Bailey has the same prominence here as L.L. Bean. We’re proud to be a part of it.”

Proud indeed. 

Providing our clients with a sense of comfort and confidence in their decisions is the foundation upon which our brand stands. Dedicated to serving local residents, we are grateful to the people and place that has played a significant role in our success. 

F.O. Bailey Company has over two centuries of Maine momentum, and it's only the beginning.

Whether buying or selling Maine real estate, our team knows this state and is here to help. We'd be thrilled to guide you through your Maine real estate journey. Connect with us today!

Beginnings of a Dynasty

  • 1819

    Henry Bailey Opened General Merchandise Store

    Old photo of port

    In 1819, when young Henry Bailey opened a general merchandise store on Ingraham’s Wharf in Portland and began auctioning salvaged goods on the street out front, James Monroe was serving as our country’s fifth president. Maine was still a part of Massacchsetts (it wouldn’t become a state until 1820), and construction on the Erie Canal had only recently begun. Henry Wadsworth Longfellow, Portland’s native son and America’s most beloved poet, was only 12 years old. The country was still very young, but there was a great sense of optimism about the future.

  • 1827

    Bailey Company Diversified Product

    Bailey Company Diversified Product

    In 1827 the Bailey Company diversified and began manufacturing rolltop desks and display cabinets for stores. This required a move to a new, larger facility on Exchange Street, where it operated for the next hundred years. In the smuggling days, and in the bankruptcy-and-seizure days of the Civil War era, the company was forced to make money in myriad ways simply to survive, but always found the auctioneering business to be a particularly good money maker.

    Bailey Company Diversified Product
  • 1866

    The Great Fire of 1866

    The Great Fire of 1866

    By 1866 Portlanders could look back on nearly a century of astonishing progress. Their port had grown from a frontier mast landing into a serious cultural and economic rival of Boston. Fast becoming Canada’s winter rail-head, “the Forest City” ranked fourth in imports and fifth in exports among American cities. Rich, proud, vital, and confident, Portlanders seemed to march in lock-step with national events.

    But then the Great Fire of 1866 devastated the city. In less than 24 hours, the heart of a great American port city was laid in ruins, including the store operated by Henry Bailey. The grim statistics of 10 million dollars in property loss and 12,000 people left homeless translated into the worst urban fire in America to that date.

    A newly rebuilt Exchange Street as it looked after the Great Fire of 1866

  • 1867

    Out of the Ashes: F.O. Bailey Carries On the Family Business

    The Bailey Trotting Sleigh The Bailey Trotting Sleigh

    In 1867, the year after the Great Fire, Henry Bailey died. Both the city and the Bailey Company would make an astonishing recovery, however. A rebuilding spirit of pride and determination took over as new Victorian business blocks of brick, stone, and cast iron arose Phoenix-like from the ashes. The Bailey Company was carried on in 1867 by Henry’s son, Frederick Orville Bailey, in new premises on Exchange Street. That same year, F.O. Bailey took as a partner a young farm boy from Poland, Maine named Charles W. Allen.

    The Bailey Carriage Company c 1900 The Bailey Carriage Company c 1900

    A big but now-forgotten enterprise of the F.O. Bailey Company during the nineteenth century was the sleigh and racing sleds business, reputed to be among the best in the nation, and the manufacture of fine horse carriages from the company’s facilities at the corner of Market and Middle Streets. Anything and everything having to do with horses and the carriage trade was manufactured and sold here.

  • 1901

    F.O. Bailey Enters Automobile Business

    In 1901, F.O. Bailey even went into the automobile business, selling cars costing from $600 to $6,000, when Bailey and Allen formed the Maine Motor Carriage Company at the corner of Free and South Streets. While business was brisk, with sales of about $200,000 in just three years, they seemed to have misjudged the market for what was then seen as a passing fad. In 1906, young Neal W. Allen wrote as follows about the family automobile business:
    “In all probability the high water mark of the car business will be reached by about 1908. The market will soon be oversupplied with machines. When the present great demand for automobiles is past, the car business will settle down to somewhat the same basis as carriages and sleds.”

    The Maine Motor Carriage Company at Free and
                                  South Streets The Maine Motor Carriage Company at Free and South Streets

  • 1912

    The Allen Family Takes Over

    In 1912, Charles W. Allen died and the firm was incorporated by Frederick O. Bailey as the F.O. Bailey Company, Inc., with Mr. Allen’s son, Neal W. Allen elected as president.

    The Allen Family Takes Over
  • 1928

    F.O. Bailey Company Moves to Free & South Street Location

    IN 1928, after more than a hundred years of doing business on Exchange Street, the F.O. Bailey Company moved to the Free and South Street location.

  • 1933

    F.O. Bailey Company Manufactures Fine Store Fixtures

    In 1933, after years of being a manufacturer of show cases, in addition to the retail furniture and auctioneering businesses, the F.O. Bailey Company actively began the manufacture of fine store fixtures, which could be found installed in many of the most progressive stores throughout New England.

  • 1941 - 1945

    The War Years

    An F.O. Bailey Company truck making deliveries to the United States Air Force An F.O. Bailey Company truck making deliveries to the United States Air Force

    The F.O. Bailey Company was more active than ever in serving war-time Portland and continued on a larger scale to supply Maine people with furniture of all kinds, to ship antiques throughout the nation, and to build finer and more beautiful stores and restaurants throughout New England. A 1943 company brochure proclaimed:

    “Our purpose will be, first of all, to do everything within our power to assure victory; Second, to continue to give every customer quality merchandise and efficient and reliable service so that merchants using the products of our cabinets mill, clients for whom we act as agents or auctioneers and buyers or sellers of antiques, may have complete confidence in our fairness and integrity.”

  • 1946 - 1976

    The Post-War Period

    he Post-War Period

    Some longtime employees of the F.O. Bailey Company gathered at the Roma Cafe in 1979 to celebrate the 160th birthday of the company. Seated were, from left, Barbara A. Atwood and Merritt S. Higgins. Standing, Carmine (Jack) Piscopo, Franklin B. Allen, former president, Herman J. Bouchard, Joy Piscopo, Enos E. Johnson, Francesco Palanda, Hilding A. Berg, and Malcolm A. Johnson.

  • 1977 - 2014

    The Piscopo Family Era

    The Woodman Building on Middle Street c 1887 The Woodman Building on Middle Street c 1887
    Home of the F.O. Bailey Company for many years.

    In 1977, Allen family descendants Charles and Franklin Allen were running the company, but were also looking for a buyer. By then the company had moved from its old Free Street headquarters and was happily situated at 141 Middle Street at the top of the Old Port district, one of the major Victorian business blocks to rise from the ashes of the Great Fire. Erected in 1867 to house the wholesale dry goods firm of Woodman, True and Co, the Woodman Building occupied the corner position of the city’s most impressive row of post fire commercial architecture, all three units of which were the work of the local architect George M. Harding.

    Jack and Joy Piscopo met with the Allens several times before a deal was struck, and then purchased the business. For the next twenty-five years the Piscopos operated the F.O. Bailey Company from the Middle Street location, a period described by Joy Piscopo as “a golden age of antique and estate auctions in Maine.”

    In 2004, the Piscopos closed up shop in downtown Portland and moved to a new home in Falmouth, spurred by the changing business atmosphere on Middle Street, the new realities of the auction business, and a desire to downsize their lives. Here they operated for the next ten years.


    Auctioneer's receipt for the sale of a painting.  December 8, 1879 and page from the Bailey Company catalog of 1892 Auctioneer's receipt for the sale of a painting. December 8, 1879 and page from the Bailey Company catalog of 1892

  • 2014 - Present

    The Jones Family Continues the Legacy

    2019 - Most expensive sale in the history of Falmouth, Maine - David Jones and Thomas Gadbois represented the buyer and seller, respectively, for the sale of 153 Foreside Road in Falmouth Foreside. It was a 9,300 square foot contemporary waterfront estate. This was the most expensive single-family home ever sold in Falmouth.

    2020 - The most expensive sale in the history of Portland, Maine. Once again, David Jones and Thomas Gadbois represented the buyer and seller, respectively. 181 Western Promenade, is considered the crown jewel of Portland. This was the most expensive single-family home ever sold in Portland.

Continuing the Legacy

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