Find your Rental Paradise in the Caribbean, St. John US Virgin Islands, St. Maarten, Stowe, VT, Bretton Woods, NH and Sunday River, ME.

Meet the Owners: John F. Gallagher And the late Susan J. Gilmore

John with Don Imus Above: John with embattled radio/tv talk show host "Imus in the Morning" Don Imus
Above: Owner John Gallagher, his daughter Rachael and actress Jane Fonda taken recently in New York City.

Sadly, Susan Gilmore Gallagher passed away February 2008 after a long bout with stomach cancer.

Obituary on the late home owner Susan Gilmore-Gallagher

The 3 Stowe VT houses, 2 Bretton Woods houses, 2 villas in St. Maarten, and 2 houses on St. John are all owned by John and Susan.

Because we rent them ourselves (with no brokers or villa agents), we’re able to offer you prices often a $1,000 a week less than a comparable luxury house. (in the case of La Perla our magnificent oceanfront villa, the savings maybe be $ 2,000 a week or more).

John is entering his 50's. We’re the founders of East-West Mortgage Company a large lender in New England, which we sold to a bank a few years ago.

These days, we operate Gallagher Commercial Real Estate and Development a private lender on real estate and venture capital Deals which we’ve done for the past 20 years. Of course we’re always buying new vacation houses in trophy Locations and fixing them up with extensive renovations.

We both grew up in Massachusetts and now live in Manchester by the Sea on the north shore, 20 miles from Boston with our 3 little kids, 2 mini poodles (Pierre and Harrington) and 2 cats.

A little history!

John is a graduate of Univ. of Mass/Amherst and spent many of his early years in The radio business at WAAF and WAAB in Worcester, first as a DJ while in college and then as an executive. John grew up near Holy Cross College and lived in Worcester for many years until moving to the North Shore of Massachusetts.

After a decade in radio, he founded a number of business, eventually starting East-West Mortgage Co. and I sold my house.com in the mid 80’s. East-West became a mortgage powerhouse throughout New England and was doing $ 2 billion per year in residential mortgages when John and Susan sold it.

Within a year of John’s departure from East-West the company went from 324 employees to less than 50 so one can see what happens when a ship has no captain.

We always loved to travel in the Caribbean so we decided to buy a house.

Then we bought 2 six bedroom ski houses in Vermont with big views of the ski area and lifts.

Then we bought another St. Maarten house. And we recently bought six oceanfront lots at Dawns Beach on St. Maarten (possibly the best beach on the island). Maybe we’ll build on them and maybe just hold them for an investment. Not sure yet.

New Rental Houses Coming Soon:

On the beautiful island of St. John in the U.S. Virgin Islands
We now own 2 houses.

The 5 BR on the east end has been totally renovated and has gorgeous Ocean views.  It’s nice and quiet on the east end of St. John which is about a 25 minute ride from Cruz Bay where the ferry goes back and forth to St. Thomas.

We also have a 3 BR house at Coral Bay (it’s about a 7 minute ride between our Houses) which we’re now renovating adding a pool and large outdoor patio with outdoor cooking built in.  This house also has panoramic ocean views of Coral Bay and the beautiful Caribbean waters.

Our properties are on the quiet side of St. John, where donkeys and wild goats outnumber people. If Jimmy Buffet is on St. John, this is likely where you’ll find him. (and don’t be surprised if you do)…(as well as his pal Kenny Chesney who lives on St. John full time)

Above: Susan, John and daughter Rachael with Mass. Governor Mitt Romney (who ran for President)
Above: John, having a cocktail on the patio at la perla

When we buy a vacation house we look for a few basic things:

  • Superior location
  • Awesome views
  • Proximity to activities (skiing, swimming, etc.)
  • A big house that needs total renovation
  • A private setting….quiet and relaxing
  • No (violent) crime
  • Friendly local people

With enough money you can do anything to a house. But you really can’t change the land.

After renovating the house, we then buy all new furniture at the big manufacturers in North Carolina usually. Then we have it shipped by container to the house.

For the Caribbean houses, we buy top of the line appliances, light fixtures, tiles, etc. in Miami and have them shipped over to St. Maarten.

Our ski houses we make warm and cozy with a lot of carpeting, heat in the floors when possible (we love radiant heat) and a huge fireplace.

Down in the Caribbean, it’s just the opposite. We make the houses cool with a lot of tiles, cross ventilation and air conditioning in all bedrooms. And a lot of outdoor living area with huge patios and comfortable lounge chairs.

When we used to rent others’ houses years ago, we could never understand the owners’ locking up the booze. Or arriving to an empty house on a dark Friday night. So we cured both problems by having our housekeeper buy first night staples for our guests such as milk, bread, coffee, cereal, beers, bottle of wine, etc.


Above: John and daughter Jennifer after she had her hair braided on st. Maarten

Above: Susan having lunch on the patio at La perla after overseeing $500k in renovations. How'd we get the men to show up every day and get the job done? We passed out $20 bills to the best workers every day, gave them free Red Bulls and Cokes to keep their energy up, and free beers every day at 4pm when work was done.

Above: East-West mortgage folks with John Kerry's wife Theresa. John on far right.

Above: Home owners susan (left) and john (far right) with the Imus in the morning crew, newsman Chuck McCord (mid-left) and Bernard (mid right).

Above: John took 30 of his 300 employees at East-West Mortgage for a tour of Fenway Park right after John Henry bought the team.

Above: John (right) with Joe Kennedy, son of Ethel and Bobby kennedy. While not a Democrat, John schmoozes with Joe Kennedy at the Kennedy compound Hyannis Cape Cod.

Above: Remember hearing those zillions of radio ads for East-West Mortgage Featuring John and jen last ten years??? Well John was the CEO of the company, and here he is with "Jen" on the left. On far right is famous Record company executive Jerry Brenner at John's 50 th Birthday party. (Jerry has received over 100 gold and platinum albums from the Major labels and knew John 30 years ago when John was a DJ and Executive at WAAF in Worcester)

Above: Golf foursome at the kennedy compound Hyannisport included Running Back legend Gale Sayers here with john (not pictured Bill Russell Celtics)

Above: Being greeted by Senator Ted Kennedy at the Kennedy compound Hyannisport Cape Cod for a John Kerry fundraiser
John with Senetor John Kerry
Above: John gives some advice to Democratic Presidential nominee John Kerry
John and Susan with President Bush
Above: John and Susan with President George W. Bush
John with former President George Bush Sr.
Above: John with President Bush (Sr.). Not discussed was the assassination of President Kennedy and new recent disclosures that E Howard Hunt, Richard Helms and other rogue CIA/mafia figures may have been involved (Bush was also a CIA director). Hunt claimed on his death bed a short while ago (April 2007) that Jack Ruby was paid by Chicago mafiosa to silence Oswald, and that the Kennedy event was triggered by CIA operatives upset about Kennedy’s failure to fully support the Bay of Pigs/Cuba invasion.
John with Senetor John Kerry
Above: John takes East-West Mortgage execs out to boston's famous Olives restaurant with celebrated chef Todd English
John and Susan with President Bush
Above: Home owner John with Georgia Senator Max Cleland at John Kerry's house in Boston's Beacon Hill. Max lost both legs while serving in Viet Nam.

Above: Remember the movie: The Sentinel, starring Michael Douglas and Kim Basinger ? Here's film star David Rasche (center) who played President of the U.S. in the film at charity golf event with Rob Babcock VP at TD BankNorth and homeowner John

Above: TD BankNorth VP Rob Babcock, NBA all star Gus Williams, and homeowner John at the charity golf fundraiser for the Barton Center of Oxford Mass for Diabetic children June 2007
John and his daughter with Tim Russett
Above: The late Tim Russert. Former host of NBC's Meet the Press asks John and Daughter Rachael if he can join them at the new St. John house(s) in the Virgin Islands.
John and his daughter with Tim Russett
Above: The Gallaghers at the Kiss 108 concert with pop superstar Avril Lavigne Backstage

Above: John with Talk Radio Personality Bill O'Reilly

Have a super time and drop us a line or a digital photo and be sure you have fun! Life’s too short not to.

Best Personal Regards,

Owners and Bon Vivants



View Our Guest Book Sign our Guest Book

testimonials

  • (stayed at Stowe VT house 911 Notchbrook Sept 2007)



    Hi John,



    I am writing to tell you about .... Read All

    By: Anne C.
  • I found your web site to be very informative not only about the rental properties but also about the island

    By: Kim Belmont
  • We just wanted to drop you a quick note to thank you for a fabulous long weekend in Bretton Woods, # 5 Presidential Oct 8-12, 2009.


    Read All

    By: Jim & Carolyn D.
  • A vacation house on steroids !



    (stayed at 911 Notchbrook, Stowe VT)



    a truly relaxing vacatio .... Read All

    By: guests from Canada
  • (stayed at 78 Dawns Beach estates March 2007)



    David and I want to thank you for sharing your home with us and our friend .... Read All

    By: David and Joanne
  • John/Susan (re: house # 78 Dawns Beach Estates)



    On behalf of our extended family, I wanted to let you know what a great .... Read All

    By: Sandra
  • (stayed at La Perla in St. Maarten Jan 2009)



    John, What an incredible spot you have there.

    .... Read All

    By: Louise C.
  • just wanted to let you know what a great time we had at La Perla.

    We enjoyed everything about the place and were amazed at the
    Read All

    By: Sandy M
  • We have stayed at the house at 1936 Notchbrook 3 times...each time has been wonderful. Thank you so much! Can't wait to come back!

    By: Tara McDonough
  • We were in Wild Jasmine last week. It was absolutely the most beautiful spot imaginable. The house was incrdible. We did miss the computer but that .... Read All

    By: Al Morier
  • John,



    thank you so much for our stay at La perla (St. Maarten).



    The house was great and we h .... Read All

    By: Chris M.
  • (stayed at Stowe fall 2008)



    Received your e-mail today about upcoming availability for your vacation rentals and realize .... Read All

    By: Gail T.
  • (stayed at St. john 4 br house)(March 2008)



    The beauty of this island amazes us daily.



    The b .... Read All

    By: Carla & Russ
  • (stayed at Stowe house 1936 Notchbrook Oct 2008)



    Our visit to Vermont is over but I wanted to send you guys a note to te .... Read All

    By: Tracie
  • (stayed at La Perla, St. Maarten house)



    What we liked best on our recent vacation at your house:


    Read All

    By: Annette and Steve S.
  • (stayed at St. John house U.S. Virgin Islands, Wild Jasmine)



    Dear John,



    Thank you so much fo .... Read All

    By: Bob A.
  • (stayed at 34 Forest, Bretton Woods NH Feb 2007)



    Hi John and Susan,



    We just got back from st .... Read All

    By: Jennifer L
  • The St Maarten properties are beautiful!!

    By: Jim Johns
  • Dear John and Susan



    I have been meaning to take a moment since we returned to tell you what an awesome time our family h .... Read All

    By: Denise
  • Great house- Pres.5 in Bretton Woods! Plenty of room for all of us-accomodations are great! We had so much room and everything we needed.

    Read All

    By: joyce
  • John - Thank you so much for allowing us to stay at La Perla! It was a WONDERFUL stay (May 10-17). The house is AWESOME! I will be telling MANY people .... Read All

    By: Lisa Ruhlman and Crew
  • (stayed at Sunday River, Maine house Jan 2010)



    Our group had an awesome stay at the house. Thanks for the great experien .... Read All

    By: Angelica
  • (stayed at 5 br st. john house March 2008)



    Hi all,



    We had a fantastic vacation at your lovel .... Read All

    By: carla f.
  • Hi John,



    We rented your place at Dawns beach St. Maarten last year and now we're looking to return this .... Read All

    By: Heidi
  • (stayed at St. John 5 br house April 2008)



    We had a fabulous vacation here at Wild Jasmine. I hope to be back.

    By: Meg from Essex, Massachusetts
  • Hi there!







    Just wanted to let you know we had a GREAT time in St. Maarten largely due to La .... Read All

    By: Kim G
  • We just spent a "Girls Weeked" at 34 Forest Cottage. Canopy Tour at Bretton Woods is not too be missed !! House was clean First off it is .... Read All

    By: Donna White
  • Lookong forward to our vacation in Coral Bay!

    By: TAMBRA BURKE-LEIZEAR
  • Hello there....just returned from our wonderful stay at #5 Presidential. The view alone of Mt. Washington made the trip! What a fantastic view! We p .... Read All

    By: Carol
  • (stayed at St. John 4 BR house March 2008)



    this is a piece of paradise we'll always remember.

    .... Read All

    By: Claire








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