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December 1, 2014

How Can I Avoid Paying Taxes?

John A. Viterittiby John A. Viteritti
in Real Estate
Home Real Estate

Human nature being what it is, nobody likes to pay taxes. Certainly, no more than they have to. Real estate does offer some opportunities along those lines.

The tax benefits that most primary home owners are familiar with are the deductibility of real estate taxes and mortgage interest on their primary residences up to certain limits. Points, which represent pre-paid interest, are also deductible. Each point is equal to one percent of the loan. When the property is sold, the seller may also deduct certain closing costs incurred when the property was purchased. An owner of a second or vacation property may deduct property taxes and interest up to certain limits. They may lease their vacation homes in any given tax year for a period of less than fifteen days without income reporting requirements. If the owner leases the property for a period greater than fourteen days, the vacation home is considered an income producing property and taxed accordingly.

The change in the Tax Law in 1997 was significant with respect to profit on the sale of a home occupied as a primary residence for two of any of the five years prior to the sale. It allows for the deduction of a gain up to $250,000 for a single filer, and up to $500,000 for a married couple filing a joint return. Where there is more than one single filer, each may deduct up to $250,000 not to exceed $500,000 over all. With respect to the married couple filing jointly, only one spouse must own the property to be eligible for the $500,000 marital deduction. Same-sex married couples are eligible for the marital deduction as a result of the Supreme Court decision regarding the Defense of Marriage Act. The exclusion may be taken every two years. It is also possible to qualify for a proportionate deduction if the home has to be sold before the two year occupancy requirement. The eligibility is allowed under hardship conditions delineated in the Tax Code.

In addition to the exclusions from capital gains, the cost of capital improvements made to the home while occupied as a primary residence may be added to the adjusted cost basis along with certain closing costs incurred when the property was purchased, including the 1% New York State “Mansion Tax” on the purchase price of one million dollars or more for one, two, or three unit building, including residential condominiums and cooperatives. The payment of the 2% Community Preservation Fund Tax, (Peconic Tax), may also be added to the adjusted cost basis. Qualified first-time homebuyers in Southampton, Shelter Island, East Hampton and Southold are exempt from paying the tax upon making application to the Towns.

New York State STaR Program, (School Tax Relief), allows a reduction from the school tax portion of the property’s real estate taxes on a primary residence. In order to be eligible, the household income may not exceed $500,000. The Enhanced STaR exemption is available if at least one owner is at least sixty-five years of age and the adjusted household income does not exceed $81,900. This amount is scheduled to increase in 2015 to $83,300.

For investment properties, Section 1031 of the Federal Tax Code allows for the deferment of taxes due on the exchange of investment properties. The properties must be of “like kind” meaning investment properties including unimproved properties intended for commercial development, income producing residential properties, and other qualified properties identified in the Tax Code. These exchanges have to be conducted through a qualified intermediary. The replacement properties must be identified within forty-five days and the exchange conducted within one hundred and eighty days. Where the value of the properties are not equal, the owner of the lesser valued property must pay “boot” – personal property to even out the exchange.

Each of these tax issues is more complex than articulated in this article, and a tax lawyer or accountant should be consulted before attempting to utilize any of these tax benefits.

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Billy Joel’s Beachfront Sagaponack Estate Closes For $19M: This Week’s Top Hamptons Real Estate Transfer

Billy Joel's Beachfront Sagaponack Estate Closes For $19M: This Week's Top Hamptons Real Estate Transfer

  • Every year at the Hamptons International Film Festival, there is a film that captures the local East End experience. This year, many believe that film is ON THE END, written and directed by Ari Selinger. In a half-hour Zoom call, Ari Selinger shared the story of how his debut writer-director indie-drama film came about.⁠
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He said, “I was location scouting all over New York, and I found myself on Navy Road (Montauk) back in 2011 with my production designer friend. We were two 20-year-old film students (NYU) looking for a shoddy auto repair shop that we could use to shoot a film. There I met this guy, Tom, in front of his very dirty property. He was fixing a car. He came up to the window and not only told us about numerous people to talk to… he just knew all these names, and he just seemed to be a resource. He’d always be whispering in my ear about this thing he was going through with the town, about this battle, about him trying to keep his house. And it totally went over my head at the time. I did not know very much about zoning laws and property values, and maybe I was a little bit cavalier about it, but back in 2016, there was a big piece in the New York Times on his story.”⁠
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Read the full article at Hamptons.com (Link in Bio)⁠
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#ontheend #indie #hamptonsfilmfestival #HIFF #filmfestival #easthampton #local
  • Sag Harbor resident, actor, writer, and teacher Josh Pais has spent decades exploring what it means to be fully present—on screen and in life. Known for his roles in Joker, Ray Donovan, the original Teenage Mutant Ninja Turtles, and many others, he has more than 150 film and television credits to his name. He has now turned his focus inward with his new memoir, Lose Your Mind: The Path to Creative Invincibility, which was released on September 30, 2025.⁠
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Drawing on his years of experience as founder of the Committed Impulse training method, Josh offers readers a bold invitation to release self-judgment, lean into all feelings, and connect with the spontaneous energy that fuels authentic creativity. His message—both playful and profound—challenges the myth of “good” and “bad” emotions and instead celebrates the full spectrum of human experience.⁠
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Josh will visit Sag Harbor for a reading and book signing this Sunday, October 12th from 4:00–5:30 p.m. at Grenning Gallery (26 Main Street, Sag Harbor). ⁠
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📸: Commune Media⁠
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Read the full interview at Hamptons.com (Link in Bio)⁠
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#hamptons #joshpais #book #sagharbor #author #actor
  • @linamxn at the Sag Harbor Music Festival! @sagharbormusic 

The four day festival kept the music going over 4 days at various stages in Sag Harbor. 

#sagharbormusicfestival #sagharbor #hamptons #livemusic #linamaxine #local
  • Grab your furry friend and take a stroll to Main Beach with ARF!

Check out the Top Hamptons Events This Weekend!

🐾 ARF’s Stroll to the Sea Dog Walk
📅 When: Saturday, October 11, 2025 | 9AM–12PM
📍 Where: Mulford Farm, 10 James Lane, East Hampton, NY

Enjoy vendors, contests, and giveaways before strolling to Main Beach.

🥣 Chowdah Chowdown
📅 When: Saturday, October 11, 2025 | 12PM–3PM
📍 Where: Springs Tavern and Grill, 15 Fort Pond Blvd, East Hampton, NY

All-you-can-eat chowder and soup from 20 local chefs, plus live music and a mocktail bar — all to benefit the Springs Food Pantry!

🍺 SagtoberFest
📅 When: Sat, Oct 11 – Sun, Oct 12, 2025 | 12PM–8PM
📍 Where: Kidd Squid, 11 Spring St, Sag Harbor, NY

Celebrate Oktoberfest Sag Harbor–style! Enjoy bratwurst, pretzels, oysters, pumpkin stew, and live music by Jon Divello, Woody Boley, Greg McMullen & Jake Lear.

🎬 33rd Hamptons International Film Festival
📅 When: Thurs, Oct 9 – Mon, Oct 13, 2025 | 9AM–10PM
📍 Where: Various Locations

The 33rd edition of HIFF brings a world-class lineup of narrative and documentary films, features, and shorts from around the globe. 

🍪 Levain Bakery: Book Talk & Signing
📅 When: Saturday, October 11, 2025 | 12PM–1PM
📍 Where: BookHampton, 41 Main Street, East Hampton, NY

Meet Levain Bakery cofounders Pam Weekes & Connie McDonald and grab their new book.

🌿 26th Annual Long Pond Greenbelt Celebration
📅 When: Saturday, October 11, 2025 | 10AM–1PM
📍 Where: SOFO Museum, 377 Bridgehampton–Sag Harbor Tpk, Bridgehampton, NY

Enjoy games, crafts, guided walks, face painting, and ice cream!

🎉 CMEE’s Big Birthday Bash!
📅 When: Saturday, October 11, 2025 | 10AM–12PM
📍 Where: SOFO, 376 Bridgehampton–Sag Harbor Tpk, Bridgehampton, NY

Join for crafts, treats, dance, and play!

🛋️ Hub Home Grand Opening Party & Open House
📅 When: Friday, October 10, 2025 | 6PM–9PM
📍 Where: HUB Home, 2183 Montauk Hwy, Bridgehampton, NY

Celebrate the grand opening of HUB Home, a curated consignment shop with luxury furnishings, art, and décor.

Check out more events at Hamptons.com (Link in Bio)
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#hamptons #arf #community #stephentalkhouse #dining #hamptonsfilmfestival
  • The 33rd Hamptons International Film Festival kicked off last Friday with the U.S. premiere of A24’s Eternity starring Elizabeth Olsen, Miles Teller, and Callum Turner.⁠
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Elizabeth Olsen attended the premiere on Friday, and on Saturday sat down with IndieWire’s Editorial Director Kate Erbland at the Sag Harbor Cinema as a part of the festival’s “A Conversation With” series. Later that day, the second “A Conversation With” took place as Ethan Hawke and moderator Alison Stewart talked about Blue Moon, as well as Hawke’s filmography. ⁠
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Sydney Sweeney received the festival’s Achievement in Acting Award following the U.S. premiere of her film Christy in East Hampton. ⁠
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Notable Guests included: Alessandro Nivola, Alec Baldwin, Amanda Peet, Tonatiuh, Miriam Shor, Lois Smith, Tim Blake Nelson, Mareille Enos, Bob Balaban, E. Jean Carroll, Roberta Kaplan, Ellen Barkin, Bernie Telsie, Bill Condon.⁠
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📸: Jess Dalene⁠
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Check out the full gallery at Hamptons.com (Link in Bio)⁠
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#hiff #hamptonsinternationalfilmfestival #film #elizabetholsen #sydneysweeney #hamptons #hamptonsfilm⁠
  • When: Fri, Oct 3rd – Sun, Oct 5th, 2025
8am – 5pm

Where: Levain Bakery, 354 Montauk Hwy, Wainscott, NY

Levain Bakery is introducing a new cookie for a limited time: Peanut Butter Dark Chocolate Chip – a decadent mix of creamy and chunky peanut butter with rich dark chocolate chunks. Originally created to celebrate the opening of Levain’s Beverly Hills Bakery, this indulgent new flavor will now be available for just three days only, October 3–5, at all retail bakery locations.

To make the weekend even sweeter, guests who purchase a cookie will receive a Levain Bakery mini tote (while supplies last), a fan-favorite collectible sure to go quickly.

#levain #levainbakery #cookie #minitote #tote #hamptons
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