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Hamptons.com
July 28, 2020

Minimalizing Capital Gains with Estate Planning

rschlackby rschlack
in Real Estate
Home Real Estate

Real property in the Hamptons has always enjoyed a steady increase in value. But with this increase in value, owners may incur a substantial tax bill from the capital gain in their real property if and when they decide to sell. Federal long-term term capital gains are taxed at the rate of 0%, 15% or 20%, depending on the seller’s income and marital status. In addition, New York capital gains are taxed as ordinary income. Fortunately, if the property being sold is a primary residence in which the seller has resided for 2 or more years, the seller can claim the benefit of a $250,000 exclusion ($500,000 for a married couple). In addition, sellers can deduct any capital improvements they have made over the years.

Even for a modest couple living on the East End, the capital gain is a huge consideration when contemplating a sale. For example, consider the case where a married couple owns a primary residence in Sag Harbor. In 1979 they purchased the property for $100,000 and, over the years, expended $400,000 on home improvements. The basis for capital gain purposes is therefore $500,000. Assume they now receive an offer to sell and will net $3 million after closing costs. Each spouse can claim each a $250,000 exemption from capital gains, shielding $500,000 from capital gains tax. Accordingly, the gain on which they will be taxed is $2 million dollars, resulting in a substantial tax bill.

How can this hefty capital gains tax be avoided? One method is to wait until one spouse passes away and the surviving spouse receives a step-up in basis for one-half the value of the home. This is possible because at death, all property owned by the decedent spouse, not just the primary residence, gets an increase in basis equal to fair market value as of the date of death. So, in our example above, when the first spouse dies, that spouse’s one-half gets stepped up to $1.5 million. At a subsequent sale, the surviving spouse’s basis is $250,000 plus the $250,000 exemption. This, coupled with the step-up received at the first spouse’s death, places the basis in the real property at $2 million. Thus, the surviving spouse only pays capital gains on $1 million, resulting in a significant savings.

However, there may be a way to save even more capital gains – in fact even reduce the tax to zero. The surviving spouse may be able to avoid all capital gains tax on a sale if they purchased the property before 1977. In that case, there is a 100% step-up in basis at the death of the first spouse. The “catch” is that you are only able to get the full step-up in basis at the death of the first spouse if that now deceased spouse contributed all the money to the purchase of the property. These were the facts of the now famous Gallenstein case where the Court found in favor of the tax payer and awarded a 100% step-up in cost basis at the death of the first spouse for a property that had been purchased pre-1977 when Congress changed the tax law.

In order for this “double” step up in basis to apply, the deed must have been continuously in both names pre-1977 until the death of the first spouse. Transferring the deed will negate this benefit, even if the deed is later transferred back into both names. The moral of the story is always review the chain of title of the deed. If it is owned by both spouses before 1977, speak to an attorney before making any changes to the deed.

What if the house was not purchased before 1977 or if there had been a change to the deed? A 100% step up in basis at the death of either spouse can still be achieved by placing the home or property into a joint revocable trust. If drafted properly, the surviving spouse can completely eliminate capital gains tax on a sale after the death of either spouse, regardless of who contributed to the purchase of the property. Also, any assets, real or personal property, owned by the trust will get a 100% step up.

Any such trust must be part of a comprehensive estate plan that considers estate taxes as well. Potential estate taxes are especially relevant now, with large government spending. In a post-COVID and post-election society, we may well see a reduction in estate tax exemptions. For high value estates, a varied approach that does not place all assets into a joint trust is necessary if both spouses’ estate tax exemptions must be captured, as the estate tax rates are higher than long-term capital gains tax rates.

Estate planning is nuanced, there are pros and cons to every estate planning technique. It is important to review your specific situation and goals with an experienced estate planning attorney to ascertain the most beneficial choice for you.

For more information, visit burnerlaw.com.

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LOCAL EVENTS

Events

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Art in Action (Zoom Sessions)

March 13 @ 10:30 AM - March 13 @ 11:30 AM
279 Montauk Highway Water Mill, NY 11976 United States
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The Modern Marionette Company – Martha Graham with Kim Profaci

March 13 @ 04:30 PM - March 13 @ 06:00 PM
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3v3 Co-ed Basketball Tournament for Grades 6–8

March 13 @ 05:00 PM - March 13 @ 08:00 PM
Ross School, 18 Goodfriend Drive, East Hampton, NY 11937
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HamptonsFilm X Guild Hall: Winter Classic “Paths of Glory”

March 13 @ 07:00 PM - March 13 @ 09:00 PM
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The Irish Tenors

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A New Kind of Hand Sanitizer, #InYaHands, Hits the Market

A New Kind of Hand Sanitizer, #InYaHands, Hits the Market

  • Check out the Top Hamptons Events This Weekend!⁠
⁠
🎬 HamptonsFilm X Guild Hall: Winter Classic Series – “Paths of Glory”⁠
📅 Friday, March 13⁠
⏰ 7 PM⁠
📍 Guild Hall – East Hampton⁠
HamptonsFilm and Guild Hall’s Winter Classic Series returns with HamptonsFilm Co-Chair Alec Baldwin and Chief Creative Officer David Nugent presenting Stanley Kubrick’s 1957 epic Paths of Glory, starring Kirk Douglas.⁠
⁠
☘️ Westhampton Beach St. Patrick’s Day Parade⁠
📅 Saturday, March 14⁠
⏰ 12 PM – 3 PM⁠
📍 Main Street – Westhampton Beach⁠
Celebrate St. Patrick’s Day with the whole community!⁠
⁠
🍀 St. Patrick’s Day at the Sunset Social Club⁠
📅 Saturday, March 14⁠
⏰ 2 PM⁠
📍 Sunset Theater – Westhampton Beach⁠
Keep the celebration going with Irish coffee and perfectly poured Guinness.⁠
⁠
🛍 Sag Saturday⁠
📅 Saturday, March 14⁠
⏰ All Day⁠
📍 Sag Harbor Village⁠
A celebration of culture, cuisine, community, and shopping in the heart of Sag Harbor.⁠
⁠
🥾 Barcelona Neck Preserve Hike⁠
📅 Saturday, March 14⁠
⏰ 10 AM – 12 PM⁠
📍 Sag Harbor Golf Course – Sag Harbor⁠
A scenic hike featuring views of Cedar Point Lighthouse and the surrounding natural beauty.⁠
⁠
🧘 A Morning of Mindfulness & Stillness⁠
📅 Saturday, March 14⁠
⏰ 11 AM – 12 PM⁠
📍 Dragon Hemp Apothecary – Sag Harbor⁠
A meditative morning guided by Reiki Master Marissa Kerwin with products designed to support relaxation and clarity.⁠
⁠
🎥 The Oscars: Live from Sag Harbor⁠
📅 Sunday, March 15⁠
⏰ 5:30 PM – 10 PM⁠
📍 Sag Harbor Cinema⁠
Walk the red carpet, vote in the Oscars ballot, and compete for best dressed. VIP tickets include cocktails and canapés.⁠
⁠
🦭 Seal Cruise in Southampton⁠
📅 Sunday, March 15⁠
⏰ 12 PM – 2 PM⁠
📍 Stony Brook Marine Station – Southampton⁠
Join a CRESLI scientist for a two-hour expedition observing seals in Shinnecock Bay.⁠
⁠
🎷 Generations of Jazz: Women in Modern Jazz⁠
📅 Sunday, March 15⁠
⏰ 2 PM – 3:30 PM⁠
📍 St. Ann’s Episcopal Church – Bridgehampton⁠
A multi-generational ensemble celebrating the power of female voices in modern jazz.⁠
⁠
#hamptons #stpatricksday #weekend⁠
  • The Center for Family Services Palm Beach County held its signature fundraiser, The Old Bags Luncheon™, at the iconic Breakers Palm Beach. Palm Beach County continues to experience a growing need for accessible mental health services, with families facing challenges such as economic hardships, trauma, and mental health disparities. The Center for Family Services serves as a beacon of hope, offering these families the resources and professional care needed to overcome adversity.⁠
⁠
The Center’s annual signature event combines fashion, philanthropy, and social engagement, attracting some of the most influential individuals in the region to support the organization’s critical work. This year’s event sold out in record time and had a long wait list. ⁠
⁠
This year, the 2026 OBL Celebrity Speaker was Priscilla Presley – cultural icon, actress, and philanthropist who brought her singular story and passion for advocacy to The Breakers ballroom.⁠

📸: @andrewwerner 
⁠
Read the full article at Hamptons.com (Link in Bio)⁠
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#oldbagsluncheon #palmbeach #priscillapresley #robertjames
  • Check out the Top Hamptons events This Weekend!⁠
⁠
🎨 2026 Student Exhibition Preview Day⁠
📅 Saturday, March 7 | ⏰ 11am–5pm⁠
📍 Parrish Art Museum, Water Mill⁠
Saturday is for the arts! Enjoy exhibition previews, a drop-in drumming circle, imagination play workshops, and a performance by the Southampton String Ensemble.⁠
⁠
🎻 Fiddler’s Green: A Traditional Irish Music Concert⁠
📅 Saturday, March 7 | ⏰ 1–2:30pm⁠
📍 Southampton History Museum, Southampton⁠
Fiddler’s Green brings the traditional music of Ireland to the East End.⁠
⁠
🍀 Pot O’ Gold Catapult Workshop⁠
📅 Saturday, March 7 | ⏰ 3–6pm⁠
📍 Children’s Museum of the East End, Bridgehampton⁠
Kids can build a catapult and launch gold coins into the lucky pot.⁠
⁠
🎸 Gene Casey and the Lone Sharks⁠
📅 Saturday, March 7 | ⏰ 8–10pm⁠
📍 Bay Street Theater, Sag Harbor⁠
Dubbed “the house band of the Hamptons,” the group brings their iconic country sound to the stage.⁠
⁠
🥣 Project MOST’s Empty Bowls⁠
📅 Sunday, March 8 | ⏰ 12–3pm⁠
📍 Amagansett American Legion Post 419⁠
Taste soups crafted by local chefs while supporting vital programs for children and families. Plus live music, a 50/50 raffle, and family fun.⁠
⁠
🎤 “Sing-Along the American Songbook” Jazz Jam⁠
📅 Sunday, March 8 | ⏰ 2–5pm⁠
📍 Southampton Cultural Center⁠
Celebrating Women’s History Month with vocalists Ludmilla Benevides and Vanessa Trouble, joined by Jane Hastay, Iris Ornig, and Carl Sarafina.⁠
⁠
🥘 Spanish Tapas & Paella Cooking Class⁠
📅 Sunday, March 8 | ⏰ 3:30–6:30pm⁠
📍 R.AIRE, Hampton Bays⁠
Cook alongside Chef Alex, enjoy wine pairings, and dine together afterward.⁠
⁠
🥾 Montauk Loop Hike⁠
📅 Saturday, March 7 | ⏰ 10am–12:30pm⁠
📍 Montauk Lighthouse⁠
Explore scenic trails and keep an eye out for harbor seals.⁠
⁠
🎬 Hoppers in IMAX⁠
📍 Southampton Playhouse⁠
Follow Mabel as her consciousness transfers into a robotic beaver and she enters the animal world.⁠
⁠
📚 BookHampton Book Club: Vigil⁠
📅 Tuesday, March 10 | ⏰ 4pm⁠
📍 LongHouse Reserve, East Hampton⁠
Join fellow readers to discuss George Saunders’ newest book.⁠
⁠
Visit Hamptons.com for more events!⁠
⁠
#weekend #hamptons #hoppers #events #books
  • Quogue Wildlife Refuge held its beloved “Light The Night” trail walk. I’ve heard through the grapevine that the annual walk is magical, peaceful, and paints the dreaded cold winter nights in a whole new light (literally).⁠
⁠
The community braced the cold, freezing temperatures as they followed a lantern trail and entered a quaint marketplace with a Hamptons Coffee Company booth serving delicious, complimentary hot chocolate in reusable mugs, a merch booth with an impressive selection of animal stickers, beanies, pins, maps, stuffed animals, and my personal favorite, a bandana with a map of the Refuge. A must-have for any wildlife fanatic.⁠
⁠
📸: Quogue Wildlife Refuge & Dennis Maroulas & Hamptons.com⁠
⁠
Read the full article at Hamptons.com (Link in Bio)⁠
⁠
#quoguewildliferefuge #lightthenight #trail #community
  • As the Hamptons’ ultra-luxury sector accelerates—with sales above $20 million doubling year-over-year—an architecturally significant coastal contemporary estate has entered the market at $32 million.⁠
⁠
Located at 200 Rose Hill Road in Water Mill, the newly constructed residence spans approximately 19,000 square feet across three levels and is set on 2.29 landscaped acres overlooking a 65-acre agricultural reserve. Mecox Bay lies at the end of the street, with Atlantic Ocean beaches just moments beyond.⁠
⁠
Recently acquired by Moskow Management Trust and offered fully furnished, the gated estate is exclusively represented by Vince Horcasitas of Saunders & Associates.⁠
⁠
@vinceinthehamptons⁠
@hamptonsrealestate⁠
⁠
Read the full article at Hamptons.com (Link in Bio)⁠
.⁠
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#hamptons #realestate #luxury #watermill
  • Check out the Top Hamptons Events This Weekend!⁠
⁠
From art openings to live music and family fun — here’s what’s happening:⁠
⁠
🖼 Opening Reception: Reclaiming Death Exhibition⁠
📍 Ma’s House, Southampton⁠
🕔 Saturday, Feb 28 | 5–8PM⁠
A powerful group exhibition featuring 20 artists exploring personal and cultural end-of-life practices.⁠
⁠
🎬 2026 Oscar-Nominated Short Films at Sag Harbor Cinema⁠
🕗 Saturday, Feb 28 | 8–10PM⁠
Catch this year’s Oscar-nominated Animated, Documentary, and Live Action shorts.⁠
⁠
👨‍👩‍👧 Family Day at Guild Hall⁠
🕐 Saturday, Feb 28 | 1–3PM⁠
Stop-motion films, tours, and hands-on activities for all ages.⁠
⁠
🥾 Four Ponds Hike⁠
📍 Long Pond Greenbelt Nature Center, Bridgehampton⁠
🕙 Saturday, Feb 28 | 10AM–12PM⁠
A scenic 3.5-mile hike with pond views.⁠
⁠
🎸 The Surfcasters: A Led Zeppelin Celebration at Bay Street Theater⁠
🕗 Saturday, Feb 28 | 8–10PM⁠
Classic rock energy all night long.⁠
⁠
🎻 Clarice Jensen Live at The Church⁠
🗓 Sunday, March 1 | 3–4:30PM⁠
A contemporary classical performance from her latest album.⁠
⁠
🎨 Clay Workshop for Kids⁠
📍 Mudita, Water Mill⁠
🕚 Saturday, Feb 21 | 11AM–12PM⁠
Hands-on creative fun with clay.⁠
⁠
🎤 The Seismatics at Stephen Talkhouse⁠
🗓 Feb 27 | 8PM⁠
Modern + classic rock hits.⁠
⁠
🍷 Wine Wednesday at Nick & Toni’s⁠
🗓 March 4 | 5:30–7PM⁠
Discover highlights from Frederick Wildman.⁠
⁠
Check out more events at Hamptons.com (Link in Bio)⁠
.⁠
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#hamptons #arts #oscars #easthamptons #weekend
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