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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

22
Dec
22
Dec
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02
Jan

Holiday Camp at The Green School

December 22 @ 09:00 AM - January 2 @ 03:00 PM
The Green School, 287 Merchant's Path, Sagaponack NY 11962
23
Dec
23
Dec
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23
Dec

Popsicle Stick Sled

December 23 @ 02:30 PM - December 23 @ 03:30 PM
The Hampton Library
24
Dec
24
Dec
-
24
Dec

Celebrate Christmas Eve at Nick & Toni’s

December 24 @ 05:00 PM - December 24 @ 09:00 PM
136 N. Main St., East Hampton, NY 11937
24
Dec
24
Dec
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24
Dec

FĒNIKS in Southampton to Offer a Taste of Seven Fishes on Christmas Eve

December 24 @ 06:00 PM - December 24 @ 09:00 PM
75 Jobs Lane, Southampton, NY, 11968
27
Dec
27
Dec
-
27
Dec

Saturday Camp AM and Extended Day Drop Off: 12/27 Gnome Workshop at the Green School!

December 27 @ 09:00 AM - December 27 @ 03:00 PM
The Green School, 287 Merchants Path, Sagaponack, NY 11962
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A New Kind of Hand Sanitizer, #InYaHands, Hits the Market

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

  • 🎄 This Weekend in the Hamptons 🎶✨⁠
⁠
🎷 Hamptons JazzFest Presents: NYC Spirits⁠
📅 Fri, Dec 19 | ⏰ 6:30–9pm⁠
📍 Masonic Temple, Sag Harbor⁠
An evening of world-class jazz⁠
⁠
🎻 Candlelight: Christmas Carols on Strings⁠
📅 Sat, Dec 20 | ⏰ 6–7pm⁠
📍 Guild Hall, East Hampton⁠
A magical concert where music and visuals meet⁠
⁠
🍷 Winter Wonderland at Wölffer Estate Vineyard⁠
📅 Sun, Dec 21 | ⏰ 11am–2pm⁠
📍 Sagaponack⁠
Festive drinks, cozy firepits & family fun⁠
⁠
🕎 Pop-Up Chanukah: Eitan Levine⁠
📅 Sun, Dec 21 | ⏰ 5–7pm⁠
📍 Guild Hall, East Hampton⁠
Comedy, community & a menorah lighting⁠
⁠
🚂 The Polar Express⁠
📅 Sat, Dec 20 – Sun, Dec 21⁠
📍 Southampton Playhouse⁠
A holiday classic on the big screen⁠
⁠
❄️ Igloos by the Sea at Gurney’s⁠
📅 Fri, Dec 19 – Mon, Dec 20 | ⏰ 5pm & 7pm⁠
📍 Montauk⁠
Heated oceanfront igloos with festive bites & cocktails⁠
⁠
📚 Light, Sand and Sea Book Signing⁠
📅 Sat, Dec 20 | ⏰ 5–8pm⁠
📍 Baker House 1650, East Hampton⁠
A Hamptons-centered book celebrating local artists⁠
⁠
🎶 Consonance Music Ensemble at Marders⁠
📅 Sat, Dec 20 | ⏰ 1–3pm⁠
📍 Bridgehampton⁠
Holiday shopping with live music⁠
⁠
👉 Click the link in bio for more events⁠
⁠
#hamptons #guildhall #holidays #hanukkah #booksigning igloos livemusic winterwonderland wolffer
  • The Southampton Playhouse, located at 43 Hill Street in Southampton, has quickly reestablished itself as one of the East End’s most vibrant cultural spaces. After an extensive renovation and a reimagining of its mission, the beloved historic theater is once again bringing people together through film, conversation, and community.⁠
⁠
Under the leadership of Executive Director Maria A. Ruiz Botsacos and Artistic Director Eric Kohn, the Playhouse has evolved into a dynamic hybrid of state-of-the-art cinema and community arts hub—offering everything from IMAX blockbusters and 35mm classics to live performances, themed series, and exclusive talks with filmmakers.⁠
⁠
Read the full interview at Hamptons.com (Link in Bio)⁠
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#southampton #southamptonplayhouse #hamptons #film
  • On Saturday, December 13th @heartofthehamptons held their annual Polar Bear Plunge at Coopers beach in Southampton. 

The whole community came together for treats and plunged for a great cause ❄️

#polarbearplunge #coopersbeach #southampton #heartofthehamptons
  • HamptonsFilm announced that the 34th annual edition of the Hamptons International Film Festival will take place October 2-12, 2026. The 11-day festival will feature screenings and events across the Hamptons.⁠
⁠
HamptonsFilm announced that the 34th annual edition of the Hamptons International Film Festival will take place October 2-12, 2026. The 11-day festival will feature screenings and events across the Hamptons.⁠
⁠
The festival will begin accepting submissions via FilmFreeway in February. ⁠
⁠
“As we look ahead to the 34th edition of the Hamptons International Film Festival, we’re excited to continue to bring audiences eleven days of screenings and events across the East End,” said David Nugent, Chief Creative Officer of HamptonsFilm. “Each year, our filmmakers and audiences inspire us to grow, experiment, and celebrate bold new voices in cinema. With submissions opening in February and an exciting slate of year-round programs, from our Screenwriters Lab to SummerDocs and our beloved outdoor screenings, we can’t wait to welcome everyone back this October.”⁠
⁠
⁠
Read the full article at Hamptons.com (Link in Bio)

#hamptonsfilm #filmfestival
  • Check out the Top Hamptons Events This Weekend!

Hampton Ballet Theatre School’s 16th Annual Nutcracker at Guild Hall
When: Fri, Dec 12 – Sun, Dec 14, 2025 • 7pm, 12pm & 5pm
Where: Guild Hall, 158 Main Street, East Hampton, NY
Get into the holiday season with a timeless ballet!

Polar Bear Plunge in Southampton
When: Sat, Dec 13, 2025 • 9am–11am
Where: Coopers Beach, 268 Meadow Lane, Southampton, NY
Celebrate 22 years of getting freezing for a reason! 

Holiday Tour of the Inns
When: Sat, Dec 13, 2025 • 1pm–4pm
Where: East Hampton, NY
Enjoy festive décor and treats across East Hampton’s charming inns.

A Holiday Moment in The Hamptons
When: Sat, Dec 13, 2025 • 2pm–6pm
Where: 26 Montauk Highway, Amagansett, NY
Walk through the evergreens and enjoy cocoa, cider & treats benefiting the Eleanor Whitmore Early Childhood Center.

Amagansett Life-Saving Station’s 3rd Annual Tree Lighting & Toy Drive
When: Sat, Dec 13, 2025 • 4pm–5:30pm
Where: 160 Atlantic Ave, Amagansett, NY
Arts & crafts, cookies, hot chocolate, music — and bring an unwrapped gift for the Kiwanis Toy Drive!

A Christmas Carol: A Live Radio Play — Hampton Theatre Company
When: Fri, Dec 12 – Sun, Dec 14, 2025 • 7pm & 2:30pm
Where: Quogue Community Hall, 125 Jessup Ave, Quogue, NY
A festive classic returns for one weekend only!

Pop-Up Chanukah at Herrick Park
When: Sun, Dec 14, 2025 • 4pm–6pm
Where: Herrick Park, 67 Newtown Ln, East Hampton, NY
Celebrate with songs, donuts, gifts for kids, a dreidel drop & the lighting of the public menorah.

Breakfast with Santa at The Hampton Maid
When: Sun, Dec 14, 2025 • 8am–1pm
Where: 259 E Montauk Hwy, Hampton Bays, NY

Montauk Holiday Concert
When: Sun, Dec 14, 2025 • 3pm & 4pm
Where: Saint Therese of Lisieux, 67 S Essex St, Montauk, NY
Enjoy holiday classics!

Santa Selfies with Birds of Prey
When: Sat, Dec 13, 2025 • 1pm–3pm
Where: Marders, 120 Snake Hollow Rd, Bridgehampton, NY
Meet rescue birds from the Evelyn Alexander Wildlife Center!

Gifts & Carols at the Nathaniel Rogers House
When: Sat, Dec 13, 2025 • 4pm–6pm
Where: 2539 Montauk Hwy, Bridgehampton, NY
Sing along with the Dickens Carolers!

For all event details, see the link in bio. 

#hamptons
  • Saunders & Associates once again demonstrated its commitment to the East End community with the 12th Annual Thanksgiving Donation Drive, which this year reached a record-breaking milestone. ⁠
⁠
Coinciding with Giving Tuesday, the campaign raised an impressive $62,000 for Hamptons food pantries—making it the most successful drive to date and significantly expanding support for local families during the holiday season.⁠
⁠
As the Hamptons’ leading real estate brokerage, Saunders & Associates’ annual Thanksgiving Donation Drive underscores the firm’s longstanding commitment to supporting the Hamptons community all year long.⁠
⁠
Read the full article at Hamptons.com (Link in Bio)⁠
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#hamptons #saunders #community #foodpantries
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