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Hamptons.com
February 3, 2015

To Buy Or Not To Buy A Vacation Home?

Rocco A. Carrieroby Rocco A. Carriero
in Real Estate
Home Real Estate

You’ve always wanted to own a vacation home, and now you finally feel ready to make that purchase. Before you put an offer in for a cabin on the lake or condo in the mountains, consider the realities of owning a second property. Here are a few questions to think about before you finalize your plans.

Can you afford it?

Owning a second home entails additional expenses such as:

  • Furniture or other household items
  • Travel costs like airfare or wear and tear on your vehicle
  • Annual repairs or improvements to the property
  • Recreational desires such as a boat, winter skis or kayaks
  • Utilities including heat, air conditioning, water, internet and cable if you choose to have it
  • A security system for when you’re away

    If your primary residence is more than a few hours away from your vacation home, or if you plan to rent out your vacation home, you also may need to hire someone to manage the property.

    Is the location right?

    Naturally, you have an idea of where you’d like your vacation home to be located. But, have you given much thought to what that means in terms of year-round use? Homes in areas where temperatures dip below freezing need to be winterized and monitored to avoid frozen pipes. Where there’s snowfall, there’s shoveling and plowing to manage. Distance is also a key consideration, along with the relative ease of getting there. Have you chosen a location and property that will grow in value or will it be hard to sell when the time comes? These are all important questions to answer as you consider purchasing another home.

    Would renting be a better option?

    You don’t have to buy a vacation home to get away on a regular basis. A short-term rental property can provide the comforts of a home without the obligations of ownership. Rather than be tied to one place, you can try new locations and accommodations when you take a vacation. You can search online for everything from barebones apartments to sprawling homes, with rental options by the day, week or month. Alternately, if you do move forward with the purchase of a vacation home, you may want to explore listing your property as a rental when it’s not in use. If your vacation home is in a high demand area, you might be able to generate an income stream — but don’t forget to factor in the costs of managing the property from afar.

    How will your taxes be affected?

    Different tax rules apply to owning a second home, which can be somewhat complex depending on a variety of factors. Whether or not you rent the home, property taxes and mortgage interest are a few items that could affect your tax return. You’ll want to consult with a tax advisor to sort out the details and discuss how your taxes will be affected if you purchase another home.

    There are a lot of factors to think about before purchasing a vacation home. Consider working with a financial professional to determine how buying a second home will affect your longer-term financial plan.

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🖼 Opening Reception: Reclaiming Death Exhibition⁠
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🎬 2026 Oscar-Nominated Short Films at Sag Harbor Cinema⁠
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👨‍👩‍👧 Family Day at Guild Hall⁠
🕐 Saturday, Feb 28 | 1–3PM⁠
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🕙 Saturday, Feb 28 | 10AM–12PM⁠
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🎸 The Surfcasters: A Led Zeppelin Celebration at Bay Street Theater⁠
🕗 Saturday, Feb 28 | 8–10PM⁠
Classic rock energy all night long.⁠
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🎻 Clarice Jensen Live at The Church⁠
🗓 Sunday, March 1 | 3–4:30PM⁠
A contemporary classical performance from her latest album.⁠
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🎨 Clay Workshop for Kids⁠
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🕚 Saturday, Feb 21 | 11AM–12PM⁠
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🎤 The Seismatics at Stephen Talkhouse⁠
🗓 Feb 27 | 8PM⁠
Modern + classic rock hits.⁠
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🍷 Wine Wednesday at Nick & Toni’s⁠
🗓 March 4 | 5:30–7PM⁠
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#hamptons #arts #oscars #easthamptons #weekend
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So, if you’re looking for a clear, uncluttered, and elevated cannabis experience, Charlie Fox is for you. If you’re a first-timer, excited to explore cannabis (now legal in New York), or a lifelong enjoyer who’s looking for the best cannabis on the East End, find it at Charlie Fox Dispensary.⁠
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New to Southampton in 2026, Charlie Fox Dispensary is elevating the Hamptons’ luxury wellness/cannabis space with edibles (and drinkables) for every occasion, CBD+, premium vapes and pre-rolls, wellness topicals and remedies, the best flower in the Hamptons, and accessories you won’t have to hide when you entertain.⁠
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The local couple, who also own The Clam Bar and Sett Coffee, both located in Amagansett, are excited to introduce a refreshed concept that honors The Corner Bar’s storied past while ushering in a new era. The vision preserves The Corner Bar’s beloved, old-school neighborhood charm while updating the design, brand, and menu for a more modern sensibility. Guests can expect a thoughtfully designed space with an approachable vibe – timeless, local, and familiar.⁠
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Read the full article at Hamptons.com (Link in Bio)⁠
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    • This past week, Share the Harvest Farm welcomed a sold-out gathering of women to Wölffer Estate for its “Share the Love” Galentine’s Wine Charm Workshop, an evening of creativity, connection, and community in support of the farm’s mission to fight food insecurity on the East End.⁠
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Held at the iconic Wölffer Estate in Sagaponack, guests mingled over Rosé before designing custom wine charms under the guidance of Madison Powell of EAST + PALM. The thoughtfully curated charm bar featured botanical, coastal, and Valentine’s Day-inspired elements, with every detail reflecting EAST + PALM’s signature attention to detail. ⁠
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Kick off the weekend with Wölffer’s rosé and live music by Tom Wardle.⁠
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⛸ Katy’s Courage Fundraiser at Buckskill Winter Club⁠
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A full day of fun, community, and giving back.⁠
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    • Palm Tree Music Festival, the ultimate Hamptons party, returns for its sixth edition on Saturday, June 27th at the Shinnecock Reservation in Southampton. Known for blending world-class music with laid-back luxury,  the one‑day festival once again brings together an electric lineup and an atmosphere that captures summer at its absolute best. This year’s lineup includes headlining performances by Palm Tree Crew Co-Founder Kygo, The Chainsmokers, and Disco Lines, alongside additional sets by It’s Murph, Xandra, Will Sass, and Brooke Brazelton.⁠
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“The Hamptons has always been at the heart of the Palm Tree Music Festival story,” said Palm Tree Crew Co-Founder Myles Shear. “The energy from the fans and the local community makes this show truly special. We’re thrilled to return for our sixth year and have a lot in store to take this experience to new heights for another unforgettable celebration.”⁠
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