A Season of Closings and New Beginnings
October 29, 2025
The one I sold, the one I bought, and what I learned
Dear friends,
October is typically a sad time in my world.
I grew up in a climate with lush green leaves reflecting sunshine from January to December and thick canopies that shielded me from the hot and high sun in October.
And so, for the past 16 years since I moved to NYC, when October rolls around, while I see the leaves turn golden and red and appreciate the visual feast nature puts on, melancholy fills my heart as I dread the next six months of barren branches and lip-bursting wind.
This October, for the first time since becoming a New Yorker, I find my heart filled with something else: so much hope, pinching-myself-to-see-if-it’s-true happiness, and bucket loads of gratitude.
At the Waldorf Astoria New York’s condo amenities reveal, by the stunning Starlight Pool
Two Houses, Two Stories ❤️
Within a few weeks, I closed on two very different homes — one I sold for a special family who I have helped on multiple occasions in the past few years, and one I bought for my own family as an investment and vacation home.
It’s a full-circle moment — helping someone sell their family home, and finally getting to plant roots of my own in my beloved upstate New York, building the real estate portfolio I’ve been dreaming of.
The full-circle spirit of this serendipitous timing continues, as I was even able to adopt some of my seller’s lovely furniture and give them a new life in my new place!!
✨🏡✨
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The One I Sold: A Story of Letting Go
You may remember, I shared a lot with you about this gem of a mid-century modern home in Rye, a NYC suburb ten minutes away from where my husband grew up in Mamaroneck.
In early October, I had the privilege of helping my sellers say goodbye to this piece of art that they reimagined with acclaimed architect Deborah Berke, so they can start their next exciting chapter somewhere new. Through working with different members of the family over the years, I had heard so many little moments that make a house feel alive — Thanksgiving turkey carved on the kitchen island, summer sunshine on the pool deck, and quiet mornings with coffee and the paper.
Enlisting the help of my colleague Stacey Rechler, a Westchester expert, we strategically took a multi-phase approach by testing the private market and incorporating its feedback into our full launch. Once we listed publicly, we got the home’s beautiful story told everywhere: the Robb Report, Cottage & Gardens, @zillowgonewild and even a full page in the New York Post!
The property captured the attention of buyers from London to California, from Germany to the Hamptons, many of whom were lovers of this style of mid-modern century architecture. We were able to discern the right buyer — someone who saw not just the 14-feet glass walls in the great room, but the life they were going to build within those walls.
Calling my clients to share the news of the closing was emotional, but also joyful. Because every closing is really a new beginning, for both the sellers who can now look forward to writing their next chapter with the sales proceeds, and for the buyers who are ready to start writing their own story in this home.
The One I Bought: A Dream Come True in the Hudson Valley
I alluded to this in my last letter in September, but I wanted to wait until it was official to scream it from the top of my lungs: I bought a home in upstate New York!
No, I’m not moving upstate! I can’t imagine leaving New York City!
But I am excited to make it official with a part of New York that has stolen my heart for the past five years –ever since I discovered the Hudson Valley during the pandemic NYC lockdown. It’s the place where my husband and I got engaged, married, and where we come to unwind, relax, reflect, connect with nature, and now, where we are growing our real estate portfolio!
The competition was fierce, and it gave me new-found perspectives on my buyers’ experiences bidding on hyper competitive homes.
Within the first weekend of showings, the seller received six offers.
I used everything in my toolbox: winning over the listing agent, writing a love letter to the seller, having the local community vouch for us, and more.
Still - we weren’t the winning offer.
Though sad, I was at peace, because I had followed my own advice that I give my buyers in a multiple-bid situation. “Offer the price that when you go above it and get the home, you might not be happy waking up in it every day as you are wondering if you overpaid.”
Then two days later, I received a call from the listing agent: the two highest offers had various issues. Do we still want the house?
An ocean of emotions washed over me.
Story continues below...
Lucky number 13!
Third time is the charm! I found out about this wonderful news that I had made the top Douglas Elliman New York City agents list for the third time this year (out of 2,000+ agents) the day before I closed on my upstate property, on four hours of sleep and had multiple client events and signed a new sales exclusive. Life has been full of colors and milestones lately, and I don’t take any of it for granted!
Worry and frustration: We had just set plans in motion on the assumption that we weren’t getting this home. Changing plans would involve tough conversations with multiple people we care about deeply.
Annoyed: Why didn’t they pick me first? They didn’t want me before - do I still want them back?
Confusion and uncertainty: they asked us to increase our bid by 5% to be the winner. Should we do it? Or should we stick to the number that we discussed and felt at peace with, and risk losing the house for the second time?
At the same time, a narrow, wavering stream of joy also started flowing in my heart. I told the listing agent to give us until the end of that day, buying us a few hours to decide.
My husband and I were visiting his parents when I got the call, so we didn’t have time to be alone to digest together. We continued with our plan that day and took a field trip with his family. When we got home, I took a hot shower, my thoughts racing. I imagined sitting on that porch, watching the sunlight filtering through the leaves, the shadows of the leaves swaying on the garden filled with native plants and flowers, birds, bees and butterflies.
I saw us having friends and family laughing and eating around a round table in the corner of the living/dining room, the white casement window on one side looking out to views of the Catskills mountains, the same mountains where we got married, and the windows on two other sides with views of the forest and the garden. And I knew in my heart that it was a yes for me.
Thankfully, my husband felt the same way. We went for it. The story of actually getting in contract and to the closing table will be for another day, but I wanted to share my personal story of almost losing a bidding war with you, because being in this position myself makes me appreciate on a deeper level what my clients go through, and it helps me better advise them. The fact that I felt no regret when I first lost the bidding war shows me the power of understanding my boundaries.
Getting a second chance after having lost out, then realizing I was willing to go up an extra 5% to win the bid, showed me that with the additional certainty of a concrete number, I felt comfortable increasing my offer.
It wasn’t that I wasn’t capable or willing to go up 5% in the first place, had I known that it would get me the house. But in a bidding war, the buyer doesn’t know what they are up against, and the uncertainty is what shaped my initial decision, one that I felt good about.
In our new upstate garden the morning of our closing
What These Two Homes Taught Me
This is what I learned: When I do my job right, you will feel confident and comfortable whether or not you “lose out” on one particular house or offer.
As a real estate advisor, my role is to increase your feeling of certainty through negotiations with the other side.
As a seller’s agent, my role is to help you remain agile and incorporate market feedback to get the most (and highest) offers.
As a buyer’s agent, my role is to glean more insight on the seller’s psychology and the competitive landscape of a particular deal, along with market knowledge, so you can make an informed decision on what to offer. And if the situation evolves (like when I got my second chance), I can help guide you to reassess and refocus, and maintain the flexibility to win the home you truly love.
I love my job as a real estate advisor, and I am always reflecting on how to hone my skills to better guide my clients.
If you’re thinking about your next chapter — whether that means selling, buying, renting or just daydreaming — I’m always here to talk it through with honesty and care.
With gratitude,
Judy
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