Real Life – Reconnecting in a Disconnected World
On a recent walk through my neighborhood, I saw something that struck me. A well-dressed individual had parked their car, popped open the hatch, grabbed a few bags, and walked into a nearby home. It was a delivery—groceries, maybe food. Nothing unusual these days. But for some reason, it stayed with me.
It reminded me how insular our lives can become. With a few clicks, we can get just about anything delivered—no need to leave home or interact. At first, that feels like convenience. But it also feels like a loss.
Humans are social by nature. For most of history, community and connection weren’t optional—they were daily life. Now, too often, they’re afterthoughts. Social media has made this worse. We’ve all seen people glued to screens, death-scrolling reels of other people doing things. The algorithm is so good—and so destructive—that our only hope is to turn it off.
That moment made me realize: I want more real in my life. More face-to-face time, less screen time. More love, fewer likes. So, I’ve recommitted to checking in and showing up—in person.
And with that spirit, I’m re-launching Coffee & Conversations. Starting Monday, July 7, I’ll be hosting an open coffee hour on the first Monday of each month. No agenda—just connection, conversation, and caffeine. Come say hello, bring a friend, and stay as long as you’d like. First beverage is on me.
Let’s Make “Neighbor” a Verb!
Forage Market
Monday, July 7
8:00 AM – 9:00+ AM
123 Washington Avenue, Portland
Community & Connection – Join Us Next Weekend!
Benchmark Real Estate is proud to be a lead sponsor of two incredible community events happening next weekend—and we’d love for you to join us.
Saturday, June 19-22 – Drive Fore Kids
Taking place at Falmouth Country Club, Drive Fore Kids is Northern New England’s premier celebrity golf tournament, benefiting Barbara Bush Children’s Hospital and the Dempsey Center. We’ll be posted up in our Benchmark Box in the Fan Zone—come find us, connect, and enjoy the action.
Want VIP Access?
We’re giving away two VIP tickets for Saturday to join me and other Benchmark guests. To enter the drawing, just reply to this email—simple as that.
Sunday, June 22 – East Bayside Trail Festival
Hosted by Portland Trails and Portland Downtown, this event celebrates the people, places, and local businesses that make Portland’s trail network so unique. Enjoy live music, family activities, local food & drink, and more—all happening along the beautiful East Bayside Trail. Benchmark is a proud supporter of both organizations and the mission to create a more walkable, connected Portland.Come for one, come for both—we hope to see you out there!
At Benchmark, we believe real estate is about more than buildings—it’s about building community. Thanks for supporting us as we continue to invest in the people and places that make Maine special.
BIG LOVE – Last Call…
This is your last chance to enter our BIG LOVE giveaway! One lucky winner (plus a guest) will join me, Amy, and Maddie to see Michael Franti & Spearhead on Friday, July 19 at Snow Pond Center for the Arts. It’s joyful, family-friendly, and packed with good vibes—Maddie has even made it on stage!
Friday, July 19
Snow Pond Center for the Arts, Sidney, ME
Doors at 5 | Show at 6 PM
michaelfranti.com
We're giving away:
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Show tickets
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Chauffeured limo transportation
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Dinner with us!
How to enter:
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Post a testimonial on Facebook and tag me and Benchmark Real Estate
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Drop a quick review in Google and Zillow
Share a story—transaction, referral, community impact. We’ll pick a winner soon!
Re-valuation – Portland’s New Property Values
If you own property in Portland, you’ve probably received a notice from Tyler Technologies—hired (again) by the city to conduct a revaluation. Based on your calls and emails, this rollout caused serious concern, confusion, and even panic.
What’s the issue?
Tyler’s assessments rely on drive-by reviews and public data, often using outdated images. No interior visits. That leads to inaccurate valuations.
We recently helped a West End owner whose multi-family with low rents and deferred maintenance was compared to pristine, high-rent comps. We’re now helping them appeal and reduce the value.
The Rollout Problem:
Notices showed only value increases—not estimated taxes owed. Some saw values double or triple, with no idea what their tax bill would be. We’re in touch with city assessors to push for transparency.
Need Help? I’ve Got You.
We’ll review your notice, provide comps, and issue a quick opinion of value.
Email: tom@benchmarkmaine.com
Text: 207-939-0185
Include a photo or copy of your reval notice—we’ll respond ASAP.
Anne’s Story – This Sale Felt So Good!
43 Hersey St., Portland – Sold for $950,000
“After two years of considering a move, I finally found the perfect next home—but buying it meant selling my beloved Portland house fast. Tom Landry at Benchmark made it happen. He jumped in immediately, handled the value, porch repairs, staging, painting, and packing—everything. Thanks to the team, we listed and closed ahead of schedule, and I got my dream home. Absolutely top-notch service start to finish.”
— Anne Gresinger
Market Update - Tom's Take - Top Sales
Single-family homes - This segment in Portland’s real estate market is showing remarkable resilience.
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Median sale price: Down only modestly, showing stability in prices.
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Number of sales: Up sharply month-over-month and up slightly year-over-year — jumping to 44, which is a 22.2% increase from last month and 7.3% higher than the same month in 2024.
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Days on market: Up modestly to 7 days, which seems like a big jump at 16.7%, but is just one more day than last year. Small jumps on low numbers can look large in percentages.
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Active inventory: A key metric we’re watching closely. Inventory jumped a whopping 82.4% month-over-month (vs. April 2025) and 34.8% year-over-year (vs. May 2024). This trend is influencing all market segments.
Condos - We’re seeing significant softening in the condo market — the second month in a row with this trend, which we’ll continue to monitor over the summer. Economic uncertainty may motivate some owners, especially older buyers, to downsize or consolidate second/third homes.
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Median sale price: Dropped 25.3% vs. April and 23.4% vs. May of last year. While high and low sales can skew this, it’s notable.
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Number of sales: Up compared to last month but down compared to last year.
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Days on market: Up sharply — from 15 days in April to 17 days now, and up from 11 days last year. Again, small differences show as big percentage changes.
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Active inventory: Up significantly — from 70 units in April 2025 to 83 units in May 2025, a 21% increase year-over-year.
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Price per square foot: Down 18.4% vs. April and down nearly 24% vs. May last year.
Multi-Family Homes - This segment always shows more variability due to fewer sales. A few large transactions can swing the stats.
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Number of sales: Up slightly from 10 to 13 month-over-month.
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Median sale price: Down slightly month-over-month but up slightly year-over-year, suggesting some stability.
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Active inventory: Down — possibly reflecting that multi-family owners are holding off on selling performing assets, especially with recent news highlighting slower sales in this category.
Bottom Line - It’s Time for Adult Conversations. This is a market that calls for honest, informed discussions with both buyers and sellers.
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Buyers - may not always score a deal, but there are opportunities, especially if they’re willing to roll up their sleeves and invest some sweat equity.
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Sellers - need to think strategically. Pricing slightly under can still create the magic of multiple offers and over-asking results. But it's not guaranteed, and that uncertainty requires realism.
Top Mainland Sale: 375 Spring St. 5br, 3.5bth, 5,930sf, $2,400,000
Single-Family Stats
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Median Sale Price: $569,000 (-.2% MoM from $570,000 in April ‘25 and -8.2% YoY from $620,000 in May ‘24)
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Sales: 44 (+22.2% MoM from 36 in April ’25 and +7.3% YoY from 41 in May ’24)
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Median DOM: 7 days (+16.7% MoM from 6 in April ’25 and +16.7% YoY from 6 in May of ’24)
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Price/Sq. Ft.: $402 (+9.4% MoM from $367 in April ’25 and +4.6% YoY from $384 in May of ’24)
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Active Inventory: 62 (+82.4% MoM from 45 in April ’25 and +34.8 YoY from 46 in May of ’24)
Top Sale: 387 Commercial St #708, 3br, 2.5bth, 2,005sf, $2,995
Condos Stats
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Median Sale Price: $465,000 (-25.3% MoM from $622,500 in April ’25 and -23.4% YoY from $607,000 in May of ‘24)
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Sales: 31 (+40.9 MoM from 22 in April ’25 and -11.4% YoY from 35 in May of ’24)
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Median DOM: 17 days (+17.2% MoM from 15 in April ’25 and +54.5% YoY from 11 in May of ’24)
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Price/Sq. Ft.: $440 (-18.4% MoM from $539 in April of ’25 and -23.9% YoY from $578 in May of ’24)
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Active Inventory: 83 (+29.7% MoM from 70 in April of ’25 and +22.1% YoY from 68 in May of ’24)
Top 2-4 Unit Sale: 74 St Melbourn St. 3 units, updated, 3,288sf, $1.4M
Multi-Family Stats
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Median Sale Price: $810,000 (-9.5% MoM from $895,000 in April of ’25 and +.6% YoY from $805,000 in May of ’24)
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Sales: 13 (+30% MoM from 10 in April of ’25 and +44.4% YoY from 9 in May of ’24)
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Median DOM: 8 days (-44.8% MoM from 15 in April of ’25 and -11.1% YoY from 9 in May of ’24)
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Active Inventory: 26 (-3.7% MoM from 28 in April of ’25 and -23.5% YoY from 34 in May of ’24)
Thank you for all the connections and see you soon!
Tom's Cell: 207-939-0185 | Office: 207-775-0248
Email: landryteam@benchmarkmaine.com
