20 Oak Street, Piermont, NY
Winning a Historic Cottage with Smart Strategy and Clear Vision
When we found 20 Oak Street, it stood out immediately. A charming 200-year-old cottage tucked into the hillside of Piermont—full of history, character, and storybook appeal. It didn’t come with land, but it came with opportunity.
We knew from the start that competition would be strong. The property had broad appeal and serious potential. So we moved quickly—and strategically.
Offer Strategy
We submitted a best and highest offer that included:
Initial offer of $480,000
Highest & best set at $100,000 over asking for my realtor to use to negotiate
A $100,000 FHA 203(k) renovation loan
20% down
No inspection contingency
No mortgage contingency
This gave us a competitive edge. We weren’t just offering the highest price—we were also offering certainty and speed. The seller accepted our offer, the contract was signed, and escrow was funded.
Due Diligence: FOIL Request & Legal Review
Before the offer was even accepted, we filed a FOIL (Freedom of Information Law) request with the local building department. Through that request, we uncovered:
An open permit from 2012
An outstanding violation tied to that permit
This became critical during contract review. The seller’s draft contract included language stating they would not be responsible for clearing open permits. Because we had already done our homework, we were able to push back immediately. The seller was made aware that the permit and violation were on record, and we successfully had that stipulation removed from the contract—ensuring both issues would be cleared before closing.
Renovation Plan
Because the lot has no yard or exterior space, we focused on enhancing livable square footage within the existing footprint and adding rooftop access:
Add a Widow’s Walk rooftop terrace with structural supports tied into the primary bedroom below
Redesign the compact first floor into a dedicated guest suite or short-term rental unit (Airbnb)
Upgrade the top-floor primary suite during construction of the rooftop
Preserve the kitchen and living area on the main level with light, high-impact upgrades
Install ductless mini-split air conditioning for year-round comfort
Semi-finish the detached garage into an office/flex guest space with a dedicated laundry area in back
The Process
The original plan was to purchase using an FHA 203(k) loan and finance $100,000 worth of renovations to match the home’s character with thoughtful improvements. Everything was moving forward until underwriting refused to count the rental income as the income was not on the previous years taxes. Even with a signed lease agreement in place, they required a full year of rental history, which I couldn’t provide.
At that point, the mortgage company quickly pivoted to a conventional renovation loan. That came with its own set of demands:
Bring down the debt-to-income ratio fast, which meant paying off all credit card balances.
Raise the credit score significantly in a short amount of time.
Then the appraisal came in at $600,000—less than the $650,000 total loan amount. Because of that, there would be a PMI. We filed a Reconsideration of Value with supporting evidence showing what the property would be worth post-renovation. The appraiser adjusted the value to $615,000. It wasn’t the full bump we wanted, but enough to reduce the PMI slightly. When the mortgage is refinanced into a lower interest rate, the PMI will fall off altogether.
Because I’d be subject to PMI either way due to the appraisal, we chose to put $120,000 down instead of more, preserving liquidity.
Key Details
Purchase Price: $575,000
Renovation Loan Amount: $75,000
Total Loan Amount: $650,000
Down Payment: $120,000
Appraisal Value After ROV: $615,000
Square Footage: 1,008 sq ft
Bedrooms / Baths: 2 beds, 2 full baths
Year Built: c.1820
Annual Taxes: ~$11,048
Financing: Shifted from FHA 203(k) to conventional renovation loan
PMI: Small, expected to be removed after refinance
Lot Size: 0.02 acres + separate lot at 11 Elm Street
Parking: One-car garage + 2-car parking pad and shed
School District: South Orangetown
Notable Features: Two fireplaces, wide-plank flooring, upper-level river views
Takeaway
This deal was a perfect example of how every purchase has its surprises. You can go in with a plan, but success often comes down to how quickly and thoroughly you respond when that plan has to change. In the end, we walked away with a historic cottage full of soul, a renovation budget ready to work, and a strategy in place to keep building equity over time.
For more information on this or other renovation-focused real estate opportunities, please reach out directly.