The islands that define Sarasota’s identity as a Gulf Coast destination are not aspirational real estate — they are active, transacting Super-Jumbo markets. Bird Key, tucked between downtown Sarasota and St. Armands Circle, carries a median home price of $4.695 million. Casey Key — the most private of Sarasota’s barrier islands, a narrow Gulf-front strip with approximately 100 homes and no commercial presence — trades at $4 million and above for essentially every transaction. Longboat Key’s equity-club enclaves price from $3 million to $25 million depending on Gulf frontage and amenity package. The Rosewood Residences on Lido Key — 65 beachfront residences, the first exclusively residential property under the Rosewood brand — starts at $6.8 million. The top sale on Siesta Key in 2025 was a Gulf-front estate at $10.5 million.
These are not outlier transactions. They are the normal price range for buyers who have identified Sarasota’s barrier islands as their destination and are approaching the purchase with the financial resources to execute. The defining characteristic of this buyer is not simply their net worth — it is the complexity of their financial profile. Wealth-migration buyers from the Northeast and Midwest often arrive with investment portfolio assets, business sale proceeds, and retirement accounts that do not appear as current earned income. Buyers transitioning from a career to retirement may have significant asset wealth alongside minimal W-2 documentation. Buyers who recently sold businesses have capital that needs to be structured into qualification.
Super-Jumbo programs exist for all of these profiles. The critical variable is matching the right documentation approach to the income structure — and doing it before making an offer, not after one is accepted.
Ryan Lehrman, NMLS #235295, structures Super-Jumbo financing for Sarasota’s barrier island and upper-tier waterfront market with the documentation fluency, program depth, and confidential service that transactions at this level require.
Super-Jumbo mortgages are loans generally above $3 million. In Sarasota, this tier encompasses the full range of meaningful purchases on Bird Key, Casey Key, Gulf-front Longboat Key, the upper tier of Siesta Key’s waterfront market, and the new generation of barrier island luxury residences — Rosewood Residences Lido Key, Aria Longboat Key, Sage Longboat Key, The St. Regis Longboat Key — priced between $3 million and $15 million. It also includes construction loans for estate-scale teardown-and-rebuild projects on Siesta Key, Lido Key, and Longboat Key parcels where land value alone crosses the Super-Jumbo threshold.
Super-Jumbo loans are not purchased by Fannie Mae or Freddie Mac. They are portfolio loans held by the originating lender, underwritten according to that lender’s own guidelines. The difference between a lender with an active Super-Jumbo practice and one who handles these transactions occasionally is substantial at this loan size. Underwriting depth, appraiser network, documentation frameworks, and closing execution all reflect whether the lender has genuine experience with this product.
Sarasota’s Super-Jumbo borrowers typically include some combination of:
Retirement-transition buyers converting a career’s worth of investment wealth into a Gulf Coast primary residence
Business sale liquidity — buyers who recently exited a business and are deploying proceeds into real estate and lifestyle
Northeast and Midwest wealth-migration buyers with investment portfolios, trust income, or deferred compensation structures
Current-income earners — physicians, executives, attorneys, and financial professionals with strong compensation structures who are purchasing at the upper tier of the barrier island market
Designed for direct purchases of Gulf-front and bay-front estates on Sarasota’s barrier islands. These programs accommodate purchases from $3 million through $15 million and above, with loan-to-value structures calibrated to high-value coastal collateral and underwriting that accounts for the limited comparable sale base in Sarasota’s most exclusive submarkets. Gulf frontage footage, dock configuration, water depth, and barrier island-specific attributes affect valuation in ways that require appraisers with direct local experience.
For buyers whose primary financial strength is held in investment portfolios, retirement accounts, or recently realized business sale proceeds rather than current earned income. Asset depletion calculates qualifying monthly income by dividing eligible assets over a loan term divisor — allowing a buyer with $4 million in eligible assets and modest current W-2 income to qualify for a $2 million to $3 million Super-Jumbo loan that reflects actual financial capacity. This is one of the most frequently used pathways for Sarasota’s retirement-transition and wealth-migration buyer base.
For buyers with deferred compensation, partnership distributions, business ownership income, or consulting and advisory earnings that are real and consistent but require documentation beyond a W-2. Bank statement programs — using 12 or 24 months of personal or business statements — provide an alternative documentation pathway for buyers whose tax returns are reduced by legal business deductions. Two years of consistent distributions or deposits document the income pattern; the bank statement approach captures what actually flows into personal accounts.
For buyers commissioning estate-scale custom homes on Gulf-front or canal-front barrier island parcels — typically through teardown-and-rebuild projects on Siesta Key, Lido Key, and Longboat Key, where land acquisition and construction cost together push the project into Super-Jumbo territory. A single closing locks the permanent rate before construction begins on a project that may take 18 to 30 months to complete.
Bird Key
Sarasota's most exclusive non-barrier island community, accessible by a private causeway between the Ringling Causeway and the mainland. Bird Key has approximately 600 homes on deep canals and Sarasota Bay, with just 31 active listings at any given time and a median home price of $4.695 million. The community's combination of deep-water dockage, bay access, and proximity to downtown Sarasota and St. Armands Circle is unique — it is the only Sarasota community where buyers can walk to a world-class dining and shopping district while maintaining a private waterfront estate address. Days on market at Bird Key average 68 — the tightest of Sarasota's luxury submarkets.
Casey Key
Florida's Gulf Coast answer to private island living. Approximately 100 homes on a three-mile barrier island strip with no commercial development, no through traffic, and access limited to residents and invited guests. Every significant transaction on Casey Key is a Super-Jumbo purchase. The median price sits above $4 million and the island's extraordinary scarcity — no new lots, no expansion possible — supports pricing at levels that resist market corrections. Buyers here are specifically seeking the most private Gulf front address available in Sarasota County, and they typically arrive with liquid capital rather than financing requirements. When financing is used, portfolio lending and asset depletion are the standard tools.
Longboat Key — Gulf-Front and Equity-Club Enclaves
The equity-club tier of Longboat Key, anchored by the Longboat Key Club and Bay Isles community, produces the Gulf Coast's most concentrated collection of private-club waterfront estates outside of the Palm Beach corridor. Gulf-front estates and club residences trade at $3 million to $25 million. New construction luxury deliveries including Aria Longboat Key, Sage Longboat Key, and The St. Regis Longboat Key are capturing buyers who want both Longboat Key's established prestige and new construction quality without the structural inspection and reserve uncertainty of older buildings. Luxury condo closes on Longboat reached nearly $10 million in mid-2025.
Lido Key — Rosewood Residences and Gulf-Front Estates
The Rosewood Residences at 930 Benjamin Franklin Drive — 65 beachfront residences on 230 feet of Gulf frontage, starting at $6.8 million — represents the first exclusively residential Rosewood-branded property in the world, delivered in 2025 and 2026. With $239 million in total sales at announcement, the project established a new benchmark for Lido Key. Gulf-front single-family estates on the island produced a $4.85 million headline sale in late 2025. Lido Key's walkable proximity to St. Armands Circle adds a lifestyle dimension to waterfront ownership that other Sarasota islands do not provide.
Siesta Key — Gulf-Front Estate Tier
While Siesta Key's median has corrected from pandemic highs, its Gulf-front estate segment is a genuine Super-Jumbo market. The 2025 top sale — a Gulf-front estate at $10.5 million — reflects sustained demand at the island's upper tier even as mid-market inventory adjusts. Canal-front estates with private docks in the $3 million to $7 million range represent the active Super-Jumbo transaction tier. Buyers at this level are purchasing for the combination of Siesta Key's remarkable quartz sand beach — consistently rated among the best in the world — and a private waterfront address with boating access.
Super-Jumbo programs through $10 million and beyond for Sarasota's barrier island and waterfront estate market
Asset depletion and portfolio income programs for retirement-transition and wealth-migration buyers
Business owner and bank statement documentation for buyers whose tax returns understate actual cash-generating capacity
Construction-to-Permanent Super-Jumbo for barrier island teardown projects on Gulf-front and canal-access parcels
Appraiser network experienced in Sarasota barrier island comparable sales — Gulf frontage, dock configuration, and island-specific valuation
Discreet, confidential service for high-net-worth clients
Ryan Lehrman, NMLS #235295
Credit Profile: 720 to 740 minimum for most Super-Jumbo programs, with best pricing at 760 and above. Buyers with investment-based income profiles benefit from a pre-consultation to confirm program fit before any application.
Income Documentation: Full tax return documentation for W-2 and self-employed borrowers. K-1s and partnership agreements for business owners and fund investors. Bank statement programs for buyers with tax return income that understates actual cash flow. Asset depletion schedules for buyers with substantial investment, retirement, or business sale proceeds.
Loan-to-Value: Most Super-Jumbo programs allow 65% to 75% LTV. Loans above $5 million typically require 25% to 35% down. Coastal barrier island collateral — particularly Gulf-front property — may have specific LTV parameters reflecting both value and insurance cost considerations.
Reserves: 12 to 24 months PITI in liquid or near-liquid assets. Investment and retirement accounts count at 60% to 70% of market value for reserve purposes. Florida insurance costs — which can add $15,000 to $40,000 per year for Gulf-front barrier island properties — are factored into PITI calculations.
Confidential Consultation — A private, pre-offer conversation about the property, loan amount, income structure, and the right documentation approach. For Bird Key, Casey Key, and the Longboat Key equity-club tier, seller communities are small and preparation matters.
Documentation Planning — Ryan identifies the documentation path — tax returns, bank statements, asset depletion schedules, or a combination — and outlines what is needed before underwriting begins.
Appraisal and Property Review — Barrier island appraisals require appraisers with direct experience in the specific island's comparable sale base. Gulf frontage footage, dock configuration, water depth, and proximity to St. Armands Circle or the Longboat Key Club are variables that general appraisers may not weight accurately.
Underwriting and Conditions — Ryan maintains direct communication throughout underwriting, addresses conditions promptly, and coordinates with the buyer's legal and financial advisors.
Closing — Sarasota Super-Jumbo closings frequently involve attorneys, out-of-state or international parties, and time-sensitive coordination. Ryan manages the timeline to close on the date the purchase contract requires.
Yes, through asset depletion and pension income documentation. Your documented pension payment contributes directly to qualifying income. Your $3.5 million brokerage account generates qualifying income through the asset depletion calculation — dividing eligible assets over the loan term to produce a monthly income figure. Between pension income and asset depletion, most buyers in this profile qualify for the loan amount they need without requiring current W-2 employment. The consultation conversation documents your specific numbers before any application is submitted.
Windstorm and flood insurance premiums for Gulf-front barrier island properties in Sarasota can be substantial — $15,000 to $40,000 annually or more for high-value Gulf-front homes, depending on age, construction type, elevation, and flood zone designation. These costs are included in the PITI calculation that determines your debt-to-income ratio. For Super-Jumbo buyers with strong asset profiles, insurance costs are rarely a disqualifying factor — but they are a real carrying cost that belongs in the total cost of ownership conversation. New construction homes with current impact-resistant windows, elevated foundations, and modern construction standards typically qualify for better insurance terms than older buildings.
The Rosewood Residences are a pre-construction purchase that delivers in 2025 and 2026. Financing for these purchases is typically arranged in the 60 to 90 days before the scheduled closing date, once the unit is nearing completion and a final appraised value can be established. Buyers who entered contracts at announcement are now approaching the financing window. Given the $6.8 million starting price, Super-Jumbo financing is required for any leveraged purchase. The specific program — fixed rate, adjustable rate, asset depletion, or bank statement — should be identified and pre-approved well before the anticipated closing date.
Super-Jumbo transactions benefit from early engagement. Let’s have a confidential conversation about your property and financial profile.
Originally from Harrisburg, Pennsylvania, I moved to Phoenix to attend Arizona State University and have proudly called Phoenix home ever since.
My journey into the mortgage industry began with a friend’s encouragement, who saw how my energy and people-first mindset could make a difference. He was right — I found my calling.
I’ve always embraced what makes me different. With ADHD as my secret weapon, I thrive in fast-paced, detail-heavy environments. I’ve built my career on clear communication, creative problem-solving, and putting clients first, always.
Outside of work, my greatest motivation is my wife and three amazing kids. I’d be honored to help guide you through your lending journey with care, clarity, and commitment.
Who we are
Our website address is: https://loansbylehrman.com/
Embedded content from other websites
Articles on this site may include embedded content (e.g. videos, images, articles, etc.). Embedded content from other websites behaves in the exact same way as if the visitor has visited the other website.
These websites may collect data about you, use cookies, embed additional third-party tracking, and monitor your interaction with that embedded content, including tracking your interaction with the embedded content if you have an account and are logged in to that website.
SMS Privacy
I respect your privacy. I will not share or use your mobile number for any other purpose. I will only use information you provide to transmit text messages. Nonetheless, I reserve the right at all times to disclose any information as necessary to satisfy any law, regulation or governmental request, to avoid liability, or to protect my rights or property. When you complete forms online or otherwise provide me information in connection with the Service, you agree to provide accurate, complete and true information. You agree not to use a false or misleading name or a name that you are not authorized to use. If I, in my sole discretion, believe that any such information is untrue, inaccurate or incomplete, I may refuse you access to the Service and pursue any appropriate legal remedies.
Analytics tracking
Our website uses analytics tools such as Google Analytics to better understand how visitors interact with our site. These tools collect data through cookies and similar technologies, including information about on-site activity and, in some cases, IP addresses. We use this data to improve user experience, monitor performance, and track conversions. Visitors who prefer not to be tracked can opt out by using the Google Analytics opt-out browser add-on or other available opt-out methods.
