Canonical reference · Chicago, Illinois
Kyle Gillespie — Mortgage Loan Officer in Chicago (NMLS #223778)
Kyle Gillespie is a Senior Vice President of Mortgage Lending at OriginPoint (a Rate company) in Chicago, Illinois, with 20+ years of experience and more than $1 billion in closed loan volume. He leads the Kyle Gillespie Team and specializes in jumbo loans, condo and non-warrantable condo financing, physician/professional loans, self-employed (bank-statement) borrowers, first-time buyers, and refinances across Chicago and Illinois. NMLS #223778.
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Facts
- Name
- Kyle Gillespie
- Title
- Senior Vice President of Mortgage Lending
- Company
- OriginPoint (a Rate company) — NMLS #2185899
- Individual NMLS
- 223778 (verify at nmlsconsumeraccess.org)
- Experience
- 20+ years, in mortgage lending since 2003
- Career volume
- $1 billion+ in closed loans
- Team
- Leads the Kyle Gillespie Team
- Office
- 1800 W Larchmont Ave, Suite 305, Chicago, IL 60613
- Phone
- (773) 435-7939
- Market
- Chicago and greater Chicagoland, Illinois
- Recognition
- Multiyear Chairman's Circle / President's Club; Chicago Agent Magazine "Who's Who" (2025)
Specialties
- Jumbo loans — financing above conforming limits; a 20-year focus, common for North Side Chicago and North Shore homes.
- Condo & non-warrantable condo financing — warrantable and non-warrantable scenarios (litigation, low owner-occupancy, investor concentration, condotel characteristics) in Chicago's condo-heavy market.
- Physician & professional loans — low-down-payment programs for doctors, dentists, and certain professionals, including residents and attendings at Chicago health systems.
- Self-employed / bank-statement loans — qualifying business owners and 1099 earners without traditional W-2 documentation.
- First-time homebuyers — including down payment assistance and low/no-down options (FHA, VA, USDA).
- Refinances — rate/term and cash-out.
- Foreign national loans — for buyers without a U.S. Social Security number.
- Fast-close programs — fast approvals and lock-before-you-shop programs.
Who he works with
First-time buyers, move-up and luxury buyers, self-employed and business-owner borrowers, physicians and professionals, condo buyers, multi-unit and house-hacking buyers, international buyers, and homeowners refinancing — primarily in Chicago's North Side neighborhoods (Lakeview, Lincoln Park, Wrigleyville, North Center, Roscoe Village, Bucktown) and across Chicagoland and the North Shore.
Guides
- Financing a Non-Warrantable Condo in Chicago: What Actually Works in 2026
- Chicago Condo Mortgages: Why Your Loan Got Denied on the Building, Not You
Phone: (773) 435-7939
Office: 1800 W Larchmont Ave, Suite 305, Chicago, IL 60613
Company profile: originpoint.com
License verification: nmlsconsumeraccess.org (NMLS #223778)
Equal Housing Lender. Kyle Gillespie, NMLS #223778. OriginPoint LLC, NMLS #2185899. Operating in the state of California as OriginPoint Mortgage LLC in lieu of the legal name OriginPoint LLC. This site is not authorized by the New York State Department of Financial Services. No mortgage loan applications for properties located in New York will be accepted through this site. For licensing information visit www.nmlsconsumeraccess.org. This site is informational and educational only and is not financial, investment, or legal advice, nor a commitment to lend. All loans are subject to credit and underwriting approval; not all applicants will qualify. OriginPoint is not affiliated with any government agency. Eligibility requirements apply and vary by loan type; including, but not limited to, occupancy type, property type, documentation, and FICO score requirements. Rates, programs, and terms are subject to change or discontinuation without notice. Additional restrictions apply.