Your Trusted
Financial Planner
in Winchester, VA
Water Street Financial provides personalized financial planning and wealth management for individuals, families, and business owners in Winchester, Virginia and the Shenandoah Valley — building, preserving, and transferring wealth across generations since 2016.
Winchester, VA
Rating
LPL Financial
Financial Planning That Starts With You
At Water Street Financial, we believe your financial plan should be as unique as your life. Led by Managing Partner Ryan Oates, CFP® MBA CPFA, our Winchester, VA team takes the time to understand your goals, your concerns, and what success looks like for your family — before we ever talk about products or strategies.
Whether you’re planning for retirement, growing a business, navigating a career transition, or building generational wealth, we provide the strategic oversight and hands-on guidance to help you get there with confidence.
Learn About Our Team →
Comprehensive Financial Services
From financial planning to wealth management, our Winchester, VA team brings every piece of your financial life together under one strategy.
Financial Planning
A personalized roadmap built around your goals — not a template.
Learn More →Investment Management
Professionally managed portfolios tailored to your risk tolerance and goals.
Learn More →Retirement Planning
Social Security, pensions, TSP, 401(k), and income strategies for a confident retirement.
Learn More →Tax Planning
Proactive strategies to reduce your tax burden and keep more of what you earn.
Learn More →Estate Planning
Protect your legacy with wills, trusts, and wealth transfer strategies.
Learn More →Wealth Management
Comprehensive strategies to build, preserve, and transfer wealth across generations.
Learn More →Financial Planning for Every Stage of Life
No matter where you are in your financial journey, our Winchester, VA team has the expertise to help you move forward with confidence.
Business Owners
Tax strategies, succession planning, and retirement.
Government Employees
FERS, TSP, and federal benefits optimization.
Retirees
Income planning, Social Security, and wealth preservation.
Millennials
Budgeting, student loans, investing, and early wealth building.
Independent Women
Personalized strategies for financial independence.
Physicians
Student loan management and high-income wealth building.
Remote Workers
Multi-state taxes, benefits gaps, and retirement.
Not Sure? Take the Quiz →
Answer 5 questions and get your personalized wealth roadmap.
What Makes Us Different
Your Goals Come First
Every recommendation starts with what you’re trying to achieve — not what we’re trying to sell. We act as fiduciaries, always in your best interest.
Everything Under One Roof
Financial planning, investments, taxes, retirement, and estate planning — coordinated as one strategy, not managed in silos.
Transparent Fees, Always
No hidden costs, no surprises. We disclose all fees upfront before you commit to anything.
Local & Accessible
Our office is at 335 Westside Station Drive in Winchester, VA. We also offer virtual meetings for clients who prefer the flexibility.
Getting Started Is Simple
Schedule a Consultation
Call us, fill out the form, or take the quiz. We’ll set up a complimentary meeting — in person or virtual — to learn about you and your goals.
Get Your Custom Plan
We analyze your complete financial picture and build a personalized plan covering investments, retirement, taxes, estate, and risk — all coordinated together.
Live With Confidence
We implement, monitor, and adjust your plan as life changes. Regular reviews keep you on track. You’ll never wonder where you stand.
Trusted by Winchester, VA Families
Don’t just take our word for it. Here’s what our clients have to say about working with Water Street Financial.
Winchester, VA Is Our Home
Our office at 335 Westside Station Drive is the heart of Water Street Financial. We’ve been serving the Winchester community since 2016 — and our roots run deep. From local business owners to federal employees, retirees to young professionals, we know this community because we’re part of it.
We also serve clients throughout the Shenandoah Valley, Northern Virginia, the Eastern Panhandle of West Virginia, and nationwide through virtual meetings.
See Our Service Area →