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Ashley Calhoun Winship

Ashley Calhoun Winship

Practice areas:

Estate Planning, Probate, Tax, Corporate & Incorporation, Marriage & Prenuptials

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About Me

I am an attorney practicing in Central Florida, where I focus on Estate Planning and Trust and Estate Administration. Planning for asset growth and protection, wealth succession, and major life events (marriages, divorces, births, incapacity, and end-of-life) is critical for everyone. I provide the guidance, structure, and documentation needed to maximize wealth, minimize taxes, reduce worry, and provide security for working people and their families. Whether planning for a growing family and career, retirement, or final distribution, I provide all of the client’s estate planning needs at a predicable cost.

In addition, I have a significant amount of experience in the areas of tax exempt organizations and corporate law.

My education began at Florida Southern College, where I studied Communications and Advertising Design. After working as a graphic artist and copywriter for a few years, I attended Stetson University where I earned both an MBA and a law degree. During my tenure at Stetson, I served as an intern to Federal Magistrate Judge Thomas G. Wilson and an Articles Editor of the Stetson Law Review. Subsequently, I earned a Master of Laws in Taxation from the University of Florida College of Law, where I was a Graduate Tax Scholar and served as an editor for the Florida Tax Review.

In my free time, I enjoy writing and collaborating with my husband on creative projects. I also stay active in professional and community organizations. Currently, I am involved with two great Orlando organizations - the Central Florida Association for Women Lawyers and the George C. Young First Central Florida American Inn of Court. In the past, I have been active in organizations across the state, including The Lakeland Bar Association, Junior League, Estate Planning Councils, the Polk Museum of Art, Kiwanis, the Lakeland Chamber of Commerce, and Community Foundations, among others.


Practice Areas

Licensed since 2003

  1. Tax: 25%
    11 years
  2. Probate: 25%
    11 years
  3. Estate Planning: 25%
    11 years
  4. Corporate & Incorporation: 15%
    11 years
  5. Marriage & Prenuptials: 10%
    11 years


Payment Types:

Cash, Check, Credit Card

Attorney Endorsements

2 total

  • Emily McAlhaney Konicek

    I endorse this lawyer.


    Emily Konicek Divorce & Separation Attorney
    Relationship: Fellow lawyer in community

  • Robert John Sunner

    Ashley is an extremely intelligent and hard-working attorney. She is an incredible problem-solver and it was a pleasure working with her on numerous matters. I fully endorse her for all of your estate planning needs.


    Robert Sunner Personal Injury Attorney
    Relationship: Fellow lawyer in community

Contact Info

Winship Law, P.A.

230 S. New York Avenue.
Suite 200
Winter Park, FL, 32789


FLMember in Good Standing200305/07/2015

Professional Misconduct

We have not found any instances of professional misconduct for this lawyer.
Avvo Contributions
Legal Answers
Award NameGrantorDate Granted
Grads Made GoodFSC Chapter of ODK2006
Graduate Tax ScholarUniversity of Florida College of Law2003
Outstanding New Associate AwardStetson Law Review2002

Work Experience
TitleCompany NameDuration
AttorneyRush, Marshall, Jones and Kelly, P.A.2012 - Present
AssociateBroad & Cassel2007 - 2012
AssociateGray Robinson2004 - 2007
Student InternUS District Court, Middle District of Florida2003 - 2003
Summer AssociateGray Robinson2002 - 2002

Association NamePosition NameDuration
George C. Young First Central Florida American Inn of CourtBarrister2011 - Present
Florida Bar, Real Property, Probate and Trust Law SectionMember2011 - Present
Central Florida Association for Women LawyersDirector2009 - Present
Florida Bar, Tax SectionMember2004 - Present

Publication NameTitleDate
Matthew BenderFlorida Statutes Section 213.018: Taxpayer Problem Resolution Program2006
Matthew BenderLimitations on Actions to Collect Secured Tax Liability2006
Matthew BenderFlorida’s Taxpayer’s Bill of Rights: Where We Have Been, Where We Are Going2006
Stetson Law ReviewWinking in the Dark: The Burden of Proof for Corrective-Advertising Damages...2003
Stetson Law ReviewLocal Government Recent Developments2003

School NameMajorDegreeGraduated
University of Florida College of LawTaxLL.M - Master of Laws2004
Stetson University College of LawLawJD/MBA - Juris Doctorate and MBA2003
Florida Southern CollegeMass Comm & Ad DesignBA - Bachelor of Arts1999