Cara A. Whalen


Practice Areas

Residential and Commercial Real Estate

Business Law
Liquor Licensing and Compliance

Landlord/Tenant Law

Estate Planning

Partner, Real Estate Practice Group Leader

Cara focuses her practice in the areas of residential and commercial real estate, business, liquor licensing and estate planning. Through a vast range of experience with residential and commercial real estate transactions, she has a keen understanding of complex transactions involving all phases of leasing, acquisition, disposition and financing with individuals and business owners of various sizes. 

Cara graduated cum laude from The College of Saint Rose with a B.S. in Criminal Justice and a minor in English. She graduated from Western New England University School of Law with a dual concentration in Real Estate and Estate Planning. In her time there, Cara was awarded the CALI Award for Excellence in Real Estate Development and Estate Planning. 

Cara worked with Chicago Title Insurance Company, Commonwealth Land Title Insurance Company and Bacon Wilson, P.C., while participating in a real estate practicum. She also served as a law clerk with the Dutchess County District Attorney’s Office and Palmer District Court in Massachusetts. 

Cara has served as a member of the American Heart Association Board since 2018 and chaired the Community Impact Committee since 2019. Also since 2019, Cara has been actively involved with the Dutchess County Real Estate Charity Golf committee to raise funds for several local charities assisting people in the Hudson Valley. 

In 2020, Cara was the recipient of the Hudson Valley’s Top Forty Under 40 Mover & Shaker award. She was nominated and recognized by her peers as one of Hudson Valley’s Top Lawyers in 2022 and 2023. 

Cara is a third generation attorney and is a native to the Millbrook area.


Recent Work

  • Successfully counseled a residential real estate developer in more than 90 matters involving purchases, sales, financing, formation of entities and leases
  • Represented the purchaser in a $18,250,000 acquisition consisting of multiple structures and parcels in Dutchess County
  • Negotiated a $5,700,000 residential transaction in the Town of Washington
  • Guided the sale of a $5,600,000 residential property in the Town of Clinton containing multiple parcels and a residence
  • Represented the seller in the transfer of a $2,850,000 penthouse and $2,675,000 penthouse in New York City
  • Efficiently coordinated sales and 1031 exchanges of multi-building portfolios in excess of $4,500,000
  • Represented a commercial investor in connection with the acquisitions, negotiations of construction contracts, and leasing units of multiple buildings consisting of more than 180,000 square feet 
  • Represented a developer in securing more than $10,500,000 in construction loans for a mix-use project in Dutchess County
  • Represented a client in re-financing loans totaling $9,000,000 and the purchase of a 24-lot subdivision
  • Represented a client in the sale of a produce distribution company in New Rochelle and the acquisition and leasing of approximately 10 residential properties
  • Represented a client in the purchase and development of a $6,300,000 residential property in Northern Dutchess County

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New York State Bar Association
Dutchess County Bar Association
Hudson Valley Estate Planning Council
American Bar Association
Dutchess County Association of REALTORS
Mid-Hudson Valley Mortgage Bankers Association
National Association of Professional Mortgage Women


Western New England University School of Law, J.D.
The College of Saint Rose, B.S.

In The Community

  • American Heart Association, Board Member, and Community Impact Committee, Chair
  • Dutchess County Real Estate Charity Golf Committee, Member


New York
Southern District of New York

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