HMSLLC
Housing Management Services
Private Client Property Advisory

Strategic counsel for sophisticated property owners.

HMS provides advisory, structuring, and full-service management for second homes, investment properties, and Qualified Opportunity Zone investments across the Chesapeake Bay and the Florida Keys.

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At a glance

Boutique advisory rooted in operational experience.

HMS is a private-client property advisory firm serving sophisticated owners and investors across two coastal regions — the Chesapeake Bay and the Florida Keys. We pair structural strategy with hands-on operations, working with a small number of clients in depth rather than many at scale.

Featured Specializations

Three areas where we lead.

Most of our engagements draw on one or more of these specializations. Each is grounded in regulatory expertise, operational practice, and direct experience advising owners through the full lifecycle of their assets.

Specialization

Qualified Opportunity Zone strategy

End-to-end advisory for Opportunity Zone investors — from QOF and QOZB structuring, to property identification within designated zones, capital deployment, and the long-term hold through the year-ten exclusion. We coordinate with your tax counsel and CPA throughout the engagement.
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Specialization

Entity structuring for real estate

Multi-entity portfolio organization for owners and investors holding more than a single property. LLC structuring, holding-versus-operating company strategy, intercompany agreements, and the foundational legal architecture that protects long-term ownership.
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Specialization

Second home & vacation property structuring

Optimal ownership structures for absentee owners — rental versus personal-use analysis, tax-efficient operating frameworks, and the management infrastructure required for properties held outside primary residence states.
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Additional Services

Operational depth across the portfolio.

Property Management

Full-service oversight for residential, vacation rental, and manufactured housing communities — supported by on-the-ground vendor networks in both the Chesapeake Bay region and the Florida Keys.

Acquisition Services

Property sourcing, auction representation, due-diligence coordination, and negotiation support for owners building or expanding portfolios.

Disposition & Exit Services

Sale-side support including disposition timing, tax coordination, and year-ten exclusion elections for QOZ holdings.

Concierge

Grounds maintenance, vendor management, project oversight, and personal property services for second-home owners — across both regions we serve.

Strategic Consulting

Investment strategy, portfolio structuring, and operational improvements for owners and operators of real estate businesses.

Digital Services

Custom websites, tenant portals, and branded marketing materials for property businesses operating in the regions we serve.
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Selected Engagements

A small number of clients, served in depth.

Each engagement below illustrates a different facet of our practice. We do not maintain a public client roster; the firms shown here have permitted reference.

Qualified Opportunity Zone Fund

River Investment Group LLC

Advisory & operational support

Manufactured Housing · QOZ Investment

Lumberlost Park

Management & digital services

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Single-Family Rental · West Point, VA

KWA LLC

Acquisition, structuring & management

Florida Keys Vacation Rental

Finding Remo

Management & concierge

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Begin a Conversation

Discreet, considered, and personally delivered.

Engagements are bespoke and begin with a confidential consultation. We respond personally to every inquiry within two business days.

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