Aerial view of forested Catskill mountains

Hotel & Real Estate Development

A Development &
Investment Platform.

DD|HA is a development and investment platform focusing on ground up and value-add hotel opportunities.

Current projects Contact

The Catskill Mountains at Belleayre, Ulster County, New York.

$1B+Advisory transaction volume

$200M+Hotel real estate transacted

The firm

From advisor to principal

After three decades advising owners, lenders, and investors on hotel and real estate transactions, Tom has transitioned his focus to the principal side and now invests, develops, acquires, and manages hotel assets as a strategic partner.

Current work spans asset management and development at a luxury Catskills resort, development and investment advisory for a ±670-acre land offering at Belleayre Mountain, and capital markets and development for a ground-up boutique hotel in Lowell, Massachusetts.

Focus

Areas of focus

DD|HA is actively seeking OZ 2.0 eligible hotel re-development opportunities.

Residential

Multifamily and residential development sites and under-performing assets in supply-constrained Northeast markets, including conversion and adaptive-reuse plays.

Hotel

Existing hotels with a repositioning story and ground-up hotel development, from select-service to resort. It is the asset class we know from every side.

Land & Opportunity Zones

Entitled or entitle-able land in high-barrier markets, and projects in eligible and nominated Opportunity Zone 2.0 tracts where the new designations create durable tax-advantaged upside.

And for owners

Select advisory for the right situations

We continue to take on a limited amount of advisory work: asset management, capital markets, development advisory, and hotel tax strategy. We have advised owners on property, sales and use, occupancy, payroll, and state and federal income taxes, as well as tax-based development incentives.

Read about the Killington revaluation and related work →

Experience

Thirty years, every side of the table

A transaction record spanning three decades and every role in a hotel deal.

Since founding DD|HA in 2018, our principal has transacted more than $200 million in hotel real estate across the Northeast, and today develops the asset management strategy of a luxury Catskills resort, a ±670-acre development land offering at Belleayre Mountain, and the capitalization of a ground-up boutique hotel development.

That recent record sits on three decades of work: more than a thousand hotel assignments in 48 states for owners, developers, lenders, family offices, and municipalities, valuing, underwriting, financing, developing, repositioning, and selling every type of hotel from roadside select-service to luxury resorts and conference centers.

On the distressed side, we built and ran an asset-management and special-servicing platform for a private-equity-backed lender's $200 million portfolio of troubled hotels and non-performing loans, and carried it through the pandemic: converting loans to owned real estate, redeveloping and re-flagging assets, negotiating through bankruptcies and receiverships, and selling without outside brokers, at recoveries well above what the portfolio's condition suggested.

On the ownership side, we have acted as asset manager and partner to resort and hotel owners preparing for sale, lifting net operating income before taking the property to market; raised debt and equity for new hotel developments; and guided owners through brand, operator, and joint-venture decisions that determine what a hotel is ultimately worth.

$1B+Transaction value advised on across acquisitions, dispositions, financings, and developments

$200M+Hotel real estate personally transacted since 2018

72¢Average recovery per dollar on a distressed midscale and economy portfolio through COVID

Principal

Thomas Dolan

Tom has spent more than thirty years in hotel real estate finance, advisory, and operations. He joined HVS in 2000 and opened the firm's Boston office as Managing Partner in 2005, later founding one of its national practice groups. Over eighteen years there he completed some 1,500 self-originated assignments covering acquisitions, dispositions, financing, development, feasibility, and valuation, generating more than $25 million in revenue.

He founded DD|HA in 2018. Since then he has transacted over $200 million in hotel real estate, structured debt and equity across hotel, residential, and mixed-use assets, and served as senior advisor to a private-equity-backed lender on a $200 million distressed portfolio. He has testified as an expert witness on hotel valuation, spoken at the NYU International Hospitality Investment Conference, and taught hotel real estate as an adjunct professor at Boston University's School of Hospitality Administration.

Tom is known for finding what others miss: the operating leaks, capital missteps, and structural issues that quietly cost owners millions. Today he puts that eye to work on his own projects, and is always looking at the next one. He lives in the Boston area with his wife Jessyca and their four children.

Licensure: Licensed Real Estate Broker, New York (#10351214442) and Massachusetts (#1000683)
Education: B.S., Hotel & Restaurant Management, Northern Arizona University, summa cum laude
Teaching: Adjunct Professor, Boston University School of Hospitality Administration, 2022–2024
Speaking: NYU International Hospitality Investment Conference; Hospitality Law Conference; guest lecturer, Boston University

Contact

Contact.

For information about DD|HA, its current projects, or its advisory work, get in touch.

Phone: 516-435-4452
Email: thomas@ddha.com
Office: 36 Commerce Way, 2nd Floor
Woburn, MA 01801
Entity: DD Real Estate Advisory, LLC, d/b/a DD|HA

Current projects

What we're working on

Led by Crossroads at Belleayre Mountain, current work spans development, investment advisory, asset management, capital markets, and select tax advisory. Offering and project materials are available to qualified parties; contact thomas@ddha.com.

Development · Investment advisory

Crossroads at Belleayre Mountain

±670 acres of development land at Belleayre Mountain, offered exclusively through DD|HA.

Aerial view of Belleayre Mountain ski trails and the surrounding Catskills terrain — Belleayre Mountain and Highmount, at the Ulster–Delaware county line.

DD|HA is the exclusive advisor and broker for Crossroads: approximately 670 acres of development land abutting and proximate to Belleayre Mountain, spread across twenty-three tax parcels in the Towns of Shandaken (Ulster County) and Middletown (Delaware County), New York. The assemblage is anchored by the ±104.8-acre former Highmount Ski Center, which abuts Belleayre.

Ulster County has the fastest-growing tourism and visitor economy in New York State: visitor spending rose 10.5 percent in 2025 to $1.24 billion, 2.7 times the statewide rate. Belleayre's four-season recreation anchors the market.

The lands sit at the base of Belleayre Mountain, the state-operated ski center whose four-season recreation anchors the market, from winter skiing to the Belleayre Beach at Pine Hill Lake, minutes off the Route 28 corridor through the Catskill Park. The acreage carries a long development-planning history, with extensive environmental review and engineering work already completed on portions of the holdings.

The portfolio may be acquired in a single transaction or as subdivided parcels, and parcels can be assembled to suit through lot-line adjustments. That flexibility allows investors and developers seeking assembled acreage in a supply-constrained market with meaningful barriers to entry to build responsibly to the needs of the community, whether the concept is hospitality, residential, or other commercial use.

A confidential offering package with parcel maps, acreage, and background is available to qualified buyers under NDA.

View the marketing deck (PDF)Request offering materials

Asset management · Development

The Emerson Resort & Spa

Asset management and development of a luxury resort and spa in the Catskills.

Set on the Esopus Creek along the Route 28 corridor in Mount Tremper, New York, the Emerson Resort & Spa is the Catskills' premier independent resort. The Emerson paved the way for the region's boutique wave and was first featured on the cover of Wine Spectator in 2001. After the original inn burned down in 2005, it was rebuilt and established in 2007 as the first higher-end, modern-era resort in the Catskills.

Today the Emerson is undergoing a strategic repositioning and reinvestment, beginning with the re-envisioning of the Inn's restaurant and great room.

DD|HA serves as asset manager for the resort, overseeing financial performance, operations, capital planning, and development strategy. The work spans revenue strategy, expense discipline, capital projects, and the positioning decisions that drive long-term value for ownership.

Capital markets · Development

Lowell ground-up boutique hotel

A proposed boutique hotel development in downtown Lowell, with DD|HA leading the advisory and capitalization.

Concept rendering of the proposed Lowell boutique hotel at dusk — Concept rendering, AI-generated for illustration. Final design will differ.

Lowell is one of Massachusetts' great mill cities: a national historical park, a university city, and a downtown of brick-and-beam architecture forty minutes from Boston, with no boutique lodging to match it. DD|HA is working in capital markets and development on a ground-up boutique hotel positioned to serve the market's universities, businesses, medical institutions, and visitors.

The firm is raising the project's debt and equity and driving the development plan: feasibility and underwriting, program and brand direction, and deal structure.

Additional detail on the site, program, and timeline is available to qualified investors and partners.

Concept renderings of an industrial-style restaurant interior for the Lowell hotel — Restaurant concept imagery, AI-generated for illustration.

Inquire about the project

Advisory · Property tax

The Killington revaluation

Representing the mountain's largest hospitality and land owners through a town-wide revaluation.

When the Town of Killington completed its town-wide revaluation, the resort community's largest properties saw their assessments move sharply. DD|HA represents the Killington Mountain (Killington/Pico) and Killington Grand ownerships through the review and grievance process, along with other hotel and land owners across the market.

Resort properties are among the hardest assets to assess fairly. The real estate, the operating business, and the personal property are bound together, and separating them takes both valuation discipline and an understanding of how these businesses actually run. That is the work DD|HA brings: assessment analysis, allocation of business and intangible value, negotiation with assessors, and formal appeal where it is warranted.

It is the same discipline behind well over $10 million in property tax savings DD|HA has delivered to hotel owners over the last ten years.

For more information.

Call 516-435-4452 or write to thomas@ddha.com.