HHC Strategic ReviewOctober 2019

Comprehensive Strategic Review The Board of Directors conducted a thorough and detailed review of potential strategic alternatives to maximize shareholder valueAs part of its review process, the Board evaluated a broad range of options including a sale, joint venture or spin-off of a portion of the company's assets; a recapitalization of the company; changes in the corporate structure of the company; and a sale of the companyThe Board concluded that the best interests of shareholders are served by the Company executing a Transformation Plan under new executive leadershipAppointed Paul Layne as new CEOPaul Layne will replace David Weinreb on the BoardDavid Weinreb and Grant Herlitz to step down from the CompanyTransformation Plan will create a lean, focused, decentralized organization built around the company’s core master planned communities (‘MPCs’)

Three Pillar Transformation Plan Streamlined Organizational Structure Sale of Non-Core Assets Accelerated Growth in Core MPC Business $45 – $50mm reduction in overhead expenses, which consists of a $40 – $45mm reduction in corporate G&A and a $5mm reduction in overhead costs associated with development ~$2bn1 of non-core asset sales with estimated net cash proceeds of $600mm to be redeployed into share repurchases and development opportunities Decades-long development pipeline Includes the stabilized value of 110 North Wacker upon completion

Strategic Rationale for Business Transformation Creating Value through Focus Improved execution and expedited decision-making Empowering local teams will strengthen Company’s culture Nimble and Efficient Conservative underwriting of new development projects On-time and on-budget completion Increased Accountability Disciplined Capital Allocation Proceeds from non-core asset sales provide near-term liquiditySubstantial capital available for share repurchasesAccelerated development in core MPCs Defensive Financial Profile Corporate G&A savings increase free-cash-flow generationReduced reliance on land and condo sales in the event of a potential downturn in the economy

Paul Layne Appointed New CEO 35 years of diverse real estate operating and development experienceMost recently served as President, Central Region, which includes The Woodlands, The Woodlands Hills and Bridgeland (2012 – Present)Identified and led execution of $1.2bn of commercial development in The Woodlands, increasing The Woodlands NOI by nearly eight-foldLed the development of 110 North Wacker in ChicagoCulture carrier and collaborative leaderExecutive Vice President, Brookfield Properties (2006 – 2012)Oversaw a 9.7 million square-foot portfolio in Houston’s Central Business DistrictVice President, Trizec Properties (1993 – 2006) Paul LayneCEO Paul Layne Background CFO David O’Reilly will take on enhanced role at the companyRegional MPC leaders will have increased decision-making responsibility Management Team Update

HHC’s Strategic Path Forward Legacy HHC Holding-company structure, while critical to early stages of HHC’s development, has become increasingly redundant as the business is managed at the regional MPC-levelIncludes non-core assets which earn inadequate returns and require a disproportionate level of management attention and corporate G&A New HHC Eliminate holding-company structure to become a decentralized and focused organization Realign investment and human capital on core MPC business Columbia Core MPCs Non-Core Assets to be Monetized

Streamlined Organizational Structure Corporate headquarters to move from Dallas to The WoodlandsEliminate overhead associated with non-core assetsRealign each corporate function to drive productivity for the MPCsDecentralized regional management supported by a lean corporate footprintDecision-making guided by strong local teams with decades of experienceShare operational best practices across the regionsReinforce culture of efficiency MPC-focused organization will drive profitable growth

Reduction in Overhead Expenses $45 - $50mm Reduction in Overhead Expenses by 2021 Anticipate $38 - $40mm in one-time cash charges associated with relocation expenses, severance packages and retention payments4 Corporate G&A ($ in mm)1 Includes stock-based compensationOverhead costs associated with development properties are capitalized under GAAP

Defensive Positioning Through the Cycle A simplified and focused business reduces HHC’s reliance on land and condo sales In the event of a dramatic market downturn with no land or condo sales, we expect rental NOI to comfortably cover interest expense and steady-state corporate costs Stabilized NOI target as of Q2 2019. Excludes contribution from non-core assets and the SeaportSteady-state cash G&A incorporates 100% of target cost savings, excludes stock-based compensation expense, and includes ~$10mm of Seaport-related G&A. The Company believes this presentation is conservative given that pro forma rental income excludes Seaport NOI, while pro forma corporate costs are burdened with Seaport-related G&A Current Operating Asset NOI Pro Forma Operating Asset NOI ($ in mm):

Sale of Non-Core Assets ~$2bn1 of non-core asset sales over the next 12 to 18 monthsEstimated cash proceeds of $600mm, net of debt and transaction costsProceeds will be redeployed into share repurchases and development opportunities in the core MPCsNon-core assets under consideration have one or more of the following attributes: Located outside of the MPCs, Ward Village, Seaport Requires significant capital to develop Non-rental sources of revenue Limited competitive differentiation under HHC ownership Includes the stabilized value of 110 North Wacker upon completion Management will periodically re-evaluate the portfolio and consider monetization of additional assets that are not well suited for long-term HHC ownership

Non-Core Assets Non-Core Asset Region Annualized Q2 ’19 NOI Estimated Stabilized NOI Non-Core Assets Located Outside of the MPCs: ($ in mm) ($ in mm) 110 North Wacker Chicago - $14.4 Cottonwood Mall1 Salt Lake City - - West Windsor Central New Jersey - - Elk Grove Sacramento - - Outlet Collection at Riverwalk New Orleans $6.1 $6.5 Bridges Of Mint Hill Charlotte - - 85 South Street New York $0.4 $0.5 Monarch City Dallas - - 2007 Gulfstream G450 - - - Select MPC Assets Under Consideration MD Anderson (100 Fellowship Drive) Woodlands - $5.1 Woodlands Hospitality Portfolio Woodlands $27.3 $31.5 Non-Core Retail Assets Various MPCs $6.0 $8.1 Total $39.8 $66.1 Sold for $46mm in September 2019

Long-Term MPC Value Creation Model NOI Cash Flow Development Land Appreciation Growing stream of recurring rental income Densification improves desirability of MPCs and increases land values 2011 vs. 2019E Residential Land Price / Acre NOI in mm:1 $55 Cash flows from NOI and land and condo sales fund commercial development Equity for Development Spend Land and Condo Sales NOI Excludes contribution from Seaport DistrictRepresents Q2 2019 annualized $216 2 +393% Increase

Focused Growth in Core MPCs | The Woodlands 7 million square feet of near-term identified parcels:>1 million square feet of office>1,000 multi-family units500K square feet of retail600 hotel roomsSignificant underlying demandExisting 2.3 million square-foot office portfolio is 95% leasedExisting multi-family portfolio is 96% leasedHughes Landing office & hotel (F)Waterway office opportunities (B & C)Office build-to-suit opportunitiesExpand multi-family offerings and locationsHealthcare-related, retail & self-storage development opportunities Commercial Development Pipeline

Focused Growth in Core MPCs | Summerlin Commercial Development Pipeline 8 million square feet of near-term identified commercial development opportunities5 million square feet of office / 5,600 multi-family units / 100K square feet of neighborhood retailExisting office portfolio is currently 99% leasedDowntown Summerlin office, hotel and multi-family offerings (A)Expand development locations outside of Downtown Summerlin (B & C)Expand development product types to potentially include retail, office build-to-suit, self-storage, homes-for-rent and healthcare-related offerings Aristocrat & Near-Term Commercial Development Opportunities (B) Downtown Summerlin (A) Future Long-Term Commercial Development Opportunities (C)

Focused Growth in Core MPCs | Columbia Merriweather District 4.5 million square feet of near-term development:>2 million square feet office / 1,900 multi-family units 320K square feet of retail / 210 hotel rooms Lakefront District Potential to develop >800 multi-family unitsSupplement with ~750K square feet of office, retail and healthcare-related opportunities

Focused Growth in Core MPCs | Ward Village Completed Completed Completed Completed Completed Completed UnderConstruction2021 2023 2023 2023 2023 2024 2023 2025 2025 2026 2028 2024 Under Construction 2022 5 condo projects completed, 4 in Ward Village2 condo projects under construction (A’ali’i and Ko’ula)A’ali’i is 82% pre-soldKo’ula is 64% pre-soldReadying Victoria Place (newest condo project) for pre-sales in early 2020Greater than 6 million square feet of remaining entitlementsStrong balance of front, 2nd and 3rd row remain to be developedModestly accelerate condo development over time Continue redevelopment of ground floor retail Monitor potential for hotel / condo-hotel opportunities Development Highlights

Update on Seaport Complete development of Tin Building, which will drive significant traffic to the Seaport DistrictLease remaining office space in Pier 17 and Fulton Market BuildingComplete openings and stabilize restaurant operationsFinalize plan for 250 Water Street and remaining air rights As the Seaport is closer to achieving a critical mass of offerings, the Company will consider partnering with third parties to reduce its equity commitment Roadmap to Stabilization

Summary Highlights The business is continuing to perform well across all segments. The Company looks forward to announcing Q3 2019 results on November 4, 2019 New LeadershipStreamlined Organizational Structure Resulting in $45 - $50mm Reduction in Overhead Expenses~$2bn of Non-Core Asset SalesAccelerated Growth in Core MPC Business

Appendix

Reconciliation of Net Operating Income to Net income