The Olive Real Estate Group Inc. Legacy: 5 Key Developments Shaping Colorado Springs In 2025
Olive Real Estate Group Inc. continues its decades-long dominance in the Colorado Springs commercial real estate market, with 2025 marking a period of strategic growth, significant urban redevelopment projects, and a reflection on the company's foundational legacy. As of late 2025, the firm remains the largest full-service commercial real estate company in the Pikes Peak region, specializing in crucial sectors like office, industrial, and retail properties.
The firm's operations, which began in earnest in 1993, have been instrumental in shaping the city's built environment, from major retail centers to downtown urban renewal initiatives. The latest market reports from the first half of 2025 indicate that while national trends show fluctuation, the Colorado Springs commercial sector, which Olive Real Estate Group Inc. helps to define, remains resilient, showcasing continued investment interest and low vacancies in key areas.
The Founders' Legacy and Current Leadership Profile
The history of Olive Real Estate Group Inc. is deeply intertwined with the careers of several prominent real estate professionals who established the firm as a regional powerhouse. The company, as it is known today, was officially founded in 1994, building on the success of The Olive Company, which was formed by John Olive in 1981.
John Olive: The Founder
- Role: Founder and namesake of Olive Real Estate Group, Inc.
- Background: A New Jersey native and graduate of the prestigious United States Air Force Academy (USAFA).
- Early Career: Formed The Olive Company in 1981, focusing on the development of office and retail properties, and was a key player in numerous foundational developments across the region.
James "Jim" DiBiase: Principal and Project Leader
- Role: Principal of Olive Real Estate Group since 1992.
- Reputation: Recognized as one of Colorado Springs' leading real estate professionals, with a focus on brokerage, development, and third-party projects.
- Key Involvement: Has played a central role in major downtown revitalization efforts, including the Tejon and Costilla Urban Renewal Plan.
Honoring Co-Founder James Justus (1945–2025)
A significant event in 2025 was the passing of co-founder James Justus. Jim Justus co-founded the group in 1994 and served as the President and Managing Broker until 2023. His leadership was instrumental in shaping the company's culture and its extensive portfolio, leaving a lasting impact on the Colorado Springs commercial landscape.
Other founding members who contributed to the firm's structure in 1994 included John Winsor, Charley Conrad, Tom Cone, and Stan Kensinger, solidifying a team of seasoned experts in commercial brokerage and property management.
2025 Market Resilience: Insights from the Pikes Peak Region
The firm’s deep local knowledge allows it to provide highly specific market analysis, showcasing the unique strength of the Pikes Peak region's economy. The first half of 2025 saw the Colorado Springs commercial real estate market demonstrating notable resilience, a trend that continues to attract major corporations, investors, and retailers to the area.
Industrial Sector Strength:
The industrial market, a key focus for Olive Real Estate Group Inc., has remained particularly robust. Despite national economic headwinds, the industrial vacancy rate in the Colorado Springs area has remained stable, with a positive net absorption of hundreds of thousands of square feet over the past year. This sustained demand underscores the region's appeal for logistics and light manufacturing.
Office Market Trends:
While the office sector nationwide faces challenges, the Colorado Springs office market has benefited from resilient tenant demand. Olive Real Estate Group Inc. continues to manage and lease a diverse portfolio of office spaces, navigating the current climate with strategic leasing and property management services.
Retail Development Momentum:
The retail arena remains a hotbed of activity. The company is actively involved in the acquisition of land and development of new retail centers, catering to the expanding population base. This includes development projects like Albertson's anchored shopping centers in both Colorado Springs and Pueblo, demonstrating a regional reach.
Five Major Developments & Initiatives Driving 2025 Growth
Olive Real Estate Group Inc.'s current portfolio highlights a strategic focus on high-impact, mixed-use, and commercial projects that are fundamentally changing the urban fabric of Colorado Springs. These developments represent the firm's commitment to long-term regional growth.
- The Tejon and Costilla Urban Renewal Plan: Principal Jim DiBiase is a key figure in the development team for this significant urban renewal project. This initiative is designed to revitalize a central part of the city, demonstrating the firm's involvement in complex, public-private partnerships aimed at civic improvement and economic stimulus.
- Downtown Marriott-Branded Hotel Development: Reflecting a strong belief in the future of downtown Colorado Springs, Olive Real Estate Group Inc., through Jim DiBiase, is part of the development team breaking ground on a major Marriott-branded hotel. This project is a crucial component of increasing hospitality and commercial activity in the core business district.
- New Retail Development: Phase II Leasing: The firm is actively managing the "NOW LEASING" phase for a new retail development located at the Northeast Corner of Meridian Road & Stapleton Drive. This expansion is a direct response to the growing need for modern retail and commercial space outside the immediate downtown area.
- Aeroplaza Drive & Fountain Pre-Leasing: Another significant pre-leasing initiative is underway at the Southwest Corner (SWC) of Aeroplaza Drive and Fountain. This focus on securing tenants early for new commercial properties underscores the proactive brokerage and development strategy of the firm in high-growth corridors.
- Strategic Portfolio Acquisitions: The firm continues to facilitate strategic acquisitions for clients looking to expand their Colorado Springs portfolio. These deals often involve assets in excellent, diverse markets, reflecting the company’s expertise in identifying and securing prime commercial properties across all sectors (office, industrial, retail, and land).
The Full-Service Advantage: Brokerage and Property Management
What sets Olive Real Estate Group Inc. apart is its comprehensive, full-service model. Being the largest of its kind in the region, the company provides far more than simple transaction services; it offers end-to-end solutions for commercial property owners and investors.
Commercial Brokerage: The firm’s team of commercial brokers, including long-time directors like John Winsor, specializes in leasing and sales across all property types—from securing office space for burgeoning tech companies to facilitating the sale of large industrial parks. Their deep local network ensures clients have access to the best available properties.
Property Management: A core component of their offering is property management. This service ensures that commercial properties remain valuable assets, handling everything from tenant relations and lease administration to physical maintenance and financial reporting, thereby maximizing returns for property owners in the Pikes Peak region.
Topical Entities & Keywords
Olive Real Estate Group Inc., Colorado Springs commercial real estate, Pikes Peak region, commercial brokerage, property management, office market, industrial properties, retail development, John Olive, James DiBiase, James Justus, John Winsor, Charley Conrad, Tom Cone, Stan Kensinger, Tejon and Costilla Urban Renewal Plan, Marriott-branded hotel, Meridian Road & Stapleton Drive, Aeroplaza Drive & Fountain, full-service commercial real estate, land acquisition, El Paso County, USAFA graduate.
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