- Racing Including Track Operations, Middleburg
- Radio Stations & Broadcasting Companies, Middleburg
- Real Estate, Middleburg - Agent, Broker & Companies
- Real Estate Agent - Property Lessors, Middleburg
- Real Estate Management, Middleburg
- Real Estate Services, Middleburg
- Recreational Equipment & Supplies Companies, Middleburg
- Religious Education, Middleburg
- Religious Organizations, Middleburg
- Repair Services, Middleburg
- Research Services, Middleburg
- Residential, Middleburg
- Residential Apartments, Middleburg
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- Residential Construction Contractors, Middleburg - General Contractors
- Resorts & Hotels, Middleburg
- Restaurant & Lounge, Bar, Or Pub, Middleburg
- Restaurants/Food & Dining, Middleburg
- Retail Book Stores, Middleburg
- Retreat Facilities & Houses, Middleburg
- Riding & Rodeo Services, Middleburg
- Riding Apparel & Equipment, Middleburg
- Rodeo & Equestrian Equipment & Supplies, Middleburg
- Roofing Consultants, Middleburg - Roofing Companies
- Roofing Contractors, Middleburg - Roof Repair, Cleaning, Installation & Maintenance - Roofers
- Rv Parks, Middleburg
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