Property Management for Peace of Mind

Providing trustworthy, professional property management across Western, Central and New Haven Connecticut, as well as Putnam, Dutchess, and Westchester Counties in New York - helping you protect your investment and reclaim your time.

Brownstone townhouse with ornate carved window trim, wooden front door, potted plants, and flower boxes in a city neighborhood.

Comprehensive Services Offered

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Property Maintenance & Care

  • 24/7 Response to Maintenance Emergencies

  • Coordination of All Repairs with Vetted, Insured Vendors

  • Proactive Property Inspections & Preventative Maintenance Plans

  • Management of Landscaping, Snow Removal, and other services

  • Owner Approval for All Major Expenses

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Tenant Management

  • Full Tenant Relations & Communication

  • Rigorous Tenant Screening (Credit, Criminal, Eviction History, Income Verification)

  • Connecticut-Compliant Lease Preparation & Execution

  • Seamless Tenant Move-In & Move-Out Process

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Financial Management

  • Market Analysis & Optimal Rent Pricing

  • Diligent Rent & Fee Collection

  • Detailed Monthly & Annual Financial Reporting

  • Management of All Property-Related Bills

About
our company

Founded by Robert Hughes, a seasoned corporate finance professional and real estate investor, Pillar & Pine combines the strategic insight of an investor with the hands-on care of an owner. With nearly a decade of personal real estate experience and over 20 years in corporate finance, Robert created this company to provide the kind of high-touch, value-driven service he always looked for in a property manager.

We serve Western and Central Connecticut, as well as Putnam, Dutchess, and Westchester Counties in New York, partnering with owners of multifamily and single-family rental properties to deliver responsive, proactive, and personalized management. Whether you’re a local landlord or an out-of-state investor, we treat your property like it’s our own—because that’s how we’ve built success for ourselves.

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