Windward Properties

What Windward Properties does

Windward Properties is a privately held, full-service residential real estate brokerage and property management firm headquartered in Kailua, Oahu, Hawaii. Founded in 2005 by Principal Broker and Owner Hillary Sibley and her husband, the company operates with a six-person team — the Principal Broker/Owner, a Broker-in-Charge (Ellie Ambrocio), and four REALTORs — serving residential buyers, sellers, and investors across Oahu (with a nascent presence on Kauai). Its service offering spans the full transaction lifecycle, from listing and market research through escrow, alongside a recurring property management line covering tenant management, maintenance coordination, and rent collection for owners of single-family homes, condos, townhouses, and multi-family properties.

The company's go-to-market is fundamentally agent-led and direct: full-cycle agents handle each transaction personally, supplemented by a website (windwardproperties.com) that functions as the primary marketing surface for listings, testimonials, and lead capture. Pricing is commission-based on transactions (not publicly disclosed) with property management fees negotiated individually. The firm has differentiated itself through deep local market knowledge and a deliberate focus on military families stationed at MCBH, Schofield Barracks, and Wheeler, supported by multiple agents with Marine Corps and Coast Guard backgrounds. It has selectively built adjacent partnerships (e.g., Philpotts Interiors for turnkey staging) and operates no proprietary technology platform, relying instead on standard real estate website tools and personal agent relationships to drive activity.

Name

Windward Properties

Legal name

Windward Properties

Website

https://windwardproperties.com

Company type

Private

Founded year

2005

Operating status

Operating

Headcount range

1–10 employees

Short description

Windward Properties is a privately held, full-service residential real estate brokerage and property management firm founded in 2005, serving buyers, sellers, and rental property owners on Oahu, Hawaii with a six-agent team led by Principal Broker Hillary Sibley.

Ownership category

akta.pro rank

Product category

Residential Real Estate Brokerage and Property Management

NAICS

Real Estate Property Managers (53131), Residential Property Managers (531311)

SIC

Real Estate Agents & Managers (For Others) (6531)

akta.pro primary industry

Full-Service Vacation Rental Property Management (BPAJAIAA)

Keywords

• Residential real estate
• Property management
• Home buying
• Home selling
• Rental management

Headquarters

HQ city

Kaneohe

HQ country

United States

HQ region

North America

Offices1 record

Markets served

GTM type

B2C

Offering type

Services

Cost components

Personnel, Operations, Marketing or Sales

Revenue model

1. Real Estate Sales Commissions: Traditional real estate commission-based revenue from helping buyers and sellers complete residential property transactions on Oahu. Agents facilitate the entire transaction process.
2. Property Management Services: Ongoing property management services for rental properties, including tenant management, maintenance coordination, and payment processing for property owners.

Pricing tiers

Go-to-market motion1 record

Distribution channels1 record

Marketing channels3 records

Core offering

Windward Properties is an elite, full-service residential real estate and property management company serving the Hawaiian island of Oahu. Agents assist buyers, sellers, and investors through the entire residential property transaction lifecycle, and provide ongoing property management for rental owners including tenant management, maintenance coordination, and rent collection. The company operates through a small six-person agent team led by the founder/Principal Broker, handling single-family homes, condos, townhouses, and multi-family properties.

Differentiator

Problem solved

Functional benefit

Quantifiable outcome

• Satisfied customers consistently highlight professional service, attention to detail, and successful transaction outcomes across multiple testimonials

Named customers8 records

Segments3 records

Ideal customer profiles3 records

Technology focussed No

API detail

Has API

No

API docs

API detail

Core technology

AI maturity

App detail

Partnerships

One partnership is on record.

• Philpotts InteriorsminorStrategic or Co-development PartnerInterior design firm Philpotts Interiors was engaged to curate materials and finishes for a turnkey listing (Exquisite Turnkey Home in Tropical Setting), demonstrating collaboration for high-end property staging and presentation.

Scale indicators3 records

Recent moves6 records

Expansion highlights5 records

Broad incumbents

• Compass Hawaii: Tech-forward national brokerage with active Hawaii operations. Competes on premium-segment listings and brings proprietary technology that contrasts with Windward's minimal-tech profile.
• Keller Williams Realty Hawaii: Franchise arm of the large national brokerage operating across Hawaii. Competes for the same residential inventory pool and uses a similar agent-based model, but at materially greater scale and brand-recognition.
• Coldwell Banker Island Properties: Hawaii arm of the national Coldwell Banker network offering residential brokerage and property management across the islands. Competes for the same Oahu residential clients at much larger scale.
• Sotheby's International Realty Hawaii: Luxury-leaning international brand with Hawaii offices focused on high-end residential inventory. Adjacent competitor for premium Oahu listings Windward also services.
• Berkshire Hathaway HomeServices Hawaii Realty: Major national brand with significant Hawaii presence providing residential sales and relocation services. Overlaps with Windward on buyer/seller representation, particularly military relocation transactions.

Direct peers

• Locations Hawaii: Locally founded Hawaii residential brokerage with full-service buyer/seller representation on Oahu and other islands. Closely matches Windward's boutique, locally-rooted value proposition.
• Hawaii Life Real Estate Brokers: Hawaii-focused boutique brokerage operating across multiple Hawaiian islands. Most directly comparable to Windward Properties in mission and geographic focus, though at significantly larger scale and with a luxury-leaning brand.

Emerging players

• eXp Realty Hawaii: Cloud-based brokerage with active Hawaii agents and a low-overhead model that competes on agent recruitment economics. A potential disruptor to traditional boutique models like Windward.
• Help-U-Sell Honolulu: Discount-fee brokerage model with Hawaii operations. Competes on commission rate rather than full-service positioning — a partial competitor for price-sensitive Oahu sellers.

Others

• Honolulu Board of REALTORS (MLS / referral network): Not a direct competitor but the dominant Oahu MLS and referral infrastructure that Windward Properties and all Hawaii brokerages transact through; relevant ecosystem participant for any peer-comparison context.

Market position

Strengths4 records

Weaknesses4 records

Competitive moat4 records

Key risks6 records

Key highlights6 records

Customer concentration

• Facebookfacebook.com/AmbrocioTeam
• LinkedInlinkedin.com/company/windwardproperties

Revenue estimate

Valuation estimate

Number of profiles

Profiles6 records

Funding overview

Funding rounds

Investors

Funding detail is available on the Subscription and Enterprise plan.Contact sales →

M&A

Investments

M&A and investment is available on the Subscription and Enterprise plan.Contact sales →

Frequently asked questions about Windward Properties