Oakline Properties / Alpine Investors Acquire Four Star Realty

Alpine Investors Launches Oakline Properties Platform

September 25, 2025

Real Estate

Alpine Investors launched Oakline Properties, a new platform to partner with and scale property and association management businesses across the United States. Oakline will partner with outsourced managers (including Cirrus Asset Management) to drive growth through cross-platform lead generation, service expansion, tech enablement and talent, led by CEO Amanda Sayigh.

Oakline Properties Acquires Drucker + Falk

December 19, 2025

Real Estate

Oakline Properties, a portfolio company of Alpine Investors, has acquired Drucker + Falk, a Top-50 NMHC multifamily and commercial property management firm. The transaction brings D+F into Oakline's platform (increasing the platform to 65,000+ units managed) while the Drucker and Falk families will remain actively involved in the business.

NextTrip Acquires Five Star Alliance

April 14, 2025

E-Commerce

NextTrip completed the acquisition of the remaining 51% stake in luxury online travel agency Five Star Alliance, making NextTrip the sole owner. The deal will integrate Five Star Alliance's inventory and expertise to bolster NextTrip's luxury travel offerings and support growth across B2C and B2B travel segments.

Alfred Acquires RKW Residential

March 8, 2022

Real Estate

Alfred, the U.S. residential technology and property-management platform, has acquired RKW Residential and raised a $125 million strategic financing round led by Rialto Capital. The acquisition accelerates Alfred's expansion in the Southeastern U.S. and enables broader deployment of its AlfredOS platform across RKW’s ~30,000 managed single-family and multifamily units.

Merz Lifecare Acquires Majority Stake in WindStar Medical from Oakley Capital

October 7, 2024

Consumer Products

Oakley Capital Fund IV has agreed to combine its portfolio company WindStar Medical with Merz Lifecare, with the Merz Group taking a majority stake in the new holding. The transaction — subject to regulatory approvals — will create a leading provider of OTC health, wellbeing and beauty products in the DACH region and continues Oakley’s support of WindStar following its 2020 investment.

Roundhouse Acquires Multiple Multifamily Properties, Adding 1,530 Units Across the Western U.S.

September 11, 2024

Real Estate

Boise-based multifamily developer and operator Roundhouse acquired several apartment communities in 2024 — including Cycle Apartments (Fort Collins, CO), Clovis Point (Longmont, CO), Eagle's Landing Apartments (Idaho Falls, ID) and Sentral First Hill (Seattle, WA) — adding a total of 1,530 Class A units to its portfolio. The company said the transactions are part of more than $300 million in acquisitions (and $150 million in development groundbreakings) this year as it expands its presence across Western U.S. markets.