Who we are

Doolings Home Services

Drew Dooling,
Owner

Drew Dooling is the owner of Doolings Home Services, a trusted provider of residential and community property services in Naples, Florida. Drew holds a Bachelors degree in Communications and a Business Minor from Wingate University. Drew is also a former collegiate athlete who played a key role on the Men’s Soccer Team — an experience that sharpened his discipline, leadership, and drive.

Drew brings over 10 years of operational and customer service experience from his career at Goodyear, including five years as General Manager, where he led high-performing teams and delivered consistent, quality service.

Since acquiring the company in 2012, Drew has overseen it’s evolution from a homewatch-focused business into a specialized service partner for high-end condominiums and residential communities. Today, Doolings Home Services serves multiple condominium associations across Naples, maintaining meticulous standards in cleaning and property oversight. While the company still provides select homewatch services for a small group of C-suite executives, its core focus has shifted to supporting large-scale properties with reliable, professional care.

Drew is a dedicated husband and father of two, and he approaches every client relationship with the same level of care, consistency, and attention to detail he values in his own home.

Who We Serve:

Seville at Pelican Marsh -

Seville at Pelican Marsh is a 84 home attached villa neighborhood located in the central portion of Pelican Marsh. 

Portside Club -

Portside Club at Moorings is located approximately 1 mile southeast of the shopping and restaurants at the Village on Venetian Bay and less than 1 mile east of Moorings Beach.The Portside Club is a 3-story building with a total of 24-units.

Camelot Club -

Camelot Club of Naples, INC is a condominium association located at 3055 Riviera Drive, Naples, FL 34103. The Camelot Club is a 3-story building with a total of 24-units.

Steeplechase -

Steeplechase of Naples is a non-gated community within Kings Lake comprised of two-story building coach homes on a circle drive with 1-car attached garages, community pool, underground utilities, concrete block construction, screened lanais, clubhouse, tile roofs with courtyard and lake views.Total of 72-units.

Lakewood Country Club -

We service 2 three-story buildings, each 30 units and the community pool.

Valley Stream -

At Valley Stream we service 3 buildings, totaling 36 units, and the community pool.

Somerset -

An upscale community in the Moorings, with their own private beach. We service 6 buildings, including the community pool & bathrooms.

The Willows Condominiums -

Willows at Park Shore is located approximately 1-mile south of the shopping and restaurants at the Waterside Shops and a similar distance east of Park Shore Beach. Willows is a secure building within Park Shore comprised of two-story building condominiums on a corner lot with covered parking, community pool, underground utilities, screened lanais, flat roof (modified bitumen roof) with courtyard views. The Willows has 22-condominium units and a large community pool (40-feet).

Heritage Greens - Clubhouse

Heritage Greens is a semi-gated community surrounded by Arrowhead Golf Course. Homes include villa, coach home and single family style living with beautiful views of lakes, natural preserve areas and golf course views.

Crestview at Heritage Greens-

Crestview Condominium at Heritage Greens offers low-rise condominiums with great views of the fairways and emerald lakes.

Luxury Clubhomes at Heritage Greens-

Luxury villas situated in a semi-private community, located within Heritage Greens.

Bay Laurel Estates at Pelican Marsh -

Bay Laurel Estates at Pelican Marsh is a luxury single-family home community located at the southern end of Pelican Marsh best accessed from the Vanderbilt Beach Road entrance. This gated subdivision consists of 38 luxury home sites with 36 homes constructed and two privately-owned vacant lots remaining.

Homewatch:

Doolings Home Services still offers homewatch services to those who wish. Currently, our limited availability for homewatch clients is fulfilled by c-suite executives with a combined property value over $15 million.