21169 Oakley Court A $5.5 Million Remarkable Golf Course Estate in Boca Raton

Date of Publishing: January 5, 2026

Set behind the gates of Boca Grove Plantation, one of South Florida’s most established private country club communities, 21169 Oakley Court has returned to the market with an asking price of $5.5 million, positioning itself among the most compelling options currently available for buyers seeking a truly expansive home in Boca Raton for sale. Occupying more than half an acre and overlooking manicured fairways, the estate blends classic proportions with modern infrastructure upgrades, offering both scale and longevity in a market increasingly defined by scarcity.

Golf course views from the backyard of 21169 Oakley Court in Boca Raton

Luxury Houses Magazine has reviewed public records, listing data, and market activity surrounding 21169 Oakley Court, confirming that properties of this size and placement within Boca Grove rarely surface, particularly those offering uninterrupted golf course views combined with over 8,000 square feet of interior living space.

A Grand Residence Built for Enduring Living

Originally constructed in 1993, 21169 Oakley Court reflects an era when luxury estates in Florida were designed with generous room dimensions, formal entertaining spaces, and long-term livability in mind. The residence encompasses 8,296 square feet of interior space across a multi-level layout, featuring six ensuite bedrooms, seven full bathrooms, and one half bath, alongside a dedicated office and a four-car garage.

From the moment one enters, the home communicates scale without excess. Large-format marble and wood flooring anchor the primary living areas, while expansive windows frame tranquil views of the golf course beyond. Rather than chasing trends, the interior prioritizes proportion, natural light, and flow, qualities that remain increasingly valued among discerning buyers navigating the Boca Raton real estate landscape.

According to Aviva Bennett of EXP Realty LLC, the property’s appeal lies in its balance. “Homes like 21169 Oakley Court resonate with buyers who want elegance without formality becoming overwhelming,” Bennett told Luxury Houses Magazine. “The layout works beautifully for entertaining, but it’s equally comfortable for daily living, which is something many newer builds struggle to achieve at this scale.”

SEE MORE: A $17.8 Million Cape Dutch Estate in Palm Beach’s North End with Timeless Architectural Appeal

Modern Infrastructure Beneath a Classic Exterior

While the home’s architecture reflects timeless design, its mechanical systems have been meaningfully updated. A new roof installed in 2020, a five-zone air conditioning system, and a full-house generator provide peace of mind and year-round comfort, an increasingly critical consideration for luxury buyers evaluating Boca Raton homes for sale.

These upgrades allow the estate to compete favorably with newer construction, particularly within established country club communities where lot sizes and privacy are difficult to replicate today. The presence of a whole-house generator further elevates the property’s resilience, aligning with expectations at the upper tier of the Boca Raton market.

A Property with a Documented Legacy

The transactional history of 21169 Oakley Court mirrors the broader trajectory of high-end residential values in Boca Raton. Public records indicate the home sold for approximately $1.75 million in the mid-1990s, later trading hands at $2 million in 2005 before entering the modern luxury bracket with a $4.7 million sale in 2022. Its current listing at $5.5 million, introduced in December 2025, reflects both market appreciation and the estate’s enduring relevance.

Luxury Houses Magazine attempted to contact the homeowner to gain additional insight into the property’s evolution over the years, but no response was received. The lack of public commentary is consistent with the discreet ownership profile often associated with long-standing Boca Grove residents.

SEE MORE: $6.7 Million Brand New Waterfront Masterpiece Offering Direct Gulf Access and Sunset Views on Marco Island

Golf Course Living Without Compromise

Positioned along the fairways of Boca Grove Plantation, 21169 Oakley Court benefits from one of the community’s most desirable settings. Boca Grove is widely recognized for its Jim Fazio–designed 18-hole championship golf course, notable for its walkable layout and the absence of mandatory tee times, a rarity among South Florida private clubs.

21169 Oakley Court A 5.5 Million Remarkable Golf Course Estate in Boca Raton 10

Beyond golf, the gated community offers a comprehensive lifestyle framework, including tennis and pickleball courts, a modern fitness center, multiple dining venues, and a calendar of social programming that appeals to both full-time residents and seasonal homeowners. For buyers prioritizing privacy without isolation, Boca Grove continues to rank among the most established options in Boca Raton real estate.

“Buyers are increasingly focused on community quality rather than sheer novelty,” Bennett explained in a separate conversation with Luxury Houses. “Boca Grove has matured beautifully. It offers consistency, discretion, and a strong sense of place, attributes that are difficult to engineer from scratch.”

Interior Spaces Designed for Scale and Function

Inside the residence, rooms unfold in a sequence that favors both grand entertaining and private retreat. The expansive kitchen anchors the main level, offering ample workspace, professional-grade appliances, and sightlines into adjacent living and dining areas. The primary suite, located on the main level, spans more than 1,000 square feet and functions as a private wing, complete with generous closet space and a spa-like bath.

Upstairs living areas provide flexibility for family use or guest accommodations, while the dedicated office reflects the increasing importance of work-from-home functionality among luxury buyers. Throughout the home, ceiling heights and room dimensions reinforce a sense of openness that remains difficult to achieve in contemporary builds constrained by smaller lots.

SEE MORE: $24.9 Million Exceptional Waterfront Estate Showcases Elite Living in Miami’s Bay Point

Location, Connectivity, and Everyday Convenience

While Boca Grove offers a self-contained lifestyle, 21169 Oakley Court also benefits from proximity to Boca Raton’s broader amenities. The estate lies minutes from Town Center at Boca Raton, Mizner Park, and a wide selection of upscale dining destinations, cultural institutions, and private schools. Access to the Florida Turnpike and Interstate 95 ensures convenient connectivity to Palm Beach and Fort Lauderdale, further enhancing the property’s appeal as a home in Boca Raton for sale suited to both primary and secondary residency.

Market observers consulted by Luxury Houses Magazine note that inventory within gated golf communities remains constrained, particularly for homes exceeding half an acre with unobstructed views. This dynamic continues to support pricing resilience in the upper segment of the Boca Raton market.

A Compelling Opportunity in Boca Raton Real Estate

As luxury buyers recalibrate priorities toward space, privacy, and long-term value, 21169 Oakley Court stands out as a residence that delivers on all three. Its blend of architectural scale, infrastructure upgrades, and community prestige positions it as one of the more compelling Boca Raton homes for sale currently available at this price point.

Represented by Aviva Bennett of EXP Realty LLC, the estate offers a rare chance to secure a legacy property within one of Boca Raton’s most established private enclaves, an opportunity that continues to resonate in today’s evolving luxury real estate landscape. To know more information about this property, view on Zillow listing.

For inquiries or to schedule a private showing, please contact:

Aviva Bennett
347-721-6516
EXP Realty LLC

* This property might not for sale at the moment you read this post; please check property status at the above Zillow or Agent website links*

A $5.5 Million Remarkable Golf Course Estate Elevating Luxury Living in Boca Raton