Oakley Greene is an established villa-style condominium community located within The Highlands section of The Meadows in Sarasota, Florida. Featuring 64 residences, two heated swimming pools, mature landscaping, and scenic golf-course surroundings, Oakley Greene offers spacious, low-maintenance villa living within one of Sarasota’s most recognizable master-planned communities.
Developed primarily in 1986, Oakley Greene is known for its generously sized single-story villas, private courtyard entrances, attached two-car garages, and attractive natural views. Its setting within The Highlands provides a peaceful residential atmosphere with convenient access to shopping, dining, golf, recreation, and Sarasota’s beautiful Gulf Coast beaches.
Oakley Greene Villas & Residences
Oakley Greene consists of 64 villa-style condominium residences featuring spacious floor plans designed for comfortable single-level living. Many homes offer two or three bedrooms, two bathrooms, and approximately 1,600 to 1,950 square feet of air-conditioned living space, depending on the floor plan and property.
Interior features may include vaulted or tray ceilings, spacious living and dining areas, wood-burning fireplaces, split-bedroom layouts, walk-in closets, and large primary suites. Many residences feature open kitchens, breakfast areas, and expansive windows that provide natural light and views of the surrounding landscaping.
Private courtyard entrances are a distinctive feature of Oakley Greene. These outdoor spaces create an inviting approach to the home and may provide room for gardening, seating, or outdoor dining. Attached two-car garages offer convenient parking and additional storage.
Screened and enclosed lanais extend the living areas outdoors, with some residences enjoying golf-course, lake, wooded, or landscaped views. Many villas have undergone renovations to kitchens, bathrooms, flooring, appliances, and other interior finishes.
Maintenance-Friendly Villa Living
Oakley Greene combines the spaciousness and privacy associated with single-family-style villas with the convenience of condominium ownership. Although the residences are commonly marketed as villas, they are legally organized as condominiums under Oakley Green Condominium Association.
The condominium association oversees shared property responsibilities and maintenance services according to its governing documents. Association fees may include exterior building maintenance, roof-related maintenance, landscaping, irrigation, pest control, insurance on covered common elements, private road upkeep, and maintenance of the neighborhood swimming pools.
This arrangement appeals to buyers seeking a more convenient residential lifestyle, including seasonal homeowners who prefer a lock-and-leave Florida property.
Buyers should review the current condominium budget, reserves, insurance coverage, assessments, roof responsibilities, exterior maintenance obligations, leasing restrictions, and pet policies before purchasing. Specific services and owner responsibilities are determined by the association’s governing documents.
Oakley Greene Community Amenities
Oakley Greene offers an attractive neighborhood setting with mature trees, peaceful residential streets, and two heated swimming pools. Residents enjoy convenient recreational facilities without needing a golf membership to use the neighborhood pools.
- Two heated neighborhood swimming pools
- 64 villa-style condominium residences
- Spacious single-story floor plans
- Attached two-car garages at many residences
- Private courtyard entrances and patios
- Screened or enclosed lanais
- Golf-course, lake, wooded, and landscaped views at select properties
- Mature oak trees and tropical landscaping
- Association-maintained common areas
- Convenient access to The Meadows walking and biking trails
- Nearby golf, tennis, pickleball, and fitness facilities
The combination of generous interior space, two community swimming pools, scenic surroundings, and association-provided maintenance makes Oakley Greene an appealing option for buyers seeking an established Sarasota villa community.
The Meadows Lifestyle & Recreational Amenities
Oakley Greene residents are also part of the larger Meadows community, known for its mature oak trees, landscaped open spaces, scenic waterways, and extensive recreational opportunities.
The Meadows features approximately 14 miles of walking and biking trails, more than 85 lakes and waterways, and substantial green space throughout the master-planned community.
Through The Meadows Community Association’s Renaissance Access program, qualifying residents may participate in recreational facilities and activities that include:
- Community fitness and wellness facilities
- Community swimming pool
- Tennis and pickleball facilities
- Dog park and playground
- Basketball court
- Community clubs and organized social activities
- Scenic walking and biking trails
- Golf opportunities within The Meadows
Certain recreational facilities and activities require registration, additional fees, or other arrangements. Residents should confirm current access requirements and program availability with The Meadows Community Association.
Golf at The Meadows
Golf remains an important part of The Meadows lifestyle, particularly throughout The Highlands, where scenic fairways and mature landscaping contribute to the area’s attractive residential surroundings. Select Oakley Greene residences enjoy beautiful golf-course views.
Golf membership is not required to own an Oakley Greene villa. Golf is available through Meadows Golf Club, which features The Meadows and The Groves golf courses, with public play, resident benefits, and optional participation programs.
Qualifying Renaissance Access cardholders may receive discounted rates and priority booking privileges. Residents interested in golf should verify current course availability, greens fees, resident benefits, and optional programs directly with Meadows Golf Club.
Oakley Greene Sarasota Location
Oakley Greene is located in The Highlands section of The Meadows within Sarasota’s 34235 zip code. Residences are situated along Oakley Greene and portions of Highland Oaks Drive, with access from Longmeadow through the Highlands neighborhood. Nearby Honore Avenue provides convenient connections to University Parkway, Fruitville Road, and Interstate 75.
The nearby University Town Center shopping and dining district offers an extensive selection of retail stores, restaurants, entertainment destinations, medical facilities, and everyday conveniences.
Nathan Benderson Park is also within driving distance, providing opportunities for walking, cycling, rowing, paddling, and outdoor events. Additional shopping, grocery stores, and healthcare services are available throughout the University Parkway and Fruitville Road corridors.
Downtown Sarasota & Gulf Coast Beaches
Oakley Greene residents can explore Downtown Sarasota, known for its waterfront parks, restaurants, theaters, art galleries, performing arts venues, and cultural attractions.
The beautiful Gulf Coast beaches of Lido Key and Siesta Key are also within driving distance. Residents can enjoy swimming, boating, fishing, beach walks, and waterfront dining while returning home to Oakley Greene’s peaceful residential surroundings.
Similar Villa Communities in The Meadows
- Highland Park – An intimate 20-residence condominium neighborhood in The Highlands featuring spacious freestanding villas, attached two-car garages, and maintenance-friendly living.
- Chatsworth Greene – A 66-residence villa-style condominium community offering spacious floor plans, a neighborhood swimming pool, and scenic golf-course surroundings.
- Hadfield Greene – An established Highlands villa community featuring spacious residences, mature landscaping, and a comfortable low-maintenance lifestyle.
- Penshurst Park – A 42-residence villa community within The Highlands offering attractive golf-course surroundings and convenient access to Meadows amenities.
- Kingsmere – A 56-residence villa-style condominium community featuring private courtyards, a neighborhood pool, and scenic golf-course views.
Oakley Greene Villas for Sale | The Meadows Sarasota Florida
Explore current Oakley Greene villas for sale below. With just 64 residences, available inventory may be limited in this established neighborhood. Buyers seeking similar spacious villas or maintenance-friendly properties can also explore additional homes and condominiums throughout The Meadows Sarasota.
Frequently Asked Questions About Oakley Greene
Where is Oakley Greene located in Sarasota?
Oakley Greene is located in The Highlands section of The Meadows in Sarasota, Florida 34235. Residences are situated along Oakley Greene and Highland Oaks Drive, with access from Longmeadow near Honore Avenue.
How many residences are in Oakley Greene?
Oakley Greene consists of 64 villa-style condominium residences. Developed primarily in 1986, the neighborhood features spacious single-story homes, attached garages, private courtyards, and mature landscaping.
Are Oakley Greene villas legally condominiums?
Yes. Although Oakley Greene residences are commonly marketed as villas, they are legally organized as condominiums. Owners are subject to the neighborhood condominium association’s governing documents and The Meadows Community Association’s applicable master requirements.
Does Oakley Greene have community swimming pools?
Yes. Oakley Greene features two heated neighborhood swimming pools. Residents can enjoy these community amenities without purchasing a golf membership, subject to applicable condominium association rules.
How large are Oakley Greene villas?
Many Oakley Greene villas offer approximately 1,600 to 1,950 square feet of air-conditioned living space, typically with two or three bedrooms, two bathrooms, and attached garages. Individual floor plans, renovations, and features vary.
Interested in Oakley Greene or another villa community within The Meadows? Contact Wendy Lynn | eXp Realty for assistance comparing available villas, condominium fees, maintenance responsibilities, recreational amenities, and other Sarasota real estate opportunities.

