Highland Park is an intimate villa-style condominium neighborhood located within The Highlands section of The Meadows in Sarasota, Florida. Featuring just 20 freestanding residences, Highland Park combines the privacy and spaciousness of detached homes with the convenience of condominium ownership and association-provided maintenance.
Developed in 1988, Highland Park is known for its generous floor plans, attached two-car garages, mature oak trees, and peaceful residential setting. Unlike many attached villa communities throughout The Meadows, these residences have no shared walls, creating an appealing alternative for buyers seeking single-family-style living with fewer exterior maintenance responsibilities.
Highland Park Villas & Residences
Highland Park consists of 20 detached villa-style condominium residences designed for comfortable single-level living. Homes commonly feature two or three bedrooms, two or more bathrooms, and approximately 2,000 to 2,400 square feet of air-conditioned living space, depending on the floor plan.
Many residences feature cathedral or vaulted ceilings, spacious great rooms, formal dining areas, wood-burning fireplaces, built-in wet bars, and generous primary suites. Large windows and sliding glass doors bring natural light into the living areas while connecting the interiors to private outdoor spaces.
Attached two-car garages provide additional storage and convenience. Depending on the property, villas may feature courtyard-style entrances, spacious laundry rooms, walk-in closets, screened lanais, and attractive landscaped views.
Over the years, individual residences have received updates to kitchens, bathrooms, flooring, appliances, and other interior finishes. Buyers can find a variety of renovation styles and opportunities to personalize these spacious homes.
Freestanding Villas & Condominium Ownership
One of Highland Park’s most distinctive characteristics is its freestanding villa design. Although the residences resemble detached single-family homes, Highland Park is legally organized as a condominium under Highland Park Condominium Association.
Unlike traditional attached condominium villas, Highland Park residences do not share common walls with neighboring homes. This design offers greater separation between residences while retaining the benefits of association-managed property maintenance.
The condominium association oversees shared property responsibilities and maintenance services according to its governing documents. Association fees may include exterior building maintenance, landscaping, insurance on covered common elements, pest control, private road maintenance, and other shared expenses.
Buyers should review the current condominium budget, reserves, insurance coverage, special assessments, roof responsibilities, exterior maintenance obligations, pet policies, and rental restrictions before purchasing. Specific services and owner responsibilities are determined by the association’s governing documents.
Highland Park Community Amenities
Highland Park offers a quiet residential atmosphere with spacious villas, attractive landscaping, and convenient access to the recreational opportunities throughout The Highlands and The Meadows.
- 20 freestanding villa-style condominium residences
- Detached homes without shared walls
- Spacious single-story floor plans
- Attached two-car garages
- Private courtyards and screened or enclosed lanais at select residences
- Mature oak trees and tropical landscaping
- Scenic landscaped and natural surroundings
- Association-maintained common areas
- Convenient access to walking and biking trails
- Nearby golf, tennis, pickleball, swimming, and fitness facilities
The combination of detached residences, generous interior space, and maintenance-friendly ownership creates an appealing setting for full-time homeowners and seasonal residents alike.
The Meadows Lifestyle & Recreational Amenities
Highland Park residents are part of the larger Meadows community, known for its mature landscaping, expansive green 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 beautifully maintained natural surroundings throughout the master-planned community.
Through The Meadows Community Association’s Renaissance Access program, qualifying residents may enjoy recreational facilities and activities that include:
- Community fitness and wellness facilities
- Junior Olympic-sized swimming pool
- Tennis and pickleball facilities
- Dog park and playground
- Basketball court
- Community clubs and organized social activities
- Walking and biking trails
- Golf opportunities within The Meadows
Certain recreational facilities and activities require registration, additional user 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 established fairways and mature landscaping contribute to the area’s attractive residential surroundings.
Golf membership is not required to own a Highland Park villa. Golf is available through Meadows Golf Club, which operates The Meadows and The Groves golf courses with public play, resident benefits, and optional participation programs.
Residents interested in golf should verify current course availability, greens fees, booking privileges, resident discounts, and optional programs directly with Meadows Golf Club.
Highland Park Sarasota Location
Highland Park is located in The Highlands section of The Meadows within Sarasota’s 34235 zip code. The neighborhood is situated along the residential street named Highland Park, accessed from Longmeadow via Hadfield Drive and Highland Oaks Drive. 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
Highland Park residents can explore Downtown Sarasota, known for its waterfront parks, restaurants, theaters, art galleries, cultural attractions, and performing arts venues.
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 before returning to the peaceful surroundings of Highland Park.
Similar Villa Communities in The Meadows
- Chatsworth Greene – A 66-residence villa-style condominium community in The Highlands featuring spacious floor plans, attached garages, and scenic golf-course surroundings.
- Hadfield Greene – An established villa community within The Highlands offering spacious residences, attractive natural surroundings, and maintenance-friendly living.
- Oakley Green – A 64-residence Meadows neighborhood featuring villa-style homes, established landscaping, and a convenient residential setting.
- Kingsmere – An established 56-residence villa community offering comfortable floor plans, mature landscaping, and access to Meadows recreational amenities.
- Penshurst Park – A 42-residence villa community within The Highlands featuring spacious homes, attractive golf-course surroundings, and convenient access to recreational facilities.
Highland Park Villas for Sale | The Meadows Sarasota Florida
Explore available Highland Park villas for sale below. With only 20 freestanding residences, available inventory can be very limited. Buyers seeking similar detached villa-style homes or maintenance-friendly residences can also explore additional properties throughout The Meadows Sarasota.
Frequently Asked Questions About Highland Park
Where is Highland Park located in Sarasota?
Highland Park is located in The Highlands section of The Meadows in Sarasota, Florida 34235. The neighborhood is accessed from Longmeadow via Hadfield Drive and Highland Oaks Drive, near Honore Avenue.
How many residences are in Highland Park?
Highland Park consists of just 20 freestanding villa-style condominium residences. Developed in 1988, the neighborhood features spacious single-story homes, attached garages, and mature landscaping.
Are Highland Park villas attached or detached?
Highland Park villas are freestanding residences without shared walls. Although they offer the appearance and privacy of detached single-family homes, they are legally organized as condominiums.
How large are Highland Park villas?
Highland Park residences commonly offer approximately 2,000 to 2,400 square feet of air-conditioned living space, with two or three bedrooms, two or more bathrooms, and attached two-car garages. Individual layouts and features vary.
Is golf membership required to live in Highland Park?
No. Golf membership is not required to purchase or own a Highland Park residence. Meadows Golf Club offers public play at The Meadows and The Groves golf courses, along with resident benefits and optional golf programs.
Interested in Highland Park 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.

