Oakmont Village Homes with Pickleball Amenities

Welcome to Oakmont Village, a vibrant and welcoming subdivision nestled in the heart of Fort Myers, Florida, in Lee County. This charming community is designed for those who seek a blend of comfort, convenience, and an active lifestyle. With its picturesque streets and beautifully landscaped properties, Oakmont Village offers an inviting atmosphere that feels like home from the moment you arrive.

One of the standout features of Oakmont Village is its commitment to promoting an active lifestyle, particularly for pickleball enthusiasts. Residents here enjoy access to top-notch pickleball amenities, making it easy to connect with neighbors while engaging in friendly competition. Whether you’re a seasoned player or just looking to learn the ropes, the community’s pickleball courts provide the perfect setting to enjoy this popular sport.

The homes in Oakmont Village are thoughtfully designed, boasting modern features and spacious layouts that cater to a variety of lifestyles. With a range of options available, from cozy single-family homes to more expansive residences, there’s something for everyone. Many properties come with lush backyards, perfect for relaxing or entertaining after a day of pickleball.

In addition to its recreational offerings, Oakmont Village is conveniently located near shopping, dining, and entertainment options, ensuring that residents have everything they need right at their fingertips. With beautiful weather year-round, outdoor enthusiasts can enjoy the nearby parks, nature trails, and stunning Gulf Coast beaches.

Discover the charm of Oakmont Village, where community spirit and an active lifestyle come together in perfect harmony. Your dream home awaits in this delightful Fort Myers subdivision!

Newest Oakmont Village Homes with Pickleball Amenities

$194,500

2 Beds ⋅ 2 Baths ⋅ 2026034708 MLS

Incredible Opportunity Awaits! Bring Offers. SELLER Credit to Buyers for pre-paids and or Closing Costs! Seller is offering Owner Carry/Lease option. Welcome to Hideaway Country Club, the crown jewel of Florida's golf scene, proudly ranked as the #1 Par-67 Course! Enjoy the luxury of no trail fees with your resident-owned golf cart, plus access to fantastic amenities like tennis courts, a state-of-the-art workout facility, and a stunning clubhouse and restaurant that’s perfect for socializing. This end unit condo boasts breathtaking views of the golf course and serene waters. Just a quick drive away, you'll discover the picturesque beaches of Sanibel, Captiva, and Fort Myers Beach. Plus, it’s pet-friendly—your furry friends are welcome too! You'll appreciate the deeded brand-new carport and dedicated golf cart parking, complete with ample storage right next to your carport. The building has been revitalized with a new roof and fresh exterior paint, all completed in 2025.Step inside this beautiful, move-in ready 1370 sq. ft. condo, and you’ll be greeted by an all-new kitchen featuring elegant shaker-style cabinets, stunning granite countertops, and brand-new LG stainless steel appliances. Both bathroom vanities, granite countertops, and plumbing fixtures are brand new! Enjoy modern upgrades like new interior doors with brushed nickel hardware, keyless entry, and a fresh coat of paint throughout, along with stylish new ceiling fans. And that’s not all! Your HOA fees include CABLE and INTERNET, making this the perfect blend of comfort and convenience. Ready to see your dream home? Let’s talk about the furnishings and make this beauty yours!

5805 Trailwinds DR Unit 326, Fort Myers

$170,000

3 Beds ⋅ 2 Baths ⋅ 2026025369 MLS ⋅ Oakmont Village BLDG.

Welcome to this charming turnkey 3-bedroom, 2-bathroom first-floor condo located in the heart of Fort Myers within the desirable Hideaway Country Club community. Enjoy peaceful golf course views from your private screened lanai overlooking the lush green fairways, complete with convenient electric shutters for added protection and peace of mind. This well-maintained home features numerous updates, including a new AC system installed in 2023, a dishwasher replaced in 2024, updated countertops, and convenient pull-out drawers that maximize kitchen storage and functionality. The spacious floor plan offers comfortable living with the added convenience of an in-unit washer and dryer. Outside, you’ll appreciate the covered carport for your vehicle, a separate golf cart carport, and a private storage shed for all your extras. Whether you’re looking for an active lifestyle or a relaxing retreat, Hideaway Country Club has something for everyone. Residents enjoy access to pickleball, tennis, a community pool, exercise room, on-site restaurant, and a variety of social activities. Golf enthusiasts will love having access to the course, with memberships available separately and not bundled into ownership. Don’t miss this opportunity to own a move-in-ready condo in one of Fort Myers’ most sought-after golf communities!

5905 Trailwinds DR Unit 812, Fort Myers

$239,900

2 Beds ⋅ 2 Baths ⋅ 2026018493 MLS ⋅ Oakmont Village BLDG.

Beautiful 2 BR + Den condo that has been totally updated. The home comes turnkey with newer furniture. Golf cart parking at your door. The lanai is glassed in and can be used as a breakfast room with a coffee bar and plenty of extra storage. The view out the lanai windows is the manicured landscaping, lakes and the golf course. Heated pool, fitness center, clubhouse/restaurant. If you do not play golf there are plenty of other activities to keep you busy. If you play golf this is the best golf value in SW Florida, manicured golf course, no cart or trail fees when you own your golf cart, lowest membership fees. This quiet and friendly community has a lot to offer. It is conveniently located for restaurants, grocery stores, shopping, a theatre, baseball, downtown, and the airport.

5805 Trailwinds DR Unit 314, Fort Myers

$164,900

3 Beds ⋅ 2 Baths ⋅ 2026011949 MLS ⋅ Oakmont Village BLDG.

Welcome to Oakmont Village! This desirable 2nd-floor condo at 15785 Trailwinds Drive #222 offers peaceful golf course views from your private screened balcony—perfect for morning coffee or evening relaxation. Inside, you’ll find a spacious layout with a generously sized kitchen featuring ample cabinetry and workspace, ideal for cooking and entertaining. The living area is enhanced by a cozy fireplace, adding warmth and charm. Additional highlights include a covered carport, dedicated golf cart port, and extra storage located just outside the unit—all conveying with the sale. Enjoy comfortable Florida living in a well-maintained community close to shopping, dining, and recreation. Living in Oakmont Village means you’re immersed in a vibrant community centered around top-tier golfing, scenic lakes, and a richly social lifestyle. Don’t miss this opportunity to combine comfort, view-rich living, and resort-style amenities.

5785 Trailwinds DR Unit 222, Fort Myers

$169,900

3 Beds ⋅ 2 Baths ⋅ 2025005046 MLS ⋅ Oakmont Village BLDG.

Price Improvement! This beautifully maintained first-floor end unit an incredible opportunity in The Hideaway Country Club. Featuring brand new Luxury Vinyl Plank flooring installed in the main living areas and kitchen in January 2026, this spacious 3-bedroom, 2-bath condo offers a light, coastal feel with stunning lake and golf course views from multiple rooms. The desirable end-unit location provides additional privacy and natural light, while the air-conditioned Florida Room creates extra year-round living space perfect for relaxing or entertaining. The updated guest bathroom adds a modern touch, and the home is being offered mostly furnished with only a few exclusions, making it easy to start enjoying the Southwest Florida lifestyle right away. Additional features include a designated covered parking space, golf cart parking space, private exterior storage closet, plus access to a shared workshop and garden room available for residents. Oakmont Village residents also enjoy a sparkling village pool and patio area just steps away. The Hideaway Country Club offers optional golf and tennis memberships, clubhouse dining, and a welcoming active community atmosphere all centrally located near shopping, dining, beaches, RSW Airport, and everything Fort Myers has to offer. Don’t miss your chance to own one of the best values and lowest priced 3-bedroom condos in this sought-after community!

5905 Trailwinds DR Unit 816, Fort Myers

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