Oakmont Village Real Estate

Welcome to Oakmont Village, a charming subdivision nestled in the heart of Fort Myers, Florida. This delightful community offers a perfect blend of tranquility and convenience, making it an ideal destination for families, retirees, and everyone in between.

Oakmont Village is characterized by its picturesque tree-lined streets, beautifully manicured lawns, and a warm, welcoming atmosphere. The neighborhood is thoughtfully designed to foster a sense of community, with friendly neighbors and a variety of social activities that bring residents together. Whether you’re enjoying a leisurely stroll or gathering at one of the community events, you’ll quickly feel at home in this inviting enclave.

One of the standout features of Oakmont Village is its prime location. Situated in Lee County, residents enjoy easy access to the vibrant city of Fort Myers, where an array of shopping, dining, and entertainment options await. From charming boutiques to delectable restaurants, there’s something for everyone just a short drive away. Additionally, the stunning Gulf Coast beaches are only minutes away, offering endless opportunities for sun-soaked days and breathtaking sunsets.

Families will appreciate the nearby schools and recreational facilities, providing ample opportunities for children to thrive. With parks, playgrounds, and sports fields in close proximity, outdoor enthusiasts will find plenty of ways to stay active and enjoy Florida’s year-round sunshine.

Oakmont Village is not just a place to live; it’s a lifestyle. Discover the joys of community living in this idyllic Fort Myers neighborhood, where every day feels like a vacation. Come experience the charm of Oakmont Village—your perfect Florida home awaits!

Newest Listings in Oakmont Village

$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

$224,900

2 Beds ⋅ 2 Baths ⋅ 2026024416 MLS ⋅ Oakmont Village BLDG.

WOW WHAT A GOLF AND LAKE VIEW! GREAT 1st FLOOR 2 BR 2 BATH FURNISHED CONDO IN GATED GOLF COMMUNITY WITH ALL THE AMENITIES. BEST OPTIONAL MEMBERSHIP GOLF CONDO IN SW FLORIDA. LOW MEMBERSHIP FEES AND NO CART OR TRAIL FEES IF YOU OWN A GOLF CART. GOLF CART PARKING SPACE INCLUDED. GREAT AMENITIES, GOLF, TENNIS, FITNESS, HEATED POOL, CLUBHOUSE/RESTAURANT AND ALL THE SOCIAL ACTIVITIES YOU COULD WANT TO LIVE THE FLORIDA LIFESTYLE. COMMUNITY IS CONVENIENT TO EVERYTHING, BEACHES, SHOPPING, RESTAURANTS, BASEBALL, AIRPORT, DOWNTOWN ETC. PET FRIENDLY COMMUNITY, MAX 2 pets, no weight limit, no aggressive breeds.

5845 Trailwinds DR Unit 515, Fort Myers

$199,900

2 Beds ⋅ 2 Baths ⋅ 2026019974 MLS

PRICE IMPROVED & MOTIVATED! LEASE OPTION available ask an Agent for terms. Rare opportunity to own a stunningly upgraded end-unit in the "crown jewel" of Florida golf community proudly ranked as the #1 Par-67 Course! The seller is highly motivated to close, offering a beautifully renovated interior featuring all-new Kitchen Cabinets & vanities including luxury granite counter tops and fixtures. Stylish flooring, upgrade wood trim thru=out, and premium LG appliances. Located in Hideaway Country Club, you’ll enjoy a resident-owned cart experience with no trail fees and optional Golf Membership. Community world-class amenities like Har-Tru tennis courts and a state-of-the-art fitness center. This unit comes with a deeded new carport, dedicated golf cart parking, and ample storage. Screen in w/full length windows on Lanai adds a bonus room with views to die for. No Flood Insurance needed. The seller is looking for a smooth sale—bring all reasonable offers and start living the Florida lifestyle now! Creative Financing is always possibility.

5805 Trailwinds DR Unit 326, 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 airpot.

5805 Trailwinds DR Unit 314, Fort Myers

$179,900

2 Beds ⋅ 2 Baths ⋅ 2026008261 MLS ⋅ Oakmont Village BLDG.

Welcome to The Hideaway Country Club, one of the best kept secrets, with a beautiful Golf Course, a beautiful Club House and Restaurant, Tennis Courts, beautiful Pools iwithin each community, and many other activities to keep you as busy as you want. Golf and Tennis are not required. Best golf value in SW Florida. Convenient to everything in Fort Myers. This is a great 2 bedroom, and 2 bath Unit and No carrying groceries and furniture up steps, since you are on the 1st floor. This is an unbeatable value with a view that is hard to find. The view has 3 Fountains and Lakes with lots of open space. Come and have a look and you will not be disappointed. Storm shutters on all the windows and golf cart parking space at your door.

5825 Trailwinds DR Unit 414, Fort Myers

$269,000

3 Beds ⋅ 2 Baths ⋅ 2026001626 MLS ⋅ Oakmont Village BLDG.

Sunset views set the tone for this beautifully maintained 3-bedroom, 2-bath condo located in a premier gated golf course community. Designed for both comfort and entertaining, this spacious residence features an open-concept layout, generously sized bedrooms, and a private primary suite with walk-in closet and en-suite bath. The fully equipped kitchen flows seamlessly into the living area and large enclosed sunroom, the perfect place to relax and enjoy breathtaking evening skies. Convenience abounds with an assigned covered parking space close to the unit, plus a deeded covered golf cart space. Residents enjoy access to multiple resort-style pools, a restaurant and bar, clubhouse with fitness center, game rooms, meeting spaces, golf course, tennis courts, and more. Ideally located near shopping, dining, recreation, major highways, and just a short drive to the beach. Recent community improvements include village paving completed Spring 2026, building freshly painted Fall 2025, and a new roof installed in 2024.

5825 Trailwinds DR Unit 425, Fort Myers

$205,000

3 Beds ⋅ 2 Baths ⋅ 2025009145 MLS

Welcome to this turnkey, move-in ready top-floor condo in the highly desirable Hideaway Country Club, offering the perfect blend of comfort, convenience, and the Florida lifestyle. This beautifully maintained Fort Myers condo features a BRAND NEW A/C (2026) with a 10-year warranty, NO current assessments, and elevator access—a rare and highly sought-after feature within the community. Enjoy breathtaking views of the beautifully manicured 18-hole golf course and three tranquil fountains from your private lanai, creating the perfect setting to relax with your morning coffee or unwind after a day on the course. As an added bonus, the sale includes a private golf cart, allowing you to enjoy the community with no trail fees when you own your own cart. Hideaway Country Club offers an exceptional lifestyle with recently renovated amenities, including a clubhouse, restaurant, bar, fitness center, clay tennis courts, and an active social calendar. The village pool and patio are just steps from your building, making it easy to enjoy Florida's sunshine year-round. Ideally located in the heart of Fort Myers, you'll be just minutes from US-41, Daniels Parkway, RSW International Airport, Bell Tower Shops, Gulf Coast Medical Center, restaurants, shopping, entertainment, and Southwest Florida's beautiful Gulf beaches. Whether you're looking for a full-time residence, seasonal retreat, or low-maintenance golf community home, this exceptional condo checks all the boxes. With no current assessments, a brand-new A/C, elevator access, stunning golf course views, and outstanding community amenities, this is an opportunity you won't want to miss. Schedule your private showing today!

5845 Trailwinds DR Unit 531, 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

$160,900

3 Beds ⋅ 2 Baths ⋅ 224070205 MLS ⋅ Oakmont Village BLDG.

this is a very desirable first floor unit in one of ft Myers most uniquely located gated golf course community. we have it all here tennis golf swimming dining you never have tp leave. dont miss this one. thi is a model d unit one of the most desirable floor plans

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The data relating to real estate for sale on this web site comes in part from the Broker Reciprocity Program (BR Program) of M.L.S. of Naples, Inc. Properties listed with brokerage firms other than this company are marked with the BR Program Icon or the BR House Icon and detailed information about them includes the name of the listing brokers. The properties displayed may not be all the properties available through the BR Program. The information provided is for consumers’ personal, non-commercial use and may not be used for any other purpose.