Oakmont Village Condos For Sale

Entry-Level
Ultra LuxuryAbove $1,000 per SqFt
High-End$650 - $1,000 per SqFt
Mid-Tier$400 - $650 per SqFt
Premium$300 - $400 per SqFt
Entry-LevelBelow $300 per SqFt
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Shows who has more leverage in the market
0–30 favors buyers
30–100 favors sellers
Selling Speed
4.17
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Shows how quickly homes are being absorbed by buyers
20%+ Fast
8–19.9% Steady
Below 8% Slow
Inventory Supply
24
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0–3 Low
3–6 Balanced
6+ High
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2+/mo Active
0.75–1.99/mo Steady
Below 0.75/mo Quiet
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Community rating based on resident and buyer reviews
4.5+ Excellent
4.0–4.49 Good
3.0–3.99 Average
Below 3.0 Below Average
Results 11 of 11
Oakmont Village, 5905 Trailwinds Dr #816, Fort Myers, Florida 33907, image 1
Oakmont Village, 5905 Trailwinds Dr #816, Fort Myers, Florida 33907, image 2
Oakmont Village, 5905 Trailwinds Dr #816, Fort Myers, Florida 33907, image 3
$169,900 $5K
  • 3 Beds
  • 2 Baths
  • 1,330 SqFt
  • $128/SqFt
Entry-Level
Condo for sale in Oakmont Village
5905 Trailwinds Dr #816, Fort Myers, FL 33907
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!
Oakmont Village, 5885 Trailwinds Dr #712, Fort Myers, Florida 33907, image 1
Oakmont Village, 5885 Trailwinds Dr #712, Fort Myers, Florida 33907, image 2
$160,900 $14K
  • 3 Beds
  • 2 Baths
  • 1,169 SqFt
  • $138/SqFt
Entry-Level
Condo for sale in Oakmont Village
5885 Trailwinds Dr #712, Fort Myers, FL 33907
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
Oakmont Village, 5785 Trailwinds Dr #222, Fort Myers, Florida 33907, image 1
Oakmont Village, 5785 Trailwinds Dr #222, Fort Myers, Florida 33907, image 2
Oakmont Village, 5785 Trailwinds Dr #222, Fort Myers, Florida 33907, image 3
$164,900 $11K
  • 3 Beds
  • 2 Baths
  • 1,169 SqFt
  • $141/SqFt
Entry-Level
Condo for sale in Oakmont Village
5785 Trailwinds Dr #222, Fort Myers, FL 33907
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.
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Oakmont Village, 5845 Trailwinds Dr #531, Fort Myers, Florida 33907, image 1
Oakmont Village, 5845 Trailwinds Dr #531, Fort Myers, Florida 33907, image 2
Oakmont Village, 5845 Trailwinds Dr #531, Fort Myers, Florida 33907, image 3
$205,000 $5K
  • 3 Beds
  • 2 Baths
  • 1,436 SqFt
  • $143/SqFt
Entry-Level
Condo for sale in Oakmont Village
5845 Trailwinds Dr #531, Fort Myers, FL 33907
This turnkey, move-in ready third-floor condo in the hideaway country club is a standout opportunity—now featuring a brand new ac (2026) with a 10-year warranty and no assessments for added peace of mind. The building offers elevator access—rare within the community—and showcases sweeping views of the golf course and three fountains. Centrally located in the heart of fort myers, just minutes from daniels parkway and us-41, the hideaway delivers both convenience and lifestyle. Residents enjoy an 18-hole golf course, clay tennis courts, and recently renovated amenities including a clubhouse, restaurant, bar, and fitness center. The unit includes a private golf cart—no trail fees when you own it. The village pool and patio are just steps away, perfect for easy relaxation and social time. A friendly, active community with no current assessments makes this a smart and stress-free choice.
Oakmont Village, 5905 Trailwinds Dr #812, Fort Myers, Florida 33907, image 1
Oakmont Village, 5905 Trailwinds Dr #812, Fort Myers, Florida 33907, image 2
Oakmont Village, 5905 Trailwinds Dr #812, Fort Myers, Florida 33907, image 3
$170,000
  • 3 Beds
  • 2 Baths
  • 1,169 SqFt
  • $145/SqFt
Entry-Level
Condo for sale in Oakmont Village
5905 Trailwinds Dr #812, Fort Myers, FL 33907
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!
Oakmont Village, 5805 Trailwinds Dr #326, Fort Myers, Florida 33907, image 1
Oakmont Village, 5805 Trailwinds Dr #326, Fort Myers, Florida 33907, image 2
Oakmont Village, 5805 Trailwinds Dr #326, Fort Myers, Florida 33907, image 3
$199,900 $9K
  • 2 Beds
  • 2 Baths
  • 1,370 SqFt
  • $146/SqFt
Entry-Level
Condo for sale in Oakmont Village
5805 Trailwinds Dr #326, Fort Myers, FL 33907
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.
Oakmont Village, 5845 Trailwinds Dr #515, Fort Myers, Florida 33907, image 1
Oakmont Village, 5845 Trailwinds Dr #515, Fort Myers, Florida 33907, image 2
Oakmont Village, 5845 Trailwinds Dr #515, Fort Myers, Florida 33907, image 3
$224,900
  • 2 Beds
  • 2 Baths
  • 1,435 SqFt
  • $157/SqFt
Entry-Level
Condo for sale in Oakmont Village
5845 Trailwinds Dr #515, Fort Myers, FL 33907
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.
Oakmont Village, 5825 Trailwinds Dr #414, Fort Myers, Florida 33907, image 1
Oakmont Village, 5825 Trailwinds Dr #414, Fort Myers, Florida 33907, image 2
Oakmont Village, 5825 Trailwinds Dr #414, Fort Myers, Florida 33907, image 3
$179,900
  • 2 Beds
  • 2 Baths
  • 1,098 SqFt
  • $164/SqFt
Entry-Level
Condo for sale in Oakmont Village
5825 Trailwinds Dr #414, Fort Myers, FL 33907
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.
Oakmont Village, 6184 Michelle Way #213, Fort Myers, Florida 33919, image 1
Oakmont Village, 6184 Michelle Way #213, Fort Myers, Florida 33919, image 2
Oakmont Village, 6184 Michelle Way #213, Fort Myers, Florida 33919, image 3
$109,000
  • 1 Beds
  • 1 Baths
  • 653 SqFt
  • $167/SqFt
Entry-Level
Condo for sale in Oakmont Village
6184 Michelle Way #213, Fort Myers, FL 33919
Fully furnished and ready to move right in! This turnkey 1br/1ba condo has an ideal location in a highly desired and welcoming community. Enjoy your morning coffee and beautiful sunsets with exceptional view of lake and fountain from your private screened in balcony. Grounds are beautifully maintained. Low maintenance living for seasonal or full-time residents with low condo association dues. Amenities include sparkling heated pool, pickle ball, shuffleboard, tennis, bbq area, bike storage, and clubhouse with large meeting space, library and full kitchen to enjoy potlucks. Friendly and active community to socialize or just relax. Recent improvements include all new roofs, soffits, fascia, and gutters on all buildings in 2023/2024. Parking lots and tennis/pickle ball courts were also recently resurfaced. No flooding from hurricanes including hurricane ian most recently (2022). Now’s the time to take advantage of this great opportunity to enjoy the southwest florida lifestyle at an affordable price. Schedule your private tour today! Ideal location only 15 minutes from fort myers beach and sanibel island. Martinique is within walking or bike riding distance from shopping at publix, dining, entertainment at barbara b. Mann and everyday conveniences.
Oakmont Village, 5805 Trailwinds Dr #314, Fort Myers, Florida 33907, image 1
Oakmont Village, 5805 Trailwinds Dr #314, Fort Myers, Florida 33907, image 2
Oakmont Village, 5805 Trailwinds Dr #314, Fort Myers, Florida 33907, image 3
$239,900
  • 2 Beds
  • 2 Baths
  • 1,435 SqFt
  • $167/SqFt
Entry-Level
Condo for sale in Oakmont Village
5805 Trailwinds Dr #314, Fort Myers, FL 33907
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.
Oakmont Village, 5825 Trailwinds Dr #425, Fort Myers, Florida 33907, image 1
Oakmont Village, 5825 Trailwinds Dr #425, Fort Myers, Florida 33907, image 2
Oakmont Village, 5825 Trailwinds Dr #425, Fort Myers, Florida 33907, image 3
$269,000
  • 3 Beds
  • 2 Baths
  • 1,436 SqFt
  • $187/SqFt
Entry-Level
Condo for sale in Oakmont Village
5825 Trailwinds Dr #425, Fort Myers, FL 33907
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.

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Results 2 of 2
Whiskey Creek 2, 6136 Whiskey Creek Dr #521, Fort Myers, Florida 33919, image 1
Whiskey Creek 2, 6136 Whiskey Creek Dr #521, Fort Myers, Florida 33919, image 2
Whiskey Creek 2, 6136 Whiskey Creek Dr #521, Fort Myers, Florida 33919, image 3
$119,900
  • 1 Beds
  • 1 Baths
  • 752 SqFt
  • $159/SqFt
Condo for sale in Whiskey Creek 2
6136 Whiskey Creek Dr #521, Fort Myers, FL 33919
Discover easy florida living in this charming 1-bedroom, 1-bath condo nestled within the sought-after whiskey creek community. Conveniently located in the heart of fort myers, you'll be just minutes from beautiful gulf beaches, popular restaurants, shopping destinations, and everyday conveniences. Inside, the thoughtfully designed 752-square-foot floor plan offers an inviting and open living space enhanced by tile and laminate flooring throughout. The screened lanai provides the perfect spot to enjoy your morning coffee or unwind after a day in the sun. The spacious primary bedroom offers a comfortable retreat, while the versatile layout provides ample room for guests and everyday living. The kitchen is functional and well-maintained, featuring plenty of workspace and storage, with the opportunity to add your own personal touches over time. Additional conveniences include an in-unit washer and dryer, custom shelving in the laundry area for added organization, and a covered parking space. Residents enjoy access to a variety of community amenities, including a sparkling pool, pickleball courts, and tennis facilities. Whether you're searching for a seasonal escape, investment opportunity, or full-time residence, this well-maintained whiskey creek condo offers comfort, convenience, and an unbeatable location.
Whiskey Creek 2, 6146 Whiskey Creek Dr #713, Fort Myers, Florida 33919, image 1
Whiskey Creek 2, 6146 Whiskey Creek Dr #713, Fort Myers, Florida 33919, image 2
Whiskey Creek 2, 6146 Whiskey Creek Dr #713, Fort Myers, Florida 33919, image 3
$119,999
  • 2 Beds
  • 2 Baths
  • 956 SqFt
  • $126/SqFt
Condo for sale in Whiskey Creek 2
6146 Whiskey Creek Dr #713, Fort Myers, FL 33919
Snowbirds, seasonal buyers, and investors , spacious 2-bed, 2-bath second-floor condo in one of fort myers' most established communities. Bright open living and dining area opens to a private screened lanai with peaceful courtyard views, perfect for morning coffee in the florida sun. Stainless steel appliances in the eat-in kitchen, generous storage, and a layout ready for your personal touches. An unbeatable central location near the caloosahatchee river, downtown river district, rsw airport, and gulf beaches.

Subdivision Amenities

Bike And Jog Path
Bike Storage
Bocce Court
Business Center
Car Wash Area
Clubhouse
Common Laundry
Community Room
Electric Vehicle Charging
Fitness Center
Golf Course
Guest Room
Hobby Room
Internet Access
Library
Park
Pickleball
Play Area
Pool
Private Membership
Putting Green
Restaurant
See Remarks
Shopping
Shuffleboard Court
Sidewalk
Spa/Hot Tub
Storage
Streetlight
Tennis Court(s)
Underground Utility
Barbecue
Bocce Court
Clubhouse

Community Residences

Stack/LineFloorExposureView
01‑/‑1,193
Stack/Line: 01
Floor:
Bed/Bath: ‑/‑
Size SqFt: 1,193
Exposure:
View:

Frequently Asked Questions

Comparable & Nearby Subdivisions

ComparableNearby
Entry-Level
Fort Myers, FL 33919
For Sale (3)
$120K - $130K

Schools

Scores

Walk Score®
Car-Dependent. Almost all errands require a car
8

100
Bike Score®
Very Bikeable. Biking is convenient for most trips
70

100
Sound Score®
Very quiet
86

100
Airport Score
Close to airports. Noticeable airport activity
1

100
Traffic Score
Congested area. Frequent traffic delays
17

100
Local Score
Limited local amenities nearby
0

100

The Hideaway Country Club Communities in Fort Myers, FL

Fort Myers
Entry-Level
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