Fort Myers, FL 33907
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Oakmont Village Condos Sold
Results 29 of 47
Last Sold Date
Sold - May 28, 2026
$147,500$31K
- 2 Beds
- 2 Baths
- 1,098 SqFt
- $134/SqFt
- $517/mo HOA
Entry-Level
Condo sold in Oakmont Village5765 Trailwinds Dr #111, Fort Myers, FL 33907
Listing Courtesy Of: LPT Realty, LLC
Sold - May 12, 2026
$200,000$49K
- 2 Beds
- 2 Baths
- 1,100 SqFt
- $182/SqFt
Entry-Level
Condo sold in Oakmont Village5905 Trailwinds Dr #824, Fort Myers, FL 33907
Listing Courtesy Of: Treeline Realty Corp
Sold - Mar 24, 2026
$180,000$89K
- 3 Beds
- 2 Baths
- 1,169 SqFt
- $154/SqFt
Entry-Level
Condo sold in Oakmont Village5925 Trailwinds Dr #912, Fort Myers, FL 33907
Listing Courtesy Of: Loyal Real Estate Services
Sold - Dec 30, 2025
$235,000$25K
- 3 Beds
- 2 Baths
- 1,435 SqFt
- $164/SqFt
Entry-Level
Condo sold in Oakmont Village5865 Trailwinds Dr #623, Fort Myers, FL 33907
Listing Courtesy Of: Royal Shell Real Estate, Inc.
Sold - Sep 29, 2025

$170,000$70K
- 2 Beds
- 2 Baths
- 1,373 SqFt
- $124/SqFt
Entry-Level
Condo for sale in Oakmont Village5925 Trailwinds Dr #926, Fort Myers, FL 33907
Listing Courtesy Of: Jones & Co Realty
Sold - Sep 22, 2025
$275,000$20K
- 3 Beds
- 2 Baths
- 1,331 SqFt
- $207/SqFt
- $493/mo HOA
Entry-Level
Condo for sale in Oakmont Village5865 Trailwinds Dr #613, Fort Myers, FL 33907
Listing Courtesy Of: Beycome of Florida LLC
Sold - May 14, 2025
$212,000
- 2 Beds
- 2 Baths
- 1,372 SqFt
- $155/SqFt
Entry-Level
Condo for sale in Oakmont Village5925 Trailwinds Dr #911, Fort Myers, FL 33907
Listing Courtesy Of: Cypress Realty Inc.
Sold - May 7, 2025

$175,000$25K
- 2 Beds
- 2 Baths
- 1,098 SqFt
- $159/SqFt
Entry-Level
Condo for sale in Oakmont Village5845 Trailwinds Dr #523, Fort Myers, FL 33907
Listing Courtesy Of: Re/Max Sunshine
Sold - Apr 17, 2025
$209,900$30K
- 2 Beds
- 2 Baths
- 1,373 SqFt
- $153/SqFt
Entry-Level
Condo for sale in Oakmont Village5805 Trailwinds Dr #316, Fort Myers, FL 33907
Listing Courtesy Of: Cypress Realty Inc.
Sold - Apr 3, 2025

$240,000$35K
- 2 Beds
- 2 Baths
- 1,435 SqFt
- $167/SqFt
Entry-Level
Condo for sale in Oakmont Village5965 Trailwinds Dr #1123, Fort Myers, FL 33907
Listing Courtesy Of: Cypress Realty Inc.
Sold - Mar 27, 2025
$210,000
- 2 Beds
- 2 Baths
- 1,370 SqFt
- $153/SqFt
Entry-Level
Condo for sale in Oakmont Village5865 Trailwinds Dr #621, Fort Myers, FL 33907
Listing Courtesy Of: Keller Williams Realty Fort Myers and the Islands
Sold - Mar 11, 2025

$160,000
- 3 Beds
- 2 Baths
- 1,193 SqFt
- $134/SqFt
Entry-Level
Condo for sale in Oakmont Village5865 Trailwinds Dr #613, Fort Myers, FL 33907
Listing Courtesy Of: Century 21 Selling Paradise
Sold - Mar 7, 2025

$290,000$11K
- 3 Beds
- 2 Baths
- 1,450 SqFt
- $200/SqFt
- $593/mo HOA
Entry-Level
Condo for sale in Oakmont Village5965 Trailwinds Dr #1115, Fort Myers, FL 33907
Listing Courtesy Of: Beycome of Florida LLC
Sold - Nov 15, 2024

$205,000$10K
- 2 Beds
- 2 Baths
- 1,098 SqFt
- $187/SqFt
Entry-Level
Condo for sale in Oakmont Village5965 Trailwinds Dr #1121, Fort Myers, FL 33907
Listing Courtesy Of: Cypress Realty Inc.
Sold - Apr 8, 2024

$307,000
- 2 Beds
- 2 Baths
- 1,435 SqFt
- $214/SqFt
Entry-Level
Condo for sale in Oakmont Village5765 Trailwinds Dr #114, Fort Myers, FL 33907
Listing Courtesy Of: Cypress Realty Inc.
Sold - Feb 2, 2024

$200,000
- 3 Beds
- 2 Baths
- 1,332 SqFt
- $150/SqFt
Entry-Level
Condo for sale in Oakmont Village5785 Trailwinds Dr #215, Fort Myers, FL 33907
Listing Courtesy Of: Florida Local Real Estate LLC
Sold - Jan 29, 2024

$250,000
- 2 Beds
- 2 Baths
- 1,373 SqFt
- $182/SqFt
Entry-Level
Condo for sale in Oakmont Village5905 Trailwinds Dr #814, Fort Myers, FL 33907
Listing Courtesy Of: Jones & Co Realty
$174,900
- 2 Beds
- 2 Baths
- 893 SqFt
- $196/SqFt
Entry-Level
Condo for sale in Oakmont Village6184 Michelle Way #151, Fort Myers, FL 33919
Listing Courtesy Of: Robert D. Allman
Sold - Aug 28, 2023

$320,000
- 3 Beds
- 2 Baths
- 1,436 SqFt
- $223/SqFt
Entry-Level
Condo for sale in Oakmont Village5845 Trailwinds Dr #526, Fort Myers, FL 33907
Listing Courtesy Of: Jones & Co Realty
Sold - Jun 30, 2023

$245,000
- 3 Beds
- 2 Baths
- 1,435 SqFt
- $171/SqFt
Entry-Level
Condo for sale in Oakmont Village5865 Trailwinds Dr #612, Fort Myers, FL 33907
Listing Courtesy Of: Cypress Realty Inc.
Sold - Jun 16, 2023

$295,000
- 3 Beds
- 2 Baths
- 1,332 SqFt
- $221/SqFt
Entry-Level
Condo for sale in Oakmont Village5985 Trailwinds Dr #1225, Fort Myers, FL 33907
Listing Courtesy Of: Florida Complete Realty
Sold - Mar 20, 2023

$309,900
- 2 Beds
- 2 Baths
- 1,373 SqFt
- $226/SqFt
Entry-Level
Condo for sale in Oakmont Village5845 Trailwinds Dr ## 533, Fort Myers, FL 33907
Listing Courtesy Of: Jones & Co Realty
Sold - Feb 28, 2023

$282,000
- 2 Beds
- 2 Baths
- 1,370 SqFt
- $206/SqFt
Entry-Level
Condo for sale in Oakmont Village5845 Trailwinds Dr #514, Fort Myers, FL 33907
Listing Courtesy Of: Cypress Realty Inc.
$305,000
- 3 Beds
- 2 Baths
- 1,436 SqFt
- $212/SqFt
Entry-Level
Condo for sale in Oakmont Village5765 Trailwinds Dr #124, Fort Myers, FL 33907
Listing Courtesy Of: Cypress Realty Inc.
$205,000
- 2 Beds
- 2 Baths
- 1,098 SqFt
- $187/SqFt
Entry-Level
Condo for sale in Oakmont Village5905 Trailwinds Dr #813, Fort Myers, FL 33907
Listing Courtesy Of: LVCC Real Estate Inc
$320,000
- 3 Beds
- 2 Baths
- 1,435 SqFt
- $223/SqFt
Entry-Level
Condo for sale in Oakmont Village5865 Trailwinds Dr #614, Fort Myers, FL 33907
Listing Courtesy Of: Cypress Realty Inc.
$300,000
- 2 Beds
- 2 Baths
- 1,435 SqFt
- $209/SqFt
Entry-Level
Condo for sale in Oakmont Village5845 Trailwinds Dr #512, Fort Myers, FL 33907
Listing Courtesy Of: Cypress Realty Inc.
$269,000
- 3 Beds
- 2 Baths
- 1,436 SqFt
- $187/SqFt
Entry-Level
Condo for sale in Oakmont Village5925 Trailwinds Dr #912, Fort Myers, FL 33907
Listing Courtesy Of: Jones & Co Realty
$235,000
- 2 Beds
- 2 Baths
- 1,370 SqFt
- $172/SqFt
Entry-Level
Condo for sale in Oakmont Village5925 Trailwinds Dr #921, Fort Myers, FL 33907
Listing Courtesy Of: Cypress Realty Inc.
Community Snapshot
1 – 3 BR
Bedrooms
1992
Year Build
2
Total Floors
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
Storage
Streetlight
Tennis Court(s)
Underground Utility
Barbecue
Bocce Court
Clubhouse
HOA Cost Benchmark
$0.42 / Sq.Ft.
Monthly ownership cost
↓7%below peers
↑83%above city avg
Lower than peers, higher than the city average
Frequently Asked Questions
Market Peers
Matched by price tier, HOA, and lifestyle
$219,900
Condo for sale in Sunset Cove At The Landings
9900 Sunset Cove Ln #114, Fort Myers, FL 33919
Listing Courtesy Of: Rossman Realty Group Inc
$244,000
Condo for sale in SeaBreeze
11921 Seabreeze Cove Ln #107, Fort Myers, FL 33908
Listing Courtesy Of: RE/MAX Trend
Preconstruction in Fort Myers
Show AllComparable & Nearby Subdivisions
Schools
| School | Type | Grades | Distance | Rating |
|---|---|---|---|---|
Public | PK-5 | 0.68 mi | ||
Private | KG-12 | 1.47 mi | ||
Public | PK-5 | 1.55 mi | ||
Charter | KG-8 | 1.68 mi | ||
Private | 1-12 | 1.71 mi | ||
Public | KG-12 | 1.85 mi | ||
Public | PK-12 | 1.85 mi | ||
Public | 6-12 | 1.85 mi | ||
Public | KG-5 | 1.85 mi | ||
Private | PK-11 | 1.96 mi | ||
Private | PK-6 | 1.96 mi | ||
Private | PK-12 | 2.16 mi | ||
Charter | 9-12 | 2.17 mi | ||
Public | PK-5 | 2.32 mi | ||
Private | PK-KG | 2.32 mi | ||
Private | PK-6 | 2.53 mi | ||
Public | PK-5 | 2.58 mi | ||
Private | PK-8 | 2.60 mi | ||
Private | KG | 2.77 mi | ||
Private | PK-2 | 2.99 mi | ||
Public | 6-8 | 3.17 mi | ||
Public | 6-8 | 3.22 mi | ||
Private | UG | 3.23 mi | ||
Public | PK-5 | 3.26 mi | ||
Public | 6-8 | 3.30 mi | ||
Charter | 7-12 | 3.39 mi | ||
Public | 9-12 | 3.54 mi | ||
Public | 9-12 | 3.95 mi | ||
Public | PK-5 | 4.24 mi | ||
Public | PK-5 | 4.36 mi |
Scores
8
100
70
100
86
100
1
100
17
100
0
100
The Hideaway Country Club Communities in Fort Myers, FL
Community Residences
| Stack/Line | Floor | Bed/Bath | Size SqFt | Exposure | View |
|---|---|---|---|---|---|
| 01 | ‑/‑ | 1,193 |
Stack/Line: 01
Floor:
Bed/Bath: ‑/‑
Size SqFt: 1,193
Exposure:
View:
All Fort Myers, FL Entry-Level Entry-Level Homes & Condos
- Abaco At Tortuga Condo0
- Alabama Grove Terrace House6
- Allen Park House0
- Allerton House Condo1
- Alta Mar Condo4
- Amberwood Lake Mixed0
- Amblewind House0
- Andros At Tortuga Condo0
- Arborwood Preserve Mixed14
- Ariel At The Landings Condo4
- Arlington House0
- Aster Place House6
- Augusta Condo1
- Avalon Bay Mixed0
- Avalon Preserve Mixed4
- Aviano Condo0
- Avila Mixed1
- Baltusrol Village Condo2
- Banyan Bay House3
- Banyan Cove House0
- Bay Haven At Coco Bay Mixed1
- Bay Woods Mixed1
- Bayshore Commons Townhouse0
- Bayshore Park House0
- Beachwalk Isles House4
- Beau Rivage Condo10
- Bell Tower Park Mixed6
- Bella Casa Condo0
- BellaSol Condo7
- Bellagio House1
- Bellaire Estates House0
- Bellamar At Beachwalk Condo5
- Belle Vue Park House2
- Belmont Heights House0
- Ben Davis Park House0
- Ben-Mar Condo0
- Bentley Crossing House16
- Berkshire House Condo0
- Billys Creek Estates House0
- Biscayne Estates House0
- Blackhawk House1
- Bonair House0
- Bonavie Cove Villa6
- Botanica Lakes House14
- Bowling Green House3
- Bramble Cove House1
- Brandywine At Myerlee Mixed12
- Breezewood House0
- Briarcrest House1
- Bridgetown Mixed14
- Bridgeway Condo0
- Brighton Pointe House0
- Bristol Bay Condo0
- Bristol Parc House1
- Broadview Manor House0
- Brookhill House1
- Brookshire Village Mixed1
- Buckingham House0
- Buckingham House0
- Buckingham House1
- Buckingham House0
- Buckingham House0
- Buckingham House1
- Buckingham Park House1
- Buckingham Park House0
- Buckingham Park House0
- Buckingham Park House0
- Buckingham Park House0
- Buckingham Park House0
- Buckingham Park House0
- Buckingham Park House1
- Buckingham Park House1
- Buckingham Park House0
- Callaway Greens House2
- Caloosa Bayview Mixed7
- Caloosa Creek House3
- Caloosa Trace House0
- Calusa Palms Mixed3
- Camarelle House4
- Cambridge Place House4
- Camden Square House0
- Campbell Acres House0
- Candlewood Lake Estates House0
- Cape Coral Mixed0
- Cardinal Cove Condo3
- Carillon Woods House0
- Carlton Grove House2
- Carriedale Gardens Condo1
- Carver Park House5
- Casa Bella Condo2
- Casa Del Lago House6
- Casamada House0
- Casella Mixed1
- Castalina Mixed5
- Catalina Isles House4
- Central Park South Mixed3
- Centre Court Condo1
- Champion's Green Condo0
- Chula Vista Manor House0
- Citrus Creek House0
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