ONE-OF-A-KIND FORT MYERS ESTATE — PRICED TO PERSONALIZE!
Welcome to this seldom found, one-owner custom-built colonial style estate, tucked away in one of Fort Myers’ most prestigious hidden neighborhoods. Situated at the end of a quiet cul-de-sac on an oversized lot, this impressive pool home offers over 5,000 sq. ft. of living space, 4 spacious bedrooms, 2 offices/den spaces, 3 full baths, 2 half baths, beautiful real wood floors, a circular driveway with 3-car garage, and a private pool.
The grand two-story foyer opens to an oversized living room featuring a wood-burning fireplace and dramatic wood staircase—a truly memorable setting for holiday gatherings. The spacious primary suite includes a bay-window sitting area and French doors leading to the rear brick patio. Above, a conveniently located office/exercise room provides additional flexibility and could easily accommodate a variety of lifestyle needs. Another generously sized office/den on the main level offers even more space for working from home, hobbies, or guests. The expansive kitchen with wood cabinetry and breakfast nook overlooks the family room, where a wall of glass sliders opens to the pool and outdoor entertaining area with easy access to ½ pool bath.
Adjacent to the kitchen, the formal dining room has been creatively enjoyed as a music room, offering yet another example of the home’s versatility and ability to adapt to your lifestyle.
Upstairs offers 3 additional bedrooms, 2 baths, and a versatile bonus room ideal for a media room, playroom, gym, or guest space. Priced to accommodate your vision and individual tastes, this well-loved home offers an exceptional opportunity to transform a custom estate into your dream home.
Enjoy community amenities including tennis, pickleball, dog park, playground, and BBQ/picnic areas etc.
All conveniently located near top-rated schools, shopping, beaches, hospitals, and I-75, this remarkable property offers the best of both worlds—the grandeur and privacy of an estate home with easy access to everything Fort Myers has to offer. Ready to make memories for generations.
Active
$1,100,000
23 Winewood Ct, Fort Myers, FL 33919
4beds
5,300sqft
Single Family Residence
Built in 1991
0.42 Acres Lot
$1,019,900 Zestimate®
$208/sqft
$149/mo HOA
What's special
Private poolBay-window sitting areaDramatic wood staircaseRear brick patioBreakfast nookSpacious primary suiteOversized lot
- 6 days
- 730
- 59
Likely to sell faster than
Zillow last checked:
Listing updated:
Listed by:
Cookie Kermer Douglas 239-410-1929,
John R. Wood Properties
Source: Florida Gulf Coast MLS,MLS#: 2026036646
Originating MLS: Florida Gulf Coast
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 5
- Full bathrooms: 3
- 1/2 bathrooms: 2
Rooms
- Room types: Den, Exercise Room, Family Room
Heating
- Central, Electric
Cooling
- Central Air, Ceiling Fan(s), Electric
Appliances
- Included: Dryer, Dishwasher, Microwave, Refrigerator, Washer
- Laundry: Washer Hookup, Dryer Hookup, Inside, Laundry Tub
Features
- Built-in Features, Breakfast Area, Separate/Formal Dining Room, Dual Sinks, Entrance Foyer, French Door(s)/Atrium Door(s), Fireplace, High Ceilings, Main Level Primary, Sitting Area in Primary, Shower Only, Separate Shower, Walk-In Closet(s), Den, Exercise Room, Family Room
- Flooring: Carpet, Tile, Wood
- Doors: French Doors
- Windows: Other, Sliding
- Has fireplace: Yes
Interior area
- Total structure area: 6,473
- Total interior livable area: 5,300 sqft
Video & virtual tour
Property
Parking
- Total spaces: 3
- Parking features: Attached, Circular Driveway, Garage, Garage Door Opener
- Attached garage spaces: 3
- Has uncovered spaces: Yes
Features
- Levels: Two
- Stories: 2
- Exterior features: Sprinkler/Irrigation, None, Other
- Has private pool: Yes
- Pool features: In Ground
- Has view: Yes
- View description: Landscaped
- Waterfront features: None
Lot
- Size: 0.42 Acres
- Features: Cul-De-Sac, Oversized Lot, Sprinklers Automatic
Details
- Parcel number: 034524P302200.0430
- Lease amount: $0
- Zoning description: AA
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Two Story
- Property subtype: Single Family Residence
Materials
- Brick, Stucco, Wood Frame
- Roof: Shingle
Condition
- Resale
- Year built: 1991
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
- Utilities for property: Cable Available
Community & HOA
Community
- Features: Gated
- Condo and coop fee: $0
- Membership fee: $0
- Subdivision: CARILLON WOODS
HOA
- Has HOA: Yes
- Amenities included: Dog Park, Barbecue, Picnic Area, Pickleball, Tennis Court(s), Management
- Services included: Association Management, Recreation Facilities
- HOA fee: $1,791 annually
- HOA phone: 239-344-8733
Location
- Region: Fort Myers
Financial & listing details
- Price per square foot: $208/sqft
- Tax assessed value: $1,099,718
- Annual tax amount: $8,541
- Date on market: 8/31/2026
- Cumulative days on market: 7 days
- Listing terms: All Financing Considered,Cash
- Ownership: Single Family
Estimated market value
$1,019,900
$969,000 - $1.07M
$4,008/mo
Price history
| Date | Event | Price |
|---|---|---|
| 8/31/2026 | Listed for sale | $1,100,000+1366.7%$208/sqft |
Source: | ||
| 2/1/1988 | Sold | $75,000$14/sqft |
Source: Agent Provided Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $8,541 +2.3% | $510,026 +2.9% |
| 2024 | $8,351 +1.6% | $495,652 +3% |
| 2023 | $8,223 +0.5% | $481,216 +3% |
| 2022 | $8,181 -2.1% | $467,200 +3% |
| 2021 | $8,353 -0.9% | $453,592 +1.4% |
| 2020 | $8,430 +0.6% | $447,329 -41.6% |
| 2019 | $8,383 | $765,513 +78.4% |
| 2018 | $8,383 +1.8% | $429,119 +2.1% |
| 2017 | $8,237 -0.3% | $420,293 -42.1% |
| 2016 | $8,263 +2.4% | $725,735 +14.3% |
| 2015 | $8,072 -0.6% | $635,192 +8.2% |
| 2014 | $8,123 +0.7% | $587,001 +12.7% |
| 2013 | $8,063 +4.5% | $520,949 +29.9% |
| 2012 | $7,714 +3.5% | $401,105 -20.4% |
| 2011 | $7,454 +0% | $503,657 +36.1% |
| 2010 | $7,451 -6.4% | $370,110 -20.7% |
| 2009 | $7,957 +7.8% | $466,860 -30% |
| 2007 | $7,380 -2.7% | $667,370 +2.5% |
| 2006 | $7,582 -5.5% | $651,410 +26.2% |
| 2004 | $8,023 -3.6% | $516,060 +13.2% |
| 2003 | $8,322 +4.1% | $456,020 +1.8% |
| 2002 | $7,991 | $448,130 +15.1% |
| 2000 | -- | $389,370 |
Find assessor info on the county website
Monthly payment
Est. payment






