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$1,100,000

23 Winewood Ct

Fort Myers, FL
Pending With Contingencies
4
Bedrooms
4.0
Bathrooms
6,473
Square Feet
0.42
Lot Size (acres)
1991
Year Built
34
Days On Market

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.

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Listing Information

Listing Updated
25 days ago
Listed By
Cookie Kermer Douglas, 2394101929 · John R. Wood Properties, 2393332411
MLS#
2026036646
Source
Multiple Listing Service of Bonita SpringsEstero
Status
Pending With Contingencies

Facts & Features

Location

Community Information

Address
23 Winewood Ct, Fort Myers, FL 33919
City
Fort Myers
County
Lee
Neighborhood
CARILLON WOODS
Zip Code
33919

Architecture

Bedrooms
4
Bathrooms
4.0
Stories
2
Year Built
1991
Construction Materials
Stucco, Brick
Building Area
6,473 sq. ft.
Roof
Shingle
Levels
Two
Garage
Yes
Garage Spaces
3
Parking Features
Attached, Garage Door Opener, Garage, Circular Driveway

Features & Amenities

Interior Features
Walk-In Closet(s), Entrance Foyer
Appliances
Dryer, Dishwasher, Microwave, Refrigerator, Washer
Flooring
Tile, Carpet, Wood
Community Features
Gated, Tennis Court(s), Park
Cooling
Ceiling Fan(s), Electric
Heating
Fireplace(s), Electric, Central

Property Features

Lot Size
0.42 Acres
Lot Features
Cul-De-Sac
Utilities
Cable Available
Zoning
AA

Square Footage

Total
5,300 sq. ft.

Tax & Financial Information

List Price
$1,100,000
Annual Taxes
$8,541

Schools

100/100
Unity Charter School Of Fort Myers
Grades M–M · 1.1 mi
City
Fort Myers
Students
247
Parent reviews
2.5★ avg · 4 reviews
Student body
47% Hispanic / Latino · 29% Black · 19% White
Free/reduced lunch
77%
Phone
(239) 333-0766
77/100
Tanglewood Elementary School
Elementary · Grades PK–05 · 0.5 mi
City
Fort Myers
Students
783
Parent reviews
5.0★ avg · 1 review
Student body
49% White · 30% Hispanic / Latino · 13% Black
Free/reduced lunch
42%
Phone
(239) 936-0891
74/100
Allen Park Elementary School
Elementary · Grades PK–05 · 2.4 mi
City
Fort Myers
Students
984
Parent reviews
4.4★ avg · 5 reviews
Student body
34% White · 30% Hispanic / Latino · 27% Black
Free/reduced lunch
52%
Phone
(239) 936-1459
66/100
Villas Elementary School
Elementary · Grades PK–05 · 1.6 mi
City
Fort Myers
Students
862
Parent reviews
4.0★ avg · 1 review
Student body
65% Hispanic / Latino · 18% White · 12% Black
Free/reduced lunch
70%
Phone
(239) 936-3776
54/100
Florida Southwestern Collegiate High School
High · Grades 09–12 · 1.9 mi
City
Fort Myers
Students
401
Student body
58% White · 27% Hispanic / Latino · 9% Black
Free/reduced lunch
30%
Phone
(239) 432-6767
53/100
Orangewood Elementary School
Elementary · Grades PK–05 · 1.6 mi
City
Fort Myers
Students
595
Student body
41% Hispanic / Latino · 34% Black · 19% White
Free/reduced lunch
61%
Phone
(239) 936-2950
50/100
Pace School For Girls
High · Grades 06–12 · 2.4 mi
City
Fort Myers
Students
52
Student body
46% Hispanic / Latino · 29% White · 23% Black
Free/reduced lunch
100%
Phone
(239) 425-2366
48/100
Lee County Acceleration Academies
High · Grades 08–12 · 1.8 mi
City
Fort Myers
Phone
(872) 240-2025

School ratings are provided for informational purposes only and are subject to change. Attendance boundaries are for reference only — contact the school or district directly to verify enrollment eligibility.

Historical Data

Price History

DateEventPrice
08/31/2026Listed for sale$1,100,000

Listed by Cookie Kermer Douglas · John R. Wood Properties · 2393332411

Listing information provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed by the MLS. The listing broker’s offer of compensation is made only to participants of the MLS where the listing is filed. Copyright 2026, Multiple Listing Service of Bonita SpringsEstero. All rights reserved.

Last Updated: September 8, 2026 at 7:37 PM | Source: Multiple Listing Service of Bonita SpringsEstero | MLS#: 2026036646

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