Welcome to 4018 Cherrybrook Loop in the gated community of San Simeon! This beautifully updated Mediterranean-style townhome offers over 1,900 square feet of living space, 3 spacious bedrooms, 2.5 baths, and a 2-car garage—all surrounded by lush landscaping and preserve views for ultimate privacy. Step inside to find an inviting layout with high ceilings, fresh paint, new blinds, and stunning wood-accented walls. The fully renovated kitchen features solid wood cabinetry, a stylish tile backsplash that makes the space pop, new stainless-steel appliances, and a functional breakfast area. Bathrooms have been completely updated, and the home includes newer carpet throughout. The primary suite is generously sized with a large walk-in closet, dual sinks, a soaking tub, and a separate shower. One guest bedroom offers a built-in Murphy bed and connects to a convenient Jack-and-Jill bath—perfect for guests or a home office setup. Enjoy peace of mind with a brand-new roof (2024), impact-resistant windows and doors (including the garage door), and replaced window springs for smooth operation. The spacious two-car garage has high ceilings with attic access, ideal for additional storage or overhead racks. Outside, relax on your screened lanai overlooking the preserve, where you’ll never have to worry about neighbors behind you. San Simeon offers sidewalks on both sides of the street and an active, welcoming atmosphere. The low HOA fee of $441/month covers irrigation water, lawn and landscape maintenance, exterior pest control, trash removal, and access to resort-style amenities—including a clubhouse, community pool and spa, fitness center, playground, and community room—plus high-speed internet. Best of all, this home has no CDD fee and is not located in a flood zone, offering extra peace of mind and lower carrying costs. Located off Winkler Avenue, San Simeon offers a prime Fort Myers location close to everything: The Forum shopping center, Colonial Blvd, Metro Parkway, Six Mile Cypress, and I-75 are all minutes away. You’re less than 10 minutes from RSW Airport and Downtown Fort Myers, and just 30–40 minutes to the white sands of Fort Myers Beach. Whether you’re looking for comfort, convenience, or long-term value, this upgraded townhome checks every box. Come see why 4018 Cherrybrook Loop stands out as one of the most desirable homes in San Simeon!
Active
Price cut: $20K (11/7)
$350,000
4018 Cherrybrook Loop, Fort Myers, FL 33966
3beds
1,929sqft
Est.:
Townhouse
Built in 2007
4,268.88 Square Feet Lot
$-- Zestimate®
$181/sqft
$441/mo HOA
What's special
Screened lanaiFully renovated kitchenFresh paintHigh ceilingsPreserve viewsNewer carpetJack-and-jill bath
- 34 days |
- 333 |
- 37 |
Zillow last checked: 8 hours ago
Listing updated: November 07, 2025 at 05:48am
Listed by:
Rick Harrison 239-310-5478,
Realty One Group MVP
Source: Florida Gulf Coast MLS,MLS#: 2025018903
Originating MLS: Florida Gulf Coast
Tour with a local agent
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 3
- Bathrooms: 3
- Full bathrooms: 2
- 1/2 bathrooms: 1
Rooms
- Room types: Bathroom, Screened Porch
Heating
- Central, Electric
Cooling
- Central Air, Electric
Appliances
- Included: Dryer, Dishwasher, Freezer, Disposal, Microwave, Refrigerator, Washer
- Laundry: Inside
Features
- Breakfast Area, Bathtub, Dual Sinks, High Ceilings, Living/Dining Room, Pantry, Separate Shower, Cable TV, Upper Level Primary, Walk-In Closet(s), Window Treatments, High Speed Internet, Bathroom, Screened Porch
- Flooring: Carpet, Tile
- Windows: Single Hung, Impact Glass, Window Coverings
Interior area
- Total structure area: 2,382
- Total interior livable area: 1,929 sqft
Video & virtual tour
Property
Parking
- Total spaces: 2
- Parking features: Attached, Driveway, Underground, Garage, Paved, Two Spaces, Garage Door Opener
- Attached garage spaces: 2
- Has uncovered spaces: Yes
Features
- Levels: Two
- Stories: 2
- Patio & porch: Lanai, Patio, Porch, Screened
- Exterior features: Security/High Impact Doors, Sprinkler/Irrigation, Patio
- Pool features: Community
- Has view: Yes
- View description: Preserve
- Waterfront features: None
Lot
- Size: 4,268.88 Square Feet
- Dimensions: 50 x 101 x 35 x 101
- Features: Corner Lot, Rectangular Lot, Sprinklers Automatic
Details
- Parcel number: 334425P100700.0890
- Lease amount: $0
- Zoning description: B-1
Construction
Type & style
- Home type: Townhouse
- Architectural style: Coach/Carriage,Two Story
- Property subtype: Townhouse
Materials
- Block, Concrete, Stucco
- Roof: Tile
Condition
- Resale
- Year built: 2007
Utilities & green energy
- Sewer: Assessment Paid, Public Sewer
- Water: Assessment Paid, Public
- Utilities for property: Cable Available, High Speed Internet Available
Community & HOA
Community
- Features: Gated, Street Lights
- Security: Security Gate, Gated Community, Security System, Smoke Detector(s)
- Subdivision: TOWNHOMES OF SAN SIMEON
HOA
- Has HOA: Yes
- Amenities included: Clubhouse, Fitness Center, Playground, Pool, Spa/Hot Tub, Sidewalks, Management
- Services included: Association Management, Cable TV, Irrigation Water, Legal/Accounting, Maintenance Grounds, Pest Control, Reserve Fund, Street Lights, Trash
- HOA phone: 239-454-1101
- Second HOA fee: $441 monthly
- Condo and coop fee: $0
- Membership fee: $0
Location
- Region: Fort Myers
Financial & listing details
- Price per square foot: $181/sqft
- Tax assessed value: $303,363
- Annual tax amount: $2,526
- Date on market: 11/7/2025
- Listing terms: All Financing Considered,Cash,FHA,VA Loan
- Ownership: Single Family
Estimated market value
Not available
Estimated sales range
Not available
Not available
Price history
Price history
| Date | Event | Price |
|---|---|---|
| 11/7/2025 | Price change | $350,000-5.4%$181/sqft |
Source: | ||
| 8/11/2025 | Price change | $2,400-4%$1/sqft |
Source: Zillow Rentals Report a problem | ||
| 7/26/2025 | Listed for rent | $2,500$1/sqft |
Source: Zillow Rentals Report a problem | ||
| 11/12/2024 | Price change | $370,000+2.8%$192/sqft |
Source: | ||
| 10/30/2024 | Listed for sale | $360,000+43.5%$187/sqft |
Source: Owner Report a problem | ||
Public tax history
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2024 | $2,526 -46.1% | $178,019 -32.1% |
| 2023 | $4,688 +87.2% | $262,297 +56.3% |
| 2022 | $2,505 +1.2% | $167,800 +3% |
Find assessor info on the county website
BuyAbility℠ payment
Est. payment
$2,661/mo
Principal & interest
$1689
HOA Fees
$441
Other costs
$531
Climate risks
Neighborhood: 33966
Nearby schools
GreatSchools rating
- 4/10Ray V. Pottorf Elementary SchoolGrades: PK-5Distance: 0.3 mi
- 5/10Paul Laurence Dunbar Middle SchoolGrades: 6-8Distance: 0.6 mi
- 1/10Dunbar High SchoolGrades: 9-12Distance: 1.9 mi
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