One or more photo(s) has been virtually staged. Welcome to 5365 Bowman Drive, an extensively updated and thoughtfully curated residence in one of Winter Garden’s most desirable communities. Blending architectural presence, meaningful recent upgrades, and unforgettable lifestyle features, this home offers a rare opportunity to own something truly special. A dramatic two-story foyer sets the tone upon entry, opening to an equally stunning two-story living room filled with natural light and architectural volume. The expansive layout creates an immediate sense of openness while maintaining warmth and livability throughout. In preparation for listing, the home has undergone substantial enhancements designed for both comfort and long-term peace of mind. Two brand-new HVAC systems ensure efficient climate control year-round. The exterior has been meticulously refreshed with professional stucco refinishing and a full repaint, delivering crisp curb appeal and a refined aesthetic. The driveway has been extended to comfortably accommodate an additional full-size vehicle with added maneuvering space — a rare and practical upgrade. Inside, fresh interior paint and brand-new carpet throughout create a clean, cohesive, move-in-ready presentation. The kitchen is well-appointed for both everyday living and entertaining, featuring a gas range that will delight culinary enthusiasts. An intelligently designed floor plan includes an isolated guest suite with its own full bath, offering privacy and flexibility for visitors or multigenerational living. Entertainment and leisure take center stage in this home. A custom Star Wars-themed theatre room creates a truly immersive cinematic experience — a one-of-a-kind feature that transforms movie nights into events. Step outside to your private outdoor retreat, where a heated saltwater pool and screened-in lanai invite year-round enjoyment. The backyard backs to a peaceful retention pond, offering added privacy and tranquil views. The oversized garage provides generous storage and flexibility for vehicles, hobbies, or recreational equipment. And as a uniquely Central Florida bonus, rocket launches from Cape Canaveral can be viewed right from your own front doorstep — an awe-inspiring experience that never gets old. Ideally located just minutes from Winter Garden Village, Historic Downtown Winter Garden, the West Orange Trail, and world-renowned theme parks including Walt Disney World, this home offers exceptional convenience while maintaining the charm and tranquility of a well-established neighborhood. 5365 Bowman Drive is more than a residence — it is a lifestyle property that seamlessly combines thoughtful upgrades, architectural elegance, resort-style amenities, and an extraordinary location. An exceptional offering in the heart of Winter Garden.
Sold for $1,150,000
$1,150,000
5365 BOWMAN DRIVE, WINTER GARDEN, FL 34787
4beds
4,000sqft
Single Family Residence
Built in 2015
9,139 Square Feet Lot
$1,154,700 Zestimate®
$288/sqft
$4,398 Estimated rent
Home value
$1,154,700
$1.06M - $1.26M
$4,398/mo
Zestimate® history
Owner options
List your home for rent
$4,398/mo
Rent Zestimate®
Find your next renter with Zillow Rental Manager. Plus, with online applications, you can quickly screen prospective tenants – for free.
$4,398/mo
Rent Zestimate®
Refinance and save
$8,553/mo
Est. payment
Refinancing to a lower rate could help reduce your monthly payments and save thousands over the life of the loan.
$8,553/mo
Est. payment
Explore your selling options
Work with a Zillow partner agent
Leverage their expertise and Zillow's premium Showcase listings to get your home seen by more buyers.
Get startedList with your own agent
Get your home in front of millions of buyers by listing it on Zillow.
Learn how to do itSell it yourself
Take full control of how buyers see your home on Zillow by listing For Sale by Owner (FSBO).
List your homeWhat's special
Dramatic two-story foyer
Zillow last checked:
Listing updated:
Listed by:
William Skinner 303-547-5659,
FORTERA REALTY LLC 303-547-5659
Bought with:
Irhelma Pieterse, 3111320
STOCKWORTH REALTY GROUP
Source: Stellar MLS,MLS#: O6383338
Originating MLS: Orlando Regional
Originating MLS: Orlando Regional
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 4
- Full bathrooms: 3
- 1/2 bathrooms: 1
Rooms
- Room types: Attic, Breakfast Room Separate, Den/Library/Office, Family Room, Dining Room, Loft, Media Room, Storage Rooms
Primary bedroom
- Features: Ceiling Fan(s), En Suite Bathroom, Dual Closets
- Level: First
Bedroom 2
- Features: Walk-In Closet(s)
- Level: Second
Bedroom 3
- Features: Walk-In Closet(s)
- Level: Second
Bedroom 4
- Features: Walk-In Closet(s)
- Level: Second
Primary bathroom
- Features: En Suite Bathroom, No Closet
- Level: First
Bathroom 2
- Features: No Closet
- Level: First
Bathroom 3
- Features: No Closet
- Level: Second
Bathroom 4
- Features: No Closet
- Level: Second
Kitchen
- Features: Pantry, Kitchen Island, Granite Counters, Tall Countertops
- Level: First
Living room
- Level: First
Heating
- Central
Cooling
- Central Air
Appliances
- Included: Cooktop, Dishwasher, Disposal, Microwave, Range, Refrigerator, Tankless Water Heater
- Laundry: Laundry Room
Features
- Built-in Features, Ceiling Fan(s), Coffered Ceiling(s), Crown Molding, Dry Bar, Eating Space In Kitchen, High Ceilings, Open Floorplan, Primary Bedroom Main Floor, Smart Home, Thermostat, Walk-In Closet(s)
- Flooring: Carpet, Porcelain Tile
- Doors: Outdoor Grill, Sliding Doors
- Windows: Blinds, Shutters, Window Treatments
- Has fireplace: Yes
- Fireplace features: Family Room, Insert
Interior area
- Total structure area: 4,000
- Total interior livable area: 4,000 sqft
Property
Parking
- Total spaces: 3
- Parking features: Garage Door Opener, Garage Faces Side, Golf Cart Parking, Guest, Off Street, Oversized, Parking Pad
- Attached garage spaces: 2
- Carport spaces: 1
- Covered spaces: 3
- Has uncovered spaces: Yes
Features
- Levels: Two
- Stories: 2
- Patio & porch: Enclosed, Front Porch, Rear Porch
- Exterior features: Dog Run, Fire Pit, Irrigation System, Lighting, Outdoor Grill, Private Yard, Rain Gutters, Sidewalk
- Has private pool: Yes
- Pool features: Child Safety Fence, Chlorine Free, Gunite, Heated, In Ground, Lighting, Pool Alarm, Salt Water, Screen Enclosure, Tile
- Fencing: Fenced
- Has view: Yes
- View description: Garden, Park/Greenbelt, Pool, Water
- Water view: Water
- Waterfront features: Lake, Lake Privileges
Lot
- Size: 9,139 Square Feet
- Features: In County, Key Lot, Landscaped, Near Public Transit, Oversized Lot, Private, Sidewalk
- Residential vegetation: Fruit Trees, Mature Landscaping, Trees/Landscaped
Details
- Parcel number: 202327584600500
- Zoning: P-D
- Special conditions: None
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Mediterranean
- Property subtype: Single Family Residence
Materials
- Block, Stucco, Wood Frame
- Foundation: Slab
- Roof: Shingle
Condition
- New construction: No
- Year built: 2015
Details
- Builder name: Taylor Morrison
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
- Utilities for property: Cable Connected, Electricity Connected, Sewer Connected, Street Lights, Water Connected
Community & HOA
Community
- Features: Community Boat Ramp, Lake, Private Boat Ramp, Water Access, Clubhouse, Community Mailbox, Deed Restrictions, Dog Park, Fitness Center, Golf Carts OK, Park, Playground, Pool, Sidewalks
- Security: Security System Owned, Smoke Detector(s)
- Pet fee: $0 monthly
- Subdivision: OVERLOOK 2/HAMLIN PH 1 & 6
HOA
- Has HOA: Yes
- Amenities included: Clubhouse, Fence Restrictions, Park, Playground, Pool
- Services included: Community Pool, Manager, Trash
- HOA fee: $215 monthly
- HOA name: Castle Group, Melissa Glenn
- HOA phone: 407-654-2899
Location
- Region: Winter Garden
Financial & listing details
- Price per square foot: $288/sqft
- Tax assessed value: $938,252
- Annual tax amount: $15,677
- Date on market: 2/18/2026
- Cumulative days on market: 2 days
- Ownership: Fee Simple
- Total actual rent: 0
- Electric utility on property: Yes
- Road surface type: Paved, Asphalt
Price history
| Date | Event | Price |
|---|---|---|
| 4/9/2026 | Sold | $1,150,000$288/sqft |
Source:  Stellar MLS #O6383338 Report a problem | ||
| 2/20/2026 | Pending sale | $1,150,000$288/sqft |
Source: Stellar MLS #O6383338 Report a problem | ||
| 2/18/2026 | Listed for sale | $1,150,000+0.4%$288/sqft |
Source: Stellar MLS #O6383338 Report a problem | ||
| 11/5/2025 | Listing removed | $1,145,000$286/sqft |
Source: Stellar MLS #O6312394 Report a problem | ||
| 11/5/2025 | Price change | $1,145,000-0.4%$286/sqft |
Source: Stellar MLS #O6312394 Report a problem | ||
| 10/18/2025 | Price change | $1,149,900-3.8%$287/sqft |
Source: Stellar MLS #O6312394 Report a problem | ||
| 9/18/2025 | Price change | $1,195,000-4.4%$299/sqft |
Source: Stellar MLS #O6312394 Report a problem | ||
| 8/30/2025 | Price change | $1,250,000-2%$313/sqft |
Source: Stellar MLS #O6312394 Report a problem | ||
| 5/27/2025 | Price change | $1,275,000-1.5%$319/sqft |
Source: Stellar MLS #O6312394 Report a problem | ||
| 4/6/2023 | Pending sale | $1,295,000$324/sqft |
Source: Stellar MLS #O6073638 Report a problem | ||
| 2/22/2023 | Price change | $1,295,000-2.3%$324/sqft |
Source: Stellar MLS #O6073638 Report a problem | ||
| 1/30/2023 | Price change | $1,325,000-1.9%$331/sqft |
Source: Stellar MLS #O6073638 Report a problem | ||
| 1/5/2023 | Listed for sale | $1,350,000+40.6%$338/sqft |
Source: Stellar MLS #O6073638 Report a problem | ||
| 5/25/2016 | Sold | $960,337+94.9%$240/sqft |
Source: Agent Provided Report a problem | ||
| 11/23/2015 | Sold | $492,800$123/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2024 | $15,677 +112.7% | $938,252 +94.2% |
| 2023 | $7,371 +4.6% | $483,255 +4.1% |
| 2022 | $7,045 +1.3% | $464,325 +3% |
| 2021 | $6,952 +0.7% | $450,801 +1.6% |
| 2020 | $6,901 +1.1% | $443,591 +2.3% |
| 2019 | $6,824 +0.7% | $433,618 +1.9% |
| 2018 | $6,774 0% | $425,533 +1.6% |
| 2017 | $6,774 +1.5% | $418,993 +2.6% |
| 2016 | $6,677 -0.1% | $408,209 +807.1% |
| 2015 | $6,681 | $45,000 |
Find assessor info on the county website
Neighborhood: 34787
Nearby homes
- $771,9004 bd3 ba2.7k sqft5359 Bowman Dr, Winter Garden, FL 34787Off Market
- $798,5004 bd4 ba3.2k sqft5371 Bowman Dr, Winter Garden, FL 34787Off Market
- $907,0004 bd4 ba4k sqft5353 Bowman Dr, Winter Garden, FL 34787Off Market
- $946,0004 bd4 ba4.1k sqft5377 Bowman Dr, Winter Garden, FL 34787Off Market
- $1,956,5005 bd7 ba5.6k sqft5364 Bowman Dr, Winter Garden, FL 34787Off Market
- $1,462,9005 bd6 ba5.6k sqft5364 Bowman, Winter Garden, FL 34787Off Market
- $724,8003 bd2 ba2.8k sqft5347 Bowman Dr, Winter Garden, FL 34787Off Market
- $743,9003 bd2 ba2.9k sqft5383 Bowman Dr, Winter Garden, FL 34787Off Market
Nearby schools
GreatSchools rating
- 9/10Independence ElementaryGrades: K-5Distance: 1.1 mi
- 9/10Bridgewater Middle SchoolGrades: 6-8Distance: 1 mi
- 6/10Horizon High SchoolGrades: 9-12Distance: 3.6 mi
Schools provided by the listing agent
- Elementary: Independence Elementary
- Middle: Bridgewater Middle
- High: Horizon High School
Source: Stellar MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
Get a cash offer in 3 minutes
Find out how much your home could sell for in as little as 3 minutes with a no-obligation cash offer.
Estimated market value
$1,154,700
Get a cash offer in 3 minutes
Find out how much your home could sell for in as little as 3 minutes with a no-obligation cash offer.
Estimated market value
$1,154,700
- Florida
- Orange County
- Winter Garden
- 34787
- 5365 BOWMAN DRIVE
Nearby cities
Nearby neighborhoods
Nearby zip codes
Other Winter Garden Topics
