Windsor Hills Resort is one of my favorite resorts to own a vacation home in all of Central Florida. Please scroll all the way down to see all the active listings!
Windsor Hills is located just minutes from Walt Disney World & other top vacation attractions!
Windsor Hills Resort Homes for Sale Near Disney (Airbnb Investment Ready)
Buy in one of Orlando’s most in-demand vacation rental communities, just minutes from Disney. Whether you’re an investor or second-home buyer, Windsor Hills offers proven rental performance, strong occupancy, and long-term value.
Work with a local expert who doesn’t just sell homes, but actively owns and manages them.
⭐ 4.8+ Airbnb rating
🏡 100+ vacation homes managed (FunStay Florida)
💰 Real rental data, not estimates
Why Windsor Hills Is One of Orlando’s Top Airbnb Communities
Windsor Hills is not just another neighborhood. It’s a purpose-built vacation rental ecosystem designed for short-term rental success.
Located just 1.5 miles from Walt Disney World, this gated resort community consistently attracts families, groups, and international travelers looking for convenience and experience.
What makes Windsor Hills stand out:
- STR-friendly zoning (Airbnb & VRBO allowed)
- Close proximity to Disney, Universal, and attractions
- Resort-style amenities that drive bookings
- Strong global demand year-round
This combination is why Windsor Hills continues to outperform many other Orlando communities.
Why Guests Choose Windsor Hills (And Why It Matters for ROI)
Amenities aren’t just “nice to have”. They directly impact occupancy, nightly rates, and guest satisfaction.
Windsor Hills delivers a resort-level experience that drives repeat bookings:
- Resort-style pool with water slide and spa
- 40-seat movie theater
- Fitness center and sports courts
- Game rooms and entertainment areas
- Gated community with 24/7 security
These features increase:
- Booking demand
- Guest satisfaction
- Review scores
- Revenue potential
Windsor Hills Airbnb Income Potential (2026 Data)
Windsor Hills is one of the few Orlando communities with proven, consistent rental performance.
Typical performance ranges:
- Occupancy: ~65%–75% annually
- Peak season premiums: +20–40%
- Strong ADR due to location and amenities
Estimated rental income:
- 3-bedroom: ~$38K–$48K/year
- 4-bedroom: ~$50K–$65K/year
- 5–6 bedroom pool homes: ~$65K–$90K/year
Buyers are not just purchasing a home. They’re acquiring a cash-flowing asset.
Windsor Hills Homes for Sale (Current Market Snapshot)
Windsor Hills offers a wide range of property types:
- Condos: ~$275K–$340K
- Townhomes: ~$375K–$420K
- Single-family pool homes: ~$550K–$720K+
Most in-demand properties include:
- 4–6 bedroom pool homes
- Updated interiors
- Themed bedrooms
- Turnkey Airbnb-ready setups
The right property can significantly outperform the market average.
Work With an Airbnb-Focused Realtor (Not Just Any Agent)
Most realtors:
❌ Sell homes based on comps
❌ Don’t understand Airbnb performance
❌ Don’t target investor buyers
Mike Chen is a true Airbnb STR Realtor.
- Owns multiple homes in Windsor Hills
- Manages 100+ vacation rentals (FunStay Florida)
- Uses real booking data to guide decisions
- Helps from purchase → setup → first booking
This is the difference between buying a property and building a profitable investment.
Traditional Realtor vs Airbnb Investment Specialist
| Feature | Traditional Realtor | Mike Chen (STR Specialist) |
| Understands Airbnb revenue | ❌ | ✅ |
| Uses real rental data | ❌ | ✅ |
| Targets investor buyers | ❌ | ✅ |
| Helps with setup & management | ❌ | ✅ |
| Maximizes ROI | ❌ | ✅ |
What Drives Property Value in Windsor Hills
Not all homes perform the same, even in the same community. When determining the Windsor Hills market value, these are the key drivers:
- Private pool & outdoor space
- Bedroom count (larger homes = higher revenue)
- Themed rooms (family appeal)
- Updated interiors
- Proximity to clubhouse
- Rental performance history
Based on these factors, two similar homes can have property values that differ by tens of thousands of dollars.
Location Advantage (Minutes From Everything)
Windsor Hills is positioned in one of the most strategic locations in Central Florida:
- Disney World: ~5–10 minutes
- Universal Studios: ~16–22 miles
- SeaWorld: ~11 miles
- Orlando International Airport: ~25 miles
This proximity is a major driver of booking demand.
Get Your Windsor Hills Investment Analysis
Before you buy, understand the numbers.
We provide:
- Estimated rental income
- ROI projections
- Occupancy insights
- Property recommendations
- Community comparisons
Request Your Free Investment Report
Ready to Buy in Windsor Hills Resort?
If you’re serious about investing in Orlando vacation rentals, Windsor Hills is one of the strongest opportunities available, but only if you buy the right property.
Work with a local expert who understands both real estate and Airbnb performance.
📞 Call or text Mike Chen
📧 Email: [email protected]
INTERESTED IN BUYING OR SELLING IN WINDSOR HILLS RESORT?
WINDSOR HILLS HOMES FOR SALE
My name is Mike Chen and I’m a Realtor and vacation homeowner in the Orlando, FL area. I absolutely love Orlando and I would love to have a chat with you about buying or selling in this growing and exciting city. My wife and I are also owner-operators of a very successful vacation rental business, FunStay Florida Vacation Homes. Read our story on how we got started HERE and contact us to chat about your dream.
I specialize in:
- Purchase and sale of income-producing vacation homes
- Orlando area investment homes
- Running a vacation home business
- Setting up your vacation home for guests (design, furniture package, remodeling, etc)
NEED A PROPERTY MANAGEMENT COMPANY TAKE CARE YOUR VACATION RENTAL AT WINDSOR HILLS RESORT?
Our Management Services. Give me a call 503-888-8070!
Planning on buying a home in Windsor Hills Resort as a vacation rental? Your property manager plays a critical role in the direct success of your vacation rental business. Managing your short-term rental properties can be a time-consuming and stressful business for owners/hosts. Guests expect hotel quality amenities, personal yet professional service, and 24-hour support when booking a vacation rental. We are experienced property managers and hosts. We started our journey by owning just one property 2 years ago and now we have grown to 5 properties in the area. Do you need an experienced property management company to take care of your short-term rentals? Please read HERE to see why we are the right property managers for you.
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