Stacy Ann Stephens • REALTOR® & Licensed Mortgage Broker • Winter Park, FL
Four Seasons Condominiums Winter Park: What Buyers Need to Know in 2026
The community most Winter Park condo buyers overlook — and the one that just might change everything about what you thought you could afford here.
Hi, I’m Stacy Ann Stephens, a local REALTOR and licensed mortgage broker serving Winter Park and Central Florida. If you’ve been condo hunting in Winter Park and keep seeing prices that make your eyes water, I want to introduce you to a 20-acre community that quietly delivers exceptional value.
Located at 200 Saint Andrews Blvd, Winter Park, FL 32792, Four Seasons Condominiums sits squarely inside Winter Park city limits. That means you get real Winter Park services, parks, and one of Orange County’s strongest public school districts — without the premium price tag of newer construction.
Here, 1-bedroom condos often start in the low $150s, while spacious 2- and 3-bedroom units and townhomes typically fall in the $250s to $300s+. In this zip code, that’s a genuine opportunity.
Resort-Style Amenities Most Communities Only Dream About
Built in 1970 and lovingly maintained for over five decades, Four Seasons feels like a private resort. Spread across 20 beautifully landscaped acres, you’ll find:
- Three sparkling swimming pools positioned throughout the property (no fighting for lounge chairs)
- Tennis courts and classic shuffleboard courts
- A newly renovated fitness center and welcoming clubhouse
- Community library and events space perfect for book clubs or neighbor gatherings
- Onsite management team available Monday through Friday
- Pet-friendly policy (cats and dogs welcome with reasonable size limits)
- Covered carport parking with assigned spaces
The HOA fee is one of the smartest parts of owning here. It covers water, sewer, trash, pest control, grounds maintenance, pool care, building insurance, and reserves. For most owners, electricity is your only separate utility bill — making monthly costs predictable and manageable.
A Walkable Winter Park Location That’s Hard to Beat
Four Seasons offers walkability that many Winter Park addresses simply don’t. You’re steps from the scenic Cady Way Trail and Ward Park. A short stroll takes you to Publix, Sprouts Farmers Market, Aldi, Starbucks, and Panera Bread.
Historic Park Avenue with its boutiques, restaurants, and charm is just five minutes by car. AdventHealth Winter Park and the Center for Health and Wellbeing are nearby, and major highways (SR-436, FL-417, and FL-408) make commuting straightforward. Orlando International Airport sits about 25 minutes away.
This combination of peaceful community living with everyday conveniences is exactly why so many of my buyers fall in love with the area.
Top-Rated Schools: A Game-Changer for Families
For many families I work with, schools are the deciding factor. Four Seasons is zoned for Brookshire Elementary, Glenridge Middle School, and Winter Park High School — consistently ranked among the best public schools in Orange County.
Parents tell me this school pipeline gives them confidence that their kids are getting a strong education while still enjoying the benefits of condo living (no yard to maintain on busy school nights).
The Financing Advantage Most Buyers Miss
Here’s something unique: I’m not just your REALTOR — I’m also a licensed mortgage broker (NMLS #1933745 | Jhenesis Mortgage NMLS #2532705). That means we handle both your home search and your financing under one roof.
Condo financing has specific guidelines that differ from single-family homes. I personally review every Four Seasons purchase for my clients so there are no surprises at closing. Whether you’re a first-time buyer, downsizing, or investing, I’ll help you understand your options clearly.
Free Mortgage Payment Calculator & HOA Estimator
Want to see what ownership at Four Seasons could actually cost you each month? I’ve created a simple, accurate calculator that factors in current pricing, typical HOA fees, property taxes, and insurance.
Try the Four Seasons Ownership Calculator → (Embedded tool or link to interactive calculator on realtorstephens.com)
Enter your down payment, credit scenario, and preferred unit size to get a personalized monthly payment estimate — including the utility-inclusive HOA.
Is Four Seasons Right for You?
This established community offers a rare mix: genuine Winter Park living, strong amenities, excellent schools, and pricing that still makes financial sense in 2026. It’s ideal for first-time buyers, young professionals, families, retirees, and investors alike.
Call or Text Me at 407-603-1664
Let’s schedule a private tour of available units at Four Seasons Condominiums.
Frequently Asked Questions About Four Seasons Condominiums
What is the price range for condos at Four Seasons Winter Park?
1-bedroom units often start in the $150s, while 2- and 3-bedroom condos and townhomes typically range from the $250s to low $300s depending on condition and upgrades.
What does the HOA fee cover at Four Seasons?
The HOA includes water, sewer, trash, pest control, grounds maintenance, pool upkeep, building insurance, and reserves. Most residents only pay electricity separately.
Which schools serve Four Seasons Condominiums?
Residents are zoned for Brookshire Elementary, Glenridge Middle, and Winter Park High School — some of Orange County’s top public schools.
Is Four Seasons pet-friendly?
Yes. The community welcomes cats and dogs with size limits that apply.
How close is Four Seasons to Park Avenue?
Park Avenue is approximately five minutes by car. The community itself is highly walkable to grocery stores, restaurants, and parks.
Ready to Explore Four Seasons Condominiums?
If you’re tired of overpriced options and want a true Winter Park lifestyle with smart economics, let’s talk. I’ll show you current listings, run the numbers together, and make sure the financing works for your goals.
Schedule Your Private Showing – Call/Text 407-603-1664