Four Seasons Condominiums
Winter Park, Florida
200 Saint Andrews Blvd, Winter Park, FL 32792
An established 20-acre community within the Winter Park city limits — tree-lined, amenity-rich, and zoned for top-rated schools. Condos from the $150s. Townhomes to the $300s. One trusted advisor for buying, selling, and financing.
About the Community
Winter Park Living, Without the Winter Park Price Tag
Let me be straight with you: Four Seasons Condominiums is one of the best-kept secrets in Central Florida. You get an official Winter Park address — inside city limits — with top-rated schools, walkable lifestyle, and resort-style amenities at a fraction of what a single-family home in this zip code costs.
Built in 1970 and set across approximately 20 beautifully maintained acres, this community has the kind of mature trees, tranquil courtyards, and established neighborhood feel that new construction simply can’t replicate. The HOA handles water, sewer, trash, pest control, grounds maintenance, and pool upkeep — so your weekends belong to you.
Whether you’re a first-time buyer ready to stop renting, a retiree looking to downsize without sacrificing quality of life, a parent prioritizing school district, or an investor looking for a low-cost entry into a high-demand rental market — Four Seasons checks every box.
And because I’m both your Realtor® and your Mortgage Broker, you have one person — one phone call — to handle both the home search and the financing. That’s not convenience, that’s strategy.
City of Winter Park
Official Winter Park incorporation — access to city services, parks, and events.
A+ School District
Brookshire Elementary, Glenridge Middle & Winter Park High School.
20 Acres of Green
Mature oaks, manicured courtyards, and resort-style grounds.
3 Swimming Pools
Multiple pools across the property — no waiting, no crowds.
HOA Includes Utilities
Water, sewer, trash, pest control, grounds & pool maintenance included.
Onsite Management
Dedicated management team on property Monday–Friday.
Pet-Friendly
Cats and dogs welcome — see HOA rules for size/number details.
Assigned Parking
Covered carport spaces available with unit assignments.
Resort-Style Living
Amenities That Make Every Day Feel Like a Weekend
This isn’t just a place to sleep — it’s a lifestyle. Four Seasons delivers the kind of amenity package you’d expect from a luxury property, at a price that still makes your mortgage broker smile.
3 Swimming Pools
Multiple pools scattered across the 20-acre community — always one nearby.
Tennis Courts
Regulation tennis courts for residents and their guests.
Fitness Center
Newly renovated fitness room — skip the gym membership.
Shuffleboard Courts
A classic community favorite — social, fun, and always free.
Clubhouse & Library
Newly renovated events area with a cozy community library.
Laundry Facilities
Laundry facilities on property — many units also have in-unit W/D.
Beautifully Maintained Grounds
Mature landscaping, majestic oaks, and park-like courtyards.
Onsite Management
Dedicated management available Mon–Fri for quick assistance.
Find Your Fit
Condos & Townhomes for Every Stage of Life
From the efficient 1-bedroom to the spacious 3-bedroom and the multi-story townhome — Four Seasons has a floorplan for first-time buyers, downsizers, and investors alike.
1-Bedroom Condo
From the $150s–$180s
Screened patio, walk-in closet, pool views in select units. HOA covers water, sewer, trash & pest control. Ideal for first-time buyers and rental investors.
2-Bedroom Condo
From the $180s–$260s
Corner units available with expansive pool and green space views. Open-concept layouts, screened patios, updated kitchens in renovated units. The #1 choice for downsizers and couples.
3-Bedroom Condo
From the $250s–$300s+
Rare find in this community. Spacious split-bedroom layouts with generous living/dining areas and screened patios. Strong rental demand from UCF, Full Sail, and Rollins College proximity.
2-Bedroom Townhome
From the $220s–$300s+
Multi-level living with private patio, carport, and the feel of a single-family home. Popular with young professionals and small families. Corner units go fast.
Prime Location
Walk to Almost Everything. Drive to the Rest.
Here’s what I love telling buyers: when I say this community is walkable, I actually mean it. From your front door, you’re minutes from groceries, the trail, the gym, and medical care — without ever getting on the highway.
🛒 Shopping & Groceries
🌿 Parks & Wellness
🏥 Medical
⛳ Recreation
🎓 Universities Nearby
🚗 Major Roads & Travel
Top-Rated Public Schools
One of Winter Park’s Most Desired School Districts
For families, this is non-negotiable. Four Seasons is zoned for the Winter Park school pipeline — one of the most sought-after public school tracks in Orange County.
Brookshire Elementary
A nurturing, community-centered elementary with strong academics and family involvement.
Glenridge Middle School
Comprehensive middle school curriculum with arts, athletics, and advanced programs.
Winter Park High School
Consistently ranked among Orange County’s top public high schools — AP programs, collegiate athletics, and an active alumni network.
* School zoning is subject to change. Verify current assignments with Orange County Public Schools before purchasing.
Thinking About Selling Your Four Seasons Condo?
The market for Winter Park condos is active — and buyers are specifically searching this community. I know Four Seasons inside and out, I have direct access to the buyer pool, and as your agent AND mortgage broker, I can even help qualified buyers get pre-approved so your deal doesn’t fall apart at the finish line.
Jhenesis Mortgage · NMLS #2532705
Financing That Works as Hard as You Do
Here’s the advantage most buyers don’t realize they have access to: your Realtor is also your Mortgage Broker. I can pre-approve you, structure your loan, and negotiate your contract — under one roof, with one trusted advisor who has skin in the game from day one.
Four Seasons units are condo-association properties, which means financing has specific guidelines. I know exactly which loan products work here — and I’ll get you to the closing table without surprises.
Conventional Condo Loans
Best for buyers with good credit and 3–20% down. Competitive rates, flexible terms. Condo association warrantability requirements apply — I’ll handle the review.
FHA Condo Loans
As low as 3.5% down for qualified buyers. FHA spot approval may be available for non-FHA-approved buildings. Ask me about eligibility.
VA Condo Loans
Veterans and active military may qualify for zero down financing on approved condos. Only ~15% of veterans use this benefit — let’s make sure you’re not leaving it on the table.
Refinancing & Cash-Out
Already own at Four Seasons? With home values strong and equity built, now may be the time to refinance, lower your rate, or access cash for renovations or other investments.
DSCR & Investor Loans
Buying as a rental investment? DSCR loans qualify on the property’s rental income — not your personal tax return. Great for self-employed investors or those building a portfolio.
Stacy Ann Stephens | Mortgage Broker | NMLS #1933745 | Jhenesis Mortgage NMLS #2532705 | jhenesismortgage.com
✦ Exclusive Tool
Monthly Payment Estimator
Get a quick snapshot of what your Four Seasons unit could cost per month. Adjust the numbers to explore different scenarios.
* Estimate only. Does not include homeowner’s insurance, PMI (if applicable), or closing costs. Rates change daily. For a personalized quote, contact Stacy Ann Stephens, NMLS #1933745.
Already a Resident?
Helpful Resources for Four Seasons Homeowners
Whether you’re managing your HOA documents, closing on a sale, or paying your assessments — here are the official links you need, all in one place.
Community Documents
Access official HOA documents, bylaws, rules & regulations, and community policies on the Four Seasons COA website.
View Documents →Closing Documents
Buying, selling, or refinancing your Four Seasons condo? Order your official HOA closing document package through Sentry Management.
Order Documents →HOA Payments
Pay your Four Seasons monthly assessments online quickly and securely through the ClickPay resident payment portal.
Make a Payment →Got Questions?
Everything You Need to Know About
Four Seasons Winter Park
Four Seasons Condominiums is located at 200 Saint Andrews Blvd, Winter Park, FL 32792, within the official City of Winter Park limits — not just the Winter Park mailing address. The community sits just off Aloma Avenue, near the intersection of SR-436 (Semoran Blvd), giving residents excellent access to shopping, dining, and major roadways while still enjoying Winter Park’s quiet, tree-lined character. It is approximately 25 minutes from Orlando International Airport.
HOA fees at Four Seasons vary by unit size and type, but typically cover water, sewer, trash, pest control, pool maintenance, grounds maintenance, recreational facilities, escrow reserves, building insurance, and management. This “utility-included” structure makes monthly budgeting predictable — your electric bill is often your only separate utility. Contact me for current HOA fee specifics on any active listing, as fees vary unit to unit.
Four Seasons is currently zoned for Brookshire Elementary School, Glenridge Middle School, and Winter Park High School — three of Orange County’s most sought-after public schools. This school pipeline is one of the primary reasons families and investors target this community. Always verify zoning directly with Orange County Public Schools before purchasing, as boundaries can change.
Four Seasons offers 1-bedroom condos, 2-bedroom condos, 3-bedroom condos, and 2-bedroom/1.5-bath townhomes. Condos range from approximately 725 to 1,322 square feet in flat configurations, while the townhomes offer multi-story living with private patios. Units were built in 1970 and many have been renovated with modern finishes — granite counters, updated kitchens, new flooring, and in-unit washer/dryers. Prices typically range from the $150s to the $300s depending on size and condition.
Yes — and here’s why: Four Seasons has strong rental demand driven by its proximity to Full Sail University, Rollins College, UCF, and AdventHealth Winter Park. Historically, 1-bedroom units have rented for around $1,350–$1,500/month, and larger units command more. The low purchase price point combined with HOA-included utilities makes this a strong cash-flow candidate. As your mortgage broker, I can also walk you through DSCR loan options that qualify based on rental income — not your personal tax return. Check the payment calculator above to model your numbers.
Condo financing has specific guidelines that differ from single-family home loans. The condo project must meet warrantability requirements for conventional loans, or FHA spot approval may be available for FHA loans. VA loans are also an option for eligible veterans if the project meets VA condo requirements. As a licensed Mortgage Broker (NMLS #1933745) with experience in condo financing, I handle this review for every buyer I work with. Email me directly or visit jhenesismortgage.com to get pre-qualified before you shop.
Most condos in Winter Park are either priced out of reach for first-time buyers, or lack the amenity infrastructure that makes community living enjoyable. Four Seasons offers something rare: a true Winter Park city address, top-rated schools, 20 acres of maintained green space, 3 pools, a fitness center, tennis courts, and utility-included HOA — all starting from the $150s. Add proximity to Cady Way Trail, Aloma Avenue shopping, Park Avenue, and three major universities, and you have a community that punches well above its price point.
Great question — and you may be pleasantly surprised. I offer a free Comparative Market Analysis (CMA) for Four Seasons owners that shows you exactly what similar units have sold for and what your unit could fetch in today’s market. I also know who the active buyers are. Email me at stacyann@realtorstephens.com or call 407-603-1664 to request yours today — no obligation, no pressure.
Stacy Ann
Stephens
REALTOR® & Mortgage Broker
One Agent. One Lender.
Your home search and your financing — handled by one trusted advisor.
Why Work With Me?
I know what it feels like to be new to a country, navigate an unfamiliar market, and try to figure out if homeownership is even possible for someone in your situation. I’ve been there. My Jamaican background and firsthand experience through the 2008 housing crisis didn’t discourage me from real estate — it turned me into the advisor I needed but didn’t have.
Today, I’m both a licensed Florida Realtor® at Keller Williams Winter Park and a licensed Mortgage Broker at Jhenesis Mortgage. That means when you work with me on your Four Seasons purchase, I’m managing your search, negotiating your contract, and structuring your loan — with full visibility across both sides of the transaction. You don’t have to wonder if your agent and lender are talking. They’re the same person.
Stacy Ann Stephens · REALTOR® · Keller Williams Realty Winter Park · 147 W Lyman Ave, Winter Park FL 32789 · BK3393979
Ready to Make Your Move
at Four Seasons?
Whether you’re buying your first home, downsizing, investing, or selling — I’m here to guide you from “what’s possible?” to keys in hand. Let’s start with a conversation.
📞 407-603-1664 · stacyann@realtorstephens.com · realtorstephens.com