The Lock-and-Leave Life Is Calling —
Park Avenue Is Right Outside Your Door
A deep dive into Winter Park’s most sought-after condos and townhomes — The Cloisters, Winterset, Interlachen Place, Park Aire, Lake Killarney, and more — from someone who actually knows these buildings.
Let me be honest with you for a second. Park Avenue in Winter Park doesn’t need a sales pitch. If you’ve ever walked it — the Spanish moss, the sidewalk cafés, the Farmers’ Market on a Saturday morning, the way the light hits Lake Osceola at dusk — you already get it. What I can tell you is this: there’s a very specific kind of buyer and seller who’s been quietly paying attention to the condos and townhomes within walking distance of it, and the search activity and sales volume I’m seeing right now in 32789 tells me that window won’t stay open much longer.
Whether you’re a retiree ready to trade your lawn for a morning walk to brunch, a second-home buyer who wants a real address (not just an Airbnb), a Rollins College parent who’s done the math on rent vs. owning, or someone who simply wants to live beautifully without dealing with maintenance headaches — this guide is written for you. Let’s talk about what’s actually available, what the market looks like, and why now matters.
The Communities You Need to Know — And What Makes Each One Different
Not all Park Avenue-adjacent condos are created equal. Some sit right on the water. Some are a 4-minute walk to brunch. Some are art deco gems with character you simply can’t replicate in new construction. Here’s my honest breakdown of the buildings generating the most attention right now.
The Cloisters
100 S. Interlachen Ave · 32789
A 6-story lakefront community on Lake Osceola — literally two blocks from Park Avenue. Units run 900–1,950 sq ft, priced roughly $565K–$939K+ with recent closed sales in that range. You get lake views, boat docks, a heated pool, a putting green, and a full-time on-site manager. This is the “lives like a private residence without the private residence problems” building. Rarely available. High absorption when priced right.
Interlachen Place
147 Interlachen Place · 32789
One block from Central Park and Park Avenue — and it shows in demand. Bright, single-floor units with private elevator access, secured underground parking, and a lifestyle that says “I live here, I don’t just visit.” If walkability is your #1 criteria, this is the building conversation starts at.
Park Aire
N. Park Ave · 32789
The retro-chic classic — an art deco-style building right on North Park Avenue. Fully renovated units with wood floors and picture windows that look out on Casa Feliz and St. Margaret Mary. If you want soul, character, and an address that actually says “Park Avenue” — this is it. Priced more accessibly than the lakefront buildings, making it a strong entry point into the corridor.
Winterset (Village of Winterset)
32789 Corridor
A gem in the heart of the city — renovated in 2024, with private storage and easy walkability to restaurants and shops. Ample parking (a legitimate luxury near Park Avenue). Units here appeal to buyers who want the downtown Winter Park energy without being right on the avenue.
Lake Killarney Communities
Lakeside Manor, Killarney Bay, Chateaux du Lac · 32789
Spring-fed Lake Killarney — 239 acres — just one block from Winter Park Village and about a mile from Park Avenue. Lakefront pools, boat ramps, clubhouses, and some of the best value-per-square-foot in the corridor. Killarney Bay is particularly active right now with buyers who want water access at a more approachable price point.
Lachen House, Park West & Others
Various · 32789
Lachen House (rare ground-floor units, priced ~$635K), Park West (2,000+ sq ft townhome-style units near the Farmers’ Market zone), and several boutique buildings rounding out the 1.5-mile ring around Park Ave. These fly under the radar — which is exactly why my buyers find value there.
| Community | Distance to Park Ave | Price Range (Active) | Best For | Standout Feature |
|---|---|---|---|---|
| The Cloisters | ~2 blocks | $565K – $940K+ | Retirees, 2nd home, downsizers | Lake Osceola, boat docks, putting green |
| Interlachen Place | 1 block | $600K – $850K | Walk-everywhere buyers | Elevator, underground parking, Central Park steps away |
| Park Aire | On Park Ave | $300K – $550K | Entry buyers, investors, 2nd home | Art deco character, Park Ave address |
| Winterset | ~3–5 min walk | $400K – $650K | Full-time residents, downsizers | Renovated, ample parking, village vibe |
| Lake Killarney | ~1 mile | $170K – $700K+ | All buyers — widest range | Waterfront access, boat ramp, best value/sqft |
| Lachen House | Downtown core | ~$635K | Discerning buyers seeking rare units | Ground-floor rarity, quick close available |
Who’s Actually Buying These Condos — And Why It Matters to You
I work with a really specific set of people in this corridor, and understanding who’s competing for these units helps you position yourself — whether you’re buying or selling.
The Wealthy Retiree / Downsizer Done with the 4,000 sq ft and the landscaping company. They want Lake Osceola views, a heated pool, and the Saturday Farmers’ Market within walking distance. The Cloisters and Interlachen Place are ground zero for this buyer.
The Second Home Buyer Northeast or Midwest primary home, Winter Park is the lifestyle escape. Lock and leave. No yard. Good HOA. Walk to dinner. These buyers are increasingly active and they move fast when the right unit appears.
Rollins College Parents Smart money: buy a 2-bed condo instead of paying $3,000+/month in rent for 4 years. Kid lives in one room, rent out the second. After graduation, sell or keep as an investment. Rollins is 0.3 miles from The Cloisters.
The Lifestyle Buyer Comes in many forms — the remote worker who wants walkable, the couple who sold their suburbs house, the professional who values time over square footage. Park Aire and Winterset are especially popular with this group.
The Investor DSCR loan eligible, rental-income focused. Lake Killarney offers some of the best cap rate potential in the corridor at lower price points. Some units here also appeal as furnished executive rentals — a strong income play in a market with real demand drivers.
International & ITIN Buyers Winter Park’s cultural scene, walkability, and proximity to Orlando International make this a genuine target market. Foreign national and ITIN financing options exist — and I do both real estate and mortgage brokering, so I can help you navigate that from one conversation.
— Stacy Ann Stephens
What the Market Is Actually Doing Right Now (Spring 2026)
I’ve been watching 32789 closely, and here’s what the numbers and my own client activity are telling me:
Search volume is up. The specific buildings in this 1.5-mile Park Avenue corridor — The Cloisters, Winterset, Interlachen Place, Park Aire, Lake Killarney — are showing meaningfully higher search activity and more units going under contract compared to 18 months ago. That’s not an accident. It’s lifestyle migration meeting limited inventory in one of Central Florida’s most genuinely walkable neighborhoods.
The Cloisters is a benchmark. Recent sales at The Cloisters ranged from $540,000 to $939,000, with a median sale price around $685,000 and a median price per square foot near $577. With only a handful of active listings at any given time, the absorption rate sits around 2.4 months of inventory — meaning this is a seller’s market within a building people rarely leave voluntarily.
Price per square foot is strong but not irrational. The median list price for Cloisters Condominiums in early 2025 reached approximately $1.09M at peak, with some moderation since — but the corridor overall is holding value well, especially for lakefront and walkable units.
Lake Killarney is the value play. Just one block from Winter Park Village and about a mile from Park Avenue, Lake Killarney communities like Killarney Bay offer renovated 2-bed/2-bath condos with lakefront pool access at price points well below the Interlachen Corridor — making it particularly compelling for investors and value-conscious buyers who still want the Winter Park lifestyle.
What this means if you’re selling: Condition and pricing precision matter more than ever. A fully updated unit priced right in this corridor doesn’t sit. An overpriced one or one that shows poorly will linger. If you’re thinking about selling in 2026, call me before you list — I’ll tell you exactly how to position it.
What this means if you’re buying: The buyers I’m working with right now are not waiting for a dip that may not come. They’re moving on quality units when they appear. The best units in The Cloisters and Interlachen Place go with minimal days on market when priced correctly.
Why Winter Park Specifically — And Why This Corridor Over Everything Else in Central Florida
I sell real estate all over Central Florida. I choose to be based in Winter Park because it’s different — and the condo corridor around Park Avenue is the most concentrated expression of what makes it different.
You can explain the lifestyle with a list, but it lands better if you just picture it: Saturday morning, you walk to the Park Avenue Farmers’ Market, stop at a sidewalk café, spend an hour at the Morse Museum looking at Tiffany glass, then walk home along the lake. That’s not a vacation. That’s a Tuesday if you live in this zip code.
A few specifics worth knowing:
- Rollins College is under a mile from The Cloisters — a genuine driver of steady rental and resale demand in this corridor.
- AdventHealth Orlando is about 2.8 miles away — important for retiree buyers and families.
- The Alfond Inn, one of Central Florida’s most celebrated boutique hotels, sits immediately adjacent to The Cloisters on Interlachen Ave. That’s not a coincidence — it’s a signpost of the neighborhood’s character.
- Publix is 1 mile away at Winter Park Village. Target is nearby. Whole Foods and independent restaurants line the avenue. This is a genuinely walkable lifestyle — not “walkable” in the Florida suburban sense of the word.
- SunRail access, proximity to I-4, and about 15 miles to Orlando International Airport make this a practical choice, not just a romantic one.
- No state income tax. I say it because it still matters — especially to second-home buyers migrating from the Northeast or Midwest.
🔍 Browse Active Listings Now
View all current condos and townhomes for sale in ZIP 32789 — updated in real time from the MLS.
View Active Listings →Frequently Asked Questions
Real questions from buyers, sellers, and investors — answered honestly.
What condos near Park Avenue in Winter Park are the most walkable?
The closest condos to Park Avenue itself are Park Aire (on North Park Ave), Interlachen Place (one block from Central Park), and The Cloisters (two blocks from the avenue on Interlachen Ave, adjacent to the Alfond Inn). These three buildings give you the highest walkability scores — you can be at the Saturday Farmers’ Market, a café, or the Morse Museum of American Art without ever starting a car.
How much does a condo near Park Avenue in Winter Park, FL cost?
It depends on the building and how close to the water you want to be. Park Aire offers entry points in the $300K–$550K range for 1-2 bedroom units. The Cloisters runs $565K–$939K+ for 2-3 bedrooms with lake views. Interlachen Place and boutique buildings like Lachen House sit in the $600K–$850K range. Lake Killarney communities offer the widest range — from under $200K for a 1-bed entry point up to $700K+ for lakefront townhomes.
Market conditions evolve, so I always recommend a current pricing conversation before you assume a listing is out of reach — or in reach. Call me directly at 407-603-1664.
Is The Cloisters in Winter Park a good investment?
The Cloisters has historically held and appreciated in value well — lakefront inventory in a walkable, high-demand zip code doesn’t appear frequently. With a current absorption rate of around 2.4 months of inventory and recent median sales near $685,000, it’s not a “flip and flip fast” building — it’s a quality long-term hold or lifestyle-use property. If you’re evaluating it as a rental, note that HOA rules vary and I’d review restrictions with you before you buy for that purpose. As your real estate AND mortgage broker, I can model both scenarios for you.
Can Rollins College parents buy a condo instead of renting for their student?
Yes — and it’s a strategy I actively discuss with parents. Rollins College is less than 0.3 miles from The Cloisters. A 2-bedroom condo purchase allows your student to live in one room while the second bedroom generates rental income to offset your mortgage payment. When they graduate, you sell or keep the property as an investment. Over a 4-year timeline, the math often favors ownership significantly over paying rent into a void. I can run the numbers with you — just call or email.
What is the best condo community near Park Avenue for a second home buyer?
It depends on what you want your second home to do for you. If you want a true lock-and-leave with the highest lifestyle amenity package, The Cloisters is hard to beat — on-site manager, heated pool, lake access, adjacent to the Alfond Inn. If walkability is the priority, Interlachen Place or Park Aire. If you want water access at a more moderate price point, Lake Killarney communities offer excellent value. I’m happy to match you to the right building based on how you plan to use it — schedule a call and we’ll figure it out in 20 minutes.
Are there condo financing options for international buyers or ITIN holders near Park Avenue?
Yes — and this is actually one of my specialties. I am both a licensed Florida Real Estate Broker and a licensed Mortgage Broker (NMLS #1933745) operating under Jhenesis Mortgage. I work with foreign national loan programs and ITIN-based financing for buyers who don’t have a U.S. Social Security number. Florida’s Central corridor, including Winter Park, is one of the most popular markets for Latin American and international buyers — and I’m actively building bilingual resources to serve this community. Reach me at 407-603-1664 or [email protected].
I want to sell my condo near Park Avenue — how do I get the best price?
Three things move the needle most in this corridor: condition (updated kitchens and baths matter enormously in this buyer pool), pricing precision (these buildings have real comps and buyers who’ve done their homework), and marketing reach (the buyer for your Cloisters unit may be in Chicago or São Paulo — your listing needs digital visibility that reaches them). I handle all three. Call me for a complimentary seller consultation before you make any decisions: 407-603-1664.
What are HOA fees like in Winter Park condos near Park Avenue?
HOA fees vary meaningfully by building and what’s included. At The Cloisters, fees cover water, trash, building insurance, pool, and the on-site manager — so your all-in monthly cost is predictable even if the fee line looks higher than a bare-bones HOA. Before we write an offer on any unit, I always pull the HOA docs, review financials, check reserve adequacy, and flag any pending special assessments. This is standard practice in my buyer representation — you won’t be surprised at closing or six months after.
Ready to Talk? Let’s Find Your Place on Park Avenue.
Whether you’re buying, selling, or still in the “I’m just curious” stage — I’m a straight-shooter and I won’t waste your time. Schedule a call, text me directly, or shoot me an email. I respond fast.
Stacy Ann Stephens is a licensed Florida Real Estate Broker affiliated with Keller Williams Realty Winter Park and a licensed Florida Mortgage Broker (NMLS #1933745) operating under Jhenesis Mortgage. Market data referenced reflects publicly available MLS information and third-party sources as of the article publication date and is subject to change. This content is for informational purposes only and does not constitute legal, financial, or tax advice. Always consult licensed professionals for your specific situation.
© 2026 Realtor Stephens · 147 W Lyman Ave, Winter Park, FL 32789