Now Listed — 250 Cortland Avenue, Winter Park, FL 32789 | $950,000 | Entry-Level Luxury on One of Winter Park’s Most Coveted Streets
Represented by Chris Creegan | Creegan Group | Winter Park’s Highest-Producing Luxury Brokerage | 2025 Broker of the Year
There is a version of Winter Park real estate that most people dream about but assume is out of reach. The brick-lined streets. The canopy of mature oaks. The quiet residential character that exists just steps from the boutiques, restaurants, and cultural energy of Park Avenue. The kind of neighborhood where your neighbors’ homes are measured in millions and the street itself feels like a destination.
250 Cortland Avenue puts that version of Winter Park within reach — at a price point that makes it one of the most compelling entry points into the Winter Park luxury market available today.
Listed at $950,000, this meticulously maintained 3-bedroom, 2-bath home sits on one of Winter Park’s most picturesque tree-lined brick streets, surrounded by multi-million-dollar homes, minutes from downtown, and steps from everything that makes Winter Park one of the most desirable communities in all of Florida.
The Address — Why Cortland Avenue Is One of Winter Park’s Most Sought-After Streets
Cortland Avenue is the kind of street that Winter Park residents point to when they want to explain what makes this city different from every other community in Central Florida. The brick-paved road — one of many that define Winter Park’s historic residential character — runs through a neighborhood where homes routinely trade at $1.3 million, $2 million, and beyond. The tree canopy is established and mature. The homes are set back from the street with thoughtful landscaping that gives the block the timeless quality of a neighborhood that has been cared for across generations.
This is a street where buyers who can afford to live anywhere in Central Florida choose to live. The neighbors at 250 Cortland Avenue are not entry-level buyers. They are the executives, professionals, and families who have made Winter Park their long-term home and chosen Cortland Avenue specifically — because this address represents the quiet, walkable, architecturally gracious version of luxury that Winter Park has always been known for.
To purchase at 250 Cortland Avenue at $950,000 is to gain access to a street and a neighborhood that comparably priced properties in Winter Park simply cannot replicate. The street itself is the asset.
The Home — 2,114 Square Feet of Move-In Ready Luxury
250 Cortland Avenue offers 3 bedrooms, 2 full bathrooms, and 2,114 square feet of living space on an 8,279-square-foot lot — a comfortable, well-proportioned residence designed for the way buyers at this level actually want to live.
A Split Floor Plan Built for Privacy and Flexibility
The home’s split-bedroom floor plan separates the primary suite from the secondary bedrooms — the configuration that buyers who work from home, host visiting family, or simply value privacy between sleeping spaces have come to expect at this price point. The layout creates natural separation within a home that lives efficiently without wasted space.
Brazilian Rosewood Floors — The Detail That Sets the Tone
The moment you enter the living areas, the Brazilian Rosewood hardwood floors communicate something clearly: this home was finished with an attention to material quality that the price does not fully reflect. Brazilian Rosewood is a premium hardwood choice that is increasingly rare to find in residential installations — its rich grain, warm tonality, and durability make it a flooring selection typically reserved for custom homes at significantly higher price points.
The quarry tile that flows through the kitchen, bathrooms, and hallways complements the Rosewood with a durable, health-conscious finish that performs in the Florida climate while maintaining a cohesive, elevated aesthetic throughout.
New Roof — The Investment Already Made
A new roof on a home in this price range is a significant detail that buyers should not overlook — because it is a major capital expenditure that the seller has already absorbed. Roof replacement in Central Florida can run $20,000–$40,000 or more depending on the size and material. That cost does not exist on this property. Buyers can budget, plan, and commit with the confidence of knowing the home’s most critical protective system has been recently addressed.
Pool and Spa — Private Outdoor Living, Florida Style
The sparkling swimming pool and spa, enclosed by a privacy PVC fence and connected to an enclosed lanai, create an outdoor living experience that is genuinely resort-quality for a home at this price.
This is the Central Florida outdoor lifestyle at its most functional — a private pool retreat where you can entertain, decompress, or spend a Saturday afternoon entirely detached from the world outside the fence line. The enclosed lanai bridges interior and exterior in the way that Florida living demands: sheltered from the elements, open to the pool, and designed for year-round use.
Oversized Two-Car Garage and Fully Landscaped Grounds
The oversized two-car garage is a practical amenity that belies the home’s classic-neighborhood character — there is genuine storage and vehicle capacity here, not a tight afterthought. The fully landscaped yard with irrigation system keeps the exterior in the condition the street demands without requiring weekend maintenance from the homeowner.
This is a home that has been maintained to a standard consistent with the neighborhood around it — and that consistency shows.
The Location — Steps from Downtown Winter Park, Rollins College, and the Best of Central Florida Living
The proximity of 250 Cortland Avenue to Park Avenue is the location story. Cortland Avenue puts you within walking distance of downtown Winter Park’s Park Avenue district — the boutique-lined, restaurant-dense, culturally rich main street that serves as the social and commercial heart of Winter Park and one of the most distinctive urban environments in all of Central Florida.
Park Avenue — Your Neighborhood’s Main Street
Park Avenue is not a strip mall with a parking lot. It is a curated collection of independent boutiques, James Beard-recognized restaurants, sidewalk cafés, specialty retailers, and galleries that line both sides of a walkable street flanked by Central Park — a full city block of green space that hosts the Winter Park Farmers Market every Saturday morning.
From 250 Cortland Avenue, Park Avenue is not a drive. It is a walk. That distinction — the ability to leave the house on foot for dinner, coffee, the farmers market, or a Saturday evening stroll — is one of the most sought-after and genuinely rare lifestyle features in all of Central Florida real estate. It is the reason Winter Park commands premium pricing relative to every surrounding community. And at 250 Cortland Avenue, it is included.
Rollins College — The Institutional Heart of the Neighborhood
Rollins College, one of Florida’s most prestigious liberal arts institutions, sits at the edge of Park Avenue and defines the character of the surrounding residential neighborhood. The college’s Spanish-Mediterranean architecture, lakefront campus on Lake Virginia, and century-long presence in Winter Park give the area an academic and cultural density that is simply not replicable in any other Central Florida market.
For buyers relocating from urban college towns — Boston, Chicago, Philadelphia, Washington D.C. — the combination of Rollins College and Park Avenue creates a neighborhood texture that feels familiar and grounded in the kind of institutional culture they are accustomed to. For families, the proximity to one of Florida’s top-ranked private colleges is a long-term community asset.
The Winter Park Chain of Lakes — Minutes Away
Lake Mizell, part of the celebrated Winter Park chain of lakes, is immediately adjacent to the Cortland Avenue neighborhood. The Winter Park chain of lakes — a connected system of spring-fed lakes including Lake Virginia, Lake Osceola, Lake Maitland, and others — is the defining natural asset of the Winter Park community and one of the primary reasons that lakefront real estate here commands some of the highest prices in all of Florida.
Boat ramp access to the Winter Park chain of lakes is minutes from Cortland Avenue — meaning that the weekend lake lifestyle, the chain-of-lakes boat tour, and the sunset-on-the-water experience that Winter Park is nationally recognized for are all accessible to residents of 250 Cortland Avenue without requiring lakefront ownership.
Highway Access — Connected Without Being Congested
Cortland Avenue’s position in Winter Park provides exceptional access to the Central Florida highway network — I-4, SR-408, and US-17-92 — without situating the home in a high-traffic, high-noise corridor. The result is the combination that every buyer in this market is searching for: a quiet, residential, tree-lined street that is simultaneously within minutes of every convenience the metro offers.
Downtown Orlando — 10 to 15 minutes. Orlando International Airport — 25 minutes. AdventHealth Winter Park, AdventHealth Orlando, and Orlando Health/ORMC — within practical commuting range for physicians, healthcare executives, and hospital staff. Maitland, Baldwin Park, College Park, and the broader Orlando metro — all accessible without the highway fatigue that defines commuting from Orlando’s outlying suburbs.
Top-Rated Schools — The Family Buyer’s Checklist, Checked
250 Cortland Avenue sits within access to Winter Park’s highly regarded public schools — consistently among the strongest in Orange County — as well as proximity to Lake Highland Preparatory School, one of Central Florida’s most recognized K-12 institutions. For families making a long-term residential decision with children’s education as a primary criterion, the school access from this address is a significant differentiator.
The Market Opportunity — Entry-Level Luxury in a Multi-Million Dollar Neighborhood
The phrase “entry-level luxury” carries real meaning on Cortland Avenue. The homes surrounding 250 Cortland Avenue trade in ranges that dwarf the $950,000 ask — with neighboring properties on the same street listed and sold in the $1.3 million to $2 million-plus range. The estate-scale homes, the architecturally significant properties, and the Winter Park lakefront estates that define this neighborhood’s price ceiling are measured in multiples of what 250 Cortland Avenue is asking.
That price context matters for buyers — because purchasing the most accessible home on one of Winter Park’s most desirable streets is not a compromise. It is a strategy. It is the real estate principle that buyers in every premium market understand: the least expensive home on the most desirable street appreciates toward its neighbors, not away from them.
The buyer for 250 Cortland Avenue is not buying a $950,000 home in a $950,000 neighborhood. They are buying a $950,000 home on a multi-million-dollar street, in one of the most consistently appreciating residential markets in Central Florida, within walking distance of the amenities that define why Winter Park commands premium pricing in the first place.
That is the opportunity. And at $950,000, it is the most accessible it is going to be.
Why Creegan Group — The Team That Knows This Market Better Than Anyone
250 Cortland Avenue is listed by Creegan Group — Winter Park’s highest-producing luxury brokerage, represented by Chris Creegan, the 2025 Orlando Real Producers Broker of the Year and a Top 40 Nationwide Real Estate Team by RealTrends.
Chris Creegan lives in Winter Park. He knows Cortland Avenue not as an address in a database but as a street he has sold on, walked past, and watched evolve across years of deep market participation. The relationships, the off-market knowledge, the understanding of what buyers in this specific neighborhood are looking for — that depth of local knowledge is what separates the result a Creegan Group listing achieves from what a general-market brokerage produces.
For buyers interested in 250 Cortland Avenue, Creegan Group’s infrastructure delivers a clear advantage: access to a buying process backed by 1,000+ verified five-star reviews, expert negotiation, and a team that has closed more Winter Park luxury transactions than any comparable brokerage in the market.
For sellers watching this listing from other Winter Park properties — this is what Creegan Group brings to your address too.
Schedule a Private Showing
250 Cortland Avenue, Winter Park, FL 32789 is available now at $950,000. Given the address, the price point, and the depth of demand in the Winter Park luxury market, we expect this home to generate significant qualified interest quickly.
Private showings are available by appointment. All buyers are pre-qualified prior to scheduling, in respect of the seller’s time and privacy.
📞 407.622.1111 🌐 www.CreeganGroup.com 📍 439 Lake Howell Road, Maitland, FL 32751
Ask for the Creegan Group listing team for 250 Cortland Avenue.
Listing information reflects MLS data as of the date of this post. All property details, square footage, and specifications are believed accurate but are not warranted. Buyers are encouraged to independently verify all information. Creegan Group is the listing brokerage for 250 Cortland Avenue, Winter Park, FL 32789.