Under Contract in 16 Days — How Creegan Group Succeeded after taking over a listing that expired after 8 months at 1560 Woodland Avenue, Winter Park
Creegan Group | Winter Park Luxury Specialists | 1560 Woodland Avenue, Winter Park, FL 32789 | $1,850,000
Eight months is a long time to wait for a sale that didn’t happen.
The owners of 1560 Woodland Avenue, Winter Park, FL 32789 had been through that experience — a property that sat on the market under another brokerage for the better part of a year, accumulating days, generating questions, and delivering no sale. A home in one of Winter Park’s most established and desirable luxury neighborhoods, priced at $1,850,000, with five bedrooms, a pool, a spa, and a brick-paved address that places it within minutes of Park Avenue — and it never found a buyer.
Then they called Creegan Group.
Sixteen days later, it was under contract.
That is not luck. That is not a coincidence of timing. It is the direct result of what happens when the right brokerage — with the right marketing infrastructure, the right buyer network, and the right understanding of what the Winter Park luxury market demands — takes over a listing and executes with precision.
This is that story.
The Property — 1560 Woodland Avenue, Comstock Park, Winter Park
1560 Woodland Avenue sits in Comstock Park, one of Winter Park’s most historically significant and prestigious residential neighborhoods — a community anchored by grand estates dating to the 1880s, defined by camphor tree-lined streets, and recognized among the top 15% highest-income residential neighborhoods in the entire United States.
Comstock Park’s position off Bonita Drive places it at the true heart of Winter Park — a short drive from Park Avenue’s boutique retail and dining, Rollins College, the Winter Park Farmers Market, the Winter Park Racquet Club, and the lakefront lifestyle that defines the 32789 zip code. This is not a peripheral luxury address. It is the genuine interior of Winter Park’s most coveted residential fabric.
The home itself is a 3,851-square-foot, two-story residence built in 1990 on an 11,761-square-foot lot — positioned on a picturesque brick-paved street that communicates the neighborhood’s permanence and character the moment you turn onto it. A spacious circular driveway announces the property before you step inside. From there, the home delivers on every expectation its address sets:
- 5 bedrooms and 4.5 bathrooms — a floor plan that serves families, executives, and buyers with lifestyle flexibility requirements
- Functional split floor plan — thoughtfully designed to provide both connected living spaces and private retreats within the same footprint
- Pool and spa — the resort-style outdoor living that Winter Park buyers at this price point consider essential, not optional
- Separate in-law suite with private entrance — a genuinely rare feature at this price point, offering flexibility for multigenerational living, a private home office, a guest suite with true independence, or a professional workspace that does not intrude on the home’s main living experience
- Brick-paved street, circular driveway, established landscaping — the curb presence and neighborhood character that frame a home’s first impression
At $1,850,000, this is a property positioned at the intersection of Winter Park’s core luxury market and genuine lifestyle value — the kind of home that attracts a broad, qualified buyer pool from the dual-income professional family to the downsizing estate buyer seeking quality over square footage to the relocating executive who wants to be inside Winter Park proper from day one.
Eight Months Listed — and No Contract. Why?
Before addressing how Creegan Group solved this problem, it is worth being honest about why the problem existed in the first place.
When a well-located property in a strong market sits for eight months without an accepted offer, the cause is almost never the home itself. At $1,850,000 in Comstock Park with a pool, a guest suite, and a brick-paved Winter Park address, this home had every ingredient for a successful sale. The market exists for properties like this. The buyers are out there.
The issue is almost always one of three things — and often a combination of all three.
Presentation. How a home is photographed, videographed, and digitally presented determines the quality and volume of buyer interest it generates in the first critical weeks of a listing. Buyers in the $1.5 million to $2 million range are not casually browsing. They are evaluating multiple properties simultaneously, often from across the country, and they are making showing decisions based almost entirely on the quality of a listing’s digital presentation. Weak photography, no video, no virtual tour — these are not minor gaps. They are the primary reason qualified buyers pass over properties they should be scheduling to see.
Marketing reach. Listing a property on the MLS and Zillow is necessary but insufficient in the current luxury market. The buyer for 1560 Woodland Avenue might be a local move-up buyer — but they might just as easily be a relocating professional from Chicago, a New York buyer transitioning to Florida, or a current Florida resident upgrading from another market. Reaching all of these buyer profiles requires a national and international digital advertising presence — Google, Meta, programmatic networks, retargeting — not just an MLS entry.
Buyer pipeline access. The most qualified buyers in the Winter Park luxury market are not all browsing public listings. Many of them are connected to specific agents who know their criteria and actively source properties on their behalf. If a listing does not reach those agents — through professional relationships, network marketing, and the kind of brokerage-to-brokerage communication that happens at the professional level — it is invisible to a meaningful segment of the most qualified buyer pool.
Eight months on the market under a different brokerage meant that potentially one or more of these elements was missing. When Creegan Group took the listing, we addressed all three.
What Creegan Group Did Differently in 16 Days
We Relaunched the Property — Not Just Re-Listed It
There is a meaningful difference between re-listing a property and relaunching it. Re-listing means updating the listing date and hoping for different results. Relaunching means treating the property as if it were coming to market for the first time — with a fresh marketing strategy, fresh presentation assets, and a clear plan for reaching the buyers who had not yet seen it.
That is exactly what Creegan Group executed for 1560 Woodland Avenue.
New professional photography — capturing the home’s architectural character, its outdoor living spaces, the pool and spa, and the brick-paved streetscape that frames its curb appeal.
Cinematic video — a professional, narrative-driven property film that communicated the lifestyle the home offers rather than simply walking through its rooms.
Interactive virtual tour — giving the out-of-state and remote buyers who are a significant segment of Winter Park’s buyer pool the ability to experience the home completely before scheduling a showing.
Dedicated property website — a standalone digital presence built around this specific home, shareable across every platform and designed to capture buyer interest and convert it to showing requests.
Zillow Showcase placement — elevated Zillow display generating significantly more buyer impressions than a standard listing — backed by Creegan Group’s 1,000+ reviews, Premier Agent designation, and Top Agent recognition on the platform.
We Put It in Front of the Right Buyers — Immediately
Creegan Group’s buyer pipeline is unlike anything else in the Winter Park market. On the day the listing launched, it was introduced to:
- Our active database of qualified buyers who had expressed interest in Winter Park luxury properties in the $1.5 million to $2 million range
- Our 600+ monthly incoming leads — buyers arriving through Zillow Flex, HomeLight Elite, Dave Ramsey ELP, and our corporate relocation network — who match the profile of a 1560 Woodland Avenue buyer
- Our national and international digital advertising campaigns, which put the property in front of qualified buyers by income, location, behavioral data, and search intent across Google, Meta, and programmatic networks
- Our professional agent network — the relationships with buyer’s agents in Winter Park and in the feeder markets (New York, Chicago, Miami, Atlanta) whose clients are actively targeting a Winter Park purchase
By the time a buyer found 1560 Woodland Avenue on Zillow organically, it had already been presented to hundreds of qualified buyers through channels that most brokerages do not have access to.
We Leveraged Our Winter Park Market Position
Creegan Group is not a brokerage that occasionally sells in Winter Park. We are Winter Park’s luxury specialists — a brokerage whose leadership lives in the city’s most exclusive residential corridor, whose agents are embedded in the community’s professional and social fabric, and whose transaction record at the top of the market is among the strongest of any brokerage operating in this zip code.
That market position matters when re-launching a property that has accumulated days. Buyers and their agents pay attention to which brokerage is representing a listing — and when Creegan Group’s name goes on a property in Winter Park, it signals something specific: that this listing is being handled with a level of professional intention and marketing infrastructure that demands attention.
Sixteen days after we took the listing — 1560 Woodland Avenue was under contract at $1,850,000.
The Comstock Park Advantage — Why This Neighborhood Holds Its Value
For buyers unfamiliar with Winter Park’s residential geography, Comstock Park deserves specific attention as one of the most durably valuable neighborhoods in the market.
The neighborhood’s history is part of what makes it exceptional. Bonita Drive — the corridor that anchors Comstock Park — was originally a camphor tree-lined alley leading to “Eastbank,” the three-story Queen Anne estate constructed in 1883 by William C. Comstock, a Chicago businessman whose vision helped shape early Winter Park’s character. The Comstock-Harris House at 724 Bonita Drive remains one of the most historically significant residential structures in the city.
That legacy of permanence is embedded in Comstock Park’s residential character today. The neighborhood is home to some of Winter Park’s most established families — executives, professionals, business owners, and civic leaders who have chosen this specific location because of its combination of walkability to Park Avenue and Rollins College, its established street trees and neighborhood aesthetic, its proximity to the Winter Park Chain of Lakes, and the genuine community character that newer developments cannot replicate.
Demographically, Comstock Park ranks among the top 15% of highest-income neighborhoods in the United States — with more than 80% of its working residents employed in executive, management, and professional occupations. More than 96% of American neighborhoods have fewer large 4-to-5+ bedroom homes as a share of their residential stock. This is a neighborhood built for buyers who want a specific and significant quality of life — and who are prepared to invest in it.
For sellers in Comstock Park, this demographic reality translates into consistent buyer demand from the most qualified buyer profiles in the market. For buyers, it means purchasing into a neighborhood whose long-term value is anchored by exactly the kind of community it has always been.
The Broader Winter Park Market — Why Now Is the Right Moment
The pending sale of 1560 Woodland Avenue at $1,850,000 reflects a Winter Park luxury market that is performing with exactly the strength and selectivity that makes it one of the most compelling residential investment environments in Florida.
Winter Park’s median home price of approximately $619,000 understates the community’s luxury ceiling, which extends well above $10 million in The Vias and lakefront estate corridor. The market is not monolithic — it rewards properties that are presented and marketed correctly, and it punishes those that are not. The 8-month-then-16-days story of 1560 Woodland Avenue is a case study in exactly this reality.
Buyers in today’s Winter Park market are sophisticated. They have access to more information than ever before — market data, listing history, price reduction history, days on market — and they use it. A property that has sat for eight months has a stigma that accumulates over time. Breaking through that stigma requires more than a new listing date. It requires a fresh strategy, a genuine marketing relaunch, and the brokerage credibility to signal to the buyer community that something different is happening.
That is what Creegan Group provides — and that is what we delivered for the sellers of 1560 Woodland Avenue.
If Your Winter Park Home Has Been Sitting — Or If You Haven’t Listed Yet
The story of 1560 Woodland Avenue is not unusual in our experience. Creegan Group has successfully re-launched and sold properties across Winter Park, Maitland, and the greater Central Florida luxury market that had languished under previous representation — often achieving contracts within weeks of taking over listings that had accumulated months of market time.
If your home has been listed without results, we would welcome an honest conversation about why — and what a Creegan Group relaunch would look like for your specific property.
If your home has not yet been listed, and you are considering selling in the Winter Park or Maitland luxury market, the story of 1560 Woodland Avenue makes a clear case for why your choice of brokerage is the single most consequential decision in your sale process.
We are Winter Park’s luxury specialists. Not by title — by transaction record, by community presence, by the buyer network we have built, and by the results we produce for our clients. Results like 16 days to contract on a home that another brokerage could not sell in 8 months.
📞 407.622.1111 🌐 www.CreeganGroup.com 📍 439 Lake Howell Road, Maitland, FL 32751
Contact us for a confidential consultation on your Winter Park or Maitland property.
Transaction details reflect publicly available MLS data as of the date of this post. Market statistics sourced from ORRA, Florida Realtors, and MLS-based data as of March 2026. All statistics subject to change. Prior listing history referenced is publicly available MLS data.