Under Contract in 16 Days — 1560 Woodland Avenue, Winter Park | $1,850,000 | Creegan Group
Creegan Group | Winter Park Luxury Specialists | 1560 Woodland Avenue, Winter Park, FL 32789 | $1,850,000
1560 Woodland Avenue, Winter Park, FL 32789 went under contract sixteen days after Creegan Group listed it at $1,850,000.
A five-bedroom, four-and-a-half-bathroom home with a pool and spa, situated on an 11,761-square-foot lot on a brick-paved street in Comstock Park — one of Winter Park’s most established and desirable residential neighborhoods, minutes from Park Avenue, Rollins College, and the Winter Park Chain of Lakes.
The story of this listing is the story of what Creegan Group’s Winter Park luxury marketing platform produces when it is deployed at full capacity for a property in a market we know intimately.
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.
How Creegan Group Brought 1560 Woodland Avenue to Contract in 16 Days
A 16-day path from listing to contract on a $1,850,000 home is the product of a marketing and buyer-engagement process executed with precision. Here is what we did for 1560 Woodland Avenue — and what we do for every Winter Park luxury listing we represent.
A Full-Platform Relaunch on Day One
Every Creegan Group Winter Park luxury listing receives a full marketing relaunch on day one — fresh photography, fresh video, fresh digital presentation assets, and a coordinated launch across every channel where the qualified buyer for the property is likely to encounter it.
For 1560 Woodland Avenue, that included:
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 one of the deepest 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 Trusted Pro, 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 complement standard MLS syndication.
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 launching a luxury listing. Buyers and their agents pay attention to which brokerage is representing a property — 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 listed 1560 Woodland Avenue — it 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 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 Via neighborhoods and lakefront estate corridor. The market is not monolithic — it rewards properties that are presented and marketed correctly, and it places a meaningful penalty on properties that are not.
Buyers in today’s Winter Park market are sophisticated. They have access to more information than ever before — market data, listing history, days on market — and they use it. Launching a property correctly the first time matters. That means a clear pricing strategy, a fully developed marketing presentation on day one, and a coordinated rollout to the buyer channels most likely to produce qualified showing activity in the first critical weeks.
That is what Creegan Group provides — and that is what we delivered for the sellers of 1560 Woodland Avenue.
If You Are Considering a Winter Park or Maitland Luxury Sale
If you own a luxury home in Winter Park, Maitland, or Baldwin Park and you are considering a sale, the story of 1560 Woodland Avenue makes a clear case for what’s possible when the right marketing platform meets the right Winter Park property.
We would welcome an honest conversation about your home — what it would realistically achieve in the current market, what a Creegan Group listing process would look like for your specific property, and how the variables that matter most in your micro-market would shape our recommended approach.
We are Winter Park’s luxury specialists — by transaction record, by community presence, by the buyer network we have built, and by the results we produce for our clients.
📞 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. Creegan Group is a licensed Florida real estate brokerage. Past performance is not a guarantee of future results.