Creegan Group Recognized as the Premier Luxury Real Estate Brokerage Serving Winter Park and Maitland, Florida
FOR IMMEDIATE RELEASE
MAITLAND, FL — March 2026 — Creegan Group, Central Florida’s top-producing real estate brokerage, has cemented its position as the leading luxury real estate firm serving the Winter Park and Maitland markets — two of the most prestigious and consistently in-demand residential communities in the state of Florida. With a resume of closed luxury transactions, significant high-net-worth client relationships, and a deeper footprint in these markets than other competing brokerages, Creegan Group’s recognition as the premier luxury choice in this corridor reflects years of consistent production, investment, and client results at the highest level.
Headquartered at 439 Lake Howell Road in Maitland — directly in the heart of the market it serves — Creegan Group brings a level of local expertise, professional infrastructure, and luxury marketing capability that no out-of-market firm or large national franchise can replicate in this specific corridor.
About the Winter Park and Maitland Luxury Market
Winter Park and Maitland represent the gold standard of residential living in the greater Orlando metro — and among the most coveted addresses in all of Florida.
Winter Park is defined by its brick-lined streets, its collection of nationally recognized boutiques and restaurants along Park Avenue, its acclaimed Rollins College, and its extraordinary lakefront real estate. The Butler Chain of Lakes — interconnected waterways threading through some of Winter Park’s most exclusive neighborhoods — anchors a lakefront real estate market where properties routinely sell between $2 million and $10 million and beyond. The median home price in Winter Park is approximately $619,000, but the community’s luxury ceiling is among the highest in the state. Neighborhoods including Genius Drive, Vía Tuscany, and the streets fringing Lake Maitland and Lake Sue represent some of the most significant residential real estate assets in Central Florida.
Maitland has emerged as the surprise performer of the Central Florida luxury market — appreciating at 11.5% year-over-year as of early 2026, outpacing even Winter Park’s historically strong appreciation curve. With a median home price approaching $542,000, Maitland’s combination of established lakefront estates, proximity to Orlando’s technology and financial services employment corridor, and genuine neighborhood character has attracted an increasingly discerning buyer — one who has often specifically chosen Maitland over Winter Park as a more private, less trafficked, and in many cases more value-accretive alternative.
Together, these two markets form the most concentrated collection of high-net-worth residential real estate in the Central Florida region — and the market where Creegan Group has invested most deeply in building a dominant luxury presence.
Creegan Group’s Luxury Production Record
Creegan Group’s position in the Winter Park and Maitland luxury market is not a claim — it is a production record.
- 77 recently closed sales above $1,000,000 across Central Florida in recent years, with a significant concentration in the Winter Park and Maitland corridor
- 15 recently closed sales above $2,000,000, including multiple transactions in Winter Park’s lakefront neighborhoods
- A recent landmark sale at $5,100,000 — among the most significant residential transactions in the market
- $2 billion+ in total career sales across Central Florida, with Winter Park and Maitland representing the brokerage’s home market
- High per-agent production
- Top 40 Nationwide — RealTrends, the industry’s most widely cited independent production ranking
- 2025 Broker of the Year — Orlando Regional REALTOR® Association, the market’s most prestigious professional recognition
“Winter Park and Maitland are where our roots are and where our commitment runs deepest,” said Chris Creegan, Broker/Owner of Creegan Group. “These are markets that demand more than a license and a lockbox. High-net-worth buyers and sellers expect a professional who understands the nuance of luxury real estate — the right pricing strategy, the right marketing approach, the right network of buyers, and the discretion and professionalism that significant transactions require. That is what Creegan Group delivers in this market every day.”
What Defines Creegan Group’s Luxury Service in This Market
High-Net-Worth Client Network and Off-Market Access
Creegan Group’s standing in the Winter Park and Maitland luxury community is built on years of trusted relationships with the region’s most significant buyers and sellers — executives, physicians, attorneys, entrepreneurs, and investors who have worked with our team on multiple transactions and refer their peers to us specifically because of the results we produce.
This network provides two distinct advantages. First, it gives Creegan Group sellers access to a pre-qualified, discreet audience of buyers for whom privacy is a priority — buyers who prefer to purchase through a trusted professional relationship rather than a public listing process. Second, it gives Creegan Group buyers access to properties that never reach the open market — or that reach it only after our clients have had the opportunity to act.
In a market like Winter Park, where the most significant lakefront estates and private-drive residences are held by owners who value discretion above maximum public exposure, off-market access is not a peripheral benefit — it is often the only path to the most exceptional properties.
Luxury Marketing That Performs at the Highest Level
Creegan Group’s marketing infrastructure is calibrated specifically for luxury real estate — and no local competitor deploys it at a comparable scale.
Zillow Showcase — Creegan Group’s listings appear on Zillow’s premium display format, generating significantly more buyer engagement than standard listings at equivalent price points. Our 1,000+ verified client reviews and Premier Agent designation give our listings the credibility signal that luxury buyers use to evaluate agent quality before they make contact.
Dedicated property websites — Every listing receives a purpose-built digital presence — a standalone property website professionally designed to present the home’s photography, video, floor plan, and neighborhood story at its full potential.
Cinematic video production — Professional, narrative-driven video for every listing, designed to reach buyers who respond to story and lifestyle as much as to specifications.
National and international advertising — AI-powered campaigns across Google, Meta, programmatic networks, and international platforms reaching buyers by income, behavioral data, and intent — including the out-of-state and international buyer pool that is an active and significant presence in the Winter Park and Maitland luxury market.
Retargeting — Buyers who engage with a Creegan Group luxury listing continue to encounter it across their digital experience until they are ready to act — a sustained presence that single-exposure listings cannot replicate.
Private network marketing — Before any public listing, Creegan Group luxury properties are introduced to our curated database of qualified buyers, active investors, relocation clients, and professional agent relationships throughout Central Florida and nationally.
The Luxury Buyer Demographic Creegan Group Serves
The Winter Park and Maitland luxury buyer is not a single profile — and Creegan Group’s reach reflects that diversity.
Corporate relocations — Senior executives and C-suite professionals arriving from major metro markets (New York, Chicago, San Francisco, Boston) who are specifically targeting Winter Park and Maitland as their Florida landing point because of the lifestyle, the schools, and the community character.
Domestic high-net-worth buyers — Investors, entrepreneurs, and professionals already in Florida who are upgrading from other Central Florida markets — from Dr. Phillips, Windermere, or Lake Mary — to the specific lifestyle that Winter Park and Maitland offer.
International buyers — Latin American buyers (particularly from Colombia, Venezuela, Brazil, and Mexico) who have historically viewed Winter Park as one of the most desirable Florida residential addresses; Canadian buyers targeting Central Florida as a primary or secondary residence; and European buyers, particularly from the U.K., Germany, and Scandinavia, who are active in the Florida luxury market.
Estate and legacy transactions — Long-term Winter Park and Maitland homeowners navigating estate sales, downsizing, or the transition of generational properties that require the kind of professional discretion and market expertise that Creegan Group specifically provides.
Creegan Cares and Cash Offer Programs — Unique Advantages for Luxury Sellers
Even in the luxury segment, Creegan Group’s proprietary seller programs provide meaningful differentiation.
The Creegan Cares pre-listing program — through which Creegan Group fronts the cost of pre-listing improvements with no interest and no upfront cost to the seller — is particularly relevant for estate properties where significant preparation can meaningfully impact both speed of sale and final sale price. A $4,500 worth of fresh paint and professional staging on a $2.5 million property can generate a return that vastly outpaces the investment. Creegan Cares removes the friction of that investment entirely.
Creegan Group’s cash offer program — the most robust in Central Florida — is equally available to luxury sellers, including the Buy Before You Sell equity advance program for sellers needing to unlock proceeds for a purchase, and the Sell Now, Maximize Later structure for sellers who want cash certainty combined with potential participation in retail upside.
Creegan Group’s Commitment to the Winter Park and Maitland Community
Creegan Group’s investment in Winter Park and Maitland extends beyond individual transactions. Our team is actively involved in the communities we serve — supporting local organizations, events, and initiatives that reflect our genuine connection to the places where our clients live and raise their families.
This is not a brokerage that opened an office here because the demographics were favorable. Creegan Group’s Maitland headquarters has been the center of our operation since the beginning — and our knowledge of these communities, their neighborhoods, their history, and their trajectory is the product of years of daily presence rather than market research.
“We live here. We work here. We raise families here,” Creegan said. “When we tell a buyer that Maitland is outperforming the metro in appreciation, or that a specific street in Winter Park commands a premium that the comps don’t fully capture, we’re saying that because we’ve closed the transactions that prove it. That’s what local expertise actually means.”
About Creegan Group
Creegan Group is a full-service luxury real estate brokerage headquartered in Maitland, Florida, serving buyers and sellers throughout Central Florida including Orange, Seminole, Lake, Osceola, and Polk counties. The brokerage is led by Chris Creegan, 2025 Broker of the Year (Orlando Regional REALTOR® Association), who is ranked in the Top 40 nationally by RealTrends and has generated more than $2 billion in career sales. Creegan Group’s 50+ full-time agents close more than 500 homes per year and bring in over 600 qualified leads per month through the industry’s most respected platforms — Zillow Premier Agent (Flex), HomeLight Elite, Dave Ramsey Endorsed Local Provider, and national corporate relocation networks. Creegan Group offers exclusive seller programs including Creegan Cares pre-listing preparation and Central Florida’s most comprehensive cash offer program.
For media inquiries or to schedule an interview with Chris Creegan: 📞 407.622.1111 📧 [email protected] 🌐 www.CreeganGroup.com 📍 439 Lake Howell Road, Maitland, FL 32751
Market data sourced from ORRA, Florida Realtors, Zillow, and MLS-based sources as of March 2026. Production figures reflect Creegan Group closed transactions through early 2026. All statistics subject to change.