Dommerich Estates, Lake Sybelia, and canal access into the Winter Park chain. Sean or Barb, never a handoff.
The Maitland Story
Maitland is Central Florida's sleeper luxury market -- quietly situated between Winter Park and Altamonte Springs, with lakefront estates that trade at a meaningful discount to their Winter Park equivalents. Lake Sybelia and Lake Catherine properties deliver the same water views, the same privacy, and the same mature tree canopies for meaningfully less. For buyers who know, Maitland is the smart move.
Find your perfect lifestyle
Listings updated
Luxury homes for sale in Maitland are Central Florida's best-kept value play: Dommerich Estates and the Lake Sybelia and Lake Minnehaha streets share canal access into the Winter Park chain at values meaningfully below bordering Winter Park on a per-foot basis. The luxury tier runs from $800,000 renovated mid-century homes to $2 million-plus chain-access lakefront. For buyers who want Winter Park geography, schools adjacency, and water without Via-district pricing, Maitland luxury real estate is the analytical answer.
Water is the reason most buyers look at Maitland. Lake Maitland, Lake Sybelia and Lake Minnehaha are on our Maitland waterfront homes page, and the Maitland canal front guide shows how the canals tie into the Winter Park chain. The few homes at the very top are under Maitland homes over $2 million. Own here already? See how we handle selling a home in Maitland.
Selling an inherited or estate home? See our Orange County probate guide.
Median sold price, price per square foot, market pace, and months of supply for the 10 Central Florida markets we serve, updated monthly from Stellar MLS closed sales. Data through September 2026.
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Median Sold Price, September 2026
Median Price Per Sq Ft
Closed in September
Median Days on Market
List Price vs. Sold Price %
Half of September sales closed at or above this share of the final asking price
Months of Supply
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In September 2026 the median sold price for a single-family home in Maitland was $550,000, with 31 homes closed, 20 median days on market and 97.1% of last list price. Data from Stellar MLS InfoSparks.
Where to Look in Maitland
Relocating with kids? See public, charter, and private schools in Maitland and find what an address is zoned for.
With 60+ combined years in Central Florida, Sean & Barb work with luxury buyers and sellers, physicians relocating to the region, and the attorneys who refer estate and divorce property.
I've had the honor of working with physicians and executives relocating to Central Florida, helping them land quickly and confidently in communities that fit their lives. Honesty, discretion, and a genuine investment in your outcome - every time.
Tell us your timeline and your wish list. We will send you Maitland homes that fit, including ones the portals do not show, and there is no pressure and no obligation.
Thank you. Sean or Barb will be in touch shortly.
