Living in Maitland, FL: Who It Fits, and Who Should Look Elsewhere

Maitland's median price is $515,000, and almost no house in Maitland sells for that. A quarter of what closes here is condos at about $236,000, and they pull the headline down to a number that describes neither the condo nor the house. The single-family median is $592,500, and on the Orange County side, where the 1960s lake streets are, it is $725,000. This page starts by separating those, because a buyer who walks in with the portal's number is $200,000 short before the first showing.

Who Maitland Fits, and Who It Doesn't

Strong fit: buyers who want Winter Park's lake neighborhoods and 1960s houses at a price Winter Park no longer offers, because Dommerich Estates and Highland Park Estates closed at $732,000 to $750,000 in about a week against a $625,000 asking median next door; anyone whose commute runs on I-4 or Maitland Boulevard, since the mean commute here is among the shortest of any town on this list; buyers who want the Seminole County schools with a Maitland address, because the Seminole side closed 93 houses at $510,000, $215,000 under the Orange side; and condo buyers who want the zip code without the house price, with 83 closings at $236,000 and the lakefront Moorings at $525,000.

Weaker fit: anyone who wants new construction, because seven new homes closed here in a year and there is no subdivision being built; buyers who want a large modern house, since the median house here was built in 1968 and is about 2,060 square feet, and the ones over $800,000 are mostly the same era; buyers who read the $515,000 median as a house budget, because at that number the choice is a Seminole-side house or an Orange-side condo, not an Orange-side house; and anyone who needs inventory to choose from, because 95 active listings is one of the thinnest markets in this series and the good houses go in a week.

Still deciding between towns? We pulled the closed sales around a $725,000 budget and put Maitland side by side with its neighbors: what $725,000 actually buys in each. Square footage, bedrooms, year built, and how many came with a pool.

Maitland sits across two counties and they price differently, so there are two of these. The Seminole County side runs closer to $500,000: what $500,000 buys on that side.

Where Is Maitland, and What Makes It Different?

Maitland sits directly north of Winter Park on the chain of lakes, split between Orange and Seminole counties, with I-4 and Maitland Boulevard on its west side and 17-92 running through it. The old town is the 1950s and 1960s streets around Lake Maitland, Lake Sybelia and Lake Minnehaha; the north edge past the county line is Seminole and the same era at a lower price. The mean commute is 22.2 minutes, among the shortest on this list, because downtown Orlando is a short run down I-4 and the Maitland Center offices are inside the city. The population grew 8.5 percent since 2019 with almost no new houses built, which is why 95 active listings is all there is.

Maitland Housing Market Snapshot (2026)

Over the last twelve months 353 homes sold in Maitland at a median of $515,000, up 5.1% against the twelve months before. In July 2026, 30 homes closed at a median of $557,450 and the typical one went under contract in 15 days. One month is too small a sample to read a direction from, which is why the twelve-month figure leads here. There are 95 active residential listings as of September 23, 2026, with a median asking price of $484,000, or $267 per square foot.

Best Neighborhoods in Maitland, FL: Communities to Know

Maitland divides by county line first and by product second, and the county line runs through the middle of it.

• The Orange County lake streets: Dommerich Estates, Highland Park Estates and the Lake Maitland and Lake Sybelia shores, the top of the market: Orange-side houses closed at $725,000 and $322 per square foot with a 1967 median build year; Dommerich Estates closed 7 at $750,000 in a median of 7 days and Highland Park Estates 6 at $732,000 in 9, and the 71 sales over $800,000 citywide ran at $988,000
• The Seminole County side: English Estates, Northgate and the streets north of the line, the same era at a lower price: 93 houses at $510,000 and $272 per square foot; English Estates closed 19 at $509,000 to $525,000 and Northgate 8 at $505,000, all in about three weeks, and these carry the Seminole County school assignment
• The 1990s and 2000s pockets: Winfield, the Enclave at Maitland and Druid Hills Park, the small newer-build slice: Winfield closed 9 at $415,000, the Enclave townhomes 10 at $437,500, and Druid Hills Park 7 at $385,000, which is where a buyer under $450,000 finds a house here
• The condos, a quarter of the market: 83 closings at $236,000 in 44 days; Lake Maitland Terrace at $245,000 on 816 square feet, the Visconti buildings at $194,500 to $220,000, and the lakefront Moorings on Lake Maitland at $525,000, the most expensive square footage in the city at $412 per foot

Know which county the address is in before you look at the price. The same 1965 house is worth about $215,000 more south of the line than north of it, and the schools change with it.

The 15 communities in Maitland where the most homes have sold over the last twelve months, each with its own page:

• English Estates
• Visconti East
• Winfield
• Druid Hills Park
• Maitland Grove
• Northgate
• Visconti West
• Carrington Park A Condo
• Dommerich Hills
• Dommerich Hills
• Dommerich Woods
• Oakland Shores
• English Woods
• Hollieanna Shores
• Brittany Gardens

Another 82 Maitland communities have their own page too. You can also browse every Maitland listing in one place.

Maitland vs. Winter Park vs. Longwood: The Honest Comparison

Winter Park is the reference point for everything here: a higher asking median, a higher price per square foot, and the downtown Maitland does not have, and the Orange-side lake streets are the closest thing to Winter Park a buyer can get without paying for the name. Longwood is the other direction, further up I-4 with a lower asking median, a lower income and a longer commute. Maitland is the one of the three with the shortest commute and the thinnest inventory.

Schools, Commute, and Day-to-Day Life

Orange County Public Schools (Seminole County Public Schools on the Seminole side) serves the city, and assignment varies by address rather than by city name, so confirm the zoning for the specific property before you buy on a school reputation.

Mean travel time to work is 22.2 minutes, against 23.8 from Winter Park.

Is Maitland, FL Safe?

Maitland's reported violent crime rate is 238.2 per 100,000 residents against 280.8 for Florida as a whole, about 15% below the state figure. That is a real difference and it is one of the things buyers here are paying for. The same caveat applies in reverse though: rates are measured against resident population, so a town that few people commute into will tend to look better than a comparable one that they do.

For someone living in a residential neighborhood here, the practical picture is the one common to most of Central Florida: vehicle break-ins and package theft rather than violence. The habits that matter are locking the car and closing the garage.

Figures are reported offenses from the FBI Crime Data Explorer for the Maitland Police Department (ORI FL0480200), 2023, the most recent year that agency reported in a usable form. Reporting years differ between agencies, so this is compared to the Florida rate for the same year and is not comparable to another town's page.

Cost of Living in Maitland, FL

Housing is the line that moves a Central Florida budget. Maitland's median asking price is $484,000 against a median household income of $93,318, which puts a home at about 5.19 times household income here. That ratio, rather than the sticker price, is the number worth carrying between towns, and it is why a cheaper town is not automatically a more affordable one.

Florida charges no state income tax, so the property tax line matters more here than it would elsewhere, and a homestead exemption reduces the taxable value of a primary residence. Millage varies by taxing district, so treat any single quoted rate as an estimate until the specific parcel is checked.

Frequently Asked Questions

Is Maitland, FL a good place to live?

It depends on whether your income comes with you. The median asking price is $484,000 and the mean commute is 22.2 minutes, both favorable, but the median household income here is $93,318, which puts housing at 5.19 times income. For remote workers and retirees that trade is strong. For someone competing in the local job market it is tighter than the sticker price suggests.

What is the median home price in Maitland, FL?

The median sale price was $557,450 in July 2026 across 30 closed sales. Over the last twelve months 353 homes sold at a median of $515,000, up 5.1% against the twelve months before. The median asking price across 95 active listings is $484,000, or $267 per square foot.

Is Maitland cheaper than Winter Park?

On the asking median, yes: $484,000 against $625,000. Measured against household income, Maitland is at 5.19 times income and Winter Park at 6.37, so on that basis Maitland is the more affordable of the two. See what $725,000 buys in each town.

Is Maitland, FL safe?

The reported violent crime rate runs about 15% below the Florida average, though city rates are measured against resident population while the offense count includes everyone passing through. For residents, the realistic risk is vehicle and package theft rather than violence.

What is the cost of living in Maitland, FL?

Housing is the deciding line. A median asking price of $484,000 against a median household income of $93,318 puts a home at roughly 5.19 times income, and Florida charges no state income tax, which shifts weight onto the property tax line.

What school district serves Maitland, FL?

Orange County Public Schools (Seminole County Public Schools on the Seminole side). Assignment varies by address within the city, so confirm the zoning for the specific property.

Thinking About a Move to Maitland?

I work these four counties every week and I will tell you when a town is wrong for you. If you want the numbers for your budget before you tour anything, start with what $725,000 buys across Maitland and its neighbors, or call me at 407-616-9019.

You can also browse homes for sale in Maitland, which updates with current inventory.