Maitland Real Estate

Maitland’s Quiet, Connected Suburb Beside Winter Park

Older homes, new mixed-use living, lakes, and a true neighborhood feel minutes from Orlando

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Maitland, Florida Overview

So there’s a new Foxtail in Horizon West near my house. Obviously there’s one—there’s—they’re everywhere, right? And so I’m still drinking Starbucks because they still haven’t called me to give me a sponsorship. Wasp—sorry—it was like right near you. Oh they should call me, come on call me. Anyway, it’s my ongoing… On our channel, we’ve been digging into a lot of different areas around Orlando. We’ve done Winter Park, Winter Garden, many of the main spots but there’s a lot of cool pocket cities that support some of these bigger areas. And as pricing goes up, you’re going to want to figure out what your other options are, and so today we’re getting into Maitland, Florida.

Exploring Maitland With a Local

I’m going to actually meet with one of my agent partners who lives in Maitland and talk a little bit about the town. Let’s get into it. So Lindsay, yes—where are we? We’re in Maitland, Florida here at Enzian Theatre. We’re looking at the Eden Bar—super cool place to hang out over the weekend. Actually a few people having lunch right now. Super tranquil but you’re in the middle of a bustling town. So driving around… you ready? Yeah—I didn’t hear it. Okay.

Maitland’s Neighborhood Feel

So driving around, there’s not a ton of chains—this is like this quaint kind of thing, right? Is that what Maitland is all about? Yeah, it’s definitely that neighborhood feel. You’re really close to a lot of the big attractions—only about 20 minutes to downtown, an hour to the beach, maybe 40 minutes to Disney—but it’s super quiet and really comfortable.

Why People Choose Maitland

So why Maitland? Why would people choose to live here? The proximity—minutes from popular areas like Winter Park where people are being priced out—but still within a lot of the top-rated school districts. Close to the highway, beaches, Disney, downtown. Far enough from the hustle and bustle but still convenient.

Resident Experience

So how long have you lived in Maitland? Just about a year and a half. Where were you before that? Winter Park—so just a hop, skip, and a jump away. A lot of people call about Winter Park and then find out the average price is a million dollars and look for alternatives. Maitland offered more house for the money while keeping access to the same shops, restaurants, and lifestyle.

There’s a lot of new construction, rentals, and demand—one community is right off the SunRail station, perfect for young professionals commuting downtown.

HOAs, Taxes, and Affordability

HOAs in Maitland? A lot of communities have super affordable, low HOAs. Lindsay’s community is $30 a year—just neighbors looking out for each other and planning events. Affordability comes from lower home prices, low HOAs, and in Seminole County, lower taxes.

Schools in Maitland

Schools can be confusing because Maitland covers both Orange and Seminole counties. City of Maitland is Orange County, so you get Winter Park schools. Some neighborhoods fall into Seminole. There are also many private options including Jewish Community Center programs and Orangewood Christian Academy.

Real Estate Options

Maitland offers primarily single-family homes, established townhomes, condos, and lots of rentals. New developments bring that live-work vibe with shops below and residences above. Most single-family homes are older—60s and 70s ranches with character—which many people love. Compared to Winter Park, Maitland offers similar styles but more affordability, more land, and more recent renovations for the same price point.

Winter Park mid-century ranches start in the upper $300s, while Maitland may offer similar homes already updated. High-end properties run $1–2 million depending on lakefront. Prices are rising—it’s a desirable area.

Lifestyle and Things to Do

Maitland is all about the outdoors—lakes, biking, walking paths like Lake Lily where families gather. Farmers market every week, art festivals with contemporary pieces, jewelry, and more. It’s peaceful and community-oriented.

Independence Square & Community Events

Independence Square is new in the last few years. They shut it down for street fairs and events with string lights—super cute. It’s a great community space with residences nearby and tons of restaurants. You can bring food, hang out, enjoy the park, and embrace the outdoor lifestyle. “I’m crossing the road now—how many chickens crossed?”

Wrapping Up

Thanks for taking me around your town. If somebody wants to get a hold of you to buy a house in Maitland or surrounding areas, how do they get ahold of you? “They can email me at lindsay@poseygroup.com.” Make sure you hit the subscribe button as we put out multiple videos every week about life in Central Florida. See you in the next video.

Maitland

Maitland sits just north of Downtown Orlando and directly beside Winter Park, offering a quieter, more neighborhood-focused alternative to its pricier neighbor. Residents highlight Maitland’s convenience—roughly 20 minutes to Downtown Orlando, about 40 minutes to Disney, and easy access to the beach and major highways. That proximity, combined with a calmer pace and strong school access across Orange and Seminole counties, makes it a consistent favorite for buyers wanting “close to everything” without being in the middle of it.

The housing mix spans mid-century ranches on established streets, older single-family homes with character, renovated properties from the past decade, and newer mixed-use developments offering live-work convenience near SunRail. Maitland’s charm shows through its walkable pockets: Lake Lily Park, local restaurants, the Enzian Theater, and new community squares with string-lit evenings and seasonal events. Outdoor living, bike paths, low HOA fees, nearby lakes, and neighborhood festivals all reinforce a lifestyle that feels grounded and community-driven. For buyers priced out of Winter Park or those wanting more house and land for the budget, Maitland is one of the most compelling options in the Orlando metro.

Real Estate Statistics

Average Price	$548K
Lowest Price	$1.2K
Highest Price	$11M
Total Listings	178
Avg. Days On Market	92
Avg. Price/SQFT	$231

Property Types (active listings)

Winter Garden Highlights

01
Minutes from Winter Park and Downtown Orlando but tucked away from the bustle.
02
Strong mix of older ranch homes, established communities, and newer mixed-use living.
03
Lakes, walking paths, and outdoor-centric lifestyle anchored around Lake Lily.
04
Low-fee HOAs and lower taxes in parts of Seminole County.
05
SunRail access, quick highway connections, and fast commutes to Orlando employers.urs.
06
Established charm with art festivals, local restaurants, and a growing downtown square.

Quick Facts

Price range: Older ranch homes often from ~$450K–$600K depending on updates; larger renovated homes and lake-adjacent options typically $700K–$1M+; premium or lakefront properties can reach $1M–$2M+
Home types: Established single-family, townhomes, mixed-use residences, older ranch homes
Commute: ~20 minutes to Downtown Orlando; ~40 minutes to Disney; ~1 hour to the beach
Schools: District-served; verify zoning (Orange + Seminole coverage varies by address)

Explore Maitland Homes

Browse the newest Maitland homes—from renovated mid-century ranches to newer mixed-use residences near SunRail. Create a Save Search to get instant alerts when matching homes hit the market.

Properties in Maitland

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$10,950,000

↓ $1,000,000

1640 East Adams Drive, MAITLAND

5 Beds 8 Baths 8,174 SqFt Residential MLS® # O6304588

$4,999,000

360 Lake Seminary Circle, MAITLAND

5 Beds 8 Baths 6,466 SqFt Residential MLS® # O6362152

$3,990,900

1250 North Maitland Avenue, MAITLAND

0 Beds 0 Baths 0 SqFt Land MLS® # O6222186

$3,900,000

1770 East Adams Drive, MAITLAND

0 Beds 0 Baths 0 SqFt Land MLS® # O6313981

$2,995,000

$1,975,000

631 Lake Catherine Drive, MAITLAND

3 Beds 3 Baths 2,351 SqFt Residential MLS® # O6366479

New

$1,799,000

105 Tangelo Court, MAITLAND

5 Beds 5 Baths 3,203 SqFt Residential MLS® # O6364116

$1,700,000

↓ $100,000

255 West George Avenue, MAITLAND

5 Beds 4 Baths 4,814 SqFt Residential MLS® # O6275397

$1,485,000

123 Hollie Court, MAITLAND

3 Beds 3 Baths 2,004 SqFt Residential MLS® # O6357907

$1,419,000

↓ $76,500

755 Cranes Court, MAITLAND

5 Beds 5 Baths 4,566 SqFt Residential MLS® # O6299581

View All 174 Results

Winter Park

Nearby Communities

Winter Garden Real Estate FAQs

How does St. Cloud differ from Lake Nona, Kissimmee, and Harmony for lifestyle?

St. Cloud offers a quieter, more traditional suburban feel than Lake Nona’s high-density, master-planned growth. It has more land, more space between communities, and a notably calmer pace, especially outside the Narcoossee corridor. Compared to Kissimmee, St. Cloud feels less tourism-driven and more residential. Harmony is more intentionally master-planned and HOA-structured, while St. Cloud blends historic core, lakeside living, rural pockets, and fast-growing new construction along 192 and Narcoossee.

What are the biggest differences between the three major St. Cloud sub-areas—Historic Downtown, Narcoossee Corridor, and East St. Cloud?

Historic Downtown St. Cloud: 1930s–1960s homes, established streets, oak canopy, walkability to lakeside parks and local shops. Pride-of-ownership neighborhoods and unique architecture.
Narcoossee Corridor: Fastest-growing section; newer construction, townhomes, modern single-family, and the closest access to Lake Nona and Medical City. Higher pricing and demand.
East St. Cloud / 192 Corridor: Larger land parcels, new-construction communities, acreage, and quieter rural-feeling pockets; more space and lower prices than Narcoossee.

What should buyers know about St. Cloud’s older homes vs. new construction?

Historic homes near downtown can offer charm, larger lots, and renovation potential, but may require updates to roofs, windows, plumbing, and electrical. New construction in St. Cloud—especially near Narcoossee—tends to be more affordable than Lake Nona but may come with CDD fees, smaller lots, and more uniform layouts. St. Cloud is one of the few Orlando suburbs where you can choose between walkable historic character and modern master-planned builds at scale.

How competitive is St. Cloud’s resale market?

It depends on the area. Homes in the Narcoossee corridor—especially those under 10–12 years old—move quickly due to Lake Nona proximity and Medical City job access. Renovated homes near downtown St. Cloud also sell fast because of lot size and lakeside lifestyle. East St. Cloud has more inventory and larger neighborhoods, giving buyers more room to negotiate.

How does the commute from St. Cloud compare to Lake Nona or Kissimmee?

Narcoossee-based communities can reach Lake Nona Medical City in 10–15 minutes and MCO in ~25 minutes. Historic St. Cloud and East St. Cloud are farther out and see more congestion on 192 but offer more space and lower pricing. St. Cloud residents working in Lake Nona find the commute far more predictable than I-4 or 417–dependent corridors elsewhere.

What is the lakeside lifestyle like in St. Cloud?

St. Cloud is one of the only Orlando-area suburbs with a true lakeside downtown. Lakefront Park offers walking paths, boat ramps, fishing piers, beaches, and sunset views. It's a unique lifestyle draw—especially for buyers who like boating and want water access without Windermere-level pricing.

Are there areas of St. Cloud with larger lots or semi-rural living?

Yes. East St. Cloud and parts of Hickory Tree Road offer half-acre to multi-acre parcels, horse-friendly zoning in some pockets, and custom homes. These areas appeal to buyers priced out of similar land in Lake Nona or the eastern Orange County rural boundary.

What should buyers know about HOAs and CDDs in St. Cloud?

Most historic and older neighborhoods have no HOA. Newer communities—especially along Narcoossee—frequently include both HOAs and CDDs to fund infrastructure. CDD fees here tend to be lower than Lake Nona but higher than East St. Cloud. Always compare total monthly cost when choosing between older vs. new-build areas.

What types of new construction are available, and how do builders differ?

St. Cloud has a wide builder mix: Lennar, DR Horton, Dream Finders, Pulte, LandSea, and Taylor Morrison all have a footprint. Lennar tends to offer move-in-ready packages; Pulte and Taylor Morrison provide more design flexibility; Dream Finders delivers competitive pricing; and LandSea brings more modern elevations. Narcoossee communities command higher premiums due to Lake Nona access.

Who is St. Cloud the best fit for?

Buyers who want newer construction without Lake Nona prices, families wanting space and strong community feel, commuters heading to Medical City or the airport, lovers of lakeside recreation, and those wanting a mix of suburban + small-town charm. St. Cloud strikes a rare balance between affordability, lifestyle, and proximity to growth corridors.

Enzian Theater, a non-profit cinema located in Maitland, Florida

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