Homes for Sale $300K to $500K in Maitland, FL
This page tracks every Maitland listing with an asking price between $300,000 and $500,000, by community, with live counts and asking prices. Prices are asking prices from the MLS, not values, and the list changes with every refresh.
25 homes listed between $300,000 and $500,000 are for sale or pending in Maitland, FL today across 21 communities. The median asking price is $389,900, from $300,000 to $499,900. Listings in Maitland without that feature have a median of $567,500. Most listings right now: Lake Maitland Terrace Apts (4), Moorings On Lake Maitland Condo (2), Forest Brook 4Th Sec (1). Updated October 2, 2026 from the MLS.
Live $300k–$500k homes in Maitland: the listings
14 active listings match today (18% of Maitland inventory), median asking $364,500, $295/sq ft, median 34 days on market. Photo cards link to the listing; refreshed nightly.
Newest $300k–$500k homes in Maitland
The most expensive $300k–$500k homes in Maitland
| Listing | Asking | Sq ft | Community |
|---|---|---|---|
| 2464 Hunterfield Road | $490,000 | 1,920 | — |
| 204 Quayside Circle #201 | $467,000 | 1,270 | Moorings On Lake Maitland Condo |
| 761 Robinhood Drive | $450,000 | 1,154 | Greenwood Gardens |
| 27 N Calhoun Avenue | $440,000 | 1,809 | coopers |
| 1010 Winderley Place #149 | $429,900 | 1,651 | Villas Lake Destiny |
| 1140 S Orlando Avenue #H3 | $389,900 | 816 | Lake Maitland Terrace Apartments |
| 1994 Kenaston Road #1994 | $389,000 | 2,103 | Ultra Vista Condo |
| 1033 Hamlet Drive | $340,000 | 1,146 | Hamlet At Maitland |
| 2362 Sierra Lane | $340,000 | 1,343 | Sierra Condominiums |
| 210 Magnolia Road #207 | $339,000 | 1,013 | Maitland House |
$300K–$500K Homes by price
| Band | For sale | Share |
|---|---|---|
| $300K–$500K | 14 | 100% |
Maitland homes $300K–$500K by community
Click a community for its full guide: prices, HOA reality, insurance posture and the homes for sale.
| Community | Homes $300K–$500K | New build | Median list | From |
|---|---|---|---|---|
| Lake Maitland Terrace Apts | 4 | 0 | $332,500 | $315,000 |
| Moorings On Lake Maitland Condo | 2 | 0 | $421,000 | $375,000 |
| Forest Brook 4Th Sec | 1 | 0 | $499,900 | $499,900 |
| English Estates Unit 2 | 1 | 0 | $490,000 | $490,000 |
| English Estates Unit 3 | 1 | 0 | $475,000 | $475,000 |
| Lakewood Shores | 1 | 0 | $465,000 | $465,000 |
| Floridahaven 1St Add | 1 | 0 | $460,000 | $460,000 |
| Greenwood Gardens Sec 01 | 1 | 0 | $450,000 | $450,000 |
| Coopers Sub | 1 | 1 | $440,000 | $440,000 |
| Winfield | 1 | 0 | $435,000 | $435,000 |
| Villas Lake Destiny | 1 | 0 | $429,900 | $429,900 |
| Enclave/Maitland A-F | 1 | 0 | $405,000 | $405,000 |
| English Woods | 1 | 0 | $394,000 | $394,000 |
| Ultra Vista Condo | 1 | 0 | $389,000 | $389,000 |
| Winfield Ut 1 | 1 | 0 | $370,000 | $370,000 |
| Branch Tree | 1 | 0 | $355,000 | $355,000 |
| Hamlet At Maitland | 1 | 0 | $340,000 | $340,000 |
| Sierra Condo Ph 2 | 1 | 0 | $340,000 | $340,000 |
| Maitland House | 1 | 0 | $339,000 | $339,000 |
| Eaton Estates | 1 | 0 | $335,900 | $335,900 |
| Eatonville Lawrence | 1 | 0 | $300,000 | $300,000 |
Where this band sits in the market
The answer block above shows how the median of this band compares with the rest of the city’s listings, which tells you whether $300,000–$500,000 is the middle of the market here or the top of it. Within the band, compare on price per square foot and year built: newer subdivisions usually price higher per foot with lower expected maintenance, older ones the reverse. Each community page carries the HOA and CDD picture, the year-built range and the sales history, so two homes at the same price can be told apart in a few minutes.
Questions to ask about any listing in this band
What are the total monthly carrying costs (taxes, insurance, HOA, CDD) and how do they compare with a similar home two communities over? What is the age of the roof, HVAC and water heater? Is the community’s HOA financially healthy (reserves, no pending assessment)? How many days has the listing been on the market and has the price moved? A local agent who works the area will know which communities in this band are trading at asking and which are negotiating.
Common questions
How many homes listed between $300,000 and $500,000 are for sale in Maitland?
What do homes $300K–$500K cost in Maitland?
Which Maitland community has the most homes $300K–$500K for sale?
What is the monthly payment on a $400,000 home?
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Homes $300K–$500K in nearby Orange County cities
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Live data: Stellar MLS, refreshed with every MLS pull; this page rebuilds on every ship. Community-level aggregates only: active and pending residential listings in Maitland, FL whose MLS record reports an asking price between $300,000 and $500,000. Prices are asking prices, not values. Property features and prices only; nothing on this page describes residents. Equal Housing Opportunity.