Skip to content
Representative architectural illustration, not an actual property photograph, of single-story and two-story homes amid mature trees, evoking Highland Park Estates in Maitland, Florida.

Maitland, Orange County, Florida

Highland Park Estates homes for sale

Find Highland Park Estates homes for sale. Compare layouts, settings and ownership details to focus your shortlist.

Browse Highland Park Estates homes by price

Choose a budget to explore homes within this area's search boundary.

Highland Park Estates market snapshot

Current homes for sale and median asking price for Highland Park Estates and its First Addition.

For sale now
2
Median asking price
$962,000

An established neighborhood within Maitland

When comparing Highland Park Estates homes for sale, we help you look beyond construction dates in this established detached-home neighborhood in Maitland, Orange County, Florida. Older single-story homes and later-built houses offer different layouts and levels of updating. This search covers the recorded original subdivision and First Addition, separately from Dommerich Hills. Thunderbird Trail and Mohican Trail provide examples of neighborhood addresses, not a complete perimeter or blanket inclusion of either street. For broader lifestyle context, Winter Park is a separate city, where Central Park on Park Avenue offers another destination to consider alongside Maitland's own parks and facilities.

Compare the home, not just its construction year

These neighborhood examples illustrate different home forms, not current availability or features shared by every property.

Aspect1963 single-story: 2020 Thunderbird Trail2017 two-story: 1991 Mohican Trail
LayoutSingle-story living; compare bedroom separation and how the kitchen connects to shared rooms.Two-story living; check bedroom locations and how stairs fit your daily routine.
Living area2,069 square feet of living area; keep conditioned space separate from total building area.4,016 square feet of living area; assess room usefulness, not just the larger footprint.
Renovation historyOriginal age and updating are separate: review documented system replacements and additions.Later construction still warrants a review of maintenance, alterations and current condition.
Outdoor space and garageThis example has a pool; compare remaining yard and garage capacity individually.Check usable yard, parking and any pool separately; a larger house does not establish these features.

Maitland parks and recreation for everyday living

These municipal parks offer recreation beyond your yard. They are public facilities, not subdivision-owned amenities or benefits included with a home purchase.

  • Maitland Community Park

    At 1400 Mayo Avenue, tennis and basketball courts, playgrounds and a half-mile walking trail give you options for exercise and outdoor time.

  • Minnehaha Park

    At 1001 East Horatio Avenue, enjoy four pickleball courts, tennis, a walking path and the Nina Canal boardwalk as part of your recreation routine.

  • Fort Maitland Park

    At 900 South Orlando Avenue, the municipal boat ramp offers public access. Motorized-vessel boat passes and trailer-parking charges are separate.

Compare other local homes

Compare Dommerich Estates homes for sale and Dommerich Hills homes for sale. Compare layouts, documented improvements and usable outdoor space across these distinct Maitland communities. Confirm each home's actual water rights, utility arrangements and ownership obligations rather than transferring assumptions from a nearby neighbourhood.

FAQs: choosing the right Highland Park Estates home

FAQs: ownership, schools and local sales

Recent sales near Highland Park Estates

40 properties sold within half a mile in the last 12 months · median $587,500

Gaby Sadler, Property Specialist

Gaby Sadler

Property Specialist, Serhant

Find Highland Park Estates homes for sale with Gaby

Tell me your priorities and budget. I'll help you compare Highland Park Estates homes for sale, review the details that matter to your shortlist and arrange viewings.

Find the home that fits your Maitland plans

As you explore Highland Park Estates homes for sale, start with the spaces you will use most: bedrooms, shared living areas, garage storage and the yard. Speak with Gaby about comparing layouts, updating and outdoor space across your shortlist. We can help you focus your search on those priorities and identify the property details worth reviewing before you take the next step toward a home in Maitland.

Browse homes for sale