- 4 beds
- 3 baths
- 2,033 sqft

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.
Highland Park Estates homes for sale
2 listingsBrowse 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.
| Aspect | 1963 single-story: 2020 Thunderbird Trail | 2017 two-story: 1991 Mohican Trail |
|---|---|---|
| Layout | Single-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 area | 2,069 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 history | Original 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 garage | This 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
2112 Chippewa Trail4 bed · 4 bath · 2,407 sqft
$875,000
Sold Oct 2, 2026
823 Woods Court3 bed · 2 bath · 2,145 sqft
$910,000
Sold Oct 2, 2026
624 Tuscarora Trail5 bed · 3 bath · 3,370 sqft
$932,300
Sold Sep 30, 2026
1511 Glastonberry Road5 bed · 3 bath · 2,376 sqft
$520,000
Sold Sep 9, 2026

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.
Explore more
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