Highland Park Estates
Homes for Sale in Maitland, FL
All 109 homes for sale in Maitland, FL · median $460,000 · 58 homes for sale in 32751 · Orange County homes for sale
True comps, carrying-cost math, and listings before the portals.
As of September 2026, the MLS records 10 closed sales in Highland Park Ests 1St Add in Maitland, FL since 2009, the most recent in October 2021. Across Maitland as a whole, 156 homes closed in the last 12 months at a median of $515,000, 29 median days on market, with 28 homes for sale today. At that median and Orange County's FY2025-26 rate of 16.67 mills, annual property tax runs about $8,590 ($7,910 with the full homestead exemption).

Highland Park Estates Add is a mid-century established pocket in Maitland, with a median build year of 1965 and homes stretching from 1959 to 2016. In a subdivision this age, condition is the price story: two houses on the same street can sit far apart on value depending on whether the systems, roof, and interior have been brought current or left original. Square footage helps — the median home runs about 2,157 living square feet, which is real space to work with — but what actually sets the number is how much updating the next owner has to fund themselves.
With no closings in the current window, there is no fresh sold comp to anchor to, so pricing here leans on condition and older data rather than a hot recent trade. That cuts both ways. A seller with a genuinely renovated home has room to make a case; a buyer should slow down, underwrite the deferred maintenance honestly, and not assume a headline number reflects a turnkey house. The 84.3% homestead share tells you this is a lived-in, owner-occupied block rather than an investor-churned one, which tends to mean tightly held inventory and homes that come to market on the owner's timeline.
Nearby homes for sale
No active listings inside Highland Park Ests 1St Add right now. These are the 6 closest homes on the market, by straight-line distance from the community's center; some may sit just outside its boundary.
Listing data from the MLS feeds named on each listing page; deemed reliable but not guaranteed. Refreshed nightly.
The 60-Second Overview
This is an established Maitland neighborhood of primarily 1960s-era homes on a decent footprint, held mostly by owner-occupants — the kind of place where the value spread comes down to how far each individual house has been updated.
Stellar MLS sales records identify 126 homes in Highland Park Estates that have changed hands since 2004, built between 1960 and 2007 (median 1965), with a median living area of about 2,194 sq ft and a typical 4-bedroom, 2.5-bath layout; 100% are single-family homes. Source: Stellar MLS closed-sale history compiled by Momentum Research; counts reflect homes with a recorded MLS sale, not every home in the community.
Pre-construction details are compiled from public records, builder announcements and builder listings, and are subject to change without notice; figures are deemed reliable but not guaranteed. Momentum Research figures are our own analysis. This page describes homes, pricing and community attributes, not residents.
Who Highland Park Estates is best for.
Best for
- Buyers wanting an established Maitland location with generous living space around the 2,100-square-foot mark
- Renovation-minded buyers who can budget for roof, HVAC, and system updates on an older home
- Long-hold owners comfortable in a low-turnover, owner-occupied neighborhood
Probably not for
- Buyers who need a modern, turnkey home with no deferred maintenance
- Investors looking for quick flips backed by fresh, frequent comps
- Buyers who require a tight, data-heavy valuation before committing
The market around Highland Park Estates
Highland Park Estates is too small for its own price trend, so here is the market around it.
In ZIP 32751, 137 homes are on the market and 35% are under contract — a fast-moving corner of Maitland.
Across Orange County, 5,909 homes are active and 1,877 pending (24% under contract).
In ZIP 32751 (Maitland), 295 homes closed in the last 12 months at a median of $480K ($261/sq ft), down 0.3% year over year, with a median 30 days on market. Right now 31 active and 17 pending listings put supply at about 3.2 months — a healthy market. See the live ZIP 32751 housing market and the Orange County market.
ZIP and county figures describe the wider market, not Highland Park Estates specifically. Momentum Research analysis of MLS records.
The Highland Park Estates buying strategy.
If we were buying in Highland Park Estates today, this is the order of operations we would run for our clients.
Underwrite the condition first. Price the roof, HVAC, and systems honestly before judging any list price; condition swings value here more than square footage alone.
Match the home to real comps. Recent sales of similar condition and lot, not the asking price, tell you what a home is worth.
Move deliberately, not desperately. Neither side has a decisive edge, so a well-prepared, fairly-priced offer wins without overpaying.
Line up financing and inspection early. A pre-approval and an inspection plan let you act fast and negotiate from evidence.
Keep an agent in your corner. The listing agent works for the seller; we represent you and prepare a hand-built valuation before any offer in Highland Park Estates.
A condition-driven mid-century pocket
With 166 homes and a median build year of 1965, this is a small, mature subdivision where the housing stock predates open-plan expectations and modern energy standards. The 1959–2016 range means you'll find original mid-century houses alongside occasional newer infill, so no two listings should be read as interchangeable. Budget your diligence around age: roof, HVAC, plumbing, electrical, and windows are the line items that move the math on a home from this era.
The high homestead share — roughly 84% — signals stability in who holds these homes long-term, which typically translates to lower turnover and fewer distressed sales. For a buyer that means patience: the right house may not be listed the week you start looking. For a seller it means your competition is thin but discerning, and the buyers who show up will price your home against its condition, not just its address.
The location and the amenities are priced into every listing in Highland Park Estates. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
A neighborhood with no recent closings and a wide condition spread is exactly where a generic online estimate fails you. We price from the house in front of us — systems, updates, and true living space — not from a stale average, and we help buyers separate a cosmetically dressed listing from one that's been genuinely brought current. On the sell side, we position a renovated home to stand out in thin, tightly held inventory.
Highland Park Estates in 15 seconds.
HOA, CDD & Fees
- HOA status not on record. Verify any dues before you offer
- Any club/amenity membership is billed separately
Confirm the current HOA dues, exactly what they cover, and any CDD bond or special assessment for a specific address before you offer.
Tools for a Highland Park Estates buy.
Free calculators to pressure-test the real cost before you tour.
Selling here is won on condition and pricing to real comps, not an automated estimate. The right number comes from closed Highland Park Estates sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Highland Park Estates, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Highland Park Estates home worth?
Get a no-obligation home value based on real comparable sales in Highland Park Estates, not an automated guess. Tell us about your home and we will personally prepare your numbers and a pricing strategy. No obligation, no spam.
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Should you buy in Highland Park Estates?
An honest fit check. We will tell you when it is not your community.
Data sources & freshness
| Under-contract shares | Stellar MLS records, as of 2026-09-08 |
| Historical depth | Closed-sale records back to 2009 (10 transactions analyzed) |
Verify the primary sources yourself: Florida DOR · U.S. Census · FEMA flood maps · Citizens Property Insurance.
Momentum Research figures are our own analysis of Stellar MLS records; MLS data is deemed reliable but not guaranteed. Methodology: how Momentum market scores are computed. Market metrics describe homes for sale and recent sales, not residents.
Own a home here?
You just read the data. Now see what your home is worth.
The numbers on this page move markets in the aggregate. The number that matters to you is what a buyer pays for your address. Momentum sells for 1.25% above the Stellar MLS member average and 8 days faster, and we’ll price yours against live local comps.
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Common questions about Highland Park Estates
Where is Highland Park Estates?
Highland Park Estates is a community in Maitland, Orange County, Florida, ZIP 32751.
Are there homes for sale in Highland Park Estates right now?
No active listings inside Highland Park Estates at the last feed refresh. The nearest homes for sale, with distances from the community, are shown on this page and refreshed nightly.
Does Highland Park Estates have an HOA or CDD?
No HOA is on record for Highland Park Estates in our data. Verify dues, what they cover, and any special assessment for a specific address before you offer.
Answers are generated from county property records, MLS feeds and the figures on this page, as of the page date; deemed reliable but not guaranteed.
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