How to Find the Best Real Estate Agent in Highland Lakes, Leesburg
In Highland Lakes, recent sales run a median of about $251,000 ($162/sq ft), typically closing in about 87 days — so accurate local pricing and comparable-sales knowledge are what separate a strong Highland Lakes agent from an average one.
Highland Lakes recorded 58 closings in the last 12 months at a median of $251,000, averaging 87 days on market — the numbers any agent you interview here should already know. This guide covers what makes a great Highland Lakes real estate agent, the questions to ask before you hire, the current Highland Lakes market in detail, and how to connect with a proven local expert. See the Highland Lakes neighborhood guide for homes and lifestyle.
What makes a great real estate agent in Highland Lakes
The best Highland Lakes agents share four things: local sales experience (they’ve actually closed deals here), pricing accuracy built on real comps, marketing that reaches the right buyers, and negotiation that protects your money. In Highland Lakes, homes can take time to sell (a median of 87 days on market), so marketing reach and negotiation make the difference.
That local nuance is why a Highland Lakes specialist beats a generalist: they know the streets, the HOAs, the school zones, and what buyers here will and won’t pay for.
Recent market activity in Highland Lakes
A great agent works from data, not guesswork. Here’s the current snapshot for Highland Lakes (from Momentum’s MLS data, as of 2026-08-30):
Market read: Balanced Market. Use these numbers to pressure-test any agent you interview — a true local will know them cold.
Recent sales in Highland Lakes
Real homes recently closed in Highland Lakes — the kind of comps a great local agent prices from:
| Address | Details | Sold |
|---|---|---|
| 26010 Newcombe Circle | 3 bd / 2 ba · 1,903 sqft · closed 2026-08-27 | $290,000 |
| 5636 Laver Street | 2 bd / 2 ba · 1,497 sqft · closed 2026-08-25 | $252,400 |
| 42039 Cherry Avenue | 3 bd / 2 ba · 1,398 sqft · closed 2026-07-30 | $255,000 |
| 42051 Cherry Avenue | 3 bd / 2 ba · 1,398 sqft · closed 2026-07-26 | $250,000 |
| 25948 Newcombe Circle | 3 bd / 2 ba · 1,388 sqft · closed 2026-07-21 | $245,000 |
| 5506 Rosewall Circle | 2 bd / 2 ba · 1,120 sqft · closed 2026-07-10 | $195,000 |
Listings courtesy of Stellar MLS as distributed by MLS GRID. Recent closed sales shown for market context.
Where Highland Lakes sales actually landed, 2024–2026
Of the 117 recorded Highland Lakes closings since 2024, half landed between $230,000 and $280,000 (the middle two quartiles); the lowest recorded sale was $32,970 and the highest $347,500. If your home sits outside the middle band, the reason usually shows up in the size table below before it shows up in condition.
| Sold price band | Share of closings | Sales |
|---|---|---|
| Under $200,000 | 11 (9%) | |
| $200,000 – $233,333 | 20 (17%) | |
| $233,333 – $266,667 | 40 (34%) | |
| $266,667 – $300,000 | 31 (26%) | |
| None and up | 15 (13%) |
What homes of your size have sold for in Highland Lakes
The same recorded closings, split into thirds by living area. Find the row your home falls in: the $/sqft figure times your square footage is the recorded-sales bracket for homes like yours here — a starting range from real closings, not a valuation of your specific property. Smaller homes here have been selling at a higher price per square foot than larger ones ($187 vs $142) — the usual pattern, since lot, kitchen and baths do not scale with floor area.
| Size group | Median $/sqft | Median sold | Sold range | Sales |
|---|---|---|---|---|
| Smaller homes 672–1,347 sq ft | $187 | $217,000 | $43,100 – $290,000 | 39 |
| Mid-size homes 1,360–1,660 sq ft | $169 | $260,000 | $32,970 – $314,000 | 39 |
| Larger homes 1,692–2,498 sq ft | $142 | $285,000 | $230,000 – $347,500 | 39 |
How Highland Lakes compares to its neighbors
Pricing a home means knowing the alternatives buyers are weighing. The five nearest tracked communities, side by side:
| Community | Median | $/sq ft | DOM | Momentum Score |
|---|---|---|---|---|
| Highland Lakes | $251,000 | $162 | 87 d | 66 |
| HIGHLAND LAKES SUB | $285,000 | $149 | 44 d | 60 |
| LEGACY OF LEESBURG | $304,000 | $171 | 102 d | 64 |
| LEGACY/LEESBURG UN #7 | $288,000 | $193 | – | 50 |
| WINDSONG AT LEESBURG | $342,000 | $163 | 58 d | 53 |
| LEGACY LEESBURG | $310,000 | $172 | – | 58 |
Momentum Score is Momentum Realty’s proprietary 0-100 community market rating. Figures from Momentum’s MLS data, as of 2026-08-30.
What is on the market in Highland Lakes right now
From the live MLS feed as of 2026-09-03: 14 active listings (plus 3 pending) asking from $215,000 to $374,900, median $289,450; 5 of 14 have been on the market over 60 days (median 22 days so far); the homes listed or recently sold were built between 1990 and 2026 (median 1994), 2 of them new construction; 26 of 29 listed or recently sold homes report an HOA, median $135/mo; 4 of 27 geocoded listed or recently sold homes sit inside a FEMA special flood hazard zone (A/V), which buyers’ lenders will price into insurance; median elevation 91 ft; the features listings here most often name are Clubhouse, Pool, Fitness Center, Tennis Court(s), Gated and Deed Restrictions. For a seller this is the competition a buyer will tour alongside your home; for a buyer, the stale share is where negotiating room usually is. See the current Highland Lakes listings →
Which way this market is moving
Active inventory across Lake County has held roughly flat over the past year (-1%). About 30% of county listings currently carry a price cut, which tells you how much negotiating room the average seller has already conceded. Highland Lakes itself has appreciated about 0% over the period Momentum’s MLS data tracks — a community-level trend, not the county average. A strong local agent will reconcile these numbers with what is happening on your exact street before recommending a price.
What it costs to own in Highland Lakes
On a median-priced Highland Lakes home ($251,000), property taxes at Lake County’s typical millage of 16.6465 run roughly $3,346 a year with the homestead exemption applied — before any CDD or special-district charges, which vary by community.
The average Citizens Property Insurance premium in Lake County is about $1,756 a year (April 2026 filings); private-market quotes differ, and a good agent will tell you which carriers are actually writing here.
Run the real numbers before you commit: what selling nets you, whether your Save Our Homes benefit moves with you, and rent vs buy in Lake County.
At Highland Lakes’s $251,000 median and Lake County’s adopted 16.65 mills (FY2025-26), a home assessed at that price carries roughly $4,180 a year in property tax before exemptions, or about $3,510 with the full Florida homestead exemption — a buyer’s first-year figure; a long-time owner’s Save Our Homes cap can be far lower, which is one reason resale taxes jump at closing. Municipal and special-district millage varies inside the county; see the Lake County tax page.
Rents and the investor math
Typical asking rent across Lake County sits near $2,061 a month (Zillow’s rent index). Rents are moving about 1.2% year over year. County-level yield math pencils to roughly a 6.81% cap rate on typical numbers, before expenses. Home prices run about 5.19x the county’s median household income, the affordability backdrop every buyer here negotiates inside. If you are weighing an investment purchase in Highland Lakes, ask your agent for community-level rent comps rather than county averages — the spread between communities is wide.
Who is moving to Lake County, and what they earn
The county gained a net 12,855 people in the latest IRS county-migration year. Households moving IN average $80,711 in income versus $59,346 for those moving out — movers arriving here earn more than those leaving, which shapes what sellers can ask and what buyers compete against. The biggest out-of-state feeder markets are NY, CA, NJ. Median household income in Lake County has grown about 35% since 2018 ($69,956 now). Population is up about 19% over the same stretch. An agent who knows these flows can tell you which way demand in Highland Lakes is actually pointing, not just where prices have been.
Sources: IRS SOI county-to-county migration; U.S. Census income and population estimates. County-level data for context; community demand varies within the county.
School context you can verify: the Lake County school district earned a district grade of A from the Florida Department of Education (2025-26) and has held an A since 2025. Attendance zones vary by address, so confirm the zoned schools for any specific home with the district.
14 for sale · 3 pending — the inventory any agent you interview should already know street by street.
See every 2 listing, with full data ›
Listings courtesy of Stellar MLS as distributed by MLS GRID. Deemed reliable but not guaranteed. Listings shown as of 2026-09-05; prices and availability change.
If you’re buying in Highland Lakes
Come pre-approved, not pre-qualified, and be ready to move within days of a new listing. In a market like Highland Lakes’s, your agent’s job is speed and terms: escalation strategy, appraisal-gap planning, and knowing which contingencies you can safely keep. Ask any agent you interview how their last three Highland Lakes buyers won.
If you’re selling in Highland Lakes
You have leverage, but overpricing still kills momentum — homes that sit past the median days on market start fielding lowball offers. Price at the data, prep properly, and make buyers compete in week one. Your listing agent’s first-week marketing plan matters more than their commission number.
Questions to ask before you hire a Highland Lakes agent
- How many homes have you sold in or near Highland Lakes in the last year — the community recorded 58?
- How would you price my home against the $162 per square foot Highland Lakes closings have averaged — and the size-band table above?
- Homes here have been taking about 87 days to go under contract — what is your plan for the first two weeks?
- With about 2.7 months of supply in Highland Lakes, is this a market where you would advise me to negotiate or hold firm?
- How and how often will you communicate with me?
- Can you share recent client references?
Why community expertise matters in Highland Lakes
Inside Highland Lakes itself, recorded closings have run from $187 per square foot on the smaller homes to $142 on the larger ones — a gap of 31% that a community average hides. An agent who prices from the size table above, not the headline median, is the difference between a home that lingers and one that sells for more, faster.
Top listing agents vs. buyer’s agents in Highland Lakes
If you’re selling in Highland Lakes, a top listing agent’s pricing, staging, and marketing are what win top dollar — the same skills behind a strong home sale. If you’re buying, a sharp buyer’s agent protects you in negotiation and inspections. The best Highland Lakes Realtors do both well; ask any agent you interview which side they’re strongest on and how they’d handle yours.
Meet your local expert
Brittany co-founded Momentum Realty, a RealTrends 500 brokerage (ranked #440 in the U.S.) with 320+ agents and $3.5B+ in closed sales across Florida. Tell her what you’re looking for and she’ll connect you with the right local Momentum specialist — and make sure you’re taken care of from first call to closing.
“I have now worked with Brittany and the Brooks Group / Momentum Realty to both buy and sell a property over the past 3 years. I had an outstanding experience.” — A. Lloyd, Zillow
Related Highland Lakes resources
- Homes for sale & Highland Lakes neighborhood guide
- Lake County real estate market
- Sell your Highland Lakes home with a local expert
- Lake County homestead exemption
Common questions
How do I find the best real estate agent in Highland Lakes?
What questions should I ask a Highland Lakes agent before hiring them?
Does Momentum Realty cover Highland Lakes?
What happens after I ask to be matched?
What is the median home price in Highland Lakes?
Is Highland Lakes a buyer market or a seller market right now?
What should I budget beyond the mortgage in Highland Lakes?
What do homes of my size sell for in Highland Lakes?
Is Highland Lakes in a flood zone?
Does Highland Lakes have an HOA, and how much is it?
How much are property taxes in Highland Lakes?
Market figures are aggregates from Momentum Realty’s MLS data for Highland Lakes, as of 2026-08-30, and will change over time. This is general guidance on how to choose an agent, not a ranking or endorsement of any individual. Equal Housing Opportunity.