Highland Crest
Homes for Sale in Sarasota, FL
All 2,388 homes for sale in Sarasota, FL · median $549,900 · Sarasota County homes for sale
True comps, carrying-cost math, and listings before the portals.
Nearby homes for sale
No active listings inside Highland CrestHomes for Sale in Sarasota, FL 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.
As of September 2026, the MLS records 45 closed sales in Highland Crest in Sarasota, FL since 2004, the most recent in December 2025. Recorded prices since 2024 ran from $250,000 to $276,000 (median $250,000), on homes of 1,220 to 1,558 sq ft. Across Sarasota as a whole, 6 homes closed in the last 12 months at a median of $503,500, 57 median days on market, with 28 homes for sale today. At that median and Sarasota County's FY2025-26 rate of 13.48 mills, annual property tax runs about $3,370 ($2,840 with the full homestead exemption).
The market around Highland Crest
Highland Crest is a small community — 70 recorded sales on file, most recently in 2025 — too few for its own price trend. Here is the market around it.
In ZIP 33853, 80 homes are on the market and 24% are under contract — a steady corner of Sarasota.
Across Sarasota County, 4,856 homes are active and 1,589 pending (25% under contract).
Homes here are single family residence.
ZIP and county figures describe the wider market, not Highland Crest specifically. Momentum Research analysis of MLS records.
Schools
- Sarasota County Public Schools
- Verify the zoned schools by address
- Magnet and choice options may be available
- Polk County Public Schools (verify by address) · Public
- Confirm zoned elementary, middle, and high · By address
- Charter and choice options may apply · Choice
Zoned schools reflect the assignments reported on recent Highland Crest listings and can change; always confirm with Sarasota County Public Schools for a specific address.
Buying with schools in mind? We can confirm the exact zoned schools for any Highland Crest address.
The Highland Crest buying strategy.
If we were buying in Highland Crest 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 Crest.
A closer look at the Highland Crest market
The housing stock is 122 homes built between 1923 and 2020, and 55% of parcels are homesteaded — the owner-occupancy proxy in the Florida DOR assessment roll.
The location and the amenities are priced into every listing in Highland Crest. The deal is won or lost on condition, the comps, and the renovation math.
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 Crest 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 Crest sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Highland Crest, 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 Crest home worth?
Get a no-obligation home value based on real comparable sales in Highland Crest, not an automated guess. Tell us about your home and we will personally prepare your numbers and a pricing strategy. No obligation, no spam.
See homes for sale in Highland Crest on the map →
Highland Crest Market Scorecard
Highland Crest is currently a thin data market. Limited supply, a median asking price of n/a.
Go deeper: true cost calculator · affordability calculator.
Live data: Stellar MLS, distributed by MLS GRID, refreshed twice daily. Typical value: Zillow Research. Market metrics only; these describe homes for sale and recent sales, not residents.
Frequently Asked Questions
How many homes are in Highland Crest?
What share of Highland Crest is owner-occupied?
When were the homes in Highland Crest built?
Do cash buyers compete in Highland Crest?
What schools serve Highland Crest?
Who is the best real estate agent for Highland Crest?
How do I find a top Sarasota real estate agent who knows Highland Crest?
Can Momentum Realty connect me with an agent for Highland Crest?
Data sources & freshness
| Live listings | Stellar MLS, refreshed twice daily (last: September 16, 2026) |
| Housing stock & ownership | Florida DOR assessment roll (street-list match (4 streets, ZIP 33853/33859/34232/34239)) |
| Under-contract shares | Stellar MLS records, as of 2026-08-01 |
| Schools | 2025-26 district assignments + FLDOE school grades; verify with the district |
| Historical depth | Closed-sale records back to 2004 (45 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 your area comps.
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More Sarasota & Sarasota County guides
Compare before you commit - every guide covers pricing, HOA/CDD, insurance posture, and fit. Browse all of Sarasota County or the full Neighborhood Finder.
See how Highland Crest fits the bigger picture — live prices, inventory, and Momentum Scores: