Highland Woods
Homes for Sale in Dunedin, FL
All 286 homes for sale in DUNEDIN, FL · median $414,500 · 226 homes for sale in 34698 · Pinellas County homes for sale
True comps, carrying-cost math, and listings before the portals.
Over the 12 months ending 2026-09-20, 4 recorded sales closed at a median of $854,500, $251 per square foot, a median 11 days on market, sellers accepting 97% of original asking (+0% versus the prior year). Homes listed or recently sold were built 2001 - 2003; 6 of 6 report an HOA (median $99/mo); none of the 6 geocoded homes sit in a FEMA special flood hazard zone (median elevation 62 ft). At the median price and Pinellas County's FY2025-26 rate of 19.39 mills, annual property tax runs about $16,570 ($15,750 with the full homestead exemption).
Highland Woods right now
🟡 Still climbing. The trailing-12-month median ($854K) is up 0.3% from the prior 12 months ($852K). With about 3 sales a year, a single closing can swing this number, so read the level and the decade, not one year's move.Momentum Research, record-level Stellar MLS closed sales, 12-month windows ending September 20. Confidence: Low (4 and 8 sales in the two windows).
Jump to: Price history & scorecard · Homes for sale · Schools · FAQ
· Updated October 2, 2026 · Live data: Stellar MLS, refreshed twice daily · MLS facts carry their source; interpretation lines are Momentum Research · Data sources & freshness
Nearby homes for sale
No active listings inside Highland Woods 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
Highland Woods market snapshot (as of September 20, 2026): the median sale price is about $854K ($251 per sq ft over the trailing 12 months of closed sales), and a median 12 days on market for closed sales. The trailing-12-month median is up 0% from the prior 12 months, computed from record-level Stellar MLS closed sales (4 closings in the current window).
In ZIP 34698 (DUNEDIN), 701 homes closed in the last 12 months at a median of $380K ($301/sq ft), up 1.1% year over year, with a median 56 days on market. Right now 130 active and 33 pending listings put supply at about 3.8 months - a balanced market. See the live ZIP 34698 housing market and the Pinellas County market.
County records show 11 qualified sales in Highland Woods across 2024 - 2025 (5 in 2024, 6 in 2025), median $860,000 - the last recorded sale per parcel on the Florida DOR 2025 assessment roll, independent of the MLS.
Highland Woods is a community of 166 homes in Dunedin, Pinellas County, built between 2001 and 2007 (median 2003.0), with a median living area of about 3,398 square feet. 87% of parcels are homesteaded, the owner-occupancy proxy in the Florida DOR assessment roll (2025 roll, public records).
The setting & the homes.
Aerial and on-site photos of Highland Woods. Swipe to explore the community.
Swipe or use the arrows → tap any photo to enlarge
Photos from Stellar MLS listings in Highland Woods; content deemed reliable but not guaranteed.
Price History: What Homes Here Have Actually Sold For
Median sale price over the trailing 12 months ending September 20 of each year, from record-level Stellar MLS closed sales. Same methodology as every appreciation figure on this page: the 2026 point ($854K) IS the median in the snapshot above, and the move from 2025 ($852K) IS the +0.3% one-year change.
Windows contain 0 to 8 sales each (4 in the current window); every figure carries its sample size, and thin markets swing on single closings. Based on Stellar MLS data distributed by MLS GRID for the period 2006 through 2026. Deemed reliable but not guaranteed.
The real cost & risk here
Before the list price, the Florida math the portals skip. These are Pinellas County typicals — your exact home, flood zone, and insurance quote will vary, so verify each before you offer.
Check it for your address: look up your flood zone (FEMA) · insurance by county · true-cost calculator · Pinellas County scorecard.
County typicals from Momentum’s Florida housing data (Zillow & Realtor.com aggregates, Census, FRED), updated monthly; insurance modeled. Flood zone is property-specific — always confirm via FEMA.
22% of homes for sale in ZIP 34698 are already under contract (under contract ÷ under contract + active listings) — a read on how much of the available inventory buyers have already claimed. Source: MLS data (2026-10-01).
Highland Woods Market Scorecard
Highland Woods is currently a balanced market., and homes go under contract in about 0 days.
Go deeper: ZIP market scorecard · county scorecard · true cost calculator · affordability calculator.
Live data: Stellar MLS, refreshed twice daily. Market metrics only; these describe homes for sale and recent sales, not residents.
Housing distress & ownership in Highland Woods, DUNEDIN
Who owns here, how much is not owner-occupied, and how much for-sale inventory is under distress.
Source: Momentum Realty Research. Ownership & parcels from the FL DOR 2025 tax roll; distress from MLS active-listing status/remarks; price from MLS closed sales. Based on Stellar MLS data distributed by MLS GRID for the period October 2026 through October 2026. Deemed reliable but not guaranteed.
Homes For Sale Right Now in Highland Woods
Live MLS inventory for Highland Woods. Every active listing, what is under contract right now, and the last 12 months of closed sales, refreshed twice a day. Closed comps beat an algorithm's guess every time.
Active and pending Highland Woods listings as of 2026-10-01, priced high to low. Based on Stellar MLS data distributed by MLS GRID for the period 2006 through 2026. Tap any home to ask about it.
Highland Woods on the map.
Every active, pending, and recently sold home, plotted. Toggle the layers and tap a home for the details.
Listing locations from Stellar MLS. Map data © OpenStreetMap, tiles © CARTO.
Life at Highland Woods
- Deed Restrictions · reported on 3 of 3 listings
- Gated Community - No Guard · reported on 3 of 3 listings
- Irrigation-Reclaimed Water · reported on 3 of 3 listings
- Gated · reported on 2 of 3 listings
- Fence Restrictions · reported on 1 of 3 listings
- No Truck/RV/Motorcycle Parking · reported on 1 of 3 listings
Community amenities as reported across Stellar MLS listings in this community; deemed reliable but not guaranteed. Verify current amenities and access with the HOA.
Schools
- Pinellas County Public Schools
- Verify the zoned schools by address
- Magnet and choice options may be available
- Garrison-Jones Elementary (verify by address)FLDOE grade A · Public
- Dunedin Highland Middle (verify by address)FLDOE grade A · Public
- Dunedin High (verify by address)FLDOE grade A · Public
Grades are official Florida Department of Education school grades for 2025-26. Assignments are reported as of the 2025-26 year and can change; always confirm with Pinellas County Public Schools for a specific address.
Buying with schools in mind? We can confirm the exact zoned schools for any Highland Woods address.
The Highland Woods buying strategy.
If we were buying in Highland Woods 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 Woods.
A closer look at the Highland Woods market
At a median of $251 per square foot, Highland Woods prices sit in a fairly defined band, so condition and updates — more than the list price — tend to separate one home from the next.
The housing stock is 166 homes built between 2001 and 2007, and 87% 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 Woods. The deal is won or lost on condition, the comps, and the renovation math.
Momentum Buy Score.
Our proprietary 0 to 10 read across the factors that decide how a home in Highland Woods buys, holds, and resells. Momentum Research; not an appraisal.
Momentum Intelligence Scores are our proprietary, qualitative assessment on a 0 to 10 scale, built from the record-level market data on this page. They are a framework for comparing communities, not a guarantee of future value and not advice on a specific home; unlike an automated value estimate they do not price your home, they grade the community on evidence you can inspect. Composite is the plain average of the 3 factors (7.7). Basis: Recent Direction +0.3% year-over-year; Owner Commitment 87% owner-occupied; Pricing Power 97.4% sale-to-list. Refreshed with each data update.
HOA, CDD & Fees
- HOA dues reported around $99/month (about $1,188/yr) · median of 95 MLS listings, most billed twice a year
- Any club/amenity membership is billed separately
Listings in this community report association dues of about $99 per month ($1,188 a year) - the median AssociationFee across 95 MLS records, normalised to a monthly figure; most are billed twice a year. Dues change with budgets and can differ by section or product type; confirm the current figure with the association before you offer. Source: MLS listing records, 2026-10.
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 Woods 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 Woods sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Highland Woods, 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 Woods home worth?
Get a no-obligation home value based on real comparable sales in Highland Woods, 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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Frequently Asked Questions
What is the median home price in Highland Woods?
How long do homes in Highland Woods take to sell?
How many homes are in Highland Woods?
What share of Highland Woods is owner-occupied?
When were the homes in Highland Woods built?
What schools serve Highland Woods?
Who is the best real estate agent for Highland Woods?
How do I find a top Dunedin real estate agent who knows Highland Woods?
Can Momentum Realty connect me with an agent for Highland Woods?
Where is Highland Woods, and what county is it in?
Data sources & freshness
| Live listings | Stellar MLS, refreshed twice daily (last: October 1, 2026) |
| Community market stats | Stellar MLS closed sales, 12-month windows ending September 20, 2026 |
| Housing stock & ownership | Florida DOR assessment roll (street-list match (5 streets, ZIP 34698)) |
| Under-contract shares | Stellar MLS records, as of 2026-09-20 |
| Schools | 2025-26 district assignments + FLDOE school grades; verify with the district |
| Historical depth | Closed-sale records back to 2006 (51 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.
Looking to buy here? Search homes for sale →
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See how Highland Woods fits the bigger picture — live prices, inventory, and Momentum Scores:
More on Highland Woods
- Home values · What homes in Highland Woods actually sell for
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