Highland Woods
Homes for Sale in Dunedin, FL
True comps, carrying-cost math, and listings before the portals.
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
Highland Woods
Highland Woods
Highland Woods
Highland Woods
Highland Woods
Highland WoodsThe market around Highland Woods
Highland Woods is a small community — 76 recorded sales on file, most recently in 2025 — too few for its own price trend. Here is the market around it.
In ZIP 34698, 329 homes are on the market and 20% are under contract — a steady corner of Dunedin.
Across Pinellas County, 6,999 homes are active and 1,872 pending (21% under contract).
Homes here are single family residence.
ZIP and county figures describe the wider market, not Highland Woods specifically. Momentum Research analysis of MLS records.
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 August 2026 through August 2026. Deemed reliable but not guaranteed.
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
The housing stock is 174 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.
HOA, CDD & Fees
- Mandatory HOA. Confirm current dues
- 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 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.
See homes for sale in Highland Woods on the map →
Frequently Asked Questions
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?
Nearby Communities
Explore more neighborhoods near Highland Woods with Momentum Realty’s local guides.
Data sources & freshness
| Live listings | Stellar MLS, refreshed twice daily (last: August 2, 2026) |
| Housing stock & ownership | Florida DOR 2025 assessment roll (community parcel extract) |
| 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 2006 (3 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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