Gated Communities in Oldsmar, FL
Looking for gated communities in Oldsmar, FL? Momentum tracks 10 Oldsmar communities with evidence of gated community living, each with MLS-derived pricing and market pace below — plus the local questions worth asking before you buy, and a direct line to an agent who works these communities.
Oldsmar gated communities at a glance
The communities, by recent sales activity
| Community | City | Median price | 1-yr change | Days on mkt |
|---|---|---|---|---|
| East Lake Woodlands · agent | Oldsmar | $151,000 | – | 85 d |
| Bay Arbor · agent | Oldsmar | $580,000 | – | 72 d |
| Laurel Oaks at East Lake · agent | Oldsmar | $344,000 | – | – |
| Seaside Estates · agent | Oldsmar | $504,000 | – | 100 d |
| Quail Forest · agent | Oldsmar | $334,000 | – | 87 d |
| Estuary of Mobbly Bay · agent | Oldsmar | $1.24M | – | – |
| Deerpath · agent | Oldsmar | $927,000 | – | – |
| Tuscany Woods South · agent | Oldsmar | $351,000 | – | – |
| Diamond Crest · agent | Oldsmar | $1.09M | – | – |
| Cross Pointe · agent | Oldsmar | $699,000 | – | – |
Communities are listed by recent closing volume in Momentum’s MLS data. Figures are aggregates, change over time, and are deemed reliable but not guaranteed.
What gates change about ownership
Controlled access typically comes with a manned gate, a transponder system, or both — funded through HOA dues. Expect guest-access procedures, delivery and contractor rules, and in some communities rental restrictions. Review the HOA budget for how the gate and any roving patrol are funded, and whether roads are private (the HOA maintains them — another line in the dues) or public.
Due diligence before you buy behind a gate
Request the HOA documents early: budget, reserves, rules, and the last two years of meeting minutes. Private roads, gates and common areas are owner-funded, so thin reserves become special assessments. Our buyer closing costs calculator helps you model dues and assessments into the real monthly cost.
What it costs to own here
At Pinellas County’s typical combined millage of 19.39 mills, a purchase at $542,000 (the median across these Oldsmar gated communities) generates roughly $10,507 a year in property tax before exemptions — about $876 a month. Florida resets the assessed value to roughly your purchase price, so the seller’s current bill is not a preview of yours; a homesteaded owner then gets the $25,000–$50,000 exemption and the 3% Save Our Homes cap going forward. Citizens Property Insurance policies in Pinellas County average about $1,911 a year ($159 a month) — private-market quotes vary with roof age and wind mitigation, so price coverage before your inspection window closes. All-in, our county model puts the typical monthly cost of ownership in Pinellas County near $2,236 (principal and interest on the typical home, tax, and insurance).
Run your exact numbers: the property tax after purchase calculator uses Pinellas County’s verified millage, and the buyer closing costs calculator builds the full cash-to-close.
Demand and supply in Pinellas County right now
In the most recent IRS migration data (2022-2023), Pinellas County lost a net 1,182 people to relocation, with the largest inbound flows from NY, CA, NJ. Households moving IN reported average incomes of $95,596 versus $74,796 for those leaving — the income mix of demand, straight from tax filings. Population is up about 0.3% over the recent multi-year window. On the supply side, builders pulled 4,198 residential permits in Pinellas County in 2025 (1,376 single-family), up 59.8% year over year. Permits are tomorrow’s inventory: a shrinking pipeline supports prices, a swelling one hands buyers leverage. Our valuation model reads the county as overvalued by about 7.5% versus its income-and-rent fundamentals.
Live inventory, refreshed nightly from the MLS.
Live gated-community listings in Oldsmar
54 active listings carry the flag today (41% of Oldsmar inventory), median asking $267,500, $210/sq ft, median 45 days on market. Photo cards link to the listing; refreshed nightly.
Newest gated community homes in Oldsmar
The most expensive gated community homes in Oldsmar
| Listing | Asking | Sq ft | Community |
|---|---|---|---|
| 50 Willowood Lane | $1,499,900 | 4,475 | Deerpath |
| 1723 Captiva Drive | $830,700 | 2,736 | Cross Pointe |
| 1730 Captiva Drive | $775,000 | 2,523 | Cross Pointe |
| 80 Foxfire Lane | $719,000 | 2,584 | east lake woodlands |
| 10 Arbor Lane | $669,000 | 2,318 | east lake woodlands |
| 550 Palmdale Drive | $599,000 | 2,211 | east lake woodlands |
| 212 Arbor Woods Circle | $599,000 | 2,030 | Bay Arbor |
| 380 Rosalind Lane | $599,000 | 2,423 | Bay Arbor |
| 140 Brent Circle | $545,000 | 1,791 | Seaside Estates |
| 119 Brent Circle | $525,000 | 1,834 | Seaside Estates |
Gated Community Homes by price
| Band | For sale | Share |
|---|---|---|
| Under $300K | 30 | 56% |
| $300Kâ$500K | 13 | 24% |
| $500Kâ$750K | 8 | 15% |
| $750Kâ$1M | 2 | 4% |
| $1M+ | 1 | 2% |
Oldsmar gated community homes by community
Click a community for its full guide: prices, HOA reality, insurance posture and the homes for sale.
| Community | Gated Community Homes | New build | Median list | From |
|---|---|---|---|---|
| East Lake Woodlands Condo | 11 | 0 | $204,000 | $145,000 |
| Seaside Estates | 10 | 0 | $492,500 | $374,000 |
| East Lake Woodlands Cluster Homes | 10 | 0 | $294,900 | $235,000 |
| East Lake Woodlands Cypress Estates | 7 | 0 | $185,000 | $165,000 |
| East Lake Woodlands | 6 | 0 | $634,450 | $189,999 |
| Bayside Terrace | 4 | 0 | $433,500 | $380,000 |
| East Lake Woodlands Woodlake Run | 4 | 0 | $194,250 | $175,000 |
| Cross Pointe | 3 | 0 | $830,700 | $775,000 |
| Heatherwood Unit One Condo | 3 | 0 | $329,900 | $279,900 |
| Kingsmill | 2 | 0 | $577,450 | $569,900 |
| East Lake Woodlands Patio Homes | 2 | 0 | $389,949 | $379,999 |
| East Lake Woodlands Pinewinds | 2 | 0 | $332,450 | $239,900 |
| Countryside Key | 2 | 0 | $252,250 | $229,500 |
| Deerpath Unit One | 1 | 0 | $1,499,900 | $1,499,900 |
| Diamond Crest | 1 | 0 | $1,350,000 | $1,350,000 |
| Aberdeen Unit Two | 1 | 0 | $1,025,000 | $1,025,000 |
| Aberdeen Unit One | 1 | 0 | $935,000 | $935,000 |
| Warwick Hills | 1 | 0 | $829,000 | $829,000 |
| Stonebriar | 1 | 0 | $729,900 | $729,900 |
| Parcel B - The Pinnacle | 1 | 0 | $640,000 | $640,000 |
| Bay Arbor Unit 1A | 1 | 0 | $599,000 | $599,000 |
| Bay Arbor | 1 | 0 | $599,000 | $599,000 |
| Hunters Trail Twnhms | 1 | 0 | $495,000 | $495,000 |
| Bayside Terrace - Pt Rep | 1 | 0 | $375,000 | $375,000 |
| Tuscany Woods South | 1 | 0 | $330,000 | $330,000 |
| Quail Forest Cluster Homes | 1 | 0 | $288,000 | $288,000 |
| Meadows Of East Lake Woodlands | 1 | 0 | $179,950 | $179,950 |
| East Lake Woodlands Condo Unit 7 | 1 | 0 | $175,000 | $175,000 |
Explore more of Oldsmar
- Gated Communities in Pinellas County
- Golf Course Communities in Oldsmar
- Townhome Communities in Oldsmar
- Find the best agent in Oldsmar
- Best neighborhoods in Oldsmar
Run the numbers in Pinellas County
- Find the best agent in Pinellas County
- Get a cash offer in Pinellas County
- Pinellas County housing scorecard
- What would selling net you
- Buyer closing costs calculator
Common questions
How many gated communities does Oldsmar, FL have?
What do homes in Oldsmar gated communities cost?
How does Momentum classify a community as one of the gated communities?
How much is home insurance in Pinellas County?
What are property taxes like in Pinellas County?
Community classifications are compiled from MLS-reported amenities, verified amenity records and MLS build-year data, as of 2026-06-16; they are informational, change over time, and are deemed reliable but not guaranteed — verify details with each association. Not an offer of housing to any protected class to the exclusion of others. Equal Housing Opportunity.