106 WINDWARD PLACE, OLDSMAR, FL, 34677
Active34 days on marketListed Jun 19, 2026MLS #TB8521469
About this home
106 WINDWARD PLACE
Welcome to 106 Windward Place, a two bedroom two bathroom condominium located in the Meadows at East Lake Woodlands. One of Oldsmar‘s most sought after gated communities. This is a bank owned (REO) property, an excellent opportunity for homeowners, investors, or buyers looking to customize a home of their own taste. The functional floor plan features a spacious, living and dining area, split bedroom, layout, and a private setting within the community. The Meadows offers beautifully maintained grounds, mature landscaping, and a peaceful residential atmosphere. Residents enjoy convenient access to shopping, dining, golf, parks, Tampa International Airport and the Beautiful Gulf beaches. Whether you are searching for a primary residence, seasonal getaway or investment property 106 Windward Place offers outstanding value and the chance to own within the desirable East Lake Woodlands community. Property is being sold as is.
Facts & features
The home at a glance
2
Bedrooms
2
Bathrooms
879
Sqft
1984
Year built
One
Levels
$205
Per sqft
Inside
Outside & construction
Community & fees
Utilities & systems
The numbers
What it really costs
Built from this home's actual numbers — the most recent property-tax bill on record — not generic estimates.
$1,374 /mo · 3.5% down FHA, 30-yr fixed at 6%
The assumptions
FHA is the default here because it gets you in the door with just 3.5% down. Switch to Conventional or VA below.
These numbers assume a generic buyer — your credit, down payment and loan program change them. Get the real quote in minutes:
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Run your own numbers
Estimated payment
$1,374/mo
Includes FHA mortgage insurance and the financed 1.75% upfront premium. Taxes reflect the most recent bill on record; insurance is a typical-Florida estimate. Your lender’s numbers will differ. CENTURY 21 Edge partners with Florida’s best lenders.
Value check
Is the price right?
The internet’s favorite home-value number comes from a single automated model that has never seen the street, the finishes, or the view — which is why it routinely misses by tens of thousands of dollars. The edgeAI estimate combines multiple independent data sources with our team’s on-the-ground expertise in this exact market.
vs edgeAI estimate
+4.9%
$/sqft vs Oldsmar actives
$205 vs $228
Days on market
34 vs 43 typical
Where $205/sqft sits among the 155 Oldsmar actives
The edgeAI estimate is a starting point, not an appraisal or a broker price opinion. It is generated from public records, listing data and market modeling, and is subject to change once a licensed real estate professional personally inspects the property. Condition, floor, view and lot are not fully captured by any model — ask us for a full comparative market analysis.
Where it sits
Inside East Lake Woodlands
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Get to know Oldsmar. See the full Oldsmar guide →
East Lake Woodlands — neighborhood snapshot
Population
7,647
Median age
53
Median income
$107,049
Median home value
$399,307
Avg household
2
Households w/ children
583
For the school run
Pinellas County School District
School assignments and ratings via edgeAI — always verify with the district.
The numbers that matter
The Oldsmar market
$360K → $355K
Oldsmar median sold, yr/yr
96.3%
Sale-to-list ratio (12 mo)
94 of 155
Oldsmar actives have cut their price
Median sold price, Oldsmar, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 31% below the OLDSMAR 34677 median. See the full Oldsmar market guide →
Paper trail
This home's history
Reality check
What actually sold near 106 WINDWARD PLACE
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Jul ’26$570,000
100 ARBOR LANE · same community
3 bd · 2 ba · 1,852 sqft · $308/sqft · 8 DOM
Sold · Aug ’25$475,000
50 WATER OAK WAY · same community
3 bd · 2 ba · 1,921 sqft · $247/sqft · 59 DOM
Sold · Oct ’25$635,000
455 HICKORYNUT AVENUE · same community
3 bd · 2 ba · 1,943 sqft · $327/sqft · 1 DOM
Closed-sale data from the MLS, last 12 months, selected for similarity in size and location. No two homes are identical — ask us for a full comparative analysis.
Your home team
The pros in your corner
Buying a home is two conversations — the home and the money. Here’s who handles each, side by side, already working together.
Your agent
David Ramirez
Real Estate Agent · CENTURY 21 Edge
Tours, negotiation, and every question about 106 WINDWARD PLACE — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 106 WINDWARD PLACE — before you fall in love.
See it in person
Schedule a tour
Pick a day that works — this goes straight to David's phone and CRM.
Straight answers
106 WINDWARD PLACE FAQs
What would the monthly payment be for 106 WINDWARD PLACE?+
With 3.5% down on a 30-year FHA loan at 6%, the all-in payment lands around $1,374/mo — principal and interest, the actual property-tax bill and typical Florida insurance. The payment calculator on this page lets you switch loan type (FHA, Conventional, VA) and adjust the down payment, rate and term.
What are the property taxes on 106 WINDWARD PLACE?+
The most recent tax bill on record (2025) was $896. A new owner's bill can differ once the sale price resets the assessed value — we can walk you through what to expect.
Are pets allowed at 106 WINDWARD PLACE?+
The listing reports pets: Yes. Communities often layer on breed or weight rules — we'll verify the specifics with the association before you commit.
How does the price compare to other homes in Oldsmar?+
At $179,950, this home is listed about 47% below the Oldsmar median of $342,450. The market section on this page shows how the area is trending.
Which schools are assigned to 106 WINDWARD PLACE?+
Forest Lakes Elementary School (elementary), Joseph L. Carwise Middle School (middle), East Lake High School (high) — Pinellas County School District. Always verify school assignments with the district before relying on them.
Keep looking
Similar homes nearby
Listing courtesy of TAMPA BAY SIGNATURE PROPERTIES, LLC · Christi Watson. MLS #TB8521469.
IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data is deemed reliable but is not guaranteed accurate by Stellar MLS.
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