28809 BENNINGTON DRIVE, WESLEY CHAPEL, FL, 33544
Active313 days on marketListed Nov 13, 2025MLS #TB8447899
About this home
28809 BENNINGTON DRIVE
Back on the market!!!!! DO NOT MISS OUT ON THIS OPPORTUNITY!!!!! Luxury Country Retreat Minutes from Wesley Chapel’s Best Shopping and Dining!!! Experience the perfect blend of serene country living and modern luxury in this beautifully remodeled estate, ideally located just 10 minutes from I-75 and premier destinations such as The Grove at Wesley Chapel, the new Target and The Crates, The Shops at Wiregrass, and Tampa Premium Outlets. Set on a fully fenced 3-acre lot, this property offers the freedom to bring your horses, goats, chickens, or any of your favorite outdoor toys—creating the lifestyle you’ve always dreamed of. Step inside the main residence and be welcomed by soaring high ceilings, an open-concept layout, and abundant natural light that fills every room. The home features 4 spacious bedrooms and 3 full bathrooms, including a luxurious owner’s suite and a private mother-in-law suite, ideal for multigenerational living or hosting long-term guests. The gourmet kitchen features a walk-in pantry and opens seamlessly to the living and dining areas—perfect for both everyday living and elegant entertaining. The elegant family room centers around a stunning gas and wood-burning fireplace, creating a warm and inviting ambiance. Double sliding doors open to an expansive courtyard oasis—the perfect setting for entertaining family and friends or unwinding with a glass of wine as you take in the tranquil sounds of nature. The courtyard features a built-in outdoor kitchen (appliances not included), offering endless potential for your custom touches. Meticulously updated in 2023, this home boasts modern comforts and peace of mind with upgrades including: New tankless water heater (2023), whole-house water filtration system (2023), all new appliances (2023), roof replaced in 2021, propane tank system serving the entire home. A standout feature of this property is the impressive 1,100-sqft detached garage, offering space for up to four vehicles, equipment, or recreational toys. Above the garage sits a brand-new, fully equipped guest apartment, complete with its own kitchen, bathroom, private entrance, and parking—ideal for guests, extended family, or potential rental income. (The full apartment square footage, 1,100 is not included in main house sqft). If you’ve been searching for that rare combination of luxury, space, privacy, and convenience, LOOK NO FURTHER!!!. This estate offers the best of both worlds—peaceful country charm just minutes from the heart of Wesley Chapel’s vibrant lifestyle!!!. SCHEDULE YOUR SHOWING TODAY!!!
Facts & features
The home at a glance
5
Bedrooms
4
Bathrooms
2,924
Sqft
3.03 ac
Lot size
4
Garage
1999
Year built
One
Levels
$282
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.
$5,212 /mo · 10% down Conventional, 30-yr fixed at 6%
The assumptions
Above the FHA loan limit for our service areas, so Conventional is the default. VA buyers: switch below — $0 down.
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
FHA isn’t available at this price — the loan would exceed the $541,287 FHA limit for our service areas.
Estimated payment
$5,212/mo
Includes estimated PMI — it drops off once you reach 20% equity. 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.
$/sqft vs Wesley Chapel actives
$282 vs $199
Days on market
313 vs 50 typical
Where $282/sqft sits among the 400 Wesley Chapel 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 Plantation Pines
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Get to know Wesley Chapel. See the full Wesley Chapel guide →
Plantation Pines — neighborhood snapshot
Population
978
Median age
50
Median income
$143,156
Median home value
$597,600
Avg household
2
Households w/ children
98%
For the school run
Pasco County School District
School assignments and ratings via edgeAI — always verify with the district.
The numbers that matter
The Wesley Chapel market
$440K → $432K
Wesley Chapel median sold, yr/yr
97.9%
Sale-to-list ratio (12 mo)
280 of 400
Wesley Chapel actives have cut their price
Median sold price, Wesley Chapel, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 146% above the WESLEY CHAPEL 33544 median. See the full Wesley Chapel market guide →
Paper trail
This home's history
Reality check
What actually sold near 28809 BENNINGTON DRIVE
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Dec ’25$695,000
3719 LODGE POLE LANE · same community
4 bd · 2 ba · 2,193 sqft · $317/sqft · 13 DOM
Sold · Aug ’26$330,450
10750 NW 190TH STREET · same community
4 bd · 2 ba · 1,875 sqft · $176/sqft · 126 DOM
Sold · Feb ’26$760,000
27641 LINCOLN PLACE
4 bd · 3.5 ba · 2,871 sqft · $265/sqft · 0 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
Jillian Kobylesky
Real Estate Agent · CENTURY 21 Edge
Tours, negotiation, and every question about 28809 BENNINGTON DRIVE — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 28809 BENNINGTON DRIVE — before you fall in love.
See it in person
Schedule a tour
Live availability from Jillian's calendar — pick a time and it's booked. Confirmation lands in your inbox immediately.
Straight answers
28809 BENNINGTON DRIVE FAQs
What would the monthly payment be for 28809 BENNINGTON DRIVE?+
With 10% down on a 30-year Conventional loan at 6%, the all-in payment lands around $5,212/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 28809 BENNINGTON DRIVE?+
The most recent tax bill on record (2024) was $3,530. A new owner's bill can differ once the sale price resets the assessed value — we can walk you through what to expect.
How does the price compare to other homes in Wesley Chapel?+
At $824,500, this home is listed about 90% above the Wesley Chapel median of $435,000. The market section on this page shows how the area is trending.
Which schools are assigned to 28809 BENNINGTON DRIVE?+
Quail Hollow Elementary School (elementary), Wesley Chapel High School (high), Thomas E. Weightman Middle School (middle) — Pasco County School District. Always verify school assignments with the district before relying on them.
The brief
Three things that matter here
01Positioned at the premium end
$824,500 runs 146% above the WESLEY CHAPEL 33544 median — but at 2,924 sqft it's also 41% larger than the typical Wesley Chapel listing.
02Time on market is leverage
313 days on market against a Wesley Chapel median of 50 — sellers in this position are usually ready to negotiate.
03The price has already moved
Listed at $899,900, now $824,500 — a $75K cut. The full history is in the market section below.
Keep looking
Similar homes nearby
Listing courtesy of INVESTOR CORNER REALTY LLC · Yuneisy Hernandez. MLS #TB8447899.
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.
Never miss a listing
New Wesley Chapel homes, in your inbox
Like 28809 BENNINGTON DRIVE but not quite? A daily digest of every new listing in Wesley Chapel — straight from the MLS, hours after it goes live. Unsubscribe anytime.
Just watching this one home? Ask Jillian to ping you on any price or status change →