2248 HILLSHIRE DRIVE, ORLANDO, FL, 32828
Active77 days on marketListed May 18, 2026MLS #O6408756
About this home
2248 HILLSHIRE DRIVE
Beautifully maintained 4-bedroom, 2-bath pool home nestled on a serene pond and conservation lot — truly your own little piece of paradise in Southeast Orlando. The backyard is a private retreat featuring elegant cast iron fencing draped in fragrant jasmine, creating a peaceful setting perfect for relaxing, entertaining, or enjoying the water views and fishing right from your backyard. This move-in ready home has been thoughtfully updated throughout. Exterior was freshly painted in 2020, roof replaced in December 2019, and the entire interior was repainted in 2022 with cheerful coastal-inspired “Key West” colors and beach-themed charm. The covered lanai features brand new screens installed in 2023 along with a new patio door, while the pool deck and porches have been freshly refinished with Sherwin-Williams pool deck paint. Located within a gated, guard-monitored community offering added privacy and security, with driver’s license verification and owner approval required for entry. Conveniently situated just 30 minutes to Downtown Orlando, Disney, and countless Central Florida attractions, plus only 30–45 minutes to the beaches via SR 528 and I-95. Waterford Lakes shopping, dining, and entertainment are just 15 minutes away. Enjoy Florida living at its finest with beautiful views, thoughtful updates, and an unbeatable location.
Facts & features
The home at a glance
4
Bedrooms
2
Bathrooms
1,877
Sqft
0.14 ac
Lot size
2
Garage
2001
Year built
One
Levels
$264
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 and the real association fee — not generic estimates.
$3,882 /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
$3,882/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
−3.8%
$/sqft vs STONEYBROOK
$264 vs $228
Days on market
77 vs 40 typical
Where $264/sqft sits among the 13 homes for sale in STONEYBROOK
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 Stoneybrook Master Of Orlando
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Get to know Orlando. See the full Orlando guide →
Stoneybrook Master Of Orlando — neighborhood snapshot
Population
6,159
Median age
32
Median income
$118,434
Median home value
$557,010
Avg household
3
Households w/ children
1,013
For the school run
Orange County School District
School assignments and ratings via edgeAI — always verify with the district.
The numbers that matter
The Orlando market
$400K → $409K
Orlando median sold, yr/yr
97.0%
Sale-to-list ratio (12 mo)
9 of 13
STONEYBROOK have cut their price
Median sold price, Orlando, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 13% above the ORLANDO 32828 median. See the full Orlando market guide →
Paper trail
This home's history
Reality check
What actually sold near 2248 HILLSHIRE DRIVE
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Oct ’25$490,000
14700 CHADBURY COURT · same community
4 bd · 2 ba · 1,881 sqft · $260/sqft · 113 DOM
Sold · Aug ’25$335,000
362 FAIRWAY ISLES LANE · same community
2 bd · 2 ba · 1,861 sqft · $180/sqft · 53 DOM
Sold · Dec ’25$455,000
14732 HUNTLEY DRIVE · same community
4 bd · 2 ba · 1,847 sqft · $246/sqft · 13 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 2248 HILLSHIRE DRIVE — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 2248 HILLSHIRE DRIVE — 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
2248 HILLSHIRE DRIVE FAQs
What would the monthly payment be for 2248 HILLSHIRE DRIVE?+
With 3.5% down on a 30-year FHA loan at 6%, the all-in payment lands around $3,882/mo — principal and interest, the actual property-tax bill, the $251/mo association fee 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.
How much are the HOA fees at 2248 HILLSHIRE DRIVE?+
The association fee works out to $251 per month. Ask us for the full association documents — they spell out exactly what the fee covers.
What are the property taxes on 2248 HILLSHIRE DRIVE?+
The most recent tax bill on record (2025) was $4,017. 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 2248 HILLSHIRE DRIVE?+
The listing reports pets: Breed Restrictions, Cats OK. 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 Orlando?+
At $495,500, this home is listed about 25% above the Orlando median of $394,900. The market section on this page shows how the area is trending.
Which schools are assigned to 2248 HILLSHIRE DRIVE?+
Stone Lakes Elementary (elementary), Timber Creek High (high), Avalon Middle (middle) — Orange County School District. Always verify school assignments with the district before relying on them.
The brief
Four things that matter here
01Positioned at the premium end
$495,500 runs 13% above the ORLANDO 32828 median — but at 1,877 sqft it's also 17% larger than the typical Orlando listing.
02Waterfront living
This home sits directly on the water — the single scarcest feature in Florida inventory and the strongest long-term value anchor.
03Strong assigned schools
Stone Lakes Elementary, Timber Creek High, Avalon Middle — Stone Lakes Elementary rates 4 of 5. Always verify assignments with the district.
04The price has already moved
Listed at $511,500, now $495,500 — a $16K cut. The full history is in the market section below.
Keep looking
Similar homes nearby
Listing courtesy of CHARLES RUTENBERG REALTY ORLANDO · Diane Molaka. MLS #O6408756.
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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