442 BRIERCLIFF DRIVE, ORLANDO, FL, 32806
Active137 days on marketListed Mar 19, 2026MLS #O6390631
About this home
442 BRIERCLIFF DRIVE
Timeless charm meets refined living in this beautifully updated historic home in the heart of Delaney Park, complete with a detached guest house and thoughtfully designed living spaces. Offering 4 bedrooms, 4 bathrooms, and 2,688 square feet, this residence blends classic character with modern comfort in one of downtown Orlando’s most desirable neighborhoods. Inside, a welcoming living room with a built-in wood-burning fireplace creates a warm focal point and flows seamlessly into the separate dining room, both highlighted by wood flooring. Just beyond, the kitchen is designed for both everyday living and entertaining, featuring custom cabinetry, stone countertops, stainless steel appliances, a spacious island, dry bar, and generous cabinet and counter space. The kitchen overlooks a stunning family room with vaulted ceilings and an abundance of large windows and doors that fill the space with natural light while offering views of the backyard. The main level includes two bedrooms and two full bathrooms, providing flexibility for a variety of living arrangements. Upstairs, the private primary suite serves as a peaceful retreat with large built-in closets and a beautifully renovated en suite bathroom featuring dual sinks, a spacious glass walk-in shower with a built-in bench, and a separate soaking tub. The detached guest house includes a full bathroom, air conditioning, and a convenient kitchenette, providing a perfect space for guests, work, or hobbies. The fenced backyard with a large stone porch is ideal for entertaining or quiet evenings outdoors. Perfectly situated in the heart of downtown Orlando, this home offers effortless access to dining, shopping, and major roadways, with world-famous theme parks and Orlando International Airport just a short drive away—combining timeless elegance with modern city living. Mortgage savings may be available for buyers of this listing.
Facts & features
The home at a glance
4
Bedrooms
4
Bathrooms
2,688
Sqft
0.17 ac
Lot size
1925
Year built
Two
Levels
$331
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.
$6,414 /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
$6,414/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 N/A
$331 vs $288
Days on market
137 vs 40 typical
Where $331/sqft sits among the 245 homes for sale in N/A
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 Delaney Park
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Get to know Orlando. See the full Orlando guide →
Delaney Park — neighborhood snapshot
Population
1,214
Median age
43
Median income
$132,331
Median home value
$541,609
Avg household
2
Households w/ children
175
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)
106 of 245
N/A have cut their price
Median sold price, Orlando, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 104% above the ORLANDO 32806 median. See the full Orlando market guide →
Paper trail
This home's history
Reality check
What actually sold near 442 BRIERCLIFF 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$530,000
4933 ROUND LAKE ROAD · same community
3 bd · 2.5 ba · 2,632 sqft · $201/sqft · 111 DOM
Sold · Dec ’25$254,000
Carr 156 KM 12.1 INT BO. PALO HINCADO · same community
5 bd · 2.5 ba · 2,510 sqft · $101/sqft · 79 DOM
Sold · Mar ’26$1,275,000
16422 SPRING VALLEY ROAD · same community
4 bd · 3 ba · 3,141 sqft · $406/sqft · 70 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 442 BRIERCLIFF DRIVE — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 442 BRIERCLIFF 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
442 BRIERCLIFF DRIVE FAQs
What would the monthly payment be for 442 BRIERCLIFF DRIVE?+
With 10% down on a 30-year Conventional loan at 6%, the all-in payment lands around $6,414/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 442 BRIERCLIFF DRIVE?+
The most recent tax bill on record (2025) was $13,489. 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 442 BRIERCLIFF DRIVE?+
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 Orlando?+
At $889,000, this home is listed about 125% above the Orlando median of $394,900. The market section on this page shows how the area is trending.
Which schools are assigned to 442 BRIERCLIFF DRIVE?+
William R Boone High (high), Blankner K-8 (elementary) — Orange County School District. Always verify school assignments with the district before relying on them.
The brief
Five things that matter here
01Positioned at the premium end
$889,000 runs 104% above the ORLANDO 32806 median — but at 2,688 sqft it's also 68% larger than the typical Orlando listing.
02Trees/Woods views
The trees/woods view is part of what you're buying — views hold value independently of the structure.
03Time on market is leverage
137 days on market against a Orlando median of 40 — sellers in this position are usually ready to negotiate.
04Strong assigned schools
William R Boone High, Blankner K-8 — Blankner K-8 rates 4 of 5. Always verify assignments with the district.
05The price has already moved
Listed at $950,000, now $889,000 — a $61K cut. The full history is in the market section below.
Keep looking
Similar homes nearby
Listing courtesy of REDFIN CORPORATION · Wylie Devlin. MLS #O6390631.
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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