Single Family Residence at 442 BRIERCLIFF DR, ORLANDO
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$875,000

442 BRIERCLIFF DR
ORLANDO, FL 32806
Listed by Wylie Devlin · REDFIN CORPORATION
Bedrooms
4
Bathrooms
4
Living area
2,688 sqft
Year built
1925

About this home

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.

Highlights

Fireplace

Property details

MLS
Stellar MLS
MLS #
MFRO6390631
Property type
Single Family Residence
Subdivision
N/A
Status
Active
Days on market
164
On market date
March 19, 2026
Stories
N/A
Total bathrooms
4
Garage spaces
N/A
Parking spaces
N/A
Lot size
0.17 acres
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Nearby schools

Within 10 miles. School directory data from the National Center for Education Statistics (NCES), accessed via the Urban Institute Education Data API. Local Score is calculated by INNOVATE Real Estate; where a state rating is shown, it comes from that state's own official school report card.

Elementary
BLANKNER K-8
0.93 mi away · Grades -1-8
Nearest school -- attendance-zone data not available here
4.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
810
Student:teacher ratio
14.7:1
District
ORANGE
Middle
HOWARD MIDDLE
1.26 mi away · Grades 6-8
Nearest school -- attendance-zone data not available here
2.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
950
Student:teacher ratio
18.6:1
District
ORANGE
High
ESE TRANSITION
0.57 mi away · Grades 12
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
129
Student:teacher ratio
7.6:1
District
ORANGE

Walkability

Blended score for ORLANDO's center, calculated by INNOVATE Real Estate from two sources: the EPA's National Walkability Index (street network, transit, land-use mix) and Google Places amenity data (what's actually reachable on foot from this point). 60% EPA National Walkability Index + 40% nearby-amenity density (Google Places).

87
Highly walkable
out of 100
EPA National Walkability Index
16.2 / 20 -- Most walkable
Google Places amenity density
95 / 100
Restaurants & cafes20
Grocery stores3
Parks20
Schools12
Transit stops20
Pharmacies10

Market position

How this listing compares to current activity in ORLANDO, from live MLS data.

On the market 164 days -- 58 more days than ORLANDO's current average of 106 days.
For reference, the median list price across 7,978 active listings in ORLANDO right now is $250,000.

Mortgage calculator

Estimate only - actual rate and payment depend on your lender, credit, and loan program.

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Adjust tax / insurance estimates
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/mo
Est. monthly payment
$5,419/mo
$175,000 down
$700,000 loan
Principal & interest$4,540
Property tax (est.)$729
Home insurance (est.)$150

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Data source: Listing information provided by Stellar MLS (mfrmls) via Trestle/CoreLogic. Last updated August 30, 2026.

Information herein deemed reliable but not guaranteed; all measurements, school assignments, HOA fees, taxes, and feature lists are approximate and should be independently verified. Equal Housing Opportunity.