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Active · Single Family

442 BRIERCLIFF DRIVE

ORLANDO, FL 32806

Beds
4 beds
Baths
4 baths
Area
2,688 sqft
Single FamilyBuilt 19257,267 sqft lotCentral, ElectricCentral AirFireplace$316/sqft3 days on market

Location

About this home

A rare opportunity to own a beautifully renovated historic home with a detached guest house in the heart of Delaney Park. Set on a charming residential street surrounded by some of Downtown Orlando’s most sought-after neighborhoods, this 4-bedroom, 4-bath residence offers 2,688 square feet of thoughtfully designed living space with a seamless blend of original character and modern updates. From the moment you enter, the home feels warm and inviting, with beautiful wood floors, a spacious living room with a wood-burning fireplace, and a separate dining area ideal for entertaining. The updated kitchen serves as the centerpiece of the home, featuring custom cabinetry, stone countertops, stainless steel appliances, a large center island, dry bar, and abundant storage. The kitchen opens directly to an impressive vaulted family room surrounded by oversized windows and glass doors, creating a bright and airy gathering space with views of the private backyard. The first floor also offers two bedrooms and two full bathrooms, providing excellent flexibility for guests, family, or a home office. Upstairs, the primary suite offers a private retreat with generous built-in closet space and a beautifully updated bathroom featuring dual vanities, a large glass-enclosed walk-in shower with built-in bench, and a separate soaking tub. An additional bedroom and full bathroom complete the upper level. Adding exceptional versatility, the detached guest house includes its own full bathroom, air conditioning, and kitchenette. Whether used for guests, extended family, a private office, creative space, or an additional living area, this separate structure adds a level of flexibility rarely found in the neighborhood. Outside, the fenced backyard and expansive stone porch create an inviting setting for outdoor dining, entertaining, or relaxing in privacy. The location is equally impressive, placing you minutes from Lake Davis, Lake Cherokee, Delaney Park, Thornton Park, Downtown Orlando, restaurants, coffee shops, shopping, and major roadways, while Orlando International Airport and Central Florida’s world-famous attractions are easily accessible. A distinctive home, an exceptional location, and the flexibility of a detached guest house make 442 Briercliff Drive a truly special Delaney Park offering.

Facts & features

Interior

Bedrooms
4
Bathrooms
4
Living area
2,688 sqft
Heating
Central, Electric
Cooling
Central Air
Flooring
Tile, Wood
Fireplace
Yes
Features
Built-in Features, Ceiling Fans(s), Dry Bar, Eat-in Kitchen, High Ceilings, Other…
Appliances
Dishwasher, Microwave, Range, Refrigerator

Exterior & lot

Lot size
7,267 sqft (0.17 ac)
Roof
Shingle
Construction
Stucco, Frame
Exterior
Lighting, Other, Sidewalk

Financial

Annual tax
$13,489 (2025)
Price / sqft
$316/sqft

Utilities

Water
Public
Sewer
Public Sewer
Utilities
Cable Available, Electricity Connected, Sewer Connected, Water Connected

Property

Property type
Single Family
Year built
1925
Subdivision
ACREAGE
County
Orange

Assigned schools

Elementary
Blankner Elem
Middle
Blankner School (K-8)
High
Boone High

Listing

Status
Active
Days on market
3 days
MLS #
MFR811101774
Source
Stellar MLS

Listed by Michael Dudley · HOPKEY REALTY

Listing data provided by Stellar MLS. Information deemed reliable but not guaranteed.

Estimate your monthly cost

PITI + HOA
Estimated monthly payment$5,422/mo
Principal & interest
$4,298/mo
Property tax
$1,124/mo
Home insurance
Left out until you enter a quote

Opens at 20% down over 30 years at 6.5%, the same assumptions as the answers below. Property tax is this listing's own 2025 bill. Insurance is left out until you enter a quote, because Florida premiums turn on roof age, elevation and carrier. Every field is editable.

Ask about this property

Answered from this listing’s own figures and the sales around it.

Similar homes nearby

Homes for sale in ORLANDO within the same price band.

9793 LAKE GEORGIA DRIVEActive
$950,000
9793 LAKE GEORGIA DRIVE
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1011 JUEL STREETActive
$682,000
1011 JUEL STREET
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3 beds3 baths1,680 sqft
19682 QUINLAN STREETActive
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19682 QUINLAN STREET
ORLANDO, FL 32833
5 beds5 baths3,528 sqft

Price history

From the property’s MLS record.

DateEventPriceChange
Sep 18, 2026Listed$850,000

Neighbourhood

The schools below come from the MLS record for this home. Walking, transit and cycling figures for ORLANDO, FL are not connected yet, so this page does not show them.

Elementary school
Blankner Elem
Assigned school from the MLS record
Middle school
Blankner School (K-8)
Assigned school from the MLS record
High school
Boone High
Assigned school from the MLS record

Frequently asked questions

What would 442 BRIERCLIFF DRIVE, ORLANDO cost per month?

About $5,422 a month: $4,298 principal and interest, $1,124 property tax. That assumes 20% down at 6.5% over 30 years, and leaves out insurance.

Is 442 BRIERCLIFF DRIVE, ORLANDO priced fairly?

Comparable homes nearby put it between $1,009,935 and $1,161,969, with $1,085,952 in the middle. Those are asking prices, not closed sales: 8 properties of the same type within three miles, each within 20% of this one's size and a bedroom either way, at a median of $404 a square foot.

How does 442 BRIERCLIFF DRIVE, ORLANDO compare to nearby homes?

8 comparable properties within three miles. The nearest: 1413 OSCEOLA COURT, ORLANDO, FL at $1,300,000, 3,201 sq ft, 0.15 miles away; 210 PHILLIPS PLACE, ORLANDO, FL at $865,000, 2,995 sq ft, 0.21 miles away; 219 WHITTIER CIRCLE, ORLANDO, FL at $950,000, 2,272 sq ft, 0.28 miles away.

How long has 442 BRIERCLIFF DRIVE, ORLANDO been on the market?

1 day on the market.

Has the price of 442 BRIERCLIFF DRIVE, ORLANDO changed?

The price has not moved since it was listed.

How big is 442 BRIERCLIFF DRIVE, ORLANDO?

4 bed, 4 bath, 2,688 square feet. That is $316 a square foot.

What year was 442 BRIERCLIFF DRIVE, ORLANDO built?

Built in 1925.

What is the HOA fee at 442 BRIERCLIFF DRIVE, ORLANDO?

The feed lists no association fee for this property.

What are the property taxes at 442 BRIERCLIFF DRIVE, ORLANDO?

Property tax works out to about $1,124 a month, $13,489 a year, on the 2025 assessment.

Is 442 BRIERCLIFF DRIVE, ORLANDO still available?

It is still on the market.