Search Results

Save
Ask
Tour
Hide
Share
$950,000
New Listing

442 BRIERCLIFF DRIVE
ORLANDO, FL 32806

For Sale|Single Family Residence|Active
4
Beds
4
Total Baths
4
Full Baths
2,688
SqFt
$353
/SqFt
1925
Built
County:
Orange
Call Now: 407-237-3331
Is this the listing for you? We can help make it yours.
407-237-3331
Upcoming Open Houses
Sat, Mar 21, 11:00 AM - 1:00 PM
442 BRIERCLIFF DRIVE442 BRIERCLIFF DRIVE442 BRIERCLIFF DRIVE442 BRIERCLIFF DRIVE
Save
Ask
Tour
Hide
Share

Mortgage Calculator

Monthly Payment (Est.)

$4,334
Calculator powered by Showcase IDX, a Constellation1 Company. Copyright ©2026 Information is deemed reliable but not guaranteed.

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.

Save
Ask
Tour
Hide
Share
Listing Snapshot
Price 
$950,000
Days On Site 
0 Days
Bedrooms 
4
Inside Area (SqFt) 
2,688 sqft
Total Baths 
4
Full Baths 
4
Partial Baths 
N/A
Lot Size 
0.17 Acres
Year Built 
1925
MLS® Number 
O6390631
Status 
Active
Property Tax 
$13,489
HOA/Condo/Coop Fees 
N/A
Sq Ft Source 
Public Records
Friends & Family
Recent Activity
6 hours agoListing updated with changes from the MLS®
6 hours agoListing first seen on site
General Features
Acres 
0.17
Direction Faces 
North
Levels 
Two
Parking 
DrivewayElectric Vehicle Charging Station(s)
Pets 
Yes
Property Sub Type 
Single Family Residence
Sewer 
Public Sewer
SqFt Total 
2868
Utilities 
Cable AvailableElectricity ConnectedSewer ConnectedWater Connected
Water Source 
Public
Zoning 
R-1/T/AN
Interior Features
Appliances 
DishwasherMicrowaveRangeRefrigerator
Basement 
Crawl Space
Cooling 
Central Air
Fireplace 
Yes
Fireplace Features 
Living RoomWood Burning
Flooring 
TileWood
Furnished 
Unfurnished
Heating 
CentralElectric
Interior 
Built-in FeaturesDry BarEat-in KitchenHigh CeilingsOtherStone CountersVaulted Ceiling(s)
Laundry Features 
InsideLaundry Room
Family Room 
Level - FirstFeatures - Ceiling Fan(s)
Kitchen 
Level - FirstFeatures - Kitchen Island
Living Room 
Level - First
Master Bathroom 
Level - SecondFeatures - Double Vanity
Master Bedroom 
Level - SecondFeatures - Ceiling Fan(s)
Save
Ask
Tour
Hide
Share
Exterior Features
Construction Details 
StuccoFrame
Exterior 
LightingOther
Fencing 
FencedWood
Other Structures 
Guest House
Patio And Porch 
Rear Porch
Roof 
Shingle
Community Features
Financing Terms Available 
CashConventionalFHAVA Loan
MLS Area 
32806 - Orlando/Delaney Park/Crystal Lake
Roads 
AsphaltPaved
Township 
22
Listing courtesy of REDFIN CORPORATION (407) 463-1014



Listing information is provided by Participants of the Stellar MLS. IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. Properties displayed may be listed or sold by various participants in the MLS Copyright 2026, Stellar MLS.
Last checked: 2026-03-19 04:17 PM EDT

Neighborhood & Commute
Source: Walkscore
Disclosure: Community information and market data powered by Constellation Data Labs. Information is deemed reliable but not guaranteed.
Save
Ask
Tour
Hide
Share

Compare listings

Compare