442 BRIERCLIFF DRIVE
ORLANDO, FL 32806
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- 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.
Price history
From the property’s MLS record.
| Date | Event | Price | Change |
|---|---|---|---|
| Sep 18, 2026 | Listed | $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.
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.
