REAL ESTATE
For agentsBuySellInternationalCryptoJournal
ENES
ENES
For agentsBuySellInternationalCryptoJournal414.712.6275
REAL ESTATE
For agentsBuySellInternationalCryptoJournal
ENES
ENES
For agentsBuySellInternationalCryptoJournal414.712.6275
REAL ESTATE
For agentsBuySellInternationalCryptoJournal
ENES
ENES
For agentsBuySellInternationalCryptoJournal414.712.6275
← Back to search

For sale· 43 days on market

442 BRIERCLIFF Drive, Orlando, FL 32806

MLS# O6441912·Courtesy of HOPKEY REALTY

$849,000

≈ Estimated $5,560/mo estimated

·4 bd·, 4 ba·, 2,688 sq ft·, 0.17 ac lot

1 / 71of 71 photos
4
Bedrooms
4
Bathrooms
2,688
Sq ft
0.17 ac
Lot size
1925
Year built
$316
Per sq ft
  • Residential
  • Built 1925

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 full
Living area
2,688 sqft

Property

Type
Residential
Year built
1925
Lot size
0.17 acres

Financial

Annual taxes
$13,489
Price / sqft
$316

Estimate your monthly payment

$169,800
%
%
yrs

$5,560/ month estimated

  • Principal & interest$4,428
  • Property tax$778
  • Insurance$354

Illustrative estimate — not a lending offer.

Investor tools

See flip, rental and BRRR numbers for this home.

Location

Orlando, FL

Ask me about 442 BRIERCLIFF Drive

Call, text, or send a message. I'll answer myself, same day, in English or Spanish.

Call or text 414.712.6275Ask a question

Pedro Rivera

My agent · 414.712.6275

Choose a day

        

Choose a time of day

Free, no obligation · I confirm within the hour during business hours.

CallText

Listing data courtesy of HOPKEY REALTY. My request routes to Pedro Rivera in DashBrew CRM.

Stellar MLS

reThought Real Estate does not guarantee listing accuracy.

Property information is provided 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.

Pedro Rivera
Pedro RiveraAs seen on · Media coverage
TMJ4Telemundo WisconsinCBS 58 Wisconsin
REAL ESTATE
CALL OR TEXT · HABLAMOS ESPAÑOL
414.712.6275
Pedro J Rivera, Broker & Founder
reThought Real Estate · Kissimmee, FL & Milwaukee, WI
Email
BUY
Orlando homesKissimmee homesMilwaukee homesBuying process
SELL
My home's valueListing processSeller's guide
AREAS
OrlandoKissimmeeSt. CloudMilwaukeeWauwatosaAll areas →
MORE
For agentsInternational projectsCryptoCalculatorsJournalWho is Pedro?
© 2026 PEDRO J RIVERA · BROKER, reTHOUGHT REAL ESTATE · LIC FL & WI
LIC FL & WIPRIVACYTERMSEQUAL HOUSING
Call Direct: 414.712.6275WhatsApp

$849,000

4 bed, 4 bath, 2,688 sqft

Request showing

Similar homes nearby

1269 WELSON Road

$3,400/mo

5 bd · 4.5 ba · 2,068 sqft

1269 WELSON Road

Courtesy of FLATFEE.COM

5344 LORILAWN Drive

$2,150/mo

3 bd · 2 ba · 1,630 sqft

5344 LORILAWN Drive

Courtesy of UNLOCK REALTY GROUP INC

8238 CYERS Lane

$324,900

3 bd · 2.5 ba · 1,380 sqft

8238 CYERS Lane

Courtesy of HAMPTON WINDSOR REALTY LLC

Around Orlando

Homes for sale in Orlando

As of Nov 7

Asking prices in Orlando run from $9,900 to $20,000,000. The middle ask is $368,030. This home asks $849,000.

Middle ask $368,030
This home $849,000
$9,900$20,000,000
Homes for sale
4,518
Middle ask
$368,030
New this week
185

These numbers use homes for sale only.

See the Orlando market report