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4427 Gilpin Way

ORLANDO, FL 32812

3 beds
2 baths
1,592 sqft
10,064 sqft lot
$244 per sqft
1961 build
– on site

Step into the opportunity of a lifetime with this classic 1961 ranch-style gem nestled in highly sought-after Conway Hills. With solid bones and timeless charm, this 3-bedroom, 2-bath home is primed for a stylish revival into a true mid-century modern masterpiece. Boasting over six decades of character and care, this home already features essential upgrades including: New repipe (2024) Roof replaced (2017) Efficient solar panels to slash your electric bill Liquid siding for added durability and weather protection Drain field redone (2014) Automatic sprinkler system powered by a separate well Well-maintained A/C system All wrapped in stucco walls and surrounded by mature Florida landscaping. Inside, the spacious living room invites you in with a statement fireplace, tons of natural light, and original architectural lines begging to be showcased. A sunken bonus room adds extra flair and flexibility—perfect for entertaining, a studio, or home office. The kitchen maintains its vintage soul with a built-in oven, cooktop, and charming window-over-sink view. Just steps away, a versatile dining area sets the stage for dinners, game nights, or your next design vision. The primary suite features a private bath and walk-in closet, while two additional bedrooms afford cozy quarters or creative space to make your own. Outside, the fenced backyard is your canvas—whether you dream of a tropical retreat, garden oasis, or sleek patio space. The enclosed Florida room offers year-round comfort for lounging or entertaining. Rounding out the home is a 2-car carport, with easy-access laundry tucked conveniently in the rear. All of this is just minutes from everywhere you want to be: 15 minutes to Downtown Orlando or Orlando International Airport 20 minutes to Universal, SeaWorld, and UCF 35 minutes to Disney 45 minutes to Cocoa or New Smyrna Beach Ready to reimagine this retro beauty? Bring your vision, your vibe, and your personal tou ch.0. Mid-century magic awaits—schedule your private showing today!

Listing courtesy of STELLAR_MLS / PREMIUM PROPERTIES REAL ESTATE

Last checked: Checking… • Last updated Jul 7, 2025 •

MLS# O6324459 —

The Building

Year Built:

1961
New Construction:

false
Construction Materials:

Block
Levels:

One
Stories Total:

1
Roof:

Shingle
Foundation Details:

Slab
Window Features:

Aluminum Frames
Building Area Total:

1592
Building Area Units:

Square Feet
Building Area Source:

Public Records

Interior

Interior Features:

Ceiling Fan(s)
Flooring:

Carpet
Fireplace:

true
Fireplace Features:

Decorative

Room Dimensions

Living Area:

1592
Living Area Units:

Square Feet
Living Area Source:

Public Records

Location

Directions:

Go North on Conway Rd from Hoffner, Turn Right on Gilpin, House on Left.
Latitude:

28.49039
Longitude:

-81.32956
Coordinates:

-81.32956, 28.49039

The Property

Parcel Number:

172330167502300
Property Type:

Residential
Property Subtype:

Single Family Residence
Lot Size Acres:

0.23
Lot Size Area:

10064
Lot Size SqFt:

10064
Lot Size Units:

Square Feet
Total Acres:

0 to less than 1/4
Zoning:

R-1A
Direction Faces:

South
View:

false
Exterior Features:

Irrigation System
Fencing:

Chain Link
Water Source:

Public
Road Responsibility:

Public Maintained Road
Road Surface Type:

Concrete
Flood Zone Code:

X
Additional Parcels:

false
Homestead:

true
Lease Restrictions:

true
Land Lease:

false

Listing Agent

Contact info:

Taxes

Tax Year:

2024
Tax Lot:

30
Tax Block:

B
Tax Legal Description:

CONWAY HILLS UNIT NO 4 Y/6 LOT 30 BLK B
Tax Book Number:

Y-6
Tax Annual Amount:

$2,634.46

Beds

Bedrooms Total:

3

Baths

Total Baths:

2
Total Baths:

2
Full Baths:

2

The Listing

Virtual Tour URL Unbranded:

https://www.propertypanorama.com/instaview/stellar/O6324459
Special Listing Conditions:

None

Heating & Cooling

Heating:

Central
Heating:

true
Cooling:

Central Air
Cooling:

true

Utilities

Utilities:

Cable Available
Sewer:

Septic Tank

Appliances

Appliances:

Built-In Oven
Laundry Features:

Laundry Room

Schools

Elementary School:

Shenandoah Elem
Middle Or Junior School:

Conway Middle
High School:

Boone High

The Community

Subdivision Name:

CONWAY HILLS
Senior Community:

false
Waterview:

false
Water Access:

false
Waterfront:

false
Pool Private:

false
Association:

false
Ownership:

Fee Simple

Parking

Garage:

false
Attached Garage:

true
Carport:

true
Carport Spaces:

2
Covered Spaces:

2
Open Parking:

true
Parking Features:

Driveway

Monthly cost estimate

Asking price

$390,000

Expense	Monthly cost
Mortgage	$2,088
Taxes	$219
Insurance	$107
Utilities	$191 See report
Total	$2,605/mo.^*
	^*This is an estimate

Explore the Area

My Commute

From

Walk Score®

Provided by WalkScore® Inc.

Bike Score®

Provided by WalkScore® Inc.

Soundscore™

Provided by HowLoud

Air Pollution Index

Provided by ClearlyEnergy

Sale history

Date	Event	Source	Price
7/5/25 Jul 5, 2025	Listed / Active	STELLAR_MLS	$390,000
5/23/24 May 23, 2024	Price Changed	STELLAR_MLS
5/1/24 May 1, 2024	Listed / Active	STELLAR_MLS

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This house located in Conway Hills, Conway, FL 32812 is currently for sale for $390,000. 4427 Gilpin Way is a 1,592 square foot house with 3 beds and 2 baths that has been on Estately for 7 days. 4427 Gilpin Way is in the Conway Hills neighborhood of Conway and has a WalkScore® of 43, making it car-dependent. This house is in the attendance area of Conway Middle School, Boone High School, Shenandoah Elementary School, Cornerstone Charter Academy High School, and Cornerstone Charter Academy K-8.

Listing Courtesy of: STELLAR_MLS and PREMIUM PROPERTIES REAL ESTATE.

Based on information from the My Florida Regional MLS DBA Stellar MLS 2025.

All information provided is deemed reliable but is not guaranteed and should be independently verified. Stellar MLS, Estately and their affiliates provide the MLS and all content therein “AS IS” and without any warranty, express or implied. The information included in this listing is provided exclusively 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. The information on each listing is furnished by the owner and deemed reliable to the best of his/her knowledge, but should be verified by the purchaser. Stellar MLS and Estately assume no responsibility for typographical errors, misprints or misinformation. This property is offered without respect to any protected classes in accordance with the law. For any questions please call (407) 499-8911.