Homestead living in the quaint Regal Oak Shores neighborhood with lake-access minutes away! Beautifully updated and move-in ready, this spacious 4-BEDROOM, 3-FULL BATH, POOL home features a bright open layout, modern finishes throughout, and a private in-law suite—ideal for guests or multi-generational living. Enjoy outdoor living with a screened-in sparkling pool and plenty of patio space to entertain. The unique backyard setup features four raised garden beds, a cozy chicken coop alongside a functional garden workshop. This versatile space offers fresh eggs daily and a dedicated area for gardening or DIY projects, all set in a peaceful, green environment with a variety of fruit trees in the backyard—perfect for sustainable living enthusiasts. Don’t wait too long, this house will not last!
Sold for $495,000
$495,000
1558 REGAL OAK DRIVE, KISSIMMEE, FL 34744
4beds
1,811sqft
Single Family Residence
Built in 1984
0.34 Acres Lot
$479,700 Zestimate®
$273/sqft
$2,881 Estimated rent
Home value
$479,700
$432,000 - $532,000
$2,881/mo
Zestimate® history
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$3,305/mo
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List your homeWhat's special
Pool homeModern finishesPrivate in-law suiteFunctional garden workshopBright open layoutPlenty of patio spaceCozy chicken coop
Zillow last checked:
Listing updated:
Listed by:
Taryn Riley 407-868-3250,
REAL BROKER, LLC 855-450-0442
Bought with:
Robert Christiano, 3157421
COLDWELL BANKER RESIDENTIAL RE
Source: Stellar MLS,MLS#: O6294494
Originating MLS: Orlando Regional
Originating MLS: Orlando Regional
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 3
- Full bathrooms: 3
Primary bedroom
- Features: Ceiling Fan(s), Dual Closets
- Level: First
- Area: 132 Square Feet
- Dimensions: 11x12
Other
- Features: Built-In Shelving, En Suite Bathroom, Wet Bar, Built-in Closet
- Level: First
- Area: 320 Square Feet
- Dimensions: 20x16
Bedroom 2
- Features: Ceiling Fan(s), Coat Closet
- Level: First
- Area: 110 Square Feet
- Dimensions: 11x10
Bedroom 3
- Features: Ceiling Fan(s), Coat Closet
- Level: First
- Area: 110 Square Feet
- Dimensions: 11x10
Bathroom 1
- Features: En Suite Bathroom, Shower No Tub, Single Vanity, Window/Skylight in Bath, No Closet
- Level: First
- Area: 42.5 Square Feet
- Dimensions: 8.5x5
Bathroom 2
- Features: Single Vanity, Tub With Shower, Window/Skylight in Bath, No Closet
- Level: First
- Area: 43.5 Square Feet
- Dimensions: 8.7x5
Bathroom 3
- Features: En Suite Bathroom, Shower No Tub, Single Vanity, No Closet
- Level: First
- Area: 39.96 Square Feet
- Dimensions: 7.4x5.4
Dining room
- Level: First
- Area: 100 Square Feet
- Dimensions: 10x10
Kitchen
- Features: Breakfast Bar, Built-In Shelving, Pantry
- Level: First
- Area: 110 Square Feet
- Dimensions: 10x11
Living room
- Features: Coat Closet
- Level: First
- Area: 192 Square Feet
- Dimensions: 12x16
Heating
- Central, Electric
Cooling
- Central Air
Appliances
- Included: Dishwasher, Disposal, Dryer, Electric Water Heater, Microwave, Range, Range Hood, Refrigerator, Washer
- Laundry: In Garage
Features
- Ceiling Fan(s), Chair Rail, High Ceilings, Living Room/Dining Room Combo, Open Floorplan, Solid Surface Counters, Solid Wood Cabinets, In-Law Floorplan
- Flooring: Laminate, Tile
- Doors: Sliding Doors
- Windows: Window Treatments
- Has fireplace: Yes
- Fireplace features: Living Room, Masonry, Wood Burning
Interior area
- Total structure area: 2,554
- Total interior livable area: 1,811 sqft
Property
Parking
- Total spaces: 2
- Parking features: Boat, Driveway, Garage Door Opener, Oversized
- Attached garage spaces: 2
- Has uncovered spaces: Yes
- Details: Garage Dimensions: 18x21
Features
- Levels: One
- Stories: 1
- Patio & porch: Covered, Enclosed, Front Porch, Rear Porch, Screened
- Exterior features: Irrigation System, Private Mailbox, Rain Gutters
- Has private pool: Yes
- Pool features: Fiberglass
- Spa features: In Ground
- Fencing: Fenced,Wood
- Has view: Yes
- View description: Garden
Lot
- Size: 0.34 Acres
- Features: Landscaped, Veg. (Productive) Garden
- Residential vegetation: Fruit Trees, Mature Landscaping
Details
- Additional structures: Storage, Workshop
- Parcel number: 022629479100010190
- Zoning: ORS1
- Special conditions: None
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Traditional
- Property subtype: Single Family Residence
Materials
- Brick, Wood Frame
- Foundation: Slab
- Roof: Shingle
Condition
- New construction: No
- Year built: 1984
Utilities & green energy
- Sewer: Septic Tank
- Water: Public
- Utilities for property: BB/HS Internet Available, Cable Available, Electricity Connected, Phone Available
Community & HOA
Community
- Pet fee: $0 monthly
- Subdivision: REGAL OAK SHORES UNIT 4
HOA
- Has HOA: No
Location
- Region: Kissimmee
Financial & listing details
- Price per square foot: $273/sqft
- Tax assessed value: $339,000
- Annual tax amount: $3,347
- Date on market: 5/1/2025
- Cumulative days on market: 31 days
- Listing terms: Cash,Conventional
- Ownership: Fee Simple
- Total actual rent: 0
- Electric utility on property: Yes
- Road surface type: Paved, Asphalt
Price history
| Date | Event | Price |
|---|---|---|
| 7/16/2025 | Sold | $495,000$273/sqft |
Source:  Stellar MLS #O6294494 Report a problem | ||
| 6/15/2025 | Pending sale | $495,000$273/sqft |
Source: Stellar MLS #O6294494 Report a problem | ||
| 5/30/2025 | Listed for sale | $495,000$273/sqft |
Source: Stellar MLS #O6294494 Report a problem | ||
| 5/25/2025 | Pending sale | $495,000$273/sqft |
Source: Stellar MLS #O6294494 Report a problem | ||
| 5/16/2025 | Listed for sale | $495,000$273/sqft |
Source: Stellar MLS #O6294494 Report a problem | ||
| 5/8/2025 | Pending sale | $495,000$273/sqft |
Source: Stellar MLS #O6294494 Report a problem | ||
| 5/1/2025 | Listed for sale | $495,000+80%$273/sqft |
Source: Stellar MLS #O6294494 Report a problem | ||
| 1/16/2020 | Sold | $275,000-3.5%$152/sqft |
Source: Public Record Report a problem | ||
| 12/3/2019 | Pending sale | $284,900$157/sqft |
Source: ASSIST 2 SELL FOUTZ REALTY #O5827927 Report a problem | ||
| 11/23/2019 | Listed for sale | $284,900$157/sqft |
Source: ASSIST 2 SELL FOUTZ REALTY #O5827927 Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $3,527 +5.4% | $339,000 +5.7% |
| 2024 | $3,347 +3.7% | $320,800 +7.5% |
| 2023 | $3,229 +4.4% | $298,300 +20.8% |
| 2022 | $3,093 +0.8% | $247,000 +15.5% |
| 2021 | $3,068 +63.7% | $213,800 +6.1% |
| 2020 | $1,874 +2.1% | $201,500 +9.9% |
| 2019 | $1,836 | $183,400 +44.6% |
| 2018 | $1,836 +5.4% | $126,809 +2.1% |
| 2017 | $1,741 +0.5% | $124,201 +2.1% |
| 2016 | $1,733 +1.7% | $121,647 +0.7% |
| 2015 | $1,705 +1.6% | $120,802 +0.8% |
| 2014 | $1,677 | $119,844 +1.5% |
| 2013 | -- | $118,073 +1.7% |
| 2012 | -- | $116,100 -5.7% |
| 2011 | -- | $123,100 -4.6% |
| 2010 | -- | $129,100 -17.1% |
| 2009 | -- | $155,800 -30.3% |
| 2008 | -- | $223,500 -3% |
| 2007 | -- | $230,300 +15.5% |
| 2006 | -- | $199,400 +29.3% |
| 2005 | -- | $154,200 +19.2% |
| 2004 | -- | $129,400 |
| 2003 | -- | $129,400 +5.5% |
| 2002 | $1,593 +2.1% | $122,615 +1.6% |
| 2001 | $1,561 +1.6% | $120,684 +3% |
| 2000 | $1,537 | $117,169 |
Find assessor info on the county website
Neighborhood: 34744
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Nearby schools
GreatSchools rating
- 4/10Partin Settlement Elementary SchoolGrades: PK-5Distance: 3.7 mi
- 7/10Neptune Middle SchoolGrades: 6-8Distance: 2.9 mi
- 4/10Osceola High SchoolGrades: 9-12Distance: 3.7 mi
Schools provided by the listing agent
- Elementary: Partin Settlement Elem
- Middle: Neptune Middle (6-8)
- High: Osceola High School
Source: Stellar MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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Estimated market value
$479,700
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Estimated market value
$479,700
- Florida
- Osceola County
- Kissimmee
- 34744
- 1558 REGAL OAK DRIVE
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