Recently Viewed Properties
See This Home
Save This Listing
Close

View All Photos

$939,000 -$10,999 (-1.16%) Price Reduced

  • For Sale
  • Active
  • Single Family
  • 4 Beds
  • 3 Full Baths
  • 1 Partial Bath
  • 2,518 Sq. Ft.
  • Updated 11 hours ago
See This Home
Save This Home
See This Home
Save This Home
Welcome home to this STUNNING two-story Baldwin Park home (4 Bedrooms + 3.5 Bathrooms + Office) showcasing OVER $180,000 in upgrades - ROOF REPLACED (2023), KITCHEN UPGRADED (Relocated and expanded island, replaced granite, appliances, added pendant lighting and under cabinet lighting), A/C UNIT REPLACED (2018), WATER HEATER REPLACED (2020), PRIMARY BATHROOM REMODELED (Replaced cabinets, enlarged the shower, replaced all tile, and added new granite), Closet Systems added (in Primary + Laundry + Garage), New Gutters, Plantation Shutters, and an Electric Vehicle Charging Outlet installed. Inside, an abundance of natural light highlights the meticulous renovations and elevated finishes throughout the home. Downstairs, you'll enjoy the spacious dining area, an office, and a kitchen/great room combination that's ideal for both entertaining and everyday living. The upstairs has a great split floor plan! The loft area provides flexible space and separates the primary suite from the additional 3 bedrooms (two of which share a Jack and Jill bath). The private primary suite serves as a serene retreat, showcasing a fully renovated spa-inspired bathroom with refined finishes and a calming ambiance. This home blends modern sophistication with the timeless charm of one of Orlando's most sought-after communities. Every detail has been thoughtfully curated to create a space that is both elegant and effortlessly livable. The extended front patio is the perfect setting for morning coffee or relaxing evenings in this picturesque neighborhood. Every Baldwin Park neighbor has access to the Gigabit Fiber internet by Hotwire Fision which is included in the community association and provides exceptional connectivity. This home is perfectly positioned in the heart of Baldwin Park and is move-in-ready. Come enjoy the tree-lined streets, scenic parks, playgrounds, community pools, and fitness centers, with easy access to the Village Center's shops, dining, and entertainment - all while being minutes from Downtown Orlando, Winter Park, and the executive airport. Take advantage of this rare opportunity to experience modern luxury and classic Baldwin Park living in one beautifully updated home.

Full Property Details for 5416 Penway Dr

General

  • Price: $939,000
  • HOA FEE: $93/month
  • HOA FEE FREQ.: Semi-Annually
  • Taxes: $7,918 (2024)
  • Status: Active
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: O6357821
  • Updated: 6/9/2026
  • Added to Site: 215 day(s) ago

Rental Information

  • Min. Lease: 6 Months

Interior

  • Number of Rooms: 10
  • Interior Features: Built-in Features, Ceiling Fan(s), Eating Space In Kitchen, Kitchen and Family Room Combination, Open Floorplan, PrimaryBedroom Upstairs, Stone Counters, Thermostat, Walk-In Closet(s), Window Treatments
  • Appliances: Dishwasher, Disposal, Dryer, Electric Water Heater, Microwave, Range, Refrigerator, Washer, Water Filtration System
  • Flooring: Carpet, Tile, Hardwood

Rooms

Bathrooms

  • Total Bathrooms: 4
  • Full Bathrooms: 3
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 4

Other Rooms

  • Laundry: Laundry Room

Additional Information

  • Shared Amenities: Clubhouse, Fitness Center, Park, Playground, Pool, Racquetball, Recreation Facilities, Trail(s)
  • Security/Safety: Security System, Smoke Detector(s)

Exterior

  • Exterior Features: Irrigation System, Lighting, Rain Gutters, Sidewalk
  • Deck/Patio: Covered, Front Porch
  • Porch/Patio/Deck: Covered, Front Porch

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Covered Spaces: 2
  • Parking Features: Alley Access, Driveway, Garage Door Opener, Garage Faces Rear

Location

  • Area: 32814 - Orlando
  • County: Orange
  • Development Name: 32814 - Orlando
  • Subdivision: BALDWIN PARK UNIT 9A
  • Driving Directions: From FL 408 E, take Exit 14 and merge onto Lake Underhill Road. Turn left onto FL 436 / S Semoran Blvd. Turn right onto Old Cheney Highway. Turn right onto Truman Road. Turn left onto Shea Street. Turn left onto Penway Drive.
  • Direction Faces: West

School Information

  • Elementary School: Baldwin Park Elementary
  • Middle School: Glenridge Middle
  • High School: Winter Park High

Community

  • Community Name: 32814 - Orlando
  • Community Features: Clubhouse, Deed Restrictions, Fitness Center, Park, Playground, Pool, Sidewalks
  • Optional Amenities: Clubhouse, Fitness Center, Park, Playground, Pool, Racquetball, Recreation Facilities, Trail(s)
  • Association: Yes
  • Assoc. Name: Stacey Fryrear / Sentry Management
  • Assoc. Fees Include: Community Pool, Internet, Manager, Recreational Facilities
  • Pet Restrictions: Verify w/HOA.

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Central, Electric

Utilities

  • Sewer: Public Sewer
  • Water: Public
  • Utility Description: Electricity Connected, Public, Sewer Connected, Water Connected

Structural Information

  • Exterior Const.: Block, Concrete, Stucco
  • Roof: Shingle
  • Windows: Window Treatments
  • Stories/Levels: Two
  • Square Feet: 2,518
  • Sq. Ft. Source: Public Records
  • Year Built: 2006

Lot Features

  • Lot Size (Acres): 0.07
  • Lot Size (Sq. Ft.): 3,000
  • Lot Size: 3000
  • Lot Dimensions: x
  • Frontage: Street Paved
  • Street/Road Desc.: Paved, Asphalt
  • Fencing (Description): Fenced, Vinyl

Financial Considerations

  • Association Fee: $556
  • Assoc Fee Freq.: Semi-Annually
  • Assoc Fee Desc.: Required
  • CDD: Yes
  • Tax Amount: $7,918.11
  • Tax Year: 2024

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: BALDWIN PARK UNIT 9A 59/71 LOT 1340
  • Flood Zone Info: X
  • APN: 212230053001340
  • Property ID: 212230053001340
  • Block/Lot/Section: 1

Listed by Exp Realty Llc

Quickly Find Out More

* Indicates a required field

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Send Message, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If an Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby’s International Realty®). I acknowledge that I have read and agree to the Terms of Use and Privacy Notice.

We Value Your Privacy

Listing agent

— 5416 Penway Dr —

  • Exp Realty Llc

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 5416 Penway Dr

School District:Orange County School District
NameGradesDistance
Baldwin Park Elementary School
1750 Common Way Road, Orlando, FL 32814
PK-51 mi
Glenridge Middle School
2900 Upper Park Road, Orlando, FL 32814
6-81.4 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 5416 Penway Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
6/09/2026
Price Reduced
$939,000
-1.16%
MLS
4/30/2026
Price Reduced
$949,999
-1.76%
MLS
4/11/2026
Price Reduced
$967,000
-2.81%
MLS
3/10/2026
Price Reduced
$995,000
-2.92%
MLS
2/21/2026
Price Reduced
$1,024,900
-2.39%
MLS
2/06/2026
Price Reduced
$1,049,999
-4.55%
MLS
1/22/2026
Price Reduced
$1,099,999
-3.51%
MLS
11/07/2025
Listed
$1,140,000
162.07%
MLS
3/04/2015
Sold
$435,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 5416 Penway Dr

Year
Property Taxes
Change
Tax Assessment
Change
2025
$8,157
3%
$426,799
6%
2024
$7,918
5%
$403,866
3%
2023
$7,524
4%
$392,103
6%
2021
$7,209
-2%
$369,595
-3%
2022
$7,338
2%
$380,683
4%
2021
$7,209
2%
$364,492
2%
2019
$7,094
—
$356,297
2%
2018
$7,100
1%
$349,654
2%
2017
$7,022
—
$342,462
2%
2016
$6,998
-22%
$335,418
-13%
2015
$8,946
5%
$386,688
9%
2014
$8,539
14%
$356,376
10%
2013
$7,516
—
$323,978
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 5416 Penway Dr

$
Down Payment
%
$
%

$
$
$

*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Listed by Exp Realty Llc

Similar Properties near 5416 Penway Dr

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

Lot #21 Karolina Ave, Winter Park, FL 32789 - Photo 1
$944,890

Lot #21 Karolina Ave  Winter Park, FL 32789

  • Single Family
  • Active
  • 4
    Beds
  • 4
    Total Baths
  • 2,662
    Sq. Ft.
Listed by Compass Florida Llc
1217 Cloverlawn Ave, Orlando, FL 32806 - Photo 1
$945,000

1217 Cloverlawn Ave  Orlando, FL 32806

  • Single Family
  • Active
  • Updated 6 days ago
  • 4
    Beds
  • 4
    Total Baths
  • 2,872
    Sq. Ft.
Listed by Real Broker, Llc
1907 Mae St, Orlando, FL 32806 - Photo 1
$919,900

1907 Mae St  Orlando, FL 32806

  • Single Family
  • Active
  • 4
    Beds
  • 4
    Total Baths
  • 2,810
    Sq. Ft.
Listed by Exit Realty Premier Legacy
[Address not provided], Orlando, FL 32806 - Photo 1 Price Reduced
-$34,500 (-3.63%)
$915,000

[Address not provided]  Orlando, FL 32806

  • Single Family
  • Active
  • Updated 15 hours ago
  • 4
    Beds
  • 4
    Total Baths
  • 2,995
    Sq. Ft.
Listed by Simplicity: A Re Brokerage Co

Just Listed near 5416 Penway Dr

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

241 W Lake Sue Ave, Winter Park, FL 32789 - Photo 1 Price Reduced
-$100,000 (-8.33%)
$1,100,000

241 W Lake Sue Ave  Winter Park, FL 32789

  • Single Family
  • Active
  • Updated 1 day ago
  • 3
    Beds
  • 3
    Total Baths
  • 2,304
    Sq. Ft.
Listed by Ken Dalton (407) 928-8587
2240 Venetian Way, Winter Park, FL 32789 - Photo 1 Just Listed
$3,500,000

2240 Venetian Way  Winter Park, FL 32789

  • Single Family
  • Active
  • Updated 4 days ago
  • 4
    Beds
  • 4
    Total Baths
  • 4,036
    Sq. Ft.
Listed by John Hurlburt (407) 579-3168
413 W Morse Blvd, Winter Park, FL 32789 - Photo 1 Just Listed
$2,695,000

413 W Morse Blvd  Winter Park, FL 32789

  • Townhouse
  • Active
  • Updated 3 days ago
  • 3
    Beds
  • 4
    Total Baths
  • 3,048
    Sq. Ft.
Listed by A.V. Blalock (407) 579-9056
700 Melrose Ave, Winter Park, FL 32789 - Photo 1 Just Listed
$235,900

700 Melrose Ave  #F 21  Winter Park, FL 32789

  • Condo
  • Active
  • Updated 3 days ago
  • 1
    Bed
  • 1
    Total Bath
  • 787
    Sq. Ft.
Listed by Fannie Hillman & Associates

Price Reduced near 5416 Penway Dr

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

241 W Lake Sue Ave, Winter Park, FL 32789 - Photo 1 Price Reduced
-$100,000 (-8.33%)
$1,100,000

241 W Lake Sue Ave  Winter Park, FL 32789

  • Single Family
  • Active
  • Updated 1 day ago
  • 3
    Beds
  • 3
    Total Baths
  • 2,304
    Sq. Ft.
Listed by Ken Dalton (407) 928-8587
3135 Heartleaf Pl, Winter Park, FL 32792 - Photo 1 Price Reduced
-$5,100 (-0.77%)
$659,900

3135 Heartleaf Pl  Winter Park, FL 32792

  • Single Family
  • Active
  • Updated 3 days ago
  • 4
    Beds
  • 3
    Total Baths
  • 2,749
    Sq. Ft.
Listed by Shirley Jones (407) 719-9180
1438 Tierra Cir, Winter Park, FL 32792 - Photo 1 Price Reduced
-$5,100 (-0.97%)
$519,900
Open House

1438 Tierra Cir  Winter Park, FL 32792

  • Single Family
  • Active
  • Updated 5 days ago
  • 3
    Beds
  • 2
    Total Baths
  • 1,627
    Sq. Ft.
Listed by Tony Nicolas (630) 514-9342
1261 Indiana Ave, Winter Park, FL 32789 - Photo 1 Price Reduced
-$4,100 (-0.76%)
$534,900
Open House

1261 Indiana Ave  Winter Park, FL 32789

  • Townhouse
  • Active
  • Updated 16 hours ago
  • 3
    Beds
  • 3
    Total Baths
  • 1,660
    Sq. Ft.
Listed by Fannie Hillman & Associates

Recent Sales near 5416 Penway Dr

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

5460 Penway Dr, Orlando, FL 32814 - Photo 1 Sold
$1,025,000

5460 Penway Dr  Orlando, FL 32814

  • Single Family
  • Closed
  • Updated 8 days ago
  • 4
    Beds
  • 4
    Total Baths
  • 2,590
    Sq. Ft.
Listed by Ingrid Livingston
Sold by Andrew Livingston
4474 Twinview Ln, Orlando, FL 32814 - Photo 1 Sold
$975,000

4474 Twinview Ln  Orlando, FL 32814

  • Townhouse
  • Closed
  • 4
    Beds
  • 4
    Total Baths
  • 3,197
    Sq. Ft.
Listed by Fannie Hillman & Associates
Sold by The Agency Fl
1954 Meeting Pl, Orlando, FL 32814 - Photo 1 Sold
$865,000

1954 Meeting Pl  Orlando, FL 32814

  • Townhouse
  • Closed
  • 4
    Beds
  • 3
    Total Baths
  • 2,410
    Sq. Ft.
Listed by Hogan Realty Group Inc
Sold by Mainframe Real Estate
4001 Corrine Dr, Orlando, FL 32814 - Photo 1 Sold
$865,000

4001 Corrine Dr  Orlando, FL 32814

  • Single Family
  • Closed
  • 4
    Beds
  • 4
    Total Baths
  • 2,965
    Sq. Ft.
Listed by Lpt Realty, Llc
Sold by Keller Williams Winter Park

5416 Penway Drive, Orlando, FL 32814 (MLS# O6357821) is a Single Family property with 4 bedrooms, 3 full bathrooms and 1 partial bathroom. 5416 Penway Drive is currently listed for $939,000 and was received on November 07, 2025. Want to learn more about 5416 Penway Drive? Do you have questions about finding other Single Family real estate for sale in Orlando? You can browse all Orlando real estate or contact a Coldwell Banker agent to request more information.

Tour this property