Recently Viewed Properties
See This Home
Save This Listing
Close

$1,325,000

  • Sold
  • Closed
  • Single Family
  • 3 Beds
  • 2 Full Baths
  • 1 Partial Bath
  • 2,960 Sq. Ft.
See This Home
Save This Home
See This Home
Save This Home
This breathtaking Spanish-style home, winner of First Place for Design by the American Society of Interior Designers in 2020, is a true masterpiece. Designed by HGTV Designer of the Year John McClain, it blends modern luxury with timeless charm. The magazine-worthy kitchen-featured on Southern Living's website-boasting Sherwin William's 2021 color of the year, the custom Urbane Bronze cabinetry acts as a chic anchor in the heart of the home while allowing the porcelain tile backsplash, quartz countertops, and modern fixtures to complete this statement piece. A gas range, custom-built hood vent, and private patio off the eat-in kitchen make this the ultimate chef's dream. Designed for entertaining, the spacious family room features wood ceiling beams, a striking tiled fireplace, and built-ins with a hidden bar lined with festive glass-beaded wallpaper and sleek quartz countertops. The formal living room, highlighted with a stunning fireplace with wood mantle flows effortlessly through french doors to a flex room with panoramic windows overlooking the spacious backyard and pool, perfect for a home gym, office, or Florida room. Outside, enjoy a heated pool with color-changing lights and a soothing waterfall, a newly built screened-in patio, and a brick paver pool deck surrounded by lush landscaping. The fully fenced backyard is a private oasis, perfect for family and pets. Even the downstairs half bath is a designer statement with wallpaper, a mirrored tile wall, and a solid wood vanity. The stunning staircase, accented with classic Spanish tile, leads to the owner's suite offering quartz counters, dual sinks, a walk-in closet, and a spacious walk-in shower, while the secondary bedrooms share a well-appointed bath upstairs as well. Featured in Interior Appeal Magazine and Haven Orlando Magazine, this extraordinary home is located in one of Orlando's most desirable neighborhoods, just minutes to Florida Hospital, Lake Highland Prep, Winter Park's Park Avenue, Mills50 shopping and dining, Fresh Market, and more. Enjoy peace of mind with a new roof in 2021, two new A/C's, stove, whole house painting, and upstairs walnut wood flooring all in 2018, as well as a new dishwasher in 2020. Too many upgrades to mention them all...see attached for a complete list. Don't miss this rare opportunity - schedule your private tour today!

Full Property Details for 3308 Middlesex Rd

General

  • Sold For: $1,325,000
  • Taxes: $17,240 (2024)
  • Status: Closed
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: O6282612
  • Added to Site: 309 day(s) ago

Rental Information

  • Min. Lease: No Minimum

Interior

  • Number of Rooms: 10
  • Interior Features: Ceiling Fan(s), Kitchen and Family Room Combination, Solid Surface Counters, Solid Wood Cabinets, Stone Counters, Tray Ceiling(s)
  • Fireplace: Yes
  • Fireplace(s): Gas
  • Appliances: Convection Oven, Cooktop, Dishwasher, Microwave, Range, Refrigerator
  • Flooring: Carpet, Tile, Hardwood

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Full Bathrooms: 2
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 3

Other Rooms

  • Laundry: Inside, Laundry Room

Additional Information

  • Pool: Yes
  • Private Pool: Yes
  • Pool Description: Gunite, In Ground, Lighting, Salt Water

Exterior

  • Exterior Features: Irrigation System, Sidewalk
  • Deck/Patio: Rear Porch, Screened
  • Porch/Patio/Deck: Rear Porch, Screened

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Covered Spaces: 2
  • Parking Features: Garage Door Opener

Location

  • Area: 32803 - Orlando/Colonial Town
  • County: Orange
  • Development Name: 32803 - Orlando/Colonial Town
  • Subdivision: ORWIN MANOR
  • Driving Directions: From Mills and Chichester, head east on Chichester. Left on Middlesex and house is on the left.
  • Direction Faces: South

School Information

  • Elementary School: Audubon Park K8
  • Middle School: Audubon Park K-8
  • High School: Edgewater High

Community

  • Community Name: 32803 - Orlando/Colonial Town

Heating & Cooling

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

Utilities

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

Structural Information

  • Architectural Info: Mediterranean
  • Architectural Style: Mediterranean
  • Exterior Const.: Stucco, Wood Frame
  • Roof: Tile
  • Stories/Levels: Two
  • Square Feet: 2,960
  • Sq. Ft. Source: Public Records
  • Living Area: 2,960 Sq. Ft.
  • Year Built: 1988

Lot Features

  • Lot Size (Acres): 0.22
  • Lot Size (Sq. Ft.): 9,801
  • Lot Size: 9801
  • Frontage: Street Paved
  • Street/Road Desc.: Paved, Asphalt
  • Fencing (Description): Fenced

Financial Considerations

  • Tax Amount: $17,240.37
  • Tax Year: 2024

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: ORWIN MANOR LAKE SHORE SECTION M/104 BEG50 FT E OF NW COR LOT 22 RUN E 75 FT S51.83 FT S 58 DEG W 88.2 FT N 98.9 FT TOPOB & BEG NW COR OF LOT 22 RUN E 50 FTS 98.9 FT S 58 DEG W 28.3 FT N 14 DEG W106.7 FT N 10 FT TO POB BLK 36 IN SEC 18-22-30 NW1/4
  • Flood Zone Info: X
  • APN: 122229644436220
  • Property ID: 122229644436220
  • Block/Lot/Section: 36

Listed by Stockworth Realty Group
Sold by Key Realty Group Llc

Listing agent

— 3308 Middlesex Rd —

  • Stockworth Realty Group

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 3308 Middlesex Rd

School District:Orange County School District
NameGradesDistance
Audubon Park School
1500 Falcon Drive, Orlando, FL 32803
PK-81.3 mi
Edgewater High School
3100 Edgewater Drive, Orlando, FL 32804
9-122.1 mi
Winter Park High School
2100 Summerfield Road, Winter Park, FL 32792
9-122.2 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 3308 Middlesex Rd

Date
Details
Price
Change
Source
10/17/2025
Sold
$1,325,000
-1.85%
MLS
7/12/2025
Price Reduced
$1,350,000
-6.9%
MLS
5/09/2025
Price Reduced
$1,450,000
-4.92%
MLS
3/13/2025
Listed
$1,525,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Listed by Stockworth Realty Group
Sold by Key Realty Group Llc

Similar Properties near 3308 Middlesex Rd

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

1007 Bennett Rd, Orlando, FL 32814 - Photo 1
$1,250,000

1007 Bennett Rd  Orlando, FL 32814

  • Single Family
  • Active
  • 3
    Beds
  • 3
    Total Baths
  • 3,099
    Sq. Ft.
Listed by Listwithfreedom.Com
3807 S Semoran Blvd, Orlando, FL 32822 - Photo 1
$1,400,000

3807 S Semoran Blvd  Orlando, FL 32822

  • Single Family
  • Active
  • 3
    Beds
  • 3
    Total Baths
  • 2,431
    Sq. Ft.
Listed by Mbt Realty Llc
808 Edgewater Dr, Orlando, FL 32804 - Photo 1 Price Reduced
-$50,000 (-3.85%)
$1,249,999
Open House

808 Edgewater Dr  Orlando, FL 32804

  • Single Family
  • Active
  • Updated 3 days ago
  • 3
    Beds
  • 4
    Total Baths
  • 2,413
    Sq. Ft.
Listed by The Agency Orlando
1540 Miller Ave, Winter Park, FL 32789 - Photo 1
$1,399,900

1540 Miller Ave  Winter Park, FL 32789

  • Single Family
  • Active
  • 4
    Beds
  • 4
    Total Baths
  • 2,984
    Sq. Ft.
Listed by Re/Max Exclusive Collection

Just Listed near 3308 Middlesex Rd

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

5117 Stratemeyer Dr, Edgewood, FL 32839 - Photo 1 Just Listed
$479,990
Open House

5117 Stratemeyer Dr  Edgewood, FL 32839

  • Single Family
  • Active
  • Updated 10 hours ago
  • 4
    Beds
  • 3
    Total Baths
  • 2,180
    Sq. Ft.
Listed by Keller Williams Winter Park
1552 Florentino Ln, Winter Park, FL 32792 - Photo 1 Just Listed
$364,900

1552 Florentino Ln  Winter Park, FL 32792

  • Townhouse
  • Active
  • Updated 6 days ago
  • 3
    Beds
  • 3
    Total Baths
  • 1,682
    Sq. Ft.
Listed by Nohora Gomez Pro Group (407) 647-1211
1602 Alabama Dr, Winter Park, FL 32789 - Photo 1 Just Listed
$1,250,000

1602 Alabama Dr  #403  Winter Park, FL 32789

  • Condo
  • Active
  • Updated 1 day ago
  • 2
    Beds
  • 2
    Total Baths
  • 1,402
    Sq. Ft.
Listed by Corcoran Premier Realty
1221 Richmond Rd, Winter Park, FL 32789 - Photo 1 Just Listed
$5,250,000

1221 Richmond Rd  Winter Park, FL 32789

  • Single Family
  • Active
  • Updated 15 hours ago
  • 5
    Beds
  • 6
    Total Baths
  • 5,164
    Sq. Ft.
Listed by Premier Sotheby's Intl. Realty

Price Reduced near 3308 Middlesex Rd

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

422 S Ranger Blvd, Winter Park, FL 32792 - Photo 1 Price Reduced
-$10,100 (-1.94%)
$509,900

422 S Ranger Blvd  Winter Park, FL 32792

  • Single Family
  • Active
  • Updated 2 days ago
  • 4
    Beds
  • 2
    Total Baths
  • 1,680
    Sq. Ft.
Listed by David Perez (407) 701-1482
2215 Marsh Sedge Ln, Winter Park, FL 32792 - Photo 1 Price Reduced
-$24,100 (-3.02%)
$774,900
Open House

2215 Marsh Sedge Ln  Winter Park, FL 32792

  • Single Family
  • Active
  • Updated 3 days ago
  • 5
    Beds
  • 3
    Total Baths
  • 2,646
    Sq. Ft.
Listed by Exp Realty Llc
428 Selkirk Dr, Winter Park, FL 32792 - Photo 1 Price Reduced
-$15,000 (-2.31%)
$635,000
Open House

428 Selkirk Dr  Winter Park, FL 32792

  • Single Family
  • Active
  • Updated 3 days ago
  • 4
    Beds
  • 3
    Total Baths
  • 1,782
    Sq. Ft.
Listed by Redfin Corporation
1531 Lawndale Cir, Winter Park, FL 32792 - Photo 1 Price Reduced
-$6,000 (-1.55%)
$380,000
Open House

1531 Lawndale Cir  Winter Park, FL 32792

  • Single Family
  • Active
  • Updated 5 days ago
  • 3
    Beds
  • 2
    Total Baths
  • 1,300
    Sq. Ft.
Listed by Top Value Properties Llc

Recent Sales near 3308 Middlesex Rd

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

1742 Barcelona Way, Winter Park, FL 32789 - Photo 1 Sold
$1,480,000

1742 Barcelona Way  Winter Park, FL 32789

  • Single Family
  • Closed
  • 5
    Beds
  • 8
    Total Baths
  • 3,626
    Sq. Ft.
Listed by Kelly Price & Company Llc
Sold by Premier Sotheby's Intl. Realty
1245 Munster St, Orlando, FL 32803 - Photo 1 Sold
$1,200,000

1245 Munster St  Orlando, FL 32803

  • Single Family
  • Closed
  • 4
    Beds
  • 3
    Total Baths
  • 2,772
    Sq. Ft.
Listed by Keller Williams Winter Park
Sold by Florida Executive Realty
1600 Barcelona Way, Winter Park, FL 32789 - Photo 1 Sold
$1,305,000

1600 Barcelona Way  Winter Park, FL 32789

  • Single Family
  • Closed
  • 4
    Beds
  • 4
    Total Baths
  • 3,014
    Sq. Ft.
Listed by Lpt Realty, Llc
Sold by Stellar Non-Member Office
1400 S Pennsylvania Ave, Winter Park, FL 32789 - Photo 1 Sold
$1,300,000

1400 S Pennsylvania Ave  Winter Park, FL 32789

  • Single Family
  • Closed
  • Updated 10 days ago
  • 4
    Beds
  • 3
    Total Baths
  • 2,310
    Sq. Ft.
Listed by Jack Keller Inc
Sold by Stellar Non-Member Office

3308 Middlesex Road, Orlando, FL 32803 (MLS# O6282612) is a Single Family property that was sold at $1,325,000 on October 17, 2025. Want to learn more about 3308 Middlesex Road? 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.