3308 Middlesex Rd, Orlando, FL 32803
SOLD
OCT 17, 2025

3308 Middlesex Rd
Orlando, FL 32803

Orwin Manor
  • 3 Beds
  • 2.5 Baths
  • 2,960 sqft

$1,325,000

Last Sold: Oct 17, 2025
2% below list $1.35M
$448/sqft
Est. Refi. Payment $9,016/mo*
Refinance Your Home

$1,325,000

Last Sold: Oct 17, 2025
2% below list $1.35M
$448/sqft
Est. Refi. Payment $9,016/mo*
Refinance Your Home
3 Beds
2.5 Baths
2,960 sqft

Local Information

  • Map ViewExplore the area around 3308 Middlesex Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

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!
3308 Middlesex Rd, Orlando, FL 32803 is a 3 bedroom, 3 bathroom, 2,960 sqft single-family home in Orwin Manor, built in 1988. It last sold for $1,325,000 on Oct 17, 2025 (2% below the $1,350,000 asking price). It is currently off market. The Trulia Estimate is $1,333,100, with a rent estimate of $4,526/month.

Home Highlights

Parking
2 Car Garage
Outdoor
Porch, Pool
View
No Info
HOA
None
Price/Sqft
$448/sqft
Listed
180+ days ago

Home Details for 3308 Middlesex Rd

Interior Features

Interior Details
Number of Rooms: 10Types of Rooms: Primary Bedroom, Bedroom 2, Bedroom 3, Primary Bathroom, Dinette, Dining Room, Family Room, Kitchen, Living Room, Office
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 3Number of Bathrooms (full): 2Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 2960 Square Feet
Appliances & Utilities
Utilities: Cable Connected, Electricity Connected, Sewer Connected, Water ConnectedAppliances: Convection Oven, Cooktop, Dishwasher, Microwave, Range, RefrigeratorDishwasherLaundry: Inside,Laundry RoomMicrowaveRefrigerator
Heating & Cooling
Heating: Central,ElectricHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Central
Fireplace & Spa
Fireplace: GasHas a FireplaceNo Spa
Gas & Electric
Has Electric on Property
Windows, Doors, Floors & Walls
Flooring: Carpet, Tile, Hardwood
Levels, Entrance, & Accessibility
Stories: 2Levels: TwoFloors: Carpet, Tile, Hardwood
View
No View

Exterior Features

Exterior Home Features
Roof: TilePatio / Porch: Rear Porch, ScreenedFencing: FencedVegetation: Trees/LandscapedExterior: Irrigation System, SidewalkFoundation: SlabHas a Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas an Attached GarageParking Spaces: 2Parking: Garage Door Opener
Pool
Pool: Gunite, In Ground, Lighting, Salt WaterPool
Frontage
Road Surface Type: Paved, AsphaltNot on Waterfront
Water & Sewer
Sewer: Public Sewer

Days on Market

Cumulative Days on Market: 175

Property Information

Year Built
Year Built: 1988
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Mediterranean
Building
Construction Materials: Stucco, Wood FrameNot a New ConstructionNot Attached PropertyNo Additional Parcels
Property Information
Parcel Number: 122229644436220

Price & Status

Price
List Price: $1,350,000Price Per Sqft: $448/sqft
Status Change & Dates
Off Market Date: Thu Sep 04 2025

Active Status

MLS Status: Sold

Media

Location

Direction & Address
City: ORLANDOCommunity: ORWIN MANOR
School Information
Elementary School: Audubon Park K8Jr High / Middle School: Audubon Park K-8High School: Edgewater High

Building

Building Area
Building Area: 4031 Square Feet

Community

Not Senior Community

HOA

Association for this Listing: Orlando RegionalNo HOA

Lot Information

Lot Area: 9801 sqft

Listing Info

Special Conditions: None

Offer

Listing Terms: Cash, Conventional, FHA, VA Loan

Business

Business Information
Ownership: Fee Simple

Miscellaneous

Mls Number: O6282612Showing Advance Notice: 24Showing Requirements: 24 Hour Notice, See Remarks, ShowingTimeUniversal Property Id: US-12095-N-122229644436220-R-N
Last check for updates: about 3 hours ago
Listed by Julie Bettosini, PA, (321) 689-9594
STOCKWORTH REALTY GROUP, (407) 909-5900
Bought with: Desiree Mellott, (863) 241-8096, KEY REALTY GROUP LLC, (863) 241-8096
Originating MLS: Orlando Regional
Source: Stellar MLS, MLS#O6282612
IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. Some IDX listings have been excluded from this website.
Listing Information presented by local MLS brokerage: Zillow, Inc - (407) 904-3511

Price History for 3308 Middlesex Rd

DatePriceEventSource
10/17/2025$1,325,000Sold
Stellar MLS #O6282612
09/05/2025$1,350,000PendingStellar MLS #O6282612
07/12/2025$1,350,000PriceChange
Stellar MLS #O6282612
05/09/2025$1,450,000PriceChange
Stellar MLS #O6282612
03/14/2025$1,525,000Listed For SaleStellar MLS #O6282612
03/01/2021$1,040,000Sold
Stellar MLS #O5914328
01/14/2021$1,049,000PendingStellar MLS #O5914328
01/04/2021$1,049,000Listed For SaleAgent Provided
09/01/2018$715,000Sold
N/A
06/28/2018$789,000Listed For SaleAgent Provided
07/31/2015$625,000Sold
N/A
07/06/2015$650,000PendingToActiveAgent Provided
07/06/2015$650,000PendingAgent Provided
07/02/2015$650,000PendingToActiveAgent Provided
06/28/2015$650,000PendingAgent Provided
03/14/2015$650,000PriceChange
Agent Provided
01/17/2015$690,000PriceChange
Agent Provided
11/14/2014$739,000PriceChange
Agent Provided
07/26/2014$789,000PriceChange
Agent Provided
06/15/2014$819,000Listed For SaleAgent Provided
06/18/1996$277,000Sold
N/A

Market trends in Orlando

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$381K
$9.25KMoM
Sale-to-List Price
98.0%
0.1%MoM
Price per sq ft
$232
$1MoM
Available listings
4173
53MoM
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Property Tax and Assessment

Year2024
Tax$17,240
Assessment$1,077,790
Home facts updated by county records

Comparable Sales for 3308 Middlesex Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
3223 Middlesex Rd, Orlando, FL
0.07
Single-Family Home
$1,466,580
03/30/26
3
3
2,159
1516 Nottingham St, Orlando, FL
0.02
Single-Family Home
$860,000
05/18/26
4
3
2,080
1245 Munster St, Orlando, FL
0.29
Single-Family Home
$1,200,000
11/20/25
4
3
2,772
1513 Nottingham St, Orlando, FL
0.06
Single-Family Home
$1,750,000
12/10/25
4
3.5
2,907
1232 Ayrshire St, Orlando, FL
0.30
Single-Family Home
$1,800,000
09/25/25
4
3
3,122
1400 S Pennsylvania Ave, Winter Park, FL
0.35
Single-Family Home
$1,300,000
01/02/26
4
3
2,310
1213 Richmond Rd, Winter Park, FL
0.51
Single-Family Home
$1,150,000
09/12/25
4
3
3,204
1600 Barcelona Way, Winter Park, FL
0.35
Single-Family Home
$1,305,000
11/05/25
4
3.5
3,014
1919 Lakeside Dr, Orlando, FL
0.57
Single-Family Home
$1,875,000
10/28/25
3
2.5
2,633

Nearby homes

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Assigned Schools

These are the assigned schools for 3308 Middlesex Rd.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

Neighborhood Overview

Orwin Manor
See Local Highlights
Neighborhood stats provided by third party data sources.

What Locals Say about Orwin Manor

At least 34 Trulia users voted on each feature.

  • 92 % Say there are sidewalks

  • 88 % Say it's dog friendly

  • 85 % Say parking is easy

  • 81 % Say car is needed

  • 77 % Say yards are well-kept

  • 68 % Say there's holiday spirit

  • 68 % Say they plan to stay for at least 5 years

  • 64 % Say people would walk alone at night

  • 59 % Say streets are well-lit

  • 56 % Say it's quiet

  • 55 % Say it's walkable to restaurants

  • 50 % Say it's walkable to grocery stores

  • 48 % Say neighbors are friendly

  • 45 % Say kids play outside

  • 41 % Say there's wildlife

  • 32 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Sallymac
    "Great location. Heart of town! Great neighbors, great walking neighborhood, acres to Mead Garden and walkable to many nearby shops and restaurants , "
    0
    Flag
  • Sallymac
    "I have lived her for 19 months. We are so happy. We walk to Mead Gardens. Friendly neighbors and great tree lined streets! "
    0
    Flag
  • Blessedandres
    "We have a church nearby. St Johns Lutheran Church. Most of the activities are nearby. The streets are not well lit though. Its very dark at night."
    1
    Flag
  • King F.
    "Location, Location, Location. Rose Isle/Beverly Shores is within minutes of downtown Winter Park with direct access to downtown Orlando, I-4, and Florida Hospital. It's one of the most sought after neighborhoods in the entire area, on the shores of Winter Park Lake Sue."
    1
    Flag
  • Sliotta
    "The location of the neighborhood is ideally located between downtown Orlando, Winter Park. Also offers great access to I-4z"
    0
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Off Market Homes Near 3308 Middlesex Rd

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