3308 MIDDLESEX ROAD, Orlando, FL 32803
OFF MARKET

$1,313,300

Trulia Estimate
  • 3 Beds
  • 2.5 Baths
  • 2,960 sqft

3308 MIDDLESEX ROAD, Orlando, FL 32803

Orwin Manor
Est. Refi. Payment $9,354/mo*
Refinance Your Home
Currently Off Market - Sold Oct 17, 2025 for $1,325,000

Home Value

Trulia Estimate
$1.31M
Since last month
Decreased$5K (-0.3%)
Since last year
Increased$31K (+2.4%)
Since last sale
Decreased$13K (-1%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +96% in the last 10 years
MonthEstimated value
2026
September 2026$1.31M
August 2026$1.32M
July 2026$1.33M
June 2026$1.34M
May 2026$1.33M
April 2026$1.32M
March 2026$1.3M
February 2026$1.31M
January 2026$1.32M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
3223 MIDDLESEX ROAD, Orlando, FL
0.07
Single-Family Home
$1,466,580
03/30/26
3
3
2,159
1516 NOTTINGHAM STREET, Orlando, FL
0.02
Single-Family Home
$860,000
05/18/26
4
3
2,080
1245 MUNSTER STREET, Orlando, FL
0.29
Single-Family Home
$1,200,000
11/20/25
4
3
2,772
1500 NOTTINGHAM STREET, Orlando, FL
0.02
Single-Family Home
$1,825,000
07/31/26
5
3.5
2,976
1513 NOTTINGHAM STREET, Orlando, FL
0.06
Single-Family Home
$1,750,000
12/10/25
4
3.5
2,907
1216 CHICHESTER STREET, Orlando, FL
0.29
Single-Family Home
$1,295,000
08/17/26
3
2
2,366
1232 AYRSHIRE STREET, Orlando, FL
0.30
Single-Family Home
$1,800,000
09/25/25
4
3
3,122
3300 SHERWOOD ROAD, Orlando, FL
0.19
Single-Family Home
$950,000
09/04/26
3
2
1,673
1224 NOTTINGHAM STREET, Orlando, FL
0.27
Single-Family Home
$900,000
07/31/26
3
2
1,560

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
1500 NOTTINGHAM STREET, Orlando, FL 32803
0.02
$1,825,000
5
3.5
2,976
Recently Sold
1516 NOTTINGHAM STREET, Orlando, FL 32803
0.02
$860,000
4
3
2,080
Recently Sold
3223 MIDDLESEX ROAD, Orlando, FL 32803
0.07
$1,466,580
3
3
2,159
Recently Sold
1426 NOTTINGHAM STREET, Orlando, FL 32803
0.06
$2,640,300
4
4.5
3,837
Off Market
1513 NOTTINGHAM STREET, Orlando, FL 32803
0.06
$1,750,000
4
3.5
2,907
Recently Sold
3322 LAKE SHORE DRIVE, Orlando, FL 32803
0.07
$2,479,200
3
2.5
2,633
Off Market
1411 NOTTINGHAM STREET, Orlando, FL 32803
0.10
$2,400,000
5
4
4,001
Recently Sold
1400 NOTTINGHAM STREET, Orlando, FL 32803
0.11
$3,177,900
5
5.5
4,369
Off Market
3202 MIDDLESEX ROAD, Orlando, FL 32803
0.12
$1,736,700
4
2.5
2,817
Off Market
914 GROVER AVENUE, Winter Park, FL 32789
0.18
$497,200
2
1
1,209
Off Market
3300 SHERWOOD ROAD, Orlando, FL 32803
0.19
$950,000
3
2
1,673
Recently Sold

Local Information

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

Home Highlights

Single-Family Home
Built in 1988
2,960 sqft
$444/sqft
2 Car Garage

About this House

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 ROAD, 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). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,313,300, with a rent estimate of $5,034/month.
Last check for updates: about 23 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

Home Details for 3308 MIDDLESEX ROAD

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: $1,350,000
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

Price and Tax history

DateEventPrice
Oct 17, 2025
Source: Stellar MLS #O6282612
Sold
$1,325,000
Sep 5, 2025
Source: Stellar MLS #O6282612
Pending
$1,350,000
Jul 12, 2025
Source: Stellar MLS #O6282612
PriceChange
$1,350,000
Price decreased by 7%
May 9, 2025
Source: Stellar MLS #O6282612
PriceChange
$1,450,000
Price decreased by 5%
Mar 14, 2025
Source: Stellar MLS #O6282612
Listed For Sale
$1,525,000

Market trends in Orlando

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$387K
$2.53KMoM
Sale-to-List Price
98.1%
Price per sq ft
$233
$1MoM
Available listings
4176
24MoM

Around this home

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
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 3308 MIDDLESEX ROAD

  • What is 3308 MIDDLESEX ROAD estimated to be worth?
    Trulia's estimated value for 3308 MIDDLESEX ROAD in Orlando, FL is $1,313,300.
  • What is the price history for 3308 MIDDLESEX ROAD?
    3308 MIDDLESEX ROAD in Orlando, FL last sold for $1,325,000 in October 2025.
  • Is Orlando a buyer's or seller's market?
    Orlando is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Orlando?
    The median sale price in Orlando is $387K. That is up $2.53K from the prior month.
  • Does 3308 MIDDLESEX ROAD have air conditioning?
    Yes, 3308 MIDDLESEX ROAD in Orlando, FL has air conditioning.
  • Does 3308 MIDDLESEX ROAD have a pool?
    Yes, 3308 MIDDLESEX ROAD in Orlando, FL has a pool.

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