3333 Middlesex Rd, Orlando, FL 32803
OFF MARKET

$976,600

Trulia Estimate
  • 3 Beds
  • 2 Baths
  • 1,688 sqft

3333 Middlesex Rd, Orlando, FL 32803

Orwin Manor
Est. Refi. Payment $6,793/mo*
Refinance Your Home

Home Value

Trulia Estimate
$977K
Since last month
Increased$38K (+4%)
Since last year
Increased$118K (+13.8%)
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 +131% in the last 10 years
MonthEstimated value
2026
August 2026$975K
July 2026$937K
June 2026$992K
May 2026$964K
April 2026$950K
March 2026$955K
February 2026$947K
January 2026$940K
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
1516 NOTTINGHAM STREET, Orlando, FL
0.05
Single-Family Home
$860,000
05/18/26
4
3
2,080
3308 MIDDLESEX ROAD, Orlando, FL
0.04
Single-Family Home
$1,325,000
10/17/25
3
2.5
2,960
1224 NOTTINGHAM STREET, Orlando, FL
0.31
Single-Family Home
$900,000
07/31/26
3
2
1,560
1313 S DENNING DRIVE, Winter Park, FL
0.36
Single-Family Home
$300,000
03/27/26
3
2
1,700
1201 NOTTINGHAM STREET, Orlando, FL
0.40
Single-Family Home
$675,000
03/09/26
3
2
1,696
3223 MIDDLESEX ROAD, Orlando, FL
0.09
Single-Family Home
$1,466,580
03/30/26
3
3
2,159
1347 ORCHID AVENUE, Winter Park, FL
0.41
Single-Family Home
$445,000
03/20/26
4
2
1,490
1216 CHICHESTER STREET, Orlando, FL
0.34
Single-Family Home
$1,295,000
08/17/26
3
2
2,366
1105 NOTTINGHAM STREET, Orlando, FL
0.45
Single-Family Home
$668,500
03/04/26
3
2
1,595
1550 NORFOLK AVENUE, Winter Park, FL
0.53
Single-Family Home
$695,000
06/05/26
3
2
1,762

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
3322 LAKE SHORE DRIVE, Orlando, FL 32803
0.04
$2,459,300
3
2.5
2,633
Off Market
3308 MIDDLESEX ROAD, Orlando, FL 32803
0.04
$1,319,400
3
2.5
2,960
Off Market
1516 NOTTINGHAM STREET, Orlando, FL 32803
0.05
$860,000
4
3
2,080
Recently Sold
1500 NOTTINGHAM STREET, Orlando, FL 32803
0.06
$1,825,000
5
3.5
2,976
Recently Sold
1513 NOTTINGHAM STREET, Orlando, FL 32803
0.08
$1,750,000
4
3.5
2,907
Recently Sold
3223 MIDDLESEX ROAD, Orlando, FL 32803
0.09
$1,466,580
3
3
2,159
Recently Sold
1426 NOTTINGHAM STREET, Orlando, FL 32803
0.10
$2,650,900
4
4.5
3,837
Off Market
1411 NOTTINGHAM STREET, Orlando, FL 32803
0.14
$2,400,000
5
4
4,001
Recently Sold
1711 BARCELONA WAY, Winter Park, FL 32789
0.16
$2,010,000
5
3
3,669
Recently Sold
3202 MIDDLESEX ROAD, Orlando, FL 32803
0.16
$1,693,000
4
2.5
2,817
Off Market
1400 NOTTINGHAM STREET, Orlando, FL 32803
0.15
$3,188,000
5
5.5
4,369
Off Market
1742 BARCELONA WAY, Winter Park, FL 32789
0.17
$1,470,700
5
7
3,626
Off Market

Local Information

  • Map ViewExplore the area around 3333 Middlesex Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1950
Living Area
1,688 sqft
Price/Sqft
$579
Parking
Garage

About this House

This single-family home is located at 3333 Middlesex Rd, Orlando, FL. 3333 Middlesex Rd is in the Orwin Manor neighborhood in Orlando, FL and in ZIP code 32803. This property has 3 bedrooms, 2 bathrooms and approximately 1,688 sqft of floor space. This property has a lot size of 9336 sqft and was built in 1950.
3333 Middlesex Rd, Orlando, FL 32803 is a 3 bedroom, 2 bathroom, 1,688 sqft single-family home in Orwin Manor, built in 1950. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $976,600, with a rent estimate of $2,832/month.

Home Details for 3333 Middlesex Rd

Interior Features

Heating & Cooling
Heating: Forced AirCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 1

Exterior Features

Exterior Home Features
Roof: Composition
Pool
Pool
Parking & Garage
GarageParking: Garage

Property Information

Year Built
Year Built: 1950Year Updated: 1970
Property Type / Style
Property Type: Single Family Home

Community

Units in Building: 1

Lot Information

Lot Area: 9336 sqft

Price and Tax history

YearProperty taxTax assessment
2024
$4,136
$631,833
Home facts updated by county records

Market trends in Orlando

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$384K
$3.67KMoM
Sale-to-List Price
98.1%
0.1%MoM
Price per sq ft
$233
$1MoM
Available listings
4195
15MoM

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 3333 Middlesex Rd

  • What is 3333 Middlesex Rd estimated to be worth?
    Trulia's estimated value for 3333 Middlesex Rd in Orlando, FL is $976,600.
  • 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 $384K. That is up $3.67K from the prior month.
  • What do residents say about the Orwin Manor neighborhood?
    Residents describe the Orwin Manor neighborhood in Orlando, FL as pedestrian-friendly, dog-friendly, and easy to park in. See recently sold homes in Orwin Manor, Orlando.
  • Does 3333 Middlesex Rd have air conditioning?
    Yes, 3333 Middlesex Rd in Orlando, FL has air conditioning.
  • Does 3333 Middlesex Rd have a pool?
    Yes, 3333 Middlesex Rd in Orlando, FL has a pool.

Explore by feature - Pet Friendly

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Explore by feature - Outdoor Space

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Apartments for Rent

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Off Market Homes Near 3333 Middlesex Rd

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