3206 Middlesex Rd, Orlando, FL 32803
Property image
Property image
OFF MARKET

3206 Middlesex Rd
Orlando, FL 32803

Orwin Manor
  • 3 Beds
  • 4 Baths
  • 3,685 sqft (on 0.57 acres)

$2,161,000

Trulia Estimate
as of Jul 9, 2026
Est. Refi. Payment $14,736/mo*
Refinance Your Home

$2,161,000

Trulia Estimate
as of Jul 9, 2026
Est. Refi. Payment $14,736/mo*
Refinance Your Home
3 Beds
4 Baths
3,685 sqft
(on 0.57 acres)

Local Information

  • Map ViewExplore the area around 3206 Middlesex Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

Own a one of kind mid-century gem with numerous upgrades and gorgeous improvements. Beautifully situated on two full lots, this home features magnificent landscaping with a newly resurfaced tiled pool and waterfall surrounded by lush tropical plants. A multilevel coy pond and waterfall graciously frame the open and spacious split floor plan. All new architectural landscape lighting lends storybook enchantment.....You won't want to leave. Chandelier does not convey. Washer and dryer do not convey. Sauna and Gazebo are "as is."
3206 Middlesex Rd, Orlando, FL 32803 is a 3 bedroom, 4 bathroom, 3,685 sqft single-family home in Orwin Manor, built in 1957. It last sold for $880,000 on Oct 10, 2008. It is currently off market. The Trulia Estimate is $2,161,000, with a rent estimate of $4,967/month.

Home Highlights

Parking
No Info
Outdoor
Pool
View
No Info
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 3206 Middlesex Rd

Interior Features

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

Property Information

Year Built
Year Built: 1957Year Updated: 1985
Property Type / Style
Property Type: Single Family Home

Exterior Features

Pool
Pool

Community

Units in Building: 1

Lot Information

Lot Area: 0.57 acres

Price History for 3206 Middlesex Rd

DatePriceEventSource
05/04/2010$895,000ListingRemovedAgent Provided
10/10/2008$880,000Sold
Stellar MLS #O4834377
08/24/2008$895,000PriceChange
Agent Provided
05/24/2008$899,000Listed For SaleAgent Provided
10/16/2007$700,000Sold
Stellar MLS #O4791163

Market trends in Orlando

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$371K
$4.33KMoM
Sale-to-List Price
97.9%
0.1%MoM
Price per sq ft
$231
$1MoM
Available listings
4113
23MoM
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Property Tax and Assessment

Year2024
Tax$12,041
Assessment$1,229,653
Home facts updated by county records

Comparable Sales for 3206 Middlesex Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
3223 Middlesex Rd, Orlando, FL
0.04
Single-Family Home
$1,466,580
03/30/26
3
3
2,159
1426 Nottingham St, Orlando, FL
0.06
Single-Family Home
$2,668,150
09/17/25
4
4.5
3,837
3308 Middlesex Rd, Orlando, FL
0.08
Single-Family Home
$1,325,000
10/17/25
3
2.5
2,960
1513 Nottingham St, Orlando, FL
0.12
Single-Family Home
$1,750,000
12/10/25
4
3.5
2,907
1516 Nottingham St, Orlando, FL
0.10
Single-Family Home
$860,000
05/18/26
4
3
2,080
1600 Barcelona Way, Winter Park, FL
0.42
Single-Family Home
$1,305,000
11/05/25
4
3.5
3,014
215 Salvador Sq, Winter Park, FL
0.43
Single-Family Home
$1,000,000
11/03/25
4
3.5
2,565
1411 Nottingham St, Orlando, FL
0.10
Single-Family Home
$2,400,000
06/26/26
5
4
4,001
1245 Munster St, Orlando, FL
0.21
Single-Family Home
$1,200,000
11/20/25
4
3
2,772
319 Santiago Dr, Winter Park, FL
0.36
Single-Family Home
$1,900,000
02/20/26
4
4.5
3,515

Nearby homes

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Assigned Schools

These are the assigned schools for 3206 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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Homes for sale near 3206 Middlesex Rd

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Off Market Homes Near 3206 Middlesex Rd

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