3209 Middlesex Rd, Orlando, FL 32803
Property image
Property image
OFF MARKET

3209 Middlesex Rd
Orlando, FL 32803

Orwin Manor
  • 4 Beds
  • 4 Baths
  • 3,374 sqft (on 0.37 acres)

$1,978,300

Trulia Estimate
as of Jul 26, 2026
Est. Refi. Payment $13,725/mo*
Refinance Your Home

$1,978,300

Trulia Estimate
as of Jul 26, 2026
Est. Refi. Payment $13,725/mo*
Refinance Your Home
4 Beds
4 Baths
3,374 sqft
(on 0.37 acres)

Local Information

  • Map ViewExplore the area around 3209 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
1959
Lot Size
0.37 acres
Living Area
3,374 sqft
Price/Sqft
$586
Parking
Garage

About this House

Beverly Shores Stunner! A Breathtaking Backyard, Light-Filled Living Spaces, and Gorgeous Hardwood Floors are a few of the extraordinary features that resonate quality and define upscale living in this charming home in the heart of the highly sought-after Rose Isle neighborhood. The ivy-adorned entryway will beckon you inside to a lifestyle of relaxed sophistication with granite countertops, Bosch stainless steel appliances, two woodburning fireplaces, plantation shutters, crown molding, and other meticulously appointed finishes. An ideal floor plan for entertaining large groups both inside and outside! Invite your guests through either of two sets of french doors onto a spacious covered lanai that overlooks an inviting pool and perfectly landscaped backyard and garden that rivals any 5-star resort. Minutes from Winter Park shopping and restaurants, Loch Haven Museums, Lake Highland Prep, and Florida Hospital.
3209 Middlesex Rd, Orlando, FL 32803 is a 4 bedroom, 4 bathroom, 3,374 sqft single-family home in Orwin Manor, built in 1959. It last sold for $800,000 on Sep 19, 2017. It is currently off market. The Trulia Estimate is $1,978,300, with a rent estimate of $4,715/month.

Home Details for 3209 Middlesex Rd

Interior Features

Heating & Cooling
Heating: Forced AirAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Interior Details
Types of Rooms: Walk In Closet, Dining Room
Appliances & Utilities
DishwasherDisposalDryerMicrowave
Fireplace & Spa
Fireplace
Levels, Entrance, & Accessibility
Floors: Tile, Hardwood

Exterior Features

Exterior Home Features
Roof: CompositionDeckPatioPorch
Pool
Pool
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 1959Year Updated: 1999
Property Type / Style
Property Type: Single Family Home

Community

Units in Building: 1

Lot Information

Lot Area: 0.37 acres

Price History for 3209 Middlesex Rd

DatePriceEventSource
09/19/2017$800,000Sold
N/A
07/05/2017$825,000PendingAgent Provided
07/01/2017$825,000Listed For SaleAgent Provided
10/01/2016$869,000ListingRemovedAgent Provided
08/29/2016$869,000PriceChange
Agent Provided
08/13/2016$889,000PendingAgent Provided
05/25/2016$889,000Listed For SaleAgent Provided
07/08/2011$695,000Sold
Stellar MLS #O5049840
12/03/2010$775,000ListingRemovedAgent Provided
08/05/2010$775,000Listed For SaleAgent Provided

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$15,200
Assessment$1,158,806
Home facts updated by county records

Comparable Sales for 3209 Middlesex Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
1513 Nottingham St, Orlando, FL
0.16
Single-Family Home
$1,750,000
12/10/25
4
3.5
2,907
3223 Middlesex Rd, Orlando, FL
0.06
Single-Family Home
$1,466,580
03/30/26
3
3
2,159
1516 Nottingham St, Orlando, FL
0.14
Single-Family Home
$860,000
05/18/26
4
3
2,080
1245 Munster St, Orlando, FL
0.17
Single-Family Home
$1,200,000
11/20/25
4
3
2,772
1426 Nottingham St, Orlando, FL
0.11
Single-Family Home
$2,668,150
09/17/25
4
4.5
3,837
215 Salvador Sq, Winter Park, FL
0.46
Single-Family Home
$1,000,000
11/03/25
4
3.5
2,565
3308 Middlesex Rd, Orlando, FL
0.12
Single-Family Home
$1,325,000
10/17/25
3
2.5
2,960
1600 Barcelona Way, Winter Park, FL
0.46
Single-Family Home
$1,305,000
11/05/25
4
3.5
3,014
1232 Ayrshire St, Orlando, FL
0.19
Single-Family Home
$1,800,000
09/25/25
4
3
3,122
1411 Nottingham St, Orlando, FL
0.15
Single-Family Home
$2,400,000
06/26/26
5
4
4,001

Nearby homes

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Assigned Schools

These are the assigned schools for 3209 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
    Flag

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Homes for sale near 3209 Middlesex Rd

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Off Market Homes Near 3209 Middlesex Rd

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