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Judson Osbon

Judson Osbon
Real Estate Agent (Salesperson)
Winter Garden FL

Salesperson (FL: 3366745)

10 years experience

REALTOR® 4 Active Listings Serves Orange County, FL
View on Realtor.com

Contact Information

Brokerage
Re/Max Prime Properties
Office Address
13848 Tilden Rd
Winter Garden, FL  34787
(Orange County)
Office Phone
407-347-4512
Office Fax
941-203-8633
Mobile
407-955-1672
Email
theo*********@*****.com
Show Email for $5

Service Areas

Bay Hill: FL Lake Buena Vista: FL Golden Oak: FL Bay Lake: FL Horizon West: FL Doctor Phillips: FL Groveland: FL Clermont: FL Four Corners: FL Gotha: FL Lake Butler: FL Windermere: FL Killarney: FL Oakland: FL Winter Garden: FL Tildenville: FL Minneola: FL Montverde: FL Ferndale: FL Orlando: FL

About Judson Osbon

At the age of 23, he purchased his first home and began a successful house-hacking venture, renting out two additional bedrooms long before the term gained popularity. After meeting his future wife, he transitioned from shared living to a more private space, ultimately undertaking a complete renovation of the property over a decade. As a hands-on individual, he managed all aspects of the project, including leveling the pier and beam foundation. The sale of this home provided the financial means for a seamless relocation to Florida.

Currently, he serves as a Realtor in Florida, driven by a passion for buy-and-hold investment strategies. After years of experience as a residential agent and absorbing insights from numerous BiggerPockets podcasts, he overcame his tendencies toward analysis paralysis and shiny object syndrome. In 2021, he made his first investment by acquiring a duplex, followed shortly by the purchase of a new construction home, which allowed him to convert his previous residence into a profitable rental property.

He takes particular pleasure in assisting new and first-time investors in their property searches, fostering growth and success together.

Orange County, FL Real Estate Market Analysis (Single Family Homes)

$779,154
Avg. Listing Price
From Judson's portfolio
3.8 / 3.0
Avg. Beds/Baths
Typical property size
2,426 sf
Avg. Square Footage
Interior living space
5749
Active Listings
Current inventory

Orange County, Florida stands as one of the most dynamic and complex real estate markets in the Southeast, driven by the powerful economic engines of tourism, aerospace, and technology. Home to Walt Disney World, Universal Studios, and a thriving metropolitan area centered around Orlando, this market attracts everyone from international investors seeking vacation rental properties to young professionals relocating for career opportunities in the region's booming tech corridor.

What makes Orange County particularly fascinating is its remarkable agent density, with 40,940 total actively licensed agents serving the region's diverse real estate needs. This substantial professional network, all equipped with email contact information, reflects the market's sophistication and the high volume of transactions flowing through communities ranging from luxury lakefront properties in Windermere to urban condominiums in downtown Orlando.

Major Orange County, Florida Real Estate Markets

The Orlando metropolitan area dominates Orange County's real estate landscape, encompassing everything from the tourist corridor along International Drive to the upscale communities of Winter Park and Maitland. Each submarket serves distinct buyer profiles: vacation home investors gravitate toward properties near theme parks in areas like Kissimmee and Bay Lake, while permanent residents often prefer established neighborhoods in Apopka, Ocoee, and Belle Isle that offer better schools and community amenities.

Beyond Orlando proper, emerging markets in places like Horizon West and the Dr. Phillips area have become hotbeds for new construction and master-planned communities. These regions attract families and retirees seeking modern amenities and proximity to employment centers, while historic areas like Eatonville and Conway offer more affordable entry points into the Orange County market with their own unique character and revitalization potential.

Market Dynamics and Geographic Complexity

Orange County's real estate market operates on multiple speed settings simultaneously, creating unique challenges for agents and opportunities for savvy businesses. The vacation rental market moves at breakneck pace, with properties in prime tourist areas changing hands quickly and often sight unseen by out-of-state investors. Meanwhile, the traditional residential market follows more predictable seasonal patterns, with snowbird migration and theme park employment cycles driving distinct busy periods throughout the year.

Geographic complexity adds another layer of intrigue, as lakefront properties command premium prices in communities like Lake Nona and Celebration, while urban infill projects in areas like Parramore and Colonialtown are reshaping downtown Orlando's residential landscape. This diversity means agents must navigate everything from million-dollar estates to first-time buyer condominiums, often within the same ZIP code, requiring specialized knowledge that varies dramatically by micromarket.

Why Businesses Need Orange County, Florida Agent Contact Data

With 40,940 actively licensed agents operating across Orange County's multifaceted market, businesses in real estate services, financial services, and construction face the challenge of identifying and reaching the right professionals for their specific offerings. Whether you're a mortgage lender seeking agents who work with international buyers, a home inspector targeting new construction specialists, or a property management company looking to connect with vacation rental focused agents, having comprehensive contact data becomes essential for efficient business development.

The sheer scale and diversity of Orange County's agent population means that successful business outreach requires precision targeting rather than broad-brush approaches. Companies that can effectively segment and communicate with specific agent groups—such as those specializing in luxury properties, commercial real estate, or first-time buyer programs—will find significantly better response rates and partnership opportunities in this competitive but lucrative market environment.

Current Property Listings

As of 2/13/2026, Judson Osbon has 4 properties for sale in Winter Garden and surrounding areas.

$149,900

Listed 2025-08-29

28803 Hubbard St
Leesburg, FL  34748

Beds: 4.0
Baths: 2.0
Sq Ft: 1,728
Lot: 14,810 sf
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$750,000

Listed 2023-12-09

12 Lee St
Ocoee, FL  34761

Beds: 3.0
Baths: 2.0
Sq Ft: 1,648
Lot: 196,020 sf
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$415,000

Listed 2026-01-09

435 Loblolly Ln
Orlando, FL  32825

Beds: 3.0
Baths: 2.5
Sq Ft: 1,634
Lot: 4,792 sf
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$269,000

Listed 2025-04-25

2763 E Waco Dr
Deltona, FL  32738

Beds: 3.0
Baths: 2.0
Sq Ft: 1,266
Lot: 10,019 sf
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Current Property Rentals

As of 2/13/2026, Judson Osbon has the following rental properties available in Winter Garden and surrounding areas.

$2,950

Listed 2025-10-27

3024 Armstrong Ave
Clermont, FL  34714

Beds: 4.0
Baths: 3.0
Sq Ft: 2,274
Lot: 6,098 sf
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$3,000

Listed 2026-02-03

7902 Syracuse Dr
Clermont, FL  34714

Beds: 4.0
Baths: 2.5
Sq Ft: 2,536
Lot: 5,663 sf
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$3,000

Listed 2026-02-03

2345 Treasure Hill St
Clermont, FL  34715

Beds: 4.0
Baths: 2.5
Sq Ft: 2,082
Lot: 4,792 sf
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$2,625

Listed 2025-11-12

157 Loblolly Ln
Davenport, FL  33837

Beds: 4.0
Baths: 2.0
Sq Ft: 2,234
Lot: 11,326 sf
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