- Agent Pronto
- Florida
- Winter Garden
- Reuben Simmonds
Looking to sell your property, buy a new home, or just need some expert real estate advice?
With over 26 years of real estate experience and more than 520 closed career transactions, Reuben Simmonds is a seasoned Central Florida real estate professional and U.S. military veteran with Blair Realty Group. Reuben delivers tailored, high-performance real estate services to home buyers and sellers across West Orange and South Lake Counties.
Specializing in high-velocity communities including Winter Garden (34787), Horizon West, Ocoee, Clermont, and Windermere, Reuben combines deep local market expertise with an in-depth understanding of military relocations, VA loan processes, and move-up buyer strategies. Whether assisting military families utilizing their VA home benefits or helping local homeowners maximize their listing equity, Reuben leverages a quarter-century of proven negotiation power to ensure seamless communication, fast execution, and outstanding results from offer to closing.
- 7
- Recent sales
- $185K-$1.72M
- Price range
- $275K
- Median price
- 26
- Years experience
Recent Listings & Sales
| Address | Sold Date | Sold Price | Represented |
|---|---|---|---|
|
520 Georgetown Dr
Casselberry, FL 32707
|
8/12/2026 | $184,800 | Seller |
|
4664 Pleasant Valley Ct
Orlando, FL 32811
|
4/1/2026 | $275,000 | Buyer |
|
6816 SW 4th Pl
Gainesville, FL 32607
|
7/1/2025 | $1,720,000 | Buyer |
|
1130 E Bay St
Winter Garden, FL 34787
|
5/28/2025 | $210,000 | Seller |
|
6088 Terrell Rd
Mount Dora, FL 32757
|
11/6/2024 | Not available | Buyer |
Transaction History *
Seller Deals
- Total Deals
- 1
- Total Value
- $184,800
- Median Sale Price
- -
- Price Range
- -
Buyer Deals
- Total Deals
- 1
- Total Value
- $275,000
- Median Sale Price
- -
- Price Range
- -
Sales Volume Timeline
Seller Deals
- Total Deals
- 2
- Total Value
- $394,800
- Median Sale Price
- $197,400
- Price Range
- $185K - $210K
Buyer Deals
- Total Deals
- 3
- Total Value
- $1,995,000
- Median Sale Price
- $997,500
- Price Range
- $275K - $1.72M
Sales Volume Timeline
Seller Deals
- Total Deals
- 4
- Total Value
- $1,227,800
- Median Sale Price
- $274,750
- Price Range
- $185K - $494K
Buyer Deals
- Total Deals
- 3
- Total Value
- $1,995,000
- Median Sale Price
- $997,500
- Price Range
- $275K - $1.72M
Sales Volume Timeline
Ratings & Reviews
5.0
(3)
I needed to sell my current home and buy new construction simultaneously. That's complicated. That's risky. Reuben managed both. He stayed on top of the build with weekly updates. He helped me switch lenders when needed. He sold my previous home for MORE than asking price. Everything went smoothly.
Source: Agent
I was making $7.50 an hour. Homeownership felt impossible. I didn't understand credit. I didn't know where to start. Reuben didn't just sell me a home—he educated me on credit, connected me with the right lender, and guided me through every step. I bought my home. 24 years later, I'm still living in it. That's not just a transaction—that's a life changed.
Source: Agent
I've been working with Reuben for 25 years—from my first home purchase to four successful transactions. What makes him different? He doesn't just sell homes; he teaches you how to build wealth through real estate. My starter home became a stepping stone. Each sale was profitable. Each purchase was strategic. Now my mother, brother, and sons all use his services. When Reuben says "your realtor for life," he means it.
Source: Agent
Professional Info
Brokerage
5401 South Kirkman Road
Orlando, FL 32819
Licensed
FL SL680620
Awards
- Top Producer 2021 & 2025
Specialties
- Age-restricted communities
- First-time buyers
- Foreclosures & Short sales
- Luxury properties
- Military
- Recreation & Vacation
- Relocation
Hobbies
- Family
- Fitness & Exercise
- Sports
Top Cities *
Winter Garden
- 2 sales past 3 years
- 78 days on market
- $210K median price
Casselberry
- 1 sales past 3 years
- 237 days on market
- $185K median price
Gainesville
- 1 sales past 3 years
- $1.72M median price
Service Areas (28 cities)
* Sales data is calculated based on transaction information available to Agent Pronto at the time of publishing and may not accurately reflect all transactions for a given agent.