Harry Pool, III Real Estate Agent - COLDWELL BANKER REALTY

1761 Legion Dr, Winter Park, FL For Sale $3,265,000 - listed by Harry Pool, III — For Sale $3,265,000

Harry Pool, III listing agent for 39545 Harbor Hills Blvd, Lady Lake, FL - sold for $570,000 — Sold $570,000

1427 Benwick Way, Casselberry, FL For Rent $2,300/month - listed by Harry Pool, III — For Rent $2,300/month

Harry Pool, III buyer's agent for 4346 Daubert St, Orlando, FL - sold for $400,000 — Sold $400,000

Harry Pool, III

Winter Park FL

COLDWELL BANKER REALTY

20 Closed Sales

$16.7M Total Value

$145K - $6.1M Price Range

$835.5K Average Price

Prior 5 years

About Harry

Harry Pool is a professional Realtor in Winter Park, FL. His sole objective is to gain the best terms for his clients through diligence, preparedness, and a keen instinct for closing a deal. He maintains a high degree of competency in all sectors of residential real estate.

Prior to entering the real estate arena, Harry spent 9 years in Investment banking at the Royal Bank of Scotland. Through his banking experience, he developed skills in asset valuation, negotiation, and alternative financing techniques. These skills and experiences combine to equip his clients with a significant advantage when it comes to buying and selling residential real estate

Harry received a BA from Rollins College in Winter Park. He and his wife, Sydney live in Winter Park with their three beautiful children, Isla, Harry IV and Gareth, and their dog Jasper. As a family they enjoy golf, Pickleball, tennis, soccer, and everything Winter Park and Central FL has to offer.

Home Types: House, Townhouse, Condo

Years of Experience: 10

Transaction History

1 Year
2 Year
5 Year

Seller Deals
Total Deals	3
Total Value	$1,705,000
Average Sale Price	$568,333
Price Range	$495K - $640K

Buyer Deals
Total Deals	1
Total Value	$400,000
Average Sale Price	$400,000

Seller Deals
Total Deals	3
Total Value	$1,705,000
Average Sale Price	$568,333
Price Range	$495K - $640K

Buyer Deals
Total Deals	1
Total Value	$400,000
Average Sale Price	$400,000

Seller Deals
Total Deals	10
Total Value	$11,162,000
Average Sale Price	$1,116,200
Price Range	$145K - $6.1M

Buyer Deals
Total Deals	10
Total Value	$5,547,890
Average Sale Price	$554,789
Price Range	$315K - $850K

5 Year View

Areas Harry is Experienced In

Harry's Listings and Deals

Harry's Active Listings

$3,265,000
- 5 Beds
- 5.5 Baths
- 4,924 Sq Ft
1761 Legion Dr

Winter Park, FL
One of the most coveted neighborhoods in all of Winter Park, this exceptional custom-built residence offers a rare combination of timeless design, modern sophistication, and an unbeatable location. Completed in 2017 and first sold in 2018, this 5-bedroom, 5.5-bath home has been meticulously maintained by its original owner and enhanced with high-end designer finishes. Much of the interior was

Harry Pool, III COLDWELL BANKER REALTY

$2,300 per month
- 3 Beds
- 2 Baths
- 1,256 Sq Ft
1427 Benwick Way

Casselberry, FL
Step into this renovated 3-bedroom, 2-bath single-family home in the desirable Camelot Subdivision. Perfectly situated near major Florida roadways, including FL-426 and FL-417, your daily commute will be a breeze. Inside, the open-concept layout showcases new luxury vinyl flooring in the main living areas and laundry room, tile flooring in the bathrooms, and plush new carpet in the spare

Harry Pool, III COLDWELL BANKER REALTY

Recently Sold

$570,000

Sold Jun 26, 2026
- 4 Beds
- 2.5 Baths
- 2,954 Sq Ft
39545 Harbor Hills Blvd

Lady Lake, FL
- 11% Below List
- 63 Days On Market
- $193/SF
- Current Est. Value $580K
Harry Pool, III COLDWELL BANKER REALTY

$495,000

Sold Dec 10, 2025
- 3 Beds
- 2 Baths
- 1,370 Sq Ft
625 S Lakemont Ave

Winter Park, FL
- 10% Below List
- 0 Days On Market
- $361/SF
- Current Est. Value $528K
Harry Pool, III COLDWELL BANKER REALTY

$640,000

Sold Dec 4, 2025
- 3 Beds
- 3 Baths
- 2,222 Sq Ft
145 Old Moss Cir

Deland, FL
- 8% Below List
- 241 Days On Market
- $288/SF
- Current Est. Value $629K
Harry Pool, III COLDWELL BANKER REALTY

$515,000

Sold Dec 4, 2023
- 3 Beds
- 2 Baths
- 1,502 Sq Ft
381 Perth Ln

Winter Park, FL
- 6% Below List
- 31 Days On Market
- $343/SF
- Current Est. Value $614K
Harry Pool, III COLDWELL BANKER REALTY

$952,000

Sold Sep 22, 2023
- 4 Beds
- 3.5 Baths
- 2,629 Sq Ft
715 Alameda St

Orlando, FL
- 5% Below List
- 98 Days On Market
- $362/SF
- Current Est. Value $994K
Harry Pool, III COLDWELL BANKER REALTY

$840,000

Sold May 11, 2023
- 3 Beds
- 3.5 Baths
- 2,219 Sq Ft
458 Piney Croft Ln

Maitland, FL
- 2% Below List
- 92 Days On Market
- $379/SF
- Current Est. Value $864K
Harry Pool, III COLDWELL BANKER REALTY

$555,000

Sold Apr 4, 2023
- 4 Beds
- 3 Baths
- 2,397 Sq Ft
605 Strihal Loop

Oakland, FL
- 3% Below List
- 6 Days On Market
- $232/SF
- Current Est. Value $575K
Harry Pool, III COLDWELL BANKER REALTY

$145,000

Sold Jul 15, 2022
- 1 Bed
- 1 Bath
- 678 Sq Ft
169 Lewfield Cir

Unit 169

Winter Park, FL
- 3% Below List
- 18 Days On Market
- $214/SF
- Current Est. Value $136K
Harry Pool, III COLDWELL BANKER REALTY

$6,100,000

Sold May 27, 2022
- 5 Beds
- 6.5 Baths
- 9,233 Sq Ft
1001 Anchorage Ct

Winter Park, FL
- 6% Below List
- 0 Days On Market
- $661/SF
- Current Est. Value $7M
Harry Pool, III COLDWELL BANKER REALTY

Other Experience

First Time Homebuyers, Investments, Military Families, Veteran's Programs, Senior Communities, Luxury Homes, New Construction, Property Management

Agent License: Florida 3359301

Harry Pool, III

(475) 258-8876

Nearby Homes

Harry Pool, III

About Harry

Transaction History

Seller Deals

Buyer Deals

Seller Deals

Buyer Deals

Seller Deals

Buyer Deals

Production Over Time

5 Year View

Areas Harry is Experienced In

Harry's Listings and Deals

Harry's Active Listings

Recently Sold

Other Experience