Drew Ross

Winter Garden FL

LAKEFIELD REALTY GROUP LLC

59 Closed Sales

$62.3M Total Value

$155K - $4.6M Price Range

$1.1M Average Price

Prior 5 years

About Drew

We've enjoyed living on the south shore of Lake Hancock for 25 years--and cannot think of a better place to raise a family and call home. As a former world water ski champion, I have become familiar with Central Florida's lakes and opportunities over the decades of experience that I've enjoyed them. I am passionate about understanding each client's goals, and working closely with them to formulate the very best strategy to accomplish them. I welcome your call to get to know each other.

Home Types: House, Condo, Lot/Land, Townhouse

Years of Experience: 22

Education: University of Central Florida, Stetson University College of Law, Rollins College

Transaction History

1 Year
2 Year
5 Year

Seller Deals
Total Deals	5
Total Value	$6,059,497
Average Sale Price	$1,211,899
Price Range	$215K - $2.2M

Buyer Deals
Total Deals	6
Total Value	$7,904,000
Average Sale Price	$1,317,333
Price Range	$199K - $4.3M

1 Year View by Quarter

Seller Deals
Total Deals	13
Total Value	$16,666,497
Average Sale Price	$1,282,038
Price Range	$155K - $2.6M

Buyer Deals
Total Deals	12
Total Value	$12,330,401
Average Sale Price	$1,027,533
Price Range	$199K - $4.3M

2 Year View by Quarter

Seller Deals
Total Deals	32
Total Value	$39,468,847
Average Sale Price	$1,233,401
Price Range	$155K - $4.6M

Buyer Deals
Total Deals	27
Total Value	$22,831,128
Average Sale Price	$845,597
Price Range	$199K - $4.3M

5 Year View

Neighborhoods Drew is Experienced In

Drew's Active Listings

$899,000
- 4 Beds
- 3.5 Baths
- 2,671 Sq Ft
8801 Fountain Palm Aly

Winter Garden, FL
Prepare to see the most decked out and finely finished townhome in Central Florida! This Toll Brothers end unit has been completely customized with over $140,000 in structural upgrades and $270,000 in design upgrades--that's right, more than $400k in upgrades, and the original sale was more than DOUBLE the price of many of the other townhomes in the community. Facing the lush landscape of the

Drew Ross LAKEFIELD REALTY GROUP LLC

$749,000
- 3 Beds
- 2 Baths
- 2,027 Sq Ft
14050 Fairway Willow Ln

Winter Garden, FL
Welcome to this beautifully maintained home in the highly sought-after Woodbridge on the Green community, overlooking West Orange Country Club and perfectly situated in the hub of Winter Garden. This waterfront home offers a blend of comfort, style, and convenience—ideal for anyone looking to enjoy the best of Central Florida living. Step inside to an inviting, light-filled layout featuring

Drew Ross LAKEFIELD REALTY GROUP LLC

$235,000
- Land
- 0.74 Acre
- $317,568 per Acre
13061 Swinney Ln

Clermont, FL
Enjoy spectacular sunsets over the lake, and approximately 277 feet of frontage along the glistening waters of Lake Pierrot--among the finest lots, offering the longest water frontage at the exclusive Tiger Paw Estates, a gated private ski lake community. Water skiers will love the location next to Lake Pierrot--a world-class private water ski lake--in a fitting setting, just across the road from

Drew Ross LAKEFIELD REALTY GROUP LLC

$2,125,000
- 4 Beds
- 4.5 Baths
- 3,751 Sq Ft
12699 Hawkstone Dr

Windermere, FL
Under contract-accepting backup offers. Welcome to Chalet du Lac, set on the exclusive and private Lake Sawyer chain of lakes in Windermere—where mornings are welcomed by sunrise over glistening waters dancing through a veil of Cypress trees and Spanish moss. Nestled along the western shoreline of Lake Sawyer within an enclave of custom-built lakefront homes, Chalet du Lac features 4 bedrooms and

Drew Ross LAKEFIELD REALTY GROUP LLC

$1,595,000
- 3 Beds
- 2 Baths
- 2,354 Sq Ft
10400 Lake Cottage Ln

Orlando, FL
Under contract-accepting backup offers. Nestled in the Cypress trees on the northern tip of a secluded Peninsula on Lake Sheen, yet within the gated community of Lake Sheen Reserve, Pineapple Pointe on Lake Cottage Lane exudes character while providing the ultimate private butler chain getaway. Reminiscent of a bygone era where the lakehouse experience meant a quiet sense of peace, Pineapple

Drew Ross LAKEFIELD REALTY GROUP LLC

$359,900
- 3 Beds
- 2.5 Baths
- 1,590 Sq Ft
13705 Golden Russet Dr

Winter Garden, FL
Under contract-accepting backup offers. Welcome to The Orchard, a tidy gated community of townhomes in sought-after Winter Garden. This residence blends modern comfort with low-maintenance living, offering a bright, open layout that feels inviting from the moment you step inside. Thoughtful upgrades elevate every space—stylish flooring, fresh finishes, and a contemporary color palette create a

Drew Ross LAKEFIELD REALTY GROUP LLC

Recently Sold

$419,497

Sold Feb 26, 2026
- 3 Beds
- 2.5 Baths
- 1,624 Sq Ft
14814 Peekskill Dr

Winter Garden, FL
- $258/SF
- 4 Days On Market
- Current Est. Value $413K
Drew Ross LAKEFIELD REALTY GROUP LLC

$2,150,000

Sold Jul 10, 2025
- 7 Beds
- 4.5 Baths
- 5,300 Sq Ft
6245 Little Lake Sawyer Dr

Windermere, FL
- 14% Below List
- $406/SF
- 193 Days On Market
- Current Est. Value $2M
Drew Ross LAKEFIELD REALTY GROUP LLC

$2,100,000

Sold Jun 10, 2025
- 5 Beds
- 6 Baths
- 5,030 Sq Ft
15168 Shonan Gold Dr

Winter Garden, FL
- 24% Below List
- $417/SF
- 273 Days On Market
- Current Est. Value $2M
Drew Ross LAKEFIELD REALTY GROUP LLC

$1,175,000

Sold May 20, 2025
- Land
- 1.45 Acre Lot
14653 Isleview Dr

Horizon West, FL
- 22% Below List
- 9 Days On Market
- Current Est. Value $1M
Drew Ross LAKEFIELD REALTY GROUP LLC

$555,000

Sold Feb 24, 2025
- 4 Beds
- 2 Baths
- 1,839 Sq Ft
817 Rosemere Cir

Orlando, FL
- 6% Below List
- $302/SF
- 164 Days On Market
- Current Est. Value $486K
Drew Ross LAKEFIELD REALTY GROUP LLC

$622,000

Sold Nov 26, 2024
- 3 Beds
- 3 Baths
- 2,758 Sq Ft
7927 Winter Wren St

Winter Garden, FL
- 4% Below List
- $226/SF
- 115 Days On Market
- Current Est. Value $588K
Drew Ross LAKEFIELD REALTY GROUP LLC

$2,200,000

Sold Sep 12, 2024
- 6 Beds
- 5.5 Baths
- 4,817 Sq Ft
15162 Shonan Gold Dr

Winter Garden, FL
- 8% Below List
- $457/SF
- 79 Days On Market
- Current Est. Value $2M
Drew Ross LAKEFIELD REALTY GROUP LLC

$1,075,000

Sold Aug 2, 2024
- 5 Beds
- 4.5 Baths
- 3,585 Sq Ft
12844 Bellerive Dr

Clermont, FL
- 10% Below List
- $300/SF
- 53 Days On Market
- Current Est. Value $1M
Drew Ross LAKEFIELD REALTY GROUP LLC

$2,600,000

Sold Jul 19, 2024
- 4 Beds
- 5.5 Baths
- 6,780 Sq Ft
14645 Isleview Dr

Winter Garden, FL
- 9% Below List
- $383/SF
- 0 Days On Market
- Current Est. Value $4M
Drew Ross LAKEFIELD REALTY GROUP LLC

Awards and Designations

Top REALTOR®
NAR - National Association of Realtors

Agent License: Florida #3053364

Drew Ross

(689) 220-5520

LAKEFIELD REALTY GROUP LLC

(689) 220-5520

Homes for Sale by City

Drew Ross

About Drew

Transaction History

Seller Deals

Buyer Deals

Production Over Time

1 Year View by Quarter

Seller Deals

Buyer Deals

Production Over Time

2 Year View by Quarter

Seller Deals

Buyer Deals

Production Over Time

5 Year View

Neighborhoods Drew is Experienced In

Drew's Listings and Deals

Drew's Active Listings

Recently Sold

Awards and Designations