Lisa Bennett Real Estate Agent - WINDSOR REALTY GROUP INC

502 Palm Dr, Winter Garden, FL For Sale $699,700 - co-listed by Lisa Bennett — For Sale $699,700 • Co-Listing Agent

Lisa Bennett listing agent for 1405 Snowden St, Ocoee, FL - sold for $290,000 — Sold $290,000

148 Roper Dr, Winter Garden, FL Under Contract $795,000 - listed by Lisa Bennett — Under Contract $795,000

Lisa Bennett buyer's agent for 356 Black Springs Ln, Winter Garden, FL - sold for $520,000 — Sold $520,000

519 Teagarden Ct, Winter Garden, FL For Sale $857,000 - listed by Lisa Bennett — For Sale $857,000

Lisa Bennett

Winter Garden FL

WINDSOR REALTY GROUP INC

41 Closed Sales

$22.4M Total Value

$207.5K - $2.1M Price Range

$546.4K Average Price

Prior 5 years

About Lisa

Bennett is a lifelong resident of Winter Garden and has been married to her husband, Greg, for 21 years. The Bennetts have four children: Billy, Heather, Cael, and Noah; and six grandchildren: Bryson, Shalynn, Faith, Cace, Cade, and Grayden. She graduated from Calvary High School in 1981 and attended Valencia Community College. She has been the co-owner/broker of Windsor Realty Group Inc. in Winter Garden for 15 years. Bennett has served District One for four years and formerly served on the city's Architectural Review Board. She is a past president of the Rotary Club of Winter Garden and a past chair of the board of Hope Charter School.

Home Types: House, Townhouse, Lot/Land

Years of Experience: 22

Education: Valencia College

Transaction History

1 Year
2 Year
5 Year

Seller Deals
Total Deals	10
Total Value	$4,319,000
Average Sale Price	$431,900
Price Range	$275K - $880K

Buyer Deals
Total Deals	2
Total Value	$1,369,000
Average Sale Price	$684,500
Price Range	$520K - $849K

1 Year View by Quarter

Seller Deals
Total Deals	16
Total Value	$9,011,100
Average Sale Price	$563,194
Price Range	$275K - $2.1M

Buyer Deals
Total Deals	4
Total Value	$2,916,710
Average Sale Price	$729,178
Price Range	$385K - $1.2M

Seller Deals
Total Deals	33
Total Value	$17,175,600
Average Sale Price	$520,473
Price Range	$27K - $2.1M

Buyer Deals
Total Deals	8
Total Value	$5,226,710
Average Sale Price	$653,339
Price Range	$285K - $1.2M

5 Year View

Areas Lisa is Experienced In

Lisa's Listings and Deals

Lisa's Active Listings

$857,000
- 4 Beds
- 3 Baths
- 3,061 Sq Ft
519 Teagarden Ct

Winter Garden, FL
New Price~ A Private Creekside Retreat nestled in the heart of North Winter Garden-where your backyard feels like a nature getaway* yet downtown Plant Street is a quick golf cart ride! Situated in an intimate cul-de-sac community of only 9 homes! With super low HOA, This Custom-built 4 Bedroom 3 Bath Home with Bonus Room offers Oversized Bedrooms & walk in closets with plenty of storage in a

Lisa Bennett WINDSOR REALTY GROUP INC

$495,000
- 3 Beds
- 2 Baths
- 1,716 Sq Ft
516 S Highland Ave

Winter Garden, FL
**Back on the market! Buyer's contingency fell through- New Price to sell **Some Photos virtually staged. Solidly built mid-century home in an exceptional Downtown Winter Garden location, just moments from Plant Street shopping and dining, Crooked Can Brewing Company, Garden Theatre, the splash pad, and all the charm of the golf cart district. Enjoy dinner downtown, then take your golf cart to

Lisa Bennett WINDSOR REALTY GROUP INC

Co-Listing Agent

$699,700
- 4 Beds
- 2.5 Baths
- 3,009 Sq Ft
502 Palm Dr

Winter Garden, FL
Experience the perfect blend of comfort, charm, and functionality in this beautiful Winter Garden home! Featuring 4 bedrooms and 2.5 baths, this spacious residence offers an impressive second-story loft and a versatile fourth bedroom with its own half bath—perfect for guests, a media room, or flexible living space. The thoughtfully designed first floor features a private primary suite with an

Lisa Bennett WINDSOR REALTY GROUP INC

$795,000

Under Contract
- 3 Beds
- 2 Baths
- 1,807 Sq Ft
148 Roper Dr

Winter Garden, FL
Under contract-accepting backup offers. Virtually Staged. Prime North Winter Garden Location with Lake Apopka Views! This solidly built block home offers an ideal combination of location, updates, flexible outdoor living, and unique extras. Enjoy views of Lake Apopka and Bradford Park, while being just a quick golf cart ride from the shops, restaurants, and entertainment of Downtown Winter

Lisa Bennett WINDSOR REALTY GROUP INC

Recently Sold

$290,000

Sold Apr 3, 2026
- 3 Beds
- 2 Baths
- 1,124 Sq Ft
1405 Snowden St

Ocoee, FL
- 3% Below List
- 5 Days On Market
- $258/SF
- Current Est. Value $288K
Lisa Bennett WINDSOR REALTY GROUP INC

$880,000

Sold Jan 26, 2026
- 4 Beds
- 5 Baths
- 3,105 Sq Ft
914 Elysium Blvd

Mount Dora, FL
- 20% Below List
- 156 Days On Market
- $283/SF
- Current Est. Value $873K
Lisa Bennett WINDSOR REALTY GROUP INC

$360,000

Sold Jan 12, 2026
- 3 Beds
- 2 Baths
- 1,550 Sq Ft
620 Caborca Ct

Ocoee, FL
- 4% Below List
- 7 Days On Market
- $232/SF
- Current Est. Value $361K
Lisa Bennett WINDSOR REALTY GROUP INC

$352,000

Sold Dec 15, 2025
- 3 Beds
- 2.5 Baths
- 1,638 Sq Ft
1386 Scarlet Oak Loop

Winter Garden, FL
- 5% Below List
- 7 Days On Market
- $215/SF
- Current Est. Value $363K
Lisa Bennett WINDSOR REALTY GROUP INC

$375,000

Sold Nov 21, 2025
- 3 Beds
- 2 Baths
- 1,765 Sq Ft
2600 Twisting Sweetgum Way

Ocoee, FL
- 2 Days On Market
- $212/SF
- Current Est. Value $382K
Lisa Bennett WINDSOR REALTY GROUP INC

$335,000

Sold Nov 6, 2025
- 3 Beds
- 2 Baths
- 1,679 Sq Ft
16406 Blooming Cherry Dr

Groveland, FL
- 9% Below List
- 129 Days On Market
- $200/SF
- Current Est. Value $341K
Lisa Bennett WINDSOR REALTY GROUP INC

$275,000

Sold Jul 30, 2025
- 2 Beds
- 2 Baths
- 1,265 Sq Ft
13225 Fountainbleau Dr

Clermont, FL
- 8% Below List
- 5 Days On Market
- $217/SF
- Current Est. Value $277K
Lisa Bennett WINDSOR REALTY GROUP INC

$621,400

Sold May 16, 2025
- 4 Beds
- 2 Baths
- 2,516 Sq Ft
13607 Zori Ln

Windermere, FL
- 1% Below List
- 75 Days On Market
- $247/SF
- Current Est. Value $630K
Lisa Bennett WINDSOR REALTY GROUP INC

$775,000

Sold Apr 10, 2025
- 3 Beds
- 2 Baths
- 1,976 Sq Ft
11207 Roberson Rd

Winter Garden, FL
- 2 Days On Market
- $392/SF
- Current Est. Value $737K
Lisa Bennett WINDSOR REALTY GROUP INC

Awards and Designations

NAR - National Association of Realtors

Frequently Asked Questions

Who is Lisa Bennett, and what is their real estate background?

How many homes has Lisa Bennett sold in Winter Garden, FL?

What is Lisa Bennett's track record representing buyers?

What is Lisa Bennett's track record as a listing agent?

What areas does Lisa Bennett serve?

How can I contact Lisa Bennett?

Lisa Bennett

(689) 220-3463

WINDSOR REALTY GROUP INC

(689) 220-3463

Nearby Homes

Lisa Bennett

About Lisa

Transaction History

Seller Deals

Buyer Deals

Production Over Time

1 Year View by Quarter

Seller Deals

Buyer Deals

Seller Deals

Buyer Deals

Production Over Time

5 Year View

Areas Lisa is Experienced In

Lisa's Listings and Deals

Lisa's Active Listings

Recently Sold

Awards and Designations

Frequently Asked Questions

Who is Lisa Bennett, and what is their real estate background?

How many homes has Lisa Bennett sold in Winter Garden, FL?

What is Lisa Bennett's track record representing buyers?

What is Lisa Bennett's track record as a listing agent?

What areas does Lisa Bennett serve?

How can I contact Lisa Bennett?