Jackie O'Leary Real Estate Agent - FANNIE HILLMAN & ASSOCIATES

2051 Dyan Way, Maitland, FL For Sale $830,000 - co-listed by Jackie O'Leary — For Sale $830,000 • Co-Listing Agent

Jackie O'Leary listing agent for 4720 Gardenbrook Ln, Orlando, FL - sold for $310,000 — Sold $310,000

5550 E Michigan St Unit 3216, Orlando, FL For Rent $1,500/month - listed by Jackie O'Leary — For Rent $1,500/month

Jackie O'Leary buyer's agent for 2625 Park Place Dr, Winter Park, FL - sold for $1,900,000 — Sold $1,900,000

Jackie O'Leary

Winter Park FL

FANNIE HILLMAN & ASSOCIATES

16 Closed Sales

$10.9M Total Value

$260K - $1.9M Price Range

$680K Average Price

Prior 5 years

About Jackie

407.718.0887 is my cell number

Home Types: House, Condo

Years of Experience: 21

Transaction History

1 Year
2 Year
5 Year

Seller Deals
Total Deals	2
Total Value	$704,990
Average Sale Price	$352,495
Price Range	$310K - $395K

Buyer Deals
Total Deals	1
Total Value	$1,900,000
Average Sale Price	$1,900,000

Seller Deals
Total Deals	5
Total Value	$1,681,990
Average Sale Price	$336,398
Price Range	$260K - $422K

Buyer Deals
Total Deals	2
Total Value	$2,505,000
Average Sale Price	$1,252,500
Price Range	$605K - $1.9M

Seller Deals
Total Deals	10
Total Value	$5,039,490
Average Sale Price	$503,949
Price Range	$260K - $1.6M

Buyer Deals
Total Deals	6
Total Value	$5,839,900
Average Sale Price	$973,317
Price Range	$605K - $1.9M

5 Year View

Areas Jackie is Experienced In

Jackie's Listings and Deals

Jackie's Active Listings

Co-Listing Agent

$830,000
- 5 Beds
- 4 Baths
- 3,136 Sq Ft
2051 Dyan Way

Maitland, FL
Fantastic Maitland location! Situated on quiet cul-de-sac, this one-story 5 bedroom/4 bath, 3,136 sq ft ranch-style home is a short walk to A-rated Dommerich Elementary, Maitland Middle and Winter Park High. This one-story home sits on .29 of an acre that backs up to the preserved conservation. Functional floor plan with separate formal living and dining rooms, perfect for entertaining. Eat-in

Jackie O'Leary FANNIE HILLMAN & ASSOCIATES

$1,500 per month
- 2 Beds
- 2 Baths
- 1,107 Sq Ft
5550 E Michigan St

Unit 3216

Orlando, FL
Bright and light unit, very Spacious with 2 Bedrooms and 2 Baths, Split Floorplan and overlooks the Pool. This 2nd floor unit has its own Laundry Room with washer and dryer right off the Kitchen. Easy access to this unit as well, it sits a few short feet from the front stairwell, no need to wind all around the building! Beautiful Resort Amenities including GYM, POOL, HOT TUB and RECREATION ROOM.

Jackie O'Leary FANNIE HILLMAN & ASSOCIATES

Recently Sold

$310,000

Sold Dec 4, 2025
- 2 Beds
- 2 Baths
- 1,070 Sq Ft
4720 Gardenbrook Ln

Orlando, FL
- 18 Days On Market
- $290/SF
- Current Est. Value $310K
Jackie O'Leary FANNIE HILLMAN & ASSOCIATES

$394,990

Sold Nov 21, 2025
- 3 Beds
- 2 Baths
- 1,519 Sq Ft
5618 Arnold Zlotoff Dr

Orlando, FL
- 5% Below List
- 83 Days On Market
- $260/SF
- Current Est. Value $395K
Jackie O'Leary FANNIE HILLMAN & ASSOCIATES

$260,000

Sold Jun 6, 2025
- 2 Beds
- 1 Bath
- 710 Sq Ft
151 N Orlando Ave

Unit 115

Winter Park, FL
- 9% Below List
- 28 Days On Market
- $366/SF
Jackie O'Leary FANNIE HILLMAN & ASSOCIATES

$422,000

Sold Mar 31, 2025
- 3 Beds
- 1.5 Baths
- 1,436 Sq Ft
2000 N Westmoreland Dr

Orlando, FL
- 20% Below List
- 103 Days On Market
- $294/SF
Jackie O'Leary FANNIE HILLMAN & ASSOCIATES

$547,500

Sold Apr 30, 2024
- 2 Beds
- 2 Baths
- 1,092 Sq Ft
112 Tangelo Ct

Maitland, FL
- 4% Below List
- 10 Days On Market
- $501/SF
- Current Est. Value $555K
Jackie O'Leary FANNIE HILLMAN & ASSOCIATES

$525,000

Sold May 12, 2022
- 3 Beds
- 2.5 Baths
- 1,641 Sq Ft
1126 Washington Ave

Unit 9A

Winter Park, FL
- 17 Days On Market
- $320/SF
- Current Est. Value $542K
Jackie O'Leary FANNIE HILLMAN & ASSOCIATES

$1,560,000

Sold Apr 14, 2022
- 3 Beds
- 3.5 Baths
- 3,112 Sq Ft
101 S New York Ave

Unit 312

Winter Park, FL
- 2% Below List
- 42 Days On Market
- $501/SF
- Current Est. Value $2M
Jackie O'Leary FANNIE HILLMAN & ASSOCIATES

$380,000

Sold Mar 7, 2022
- 2 Beds
- 1 Bath
- 876 Sq Ft
1500 Bennett Rd

Orlando, FL
- 9 Days On Market
- $434/SF
- Current Est. Value $453K
Jackie O'Leary FANNIE HILLMAN & ASSOCIATES

Other Experience

First Time Homebuyers, Investments, Luxury Homes, Property Management, Foreclosures

Agent License: Florida 3144118

Jackie O'Leary

(888) 861-5907

Nearby Homes

Jackie O'Leary

About Jackie

Transaction History

Seller Deals

Buyer Deals

Seller Deals

Buyer Deals

Seller Deals

Buyer Deals

Production Over Time

5 Year View

Areas Jackie is Experienced In

Jackie's Listings and Deals

Jackie's Active Listings

Recently Sold

Other Experience