
Get to know Jessica Overstreet-Olive
Born and raised in Central Florida, I've watched it transform from a cow town into a thriving city! I am a University of Central Florida alumni and have worked in regulatory industries for nearly 25 years. With experience in title, insurance and real estate, I have been immersed in all facets of property investment. After achieving my aspirations in insurance, I sold my agency and devoted my insurance and title acumen solely to real estate. It ha...
Jessica Overstreet-Olive's listings & sales (21)
For Sale
Sold (21)
Address | Sold date | Closing price | Represented | Flag Sale |
|---|---|---|---|---|
| 10/15/2025 | $314,900 | Buyer | ||
| 3/31/2025 | $379,000 | Buyer | ||
| 11/26/2024 | $515,000 | Buyer | ||
| 11/12/2024 | $1,250,000 | Buyer and Seller | ||
| 10/25/2024 | $989,000 | Buyer |
Jessica Overstreet-Olive's reviews (5)
Write a review- Highly likely to recommend||5.05.0
10/21/2025 - Kara Pepper
Bought a Single Family home in 2025 in Gotha, FL.Local knowledgeProcess expertiseResponsivenessNegotiation skillsJessica did an outstanding job taking care of us! She was immediately responsive, transparent, kind, friendly, and overall super knowledgeable. She helped us every step of the way and we got our first home thanks to her! - Highly likely to recommend||5.05.0
10/21/2025 - Guglielmo Garavini
Bought a Single Family home in 2025 in Gotha, FL.Local knowledgeProcess expertiseResponsivenessNegotiation skillsJessica was amazing in helping us buy our home. She really knows the area and helped us come up with a great offer while keeping future value in mind. She negotiated a big credit from the seller and made the whole process easy. She always replied qui... - Highly likely to recommend||5.05.0
8/6/2024 - loeycooper22
Prattville, AL.Local knowledgeProcess expertiseResponsivenessNegotiation skillsEven though we were on opposite sides of the real estate transaction, Jessi was wonderful to work alongside. She advocated for her client, genuinely cared about facilitating a smooth process for all parties, and was a true professional each step of ... - Highly likely to recommend||5.05.0
4/24/2024 - zuser20150505093210678
Bought a Single Family home in 2024 in Delaney park, Orlando, FL.Local knowledgeProcess expertiseResponsivenessNegotiation skillsJessica helped us find our first home. She was extremely responsive during the whole process and her team was able to help us solve the challenges that were preventing us from moving forward as first-time home buyers. We were able to close on the hom... - Highly likely to recommend||5.05.0
4/19/2024 - tijanilaksmana25
Bought a Townhouse home in 2023 in Windermere, FL.Local knowledgeProcess expertiseResponsivenessNegotiation skillsJessi is absolutely delightful to work with! She helped me search for the home I wanted with all the amenities and location I needed. Even after we closed on our house, Jessi and I kept in contact. She went above and beyond by giving me recommendatio...








