The best way to find top real estate agents in Windy Hill, Jacksonville, FL

We analyze thousands of real estate agents in Jacksonville’s Windy Hill neighborhood and nationwide to find you proven local professionals, for free.

Real estate in Jacksonville’s Windy Hill neighborhood.

Compare top Windy Hill real estate agents.

Agent Pronto analyzes transaction data, agent specialties, and client reviews to handpick the best agents in your area. Updated for April 2026. *


* Sales data is calculated based on transaction information available to Agent Pronto at the time of publishing and may not accurately reflect all transactions for a given agent.

The easiest way to find a top agent you can trust.

Sell faster. Buy smarter. Get matched with proven agents who know your market—all for free.

Tell us what you need.
Answer a few quick questions about your real estate goals.
Get matched.
We’ll find you top local agents based on performance, expertise, and customer reviews.
Connect and compare.
Review your personalized recommendations and choose who’s right for you.
Move forward with confidence.
Whether you’re buying, selling, or both, you’ll have a proven expert on your side.
Agent profile screenshot
Agent profile screenshot

Windy Hill real estate Market Report.

Information and statistics on the latest trends in the Windy Hill real estate market, updated for April 2026. *

Windy Hill’s housing supply is relatively limited, with 54 homes on the market in March 2026 and 39 new listings during the month. Contract activity is slower, as pending sales reached 32 for the period. Compared with last year, new listings are down 38.1 percent and pending sales are down 11.11 percent, reflecting softer overall movement.

Home values and asking prices are adjusting to these conditions. The typical home value in Windy Hill is about $195,000, which is 13.33 percent lower than a year ago and down 3.94 percent from the prior month, while the median list price is $209,900 after a 6.71 percent monthly decline. By contrast, Jacksonville overall shows a typical home value of $300,000 with only a 1.64 percent annual dip, highlighting Windy Hill’s steeper pullback.

Homes are taking longer to sell, with the median days on market at 124 in March and up more than 61 percent from the previous month and 85.07 percent year over year. Even so, conditions still lean toward sellers, with a market gauge of 17 and only about 4.76 percent of sales closing above list price, plus an average sale-to-list ratio of 0.96 that points to moderate negotiation. Looking ahead to April, projections show a typical home value of $191,000, a median list price of $202,350, and inventory near 55, and both buyers and sellers can turn to Agent Pronto to connect with a local expert who understands these trends and can guide their next move.

Real estate in Jacksonville’s Windy Hill neighborhood.
17
Seller’s Market
Seller’s Market
Buyer’s Market
0
25
50
75
100

Market gauge is calculated based on the the number of active listings divided by home sales over the most recently available reporting period.

* Data provided by Redfin, a national real estate brokerage.

Learn more about what Windy Hill has to offer.

Windy Hill offers residents a welcoming, close-knit community with easy access to parks, schools, shopping, and efficient commutes, all wrapped in a relaxed, family-friendly vibe.

Windy Hill in Jacksonville stands out for its blend of established residential streets, major employment centers, and quick access to everyday conveniences. Unlike nearby beach communities or historic districts, it offers a practical, central location between Downtown Jacksonville and the Southside, with a wide mix of single family homes, townhomes, and apartments that appeal to a range of budgets and lifestyles.

Residents appreciate being minutes from shopping and dining along Southside Boulevard and the St. Johns Town Center, while still having neighborhood parks and schools close by. Windy Hill Elementary School and nearby Twin Lakes Academy Middle give families local public education options, and commuters value straightforward routes to Interstate 95 and JTA bus connections. Outdoor time often centers around area green spaces and larger regional destinations such as Hanna Park.

For buyers, understanding how Windy Hill compares to other nearby neighborhoods like Baymeadows or Mandarin can shape pricing expectations and competition. Sellers benefit from knowing current demand from renters and relocating professionals tied to local business hubs. In a neighborhood where convenience and value drive interest, timing and preparation matter. Agent Pronto connects both buyers and sellers with an agent who knows Windy Hill’s trends and can help them move at the right moment.

Find your Windy Hill real estate agent today →


Trusted by over 500,000 buyers and sellers.

See why so many people rely on Agent Pronto to make their real estate journey a success.

“I had a great experience working with Cat in Jacksonville, FL. She took the time to understand my needs, quickly identified the right home, and helped coordinate multiple visits while making sure all my questions were clearly addressed with the seller. Throughout the process, she was extremely responsive and proactive, connecting me with trusted professionals for inspections and other needs. She also went the extra mile by helping arrange care for the home since I won’t be moving in right away. Overall, a smooth and well-supported experience—I highly recommend Cat!”

Lei Xu · Saint Johns, FL

Photo of Cathleen Cornish
The Real Brokerage Real Broker LLC
“Casey did an outstanding job selling our home! From start to finish, everything was handled with professionalism, clear communication, and real expertise. The process was smooth, stress-free, and we couldn’t be happier with the results. Highly recommend Casey to anyone looking to buy or sell!”

Lachelle Tison · Green Cove Springs, FL

Photo of Casey Clearman
Century 21 Lighthouse Realty
“Nicole is awesome sauce! Best realtor EVER! We love her. I highly recommend her! Super knowledgeable, and helpful. She knows how to get it done....and fast!! 👏 Bravo 👏 Thank you so much 🙂”

Crystal Perrone · Hastings, FL

Photo of Nicole Pasquale
Century 21 C21 Integra
“Jose worked tirelessly for a couple of years searching for a very unique property that would meet my needs. He went out of his way to accommodate all my many requests for showings, info, etc.”

Susie Scott · Jacksonville, FL

Photo of Jose Gonzalez
One Sotheby's International Realty
“Cyndy was great to work with and managed all the pieces to get us to market, from presentation, pictures and pricing. Excellent in the offer and negotiations with the buyers. Smooth and painless!”

Beth · Ponte Vedra Beach, FL

Photo of Cyndy Tomassetti
Engel & Völkers Jacksonville Beach
“Yuranhi Quinones was absolutely amazing throughout my home buying process. She was professional, knowledgeable, and always available to answer my questions. Her dedication and support made everything smooth and stress-free. I’m so grateful for her help in finding my new home – highly recommend!”

Alexis · Jacksonville, FL

Photo of Yuranhi Quinones
Century 21 Integra
“Lara was amazing from start to finish. This was my first time selling and she made this such an easy process.”

Kevin S. · St. Johns County, FL

Photo of Lara  Hoffman
RE/MAX UNLIMITED
“Zach has been nothing but 100% professional. He answers all correspondence quickly and effectively. I must also say that his ability to get a deal finished is unparalleled. He truly has a gift with working in real estate.”

Christopher · Jupiter, FL

Photo of The Greenberg Group
Coastal Real Estate Professionals LLC
“The agent, Patricia, was professional, energetic, and empathetic to my needs. She went the extra mile to make sure I had the place that was right and then made sure all details were taken care of, so I could move in without worry.”

Harry K. · Tampa, FL

Photo of Patricia Pearlman
Madison Allied
“There are not enough words to express how amazing Jody was in helping us find our new home. From the moment we met him, we knew he was the best. Not only is he extremely knowledgeable in his field, he truly cares for you and what you are looking for. He was available to us 24/7 whether it was to show us a property or just answer questions. We have bought and sold many homes and his care and attention to detail was absolutely the best. We would highly recommend that anyone who is looking for the best, use Jody!”

Jane Patri Thomason · Jacksonville, FL

Photo of Jody Hanks
Century 21 Lighthouse Realty
“Lesley was amazing to work with. She guided me throughout the process with honesty, professionalism, and excellent communication. I would highly recommend her to anyone looking to buy or sell a home.”

Karen Leblang · Jacksonville, FL

Photo of Lesley Barlow
Engel & Völkers Jacksonville Beach
“Tonya did a great job. She kept up informed throughout the process.”

Gary M W. · Bryceville, FL

Photo of Tonya Rice
Palm III Realty Inc
“Larry is by far the most AMAZING Realtor. He was always very responsive to my calls, texts, request, etc. We built up such a great relationship through this crazy process, that even after we closed on our new home, he reached out to check on us. He is always looking to get the best deal for his clients. He is like family now to us and will always have his own seat next to the firepit in our backyard. I would DEFINETLY recommend Larry to anyone and everyone looking to buy or sell. AMAZING.. Can't say enough Great things about Larry.”

Kathleen and Joe · Wheaton, IL

Photo of Larry Lazar
Charles Rutenberg Realty Charles Rutenberg
“Please see the previous comments. Tiffany is the best and truly world class! Tiffany was so wonderful to work with. She knew everything we needed and led us through a very unusual market with results beyond our expectations! We would not have trusted anyone else and she was gracious and kind even when we may not have been. We have referred our friends to work with her, she is the best. Grateful to her and the team.”

Michael Hathway · Lawrenceville, GA

“We had an excellent experience with Donna. She was very responsive and always available. Would give us great advice. We enjoyed working with her and would highly recommend her to anyone looking or selling property! ”

Michele T. · Jacksonville, FL

Photo of Donna Quarto
Florida Homes Realty & Mortgage
“Excellent job”

Blanca Luis · Miami, FL

Photo of The Lebron Team
RE/MAX Premier Realty
“Ryan Ford was excellent!!”

Karen R. · St. Augustine, FL

Photo of Ryan Ford
Watson Realty Corp

Frequently Asked Questions

There are more than 2 million real estate agents across the U.S., and you want to be sure the one you partner with is an experienced and trustworthy professional with strong local expertise covering the housing market in and around Windy Hill. Working with a proven agent will help you sell your home faster and for more money, and help you find your dream home at the best possible price.


Looking for an agent in a different Jacksonville neighborhood?

We’ll match you with top-rated real estate agents in just about any city—wherever your next move takes you.