“A pleasure to work with. She was knowledgeable, professional, kind. Answered all our questions and spent time explaining the procedure of the closing with us. We were 2 100% satisfied with Nicole.”
Century 21 C21 Integra
- Agent Pronto
- Florida
- Jacksonville
- Windy Hill
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.
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 June 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.
Windy Hill real estate Market Report.
Information and statistics on the latest trends in the Windy Hill real estate market. *
Latest Rolling 3-Month Snapshot
Mar 1, 2026 - May 31, 2026
Median sale price
$211K
+8.2%
from
Q1 '26
Median list price
$237K
+7.6%
from
Q1 '26
Active listings
87
-2.2%
from
Q1 '26
Homes sold
33
+57%
from
Q1 '26
New pendings
47
+52%
from
Q1 '26
New listings
42
+7.7%
from
Q1 '26
Quarterly Pricing Trends for Windy Hill
Rolling three-month data ending on quarter boundaries when available.
Median sale price
Median list price
Quarterly Pricing Trends for Windy Hill
Rolling three-month data ending on quarter boundaries when available.
Median sale price
Median list price
Quarterly Pricing Trends for Windy Hill
Rolling three-month data ending on quarter boundaries when available.
Median sale price
Median list price
Quarterly Inventory and Sales Activity for Windy Hill
Rolling three-month supply and activity totals for the selected period.
Active listings
Homes sold
New pendings
New listings
Quarterly Inventory and Sales Activity for Windy Hill
Rolling three-month supply and activity totals for the selected period.
Active listings
Homes sold
New pendings
New listings
Quarterly Inventory and Sales Activity for Windy Hill
Rolling three-month supply and activity totals for the selected period.
Active listings
Homes sold
New pendings
New listings
19
Seller’s Market
Seller’s Market
Buyer’s Market
0
20
40
60
80
100
0
25
50
75
100
Market gauge is calculated using active listings and pending sales from the most recently available reporting period (Mar 2026 - May 2026).
Inventory in Windy Hill has tightened in this rolling three-month view, with active listings down about a third from a year ago. Fewer owners are listing, as new listings have fallen more than 35 percent year over year. Even with leaner supply, homes sold are still only modestly below last year, and pending sales are almost flat.
Contract flow has recently picked up, with pending sales jumping more than 50 percent compared with the prior three-month period. Median days on market, now at 91 days, have shortened sharply over the past few months, yet they remain far longer than in recent years, suggesting buyers still have time to evaluate options.
Pricing has eased from last year despite lower inventory, with the typical home value down slightly year over year and the share of homes selling above list shrinking to just over 3 percent. Windy Hill also sits at a lower price point than Jacksonville overall, where the median sale price is above $300,000, which may attract value-focused buyers. Months of supply has dropped back under five months, reinforcing the area’s seller-leaning conditions even as the average sale-to-list ratio hovers around 95 percent. In this shifting environment, both buyers and sellers can benefit from Agent Pronto’s help connecting with a skilled local agent who understands these trends.
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.
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.
“Zachary Greenberg was the correct choice. He was knowledgeable, he communicated as the process evoleved. His whole staff was as well. I felt my interests were being met. Alex Paganucci”
Coastal Real Estate Professionals LLC
“We truly can’t say enough about our experience working with Cyndy over the past two years. From the very beginning, she committed to helping us find the right home in Jacksonville—even though we were still in the process of selling our home in Key Largo, which took much longer than expected. For two full years, she stood by us, showing us countless homes, always with patience, professionalism, and a genuine desire to help us find the perfect fit. At no point did we ever feel like “just another client.” She never rushed us, never pressured us, and always gave honest, thoughtful guidance as we navigated different neighborhoods, price points, and changing market conditions. What really sets her apart is her consistency and dedication. Many realtors might have moved on given the uncertainty and length of our timeline, but she never did. She stayed committed to us every step of the way, always making time when we were in town and keeping us informed from afar. We HIGHLY recommend Cyndy!”
Engel & Völkers Jacksonville Beach
“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!”
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!”
Century 21 Lighthouse Realty
“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.”
One Sotheby's International Realty
“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!”
Century 21 Integra
“Lara was amazing from start to finish. This was my first time selling and she made this such an easy process.”
RE/MAX UNLIMITED
“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.”
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!”
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.”
Engel & Völkers Jacksonville Beach
“Tonya did a great job. She kept up informed throughout the process.”
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.”
Charles Rutenberg Realty Charles Rutenberg
“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! ”
Florida Homes Realty & Mortgage
“Excellent job”
RE/MAX Premier Realty
“Ryan Ford was excellent!!”
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.
-
Choosing a real estate agent to help you buy or sell property is one of the most important decisions you’ll make in your lifetime. You want to make sure your agent is an expert in your area, has a proven record helping people buy and sell similar homes to yours, and is well regarded by their previous clients. Let us know a few details about the property you are selling or the kind of home you want to buy, and Agent Pronto will match you with trusted real estate agents that have the experience you need. And before you interview an agent, check out our top five questions to ask a buyer’s agent and listing agent.
-
We consider performance metrics, close rates, specialties, and client reviews to qualify the best full-time agents. We then take the information you provide about the home you are selling or the kind of home you want to buy, and analyze the top local agents with the right experience for your specific needs. For more than a decade, we've helped hundreds of thousands of home buyers and sellers find the right agent. Get started now and find the perfect real estate agent.
-
No. Agent Pronto is a free service for home buyers and sellers and you are under no obligation to work with our recommended agents. Find your Windy Hill Realtor® or real estate agent today.
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.