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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 November 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.

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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

Jul 1, 2026 - Sep 30, 2026

Median sale price
$269K
+26% from Q2 '26
Median list price
$213K
-12% from Q2 '26
Active listings
112
+15% from Q2 '26
Homes sold
32
-14% from Q2 '26
New pendings
34
-24% from Q2 '26
New listings
62
+29% from Q2 '26

Quarterly Pricing Trends for Windy Hill

Rolling three-month data ending on quarter boundaries when available.

Quarterly Pricing Trends for Windy Hill Q4 '21 Q4 '22 Q4 '23 Q4 '24 Q4 '25 Q3 '26 Median sale price in Oct 2021 - Dec 2021: $211K Median sale price in Jan 2022 - Mar 2022: $226K Median sale price in Apr 2022 - Jun 2022: $248K Median sale price in Jul 2022 - Sep 2022: $258K Median sale price in Oct 2022 - Dec 2022: $215K Median sale price in Jan 2023 - Mar 2023: $225K Median sale price in Apr 2023 - Jun 2023: $240K Median sale price in Jul 2023 - Sep 2023: $247K Median sale price in Oct 2023 - Dec 2023: $254K Median sale price in Jan 2024 - Mar 2024: $248K Median sale price in Apr 2024 - Jun 2024: $259K Median sale price in Jul 2024 - Sep 2024: $232K Median sale price in Oct 2024 - Dec 2024: $230K Median sale price in Jan 2025 - Mar 2025: $220K Median sale price in Apr 2025 - Jun 2025: $227K Median sale price in Jul 2025 - Sep 2025: $200K Median sale price in Oct 2025 - Dec 2025: $207K Median sale price in Jan 2026 - Mar 2026: $195K Median sale price in Apr 2026 - Jun 2026: $213K Median sale price in Jul 2026 - Sep 2026: $269K Median list price in Oct 2021 - Dec 2021: $222K Median list price in Jan 2022 - Mar 2022: $237K Median list price in Apr 2022 - Jun 2022: $250K Median list price in Jul 2022 - Sep 2022: $239K Median list price in Oct 2022 - Dec 2022: $230K Median list price in Jan 2023 - Mar 2023: $250K Median list price in Apr 2023 - Jun 2023: $249K Median list price in Jul 2023 - Sep 2023: $260K Median list price in Oct 2023 - Dec 2023: $221K Median list price in Jan 2024 - Mar 2024: $246K Median list price in Apr 2024 - Jun 2024: $256K Median list price in Jul 2024 - Sep 2024: $235K Median list price in Oct 2024 - Dec 2024: $200K Median list price in Jan 2025 - Mar 2025: $232K Median list price in Apr 2025 - Jun 2025: $220K Median list price in Jul 2025 - Sep 2025: $225K Median list price in Oct 2025 - Dec 2025: $223K Median list price in Jan 2026 - Mar 2026: $210K Median list price in Apr 2026 - Jun 2026: $242K Median list price in Jul 2026 - Sep 2026: $213K Oct 2021 - Dec 2021 Median sale price $211K Median list price $222K Jan 2022 - Mar 2022 Median sale price $226K Median list price $237K Apr 2022 - Jun 2022 Median sale price $248K Median list price $250K Jul 2022 - Sep 2022 Median sale price $258K Median list price $239K Oct 2022 - Dec 2022 Median sale price $215K Median list price $230K Jan 2023 - Mar 2023 Median sale price $225K Median list price $250K Apr 2023 - Jun 2023 Median sale price $240K Median list price $249K Jul 2023 - Sep 2023 Median sale price $247K Median list price $260K Oct 2023 - Dec 2023 Median sale price $254K Median list price $221K Jan 2024 - Mar 2024 Median sale price $248K Median list price $246K Apr 2024 - Jun 2024 Median sale price $259K Median list price $256K Jul 2024 - Sep 2024 Median sale price $232K Median list price $235K Oct 2024 - Dec 2024 Median sale price $230K Median list price $200K Jan 2025 - Mar 2025 Median sale price $220K Median list price $232K Apr 2025 - Jun 2025 Median sale price $227K Median list price $220K Jul 2025 - Sep 2025 Median sale price $200K Median list price $225K Oct 2025 - Dec 2025 Median sale price $207K Median list price $223K Jan 2026 - Mar 2026 Median sale price $195K Median list price $210K Apr 2026 - Jun 2026 Median sale price $213K Median list price $242K Jul 2026 - Sep 2026 Median sale price $269K Median list price $213K
Median sale price
Median list price
* Data provided by Redfin, a national real estate brokerage.
33
Seller’s Market
Seller’s Market
Buyer’s Market
0
25
50
75
100

Market gauge is calculated using active listings and pending sales from the most recently available reporting period (Jul 2026 - Sep 2026).

Windy Hill is seeing more homes come to market in this rolling three-month view, with new listings up notably from a year ago. Even with that increase, active inventory is slightly lower than last year, and the area holds about seven months of supply, much higher than Jacksonville overall. Fewer homes are going under contract and closing than a year ago, as homes sold and pending sales have both declined year over year.

Prices are moving differently than activity levels. The typical home value is up strongly compared with this time last year, even as the median list price has edged down year over year, suggesting sellers may be pricing more conservatively to attract buyers. Despite slower sales, the average sale-to-list ratio has ticked up slightly over the past year, and a larger share of homes are now closing above asking than a year ago.

Homes are not lingering as long as they were recently, with median days on market down from both three months ago and last year, and roughly one in five listings go off the market within two weeks. Compared with the broader Jacksonville market, Windy Hill’s inventory looks looser, but values here are still below the citywide typical sale price. Buyers navigating these mixed signals and sellers trying to price correctly can both benefit from Agent Pronto’s help in finding the right local real estate agent.



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.

“Cat Cornish is simply the best! From our initial conversations about possibly moving to the area to the quickly ramped up "we're ready to move now," she has managed the process flawlessly. Buying a home and relocating from another state is stressful, and Cat has made everything as smooth and enjoyable as possible. She has gone above and beyond time and time again! She knows her stuff, communicates well, and gets things done. My family is moving to a place we never thought we could live and into a home that is perfect for our family, and we coudn't have done it without Cat's help.”

Marc Gurley · Ponte Vedra, FL

Photo of Cathleen Cornish
The Real Brokerage Real Broker LLC
“We are a military family, transferring from another state. Knowing this, and knowing it would be improbable for us to travel to see homes prior to purchasing, Adrian and team was very helpful in all aspects of helping us in purchasing our new home! Their personal touches in understanding our wants and needs made the experience so much smoother. They went above and beyond to ensure our requests were met in a timely manner. We appreciate everything they did to assist us through this normally stressful process. I highly recommend them to anyone planning to purchase a home in the future.”

rrq1205 ·

Photo of Adrian Gentry
Sieva Realty
“Zack from the first time we met in 2024 worked in my best interest and help our family get what we needed and as our family grew we called him again to help us find a house that better fit our needs he and Arnold worked to find exactly what we were looking for they listen and found it . In the first week grateful for them and will let anyone I know to give him a call , If you are looking for a home or rental him and his team are who you need to go with they did a outstanding job”

Joseph Cuba · Port Saint Lucie, FL

Photo of The Greenberg Group
Coastal Real Estate Professionals LLC
“Mable was very helpful throughout the entire process and listened to our wants and needs in a home. She was respectful of our budget and provided options that were reasonable for what we could afford. She was very responsive and was always ready to tour homes we were interested in. She also helped with finding options for loans, inspections, etc which eased a lot of the stress because we knew we didn’t have to figure it out all by ourselves. My wife and I are very happy with the home she helped us find!”

ryancarlo314 ·

Photo of Mable Washington
Watson Realty Corp Watson Realty
“Amanda Romeo and her team where the best. Made our process so simple and smooth. Would definitely recommend 100% They also recommended great lenders. This team is so knowledgeable.”

user87412121 ·

Photo of Welch Team Keller Williams
Keller Williams St Johns
“I highly recommend Christine to anyone looking to buy a home! She was professional, knowledgeable, and incredibly helpful throughout the entire process. Christine made everything smooth and stress-free by keeping us informed and answering all of our questions along the way. If you’re looking for a realtor who truly cares about her clients and goes above and beyond, Christine is the perfect choice!”

Megan Spikol ·

Photo of Kurt Bogart
Endless Summer Realty
“Tiona worked with us as first-time home buyers. She was extremely informative, responsive, and patient as we went through a stressful process in a crazy market! She had plenty of resources for us at every step of the way. She will be honest on things she is not 100% sure of, and will refer you to an expert to make a solid decision. She was available to us at absolutely any time of day and worked with our chaotic night shift hours. She is such a sweet person to work with and I am so thankful she helped us find our first home.”

Meggan Lake ·

Photo of 1st Class Real Estate
1st Class Real Estate Premier Group
“Melissa and her team are absolutely AMAZING!!! I personally have used Melissa and her team 3 times in the last seven years to buy and sell homes, and every experience has been great. Melissa and the team go out of there to make sure every detail is covered. They will fight for you to get you the best deal. I would refer them to anyone anytime. From initial contact, to viewing the property, to drawing up the contract. Everything flawlessly done.”

swartzonstjames ·

Photo of Melissa Ricks
Engel & Völkers Engel & Volkers Jacksonville
“Very professional, made sure that I was included in every step of the process and that I understood it completely. She is very attentive, honest and hardworking. I could not have asked for anyone better to help me. I highly recommend her”

kathrina torres ·

Photo of Heather Denmark
Keller Williams Realty Atlantic Partners St. Augustine
“Jennifer was the BEST! Hands down!! She is very knowledgeable of the area, weather, and other factors needed in buying or selling a house. She deals with the same issues home buyers or sellers were dealing with since she lives locally. Her input was well appreciated! She is also in immediate communication with you concerning issues that arise. She is very empathetic to your needs and will strive to get you the best deal possible. We are SO glad she was our realtor! You won't be disappointed!”

jbro8776 ·

Photo of Watson Realty Corp.
Watson Realty Corp.
“Natasha did an outstanding job for us. She went above and beyond the call of duty. She kept us informed on the process even though we were buying from out of state. Kept us updated on any changes that occurred. I would definitely recommend Natasha to anyone who needed a realtor. We can't say enough good about her. We had NO negative dealings with her at all.”

Michael Harden ·

Photo of CrossView Realty
CrossView Realty
“We truly could not have asked for a better real estate agent than Heather Strazinsky. From beginning to end, she was incredibly knowledgeable, responsive, patient, and genuinely wonderful to work with. We always felt like she had time for us—whether we had a question, needed advice, or wanted to take a look at something. She made a stressful process feel so much easier. Heather is excellent at what she does and was someone we completely trusted to guide us through the process. Just as importantly, she is kind, down-to-earth, and such a pleasant person to be around. We had our kids along with us throughout the process, and she was always so patient and wonderful with them. They absolutely loved her and were always happy to see her, which meant so much to us. We are so grateful for all of the time and care Heather put into helping us find our home. We would recommend her without hesitation to anyone looking for an agent. She truly went above and beyond for our family, and we feel very fortunate that we had her in our corner.”

Rachel McDermott ·

Photo of Heather Strazinsky
Momentum Realty
“Aimee was amazing throughout the whole process and wasn't afraid to "get her hands dirty" when needed. She always made us feel like she had our backs and held our best interests in mind, and fought for them! You can tell she has expert knowledge of the industry and the areas that she operates in. Highly recommend Aimee to anyone looking to buy and/or sell!”

mike lawrence huffman ·

Photo of Aimee Heckelman
Signature Realty Associates
“Tiffany is an All-Star real estate agent. She's from the area so is very knowledgable about the local market. She listens and teaches you about the home buying process and keeps you updated on each step. She responds to every call, text, and email within ten minutes and usually sooner. She makes you aware of things you need to focus on and is always looking out for your best interest. She has referrals for practically everything you may need including lenders, insurance, inspectors, and plumbers. These partners are also extremely nice and helpful in their particular area. She takes the lead when working with these partners as much as you need. All of these things demonstrate her hard work and dedication. If you select a different real estate agent then chances are you're settling for second best.”

Jack Madden ·

Photo of Tiffany Riley
Momentum Realty
“Tracy you're awesome, as a first time home buyer I was a little nervous to say the least but, I wanted to get back in the market looking for a new home, I was lucky enough to get Tracy . I told her what I was looking for and she got back to me with very nice properties and also gave me a couple more options to take a look at, She was able to show me the properties on a Sunday with very short notice. I was able to get all of my questions answered. She has made my home buying process so seamless, She's a great negotiator because my offer was countered however her due diligence and the back and forth got me to a point where I could live with the numbers and I was ready to close the deal, I cried, it was a fight, but Tracy was the right person. We saw the proprty on. Sunday and went under contract the next Thursday, I'm just taking it all in. I couldnt have asked for a better Agent, would I recommend Tracy, I've already have to two of my relatives. Tracy you rock and thank you for helping me get out of my horrid apartment living situation an into my own little Bungalow with peace and quiet!! Thank you so much.”

FELICIA SOLOMON ·

Photo of The Trinity Home Team
The Trinity Home Team @ LPT REALTY
“Working with Win Wilson has been one of the best decisions I've made in real estate. Over the years, she has helped me purchase homes, sell properties, and navigate every step of the process with professionalism, expertise, and integrity. What sets Win apart is not only her deep knowledge of the housing market and real estate transactions, but also her ability to help clients see opportunities and risks from different perspectives. She takes the time to understand your goals, provides honest advice, and ensures you make informed decisions rather than simply pushing a transaction forward. Her knowledge of homes, market trends, pricing strategies, negotiations, and the overall buying and selling process is exceptional. No matter the situation, she brings valuable insights, strong communication, and a level of dedication that is hard to find. I've worked with many professionals over the years, and I can confidently say that Win is truly the best of the best. I highly recommend her to anyone looking to buy or sell a home. You will be in excellent hands.”

chenyuan93 ·

Photo of Crystal Doxtator
LoKation Real Estate
“Casey was very knowledge and easy to work with. Kept me up to date and talked me through all the steps since it was my first time selling a house. He was on my side the entire time.”

Kathryn Greulich ·

Photo of Casey Clearman
Century 21 Lighthouse Realty
“Toneesha was very delightful to work with. She was attentive to all my needs and wants in purchasing my very 1st home. Toneesha’s wealth of knowledge and background as well as growing up in the state of Florida sets her aside from others! Please please do yourself a favor and reach out to her for all your real estate needs. Thank me later!”

Vickie Bolden ·

Photo of Toneesha Singleton
Florida Homes Realty & Mortgage
“Susan was wonderful to work with. She is down to earth and works hard on your behalf. She is professional and knows the market. I bought a home in Florida, all the way from North Carolina, without seeing it in person. Susan showed my daughter the home and it’s exactly what I was looking for. I moved into it this week and it’s a perfect home for me. Susan never runs out of energy and cares about you throughout the whole process. I don’t plan to buy another home, but if I did, I would definitely call Susan!”

Stacey Permenter ·

Photo of Susan Kennedy
Coldwell Banker Vanguard Realty
“We loved working with Chrissy! As first-time homebuyers, we truly felt like we were in capable hands and had someone in our corner throughout the entire process. She made such a big milestone feel so much easier to navigate. We would absolutely recommend Chrissy to anyone looking to buy or sell a home!”

Allie Wade ·

Photo of Chrissy Henry
Keller Williams Jacksonvile

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.


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