Windy Hills
Homes for Sale in Jacksonville, FL
True comps, carrying-cost math, and listings before the portals.
Windy Hills is a small, older Jacksonville pocket — 111 homes with a median build year of 1957 and a median footprint around 1,248 square feet. With a build range stretching from 1950 to 2021, price here is driven less by a common floor plan and more by condition: what has been renovated, what has been left original, and what has been rebuilt on an existing lot. Expect a wide spread rather than a tidy comp set, and read each listing on its own merits.
Just over half the homes carry a homestead exemption (about 53%), which points to a core of longer-term owner-occupants alongside a rental and investor presence. For a seller, that mix means your buyer pool spans owner-occupants and investors, so presentation and condition matter. For a buyer, it means you should underwrite each property individually — the small size of this community and the age of the stock reward careful inspection over assumptions.
Figures in this note are as of July 12, 2026. The live market numbers elsewhere on this page update nightly and are newer.
The 60-Second Overview
Windy Hills is a compact, mid-century Jacksonville enclave in Duval County where modest square footage and a decades-wide build range make condition — not layout — the real pricing story.
Pre-construction details are compiled from public records, builder announcements and builder listings, and are subject to change without notice; figures are deemed reliable but not guaranteed. Momentum Research figures are our own analysis. This page describes homes, pricing and community attributes, not residents.
Who Windy Hills is best for.
Best for
- Renovation-minded buyers willing to underwrite an older home on its own merits
- Right-sizing buyers who want a smaller footprint and are not chasing square footage
- Investors seeking a foothold in a small, established Jacksonville pocket
Probably not for
- Buyers who need new construction or move-in-ready modern systems
- Buyers requiring larger square footage or open, contemporary layouts
- Buyers who want a deep, uniform inventory and tight, predictable comps
The market around Windy Hills
Windy Hills is too small for its own price trend, so here is the market around it.
In ZIP 32246, 237 homes are on the market and 27% are under contract — a steady corner of Jacksonville.
Across Duval County, 4,391 homes are active and 1,538 pending (26% under contract).
ZIP and county figures describe the wider market, not Windy Hills specifically. Momentum Research analysis of MLS records.
Windy Hills by the numbers
From county property records and closed MLS sales for the Windy Hills subdivision: 6 homes on record; built 1950–1976; typical size about 1,204 heated sq ft; 3 bedrooms is the median. Housing mix: single-family 100%.
| Year | Recorded sales | Median price |
|---|---|---|
| 2006 | 2 | $135,750 |
| 2007 | 1 | $96,000 |
| 2008 | 1 | $130,000 |
| 2010 | 1 | $57,400 |
| 2015 | 1 | $112,000 |
Newest recorded sale: $112,000 on 2015-12-11.
Recorded data as of 2026-09-12; counts cover addresses tagged to this subdivision in the public record, not every parcel. Not an appraisal.
Housing distress & ownership in Windy Hills, Jacksonville
Who owns here, how much is not owner-occupied, and how much for-sale inventory is under distress.
Source: Momentum Realty Research. Ownership & parcels from the FL DOR 2025 tax roll; distress from MLS active-listing status/remarks; price from MLS closed sales. Source: Data provided by realMLS. Deemed reliable but not guaranteed.
The Windy Hills buying strategy.
If we were buying in Windy Hills today, this is the order of operations we would run for our clients.
Underwrite the condition first. Price the roof, HVAC, and systems honestly before judging any list price; condition swings value here more than square footage alone.
Match the home to real comps. Recent sales of similar condition and lot, not the asking price, tell you what a home is worth.
Move deliberately, not desperately. Neither side has a decisive edge, so a well-prepared, fairly-priced offer wins without overpaying.
Line up financing and inspection early. A pre-approval and an inspection plan let you act fast and negotiate from evidence.
Keep an agent in your corner. The listing agent works for the seller; we represent you and prepare a hand-built valuation before any offer in Windy Hills.
An older, condition-driven pocket
With a median year built of 1957 and homes dating back to 1950, most of Windy Hills predates modern construction norms. The presence of homes as new as 2021 tells you infill and rebuilds have happened here, but they are the exception. A median living area near 1,248 square feet keeps this firmly in the smaller-footprint category, which tends to favor buyers looking to renovate or right-size rather than those chasing space.
The roughly 53% homestead share suggests a stable base of owner-occupants without crowding out investment activity. In a community of only 111 homes, inventory is thin by definition — when something well-updated lists, it stands out, and when something needs work, it prices accordingly. Diligence on roof, systems, and prior permit history is where buyers protect themselves in stock of this age.
The location and the amenities are priced into every listing in Windy Hills. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
A community this small with stock this old rewards local read over algorithm. We help buyers separate a genuinely updated home from cosmetic cover-up, and we help sellers position condition honestly against a buyer pool that includes both owner-occupants and investors. In Windy Hills, the work is in reading each property individually — and that is exactly what we do.
Windy Hills in 15 seconds.
Tools for a Windy Hills buy.
Free calculators to pressure-test the real cost before you tour.
Selling here is won on condition and pricing to real comps, not an automated estimate. The right number comes from closed Windy Hills sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Windy Hills, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
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Recent Developments in Windy Hills
Development, infrastructure, retail, and school activity affecting Windy Hills, tracked by our team and summarized from public reporting and official sources, with links to the original coverage. Last updated October 2026.
- October 2026Market
St. Johns County denies 4,462-acre Palm Valley farmland housing application under new state enclave law
Commissioners denied 3-2 on Sept. 15 the 4,462-acre Palm Valley application near Nocatee under the state agricultural enclave law, and the county plans to fight it in court. Another proposal of nearly 1,200 acres and about 15,000 homes south of St. Augustine was approved in August, then denied 3-2 on Sept. 28. St. Johns County has received 16 applications under the law.
What it may mean for the marketThe outcome of these applications will shape how much new housing supply can be added on rural land in the county. The site is about 11 miles southeast of Windy Hills.
Source: Jacksonville Today - September 2026Infrastructure
JEA advances about $690 million in infrastructure projects including Fulton Cut transmission line raise near JAXPORT
JEA is moving forward with three water reclamation projects (Blacks Ford in northwest St. Johns County, over $220 million; near Jacksonville International Airport, about $193 million; East Arlington, just under $165 million) and the $117 million Fulton Cut transmission line clearance over the St. Johns River near Blount Island. Fulton Cut, shared with JAXPORT and the city, is expected to finish in summer 2027 and all four projects by 2030.
What it may mean for the marketRaised power lines support larger ship access to port terminals, and new reclamation capacity supports growth in surrounding areas. The site is about 8 miles north of Windy Hills.
Source: News4JAX - September 2026Development
Gateway Jax seeks more than $70 million in city incentives for Riverfront Plaza tower and Hotel Merrydelle
Gateway Jax is requesting about $55.4 million in incentives for a 17-story, roughly $271.5 million Riverfront Plaza tower with 130 to 170 hotel rooms and 50 to 150 residences on Independent Drive. It also seeks a $15 million loan for the nearly $50 million renovation of the former Ambassador Hotel at 420 Julia Street. The Downtown Investment Authority board votes Sept. 16 and City Council has the final say.
What it may mean for the marketIf approved, the projects would add hotel rooms, residences and restaurants along the Downtown riverfront. The site is about 8 miles northwest of Windy Hills.
Source: Jacksonville Today - June 2026Infrastructure
First Coast Expressway advances as an economic-development corridor across Clay and St. Johns
The First Coast Expressway (State Road 23), a tolled beltway looping around the west and south of the Jacksonville metro, continued to open land for development along its corridor, with the final St. Johns County phase from Interstate 95 to east of County Road 2209 in progress. FDOT held a St. Johns County open house on the final phase in January 2026.
What it may mean for the marketNew limited-access highway capacity shortens commutes and opens adjacent land, changes that have historically shaped where new communities and demand concentrate. The site is about 20 miles southwest of Windy Hills.
Source: Jax Daily Record - April 2026Development
Southeast Toyota opens $170M vehicle-processing facility at JAXPORT's Blount Island, adding 400-plus jobs
Southeast Toyota Distributors dedicated a new vehicle processing facility at JAXPORT's Blount Island Marine Terminal in April 2026. The company put the investment at $170 million and said the facility created more than 400 full-time jobs, most of them hired locally.
What it may mean for the marketA large new employment center on Blount Island adds sustained local job demand, a factor that has historically supported nearby housing absorption. The site is about 8 miles north of Windy Hills.
Source: JAXPORT - February 2026Infrastructure
JAXPORT details $250M Blount Island modernization and record cargo in 2026 State of the Ports
At its February 2026 State of the Ports address, JAXPORT outlined a $250 million modernization of Blount Island's container and vehicle-handling capabilities and reported record fiscal-2025 cargo volumes. The port also said an air-draft expansion to accommodate larger ships is on track to finish by the end of 2026.
What it may mean for the marketContinued heavy investment in the Blount Island port complex anchors long-term industrial employment on the northeast side, a structural demand driver for the surrounding area. The site is about 8 miles north of Windy Hills.
Source: News4Jax
Summaries reflect public reporting and official sources linked above as of the dates shown. Project details, timelines, and approvals can change. Commentary on potential market effects is general observation, not investment advice or a prediction for any specific property. For the freshest items across the whole region, see This Week in Northeast Florida.
Frequently Asked Questions
How many homes are in Windy Hills?
What share of Windy Hills is owner-occupied?
When were the homes in Windy Hills built?
Who is the best real estate agent for Windy Hills?
How do I find a top Jacksonville real estate agent who knows Windy Hills?
Can Momentum Realty connect me with an agent for Windy Hills?
Should you buy in Windy Hills?
An honest fit check. We will tell you when it is not your community.
Nearby Communities
Explore more neighborhoods near Windy Hills with Momentum Realty’s local guides.
Data sources & freshness
| Housing stock & ownership | Florida DOR assessment roll (street-list match (1 streets, ZIP 32216/32246)) |
| Under-contract shares | realMLS records, as of 2026-10-20 |
| Historical depth | Closed-sale records back to 2002 (12 transactions analyzed) |
Verify the primary sources yourself: Florida DOR · U.S. Census · FEMA flood maps · Citizens Property Insurance.
Momentum Research figures are our own analysis of realMLS records; MLS data is deemed reliable but not guaranteed. Methodology: how Momentum market scores are computed. Market metrics describe homes for sale and recent sales, not residents.
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