Oakland Park
Homes for Sale in Winter Garden, FL
All 750 homes for sale in Winter Garden, FL · median $585,000 · Orange County homes for sale
True comps, carrying-cost math, and listings before the portals.
Market Heat
As of October 2026, Oakland Park in Winter Garden, FL has 8 homes for sale and 2 pending, asking from $610,000 to $1,644,999 (median $852,500). Over the 12 months ending 2026-08-02, 21 recorded sales closed at a median of $935,000, $368 per square foot, a median 5 days on market, sellers accepting 100% of original asking (-0% versus the prior year). Homes listed or recently sold were built 2012 - 2026 with 2 new construction; 22 of 22 report an HOA (median $208/mo); none of the 22 geocoded homes sit in a FEMA special flood hazard zone (median elevation 102 ft). At the median price and Orange County's FY2025-26 rate of 16.67 mills, annual property tax runs about $15,590 ($14,920 with the full homestead exemption).
Last 30 days in Oakland Park: 4 new listings (median asking $654,000), 2 under contract right now, 1 closed sale (median $587,000). As of October 15, 2026, Listings courtesy of Stellar MLS as distributed by MLS GRID.
Homes For Sale Right Now in Oakland Park
Live MLS inventory for Oakland Park. Every active listing, what is under contract right now, and the last 12 months of closed sales, refreshed twice a day. Closed comps beat an algorithm's guess every time.
Active · 114 daysTop listing
Active · 101 days
Active · 115 days
Active · 11 days
Active · 130 days
Active · 8 days
Active · 18 days
Active · 1 days
Pending · 20 days
Pending · 3 daysActive and pending Oakland Park listings as of 2026-10-15, priced high to low. Based on Stellar MLS data distributed by MLS GRID for the period 2008 through 2026. Tap any home to ask about it.
Oakland Park right now
🔴 Seller-leaning market. 2.8 months of supply and 14% of the inventory already under contract give sellers the pressure advantage.Why it matters: months of supply is how long today's inventory would last at today's sales pace; under-contract share is the portion of homes for sale that already have a buyer.Momentum Research analysis of Stellar MLS records, as of August 2, 2026. Confidence: High (7 active and pending listings, 21 closed sales in 12 months).
🟡 Off the recent peak. The trailing-12-month median ($935K) is down 0.2% from the prior 12 months ($937K). With about 20 sales a year, a single closing can swing this number, so read the level and the decade, not one year's move.Momentum Research, record-level Stellar MLS closed sales, 12-month windows ending August 2. Confidence: High (21 and 37 sales in the two windows).
Jump to: Price history & scorecard · Homes for sale · Schools · FAQ
· Updated October 15, 2026 · Live data: Stellar MLS, refreshed twice daily · MLS facts carry their source; interpretation lines are Momentum Research · Data sources & freshness
The 60-Second Overview
Oakland Park market snapshot (as of August 2, 2026): the median sale price is about $935K ($368 per sq ft over the trailing 12 months of closed sales), a median 5 days on market for closed sales, and 2.8 months of supply, a seller-leaning market. The trailing-12-month median is down 0% from the prior 12 months, computed from record-level Stellar MLS closed sales (21 closings in the current window).
In ZIP 34778 (Winter Garden), 27 homes closed in the last 12 months at a median of $935K ($368/sq ft), up 0.8% year over year, with a median 10 days on market. Right now 11 active and 1 pending listings put supply at about 3.2 months - a healthy market. See the live ZIP 34778 housing market and the Lake County market.
Flood zones in Oakland Park: of 18 listing addresses checked against the FEMA National Flood Hazard Layer, 100% sit outside the FEMA Special Flood Hazard Area (Zone X). Individual parcels vary - verify any specific address at msc.fema.gov. See flood zones by neighborhood in Winter Garden.
Oakland Park is a community of 705 homes in Winter Garden, Orange County, built between 2008 and 2024 (median 2019), with a median living area of about 2,665 square feet. 69% of parcels are homesteaded, the owner-occupancy proxy in the Florida DOR assessment roll (2025 roll, public records).
The setting & the homes.
Aerial and on-site photos of Oakland Park. Swipe to explore the community.
Swipe or use the arrows → tap any photo to enlarge
Oakland ParkOakland ParkOakland ParkOakland ParkOakland ParkOakland ParkOakland ParkOakland ParkPhotos from Stellar MLS listings in Oakland Park; content deemed reliable but not guaranteed.
Price History: What Homes Here Have Actually Sold For
Median sale price over the trailing 12 months ending August 2 of each year, from record-level Stellar MLS closed sales. Same methodology as every appreciation figure on this page: the 2026 point ($935K) IS the median in the snapshot above, and the move from 2025 ($937K) IS the -0.2% one-year change.
Windows contain 0 to 41 sales each (21 in the current window); every figure carries its sample size, and thin markets swing on single closings. Based on Stellar MLS data distributed by MLS GRID for the period 2008 through 2026. Deemed reliable but not guaranteed.
Oakland Park Market Scorecard
Oakland Park is currently a buyer's market. About 9.0 months of supply, a median asking price of $865,000, and homes go under contract in about 18 days.
Typical home value in the 34787 ZIP is $570,875, right around the Florida norm (Zillow Home Value Index).
Go deeper: ZIP market scorecard · county scorecard · true cost calculator · affordability calculator.
Live data: Stellar MLS, distributed by MLS GRID, refreshed twice daily. Typical value: Zillow Research. Market metrics only; these describe homes for sale and recent sales, not residents.
Oakland Park on the map.
Every active, pending, and recently sold home, plotted. Toggle the layers and tap a home for the details.
Listing locations from Stellar MLS. Map data © OpenStreetMap contributors.
Life at Oakland Park
- Clubhouse · reported on 19 of 20 listings
- Playground · reported on 19 of 20 listings
- Pool · reported on 19 of 20 listings
- Park · reported on 18 of 20 listings
- Golf Carts OK · reported on 17 of 20 listings
- Dog Park · reported on 14 of 20 listings
- Trail(s) · reported on 9 of 20 listings
- Community Mailbox · reported on 5 of 20 listings
- Deed Restrictions · reported on 4 of 20 listings
- Recreation Facilities · reported on 3 of 20 listings
- Irrigation-Reclaimed Water · reported on 2 of 20 listings
- Maintenance · reported on 1 of 20 listings
Community amenities as reported across Stellar MLS listings in this community; deemed reliable but not guaranteed. Verify current amenities and access with the HOA.
Schools
- Orange County Public Schools
- Verify the zoned schools by address
- Magnet and choice options may be available
- Tildenville Elem · Elementary
- Lakeview Middle · Middle
- West Orange High · High
Zoned schools reflect the assignments reported on recent Oakland Park listings and can change; always confirm with Orange County Public Schools for a specific address.
Buying with schools in mind? We can confirm the exact zoned schools for any Oakland Park address.
Shop the zone: Homes zoned for West Orange High High School
Recent Developments in Oakland Park
Development, infrastructure, retail, and school activity affecting Oakland Park, tracked by our team and summarized from public reporting and official sources, with links to the original coverage. Last updated October 2026.
- September 2026Development
Lake County approves 2,241-acre Panther Run rezoning for up to 2,624 homes near Clermont
The Lake County Commission voted 3-1 on Sept. 1 to rezone about 2,241 acres in the Wellness Way area, north of Sawgrass Bay Boulevard, for GT Homes. The planned unit development allows up to 2,624 residential units and more than 1 million square feet of non-residential space, with sites reserved for a future public high school and public safety facilities. Plans include extending County Road 455 and about 11 miles of public trails.
What it may mean for the marketThe plan adds long-term housing supply, employment space and new connector roads in south Lake County, with infrastructure planned ahead of residential growth. The site is about 11 miles southwest of Oakland Park.
Source: Clermont Sun - August 2026Retail & Dining
Plans for Mattel indoor water park near Lake Buena Vista Factory Stores expand to 13 acres
Updated plans for the site off State Road 535 show a 95,000-square-foot indoor water park designed by Martin Aquatic, a separate 45,000-square-foot entertainment building and nearly 900 parking spaces. The tower height rises to as much as 100 feet and still needs Orange County approval. About 200 jobs are expected, and no opening date has been announced.
What it may mean for the marketThe project would add visitor attractions, dining and roughly 200 jobs near the State Road 535 corridor, with added traffic and parking demand nearby. The project is about 13 miles southeast of Oakland Park, elsewhere in Orange County.
Source: FOX 35 Orlando - July 2026Development
Orange County opens Enclave at Canopy Park with 104 affordable units
Orange County opened The Enclave at Canopy Park, a 104-unit affordable apartment community at 4440 Canopy Park Loop developed by Archway Partners. The county contributed 3 million dollars from its Affordable Housing Trust Fund. The community includes one and two bedroom homes plus a community center, fitness center, technology lab, and EV charging.
What it may mean for the marketAdds 104 income-restricted apartment homes to the local rental supply along with new community amenities and green-certified construction. The project is about 14 miles east of Oakland Park, elsewhere in Orange County.
Source: ClickOrlando - July 2026Civic
Orange County previews new Innovation Center on West Colonial Drive
Orange County previewed its new Innovation Center at 7149 West Colonial Drive, located within the county's Multicultural Center and Senior Center complex, with an official opening set for Fall 2026. The center will offer technology programs including 3D printing and makerspace prototyping through the Orange County Library System, plus career exploration and workforce training through CareerSource Central Florida.
What it may mean for the marketAdds a county operated civic and technology facility with library and workforce programming to the West Colonial corridor. The project is about 9 miles east of Oakland Park, elsewhere in Orange County.
Source: Orange County Newsroom - June 2026Development
Mixed-use high-rise redesigned for 924 and 934 North Magnolia Avenue
A redesigned 17-story mixed-use high-rise was proposed for 924 and 934 North Magnolia Avenue in Orlando's North Quarter district by Acram Group. The project would include 350 residential units, about 3,300 square feet of ground-floor commercial space, and a parking garage with 510 spaces, replacing two 1972 office buildings. A public plaza is planned at the corner of Magnolia and Weber Street.
What it may mean for the marketWould replace two aging office buildings with 350 residences, ground floor retail, and structured parking, adding housing density and a public plaza along the Orlando Urban Trail. The project is about 15 miles east of Oakland Park, elsewhere in Orange County.
Source: Florida YIMBY - October 2025Retail & Dining
New Apopka complex with restaurants and offices set to open in 2026
A new commercial complex in Apopka with restaurants and office space is set to open in 2026, adding retail and workplace space in northwest metro Orlando.
What it may mean for the marketNew retail and office space in Apopka adds everyday conveniences and local jobs, amenity and employment factors that can support nearby housing demand. The project is about 10 miles northeast of Oakland Park, elsewhere in Orange County.
Source: GrowthSpotter
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 the Orlando Metro.
The Oakland Park buying strategy.
If we were buying in Oakland Park 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.
Come strong and clean. Homes here move, so lead with your best terms and financing ready rather than a low anchor.
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 Oakland Park.
A closer look at the Oakland Park market
At a median of $368 per square foot, Oakland Park prices sit in a fairly defined band, so condition and updates — more than the list price — tend to separate one home from the next.
Inventory runs at 2.8 months of supply, a seller-leaning market. Homes that do trade take a median 5 days on market, useful leverage on any listing that has lingered.
The housing stock is 705 homes built between 2008 and 2024, and 69% of parcels are homesteaded — the owner-occupancy proxy in the Florida DOR assessment roll.
The location and the amenities are priced into every listing in Oakland Park. The deal is won or lost on condition, the comps, and the renovation math.
Momentum Buy Score.
Our proprietary 0 to 10 read across the factors that decide how a home in Oakland Park buys, holds, and resells. Momentum Research; not an appraisal.
Momentum Intelligence Scores are our proprietary, qualitative assessment on a 0 to 10 scale, built from the record-level market data on this page. They are a framework for comparing communities, not a guarantee of future value and not advice on a specific home; unlike an automated value estimate they do not price your home, they grade the community on evidence you can inspect. Composite is the plain average of the 4 factors (7.5). Basis: Recent Direction -0.2% year-over-year; Liquidity & Demand 2.8 months of supply; Owner Commitment 69% owner-occupied; Pricing Power 99.6% sale-to-list. Refreshed with each data update.
What it really costs to own in Oakland Park
The parts of the monthly number a mortgage calculator leaves out, from the tax roll, the MLS, Citizens and FEMA. Property facts only.
| HOA dues | Median $208/month across 628 MLS listings (most billed quarterly; 2026-10-15). Dues cover what the documents say they cover; ask for the budget and reserve study. |
|---|---|
| Home and flood insurance | The average Citizens Property Insurance premium in Orange County is $1,409/yr (4,204 policies, Citizens detail by county, April 2026); private-market quotes depend on roof age, wind mitigation and construction. Flood: of 18 listing addresses checked against the FEMA flood map, 100% sit outside the high-risk zone. Statewide, a Zone X flood policy runs about $500-$700/yr and a high-risk zone $1,200-$2,500/yr (FEMA Risk Rating 2.0 averages, not quotes). |
| Roof and age | Median build year 2022 across 22 listings. Newer roofs and current wind-mitigation features usually mean the lower end of insurance quotes. |
Email me new listings in Oakland Park
One e-mail a day, only when a home lists here, with price, beds, baths and a link to every listing. Straight from the MLS feed; no account needed.
Ask an agent about Oakland Park
Have a question about the homes, fees, rules or commute here? A Momentum agent who works Oakland Park will answer, and the answer is published on this page for the next buyer.
HOA, CDD & Fees
- HOA dues reported around $208/month (about $2,496/yr) · median of 628 MLS listings, most billed quarterly
- Any club/amenity membership is billed separately
Listings in this community report association dues of about $208 per month ($2,496 a year) - the median AssociationFee across 628 MLS records, normalised to a monthly figure; most are billed quarterly. Dues change with budgets and can differ by section or product type; confirm the current figure with the association before you offer. Source: MLS listing records, 2026-10.
Confirm the current HOA dues, exactly what they cover, and any CDD bond or special assessment for a specific address before you offer.
Flood & Insurance Context
Of 18 sampled listing addresses in this community: 100% outside the FEMA Special Flood Hazard Area (Zone X/B/C).
Address-sampled; individual parcels vary - verify any specific address at msc.fema.gov. Check any address at FEMA's Flood Map Service Center, and see average home-insurance costs by Florida county.
Source: FEMA National Flood Hazard Layer, address-level lookups (n=18) · as of 2026-10
Tools for a Oakland Park 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 Oakland Park sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Oakland Park, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Oakland Park home worth?
Get a no-obligation home value based on real comparable sales in Oakland Park, not an automated guess. Tell us about your home and we will personally prepare your numbers and a pricing strategy. No obligation, no spam.
See all homes for sale in Winter Garden →
Recently off market in OAKLAND PARK
Homes in OAKLAND PARK that recently left the market. Each address opens its public-record profile: county-recorded value, property taxes, the last recorded sale, community sales history, and what is for sale nearby now. 4 on record.
- 1258 Ridge Lake Way · off market
- 720 Lake Brim Drive · off market
- 914 Trowman Alley · off market
- 944 Kylee Aly · off market
| Location | Winter Garden, Orange County, FL · ZIP 34778, 34787 |
|---|---|
| Homes in the community | 705 (FL DOR 2025 assessment roll) |
| Years built | 2008–2024 (median 2019) |
| Typical living area | 2,665 sq ft (median) |
| Home types (current listings and sales) | single-family 100% |
| Amenities listed by sellers | Clubhouse, Pool, Playground, Park, Golf Carts OK, Dog Park |
| Sale prices, last 12 months | $935,000 median across 21 closed sales · $368 per sq ft · -0.2% vs the prior 12 months |
| Days on market (closed sales) | 5 median |
| For sale right now | 6 active, 1 pending · median asking $1,160,000 · 2.8 months of supply |
| Owner-occupied (homestead) share | 69% |
Data as of August 2, 2026. Based on Stellar MLS data distributed by MLS GRID for the period 2008 through 2026; housing-stock figures from Florida Department of Revenue public records. Market figures describe homes, not residents. Cite as: Momentum Realty, “Oakland Park key facts,” movewithmomentum.com/neighborhoods/oakland-park-winter-garden, data as of August 2, 2026.
Housing distress & ownership in OAKLAND PARK, Winter Garden
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. Based on Stellar MLS data distributed by MLS GRID for the period October 2026 through October 2026. Deemed reliable but not guaranteed.
Just listed in Oakland Park
The newest homes for sale in Oakland Park right now, newest first. Each link opens the full listing with every photo, the price history and a tour request.
- 923 Colie Alley $610,000 · 3 bd · 2.5 ba · 1,786 sq ft · 1 day on market Courtesy of CFRP REALTY LLC
- 939 Kylee Alley $670,000 · 3 bd · 2.5 ba · 1,772 sq ft · 8 days on market Courtesy of HOMEVEST REALTY
- 1021 Huntspoint Street $865,000 · 4 bd · 3.5 ba · 2,445 sq ft · 11 days on market Courtesy of BHHS FLORIDA REALTY
- 910 Trowman Aly $638,000 · 3 bd · 2.5 ba · 1,650 sq ft · 18 days on market Courtesy of WATSON REALTY CORP
- 844 Oakland Park Boulevard $1,195,000 · 5 bd · 4 ba · 3,525 sq ft · 101 days on market Courtesy of COLDWELL BANKER REALTY
- 1101 Eagles Pass Way $1,644,999 · 6 bd · 5 ba · 4,104 sq ft · 114 days on market Courtesy of LAKESIDE REALTY WINDERMERE INC
Checked against the MLS Oct 15, 2026. All new listings in this market.
Every Home for Sale in Oakland Park Winter Garden Right Now (10)
All 10 active and pending Oakland Park Winter Garden listings with a detail page, newest first, refreshed twice a day from the MLS.
- 939 Kylee Alley · $670,000 · 3 bd / 2.5 ba · listed Oct 5, 2026 · listed by Homevest Realty
- 923 Allenhurst Street · $789,000 · 3 bd / 2 ba · pending · listed Oct 1, 2026 · listed by Florida Realty Marketplace
- 1021 Huntspoint Street · $865,000 · 4 bd / 3.5 ba · listed Sep 30, 2026 · listed by Bhhs Florida Realty
- 150 Hammock Preserve Loop · $879,000 · 4 bd / 3 ba · pending · listed Sep 25, 2026 · listed by Compass Florida Llc
- 910 Trowman Aly · $638,000 · 3 bd / 2.5 ba · listed Sep 19, 2026 · listed by Watson Realty Corp
- 923 Colie Alley · $610,000 · 3 bd / 2.5 ba · listed Sep 11, 2026 · listed by Cfrp Realty Llc
- 844 Oakland Park Boulevard · $1,195,000 · 5 bd / 4 ba · listed Jul 16, 2026 · listed by Coldwell Banker Realty
- 1101 Eagles Pass Way · $1,644,999 · 6 bd / 5 ba · listed Jul 16, 2026 · listed by Lakeside Realty Windermere Inc
- 925 Easley Avenue · $1,075,000 · 4 bd / 3.5 ba · listed Jul 16, 2026 · listed by Compass Florida Llc
- 907 Easley Avenue · $840,000 · 3 bd / 2.5 ba · listed Jul 16, 2026 · listed by Bhhs Florida Realty
Recently sold in Oakland Park Winter Garden
- 914 Trowman Alley · sold $587,000
- 944 Kylee Aly · sold $779,900
- 720 Lake Brim Drive · sold $1,590,000
Closed sales from the MLS; each page shows the sold price, taxes and value history.
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Frequently Asked Questions
What is the median home price in Oakland Park?
How long do homes in Oakland Park take to sell?
Is Oakland Park a buyer's or seller's market right now?
How many homes are in Oakland Park?
What share of Oakland Park is owner-occupied?
When were the homes in Oakland Park built?
Do cash buyers compete in Oakland Park?
Who is the best real estate agent for Oakland Park?
How do I find a top Winter Garden real estate agent who knows Oakland Park?
Can Momentum Realty connect me with an agent for Oakland Park?
Where is Oakland Park, and what county is it in?
Is Oakland Park in a flood zone?
Is Oakland Park a good place to live?
Data sources & freshness
| Live listings | Stellar MLS, refreshed twice daily (last: October 15, 2026) |
| Community market stats | Stellar MLS closed sales, 12-month windows ending August 2, 2026 |
| Housing stock & ownership | Florida DOR assessment roll (street-list match (44 streets, ZIP 34778/34787)) |
| Under-contract shares | Stellar MLS records, as of 2026-08-01 |
| Historical depth | Closed-sale records back to 2008 (241 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 Stellar MLS 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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See how OAKLAND PARK fits the bigger picture — live prices, inventory, and Momentum Scores:
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More on Oakland Park
- Home values · What homes in Oakland Park actually sell for