Rolling Woods
Homes for Sale in Orlando, FL
All 4,095 homes for sale in Orlando, FL · median $379,900 · 154 homes for sale in 32808 · Orange County homes for sale
True comps, carrying-cost math, and listings before the portals.
Photo via Stellar MLS
Over the 12 months ending 2026-09-20, 5 recorded sales closed at a median of $290,000, $205 per square foot, a median 36 days on market, sellers accepting 94% of original asking. Homes listed or recently sold were built 1970–1970; none of the 6 geocoded homes sit in a FEMA special flood hazard zone (median elevation 105 ft). At the median price and Orange County's FY2025-26 rate of 16.67 mills, annual property tax runs about $4,840 ($4,160 with the full homestead exemption).
| Location | Orlando, Orange County, FL · ZIP 32808 |
|---|---|
| Homes in the community | 152 (FL DOR 2025 assessment roll) |
| Years built | 1959–1975 (median 1970.0) |
| Typical living area | 1,418 sq ft (median) |
| Home types (current listings and sales) | single-family 100% |
| Sale prices, last 12 months | $290,000 median across 5 closed sales · $205 per sq ft |
| Days on market (closed sales) | 36 median |
| For sale right now | 0 active, 1 pending |
| Owner-occupied (homestead) share | 63% |
Data as of September 20, 2026. Based on Stellar MLS data distributed by MLS GRID for the period 2006 through 2026; housing-stock figures from Florida Department of Revenue public records. Market figures describe homes, not residents. Cite as: Momentum Realty, “Rolling Woods key facts,” movewithmomentum.com/neighborhoods/rolling-woods, data as of September 20, 2026.
Last 30 days in Rolling Woods: 1 closed sale (median $265,000). As of October 2, 2026, Listings courtesy of Stellar MLS as distributed by MLS GRID.
Rolling Woods is a small, established pocket of 152 homes built between 1959 and 1975, with the typical house around 1,418 square feet. At a median of $290,000 and roughly $205 per square foot, price here is driven less by size or address and more by condition and how much of the original mid-century house has been updated. Expect a wide spread between move-in-ready and project homes; two houses of the same footprint can sit far apart on price depending on systems, roof, and kitchens.
The market posture is cool. A heat score of 31 and a median of 36 days on market — just over a month — tell you sellers do not hold all the cards. Buyers have room to inspect carefully and negotiate on condition rather than chasing. Sellers should price to the realistic condition of the home from the start; the days-on-market data says overpriced listings will sit.
The 60-Second Overview
Rolling Woods market snapshot (as of September 20, 2026): the median sale price is about $290K ($205 per sq ft over the trailing 12 months of closed sales), and a median 36 days on market for closed sales.
In ZIP 32808 (Orlando), 380 homes closed in the last 12 months at a median of $257K ($194/sq ft), up 1.6% year over year, with a median 44 days on market. Right now 52 active and 32 pending listings put supply at about 4.0 months — a balanced market. See the live ZIP 32808 housing market and the Orange County market.
County records show 9 qualified sales in Rolling Woods across 2024–2025 (4 in 2024, 5 in 2025), median $285,900 — the last recorded sale per parcel on the Florida DOR 2025 assessment roll, independent of the MLS.
Rolling Woods is a community of 152 homes in Orlando, Orange County, built between 1959 and 1975 (median 1970.0), with a median living area of about 1,418 square feet. 63% of parcels are homesteaded, the owner-occupancy proxy in the Florida DOR assessment roll (2025 roll, public records).
This is a compact enclave of older, modestly sized Orange County homes where the age of the stock — nothing newer than the mid-1970s — makes inspection and renovation cost the real story behind any listing price.
The setting & the homes.
Aerial and on-site photos of Rolling Woods. Swipe to explore the community.
Swipe or use the arrows → tap any photo to enlarge
Photos from Stellar MLS listings in Rolling Woods; content deemed reliable but not guaranteed.
Who Rolling Woods is best for.
Best for
- Buyers targeting the high-$200s who want an established, smaller-footprint home
- Renovators willing to invest in updating a mid-century house
- Owner-occupant buyers who value a thin, stable inventory over volume and turnover
Probably not for
- Buyers who need newer construction or large square footage
- Anyone without budget headroom for roof, HVAC, and systems on an older home
- Investors chasing quick flips in a cooler, slower-moving market
Price History: What Homes Here Have Actually Sold For
Median sale price over the trailing 12 months ending September 20 of each year, from record-level Stellar MLS closed sales. Same methodology as every appreciation figure on this page: the 2026 point ($290K) IS the median in the snapshot above.
Windows contain 0 to 7 sales each (5 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 2006 through 2026. Deemed reliable but not guaranteed.
28% of homes for sale in ZIP 32808 are already under contract (under contract ÷ under contract + active listings) — a read on how much of the available inventory buyers have already claimed. Source: MLS data (2026-09-20).
Rolling Woods Market Scorecard
Rolling Woods is currently a balanced market..
Go deeper: ZIP market scorecard · county scorecard · true cost calculator · affordability calculator.
Live data: Stellar MLS, refreshed twice daily. Market metrics only; these describe homes for sale and recent sales, not residents.
Housing distress & ownership in Rolling Woods, Orlando
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 September 2026 through September 2026. Deemed reliable but not guaranteed.
Rolling Woods 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, tiles © CARTO.
Recent Developments in Rolling Woods
Development, infrastructure, retail, and school activity affecting Rolling Woods, tracked by our team and summarized from public reporting and official sources, with links to the original coverage. Last updated August 2026.
- 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 site is less than a mile east of Rolling Woods.
Source: Florida YIMBY - June 2026Development
Planning board approves zoning for 37-story tower at 170 East Washington Street
Orlando's Municipal Planning Board voted to approve a Planned Development amendment for a 37-story, 425-foot mixed-use tower at 170 East Washington Street across from Lake Eola Park. The project would include 252 residential units, a 221-room hotel, a three-story restaurant, and structured parking. It still requires City Council consideration before construction.
What it may mean for the marketWould add a 37 story tower with 252 residences and a hotel to the downtown skyline, replacing a prior approval for a 7 story hotel and increasing high density housing and parking supply. The site is less than a mile southeast of Rolling Woods.
Source: Florida YIMBY
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.
The Rolling Woods buying strategy.
If we were buying in Rolling Woods 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 Rolling Woods.
An older, condition-driven market
With every home dating to 1975 or earlier and a median build year of 1970, the practical question in Rolling Woods is not location but what has been done to the house. Roofs, electrical panels, plumbing, and HVAC on homes of this vintage are the line items that separate a $290,000 median sale from something well above or below it. Budget for a thorough inspection and read the improvements, not the square footage.
Roughly 63% of homes here carry a homestead exemption, which points to a stock held by owner-occupants rather than dominated by turnover or rentals. Combined with only 152 homes total and a modest closing pace, inventory is thin — when the right updated house appears, it will not necessarily linger, even in a cooler overall market.
The location and the amenities are priced into every listing in Rolling Woods. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
In a small, older community like this, the value is in reading condition correctly — knowing which updates hold value and which deferred repairs will eat your budget. We help buyers separate cosmetic from structural, and we help sellers price to the true condition of the home so it moves inside the roughly one-month window this market supports rather than sitting.
Rolling Woods in 15 seconds.
HOA, CDD & Fees
- HOA status not on record. Verify any dues before you offer
- Any club/amenity membership is billed separately
Confirm the current HOA dues, exactly what they cover, and any CDD bond or special assessment for a specific address before you offer.
Tools for a Rolling Woods 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 Rolling Woods sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Rolling Woods, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Rolling Woods home worth?
Get a no-obligation home value based on real comparable sales in Rolling Woods, not an automated guess. Tell us about your home and we will personally prepare your numbers and a pricing strategy. No obligation, no spam.
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Recently off market in Rolling Woods
Homes in Rolling Woods 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. 2 on record.
- 17247 SE 284Th Terrace · off market
- 5682 Altec Court · off market
Frequently Asked Questions
What is the median home price in Rolling Woods?
How long do homes in Rolling Woods take to sell?
How many homes are in Rolling Woods?
What share of Rolling Woods is owner-occupied?
When were the homes in Rolling Woods built?
Who is the best real estate agent for Rolling Woods?
How do I find a top Orlando real estate agent who knows Rolling Woods?
Can Momentum Realty connect me with an agent for Rolling Woods?
Where is Rolling Woods, and what county is it in?
Is Rolling Woods a good place to live?
Should you buy in Rolling Woods?
An honest fit check. We will tell you when it is not your community.
Data sources & freshness
| Live listings | Stellar MLS, refreshed twice daily (last: October 1, 2026) |
| Community market stats | Stellar MLS closed sales, 12-month windows ending September 20, 2026 |
| Housing stock & ownership | Florida DOR assessment roll (street-list match (6 streets, ZIP 32808)) |
| Under-contract shares | Stellar MLS records, as of 2026-09-20 |
| Historical depth | Closed-sale records back to 2006 (42 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.
Own a home here?
You just read the data. Now see what your home is worth.
The numbers on this page move markets in the aggregate. The number that matters to you is what a buyer pays for your address. Momentum sells for 1.25% above the Stellar MLS member average and 8 days faster, and we’ll price yours against live local comps.
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See how Rolling Woods fits the bigger picture — live prices, inventory, and Momentum Scores:
More on Rolling Woods
- Home values · What homes in Rolling Woods actually sell for
Nearby Communities
Explore more neighborhoods near Rolling Woods with Momentum Realty’s local guides.