Osprey Ridge
Homes for Sale in Kissimmee, FL
All 3,127 homes for sale in Kissimmee, FL · median $375,000 · 329 homes for sale in 34744 · Osceola County homes for sale
True comps, carrying-cost math, and listings before the portals.
As of November 2026, Osprey Ridge in Kissimmee, FL has 1 home for sale. As of November 2026, the MLS records 7 closed sales in Osprey Ridge in Kissimmee, FL since 2019, the most recent in October 2024. Across Kissimmee as a whole, 4,246 homes closed in the last 12 months at a median of $360,000, 64 median days on market, with 2,907 homes for sale today. At that median and Osceola County's FY2025-26 rate of 15.23 mills, annual property tax runs about $5,480 ($4,880 with the full homestead exemption).
Last 30 days in Osprey Ridge: 1 new listing (median asking $385,000), 1 under contract right now. As of November 13, 2026, Listings courtesy of Stellar MLS as distributed by MLS GRID.
Osprey Ridge is a small, newer pocket of 95 homes in Kissimmee, built in a tight 2018 - 2019 window. With construction that uniform and a median around 1,923 square feet, floor plans and vintage don't vary much here - so the price spread you see comes mostly from condition, lot, and updates rather than fundamentally different houses. Price everything off the median and adjust from there.
The market posture right now is thin and quiet: one active listing and no closings in the current window. That gives you very little comparable data to lean on, which cuts both ways. A seller who prices cleanly can own the spotlight with no competition; a buyer has almost nothing to triangulate against and should expect to anchor to the few closest sales available rather than a deep comp set.
Figures in this note are as of October 26, 2026. The live market numbers elsewhere on this page update nightly and are newer.
The 60-Second Overview
A compact, nearly new subdivision where the homes are closely matched in age and size, so the real differences between listings tend to show up in condition and finish rather than layout. The high homestead share - about 76% - points to a community held mostly as primary residences rather than churned as rentals.
Stellar MLS sales records identify 58 homes in Osprey Ridge that have changed hands since 2018, built between 2018 and 2019 (median 2018), with a median living area of about 1,651 sq ft and a typical 3-bedroom, 2-bath layout; 93% are single-family homes. Source: Stellar MLS closed-sale history compiled by Momentum Research; counts reflect homes with a recorded MLS sale, not every home in the community.
County records show 6 qualified sales in Osprey Ridge across 2024 - 2024, median $453,000 - the last recorded sale per parcel on the Florida DOR 2025 assessment roll, independent of the MLS.
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 Osprey Ridge is best for.
Best for
- Buying a newer home where systems and roof are of a similar, recent age
- Buyers who prefer a small, primarily owner-occupied subdivision
- Trading into a predictable mid-size floor plan without renovation surprises
Probably not for
- Needing on-site amenities like a pool, clubhouse, or gated access
- Shopping for architectural variety or an older home with character
- Wanting a deep set of recent comparable sales before committing
The market around Osprey Ridge
Osprey Ridge is too small for its own price trend, so here is the market around it.
In ZIP 34744, 447 homes are on the market and 19% are under contract — a steady corner of Kissimmee.
Across Osceola County, 4,465 homes are active and 1,093 pending (20% under contract).
In ZIP 34744 (Kissimmee), 271 homes closed in the last 12 months at a median of $390K ($212/sq ft), up 5.3% year over year, with a median 36 days on market. See the live ZIP 34744 housing market and the Osceola County market.
ZIP and county figures describe the wider market, not Osprey Ridge specifically. Momentum Research analysis of MLS records.
Homes For Sale Right Now in Osprey Ridge
Live MLS inventory for Osprey Ridge. 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 and pending Osprey Ridge listings as of 2026-11-12, priced high to low. Based on Stellar MLS data distributed by MLS GRID for the period 2019 through 2024. Tap any home to ask about it.
Schools
- Osceola County Public Schools
- Verify the zoned schools by address
- Magnet and choice options may be available
- Narcoossee Middle · Middle
- Tohopekaliga High School · High
Zoned schools reflect the assignments reported on recent Osprey Ridge listings and can change; always confirm with Osceola County Public Schools for a specific address.
Buying with schools in mind? We can confirm the exact zoned schools for any Osprey Ridge address.
Shop the zone: Homes zoned for Tohopekaliga High School
Recent Developments in Osprey Ridge
Development, infrastructure, retail, and school activity affecting Osprey Ridge, tracked by our team and summarized from public reporting and official sources, with links to the original coverage. Last updated November 2026.
- October 2026Parks & Amenities
145,000 sq ft All Sports Dome planned on Gus Road in Kissimmee
All Sports Dome Southeast plans a climate-controlled indoor inflatable dome at 3070 Gus Road with multi-sport courts, turf fields and training areas. It would be the brand's first Greater Orlando location, with an opening expected in 2027 and no exact date given.
What it may mean for the marketAn indoor sports venue would add year-round recreation and event space on Kissimmee's Gus Road area. The project is about 13 miles southwest of Osprey Ridge, elsewhere in Osceola County.
Source: What Now Orlando - October 2026Infrastructure
Turnpike widening in Osceola County runs ahead of schedule at Fortune Road Bridge
Steel beams for the new westbound Fortune Road Bridge are in place a month early as Florida's Turnpike is widened from two to four lanes each way between Partin Settlement Road and Osceola Parkway. Westbound bridge traffic is expected at the start of 2027, and the broader project targets 2031. The bridge adds bike lanes and sidewalks.
What it may mean for the marketDoubling Turnpike capacity through this stretch should ease regional commutes between Kissimmee and the Orlando area once complete. The project is about 9 miles west of Osprey Ridge, elsewhere in Osceola County.
Source: WFTV - October 2026Development
Experience Kissimmee launches Film Kissimmee commission to recruit productions
The new film commission markets Osceola County to production companies through an online database of more than 100 filming locations and has hired a location manager. Leaders say productions could become a new economic driver, citing spending on hotels, vehicles, food and crew services.
What it may mean for the marketFilm work could add temporary jobs and visitor spending for hospitality and service businesses across Osceola County. The site is about 10 miles southwest of Osprey Ridge.
Source: WFTV - September 2026Infrastructure
CFX holds public meetings on 14-mile toll road through part of Split Oak Forest
The Central Florida Expressway Authority held public meetings on Sept. 16 and 17 for a 14-mile road from State Road 417 near Boggy Creek Road in Orange County to Nova Road in Osceola County. CFX says portions could begin construction next year and that the road would ease traffic on Narcoossee Road. The agency faces a legal challenge from Orange County and is pursuing an eminent domain case.
What it may mean for the marketIf built, the road would add a new east-west route between Lake Nona and St. Cloud, changing commute options and access to east Orange and Osceola land. The site is about 4 miles northeast of Osprey Ridge.
Source: Spectrum News 13 - August 2026Civic
St. Cloud council approves $6.7 million downtown apartment and parking garage agreement
The City Council unanimously approved an agreement with Atlantic Housing Partners for apartments and a parking garage next to City Hall. The Community Redevelopment Agency contributes $6.25 million and the city $460,000. The garage would hold 450 to 500 spaces, with 250 reserved for apartment residents.
What it may mean for the marketNew downtown rental housing and public parking would add residents and parking capacity to the St. Cloud core. The project is about 7 miles south of Osprey Ridge, elsewhere in Osceola County.
Source: Spectrum News 13 - March 2026Development
Orlando approves the 380-acre Dowden Central Community Development District in Lake Nona
Orlando approved the Dowden Central Community Development District, a roughly 380-acre district in the Lake Nona area of southeast Orlando, in March 2026. The district provides the framework to build roads, drainage, utilities, and parks for future development phases.
What it may mean for the marketA new community development district lays the groundwork for large-scale growth in the Lake Nona area, a step that typically precedes new housing and commercial activity nearby. The site is about 3 miles northwest of Osprey Ridge.
Source: ClickOrlando
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 Osprey Ridge buying strategy.
If we were buying in Osprey Ridge 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 Osprey Ridge.
A uniform enclave with a thin tape
Everything here was built within a two-year stretch, with a median year built of 2019 and a median footprint just under 1,923 square feet. That consistency is useful: mechanicals, roofs, and systems are all of a similar age, and you won't be comparing a 1980s house to a brand-new one down the street. The flip side is that there's no architectural variety to shop - if you want an older home with character or a much larger plan, this isn't where you'll find it.
No community amenities surface in the current MLS listings, so treat this as an amenity-light subdivision and weigh location and the home itself accordingly. With only one home active and nothing closed in the current window, the trading data is genuinely thin - you'll be working from a small sample, and timing matters more than usual when so little is on the market.
The location and the amenities are priced into every listing in Osprey Ridge. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
In a market this thin, the comp set is small and easy to misread. We work the handful of relevant sales carefully, weigh condition against the median, and keep you from either overpaying in a vacuum or underpricing when you have no competition. On the sell side, a single active listing is an opportunity to lead on price - we help you use it.
Osprey Ridge in 15 seconds.
Tools for a Osprey Ridge 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 Osprey Ridge sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Osprey Ridge, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Osprey Ridge home worth?
Get a no-obligation home value based on real comparable sales in Osprey Ridge, 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 Osprey Ridge
Homes in Osprey Ridge 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. 1 on record.
- 3202 Surfbird Street · off market
| Location | Kissimmee, Osceola County, FL · ZIP 34744 |
|---|---|
| Homes in the community | 95 (FL DOR 2025 assessment roll) |
| Years built | 2018–2019 (median 2019) |
| Typical living area | 1,923 sq ft (median) |
| Amenities listed by sellers | Playground |
| For sale right now | 1 active, 0 pending · median asking $495,000 |
| Owner-occupied (homestead) share | 76% |
Data as of September 20, 2026. Based on Stellar MLS data distributed by MLS GRID for the period 2019 through 2024; housing-stock figures from Florida Department of Revenue public records. Market figures describe homes, not residents. Cite as: Momentum Realty, “Osprey Ridge key facts,” movewithmomentum.com/neighborhoods/osprey-ridge-kissimmee, data as of September 20, 2026.
Housing distress & ownership in Osprey Ridge, Kissimmee
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 November 2026 through November 2026. Deemed reliable but not guaranteed.
Every Home for Sale in Osprey Ridge Kissimmee Right Now (2)
All 2 active and pending Osprey Ridge Kissimmee listings with a detail page, newest first, refreshed twice a day from the MLS.
- 4561 Gadwall Drive · $385,000 · 3 bd / 2 ba · listed Nov 11, 2026 · listed by Re/Max Assured
- 4580 Gadwall Drive · $350,000 · 3 bd / 2 ba · pending · listed Sep 30, 2026 · listed by Lpt Realty, Llc
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Kissimmee guides & data
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Florida buyer guides
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16% of homes for sale in ZIP 34744 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 (2026-11-14).
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Ask an agent about Osprey Ridge
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Frequently Asked Questions
How many homes are in Osprey Ridge?
What share of Osprey Ridge is owner-occupied?
When were the homes in Osprey Ridge built?
Who is the best real estate agent for Osprey Ridge?
How do I find a top Kissimmee real estate agent who knows Osprey Ridge?
Can Momentum Realty connect me with an agent for Osprey Ridge?
Where is Osprey Ridge, and what county is it in?
Should you buy in Osprey Ridge?
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: November 12, 2026) |
| Housing stock & ownership | Florida DOR assessment roll (street-list match (3 streets, ZIP 34744)) |
| Under-contract shares | Stellar MLS records, as of 2026-09-20 |
| Historical depth | Closed-sale records back to 2019 (7 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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