Oak Grove East
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.
Photo via Stellar MLS
As of November 2026, the MLS records 11 closed sales in Oak Grove East in Kissimmee, FL since 2013, the most recent in May 2026. 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).
Oak Grove East is a small, established pocket of Kissimmee — 118 homes with a median build year of 1975 and a footprint that spans everything from mid-1950s cottages to construction as recent as 2022. That build range tells you most of what you need to know about price here: this is a condition-driven market, not a spec-sheet one. Two homes on the same street can sit far apart in value depending on roof, systems, and how much of the original 1975 stock has actually been updated.
With a homestead share around 70%, this leans owner-occupied rather than investor-churned, which tends to mean tighter inventory and homes that don't turn over casually. For a buyer, that means patience and a willingness to underwrite renovation costs. For a seller, the older median age of the housing puts a premium on documented updates — the improvements you can prove are what separate your listing from the dated comp down the block.
Figures in this note are as of July 14, 2026. The live market numbers elsewhere on this page update nightly and are newer.
Nearby homes for sale
No active listings inside Oak Grove East right now. These are the 6 closest homes on the market, by straight-line distance from the community's center; some may sit just outside its boundary.
Listing data from the MLS feeds named on each listing page; deemed reliable but not guaranteed. Refreshed nightly.
The 60-Second Overview
A compact, largely owner-occupied enclave in Osceola County where a median living area under 1,500 square feet and a build span from 1954 to 2022 mean you're really shopping individual condition, not a uniform product.
Stellar MLS sales records identify 24 homes in Oak Grove East that have changed hands since 2005, built between 1973 and 1976 (median 1974), with a median living area of about 1,365 sq ft and a typical 3-bedroom, 2-bath layout; 100% 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 3 qualified sales in Oak Grove East across 2024–2025 (1 in 2024, 2 in 2025), median $280,000 — 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 Oak Grove East is best for.
Best for
- Buyers comfortable with an older home who can underwrite renovation or systems work into their budget
- Owner-occupants seeking a compact, established neighborhood rather than a large new build
- Value-minded buyers willing to wait for the right updated listing in a thin-inventory market
Probably not for
- Buyers who require new construction and modern square footage
- Investors looking for high turnover and rental churn in a heavily homesteaded pocket
- Anyone needing move-in-ready certainty without inspecting for aging roof and systems
The market around Oak Grove East
Oak Grove East 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 Oak Grove East specifically. Momentum Research analysis of MLS records.
The Oak Grove East buying strategy.
If we were buying in Oak Grove East 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 Oak Grove East.
An older, small-footprint market
The median home here runs about 1,460 square feet — modest by current standards — and the median build year of 1975 means many of these houses have lived through multiple ownership cycles. The value question isn't square footage alone; it's whether the roof, HVAC, electrical, and plumbing have kept pace with the calendar. Homes built closer to 2022 exist in this community, but they're the exception against a mostly mid-century-to-1970s backbone.
Because inventory is thin at 118 homes and roughly seven in ten are homesteaded, well-updated listings tend to draw attention while dated ones sit until the price reflects the work needed. Buyers should budget for the gap between move-in-ready and project. Sellers should invest in the paperwork trail — permits, receipts, dates — because in a market this varied, proof of condition does the heavy lifting.
The location and the amenities are priced into every listing in Oak Grove East. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
In a market where price hinges on condition rather than a tidy price band, our job is to read each home on its own terms — pull the permit history, weigh the systems against the 1975-era median, and tell you honestly where a listing sits between project and turnkey. That's how we keep buyers from overpaying for cosmetics and help sellers get credit for the updates that matter.
Oak Grove East in 15 seconds.
Tools for a Oak Grove East 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 Oak Grove East sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Oak Grove East, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Oak Grove East home worth?
Get a no-obligation home value based on real comparable sales in Oak Grove East, 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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| Location | Kissimmee, Osceola County, FL · ZIP 34744 |
|---|---|
| Homes in the community | 118 (FL DOR 2025 assessment roll) |
| Years built | 1954–2022 (median 1975.0) |
| Typical living area | 1,460 sq ft (median) |
| For sale right now | 0 active, 0 pending |
| Owner-occupied (homestead) share | 70% |
Data as of September 20, 2026. Based on Stellar MLS data distributed by MLS GRID for the period 2013 through 2026; housing-stock figures from Florida Department of Revenue public records. Market figures describe homes, not residents. Cite as: Momentum Realty, “Oak Grove East key facts,” movewithmomentum.com/neighborhoods/oak-grove-east, data as of September 20, 2026.
Housing distress & ownership in Oak Grove East, 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.
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Kissimmee guides & data
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- Homestead exemption (Osceola County)
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Florida buyer guides
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- Florida flood insurance calculator
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Recent Developments in Oak Grove East
Development, infrastructure, retail, and school activity affecting Oak Grove East, 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 4 miles southwest of Oak Grove East, 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 site is about 2 miles southeast of Oak Grove East.
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 2 miles southeast of Oak Grove East.
Source: WFTV - September 2026Development
Orange County commissioners approve Tuscana land use plan in Shingle Creek Basin on 4-3 vote
Commissioners voted 4-3 to approve the Tuscana land use application from Shingle Creek Co-Owners LLC and Geyer Development, reversing a unanimous rejection in May 2025. The plan includes more than 1,000 hotel rooms, about 4,000 apartments and commercial buildings, with conditions for a raised road, flood mitigation and wetland protection.
What it may mean for the marketThe approval could add substantial rental housing, hotel capacity and commercial space in the Shingle Creek area, while flood-mitigation conditions will shape how and when it is built. The site is about 5 miles northwest of Oak Grove East.
Source: Spectrum News 13 - 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 site is about 8 miles northwest of Oak Grove East.
Source: FOX 35 Orlando - 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 10 miles northeast of Oak Grove East.
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 Northeast Florida.
Frequently Asked Questions
How many homes are in Oak Grove East?
What share of Oak Grove East is owner-occupied?
When were the homes in Oak Grove East built?
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Where is Oak Grove East, and what county is it in?
Should you buy in Oak Grove East?
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 2013 (11 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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