Oaks 2
Homes for Sale in Osprey, FL
All 100 homes for sale in Osprey, FL · median $734,450 · 96 homes for sale in 34229 · Sarasota County homes for sale
True comps, carrying-cost math, and listings before the portals.
Market Heat
As of October 2026, Oaks 2 Ph 2 in Osprey, FL has 5 homes for sale and 2 pending, asking from $1,495,000 to $3,700,000 (median $2,395,000). Over the 12 months ending 2026-08-02, 9 recorded sales closed at a median of $2,000,000, $553 per square foot, a median 9 days on market, sellers accepting 93% of original asking (+8% versus the prior year). Homes listed or recently sold were built 1986 - 2024; 19 of 19 report an HOA (median $133/mo); none of the 19 geocoded homes sit in a FEMA special flood hazard zone (median elevation 13 ft). At the median price and Sarasota County's FY2025-26 rate of 13.48 mills, annual property tax runs about $26,960 ($26,420 with the full homestead exemption).
Last 30 days in Oaks 2: 2 new listings (median asking $2,597,500), 2 under contract right now, 1 closed sale (median $1,612,500). As of October 16, 2026, Listings courtesy of Stellar MLS as distributed by MLS GRID.
Homes For Sale Right Now in Oaks 2
Live MLS inventory for Oaks 2. 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 · 1 daysTop listing
Active · 405 days
Active · 444 days
Active · 720 days
Active · 21 days
Pending · 0 days
Pending · 0 daysActive and pending Oaks 2 listings as of 2026-10-14, 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.
Oaks 2 right now
🟢 Still climbing. The trailing-12-month median ($2M) is up 8.1% from the prior 12 months ($1.85M) and up 245% since 2012. With about 8 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: Medium (9 and 9 sales in the two windows).
Jump to: Price history & scorecard · Homes for sale · Schools · FAQ
· Updated October 16, 2026 · Live data: Stellar MLS, refreshed twice daily · MLS facts carry their source; interpretation lines are Momentum Research · Data sources & freshness
Nearby homes for sale
No active listings inside OAKS 2 PH 2 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
Oaks 2 market snapshot (as of August 2, 2026): the median sale price is about $2M ($553 per sq ft over the trailing 12 months of closed sales), and a median 9 days on market for closed sales. The trailing-12-month median is up 8% from the prior 12 months and up 245% since 2012, computed from record-level Stellar MLS closed sales (9 closings in the current window).
In ZIP 34229 (Osprey), 229 homes closed in the last 12 months at a median of $675K ($281/sq ft), up 4.9% year over year, with a median 68 days on market. Right now 1 active and 1 pending listings put supply at about 3.0 months - a balanced market. See the live ZIP 34229 housing market and the Sarasota County market.
Oaks 2 is a community of 128 homes in Osprey, Sarasota County, built between 1986 and 2024 (median 1992.0), with a median living area of about 4,320 square feet. 73% 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 Oaks 2. Swipe to explore the community.
Swipe or use the arrows → tap any photo to enlarge
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Oaks 2Photos from Stellar MLS listings in Oaks 2; 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 ($2M) IS the median in the snapshot above, and the move from 2025 ($1.85M) IS the +8.1% one-year change.
Windows contain 0 to 20 sales each (9 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.
21% of homes for sale in ZIP 34229 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 (2026-10-17).
The Oaks Market Scorecard
The Oaks is currently a balanced market. About 5.0 months of supply, a median asking price of $2,395,000, and homes go under contract in about 405 days.
Typical home value in the 34229 ZIP is $662,508, about 42.5% above 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.
Oaks 2 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.
Schools
- Sarasota County Public Schools
- Verify the zoned schools by address
- Magnet and choice options may be available
- Sarasota County Public Schools (verify by address) · Public
- Confirm zoned elementary, middle, and high · By address
- Magnet and choice options may apply · Choice
Zoned schools reflect the assignments reported on recent Oaks 2 listings and can change; always confirm with Sarasota County Public Schools for a specific address.
Buying with schools in mind? We can confirm the exact zoned schools for any Oaks 2 address.
Shop the zone: Homes zoned for Venice Senior High High School
The Oaks 2 buying strategy.
If we were buying in Oaks 2 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 Oaks 2.
A closer look at the Oaks 2 market
At a median of $553 per square foot, Oaks 2 prices sit in a fairly defined band, so condition and updates — more than the list price — tend to separate one home from the next.
The trailing-12-month median up 8% year over year. Homes that do trade take a median 9 days on market, useful leverage on any listing that has lingered.
The housing stock is 128 homes built between 1986 and 2024, and 73% 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 Oaks 2. 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 Oaks 2 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 (7.6). Basis: Long-Term Appreciation +245% since 2012; Recent Direction +8.1% year-over-year; Owner Commitment 73% owner-occupied; Pricing Power 92.7% sale-to-list. Refreshed with each data update.
What it really costs to own in Oaks 2
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 $133/month across 620 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 Sarasota County is $2,126/yr (4,849 policies, Citizens detail by county, April 2026); private-market quotes depend on roof age, wind mitigation and construction. |
| Roof and age | Median build year 1992 across 20 listings. An original roof here would be about 34 years old; under Florida's 2022 reform (SB 2-D) carriers may require an inspection past 15 years, so budget for a roof report, and for replacement where it fails. |
Email me new listings in Oaks 2
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 Oaks 2
Have a question about the homes, fees, rules or commute here? A Momentum agent who works Oaks 2 will answer, and the answer is published on this page for the next buyer.
HOA, CDD & Fees
- HOA dues reported around $133/month (about $1,596/yr) · median of 620 MLS listings, most billed quarterly
- Any club/amenity membership is billed separately
Listings in this community report association dues of about $133 per month ($1,596 a year) - the median AssociationFee across 620 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.
Tools for a Oaks 2 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 Oaks 2 sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Oaks 2, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Oaks 2 home worth?
Get a no-obligation home value based on real comparable sales in Oaks 2, 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 Osprey →
Recently off market in OAKS 2 PH 2
Homes in OAKS 2 PH 2 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.
- 854 Macewen Drive · off market
- 916 Macewen Drive · off market
| Location | Osprey, Sarasota County, FL · ZIP 34229, 34746 |
|---|---|
| Homes in the community | 128 (FL DOR 2025 assessment roll) |
| Years built | 1986–2024 (median 1992.0) |
| Typical living area | 4,320 sq ft (median) |
| Home types (current listings and sales) | single-family 100% |
| Amenities listed by sellers | Deed Restrictions, Golf, Fitness Center, Gated, Tennis Court(s), Clubhouse |
| Sale prices, last 12 months | $2,000,000 median across 9 closed sales · $553 per sq ft · +8.1% vs the prior 12 months |
| Days on market (closed sales) | 9 median |
| For sale right now | 0 active, 0 pending |
| Owner-occupied (homestead) share | 73% |
| Zoned public schools | Sarasota County Public Schools (verify by address); Confirm zoned elementary, middle, and high; Magnet and choice options may apply |
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, “Oaks 2 key facts,” movewithmomentum.com/neighborhoods/oaks-2, data as of August 2, 2026.
Housing distress & ownership in OAKS 2 PH 2, Osprey
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 Oaks 2
The newest homes for sale in Oaks 2 right now, newest first. Each link opens the full listing with every photo, the price history and a tour request.
- 650 Oaks Creek Court $3,700,000 · 4 bd · 4 ba · 4,314 sq ft · 1 day on market Courtesy of COLDWELL BANKER REALTY
- 226 Saint James Park $1,495,000 · 3 bd · 2.5 ba · 2,591 sq ft · 21 days on market Courtesy of KELLER WILLIAMS ON THE WATER S
- 236 Saint James Park $2,700,000 · 6 bd · 6.5 ba · 6,246 sq ft · 405 days on market Courtesy of MICHAEL SAUNDERS & COMPANY
- 852 Macewen Drive $2,395,000 · 3 bd · 3.5 ba · 4,519 sq ft · 444 days on market Courtesy of GENEROUS PROPERTY
- 909 Macewen Drive $1,595,000 · 3 bd · 3.5 ba · 4,241 sq ft · 720 days on market Courtesy of GENEROUS PROPERTY
Checked against the MLS Oct 16, 2026. All new listings in this market.
Every Home for Sale in Oaks 2 Right Now (7)
All 7 active and pending Oaks 2 listings with a detail page, newest first, refreshed twice a day from the MLS.
- 650 Oaks Creek Court · $3,700,000 · 4 bd / 4 ba · listed Sep 29, 2026 · listed by Coldwell Banker Realty
- 447 E Macewen Drive · $2,750,000 · 4 bd / 4.5 ba · pending · listed Sep 11, 2026 · listed by Coldwell Banker Realty
- 222 Saint James Park · $1,800,000 · 3 bd / 3.5 ba · pending · listed Sep 11, 2026 · listed by Coldwell Banker Realty
- 226 Saint James Park · $1,495,000 · 3 bd / 2.5 ba · listed Sep 3, 2026 · listed by Keller Williams On The Water S
- 236 Saint James Park · $2,700,000 · 6 bd / 6.5 ba · listed Jul 16, 2026 · listed by Michael Saunders & Company
- 852 Macewen Drive · $2,395,000 · 3 bd / 3.5 ba · listed Jul 16, 2026 · listed by Generous Property
- 909 Macewen Drive · $1,595,000 · 3 bd / 3.5 ba · listed Jul 16, 2026 · listed by Generous Property
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Streets in this community
Street-level pages: every home on record, what sold and what is for sale on each street.
- Macewen Drive (25 homes on record)
Frequently Asked Questions
What is the median home price in Oaks 2?
How long do homes in Oaks 2 take to sell?
How many homes are in Oaks 2?
What share of Oaks 2 is owner-occupied?
When were the homes in Oaks 2 built?
Do cash buyers compete in Oaks 2?
Have Oaks 2 home prices gone up?
What schools serve Oaks 2?
Who is the best real estate agent for Oaks 2?
How do I find a top Osprey real estate agent who knows Oaks 2?
Can Momentum Realty connect me with an agent for Oaks 2?
Where is Oaks 2, and what county is it in?
Is Oaks 2 a good place to live?
Data sources & freshness
| Live listings | Stellar MLS, refreshed twice daily (last: October 14, 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 (11 streets, ZIP 34229/34746)) |
| Under-contract shares | Stellar MLS records, as of 2026-08-01 |
| Schools | 2025-26 district assignments + FLDOE school grades; verify with the district |
| Historical depth | Closed-sale records back to 2008 (147 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 OAKS 2 PH 2 fits the bigger picture — live prices, inventory, and Momentum Scores:
More on Oaks 2
- Home values · What homes in Oaks 2 actually sell for
Nearby Communities
Explore more neighborhoods near Oaks 2 with Momentum Realty’s local guides.