How many homes are for sale in Oaks?

Active MLS inventory in Oaks updates throughout the day. Browse this page for live counts, prices, and photos, or set up a saved search to be notified the moment a new home is listed.

What is the average price of a home in Oaks?

Median list prices in Oaks are computed from current MLS listings and shown on this page. Actual sold prices and HOA fees vary by floor plan and view — confirm the latest with the listing agent.

Does Oaks have an HOA?

HOA status varies by community and even by phase within the same community. Each MLS listing on this page shows the HOA fee, frequency, and what it covers. Always review the HOA documents and budget before making an offer.

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Coast 2 CoastHome Realty

Florida › Osprey › Oaks

Oaks Homes for Sale

🔒 Gated community🏊 Resort-style amenities🎓 Top-rated schools

Homes for sale

$1.2M

Average price

$407

Avg $ / sqft

203

Avg days on market

Listings Amenities Schools What's Nearby Open Houses Under Contract Solds Neighborhoods

Welcome to Oaks

Oaks in Osprey

Oaks is a resort-style community in Osprey, Florida, built by Lee Wetherington Homes between 1990–2006. Buyers choose from condominiums, single-family homes, all with access to a resort-style amenity campus featuring pool, fitness center, deed restrictions, golf, tennis court(s). Families are drawn to Gulf Gate Elementary, Brookside Middle, Riverview High and quick access to I-75, Waterside and Main Street dining, and the Gulf beaches about 40 minutes west. There are currently 36 homes for sale, with an average list price around $1.2M.

Commute to Work

See the drive time from Oaks to your office, gym, or anywhere that matters.

Know before you tour

Oaks Quick Facts

Builder

Lee Wetherington Homes

Year Built

1990–2006

Home Types

Condo · SF

Pets

Yesw/ restrictions

Rentals

Yesw/ restrictions

55+

CDD

Variesby home

Inside Oaks

For sale now

Homes For Sale in Oaks

Create a Search for OaksGet new listings the moment they hit the market

Map unavailable

ACTIVE

GATED

$235,000

DOM: 119•$395/sqft· MLS #MFRA4689838

Condo For Sale

51 MACEWEN DR #5

OSPREY, 34229

View all Windsor Lodge at the Oaks homes →

1 bd1 ba595 sqft

HOA

$425/qtr

CDD

—

Taxes

$3,079.45/yr

Laurel Nokomis ElementarySarasota MiddlePine View School

ACTIVE

GATED

$275,000

DOM: 104•$441/sqft· MLS #MFRA4690540

Condo For Sale

51 MACEWEN DR #12

OSPREY, 34229

View all Oaks homes →

1 bd1 ba623 sqft

HOA

$425/qtr

CDD

—

Taxes

$3,079.45/yr

Laurel Nokomis ElementarySarasota MiddleVenice Senior High

ACTIVE

$285,000

DOM: 119•$479/sqft· MLS #MFRA4690371

Condo For Sale

51 MAC EWEN DR #14

OSPREY, 34229

View all Oaks homes →

1 bd1 ba595 sqft

HOA

$425/qtr

CDD

—

Taxes

$2,483.44/yr

Laurel Nokomis ElementarySarasota MiddleVenice Senior High

ACTIVE

$459,900

DOM: 884•$177/sqft· MLS #MFRA4603773

Condo For Sale

401 N POINT RD #301

OSPREY, 34229

View all Meridian at the Oaks Preserve homes →

3 bd3 ba2,594 sqft

HOA

$1,100/qtr

CDD

—

Taxes

$6,783.33/yr

Gulf Gate ElementaryBrookside MiddleRiverview High

ACTIVE

$525,000

DOM: 194•$196/sqft· MLS #MFRA4681290

Condo For Sale

3621 N POINT RD #301

OSPREY, 34229

View all Meridian at the Oaks Preserve homes →

3 bd3 ba2,680 sqft

HOA

—

CDD

—

Taxes

$6,143.2/yr

Gulf Gate ElementaryBrookside MiddleRiverview High

ACTIVE

$560,000

DOM: 118•$216/sqft· MLS #MFRA4690812

Condo For Sale

409 NORTH POINT RD #401

OSPREY, 34229

View all Meridian at the Oaks Preserve homes →

3 bd3 ba2,594 sqft

HOA

$1,100/qtr

CDD

—

Taxes

$6,285.2/yr

Gulf Gate ElementaryBrookside MiddleRiverview High

ACTIVE

GATED

$599,000

DOM: 704•$291/sqft· MLS #MFRA4621353

Condo For Sale

409 N POINT RD #502

OSPREY, 34229

View all Meridian at the Oaks Preserve homes →

3 bd3 ba2,055 sqft

HOA

$1,200/qtr

CDD

—

Taxes

$4,344.82/yr

Gulf Gate ElementaryBrookside MiddleRiverview High

ACTIVE

GATED

$615,000

DOM: 569•$299/sqft· MLS #MFRA4635708

Condo For Sale

385 N POINT RD #402

OSPREY, 34229

View all Meridian at the Oaks Preserve homes →

3 bd3 ba2,055 sqft

HOA

$1,200/qtr

CDD

—

Taxes

$5,877.28/yr

Gulf Gate ElementaryBrookside MiddleRiverview High

ACTIVE

$629,000

DOM: 277•$286/sqft· MLS #MFRA4671958

Condo For Sale

401 N POINT RD #603

OSPREY, 34229

View all Meridian at the Oaks Preserve homes →

3 bd3 ba2,203 sqft

HOA

—

CDD

—

Taxes

$8,771/yr

Gulf Gate ElementaryBrookside MiddleRiverview High

ACTIVE

GATED

$690,000

DOM: 272•$313/sqft· MLS #MFRA4672342

Condo For Sale

385 N POINT RD #503

OSPREY, 34229

View all Meridian at the Oaks Preserve homes →

3 bd3 ba2,203 sqft

HOA

$1,100/qtr

CDD

—

Taxes

$7,327.07/yr

Gulf Gate ElementaryBrookside MiddleRiverview High

ACTIVE

GATED

$695,000

DOM: 74· MLS #MFRA4696023

Home For Sale

216 OSPREY POINT DR

OSPREY, 34229

View all Oaks homes →

— bd0 ba— sqft

HOA

$2,850/yr

CDD

—

Taxes

$0/yr

Laurel Nokomis ElementarySarasota MiddleVenice Senior High

ACTIVE

$699,000

DOM: 206· MLS #MFRA4679677

Home For Sale

410 BLUE GARDEN LN

OSPREY, 34229

View all Oaks homes →

— bd0 ba— sqft

HOA

$5,000/yr

CDD

—

Taxes

$2,740/yr

ACTIVE

GATED

$739,000

DOM: 17•$317/sqft· MLS #MFRA4701662

Single Family Home For Sale

299 TURQUOISE LN

OSPREY, 34229

View all Emerald Woods at Oaks homes →

3 bd2 ba2,328 sqft

HOA

$1,550/qtr

CDD

—

Taxes

$7,188.96/yr

Gulf Gate ElementaryBrookside MiddleRiverview High

ACTIVE

GATED

$749,000

DOM: 87•$368/sqft· MLS #MFRA4694468

Single Family Home For Sale

103 BISHOPS COURT RD

OSPREY, 34229

View all Oaks homes →

3 bd2 ba2,034 sqft

HOA

$1,275/qtr

CDD

—

Taxes

$3,742.76/yr

Pine View SchoolPine View SchoolPine View School

ACTIVE

GATED

$769,000

DOM: 501•$333/sqft· MLS #MFRA4645829

Single Family Home For Sale

13 BAYHEAD LN

OSPREY, 34229

View all Oaks homes →

3 bd2 ba2,310 sqft

HOA

$1,275/qtr

CDD

—

Taxes

$3,620.44/yr

Gulf Gate ElementaryBrookside MiddleRiverview High

ACTIVE

GATED

$789,000

DOM: 336•$351/sqft· MLS #MFRA4664085

Single Family Home For Sale

21 BAYHEAD LN

OSPREY, 34229

View all Bishopscourt at the Oaks Preserve homes →

3 bd2 ba2,246 sqft

HOA

$1,374/qtr

CDD

—

Taxes

$4,221.15/yr

Gulf Gate ElementaryBrookside MiddleRiverview High

ACTIVE

GATED

$795,000

DOM: 66•$286/sqft· MLS #MFRA4696459

Condo For Sale

401 N POINT RD #504

OSPREY, 34229

View all Meridian at the Oaks Preserve homes →

3 bd3 ba2,778 sqft

HOA

$1,200/qtr

CDD

—

Taxes

$8,766.9/yr

Gulf Gate ElementaryBrookside MiddleRiverview High

ACTIVE

$825,000

DOM: 374•$377/sqft· MLS #MFRA4660895

Single Family Home For Sale

599 PINE RANCH EAST RD

OSPREY, 34229

View all Bay Oaks Estates homes →

3 bd2 ba2,188 sqft

HOA

$270/yr

CDD

—

Taxes

$3,484.04/yr

Laurel Nokomis ElementaryLaurel Nokomis MiddleVenice Senior High

Lifestyle

Oaks Amenities

Life at Oaks

12 of 16 amenities

Clubhouse

Resort Pool

Fitness Center

Spa & Sauna

Lifestyle Director

Walking Trails

Dog Park

Playground

Golf

Tennis

Pickleball

Basketball

Bar / Restaurant

Boating / Water Access

Gated Entry

55+ Community

HOA & lifestyle

What's Included in Oaks

Your HOA fees include

Approx. $23–$517/mo

Guard - 24 Hour
Pool
Maintenance Grounds
Private Road
Security

Community features

◆Pool

◆Fitness Center

◆Deed Restrictions

◆Golf

◆Tennis Court(s)

◆Gated Community - Guard

◆Clubhouse

◆Street Lights

◆Buyer Approval Required

◆Playground

◆Restaurant

◆Sidewalks

◆Special Community Restrictions

Sarasota County · FL DOE Grades

Oaks Assigned Schools

School Report Card

Source: FL Dept. of Education

ABCDF

Elementary

Middle

High

Google Maps · Drive times

What's Nearby Oaks

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Open Houses in Oaks

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Pending

Homes Under Contract in Oaks

PENDING

$695,000

DOM: 384•$250/sqft· MLS #MFRA4659785

Condo For Sale

401 N POINT RD #304

OSPREY, 34229

View all Meridian at the Oaks Preserve homes →

3 bd3 ba2,778 sqft

HOA

$1,100/qtr

CDD

—

Taxes

$8,473.38/yr

Gulf Gate ElementaryBrookside MiddleRiverview High

No Image Available

PENDING

GATED

$885,000

DOM: 201•$427/sqft· MLS #MFRA4679867

Single Family Home For Sale

227 SAINT JAMES PARK

OSPREY, 34229

View all Oaks homes →

2 bd2 ba2,071 sqft

HOA

$425/qtr

CDD

—

Taxes

$4,610.52/yr

Laurel Nokomis ElementarySarasota MiddleVenice Senior High

PENDING

GATED

$1,500,000

DOM: 168•$468/sqft· MLS #MFRA4684136

Single Family Home For Sale

480 ORISKANY CT

OSPREY, 34229

View all The Oaks Club homes →

3 bd4 ba3,208 sqft

HOA

$425/qtr

CDD

—

Taxes

$6,365/yr

Laurel Nokomis ElementarySarasota MiddleVenice Senior High

PENDING

GATED

$2,650,000

DOM: 108•$501/sqft· MLS #MFRA4688291

Single Family Home For Sale

449 WEBBS COVE

OSPREY, 34229

View all Oaks homes →

4 bd4 ba5,287 sqft

HOA

$2,950/yr

CDD

—

Taxes

$10,623.25/yr

Laurel Nokomis ElementarySarasota MiddleVenice Senior High

Market report · last 12 months

Oaks Market Report

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Market

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Good to know

Oaks FAQs

Is Oaks a gated community?+

Gating varies by phase; each listing notes its access. We can confirm for any home you're considering.

What are the HOA & CDD fees?+

HOA dues run around $23–$517/mo and typically cover Guard - 24 Hour, Pool, Maintenance Grounds. A CDD assessment may also apply and appears on the annual tax bill.

Are pets and rentals allowed?+

Both are generally allowed with restrictions per the Oaks community documents — we'll pull the exact rules for any home you're considering.

Who builds in Oaks?+

Oaks features homes by Lee Wetherington Homes.

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Explore the area

Other Osprey Neighborhoods

Sarasota Beachfrom $6.4M Founders Clubfrom $2.3M Everly/Wellen Parkfrom $3.5M Watersidefrom $3.5M Country Club East At Lakewd Rnch Yy1from $1.8M Riverwalk Ridgefrom $995K Greenbrook Villagefrom $865K Bishopscourt At The Oaks Preservefrom $789K

Community guide

About Oaks

Life in Oaks

Oaks is built around an active, resort-style lifestyle. Residents enjoy pool, fitness center, deed restrictions, golf, tennis court(s). It's the kind of place where you can start the morning at the fitness center, spend the afternoon by the pool, and meet neighbors at a community event that evening.

HOA, CDD & What's Included

HOA dues in Oaks run about $23–$517 per month and typically cover Guard - 24 Hour, Pool, Maintenance Grounds, Private Road. Like many Lakewood Ranch communities, a CDD assessment may also apply and shows up on the annual tax bill. We'll walk you through the exact fees for any home you're considering so there are no surprises.

Location & What's Nearby

Set in Osprey, Oaks keeps everyday essentials minutes away — Publix and shopping at Lakewood Ranch, dining at Waterside Place and Main Street, and I-75 for an easy commute toward Sarasota, Bradenton and Tampa. Sarasota-Bradenton International Airport is roughly a half-hour away, and the white-sand Gulf beaches of Anna Maria Island and Siesta Key make for an easy day trip.

Schools & the Local Market

Oaks is served by Gulf Gate Elementary, Brookside Middle, Riverview High. With an average list price around $1.2M and homes selling close to asking, the community remains one of Osprey's most in-demand addresses. Whether you're buying your first home or right-sizing, our team can share live sold data and help you act quickly when the right home hits the market.

Your Local Oaks Advisor

Thinking about Oaks?

Get honest answers about available homes, builder incentives, HOA and CDD fees, schools, amenities, and whether Oaks is the right fit for you.

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Current MLS listings & builder incentives

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Frank Harris

Broker/Owner · Coast 2 Coast Home Realty