Heritage Oaks Golf & Country Club Sarasota, FL, real estate listings

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Heritage Oaks Golf & Country Club Sarasota, FL, real estate listings

Heritage Oaks

East of Sarasota, Heritage Oaks offers a luxury resort lifestyle. Single family homes, paired villas, condominiums were built around an 18-hole golf course. The private equity club, with full golf and tennis membership included in the purchase, is wonderful. The clubhouse and golf course have been recently renovated. There are har-tru tennis courts, fitness center, 2 restaurants, 5 pools & a gated entrance. The beautiful area features twelve miles of trails, lakes, preserves and wetlands.

View all properties for sale in this community

View SOLD properties in this community

$3,900,000
Beds: 4
Baths: 5

Premier Waterfront Opportunity in The Oaks Bayside This grand estate ...

MLS# O6305818
Status: A-Active
Listing courtesy of:
KARA MONEY LLC
$2,995,000
Beds: 4
Baths: 4

**FANTASTIC, FULLY RENOVATED ESTATE with LAKE / GARDEN VIEW is situate...

MLS# A4635707
Status: A-Active
Listing courtesy of:
GENEROUS PROPERTY
$2,795,000
Beds: 4
Baths: 3

Nestled in the prestigious gated enclave of The Oaks Bayside in Saraso...

MLS# A4642364
Status: A-Active
Listing courtesy of:
MICHAEL SAUNDERS & COMPANY
$2,500,000
Beds: 5
Baths: 5

Introducing The Grand Estate at The Oaks Bayside—a true masterpiece ...

MLS# A4647690
Status: A-Active
Listing courtesy of:
RE/MAX ALLIANCE GROUP
$2,150,000
Beds: 3
Baths: 3

**STUNNINGLY DESIGNED and UPDATED -- ARCHITECTURAL ESTATE in the covet...

MLS# A4632694
Status: A-Active
Listing courtesy of:
GENEROUS PROPERTY
$1,995,000
Beds: 4
Baths: 3

Bring your clubs and come see this beautifully remodeled home in the O...

MLS# A4639504
Status: A-Active
Listing courtesy of:
MAPP REALTY & INVESTMENT CO
$1,600,000
Beds: 3
Baths: 4

One or more photo(s) has been virtually staged. It is rare to find suc...

MLS# A4637839
Status: A-Active
Listing courtesy of:
COLDWELL BANKER REALTY
$1,045,000
Beds: 2
Baths: 2

**TURNKEY FURNISHED, ELEGANT and TRADITIONAL ESTATE by Famed Architect...

MLS# A4635743
Status: A-Active
Listing courtesy of:
GENEROUS PROPERTY
$965,000
Beds: 2
Baths: 2

**IMPRESSIVE, MOVE-IN READY, POOL HOME in the Secure and Coveted OAKS ...

MLS# A4645829
Status: A-Active
Listing courtesy of:
GENEROUS PROPERTY
$959,000
Beds: 3
Baths: 2

This incredible newly updated house with many upgrades and amenities i...

MLS# A4627082
Status: A-Active
Listing courtesy of:
MICHAEL SAUNDERS & COMPANY
$910,000
Beds: 3
Baths: 2

**STUNNING, UPDATED, MAINTENANCE-FREE Home is located in EMERALD WOODS...

MLS# A4633961
Status: A-Active
Listing courtesy of:
GENEROUS PROPERTY
$679,000
Beds: 3
Baths: 3

PRICE REDUCTION !!! Discover the epitome of Florida living on two wate...

MLS# TB8337042
Status: A-Active
Listing courtesy of:
MELANGE REAL ESTATE INC

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Active Properties Statistics

Properties On Market

Single Family: 19

Avg. Asking Price

Single Family: $1,247,574

Avg. Beds & baths

Single Family: 3/3

Avg. Asking Price Per Sqft

Single Family: $355

Sold Properties

Average Asking Price

Single Family: $1,385,986

Average Selling Price

Single Family: $1,271,429

Selling vs Asking Price

Single Family: -8.27%

Avg. Days On Market

Single Family: 59

Avg. Selling Price Per Sqft

Single Family: $361

Choose Community Market History Chart (Past 90 Days):

* These market statistics are not guaranteed to be accurate and are meant only as an estimate. Statistics for Properties are based on the previous 90 days. Contact your agent for more detailed market information.

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Featured Listings

MLS# O6305818 Property Photo

For Sale $3,900,000 MLS# O6305818

112 Osprey Point Drive
Osprey, FL 34229
Property Address

Save Property View Virtual Tour
Premier Waterfront Opportunity in The Oaks Bayside This grand estate home, perfectly positioned on a rarely available direct waterfront lot in the exclusive, gated Oaks Bayside community, offers sweeping views of Little Sarasota Bay and exceptional ...

8635 Sqft, 0.60 Acres
4 Bed, 5 Full / 1 Partial Bath
Status A-Active
Listing Courtesy of:
KARA MONEY LLC

Broker Reciprocity Compliance

MLS# A4635707 Property Photo

For Sale $2,995,000 MLS# A4635707

662 Fernwalk Lane
Osprey, FL 34229
Property Address

Save Property View Virtual Tour
**FANTASTIC, FULLY RENOVATED ESTATE with LAKE / GARDEN VIEW is situated on a SERENE, INTERIOR, CUL-DE-SAC lot with NO FLOOD concern (Zone “X”) behind the Secure Gates of the highly sought after Bayside neighborhood within The Oaks Country Club co...

4359 Sqft, 0.44 Acres
4 Bed, 4 Bath
Status A-Active
Listing Courtesy of:
GENEROUS PROPERTY

Broker Reciprocity Compliance

MLS# A4642364 Property Photo

For Sale $2,795,000 MLS# A4642364

49 Osprey Point Drive
Osprey, FL 34229
Property Address

Save Property View Virtual Tour
Nestled in the prestigious gated enclave of The Oaks Bayside in Sarasota, this Sedona-inspired retreat was recently updated from wall to wall creating a like brand new home. The estate seamlessly blends modern luxury, comfort, and serenity. With almo...

3953 Sqft, 0.40 Acres
4 Bed, 3 Full / 1 Partial Bath
Status A-Active
Listing Courtesy of:
MICHAEL SAUNDERS & COMPANY

Broker Reciprocity Compliance

MLS# A4647690 Property Photo

For Sale $2,500,000 MLS# A4647690

340 Osprey Point Dr
Osprey, FL 34229
Property Address

Save Property View Virtual Tour
Introducing The Grand Estate at The Oaks Bayside—a true masterpiece of refined living within one of Sarasota’s most prestigious gated communities. Surrounded by majestic oak trees and lush tropical landscaping, this extraordinary residence offers...

6001 Sqft, 0.78 Acres
5 Bed, 5 Full / 2 Partial Bath
Status A-Active
Listing Courtesy of:
RE/MAX ALLIANCE GROUP

Broker Reciprocity Compliance

MLS# A4632694 Property Photo

For Sale $2,150,000 MLS# A4632694

85 Sugar Mill Drive
Osprey, FL 34229
Property Address

Save Property View Virtual Tour
**STUNNINGLY DESIGNED and UPDATED -- ARCHITECTURAL ESTATE in the coveted OAKS BAYSIDE Country Club Neighborhood** on Little Sarasota Bay waters features 3 BEDS plus DEN/OFFICE, 3 FULL BATHS and incredible detail throughout including beautiful crown m...

4191 Sqft, 0.48 Acres
3 Bed, 3 Bath
Status A-Active
Listing Courtesy of:
GENEROUS PROPERTY

Broker Reciprocity Compliance

MLS# A4639504 Property Photo

For Sale $1,995,000 MLS# A4639504

67 Sugar Mill Drive
Osprey, FL 34229
Property Address

Save Property View Virtual Tour
Bring your clubs and come see this beautifully remodeled home in the Oaks Club (Bayside). Move in ready with all the amenities you need. This home boast all the room you need with 4 bedroom and a study/Bourbon room. Totally secluded back yard for enj...

4020 Sqft, 0.35 Acres
4 Bed, 3 Full / 2 Partial Bath
Status A-Active
Listing Courtesy of:
MAPP REALTY & INVESTMENT CO

Broker Reciprocity Compliance

MLS# A4637839 Property Photo

For Sale $1,600,000 MLS# A4637839

282 Shell Midden Court
Osprey, FL 34229
Property Address

Save Property View Virtual Tour
One or more photo(s) has been virtually staged. It is rare to find such an incredible combination of privacy and spectacular views as you will find in this 3 bedroom, 4.5 bath home. Located on a quiet dead-end street in The Oaks Bayside, the traditi...

3699 Sqft, 0.40 Acres
3 Bed, 4 Full / 1 Partial Bath
Status A-Active
Listing Courtesy of:
COLDWELL BANKER REALTY

Broker Reciprocity Compliance

MLS# A4635743 Property Photo

For Sale $1,045,000 MLS# A4635743

227 Saint James Park
Osprey, FL 34229
Property Address

Save Property View Virtual Tour
**TURNKEY FURNISHED, ELEGANT and TRADITIONAL ESTATE by Famed Architect, Bo MacEwen, on the Single Largest 0.32 Acre Cul De Sac Lot in the Popular SAINT JAMES PARK neighborhood in The Oaks Country Club. NEW ROOF (2024), HURRICANE IMPACT WINDOWS and S...

2071 Sqft, 0.32 Acres
2 Bed, 2 Bath
Status A-Active
Listing Courtesy of:
GENEROUS PROPERTY

Broker Reciprocity Compliance

MLS# A4645829 Property Photo

For Sale $965,000 MLS# A4645829

13 Bayhead Lane
Osprey, FL 34229
Property Address

Save Property View Virtual Tour
**IMPRESSIVE, MOVE-IN READY, POOL HOME in the Secure and Coveted OAKS PRESERVE, MAINTENANCE-FREE COMMUNITY** This residence boasts an open floor plan that is ideal for entertaining, along with a screened and spacious outdoor pool area that provides p...

2310 Sqft, 0.26 Acres
2 Bed, 2 Bath
Status A-Active
Listing Courtesy of:
GENEROUS PROPERTY

Broker Reciprocity Compliance

MLS# A4627082 Property Photo

For Sale $959,000 MLS# A4627082

21 Bayhead Lane
Osprey, FL 34229
Property Address

Save Property View Virtual Tour
This incredible newly updated house with many upgrades and amenities is the home you have been waiting for! Ideally located in the beautiful Oaks Preserve between Siesta Key and Casey Key, the private enclave is in a shaded neighborhood where reside...

2216 Sqft, 0.24 Acres
3 Bed, 2 Bath
Status A-Active
Listing Courtesy of:
MICHAEL SAUNDERS & COMPANY

Broker Reciprocity Compliance

MLS# A4633961 Property Photo

For Sale $910,000 MLS# A4633961

293 Turquoise Lane
Osprey, FL 34229
Property Address

Save Property
**STUNNING, UPDATED, MAINTENANCE-FREE Home is located in EMERALD WOODS, behind the Secure Gates of the Distinguished OAKS PRESERVE Neighborhood. Offering 3-Beds (or 2-Beds plus Den), 2-Baths and 2-Car Garage, Premium finishes abound throughout this h...

2271 Sqft, 0.20 Acres
3 Bed, 2 Bath
Status A-Active
Listing Courtesy of:
GENEROUS PROPERTY

Broker Reciprocity Compliance

MLS# TB8337042 Property Photo

For Sale $679,000 MLS# TB8337042

25555 Oaks Boulevard
Land O Lakes, FL 34639
Property Address

Save Property View Virtual Tour
PRICE REDUCTION !!! Discover the epitome of Florida living on two waterfront acres between The Outlets and Wiregrass Mall. This 3-bedroom plus den pool home offers the perfect blend of luxury and functionality. Enjoy the expansive screened porch over...

2646 Sqft, 2.02 Acres
3 Bed, 3 Full / 1 Partial Bath
Status A-Active
Listing Courtesy of:
MELANGE REAL ESTATE INC

Broker Reciprocity Compliance

Contact Chris
About Chris
Property Updates

Premier Sotheby's International Realty
4001 Tamiami Trail North, Suite 102
Naples, FL, 34103 Call Chris: 239.707.9591

Contact

The data relating to real estate for sale on this Website comes in part from the Broker Reciprocity Program (BR Program) of these sources: M.L.S. of Naples, Inc., Bonita Springs-Estero Association of REALTORS®, Southwest Florida MLS (Gulf Coast), My Florida Regional MLS DBA Stellar MLS, Sanibel and Captiva Island Association of Realtors®. Properties listed with brokerage firms other than Featured Home Listings are marked with the BR House Icon and detailed information about them includes the name of the Listing Brokers. The properties displayed may not be all the properties available through the BR Program. The data is updated every 4 hours, but can be influenced by delays from various real estate companies entering data in MLS. Some properties that appear for sale on this website may subsequently have sold or may otherwise no longer be available. All properties are subject to price or other changes without notice. For the most current information, please contact us using this form, or click on the "Request Info or Appointment" button on the search results and detailed property pages.

The source of this real property information is the copyrighted and proprietary database compilation of the © 2025 M.L.S. of Naples, Inc., © 2025 Bonita Springs-Estero Association of REALTORS®, © 2025 Southwest Florida MLS (Gulf Coast), © 2025 My Florida Regional MLS DBA Stellar MLS and © 2025 Featured Home Listings, a Florida Real Estate Brokerage. The accuracy of this information is not warranted or guaranteed. This information should be independently verified if any person intends to engage in a transaction in reliance upon it. Information last refreshed: 2025-06-04 03:18:17

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