$2,299,000
5301 Greenbrook Drive
Sarasota, FL 34238
Listing updated: May 21, 2026 at 11:30 AM ET
Property type
Year built
Lot size
Price / sq ft
HOA dues
Days on market
Garage spaces
Flood zone
About this home
Opportunities like this are rare within the exclusive Legacy Estates at Esplanade on Palmer Ranch. This exceptional two-story Gulf Coast residence offers 5 bedrooms, 4 full baths, 2 half baths, and 5,171 square feet designed for luxury living, multigenerational flexibility, executive work-from-home, and elevated entertaining. Perfectly positioned on a private corner homesite with preserve views and direct access to the Legacy Trail, the home is just a bike ride from Gulf Coast waters and nationally acclaimed Pine View School, currently ranked #12 in the nation. A dramatic gallery-style entry immediately captures attention with a striking overhead walkway connecting the upper-level wings before opening into a breathtaking two-story living room with soaring 25-foot ceilings, abundant natural light, and seamless indoor-outdoor living. The expansive three-panel sliders open to a private lanai, resort-style pool, and serene preserve backdrop with no neighbors to the rear or west. The main level features an executive office with French doors, formal dining room, guest suite, chef’s kitchen designed for entertaining, and an elegant owner’s retreat with spa-inspired bath. Upstairs, four generously sized bedrooms are thoughtfully split between two wings, each featuring private sink and vanity areas. A spacious recreational loft overlooks the grand living area and is complemented by a half bath and additional flex room ideal for a theater, study, fitness room, or secondary office. Additional luxury features include hurricane impact windows throughout, Sonos whole-home audio, abundant storage, gated security, and a spacious 3-car garage. Legacy Estates at Esplanade delivers a true resort lifestyle with the on-site Bahama Bar restaurant, resort pools and spa, fitness center with studio classes, 8 pickle ball courts, 2 tennis courts, 3 dog parks, scenic nature trails, and direct Legacy Trail access. Oscar Scherer State Park is just one mile away. More than a home, this is a private luxury retreat offering the ultimate blend of elegance, recreation, wellness, and Gulf Coast living. Schedule your private showing today!
Estimated monthly payment
Estimate only. Taxes use the listing's reported amount where available; insurance is a Florida-average estimate. Your actual payment will vary — run a full calculation or talk to a lender.
Price & listing history21 days on market
- Status: ActiveApr 30, 2026
- Listed$2,500,000Apr 30, 2026
- Price reduced$2,299,000
Facts & features
- Property type
- Residential
- Sub type
- Single Family Residence
- Status
- Active
- Days on market
- 21
- Subdivision
- Legacy Estates At Esplanade On Palmer Ranch
- County
- Sarasota
- Year built
- 2019
- Living area
- 5,171 sq ft
- Price/sq ft
- $445
- Building area
- 6,659 sq ft (Public Records)
- Lot size
- 11,430 sq ft
- Lot category
- 1/4 to less than 1/2
- Flood zone
- X (12115C0229G)
- Garage
- 3 spaces
- Pool
- Private pool
- Annual taxes
- $17,854 (2025)
- Parcel #
- 0138040038
- Zoning
- RSF1
- MLS #
- A4691224
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Interior Details
- Bedrooms
- 5
- Full bathrooms
- 4
- Half bathrooms
- 2
- Flooring
- Carpet, Laminate, Tile
- Appliances
- Cooktop, Dishwasher, Disposal, Dryer, Microwave, Refrigerator, Washer
- Interior features
- Ceiling Fans(s), Crown Molding, High Ceilings, Open Floorplan, Primary Bedroom Main Floor, Solid Surface Counters, Solid Wood Cabinets, Split Bedroom, Stone Counters, Thermostat, Walk-In Closet(s)
- Laundry
- Laundry Room
- Stories / Levels
- Two
- Direction faces
- North
Heating & Cooling
- Heating
- Central
- Cooling
- Central Air
Parking
- Garage spaces
- 3
- Attached garage
- Yes
HOA & Financial
- HOA fee
- $1,680 / Quarterly
- Monthly HOA
- $560/mo
- Total monthly fees
- $560/mo
- Total annual fees
- $6,720
- HOA name
- Castle Group/ Taylor Young
- CDD
- No
- Homestead exemption
- Yes
- Min lease term
- 3 Months
- Listing terms
- Cash, Conventional, VA Loan
- Ownership
- Fee Simple
- Available for lease
- Yes
- Lease restrictions
- Yes
- Additional lease restrictions
- See Rules and Restrictions for additional lease restrictions
- Approval process
- See Rules and Restrictions for lease approval process.
Exterior & Construction
- Exterior features
- Lighting, Outdoor Kitchen, Sidewalk, Sliding Doors
- Construction materials
- Block, Stucco
- Roof
- Tile
- Foundation
- Slab
- Pool
- Private pool
- Road surface
- Paved
Utilities
- Sewer
- Private Sewer
- Water source
- Public
- Utilities
- Electricity Connected, Natural Gas Connected, Water Connected
Community
- Pets allowed
- Breed Restrictions, Cats OK, Dogs OK
Schools
Letter grades: Florida DOE 2024–25 school grades (Orange, Seminole, Lake, Osceola, Brevard). Assigned schools from the listing agent — verify enrollment with the district.
Room Details
| Room | Level | Dimensions |
|---|---|---|
| Living Room | First | 16x22 |
| Dining Room | First | 16x12 |
| Kitchen | First | 16x13 |
| Primary Bedroom | First | 13x18 |
| Primary Bathroom | First | 13x18 |
| Office | First | 10x11 |
| Loft | Second | 28x17 |
| Media Room | Second | 15x19 |
| Bedroom 2 | Second | 15x19 |
| Bedroom 3 | Second | 14x20 |
| Bedroom 4 | Second | 11x18 |
| Bedroom 5 | Second | 13x19 |
| Balcony/Porch/Lanai | First | 44x37 |
Listing Details
- Listing date
- 2026-04-30
- On market date
- 2026-04-30
- Original list price
- $2,500,000
- Occupant type
- Owner
- MLS area
- 34238 - Sarasota/Sarasota Square
- Listing AOR
- Sarasota - Manatee
- Status changed
- 2026-04-30
- Tax legal description
- LOT 34, LEGACY ESTATES ON PALMER RANCH PHASE 2, PB 51 PG 35-42
Flood risk
Minimal-risk area outside the mapped floodplain. Flood insurance is optional and typically low-cost.
Source: FEMA flood zone reported on the listing. Confirm current designation at FEMA Flood Map Service Center.
Location
Directions
From Central Sarasota Parkway travel south on Honore Avenue. Turn right into Legacy Estates at Esplanade on Palmer Ranch Entrance, pass through gate. Follow Legacy Estates Boulevard around the turn, turn left on Greenbrook Drive, home is the last home on the left.
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Listings courtesy of Stellar MLS as distributed by MLS GRID
IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
Based on information submitted to the MLS GRID as of May 21, 2026 at 11:30 AM ET. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.
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