5301 Greenbrook Drive, Sarasota, FL 34238
Active Under Contract $2,099,999
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Under contract-accepting backup offers. 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!
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)
Clubhouse
Fence Restrictions
Fitness Center
Gated
Pickleball Court(s)
Spa/Hot Tub
Tennis Court(s)
Trail(s)
Taxes: $17,854.00
Tax Year: 2025
Association Fee: $1,680.00
Association Fee Frequency: Quarterly
Lighting
Outdoor Kitchen
Sidewalk
Sliding Doors
Cooktop
Dishwasher
Disposal
Dryer
Microwave
Refrigerator
Washer
Park/Greenbelt
Elementary School: Laurel Nokomis Elementary
Middle School: Laurel Nokomis Middle
Junior High: Laurel Nokomis Middle
High School: Venice Senior High
MLS Area: 34238 - Sarasota/Sarasota Square
Total Square Footage: 6,659
Price per Square Feet: $406.11
Total Floors: 2
Water: Public
Construction: Block, Stucco
Date Listed: 2026-04-30 00:00:00
Pool: Y
Pool Description: Heated
Private Spa: Y
Furnished: Unfurnished
Garage Description: Y
Garage Spaces: 3
Attached Garage: Y
Flooring: Carpet, Laminate, Tile
Roof: Tile
Heating: Central
Cooling: Central Air
Laundry: Laundry Room
Pets: Breed Restrictions, Cats Ok, Dogs Ok
Sewer: Private Sewer
Lot Desc.: Corner Lot
Parcel ID: 0138040038
Amenities: Clubhouse, Fence Restrictions, Fitness Center, Gated, Pickleball Court(S), Spa/Hot Tub, Tennis Court(S), Trail(S)
Listing Courtesy Of: Keller Williams On The Water S
mark.allen.quire@gmail.com
Under contract-accepting backup offers. 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!
Property Details
Price: $2,099,999
Sq Ft: 5,171
($406 per
sqft)
Bedrooms: 5
Bathrooms: 4
Partial Baths: 2
City: Sarasota
County: Sarasota
Type: Single Family
Development: Legacy Estates At Esplanade On Palmer Ranch
Acres: 0.2600
Virtual Tour/Floorplan: View
Year Built: 2019
Listing Number: A4691224
Status Code: Active Under Contract
Taxes: $17,854.00
Tax Year: 2025
Garage:
3
/
Y
Furnishings: Unfurnished
Pets Allowed: Breed Restrictions, Cats OK, Dogs OK
Total Recurring Fees: $560
Total Recurring Fee Frequency: 0.00
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)
Amenities:
Clubhouse
Fence Restrictions
Fitness Center
Gated
Pickleball Court(s)
Spa/Hot Tub
Tennis Court(s)
Trail(s)
Financial Information:
Taxes: $17,854.00
Tax Year: 2025
Association Fee: $1,680.00
Association Fee Frequency: Quarterly
Exterior Features:
Lighting
Outdoor Kitchen
Sidewalk
Sliding Doors
Equipment:
Cooktop
Dishwasher
Disposal
Dryer
Microwave
Refrigerator
Washer
View:
Park/Greenbelt
School Information:
Elementary School: Laurel Nokomis Elementary
Middle School: Laurel Nokomis Middle
Junior High: Laurel Nokomis Middle
High School: Venice Senior High
Additional Information:
MLS Area: 34238 - Sarasota/Sarasota Square
Total Square Footage: 6,659
Price per Square Feet: $406.11
Total Floors: 2
Water: Public
Construction: Block, Stucco
Date Listed: 2026-04-30 00:00:00
Pool: Y
Pool Description: Heated
Private Spa: Y
Furnished: Unfurnished
Garage Description: Y
Garage Spaces: 3
Attached Garage: Y
Flooring: Carpet, Laminate, Tile
Roof: Tile
Heating: Central
Cooling: Central Air
Laundry: Laundry Room
Pets: Breed Restrictions, Cats Ok, Dogs Ok
Sewer: Private Sewer
Lot Desc.: Corner Lot
Parcel ID: 0138040038
Amenities: Clubhouse, Fence Restrictions, Fitness Center, Gated, Pickleball Court(S), Spa/Hot Tub, Tennis Court(S), Trail(S)
Map of 5301 Greenbrook Drive, Sarasota, FL 34238
Listing Courtesy Of: Keller Williams On The Water S
mark.allen.quire@gmail.com