Last Sold Price
4 beds4,875 sqft$835/sqft
4401 Midnight Pass Rd, Sarasota, FL 34242

Description

Secluded waterfront playground on north Siesta Key. Immerse yourself in a rich and many-layered world deeply-rooted in ecology and grounded in place and community. Built on one of the highest natural grades on Siesta Key, this residence draws upon the principles of organic architecture, with interior and exterior in balanced harmony. Affectionately referred to as “Selby of Siesta,” the native landscape is sublime. Each room has a beautiful view of the outdoors where old oak trees create a filtered...Secluded waterfront playground on north Siesta Key. Immerse yourself in a rich and many-layered world deeply-rooted in ecology and grounded in place and community. Built on one of the highest natural grades on Siesta Key, this residence draws upon the principles of organic architecture, with interior and exterior in balanced harmony. Affectionately referred to as “Selby of Siesta,” the native landscape is sublime. Each room has a beautiful view of the outdoors where old oak trees create a filtered light canopy over the residence. There’s plenty of room to play, too. The oversized driveway accommodates basketball and skateboarding. The large back lawn is perfect for soccer, football and volleyball. The pool/spa with surrounding decks invite water fun and relaxation. The deep-water dock with a 16,000-lbs. boat lift and kayak/paddleboard rack get you out on the water for enjoying the salt life. Gated, private beach access for the exclusive use of Cocoanut Bayou residents. Inside, high ceilings, skylights and exceptionally large windows create an open space with a calming ambiance. The living room and family room both have fully-pocketed sliding glass doors to the covered back deck with a water view. The cook’s kitchen features two islands, a gas cooktop with downdraft ventilation, new solid-wood cabinet fronts and quartz countertops. The split floor plan has three bedrooms on one side of the home and the master suite on the other. Each of the four bedrooms has an en-suite bath and sliding glass doors to a covered balcony. The master suite features a large, private loft that can be used to your heart’s desire – a meditation room, library, yoga studio, office. From the loft’s balcony, you can see the bay, Siesta Key bridge and beyond. The home’s ground level offers a full floor of non-conforming, conditioned flex space for recreation and storage. Nature, privacy and the sea. With Sarasota Bay at your back yard and easy access to Florida’s Cultural Coast from your front door, unlock the magic of life which lies at the heart of this enchanted setting. Just 1 mile to Siesta Village and Siesta Beach, 2 miles to shopping and entertainment, 3 miles to Sarasota Memorial Hospital and 4 miles to downtown Sarasota.
LISTING CLOSED: 02/11/2021 12:00 AM

  1. Listed by Peter Laughlin • Brokerage DRE #2034955 • PREMIER SOTHEBYS INTL REALTY
    P: (941) 356-8428 peter.laughlin@premiersir.com

Property Details for 4401 Midnight Pass Road

Status
MLS #
A4486881
Days on Market
7
Taxes
$21,520 / year
HOA Fees
$600 / year
Condo/Co-op Fees
-
Property Type
MLS Type
Residential / Single Family Residence
Year Built
1994
Lot Size
0.92 AC / 39,920 SF
Architectural Style
Custom
Subdivision Name
COCOANUT BAYOU
Township
37S
Garage Spaces
3
View
Garden, Pool, Water
Waterfront
Yes
Water View
Bay/Harbor - Full
Furnished
Unfurnished

Recent comparable sales

Median sold price

$3,950,000

Avg days on market

50

Sale-to-list ratio

90.7%

Sarasota, FL

9 comparable properties found

a view of multiple houses with a yard
1/2
1

$4,325,000

Sold 04/17/26

4
Bedrooms
4,213
Square Feet
0.21
Acres
a aerial view of a house with garden space and street view
1/2
2

$4,450,000

Sold 06/02/25

4
Bedrooms
5,160
Square Feet
0.42
Acres
a view of a white house with a big yard and potted plants
1/2
3

$3,542,717

Sold 11/28/25

4
Bedrooms
4,087
Square Feet
0.19
Acres
$4,500,000 | 3920 Red Rock Way, Sarasota, FL 34231
1/2
4

$4,500,000

Sold 04/11/25

4
Bedrooms
4,144
Square Feet
0.78
Acres
a front view of a house with a yard and porch
1/100
5

$3,500,000

Sold 08/03/26

4
Bedrooms
3,996
Square Feet
0.36
Acres
a front view of a house with a yard and fountain in middle of the road
1/2
6

$3,881,000

Sold 04/28/26

4
Bedrooms
4,353
Square Feet
0.46
Acres
$3,950,000 | 1739 Cherokee Drive, Sarasota, FL 34239
1/2
7

$3,950,000

Sold 04/20/26

4
Bedrooms
4,538
Square Feet
0.46
Acres
a view of a white house with a yard and plants
1/2
8

$4,450,000

Sold 01/02/25

4
Bedrooms
4,215
Square Feet
0.34
Acres
$3,800,000 | 1460 Rebecca Lane, Sarasota, FL 34231
1/2
9

$3,800,000

Sold 10/28/24

4
Bedrooms
4,030
Square Feet
0.30
Acres

Location

Add your commute

Building Information for 4401 Midnight Pass Road

Stories2Year Built1994Building Size-Lot Size0.92 AC / 39,920 SF

Payment Calculator

$22,541 per month

30 year fixed, 6.55% Interest

Principal and Interest

$20,697

Property Taxes

$1,793

HOA Dues

$50

The Payment Calculator is for illustrative purposes only.

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Property Information for 4401 Midnight Pass Road

Summary
Location and General Information
  • Building Area Source: Owner
  • Building Area Total: 10643.0
  • Building Area Units: Square Feet
  • Direction Faces: Southwest
  • Directions: From north Siesta Key Bride, drive onto Siesta Key. Go left at light. 3rd house on left.
  • Elementary School: Phillippi Shores Elementary
  • Middle Or Junior School: Brookside Middle
  • High School: Sarasota High
  • Mls Major Change Type: Sold
  • Major Change Type: Closed
  • Listing Service: Full Service
  • Road Frontage Type: Street Paved
  • Senior Community: No
  • Subdivision Num: 870
  • SW Subdiv Community Name: Cocoanut Bayou
  • Unit Number: No
  • Street Number: 4401
  • Street Name: Midnight Pass
  • Street Suffix: ROAD
  • State: FL
  • City: SARASOTA
Parking
  • Attached Garage: Yes
  • Carport: No
  • Garage Dimensions: 35x20
  • Garage: Yes
  • Parking Features: Driveway, Garage Door Opener, Ground Level, Oversized
Taxes and HOA Information
  • Association Approval Required: No
  • Association Fee Requirement: Required
  • Association Name: Progressive Community Management
  • Association Phone: 941-921-5393
  • Association: Yes
  • CDD: No
  • Pet Size: Extra Large (101+ Lbs.)
  • Tax Book Number: 5-18
  • Tax Legal Description: LOT 29 COCOANUT BAYOU
  • Tax Lot: 29
  • Tax Year: 2020
Property
Lot Information
  • Additional Parcels: No
  • Lot Features: FloodZone, In County, Oversized Lot, Sidewalk
  • Lot Size Dimensions: 162 x 361 x 85 x 350
  • Parcel Number: 0079070002
  • Total Acreage: 1/2 to less than 1
  • Water Access: Bay/Harbor, Beach, Beach - Access Deeded
  • Water Access: Yes
  • Water Body Name: Coccoanut Bayou
  • Water Extras: Lift, Riprap
  • Water Extras: Yes
  • Water: Lift, Riprap
  • Zoning: RE2
  • Zoning Compatible: Yes
  • Living Area: 4875
  • Lot Dimensions: 162 x 361 x 85 x 350
Property and Assessments
  • Year Built Numeric: 1994
  • Building Elevator: No
  • Flood Zone Code: AE
  • Flood Zone Date: 11-04-2016
  • Flood Zone Panel: 12115C0141F
  • Homestead: Yes
  • New Construction: No
  • Public Survey Range: 17E
  • Public Survey Section: 01
  • Dock Description: Dock - Wood, Dock w/Electric, Dock w/Water Supply
Utilities
  • Sewer: Public Sewer
  • Utilities: BB/HS Internet Available, Cable Connected, Electricity Connected, Natural Gas Connected, Sewer Connected, Sprinkler Well, Water Connected
  • Water Source: Public, Well
Interior and Exterior Features
Exterior Features
  • Construction Materials: Block, Wood Frame
  • Exterior Features: Balcony, Dog Run, Hurricane Shutters, Irrigation System, Lighting, Rain Gutters, Sliding Doors
  • Fencing: Fenced
  • Foundation Details: Stilt/On Piling
  • Levels: Two
  • Patio And Porch Features: Covered, Deck, Front Porch, Rear Porch, Side Porch
  • Pool Dimensions: 37x12
  • Pool Features: Auto Cleaner, Heated, In Ground, Lighting, Outside Bath Access, Salt Water
  • Pool Private: Yes
  • Pool: Private
  • Pool Private: Yes
  • Roof: Shingle
  • Security Features: Secured Garage/Parking, Security Gate, Security Lights, Smoke Detector(s)
  • Spa Features: Heated, In Ground
  • Spa: Yes
  • Vegetation: Mature Landscaping, Oak Trees, Trees/Landscaped
  • Waterfront Features: Bay/Harbor, Bayou
  • Waterfront Feet Total: 170
  • Number Of Stories: 2
Interior Features
  • Bedrooms Total: 4
  • Bathrooms Full: 4
  • Additional Rooms: Bonus Room, Breakfast Room Separate, Den/Library/Office, Family Room, Formal Dining Room Separate, Formal Living Room Separate, Inside Utility, Loft, Storage Rooms
  • Appliances: Built-In Oven, Convection Oven, Cooktop, Dishwasher, Disposal, Dryer, Exhaust Fan, Freezer, Gas Water Heater, Microwave, Refrigerator, Washer, Water Filtration System, Water Purifier, Wine Refrigerator
  • Cooling: Central Air, Zoned
  • Fireplace Features: Gas, Family Room, Living Room, Other Room
  • Fireplace: Yes
  • Flooring: Carpet, Tile
  • Heating: Central, Electric, Zoned
  • Interior Features: Built-in Features, Ceiling Fan(s), Central Vacuum, High Ceilings, Kitchen/Family Room Combo, Open Floorplan, Skylight(s), Solid Wood Cabinets, Split Bedroom, Stone Counters, Thermostat, Walk-In Closet(s), Wet Bar
  • Laundry Features: Inside, Laundry Room
  • Living Area Source: Owner
  • Living Area Units: Square Feet
  • Room Count: 15.0
  • Water View: Yes
  • Window Features: Insulated Windows
  • Bathrooms Half: 1
Rental
Rental Information
  • Minimum Lease Period: 0
  • Pets Allowed: Yes

Property History for 4401 Midnight Pass Road

DateEvent & SourcePriceAppreciation
Feb 11, 2021

Sold (Public Record)

Public Record #689865006

$4,072,000
Feb 11, 2021

Sold (Public Record)

Public Record #1450477424

$4,072,000

+15.3% / yr

Feb 11, 2021

Sold

MFRMLS #A4486881

$4,072,000
DateEvent & SourcePrice
02/11/2021

Sold (Public Record)

Public Record #689865006

$4,072,000
02/11/2021

Sold (Public Record)

Public Record #1450477424

$4,072,000

+15.3% / yr

02/11/2021

Sold

MFRMLS #A4486881

$4,072,000

For completeness, we often displays two records for one sale: the MLS record and the public record.

Public Records for 4401 Midnight Pass Road

Taxable ValueLand$1,977,700Additions$2,149,600Total$4,127,300
Tax Record2025$47,070 ($3,922 / month)
Home Facts
Beds3Baths4.5Total Finished SqFt4,249 SqFtAbove Grade Finished SqFt4,249 SqFtStories2Lot Size39,920 SqFtStyleSingle Family ResidenceYear Built1994Year Renovated2019ZoningSKOD; RE2CountySARASOTAAPN0079-07-0002Fireplace TypeHas Fireplace

Schools near 4401 Midnight Pass Road

This home is within Sarasota.
Rating
School
Type
Grades
Distance
Public - PK to 5
Public - 6 to 8
Public - 9 to 12
Public - 9 to 12
Rating
School
Distance
Phillippi Shores Elementary School
PublicPK to 5

Brookside Middle School
Public6 to 8

Sarasota High School
Public9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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Nearby home values

AddressSold priceBedsBathsSqftLot (Sqft)
This home: 4401 Midnight Pass Road, Sarasota, FL 34242
$4,072,000
4
4,875
39,920
4
3,215
49,907
$1,520,000
4
2,611
22,245
$3,665,000
4
5,752
64,808
33,665
3
2
1,199
20,287

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the seller's discretion. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties make no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of PREMIER SOTHEBYS INTL REALTY, Peter Laughlin

The information is being provided in part by Southwest Florida Multiple Listing Service, Broker Reciprocity Program ("BR Program") of M.L.S. of Naples, Inc. ("Naples MLS"), under License No. NCOMPN2, and MarcoMls. Information deemed reliable but not guaranteed. Information is provided for consumers' personal, non-commercial use, and may not be used for any purpose other than the identification of potential properties for purchase. Copyright 2026 Southwest Florida Multiple Listing Service and MarcoMls. All Rights Reserved. The data relating to real estate for sale displayed on this website comes in part from the Broker Reciprocity Program ("BR Program") of M.L.S. of Naples, Inc. ("Naples MLS"), under License No. NCOMPN2 and MarcoMls. Properties listed with brokerage firms other than Compass are marked with the "BR House" logo. Detailed information about such properties includes the name of the brokerage firm with which the seller has listed the property. The properties displayed may not be all the properties listed with brokerage firms participating in the Naples MLS BR Program, or contained in the database compilation of Naples MLS.