Recently Viewed Properties
See This Home
Save This Listing
Close

View All Photos

$749,000 Sale Pending

  • For Sale
  • Pending
  • Lots/Land
  • 0.29 Acres
See This Home
Save This Home
See This Home
Save This Home
Under contract-accepting backup offers. Nestled on picturesque Shadow Lawn Drive, this 12,800-square-foot lot offers an exceptional canvas for your custom home. Framed by mature live oaks on the front left and back right corners, the property blends natural beauty with an enviable location. Enjoy the best of Siesta Key living-just an 8-minute stroll to the powdery sands of world-famous Siesta Beach and just over a mile to the dining and shopping of Siesta Village. Despite its proximity to these sought-after amenities, the property feels peaceful and secluded, tucked away on a quiet street removed from the island's main thoroughfares. With nearly 100 feet of street frontage and a depth of 120 feet, the lot offers a generous and flexible building footprint. Whether you envision a sleek, modern coastal retreat or a charming, classic island cottage, this is a rare opportunity to create your ideal Siesta Key home in one of its most desirable neighborhoods.

Full Property Details for 5587 Shadow Lawn Dr

General

  • Price: $749,000
  • Taxes: $2,953 (2024)
  • Status: Pending
  • Type: Lots/Land
  • Source: MidFloridaRegionalMLS
  • MLS ID: A4657583
  • Updated: 1/2/2026
  • Added to Site: 204 day(s) ago

Location

  • Area: 34242 - Sarasota/Crescent Beach/Siesta Key
  • County: Sarasota
  • Development Name: 34242 - Sarasota/Crescent Beach/Siesta Key
  • Subdivision: SIESTA ISLES
  • Driving Directions: Head west on Siesta Drive. Continue down Higel Ave. Veer left at Midnight Pass. Turn right on Shadow Lawn Way. Turn left on Shadow Lawn Drive. House is on less than 1/4 mile on the left.
  • Direction Faces: West

School Information

  • Elementary School: Phillippi Shores Elementary
  • Middle School: Brookside Middle
  • High School: Sarasota High

Community

  • Community Name: 34242 - Sarasota/Crescent Beach/Siesta Key
  • Association: Yes

Utilities

  • Sewer: Public Sewer
  • Water: None
  • Utility Description: BB/HS Internet Available, Cable Connected, Electricity Available, Public, Sewer Available, Water Connected

Structural Information

  • Current Bldg. Use: Residential

Lot Features

  • Lot Size (Acres): 0.29
  • Lot Size (Sq. Ft.): 12,800
  • Lot Size: 12800
  • Lot Dimensions: 50 x 119
  • Frontage: County Road
  • Street/Road Desc.: Asphalt

Financial Considerations

  • Price Per Acre: $2,582,759
  • Assoc Fee Desc.: Optional
  • Tax Amount: $2,953.08
  • Tax Year: 2024

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: LOT 101 SIESTA ISLES UNIT 7
  • Flood Zone Info: AE
  • APN: 107010020
  • Property ID: 107010020
Buyer's Brokerage Compensation: Contact Listing Agent
Not binding unless confirmed by separate agreement among applicable parties.

Quickly Find Out More

* Indicates a required field

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Send Message, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If an Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby’s International Realty®). I acknowledge that I have read and agree to the Terms of Use and Privacy Notice.

We Value Your Privacy

Meet the listing agents

Meet the listing agents
— 5587 Shadow Lawn Dr —

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 5587 Shadow Lawn Dr

School District:Sarasota County School District
NameGradesDistance
Phillippi Shores Elementary School
4747 South Tamiami Trail, Sarasota, FL 34231
PK-51.7 mi
Brookside Middle School
3636 South Shade Avenue, Sarasota, FL 34239
6-82.6 mi
Sarasota High School
2155 Bahia Vista Street, Sarasota, FL 34239
9-124 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 5587 Shadow Lawn Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
11/06/2025
Price Reduced
$749,000
-6.26%
MLS
8/05/2025
Price Reduced
$799,000
-6%
MLS
7/01/2025
Listed
$850,000
—
MLS
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 5587 Shadow Lawn Dr

Year
Property Taxes
Change
Tax Assessment
Change
2024
$2,953
4%
$250,111
3%
2023
$2,826
2%
$242,826
6%
2021
$2,781
-1%
$228,886
-3%
2022
$2,802
1%
$235,753
4%
2021
$2,781
5%
$225,726
2%
2019
$2,654
3%
$220,651
2%
2018
$2,582
1%
$216,537
2%
2017
$2,568
—
$212,083
2%
2016
$2,560
-2%
$207,721
1%
2015
$2,604
—
$206,277
1%
2014
$2,593
—
$204,640
1%
2013
$2,590
—
$201,616
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 5587 Shadow Lawn Dr

$
Down Payment
%
$
%

$
$

*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Similar Properties near 5587 Shadow Lawn Dr

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

5302 Las Rosas, Sarasota, FL 34242 - Photo 1
$750,000

5302 Las Rosas  Sarasota, FL 34242

  • Lots/Land
  • Active
  • 0.2
    Acres
Listed by Preferred Shore Llc
2506 Wilkinson Rd, Sarasota, FL 34231 - Photo 1
$750,000

2506 Wilkinson Rd  Sarasota, FL 34231

  • Lots/Land
  • Active
  • 0.38
    Acres
Listed by Premier Sotheby's International Realty
0 S Lockwood Ridge Rd, Sarasota, FL 34231 - Photo 1
$725,000

0 S Lockwood Ridge Rd  Sarasota, FL 34231

  • Lots/Land
  • Active
  • 0.28
    Acres
Listed by Keller Williams On The Water S
1931 Bahia Vista St, Sarasota, FL 34239 - Photo 1
$749,900

1931 Bahia Vista St  Sarasota, FL 34239

  • Lots/Land
  • Active
  • 0.23
    Acres
Listed by William Raveis Real Estate

Just Listed near 5587 Shadow Lawn Dr

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

1135 Gulf of Mexico Dr, Longboat Key, FL 34228 - Photo 1 Just Listed
$1,650,000

1135 Gulf of Mexico Dr  #605  Longboat Key, FL 34228

  • Condo
  • Active
  • Updated 6 days ago
  • 2
    Beds
  • 2
    Total Baths
  • 1,503
    Sq. Ft.
Listed by Bruce Myer Group (941) 383-6411
590 De Narvaez Dr, Longboat Key, FL 34228 - Photo 1 Just Listed
$4,123,000

590 De Narvaez Dr  Longboat Key, FL 34228

  • Single Family
  • Active
  • Updated 12 hours ago
  • 4
    Beds
  • 4
    Total Baths
  • 3,243
    Sq. Ft.
Listed by Cole Collins (941) 350-8360 and Grant Sharretts (443) 903-9413
585 Sanctuary Dr, Longboat Key, FL 34228 - Photo 1 Just Listed
$1,799,000

585 Sanctuary Dr  #B502  Longboat Key, FL 34228

  • Condo
  • Active
  • Updated 8 hours ago
  • 3
    Beds
  • 3
    Total Baths
  • 1,823
    Sq. Ft.
Listed by Pettingell Professionals (941) 383-6411
6489 Gulfside Rd, Longboat Key, FL 34228 - Photo 1 Just Listed
$14,995,000

6489 Gulfside Rd  Longboat Key, FL 34228

  • Single Family
  • Active
  • Updated 4 days ago
  • 4
    Beds
  • 5
    Total Baths
  • 6,616
    Sq. Ft.
Listed by Nicholle McKiernan (941) 928-2922 and Jules Lojacono Mackie (773) 704-1438

Price Reduced near 5587 Shadow Lawn Dr

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

603 Longboat Club Rd, Longboat Key, FL 34228 - Photo 1 Price Reduced
-$51,000 (-3.78%)
$1,299,000

603 Longboat Club Rd  #402N  Longboat Key, FL 34228

  • Condo
  • Active
  • Updated 2 days ago
  • 2
    Beds
  • 2
    Total Baths
  • 1,458
    Sq. Ft.
Listed by Kepecz-Hays (941) 366-8070 and Leah George (941) 780-0597
435 L Ambiance Dr, Longboat Key, FL 34228 - Photo 1 Price Reduced
-$300,000 (-6.26%)
$4,495,000

435 L Ambiance Dr  #J703  Longboat Key, FL 34228

  • Condo
  • Active
  • Updated 5 days ago
  • 3
    Beds
  • 3
    Total Baths
  • 2,820
    Sq. Ft.
Listed by Rhinelander - Tarantino Team (941) 383-6411
4390 Exeter Dr, Longboat Key, FL 34228 - Photo 1 Price Reduced
-$5,000 (-0.85%)
$580,000

4390 Exeter Dr  #206  Longboat Key, FL 34228

  • Condo
  • Active
  • Updated 3 days ago
  • 2
    Beds
  • 2
    Total Baths
  • 1,152
    Sq. Ft.
Listed by The VanDuren Group (941) 383-6411
2410 Harbourside Dr, Longboat Key, FL 34228 - Photo 1 Price Reduced
-$200,000 (-8.02%)
$2,295,000

2410 Harbourside Dr  #121  Longboat Key, FL 34228

  • Condo
  • Active
  • Updated 4 days ago
  • 3
    Beds
  • 4
    Total Baths
  • 3,825
    Sq. Ft.
Listed by Bruce Myer Group (941) 383-6411

Recent Sales near 5587 Shadow Lawn Dr

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

1093 Lake House Cir, Sarasota, FL 34242 - Photo 1 Sold
$650,000

1093 Lake House Cir  #C205  Sarasota, FL 34242

  • Townhouse
  • Closed
  • 2
    Beds
  • 2
    Total Baths
  • 1,352
    Sq. Ft.
Listed and Sold by Michael Saunders & Company
1055 Beach Rd, Sarasota, FL 34242 - Photo 1 Sold
$860,000

1055 Beach Rd  #B-302  Sarasota, FL 34242

  • Condo
  • Closed
  • 2
    Beds
  • 2
    Total Baths
  • 1,204
    Sq. Ft.
Listed by Preferred Shore Llc
Sold by Michael Saunders & Company
1055 Beach Road Rd, Sarasota, FL 34242 - Photo 1 Sold
$735,000

1055 Beach Road Rd  #B204  Sarasota, FL 34242

  • Condo
  • Closed
  • 2
    Beds
  • 2
    Total Baths
  • 1,204
    Sq. Ft.
Listed by Corcoran Dwellings Realty
Sold by Gallery Properties Internation
1235 Dockside Pl, Sarasota, FL 34242 - Photo 1 Sold
$800,000

1235 Dockside Pl  #108  Sarasota, FL 34242

  • Condo
  • Closed
  • 2
    Beds
  • 2
    Total Baths
  • 1,343
    Sq. Ft.
Listed and Sold by Bright Realty

5587 Shadow Lawn Drive, Sarasota, FL 34242 (MLS# A4657583) is a Lots/Land property with a lot size of 0.29 acres. 5587 Shadow Lawn Drive is currently listed for $749,000 and was received on July 01, 2025. This property is listed by Nick Gard from our St. Armands Office.Want to learn more about 5587 Shadow Lawn Drive? Do you have questions about finding other Lots/Land real estate for sale in Sarasota? You can browse all Sarasota real estate or contact a Coldwell Banker agent to request more information.

Tour this property