Recently Viewed Properties
See This Home
Save This Listing
Close

View All Photos

$209,900 Sale Pending

  • For Sale
  • Pending
  • Single Family
  • 2 Beds
  • 2 Full Baths
  • 1,276 Sq. Ft.
See This Home
Save This Home
See This Home
Save This Home
Charming villa just minutes from Siesta Key, surrounded by mature Old Florida landscaping in a private enclave of villa-style condos, close to Gulf Gate and US41. This inviting 2-bedroom, 2-bath home in Sarasota's desirable Gulf Gate area was built in 1974, blending classic Florida charm with modern comfort. The spacious layout includes a bright Florida room, screened porch, and covered carport. Recent updates feature a newer AC system, new electric panel, and water heater, plus newly paved neighborhood roads. The community offers a tennis/pickleball court and a large screened-in heated swimming pool. Not in a flood zone requiring insurance, this home is available for immediate occupancy, perfect for seasonal or year-round living. Just a 5-minute drive to world-famous Siesta Key Beach and close to shopping, dining, and entertainment, it's ideal as a permanent home, vacation retreat, or investment property.

Full Property Details for 2227 Circlewood Dr #52

General

  • Price: $209,900
  • HOA FEE: $700/month
  • Taxes: $1,530 (2024)
  • Status: Pending
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: A4661657
  • Updated: 12/10/2025
  • Added to Site: 160 day(s) ago

Rental Information

  • Min. Lease: 3 Months

Interior

  • Number of Rooms: 7
  • Interior Features: Cathedral Ceiling(s), Ceiling Fan(s), High Ceilings, L Dining, Primary Bedroom Main Floor, Solid Surface Counters, Vaulted Ceiling(s), Walk-In Closet(s), Window Treatments
  • Appliances: Dishwasher, Disposal, Dryer, Electric Water Heater, Exhaust Fan, Microwave, Range, Range Hood, Refrigerator, Washer
  • Furnishings: Unfurnished
  • Flooring: Carpet, Ceramic Tile, Laminate

Rooms

Bathrooms

  • Total Bathrooms: 2
  • Full Bathrooms: 2

Bedrooms

  • Total Bedrooms: 2

Other Rooms

  • Laundry: Laundry Room

Additional Information

  • Shared Amenities: Vehicle Restrictions
  • Spa: Yes

Exterior

  • Exterior Features: Sliding Doors, Storage
  • Deck/Patio: Patio, Porch
  • Porch/Patio/Deck: Patio, Porch

Parking

  • Carports: Yes
  • Carport: 1
  • Carport Spaces: 1
  • Covered Spaces: 1
  • Parking Features: Covered

Location

  • Area: 34231 - Sarasota/Gulf Gate Branch
  • County: Sarasota
  • Development Name: 34231 - Sarasota/Gulf Gate Branch
  • Subdivision: WOODSIDE VLG EAST
  • Driving Directions: From US 41 to Bispham Dr east to Woodside Village East. Turn left into the neighborhood and then a left at Circlewood Dr to 2227 Circlewood Dr.
  • Direction Faces: Southwest

Community

  • Community Name: 34231 - Sarasota/Gulf Gate Branch
  • Community Features: Deed Restrictions, Pool
  • Optional Amenities: Vehicle Restrictions
  • Assoc. Name: Sentry Mgmt-Gabrielle Wilson
  • Assoc. Fees Include: Community Pool, Escrow Reserves Fund, Fidelity Bond, Insurance, Maintenance Structure, Maintenance Grounds, Recreational Facilities, Sewer, Water
  • Number of Pets: 2
  • Pet Restrictions: 2, / 35lbs.

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Electric

Utilities

  • Sewer: Public Sewer
  • Water: Public
  • Utility Description: Cable Connected, Public

Structural Information

  • Exterior Const.: Block, Stucco
  • Roof: Other, Shingle
  • Common Walls: End Unit
  • Windows: Blinds, Window Treatments
  • Stories/Levels: One
  • Square Feet: 1,276
  • Sq. Ft. Source: Public Records
  • Year Built: 1974

Additional Structures

  • Other Structures: Storage

Lot Features

  • Street/Road Desc.: Asphalt

Financial Considerations

  • Assoc Fee Desc.: None
  • Condo Fee: $700
  • Condo Fee Freq: Monthly
  • Tax Amount: $1,530
  • Tax Year: 2024

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: UNIT 52 WOODSIDE VILLAGE EAST
  • Flood Zone Info: X
  • APN: 102132052
  • Property ID: 102132052

Listed by Fine Properties

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

Listing agent

— 2227 Circlewood Dr #52 —

  • Fine Properties

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 2227 Circlewood Dr #52

School District:Sarasota County School District
NameGradesDistance
Gulf Gate Elementary School
6500 South Lockwood Ridge Road, Sarasota, FL 34231
PK-50.5 mi
Riverview High School, Sarasota, FL
1 Ram Way, Sarasota, FL 34231
9-121.9 mi
Brookside Middle School
3636 South Shade Avenue, Sarasota, FL 34239
6-83.2 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 2227 Circlewood Dr #52 Get Price Alerts and Save Property

Date
Details
Price
Change
Source
11/19/2025
Price Reduced
$209,900
-8.7%
MLS
9/04/2025
Price Reduced
$229,900
-8%
MLS
8/11/2025
Listed
$249,900
168.71%
MLS
2/03/2014
Sold
$93,000
—
Public Record
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 2227 Circlewood Dr #52

Year
Property Taxes
Change
Tax Assessment
Change
2025
$1,034
-32%
$132,076
3%
2024
$1,530
9%
$128,354
3%
2023
$1,398
—
$124,616
6%
2021
$1,399
-1%
$117,462
-3%
2022
$1,409
1%
$120,986
4%
2021
$1,399
6%
$115,840
2%
2019
$1,323
9%
$113,236
7%
2018
$1,214
1%
$106,129
2%
2017
$1,204
1%
$103,946
2%
2016
$1,195
-1%
$101,808
1%
2015
$1,211
-17%
$101,100
21%
2014
$1,461
84%
$83,700
30%
2013
$792
—
$64,300
—
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 2227 Circlewood Dr #52

$
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

Listed by Fine Properties

Similar Properties near 2227 Circlewood Dr #52

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

4223 Oakhurst Cir E, Sarasota, FL 34233 - Photo 1
$210,000

4223 Oakhurst Cir E  #3025  Sarasota, FL 34233

  • Single Family
  • Active
  • 2
    Beds
  • 2
    Total Baths
  • 1,543
    Sq. Ft.
Listed by Premier Sotheby's International Realty
3227 Beneva Rd, Sarasota, FL 34232 - Photo 1
$213,500

3227 Beneva Rd  #201  Sarasota, FL 34232

  • Single Family
  • Active
  • Updated 9 days ago
  • 2
    Beds
  • 2
    Total Baths
  • 964
    Sq. Ft.
Listed by Berkshire Hathaway Homeservice
4073 Center Pointe Pl, Sarasota, FL 34233 - Photo 1 Price Reduced
-$15,000 (-6.52%)
$214,900

4073 Center Pointe Pl  Sarasota, FL 34233

  • Single Family
  • Active
  • Updated 4 days ago
  • 2
    Beds
  • 2
    Total Baths
  • 1,029
    Sq. Ft.
Listed by Apple Real Estate Llc
2121 Pueblo Cir, Sarasota, FL 34231 - Photo 1
$215,000

2121 Pueblo Cir  #V6  Sarasota, FL 34231

  • Single Family
  • Active
  • 2
    Beds
  • 2
    Total Baths
  • 1,008
    Sq. Ft.
Listed by Fine Properties

Just Listed near 2227 Circlewood Dr #52

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 3 days ago
  • 2
    Beds
  • 2
    Total Baths
  • 1,503
    Sq. Ft.
Listed by Bruce Myer Group (941) 383-6411
2109 Gulf of Mexico Dr, Longboat Key, FL 34228 - Photo 1 Just Listed
$1,125,000

2109 Gulf of Mexico Dr  #1303  Longboat Key, FL 34228

  • Condo
  • Active
  • Updated 3 days ago
  • 2
    Beds
  • 2
    Total Baths
  • 1,463
    Sq. Ft.
Listed by The Leventhal Team (941) 383-6411
3598 Fair Oaks Ln, Longboat Key, FL 34228 - Photo 1 Just Listed
$2,895,000

3598 Fair Oaks Ln  Longboat Key, FL 34228

  • Single Family
  • Active
  • Updated 3 days ago
  • 4
    Beds
  • 4
    Total Baths
  • 3,417
    Sq. Ft.
Listed by Pettingell Professionals (941) 383-6411 and The NEST Group (941) 383-6411
350 Gulf of Mexico Dr, Longboat Key, FL 34228 - Photo 1 Just Listed
$1,149,000

350 Gulf of Mexico Dr  #234  Longboat Key, FL 34228

  • Condo
  • Active
  • Updated 1 day ago
  • 3
    Beds
  • 4
    Total Baths
  • 2,513
    Sq. Ft.
Listed by The Ackerman Group (941) 780-6045

Price Reduced near 2227 Circlewood Dr #52

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

1065 Gulf of Mexico Dr, Longboat Key, FL 34228 - Photo 1 Price Reduced
-$10,000 (-1.54%)
$639,000

1065 Gulf of Mexico Dr  #302  Longboat Key, FL 34228

  • Condo
  • Active
  • Updated 4 days ago
  • 2
    Beds
  • 2
    Total Baths
  • 1,392
    Sq. Ft.
Listed by Jim Weingart (440) 623-9068
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 2 days ago
  • 3
    Beds
  • 3
    Total Baths
  • 2,820
    Sq. Ft.
Listed by Rhinelander - Tarantino Team (941) 383-6411
8119 Tabbystone Pl, University Park, FL 34201 - Photo 1 Price Reduced
-$25,000 (-5.1%)
$465,000
Open House

8119 Tabbystone Pl  University Park, FL 34201

  • Single Family
  • Active
  • Updated 23 hours ago
  • 3
    Beds
  • 2
    Total Baths
  • 1,598
    Sq. Ft.
Listed by Brandy Sheldon (941) 724-0469 and Carlye Crabtree (941) 716-9665
612 Juan Anasco Dr, Longboat Key, FL 34228 - Photo 1 Price Reduced
-$500,000 (-2.13%)
$23,000,000

612 Juan Anasco Dr  Longboat Key, FL 34228

  • Single Family
  • Active
  • Updated 22 hours ago
  • 6
    Beds
  • 9
    Total Baths
  • 9,243
    Sq. Ft.
Listed by Buky Team (941) 383-6411

Recent Sales near 2227 Circlewood Dr #52

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

6832 Woodwind Dr, Sarasota, FL 34231 - Photo 1 Sold
$235,000

6832 Woodwind Dr  #53  Sarasota, FL 34231

  • Condo
  • Closed
  • 2
    Beds
  • 2
    Total Baths
  • 1,236
    Sq. Ft.
Listed by Exit King Realty
Sold by Bluesrq Real Estate Inc
6946 Woodwind Dr, Sarasota, FL 34231 - Photo 1 Sold
$205,000

6946 Woodwind Dr  #2  Sarasota, FL 34231

  • Single Family
  • Closed
  • 2
    Beds
  • 2
    Total Baths
  • 1,475
    Sq. Ft.
Listed by The Shoreline Fl Realty Llc
Sold by Keller Williams On The Water S
2291 Pueblo Ln, Sarasota, FL 34231 - Photo 1 Sold
$180,000

2291 Pueblo Ln  #V46  Sarasota, FL 34231

  • Condo
  • Closed
  • 2
    Beds
  • 2
    Total Baths
  • 1,007
    Sq. Ft.
Listed by Waterside Realty Llc
Sold by Kw Coastal Living Iii
2259 Pueblo Ln, Sarasota, FL 34231 - Photo 1 Sold
$182,450

2259 Pueblo Ln  #V38  Sarasota, FL 34231

  • Single Family
  • Closed
  • 2
    Beds
  • 2
    Total Baths
  • 1,007
    Sq. Ft.
Listed by Debbie Hering Realty & Assoc.
Sold by Sunset Realty

2227 Circlewood Drive #52, Sarasota, FL 34231 (MLS# A4661657) is a Single Family property with 2 bedrooms and 2 full bathrooms. 2227 Circlewood Drive #52 is currently listed for $209,900 and was received on August 11, 2025. Want to learn more about 2227 Circlewood Drive #52? Do you have questions about finding other Single Family 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