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$259,000 -$10,900 (-4.04%) Price Reduced

  • For Sale
  • Active
  • Single Family
  • 2 Beds
  • 2 Full Baths
  • 1,454 Sq. Ft.
  • Updated 21 hours ago

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Open House: 12:00 PM - 3:00 PM

Saturday 10/10 12:00 PM - 3:00 PM

2590 Oswego Drive,North Port, FL 34289

2590 Oswego DriveNorth PortFL34289

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Welcome to this beautifully maintained 2-bedroom, 2-bathroom home with a den, located in the desirable active 55+ gated community of Cypress Falls in North Port. Situated on the waterfront and not in a flood zone, this lovingly cared-for home has been owned by the original owner since it was built. The home offers a wonderful Florida lifestyle, with beautiful water views, abundant natural light, and thoughtful updates throughout. The tile roof was replaced in 2025, and the interior walls and lanai are painted. A skylight fills the home with natural sunshine throughout the day and creates a charming touch in the evening as moonlight filters through. The kitchen features granite countertops and under-cabinet lighting, while the main living areas offer tile flooring while the bedrooms feature luxury laminate flooring. Both bathrooms are enhanced with glass-enclosed showers and upgraded hardware. Enjoy the outdoors from the spacious screened lanai overlooking a peaceful natural wooded area, or relax in the unique screened front entry while taking in the water views. Cypress Falls offers an exceptional resort-style lifestyle with a clubhouse, heated pool, resistance pool and spa, fitness center, tennis, pickleball, bocce ball, dog park, and even a community garden as well as an array of additional recreational, fitness, and social activities. This exceptional waterfront home combines comfort, thoughtful updates, beautiful surroundings, and resort-style amenities-offering a wonderful opportunity to enjoy the relaxed Florida lifestyle in a vibrant 55+ community.

Full Property Details for 2590 Oswego Dr

General

  • Price: $259,000
  • HOA FEE: $465/month
  • HOA FEE FREQ.: Quarterly
  • Taxes: $5,148 (2025)
  • Status: Active
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: C7529278
  • Updated: 10/7/2026
  • Added to Site: 48 day(s) ago

Rental Information

  • Min. Lease: 6 Months

Interior

  • Number of Rooms: 5
  • Interior Features: Ceiling Fan(s), High Ceilings, Split Bedroom
  • Appliances: Dishwasher, Dryer, Microwave, Range Hood, Refrigerator, Washer
  • Furnishings: Negotiable
  • Flooring: Laminate, Tile

Rooms

Bathrooms

  • Total Bathrooms: 2
  • Full Bathrooms: 2

Bedrooms

  • Total Bedrooms: 2

Other Rooms

  • Laundry: Laundry Closet

Additional Information

  • Shared Amenities: Pickleball Court(s), Pool

Exterior

  • Exterior Features: Balcony, Courtyard, Dog Run, French Doors, Irrigation System, Lighting, Tennis Court(s)

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Covered Spaces: 2

Location

  • Area: 34289 - North Port
  • County: Sarasota
  • Development Name: 34289 - North Port
  • Subdivision: CYPRESS FALLS PH 1E
  • Driving Directions: From I-75, take Exit 179 (Toledo Blade Boulevard). Travel south on Toledo Blade Boulevard approximately 1.5 miles. Turn left onto Plantation Boulevard, then turn left into the gated entrance of Cypress Falls at The Woodlands. After entering the community, continue to Oswego Drive. The property will be on your left.
  • Direction Faces: Northwest

School Information

  • Elementary School: Toledo Blade Elementary
  • Middle School: Woodland Middle School
  • High School: North Port High

Community

  • Community Name: 34289 - North Port
  • Community Features: Clubhouse, Fitness Center, Pool, Racquetball, Sidewalks
  • Optional Amenities: Pickleball Court(s), Pool
  • Association: Yes
  • Assoc. Name: Melissa "Mel' Headrick
  • Number of Pets: 2
  • Pet Restrictions: Please see community rules and regulations, no pit bulls allowed
  • Adult Community: Yes

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Central

Utilities

  • Sewer: Public Sewer
  • Water: Public
  • Utility Description: BB/HS Internet Available, Cable Connected, Electricity Connected, Sewer Connected, Underground Utilities

Structural Information

  • Exterior Const.: Block
  • Roof: Tile
  • Stories/Levels: One
  • Square Feet: 1,454
  • Sq. Ft. Source: Public Records
  • Year Built: 2017

Lot Features

  • Lot Size (Acres): 0.08
  • Lot Size (Sq. Ft.): 3,658
  • Lot Size: 3658
  • Street/Road Desc.: Concrete

Financial Considerations

  • Association Fee: $1,396
  • Assoc Fee Freq.: Quarterly
  • Assoc Fee Desc.: Required
  • CDD: Yes
  • Tax Amount: $5,148.94
  • Tax Year: 2025

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: LOT 2, BLK 19, CYPRESS FALLS PHASE 1E
  • Flood Zone Info: X
  • APN: 1115060078
  • Property ID: 1115060078
  • Block/Lot/Section: 19

Listed by Era Advantage Realty, Inc.

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Listing agent

— 2590 Oswego Dr —

  • Era Advantage Realty, Inc.

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

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Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 2590 Oswego Dr

School District:Sarasota County School District
NameGradesDistance
Toledo Blade Elementary School
1201 Geranium Avenue, North Port, FL 34288
PK-51.6 mi
North Port High School
6400 West Price Boulevard, North Port, FL 34291
9-125 mi
Woodland Middle School
2700 Panacea Boulevard, North Port, FL 34289
6-81.6 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 2590 Oswego Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
10/07/2026
Price Reduced
$259,000
-4.04%
MLS
9/24/2026
Price Reduced
$269,900
-1.85%
MLS
9/21/2026
Price Reduced
$275,000
-3.51%
MLS
8/21/2026
Listed
$285,000
40.81%
MLS
3/31/2017
Sold
$202,400
—
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 2590 Oswego Dr

Year
Property Taxes
Change
Tax Assessment
Change
2025
$5,149
—
$248,300
-9%
2024
$5,174
—
$274,200
-11%
2023
$5,172
25%
$307,500
72%
2021
$4,128
-17%
$178,500
-40%
2022
$4,978
21%
$295,900
72%
2021
$4,128
6%
$172,400
7%
2019
$3,896
5%
$161,700
3%
2018
$3,724
131%
$156,600
487%
2017
$1,614
-5%
$26,700
16%
2016
$1,693
-2%
$23,000
34%
2015
$1,725
6%
$17,160
10%
2014
$1,621
-2%
$15,600
-14%
2013
$1,661
—
$18,100
—
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.

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Listed by Era Advantage Realty, Inc.

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2590 Oswego Drive, North Port, FL 34289 (MLS# C7529278) is a Single Family property with 2 bedrooms and 2 full bathrooms. 2590 Oswego Drive is currently listed for $259,000 and was received on August 21, 2026. Want to learn more about 2590 Oswego Drive? Do you have questions about finding other Single Family real estate for sale in North Port? You can browse all North Port real estate or contact a Coldwell Banker agent to request more information.

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