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$799,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 4 Beds
  • 2 Full Baths
  • 1,567 Sq. Ft.
  • Updated 1 day ago

Next open house:

Open House: 4:00 PM - 6:30 PM

Friday 5/22 4:00 PM - 6:30 PM

5744 Winchester Street,San Diego, CA 92139

5744 Winchester StreetSan DiegoCA92139

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Join us at 5744 Winchester Street on:

  • Open House: 11:00 AM - 4:00 PM

    Saturday 5/23 11:00 AM - 4:00 PM

    5744 Winchester Street,San Diego, CA 92139
    5744 Winchester StreetSan DiegoCA92139
  • Open House: 12:00 PM - 4:00 PM

    Sunday 5/24 12:00 PM - 4:00 PM

    5744 Winchester Street,San Diego, CA 92139
    5744 Winchester StreetSan DiegoCA92139
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See This Home
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Welcome to a unique opportunity offering modern living, built-in income potential, and future upside. The main home is a fully renovated 3-bedroom, 1-bath residence thoughtfully upgraded throughout, creating a clean, turnkey space ready for immediate use. The property also includes a fully permitted 1-bedroom, 1-bath ADU, offering flexible use for rental income, multigenerational living, or additional private space. Whether you're a first-time buyer looking to offset your mortgage or an investor seeking steady cash flow, the setup offers real flexibility and versatility. Adding even more value, the property includes renderings for two future duplex units (each 4 beds, 1.5 baths) at the rear-creating a clear path for expansion and long-term upside. Four separate gas and electric meters are already installed and permitted, helping support future expansion and long-term investment potential. A solid option for buyers looking to enter the market with income in place, or for investors ready to scale with a property that's already positioned for future growth.

Full Property Details for 5744 Winchester St

General

  • Price: $799,000
  • Status: Active
  • Type: Single Family
  • Source: MRMLS
  • MLS ID: PTP2603854
  • Updated: 5/20/2026
  • Days on Market: 4 days
  • Added to Site: 3 day(s) ago

Interior

  • Rooms/Areas: All Bedrooms Down
  • Fireplace(s): None
  • Appliances: Microwave, Refrigerator, Tankless Water Heater, Electric Range, Dishwasher, Gas & Electric Range, Electric Cooktop
  • Flooring: Vinyl

Rooms

Bathrooms

  • Total Bathrooms: 2
  • Full Bathrooms: 2

Bedrooms

  • Total Bedrooms: 4

Other Rooms

  • Laundry: In Garage

Additional Information

  • Pool Description: None

Exterior

  • Deck/Patio: Front Porch

Location

  • County: San Diego
  • Driving Directions: GPS

School Information

  • School District: Other

Community

  • Community Features: Curbs

Heating & Cooling

  • Cooling Type: Ductless
  • Heating Type: Central

Utilities

  • Sewer: Septic Type Unknown

Structural Information

  • Structure Type: Single Family Residence
  • Roof: Shingle
  • Common Walls: No Common Walls
  • Disability Access: Parking
  • Entry Location: Front
  • Stories/Levels: One
  • Stories Description: One
  • Square Feet: 1,567
  • Sq. Ft. Source: Public Records
  • Year Built: 1947
  • Property Condition: Updated/Remodeled

Unit Information

  • Units in Complex: 2

Lot Features

  • Property View: Neighborhood
  • Lot Size (Acres): 0.2
  • Lot Size (Sq. Ft.): 8,712
  • Lot Size Source: Public Records
  • Zoning: R-2:MINOR MULTIPLE
  • Lot Description: 0-1 Unit/Acre
  • Fencing (Description): Chain Link, Wood

Financial Considerations

  • Price Per Sq. Ft.: $509.89

Disclosures and Reports

  • Special Conditions: Standard

Listed by ShoppingSDHouses, Delta Sivonsay and ShoppingSDHouses, Kaleen De Arcos

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Listing agents

— 5744 Winchester St —

  • Delta Sivonsay

    ShoppingSDHouses

  • Kaleen De Arcos

    ShoppingSDHouses

760-216-8505

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 5744 Winchester St

School District:San Diego City Unified School District
NameGradesDistance
Lee Elementary School, San Diego, CA
6196 Childs Avenue, San Diego, CA 92139
K-50.5 mi
Bell Middle School
620 Briarwood Road, San Diego, CA 92139
6-81.9 mi
Morse High School
6905 Skyline Drive, San Diego, CA 92114
9-122.2 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 5744 Winchester St Get Price Alerts and Save Property

Date
Details
Price
Change
Source
5/19/2026
Listed
$799,000
6.53%
MLS
6/06/2024
Sold
$750,000
—
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 5744 Winchester St

Year
Property Taxes
Change
Tax Assessment
Change
2024
$5,146
2%
$765,000
88%
2023
$5,032
3%
$407,999
2%
2022
$4,898
749%
$400,000
807%
2021
$577
1%
$44,125
1%
2020
$570
2%
$43,674
2%
2019
$560
6%
$42,819
2%
2018
$526
3%
$41,981
2%
2017
$513
2%
$41,159
2%
2016
$503
1%
$40,353
2%
2015
$496
1%
$39,748
2%
2014
$490
—
$38,970
—
2013
$489
—
$38,795
—
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 5744 Winchester St

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*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 ShoppingSDHouses, Delta Sivonsay and ShoppingSDHouses, Kaleen De Arcos

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5744 Winchester Street, San Diego, CA 92139 (MLS# PTP2603854) is a Single Family property with 4 bedrooms and 2 full bathrooms. 5744 Winchester Street is currently listed for $799,000 and was received on May 19, 2026. Want to learn more about 5744 Winchester Street? Do you have questions about finding other Single Family real estate for sale in San Diego? You can browse all San Diego real estate or contact a Coldwell Banker agent to request more information.

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