Forgot password Extend Verify Contact
NEXT Open House + more
May 22, 2026 04:00 PM - 06:30 PM PDT

5744 Winchester Street
San Diego San Diego 92139

$799,000
Residential beds: 4 baths: 2.0 1,567 sq. ft. built: 1947

Main Photo: House for sale : 4 bedrooms : 5744 Winchester Street in San Diego
Photo 1: House for sale : 4 bedrooms : 5744 Winchester Street in San Diego
Photo 2: House for sale : 4 bedrooms : 5744 Winchester Street in San Diego
Photo 3: House for sale : 4 bedrooms : 5744 Winchester Street in San Diego
Photo 4: House for sale : 4 bedrooms : 5744 Winchester Street in San Diego
Photo 5: House for sale : 4 bedrooms : 5744 Winchester Street in San Diego
Photo 6: House for sale : 4 bedrooms : 5744 Winchester Street in San Diego
Photo 7: House for sale : 4 bedrooms : 5744 Winchester Street in San Diego
Photo 8: House for sale : 4 bedrooms : 5744 Winchester Street in San Diego
Photo 9: House for sale : 4 bedrooms : 5744 Winchester Street in San Diego
Photo 10: House for sale : 4 bedrooms : 5744 Winchester Street in San Diego
Photo 11: House for sale : 4 bedrooms : 5744 Winchester Street in San Diego
Photo 12: House for sale : 4 bedrooms : 5744 Winchester Street in San Diego
Photo 13: House for sale : 4 bedrooms : 5744 Winchester Street in San Diego
Photo 14: House for sale : 4 bedrooms : 5744 Winchester Street in San Diego
Photo 15: House for sale : 4 bedrooms : 5744 Winchester Street in San Diego
Photo 16: House for sale : 4 bedrooms : 5744 Winchester Street in San Diego
Photo 17: House for sale : 4 bedrooms : 5744 Winchester Street in San Diego
Photo 18: House for sale : 4 bedrooms : 5744 Winchester Street in San Diego
Photo 19: House for sale : 4 bedrooms : 5744 Winchester Street in San Diego
Photo 20: House for sale : 4 bedrooms : 5744 Winchester Street in San Diego
Photo 21: House for sale : 4 bedrooms : 5744 Winchester Street in San Diego
Photo 22: House for sale : 4 bedrooms : 5744 Winchester Street in San Diego
Photo 23: House for sale : 4 bedrooms : 5744 Winchester Street in San Diego
Photo 24: House for sale : 4 bedrooms : 5744 Winchester Street in San Diego
Photo 25: House for sale : 4 bedrooms : 5744 Winchester Street in San Diego
Photo 26: House for sale : 4 bedrooms : 5744 Winchester Street in San Diego
Photo 27: House for sale : 4 bedrooms : 5744 Winchester Street in San Diego
Photo 28: House for sale : 4 bedrooms : 5744 Winchester Street in San Diego
Photo 29: House for sale : 4 bedrooms : 5744 Winchester Street in San Diego
Photo 30: House for sale : 4 bedrooms : 5744 Winchester Street in San Diego
Photo 31: House for sale : 4 bedrooms : 5744 Winchester Street in San Diego
Photo 32: House for sale : 4 bedrooms : 5744 Winchester Street in San Diego
Photo 33: House for sale : 4 bedrooms : 5744 Winchester Street in San Diego
Photo 34: House for sale : 4 bedrooms : 5744 Winchester Street in San Diego
Open House - May 22, 2026
04:00 PM - 06:30 PM PDT
NOTES: Open House on Friday, May 22, 2026 4:00PM - 6:30PM
Open House - May 23, 2026
11:00 AM - 04:00 PM PDT
NOTES: Open House on Saturday, May 23, 2026 11:00AM - 4:00PM
Show all 3 events
Status:
Active
Prop. Type:
Residential
MLS® Num:
306722833
Bedrooms:
4
Bathrooms:
2
Year Built:
1947
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 youre 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 rearcreating 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 thats already positioned for future growth.
Property Sub Type:
Detached
County Or Parish:
San Diego
Total Building Area:
1,567 sq. ft.
Total Floor Area:
1,567 sq. ft.
Total Bedrooms:
4
Optional Bedrooms:
4
Bathrooms:
2
Full Bathrooms:
2
Half Bathrooms:
0
Fireplace Details:
N/K
Stories:
1 Story
Num Stories:
1
Total Stories:
1
Entry Level:
2
Year Built:
1947
Age (in years):
79 year(s)
Home Owner Fees:
$0
Mello Roos Fee:
$0
Mello Roos Fee Frequency:
Year
Terms:
Cash, Conventional, FHA, VA
# Units In Community:
2
GPS
Site Influences:
Curbs
View:
Neighborhood
Appliances:
Dishwasher, Microwave, Refrigerator, Electric Range, Gas & Electric Range
Accessibility Features:
Parking
Special Listing Conditions:
Standard
Property Condition:
Updated/Remodeled
Lot Size:
8,712 sq. ft.
Parcel Number:
5872521700
Total Parking Spaces:
4
Total Garage Spaces:
0
Heating:
Forced Air Unit
Utilities:
Electricity Connected
Pool Features:
N/K
Roof:
Shingle
Interior Walls:
No Common Walls
Water Heater Type:
Tankless
Sewer Septic:
Unknown
Floor finish:
Linoleum/Vinyl
Assessments:
Unknown
Zoning:
R-2:MINOR
Fencing:
Chain Link, Wood
  • Photo 1: House for sale : 4 bedrooms : 5744 Winchester Street in San Diego
    Photo 1 of 34
  • Photo 2: House for sale : 4 bedrooms : 5744 Winchester Street in San Diego
    Photo 2 of 34
  • Photo 3: House for sale : 4 bedrooms : 5744 Winchester Street in San Diego
    Photo 3 of 34
  • Photo 4: House for sale : 4 bedrooms : 5744 Winchester Street in San Diego
    Photo 4 of 34
  • Photo 5: House for sale : 4 bedrooms : 5744 Winchester Street in San Diego
    Photo 5 of 34
  • Photo 6: House for sale : 4 bedrooms : 5744 Winchester Street in San Diego
    Photo 6 of 34
  • Photo 7: House for sale : 4 bedrooms : 5744 Winchester Street in San Diego
    Photo 7 of 34
  • Photo 8: House for sale : 4 bedrooms : 5744 Winchester Street in San Diego
    Photo 8 of 34
  • Photo 9: House for sale : 4 bedrooms : 5744 Winchester Street in San Diego
    Photo 9 of 34
  • Photo 10: House for sale : 4 bedrooms : 5744 Winchester Street in San Diego
    Photo 10 of 34
  • Photo 11: House for sale : 4 bedrooms : 5744 Winchester Street in San Diego
    Photo 11 of 34
  • Photo 12: House for sale : 4 bedrooms : 5744 Winchester Street in San Diego
    Photo 12 of 34
  • Photo 13: House for sale : 4 bedrooms : 5744 Winchester Street in San Diego
    Photo 13 of 34
  • Photo 14: House for sale : 4 bedrooms : 5744 Winchester Street in San Diego
    Photo 14 of 34
  • Photo 15: House for sale : 4 bedrooms : 5744 Winchester Street in San Diego
    Photo 15 of 34
  • Photo 16: House for sale : 4 bedrooms : 5744 Winchester Street in San Diego
    Photo 16 of 34
  • Photo 17: House for sale : 4 bedrooms : 5744 Winchester Street in San Diego
    Photo 17 of 34
  • Photo 18: House for sale : 4 bedrooms : 5744 Winchester Street in San Diego
    Photo 18 of 34
  • Photo 19: House for sale : 4 bedrooms : 5744 Winchester Street in San Diego
    Photo 19 of 34
  • Photo 20: House for sale : 4 bedrooms : 5744 Winchester Street in San Diego
    Photo 20 of 34
  • Photo 21: House for sale : 4 bedrooms : 5744 Winchester Street in San Diego
    Photo 21 of 34
  • Photo 22: House for sale : 4 bedrooms : 5744 Winchester Street in San Diego
    Photo 22 of 34
  • Photo 23: House for sale : 4 bedrooms : 5744 Winchester Street in San Diego
    Photo 23 of 34
  • Photo 24: House for sale : 4 bedrooms : 5744 Winchester Street in San Diego
    Photo 24 of 34
  • Photo 25: House for sale : 4 bedrooms : 5744 Winchester Street in San Diego
    Photo 25 of 34
  • Photo 26: House for sale : 4 bedrooms : 5744 Winchester Street in San Diego
    Photo 26 of 34
  • Photo 27: House for sale : 4 bedrooms : 5744 Winchester Street in San Diego
    Photo 27 of 34
  • Photo 28: House for sale : 4 bedrooms : 5744 Winchester Street in San Diego
    Photo 28 of 34
  • Photo 29: House for sale : 4 bedrooms : 5744 Winchester Street in San Diego
    Photo 29 of 34
  • Photo 30: House for sale : 4 bedrooms : 5744 Winchester Street in San Diego
    Photo 30 of 34
  • Photo 31: House for sale : 4 bedrooms : 5744 Winchester Street in San Diego
    Photo 31 of 34
  • Photo 32: House for sale : 4 bedrooms : 5744 Winchester Street in San Diego
    Photo 32 of 34
  • Photo 33: House for sale : 4 bedrooms : 5744 Winchester Street in San Diego
    Photo 33 of 34
  • Photo 34: House for sale : 4 bedrooms : 5744 Winchester Street in San Diego
    Photo 34 of 34
Listed by ShoppingSDHouses
Data was last updated May 20, 2026 at 09:10 PM (UTC)
Area Statistics
Listings on market:
2,956
Avg list price:
$849,000
Min list price:
$95,000
Max list price:
$16,900,000
Avg days on market:
35
Min days on market:
0
Max days on market:
1,547
Avg price per sq.ft.:
$669.19
These statistics are generated based on the current listing's property type and located in San Diego. Average values are derived using median calculations. This data is not produced by the MLS® system.
This information is deemed reliable but not guaranteed. You should rely on this information only to decide whether or not to further investigate a particular property. BEFORE MAKING ANY OTHER DECISION, YOU SHOULD PERSONALLY INVESTIGATE THE FACTS (e.g. square footage and lot size) with the assistance of an appropriate professional. You may use this information only to identify properties you may be interested in investigating further. All uses except for personal, non-commercial use in accordance with the foregoing purpose are prohibited. Redistribution or copying of this information, any photographs or video tours is strictly prohibited. This information is derived from the Internet Data Exchange (IDX) service provided by San Diego Multiple Listing Service, Inc. Displayed property listings may be held by a brokerage firm other than the broker and/or agent responsible for this display. The information and any photographs and video tours and the compilation from which they are derived is protected by copyright. Compilation © 2026 San Diego Multiple Listing Service, Inc.