5744 Winchester Street, San Diego, CA 92139
Single-family home · 2 recorded sales since 2024
Sold July 2026
Listing Agent: Delta Sivonsay (DRE #02130191) · Listing Office: ShoppingSDHouses · Contact: 760-216-8505 · Bought with: Nicole Casillas · Coldwell Banker West · MLS #PTP2603854 · Source: CRMLS
How this sale compares
5744 Winchester Street sold for $885,000 in July 2026, 2.7% under its $910,000 list price, after 20 days on the market. It was first listed at $799,000. That works out to $565 per square foot on 1,567 square feet. Across 82 closed sales in 92139 over the last 12 months, the median sold price is $723,750 and the median is $507 per square foot, 10% below this sale's $565.
| Quarter | Closed sales in 92139 | Median sold price |
|---|---|---|
| Q1 2026 | 4 | $532,500 |
| Q2 2026 | 42 | $700,000 |
| Q3 2026 | 33 | $770,000 |
| Q4 2026 | 3 | $715,000 |
Figures are MLS-reported closed sales (CRMLS); ZIP medians cover the last 12 months. Nalren does not estimate values. Recently sold in San Diego · Homes for sale in 92139
Description
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.
Listing description from the July 2026 sale, as reported to CRMLS.
Sale history
Recent sales near 5744 Winchester Street
5603 Winchester St: Sold $660,000 · 2 bd · 1 ba · 874 sqft · Jun 2026 · 0.1 mi
Black Label Realty | DRE #02078596
Buyer's agent: Miguel Gutierrez, Silverstone | DRE #022514732436 38 Reo Dr.: Sold $892,000 · Jun 2026 · 0.2 mi
Coldwell Banker West | DRE #01466994
Buyer's agent: Eleazar Cruz, eXp Realty of California, Inc. | DRE #021742702436 38 Reo Dr.: Sold $892,000 · 4 bd · 2 ba · 2,174 sqft · Jun 2026 · 0.2 mi
Coldwell Banker West | DRE #01466994
Buyer's agent: Eleazar Cruz, eXp Realty of California, Inc. | DRE #021742706031 Cumberland: Sold $590,000 · 3 bd · 2 ba · 1,120 sqft · Aug 2026 · 0.4 mi
Simon Properties R.E. | DRE #00909863
Buyer's agent: Robin Simon, Simon Properties R.E. | DRE #009098635949 Potomac: Sold $770,000 · 3 bd · 2 ba · 1,218 sqft · Aug 2026 · 0.5 mi
Compass | DRE #02018557
Buyer's agent: Ronald Rojas De Leon, eXp Realty of Southern Calif. | DRE #022159133107 Mount Miguel Dr.: Sold $835,000 · 4 bd · 2 ba · 1,712 sqft · Jun 2026 · 0.6 mi
Century 21 Affiliated | DRE #02032592
Buyer's agent: Ezequiel Bolanos, BBR Partners | DRE #021783902533 Calle Tres Lomas: Sold $793,000 · 3 bd · 2 ba · 1,188 sqft · Jul 2026 · 0.7 mi
Mike Tompkins Realty | DRE #01844465
Buyer's agent: John Olsen, Mission Realty Group | DRE #013743693047 Fleming Drive: Sold $839,000 · 4 bd · 3 ba · 1,844 sqft · May 2026 · 0.7 mi
Coldwell Banker West | DRE #00900285
Buyer's agent: Alex Ortega, Premier Agency R.E. Inc | DRE #01321114
Closed sales reported in 92139, nearest first, last 12 months. All recent sales in San Diego →