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.
Property Details
Price:
$799,000
MLS #:
PTP2603854
Status:
Active
Beds:
4
Baths:
2
Type:
Single Family
Subtype:
Single Family Residence
Neighborhood:
92139paradisehills
Listed Date:
May 19, 2026
Finished Sq Ft:
1,567
Lot Size:
8,712 sqft / 0.20 acres (approx)
Year Built:
1947
See this Listing
Schools
School District:
Other
Interior
Appliances
DW, MW, RF, ES, GER, ER, TW
Bathrooms
2 Full Bathrooms
Cooling
DUC
Flooring
VINY
Heating
CF
Laundry Features
IG
Levels
A
Main Level Bathrooms
2
Main Level Bedrooms
4
Exterior
Accessibility Features
PK
Common Walls
NCW
Community Features
CRB
Fencing
CH, WD
Parking Spots
4
Parking Total
4
Patio And Porch Features
POF
Roof
SHN
View
NE
Financial
Map
Community
- Address5744 Winchester ST San Diego CA
- CitySan Diego
- CountySan Diego
- Zip Code92139
Subdivisions in San Diego
- Bay Park
- BP
- Carmel Mountain Ranch
- Carmel Valley
- Casa Dorado 32501
- CAV
- CH
- Chula Vista
- City Heights
- Civita CIVI
- Clairemont
- CLM
- College Grove
- Crown Point
- Del Cerro
- Downtown
- Downtown Area DOWN
- DWTN
- East San Diego
- Encanto
- ENCTO
- Escala ESCL
- Hillcrest
- Imperial Beach
- Kearny Mesa
- Kensington
- La Jolla
- La Mesa
- Linda Vista
- Logan Heights
- LV
- Middletown
- Mira Mesa
- Mirador MIRD
- Mirasol MIR
- Mission Beach
- Mission Hills
- Mission Valley
- Mission Village
- Mount Helix
- Normal Heights
- North Park
- NP
- Ocean Beach
- Old Town
- Pacific Beach
- Paradise Hills
- Park Villas PKVL
- Park Vista PV
- Point Loma
- Poway
- Rancho Bernardo
- Rancho Pacifica 1 261701
- Rancho Penasquitos
- Rancho Santa Fe
- Sabre Spr
- San Carlos
- San Diego
- San Ysidro
- SANT
- Santaluz
- Scripps Ranch
- SD
- Serra Mesa
- Smoke Tree SMTR
- South Sd
- Stonebridge 3700
- Talmadge
- The Lakes LK
- Tierrasanta
- Torrey Highlands
- University City
- University Heights
- Villa Portofino 32283
- Woodcrest WT
Market Summary
Current real estate data for Single Family in San Diego as of May 27, 2026
1,802
Single Family Listed
70
Avg DOM
621
Avg $ / SqFt
$1,358,250
Avg List Price
Property Summary
- 5744 Winchester ST San Diego CA is a Single Family for sale in San Diego, CA, 92139. It is listed for $799,000 and features 4 beds, 2 baths, and has approximately 1,567 square feet of living space, and was originally constructed in 1947. The current price per square foot is $510. The average price per square foot for Single Family listings in San Diego is $621. The average listing price for Single Family in San Diego is $1,358,250.
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5744 Winchester ST
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