27 Photos

$365,000

5004 Winona Avenue

Southampton, St Louis, Missouri, 63109

MLS® 26059753 · Listed by Garcia Properties

0 bedrooms2424.00 sqftResidential Income0 days on marketBuilt 1926Lot 4238.39$3,986 taxes (2025)2 garageForced Air · Central AirFull basement
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About this property

*RARE FIND*--a two-family with a true THREE bedroom apartment! Why rent when you can own—and have someone else help pay the mortgage? This solid Southampton two-family is the ultimate first step into homeownership, combining a place to call your own with built-in rental income. Move into one unit, rent the other, and let your tenant help offset your monthly payment while you build equity instead of paying your landlord's mortgage. The location couldn't be better. You're just a short walk from neighborhood favorites like The Attic Music Bar, The Royale, Silverleaf Lounge, Bud's Pizza & Beer, The Golden Hoosier, and morning coffee runs to Piper's. Enjoy all the charm and convenience that make South City such a great place to call home. Inside, both apartments offer a comfortable, functional layout with a living room, dining room, kitchen, full bath & a charming sunroom both you & your houseplants will love. The second floor apartment has three private bedrooms & the first floor apartment has two private bedrooms. Original hardwood floors on the main level (brand new carpet upstairs), vintage fireplaces, stained glass windows, and classic architectural details add the kind of character that's hard to find in newer construction. Grab a drink and unwind on the spacious covered front porch, tackle laundry and storage with ease in the large unfinished basement, and enjoy the convenience of a garage & parking pad out back. Whether you're looking for an affordable path to homeownership, a smart investment, or both, this Southampton gem is ready to help you get ahead. Want more info? Skip the Zillow rabbithole & reach out to me, the listing agent, directly for more info or to schedule a tour.

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Estimated value

$369,227

Estimated range: $357,643 $380,810 · 3% confidence

Estimated value by month

Estimated value trend from Oct 2025 ($364,587) to Sep 2026 ($369,227)Oct 2025Sep 2026

This is an automated estimate based on MLS® market data — not an appraisal or a substitute for professional advice.

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Comparable recent sales

Sold records the MLS® data provider selected as comparable to this home — nearby recent sales at a similar price, bed count, and property type. Locations are shown at the neighborhood level only.

SoldAug 5, 2026

$389,000

Listed at $385,000

Northampton, St Louis, Missouri

0 bd · 2300.00 sqft · Residential Income

Similar properties

MLS® data for this listing last updated Sep 15, 2026.

Market snapshot

The Southampton, St Louis market

Closed sales in Southampton, St Louis over the last 12 months.

$310,000

Median sold price

28

Avg. days on market

11

Homes sold

Median sold price by month

Median sold price trend from Oct 2025 ($262,900) to Jun 2026 ($248,750)Oct 2025Jun 2026