Winter Park, FL Duplexes for sale

Updated: Sep 10

Five-Bedroom Duplex with Private Yard

1421 MICHIGAN Avenue, Winter Park, FL 32789

$586,567

2,031 sqft 0.16 AC lot

2,031 SF duplex with 0.16 acres of land
Five bedrooms and three bathrooms across two residences
Unit A: 2 bedrooms and 1 bathroom; Unit B: 3 bedrooms and 2 bathrooms
Unit B is tenant occupied through October
R‑2 zoning with public water and public sewer

View details

Updated: Aug 23

Duplex with Private Entrances

1016 ARAGON Avenue, Winter Park, FL 32789

$660,000

1,840 sqft 0.16 AC lot

Two‑unit property with 4 bedrooms, 2 full baths, and 2 half baths
1,840 square feet on a 0.16‑acre lot
R‑2 zoning in Winter Park, FL
Each unit includes two bedrooms, a Jack‑and‑Jill bath, and a half bath
Private entrances, fenced courtyard, patio, and private pool

View details

Fenced Duplex with Private Pool

1016 ARAGON Avenue, Winter Park, FL 32789

$660,000

1,840 sqft 0.16 AC lot

Two-unit residential property with separate entrances, central systems, and one occupied unit.

View details

See what stands out in Orange County

We check every for-sale listing in the county against comparable properties across the country. Most price about where you would expect. A few are worth a second look.

We check every listing here. A few are worth a second look.

Cap Rate available after sign in

NOI available after sign in

Local Demand available after sign in

Income Duplex with Fenced Yards

5427 PEACO PLACE, Winter Park, FL 32792

$550,000

1,974 sqft

Two rental units include granite counters and fenced yards, with a 3-bed 2-bath and a 2-bed 1-bath configuration.

View details

Corner-Lot Duplex

901 HARMON Avenue, Winter Park, FL 32789

$650,000

1,277 sqft 0.13 AC lot

R-2-zoned duplex with private entrances, covered driveway parking, and separate living and dining areas.

View details

Duplex Property with Corner Lot

3302 ROYAL Street, Winter Park, FL 32792

$279,900

1,197 sqft 0.14 AC lot

Three-bedroom residence with ceramic tile flooring, granite kitchen counters, and no HOA.

View details

Turn a Listing Into an Investment Snapshot Cap Rate, Potential NOI, Demand score for every listing. Go To Analytics Center

Two-Unit Duplex with Patios

726/720 N PENNSYLVANIA Avenue, Winter Park, FL 32789

$1,185,999

2,282 sqft 0.09 AC lot

Two residential units offer private fenced patios, in-unit laundry, and parking.

View details

Duplex with Separate Residences

1016 ARAGON AVENUE, Winter Park, FL 32789

$660,000

1,840 sqft

Each side offers two bedrooms, a Jack-and-Jill bath, and a half bath.

View details

Two-Bedroom Duplex Unit

2712 TORTOISE CV, Winter Park, FL 32792

$235,000

924 sqft 0.13 AC lot

Open-plan residence with ceramic tile flooring, central air, and no HOA.

View details

Single-Story Duplex Property

5781 SHALE Court, Winter Park, FL 32792

$300,000

1,086 sqft 0.20 AC lot

Two-bedroom, two-bath layout with screened outdoor space and public utilities.

View details

Corner Lot Duplex With Updates

901 HARMON AVENUE, Winter Park, FL 32789

$650,000

1,277 sqft

Duplex on a corner lot with recent roof, window, exterior paint, and updated ACs.

View details

Leased Two-Unit Duplex

2183 CRANDON AVENUE, Winter Park, FL 32789

$499,000

1,200 sqft

Two-bedroom units include private entrances, central AC, and screened patio areas.

View details

Duplex Property with Screened Patio

Winter Park, FL 32792

$300,000

One-story residential property with two bedrooms, two full bathrooms, and a covered, screened outdoor area.

View details

Duplex with Recently Replaced Roof

3128 PATEL DRIVE, Winter Park, FL 32792

$409,900

1,934 sqft

Separate two-bedroom, two-bath units feature tiled or laminate floors, appliances, laundry hookups, and partially fenced backyards.

View details

Based on your search, we've compiled 18 Potential Opportunities for your consideration. Besides 14 Active listings in Winter Park, FL, we suggest exploring several alternatives: 4 properties in Nearby Cities

Opportunities in Nearby Cities

Here are 4 Similar properties we found in Nearby Locations for your consideration.

Duplex Property with Vaulted Ceilings

1417 BELGRADE Avenue, Orlando, FL 32803

$589,999

1,650 sqft 0.15 AC lot

R-2A/T/SP-zoned property with public water and sewer, central air, and multiple outdoor living areas.

View details

Renovated Duplex with Carports

2910 DADE Avenue, Orlando, FL 32804

$599,600

1,584 sqft 0.24 AC lot

Two separate units provide kitchens, living areas, bedrooms, bathrooms, and laundry rooms.

View details

Duplex with Detached ADU

3701 VIRGINIA Drive, Orlando, FL 32803

$625,000

2,044 sqft 0.19 AC lot

Two residences share a fenced parcel with separate entrances, updated systems, and a flexible layout for rental or multigenerational use.

View details

Renovated Duplex with Carports

2910 DADE AVE, Orlando, FL 32804

$599,600

Two residential units feature equipped kitchens, private laundry rooms, living areas, and covered parking.

View details

Winter Park, FL Duplexes Market Trends and Statistics

Explore 14 duplexes for sale in Winter Park, FL, showcased through 14 active listings on our real estate platform. These investment opportunities span a total of 20,702 square feet of properties for sale, with an estimated market value of $7,626,366.

Sale prices for duplexes in Winter Park, FL start at $235,000, averaging $544,740, and reaching up to $1,185,999 — offering options for a variety of budgets and business needs. Daily updated analytics ensure you stay ahead with the latest data and market trends.

Neighborhood	Average Price
32792	$335K
32789	$709.3K

Neighborhood

Average Price

32792

$335K

32789

$709.3K

Featured Winter Park Real Estate Agencies

Realmo connects you with licensed Winter Park CRE brokers providing property specifications, local market pricing, and commercial transaction underwriting support.

Kelly Price & Company

243 West Park Avenue, Suite 100 Winter Park, FL 32789

Phone: 14076454321