INNOVATE Real Estate
Multi-Family 5+ at 421 E KENNEDY BLVD, MAITLAND
Multi-Family 5+ at 421 E KENNEDY BLVD, MAITLAND, photo 2 of 6
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6 photos

$3,500,000

421 E KENNEDY BLVD
MAITLAND, FL 32751
Listed by David Washington · CHARLES RUTENBERG REALTY ORLANDO
Bedrooms
N/A
Bathrooms
N/A
Living area
15,777 sqft
Year built
1967

About this home

Prime mixed-use commercial property perfectly situated between the vibrant cities of Maitland and Winter Park. This centrally located asset offers both visibility and versatility. The listing encompasses a 29-unit multifamily building, adjacent commercial building 429 E. Kennedy Blvd, and a commercial lot 34 N. West St —offering incredible potential for future development, expansion, or mixed-use revitalization. Whether you’re an investor or developer, this is a rare opportunity to be part of a growing community with active revitalization efforts. New roof installed in 2023.

Property details

MLS
Stellar MLS
MLS #
MFRO6330371
Property type
Multi-Family 5+
Subdivision
COOPERS SUB
Status
Active
Days on market
261
On market date
July 25, 2025
Stories
N/A
Total bathrooms
N/A
Garage spaces
N/A
Parking spaces
N/A
Lot size
0.85 acres

Location

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Nearby schools

Within 10 miles. School directory data from the National Center for Education Statistics (NCES), accessed via the Urban Institute Education Data API. Local Score is calculated by INNOVATE Real Estate; where a state rating is shown, it comes from that state's own official school report card.

Elementary
HUNGERFORD ELEMENTARY
0.35 mi away · Grades -1-5
Nearest school -- attendance-zone data not available here
4.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
249
Student:teacher ratio
13.1:1
District
ORANGE
Middle
MAITLAND MIDDLE
2.38 mi away · Grades 6-8
Nearest school -- attendance-zone data not available here
2.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
774
Student:teacher ratio
19.8:1
District
ORANGE
High
PACE CENTER FOR GIRLS
1.29 mi away · Grades 6-12
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
30
Student:teacher ratio
10.0:1
District
ORANGE

Walkability

Blended score for MAITLAND's center, calculated by INNOVATE Real Estate from two sources: the EPA's National Walkability Index (street network, transit, land-use mix) and Google Places amenity data (what's actually reachable on foot from this point). 60% EPA National Walkability Index + 40% nearby-amenity density (Google Places).

79
Walkable
out of 100
EPA National Walkability Index
15.7 / 20 -- Most walkable
Google Places amenity density
80 / 100
Restaurants & cafes20
Grocery stores0
Parks6
Schools14
Transit stops20
Pharmacies2

Market position

How this listing compares to current activity in MAITLAND, from live MLS data.

On the market 261 days -- 193 more days than MAITLAND's current average of 68 days.
For reference, the median list price across 161 active listings in MAITLAND right now is $325,000.

Mortgage calculator

Estimate only - actual rate and payment depend on your lender, credit, and loan program.

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Adjust tax / insurance estimates
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Est. monthly payment
$21,227/mo
$700,000 down
$2,800,000 loan
Principal & interest$18,161
Property tax (est.)$2,917
Home insurance (est.)$150

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Data source: Listing information provided by Stellar MLS (mfrmls) via Trestle/CoreLogic. Last updated August 19, 2026.

Information herein deemed reliable but not guaranteed; all measurements, school assignments, HOA fees, taxes, and feature lists are approximate and should be independently verified. Equal Housing Opportunity.