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Overview

2 bd3 ba1,440 sqftTriplex
TypeTriplex
HOANone listed
Built1942
Lot4,898 sqft
Living area1,440 sqft
Price / sqft$517

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Pricing, comps, HOA, the neighborhood. Answers before you fill out anything.

About this home

Ceiling Fans(s)FenceSidewalkStorageDishwasherDryerRangeRefrigerator

408 Holt Ave is a 1942-built home in Trotters Rep, Winter Park. Inside you'll find 2 bedrooms, 3 bathrooms, and 1,440 square feet of living space. Listed at $745,000 (about $517/sqft), 159 days on market. Flood zone X - outside the FEMA high-risk areas, which keeps insurance manageable.

From the listing

Rare investment opportunity in the heart of Winter Park/Rollins College area. This turnkey, fully renovated triplex is located within one of Winter Park’s highest-demand rental corridors, just steps from Rollins College, Park Avenue, and Lake Virginia. The property features three separate 1-bedroom, 1-bath units, each with its own private outdoor patio area, positioned on a charming brick street in one of Winter Park’s most walkable and desirable neighborhoods. The asset is being delivered with strong in-place cash flow. Current rents provide additional value-add potential, with at least one unit currently operating below market rental rates, creating an opportunity for future income growth and increased returns. The block construction property has undergone significant capital improvements, including updated electrical panels (2019), new hot water heater (2019), new windows (2017), and a new roof (2015). Two of the three units were completely renovated in 2019, offering updated interiors while maintaining the charm and character of the surrounding neighborhood. The front unit includes washer/dryer hookups, while the middle and rear units share a common exterior-access washer/dryer area. Utilities are currently included in the rent and have been factored into annual operating expenses. This is a rare opportunity to acquire a stabilized multifamily asset with strong rental demand driven by proximity to Rollins College, downtown Park Avenue, dining, shopping, and employment centers throughout Winter Park.

The essentials

Built
1942
Price / sqft
$517
On market
159 days
Annual tax
$5,765
Flood zone
X · Low risk
Lot
4,898 sqft
Type
Triplex

At a glance

Single family
Built 1942
4,898 sqft lot
Lot size
1,440 sqft
Living area

Payment

Est. monthly payment
$4,738/mo
Down payment (20%)
$149,000
Property taxes
$480/mo
Rate assumed
6.8% · 30 yr
View full breakdown

Details

Type
Triplex
Year Built
1942
Lot
4,898 sqft
Cooling
Wall/Window Unit(s)
Heating
Ductless
Parking
Common, Driveway, Off Street
Days on Market
159
Ceiling Fans(s)
Fence
Sidewalk
Storage
Dishwasher
Dryer
Range
Refrigerator
Washer
Elementary
Audubon Park K8
Middle
Audubon Park K-8
High
Winter Park High

Districts can re-zone, so verify directly with the district before relying on these.

Flood Zone X
Annual Tax (2025)
$5,765
Parcel #
07-22-30-8760-00-011

Taxes reflect the most recent assessment in the MLS feed. Actual tax owed can vary, so confirm with the county property appraiser before closing.

Subdivision
Trotters Rep
County
Orange
MLS Area
32789 - Winter Park
Lot Size
4,898 sqft
City LimitsStreet Brick

Price history

Date
Event
Price
5/8/2026
Listed for sale
Source: Stellar MLS #O6405857
$745,000
$517/sqft

Neighborhood

408 Holt Ave
Winter Park, FL, 32789 · 32789 - Winter Park

Market insights

Offer Insights

Choose an offer strength

List price: $745,000
$725,000 – $745,000
97.2% – 100% of listTops out right at the list price
80% of listList price
97 of the last 192 home closings in 32789 landed at this number or higher (51%). The median one sat 21 days before it went under contract, and this one is on day 159.

Sample: 192 closed home sales in 32789 over the last 8 months, Stellar MLS. A starting point, not a guarantee.

Talk through an offer with our team

Calculator

Est. monthly payment
$4,738/mo
Principal & interest$3,885
Property taxes$480
Insurance$373
Down payment20% · $149,000
Interest rate6.80%
Loan term

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Property taxes are this home's actual annual bill from the MLS, divided by twelve. Insurance estimated at 0.60%. Rate defaults to 6.8% on a 30-year fixed. Tap a pencil to use your own numbers. Estimates only, not a loan quote.

Quick answers.

Price

$745,000

$517 per sq ft

Beds and baths

2 beds, 3 baths

Size

1,440 sq ft

Time on market

159 days

Year built

1942

Monthly payment

About $4,738/mo

That is 20% down on a 30-year fixed at 6.8%, plus the home's $5,765 annual tax bill, insurance.

Flood zone

Zone X

That is outside the high-risk areas, so flood insurance is usually optional rather than required by a lender.

Offer

What should I offer?

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Brokered byTHE REAL ESTATE PRINCIPLE, INCListing agent: Brian OpreListing data from Stellar MLS, MLS# O6405857.

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