644 Winter Park Street, FL644 Winter Park Street, FL644 Winter Park Street, FL
Stellar MLS
1 / 70

$1,425,000

644 Winter Park Street

Orlando, FL 32804

Listing updated: October 1, 2026 at 3:05 PM ET

Active
Stellar MLSListing courtesy of Charles Rutenberg Realty Orlando · Molly Nichols · MLS #O6443687 · Active · 407-622-2122
5
Beds
6
Baths
3,298
Sq Ft
0.28
Acres
1950
Built
◆In-law suite◆Fireplace◆5-car garage◆$432/sqft
Single Family Residence

Property type

1950

Year built

11,996 sqft

Lot size

$432

Price / sq ft

No HOA

HOA dues

2

Days on market

5

Garage spaces

X

Flood zone

About this home

LOCATION! Exceptional opportunity in the heart of historic College Park 32804! This one-of-a-kind property offers a beautifully renovated 3-bedroom, 2/1-bath main residence PLUS a detached 896 SF, 2-bedroom, 2-bath guest house above an impressive 4-car garage/shop with lift and half bath. The main residence was extensively renovated in 2015 while preserving its classic College Park charm. Major improvements include main roof (2015), guest house roof (2025), three HVAC systems including guest house (Main house 2015, 2025 & guest house 2025), completely replumbed including all supply and drain lines replaced and completely rewired. A whole-house natural gas Generac standby generator with automatic transfer switch. The open floor plan showcases original hardwood upstairs with engineered hardwood throughout the first floor. The chef-inspired kitchen features handcrafted solid-wood cabinetry with pull-outs and soft-close drawers, granite countertops, oversized island with prep sink, breakfast bar and custom KitchenAid stand-mixer lift with dedicated outlet. Appliances include a built-in refrigerator/freezer approximately 5' wide, double convection ovens, microwave, 36" five-burner gas cooktop, dishwasher and dual-zone wine cooler. A stainless farmhouse sink with instant hot water completes the space. The expansive 22'x24' living room features a natural gas fireplace and flows into an oversized dining area. Restored original French doors with crystal knobs open to a light-filled office, plus a separate den/media room. The spacious primary suite includes a 14'x7' custom walk-in closet with built-in shelving and built in safe. The spa-inspired bath features custom solid-wood dual vanities, granite countertops, walk-in shower with three shower heads including oversized rainfall shower, and 6' whirlpool tub. The laundry room offers extensive cabinetry, counter space, utility sink, hanging rack, stacked washer and natural gas dryer. Upstairs are two additional bedrooms, full bath and huge walk-in attic. The detached building offers a 4-car garage/shop with vehicle lift and half bath. Upstairs, the 896 SF fully furnished guest house has its own entrance and address at 646 W Winter Park Street and features 2 bedrooms, 2 baths, living area, full kitchen and laundry. The almost 12,000 SF lot is surrounded by a custom block wall with electric gate and offers exceptional off-street parking, a large paver circular driveway and space for at least six vehicles. Enjoy the 18'x30' covered screened porch with custom summer kitchen, sink with hot/cold water and garbage disposal, built-in Blackstone grill connected to natural gas. The backyard also features an 14x25 paver patio with wood burning fire pit with removable cooking grate and room for a custom pool and spa. Additional features include hardwired closed-circuit security cameras with DVR, city water/sewer and metered natural gas. Adding even more versatility and future potential, the property has been verified as eligible for conversion to commercial use. Just steps from Edgewater Drive, dining, entertaining, The Packing District and minutes drive to Lake Highland Preparatory School, Bishop Moore High School and St Charles Borromeo School this rare property combines historic charm, extensive renovations, separate guest house, incredible garage/workshop space, outdoor entertaining and future-use flexibility. Schedule your private showing today!

Estimated monthly payment

Principal & interest$7,206
Property taxes$576
Home insurance (est.)$653

Estimate only. Taxes use the listing's reported amount where available; insurance is a Florida-average estimate. Your actual payment will vary — run a full calculation or talk to a lender.

Price & listing history2 days on market

  1. Status: Active
    Sep 29, 2026
  2. Listed$1,425,000
    Sep 29, 2026
  3. Price increased$1,425,000

Property Documents

Documents the listing agent has made public for this property. Free to view and download.

Facts & features

Property type
Residential
Sub type
Single Family Residence
Status
Active
Days on market
2
Subdivision
Dubsdread Add
County
Orange
Year built
1950
Living area
3,298 sq ft
Price/sq ft
$432
Building area
5,088 sq ft (Owner)
Lot size
11,996 sq ft
Lot category
1/4 to less than 1/2
Flood zone
X (12095C0235F)
Garage
5 spaces
Annual taxes
$6,913 (2025)
Parcel #
14-22-29-2244-03-221
Zoning
R-1/T/W/SP
MLS #
O6443687

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Interior Details

Bedrooms
5
Full bathrooms
4
Half bathrooms
2
Flooring
Hardwood, Wood
Appliances
Bar Fridge, Built-In Oven, Convection Oven, Cooktop, Dishwasher, Disposal, Dryer, Exhaust Fan, Gas Water Heater, Ice Maker, Microwave, Range, Range Hood, Refrigerator, Tankless Water Heater, Touchless Faucet, Washer, Wine Refrigerator
Interior features
Attic Ventilator, Dry Bar, Eat-in Kitchen, Open Floorplan, Primary Bedroom Main Floor, Solid Surface Counters, Solid Wood Cabinets, Split Bedroom, Stone Counters, Thermostat, Walk-In Closet(s), Wet Bar, Window Treatments
Laundry
Laundry Room
Stories / Levels
Multi/Split
Direction faces
North
Fireplace
Yes
In-law suite
Yes

Heating & Cooling

Heating
Heat Pump
Cooling
Central Air, Attic Fan

Parking

Garage spaces
5
Attached garage
Yes
Parking features
Bath In Garage, Boat, Circular Driveway, Oversized, Workshop in Garage

HOA & Financial

Total monthly fees
$0/mo
Total annual fees
$0
CDD
No
Homestead exemption
Yes
Min lease term
No Minimum
Listing terms
Cash, Conventional
Ownership
Fee Simple
Available for lease
Yes
Lease restrictions
No
Additional lease restrictions
Buyer and buyer’s agent to independently verify all lease and rental restrictions with the applicable municipality.

Exterior & Construction

Exterior features
Outdoor Grill, Outdoor Kitchen, Rain Gutters, Sidewalk
Construction materials
Cement Siding
Roof
Shingle
Foundation
Crawlspace, Slab, Stem Wall
Road surface
Paved

Utilities

Sewer
Public Sewer
Water source
Public
Utilities
BB/HS Internet Available, Cable Available, Cable Connected, Electricity Available, Electricity Connected, Fiber Optics, Natural Gas Available, Natural Gas Connected, Phone Available, Public, Water Available, Water Connected

Community

Pets allowed
Yes

Schools

ElementaryAPrinceton ElemGreatSchools ↗
MiddleCCollege Park MiddleGreatSchools ↗
High SchoolAEdgewater HighGreatSchools ↗

Letter grades: Florida DOE 2024–25 school grades (Orange, Seminole, Lake, Osceola, Brevard). Assigned schools from the listing agent — verify enrollment with the district.

Room Details

RoomLevelDimensions
Primary BedroomFirst15x16
Primary BathroomFirst14x9
Bedroom 2Second15x10
Bedroom 3Second13x10.5
Dining RoomFirst13x12
Living RoomFirst24x22
OfficeFirst15x8
KitchenFirst15.5x16
LaundryFirst12x8
Balcony/Porch/LanaiFirst30x18
DenFirst15.5x10.5
DinetteFirst14x10

Listing Details

Listing date
2026-09-29
On market date
2026-09-29
Original list price
$1,425,000
Occupant type
Owner
MLS area
32804 - Orlando/College Park
Listing AOR
Orlando Regional
Status changed
2026-09-29
Tax legal description
DUBSDREAD ADDITION K/1 W 1/2 LOT 22 & ALL LOT 23 BLK C

Flood risk

Minimal riskFEMA Zone XPanel 12095C0235F

Minimal-risk area outside the mapped floodplain. Flood insurance is optional and typically low-cost.

Source: FEMA flood zone reported on the listing. Confirm current designation at FEMA Flood Map Service Center.

Location

Directions

I4 to Princeton St. Take a right on Edgewater Dr. and right on W Winter Park St. Home is on right

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MLS GRID

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IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Based on information submitted to the MLS GRID as of October 1, 2026 at 3:05 PM ET. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

All or a portion of the multiple listing information is provided by Stellar MLS, from a copyrighted compilation of listings. The compilation of listings and each individual listing are © 2026 Stellar MLS. All rights reserved.

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