2381 ROXBURY ROAD Winter Park, FL $ 499,900
2381 ROXBURY ROAD
$ 499,900
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2381 ROXBURY ROAD

Winter Park, FL, 32789
$ 499,900
Bedrooms3 Baths2.0 Sq 1,785

Monthly Estimate*

$ 3,119

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Single Family Home for sale in Winter Park, FL

for $499,900 with 3 bedrooms and 2 full baths. This 1,785 square foot home was built in 1949 on a lot size of 0.28.

One or more photo(s) has been virtually staged. Live the Winter Park dream in this freshly updated 3-bedroom, 2-bath home—just steps from Lake Killarney and minutes to I-4, boutique shopping, and top dining spots. The interior has been freshly painted, creating a bright and welcoming feel throughout. The updated kitchen shines with white shaker cabinets, quartz countertops, a subway-tile backsplash, and stainless-steel appliances. It’s perfect for everyday cooking and effortless entertaining. Wood-look laminate floors flow through the spacious living and dining rooms and into the bedrooms, while the family room offers wood-look tile, a cozy fireplace, and sliding doors that open to the screened patio. Outside, a long driveway extends beyond the fenced yard to a side-entry oversized two-car garage with workshop area. Surrounded by mature trees, the backyard is a private retreat with a cozy firepit, utility shed, and a versatile concrete pad—ideal for basketball games or weekend gatherings under the stars. Zoned R-1A, the property also allows for an accessory structure such as a guest suite or studio (no kitchen permitted) Thoughtful updates, generous outdoor space, and an unbeatable location near Lake Killarney make this home a rare find. Come experience comfort, character, and convenience in the heart of Winter Park.

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Single Family Pending

Price

$ 499,900

Bedrooms

3

Full Bath

2

Property Type

Single Family

Taxes

$ 2,001

Style

Ranch

Lot Size

0.28

Year Built

1949

Town/City

Winter Park

County/Region

Orange

MLS | Web ID

O6355324

Features
Interior
Interior Amenities ceiling fan(s) stone counters thermostat
Flooring laminate tile
Fireplace Features family room wood burning
Total Stories 1
Air Conditioning Y/N yes
Heating Y/N yes
Window Features blinds
Fireplace Y/N yes
Half Baths 0
Laundry Features inside laundry room
Total Bedrooms 3
Total Baths 2
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General
Sewer septic tank
Heating central electric heat pump
Cooling central air
Utilities cable connected electricity connected public water connected
Possession close of escrow
Roof shingle
Appliances dishwasher disposal microwave range refrigerator
Zoning r-1a
Garage Spaces 2
Patio/Porch Features covered screened
Architectural Style ranch
Construction Materials block
Pets Allowed yes
Year Built 1949
Levels one
Property Subtype single family residence
Tax Year 2024
Ownership fee simple
County orange
New Construction no
Property Type residential
HOA N
Attached Garage yes
Subdivision Name glencoe sub
Facing Direction south
Garage Y/N yes
Other Structures shed(s) workshop
Total Rooms 9
Full Baths 2
Status pending
Directions from 17-92 go west on fairbanks right on cambridge blvd left on killarney left on roxbury
High School edgewater high
City winter park
Senior Community Y/N no
MLS Area 32789 - winter park
Lot Size Units square feet
Lot Size Square Feet 11989
Carport Y/N no
Listing Terms cash conventional fha va loan
Elementary School killarney elem
Land Lease Y/N no
Tax Annual Amount 2001.34
Middle/Junior High School college park middle
Additional Parcels Y/N no
Lease Considered Y/N yes
Virtual Tour https://vimeo.com/1131062818?fl=ip&fe=ec
Building Area Units square feet
Living Area Units square feet
Standard Status pending
Occupancy Type vacant
Tax Lot 22
Legal Description glencoe sub l/132 lot 22 & e1/2 lot 23 blk i
Minimum Lease 7 months
Water Access Y/N no
Additional Rooms family room formal dining room separate formal living room separate inside utility
Water View Y/N no
Flood Zone Code x
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Exterior
Exterior Amenities sidewalk sliding doors
Vegetation mature landscaping
Fencing chain link vinyl
Parking Features driveway garage door opener garage faces side oversized workshop in garage
Lot Features city lot oversized lot sidewalk
Water Source public
Lot Size Area 11989
Foundation Details slab
Building Area Total 2565
Lot Size Acres 0.28
Road Surface Type paved
Private Pool no
Waterfront Y/N no
Covered Spaces 2
Road Frontage Type street paved
Road Responsibility public maintained road
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Internal Only
Street Number 1 2381
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* Excluded Features
List By
Coldwell Banker Realty

Broker

aavastardis@live.com

Email

Affordability Calculator

$3,285
Per Month
95%
5%
0%
Monthly Principal & Interest
$3,119
Monthly Property Taxes
$167
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.375% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
3324138 Elementary School
3220615 Middle School
Edgewater High High School
Pricing History
DatePricePrice ChangeDescription
11/15/2025$499,900 -1.98% Price Down
10/26/2025$510,000 Listed Price

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2381 ROXBURY ROAD, Winter Park, FL, 32789 is a Single Family Home for sale at $499,900 with 1,785 sqft and a lot size of 0.28. 2381 ROXBURY ROAD has 3 bedrooms, 2.0 baths, and was built in 1949. The property's zip code is 32789 which is in Winter Park, FL