Nested on a spacious, tree lined lot just steps from Lake Killarney, 2361 Roxbury Road offers a rare opportunity to create your dream home in one of Winter Park’s most convenient locations. Ideally situated just off Fairbanks Avenue with quick access to I-4 , this 3 bedroom, 2 bath residence features 1723 square feet of living space and mid century character. Built in 1951, the home showcases an original pine paneled ceiling in the living room, adding warmth and architectural charm. Two large new Anderson windows fill the room with natural light and highlight the pool view. The expansive Florida room provides flexible space for entertaining or future updates. Major improvements include a resurfaced pool (2024), exterior paint (2024), new paver driveway (2024), roof (2020) and HVAC system (2019). The garage has been enclosed and currently serves as storage and utility space. Outside you’ll find a fully fenced backyard with plenty of room to enjoy the Florida lifestyle. Located on a large lot with sidewalks and mature trees, this home presents an excellent opportunity for buyers looking to personalize a property in a desirable Winter Park location. The septic system was pumped in 2026, providing peace of mind. Bring vision and make this home your own!
For sale
$599,000
2361 Roxbury Rd, Winter Park, FL 32789
3beds
1,723sqft
Single Family Residence
Built in 1951
0.28 Acres Lot
$-- Zestimate®
$348/sqft
$-- HOA
What's special
Mid century characterPool viewSpacious tree lined lotExpansive florida roomNatural lightFully fenced backyard
- 13 hours |
- 360 |
- 28 |
Zillow last checked:
Listing updated:
Listed by:
Arden Magee 407-276-1698,
ANNE ROGERS REALTY GROUP INC 407-649-4141
Source: Stellar MLS,MLS#: O6418164
Originating MLS: Orlando Regional
Originating MLS: Orlando Regional
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Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 3
- Bathrooms: 2
- Full bathrooms: 2
Rooms
- Room types: Florida Room
Primary bedroom
- Features: Built-in Closet
- Level: First
Florida room
- Features: Bar, Built-in Closet
- Level: First
- Area: 274.4 Square Feet
- Dimensions: 19.6x14
Kitchen
- Level: First
Living room
- Level: First
Heating
- Central
Cooling
- Central Air
Appliances
- Included: Dryer, Range, Refrigerator, Washer
- Laundry: In Garage
Features
- Thermostat
- Flooring: Carpet, Engineered Hardwood, Porcelain Tile
- Has fireplace: No
Interior area
- Total structure area: 1,847
- Total interior livable area: 1,723 sqft
Video & virtual tour
Property
Features
- Levels: One
- Stories: 1
- Exterior features: Private Yard, Rain Gutters
- Has private pool: Yes
- Pool features: Gunite
- Fencing: Chain Link
Lot
- Size: 0.28 Acres
- Dimensions: 81 x 149
- Residential vegetation: Mature Landscaping, Oak Trees
Details
- Parcel number: 022229299609201
- Zoning: R-1A
- Special conditions: None
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Mid-Century Modern,Ranch
- Property subtype: Single Family Residence
Materials
- Concrete
- Foundation: Slab
- Roof: Shingle
Condition
- Completed
- New construction: No
- Year built: 1951
Utilities & green energy
- Sewer: Septic Tank
- Water: Public
- Utilities for property: Cable Connected, Electricity Connected, Public, Water Connected
Community & HOA
Community
- Pet fee: $0 monthly
- Subdivision: GLENCOE SUBDIVISION
HOA
- Has HOA: No
Location
- Region: Winter Park
Financial & listing details
- Price per square foot: $348/sqft
- Tax assessed value: $296,417
- Annual tax amount: $2,184
- Date on market: 6/30/2026
- Listing terms: Cash,Conventional,FHA,VA Loan
- Ownership: Fee Simple
- Total actual rent: 0
- Electric utility on property: Yes
- Road surface type: Paved
Estimated market value
Not available
Estimated sales range
Not available
Not available
Price history
| Date | Event | Price |
|---|---|---|
| 6/30/2026 | Listed for sale | $599,000+418.6%$348/sqft |
Source:  Stellar MLS #O6418164 Report a problem | ||
| 8/6/1997 | Sold | $115,500$67/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2024 | $2,022 +7.7% | $143,288 +3% |
| 2023 | $1,877 +5.3% | $139,115 +3% |
| 2022 | $1,782 +2.3% | $135,063 +3% |
| 2021 | $1,742 +0.7% | $131,129 +1.4% |
| 2020 | $1,730 +2.4% | $129,319 +2.3% |
| 2019 | $1,689 +1.5% | $126,412 +1.9% |
| 2018 | $1,664 | $124,055 -39.4% |
| 2017 | $1,664 +2% | $204,629 +10.6% |
| 2016 | $1,631 +2% | $185,013 +6.5% |
| 2015 | $1,600 -3.9% | $173,656 +28.3% |
| 2014 | $1,665 +2.1% | $135,322 +12.4% |
| 2013 | $1,630 +1.2% | $120,434 +6% |
| 2012 | $1,611 -2.1% | $113,575 -1.5% |
| 2011 | $1,645 +4.4% | $115,305 -11.9% |
| 2010 | $1,576 | $130,928 -22.3% |
| 2009 | -- | $168,523 -12.8% |
| 2008 | $1,445 -7.7% | $193,350 -7.2% |
| 2007 | $1,566 -5.1% | $208,270 +7.9% |
| 2006 | $1,649 +2.1% | $193,084 +12.7% |
| 2005 | $1,616 +5% | $171,373 +24% |
| 2004 | $1,538 +0.9% | $138,228 +1.2% |
| 2003 | $1,525 +3.2% | $136,637 +21.1% |
| 2002 | $1,478 -1% | $112,859 +4.9% |
| 2001 | $1,494 +2.5% | $107,553 +14.9% |
| 2000 | $1,457 | $93,627 |
Find assessor info on the county website
Monthly payment
Est. payment$--/mo
Payment breakdown
Explore the cost of this home by adjusting the details. Changes won't be saved.All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
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Climate risks
Neighborhood: 32789
Nearby schools
GreatSchools rating
- 4/10Killarney Elementary SchoolGrades: PK-5Distance: 0.1 mi
- 3/10College Park Middle SchoolGrades: 6-8Distance: 1.4 mi
- 6/10Edgewater High SchoolGrades: 9-12Distance: 1.4 mi
Schools provided by the listing agent
- Elementary: Killarney Elem
- Middle: College Park Middle
- High: Edgewater High
Source: Stellar MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
A local agent can set up tours, give advice and negotiate with sellers.
- Florida
- Orange County
- Winter Park
- 32789
- 2361 Roxbury Rd
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