2361 ROXBURY ROAD, WINTER PARK, FL, 32789
Active25 days on marketListed Jun 30, 2026MLS #O6418164
About this home
2361 ROXBURY ROAD
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, solid plaster walls 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. New Anderson exterior doors improve the homes security and efficiency. The expansive Florida room provides flexible space for entertaining or future updates. Major improvements include a resurfaced Gunite pool in pebble finish (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!
Facts & features
The home at a glance
3
Bedrooms
2
Bathrooms
1,723
Sqft
0.28 ac
Lot size
1951
Year built
One
Levels
$348
Per sqft
Inside
Outside & construction
Community & fees
Utilities & systems
The numbers
What it really costs
Built from this home's actual numbers — the most recent property-tax bill on record — not generic estimates.
$3,799 /mo · 10% down Conventional, 30-yr fixed at 6%
The assumptions
Above the FHA loan limit for our service areas, so Conventional is the default. VA buyers: switch below — $0 down.
These numbers assume a generic buyer — your credit, down payment and loan program change them. Get the real quote in minutes:
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Run your own numbers
FHA isn’t available at this price — the loan would exceed the $541,287 FHA limit for our service areas.
Estimated payment
$3,799/mo
Includes estimated PMI — it drops off once you reach 20% equity. Taxes reflect the most recent bill on record; insurance is a typical-Florida estimate. Your lender’s numbers will differ. CENTURY 21 Edge partners with Florida’s best lenders.
Value check
Is the price right?
The internet’s favorite home-value number comes from a single automated model that has never seen the street, the finishes, or the view — which is why it routinely misses by tens of thousands of dollars. The edgeAI estimate combines multiple independent data sources with our team’s on-the-ground expertise in this exact market.
vs edgeAI estimate
+3.3%
$/sqft vs Winter Park actives
$348 vs $343
Days on market
25 vs 34 typical
Where $348/sqft sits among the 320 Winter Park actives
The edgeAI estimate is a starting point, not an appraisal or a broker price opinion. It is generated from public records, listing data and market modeling, and is subject to change once a licensed real estate professional personally inspects the property. Condition, floor, view and lot are not fully captured by any model — ask us for a full comparative market analysis.
Where it sits
Inside Lake Killarney
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Get to know Winter Park. See the full Winter Park guide →
Lake Killarney — neighborhood snapshot
Population
2,209
Median age
61
Median income
$68,693
Median home value
$396,822
Avg household
2
Households w/ children
107
For the school run
Orange County School District
School assignments and ratings via edgeAI — always verify with the district.
The numbers that matter
The Winter Park market
$473K → $500K
Winter Park median sold, yr/yr
96.8%
Sale-to-list ratio (12 mo)
148 of 320
Winter Park actives have cut their price
Median sold price, Winter Park, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 30% below the WINTER PARK 32789 median. See the full Winter Park market guide →
Paper trail
This home's history
Reality check
What actually sold near 2361 ROXBURY ROAD
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Jan ’26$420,000
1357 FAIRVIEW STREET
3 bd · 2 ba · 1,740 sqft · $241/sqft · 5 DOM
Sold · Mar ’26$675,000
1201 NOTTINGHAM STREET
3 bd · 2 ba · 1,696 sqft · $398/sqft · 5 DOM
Sold · Jun ’26$695,000
1550 NORFOLK AVENUE
3 bd · 2 ba · 1,762 sqft · $394/sqft · 8 DOM
Closed-sale data from the MLS, last 12 months, selected for similarity in size and location. No two homes are identical — ask us for a full comparative analysis.
Your home team
The pros in your corner
Buying a home is two conversations — the home and the money. Here’s who handles each, side by side, already working together.
Your agent
David Ramirez
Real Estate Agent · CENTURY 21 Edge
Tours, negotiation, and every question about 2361 ROXBURY ROAD — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 2361 ROXBURY ROAD — before you fall in love.
See it in person
Schedule a tour
Pick a day that works — this goes straight to David's phone and CRM.
Straight answers
2361 ROXBURY ROAD FAQs
What would the monthly payment be for 2361 ROXBURY ROAD?+
With 10% down on a 30-year Conventional loan at 6%, the all-in payment lands around $3,799/mo — principal and interest, the actual property-tax bill and typical Florida insurance. The payment calculator on this page lets you switch loan type (FHA, Conventional, VA) and adjust the down payment, rate and term.
What are the property taxes on 2361 ROXBURY ROAD?+
The most recent tax bill on record (2025) was $2,184. A new owner's bill can differ once the sale price resets the assessed value — we can walk you through what to expect.
How does the price compare to other homes in Winter Park?+
At $599,000, this home is listed about 4% below the Winter Park median of $627,000. The market section on this page shows how the area is trending.
Which schools are assigned to 2361 ROXBURY ROAD?+
Killarney Elementary (elementary), Edgewater High (high), College Park Middle (middle) — Orange County School District. Always verify school assignments with the district before relying on them.
Keep looking
Similar homes nearby
Listing courtesy of ANNE ROGERS REALTY GROUP INC · Arden Magee. MLS #O6418164.
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. Data is deemed reliable but is not guaranteed accurate by Stellar MLS.
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