276 DETMAR DRIVE, WINTER PARK, FL, 32789
Active26 days on marketListed Aug 25, 2026MLS #O6434825
About this home
276 DETMAR DRIVE
Tucked away in the heart of Winter Park, this custom-built residence seamlessly blends modern luxury with the comfort of everyday living. Thoughtfully designed with exceptional attention to detail, the home offers clean, contemporary interiors balanced by beautiful architectural elements, and abundant natural light. The main level offers two bedrooms and three full bathrooms, including a primary suite with a versatile bonus room behind French doors—perfect for a private office, gym, or additional bedroom. The ensuite features two walk-in closets, a double sink vanity, a large rainfall shower, and a soaking tub. The open-concept floorplan features a beautifully appointed kitchen with high-end appliances and custom cabinetry, flowing seamlessly with the dining area and the spacious living room, where a gas fireplace creates a welcoming gathering space. Architectural light wood ceiling beams, plantation shutters, and expansive glass sliders frame beautiful views of the outdoor living area. Upstairs, two additional bedrooms each feature private ensuite baths and balconies, complemented by a kitchenette and additional living space. This flexible layout is ideal for multigenerational living, guests, live-in staff, or simply creating a private retreat within the home. Designed for effortless indoor-outdoor living, the entire downstairs opens to a private backyard oasis featuring a sparkling saltwater pool, lush bamboo backdrop, summer kitchen, gas fireplace, and outdoor shower. The covered lanai is equipped with automatic screens, creating an inviting and comfortable space to enjoy the outdoors year-round. Beyond its sophisticated design, the home offers exceptional functionality, including an oversized two-car garage pre-wired for EV charging, whole-home surround sound, hurricane-impact windows, a whole-house Generac generator, indoor built-in sprinkler system, dual laundry rooms, and enhanced insulation for exceptional peace and quiet. The entire first floor is completely wheelchair accessible. Tastefully furnished and offered with all furnishings, this exceptional residence presents a rare combination of refined design, thoughtful functionality, and classic Winter Park charm. Ideally located just one mile from Park Avenue and minutes from Winter Park’s renowned restaurants, shops, hospitals, schools, and scenic Lake Osceola, this is a home designed for both elevated living and everyday comfort.
Facts & features
The home at a glance
4
Bedrooms
5
Bathrooms
4,202
Sqft
0.28 ac
Lot size
2
Garage
2022
Year built
Two
Levels
$857
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.
$23,950 /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
$23,950/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.
$/sqft vs Winter Park actives
$857 vs $350
Days on market
26 vs 43 typical
Where $857/sqft sits among the 349 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 Osceola Shores
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Get to know Winter Park. See the full Winter Park guide →
Osceola Shores — neighborhood snapshot
Population
221
Median age
59
Median income
$149,784
Median home value
$1,078,300
Avg household
2
Households w/ children
20%
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
$470K → $512K
Winter Park median sold, yr/yr
96.8%
Sale-to-list ratio (12 mo)
157 of 349
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 342% above the WINTER PARK 32789 median. See the full Winter Park market guide →
Paper trail
This home's history
Reality check
What actually sold near 276 DETMAR DRIVE
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Oct ’25$3,020,000
1820 ENGLEWOOD ROAD
5 bd · 5.5 ba · 4,263 sqft · $708/sqft · 70 DOM
Sold · Nov ’25$2,325,000
1268 PRESERVE POINT DRIVE
4 bd · 4 ba · 4,315 sqft · $539/sqft · 2 DOM
Sold · Feb ’26$3,600,000
1820 GLENCOE ROAD
5 bd · 6 ba · 4,055 sqft · $888/sqft · 209 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
Donna Layton
Real Estate Agent · CENTURY 21 Edge
Tours, negotiation, and every question about 276 DETMAR DRIVE — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 276 DETMAR DRIVE — before you fall in love.
See it in person
Schedule a tour
Live availability from Donna's calendar — pick a time and it's booked. Confirmation lands in your inbox immediately.
Straight answers
276 DETMAR DRIVE FAQs
What would the monthly payment be for 276 DETMAR DRIVE?+
With 10% down on a 30-year Conventional loan at 6%, the all-in payment lands around $23,950/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 276 DETMAR DRIVE?+
The most recent tax bill on record (2025) was $36,176. A new owner's bill can differ once the sale price resets the assessed value — we can walk you through what to expect.
Are pets allowed at 276 DETMAR DRIVE?+
The listing reports pets: Yes. Communities often layer on breed or weight rules — we'll verify the specifics with the association before you commit.
How does the price compare to other homes in Winter Park?+
At $3,600,000, this home is listed about 526% above the Winter Park median of $575,000. The market section on this page shows how the area is trending.
Which schools are assigned to 276 DETMAR DRIVE?+
Lakemont Elementary (elementary), Winter Park High (high), Maitland Middle (middle) — Orange County School District. Always verify school assignments with the district before relying on them.
The brief
Three things that matter here
01Positioned at the premium end
$3,600,000 runs 342% above the WINTER PARK 32789 median — but at 4,202 sqft it's also nearly 2 times the size of the typical Winter Park listing.
02Your own pool
A private pool — the feature Florida buyers ask for first, already in the ground and included in the price.
03Strong assigned schools
Lakemont Elementary, Winter Park High, Maitland Middle — Winter Park High rates 4 of 5. Always verify assignments with the district.
Keep looking
Similar homes nearby
Listing courtesy of CALL IT CLOSED INTL REALTY · Melanie Johnston. MLS #O6434825.
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.
Never miss a listing
New Winter Park homes, in your inbox
Like 276 DETMAR DRIVE but not quite? A daily digest of every new listing in Winter Park — straight from the MLS, hours after it goes live. Unsubscribe anytime.
Just watching this one home? Ask Donna to ping you on any price or status change →