Winter Park Village Homes for Sale

4 Beds ⋅ 4 Baths ⋅ Winter Park Village SubDv. ⋅ 32789 Zip Code

Architecture, design, and function come together with remarkable intention in this custom Winter Park residence designed by renowned architect Gary Hancock. From the impressive curb appeal and graceful archways to the carefully selected finishes throughout, every part of this home was designed with purpose. The result is a residence that feels sophisticated and distinctive while remaining remarkably comfortable for everyday living. Striking from the moment you arrive, the home features beautiful archways, balanced architectural lines, and a timeless exterior that immediately sets it apart. Step inside to an open, light-filled floor plan with 10-foot ceilings, expansive windows, level 5 drywall, and designer lighting throughout.An open floor plan creates an easy flow between the main living spaces, with a fireplace anchoring the living room and the adjoining dining area opening directly to the outdoor entertaining space. At the center of the home is a Italian-inspired chef’s kitchen featuring custom cabinetry, designer countertops, a paneled refrigerator, and premium induction range.The primary suite offers a private retreat with a spacious bath complete with a freestanding soaking tub, oversized walk-in shower, and a large walk-in closet. Each secondary bedroom is generously sized and includes its own en-suite bath, providing privacy and convenience for family and guests, while the bonus room and additional storage provide added flexibility. The outdoor spaces are an extension of the home, with a covered patio, fully equipped summer kitchen, sparkling pool, and expansive backyard offering plenty of room for both entertaining and relaxing. Perfectly positioned in Winter Park, this home offers easy access to Park Avenue, exceptional dining and shopping, top-rated schools, and virtually everything you need just minutes from your front door. A rare opportunity to own a custom-designed home with exceptional architecture, quality construction, and a prime Winter Park location—all at an exceptional value.

2430 Chantilly Avenue, Winter Park

$998,000

4 Beds ⋅ 4 Baths ⋅ Winter Park Village SubDv. ⋅ 32789 Zip Code

Experience the perfect blend of modern luxury, thoughtful design, and an unbeatable Winter Park location in this stunning custom residence built in 2023 by acclaimed builder Odin Homes. Showcasing over two years of gentle ownership, this exceptional home lives like new and offers a rare opportunity to own a move-in-ready custom home without the wait of new construction. Designed with sophistication and functionality in mind, this 4-bedroom, 4-bath residence features spacious living areas, designer finishes, soaring ceilings, and an open-concept floor plan ideal for both everyday living and entertaining. Every detail reflects Odin Homes' renowned craftsmanship, quality construction, and attention to detail. Perfectly situated on a beautiful homesite in one of Winter Park's most desirable neighborhoods, residents enjoy access to top-rated schools including Dommerich Elementary, Maitland Middle School, and Winter Park High School. The location offers exceptional convenience just minutes from Park Avenue's renowned dining and shopping, downtown Orlando, Winter Park Village, major employers, and area attractions. Whether you're searching for a primary residence or simply want the benefits of newer construction without the construction timeline, this exceptional custom home delivers luxury, location, and lifestyle in one of Central Florida's most sought-after communities.

1404 Border Drive, Winter Park

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Orange County › Winter Park › Winter Park Village

Winter Park Village, Winter Park

Winter Park Village is a neighborhood in north Winter Park, in the 32789 zip code, built mostly in the 1950s. Homes are block and stucco. Most homes fall between about 900 and 3,500 square feet under air, and the median lot is roughly a fifth of an acre.

Most of Winter Park Village carries no mandatory HOA.

What the homes are

Built Mostly built in the 1950s, with homes from 1956 to 2026.
Construction Block and stucco. Shingle roofs on 60% of homes.
Size Most homes fall between about 900 and 3,500 square feet under air.
Bedrooms Three bedrooms is the most common plan, then four, then two.
Lot The median lot is roughly a fifth of an acre.
HOA Most of the neighborhood carries no mandatory HOA. Confirm on a specific parcel before relying on it.

Where Winter Park Village is

Winter Park Village, centered at 28.622237, -81.333794. Drag to explore.

Street level, inside the neighborhood. Drag to look around.

Drive times below are measured on the road network from the center of Winter Park Village, not straight-line distance, in free-flowing traffic. Treat them as the floor rather than the school-run average.

Driving to	Time	Miles
Downtown Orlando	23 min	12.1
Walt Disney World	38 min	31.3
Orlando International Airport	32 min	24.5
Universal Orlando	30 min	19.3

Public schools nearby

Dommerich Elementary School 6 min, 1.9 mi
Lakemont Elementary School 6 min, 1.8 mi
English Estates Elementary School 8 min, 2.9 mi
Aloma Charter High School 8 min, 3.0 mi

Private schools nearby

Christian Education at Woodruff Academy 7 min, 2.0 mi
Lake Forrest Preparatory School 7 min, 2.3 mi
Chesterton Academy of Orlando 6 min, 2.5 mi
St. Margaret Mary Catholic School 8 min, 2.3 mi

Parks and recreation

Howell Branch Preserve 2 min, 0.5 mi
John Langdon Park 3 min, 0.8 mi
Lake Knowles Park 4 min, 1.0 mi
John Hudson Park 4 min, 1.2 mi

Groceries and errands

DG Market 3 min, 0.9 mi
Publix Super Market at Casselberry Commons 4 min, 1.3 mi
SuperFresh Market 6 min, 1.6 mi
In-N-Out Market 6 min, 2.0 mi

Useful local links

Nearest is not the same as zoned. The schools above are the closest ones to Winter Park Village by distance. School attendance zones are set by the district, change from year to year, and can differ street to street inside one neighborhood. Confirm the assignment for a specific address with Orange County Public Schools before it matters to a decision.

Places and drive times from Google, checked 20 September 2026. Businesses open and close; if something here has changed, tell me and I will correct it.

This page tracks what homes in Winter Park Village actually sold for over the last twelve months, how long they took, and what moved the price. It is built from 4 verified closed sales in the Stellar MLS feed, not from public estimates. Every figure is a net-of-concessions number, which is explained at the bottom. Updated November 2026.

Read this one loosely. Fewer than eight homes closed here in the last year, so every median on this page rests on a small sample and can swing on a single sale.

What homes sold for in Winter Park Village

$775,000Median sale price

$351Median per square foot

267 daysMedian days to contract

4Homes sold in 12 months

Sale prices ran from $425,000 to $1,395,000, which is a wide spread and the reason a single neighborhood median is a starting point rather than an answer.

By size

Home size	Sales	Median price	Median $/sq ft	Median days
2,000 to 3,000 sq ft	3	$1,000,000	$361	267 days

A price per foot taken from the whole neighborhood should never be applied straight to one house.

Price cuts and time to contract

Median days to go under contract. Shorter is better.

Never reduced 2 sales, closed at 96.7% of asking60 days

Reduced at least once 2 sales, closed at 91.6% of the reduced price420 days

Sellers who held their number went under contract in a median 60 days. Sellers who had to reduce took 420 days and still closed at 91.6% of their already reduced price, after a typical cut of $193,000.

How buyers paid

Cash 3 sales75%

Conventional 1 sale25%

Cash was 75% of purchases. A high cash share means a seller has buyers who do not depend on an appraisal, and a buyer using a loan is competing against offers that can close faster.

Questions about a specific home in Winter Park Village, or want to know what yours would sell for?
Call or text Brenden Rendo at 407-616-9019 or send a message.

About this data. Source is the Stellar MLS feed for Winter Park Village in Winter Park, Orange County, covering closed sales from 8 November 2025 through 3 November 2026, refreshed monthly and current as of November 2026. Prices are net of seller concessions, so they reflect what the seller actually received rather than the headline number. Data believed accurate but not guaranteed; listings and closings change daily.