Winter Park has a population of nearly 30,000 residents and was founded as a resort community in the early 20th century. Winter Park is known for the vibrant main street full of art galleries, museums, civic buildings, shopping & much more. Many move to Winter Park due to the bustling Park Avenue area and the beautiful homes. It's a desirable area, which started as a resort community. Of course, the close proximity to Orlando helps to attract new home buyers relocating to the area, as well.
The properties found in Winter Park include some townhomes and condominiums. However, most are single-family homes and tend to be larger with four or more bedrooms. Many homes have been custom built with luxurious amenities. There are a number of large estates located on the water in Winter Park.
The average home hitting the market in Winter Park will be listed for about $866K. However, the price range can easily get up into the millions for some of the larger estates.
With plenty of history surrounding the Langford Resort Hotel, Winter Park has been a popular destination for many years. While this specific hotel is no longer in existence, it once attracted guest, such as Ray Charles, John Denver, Dean Martin and even President Ronald Reagan. The Alfond Inn now occupies the space where the Langford used to sit.
Today, many are most attracted to the area for Park Avenue, which provides the majority of the amenities in Winter Park. Plenty of fine dining, boutique shopping and entertainment are found on Park Avenue. Some of the top spots include 310 Park South, Luma on Park and Prato.Along with the dining and shopping on Park Avenue, the city is home to a country club, historic cemetery, train station, plenty of art galleries and a beach and boat launch. Some of the most popular sites of interest in the city include:
The scenic Winter Park boat tours provide a great way to see some of the beautiful homes found throughout the community. Along with the many sites of interest, Winter Park is home to the Winter Park Sidewalk Art Festival, which is the largest and the oldest of the art festivals found in the country.
There are plenty of great schools found throughout Winter Park, Florida. From public elementary schools to well-known colleges, the area is well-known for the schools. Some of the top schools found in Winter Park include:
Casa del Mondo, known as House of the World on Park Avenue in Winter Park, is situated on Winter Park Chain of Lakes in the exclusive Twelve Oaks on a private road. Built...
One or more photo(s) has been virtually staged. This magnificent estate was originally built in 1938 with a major addition in 1999. The estate is nestled on 2 acres of pr...
Casa Bianca, the extraordinary Winter Park estate, has entered the market for the first time available in over 40 years. Perfectly positioned on the corner of Via Tuscany...
This custom built “Santa Barbara” Estate home is situated on 1.07 acres on the shores of Lake Osceola. This extraordinary, one of a kind estate was built in 1996 and off...
Contemporary living in the heart of Winter Park. This Phil Kean designed/built home is sure to be at the top of your list. Phil Kean’s distinctive signature style feature...
Pre-Construction. To be built. This Incredible Modern Transitional Home will be Breaking Ground Soon! It will be built on an Oversized Lot and is just Minutes to Park Ave...
Pristine custom Mediterranean Lakefront estate, with 5 bedrooms, 3.5 bathrooms, sandy beach (one of a kind) and 127’ on lake Osceola. Enjoy captivating views of lake Osce...
This spectacular contemporary, canal-front, home is perfect for those who appreciate the outdoors and enjoy boating on the Winter Park Chain of Lakes. Gated and sited on...
Pre-Construction. To be built. Homes don’t come along like this very often! Here’s your opportunity to own a Magnificent gated Estate on Lake Killarney- Drive up to your ...
Magnificent-Custom Mediterranean Master Piece in prime location of Winter Park.Carefully designed and built by using European influences, this gorgeous estate was planned...
Seize this rare opportunity to live in an Exquisite Downtown Winter Park Residence that is Luxury Living at its Finest. Welcome Home to this Elegant and Chic 3 story town...
Welcome home to this effortlessly bright and open, oversized, almost half-acre property with a beautiful lake view, located in one of the most precious and private spots ...
Located in the prestigious Via’s of Winter Park, this timeless home was custom-built on ½ an acre, and has been meticulously maintained by the original owners. The high-q...
Presenting an architecturally stunning, Posada Custom Homes estate in Winter Park’s Windsong community. Designed to perfection, this exquisite Spanish-Mediterranean home ...
ONE-OF-A-KIND, 8-Acre, LAKEFRONT, Paradise on Lake Howell (a private, skiable lake) in Winter Park. Over 220 FT. of LAKE FRONTGE w/ Dock & Panoramic Private Lake Views i...
Pre-Construction. To be built. Preparing to break ground on this newest Winter Park opportunity with F.G. Schaub Custom Homes. This Timeless Modern elevation offers a g...
10.26 acres located in Winter Park, Fl. 3 different parcels with 6 total structures, 2 structures are large barns / outdoor buildings with one having a large loft - large...
Under Construction. Under Construction. FG Schaub Custom Home opportunity will be ready in December 2022! Live the custom lifestyle in the highly sought-after Olde Wint...
Under Construction. Under Construction! one or more photos are renderings of the home. Brand new home in the heart of winter park. This new construction modern home is tr...
This lovely home is in the historic district of Winter Park known as College Quarter. It is well positioned on a corner lot and has a sweeping view of Lake Virginia. ...
Located in the heart of Winter Park this 0.43 acre property is approximately 125 feet wide by 150 feet deep. Discretely hidden behind a wall of podocarpus this exclusive ...
Located in the heart of Winter Park this 0.43 acre property has a lovely, one-story Santa Barbara style pool home with 2,709 square feet of air conditioned space. It is c...
Pre-Construction. To be built. This Cape Cod inspired home provides a rare pre-construction opportunity in highly coveted Winter Park. Make this modern marvel your foreve...
This spectacular home blends Santa Barbara Spanish Colonial architecture with stylish comfort and old Florida charm. Situated on an oversized 22,000-plus-square-foot lot ...
Location! Location! Location! WAREHOUSE building located in Winter Park with OFFICE and SHOWROOM space. ~ ZONED INDUSTRIAL with great exposure ~ Over 275 feet road front...
Pre-Construction. To be built. This stunning new house in Winter Park features the perfect blend of textures and clean finishes with modern warmth and undeniable sleeknes...
Under Construction. Don't miss the opportunity to live in a brand new custom designed pool home built by renowned Winter Park builder Carmen Dominguez. Warm woods and mod...
Stately Winter Park residence built by Rex-Tibbs on an oversized corner lot on Park Avenue is available and ready for a new owner! This 5-bedroom, 5-bath with office, bo...
Under Construction. Here is the perfect opportunity to purchase your very own private sanctuary in the heart of Winter Park. This exquisite transitional modern home by Pa...
Winter Park custom home on a quiet street with lake access to Winter Park Chain of Lakes on Lake Osceola at end of street. This four-bedroom, four-and-a-half-bath home is...
Enjoy the Heart and Soul of Winter Park's Original "Mr. Rogers Neighborhood". This is truly a one of a kind property. It is one of the few homes that offer Lake views w...
Days from Completion!!!! Pictures were taken on 6.28. Circular driveway will be added. Landscape work will begin shorty. Welcome to this luxury, Brand new built home in ...
Luxury lakefront living at its finest in the heart of downtown Winter Park! Nestled along the shore of beautiful Lake Virginia, this elegant 3 bed/3.5 bath, 2,714 sq ft g...
A++ Location (75% FAR) Buyer can bring their own builder (subject to HOA approval). If you want true walkability to Park Ave but don't want to sacrifice the comforts of a...
Under Construction. Fabulous new construction just a stroll from Park Avenue shopping and restaurants. Lun Dev has outdone themselves with this sophisticated and thoughtf...
On almost one acre in the heart of Winter Park, this beautiful Victorian home was extensively and meticulously remodeled and modernized in 2002 and 2011, while still reta...
Designed by Phil Kean Design Group, this stunning 3-bedroom, 3.5-bathroom townhome located in exclusive downtown Winter Park allows you to live the ultimate, turn key urb...
Pre-Construction. To be built. 5 Bed 4.5 Bath TO BE BUILT Pre Construction. This will be a looker come in to your new 4,400sq ft Winter Park house. It will have downstair...
Pre-Construction. To be built. Location, functionality, beautiful construction and a host of amenities make this the perfect place to call home. Historic oak trees drippi...
Gorgeous, Transitional Living in 32789. Masterfully designed and built to perfection, this 5 bedroom, 4.5 bathroom pool home offers modern, open living in the Heart of Wi...
The perfect executive office with a modern farmhouse design! Located in the city limits of Winter Park just 2 blocks East of I-4 on Fairbanks Ave. Ideal for any professi...
2 parcels located at Dodd Rd. and Howell Branch Rd. Winter Park, Fl Over 1 acre of redevelopment land with a future land use of OFFICE! Great location, high daily traffic...
An elegant build by Signature Homes in a prime Winter Park location a short stroll to Rollins College and Park Avenue. Lifestyle is everything and this courtyard-style ho...
Pre-Construction. To be built. Customize-to-suite this gorgeous Bermudan-style landmark home in the heart of Olde Winter Park! Presented by by Parade of Homes Winner, Wo...
Excellent opportunity to build your dream home near The Vias in Winter Park. Oversized 108x152, 0.38 acre lot. Existing structure on the site has no value - value is in t...
Excellent opportunity to build your dream home near The Vias in Winter Park. Oversized 108x152, 0.38 acre lot. Existing structure on the site has no value - value is in t...
Set in a gated little enclave on a quiet cul-de-sac in Winter Park, this custom home sports five bedrooms, three-full-and-two-half baths and a wonderful outdoor space to ...
Beautiful 1930’s Winter Park Character Home on Oversized 0.42 acre lot with privacy gate, detached mother-in law apartment, screened pool, and so much more. Originally bu...
Rare winter Park Lake Front Land .Lake Killarney . Absolutely Breath taking View . Close to All The Shops ,Restaurants , I-4 and Downtown. Build Your Dream Home On This ...
Under Construction. Completion in July 2022. Single family home and model unit. 4 bedrooms and 3.5 bathrooms equipped with an elevator. Enjoy luxury living and premium so...
Under Construction. Under Construction. Beautiful Transitional style home with a pool is being built in the beautiful Lake Forest Park neighborhood of Winter Park. This 3...
Pre-Construction. To be built. Excellent opportunity to build a modern coastal custom home with a 2 car rear entry garage in a very desirable location. This 3148 square f...
An absolute FIND! Over 1/2 acre on private Lake Sylvan a spring-fed jewel that is teaming with bass and catfish. In the middle of Old Winter Park and sited on a charming ...
An absolute FIND! Over 1/2 acre on private Lake Sylvan, a spring-fed jewel that is teaming with bass and catfish! In the middle of Old Winter Park, sited on a charming b...
A fantastic waterfront opportunity in Winter Park on the Lake Maitland Lagoon awaits. This 0.62-acre lot features 100 feet of frontage on Lake Maitland’s quiet lagoon and...
A fantastic waterfront opportunity in Winter Park on the Lake Maitland Lagoon awaits. This 0.62-acre lot features 100-feet of frontage on Lake Maitland’s quiet lagoon and...
This Winter Park pool home was built on a 0.40-acre corner lot, overlooking Lake Chelton, surrounded by brick streets and stately oak trees. This quiet neighborhood is co...
Santa Barbara 4 bedroom 4.5 bath in the heart of Winter Park. The Pool is in design and permitting phase and is not included with the price. The pool is an additional $45...
Totally renovated, “like-new” home on beautiful Henkel Circle, nestled between Lake Virginia and Like Mizell, easy walking to Park Avenue. The first floor was designed by...
Pre-Construction. To be built. To Be Built! Beachy/Modern Farmhouse for inspiration only. Bring your own builder or use our preferred builder for this lot, Vimaro Homes.
STUNNING WINTER PARK two bedroom condo oriented in the most private section of the Jewel of Winter Park! Villa Siena is located 2 blocks off Park Avenue and is directly a...
Pre-Construction. To be built. Take advantage of one of the last chances to live in Lake Killarney Shores, one of Winter Park's newest communities - a collection of 30 cu...
The first thing you will notice is how grandly this Colonial inspired home is situated on a gently arcing lot within the tree-lined streets of Quail Hollow. With nearly 4...
Pre-Construction. To be built. Take advantage of one of the last chances to live in Lake Killarney Shores, one of Winter Park's newest communities - a collection of 30 cu...
Pre-inspected. Offered for the first time in over 30 years! Winter Park’s only original, charming and completely remodeled historical farmhouse. Known as the “Harris-Edis...
Spectacular home in the great Winter Park neighborhood of Quail Hollow. Upon entering the foyer you will fall in love with the tremendous character and architectural deta...
Pre-Construction. To be built. Are you ready to enjoy this luxurious 4 Bedroom/ 4 Bathroom, two story home in Winter Park? This modern style home features an expansive i...
Walking distance to Park Avenue and ensconced in the beautiful Pennsylvania Place community of 28 homes, this property lives like a townhouse and offers a turnkey lifesty...
Pre-Construction. To be built. This impressive modern coastal farmhouse is being built by Parade of Homes award winning builder, Meridian Homes. Located on an impressive ...
Pre-Construction. To be built. Looking to purchase a new home in Winter Park? Barefoot Brothers Construction group presents this opportunity to build on a quiet street, b...
Totally renovated Modern Farmhouse looks as though Chip and Joanna Gaines had their personal touch on it! Long circle driveway and paver front porch welcomes friends to c...
busy street few blocks away from semoran blvd. nice area orf Winter Park.
This spectacular home is nestled on a quiet tree lined street of 28 Custom Homes in the desired neighborhood of Pennsylvania Place. This ideal location is just one block ...
STUNNING FLORIDA LAKEFRONT home on spring-fed LAKE BURKETT serves up the best of gorgeous views, a terrific Winter Park location, quiet community privacy, and tidy Florid...
Location! Location! Location! Don't miss out on this beautiful home in the heart of Winter Park! One block from Lake Virginia and just minutes from amazing shopping, dini...
Welcome home to 5008 Lake Howell Road. Perfectly located to all Winter Park has to offer. This is a truly unique home and offers many custom features not found in other h...
One or more photo(s) has been virtually staged. Located in the heart of Winter Park, this home has it all. It offers location and a minimal maintenance lifestyle. Built...
Permit ready and start immediately! Custom build with Rare Builders in the Charmont neighborhood of Winter Park. Seller has plans for a 4,350 SF home with 5 bedrooms an...
Welcome home to this thoughtfully renovated house in a desirable Winter Park neighborhood. Built in 1958, the property has only had two owners and has been maintained and...
High five, your search is over! This SPACIOUS, clean as a whistle, MOVE In ready, five bedrooms, three car garage, heated POOL home is located near a major road (417), b...
Enjoy Carefree living in this stunning upscale Condominium located in the heart of Winter Park in the highly sought after Casa Jardin community. Located within walking d...
Prime Winter Park Commercial Office space is ready for your healthcare practice or business! Unique well maintained corner lot boasting serenity with large oak trees and ...
One of a kind 4/3 pool home on over half an acre of land. Nestled back on a cul d sac in an established Winter Park neighborhood, this home is perfect for any stage of yo...
This distinctive and dramatic 3bedroom, 2.5 bath unit boasts custom wood cabinets, granite countertops, a walk-in butler's pantry, kitchen island, Front load washer and d...
Under Construction. Located between the shores of Lake Spier and Lake Compton you'll discover Lake Spier Crossing. This exclusive lakefront community, nestled in the hear...
Completely Renovated 3 story Townhome in Winter Park! The open concept living room and kitchen features Waterflow countertops, an oversized island, stainless steel applia...
Beautifully remodeled home in quiet Winter Park neighborhood. Fully renovated this year leaving no stone unturned, this home features all new electrical, plumbing, HVAC, ...
Gorgeous custom Mediterranean 3-level townhome in the middle of Winter Park! The incredible design and details in this residence will have you feeling like you’re living ...
Under Construction. Rare opportunity for affordable new construction in Winter Park! Construction has commenced! Walking distance to the historic Dubsdread Golf Course a...
Under Construction. Rare opportunity for affordable new construction in Winter Park! Construction has commenced! You will love the convenience of being in the hub of ac...
Unique opportunity to own a large home in Winter Park's Kings Cove subdivision. There are 4 bedrooms, 3.5 baths, an office, and a potential fifth bedroom. The entire bac...
This Kenilworth Shore, Sec. VII Winter Park Home is Move-In Ready! Completely Remodeled Inside & Out! Only Kenilworth Shores, Sec. VII has a PRIVATE Boat Ramp, Dock, Gate...
LAKEFRONT! Enjoy beautiful Lake Maitland from this charming 3rd floor FURNISHED & TURNKEY HOME at the Historic Alabama Condo located in the Vias of Winter Park. A rare o...
FULLY RENOVATED PHELPS PARK HOME !DUAL income potential - Master bedroom has separate entrance with long side driveway parking and an easily be converted into separate s...
**YOUR SEARCH STOPS HERE** GATED COMMUNITY! LOW HOA! LOCATION, LOCATION, LOCATION! This IMMACULATE 4 Bedroom, 2.5 Bath home is an absolute show stopper! This stunning sin...
This modern renovated Townhome is perfectly located where you can walk to Park Avenue, Mead Gardens, Azalea Tennis Courts & Rollins College, enjoy some of the best shoppi...
Welcome home to Via Veneto, an exclusive subdivision boasting four sprawling lakefront lots on Lake Temple. Don't miss the opportunity to design/build with local award-wi...
Welcome home to Via Veneto, an exclusive subdivision boasting four sprawling lakefront lots on Lake Temple. Don't miss the opportunity to design/build with local award-wi...
When you first walk into this immaculately updated home in Winter Park, with generous living space and custom finishes, you are greeted by a large open floor plan with a ...
Looking for a Pool home in Winter Park? You have found one! The home is newly remodeled with elegant modern features! Brand-new windows, kitchen cabinets, luxury quartz c...
David Myers 407-801-3286
Your Winter Park Real Estate Expert