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Central Florida › Orlando Metro › Orange County › Winter Park

Winter Park Florida

Winter Park Florida

Living in Winter Park

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.

Homes in Winter Park

Winter Park FountainThe 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.

Attractions and Things to Do in Winter Park

Alfond Inn in Winter Park FloridaWith 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.

Winter Park Chain of LakesAlong 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:

  • Annie Russel Theatre
  • Edward Hill Brewer House
  • Cornell Fine Arts Museum
  • Hannibal Square
  • Mead Botanical Garden
  • Kraft Azalea Park
  • Winter Park Public Library
  • Winter Park Historical Museum
  • And More!

Annie Russel Theatre at Rollins College in Winter ParkThe 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.

Education and Schools in Winter Park

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:

  • Aloma Elementary School
  • The Geneva School
  • The Parke House AcademyFull Sail University in Winter Park
  • Lakemont Elementary School
  • St. Margaret Mary Catholic School
  • Trinity Preparatory School
  • Winter Park High School
  • Full Sail University
  • Rollins College
  • Valencia Community College
  • Crealde School of Art

Winter Park Homes for Sale

1220 N Park Avenue, Winter Park image
1220 N Park Avenue, Winter Park $15,986,000

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...

  • 7 Beds
  • 5.5 Baths
  • Twelve Oaks SubDv.
  • 32789 Zip Code
1190 N Park Avenue, Winter Park image
1190 N Park Avenue, Winter Park $10,800,000

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...

  • 8 Beds
  • 5.5 Baths
  • 0000 SubDv.
  • 32789 Zip Code
1311 Via Tuscany, Winter Park image
1311 Via Tuscany, Winter Park $8,950,000 ▼

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...

  • 7 Beds
  • 6.5 Baths
  • J Kronenberger Sub SubDv.
  • 32789 Zip Code
1201 Alberta Drive, Winter Park image
1201 Alberta Drive, Winter Park $7,495,000

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...

  • 4 Beds
  • 5.5 Baths
  • Osceola Summit SubDv.
  • 32789 Zip Code
231 Chelton Circle, Winter Park image
231 Chelton Circle, Winter Park $5,500,000 ▼

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...

  • 5 Beds
  • 5.5 Baths
  • Forest Hills SubDv.
  • 32789 Zip Code
550 Palmer Avenue, Winter Park image
550 Palmer Avenue, Winter Park $4,900,000

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...

  • 5 Beds
  • 5.5 Baths
  • Osceola Place SubDv.
  • 32789 Zip Code
699 Osceola Avenue, Winter Park image
699 Osceola Avenue, Winter Park $4,495,000 ▼

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...

  • 5 Beds
  • 3.5 Baths
  • Winter Park SubDv.
  • 32789 Zip Code
1064 Howell Branch Road, Winter Park image
1064 Howell Branch Road, Winter Park $4,200,000

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...

  • 5 Beds
  • 4.5 Baths
  • Maitland Shores Second Add SubDv.
  • 32789 Zip Code
2056 Lake Drive, Winter Park image
2056 Lake Drive, Winter Park $4,194,900

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 ...

  • 5 Beds
  • 5.5 Baths
  • Lords Sub SubDv.
  • 32789 Zip Code
840 N Park Avenue, Winter Park image
840 N Park Avenue, Winter Park $3,990,000 ▼

Magnificent-Custom Mediterranean Master Piece in prime location of Winter Park.Carefully designed and built by using European influences, this gorgeous estate was planned...

  • 4 Beds
  • 4.5 Baths
  • Golfview Terrace SubDv.
  • 32789 Zip Code
125 S Interlachen Ave. Unit 1, Winter Park image
125 S Interlachen Ave. Unit 1, Winter Park — #1 $3,450,000

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...

  • 3 Beds
  • 3.5 Baths
  • South Interlachen Place 86/129 Lot 1 SubDv.
  • 32789 Zip Code
502 Genius Drive, Winter Park image
502 Genius Drive, Winter Park $3,450,000 ▼

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 ...

  • 6 Beds
  • 5 Baths
  • Windsong North Shore 43/74 SubDv.
  • 32789 Zip Code
1131 Via Lugano, Winter Park image
1131 Via Lugano, Winter Park $3,250,000 ▼

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...

  • 4 Beds
  • 4.5 Baths
  • Sicilian Shores SubDv.
  • 32789 Zip Code
1420 Holts Grove Circle, Winter Park image
1420 Holts Grove Circle, Winter Park $3,200,000

Presenting an architecturally stunning, Posada Custom Homes estate in Winter Park’s Windsong community. Designed to perfection, this exquisite Spanish-Mediterranean home ...

  • 4 Beds
  • 4.5 Baths
  • Windsong Lakeside Sec 02 43/71 SubDv.
  • 32789 Zip Code
2780 Lake Howell Lane, Winter Park image
2780 Lake Howell Lane, Winter Park $3,200,000

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...

  • 8 Beds
  • 6 Baths
  • Acreage & Unrec SubDv.
  • 32792 Zip Code
2413 Winter Park Road, Winter Park image
2413 Winter Park Road, Winter Park $3,150,000

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...

  • 5 Beds
  • 5.5 Baths
  • Parklando 03 SubDv.
  • 32789 Zip Code
5510 Howell Branch Road, Winter Park image
5510 Howell Branch Road, Winter Park $2,899,000

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...

  • Woodcrest Unit 8 SubDv.
  • 32792 Zip Code
1635 Highland Road, Winter Park image
1635 Highland Road, Winter Park $2,890,000 ▲

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...

  • 5 Beds
  • 5.5 Baths
  • Virginia Heights SubDv.
  • 32789 Zip Code
2015 N Park Avenue, Winter Park image
2015 N Park Avenue, Winter Park — Park Ave $2,749,000

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...

  • 4 Beds
  • 4.5 Baths
  • N Park Ave SubDv.
  • 32789 Zip Code
965 Lakeview Drive, Winter Park image
965 Lakeview Drive, Winter Park $2,600,000

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. ...

  • 4 Beds
  • 3.5 Baths
  • College Place Rep SubDv.
  • 32789 Zip Code
870 Georgia Avenue, Winter Park image
870 Georgia Avenue, Winter Park $2,550,000

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 ...

  • Winter Park Old Town SubDv.
  • 32789 Zip Code
870 Georgia Avenue, Winter Park image
870 Georgia Avenue, Winter Park $2,550,000

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...

  • 3 Beds
  • 2.5 Baths
  • Winter Park Old Town SubDv.
  • 32789 Zip Code
2723 Norris Avenue, Winter Park image
2723 Norris Avenue, Winter Park $2,499,000 ▲

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...

  • 4 Beds
  • 3.5 Baths
  • Parklando 02 SubDv.
  • 32789 Zip Code
1228 Mayfield Avenue, Winter Park image
1228 Mayfield Avenue, Winter Park $2,465,000

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 ...

  • 4 Beds
  • 3.5 Baths
  • Temple Heights SubDv.
  • 32789 Zip Code
4572 Palmetto Avenue Unit A, Winter Park image
4572 Palmetto Avenue Unit A, Winter Park $2,450,000

Location! Location! Location! WAREHOUSE building located in Winter Park with OFFICE and SHOWROOM space. ~ ZONED INDUSTRIAL with great exposure ~ Over 275 feet road front...

  • 4572 Palmetto Condo SubDv.
  • 32792 Zip Code
2412 Chantilly Avenue, Winter Park image
2412 Chantilly Avenue, Winter Park $2,331,000 ▲

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...

  • 5 Beds
  • 6.5 Baths
  • Winter Park Village SubDv.
  • 32789 Zip Code
1109 Oaks Blvd, Winter Park image
1109 Oaks Blvd, Winter Park $2,300,000

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...

  • 5 Beds
  • 5.5 Baths
  • Dixie Terrace SubDv.
  • 32789 Zip Code
1300 Raintree Place, Winter Park image
1300 Raintree Place, Winter Park $2,295,000 ▼

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...

  • 5 Beds
  • 5 Baths
  • Camwood Sub SubDv.
  • 32789 Zip Code
532 Worthington Drive, Winter Park image
532 Worthington Drive, Winter Park $2,200,000 ▲

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...

  • 5 Beds
  • 5.5 Baths
  • Kenilworth Shores Sec 01 SubDv.
  • 32789 Zip Code
472 Fletcher Place, Winter Park image
472 Fletcher Place, Winter Park $2,100,000

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...

  • 4 Beds
  • 4.5 Baths
  • Sorensen Heights SubDv.
  • 32789 Zip Code
215 Osceola Court, Winter Park image
215 Osceola Court, Winter Park $2,100,000

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...

  • 4 Beds
  • 3 Baths
  • Osceola Court SubDv.
  • 32789 Zip Code
281 Brewer Avenue, Winter Park image
281 Brewer Avenue, Winter Park $1,999,999 ▼

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 ...

  • 5 Beds
  • 4.5 Baths
  • Osceola Shores Sec 02 SubDv.
  • 32789 Zip Code
664 Osceola Avenue Unit 302, Winter Park image
664 Osceola Avenue Unit 302, Winter Park — 3 $1,999,000

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...

  • 3 Beds
  • 3.5 Baths
  • Perle Du Lac Condo Or 5843/4848 SubDv.
  • 32789 Zip Code
180 Whipple Avenue, Winter Park image
180 Whipple Avenue, Winter Park $1,995,000

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...

  • Greens At Park SubDv.
  • 32789 Zip Code
1156 Oaks Boulevard, Winter Park image
1156 Oaks Boulevard, Winter Park $1,995,000

Under Construction. Fabulous new construction just a stroll from Park Avenue shopping and restaurants. Lun Dev has outdone themselves with this sophisticated and thoughtf...

  • 4 Beds
  • 4.5 Baths
  • Dixie Terrace SubDv.
  • 32789 Zip Code
138 Detmar Drive, Winter Park image
138 Detmar Drive, Winter Park $1,995,000 ▼

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...

  • 6 Beds
  • 6.5 Baths
  • Eldridge & Grant Sub SubDv.
  • 32789 Zip Code
427 W Morse Boulevard, Winter Park image
427 W Morse Boulevard, Winter Park — 427 $1,900,000

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...

  • 3 Beds
  • 3.5 Baths
  • Virginia & Morse Brownstones SubDv.
  • 32789 Zip Code
102 Bell Pl, Winter Park image
102 Bell Pl, Winter Park $1,900,000

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...

  • 5 Beds
  • 4.5 Baths
  • Eastgate Sub SubDv.
  • 32792 Zip Code
130 Burks Circle, Winter Park image
130 Burks Circle, Winter Park $1,899,000

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...

  • 4 Beds
  • 4.5 Baths
  • Tangerine Court SubDv.
  • 32789 Zip Code
617 Worthington Drive, Winter Park image
617 Worthington Drive, Winter Park $1,895,000 ▼

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...

  • 5 Beds
  • 4.5 Baths
  • Kenilworth Shores Sec 06 SubDv.
  • 32789 Zip Code
1844 W Fairbanks Avenue, Winter Park image
1844 W Fairbanks Avenue, Winter Park $1,849,500 ▼

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...

  • Olympia Heights SubDv.
  • 32789 Zip Code
Howell Branch, Winter Park image
Howell Branch, Winter Park $1,800,000

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...

  • 32792 Zip Code
621 Huntington Avenue, Winter Park image
621 Huntington Avenue, Winter Park $1,795,000

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...

  • 3 Beds
  • 3.5 Baths
  • Town Of Winter Park SubDv.
  • 32789 Zip Code
280 E Lake Sue Avenue, Winter Park image
280 E Lake Sue Avenue, Winter Park $1,789,900

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...

  • 5 Beds
  • 4 Baths
  • Charmont SubDv.
  • 32789 Zip Code
1209 Sharon Place, Winter Park image
1209 Sharon Place, Winter Park $1,699,000

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...

  • Sharon Place SubDv.
  • 32789 Zip Code
1209 Sharon Place, Winter Park image
1209 Sharon Place, Winter Park $1,699,000

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...

  • 4 Beds
  • 3 Baths
  • Sharon Place SubDv.
  • 32789 Zip Code
2630 Park Place Drive, Winter Park image
2630 Park Place Drive, Winter Park $1,695,000

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 ...

  • 5 Beds
  • 3.5 Baths
  • Winter Park Place SubDv.
  • 32789 Zip Code
234 Detmar Drive, Winter Park image
234 Detmar Drive, Winter Park $1,695,000 ▼

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...

  • 4 Beds
  • 4.5 Baths
  • Osceola Shores Sec 01 SubDv.
  • 32789 Zip Code
1795 Killarney Drive, Winter Park image
1795 Killarney Drive, Winter Park $1,695,000

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 ...

  • Flamingo Shores SubDv.
  • 32789 Zip Code
508 W Swoope Avenue, Winter Park image
508 W Swoope Avenue, Winter Park $1,652,000 ▲

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...

  • 4 Beds
  • 3.5 Baths
  • Vilasa Townhomes SubDv.
  • 32789 Zip Code
2926 Parkland Court, Winter Park image
2926 Parkland Court, Winter Park $1,550,000

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...

  • 4 Beds
  • 3.5 Baths
  • Lake Forest Park SubDv.
  • 32789 Zip Code
915 N Kentucky Avenue, Winter Park image
915 N Kentucky Avenue, Winter Park $1,535,000 ▲

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...

  • 4 Beds
  • 3.5 Baths
  • Fairbanks Park SubDv.
  • 32789 Zip Code
313 Sylvan Drive, Winter Park image
313 Sylvan Drive, Winter Park $1,500,000

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 ...

  • Sylvan Park SubDv.
  • 32789 Zip Code
313 Sylvan Drive, Winter Park image
313 Sylvan Drive, Winter Park $1,500,000

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...

  • 3 Beds
  • 3 Baths
  • Sylvan Park SubDv.
  • 32789 Zip Code
910 Poinciana Lane, Winter Park image
910 Poinciana Lane, Winter Park $1,500,000 ▼

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...

  • 32789 Zip Code
910 Poinciana Lane, Winter Park image
910 Poinciana Lane, Winter Park $1,500,000 ▼

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...

  • 4 Beds
  • 3 Baths
  • Winter Park SubDv.
  • 32789 Zip Code
210 Chelton Circle, Winter Park image
210 Chelton Circle, Winter Park $1,490,000 ▼

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...

  • 4 Beds
  • 4 Baths
  • Forest Hills SubDv.
  • 32789 Zip Code
645 Pansy Avenue, Winter Park image
645 Pansy Avenue, Winter Park $1,479,000 ▼

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...

  • 4 Beds
  • 4.5 Baths
  • Villa View Park SubDv.
  • 32789 Zip Code
363 Henkel Circle, Winter Park image
363 Henkel Circle, Winter Park $1,350,000

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...

  • 5 Beds
  • 3 Baths
  • Thomas M Henkels Addition SubDv.
  • 32789 Zip Code
840 W Comstock Avenue, Winter Park image
840 W Comstock Avenue, Winter Park $1,300,000

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.

  • 4 Beds
  • 3.5 Baths
  • Winter Park SubDv.
  • 32789 Zip Code
315 E New England Avenue E Unit 12, Winter Park image
315 E New England Avenue E Unit 12, Winter Park — Villa Siena $1,300,000

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...

  • 2 Beds
  • 2 Baths
  • Villa Siena SubDv.
  • 32789 Zip Code
601 Ellen Drive, Winter Park image
601 Ellen Drive, Winter Park $1,299,000

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...

  • 4 Beds
  • 4.5 Baths
  • Lake Killarney Shores SubDv.
  • 32789 Zip Code
2164 Turkey Run, Winter Park image
2164 Turkey Run, Winter Park $1,250,000

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...

  • 5 Beds
  • 3.5 Baths
  • Quail Hollow SubDv.
  • 32789 Zip Code
603 Ellen Drive, Winter Park image
603 Ellen Drive, Winter Park $1,250,000 ▲

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...

  • 4 Beds
  • 4.5 Baths
  • Lake Killarney Shores SubDv.
  • 32789 Zip Code
1554 Harris Circle, Winter Park image
1554 Harris Circle, Winter Park $1,225,000 ▲

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...

  • 3 Beds
  • 2.5 Baths
  • Sylvan Lake Shores SubDv.
  • 32789 Zip Code
407 Turkey Run, Winter Park image
407 Turkey Run, Winter Park $1,200,000

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...

  • 4 Beds
  • 3 Baths
  • Quail Hollow SubDv.
  • 32789 Zip Code
1404 Border Drive, Winter Park image
1404 Border Drive, Winter Park $1,200,000

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...

  • 4 Beds
  • 4 Baths
  • Winter Park Village SubDv.
  • 32789 Zip Code
622 Penn Place, Winter Park image
622 Penn Place, Winter Park $1,199,000

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...

  • 3 Beds
  • 3 Baths
  • Pennsylvania Place SubDv.
  • 32789 Zip Code
2131 Loch Lomond Drive, Winter Park image
2131 Loch Lomond Drive, Winter Park $1,199,000

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 ...

  • 4 Beds
  • 4.5 Baths
  • Aloma SubDv.
  • 32792 Zip Code
1832 Pineview Circle, Winter Park image
1832 Pineview Circle, Winter Park $1,195,000

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...

  • 3 Beds
  • 3.5 Baths
  • Lakemont Heights SubDv.
  • 32792 Zip Code
1673 Mayfield Avenue, Winter Park image
1673 Mayfield Avenue, Winter Park $1,150,000 ▼

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...

  • 4 Beds
  • 4 Baths
  • Temple Estates SubDv.
  • 32789 Zip Code
Winter Park image
Winter Park $1,150,000 ▲

busy street few blocks away from semoran blvd. nice area orf Winter Park.

  • Suburban Homes SubDv.
  • 32792 Zip Code
664 Penn Place, Winter Park image
664 Penn Place, Winter Park $1,149,000

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 ...

  • 3 Beds
  • 2.5 Baths
  • Pennsylvania Place Rep SubDv.
  • 32789 Zip Code
5630 S Lake Burkett Lane, Winter Park image
5630 S Lake Burkett Lane, Winter Park $1,139,000 ▼

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...

  • 5 Beds
  • 3.5 Baths
  • Trinity Bay SubDv.
  • 32792 Zip Code
1700 Winter Park Road, Winter Park image
1700 Winter Park Road, Winter Park $1,089,000

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...

  • 3 Beds
  • 3 Baths
  • Charmont SubDv.
  • 32789 Zip Code
5008 Lake Howell Road, Winter Park image
5008 Lake Howell Road, Winter Park $975,000 ▲

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...

  • 5 Beds
  • 3.5 Baths
  • Tanglewood Rep SubDv.
  • 32792 Zip Code
792 W Swoope Avenue Unit 4, Winter Park image
792 W Swoope Avenue Unit 4, Winter Park $950,000

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...

  • 4 Beds
  • 3.5 Baths
  • Swoope Avenue Condominium Association SubDv.
  • 32789 Zip Code
205 E Rockwood Way, Winter Park image
205 E Rockwood Way, Winter Park $950,000

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...

  • Charmont SubDv.
  • 32789 Zip Code
616 Worthington Drive, Winter Park image
616 Worthington Drive, Winter Park $899,000

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...

  • 4 Beds
  • 3 Baths
  • Kenilworth Shores Sec 06 SubDv.
  • 32789 Zip Code
5325 Cypress Reserve Place, Winter Park image
5325 Cypress Reserve Place, Winter Park $899,000 ▼

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...

  • 5 Beds
  • 3.5 Baths
  • Cypress Reserve SubDv.
  • 32792 Zip Code
1248 S Pennsylvania Avenue Unit 7, Winter Park image
1248 S Pennsylvania Avenue Unit 7, Winter Park — 1248 $897,750

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...

  • 3 Beds
  • 2.5 Baths
  • Casa Jardin Condo SubDv.
  • 32789 Zip Code
167 S Edinburgh Drive, Winter Park image
167 S Edinburgh Drive, Winter Park $887,000

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 ...

  • Aloma SubDv.
  • 32792 Zip Code
2406 Tioga Trail, Winter Park image
2406 Tioga Trail, Winter Park $875,000

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...

  • 3 Beds
  • 3 Baths
  • Hills SubDv.
  • 32789 Zip Code
1250 S Pennsylvania Avenue Unit 8, Winter Park image
1250 S Pennsylvania Avenue Unit 8, Winter Park — 8 $875,000 ▼

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...

  • 3 Beds
  • 2.5 Baths
  • Casa Jardin Condo SubDv.
  • 32789 Zip Code
1915 S Lakemont Avenue Unit 1, Winter Park image
1915 S Lakemont Avenue Unit 1, Winter Park — 1 $874,000 ▲

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...

  • 3 Beds
  • 3.5 Baths
  • Maccallum Sub SubDv.
  • 32792 Zip Code
428 W Swoope Avenue, Winter Park image
428 W Swoope Avenue, Winter Park — 428 $869,000 ▼

Completely Renovated 3 story Townhome in Winter Park! The open concept living room and kitchen features Waterflow countertops, an oversized island, stainless steel applia...

  • 4 Beds
  • 3.5 Baths
  • Swoope Park SubDv.
  • 32789 Zip Code
2149 Lake Drive, Winter Park image
2149 Lake Drive, Winter Park $849,900 ▼

Beautifully remodeled home in quiet Winter Park neighborhood. Fully renovated this year leaving no stone unturned, this home features all new electrical, plumbing, HVAC, ...

  • 4 Beds
  • 3 Baths
  • Killarney Point SubDv.
  • 32789 Zip Code
903 Bungalow Avenue Unit 903, Winter Park image
903 Bungalow Avenue Unit 903, Winter Park — 903 $849,900 ▼

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 ...

  • 3 Beds
  • 2.5 Baths
  • Bungalow Park SubDv.
  • 32789 Zip Code
27 Stymie Place, Winter Park image
27 Stymie Place, Winter Park $810,000 ▲

Under Construction. Rare opportunity for affordable new construction in Winter Park! Construction has commenced! Walking distance to the historic Dubsdread Golf Course a...

  • 5 Beds
  • 3 Baths
  • Golfview SubDv.
  • 32789 Zip Code
25 Stymie Place, Winter Park image
25 Stymie Place, Winter Park $810,000 ▲

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...

  • 5 Beds
  • 3 Baths
  • Golfview SubDv.
  • 32789 Zip Code
4276 Steed Terrace, Winter Park image
4276 Steed Terrace, Winter Park $800,000 ▲

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...

  • 4 Beds
  • 3.5 Baths
  • Kings Cove SubDv.
  • 32792 Zip Code
2008 Natalen Road, Winter Park image
2008 Natalen Road, Winter Park $799,000

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...

  • 3 Beds
  • 2 Baths
  • Kenilworth Shores Sec 07 SubDv.
  • 32792 Zip Code
1602 Alabama Drive Unit 304, Winter Park image
1602 Alabama Drive Unit 304, Winter Park — 1602 $750,000 ▼

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...

  • 2 Beds
  • 2 Baths
  • Alabama Condo SubDv.
  • 32789 Zip Code
1681 Walnut Avenue, Winter Park image
1681 Walnut Avenue, Winter Park $725,000 ▲

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...

  • 3 Beds
  • 2 Baths
  • Lake Knowles Terrace SubDv.
  • 32789 Zip Code
5609 Winterbrook Way, Winter Park image
5609 Winterbrook Way, Winter Park $699,990 ▼

**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...

  • 4 Beds
  • 2.5 Baths
  • Winterbrook SubDv.
  • 32792 Zip Code
1140 Washington Avenue Unit 16, Winter Park image
1140 Washington Avenue Unit 16, Winter Park — Quarters At Winter Park $699,000 ▼

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...

  • 3 Beds
  • 2.5 Baths
  • Quarters At Winter Park Phase 2 SubDv.
  • 32789 Zip Code
1292 Howell Branch Road, Winter Park image
1292 Howell Branch Road, Winter Park $699,000 ▲

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...

  • Via Veneto SubDv.
  • 32789 Zip Code
1294 Howell Branch Road, Winter Park image
1294 Howell Branch Road, Winter Park $699,000

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...

  • Via Veneto SubDv.
  • 32789 Zip Code
2000 Whitehall Drive, Winter Park image
2000 Whitehall Drive, Winter Park $689,000

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 ...

  • 3 Beds
  • 2 Baths
  • Kenilworth Shores Sec 04 SubDv.
  • 32792 Zip Code
2344 Woodcrest Drive, Winter Park image
2344 Woodcrest Drive, Winter Park $685,000 ▲

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...

  • 4 Beds
  • 2 Baths
  • Kenilworth Estates 1st Add SubDv.
  • 32792 Zip Code
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