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Central Florida › Orlando Metro › Orange County › Winter Park › Winter Park Waterfront Homes

Winter Park Waterfront Homes for Sale

There is nothing quite like the serenity of a water view. Winter Park boasts many homes with fantastic waterfront views. Whether you are looking for a home where you can build a dock for your boat or just a tranquil pond view, Winter Park has plenty of waterfront and waterview homes for you to choose from. Below is a list of all currently available Waterview Homes in Winter Park.

Winter Park Waterfront Homes for Sale

1260 Alabama Drive, Winter Park image
1260 Alabama Drive, Winter Park $6,900,000

Rarely does a property of this caliber grace the Winter Park market. Nestled along the coveted Venetian Canal with 95 feet of pristine waterfrontage, this magnificent mas...

  • 6 Beds
  • 7 Baths
  • J Kronenberger Sub SubDv.
  • 32789 Zip Code
313 Sylvan Drive, Winter Park image
313 Sylvan Drive, Winter Park $5,500,000

Pre-Construction. To be built. This extraordinary lakefront residence on beautiful Lake Sylvan, set on a .37-acre (16,603± square foot) homesite, presents a rare opportun...

  • 4 Beds
  • 5 Baths
  • Sylvan Park SubDv.
  • 32789 Zip Code
2622 Lake Howell Lane, Winter Park image
2622 Lake Howell Lane, Winter Park $3,750,000

Welcome to an extraordinary private lakefront retreat in Winter Park, where expansive grounds, exceptional amenities, and breathtaking Lake Howell views come together in ...

  • 4 Beds
  • 3 Baths
  • Acreage & Unrec SubDv.
  • 32792 Zip Code
2240 Venetian Way, Winter Park image
2240 Venetian Way, Winter Park $3,500,000

Virtually Staged. Positioned on a quiet canal, this exceptional property features a covered boat dock with lift, offering effortless access to the renowned Winter Park Ch...

  • 4 Beds
  • 4 Baths
  • Maitland Shores 1st Add SubDv.
  • 32789 Zip Code
311 E Morse Boulevard Unit 1-5, Winter Park image
311 E Morse Boulevard Unit 1-5, Winter Park — Bldg. Number 1 $2,475,000

Quintessential Winter Park Lakefront Living with your own covered boatslip! You must see this Stunning Lakefront Penthouse Residence overlooking Lake Osceola and just two...

  • 3 Beds
  • 3 Baths
  • Phillips Circle Rep SubDv.
  • 32789 Zip Code
1415 Grove Terrace, Winter Park image
1415 Grove Terrace, Winter Park $2,200,000

Exceptional opportunity to build your dream home in one of Winter Park’s most sought-after neighborhoods! This cleared, vacant homesite is ready for construction and offe...

  • Lake Sylvan Shores SubDv.
  • 32789 Zip Code
1803 Barker Drive, Winter Park image
1803 Barker Drive, Winter Park $2,190,000

A rare opportunity awaits to own a slice of paradise on Lake Spier in beautiful Winter Park! Set on over two acres and surrounded by mature landscaping, this stunning pro...

  • 4 Beds
  • 3 Baths
  • South Lakemont Shores SubDv.
  • 32789 Zip Code
1133 Bella Lago Cove, Winter Park image
1133 Bella Lago Cove, Winter Park $2,100,000

A rare opportunity to own nearly 7 acres on the pristine shores of Private Lake Howell! This exceptional lakefront property offers the perfect setting to build your custo...

  • 32792 Zip Code
1133 Bella Lago Cove, Winter Park image
1133 Bella Lago Cove, Winter Park $2,100,000

A rare opportunity to own nearly 7 acres on the pristine shores of Private Lake Howell! This exceptional lakefront property offers the perfect setting to build your custo...

  • 3 Beds
  • 2 Baths
  • 32792 Zip Code
1420 Aloma Avenue, Winter Park image
1420 Aloma Avenue, Winter Park $1,949,500 ▼

Experience a rare expression of design-forward lakefront living on Lake Sylvan in the heart of Old Winter Park. Fully remodeled through a comprehensive, down-to-the-studs...

  • 3 Beds
  • 4 Baths
  • Sylvan Lake Shores SubDv.
  • 32789 Zip Code
313L Sylvan Drive, Winter Park image
313L Sylvan Drive, Winter Park $1,750,000

Exceptional opportunity to build on beautiful Lake Sylvan with this 0.37-acre (approximately 16,603-square-foot) lakefront homesite. Offering a picturesque waterfront set...

  • Sylvan Park SubDv.
  • 32789 Zip Code
2914 Reef Knot Place, Winter Park image
2914 Reef Knot Place, Winter Park $1,725,000

Welcome to an exceptional lakefront home in the gated community of Lake Florence Preserve, where luxury, space, and lifestyle come together in the heart of Winter Park. T...

  • 6 Beds
  • 6 Baths
  • Lake Florence Preserve SubDv.
  • 32792 Zip Code
1113 Via Del Mar, Winter Park image
1113 Via Del Mar, Winter Park $1,595,000

Exceptional opportunity in the heart of Winter Park - a truly premier and irreplaceable homesite offering rare scale, privacy, and extraordinary future build potential. T...

  • Tuscany Terrace SubDv.
  • 32789 Zip Code
1113 Via Del Mar, Winter Park image
1113 Via Del Mar, Winter Park $1,595,000

Exceptional opportunity in the heart of Winter Park — a truly premier and irreplaceable homesite offering rare scale, privacy, and extraordinary future build potential. ...

  • 3 Beds
  • 2 Baths
  • Tuscany Terrace SubDv.
  • 32789 Zip Code
1841 Lake Spier Drive, Winter Park image
1841 Lake Spier Drive, Winter Park $1,498,000 ▼

Water skiers welcome. A rare opportunity to own a thoughtfully renovated lakefront residence in Winter Park. This home is perfectly situated between Winter Park, Baldwin ...

  • 3 Beds
  • 4 Baths
  • South Lakemont Shores SubDv.
  • 32789 Zip Code
1881 Lake Spier Drive, Winter Park image
1881 Lake Spier Drive, Winter Park $1,350,000

Lakefront home on over 1 acre in Winter Park with approximately 95 feet of frontage on Lake Spier. Positioned on a private, spring-fed lake, this property presents a rar...

  • South Lakemont Shores SubDv.
  • 32789 Zip Code
1881 Lake Spier Drive, Winter Park image
1881 Lake Spier Drive, Winter Park $1,350,000

Lakefront home on over 1 acre in Winter Park with direct frontage on Lake Spier. Positioned on a private, spring-fed lake, this property presents a rare opportunity to b...

  • 3 Beds
  • 2 Baths
  • South Lakemont Shores SubDv.
  • 32789 Zip Code
240 Killarney Drive, Winter Park image
240 Killarney Drive, Winter Park $1,275,000

Own a piece of Lake Killarney, a rare opportunity to build your dream water-view estate in the heart of Winter Park. This exceptional homesite offers direct access to pri...

  • 3 Beds
  • 3 Baths
  • Killarney Estates SubDv.
  • 32789 Zip Code
230 Killarney Drive, Winter Park image
230 Killarney Drive, Winter Park $1,250,000

Own a piece of Lake Killarney, a rare opportunity to build your dream water-view estate in the heart of Winter Park. This exceptional homesite offers direct access to pri...

  • 4 Beds
  • 1 Baths
  • Killarney Estates SubDv.
  • 32789 Zip Code
2227 Howard Drive, Winter Park image
2227 Howard Drive, Winter Park $1,100,000

A rare corner lot in one of Winter Park's most established, increasingly in-demand Lake Forest Park neighborhood. This mid-century home has been meticulously maintained. ...

  • 3 Beds
  • 3 Baths
  • Lake Forest Park SubDv.
  • 32789 Zip Code
1927 S Lakemont Avenue, Winter Park image
1927 S Lakemont Avenue, Winter Park — Lake Spier $925,000

Welcome to Lake Spier Crossing with NO CDD and low HOA fees, an exclusive boutique lakefront community built by Winter Park's premier builder, Meridian Homes. Nestled bet...

  • 3 Beds
  • 4 Baths
  • Lake Spier Xing SubDv.
  • 32792 Zip Code
560 Ololu Drive, Winter Park image
560 Ololu Drive, Winter Park $899,000 ▼

Nestled on the shores of private, skiable Lake Killarney, this beautifully updated and absolutely adorable 2-bedroom, 2-bath home offers a rare opportunity to enjoy true ...

  • 2 Beds
  • 2 Baths
  • Killarney Circle SubDv.
  • 32789 Zip Code
1131 Wildmeadow Run, Winter Park image
1131 Wildmeadow Run, Winter Park $825,000

Winter Park - Located in the gated community of Hawks Crest, this 4-bedroom, 3.5-bath home offers 2,589 square feet of well-designed living space on a premium pond-view l...

  • 4 Beds
  • 4 Baths
  • Meadows At Hawks Crest SubDv.
  • 32792 Zip Code
1316 Blue Stem Lane, Winter Park image
1316 Blue Stem Lane, Winter Park $725,000

Welcome to this stunning Taylor Morrison Boca model in the highly desirable Hawks Crest gated community. This beautifully maintained 4-bedroom, 2.5-bath home offers an ex...

  • 4 Beds
  • 3 Baths
  • Landings At Hawks Crest SubDv.
  • 32792 Zip Code
1003 Lake Bell Drive, Winter Park image
1003 Lake Bell Drive, Winter Park $549,900 ▼

Rare Waterfront Opportunity in Winter Park! Discover your own slice of Florida paradise with this waterfront gem offering 94 feet of direct canal frontage on Lake Bell fo...

  • 3 Beds
  • 2 Baths
  • Albert Lee Ridge Add 02 SubDv.
  • 32789 Zip Code
720 Killarney Bay Court Unit 7-6, Winter Park image
720 Killarney Bay Court Unit 7-6, Winter Park — 7 $389,000

LAKE KILLARNEY CONDO IN WINTER PARK! Enjoy the best of Winter Park living in this beautiful 2-bedroom, 2-bath corner condo in the private lakefront community of Killarney...

  • 2 Beds
  • 2 Baths
  • Killarney Bay Condo SubDv.
  • 32789 Zip Code
151 N Orlando Avenue Unit 118, Winter Park image
151 N Orlando Avenue Unit 118, Winter Park — 118 $299,999 ▲

Investment opportunity! Discover this hidden gem—a 2-bed, 1-bath condo nestled in the heart of Winter Park. Situated in the serene Lake Killarney Condos, this property of...

  • 2 Beds
  • 1 Baths
  • Lake Killarney Condo SubDv.
  • 32789 Zip Code
151 N Orlando Avenue Unit #115, Winter Park image
151 N Orlando Avenue Unit #115, Winter Park — # 151 $285,000 ▼

Welcome to Lake Killarney Living ... Where Winter Park charm meets everyday convenience. Furniture negotiable, offering added flexibility for buyers or investors. Disc...

  • 2 Beds
  • 1 Baths
  • Lake Killarney Condo SubDv.
  • 32789 Zip Code
151 N Orlando Avenue Unit 242, Winter Park image
151 N Orlando Avenue Unit 242, Winter Park — Lake Killarney Condominiums $269,000

Virtually Staged. Experience lakefront living at its finest in this exceptional Winter Park Condominium Community overlooking beautiful Lake Killarney. Hidden gem comple...

  • 2 Beds
  • 1 Baths
  • Lake Killarney Condo SubDv.
  • 32789 Zip Code
2500 Lee Rd. Unit 222, Winter Park image
2500 Lee Rd. Unit 222, Winter Park — 1 $184,400 ▼

Rent-to-own or lease option available with negotiable terms—Lakefront Lifestyle in Winter Park—Under $200K! Live the resort life for less! This stunning, move-in ready re...

  • 1 Beds
  • 1 Baths
  • Lakeside Manor Apts Condo SubDv.
  • 32789 Zip Code
2500 Lee Road Unit 143, Winter Park image
2500 Lee Road Unit 143, Winter Park — Lakeside Manor $130,000

It doesn't get much better than this: Living in a Lakefront and Winter Park community, that is convenient to I-4 providing easy access to points north and south, downtown...

  • 1 Beds
  • 1 Baths
  • Lakeside Manor Apts Condo SubDv.
  • 32789 Zip Code
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