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Winter Park Real Estate Search

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Winter Park Listings

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 a gated estate situated on Winter Park Chain of Lakes in the the most exclusive location in ...

  • 7 Beds
  • 5.5 Baths
  • Twelve Oaks SubDv.
  • 32789 Zip Code
1190 N Park Avenue, Winter Park image
1190 N Park Avenue, Winter Park $8,500,000 ▼

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 nearly 2 acre...

  • 8 Beds
  • 5.5 Baths
  • 0000 SubDv.
  • 32789 Zip Code
1311 Via Tuscany, Winter Park image
1311 Via Tuscany, Winter Park $7,900,000 ▲

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
785 Via Lombardy, Winter Park image
785 Via Lombardy, Winter Park $5,650,000

Under Construction. Today’s Florida living at its finest in this premier 2023 new construction residence nearing completion in the heart of the Vias by Z Properties Inc. ...

  • 5 Beds
  • 5.5 Baths
  • Sicilian Shores Rep 02 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
690 N New York Avenue, Winter Park image
690 N New York Avenue, Winter Park $4,600,000

April 2022 construction! This newly constructed home is move-in ready and available for a quick closing! Do not miss the once-in-a-lifetime opportunity to own this rare...

  • 4 Beds
  • 4.5 Baths
  • Greens/Pk SubDv.
  • 32789 Zip Code
1290 Park Ave, Winter Park image
1290 Park Ave, Winter Park $4,575,000 ▼

Nestled along the shores, on approximately an acre property on Lake Maitland walking distance to downtown Park Ave, with one of the most sought-after addresses in Winter ...

  • 4 Beds
  • 3.5 Baths
  • N/A SubDv.
  • 32789 Zip Code
1106 Palmer Avenue, Winter Park image
1106 Palmer Avenue, Winter Park $4,325,000

Sitting on over a ½ acre lot on a private lane in the heart of Winter Park, this traditional and elegant estate offers ultimate privacy and is located just minutes from i...

  • 4 Beds
  • 5.5 Baths
  • Winter Park Town Of SubDv.
  • 32789 Zip Code
664 W Morse Boulevard, Winter Park image
664 W Morse Boulevard, Winter Park $4,299,000

One or more photo(s) has been virtually staged. Under Construction. “UNDER CONSTRUCTION” Completion end of May. This custom built Winter Park home is the epitome of luxu...

  • 4 Beds
  • 4.5 Baths
  • Morse And Pennsylvania SubDv.
  • 32789 Zip Code
4400 Tuscany Island Court, Winter Park image
4400 Tuscany Island Court, Winter Park $3,999,777

Welcome to Tuscany Island in Winter Park! Private gated enclave of 5 magnificent luxury estate homes, resting on the lake shore of Bear Gulley. This highly sought-after a...

  • 4 Beds
  • 5.5 Baths
  • Tuscany Island SubDv.
  • 32792 Zip Code
2138 Lake Drive, Winter Park image
2138 Lake Drive, Winter Park $3,295,000

Lakefront luxury on the beautiful shores of Lake Killarney! Custom built with attention paid to every detail, this Mediterranean oasis delivers 4 spacious bedrooms, 3 ful...

  • 4 Beds
  • 3.5 Baths
  • Killarney Point SubDv.
  • 32789 Zip Code
1824 Harland Park Drive, Winter Park image
1824 Harland Park Drive, Winter Park $3,250,000 ▼

*VIDEO TOUR & 3D TOUR AVAILABLE* It’s time to live your best life! Casa Allegra is a full-custom Spanish-villa style home designed by the awarded company Morales-Keesee D...

  • 6 Beds
  • 3.5 Baths
  • Windsong-Knowles Place SubDv.
  • 32789 Zip Code
2413 Winter Park Road, Winter Park image
2413 Winter Park Road, Winter Park $3,250,000 ▲

Pre-Construction. To be built. Under Construction, Winter Park opportunity with F.G. Schaub Custom Homes. This Timeless Modern elevation offers a grand entrance with An...

  • 5 Beds
  • 5.5 Baths
  • Parklando 03 SubDv.
  • 32789 Zip Code
1420 Holts Grove Circle, Winter Park image
1420 Holts Grove Circle, Winter Park $2,999,990 ▼

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
1064 Howell Branch Road, Winter Park image
1064 Howell Branch Road, Winter Park $2,900,000 ▼

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
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
2522 Lafayette Avenue, Winter Park image
2522 Lafayette Avenue, Winter Park $2,895,000 ▲

New Construction. Contemporary luxury masterpiece home ready to closing at the end of this year. Exclusive Architectural Design, strong structure with two-story concrete-...

  • 4 Beds
  • 3.5 Baths
  • Winter Park Village SubDv.
  • 32789 Zip Code
170 S Phelps Avenue, Winter Park image
170 S Phelps Avenue, Winter Park $2,800,000

Under Construction. Soon to be completed. A stunning modern transitional home located in the heart of Winter park minutes from Park Ave. As you enter this home through th...

  • 4 Beds
  • 4.5 Baths
  • Green Terrace SubDv.
  • 32789 Zip Code
2172 Temple Drive, Winter Park image
2172 Temple Drive, Winter Park $2,650,000

Pre-Construction. To be built. Pre-Construction, To Be Built. Elegance, comfort, and a welcoming environment blend cohesively at this modern West Indies new construction ...

  • 5 Beds
  • 4 Baths
  • Fontainebleau SubDv.
  • 32789 Zip Code
465 N Phelps Avenue, Winter Park image
465 N Phelps Avenue, Winter Park $2,600,000

Pre-Construction. To be built. Don't miss this Beautiful Pre-Construction Home In Winter Park, Minutes to Park Avenue! 6 Bedroom, 6 Bath home with Master on the First Flo...

  • 6 Beds
  • 6 Baths
  • Ethel Park SubDv.
  • 32789 Zip Code
Grove Avenue, Winter Park image
Grove Avenue, Winter Park $2,569,100 ▲

A rare opportunity to develop a quaint community in Winter Park! Conceptual work has been completed making this an ideal site for the construction of 9 custom single fami...

  • Mossy Oaks SubDv.
  • 32792 Zip Code
660 W Morse Boulevard, Winter Park image
660 W Morse Boulevard, Winter Park — Morse $2,500,000

This Home is a classically set up modern brownstone with private elevator. Situated within close distance to Hannibal Square and Park Avenue, the premiere shopping and ...

  • 3 Beds
  • 3.5 Baths
  • Morse & Pennsylvania Twnhms SubDv.
  • 32789 Zip Code
1851 Windsor Drive, Winter Park image
1851 Windsor Drive, Winter Park $2,490,000

Under Construction. Another stunning Perch built by Urban Perch-A Boutique Homebuilder. This elegant transitional home boasts a timeless yet modern feel. Large windows fl...

  • 5 Beds
  • 6.5 Baths
  • V H Musselwhites Sub 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
1318 Morton Road, Winter Park image
1318 Morton Road, Winter Park $2,360,000 ▲

Under Construction. Under Construction. Contemporary luxury masterpiece home ready to closing at the end of this year. Exclusive Architectural Design, strong structure wi...

  • 4 Beds
  • 3.5 Baths
  • Winter Park Village SubDv.
  • 32789 Zip Code
1017 Via Tuscany Oaks Way, Winter Park image
1017 Via Tuscany Oaks Way, Winter Park $2,250,000

Modern Mediterranean on a quiet cul-de-sac street off of Via Tuscany with an oversized beautiful treed lot. Spacious flexible floor plan with private owner’s suite and ho...

  • 5 Beds
  • 5.5 Baths
  • Via Tuscany Oaks SubDv.
  • 32789 Zip Code
2723 Norris Avenue, Winter Park image
2723 Norris Avenue, Winter Park $2,199,999

Pre-Construction. To be built. Pre-Construction. To be built. This Cape Cod inspired home provides a rare pre-construction opportunity in highly coveted Winter Park. Make...

  • 4 Beds
  • 3.5 Baths
  • Parklando 02 SubDv.
  • 32789 Zip Code
2015 N Park Avenue, Winter Park image
2015 N Park Avenue, Winter Park — Park Ave $2,100,000 ▼

Under Construction. New Construction Home! This modern pool home is truly one of a kind designed to wow your family and friends. Live on one of the most popular shopping ...

  • 4 Beds
  • 4.5 Baths
  • N Park Ave SubDv.
  • 32789 Zip Code
2011 N Park Avenue, Winter Park image
2011 N Park Avenue, Winter Park — Anchor Homes & Developement $2,075,000

Under Construction. New Construction Home is almost complete! This modern pool home is truly one of a kind designed to wow your family and friends. This executive pool ho...

  • 4 Beds
  • 3.5 Baths
  • Twin Acres In City Of Winter Park SubDv.
  • 32789 Zip Code
180 Whipple Avenue, Winter Park image
180 Whipple Avenue, Winter Park $1,960,000

Listing price is at appraised value as of 10/24/22 Appraisal. A++ Location (75% FAR) Buyer can bring their own builder. Only 3 Lots left! If you want true walkability...

  • 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

Under Construction. Location, functionality, beautiful construction and a host of amenities make this the perfect place to call home. Historic oak trees dripping with Spa...

  • 4 Beds
  • 4.5 Baths
  • Tangerine Court SubDv.
  • 32789 Zip Code
1531 Place Picardy, Winter Park image
1531 Place Picardy, Winter Park $1,895,000

An elegant custom home, designed & built by FG Shaub, is tucked away on a large corner lot on a pristine oak-lined street, offering incredible privacy. This home offers t...

  • 4 Beds
  • 4 Baths
  • Fontainebleau SubDv.
  • 32789 Zip Code
266 Detmar Drive, Winter Park image
266 Detmar Drive, Winter Park $1,850,000 ▼

This Beautiful Custom Mediterranean Home WALKABLE TO PARK AVENUE offers the finest of quality throughout, with custom ceilings, detailed woodwork, and hand painted accent...

  • 4 Beds
  • 4.5 Baths
  • Detmar Terrace 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
1813 Gipson Green Lane, Winter Park image
1813 Gipson Green Lane, Winter Park $1,799,932

DREAM LOT IN A RARE LOCATION! This huge 99x231x100x218 (22,527 SqFt/.517 acre) is arguably a “lifetime opportunity” for your next Estate Home on a picturesque, sought-aft...

  • Boiley Green Sub SubDv.
  • 32789 Zip Code
2325 Chantilly Avenue, Winter Park image
2325 Chantilly Avenue, Winter Park $1,775,000

Stunning pool home located on a quiet street in the heart of Winter Park includes a private backyard oasis and a detached apartment/guest house. As you step through the f...

  • 5 Beds
  • 4.5 Baths
  • Chantilly Sub SubDv.
  • 32789 Zip Code
1166 Oaks Boulevard, Winter Park image
1166 Oaks Boulevard, Winter Park $1,750,000 ▼

Custom luxurious Winter Park Estate located in the highly desirable subdivision of Dixie Terrace (walkable to Whole Foods, Winter Park Village, and Park Ave). 2018 Build,...

  • 4 Beds
  • 3.5 Baths
  • Dixie Terrace SubDv.
  • 32789 Zip Code
450 Ololu Drive, Winter Park image
450 Ololu Drive, Winter Park $1,699,000

Enjoy fabulous direct views of Lake Killarney from all living areas, kitchen & master suite. Unbelievable upscale finishes include marble flooring, imported Indonesian te...

  • 5 Beds
  • 5.5 Baths
  • Killarney Circle SubDv.
  • 32789 Zip Code
2234 Via Luna, Winter Park image
2234 Via Luna, Winter Park $1,650,000

Elegant four bedroom, three and a half-bath home in the famous Via’s of Winter Park, privately positioned on a 3 sided open corner lot. It is meticulously maintained wit...

  • 4 Beds
  • 3.5 Baths
  • Tuscany Terrace SubDv.
  • 32789 Zip Code
270 E Lake Sue Avenue, Winter Park image
270 E Lake Sue Avenue, Winter Park $1,649,900

Pre-Construction. To be built. Customize-to-suite this gorgeous warm-transitional home in the heart of Olde Winter Park! Presented by by Parade of Homes Winner, Wooten Bu...

  • 5 Beds
  • 4.5 Baths
  • Charmont SubDv.
  • 32789 Zip Code
4464 Tuscany Island Court, Winter Park image
4464 Tuscany Island Court, Winter Park $1,625,000

Enjoy the Winter Park lifestyle in this fabulous 4 bedroom, 4.5 bath home, built in 2006 with a clean and well-planned 4625 sqft floorplan. This beautiful Mediterranean s...

  • 4 Beds
  • 4.5 Baths
  • Tuscany Island SubDv.
  • 32792 Zip Code
234 Detmar Drive, Winter Park image
234 Detmar Drive, Winter Park $1,625,000 ▼

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
1130 Palmer Avenue, Winter Park image
1130 Palmer Avenue, Winter Park $1,600,000

Looking for a large lot in Winter Park with deeded lake access to the chain of lakes? Consider this your opportunity to buy an almost 15,000 sf corner lot on one of the ...

  • 3 Beds
  • 3 Baths
  • Palmer Ave Lakeside Prop SubDv.
  • 32789 Zip Code
690 Osceola Avenue Unit 504, Winter Park image
690 Osceola Avenue Unit 504, Winter Park — 505 $1,595,000

BACK ON THE MARKET!!! 3 BEDROOMS & 3 BATH split floor plan located in the highly sought-after Lake Virginia Condos nestled in the heart of Winter Park. As soon as you ent...

  • 3 Beds
  • 3 Baths
  • Lake Virginia Condo SubDv.
  • 32789 Zip Code
1209 Sharon Place, Winter Park image
1209 Sharon Place, Winter Park $1,579,000 ▼

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 $1,579,000 ▼

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
2813 Northwood Boulevard, Winter Park image
2813 Northwood Boulevard, Winter Park $1,550,000 ▼

Welcome home to this two-story contemporary pool home full of upgrades featuring four bedrooms plus a large sun-filled office, three-and-a-half baths and a two-car garage...

  • 4 Beds
  • 3.5 Baths
  • Northwood Terrace SubDv.
  • 32789 Zip Code
3520 Wilde Avenue, Winter Park image
3520 Wilde Avenue, Winter Park $1,500,000

Pre-Construction. To be built. Custom transitional estate pool home on over 1 acre lot in coveted Winter Park. Nestled on a quiet cul-de-sac, yet situated within minutes ...

  • 6 Beds
  • 5.5 Baths
  • No Subdivision SubDv.
  • 32792 Zip Code
580 Ololu Drive, Winter Park image
580 Ololu Drive, Winter Park $1,495,000

Luxury Lifestyle on Beautiful Lake Killarney. Enjoy the serenity of lakeside living on the largest and cleanest private lake in Winter Park. Lake Killarney is the hidden ...

  • 3 Beds
  • 2.5 Baths
  • Killarney Circle SubDv.
  • 32789 Zip Code
1016 Tuscany Place, Winter Park image
1016 Tuscany Place, Winter Park $1,479,000

Welcome to your mid-century modern home of endless possibilities. Situated on an oversized (.40 acre) lot in the family-friendly Tuscany Place neighborhood of “the Winter...

  • 5 Beds
  • 3.5 Baths
  • Tuscany Place SubDv.
  • 32789 Zip Code
1913 Sycamore Drive, Winter Park image
1913 Sycamore Drive, Winter Park $1,475,000

Under Construction. Under construction. New construction home in desirable Audubon Park school district. Welcome home to this timeless Traditional elevation. As you step ...

  • 4 Beds
  • 4.5 Baths
  • Northwood Terrace SubDv.
  • 32789 Zip Code
1511 Palm Avenue, Winter Park image
1511 Palm Avenue, Winter Park $1,399,000

Pre-Construction. To be built. Pre-Construction. to Be Built. You'll love this stunning brand new, 2-story Modern Mediterranean pool home located in the highly desirable ...

  • 4 Beds
  • 3.5 Baths
  • Lake Knowles Terrace Add 02 SubDv.
  • 32789 Zip Code
601 Ellen Drive, Winter Park image
601 Ellen Drive, Winter Park $1,399,000 ▲

Under Construction. 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 custom homes ...

  • 4 Beds
  • 4.5 Baths
  • Lake Killarney Shores SubDv.
  • 32789 Zip Code
776 Mcintyre Avenue, Winter Park image
776 Mcintyre Avenue, Winter Park — N/A $1,380,000 ▼

This recently remoldeded, move-in-ready 3-br, 3.5-b downtown Winter Park stunner is a short walk to Rollins College, schools, museums, galleries, Park Ave shopping, art f...

  • 3 Beds
  • 3.5 Baths
  • Trotters Rep 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. Rendering is for inspiration only. Bring your own builder or use our preferred builder, Valdara Custom Homes to select your desired floor p...

  • 4 Beds
  • 3.5 Baths
  • Winter Park SubDv.
  • 32789 Zip Code
2131 Loch Lomond Drive, Winter Park image
2131 Loch Lomond Drive, Winter Park $1,295,000 ▲

Under Construction. This impressive modern coastal farmhouse is being built by Parade of Homes award winning builder, Meridian Homes. Located on an impressive 1/4 acre lo...

  • 4 Beds
  • 4.5 Baths
  • Aloma SubDv.
  • 32792 Zip Code
Winter Park image
Winter Park $1,285,000

Build your dream home on this oversized 100 x 150 lot steps from Park Avenue. Excellent schools - Dommerich Elementary, Maitland Middle & Winter Park High

  • Camwood Sub SubDv.
  • 32789 Zip Code
3708 Vinsetta Court, Winter Park image
3708 Vinsetta Court, Winter Park $1,275,000

One or more photo(s) has been virtually staged. Welcome Home! Your search is over with this stunning 2015 built Energy-Efficient move-in ready premium corner lot 6-bedroo...

  • 6 Beds
  • 5 Baths
  • Lakeside Estates SubDv.
  • 32792 Zip Code
1741 Palmer Avenue, Winter Park image
1741 Palmer Avenue, Winter Park $1,250,000

Located in highly desired Winter Park on an oversized lot, this unique, single-story Tuscan style 3 bedroom, 3 bath home with round circular paver driveway has everything...

  • 3 Beds
  • 3 Baths
  • Jenkins Add 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
3540 Wilde Avenue, Winter Park image
3540 Wilde Avenue, Winter Park $1,200,000

Pre-Construction. To be built. Custom transitional estate pool home on over ¾-acre lot in coveted Winter Park. Nestled on a quiet cul-de-sac, yet situated within minutes ...

  • 5 Beds
  • 5.5 Baths
  • No Subdivision 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
1400 Lyndale Boulevard, Winter Park image
1400 Lyndale Boulevard, Winter Park $1,175,000

Charleston style home on picturesque tree lined corner lot secluded off of Park Avenue in quiet setting near downtown Winter Park… One owner home since originally custom ...

  • 4 Beds
  • 2.5 Baths
  • Dixie Terrace SubDv.
  • 32789 Zip Code
335 Beloit Avenue, Winter Park image
335 Beloit Avenue, Winter Park $1,150,000

Come see this beautiful home on a highly desirable street! Enter the home through the well sized foyer and right into your living room/dining room area, separated by a do...

  • 3 Beds
  • 2 Baths
  • Morseland Sub SubDv.
  • 32789 Zip Code
3720 Vinsetta Court, Winter Park image
3720 Vinsetta Court, Winter Park $1,100,000

Located within the Winter Park gated community of Lakeside Estates, this beautiful, luxury home, located on a quiet cul-de-sac, is ready to welcome a new family. This wel...

  • 6 Beds
  • 5 Baths
  • Lakeside Estates SubDv.
  • 32792 Zip Code
1117 Kenwood Avenue, Winter Park image
1117 Kenwood Avenue, Winter Park $1,100,000

Don't miss this rare opportunity to build your dream home on a fabulous lot that spans from Kenwood (front-facing) to Denning (rear-facing). This oversized, 0.39 AC lot i...

  • Dixie Terrace SubDv.
  • 32789 Zip Code
100 S Virginia Avenue Unit 316, Winter Park image
100 S Virginia Avenue Unit 316, Winter Park — Douglas Grand $995,000 ▼

ATTENTION ROLLINS PARENTS ! Welcome to The Douglas Grand, the crown jewel of Winter Park. You will find The Douglas Grand perfectly located just one block from Park Aven...

  • 3 Beds
  • 3 Baths
  • Winter Park Residentialcondominium9451/3 SubDv.
  • 32789 Zip Code
2232 Banchory Road, Winter Park image
2232 Banchory Road, Winter Park $976,000

Get Busy Living the Winter Park lifestyle! Come and experience this exquisite Winter Park home situated on an oversized corner lot. This open floor plan, modern masterpie...

  • 4 Beds
  • 3 Baths
  • Brookshire Heights 4th Add SubDv.
  • 32792 Zip Code
2119 Blossom Lane, Winter Park image
2119 Blossom Lane, Winter Park $899,999 ▼

$40,000 PRICE CORRECTION! This home is a boater’s dream! Sitting on just under a half acre lot, this sensational NEWLY RENOVATED (2022) home comes with your very own PRIV...

  • 4 Beds
  • 2 Baths
  • N/A SubDv.
  • 32789 Zip Code
1420 Aloma Avenue, Winter Park image
1420 Aloma Avenue, Winter Park $899,900 ▼

Bring your builder and create the lakefront home of your dreams in the heart of old Winter Park. With 88' of direct lake frontage, this Aloma Avenue location will elimina...

  • Sylvan Lake Shores SubDv.
  • 32789 Zip Code
1420 Aloma Avenue, Winter Park image
1420 Aloma Avenue, Winter Park $899,900 ▼

Amazing lakefront opportunity in Olde Winter Park! This stunning 1936-built home awaits your improvements, or choose to build your new dream home on the large lot with fr...

  • 2 Beds
  • 2.5 Baths
  • Sylvan Lake Shores SubDv.
  • 32789 Zip Code
5332 Cypress Reserve Place, Winter Park image
5332 Cypress Reserve Place, Winter Park $899,000 ▼

MAKE YOUR GRAND ENTRANCE to YOUR New Home in WINTER PARK'S finest GATED Community of CYPRESS RESERVE - BEAR GULLY LAKE area! YOU will be Greeted by these SPLENDID and IRR...

  • 5 Beds
  • 3.5 Baths
  • Cypress Reserve SubDv.
  • 32792 Zip Code
367 Fitzhugh Road, Winter Park image
367 Fitzhugh Road, Winter Park $895,000 ▼

Move in ready on February 10th 2023. New construction in Winter Park...Custom Built Craftsman Ranch by Main Street Builders. 4 Bedrooms+Office/3 Bath, Open Concept Kit...

  • 4 Beds
  • 3 Baths
  • Winter Park Pines Merrie Oaks SubDv.
  • 32792 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
358 W Comstock Avenue, Winter Park image
358 W Comstock Avenue, Winter Park $850,000

Residential Land Opportunity in Downtown Winter Park. Zoned R1-A this premium lot is ready for something new and exciting to be built on it. Featuring 107' road frontage ...

  • Winter Park 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
1841 Winter Park Road, Winter Park image
1841 Winter Park Road, Winter Park $799,900 ▼

Price Improvement! Location, location, location is an understatement for this 3-bedroom 2-bath Winter Park pool home! This charming home comes with a massive family spac...

  • 3 Beds
  • 2 Baths
  • Charmont SubDv.
  • 32789 Zip Code
436 W Swoope Avenue, Winter Park image
436 W Swoope Avenue, Winter Park — Swoope Townhomes $799,000

Welcome to this posh contemporary townhome just steps from famed Park Avenue in Downtown Winter Park. The sale includes a deeded parking spot in the community parking lot...

  • 4 Beds
  • 3.5 Baths
  • Swoope Park SubDv.
  • 32789 Zip Code
25 Stymie Place, Winter Park image
25 Stymie Place, Winter Park $789,990 ▼

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
1224 S Pennsylvania Avenue Unit 4, Winter Park image
1224 S Pennsylvania Avenue Unit 4, Winter Park — Casa Jardin $789,900 ▼

The long hunt is over! Step inside and immerse yourself in the modern Mediterranean space found in this 3 bed, 2 bath townhome in the heart of Winter Park. Mere minutes f...

  • 3 Beds
  • 2.5 Baths
  • Casa Jardin Condo SubDv.
  • 32789 Zip Code
27 Stymie Place, Winter Park image
27 Stymie Place, Winter Park $784,990 ▼

Under Construction. Rare opportunity for affordable new construction in Winter Park! Construction has commenced! Park Avenue, Historic Dubsdread Golf Course, and the fut...

  • 5 Beds
  • 3 Baths
  • Golfview SubDv.
  • 32789 Zip Code
1546 Minnesota Avenue, Winter Park image
1546 Minnesota Avenue, Winter Park $775,000

Look no further than this stunning modern two story home!! This NORTH FACING HOUSE is conveniently located just minutes from Downtown Winter Park, with the best dinning...

  • 4 Beds
  • 3 Baths
  • Lawndale SubDv.
  • 32789 Zip Code
1760 Oakhurst Avenue, Winter Park image
1760 Oakhurst Avenue, Winter Park $750,000 ▲

Stroll through the giant oak trees on the shady streets of Old Winter Park. This is the perfect lot to build your dream home. This desirable Winter Park location is minut...

  • 3 Beds
  • 3 Baths
  • Jenkins Second Add SubDv.
  • 32789 Zip Code
1131 Oxford Road, Winter Park image
1131 Oxford Road, Winter Park $749,999 ▲

Location Location**Virginia Heights within Winter Park luxury living! Easy walk to Park Ave. and Rollins College. Lake Virginia is one block away with storage for your k...

  • 3 Beds
  • 2 Baths
  • Virginia Heights Rep SubDv.
  • 32789 Zip Code
7909 Pleasant Pine Circle, Winter Park image
7909 Pleasant Pine Circle, Winter Park $748,000 ▼

WELCOME TO YOUR FOREVER HOME - LOCATION! LOCATION!! THIS IS A MUST SEE HOME!!! THIS METICULOUSLY GORGEOUS HOME is situated in the HEART OF WINTER PARK in the ESTABLISHED ...

  • 5 Beds
  • 4 Baths
  • Enclave At Aloma SubDv.
  • 32792 Zip Code
564 S Ranger Boulevard, Winter Park image
564 S Ranger Boulevard, Winter Park $725,000

MUST SEE stunning, COMPLETELY RENOVATED Winter Park home! Nestled on a tree-lined street in coveted Winter Park Pines neighborhood – where the mail is still hand delivere...

  • 4 Beds
  • 3 Baths
  • Winter Park Pines SubDv.
  • 32792 Zip Code
1300 Blue Stem Lane, Winter Park image
1300 Blue Stem Lane, Winter Park $699,000 ▼

KITCHEN AND BATHROOM CABINETS JUST GOT UPDATED!! Your search is over! Welcome to the exclusive gated community, Meadows at Hawk's Crest, located in sought-after Winter Pa...

  • 4 Beds
  • 3.5 Baths
  • Hawks Crest SubDv.
  • 32792 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
1702 Glenridge Way, Winter Park image
1702 Glenridge Way, Winter Park — 1702 $689,000 ▼

Come see this hidden Winter Park gem! Immaculately maintained corner lakefront townhome with two bedrooms, two baths, two-car carport and community pool! Lakeridge Townho...

  • 2 Beds
  • 2 Baths
  • Orlando Park Rep SubDv.
  • 32789 Zip Code
200 Carolina Avenue Unit 402, Winter Park image
200 Carolina Avenue Unit 402, Winter Park — Park West $679,000

Spacious and Bright 4th floor PARK WEST condo available for sale. Enjoy living in the heart of downtown Winter Park close to all the Park Avenue shops, restaurants, museu...

  • 3 Beds
  • 2 Baths
  • Park West Condo SubDv.
  • 32789 Zip Code
2620 Summerfield Road, Winter Park image
2620 Summerfield Road, Winter Park $675,000 ▼

Welcome home to this Beautiful Golfside Community. This custom, unique and one-of-a-kind WINTER PARK home backyard is adjacent to the Winter Park Pines Golf Club and tree...

  • 4 Beds
  • 2.5 Baths
  • Golfside Golf Course Sec 01 SubDv.
  • 32792 Zip Code
624 Langholm Drive, Winter Park image
624 Langholm Drive, Winter Park $669,900

This unique mid-century modern home is ready for a new owner to make it their own. Featuring hardwood floors, and spacious living room and family room, split by a firepl...

  • 3 Beds
  • 2 Baths
  • Kenilworth Shores Sec 06 SubDv.
  • 32789 Zip Code
782 S Pennsylvania Avenue Unit 1, Winter Park image
782 S Pennsylvania Avenue Unit 1, Winter Park — Unit 1 $650,000 ▼

Location, Location, Location. Spacious and well maintained 3 bed, 2.5 bath townhouse in the heart of Winter Park. Short distance from to Rollins College, Park Avenue, a...

  • 3 Beds
  • 2.5 Baths
  • Pennsylvania Station 01 Condo SubDv.
  • 32789 Zip Code
648 W Webster Avenue Unit A, Winter Park image
648 W Webster Avenue Unit A, Winter Park $649,900

DUPLEX!!! Completely Renovated Beautiful 3/2 & 3/1 Duplex Homes in the Quiet Carver Town Area of Winter Park. Renovations were professionally done and offer potential inv...

  • 6 Beds
  • Carver Town SubDv.
  • 32789 Zip Code
1122 Azalea Lane, Winter Park image
1122 Azalea Lane, Winter Park — Na $638,900

Winter Park luxury living with a lovely stroll to Park Ave, Rollins and across from the Winter Park Tennis Center. Great for living, entertaining or renting with too many...

  • 3 Beds
  • 3.5 Baths
  • Cherokee Park SubDv.
  • 32789 Zip Code
Winter Park image
Winter Park $638,000 ▼

This beautiful new two-story home in Winter Park’s exclusive gated community of Hawk’s Crest. Community has lake access with canon launch. This home was build by Taylor M...

  • 4 Beds
  • 2.5 Baths
  • Meadows At Hawks Crest SubDv.
  • 32792 Zip Code
5609 Winterbrook Way, Winter Park image
5609 Winterbrook Way, Winter Park $630,000 ▼

PRICE REDUCTION!! BUILT IN 2020, this single story home lies in the intimate gated Winter Park community of Winterbrook. Its Florida style seamlessly flows from front foy...

  • 4 Beds
  • 2.5 Baths
  • Winterbrook SubDv.
  • 32792 Zip Code
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  • Altamonte Springs
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  • Celebration
  • Clermont
  • College Park
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  • Debary
  • Deltona
  • Downtown Orlando
  • Hunters Creek
  • Lake Mary
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