Winter Park Schools and Nearby Homes for Sale and Rent

Please click on one of the below schools to see properties that are marked as being nearby those schools in the MLS.

Elementary Schools


Middle Schools

High Schools





Newest Winter Park Homes by School

  • 1828 HOWELL BRANCH ROAD, WINTER PARK, FL - MLS# O5845610

    Winter Park High - O5845610 - 1828 HOWELL BRANCH ROAD, WINTER PARK, FL 32789
    3 Days on yellowkey

    $230,000 | Single Family Home | 2 beds | 2.0 baths

    Nice, Updated house in desirable Winter Park! New appliances, New laminate floor in bedrooms. Second bedroom with its own bathroom could be used as studio apartment with a separate entrance. Large fenced backyard! No HOA! Conveniently located close to major roads, UCF, shopping and restaurants.

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    Listing is courtesy of: PREMIUM PROPERTIES R.E SERVICE

  • 2507 SWEETWATER TRAIL, WINTER PARK, FL - MLS# O5845326

    Winter Park High - O5845326 - 2507 SWEETWATER TRAIL, WINTER PARK, FL 32789
    3 Days on yellowkey

    $479,000 | Single Family Home | 4 beds | 2.5 baths

    Move in ready 4 bed/2 ½ bath Clayton built Parade of Homes! Only 3rd owner who meticulously updated home with designer touches throughout and added a master wing! Fabulous floorplan for entertaining inside/ out along with daily living! Spacious chef’s kitchen has an abundance of cabinetry and granite counter tops, built-in oven and separate cooktop with crown molding. Opens to the family room with a long breakfast bar, brick flooring, half bath and access to oversized garage. Combined dining and living room with wood flooring, fireplace, fans, and French doors to the lanai is a fabulous space for gathering. Hallway has an abundance of closets, 3 additional bedrooms and a spacious remodeled bath. Large Master Wing offers privacy and relaxation! Adjacent office/studio having French doors to the lanai is perfect for a home office. Resort bath has marble dual vanities with custom cabinetry, large jetted spa bath, walk-in shower, and walk-in closet with built-ins. Fenced backyard is outdoor paradise for year-round entertaining boasting covered brick patio with tongue & groove ceiling, pool, built-in gas grill with brick bar and sitting area, landscaping with vegetable garden, producing Haas Avocado tree and grassy area! With updated windows, flooring, baths/kitchen, paint, plumbing, Master addition and Home Warranty this home is ready for new owner! Ideal location for Dommerich, Maitland Middle, Winter Park High schools, and all that Winter Park & Maitland offer!

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    Listing is courtesy of: KELLER WILLIAMS WINTER PARK

  • 1350 RIDGEWOOD AVENUE UNIT NO, WINTER PARK, FL - MLS# O5843909

    Winter Park High - O5843909 - 1350 RIDGEWOOD AVENUE UNIT NO, WINTER PARK, FL 32789
    4 Days on yellowkey

    $1,600 | Single Family Home | 2 beds | 1.0 baths

    This home is equipped with everything you need for hassle-free living! Providing both excellent quality and value, this professionally managed and maintained home is available to lease immediately. Come see this charming ONE STORY home with 2 Beds, 1 Bath & 1 Car Garage on a corner lot. Plenty of living areas in the home, featuring an updated Kitchen, New A/C, dining area just off the Kitchen, enclosed porch with spacious backyard, bonus room off of the living room and washer/dryer in the attached garage. Included in Lease: Landscaping & Pest Control Service. Enjoy living in one of the most desirable areas of town - close to golf courses, Park Ave shopping, Winter Park Village, Enzian theater and more! Experience ease of lifestyle and in-town living! Walk or bike to area attractions -the WP Boat Tour, Rollins College or Morse Museum. Property is zoned for highly rated Winter Park schools! Pet friendly!

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    Listing is courtesy of: REGAL R.E. PROFESSIONALS LLC

  • 617 LANGHOLM DRIVE, WINTER PARK, FL - MLS# O5842881

    Winter Park High - O5842881 - 617 LANGHOLM DRIVE, WINTER PARK, FL 32789
    4 Days on yellowkey

    $549,900 | Single Family Home | 4 beds | 2.0 baths

    Charm and sophistication at its finest. This landmark Kenilworth Shores home boasts 4 bedrooms, 2 full baths, and a captivating screened in heated pool. Both efficient and private, this home allows for a low maintenance yet luxurious Winter Park lifestyle. Extensive renovations have been completed professionally including a newly remodeled kitchen laced with quartz counters, a waterfall island, shaker style cabinets, stainless steel appliances and LED recessed lighting. This stunning home is lavished with decorative custom trim work, hand scraped birch hardwood flooring, built-in cabinetry, plantation shutters, and crown molding throughout. Adjacent to the screened in Lanai, entertain and accommodate even the largest of family and social gatherings under the large covered patio adorned by tongue and groove wood inlay and recessed lighting. Enjoy the sunrise from the convenience of your plantation style front porch, overlooking your expansive fully landscaped East facing corner lot. Impeccably maintained and with a keen eye for detail, no expense was spared in the care and improvement of this property over the years. A few of the many updates include, new plumbing in 2010, a new architectural shingle roof in 2017, a remodeled kitchen in 2018, new interior lighting in 2018, and a freshly resurfaced pool in 2014.

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    Listing is courtesy of: ROBERT SLACK LLC

  • 1807 BARKER DRIVE, WINTER PARK, FL - MLS# O5843165

    Winter Park High - O5843165 - 1807 BARKER DRIVE, WINTER PARK, FL 32789
    4 Days on yellowkey

    $1,495,000 | Single Family Home | 5 beds | 3.0 baths

    Looking for a quiet & peaceful place, with a magnificent water view, look no further! This pristine home was custom built in 2004 by Bill Felkel and remains loved by the original owners. Lake Spier is one of Winter Park's cleanest, spring fed lakes. This home will always include the tranquil view of a natural habitat, since 40% of the shoreline will never be developed on the private lake. Relax on back screen porch, while others fish off the dock, or boat or swim in the clear water. Only yards away from Baldwin Park, the convenient location is a stone’s throw from shops, restaurants, a dog park, 3+ mile bike/walk path & more. With over 3,800 SF, the ideal floor-plan includes a downstairs master suite, 2nd bedroom & bathroom, and an expansive kitchen & family room, wrapped in newer widows. The spacious master suite has a sitting area, 2 walk-in closets, and French doors that lead to the back porch. The 2nd bedroom downstairs, currently used as an office, has a large walk-in closet. The downstairs includes all-natural hardwood floors, crown molding, 10-foot ceilings, and a wood burning fireplace with a gas starter. Kitchen features a breakfast bar, double oven, enormous walk-in pantry/storage area, and an open dinette area. Upstairs you will find 3 bedrooms, 1 bathroom, a bonus room & a finished attic storage room (15x10). The storage is unbelievable! Come see this fabulous home with breathtaking lake views. This is simply fabulous Florida living at its best! *Ask for a Floorplan & a Survey!

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    Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES

  • 2852 WILL O TH GREEN UNIT 4, WINTER PARK, FL - MLS# O5844836

    Winter Park High - O5844836 - 2852 WILL O TH GREEN UNIT 4, WINTER PARK, FL 32792
    4 Days on yellowkey

    $350,000 | Single Family Home | 4 beds | 2.0 baths

    WELCOME HOME to the Winter Park Pines, where the mailman delivers to your door, beautiful tree lined streets, and sidewalks made for easy access around the neighborhood or to the local parks/schools! This home is tucked away on a beautiful, quiet, tree lined street. DO NOT MISS this METICULOUSLY maintained 4 BED / 2 BATH home. You will immediately be drawn in by the welcoming front porch has as it has an inviting spot to sit and enjoy the mature landscaping. As you walk in, you will enter the foyer and formal living room with neutral tones. The living area flows into the dining area which leads you to the UPDATED KITCHEN. ALL Stainless Steel APPLIANCES, CUSTOM beautiful WOOD cabinets, GRANITE countertops and a breakfast nook. Master bedroom is generously sized with ensuite, the master bathroom has been UPDATED with step in shower. Down the hall you will find 2 additional bedrooms with large closets, and an additional large walk-in hall closet for ample storage. Off of the dining room is a LARGE BONUS ROOM/ 2nd LIVING ROOM/ or FLEX SPACE for any of your entertaining needs with a BEAUTIFUL WOOD BURNING FIREPLACE. The large 4th BEDROOM and INTERIOR LAUNDRY ROOM can be accessed from this 2nd Living area. Also feel free to entertain friends and family on the NEWLY SCREENED IN BACK PORCH. Just minutes from Cady Way Park/Pool/ Trail, Winter Pines Golf Club, Advent Health Winter Park Hospital, Center for Health and Wellbeing and ZONED for top rated Winter Park Schools. Only 10 minutes from Park Ave!

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    Listing is courtesy of: KELLER WILLIAMS WINTER PARK

  • 7628 LODGE POLE TRAIL, WINTER PARK, FL - MLS# O5844871

    Winter Park High - O5844871 - 7628 LODGE POLE TRAIL, WINTER PARK, FL 32792
    5 Days on yellowkey

    $299,000 | Single Family Home | 3 beds | 2.0 baths

    THE MOMENT YOU DRIVE UP, YOUR HEART BEGINS TO QUICKEN. This well maintained home is more than you had hoped. Contemporary double pane windows have replaced the out dated original windows (except the sliding doors). The roof was replaced in 2011 with quality architectural shingles. AND ONCE YOU OPEN THE DOOR....YOU WILL WANT TO STAY. The formal living and dining rooms combine to create the perfect environment for all the family holiday feasts. The remodeled kitchen has adequate cabinet and counter space featuring upgraded wood cabinets and fashionable granite counters. The kitchen opens to the spacious family room highlighted by the wood burning fireplace. Upmarket laminate wood floors lend a smart look to the kitchen, family and dining rooms. You know it's Florida when you sit in the family room overlooking a 19x15 screened porch with a sparkling, cooling pool beyond. Put your mind at ease knowing that the electrical circuit breaker box was replaced in 2019. The air conditioning exterior/interior units were replaced in 2014 and the water heater in 2018. Plumbing re-pipe 2005. Pool re-surface 2017. Chimney swept 2019. Add to this highly desirable schools.....perfect! THIS HOME HAS EVERYTHING YOU NEED FOR THE SIMPLE JOYS OF FAMILY, FRIENDS AND GOOD LIFE. * Click on the Tour 1 button in the upper left corner of this report to access the 3D Virtual Tour. *

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    Listing is courtesy of: IREALTY SERVICES

  • 2416 BAXTER COURT, WINTER PARK, FL - MLS# O5844889

    Lake Howell High - O5844889 - 2416 BAXTER COURT, WINTER PARK, FL 32792
    5 Days on yellowkey

    $299,999 | Single Family Home | 4 beds | 2.0 baths

    WOW! FOUR BEDROOM POOL HOME ON .44 ACRE LOT ON A QUIET CUL-DE-SAC!! This is an OUTSTANDING opportunity to own the home of your dreams!! 4 Bedroom 2 Bath split plan floor plan boasts a renovated kitchen with Corian countertops & updated cabinets/appliances with pass through to HUGE 34x14 screened patio overlooking a sparkling pool & extra large backyard that backs up to peaceful conservation area! Formal living room, dining room PLUS family room with built-ins offers plenty of living space inside. Both master & guest baths have been updated. 2 car garage, large storage shed & irrigation system from well. Extras include: Roof 2012, AC 2010, Exterior Paint 2017, hurricane garage door & NO HOA!! WELCOME HOME!

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    Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES

  • 29 STYMIE PLACE, WINTER PARK, FL - MLS# O5845184

    Edgewater High - O5845184 - 29 STYMIE PLACE, WINTER PARK, FL 32789
    5 Days on yellowkey

    $245,000 | Single Family Home | 4 beds | 2.0 baths

    This four-bedroom, two-bathroom home is located in Winter Park on a cozy street bordering the College Park area just down the road from Dubsdread Golf Course. Walk up to its broad covered front porch and swing while you take in all the possibilities for this home. Original hardwood floors in the main portion of the home (kitchen, family room, front hall, and 1st bedroom). House is a split plan with one bed and one bath on the right side of the home with an additional three beds and one bath on the left side of the home. In between the family room and largest bedroom is a great space to use as an office, a way to extend the living space or even create a dedicated ensuite master. Home is connected to natural gas and has a large single car garage with a workshop/ laundry space to its rear. The rear yard is fully fenced and has plenty of space to park your favorite toy; a boat or RV to the right of the house. Walk to the Dubstread Golf Course for a round of golf or to enjoy a meal at the award winning Tap Room.

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    Listing is courtesy of: ALL REAL ESTATE & INVESTMENTS

  • 315 E NEW ENGLAND AVENUE UNIT 23, WINTER PARK, FL - MLS# O5845038

    Winter Park High - O5845038 - 315 E NEW ENGLAND AVENUE UNIT 23, WINTER PARK, FL 32789
    5 Days on yellowkey

    $945,000 | Condo | 2 beds | 2.0 baths

    A beautiful third floor unit in the Jewel of Winter Park with a private courtyard view! Villa Siena is located 2 blocks off Park Avenue and is within comfortable walking distance to Rollins College, upscale dining, and some of the finest boutique shopping in the Orlando metropolitan area. Amenities include two underground assigned parking space and one assigned garage, a private air conditioned storage unit, luxurious community rooms, exercise facilities, roof top sitting area with a beautiful view, and much more. This charming two bedroom, two bathroom has been beautifully upgraded and includes a spacious floor plan with a gracious entertaining space, lots of natural light, and beautiful porches. This is a gorgeous offering of Winter Park living at its finest. Come enjoy the best of the Winter Park lifestyle!

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    Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES

  • WINTER PARK, FL - MLS# O5845121

    Winter Park High - WINTER PARK, FL 32792
    5 Days on yellowkey

    $1,495 | Condo | 3 beds | 2.0 baths

    One or more photo(s) has been virtually staged. This is a beautiful place with no yard work and water and trash included. It is freshly painted and all flooring tile through out the house. It has private in ground community pool. Access to best schools of Winter Park. It is close to University of Central Florida. Please call for a showing appointment.

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    Listing is courtesy of: HOME WISE REALTY GROUP INC

  • 315 E NEW ENGLAND AVENUE UNIT 22, WINTER PARK, FL - MLS# O5845246

    Winter Park High - O5845246 - 315 E NEW ENGLAND AVENUE UNIT 22, WINTER PARK, FL 32789
    5 Days on yellowkey

    $5,000 | Condo | 2 beds | 2.0 baths

    A beautiful third floor unit in the Jewel of Winter Park with a private courtyard view! Villa Siena is located 2 blocks off Park Avenue and is within comfortable walking distance to Rollins College, upscale dining, and some of the finest boutique shopping in the Orlando metropolitan area. Amenities include one underground assigned parking space and one assigned garage, a private air conditioned storage unit, luxurious community rooms, exercise facilities, roof top sitting area with a beautiful view, and much more. This charming two bedroom, two bathroom has a spacious floor plan with a gracious entertaining space, lots of natural light, and beautiful porches. This is a gorgeous offering of Winter Park living at its finest. Come enjoy the best of the Winter Park lifestyle!

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    Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES

  • 507 S LAKEMONT AVENUE, WINTER PARK, FL - MLS# O5842578

    Winter Park High - O5842578 - 507 S LAKEMONT AVENUE, WINTER PARK, FL 32792
    6 Days on yellowkey

    $529,999 | Single Family Home | 3 beds | 3.0 baths

    Beautiful Winter Park home built in 1955. This is a 4/2 pool home with 2,121 sf with hardwood floors throughout, and porcelain tile in the kitchen, laundry room and bathrooms. Bathrooms and laundry room have been remodeled. Guest bathroom includes a whirlpool tub with glass tile walls, Ronbow bathroom vanity with granite slab, vessel sink and high-end Kohler fixtures. In the master bathroom you will find porcelain tile flooring, a new frameless glass shower enclosure, and a shower system with a rainfall shower head. Popcorn ceilings are gone, with walls and ceiling freshly painted. Recently installed a new Carrier HVAC system. Freshly landscaped yard includes Zoysia sod with new plants throughout the entire property, rock landscaping in the carport area, new gutters with underground French drain system. The pool has been upgraded from chlorine to salt water with new pool equipment and glass mosaic tiles around the pool perimeter. Fenced in back yard and screened-in pool enclosure. Great school district includes Brookshire Elementary, Glenridge Middle and Winter Park High. Home is clean and ready for immediate move in. Close to Baldwin Park, Rollins College, Winter Park Hospital and Park Ave!

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    Listing is courtesy of: COLDWELL BANKER RESIDENTIAL RE

  • 230 E ROCKWOOD WAY, WINTER PARK, FL - MLS# O5843065

    Winter Park High - O5843065 - 230 E ROCKWOOD WAY, WINTER PARK, FL 32789
    6 Days on yellowkey

    $1,275,000 | Single Family Home | 5 beds | 4.0 baths

    An extraordinary opportunity to own a luxurious & contemporary designed home in the heart of the highly desired area of Winter Park! The curb appeal is magnificent w/professional landscaping, a welcoming front porch, brick streets & ample driveway parking! You will notice superiority in every detail from the stone/wood exterior, to the open, exquisite interior. This modern showplace offers 4 spacious bedrooms plus a 5th bedroom with a built in bed/closet (which can also be used as an office), 4 full bathrooms, wood flooring throughout, open concept kitchen/family room, upstairs bonus room, custom lighting, shade window treatments, climate controlled storage room, up & downstairs laundry, covered lanai w/summer kitchen & wine refrigerator, salt-water pool w/heated spa & a 2 car garage w/epoxy flooring. The kitchen boasts all high-end stainless steel Thermador appliances, gas cooktop, Cambria countertops w/a waterfall edge, built in oven & an oversized island perfect for entertaining. Enjoy tranquility & elegance in the main level master bedroom w/glass french doors open to the lanai/pool, a large walk-in closet w/a second washer/dryer inside. The peaceful en-suite features a Japanese soaking tub, spacious shower, dual sinks, custom lighting & elegant quartz countertops. A+ LOCATION! Zoned for the most desired schools in Winter Park: Audubon K-8 and Winter Park High! Centrally located w/walkability & bike-ability to local restaurants, East End Market, Park Ave., Rollins & Corrine Drive shopping!

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    Listing is courtesy of: COLDWELL BANKER RESIDENTIAL RE

  • 1608 BARCELONA WAY, WINTER PARK, FL - MLS# O5844049

    Winter Park High - O5844049 - 1608 BARCELONA WAY, WINTER PARK, FL 32789
    6 Days on yellowkey

    $1,099,000 | Single Family Home | 4 beds | 3.5 baths

    This is a wonderful opportunity to own a beautiful Winter Park pool home. Elevated on a large lot of over half an acre in the desirable Sevilla neighborhood, this home has wonderful curb appeal with park-like setting and is perfectly located just blocks from the downtown Winter Park shopping district on Park Avenue. Additionally, this residence provides easy access to downtown Orlando. The main level features a large family room with wood-burning fireplace, formal living and dining spaces, a sunroom and an eat-in island kitchen that overlooks the spacious backyard and pool area, perfect for entertaining friends or relaxing with family. The spacious master retreat has a generously sized bedroom, luxurious bath, plus there is a bonus area off the master that can be used as an office or nursery. The home also features three more bedrooms and an additional second large bonus room on the lower level that can be used as a home theater or gym. Enjoy a location with easy access to Downtown Winter Park, Downtown Orlando, and close to fantastic Winter Park schools.

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    Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY

  • 334 SCOTTSDALE SQUARE UNIT 334, WINTER PARK, FL - MLS# O5844619

    Winter Park High - O5844619 - 334 SCOTTSDALE SQUARE UNIT 334, WINTER PARK, FL 32792
    6 Days on yellowkey

    $134,900 | Condo | 3 beds | 2.0 baths

    One or more photo(s) has been virtually staged. Fantastic investment opportunity or a place to call home! Winter Park address at a great price! This condo is zoned for desirable schools and close to growing Full Sail University, Park Ave, Rollins College, short drive to UCF and airport. This spacious well maintained property features an amazing open floor plan offering a full bedroom and bathroom downstairs, access to 2 updated balconies through sliding doors on each level and 2 bedrooms with a full bathroom upstairs for convenience and privacy. New carpet throughout, fresh paint, new closet doors in selected rooms. HOA fee covers water and sewer! Under New Management! Funds to refurbish Exterior work including roofs have already been secured. Call for your private tour today!

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    Listing is courtesy of: FUTURE HOME REALTY INC

  • 870 MAYFIELD AVENUE, WINTER PARK, FL - MLS# O5844833

    Winter Park High - O5844833 - 870 MAYFIELD AVENUE, WINTER PARK, FL 32789
    6 Days on yellowkey

    $2,249,000 | Single Family Home | 6 beds | 6.0 baths

    This nicely maintained traditional style home is located on the brick-paved streets of winter park within walking distance to all shops and restaurants Winter Park has to offer. It offers 6 beds 6 full baths, all wrapped up 5921 square feet of living space. As you approach the front door from the motor court you will notice the Chicago style natural brick faced on the and the front walkway. As you enter the home you will be welcomed by the beautiful travertine foyer and beautiful paneling on the walls which exude quality. The separate formalin dining areas are beautifully accented but an all precast fireplace which makes it for a warm and cozy environment, the formal dining area is made for the entertainer in all of us, it’s big enough 12 person table dining table, it also offers a built-in wine cellar with a 200 bottle storage and a butlers pantry to boot. The family room offers hardwood oak floors, gorgeous views of the pool, a fireplace, and beautiful trim thought to give a refined feel. The Kitchen is truly where that heart is and that could be truer with this home, it’s conveniently located next to all the major rooms of the first floor, with white cabinets, granite tops and professional appliances it will surely meet your expectations. The master suite is also located on the first floor and offers its own A/C unit for your chili sleepers, vaulted ceiling and great views of the backyard. Too many items to list!!!

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    Listing is courtesy of: CORCORAN PREMIER REALTY

  • 1133 SUNSET DRIVE, WINTER PARK, FL - MLS# O5844638

    Winter Park High - O5844638 - 1133 SUNSET DRIVE, WINTER PARK, FL 32789
    7 Days on yellowkey

    $1,299,000 | Single Family Home | 3 beds | 2.5 baths

    Inspired by the architectural styles of New Orleans, 1133 Sunset Drive is a modern take on tradition. Custom details abound in this 3 story, 3 bedroom, 2.5 bathroom Double-Gallery style home. Authentic Bevolo gas lanterns from New Orleans, handmade brick from North Carolina, immaculate landscaping by Signature Landscaping and a magnificent 200 year old Live Oak tree add to the ambiance and romantic vibe of the home. An abundance of windows and French doors by Jeld-Wen bring natural light in from all directions. Custom carpentry work and hardwood floors paired with the functionality of an open floor plan are the perfect combination of traditional details and modern luxuries. The kitchen is equipped with state of the art Thermador appliances, Quartz counter tops, and a walk-in pantry. Upstairs, the master bedroom is both spacious and comfortable with a large walk-in closet, en-suite master bathroom and private second floor porch with views of the Oak tree. The third floor flex space is wired for a home theater, or could be the perfect office or game room. The back patio has a private pool and access to the 2 car garage. Schedule a tour of this custom home today.

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    Listing is courtesy of: HOTARD REALTY LLC

  • 726 WARRENTON ROAD, WINTER PARK, FL - MLS# O5844622

    Winter Park High - O5844622 - 726 WARRENTON ROAD, WINTER PARK, FL 32792
    7 Days on yellowkey

    $250,000 | Villa | 2 beds | 2.0 baths

    Fully renovated 2/2 with huge vaulted ceiling living room that could be divided to make 3rd bedroom. Wood-look tile throughout, new cabinets and appliances, granite countertops, fenced yard, gazebo, mature landscaping, one car garage, front and back patios.

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    Listing is courtesy of: REALTY 180 LLC

  • 1623 BARCELONA WAY, WINTER PARK, FL - MLS# O5844191

    Winter Park High - O5844191 - 1623 BARCELONA WAY, WINTER PARK, FL 32789
    7 Days on yellowkey

    $1,125,000 | Single Family Home | 5 beds | 5.5 baths

    Stately, French Chateau style, brick home located in Sevilla, one of Winter Park’s most desirable neighborhoods. Enter through large custom wood - double doors to a spectacular foyer with graceful curving staircase, complete with a walk-in “coat” closet and powder bath. Just off the foyer is the large formal Living room to the left and a stunning Dining room to the right that can accommodate a table for 6 or 16. Family room and Kitchen to the back of the home with a huge Florida room, all opening to the rear deck and glorious views of Mead Gardens and meandering Howell Creek. The idyllic backyard patio and pool overlook the flowing, scenic creek, surrounded by a serene nature setting and endlessly entertaining wildlife. Two large bedroom suites are also downstairs and a huge (16' x 8') laundry room off the side entry garage. Master bedroom is upstairs with beautiful views in the back. Two additional rooms and a bath are also on the second level. All rooms in this home are very spacious. Sparkling pool and spa grace the back patio. Perfect outside entertaining areas and even a cozy firepit spot sitting up high overlooking the whole backyard! Quiet established Winter Park neighborhood and on an almost half-acre, cul-de-sac lot. Just a 7-minute drive to Park Avenue!

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    Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY

  • 865 S PENNSYLVANIA AVENUE, WINTER PARK, FL - MLS# O5844460

    Winter Park High - O5844460 - 865 S PENNSYLVANIA AVENUE, WINTER PARK, FL 32789
    7 Days on yellowkey

    $485,000 | Single Family Home | 3 beds | 2.0 baths

    Located in HIGHLY desirable Winter Park “College Quarter” historic district, this home boasts plenty of CHARACTER and CHARM. Take a short walk to Rollins College and Park Avenue and enjoy the many upscale restaurants, cafes, boutiques, galleries, farmer’s market, theatre, music, entertainment and the Winter Park Chain of Lakes. TWO separate residences with a 2 bedroom 1 bathroom home featuring wood floors and crown molding throughout, a renovated kitchen and bathroom, formal dining room with a fireplace, bright and spacious living room, indoor washer/dryer and French Doors leading to a FABULOUS screened front porch, perfect for reading, relaxing or entertaining. The second apartment or MOTHER IN-LAW SUITE, offers a 1 bedroom, 1 bath featuring wood floors and crown molding throughout, full kitchen with stainless steel appliances, indoor washer/dryer and its own private deck. This lovely, well maintained home has a new roof (2017), new water heaters (one tankless), beautiful landscape, plenty of parking space and no HOA. The property is zoned R-2 for income potential, but it can also be reverted back to a large single family home. Don’t miss this GEM and come enjoy the Winter Park lifestyle!

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    Listing is courtesy of: URBAN REALTY GROUP INC

  • 1500 HARRIS CIRCLE, WINTER PARK, FL - MLS# O5844429

    Winter Park High - O5844429 - 1500 HARRIS CIRCLE, WINTER PARK, FL 32789
    9 Days on yellowkey

    $799,900 | Single Family Home | 2 beds | 2.0 baths

    AWESOME "THE TRIANGLE HOUSE" PROFESSIONALLY DECORATED! 2 fireplaces - high ceilings, a spectacular lot make a special setting for a beautiful home. Mature landscaping gives privacy and beauty to a wonderful setting. Large open living and dining area downstairs opened to a well-planned kitchen with stone floors and countertops throughout.First-floor laundry room and full bath, bay windows downstairs make this a special setting. Beautiful wood stairs and large windows make the walk to the second floor special with beautiful views. Oversized master with a stain glass window and spectacular bathroom and closet area. The master shower is oversized and the master is an office off master. Second bedroom with a full bathroom with a jacuzzi tub. Enjoy proximity to the lakes and downtown Enjoy the quality and style of the 1900's craftsmanship and the modern amenities of a new home with this one of a kind 'Triangle House'. Located in a very desirable and friendly, old Winter Park neighborhood on a brick street. Stained glass windows and doors from England. Spacious kitchen and gathering room with tongue & groove wood ceilings, and large luxurious Master bedroom & bath. Master has custom system closet built-ins. Home office off Master could double as nursery or exercise. Savannah walled garden is perfect for cozy entertaining. This is truly a remarkable home!

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    Listing is courtesy of: GILLEN & ASSOCIATES

  • 1928 HOUNDSLAKE DRIVE, WINTER PARK, FL - MLS# O5844356

    Lake Howell High - O5844356 - 1928 HOUNDSLAKE DRIVE, WINTER PARK, FL 32792
    9 Days on yellowkey

    $324,900 | Single Family Home | 5 beds | 3.0 baths

    Sprawling 2,200+ square foot, 5 BED, 3 FULL BATH Winter Park Ranch! This flowing floor plan offers both formal Living and Dining rooms, a Family Room fireplace surrounded by custom built-ins, AND a Bonus Room! With a huge open living room just perfect for movie nights and gatherings, you'll love the gray & white paint selections complimented by a few splashes of color! The kitchen has been FULLY updated so you can move right in and enjoy instantly! Stainless steel appliances, granite countertops, quality cabinetry with crown molding, an attractive backsplash, recessed lighting, and stone floors with a pass through window to your Bonus Room! A HUGE bonus room with access to the back yard is an excellent set up for entertaining or enjoy breezy Florida nights! The dry bar with granite counter top, WINE FRIDGE, and custom cabinetry is sure to impress! This split floor plan Master Suite offers a walk-in closet with custom built-in shelving and storage, a dual vanity with granite countertop, and the perfect amount of lighting! Close to many top-rated restaurants, stores, and major roadways like 417 & 408, this Winter Park Ranch home is a rare find and sure to go quickly! Contact us today for a private showing!

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    Listing is courtesy of: INNOVATIVE REALTY, LLC

  • 1821 HARLAND PARK DRIVE, WINTER PARK, FL - MLS# P4909692

    Winter Park High - P4909692 - 1821 HARLAND PARK DRIVE, WINTER PARK, FL 32789
    9 Days on yellowkey

    $995,000 | Single Family Home | 4 beds | 3.5 baths

    This luxurious Taylor Morrison residence in Windsong, one of Winter Park's most exclusive neighborhoods, is designed to be breathtaking. Be amazed by the tree-lined streets, impeccable landscaping, and sealed pavers as you pull up to your home. This pristine four-bedroom, three and a half bath home offers an open concept living and entertaining space with luxurious finishes throughout. Upon entering the front door, you will find a stunning front hall that opens up to a impressive entertaining space. The stunning master suite has recessed ceilings, walk-in closets, his and hers sinks and an opulent in suite bath with separate shower. The kitchen which faces to the spacious family room and breakfast area, features Wolf appliances, granite countertops, and Sub-Zero refrigerator. The family room doors transport you to an enclosed oasis. Feel the warm travertine tiles on your toes, mist from the outdoor mist cooling & heater system, as you walk to the salt system pool/spa, a great place to unwind after a long day. To fully enjoy the Windsong experience, this house is located close to community clubhouse,offers access to Winter Park chain-of-lake, community pontoon boat and pool. Zoned to top rated schools, and located near trendy restaurants. Additional upgrades: around house gutters, underground gutters drain, party light at the lanai enclosure, outdoor kitchen has Alfresco grill & double side burner. Front and back lanai wood ceilings.

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    Listing is courtesy of: KELLER WILLIAMS REALTY SMART 1

  • 7945 PLEASANT PINE CIRCLE, WINTER PARK, FL - MLS# O5844148

    Lake Howell High - O5844148 - 7945 PLEASANT PINE CIRCLE, WINTER PARK, FL 32792
    10 Days on yellowkey

    $499,000 | Single Family Home | 5 beds | 4.0 baths

    Spacious warm welcoming home in a gated community of Enclave at Aloma in Winter Park! This 5 bedroom 4 bath home has the curb appeal and looks brand new ! The natural lighting, open floor plan and gorgeous carpet flooring. The large kitchen includes new stainless steal appliances , granite counter tops, 42'' cabinets and an island.. The kitchen/family room combo is perfect for entertaining and both have views of the fenced backyard . First floor also includes a guest suite and full bathroom. The second story master suite is over 350 SQFT and equipped with a two large walk-in closets, two vanities, garden tub and separate shower stall. , The 3rd bedroom has it's own bathroom and walk-in closet. This home also features large bonus room for entertainment and watching movies like having your own theatre. Back yard is good size lot to build a pool and is one of the best lots in the neighborhood! Ryland, who are know for their energy-efficient design, allows for low utility bills. This community is conviniently located near shopping, dining, highway access via 417, Cross Seminole Trail, Trinity Prep, & highly rated Seminole County schools. Don’t miss this opportunity!

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    Listing is courtesy of: REGAL R.E. PROFESSIONALS LLC

  • 8077 PLEASANT PINE CIRCLE, WINTER PARK, FL - MLS# O5844184

    Lake Howell High - O5844184 - 8077 PLEASANT PINE CIRCLE, WINTER PARK, FL 32792
    10 Days on yellowkey

    $475,000 | Single Family Home | 4 beds | 3.5 baths

    One or more photo(s) has been virtually staged. Beautiful WINTER PARK 2013 construction home with NO REAR NEIGHBORS & peaceful CONSERVATION VIEWS! Covered front patio takes you to your OPEN CONCEPT LIVING & DINING. Just off the living room is a perfect DEN or playroom with double entry privacy doors. Dining room features French Doors to covered patio overlooking total conservation. Enter your SPACIOUS KITCHEN OVERLOOKING THE FAMILY ROOM with large eat-in nook & CUSTOM banquet seating bench with storage. This GORGEOUS kitchen equipped with breakfast bar, stainless steel appliances and closet pantry. UPSTAIRS LOFT separates all bedrooms, options are endless in this bonus area. Separate space with built in desk with file cabinets upstairs overlooking the LOFT. EXPANSIVE Master Retreat pulls out all the stops for your dream bedroom with HIGH CEILINGS, private en-suite bathroom with SEPARATE DUAL SINK VANITIES, both GREAT in size with plenty of counter & cabinet space, garden bathtub, shower stall and large walk-in closet. 2nd & 3rd bedroom have a shared JACK-AND-JILL bathroom with dual sink vanity and private commode with shower/tub combo. 4th upstairs bedroom shares a full bathroom with the bonus area. BEAUTIFUL luxury hardwood throughout (exception to loft) & crown molding downstairs. Enjoy your morning coffee and evening cocktails on this COVERED LANAI/PATIO with no rear-neighbors and enjoying the peaceful community setting. Property is within close proximity to shopping, restaurants, entertainment, UCF, Full Sail and major highways!

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    Listing is courtesy of: EXP REALTY LLC

  • 3087 CRANE STRAND DRIVE, WINTER PARK, FL - MLS# A4460018

    Winter Park High - A4460018 - 3087 CRANE STRAND DRIVE, WINTER PARK, FL 32792
    10 Days on yellowkey

    $308,900 | Single Family Home | 4 beds | 2.0 baths

    Step inside this newly updated Winter Park home and you might just fall in love. This home has 4 spacious bedrooms and 2 updated bathrooms. Walk-in and you automatically have a view of the private pool surrounded by a wooden fence. The kitchen is fully equipped with quartz countertops, brand new stainless steel appliances, and crown molding. A new stone fireplace is in the home to keep you cozy. Also, brand new floors and a resurfaced pool and pumps. The location could not be better as you are only miles away from all the amenities, restaurants, shops, and schools.

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    Listing is courtesy of: FLATFEE.COM

  • 2903 ROUEN AVENUE, WINTER PARK, FL - MLS# O5843830

    Winter Park High - O5843830 - 2903 ROUEN AVENUE, WINTER PARK, FL 32789
    10 Days on yellowkey

    $257,400 | Single Family Home | 3 beds | 2.0 baths

    Perfectly charming 3 bedroom, 2 bathroom, 1 car carport home located in the Winter Park city limits and zoned for A-rated Dommerich Elementary, Maitland Middle and Winter Park High School. Tree-lined streets, separate laundry area with storage and tile throughout the entertaining spaces make this house a home! The home sits on a large 0.23 acre (76’x133’) lot and provides plenty of backyard space to entertain friends and family on the outdoor patio or just let the dogs run free. With a freshly painted interior and exterior and replaced ROOF 2015, this lowest priced 3 bed/2 bath in Winter Park is ready for you to move in and make it your own. Seller will install carpet of buyer’s choice in the bedrooms. NO HOA so bring your tools, toys and trucks. Easy access to major thoroughfares, I-4 and just minutes to the area schools, Winter Park Village, Park Ave and only 20 minutes to the airport and center of Orlando. Call today for your private showing.

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    Listing is courtesy of: CREEGAN PROPERTY GROUP

  • 1067 PORTSMOUTH LANE, WINTER PARK, FL - MLS# O5844098

    Lake Howell High - O5844098 - 1067 PORTSMOUTH LANE, WINTER PARK, FL 32792
    10 Days on yellowkey

    $264,000 | Single Family Home | 3 beds | 2.0 baths

    POOLSIDE PARADISE. This home is located on a large corner lot and features a stunning tropical backyard with large open air pool, not one but two sundecks and is perfect for entertaining. The home features many upgrades which include Custom Kitchen with Granite Countertops, upgraded appliances and two storage pantries. The floorplan is also ideal for entertaining with Living Room/Dining Room combo plus a separate family room. Master bath features custom vanity, step in shower with sliding glass door, custom tile and walk in closet with custom shelving. Great sized guest bedroom with easy access to the guest bath, Screened patio overlooks the sparkling pool and you can enjoy either the sauna or the hot tub. Other updates include custom Engineered wood flooring, ceramic tile and carpet. The garage has an enclosed air conditioned laundry room that can be easily be converted back to full size garage... Mature landscaping on the property and a majestic Oak Tree in the front yard. Large backyard has new fence and Voluntary HOA means you can park your toys without the hassle. Home has newer A/C and plumbing. Great Seminole County make this the perfect starter home and it is.

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    Listing is courtesy of: RE/MAX TOWN & COUNTRY REALTY

  • 350 BRIARWOOD DRIVE, WINTER PARK, FL - MLS# O5844845

    Winter Park High - O5844845 - 350 BRIARWOOD DRIVE, WINTER PARK, FL 32789
    10 Days on yellowkey

    $525,000 | Single Family Home | 4 beds | 2.5 baths

    Located in the heart of Winter Park in the well-established community of Quail Hollow! Sitting on a large corner lot, sits this charming 1-story home featuring 4 bedrooms, split plan, 2 full baths, nearly 2200 sq.ft, foyer with tile, formal Living & Dining rooms, comfortable Family room with wood-burning fireplace, adjoining Kitchen with stainless appliances, desk, Master suite with walk-in closet & dual vanities, 3 spacious guest bedrooms, guest bath w/tub-shower, large inside laundry with storage & toilet; huge covered, screened rear porch, brick backyard open patio, partially fenced, irrigation, oversized, side-entry 2-car garage with workshop & storage; solid CBS construction. Zoned for the New Audubon Park K-8, walking distance to Blue Jacket Park & a short hop to Baldwin Park Village. Sold As Is please.

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    Listing is courtesy of: COLDWELL BANKER RESIDENTIAL RE

  • 275 N CAPEN AVENUE, WINTER PARK, FL - MLS# O5844266

    Winter Park High - O5844266 - 275 N CAPEN AVENUE, WINTER PARK, FL 32789
    10 Days on yellowkey

    $1,450 | Single Family Home | 2 beds | 1.0 baths

    This 3 ba / 2 ba 1200 sqft home features a single car garage, two full baths, large master bedroom and eat in kitchen. Less than a mile away from desirable Park Avenue, and Rollins Collage, this property features new carpet, fresh paint, washer/dryer included! All prospects must drive past property before any showings can be scheduled.

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    Listing is courtesy of: PREMIER MANAGEMENT GROUP INC

  • WINTER PARK, FL - MLS# O5844046

    Edgewater High - WINTER PARK, FL 32789
    11 Days on yellowkey

    $1,150 | 1/2 Duplex | 1 beds | 1.0 baths

    Situated on a large corner lot in the beautiful city of Winter Park, this 1 bedroom, 1 bathroom duplex is conveniently located near an abundance of shopping and restaurant locations, Florida Hospital, Rollins College, and Downtown Orlando. The property has a single covered carport, a fenced-in yard, ceiling fans, utility room, tile in the living/dining room and hard surface flooring in the bedroom. A small pet may be considered. We are here to make your time in the home as enjoyable and convenient as possible. We offer a safe and secure online portal where you can submit maintenance requests and pay online with multiple payment options, 24/7 emergency maintenance response team, and well-maintained homes. Please note the listed amenities may not be accurate.

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    Listing is courtesy of: REAL PROPERTY MANAGEMENT & REALTY INC

  • 2219 VENETIAN WAY, WINTER PARK, FL - MLS# O5843993

    Winter Park High - O5843993 - 2219 VENETIAN WAY, WINTER PARK, FL 32789
    11 Days on yellowkey

    $2,185,000 | Single Family Home | 6 beds | 6.0 baths

    Beautifully designed and custom-built by premier Winter Park builder Bill Felkel, this stunning home is situated on an oversized 0.40 acre lot in the prestigious Winter Park Via’s. This spacious two-story estate has 6,362 sf of living space, and offers 6 bedrooms and 6 full bathrooms. Downstairs exhibits a master retreat, private office, formal living and dining room spaces, utility room, kitchen overlooking the vast family room and a mud room with a second refrigerator. The upstairs embodies two separate wings. The first upstairs wing offers 4 bedrooms, 3 full bathrooms and a loft. The second upstairs features a spectacular home theater, and an enormous bonus room with a full bathroom - that can be used as a game room, an exercise room or 6th bedroom. This exclusive home includes a number of high-end finishes, gorgeous oak floors throughout, dazzling beamed ceilings, three gas fireplaces, plantation shutters, and a gourmet kitchen with stainless steel appliances and marble countertops. Other highlights include an attached two car garage, a detached one car garage, an indoor pool/spa with a wonderful seating area, as well as a fully equipped summer kitchen with retractable screens overlooking the outdoor pool. Enjoy luxury living at its finest, with just a short stroll to the Winter Park Racquet Club.

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    Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES

  • 204 N RANGER BOULEVARD UNIT 2, WINTER PARK, FL - MLS# O5843101

    Winter Park High - O5843101 - 204 N RANGER BOULEVARD UNIT 2, WINTER PARK, FL 32792
    12 Days on yellowkey

    $400,000 | Single Family Home | 4 beds | 3.0 baths

    Welcome to the Winter Park Pines, with tree-lined streets and the mailman that delivers to your door! You will not want to miss this beautifully, FULLY renovated home in this highly desired Winter Park neighborhood. It's also zoned for top-rated schools in Winter Park, plus it's minutes away from the Crosby Center, WP Advent Health hospital, the Cady Way Trail & Pool, Ward Park, Winter Pines Golf Course, plus so much more! BE PREPARED TO FALL IN LOVE with this SPLIT FLOOR PLAN AND TWO MASTER BEDROOMS. Home was COMPLETELY UPDATED in 2018. As soon as you walk into this home, you'll love the beautiful floors throughout and the open floor plan. The gorgeous kitchen features granite countertops, stainless steel appliances, large island and a breakfast bar - the perfect kitchen for hosting and entertaining! From the living area, walk out through the sliding glass doors to find a large, covered lanai and gorgous POOL! The Master Suite also includes a sliding glass door that takes you out onto the relaxing lanai. Enjoy the spacious room, large walk-in closet and beautifully UPDATED master bath! The home also features new light fixtures throughout and ceiling fans. Three additional bedrooms (including additional master with suite) are located down the hall, plus an UPDATED hall bath. Outback, enjoy your private pool and screen back patio for entertaining! Don't wait any longer - come see this amazing home TODAY!

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    Listing is courtesy of: KELLER WILLIAMS WINTER PARK

  • 916 N LAKEMONT AVENUE, WINTER PARK, FL - MLS# O5842944

    Winter Park High - O5842944 - 916 N LAKEMONT AVENUE, WINTER PARK, FL 32792
    12 Days on yellowkey

    $249,900 | Single Family Home | 3 beds | 2.0 baths

    Walking distance to Lakemont Elementary and Lakemont YMCA. NO HOA. Zoned for Winter Park schools, near places to shop and eat. This home has a screened in patio with a large fenced in yard. Close to UCF and Valencia. Great home if you're looking for your first one or a great investment.

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    Listing is courtesy of: FLORIDA HOME REALTY & INVEST

  • 860 N DENNING DRIVE, WINTER PARK, FL - MLS# O5843536

    Winter Park High - O5843536 - 860 N DENNING DRIVE, WINTER PARK, FL 32789
    12 Days on yellowkey

    $325,000 | Single Family Home | 2 beds | 1.0 baths

    Pure Potential! Excellent opportunity in Winter Park. Charming 2 bedroom, 1 bath home in the Heart of Town. Walk to Winter Park Village & more. Home has been lovingly cared for by a single family for over 30 years. Fenced yard for privacy. Open floor plan with great room. Move-in, renovate, or build new. Close to shops, restaurants, and major roadways. Schedule a showing today.

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    Listing is courtesy of: KELLY PRICE & COMPANY LLC