Winter Park FL Real Estate & Homes for Sale

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Beds:
2
Baths:
2.00
Sq.Ft.:
1,020
Status:
NEW LISTING
MLS#:
O6285553
Type:
Condo
Subdivision:
Winter Park Woods Condo
Lot size:
0.2 Acres
Year built:
1974
A broker reciprocity listing Courtesy: EXP REALTY LLC 888-883-8509
View additional info

ADDITIONAL INFORMATION

Welcome to this spacious and modern 2 bedroom, 2 bathroom condominium located in Winter Park, FL, just minutes from Full Sail University, Baldwin Park, shopping, and entertainment. This property is the perfect fit for a first-time home buyer or a great rental opportunity for $1600 per month. Huge Rental Market in this area! Upon entering the unit, you'll be greeted by an open floor plan, with a large living room. The kitchen features newer appliances and a bar top big enough for three . There is plenty of cabinet and counter space, as well as built-in storage. The master bedroom features an in-suite bathroom. The second bedroom is well-sized and adjacent to the second full bathroom. Both bathrooms are in good condition. Additional features of the unit include a large laundry room with plenty of storage, central air conditioning, and a back patio. Don't miss out on the opportunity to call this condominium home. Schedule your showing today!

Beds:
3
Baths:
2.00
Sq.Ft.:
2,114
Status:
NEW LISTING
MLS#:
O6290084
Type:
Single Family
Subdivision:
Cortland Park
Lot size:
0.19 Acres
Year built:
1981
A broker reciprocity listing Courtesy: EXP REALTY LLC 407-204-1111
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ADDITIONAL INFORMATION

Welcome to the epitome of the Winter Park lifestyle at 250 Cortland Ave, nestled among million-dollar homes on one of the most picturesque, tree-lined, brick streets in the heart of Winter Park, FL. This meticulously maintained house presents the ideal blend of luxury and comfort, with a low-maintenance, fully landscaped yard, complete with a sprinkler system, an oversized two-car garage, a sparkling swimming pool, and a spa, all enclosed for privacy by a PVC fence. Step inside this inviting three-bedroom, two-bath split floor plan home, and you're instantly captivated by the expansive view of the grand living area, the enclosed lanai, and the serene pool beyond. The residence boasts a move-in-ready condition with a host of recent upgrades, including a new roof, elegant Brazilian Rosewood floors in the living area, and durable, health-conscious quarry tile floors in the kitchen, bath, and hallways. The heart of the home, the kitchen, has been reimagined with new cabinetry and state-of-the-art appliances. Both the master and secondary bathrooms are refreshed with new vanities and modern shower doors. Additional comforts include new carpeting, vinyl flooring in select areas, ample storage with large walk-in closets, an entry hall closet, and a generous linen storage space. The thoughtful touches extend to new door hardware and upgraded lighting throughout, enhancing the overall aesthetic and functionality. Imagine retracting the 3way sliding glass doors that connect the grand living area to the lanai, and you're living the quintessential inside-outside Florida lifestyle. This home is so light and airy that no daytime lighting is required. All of this located by Lake Mizell, part of the sought after Winter Park chain of lakes. Where you can enjoy the incredible views while taking a tranquil walk along the Lake. Don't miss the opportunity to own this true neighborhood gem in Winter Park, where luxury living and convenience meet.

Beds:
4
Baths:
4.00
Sq.Ft.:
3,140
Status:
NEW LISTING
MLS#:
O6288366
Type:
Single Family
Subdivision:
Brookshire Heights 1st Add
Lot size:
0.2 Acres
Year built:
2018
A broker reciprocity listing Courtesy: PALMANO GROUP RE BROKERAGE LLC 321-214-1211
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ADDITIONAL INFORMATION

Welcome to 2536 Brookshire Ave, a spacious 4-bedroom, 3.5-bath modern farmhouse. The open floor plan enhances flow throughout, with a first-floor primary suite featuring generous his and her closets. Designer lighting and plumbing fixtures, custom interior paint, 8-foot doors, and wood-like tile floors add to the home's style. All bedrooms are pre-wired for cable and CAT 6, with surround sound in the main living areas and speaker wiring on the back porch. The gourmet kitchen has custom white shaker cabinetry with soft-close doors and drawers, an oversized granite island, and designer pendant lighting. Stainless steel appliances, including an induction cooktop and refrigerator, add to the kitchen’s high-end appeal. A built-in pantry and under-cabinet lighting with integrated outlets complete the stylish and functional space. The primary suite offers a luxurious retreat with a designer-tiled walk-in shower enclosed in custom glass, a freestanding soaking tub, and dual solid wood vanities with ample storage. This home is equipped with the latest smart technology, including a motorized retractable screen lanai, custom blackout shades in bedrooms, and a privacy-enhancing Viburnum hedge surrounding the property. A Culligan Gold Series water softener system ensures high-quality water throughout the home. The Lutron smart exterior lighting system, MyQ smart garage door opener, and Schlage smart front door lock provide convenience and security, with coded entry access from every exterior door. The home is also wired for Ethernet throughout, and a Ring doorbell enhances safety. Enjoy the spacious three-car garage with remote access. Built for efficiency and quality, this home features foam-insulated block walls, Low-E windows, and a radiant barrier roof. Two 15 SEER AC units and a programmable thermostat provide year-round comfort. Other details include a stained tongue-and-groove pine ceilings on the covered porches, a fully fenced backyard and a sprinkler system. Located within one of Winter Park’s top-rated school districts, this home is just minutes from Park Avenue, where you can enjoy upscale shopping, fine dining, and everything else this vibrant city has to offer.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,466
Status:
NEW LISTING
MLS#:
O6288258
Type:
Single Family
Subdivision:
Brookshire Heights
Lot size:
0.25 Acres
Year built:
1958
A broker reciprocity listing Courtesy: RE/MAX TOWN & COUNTRY REALTY 407-695-2066
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ADDITIONAL INFORMATION

Introducing an incredible opportunity to own a beautifully updated POOL home in Winter Park... just a block from Top-rated Brookshire Elementary School! Situated on an oversized lot with 2-car garage, this home offers the perfect blend of function, design, and comfort- boasting Mid Century Modern vibes! As you enter through the beautiful double glass doors, you are greeted by an expansive foyer that flows seamlessly into the dining room and open-concept kitchen; all of which has been tastefully updated with meal prep and entertaining in mind!! Fully equipped with all appliances, the kitchen offers modern granite countertops & breakfast bar, and beautiful wood cabinetry with soft-close features, undermount lighting & glass-front display cabinets **PLUS great storage, prep space and excellent lighting! Off of the kitchen and dining room is a dedicated living/great room with TWO sets of French Doors to access the covered patio where you can take advantage of the Florida weather nearly year-round! The master bedroom sits at the back of the home for added privacy, and offers a walk-in closet, an en-suite shared bath, and French Doors that lead to a pavered patio that overlooks the backyard oasis (while providing just the right amount of natural light!). Outside you will enjoy the sparkling pool with stone-pavered deck nestled among the large, fully-fenced yard with plenty of space to play, garden, and relax! Roof and HVAC were replaced in 2014, Pool Pump replaced in 2018. All electrical panels have been updated.

Beds:
4
Baths:
3.00
Sq.Ft.:
2,563
Status:
NEW LISTING
MLS#:
O6289847
Type:
Single Family
Subdivision:
Dubsdread Heights
Lot size:
0.16 Acres
Year built:
2020
A broker reciprocity listing Courtesy: PREMIER SOTHEBY'S INTL. REALTY 407-644-3295
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ADDITIONAL INFORMATION

Discover modern living at its finest in this stunning contemporary home in the heart of Winter Park, FL! Built in 2020, this spacious 4-bedroom, 2.5-bathroom residence offers over 2,500 sq. ft. of beautifully designed living space that is perfect for families of all sizes. The first floor features a bright, open-concept kitchen with sleek finishes, a large island, and ample storage, seamlessly flowing into a spacious living area; ideal for family gatherings and entertaining. Upstairs, the luxurious master suite offers a private retreat with a large ensuite bathroom, while three additional bedrooms provide plenty of space for guests, or a home office. At the top of the stairs, you'll find a versatile loft space, perfect for a playroom, media area, or additional lounge. Step outside to enjoy the expansive backyard, complete with a large privacy fence, offering plenty of space for families and pets to play or for hosting outdoor gatherings. This home is situated in a prime location, only a short distance to Dubsdread Golf Course. It’s also just minutes from Park Avenue, College Park, and Downtown Orlando, offering easy access to dining, shopping, and entertainment. Plus, with quick access to I-4, commuting anywhere in Central Florida is effortless. This home is truly a rare find. Don’t miss your chance to make it yours, schedule your showing today!

Beds:
3
Baths:
2.00
Sq.Ft.:
2,309
Status:
NEW LISTING
MLS#:
O6289193
Type:
Single Family
Subdivision:
Winter Park Pines
Lot size:
0.2 Acres
Year built:
1963
A broker reciprocity listing Courtesy: KELLY PRICE & COMPANY LLC 407-645-4321
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ADDITIONAL INFORMATION

Beautifully updated and FURNISHED 3-bedroom, 2-bath home in the desirable Winter Park Pines neighborhood is truly move-in ready! Fully renovated in 2019, the home boasts a range of high-end features, including hardwood flooring, designer fixtures, custom crown molding, and 5.25” baseboards throughout the majority of the home. Open floor plan is an inviting space for both living and entertaining. Wonderful chef’s kitchen, complete with Quartz countertops, large island, floor-to-ceiling cabinetry with under-cabinet lighting, soft-close doors and drawers, and stainless steel appliances, including fridge, convection oven, dishwasher, microwave, and dry bar. Skylights and double-pane windows flood the space with natural light. The spacious living and dining areas flow seamlessly. Multiple sitting areas. Large walk-in pantry, mudroom and laundry room. Great room / game room, or home office, features French doors that open onto a screened-in porch, ideal for relaxing. Outdoor patio, dry shed and privacy provided by the lush landscaping and fencing. The primary bedroom is a retreat, and features a stunning, large frameless shower, custom dual vanity with quartz countertops, and an oversized walk-in closet. Two additional bedrooms are generously sized, offering views of the front and side yards, and share an improved bathroom. This home is packed with upgrades including a new water heater (2024), new roof (2023), newer indoor electrical panel, and re-plumbing completed in 2017, along with a 2016 HVAC system. A well for 3- zoned irrigation, providing free water for your landscaping. Located just minutes from the Winter Park Pines Golf Course, Cady Way Bike Trail, pool, pickleball/tennis courts, playground, sports fields, and shopping, as well as Winter Park Hospital, this home offers the perfect blend of convenience and luxury. Zoned for Winter Park schools, with an optional HOA, it’s an excellent investment opportunity as well. Close to Rollins College and Full Sail. Enjoy mature, green trees, sidewalks for biking and walking in this charming and sought-after neighborhood.

Beds:
1
Baths:
1.00
Sq.Ft.:
549
Status:
NEW LISTING
MLS#:
O6289736
Type:
Condo
Subdivision:
Colonies
Lot size:
10.07 Acres
Year built:
1974
A broker reciprocity listing Courtesy: CASTLE & COTTAGE REALTY LLC 407-620-9405
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ADDITIONAL INFORMATION

Charming Studio Condo Near UCF & Full Sail – Ideal Investment or Cozy Retreat! Welcome to this well-maintained ground-floor studio condo, offering 549 square feet of comfortable living space in a prime location near UCF and Full Sail University. Perfect for a student, professional, or investor, this move-in-ready unit features tile flooring throughout, making it clean and easy to maintain. Enjoy a bright and open layout, a well-equipped kitchen, and a full bathroom, all designed for convenience and efficiency. Step outside to your private covered patio, where you can relax while overlooking the serene courtyard setting. Whether you’re looking for a low-maintenance home or a smart investment opportunity, this condo checks all the boxes. Schedule your showing today!

Beds:
2
Baths:
2.00
Sq.Ft.:
1,067
Status:
NEW LISTING
MLS#:
V4941401
Type:
Condo
Subdivision:
Four Seasons Condo
Lot size:
19.03 Acres
Year built:
1970
A broker reciprocity listing Courtesy: BETTER HOMES & GARDENS RE STAR 321-868-5555
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ADDITIONAL INFORMATION

FOUR SEASONS CONDO IN Winter Park is Centrally located. Great community with a clubhouse, a fitness center recently renovated, 3 swimming pools, tennis courts, and shuffleboard court. Close by you are only a short walk to Cady Way Park for baseball and soccer fields as well as other playgrounds. This 2 bedrooom/2 bath unit has been updated with laminate flooring, ceiling fans, all appliances including washer and dryer. Very close to Advent Health, Winter Park Hospital and all the shopping on Park Avenue, Rollins College, UCF, Valencia Communtiy College. 2 pets allowed :). THis is absolutely a prime location within Winter Park!

Beds:
2
Baths:
2.00
Sq.Ft.:
1,088
Status:
NEW LISTING
MLS#:
O6287695
Type:
Condo
Subdivision:
Andalucia Apts
Lot size:
0.61 Acres
Year built:
1972
A broker reciprocity listing Courtesy: FANNIE HILLMAN & ASSOCIATES 407-644-1234
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ADDITIONAL INFORMATION

Location, Location, Location - downtown Winter Park condo for under $500K! This dramatic 2 bedroom - 2 Bath ground floor unit is located on corner of Swoop and Interlachen, steps from the Winter Park 9 Golf Course and Park Avenue! Beautiful views, glassed in porch overlooking stunning landscape. This unit offers high ceilings, open, updated kitchen to living areas, sunroom (enclosed porch) large primary suite and guest room. Two full baths. Large utility room. Designer lighting. Open floor plan, light and bright! A/C 2018. The charming Andalucia complex, which consists of only 20 units, offers access to a lovely covered patio downstairs, an elevator, courtyard, and a community laundry room. The community also provides a private storage room for this unit. The roof was replaced in 2024. The exterior was painted, and new gates were installed in 2018. One covered parking space is included. Additional guest parking is available in the rear. The condo fee covers water, sewer, Spectrum WiFi and cable TV, landscaping and exterior maintenance, garbage, insurance on the exterior building, and reserves. Please note: No pets or rentals allowed. Call today for your private viewing of this special unit.

Beds:
4
Baths:
3.00
Sq.Ft.:
2,046
Status:
NEW LISTING
MLS#:
O6289998
Type:
Single Family
Subdivision:
Kenilworth Shores Sec 04
Lot size:
0.21 Acres
Year built:
1964
A broker reciprocity listing Courtesy: CHARLES RUTENBERG REALTY ORLANDO 407-622-2122
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ADDITIONAL INFORMATION

Welcome to this beautifully renovated 4-bedroom, 2.5-bath home in the heart of Winter Park, just minutes from Park Avenue’s top dining and shopping. Thoughtfully updated from top to bottom, this move-in-ready home features a brand-new AC system, luxury vinyl plank flooring throughout, and a stunning chef’s kitchen with quartz waterfall countertops, custom cabinetry, and all-new stainless steel appliances. Each bathroom has been modernized with sleek, contemporary finishes, while the spacious primary suite offers a private retreat with a beautifully updated ensuite. Outside, the fully fenced backyard provides a perfect space for relaxation or entertaining, and the two-car garage offers ample storage with easy access to the main living areas. Situated in a prime location with convenient access to I-4 and SR-417, this home blends modern elegance with unbeatable convenience. Don’t miss your chance to experience Winter Park living at its best—schedule your showing today!

Beds:
3
Baths:
3.00
Sq.Ft.:
1,801
Status:
NEW LISTING
MLS#:
O6289327
Type:
Townhouse
Subdivision:
Grayson Square
Lot size:
0.05 Acres
Year built:
2023
A broker reciprocity listing Courtesy: LPT REALTY, LLC 877-366-2213
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ADDITIONAL INFORMATION

Nestled in the coveted Grayson Square community of highly desired Winter Park, FL, 2037 Canny Cove Lane is a contemporary 3-bedroom, 2.5-bath townhome built in 2023. The open-concept layout features a stylish kitchen with stainless steel appliances, quartz countertops, and ample storage, seamlessly flowing into the spacious gathering room. The owner's suite offers a private retreat with an en-suite bathroom, complemented by two additional bedrooms and a shared full bath. Located in a gated community with amenities like a gorgeous pool and high-speed internet and cable, this property provides serene living with access to the neighboring grass space as a maintenance free yard, and side entry, full two car garage and easy access to local attractions, dining, shopping, and major highways.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,627
Status:
NEW LISTING
MLS#:
O6289675
Type:
Single Family
Subdivision:
Bel Aire Pines
Lot size:
0.23 Acres
Year built:
1981
A broker reciprocity listing Courtesy: KELLER WILLIAMS REALTY AT THE PARKS 407-629-4420
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ADDITIONAL INFORMATION

**This property qualifies for a closing cost credit up to $6,600 through the Seller’s preferred lender.**Welcome home to this 3-bedroom, 2-bathroom home located in the highly desirable Winter Park community of Bel Air Pines. Offering the perfect blend of modern amenities and classic style, this home is sure to check the boxes and more! The front screened-in porch with its charming arched detailing invites you to relax and enjoy the Florda breeze. As you enter the foyer, you’ll see the hallway to your right connecting all three bedrooms and both updated bathrooms. The open concept living and dining areas are perfect for entertaining, with plenty of natural light and a seamless flow for gatherings. The kitchen around the corner features updated white cabinetry, stainless steel appliances, and quartz countertops, offering both style and functionality. Sliding glass doors open from the living area to the backyard, extending your space for indoor-outdoor living. The spacious backyard is the perfect space to store your RV, trailer, or boat with an 8-foot privacy fence surrounding. Recent upgrades include new windows and sky lights, replumbed and new breaker box in 2015, soffit and gutters and facia and new hot water heater in 2020, all new exterior lights, and the attic has R18 pest repellent insulation. Zoned for winter Park High School, this amazing location offers amazing dining and shopping being close to Downtown Winter Park and Orlando and easy access to major highways. Schedule your private showing today!

Beds:
3
Baths:
2.00
Sq.Ft.:
1,322
Status:
NEW LISTING
MLS#:
S5122564
Type:
Single Family
Subdivision:
Eastgate Sub
Lot size:
0.19 Acres
Year built:
1956
A broker reciprocity listing Courtesy: EXP REALTY LLC 888-883-8509
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ADDITIONAL INFORMATION

This 3-bedroom, 2-bathroom single-family home in Winter Park, Florida, offers a prime location and a fantastic lot for investors or future homeowners looking to create their dream property. Located on a 0.19-acre lot (75x110) with no HOA, THE VALUE HERE LIES IN THE LAND & IT'S POTENTIAL! The property features a Florida sunroom and a carport, providing some existing space for reimagining. Whether you’re looking to fix and flip, renovate and hold, or build from the ground up, this lot provides endless possibilities for your next project. With only 0.5 miles to AdventHealth Winter Park and Winter Park Corners Plaza (restaurants, shopping, and more), and just 2 miles from Downtown Winter Park’s vibrant mix of entertainment, parks, restaurants, museums, the Winter Park Chain of Lakes, and weekend farmers markets, the location is ideal for those who want to be in the heart of it all. Don't miss taking advantage of this opportunity to invest in a prime lot in the highly desirable Winter Park area with easy access to everything the area has to offer. The possibilities are endless!

Beds:
5
Baths:
5.00
Sq.Ft.:
4,912
Status:
NEW LISTING
MLS#:
O6289369
Type:
Single Family
Subdivision:
Comstock Park
Lot size:
0.34 Acres
Year built:
2003
A broker reciprocity listing Courtesy: FANNIE HILLMAN & ASSOCIATES 407-644-1234
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ADDITIONAL INFORMATION

Nestled on a serene, brick-paved street in the heart of Winter Park, this elegant 5-bedroom, 3.2-bathroom pool home is situated on a stunning oversized lot. Custom-built in 2003, it offers a thoughtful floor plan that adapts beautifully to any lifestyle. From the moment you arrive, this home welcomes you with timeless charm and a sense of warmth. Inside, expansive windows, rich wood flooring, and exquisite millwork create an atmosphere of sophistication. Upon entering, you’re greeted by breathtaking views of the lushly landscaped backyard, complete with a sparkling pool and spa. The main level features a luxurious primary suite with picturesque views of the outdoor retreat. The primary bath is a sanctuary, offering dual sinks, a jacuzzi tub, a separate shower with dual showerheads, dual walk-in closets, and a private water closet. Adjacent to the suite is a dedicated home office, ideal for remote work or quiet study. Perfect for hosting, the spacious dining room is ready for memorable gatherings. The chef’s kitchen is a true centerpiece, outfitted with custom Busby cabinetry, GE Monogram appliances, a 6-burner gas cooktop with dual ovens, and a cozy breakfast nook that overlooks the backyard. The kitchen opens seamlessly to the family room, creating a welcoming space for everyday living and entertaining. French doors from the family room, living room, and primary bedroom provide effortless access to the backyard. The outdoor space is a true escape, featuring a sparkling pool and spa, lush greenery, and a custom summer kitchen, perfect for enjoying time with family and friends. Upstairs, four generously sized bedrooms are paired with Jack-and-Jill bathrooms, each offering dual sinks and a shared tub or shower. A cozy loft area adds flexibility to the second floor. Above the 3-car garage, a spacious bonus room doubles as a theater or playroom, and is equipped with additional storage space. Lovingly maintained by its original owner, this pristine home combines elegance and convenience, with walkability to Phelps Park, the YMCA, Interlachen Country Club, and Park Avenue. It’s a rare find in one of Winter Park’s most desirable neighborhoods.

Beds:
2
Baths:
1.00
Sq.Ft.:
912
Status:
NEW LISTING
MLS#:
O6288240
Type:
Townhouse
Subdivision:
Windward Square Sec 2
Lot size:
0.05 Acres
Year built:
1977
A broker reciprocity listing Courtesy: CREEGAN GROUP 407-622-1111
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ADDITIONAL INFORMATION

Don’t miss out on a great opportunity to own a SINGLE-STORY, LOW HOA townhouse in Winter Park’s popular Windward Square community. Imagine yourself enjoying any of its three pools, tennis courts, BBQ area, or outdoor reading benches AND being located a mere 5 minutes from grocery shopping and dining esablishments. More shopping, dining, and opportunities to just relax and watch busy shoppers are available nearby, in Winter Park’s downtown Park Avenue district. This two-bedroom, no carpet unit offers a living/dining room combo with beautiful morning light. In addition to its smartly situated full bathroom, a separate sink and dressing area is available in the master bedroom, for owner convenience. Walk-in closets are found in both bedrooms, and the townhouse has a designated laundry closet, too (washer and dryer convey). Sliding patio doors open to a fully-fenced backyard, affording privacy and the ability to garden, BBQ, or watch Fido play. An exterior storage closet provides space for yard or hobby items you own. You will love the 3-car parking pad right in front of your unit. No more searching for visitor parking spots! Just around the corner you’ll find the clubhouse and all the community amenities that give Windward Square its “easy living” reputation. Schedule your private showing today! ROOF: 2023 HVAC: 2023

Beds:
5
Baths:
5.00
Sq.Ft.:
4,770
Status:
NEW LISTING
MLS#:
O6286245
Type:
Single Family
Subdivision:
Kenilworth Shores Sec 01
Lot size:
0.3 Acres
Year built:
2025
A broker reciprocity listing Courtesy: COMPASS FLORIDA LLC 407-203-9441
View additional info

ADDITIONAL INFORMATION

Located in the heart of Winter Park this exquisite modern residence built by Vimaro Homes features almost 5,000 square feet of luxury living space. As you step through the glass front doors, you’re immediately greeted by the grandeur of the marble entry floors and custom archways, setting the tone for the exceptional finishes throughout this stunning home. From the gorgeous wood floors laid in a herring bone pattern, to the designer light fixtures, arched doorways, and beautiful mill work, no expense was spared in the construction of this remarkable residence. The chef’s kitchen features exquisite custom cabinetry, marble countertops, a massive butler’s pantry, top of the line appliances including a ILVE Nostalgie range, and a wine cellar. The great room features a wall of glass that opens to the spacious covered lanai blending the indoor and outdoor spaces. The primary bedroom suite overlooks the private back yard and features a spa bath that would rival even the most prominent spas. Last but not least there is a massive walk in closet with separate his and hers sections, and a washer and dryer. Additional features include a first-floor game room, home office, formal dining room, a second floor loft area, 4 additional bedrooms, and second floor laundry room. Situated on a spacious lot, this property features a circular driveway, and a large, fenced yard with mature landscaping, perfect for outdoor activities and entertaining. The highlight of this home is the inviting pool, providing a refreshing oasis for those hot summer days. Jump on your golf cart and within minutes you’re transported to Park Ave, with its amazing shops, fine dining, and everything else that Winter Park has to offer. Don’t miss your opportunity to own this stunning Winter Park home crafted by renowned builder Vimaro Homes.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,409
Status:
NEW LISTING
MLS#:
O6289597
Type:
Single Family
Subdivision:
Winter Park Estates
Lot size:
0.28 Acres
Year built:
1958
A broker reciprocity listing Courtesy: CENTURY 21 CARIOTI 407-354-0074
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ADDITIONAL INFORMATION

Welcome to this charming 3-bedroom, 2-bathroom single-story home, perfectly located in highly sought-after Winter Park. Situated on a beautiful corner lot, this property offers the ultimate in convenience and charm, with the added bonus of NO HOA! Ideal for first-time homebuyers or investors, this home boasts low-maintenance tile and laminate flooring throughout. The spacious living room is the heart of the home, featuring a cozy fireplace, a striking brick accent wall, and high ceilings that create an open and inviting atmosphere. The living area seamlessly flows into the dining room, which offers stunning views of the private backyard through glass sliders—perfect for indoor-outdoor living. The well-equipped kitchen includes all appliances, making it easy to move right in. Both bathrooms are beautifully designed with pedestal sinks and tiled surfaces for a sleek, clean look. The oversized 2-car side-entry garage is a standout feature, with high ceilings, a laundry room, and a dedicated workroom, offering plenty of storage and potential for projects. Conveniently located just minutes from Rollins College, Winter Park Pines Golf Course, Cady Way Trail, Downtown Winter Park and Park Avenue you’ll be surrounded by parks, shops, restaurants, and venues. This home is also zoned for top-rated schools, making it an ideal choice for families. Additional highlights include brand-new garage doors and openers (2025), AC and Air Handler (2022) and Washer and Dryer are included. This home offers an incredible opportunity in one of Winter Park's most desirable locations—schedule your showing today!

Beds:
4
Baths:
3.00
Sq.Ft.:
1,904
Status:
NEW LISTING
MLS#:
O6288529
Type:
Single Family
Subdivision:
Winter Woods Unit 02
Lot size:
0.19 Acres
Year built:
1970
A broker reciprocity listing Courtesy: COLDWELL BANKER REALTY 407-696-8000
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ADDITIONAL INFORMATION

Discover a rare investment opportunity tucked away in the heart of Winter Park, this 4-bedroom, 3-bathroom home is brimming with potential. Overlooking a green scenic golf course, this property offers a prime location, spacious layout, and endless possibilities. Whether you're looking for a home with character or a rewarding renovation project, this is a golden opportunity you don’t want to miss! As you arrive, the inviting curb appeal sets the tone. Lush landscaping and a welcoming front porch make a statement before you even step inside. The entryway leads to a formal living and dining room, ideal for gatherings or quiet moments at home. Just beyond, you’ll find the first primary suite—complete with a private full bath and walk-in closet—offering comfort and convenience. The heart of the home is the kitchen, overlooking a huge family room with eye-catching wood beams. Natural light pours in through the sliding glass doors. The second primary suite sits on the opposite side of the house, providing a private retreat with an en-suite bathroom. Two additional bedrooms share another full bath, offering ample space and flexibility. Step outside and take in the peaceful greenery views. Whether you dream of creating an outdoor entertainment area, adding a garden, or simply enjoying the open space, this backyard is ready to be transformed. This home includes a newer roof (2023), replumb (2011), HVAC (2016), however renovations are needed throughout entire home. With an optional HOA and an unbeatable location, this home places you just minutes from Park Avenue, top-rated Seminole County schools, Rollins College, UCF, Full Sail, and an array of shopping and dining options. This diamond in the rough is being sold AS IS—bring your creativity and make it shine!

Beds:
2
Baths:
2.00
Sq.Ft.:
1,020
Status:
NEW LISTING
MLS#:
O6289538
Type:
Condo
Subdivision:
Winter Park Woods Condo
Lot size:
0.2 Acres
Year built:
1974
A broker reciprocity listing Courtesy: NEXTHOME DIVERSIFIED 321-914-0014
View additional info

ADDITIONAL INFORMATION

Auction Property. Online auction starts MARCH 24, 2025 at 11 AM EST on Federa. Discover this charming 2-bedroom, 2-bathroom condo offering a wonderful opportunity to reside in a desirable Orlando neighborhood. An auction deposit is required to bid, which will be applied to the sale price of the winning bid. Sold As-is. No showings. Explore more details and register for the auction through the Federa Home App.

Beds:
5
Baths:
5.00
Sq.Ft.:
4,129
Status:
NEW LISTING
MLS#:
O6289194
Type:
Single Family
Subdivision:
Forest Hills
Lot size:
0.58 Acres
Year built:
1998
A broker reciprocity listing Courtesy: KELLY PRICE & COMPANY LLC 407-645-4321
View additional info

ADDITIONAL INFORMATION

Just Listed ~ Stunning lakefront home in Winter Park that has been completely remodeled and offers 4 bedrooms, a bonus room, and guest apartment! This home is exquisite from top to bottom and features elevated ceilings, crown moldings, designer fixtures and wall coverings. Large picture windows overlook Lake Sue from the living room, dining room, and kitchen. The kitchen is gorgeous and offers chef-grade appliances, a large center island, plenty of soft-closed cabinetry for storage, and an open-concept layout for inclusive entertaining. French doors open off the family room to seamlessly blend the indoor/outdoor living space. A covered lanai with outdoor kitchen overlooks the beautiful, resort-inspired, heated pool and spa, multi-level summer terrace with gardens, and the custom 3-hole putting course. Back inside, located on the 2nd floor, the primary suite has a Juliette balcony that overlooks the shores of Lake Sue and features an en suite bath with a double-headed shower, separate soaking tub and double-sink vanity. An oversized guest suite with private bath and two bedrooms and a hall bath complete the second floors. On the first floor is a bonus room (ideal for use as a playroom, home office, or studio), a full bath, and laundry room. Above the detached 2-car garage is an apartment with a kitchenette and full bath with walk-in shower. The expansive 0.58 acre property extends over the charming brick street and includes a large, park-like green space, shaded beneath majestic oaks, s small beach area, elongated dock, and boathouse (no lift). Located within minutes of Park Avenue, this lakefront estate is a short walk or bike ride to nearby shops and dining and is zoned for one of the best school districts in the area. Audubon Park, Baldwin Park, the Mills District, and Downtown Orlando are all within a 10-minute drive. Showings are by appointment only – schedule yours today.

Beds:
3
Baths:
3.00
Sq.Ft.:
1,762
Status:
NEW LISTING
MLS#:
O6289116
Type:
Condo
Subdivision:
Arbors/aragon
Lot size:
0.03 Acres
Year built:
2004
A broker reciprocity listing Courtesy: KELLER WILLIAMS WINTER PARK 407-545-6430
View additional info

ADDITIONAL INFORMATION

This beautifully updated 3 bedroom, 3 bath home offers a perfect blend of rustic charm and modern convenience in a highly desirable location. The open floor plan is warm and inviting, with stylish finishes and thoughtful updates that make it truly move-in ready. Each bedroom features its own ensuite bath and a spacious walk-in closet, with both upstairs suites offering the flexibility to serve as a primary retreat. Recent improvements include a brand new hot water heater, new refrigerator, an added mini-split in the garage for enhanced comfort, a water softener system, and a recently replaced A/C. The fenced backyard has been upgraded to turf for easy maintenance, complemented by a private deck—perfect for relaxing or entertaining. Two balconies, including one with a view of the Rollins College baseball field, provide additional peaceful retreats. The attached two-car garage offers both convenience and extra security. Located within walking distance of Park Avenue, Rollins College, and Hannibal Square, this home provides easy access to shopping, dining, and entertainment while maintaining a quiet and private feel. A rare opportunity in an unbeatable location—don’t miss it!

Beds:
4
Baths:
5.00
Sq.Ft.:
3,121
Status:
NEW LISTING
MLS#:
S5122502
Type:
Single Family
Subdivision:
Pelican Bay
Lot size:
0.57 Acres
Year built:
1984
A broker reciprocity listing Courtesy: TRANSCEND REALTY 407-518-7653
View additional info

ADDITIONAL INFORMATION

A True Gem on the Lake! If you've been dreaming of owning a lakefront property with a Winter Park address, this is your chance! This stunning 4-bedroom, 2.5-bathroom home in the tranquil Pelican Bay Subdivision is move-in ready and full of charm. As you approach, you'll be greeted by lush landscaping. Step through the double front doors into a welcoming foyer with beautiful wood floors and modern accents. An elegant oak staircase with iron rails leads you upstairs to three spacious bedrooms, a loft, a bathroom, and a private patio. The heart of the home lies downstairs, where you’ll find a modern kitchen with upgraded appliances, granite countertops, and wood cabinets. A large island/breakfast bar overlooks the family room, where you can take in breathtaking lake views. Enjoy formal gatherings in the separate dining and living rooms, each offering plenty of space and comfort. The downstairs primary suite boasts serene lake views and features exquisite built-in cabinets, renovated master bath with dual sinks, a large glass-enclosed walk-in shower, and an expansive walk-in closet. The screened-in lanai is the perfect place to relax or entertain, with a jacuzzi, wet bar, and plenty of counter space. Whether it’s morning coffee, afternoon relaxation, or evening sunsets, you’ll love the view of the lake all day long. The dock is an ideal spot for fishing, relaxing, or simply enjoying the tranquil surroundings. Major renovations to the home were done in 2017 including mostly new new windows throughout, dock, all bathrooms and flooring. New roof installed in 2021. This home truly has it all. Don’t miss out—schedule a tour today!

Beds:
4
Baths:
2.00
Sq.Ft.:
2,124
Status:
NEW LISTING
MLS#:
O6288881
Type:
Single Family
Subdivision:
Wrenwood Heights
Lot size:
0.21 Acres
Year built:
1972
A broker reciprocity listing Courtesy: KELLER WILLIAMS ADVANTAGE REALTY 407-977-7600
View additional info

ADDITIONAL INFORMATION

Welcome to 4991 Tangerine Ave in the heart of Winter Park! This charming 4-bedroom, 2-bathroom home offers comfortable living with no carpet throughout—perfect for easy maintenance. The spacious family and dining room combination provides an open and inviting layout, ideal for gatherings. A large, air-conditioned Florida room adds even more flexibility, ensuring plenty of space for entertaining. The generously sized bedrooms offer comfort and versatility to fit your needs. Step outside to your beautiful backyard oasis, featuring a sparkling pool and additional yard space for relaxation or recreation. With no HOA and zoning for top-rated schools, this home is a rare find in a fantastic location. Don’t miss this incredible opportunity!

Beds:
3
Baths:
2.00
Sq.Ft.:
1,050
Status:
NEW LISTING
MLS#:
O6289464
Type:
Single Family
Subdivision:
Brookshire Hgts 1st Add
Lot size:
0.2 Acres
Year built:
1959
A broker reciprocity listing Courtesy: HOME WISE REALTY GROUP, INC. 407-712-2000
View additional info

ADDITIONAL INFORMATION

Great house in sought after neighborhood. The home is close to Brookshire Elementary, Winter Park High, Cady Way trail, Cady Way pool, and Showalter Home has an inviting front porch with swing, storm door with decorative front door, open floor concept for family room, dining room and kitchen. The screened in back porch overlooks a nice fenced in yard. This home won't last long.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,867
Status:
NEW LISTING
MLS#:
O6289177
Type:
Single Family
Subdivision:
Greenview At Winter Pines
Lot size:
0.2 Acres
Year built:
1979
A broker reciprocity listing Courtesy: HOPKEY REALTY 407-454-1217
View additional info

ADDITIONAL INFORMATION

Experience luxury living in this stunning 3-bedroom, 2-bathroom pool home perfectly positioned on the 3rd hole of the golf course in Winter Park. Thoughtfully upgraded with designer details, this home blends elegance and comfort. A beautifully tiled walkway leads to an inviting interior featuring crown moldings, wood-look porcelain flooring, energy-efficient LED lighting, and stylish fixtures throughout. To the right, a versatile office/flex space with custom built-ins offers the potential for a 4th bedroom filled with natural light. The chef’s dream kitchen boasts custom soft-close cabinets with pull-out shelves, stainless steel appliances, and a massive island with extra storage, perfect for entertaining. Flowing into the family room with built-in cabinetry, a wood-burning fireplace, and surround sound, this space seamlessly connects to the expansive patio and sparkling pool with waterfall, all protected by golf ball-resistant screens and windows. The living room features built-in cabinets for additional storage and functionality. French doors create a smooth indoor-outdoor transition, ideal for gatherings. The primary suite features an extra seating area, a large converted walk-in closet (originally the 4th bedroom), and an en-suite with warm-toned tile, a walk-in shower, and designer fixtures. The additional bedrooms offer ample space, new carpeting with a 25-year warranty, and generous closets. Spray foam insulation between the trusses enhances energy efficiency and comfort year-round. For peace of mind, the home includes exterior security cameras, fresh exterior paint, an expanded concrete driveway, and a new state-of-the-art water heater. Major updates include a roof (2013), AC (2017), and full repipe (2024). Located in an area with top-rated schools, this home is perfect for families. Conveniently across from Cady Way Trail and near the Golf & Country Club, which is owned by Winter Park and hosts community events, a restaurant, and a bar, this home offers easy access to downtown Winter Park and Baldwin Park’s top restaurants, entertainment, and attractions. Don’t miss this exceptional opportunity—schedule your private tour today!

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Andrea Conner, License #BK3437731, Xome Inc., License #1043756, [email protected], 844-400-9663, 750 State Hwy 121 Bypass, Suite 100, Lewisville, TX 75067


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Winter Park Real Estate

Winter Park is located in Florida. Winter Park, Florida has a population of 29,672. Winter Park is less family-centric than the surrounding county with 27.95% of the households containing married families with children. The county average for households married with children is 31.51%.

The median household income in Winter Park, Florida is $88,688. The median household income for the surrounding county is $65,784 compared to the national median of $69,021. The median age of people living in Winter Park is 45.3 years.

Winter Park Weather

The average high temperature in July is 92 degrees, with an average low temperature in January of 49.4 degrees. The average rainfall is approximately 51.9 inches per year, with 0 inches of snow per year.

Winter Park Map

Winter Park Real Estate Market Conditions

  • Median sales price

    $468,000
    25.3%
    change since last quarter
  • # Active listings

    377
    30-day change

Winter Park Schools and Demographics

Education near Winter Park, FL

City County
High School Graduates 96.78 89.47
College Degree - 2 year 9.01 11.45
College Degree - 4 year 62.48 35.7
Graduate Degree 17.77 9.12
Expenditures per Student 12,701 12,701
Students per Teacher 17.3 17.3

Elementary Schools near Winter Park, FL

Grades Students P/T Ratio ZIP
Aloma Elementary School PK - 05 528 15.5 32792
Aspire Academy Charter KG - 05 111 8.5 32804
Audubon Park Elementary School PK - 05 1,182 14.8 32814
Brookshire Elementary School PK - 05 632 12.9 32792
Dommerich Elementary School PK - 05 603 15.1 32751
Eastbrook Elementary School PK - 05 809 14.2 32792
Fern Creek Elementary School PK - 05 326 12.1 32803
Hillcrest Elementary School PK - 05 463 14.5 32803
Hungerford Elementary School PK - 05 283 13.5 32751
Killarney Elementary School KG - 05 444 14.8 32789
Lake Silver Elementary School PK - 05 688 12.3 32804
Lake Sybelia Elementary School PK - 05 600 13.3 32751
Lakemont Elementary School KG - 05 656 14.6 32792
Orlando Science Elementary Charter KG - 05 482 15.1 32804
Princeton Elementary School PK - 05 488 13.2 32804

Middle Schools near Winter Park, FL

Grades Students P/T Ratio ZIP
Glenridge Middle School 06 - 08 1,415 18.4 32814
Maitland Middle School 06 - 08 909 18.9 32751
Robert E Lee Middle 06 - 08 1,034 17.2 32804

High Schools near Winter Park, FL

Grades Students P/T Ratio ZIP
Edgewater High School 09 - 12 1,782 20 32804
Lake Howell High School 09 - 12 2,229 19.1 32792
Winter Park High School 09 - 12 3,069 18.7 32792
Workforce Advantage Academy Charter 09 - 12 238 47.6 32803

Ungraded Schools near Winter Park, FL

Grades Students P/T Ratio ZIP
* Aloma High Charter School 09 - 12 510 42.5 32792
* Winter Park Education Center 11 - 12 0 32789
Broward Science Charter School UG - UG 0 32804
Central Florida Leadership Academy Charter 06 - 12 189 15.8 32803
Gateway 06 - 12 63 3.7 32804
Hospital Homebound PK - 12 229 4 32804
La Amistad School KG - 12 48 9.6 32751
Orlando Science Middle High Charter School 06 - 12 555 15.4 32804
Pace Center for Girls 06 - 12 34 6.8 32803
Silver Star Center 06 - 12 25 2.5 32804
Winter Park Tech AE - AE 0 32789

Demographics near Winter Park, FL

City County
Neighborhood Type Suburban
Population 29,672 1,409,949
Population Density 3,393 1,562
Median Age 45.3 35.7
People per Household 2.3 2.9
Median Household Income 88,688 65,784
Average Income per Capita 67,032 33,498

Real estate near Winter Park