Winter Park FL Real Estate & Homes for Sale

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Beds:
3
Baths:
2.00
Sq.Ft.:
2,114
Status:
Active
MLS#:
O6290084
Type:
Single Family
Subdivision:
Cortland Park
Lot size:
0.19 Acres
Year built:
1981
A broker reciprocity listing Courtesy: EXP REALTY LLC 888-883-8509
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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:
n/a
Baths:
1.00
Sq.Ft.:
549
Status:
Active
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

NEW PRICE!!! 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:
3
Baths:
2.00
Sq.Ft.:
1,230
Status:
Active
MLS#:
O6285927
Type:
Condo
Subdivision:
Goldenrod Villas Condo
Lot size:
0.03 Acres
Year built:
1984
A broker reciprocity listing Courtesy: REALTY TECH INC 407-332-9757
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ADDITIONAL INFORMATION

Great investment opportunity. Ideal for a growing family or investor. Well established neighborhood of Goldenrod Villas, 3 bedroom, 2 full bathrooms, 1,230 square feet of living area. Exterior of the home is concrete block and stucco. The eat-in-kitchen sits in the heart of the home which creates a warm and social atmosphere. Nice covered patio with back yard great for relaxing and entertaining family and friends. Come and make it your own. The HOA maintains building exterior, roof, and exterior landscape maintenance. The Community features enjoyable sparkling swimming pool and clubhouse. Great location! Conveniently located to nearby shopping, schools, banks, medical centers, and restaurants as well as easy access to major highways. Don't miss it. Priced to sell. Will Not Last!

Beds:
3
Baths:
2.00
Sq.Ft.:
1,149
Status:
Active
MLS#:
O6285607
Type:
Condo
Subdivision:
Waterfall Cove At Winter Park
Lot size:
0.41 Acres
Year built:
1966
A broker reciprocity listing Courtesy: PRIMESTATE REALTY, INC. 407-850-9494
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ADDITIONAL INFORMATION

This property located in a peaceful community IN WINTER PARK. and easy access to FL I-4 , short drive distance to Rollins College, UCF, Valencia college, Hospitals, shopping center, restaurants and Orlando Theme Park. This unit located on the second floor, it has 3 bedrooms 2, bathrooms, open floor plan. The community amenities include a large pool with lounge chairs, playground and gazebo. This property can be leased. You must see for any possibilities come and check for yourself. Registered owner is brother of the realtor. SELLER MIGHT HOLD FIRST MORTGAGE WITH A GOOD DOWN PAYMENT.

Beds:
5
Baths:
7.00
Sq.Ft.:
6,406
Status:
Active
MLS#:
O6282425
Type:
Single Family
Subdivision:
Comstock Park
Lot size:
0.36 Acres
Year built:
2024
A broker reciprocity listing Courtesy: PREMIER SOTHEBY'S INTL. REALTY 407-644-3295
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ADDITIONAL INFORMATION

New Hamptons-style residence offering a seamless blend of elegance and modern sophistication. A gated entrance opening to a circular driveway and motor court, set the stage for enjoying this exceptional estate. As you enter home, an impressive 2-story foyer with a glass-paneled staircase wraps around a temperature-controlled wine room and a transparent glass elevator, effortlessly connecting all levels including an expansive third-floor multi-purpose space. Designed for contemporary living, the thoughtfully curated floor plan features a spacious open concept kitchen/gathering room along with the dining area enjoy a wall of glass doors and picture window overlooking an expansive lanai, and serene backyard with a sparkling pool and spa. The main residence offers 4 bedrooms, private home office, and multiple flex spaces, complemented by a detached pool cabana that serves as a 5th guest retreat or versatile use building. The gourmet kitchen is an entertainer’s dream, featuring dual 10-foot stone islands, a 60-inch Wolf range, dual 36-inch Sub-Zero refrigerator and freezer columns, a warming drawer, beverage center and a 146-bottle Sub-Zero dual-zone wine cooler. A separate pantry kitchen is equipped with a Dacor induction cooktop, convection oven, additional refrigerator, microwave, dishwasher and ample cabinetry, ideal for catering and meal preparation. The 1st-level primary suite is a tranquil retreat, offering a sitting area, an all-marble bath with a glass-enclosed shower, multiple body sprays, a soaking tub, and French doors leading to a secluded Zen garden with an outdoor shower and fountain. There is also a hidden private home office near the front of home. The second level hosts 3 additional en-suite bedrooms, a generous lounge area, bar, and a well-appointed laundry room with extra storage cabinetry. As noted previously, there is also a unique 3rd level accessible by a staircase or elevator, that offers nearly 770 square feet of multi-use space. The outdoor living is elevated with a spacious lanai featuring motorized screens, a gas fireplace, dining space, and a summer kitchen with a 54-inch Coyote wood and gas grill, plus a separate burner beneath a remote-controlled louvered roof. There is also a detached cabana perfectly suited for a guest suite, fitness studio, additional office or game room, complete with a full bath, mini kitchen, and washer/dryer. Crafted with meticulous attention to detail, this home showcases Anderson windows, 10-foot solid doors, high-end lighting, plumbing and electrical fixtures, custom cabinetry built-ins, as well as Trane HVAC systems, ensuring quality and comfort... Lush landscaping, including magnolia trees, bamboo and cypress, surrounds the property, creating a private sanctuary. An attached side-entry garage features a powered car lift providing space for up to three vehicles. Ideally near Interlachen Country Club, Winter Park Racquet Club, Phelps Park/YMCA, and renowned Park Avenue. Note: Partial staging by RH and the furniture package can be purchased separately...

Beds:
2
Baths:
2.00
Sq.Ft.:
1,105
Status:
Active
MLS#:
OM695642
Type:
Condo
Subdivision:
Parkview Village
Lot size:
0.1 Acres
Year built:
1984
A broker reciprocity listing Courtesy: GLOBALWIDE REALTY LLC 352-456-9788
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ADDITIONAL INFORMATION

Condo in Winter Park, FL Welcome to 2923 Antique Oaks Cir, Unit 39 — a beautifully updated 1,105 sq. ft. first-floor condo offering 2 bedrooms, 2 bathrooms, and modern upgrades throughout. Located in the highly sought-after Winter Park School District, this property combines comfort, style, and convenience. Property Highlights: Size & Layout: Spacious 1,105 square feet with a thoughtfully designed floor plan. Updated Interiors: Recently remodeled with modern finishes, including appliances (convection oven, refrigerator, dishwasher), and washer/dryer in the interior laundry room. Outdoor Living: Relax on your private screened patio, perfect for morning coffee or evening unwinding. Community Features: Resort-Style Amenities: Enjoy a sparkling pool, a soothing hot tub, and meticulously maintained grounds. Pet-Friendly & Welcoming: Dog-friendly and community-oriented, providing a quiet and peaceful atmosphere. Prime Location: Zoned for A-rated Winter Park schools and just 2 miles away, this condo offers unmatched convenience: Walkable access to dining, shopping, and entertainment. Minutes from Park Avenue, Baldwin Park, Winter Park Hospital, and Downtown Orlando. Close to top educational institutions: Valencia College, Rollins College, Full Sail University, and UCF. With an HOA that provides excellent management and care, this is an incredible opportunity to own in a desirable and high-quality location.

Beds:
6
Baths:
4.00
Sq.Ft.:
2,284
Status:
Active
MLS#:
O6282473
Type:
Single Family
Subdivision:
Morseland Sub
Lot size:
0.19 Acres
Year built:
2015
A broker reciprocity listing Courtesy: RE/MAX TOWN & COUNTRY REALTY 407-695-2066
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ADDITIONAL INFORMATION

Welcome to this rare Winter Park gem offering unmatched flexibility and investment potential. Whether you’re looking for a turnkey rental property, a multigenerational living solution, or a home with a private in-law or student suite, this property delivers! Each spacious unit boasts 3 bedrooms and 2 bathrooms, designed with a modern, elegant aesthetic. With dual living areas, kitchens, and baths, this property offers endless possibilities for homeowners and investors alike. The interiors are thoughtfully designed with high-end finishes and contemporary touches throughout, including recessed lighting, sleek fixtures, and an open-concept layout that enhances the home’s bright and airy feel. The gourmet kitchens serve as the heart of each home, featuring 42” black cabinetry, granite or quartz countertops, decorative backsplashes, and stainless steel appliances, creating a stylish and highly functional space. The open living and dining areas offer a seamless flow, enhanced by ceramic tile and wood flooring that adds a sophisticated touch. The first-floor primary suites provide privacy and convenience, while additional bedrooms upstairs, along with a secondary living area, create a flexible layout perfect for guests, a home office, or growing families. Each bathroom is elegantly updated with sleek vanities, designer fixtures, and spa-like finishes, bringing luxury to everyday living. Strategically placed laundry areas add to the home’s functionality. Outside, the private paved backyard patios, enclosed by vinyl fencing, provide a serene space for outdoor relaxation, entertaining, or dining al fresco. The unbeatable location places you just steps from Park Avenue and Winter Park Golf Course, with easy access to the best dining, shopping, and outdoor recreation. The property is also near Rollins College, Winter Park Village, and the train station, making it a prime choice for both convenience and lifestyle. This duplex can be purchased separately or together (720 & 726 N Pennsylvania Ave) and even offers owner financing options—making it an ideal opportunity for an income-producing investment, multigenerational living, or a private in-law or student suite. Whether you’re looking to generate rental income, create a home for extended family, or enjoy a private dual-living setup, this property meets every need. Don’t miss your chance to own this exceptional property in one of Winter Park’s most sought-after locations. Schedule your private showing today!

Beds:
3
Baths:
2.00
Sq.Ft.:
1,115
Status:
Active
MLS#:
O6281659
Type:
Single Family
Subdivision:
Morseland Sub
Lot size:
0.1 Acres
Year built:
2015
A broker reciprocity listing Courtesy: RE/MAX TOWN & COUNTRY REALTY 407-695-2066
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ADDITIONAL INFORMATION

Nestled in one of Winter Park’s most sought-after locations, this 3-bedroom, 2-bathroom home seamlessly blends modern elegance with everyday comfort. From the moment you step inside, you'll be captivated by the sleek, contemporary finishes, recessed lighting, and stylish fixtures that enhance every space. The open living and dining room combo creates a bright and welcoming atmosphere, perfect for entertaining. The well-equipped kitchen is a chef’s dream, featuring quartz countertops, stainless steel appliances, and custom cabinetry, all designed to deliver both beauty and functionality. Both bathrooms are thoughtfully designed with modern vanities, sleek hardware, and spa-like finishes, creating a serene retreat. The primary suite offers a peaceful escape with its luxurious en-suite bath, while the additional bedrooms provide flexibility for guests, a home office, or family needs. Step outside to a private, paved backyard patio, enclosed by a vinyl fence, offering the perfect space for outdoor dining, entertaining, or simply unwinding. Located within walking distance to Park Avenue and Winter Park Golf Course, this home offers unparalleled access to top-tier dining, shopping, and outdoor recreation. It’s also just minutes from Rollins College, Winter Park Village, and the train station, making it an unbeatable choice for convenience and lifestyle. An exceptional opportunity, this property can be purchased separately or together with the attached home at 726 N Pennsylvania Ave—and even offers owner financing options—making it an ideal opportunity for an income-producing investment, multigenerational living, or a private in-law or student suite. Don’t miss this chance to own a modern, stylish home in the heart of Winter Park! Schedule your private showing today.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,167
Status:
Active
MLS#:
O6281654
Type:
Single Family
Subdivision:
Morseland Sub
Lot size:
0.09 Acres
Year built:
2015
A broker reciprocity listing Courtesy: RE/MAX TOWN & COUNTRY REALTY 407-695-2066
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ADDITIONAL INFORMATION

Welcome to this beautifully designed 3-bedroom, 2-bathroom home, offering a blend of modern elegance and prime location. The gourmet kitchen boasts 42” black cabinets, granite countertops, a decorative backsplash, and stainless steel appliances, making it a stunning focal point of the home. The open-concept dining and living room create a spacious feel, while ceramic tile and wood floors enhance the home's stylish appeal. The first-floor primary suite provides convenience and privacy, while the laundry room is strategically located behind the kitchen. Upstairs, you’ll find an additional living area, two bedrooms, and a full bathroom, offering a flexible layout for guests or family. Step outside to the paved backyard patio, enclosed by a private vinyl fence, perfect for relaxing or entertaining. This home is a rare find in Winter Park, walking distance to Park Ave and Winter Park Golf Course, offering easy access to the best dining, shopping, and outdoor recreation. It is also near Rollins College, Winter Park Village, and the train station, making it an unbeatable location for both convenience and lifestyle. This property can be purchased separately or together with the attached home at 720 N Pennsylvania Ave— and even offers owner financing options—making it an ideal opportunity for an income-producing investment, multigenerational living, or a private in-law or student suite. Don’t miss this incredible opportunity in one of Winter Park’s most sought-after locations, Schedule your private showing today!

Beds:
2
Baths:
2.00
Sq.Ft.:
956
Status:
Active
MLS#:
O6277579
Type:
Condo
Subdivision:
Lakeside Manor Condominium Association, Inc.
Year built:
1969
A broker reciprocity listing Courtesy: THE ANDERSON GROUP & CO PL 407-960-5657
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ADDITIONAL INFORMATION

2/2 * IMMACULATE CONDO * LOW HOA * LIVE ON LAKE KILLARNEY * ENJOY PARK AVE IN WINTER PARK * 3 MILES TO ROLLINS COLLEGE * NEW AC * NEW WATER HEATER * NEW INTERIOR PAINT * NEW LIGHTING * Immaculate updated 2 bedroom 2 bathroom Condo in a prime location on beautiful Lake Killarney, a serene oasis in Winter Park. A walkable Lake community providing Residents with direct Lake Access, Private Dock with Loungers & Seating area, Boat Slip, Private Pool, Clubhouse, Picnic Tables and Mature landscaping. Condo fully updated throughout. NEW Interior paint, NEW Water Heater, NEW AC, NEW Lighting, NEW Ceiling Fans, NEW Window Blinds, NEW Floor & Wall Tile in Primary Bathroom, NEW Modern Bathroom Vanity, NEW LED Bathroom Mirror, NEW Interior Door Hardware. In addition to Upgraded Exterior Doors and Windows. The open-plan Kitchen with dark wood cabinetry, Granite counters, Built-in wine rack and a Breakfast Bar, overlooks the spacious Living Room and Private Balcony. Enjoy your private patio area at both the front and rear of your Condo. Just one neighbor to one side, and one neighbor below, enhances your privacy. Condo features 2 large bedrooms, split-plan, each with a walk-in closet. The Principal Bedroom has an additional PRIVATE exterior entrance. The Principal Bathroom features a walk-in Shower, NEW Floor & Wall Tile, NEW Modern Bathroom Vanity, NEW LED Bathroom Mirror. The Second Bathroom includes a bath tub and shower combination, a single vanity, and tile floor. Perfectly located tranquil lakeside-living, in beautiful Lakeside Manor, is your opportunity to enjoy all that Florida has to offer, while living minutes from the exceptional Shopping and Restaurant experiences of Downtown Winter Park and Park Avenue. LOW HOA includes Lake Access, Private Dock, Pool, Water, Trash, and Designated Parking. Easy access to I4, Rollins College, Winter Park Village, Park Avenue, Downtown Orlando, and approx 20-30 mins to Orlando International Airport, Disney Springs and Universal Studios.

Beds:
4
Baths:
2.00
Sq.Ft.:
1,827
Status:
Active
MLS#:
O6271121
Type:
Single Family
Subdivision:
Casa Aloma
Lot size:
0.2 Acres
Year built:
1969
A broker reciprocity listing Courtesy: REAL ESTATE FIRM OF ORLANDO 407-581-5550
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ADDITIONAL INFORMATION

Located in the highly sought-after Casa Aloma community, this charming 1960s home offers the perfect blend of comfort, style, and convenience. Situated within a one-mile radius of all that Winter Park has to offer, this well-maintained home truly stands out in terms of location, location, location! The open floor plan is ideal for entertaining, with a spacious living room providing ample space for the whole family. The kitchen is a chef's dream, featuring stainless steel appliances, a gas stove, and a kitchen island that serves as a perfect spot for casual meals or as a serving area for family gatherings. A formal sitting room or secondary living area is conveniently located just off the kitchen, with sliding doors leading to the screened patio. The screened-in patio is perfect for unwinding after a long day, offering a relaxing space to enjoy Florida's rainy evenings. Don't forget to check out the built-in gas grill—great for outdoor cooking! The formal dining room provides an elegant space for holiday dinners or dinner parties throughout the year, with sliders leading to the patio for easy access to outdoor dining. The abundance of windows and sliders throughout the home ensures a bright, airy feel, while also showcasing the large backyard. The master bedroom is a standout feature, offering generous space and excellent closet storage. The recently updated master bath includes new flooring and a modern shower. In addition to the master suite, there are three more spacious bedrooms and a fully updated hall bath. Additional features and upgrades include Gas water heater roughly (2018) Fencing (2016) Windows and sliders (2016) Roof (2011). The backyard has a huge avocado tree as well for you lovers of avocado! This home is just minutes from shopping, top-rated schools, parks, and entertainment, including the iconic Park Avenue and Maitland shopping areas. Winter Park offers everything you need, and this home is the perfect place to enjoy it all. Don’t miss out—this move-in-ready gem is waiting for you! Schedule your showing today and make this beautiful home yours!

Beds:
3
Baths:
3.00
Sq.Ft.:
1,907
Status:
Active
MLS#:
O6266098
Type:
Townhouse
Subdivision:
Grayson Square
Lot size:
0.04 Acres
Year built:
2024
A broker reciprocity listing Courtesy: FLORIDA CONNEXION PROPERTIES 407-574-2636
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ADDITIONAL INFORMATION

Motivated seller! Brand new townhouse professionally decorated, and available today! Built in 2024, this property offers a great floorplan: with a lot of natural light and coziness. Fall in love with the modern and spacious house located in a prestigious area! Close to shops and markets this is an amazing opportunity for those looking for a quiet neighborhood but close to everything at the same time! Schedule a tour today!

Beds:
2
Baths:
2.00
Sq.Ft.:
1,105
Status:
Active
MLS#:
A4632112
Type:
Condo
Subdivision:
Parkview Village
Lot size:
0.1 Acres
Year built:
1984
A broker reciprocity listing Courtesy: FLATFEE.COM 954-965-3990
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ADDITIONAL INFORMATION

Condo in Winter Park, FL. 2923 Antique Oaks Cir, Unit 37. Updated 1,105 sq. ft. first-floor, North West corner condo. 2 bedrooms, 2 bathrooms. Located in the Winter Park School District: Updated Interiors: Recently remodeled with modern finishes, including brand-new appliances (convection oven, refrigerator, dishwasher), and a new LG stackable washer/dryer in the interior laundry room. Outdoor Living: private screened patio, pool, hot tub, and maintained grounds. Pet-Friendly & Welcoming: Dog-friendly and community-oriented, quiet and peaceful. Location: Zoned for A-rated Winter Park schools, 1 mile away. Walkable access to dining, shopping, and entertainment. Minutes from Park Avenue, Baldwin Park, Winter Park Hospital, and Downtown Orlando. Close to top educational institutions: Valencia College, Rollins College, Full Sail University, and UCF. The HOA provides excellent management and care.

Beds:
4
Baths:
5.00
Sq.Ft.:
4,636
Status:
Active
MLS#:
O6260493
Type:
Single Family
Subdivision:
Winter Park
Lot size:
0.36 Acres
Year built:
2024
A broker reciprocity listing Courtesy: PV LUXURY GROUP PA 407-861-0160
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ADDITIONAL INFORMATION

CALLING HIGHEST AND BEST BY 09/26/2025!! SELLER FINANCING AVAILABLE WITH VERY ATTRACTIVE TERMS Introducing a Unique, Stunning Modern Home A groundbreaking architectural masterpiece, this one-of-a-kind residence is built with reinforced concrete, steel, and iron framing, featuring floor-to-ceiling glass walls with no traditional windows. Designed to exceed Florida’s strictest building codes, this home follows commercial-grade construction standards, making it a bunker-style fortress unlike any other. Luxury Meets Modern Innovation Nestled in the heart of Historic Winter Park, Florida, this exceptional residence blends contemporary design with timeless elegance, offering unparalleled craftsmanship, high-end finishes, and an open-concept layout for those who appreciate architectural brilliance and luxury living. Key Features:     •    4,564 sq. ft. of living space     •    4 Bedrooms, 4.5 Bathrooms     •    Custom Costa One-Tree Solid Piece – A 16-foot steel masterpiece, a true work of art in the home’s design     •    Floor-to-ceiling impact-resistant Techno Glass walls—enhancing natural light and structural resilience     •    Imported Italian porcelain flooring throughout     •    All lighting fixtures imported from Greece, designed for maximum brightness and ambiance     •    Gourmet Chef’s Kitchen with:     •    1-inch thick Italian Quartz countertops     •    Imported Italian cabinetry     •    Extended island—ideal for entertaining     •    Top-of-the-line Wolf appliances & Sub-Zero refrigerator     •    Two Master Suites—one on each level, each with private luxury baths and custom walk-in closets     •    Private balconies crafted from exquisite boat wood, offering serene views and a tranquil retreat Exclusive Location & Lifestyle     •    Situated on a corner lot on Via Tuscany, one of Winter Park’s most exclusive and private streets     •    Just minutes from Interlachen Country Club, a historic private golf course     •    Short drive to Downtown Orlando and the best of Winter Park’s shopping, dining, and cultural experiences     •    Winter Park’s rich history and charming atmosphere make it one of Central Florida’s most desirable locations This architectural masterpiece is a true rarity, combining bunker-level resilience with breathtaking modern design. Experience the pinnacle of luxury living—schedule a private tour today.

Beds:
5
Baths:
5.00
Sq.Ft.:
3,161
Status:
Active
MLS#:
F10472583
Type:
Single Family
Subdivision:
Park Manor First Add
Year built:
2021
A broker reciprocity listing Courtesy: EXP Realty LLC 772-539-2473
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ADDITIONAL INFORMATION

Nestled in Winter Park, one of Orlando's most desirable neighborhoods, this home offers 5 spacious bedrooms & 4.5 baths, blending modern luxury with family-friendly functionality. With thoughtful design, high-end finishes, & an open-concept layout, this home is perfect for both comfortable living & elegant entertaining. As you step inside, you'll be welcomed by soaring ceilings, hardwood floors & abundant natural light. The gourmet kitchen with GE Profile Advantium appliances, large island, custom cabinetry & a walk-in pantry. The primary suite is a retreat with walk-in closet & spa-like bath with a tub, glass shower, and dual vanities. Upstairs, a large retreat is surrounded by 2 bedrooms and 2 full baths. The home also offers smart technology & energy-efficient features.

Beds:
2
Baths:
2.00
Sq.Ft.:
1,030
Status:
Active
MLS#:
O6256375
Type:
Condo
Subdivision:
Colonies
Lot size:
10.07 Acres
Year built:
1974
A broker reciprocity listing Courtesy: GRAVES REALTY 407-900-1355
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ADDITIONAL INFORMATION

Updated 2-bedroom, 2-bath condo featuring modern finishes throughout! This condo features laminate floors, sleek granite countertops, and stainless steel appliances in the kitchen. A rare find with an in-unit washer and dryer for added convenience. Step out onto the brand new deck, upgraded with durable composite decking—perfect for relaxing or entertaining. Ideally located just minutes from Full Sail University, UCF, and Valencia College, making it a prime spot. Don’t miss this stylish, move-in-ready condo!

Beds:
6
Baths:
4.00
Sq.Ft.:
3,853
Status:
Active
MLS#:
O6237975
Type:
Single Family
Subdivision:
Dixie Terrace
Lot size:
0.35 Acres
Year built:
2012
A broker reciprocity listing Courtesy: REALTY ONE GROUP MVP 800-896-8790
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ADDITIONAL INFORMATION

Listed at APPRAISED VALUE **Luxurious Winter Park Estate with Detached TWO bedroom Guest House** RENOVATED POOL HOME with NO HOA! TWO Primary Bedrooms located on the main floor! Welcome to a world of unparalleled luxury and elegance in the heart of historic Winter Park, FL. This exquisitely renovated two-story pool home, set on a sprawling corner lot, offers a rare opportunity to experience the pinnacle of sophisticated living. Boasting 6 total bedrooms, 4 bathrooms, including a detached 2-bedroom guest house, this property seamlessly blends modern amenities with timeless charm. As you step through the grand entrance, you are immediately greeted by a stunning foyer adorned with pristine travertine flooring, setting the tone for the elegance that lies ahead. The open floor plan, accentuated by soaring high ceilings, creates an inviting atmosphere perfect for both lavish entertaining and tranquil family living. The heart of the home, the gourmet kitchen, is a chef's dream come true. Featuring breathtaking quartz countertops, top-of-the-line appliances, custom cabinetry, and an in-home wine cellar, this space is as functional as it is beautiful. Whether you're preparing a casual meal or hosting a grand dinner party, the adjacent dining room provides the ideal setting for every occasion. The master suite, located on the main floor, is a sanctuary of luxury and comfort. It boasts a walk-in closet and an opulent en-suite bathroom complete with a soaking tub, separate shower, and double vanities. The remaining bedrooms are located on the second floor, offering privacy and space for family or guests. Adding to the property's appeal is a completely separate 2-bedroom guest house, accessible via a private entrance. This guest suite includes a full kitchen, cozy living room, and its own laundry room, making it perfect for extended family, visitors, or even as a private home office. The flexibility and privacy this space offers are truly unmatched. Step outside to your own private paradise, where a sparkling pool awaits. The expansive screened-in lanai and ample outdoor space make this the ultimate setting for enjoying Florida's year-round sunshine. Whether you're hosting a summer barbecue or simply unwinding after a long day, this outdoor oasis provides the perfect backdrop. Located just minutes from the renowned Park Ave, this home is nestled in one of Winter Park's most coveted neighborhoods. Enjoy the convenience of being close to award-winning restaurants, boutique shopping, and upscale entertainment options. Living here isn't just about owning a home—it's about embracing a lifestyle of luxury and convenience. This stunning property offers the perfect blend of luxury, comfort, and location. Schedule your private showing today and discover what makes this Winter Park home truly exceptional.

Beds:
3
Baths:
4.00
Sq.Ft.:
3,075
Status:
Active
MLS#:
1118718
Type:
Condo
Lot size:
0.07 Acres
Year built:
2009
A broker reciprocity listing Courtesy: Simply Real Estate 386-241-0100
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ADDITIONAL INFORMATION

This Douglas Grand luxury two-story penthouse, located in the heart of downtown Winter Park, is a one-of-a-kind gem in the condo complex. Spanning three bedrooms and three-and-a-half bathrooms, this splendid property offers both an upstairs and downstairs master suite (all bedrooms are en suite), blending the comforts of home with the vibrancy of urban living. Conveniently positioned, residents can effortlessly stroll to Central Park, Park Avenue's fine dining and shopping, the Sunrail Station, City Hall, Hannibal Square, and numerous shops and wine bars. Designed with an eye for luxury, this Regency unit boasts a spacious living room, a dining area adorned with custom wood paneling, and a serene indoor solarium - the perfect setting for a peaceful morning coffee.

Beds:
2
Baths:
2.00
Sq.Ft.:
1,018
Status:
Active
MLS#:
O6156853
Type:
Condo
Subdivision:
Parkview Village
Lot size:
0.1 Acres
Year built:
1984
A broker reciprocity listing Courtesy: YOUNG REAL ESTATE 407-904-0069
View additional info

ADDITIONAL INFORMATION

This unit was restored, with new kitchen cabinets, new ceramic tile in kitchen, living room, dining room and 2nd bathroom. It has been impeccably maintained. Walking distance from Full Sail and only 6.9 miles to UCF. Spacious bedrooms and baths and very comfortable layout. Lovely screened patio off living room. Complex offers pool, and club house. A/C unit is brand new, installed on January 2023. Great Winter Park school district, its a must see. The condo has a transferable Home Warranty with "Liberty Home Guard" that expires on 06/22/2025.

Beds:
4
Baths:
3.00
Sq.Ft.:
1,805
Status:
Active
MLS#:
O6093816
Type:
Single Family
Subdivision:
Winter Park Estates
Lot size:
0.24 Acres
Year built:
1959
A broker reciprocity listing Courtesy: COLDWELL BANKER RESIDENTIAL RE 407-647-1211
View additional info

ADDITIONAL INFORMATION

Price Reduced !! This beautiful and remodeled home is turnkey and ready to move in! Investors -- You will love the cash flow upside with this property. Updated Roof, AC, Exterior Paint, Patio, Garage, Driveway, Fence, Sprinkler System, Lighting, Flooring, Kitchen, and much more. You will enjoy entertaining your guests with this large saltwater pool with cabana, as well as yard space for your pets. Save money with No HOA, in a nice mature community. Smart home comes a split floor plan, and kitchen has a large island with granite countertops. Home features an extended driveway with room for a Small boat, Jet ski or RV. *All information is intended to be accurate but is not guaranteed.

Beds:
4
Baths:
6.00
Sq.Ft.:
3,542
Status:
Active
MLS#:
221065434
Type:
Single Family
Subdivision:
Not Applicable
Lot size:
0.24 Acres
Year built:
2021
A broker reciprocity listing Courtesy: Vonac Realty Inc Michael Griffin
View additional info

ADDITIONAL INFORMATION

Welcome to Winter Park's most recent beautiful Transitional Style, NEW CONSTRUCTION home! Precision craftsmanship showcases a harmonious blend of elegant, warm, and modern elements throughout a very spacious and fluid plan design. Large, well placed windows and sliding doors allow abundant cascading light to beautifully brighten this home, entirely, and without any compromise of privacy. There are four LUXURY en suite bedrooms, including two ENORMOUS Master Suites (one on each level). All suites have spacious walk-in closets that have been fitted with custom build-ins. A luxurious kitchen features custom solid wood cabinetry, quartz countertops and backsplash, a premium Kitchen-aid appliance ensemble, a large walk-in pantry, and an oversized eat-in kitchen island. Your dining area, adjacent to the kitchen, has expansive views that include your pool and second level grand span of a twenty-four foot ceiling. The Family Room is a wonderful gathering space...including an electric fireplace and oversized sliding glass doors that give access to your large covered lanai. Enjoy Summer Days, or evening gatherings around the travertine pool deck and cabana, with a complete outdoor kitchen.

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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


Listings courtesy of Stellar MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of {{last updated}}. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Properties displayed may be listed or sold by various participants in the MLS. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified. Listing information is provided for consumer personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. Copyright 2026, My Florida Regional MLS DBA Stellar MLS.

Andrea D. Conner, License # BK3437731, Xome Inc., License CQ1043756, [email protected], 844-400-XOME, 750 State Highway 121 Bypass, Suite 100, Lewisville, TX 75067

All listings featuring the BMLS logo are provided by BeachesMLS, Inc. This information is not verified for authenticity or accuracy and is not guaranteed. Copyright © 2026 BeachesMLS, Inc.


Andrea D. Conner, License # BK3437731, Xome Inc., License CQ1043756, [email protected], 844-400-XOME, 750 State Highway 121 Bypass, Suite 100, Lewisville, TX 75067

The data relating to real estate for sale on this web site comes in part from a cooperative data exchange program of Daytona Beach Area Association of REALTORS® Multiple Listing Service. Real estate listings held by brokerage firms other than the owner of this site are marked with the listing broker's logo or name and detailed information about such listings includes the name of the listing brokers. Copyright 2026 Daytona Beach Area Association of REALTORS® Multiple Listing Service. All rights reserved.
Andrea D. Conner, License # BK3437731, Xome Inc., License CQ1043756, [email protected], 844-400-XOME, 750 State Highway 121 Bypass, Suite 100, Lewisville, TX 75067

The data relating to real estate for sale on this Website come in part from the Broker Reciprocity Program (BR Program) of M.L.S. of Naples, Inc. Properties listed with brokerage firms other than this broker are marked with the BR Program Icon or the BR House Icon and detailed information about them includes the name of the Listing Brokers. The properties displayed may not be all the properties available through the BR Program. The accuracy of this information is not warranted or guaranteed. This information should be independently verified if any person intends to engage in a transaction in reliance upon it. Some properties that appear for sale on this website may no longer be available.



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

    $500,000
    25.3%
    change since last quarter
  • # Active listings

    294
    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