Winter Park Real Estate

Winter Park Real Estate

Welcome to the charming subdivision of Winter Park, nestled in the heart of Orange County, Florida. Known for its picturesque streets, lush greenery, and vibrant community, Winter Park is a highly sought-after location for those looking to settle in the Sunshine State.

With a perfect blend of historic charm and modern amenities, Winter Park offers residents a unique living experience. The area is renowned for its beautiful parks, upscale shopping districts, and top-rated schools, making it an ideal place for families, young professionals, and retirees alike.

Home to the prestigious Rollins College and the renowned Morse Museum, Winter Park is a cultural hub with a thriving arts scene. Residents can enjoy a variety of cultural events, art galleries, and music festivals throughout the year.

Whether you're strolling down Park Avenue, enjoying a boat ride on the Chain of Lakes, or exploring the scenic Mead Botanical Garden, Winter Park has something for everyone to enjoy. With its convenient location just minutes away from downtown Orlando and major attractions, living in Winter Park offers the perfect balance of tranquility and accessibility.

Come and discover the magic of Winter Park – where luxury living meets small-town charm in the heart of sunny Florida.

Newest Listings in Winter Park

$550,000
4 Beds ⋅ 2 Baths ⋅ Winter Park SubDv. ⋅ 32789 Zip Code
A RARE WINTER PARK OPPORTUNITY—FIRST TIME OFFERED FOR SALE SINCE THE 1980s! Whether you are an INVESTOR looking to add a multi-family property to your portfolio, an INTELLIGENT BUYER dreaming of living in one unit while collecting rental income from the other, or someone with a BIGGER VISION for the future, 655 & 657 Minnesota Ave offer plenty of possibilities! Built in 1965 and situated on a 7,000 SQ FT LOT zoned R-2 MULTI-FAMILY with PUBLIC WATER & SEWER, this classic Florida duplex offers approximately 1,548 SQ FT OF LIVING SPACE and 2,188 TOTAL SQ FT UNDER ROOF. Each approximately 774-square-foot unit features 2 BEDROOMS, 1 BATH, its own COVERED CARPORT, and an INDOOR LAUNDRY/STORAGE ROOM with plenty of extra space for tools, bikes, and all the Florida-living essentials. ORIGINAL TERRAZZO FLOORS add vintage character with NO CARPET, while NEW EXTERIOR PAINT gives the property a fresh, modern feel! Several important improvements have already been addressed, including a WHOLE-HOUSE REPIPE completed in 2025, ROOF, & UPDATED ELECTRICAL. THE FRONT UNIT, 655 Minnesota Ave, is charming and currently occupied by a LONG-TERM TENANT who has called it home for approximately 13 YEARS—providing established rental income from day one. The REAR UNIT, 657 Minnesota Ave, became VACANT on August 30th and is ready for its next chapter! This unit offers an UPDATED KITCHEN with a BUILT-IN OVEN, GLASS-TOP RANGE, and newer refrigerator, along with THREE UPDATED MINI-SPLIT A/C UNITS—one serving the living area and 1 in each bedroom. Its indoor laundry room provides additional space for garden tools and storage, and the covered carport adds convenient off-street parking. Step outside and you will find another little slice of Florida potential! The rear unit enjoys direct access to the BACKYARD with a pavered patio practically begging for Adirondack chairs, string lights, and evenings spent enjoying FLORIDA OUTDOOR LIVING. For an owner-occupant, here's where it gets interesting: MOVE INTO THE VACANT REAR UNIT while collecting rental income from the front. For an investor, the rear unit is ready to lease from day one, potentially creating a second income stream. Or, with R-2 MULTI-FAMILY ZONING, PUBLIC WATER & SEWER, and redevelopment already taking place throughout the surrounding area, explore what the future possibilities may hold for this 7,000-square-foot lot. What’s the #1 Rule in Real Estate? LOCATION, LOCATION, LOCATION: another reason this opportunity stands out! Enjoy convenient access to the heart of WINTER PARK, with PARK AVENUE'S celebrated shopping, dining, and entertainment, beautiful ROLLINS COLLEGE, and ADVENT HEALTH minutes away. Whether you're thinking about long-term investment potential or looking for a place to call home, this amazing property location keeps you connected to so much of what makes Winter Park special. INVEST. LIVE. RENT. REIMAGINE. After more than four decades with the same ownership, opportunities like this don't come along every day. Come discover 655 & 657 Minnesota Aveand start dreaming about what YOU could do with this unique Winter Park property!

657 (and 655) Minnesota Avenue, Winter Park
$995,999
4 Beds ⋅ 3 Baths ⋅ Winter Park SubDv. ⋅ 32789 Zip Code
Exceptional Winter Park Opportunity with In-Law Suite & Income Potential Discover the opportunity to own a versatile property in one of Central Florida’s most desirable locations. 471 Holt Ave. in Winter Park offers buyers something increasingly valuable: flexibility. With a private in-law suite, this property presents an exciting opportunity for multigenerational living, a guest suite, home office, or potential rental income. For homeowners, the additional living space provides the freedom to accommodate family members or guests while maintaining privacy and separation. For investors, the configuration creates the potential to generate supplemental income, subject to applicable local regulations and requirements. The property’s location adds to its appeal, placing you near Winter Park’s renowned dining, shopping, parks, cultural attractions, and vibrant community amenities. Also, just a short distance to Rollins College! Whether you’re looking to offset your mortgage, create an additional income stream, or simply secure a property with adaptable living options, this home offers a compelling combination of lifestyle and investment potential. Opportunities with this level of flexibility are hard to find. Live in the main residence, utilize the suite for family or guests, or explore its income-producing potential. 471 Holt Ave. offers the versatility today’s buyers are looking for and the potential long-term value investors appreciate. Don’t miss the opportunity to make this flexible Winter Park property your next home or investment.

471 Holt Avenue, Winter Park
$4,600,000
Winter Park SubDv. ⋅ 32789 Zip Code
Rare Winter Park redevelopment opportunity on a nearly half-acre corner parcel just minutes from Park Avenue. Zoned R-3 (Medium-Density Residential), this parcel offers outstanding residential redevelopment potential, including up to seven residential units. Ideally situated between Park Avenue and Winter Park Village, the property enjoys convenient access to renowned dining, shopping, Rollins College, cultural attractions, AdventHealth Winter Park, and major transportation corridors. Three existing residences occupy the site and contribute no value to the offering. Opportunities of this size and zoning in such close proximity to Park Avenue are exceptionally uncommon.

540 N Pennsylvania Avenue, Winter Park
$249,000
Winter Park SubDv. ⋅ 32789 Zip Code
A rare piece of land in the heart of Winter Park. Short distance to Park Ave. Approved permits for 2000 sqft under AC housing project.

669 W Comstock Avenue, Winter Park
$1,595,000
3 Beds ⋅ 3 Baths ⋅ Winter Park SubDv. ⋅ 32789 Zip Code
In the heart of Winter Park's vibrant Hannibal Square, this exceptional one-story residence, completed in 2022, offers the ideal blend of contemporary design, refined finishes and an unbeatable accessible lifestyle. Thoughtfully designed with three bedrooms, two and one-half baths, and an open-concept floor plan, the home showcases clean architectural lines, soaring ceilings and walls of glass that fill the interior with natural light while framing views of the beautifully landscaped grounds. The chef's kitchen serves as the centerpiece of the home, featuring premium Wolf and Sub-Zero appliances, custom cabinetry, a center island with seating, and workspace for everyday living and entertaining. The adjoining dining area flows seamlessly into the spacious great room, where custom-built library shelving creates a striking focal point and adds warmth and character to the modern design. Beautiful polished concrete floors extend throughout the residence, providing a cohesive and sophisticated aesthetic. Designed with privacy in mind, the split-bedroom floor plan places the primary suite in its own secluded wing. This spacious retreat offers direct access to the covered rear patio and features a beautiful bath with dual vanities, an oversized walk-in shower, private water closet, and an impressive custom walk-in closet measuring approximately 11 by 9 feet. Conveniently accessible from the primary bath and laundry room, the thoughtfully designed closet enhances everyday functionality. On opposite side of the home, two additional guest bedrooms are connected by a well-appointed Jack-and-Jill bath, while a stylish powder bath is ideally located for visitors. Outdoor living is equally inviting with a covered patio with a privacy bamboo hedge that creates a peaceful backdrop for relaxing or entertaining. An attached two-car garage completes this beautifully appointed residence. Ideally near the acclaimed restaurants, wine bars, coffee shops, and boutiques of Hannibal Square, this home offers one of Winter Park's desirable lifestyles. Visit the renowned shopping, dining, galleries and sidewalk cafés of Park Avenue, enjoy nearby Central Park and community events, or take advantage of the proximity to Rollins College, the Winter Park Farmers' Market and major roadways providing convenient access throughout Central Florida. This is a rare opportunity to enjoy nearly new construction in one of Winter Park's sought-after neighborhoods, where modern luxury and exceptional accessibility come together.

462 W Lyman Avenue, Winter Park
$2,495,000
4 Beds ⋅ 4 Baths ⋅ Winter Park SubDv. ⋅ 32789 Zip Code
Timeless elegance meets boutique craftsmanship at 541 W Canton Ave., an exceptional new construction home by Urban Perch, proudly featured in the 2025 Parade of Homes Orlando. Near Winter Park’s iconic Park Avenue, this French Quarter-inspired residence blends historic charm and rich character with elevated modern living and a refined sense of calm. From its dormer windows and custom-carved wood entry door, to its charming striped awnings and the flicker of gas lanterns, every detail of the exterior is carefully curated. Classic marble-paved patios frame the home, and a courtyard-style pool with fountain and sandblasted marble decking invites quiet relaxation or festive gatherings. Inside, soaring ceilings, beautiful hardwood floors and immersive color-drenched rooms create an inviting space that is luxurious but unpretentious, bold yet serene. The stunning staircase features a custom wrought-iron railing with an antique finish, offering a striking architectural focal point. The chef’s kitchen, a culinary sanctuary and social hub, is complete with graphite La Cornue range and pot filler, Monogram paneled refrigerator, custom plaster hood, quartzite countertops and backsplash, and grand center island that opens to a gathering room with a gas fireplace. This more relaxed living area flows effortlessly through French doors to the pool and patios, creating an ideal indoor-outdoor lifestyle. A butler’s pantry with a second refrigerator, cabinetry and prep space adds functionality, while the formal dining room, living room, and bar area with sink and built-in beverage cooler are ideal for entertaining. A beautiful downstairs powder bath features designer wallpaper, elegant sconces and custom cabinetry. The upstairs primary suite offers spa-like serenity, including a wet room complete with soaking tub framed by a picture window. Three additional bedrooms include one with an en-suite bath, while the other two share a hallway-accessible bath with double vanity and walk-in tiled shower. This masterpiece set in the heart of Winter Park, thoughtfully surrounded by lush landscaping and carefully placed privacy screens, offers polish and presence in an ideal location.

541 W Canton Avenue, Winter Park
$4,500,000
Winter Park SubDv. ⋅ 32789 Zip Code
RARE 0.48 ACRE VACANT LOT IN DOWNTOWN WINTER PARK - OFFERED AT $4,500,000! Zoned R-3, this multi-family, prime piece of land is ready for development. Luxury townhomes or condos, nothing but pure potential. Located near the intersection of N. Interlachen Avenue and Canton Avenue, this parcel is just 1-block to Park Avenue's boutique shops, award-winning restaurants, and esteemed businesses. Future residents will enjoy picturesque walks along Winter Park's famous brick streets just off the shores of the chain of lakes. Nearby attractions like the Winter Park Farmer's Market, the Winter Park Golf Course, a highly rated 9-hole gem in the center of town, Casa Feliz, Central Park, and more are all within just a few minutes stroll.

503 N Interlachen Avenue, Winter Park
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