Winter Park Homes with City View

Winter Park Homes with City View

Welcome to Winter Park, Florida—a picturesque city that embodies the charm of old-world elegance combined with modern amenities. Nestled just north of Orlando, Winter Park is renowned for its stunning lakes, lush parks, and vibrant cultural scene. With its tree-lined streets and historic architecture, this delightful city offers a unique blend of suburban tranquility and urban excitement.

One of Winter Park's most alluring features is its impressive array of homes with breathtaking city views. Imagine waking up each morning to a panoramic vista of the city skyline, framed by the natural beauty of Florida’s landscape. These homes not only provide a stunning backdrop for your daily life but also offer a sense of connection to the vibrant community below.

Winter Park boasts a rich tapestry of activities and attractions, from the scenic paths of the Chain of Lakes to the renowned Morse Museum of American Art, which showcases an exquisite collection of Tiffany glass. The city is also home to an eclectic mix of boutiques, cafes, and fine dining establishments that cater to every palate.

For those who enjoy the great outdoors, Winter Park’s parks and gardens, including the beautiful Central Park, provide ample opportunities for relaxation and recreation. Whether you’re strolling along the brick pathways or enjoying a picnic with family, the natural beauty of Winter Park is truly captivating.

Embrace the charm of Winter Park and discover the perfect home with a city view that complements your lifestyle. Here, every day is a celebration of beauty, culture, and community. Your dream home awaits!

Newest Winter Park Homes with City View

$739,000
2 Beds ⋅ 2 Baths ⋅ Park West Condo SubDv. ⋅ 32789 Zip Code
Discover the ease of Winter Park living in the highly desirable gated community of Park West, ideally located just steps from Park Avenue. From this exceptional location, charming boutiques, sidewalk cafés, award-winning restaurants, and the popular weekly farmers market are all within easy reach—giving you the freedom to leave the car behind and enjoy everything Park Avenue has to offer. This beautifully remodeled second-floor corner residence offers the privacy, comfort, and convenience you've been looking for. The thoughtfully updated kitchen features wood cabinetry and granite countertops, while both bathrooms have been tastefully remodeled. Spacious bedrooms, generous storage, and a comfortable flow throughout the home provide plenty of room for everyday living or welcoming guests. Enjoy the simplicity of a well-maintained community with beautifully landscaped grounds, a sparkling swimming pool, and tennis courts. As a corner unit, this residence also offers enhanced privacy and convenient access into and out of the building—perfect for those seeking a low-maintenance lifestyle or an easy lock-and-leave retreat. With Rollins College and Full Sail University nearby and Park Avenue just moments away, this condo puts the best of Winter Park right at your doorstep. Whether you're looking for a full-time residence, a seasonal escape, or simply a home that allows you to spend less time on maintenance and more time enjoying life, Park West offers an exceptional combination of location, comfort, and convenience.

250 Carolina Avenue Unit 205, Winter Park
$549,900
3 Beds ⋅ 2 Baths ⋅ Orwin Manor Westminster Sec SubDv. ⋅ 32789 Zip Code
Charming 1950 block bungalow in sought-after Orwin Manor! This inviting 3-bedroom, 2-bath home sits on a generous corner lot with a side-load driveway and garage, offering added breathing room, curb appeal, and convenience. A paver walkway leads to the covered front porch, setting the tone for the home’s classic character and welcoming appeal. Inside, original hardwood floors complement a renovated, generously sized kitchen—ideal for everyday living and entertaining. Recent improvements include a 2020 roof, 2021 HVAC system, plus new windows, doors, and added insulation. The dining room features French doors opening to a newly poured concrete patio and charming backyard offering loads of potential for gardening, play, pets, or creating your own private outdoor retreat. Previously utilized as an investment rental, this property presents an excellent opportunity for an owner-occupant or investor seeking a desirable Winter Park location with strong rental appeal. Enjoy close proximity to AdventHealth’s world-class Orlando campus, as well as the shopping, dining, and lifestyle destinations of Winter Park, Park Avenue, Mills 50, and downtown Orlando. A wonderful opportunity to own a character-filled home in one of the area’s most desirable central neighborhoods.

1652 Berkshire Avenue, Winter Park
$575,000
2 Beds ⋅ 3 Baths ⋅ Seville Park SubDv. ⋅ 32789 Zip Code
Brand new roof. Conveniently located between downtown Winter Park and College Park with easy access to shopping, restaurants and highways. Zoned for Audubon Park K-8 for elementary and middle school. All the amenities one could want in this luxurious townhome. Tall ceilings and doorways throughout home. Custom tile floors on the first floor with a gas fireplace in the great room. Two patios featured on the first floor, a pavered and covered rear and side patio perfect for BBQs or teatime. The kitchen is equipped with stainless and gas appliances for the chef in your family. Granite countertops throughout home. Wood stairs take you to the second floor with a generous primary bedroom, a light and bright guestroom and a bonus living space complete with a wet bar. Balcony from each suite. Washer and dryer conveniently located upstairs near the two bedrooms. There is no HOA and the home features a low maintenance yard. This townhome will not disappoint you.

1071 Aragon Avenue, Winter Park
$625,000
4 Beds ⋅ 3 Baths ⋅ Aloma SubDv. ⋅ 32792 Zip Code
Virtually Staged. Virtually Staged. Welcome to this exceptional SINGLE FAMILY-TOWNHOME with NO HOA offering the perfect blend of comfort, style, and location! Beautiful modern 4-bedroom, 2.5-bath, located in one of Winter Park's most established and sought-after neighborhoods. This spacious home features wood and laminate flooring throughout, a downstairs bonus room, a separate utility room, a private second-floor sun deck/terrace perfect for relaxing or entertaining, and a first-floor concrete patio. The contemporary kitchen is equipped with 42-inch European-style cabinetry, granite countertops, and stainless steel appliances. Residents also enjoy access to attractive community green spaces.Ideally situated within walking distance of Winter Park Hospital and AdventHealth Winter Park, this home is also just minutes from Cady Way Park, Ward Park, shopping, dining, and entertainment along Aloma Avenue and Lakemont Avenue. Conveniently located near Rollins College, Park ave, the University of Central Florida (UCF), and Full Sail University, making it an excellent choice for healthcare professionals, faculty, and other professionals. WELCOME TO YOUR NEW HOME!

2251 Nairn Drive, Winter Park
$525,000
3 Beds ⋅ 4 Baths ⋅ Quarters At Winter Park Condo SubDv. ⋅ 32789 Zip Code
Beneath mature oak trees in The Quarters at Winter Park, this townhome-style condominium presents a rare opportunity to own a spacious, architecturally distinctive residence in one of Winter Park's most established communities. Priced to reflect its as-is condition, the home offers exceptional potential for a buyer ready to personalize the space. A gated brick courtyard and covered front porch lead to light-filled living and dining areas featuring engineered hardwood flooring and a wrought-iron staircase. The kitchen offers granite countertops, a gas range and opens to the family room, where a gas fireplace and skylight create a welcoming gathering space. A private screened courtyard connects the residence to the detached two-car garage. Upstairs, the primary suite spans more than 300 square feet and features a custom walk-in closet and dual-sink en-suite bath. Two additional bedrooms include one with a private en-suite bath and another with access to a balcony overlooking the tree-lined street. Ideally just minutes from Park Avenue, Rollins College and Seven Oaks Park, this residence offers the opportunity to renovate and customize a home in one of Winter Park's most sought-after communities. Sold as is, with an inspection report available upon request.

1134 Washington Avenue Unit 13C, Winter Park
$1,849,900
3 Beds ⋅ 4 Baths ⋅ Winter Park Residential SubDv. ⋅ 32789 Zip Code
Discover luxury living in this exquisitely renovated two-story condominium, ideally situated on the third floor of the highly sought-after Douglas Grand in the heart of Winter Park. This elegant three-bedroom, three-and-one-half-bath residence seamlessly blends sophisticated design with everyday comfort. Immediately captivating, the light-filled open floor plan showcases stunning new wide-plank white oak flooring, high ceilings, detailed crown molding, and all-new designer lighting throughout. The chef’s kitchen is a showpiece, featuring crisp white cabinetry, luxurious white quartz countertops, a spacious breakfast bar island, elegant gold hardware, and a built-in desk. A charming breakfast nook offers the perfect setting for morning coffee or casual dining. French doors open to a private enclosed atrium, creating a versatile outdoor retreat ideal for alfresco dining, relaxing, or entertaining guests in style. The expansive living and dining spaces flow effortlessly, while a private first-floor bedroom with en suite bath and walkout balcony provides an ideal space for guests, multigenerational living, or a home office. Upstairs, the primary suite serves as a peaceful sanctuary, complete with an indulgent soaking tub, dual vanities, an oversized walk-in closet, and French doors leading to a large private balcony with sweeping views of Winter Park's iconic Park Avenue—perfect for enjoying sunrise coffee or evening sunsets. A second upstairs en suite bedroom offers its own private bath and generous walk-in closet. Thoughtful features include an upstairs laundry room, a spacious storage closet with potential elevator conversion for future accessibility, and a secure gated garage with two reserved parking spaces. Perfectly positioned in the heart of Winter Park, Douglas Grand places you just steps from Park Avenue, the Winter Park Farmers’ Market, Rollins College, Hannibal Square, Winter Park Golf Course, the Winter Park Tennis Center, Winter Park Village, and an array of renowned dining, shopping, and cultural attractions. Enjoy an unparalleled walkable lifestyle in one of Central Florida's most desirable communities. Notable improvements include an interior renovation (2026), front elevation windows and French doors (2024), interior paint (2024), and HVAC system (2022).

101 S New York Avenue Unit 311, Winter Park
$2,350,000
3 Beds ⋅ 3 Baths ⋅ Landmark Winter Park Condo SubDv. ⋅ 32789 Zip Code
Discover an exceptional opportunity to own a penthouse residence at The Landmark, one of downtown Winter Park's exclusive addresses. Directly along the desired brick streets of Park Avenue, this boutique condominium community consists of only 13 residences and offers an unparalleled blend of privacy, sophistication and accessible convenience. Just outside your door, enjoy acclaimed dining, boutique shopping, art galleries, sidewalk cafés, Central Park and the year-round events that have made Winter Park one of Central Florida's sought-after destinations. Behind The Landmark's secure wrought-iron gates, residents are welcomed into a beautifully landscaped courtyard centered around a timeless fountain and illuminated by dozens of gas lanterns, creating a warm and elegant atmosphere reminiscent of a European enclave. Impeccably maintained and thoughtfully designed, the community provides a peaceful retreat while remaining moments from the vibrant energy of Park Avenue. Residence J occupies a premier penthouse position and is filled with natural light, enhanced by soaring ceilings, expansive windows, and multiple French doors that open to private terraces overlooking Morse Boulevard and the surrounding downtown streetscape. The spacious floor plan is designed for comfortable daily living and effortless entertaining. The living and dining areas are anchored by a gas fireplace and flow seamlessly into the kitchen, where integrated appliances, a gas cooktop, generous workspace, and a charming breakfast area create a functional and inviting gathering space. The primary suite serves as a private sanctuary, featuring dual vanities, separate water closets, an oversized walk-in shower and a custom-designed walk-in closet. Two additional guest bedrooms provide flexibility for family and visitors. One bedroom is connected to a Jack-and-Jill bath, while the third enjoys a private en-suite bath and a Juliet balcony that captures the charm and character of downtown Winter Park from above. Additional amenities include two deeded underground parking spaces, a private climate-controlled storage room, and access to the community's shared outdoor entertaining area, complete with a summer kitchen and courtyard gathering space. Whether enjoyed as a full-time residence or a lock-and-leave retreat, this penthouse offers a rare combination of luxury, security and an unmatched Park Avenue lifestyle in the heart of Winter Park.

140 E Morse Boulevard Unit J, Winter Park
$3,500,000
3 Beds ⋅ 5 Baths ⋅ Park Hill SubDv. ⋅ 32789 Zip Code
Park Hill is one of Winter Park's most coveted addresses, a distinguished collection of luxury brownstones situated at the northern end of Park Avenue, moments from the city's finest boutiques, restaurants, cultural landmarks and the historic Winter Park Golf Course. Within this exclusive enclave, residence 649 occupies one of the community's most private settings. Beyond the stately brick courtyard and gas lantern-adorned entrance, this three-story home with a private elevator is thoughtfully scaled for refined living. Not oversized, but extraordinarily well-appointed. Ten-foot ceilings, intricate millwork and moldings and generous windows establish an ambiance of quiet elegance, while hardwood floors and designer fixtures carry that standard throughout. The open-concept main living area is built for effortless entertaining. The chef's kitchen features Wolf and Sub-Zero appliances, custom wood cabinetry, marble accents, a center island with bar seating and a wet bar with a beverage refrigerator and ice maker. The space opens directly to a private courtyard with a summer kitchen and dedicated alfresco dining area, creating a genuinely tranquil retreat that feels removed from the energy of the avenue. Upstairs, two guest suites each offer walk-in closets and en-suite baths. A dedicated laundry room and a covered terrace with a fireplace, wet bar and half bath complete the level. The third-floor primary suite provides a true sense of retreat, with two custom walk-in closets, a private balcony and a spa bath filled with natural light from windows and skylights. Dual vanities, a glass-enclosed steam shower and a soaking tub are finished throughout in premium materials. Constructed of Old Carolina brick with three-story block construction, precast exterior trim and a slate mansard roof, the residence features a two-car air-conditioned garage, ample storage and soundproof hollow core floors. With exterior maintenance managed by the association, the lifestyle here is genuinely lock-and-leave. This is a rare opportunity to own in one of Central Florida's most prestigious communities, in a location that simply cannot be replicated.

649 N Park Avenue, Winter Park
$989,500
1 Beds ⋅ 2 Baths ⋅ Village Winterset Inc SubDv. ⋅ 32789 Zip Code
Winterset is celebrated for its boutique scale, mature landscaping, and timeless Winter Park character. Residents enjoy glimpses of Lake Osceola, tranquil surroundings beneath stately oaks, and the privilege of living in a community where privacy and exclusivity are paramount. This fully remodeled Penthouse Suite's location is unmatched—one block to Park Avenue, offering effortless access to fine dining, boutique shopping, the Morse Museum, Rollins College, and the scenic Chain of Lakes. Whether you’re downsizing, escaping winter months or seeking a refined second home, this residence delivers the perfect blend of luxury, simplicity, and prestige. Designed for comfort and ease, the home welcomes you with a bright, open living space enhanced by crown molding, warm natural light, and a seamless flow ideal for both quiet escapes and intimate entertaining. The primary suite features a generous walk-in closet, while the kitchen offers modern functionality with quality appliances and thoughtful storage. This unit offers its own washer/dryer combo unit, large exterior storage closet, assigned parking space under canopy and extra open parking spaces. Please note rentals are not allowed and no pets except for Service Animals.

269 E Canton Avenue Unit 269, Winter Park
$500,000
3 Beds ⋅ 2 Baths ⋅ Eastgate Sub SubDv. ⋅ 32792 Zip Code
Set on an oversized corner lot in one of the most desirable pockets of Winter Park, this 3-bedroom, 2-bath pool home blends character, location, and opportunity. The backyard is a standout feature, with a resurfaced pool finished in Tahoe Blue PebbleTec and positioned for open sky views, a rare find in a neighborhood known for its mature tree canopy. It creates a bright, inviting outdoor space that feels both private and expansive. Inside, the home has been thoughtfully updated while still leaving room for your own design vision. The layout offers comfortable living spaces with plenty of natural light and flexibility for everyday living or entertaining. Convenience is a major highlight. Located near top-rated schools, including Lakemont Elementary School, Maitland Middle School, Winter Park High School, and just minutes from local favorites like Park Avenue, Rollins College, and the Cady Way Trail. Nearby access to the SunRail adds another layer of accessibility. This location delivers a strong mix of lifestyle and connectivity, with dining, shopping, parks, and daily essentials all close by. Offered with clear motivation due to relocation, this is a rare chance to secure a well-located pool home with long-term upside in one of Central Florida’s most established communities.

512 N Lakemont Avenue, Winter Park
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