Winter Park Homes with Park/Greenbelt View

Winter Park Homes with Park/Greenbelt View

Welcome to Winter Park, Florida – a picturesque city that beautifully blends historic charm with modern sophistication. Nestled just north of Orlando, Winter Park is renowned for its stunning lakes, lush parks, and vibrant arts scene, making it a coveted destination for families, professionals, and retirees alike. With its tree-lined streets and a delightful selection of boutique shops and gourmet restaurants, the city exudes a warm, welcoming atmosphere that feels like home.

One of Winter Park’s most appealing features is its abundance of homes with park and greenbelt views. Imagine waking up each morning to the gentle rustle of leaves and the serene sight of expansive green spaces right outside your window. These homes not only provide a tranquil backdrop for everyday living but also offer easy access to the city’s beautiful parks, such as the iconic Central Park and Mead Botanical Garden. Residents can enjoy leisurely strolls, picnics, and outdoor activities, all while being surrounded by nature’s beauty.

The architectural styles in Winter Park are as diverse as its residents, ranging from charming bungalows to luxurious estates. Many of these homes are designed to take full advantage of their scenic surroundings, featuring large windows and spacious patios that invite the outdoors in. Whether you’re looking for a cozy family home or a sophisticated retreat, Winter Park’s real estate market has something to offer everyone.

Discover the allure of Winter Park and find your dream home with breathtaking park and greenbelt views, where nature and community come together in perfect harmony.

Newest Winter Park Homes with Park/Greenbelt View

$1,495,000
Charmont SubDv. ⋅ 32789 Zip Code
A wonderful opportunity to build your dream home on one of Winter Park’s most idyllic streets. Situated on a quaint, one-way brick street with a charming park at its center, this exceptional 12,581-square-foot deep lot offers a rare combination of space, character, and location. Currently featuring a 3-bedroom, 2.5-baths, plus office home with 2,080 square feet, the property offers the flexibility to live in or rent the existing home while you finalize your plans and prepare to build. Ideally located within the highly sought-after “A” school district of Audubon K-8 and Winter Park High School, this property places you just minutes from downtown Orlando, Orlando Health, AdventHealth, and the Dr. Phillips Center for the Performing Arts. Enjoy easy access to the vibrant restaurants and shops along Corrine Drive, as well as the boutiques, dining, and charm of Park Avenue. A rare opportunity to create your ideal Winter Park residence in an extraordinary setting surrounded by convenience, character, and everything this coveted area has to offer.

150 E Reading Way, Winter Park
$575,000
2 Beds ⋅ 3 Baths ⋅ Temple Trail Village SubDv. ⋅ 32789 Zip Code
A rare opportunity in Winter Park’s coveted 32789! This stunning fee-simple townhome offers the feel of a private retreat with the architectural pedigree of Fugelberg Koch (FK Architecture), the freedom of NO HOA FEES, and an extraordinary setting overlooking the 80-acre Howell Creek Preserve. Tucked away in a highly desirable Winter Park location, this 2-story end-unit lives much larger than its 1,701 square feet and delivers a lifestyle that is truly hard to replicate. The heart of this home may just be its incredible outdoor living space. Step through the living area and onto the expansive deck, where a covered canopy creates a year-round outdoor room overlooking the lush Howell Creek Preserve. With a firepit, market lighting, and treetop views stretching across the native Florida landscape, this is the kind of space that begs you to linger—morning coffee surrounded by nature, afternoon cocktails with friends, or evenings gathered around the fire under the lights. The elevated vantage point places you virtually eye-level with the cypress canopy, creating a dreamy sense of privacy and connection to nature that is rarely found in townhome living. And perhaps best of all, this is a view that cannot be renovated into another home. Inside, soaring 14-foot ceilings and dramatic picture windows fill the living room with an abundance of natural light while framing beautiful views of the preserve. The open, airy design makes the home feel exceptionally spacious and brings the outdoors in. The stunning kitchen features gorgeous Spanish tile flooring, solid wood cabinetry, granite countertops, and a new backsplash. The dining room adds character with built-in cabinetry and French doors, while the spacious indoor laundry room provides exceptional everyday convenience. Upstairs, two generously sized bedrooms and two full bathrooms provide a comfortable private retreat. A convenient powder room is located downstairs for guests. The coveted end-unit location also offers additional outdoor space along the side of the home, beautifully enhanced with brick hardscaping and room for relaxing, grilling, entertaining, or overflow parking. Parking is another standout feature, with a one-car garage plus two designated parking spaces—a rare convenience in this setting. And then there is the location. Situated in the prestigious 32789 zip code, this home puts you within walking distance of the Winter Park Racquet Club, the Winter Park Chain of Lakes, and surrounded by some of Central Florida’s most sought-after real estate. Enjoy the best of Winter Park while coming home to your own private perch above the trees. Fee-simple ownership. No HOA fees. Exceptional architecture. Preserve views. Incredible outdoor living. Coveted Winter Park location. This is far more than a townhome—it is a lifestyle.

2881 Temple Trail, Winter Park
$599,000
3 Beds ⋅ 2 Baths ⋅ Lake Waunatta Wods SubDv. ⋅ 32792 Zip Code
MOVE IN READY! New roof, new bathrooms, new kitchen, new floors, new electrical panels and more. Located in the beautiful lake community of Lake Waunatta Woods. Large private lot on greenbelt. 3 bedroom, 2 bath POOL home with 2 masters and split floor plan. The second master has outside entrance for option to use as a mother-in-law suite or rental. Spacious living room/dining room, family room, laundry room and 2 car garage. Beautiful pool area with screened porch and two patios. Just minutes to UCF and Full Sail University. Easy access to 417 and 15 minutes to downtown Winter Park, walk to Publix and Target. Fast closing available. Don't miss this gem, pack your bags and live life in this mini retreat that you will call home!

4026 Tenita Drive, Winter Park
$650,000
2 Beds ⋅ 2 Baths ⋅ Mack Peter Rev SubDv. ⋅ 32789 Zip Code
Rare opportunity to own a charming Duplex on a corner lot in the heart of Winter Park! Located walking distance to Mead gardens and Orange Ave, and less than a mile from Park Ave. shopping and dining, this incredible investment is positioned for convenience and enjoyment! Across the street is a community garden. Whether you are looking for an investment property to add to your portfolio or a primary residence with income generating capabilities, this property has it all! New roof in 2024, and new windows and exterior paint in 2026. AC's updated in 2024 & 2025. Schedule a tour to secure this incredible investment today!

901 Harmon Avenue, Winter Park
$1,625,000
4 Beds ⋅ 4 Baths ⋅ Charmont SubDv. ⋅ 32789 Zip Code
Virtually Staged. A rare opportunity to live on a quiet one-way street overlooking a park in the heart of Winter Park. Built in 2007 and meticulously maintained, this exceptional 4-bedroom, 4-bath pool home with a dedicated office offers timeless design, thoughtful updates, and an unbeatable location. A welcoming covered front porch provides the perfect spot to enjoy your morning coffee. Inside, soaring ceilings, extensive moldings, travertine and hardwood floors, and abundant natural light create an elegant first impression. Just off the foyer, French doors open to a private office, ideal for working from home. A secondary bedroom and full bath with a walk-in shower are conveniently located on the main level. The spacious kitchen flows seamlessly into the family room and features granite countertops, solid wood soft-close cabinetry, a gas cooktop, wall oven, breakfast bar, wet bar, walk-in pantry, and a sunny breakfast nook overlooking the lanai and pool. The adjoining family room is anchored by a gas fireplace and French doors leading outdoors. The covered lanai showcases a tongue-and-groove ceiling and remote-controlled screens, creating the perfect setting for year-round entertaining. The generous first-floor primary suite offers space for a sitting area and features two custom walk-in closets, dual vanities, a soaking tub, separate shower, and private water closet. A beautiful wrought-iron staircase leads upstairs to two generous en-suite bedrooms and a cozy loft. The private backyard is designed for relaxation and entertaining, featuring a saltwater pool and spa surrounded by lush landscaping. Additional highlights include two newer HVAC systems (2022 and 2023), a gas water heater (2022), central vacuum system, built-in Home Team pest defense system, and plantation shutters throughout. Located within the highly sought-after Audubon K-8 and Winter Park High School districts, this exceptional home is ideally situated between Park Avenue and Corrine Drive, with downtown Orlando just minutes away.

341 E Reading Way, 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
$835,000
4 Beds ⋅ 4 Baths ⋅ Meadows At Hawks Crest SubDv. ⋅ 32792 Zip Code
One or more photo(s) has been virtually staged. **This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buy-down that reduces the buyer's interest rate and monthly payment.** This luxurious Modern Style home epitomizes maintenance-free living, featuring a premium, state of the art solar system YOU OWN OUTRIGHT, nearly eliminating your cost of electricity. Ask to see the bill. The premium solar system is PAID OFF with a TRANSFERABLE WARRANTY by manufacturer. This off-grid solar system comes with a WHOLE HOUSE BATTERY BACKUP, keeping your lights on when the power goes out. This home already comes wired for electric vehicles with room to expand. Excess power generated is sold back to the power company through the NET METERING program, resulting in credits back to the owners at the end of the year. The solar system also has two power monitoring systems for tracking your energy usage & production, conveniently controlled by your phone and computer. Hawks Crest is your home to community, where residents enjoy gated access into a landscaped resort atmosphere, featuring water fountains throughout, with an abundance of amenities. The clubhouse features a resort pool & kiddie pool, a fitness center, with sidewalks & playgrounds, along with the community’s private dock access to Lake Howell with a canoe/kayak launch. Now imagine, relaxing and enjoying park and pond views from your expansive lanai, soaking in the serene sunsets & manicured landscaping, all from the comfort of your spacious, 4-bedroom 3.5 bath home, including a loft upstairs, all conveniently located just a short distance from the resort clubhouse. Owners can relax and unwind while management handles all landscaping around your home, truly providing you a maintenance-free living lifestyle. Additional upgrades with this home include, commercial grade luxurious vinyl wide-plank flooring, two power monitoring systems, a whole-house water softener & filter system, and two HVAC units, all designed for comfort, convenience, and a very clean home, where you can relax. Nestled in this spacious home, you’ll find 20-foot-high ceilings with awe-inspiring views of the illuminated pond fountain, creating a serene view & relaxing atmosphere you’ll enjoy, even from the kitchen sink. Your chandelier can be lowered 20-feet to the floor for easy maintenance & cleaning, using a winch lift system in the attic.(Rated up to 200 lbs). And even watch the rockets launch at The Cape from the front yard. Uniquely designed, this home was built to withstand extreme weather, featuring a concrete/granite tile roofing system, steel reinforcement, concrete-filled block walls & slab, all anchoring to the foundation, uniquely tying everything together. Meticulously maintained by the owners, this home comes with a complete set of blueprints, along with many photos & videos taken of the home during the building process. Owners even have documents for all equipment & appliances. And the premium solar system comes with a transferable warranty that will keep the lights on when the power is out. This home features a split floor-plan, with a primary bedroom on both the first and second floors. Spanning 2,589 sq.ft., this home offers an additional 540 sq.ft. of screened-in lanai, providing a private outdoor oasis where you’ll find owners enjoying the tranquility of Florida sunsets. Schedule a showing for your buyers today! And…***Remember to see the list of the owners’ upgrades***.

1090 Wildmeadow Run, Winter Park
$899,000
Fairbanks Park SubDv. ⋅ 32789 Zip Code
Rare corner lot with stunning views of Lake Midget, located in the heart of Winter Park within an area of modern new-construction homes. This build-ready property offers an exceptional opportunity to create a custom residence in one of the city’s most desirable neighborhoods. Just minutes from Park Avenue and Winter Park Village, with easy access to premier dining, shopping, and entertainment. Lots like this are seldom available. Whether you’re envisioning a custom residence or an investment in one of Central Florida’s most desirable neighborhoods, this is a truly rare opportunity in the heart of Winter Park.

731 Midget Drive, Winter Park
Start Your Search