Winter Park Homes with Garden View

Winter Park Homes with Garden View

Welcome to Winter Park, Florida, a picturesque city known for its charming tree-lined streets, vibrant arts scene, and lush landscapes. Nestled just north of Orlando, Winter Park is a delightful blend of small-town charm and modern amenities, making it a sought-after destination for families, retirees, and professionals alike. With its rich history, Winter Park boasts a variety of architectural styles, from Mediterranean Revival to Craftsman bungalows, each echoing the city’s unique character.

One of the most appealing features of Winter Park is its stunning homes with garden views. Imagine waking up every morning to the sight of vibrant blooms and lush greenery right outside your window. These homes are designed to harmonize with nature, offering residents a tranquil retreat from the hustle and bustle of daily life. Many properties feature beautifully landscaped gardens, private patios, and spacious backyards, perfect for entertaining guests or simply enjoying a quiet evening under the stars.

Beyond the allure of these charming homes, Winter Park offers an array of outdoor activities. Explore the scenic parks, such as Central Park and Mead Botanical Garden, where you can stroll along winding paths, relax by serene lakes, and immerse yourself in the beauty of Florida’s natural landscapes. The city also boasts a thriving dining and shopping scene, with boutique shops and gourmet restaurants lining Park Avenue.

Whether you’re looking for a cozy bungalow or a luxurious estate, Winter Park’s homes with garden views provide the perfect backdrop for a serene and fulfilling lifestyle. Come discover the enchanting allure of Winter Park, where your dream home awaits!

Newest Winter Park Homes with Garden View

3 Beds ⋅ 2 Baths ⋅ Eastbrook Subd Unit No 05 SubDv. ⋅ 32792 Zip Code

Welcome to this beautifully updated 3-bedroom, 2-bath home in beautiful Winter Park! This move-in-ready property features stylish wood-look tile flooring throughout, creating a seamless, modern look that's both attractive and easy to maintain. The home has two beautifully renovated bathrooms with contemporary finishes, along with a newer A/C and a new roof in 2026. The air-conditioned laundry room has plenty of storage space. Step outside to your spacious, fully fenced backyard, where you'll find plenty of room to entertain, play, or unwind around the cozy fire pit. The generous outdoor space offers endless possibilities for gatherings, gardening, or simply enjoying Florida's beautiful weather. A rare highlight is the oversized swing gate providing convenient side-yard access with ample room to park an RV, boat, trailer, or other recreational vehicles. Best of all, there's no HOA, giving you the freedom to make the most of your property without additional HOA restrictions. Perfectly situated just minutes from Costco, grocery stores, shopping, dining, and the popular Cady Way Trail, this home offers the ideal combination of comfort, convenience, and outdoor recreation. With easy access to major roadways and everything Winter Park has to offer, this home truly has it all. Welcome home!

3562 Bougainvillea Drive, Winter Park

2 Beds ⋅ 2 Baths ⋅ Four Seasons Condo SubDv. ⋅ 32792 Zip Code

WHAT A GEM! Tucked away in a private, sought after community and so conveniently located in breathtaking Winter Park. Here’s a beautifully maintained, upgraded and move-in ready home. With 2 large bedrooms and 1.5 bathrooms, this unit spans 1,219 square feet, providing an ideal space for cozy living. Enjoy the benefits of a peaceful and friendly community, with well-manicured grounds and a welcoming atmosphere. This charming home has been tastefully updated with upgraded laminate flooring, a renovated kitchen with granite countertops, newer cabinets and a stylish backsplash. The floor plan offers a dining & family room open combination which looks out on the porch and brings in plenty of natural light. Both nicely sized bedroom suites are on the second floor and have a shared & updated bathroom. Ample storage on the back patio for your bike and all your extra toys allowing you to enjoy your weekends. This is an extremely well managed community with an onsite manager taking pride in the community and care for their residents. Four Seasons community provides super amenities including a cubhouse with library, a renovated fitness center, 3 swimming pools, tennis courts, a laundry facility steps away and shuffleboard. Walk to Cady Way Park with tennis courts, baseball and soccer fields, playgrounds, community pool and Cady Way Trail. Minutes to Advent Health Winter Park Hospital, shopping on Park Avenue, Rollins College, Valencia, Full Sail and UCF. This pet friendly community and charming condo has everything you need! Great opportunity to own in FOUR SEASONS condominiums where LOCATION, LOCATION, LOCATION is prime!

200 Saint Andrews Boulevard Unit 2904, Winter Park

4 Beds ⋅ 2 Baths ⋅ Winter Park Pines Rep SubDv. ⋅ 32792 Zip Code

Virtually Staged. Welcome to a residence where timeless design meets modern sophistication in the highly sought-after Winter Park Pines community—one of Winter Park's most established neighborhoods, celebrated for its tree-lined streets, oversized homesites, exceptional schools, and proximity to world-class dining, shopping, golf, and cultural attractions. With no HOA, this thoughtfully renovated home offers the perfect balance of refined living and everyday comfort in one of Central Florida's most desirable locations. This 1,605 sqft, 4-bedroom, 2-bath residence, has been transformed with modern finishes, upgraded systems, and thoughtful design throughout. The open-concept layout seamlessly connects the living room, dining area, and kitchen, creating a bright and inviting space ideal for both everyday living and entertaining. The interior features new luxury vinyl flooring in all main areas and fully remodeled bathrooms with floor and wall tile, elongated modern toilets, updated vanities, and premium finishes. The main bathroom includes a new bathtub, medicine cabinet, and mirror cabinet, while the master bathroom offers a glass-walled shower with a niche and a double floating vanity with mirrored cabinets. The kitchen is a true centerpiece, showcasing a large island, quartz countertops, high-end custom cabinetry with soft-close drawers, and a pantry with built-in shelving. Luxury FORNO white-and-gold appliances elevate the space, including an induction cooktop and range, hood fan, double-door refrigerator with ice maker, and a microwave built into an island drawer. The kitchen is completed with a high-end white sink bowl and garbage disposal, adding both style and functionality. Major improvements were completed with permits, including new HVAC (2026), new water heater (2026), new 200 Amps electrical panel (2026), and a full plumbing repipe (2026). Additional upgrades include new wired smoke alarms and new doors throughout. The living room features modern potlights, and all bedrooms include contemporary ceiling fans. The lanai has been renovated, offering a comfortable outdoor retreat. Exterior enhancements include an updated roof (2020), fresh interior and exterior paint, a refinished garage floor, and an upgraded garage door opener (2026). The property also features a brand-new irrigation system (2026) to keep the grounds lush and easy to maintain. Smart-home additions include a smart Blink doorbell and a smart front-door lock, providing added convenience and security. The spacious, fully-fenced backyard offers privacy and endless possibilities for outdoor enjoyment, gardening, or future enhancements. Perfectly positioned just minutes from Winter Park Pines Golf Club, Cady Way Trail, Park Avenue, Rollins College, AdventHealth Winter Park, and the boutiques, fine dining, and cafés that have made Winter Park one of Central Florida's most coveted destinations, you'll also enjoy convenient access to Downtown Orlando, Baldwin Park, major highways, Orlando International Airport, and countless entertainment venues. With meticulous renovations, modern systems, smart-home upgrades, and an unbeatable Winter Park Pines location, this home is truly move-in ready and prepared to welcome its next owner.

2833 Prince John Road, Winter Park

2 Beds ⋅ 1 Baths ⋅ Dubsdread Heights SubDv. ⋅ 32789 Zip Code

Roof 2018 | HVAC 2020| Set on a deep, tree-canopied lot in one of Winter Park's most desirable established neighborhoods, this charming single-story concrete-block home blends timeless character with everyday convenience. A grand oak shades the front lawn, helping cool the home and lower energy costs, while durable masonry construction, a dimensional-shingle roof, and a full-length driveway leading to a covered carport deliver lasting value and practical, protected parking with an attached workshop & storage room. A generous screened front porch offers a breezy, bug-free spot for morning coffee or evening relaxation before you step inside to a spacious living room featuring gleaming refinished hardwood floors and a wood-burning fireplace framed by a classic white mantel with fluted columns. A large picture window floods the room with natural light, and a graceful curved archway, one of the home's most distinctive architectural details, leads you deeper into the thoughtfully connected floor plan. The kitchen is efficiently designed with cabinetry lining both walls for ample storage, laminate counters, under-cabinet lighting, and a full stainless-steel appliance suite. A double sink offers plenty of room to work and a large window overlooks the lush backyard, with a rear door providing easy access for grilling and entertaining. The adjacent, light-filled dining room offers flexible space that works well for family meals, a home office, or a quiet reading nook. Two comfortable bedrooms feature hardwood floors, ceiling fans with lights, and built-in closets, one with built-in shelving, while the bright corner primary enjoys windows on two walls for excellent light and cross-ventilation. A full bathroom is finished with a tiled tub-and-shower combination, a wood vanity, and a frosted privacy window that brings in daylight while maintaining seclusion. Out back, a large, fully fenced yard framed by mature oaks, palms, and established privacy hedges creates a secluded, park-like retreat with ample room to garden, play, entertain, or add a pool. Just minutes from historic Park Avenue, residents enjoy boutique shopping, award-winning restaurants, sidewalk cafés, museums, and year-round community events, with nearby College Park adding popular dining, breweries, and specialty shops. Outdoor recreation abounds with Dubsdread Golf Course, Mead Botanical Garden, Kraft Azalea Garden, and numerous parks close by, plus easy access to Winter Park's scenic chain of lakes and walking trails, all without requiring waterfront ownership. Commuting is effortless thanks to convenient access to Interstate 4, Fairbanks Avenue, Lee Road, SR 426, and SR 436, providing quick connections throughout Central Florida. Downtown Orlando, the Orlando Health and AdventHealth medical campuses, and major employment centers are all within easy reach. With excellent shopping, grocery stores, entertainment, and cultural attractions nearby, this sought-after location offers the perfect balance of quiet residential living and close proximity to everything Central Florida has to offer. This listing is for a single home and lot at 846 Driver Ave, but the owner would also consider selling the adjacent home next door to the North at 844 Driver Ave. If you are interested in purchasing both homes simultaneously, contact listing agent for more details.

846 Driver Avenue, Winter Park

2 Beds ⋅ 2 Baths ⋅ Aloma Park SubDv. ⋅ 32792 Zip Code

**This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.** Welcome to 5781 Shale Court in Winter Park, a 2-bedroom, 2-bath home designed for comfortable everyday living. This one-story residence offers a practical layout with space for relaxing, dining, and hosting guests. The two-bedroom configuration provides flexibility for residents, visitors, a home office, or a hobby room, while two full bathrooms add convenience for daily routines. Outdoor living includes a covered and screened patio, creating a comfortable space to enjoy fresh air, outdoor dining, or quiet downtime while staying shaded and protected from the elements. Located in Winter Park, the home is close to shopping, dining, parks, schools, and everyday conveniences. The area offers access to nearby destinations such as Winter Park Village, Park Avenue, local recreation, and major roadways connecting to Maitland, Orlando, and surrounding Central Florida communities.

5781 Shale Court, Winter Park

4 Beds ⋅ 3 Baths ⋅ Trinity Bay SubDv. ⋅ 32792 Zip Code

Welcome to 8433 Commander Cove, ideally situated on a quiet cul-de-sac in the highly sought-after Trinity Bay community. Upon entering this spacious home you're greeted by soaring vaulted ceilings, a formal dining area, and a stunning cathedral-style front window that fills the space with natural light. The separate enclosed kitchen offers functionality and charm, with French doors leading to a covered, tiled lanai. Step outside and enjoy a large patio surrounded by mature trees and lush landscaping—an ideal setting for morning coffee, outdoor entertaining, and family barbecues. The inviting family room showcases vaulted ceilings, a grand brick fireplace, and a versatile bonus den/office with a window, perfect for working from home or additional living space. Conveniently located off the family room is an indoor laundry area and half bath. The first-floor primary suite offers privacy and comfort, featuring a dual-vanity bathroom and private French door access to the covered lanai. Upstairs, you'll find three generously sized bedrooms, each equipped with ceiling fans and ample closet space, along with a second dual-vanity full bathroom. Whether you're a first-time homebuyer or looking for room to accommodate a growing family, this home offers exceptional value and functionality. Residents of Trinity Bay enjoy access to a community pool, community playground, and a private neighborhood boat ramp with access to the Lake Burkett and Lake Martha Chain of Lakes, where boating, water skiing, fishing, and other recreational activities are welcomed. Don't miss this opportunity to own a beautiful home in one of the area's most desirable neighborhoods!

8433 Commander Cove, Winter Park

5 Beds ⋅ 6 Baths ⋅ Green Oaks Rep SubDv. ⋅ 32789 Zip Code

Long before this home stood gracefully on its prominent corner, it existed as a vision in the mind of master builder Keith D. Field. Conceived as the opposite of a production home, it was crafted with a builder’s eye for structural integrity, thoughtful flow, and a seamless connection between indoors and out. Set on a generous 91-foot wide lot, this custom residence offers 5 bedrooms and a floor plan that feels both substantial and inviting. A wide front veranda sets a timeless tone from the moment you arrive. Dark-framed windows and doors create a striking contrast, while manicured hedges and brick-paved drives enhance the classic curb appeal and highlight the home’s architectural details. Step inside and you immediately sense that this is more than just a beautiful house—it’s a home with a story. At its heart is the reclaimed pine flooring, sourced from a Florida bridge. Rich with character, worn in all the right ways, these floors bring a warmth and authenticity you simply cannot replicate with something new. A long, gracious foyer introduces the main living spaces. To your left, a handsome study/office with a brick fireplace offers an intimate retreat for working. To your right, a formal dining room with garden views comfortably accommodates twelve. A discreet swing door leads to a well-appointed wet bar and large walk-in pantry, which then opens into the expansive kitchen. The kitchen is the true hub of the home, anchored by coffered ceilings, an oversized island, a full suite of high-end appliances, abundant cabinetry, and extensive counter space. A light-filled dinette offers the perfect spot for casual meals. At the center of the home, an oversized great room draws everyone together with its tall brick fireplace, built-in display/bookshelves, and high ceilings that add volume without sacrificing warmth. Two bedrooms are thoughtfully located on the main level, including the primary suite, privately positioned in one of the quietest corners of the home. Filled with soft natural light, accentuating the detailed millwork that runs from floor to ceiling. The primary bath is a retreat in itself, featuring slate flooring, double vanity, claw-foot soaking tub, water closet, walk-in shower with rain head, and a massive custom walk-in closet. The second main-level bedroom functions beautifully as a guest suite or flexible space, with an en-suite bath that also serves as a pool bath, a built-in Murphy bed with integrated cabinetry. A back facing staircase leads to two additional en-suite bedrooms on the second level. At the top of the landing, a large built-in workstation creates an ideal homework or creative zone, and both bedrooms enjoy access to a full-length front balcony. At the back of the home, a separate staircase leads to the fifth bedroom—a wonderfully private suite with dormer windows, angled ceilings with beams, and its own en-suite bath. In addition to a walk-in closet, cleverly designed built-in storage along the walls ensures a place for everything. Off the great room, a covered lanai with tongue-and-groove wood ceiling and brick built-in grilling station creates a comfortable space for year-round relaxation. A 45-foot lap pool is anchored by a striking cabana with fireplace, evoking a resort-inspired setting for long afternoons, evening gatherings, and memorable celebrations. This is a rare opportunity to own a thoughtfully crafted estate where history, craftsmanship, and everyday comfort come together in perfect balance.

1600 Legion Drive, Winter Park

2 Beds ⋅ 1 Baths ⋅ Lakeside Manor Apts Condo SubDv. ⋅ 32789 Zip Code

**This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.** Welcome to 2500 Lee Road, Unit 220, in Winter Park, a beautifully maintained condominium offering stylish, low-maintenance living in one of Central Florida's most convenient locations. Inside, the condo features 2 bedrooms and 1 bathroom with a functional layout suited for everyday living. Thoughtfully updated throughout, this unit features a modern kitchen with stainless steel appliances, charcoal quartz countertops, and a spacious island with ample storage. The bathroom has also been updated with contemporary finishes, while the unit's clean, modern design creates an inviting atmosphere throughout. A new A/C installed in 2025 provides added comfort and peace of mind. The floorplan includes comfortable living and dining areas, while the secondary bedroom offers flexibility for guests, a home office, or additional storage. The unit overlooks a beautifully landscaped courtyard and is conveniently located near designated parking. Residents enjoy access to a variety of community amenities, including a clubhouse, pool, laundry facilities, park areas, and dock access on Lake Killarney. The lakefront setting provides a peaceful environment and an opportunity to enjoy the surrounding natural beauty. Located in the heart of Winter Park, the condo is close to shopping, dining, parks, and popular destinations such as Winter Park Village, Park Avenue, College Park, Maitland, and Downtown Orlando. With its desirable community amenities and prime Winter Park location, this move-in-ready condo offers exceptional value and convenience.

2500 Lee Road Unit 220, Winter Park

3 Beds ⋅ 2 Baths ⋅ Park West Condo SubDv. ⋅ 32789 Zip Code

Virtually Staged. Welcome to Park West Condominiums — one of Winter Park’s most coveted and rarely available condominium communities, ideally located just one block from the boutiques, dining, and charm of Park Avenue. This unique 4th floor residence offers an exceptional combination of space, privacy, and potential. Featuring 3 bedrooms and 2 bathrooms, the expansive floor plan has been enlarged by enclosing two patios, creating generous living spaces rarely found in condominium living. Vaulted ceilings, skylights, and abundant natural light enhance the open, airy feel throughout the home, while the top-floor location provides remarkable tranquility and privacy. The spacious kitchen offers ample counter space, a breakfast bar, and excellent cabinet space, while the living area is anchored by a fireplace — another uncommon feature in condo living. Large bedrooms, a sizable in-unit laundry room with extensive storage, and an oversized attic provide an extraordinary amount of storage seldom seen in comparable properties. The primary suite features vaulted ceilings, a walk-in closet, and a spacious bathroom layout. For maximum flexibility, the second bedroom, featuring a bright Sun Room alcove, connects to the primary bedroom so it could also be utilized as a private den. Recent unit improvements include a NEW HVAC system, a NEW Water Heater, and Plumbing updates. A reserved covered parking space is included, along with plentiful guest parking for visitors. Residents of Park West enjoy a secure gated entrance, community pool, tennis court, on-site community manager, and beautifully maintained grounds with extensive recent community improvements completed. Association fees include water, sewer, and trash service, creating a truly low-maintenance “lock-and-leave” lifestyle ideal for travelers or seasonal residents. While this condo presents an exciting opportunity for personalization, the location, floor plan, and features make this an exceptional offering with tremendous potential. Opportunities in Park West are exceedingly rare — this is your chance to create something truly special in the heart of Winter Park.

300 Carolina Avenue Unit 402C, Winter Park

3 Beds ⋅ 4 Baths ⋅ Pennsylvania Place Rep SubDv. ⋅ 32789 Zip Code

Located just steps to the Golf Course and Park Avenue, in downtown Winter Park, 622 Penn Place is in the highly sought after Penn Place neighborhood. One of the few homes fronting the park with beautiful views from upper and lower porches, balconies and windows. This home provides the perfect balance of quiet privacy and convenient access to everything. The heart of the home features white kitchen cabinets, New stainless steel appliances and gas cooktop, overlooking eat-in breakfast nook and family room with gas fireplace & three sets of French doors opening to a bird and butterfly paradise with a huge covered, porch. There is also a dedicated office with built-in's and wet bar. The upstairs can be reached by both Elevator or elegant staircase and houses the owner’s suite with private balcony. It includes a large bathroom with dual sinks + makeup vanity, tub & separate shower, and oversized custom closet. Two additional bedrooms split from the master, as well as upstairs laundry room. Custom built by Maroon Fine Homes and beautifully updated and maintained, the high quality details and finishes can be felt throughout - features include high ceilings, crown molding, plantation shutters, and hardwood floors throughout. New Roof, New interior/exterior paint, acp tankless gas water heater and three covered patios. Fenced/Gated yard with four zone sprinkler system, paver driveway and attached 2 car garage with back alley entry. With its unparalleled location and custom details, 622 Penn Place is a rare opportunity to own in walking distance to downtown. Don’t miss your chance to make this exceptional property your next home!

622 Penn Place, Winter Park

2 Beds ⋅ 1 Baths ⋅ Glencoe Sub SubDv. ⋅ 32789 Zip Code

**This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.** Welcome to 440 Cambridge Blvd in Winter Park, a charming 2-bedroom, 1-bath home featuring an open floorplan, an additional family room, and inviting indoor-outdoor spaces that offer both comfort and flexibility. Thoughtfully maintained and updated over time, this property combines functional living with key improvements that add long-term value and peace of mind. Inside, the open floorplan creates a bright, connected flow across the main living areas—ideal for both everyday living and entertaining. The separate family room adds valuable versatility, perfect as a media room, home office, playroom, or relaxed second living area. The bedroom layout is practical and comfortable, providing a solid foundation for personal touches and customization. Recent updates enhance both the appeal and functionality of the home, including a roof installed in 2020, HVAC system replaced in 2019, a new garage door with opener (2019), and fresh exterior paint completed in 2024. The bathroom has been refreshed with a new sink, toilet, and tub surround in 2025, offering a clean, updated feel. The outdoor spaces further elevate the property. An enclosed front porch provides a welcoming spot to enjoy a quiet morning or unwind in the evening, while the open rear patio is perfect for grilling, dining, or relaxing outdoors. The private backyard offers plenty of space to expand your vision, with strong potential to create a personalized outdoor retreat. With its solid layout, meaningful updates, and room to grow, this home presents an excellent opportunity for buyers looking to settle into a well-located property while continuing to enhance it over time. Situated in desirable Winter Park, the home benefits from a location known for its established charm, tree-lined streets, and convenient access to shopping, dining, parks, and everyday essentials, making it one of Central Florida’s most sought-after communities.

440 Cambridge Boulevard, Winter Park

1 Beds ⋅ 1 Baths ⋅ Waterfall Cove SubDv. ⋅ 32789 Zip Code

This great second floor one bedroom 1 bath condo is in the quiet community of Waterfall Cove just off LeeRoad and 17-92 intersection. Conveniently located walking distance from shopping, dining, and Winter Park Village. Close to Park Avenue,Maitland 's Lake Lilly Park with the Farmer's Market and to Rollins College. Easy I-4 access. Open floor plan, walk in closet, and stack-able washer and dryer. Assigned parkingspace. Community features swimming pool, tennis court and playground. Rent price includes use of the amenities, free basic cable TV, free internet, and pest control.

1695 Lee Road Unit B210, Winter Park

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