Winter Park Homes with Private Entrance Exterior Features

Winter Park Homes with Private Entrance Exterior Features

Welcome to Winter Park, Florida—a charming city nestled in Orange County, renowned for its picturesque landscapes and vibrant community spirit. With its tree-lined streets, beautiful parks, and a rich cultural scene, Winter Park offers a unique blend of small-town charm and metropolitan conveniences. Just a stone's throw from downtown Orlando, this delightful city is celebrated for its historic architecture, upscale boutiques, and a plethora of dining options that cater to every palate.

One of the standout features of homes in Winter Park is the availability of properties with private entrance exterior features. These homes provide a sense of exclusivity and security, allowing residents to enjoy their own space without compromising on the beauty and community spirit that Winter Park embodies. Imagine coming home to your own private sanctuary, where you can unwind after a long day, entertain friends, or simply enjoy the serene Florida weather in peace.

The architectural styles in Winter Park are as diverse as its residents, from charming bungalows to modern masterpieces. Many of these homes with private entrances boast lush landscaping, spacious patios, and inviting outdoor spaces that are perfect for hosting gatherings or enjoying quiet evenings under the stars.

Whether you're drawn to the vibrant arts scene, the nearby lakes, or the lush golf courses, Winter Park is a place where you can truly feel at home. Explore the possibilities of owning a home with a private entrance in this enchanting city, and let Winter Park welcome you to a lifestyle defined by comfort, elegance, and community.

Newest Winter Park Homes with Private Entrance Exterior Features

4 Beds ⋅ 3 Baths ⋅ Acreage & Unrec SubDv. ⋅ 32792 Zip Code

Welcome to an extraordinary private lakefront retreat in Winter Park, where expansive grounds, exceptional amenities, and breathtaking Lake Howell views come together in one special property. Set behind a private gated entrance on approximately 4.3 total acres, with roughly half of the property consisting of dry land and the balance extending into Lake Howell, this remarkable estate offers a rare combination of privacy, space, and direct lake access, yet remains just minutes from the charm of Park Avenue, Interlachen Country Club, shopping, dining, and everything Winter Park has to offer. Lake Howell provides a spectacular backdrop for everyday living and entertaining, with opportunities for boating, fishing, water sports, sunset cruises, and unforgettable days on the water. The property features its own private boat ramp, boathouse, and boat dock, making lake life exceptionally convenient. The grounds are designed for both grand entertaining and relaxed family living. A massive detached barn offers an incredible flexible space for private events, parties, gatherings, game nights, or simply creating your own ultimate entertainment venue. Fully air conditioned and featuring high ceilings, the barn provides room for additional vehicles, RVs, boats, recreational equipment, and more. It also includes a private gym and bathroom, making it a versatile addition to the property. For RV enthusiasts, the property features a full 50 amp RV hookup with water and sewer hookups. The property is Agriculture zoned and allows horses. A separate four-car detached garage with workshop provides substantial storage and workspace. A generator adds convenience and peace of mind. The expansive fenced grounds offer plenty of room for family, pets, recreation, and outdoor activities, including a large playset and a firepit with comfortable seating—the perfect setting for cool evenings, roasting marshmallows, sharing stories, and making memories together. The recently updated pool area is designed to feel like your own private resort. Enjoy the covered lanai, outdoor kitchen, pool, and stunning lake views, along with a gas fireplace that creates an inviting atmosphere for evening entertaining. The outdoor kitchen is a chef’s dream, making it easy to host everything from casual family gatherings to unforgettable waterfront celebrations. Inside, the home was thoughtfully renovated in 2016 and offers just over 3,377 square feet under air, with approximately 7,758 total square feet. Beautiful wood flooring, tile, and carpeted bedrooms create a comfortable blend of style and functionality. The Florida room provides the perfect place to relax, take in the lake views, and enjoy the natural beauty surrounding the home. The upgraded kitchen features stainless steel appliances and a Thermador range, while the spacious executive office provides an ideal work-from-home environment or private study. The residence offers four bedrooms and three bathrooms, providing generous accommodations for family and guests. With multiple indoor and outdoor gathering spaces, extraordinary storage, recreational amenities, and direct access to Lake Howell, this property is much more than a home—it is a private lifestyle estate. Whether you're looking for a peaceful waterfront sanctuary, a place to entertain on a grand scale, a family compound, or simply a rare piece of Winter Park property with exceptional lake access, this property delivers an unparalleled opportunity.

2622 Lake Howell Lane, Winter Park

3 Beds ⋅ 3 Baths ⋅ Edgewood Sub SubDv. ⋅ 32789 Zip Code

WELCOME TO CONTEMPORARY LUXURY IN THE HEART OF WINTER PARK! This stunning two-story pool residence has been beautifully remodeled from top to bottom and offers high end design, high-end finishes and an exceptional lifestyle location near East End Market, Baldwin Park, Audubon Park and all of Winter Parks charm. Behind the private gated courtyard and modern fencing, discover a thoughtfully designed home featuring custom built-ins, designer finishes, porcelain tile, custom wood-plank stairs and a dramatic modern glass railing. The beautifully appointed kitchen is designed for both entertaining and everyday living and features premium Wolf gas cooking appliances with range hood, Sub-Zero refrigerator, stainless steel wine refrigerator, microwave, stainless farmhouse sink, pantry and stylish pendant lighting. The open living areas provide a wonderful setting for gathering and entertaining. The downstairs primary suite offers convenience, privacy and direct access to the spectacular outdoor pool living area. The luxurious en-suite bath features dual vanities, custom cabinetry and mirrors, high-end designer fixtures, beautiful tile work and a spacious glass-enclosed shower. Upstairs, you will find generously sized bedrooms, custom closet spaces and a beautifully finished bonus room offers exceptional flexibility for a home office, fitness room, exercise space, storage or additional flex space. Additional features include a dedicated first floor laundry room and powder room, upstairs linen closet, designer lighting through out and a two-car garage. Step outside to your own private retreat! The covered lanai flows seamlessly to the beautiful custom pool and outdoor entertaining area featuring a gas fire pit. Mature bamboo landscaping, a fenced yard and contemporary entrance fencing create a private and inviting setting. LOCATION, LOCATION, LOCATION! Enjoy the highly desirable Winter Park lifestyle with convenient access to East End Market, local coffee shops, exceptional restaurants, specialty shopping, markets and community events. Nearby destinations include Leu Gardens, Baldwin Park, Park Avenue and Downtown Winter Park. Zoned for Audubon Park School (K-8) and Winter Park High School; buyers should verify school assignments and enrollment eligibility. This exceptional move-in-ready home combines contemporary luxury, resort-style outdoor living and one of Central Florida’s most desirable lifestyle locations!

1922 Hammerlin Avenue, Winter Park

2 Beds ⋅ 2 Baths ⋅ Parkview Village SubDv. ⋅ 32792 Zip Code

VALUE OPPORTUNITY IN WINTER PARK! Welcome to 3020 Antique Oaks Circle #129, a spacious 2-bedroom, 2-bath FIRST-FLOOR CONDO offering approximately 1,018 square feet in the conveniently located Parkview Village community in Winter Park, FL 32792. If you have been searching for an affordable Winter Park condo, investment property, renovation opportunity, first-floor condo or 2-bedroom condo in Winter Park, this property deserves your attention. The functional floor plan offers generous living space, two full bathrooms, an interior laundry area and the convenience of first-floor living. Parkview Village offers desirable community amenities including a COMMUNITY POOL, SPA, TENNIS COURTS and recreational areas, creating an appealing combination of location, convenience and value. LOCATION IS A MAJOR HIGHLIGHT! Enjoy easy access to Semoran Boulevard/436, Aloma Avenue, University Boulevard, Downtown Winter Park, Park Avenue, Rollins College, UCF and major Central Florida roadways. Shopping, restaurants, grocery stores and everyday conveniences are close by, making this an excellent option for buyers looking for a Winter Park condo close to dining, shopping, entertainment and employment centers. The property is currently served by Aloma Elementary School, Glenridge Middle School and Winter Park High School. Buyers are encouraged to independently verify current school zoning and assignments with Orange County Public Schools. IMPORTANT VALUE OPPORTUNITY: The property has known mold present in the kitchen area that requires professional remediation, and the asking price has been positioned to reflect the property's current condition and the work needed. This creates an opportunity for a buyer who is prepared to complete the necessary remediation and customize the property to their own style. Buyers are encouraged to perform their own inspections, obtain professional remediation evaluations and verify all property and association information. With a Winter Park address, first-floor location, 2 bedrooms, 2 full bathrooms, community amenities and convenient access to shopping, dining and major roadways, this condo offers significant potential for the buyer willing to address the existing condition. Bring your vision and take advantage of this affordable Winter Park condo opportunity!

3020 Antique Oaks Circle Unit 129, Winter Park

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

It doesn't get much better than this: Living in a Lakefront and Winter Park community, that is convenient to I-4 providing easy access to points north and south, downtown Winter Park, shopping, fine dining, and the price can't be beat. The HOA dues includes water, trash pickup, a full package from Spectrum including internet. Lakeside Manor is situated on the north side of Lake Killarney, a 239 acre lake that is perfect for sailing, motor boating and skiing. The lush courtyard, lakeside pool, clubhouse and gazebo, updated dock and private boat ramp make this a serene place to enjoy the best of Central Florida in a noisy world. This one bedroom condo is in original condition, with 3 year old A/C unit, and is ready for your personal touches to make it your own.

2500 Lee Road Unit 143, Winter Park

3 Beds ⋅ 4 Baths ⋅ Dixie Terrace SubDv. ⋅ 32789 Zip Code

Set along one of Winter Park’s charming brick streets just steps from Park Avenue, this beautifully maintained home pairs refined design with an exceptional location. Impressive curb appeal sets the tone, while thoughtfully curated interiors create a home that feels both elevated and inviting. Inside, the main living space centers around a custom entertainment wall with built-in shelving and an electric fireplace. The adjoining kitchen is equally impressive, featuring quartz countertops, a statement La Cornue range, paneled refrigerator, and a cleverly hidden walk-in pantry. A sun-filled breakfast nook provides a casual dining space, while sliding glass doors create a seamless connection to the outdoor living areas. For larger gatherings, the spacious formal dining room offers an elegant setting for entertaining, and a well-designed mudroom and laundry combination adds everyday functionality. The primary suite is a private retreat with generous proportions and a beautifully appointed spa-inspired bath. A custom trough-style sink, separate makeup vanity, oversized walk-in shower, freestanding soaking tub, and expansive walk-in closet create a space that feels luxurious yet highly functional. Two additional bedrooms are both ensuite, offering privacy and comfort for family and guests. Outdoors, the home truly impresses. A lush wall of mature bamboo surrounds the backyard, creating an unexpected sense of privacy just moments from the heart of Winter Park. The resort-style pool features a sun shelf and built-in seating, while a pergola provides the perfect setting for al fresco dining and relaxed evenings outdoors. For the car enthusiast there is a car lift in the garage allowing for storage of up to 3 vehicles. The location is difficult to match, just steps from the shops, restaurants, and energy of Park Avenue and minutes from Hannibal Square, Winter Park Village, Park Maitland School, and the Enzian Theater. Beautifully maintained, thoughtfully designed, and positioned in one of Winter Park’s most desirable locations, this is a rare opportunity to enjoy an exceptional lifestyle in the heart of it all.

751 Pansy Avenue, Winter Park

4 Beds ⋅ 4 Baths ⋅ Seville Park SubDv. ⋅ 32789 Zip Code

This "Investment Opportunity" duplex is centrally located on a quiet, tree lined, brick street, close to shopping, restaurants, downtown Winter Park, Rollins College & Mead Gardens. It has a total of 4 bedrooms, 2 full baths & 2 half baths. Each unit has 2 bedrooms with a Jack & Jill bath, and 1 half bath. Live in one side while a tenant lives in the other.

1016 Aragon Avenue, Winter Park

4 Beds ⋅ 4 Baths ⋅ Seville Park SubDv. ⋅ 32789 Zip Code

This "Investment Opportunity" Duplex is centrally located on a quiet tree lined, brick street, close to shopping, restaurants, downtown Winter Park, Rollins College & Mead Gardens. It has a total of 4 Bedrooms, 2 full baths & 2 half baths. Each unit has 2 bedrooms with a Jack & Jill bath, and 1 half bath. Live in one side while a tenant (now occupied) lives in the other.

1016 Aragon Avenue, Winter Park

5 Beds ⋅ 5 Baths ⋅ Kenilworth Shores Sec 06 SubDv. ⋅ 32789 Zip Code

Under Construction. Located in the Kenilworth Shores neighborhood, this stunning new residence brings an elevated level of new construction to an increasingly desirable pocket of Winter Park. A sophisticated modern farmhouse façade creates an impressive first impression, framed by a sweeping double-entry curved driveway that gives the home a commanding yet welcoming presence. Inside, the open-concept design is both polished and remarkably livable. A dedicated home office sits just off the entry, while the expansive main living space is anchored by a statement entertainment wall with an electric fireplace. Pocketing sliders disappear to create a seamless connection to the covered lanai and backyard, extending the home’s entertaining spaces outdoors. At the center of it all, the chef’s kitchen features Taj Mahal countertops, an oversized island, custom cabinetry, and a complete suite of Stainless steel appliances. A generous dining area and large walk-in pantry add to the home’s effortless functionality. One of the floor plan’s greatest advantages is the inclusion of two bedrooms on the main level, a rarity in Winter Park. The primary suite is particularly impressive, offering a true sense of retreat with a spa-inspired bath featuring dual vanities, a freestanding soaking tub, an oversized walk-in shower, and an expansive custom closet with a center island. The additional downstairs bedroom provides flexibility for guests or multigenerational living. Upstairs, three additional generously sized bedrooms are served by two full baths and a dedicated laundry room, along with an air-conditioned bonus room that easily functions as a sixth bedroom, theater, game room, or fitness studio. In all, the home offers five bedrooms, four and a half baths, a private office, and a climate-controlled bonus space, giving families room to spread out without compromise. The backyard was designed to feel like a private resort. A covered lanai and dedicated cabana with a full summer kitchen overlook the large pool and spa, while generous lawn space provides something increasingly difficult to find in newer Winter Park construction. Located minutes from Park Avenue's shops, cafes, and restaurants and close to Advent Health Winter Park, Cady Way Park, and the YMCA, this home offers an exceptional location. For those seeking new construction without compromising on space, location, or lifestyle, this is a Winter Park home that checks the boxes that matter.

648 Worthington Drive, Winter Park

2 Beds ⋅ 2 Baths ⋅ Mead Garden Condominium SubDv. ⋅ 32789 Zip Code

Located just minutes from Winter Park's famed Park Avenue, this charming 2 bed, 2 bathroom corner condominium features a light and bright open floor plan, updated finishes, views of Mead Gardens, and one of Central Florida's most sought after locations! As you enter the front door, you are immediately welcomed by views of Mead Botanical Gardens, Khaki oak wood-look luxury vinyl floors, an open living/dining room combo, a private balcony with garden views and kitchen with freshly painted cabinets and stainless steel appliances. Off of the family room, 2 spacious bedrooms including a master suite with a renovated bathroom, and a second bedroom with private access. Everyday is a vacation when you can start your day off with a coffee on the private balcony, cool off on a warm summer's day in the pool and end it with a walk through the 48 acre natural enclave just next door as the sun sets. Zoned for A rated schools including Audobon Park and Winter Park High school and located just minutes from world class shopping, dining and entertainment in historic downtown Winter Park, Downtown Orlando, and College Park. Schedule your showing Today!

1250 S Denning Dr Unit Unit 233, Winter Park

6 Beds ⋅ 5 Baths ⋅ Timberlane Shores SubDv. ⋅ 32789 Zip Code

Under Construction. Beautifully composed from every angle, this extraordinary residence captures something increasingly rare in new construction: a genuine sense of character, permanence, and architectural identity. Designed by Gary Hancock and meticulously executed by Vimaro Homes, this home features extraordinary materials, bespoke details, and spaces that feel equally refined and inviting. Set on a large corner homesite in Timberlane Shores, the residence enjoys an uncommon sense of openness, complemented by beautiful lake views from its upper levels. Inside, a striking marble mosaic foyer introduces interiors where every finish has been carefully considered. The main living room is a showpiece, featuring illuminated tray ceilings, extensive custom millwork, a bespoke built-in feature wall, and a fireplace wrapped in Calacatta marble. Expansive pocketing sliders disappear to seamlessly connect the living space with the covered lanai, creating an effortless transition between indoor and outdoor entertaining. At the heart of the home is a chef's kitchen designed to be a true showpiece. Calacatta marble countertops, custom inset cabinetry, a statement ILVE range, paneled built-in refrigerator, and a full suite of Thermador appliances establish an exceptional level of finishes. Just beyond, a large secondary prep kitchen provides plenty of additional storage. A charming breakfast nook offers a more intimate setting for everyday dining, while the formal dining room has been designed for memorable evenings, complemented by a sophisticated bar and glass-enclosed wine display. The first-floor primary suite is a true retreat with direct access to the lanai, custom millwork, illuminated tray ceilings, and an impressive sense of scale. Its spa-inspired bath is finished with marble flooring, Perrin & Rowe fixtures, dual vanities, a freestanding soaking tub, and an oversized walk-in shower. Completing the suite are designated his-and-hers closets, providing an exceptional amount of storage and functionality. An additional main-level bedroom can be used as a guest suite, private office, or library. Upstairs, the home continues to impress with four additional bedrooms and a spacious second living area. Above, a third-floor bonus space provides yet another dimension of flexibility and can be transformed into a private gym, game room, media room, or secluded retreat. From the upper levels, glimpses of the nearby lake further reinforce the home's special setting. Outdoors, the residence was created to embrace the Central Florida lifestyle. The outdoor spaces were conceived as a true extension of the home, with a covered terrace that creates an inviting setting for everything from relaxed afternoons to evening gatherings. Retractable screens allow the space to be enjoyed throughout the year, while a beautifully appointed summer kitchen makes outdoor dining effortless. Beyond, the pool is framed by an oversized patio, manicured grounds, and thoughtfully layered landscaping. This home offers a location that is difficult to replicate. Tucked within the peaceful enclave of Timberlane Shores, the home is just minutes from Park Avenue's shopping and dining, while remaining within walking distance of Blue Jacket Park and the dining, shopping, and lifestyle of Baldwin Park. The property is also zoned for the highly desirable Audubon Park K-8 School. IF PURCHASED EARLY, THE INTERIOR OF THIS HOME CAN BE CUSTOMIZED TO THE NEW OWNERS PERSONAL TASTE. CALL FOR ADDITIONAL DETAILS.

620 Virginia Drive, Winter Park

5 Beds ⋅ 6 Baths ⋅ Park Grove SubDv. ⋅ 32789 Zip Code

Under Construction. Designed to capture the timeless character of Olde Winter Park while delivering an extraordinary level of modern luxury, this is a truly one-of-a-kind residence by Vimaro Homes. Set within the highly sought-after Park Grove neighborhood and designed by renowned architect Gary Hancock, the home makes an unforgettable first impression with a stately front façade, manicured grounds, dual porte cochere’s, and a motor court leading to a two-car garage. Every element has been thoughtfully considered to create a residence that feels as though it has always belonged in Winter Park. Inside, exceptional craftsmanship takes center stage. A marble mosaic entry introduces interiors defined by chevron-pattern hardwood flooring, refined millwork, natural stone, and carefully curated finishes. The floor plan is equally impressive, balancing grand entertaining spaces with an effortless sense of livability. The main level features a dedicated library/home office, formal dining room, and expansive gathering room overlooking the private courtyard. At the heart of the home, the chef’s kitchen pairs Calacatta marble countertops with a full suite of Thermador appliances, a statement ILVE range, and an oversized butler’s pantry offering exceptional prep and storage space. The first-floor primary suite is a private retreat with direct access to the courtyard and an incredible spa-inspired bath finished in marble. Dual vanities, Perrin & Rowe fixtures, a freestanding soaking tub, walk-in shower, and an expansive dressing room elevate the suite to another level. Upstairs, four generously proportioned bedrooms each feature an ensuite bath and walk-in closet, surrounding a spacious central loft ideal for an additional living or entertaining space. Continuing to the third level, a fully finished attic space provides an unexpected bonus room perfectly suited for a private gym or a game room. The outdoor living experience is just as remarkable. At the center of the home is a spectacular courtyard-style pool, creating a private resort atmosphere framed by the residence and lush landscaping. An expansive covered cabana provides multiple areas for dining and lounging, complemented by a fireplace and full summer kitchen for year-round entertaining. Beyond the courtyard, ample yard space adds another layer of usability rarely found with such an intimate outdoor design. This home also offers the rare opportunity to enjoy one of Winter Park’s most desirable residential settings while remaining within walking distance of the boutiques, acclaimed restaurants, cafés, and vibrant atmosphere of Park Avenue. Hannibal Square and Winter Park Village are also just moments away, placing some of the city’s best dining, shopping, and entertainment within effortless reach. Timeless in its architecture and uncompromising in its execution, this home is destined to become one of Winter Park’s most distinguished residences. Renderings are artistic interpretations. Features and finishes may vary from final construction.

857 Brock Street, Winter Park

4 Beds ⋅ 5 Baths ⋅ Charmont SubDv. ⋅ 32789 Zip Code

Under Construction. Perfectly positioned along one of Winter Park's most picturesque tree-lined cobblestone streets, this exceptional new construction residence offers a rare opportunity to own a home where timeless architecture, refined craftsmanship, and an unrivaled location come together. A striking marble mosaic foyer creates an unforgettable first impression, immediately setting the tone for the level of detail found throughout the residence. Just off the entry, a dedicated home office provides the ideal space for working remotely or enjoying a quiet retreat. Beyond, the thoughtfully designed floor plan unfolds into expansive living spaces filled with natural light and connected by effortless flow. The great room serves as the heart of the home, highlighted by a custom-built entertainment wall with integrated LED lighting, a sleek electric fireplace, and oversized sliding glass doors that blur the line between indoor and outdoor living. Designed for both everyday living and elegant entertaining, the chef's kitchen is a showpiece. Taj Mahal quartzite countertops are paired with an exceptional suite of Thermador appliances, including a paneled built-in refrigerator, while extensive custom cabinetry provides an abundance of storage without compromising the clean, sophisticated aesthetic. The adjoining dining room creates an inviting setting for gatherings and is complemented by a beautifully appointed dry bar complete with a wine refrigerator, making entertaining effortless. Privately situated on the main level, the primary suite is a true retreat with direct access to the lanai through expansive sliding glass doors. The spa-inspired bath showcases exquisite marble mosaic tile, dual vanities, a freestanding soaking tub, an oversized walk-in shower, and a generous custom walk-in closet, creating a space that feels both luxurious and serene. Upstairs, three spacious guest bedrooms are thoughtfully arranged alongside a comfortable secondary living area and an expansive bonus room, offering remarkable flexibility for a media room, game room, fitness studio, or additional gathering space. The outdoor living experience is equally impressive. A spacious covered lanai is designed for year-round enjoyment, featuring a fully equipped summer kitchen, generous space for alfresco dining and entertaining, a sparkling pool and spa, and ample green space for recreation or relaxation. While the home's finishes and craftsmanship are exceptional, it is the location that truly sets it apart. Enjoy the rare privilege of walking to the boutiques, award-winning restaurants, and vibrant atmosphere of Park Avenue, the campus of Rollins College, Virginia Park, and the acclaimed East End Market. Zoned for highly sought-after Audubon K-8 and surrounded by the charm and character of the Lake Sue District, this is more than a home; it's a statement of luxury Winter Park living.

361 E Kings Way, Winter Park

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