Winter Park Homes with Private Pool type

Winter Park Homes with Private Pool type

Welcome to Winter Park, Florida – a picturesque city known for its enchanting tree-lined streets, vibrant cultural scene, and stunning lakes. Nestled just north of Orlando, Winter Park is a hidden gem that seamlessly blends small-town charm with modern conveniences. With its rich history, celebrated art galleries, and delightful boutiques, residents and visitors alike find themselves captivated by the city's unique allure.

One of the standout features of Winter Park is its lush landscape, which provides a perfect backdrop for relaxation and recreation. The city boasts a variety of parks, including the famous Central Park, where you can enjoy leisurely strolls, picnics, and community events. The nearby Winter Park Chain of Lakes offers opportunities for boating, fishing, and scenic views that will take your breath away.

For those seeking the ultimate in luxury and comfort, homes with private pools are a sought-after treasure in Winter Park. Imagine stepping into your own backyard oasis, where you can unwind under the Florida sun or host memorable gatherings with family and friends. These stunning properties often feature expansive outdoor living spaces, beautifully landscaped gardens, and state-of-the-art amenities, providing a perfect blend of relaxation and entertainment.

Whether you're looking for a cozy retreat or a spacious family home, Winter Park's real estate market offers a diverse selection of options to suit every lifestyle. Embrace the charm of Winter Park and discover the joys of living in a community that truly feels like home. Come explore the possibilities, and let your dream of owning a home with a private pool become a reality in this enchanting city!

Newest Winter Park Homes with Private Pool type

4 Beds ⋅ 4 Baths ⋅ Winter Park Village SubDv. ⋅ 32789 Zip Code

Under Construction. UNDER CONSTRUCTION | LUXURY NEW BUILD | Presented by LUIH Luxury Homes Welcome to 2417 Chantilly Avenue, an exceptional luxury new construction residence in beautiful Winter Park, Florida, where sophisticated design, elevated finishes, and effortless indoor-outdoor living come together. This stunning 4-bedroom, 3.5-bath home features an expansive open-concept floor plan enhanced by upgraded luxury finishes and engineered hardwood flooring throughout. At the heart of the home, the chef-inspired kitchen is designed to impress with premium Thermador appliances, an oversized island, beautiful cabinetry, generous prep space, and a seamless connection to the main living and entertaining areas. The first-floor primary suite offers a private retreat with direct access to the backyard and pool, creating a tranquil connection to the home's outdoor spaces. Step outside and discover your own private oasis. The beautifully designed backyard features a sparkling pool and summer kitchen, providing the perfect setting for entertaining, dining al fresco, or simply relaxing in the Florida sunshine. With 4 bedrooms, 3.5 baths, sophisticated finishes, an open and inviting layout, and exceptional indoor-outdoor living, 2417 Chantilly Avenue delivers the elevated lifestyle today's luxury buyer is looking for—all in one of Winter Park's most desirable locations.

2417 Chantilly Avenue, Winter Park

4 Beds ⋅ 3 Baths ⋅ Quail Run SubDv. ⋅ 32792 Zip Code

Welcome home to this beautifully maintained 4-bedroom, 3-bath pool home, tucked away at the end of a quiet cul-de-sac in Winter Park's Quail Run! From the moment you step inside, vaulted ceilings and abundant natural light create a bright, open, and inviting atmosphere. Fresh interior paint and 5-inch baseboards add a crisp, polished finish throughout. Designed with both everyday living and entertaining in mind, the home offers formal living and dining rooms along with an upgraded kitchen that opens seamlessly to the large family room. The kitchen features granite countertops, stainless steel appliances, a built-in pantry, and an expansive breakfast bar perfect for casual dining and gathering with family and friends. The primary suite offers a relaxing retreat, complete with a stylish barn door leading into the spacious bath that features his-and-hers wardrobes, dual vanities, a large custom built-in storage closet, soaking tub, walk-in shower, and private water closet. Bedroom closets throughout the home are equipped with storage systems for added organization. The renovated pool bath provides convenient direct access to the outdoor living area. An interior laundry room offers additional cabinet storage, and the washer and dryer convey. Step outside and discover an incredible amount of versatile living and entertaining space. The HUGE Florida room is fully paved and features vinyl sliding windows plus its own mini-split system, allowing you to enjoy the space comfortably in a variety of seasons. Beyond it, the fully paved patio leads to a beautiful newer pool surrounded by travertine, lush landscaping, and a tranquil water feature. An additional outdoor paved entertaining pad/pergola combination overlooks the expansive, fully sodded and fenced backyard, creating a peaceful setting for relaxing, hosting, or enjoying Florida living year-round. The property also offers exceptional parking and storage flexibility with an additional paved parking area beside the driveway as well as another paved pad tucked behind the white PVC privacy fence. Additional features include an irrigation system supplied by a well, and an architecural shingle roof, complete with gutters and downspouts. With its spacious layout, impressive outdoor living areas, beautiful pool, abundant natural light, and peaceful cul-de-sac setting, this Winter Park home offers the perfect combination of comfort, functionality, and Florida lifestyle!

4599 Whimbrel Place, Winter Park

4 Beds ⋅ 5 Baths ⋅ J Kronenberger Sub SubDv. ⋅ 32789 Zip Code

Set on a generous corner lot, this stunning single-story pool home in Winter Park has been beautifully remodeled and offers the kind of effortless, one-level living that's genuinely hard to find. Step through the foyer and the floor plan flows naturally into the gourmet kitchen, through the open family and living spaces, past a flexible home office/den, and out to the backyard, where multiple exits blur the line between indoor and outdoor living. The kitchen is anchored by a substantial island with breakfast bar seating, while a Thermador natural gas cooktop takes center stage, complemented by stainless steel appliances, solid wood cabinetry, a wine refrigerator, and granite countertops — a space equally suited to quiet mornings or full-scale entertaining. The home offers 4 bedrooms, 4.5 bathrooms, and a home office/bonus room, thoughtfully organized in a triple split plan that frames the open-concept gathering areas. Three bedrooms enjoy private en-suite baths, the fourth sits directly beside the hall bath, and the office/bonus room is adjacent to the guest half bath — everyone has a bathroom of their own. The primary suite offers its own private retreat, complete with a luxurious en-suite bath and a spacious walk-in closet appointed with custom built-ins. Outside, a custom inground pool and spacious patio are framed by mature hedges for true backyard privacy, while natural gas fuels an outdoor firepit for evenings well past sunset. Recent updates include outdoor perimeter lighting, a rear fence, privacy hedges, and irrigation. All of this sits on a 0.34-acre lot, with a gracious circular drive off Palmer Avenue for guests and a separate garage and driveway entrance off Temple Drive for everyday comings and goings. A paver path connects the home to its 2-car detached garage, with ample additional parking between the front circular drive and rear driveway — perfect for year-round entertaining. Just moments from Phelps Park, the Winter Park Racquet Club, and the historic beauty of Kraft Azalea Garden, with the shops, restaurants, and farmer's market of Park Avenue close at hand — this is single-story Winter Park living at its very best.

1271 Palmer Avenue, Winter Park

4 Beds ⋅ 2 Baths ⋅ Winter Woods Unit 01 SubDv. ⋅ 32792 Zip Code

Welcome to turnkey Winter Park living! This beautifully maintained 4-bedroom + office, 2,092 SF pool home features brand-new living room flooring, a roof only 4 years old, newer A/C, NO HOA, and a private in-ground pool. Step inside to a bright, open-concept layout with abundant natural light, granite countertops, modern appliances, generous cabinet space, and a cozy wood-burning fireplace. The spacious primary suite offers pool views, while the oversized enclosed Florida room/lanai creates the perfect setting for entertaining and year-round indoor/outdoor living. Outside, enjoy a fully fenced and landscaped backyard, private pool, irrigation system, attached 2-car garage, and additional parking. Vacant and move-in ready—bring your furniture and start enjoying the Florida lifestyle! Ideally located in the desirable Winter Woods/Lake Howell area, with convenient access to SR-417, I-4, SR-436, Howell Branch Road, Downtown Orlando, Winter Park shopping and dining, UCF, Orlando International Airport, parks, golf courses, and highly regarded Seminole County schools. Pool. No HOA. Major updates. Prime Winter Park location. Move-in ready. This home delivers the space, lifestyle, and convenience today’s buyers are looking for.

2217 Sussex Road, Winter Park

4 Beds ⋅ 3 Baths ⋅ Brookshire Heights 4th Add SubDv. ⋅ 32792 Zip Code

Virtually Staged. Fully renovated from top to bottom, this 4-bedroom, 3-bathroom Winter Park home pairs a bright, light-filled interior with a private pool made for Florida living. Large windows carry natural light through the main living spaces, and the big-ticket items are already done — new roof (2025) and new AC (2025) — so buyers get an established Winter Park address without the deferred maintenance. The kitchen is the centerpiece: gourmet-grade, fully renovated, with quartz countertops and new appliances built for someone who actually cooks. New flooring runs throughout the home, with tile in all three bathrooms for a clean, easy-care finish. Out back, a screened lanai opens onto the pool — shade and bug-free comfort for morning coffee or evening swims, with the pool itself as the yard’s focal point.

618 Blairshire Circle, Winter Park

4 Beds ⋅ 2 Baths ⋅ Eastbrook Sub Unit 16 SubDv. ⋅ 32792 Zip Code

VIRTUALLY STAGED! EXCEPTIONAL POOL HOME IN EASTBROOK! Welcome to Conifer Avenue, where pride of ownership, and an unbeatable Winter Park-area location come together beautifully. This impressive pool home offers an outstanding opportunity to own a well-maintained residence in the highly sought-after Eastbrook community. This FOUR BEDROOM 2 Bath home offers almost 2200 square feet! Split bedroom plan PLUS 21 x 12 office/bonus room; formal living, dining & family rooms;2024 NEW HVAC-POOL PUMP 2025-ROOF 2019-zoned for excellent Seminole County Schools! Oversized 20 x 22 two car garage with additional storage space. Extras include: updated windows; all appliances including washer & dryer; quaint front porch. Call for your private showing! Step outside and discover your own private retreat! Multiple sets of sliding glass doors open to the large screened-in lanai, sparkling swimming pool, and expansive pool deck, creating an exceptional indoor-outdoor living and entertaining space. The nearly quarter-acre lot is fully fenced, offering plenty of room for pets, play, gardening, and outdoor enjoyment. The oversized two-car garage provides generous parking and an abundance of storage options. This is truly an entertainer's dream home—whether you're hosting friends around the pool, enjoying a quiet evening outdoors, or simply relaxing in your own private backyard oasis. And then there's the LOCATION! LOCATION! LOCATION! Convenient access to I-4 and SR 417 makes traveling throughout Central Florida a breeze, with easy access toward Orlando's attractions, Disney, the beaches, shopping, dining, and entertainment. Enjoy being close to the charm of Historic Downtown Winter Park and Park Avenue, including its fabulous restaurants, boutique shopping, cultural attractions, and popular weekly Farmers Market. SunRail is also conveniently nearby, providing another great transportation option throughout Central Florida.

2301 Conifer Avenue, Winter Park

3 Beds ⋅ 2 Baths ⋅ Suburban Homes First Add SubDv. ⋅ 32792 Zip Code

Location, location, location! Discover this beautiful, meticulously maintained home in a highly desirable Winter Park neighborhood, conveniently located near excellent schools. Enjoy vinyl flooring throughout—no carpet! The gorgeous, upgraded kitchen features quartz countertops, an oversized island, recessed lighting, and stainless-steel appliances. The beautifully updated bathrooms also feature quartz countertops. Fresh landscaping enhances both the front and backyard. Step outside and enjoy your private swimming pool and fully fenced backyard—the perfect setting for relaxing and entertaining. NO HOA and NO CDD! Conveniently located minutes to UCF, Full Sail, Barry University, Valencia, multiple grocery stores and pharmacies, Winter Park’s scenic Park Avenue, Downtown Orlando, and Orlando International Airport.

4870 Seminole Avenue, Winter Park

5 Beds ⋅ 5 Baths ⋅ Forrest Hills SubDv. ⋅ 32789 Zip Code

Virtually Staged. Under Construction. Introducing THE READING RESIDENCE, an extraordinary NEW-CONSTRUCTION ESTATE by renowned luxury builder VIMARO HOMES, ideally situated at 250 WEST READING WAY IN WINTER PARK. Encompassing approximately 4,853 SQUARE FEET, WITH 5,922 TOTAL SQUARE FEET OF CONSTRUCTION, this FIVE-BEDROOM, FOUR-AND-ONE-HALF-BATH residence is a masterful expression of elevated design, uncompromising craftsmanship, and effortless Florida luxury. Vimaro Homes approaches every project with a singular philosophy: “The goal isn’t to spend less. The goal is to build something worth more.” That commitment to quality and value will be evident throughout this exceptional home, where thoughtful details, generous proportions, and refined finishes come together to create something truly remarkable. The main level delivers refined living and exceptional entertaining spaces, with SOARING CEILINGS enhancing the expansive living room and open kitchen and dining area. A substantial center island, generous pantry, dedicated laundry room, mudroom, and PRIVATE HOME OFFICE bring beauty, convenience, and functionality to the thoughtfully planned interior. The magnificent FIRST-FLOOR PRIMARY SUITE offers a private sanctuary with an impressive walk-in closet and spa-inspired bathroom featuring DUAL VANITIES, A FREESTANDING SOAKING TUB, AN OVERSIZED SHOWER, and a private water closet. Upstairs, a spacious SECOND GATHERING ROOM provides another inviting destination for relaxation and entertainment. A generous JUNIOR PRIMARY SUITE includes its own walk-in closet and private bathroom, while three additional bedrooms and two beautifully planned bathrooms—including a convenient JACK-AND-JILL BATH—provide exceptional comfort and privacy. Created to celebrate Florida’s coveted indoor-outdoor lifestyle, the residence opens to an expansive COVERED GRAND LANAI and fully equipped SUMMER KITCHEN overlooking the planned RESORT-STYLE POOL. This private outdoor retreat will provide an exquisite setting for alfresco dining, elegant entertaining, and sun-filled afternoons. A DETACHED GARAGE completes the beautifully composed property. The exceptional location places the best of WINTER PARK within easy reach, including celebrated dining, upscale shopping, picturesque parks, renowned museums, cultural destinations, and the timeless charm of PARK AVENUE. Currently under construction, THE READING RESIDENCE represents a rare opportunity to own a signature luxury home created with purpose, precision, and an unwavering dedication to quality. More than simply a home, this is a distinctive expression of the Vimaro Homes philosophy—GREAT HOMES ARE BUILT BY CREATING LASTING VALUE.

250 W Reading Way, Winter Park

4 Beds ⋅ 2 Baths ⋅ Tanglewood Sec 3 Rep SubDv. ⋅ 32792 Zip Code

**RARE WINTER PARK OPPORTUNITY!** Bring your vision to this 1959 block home situated on a spacious 0.25-acre lot in the City of Winter Park, with the prestigious Interlachen Country Club golf course directly behind the property. Whether you choose to renovate the existing 4-bedroom, 2-bath home or pursue a complete redevelopment, this property offers an exceptional opportunity to create something special in a highly desirable location. The existing home features solid block construction, 4 bedrooms, 2 bathrooms, a concrete swimming pool, and a 2019 roof, providing a great starting point for renovation or redevelopment. The generous lot and established location offer plenty of potential for a new custom residence designed to take advantage of the surrounding Winter Park lifestyle and golf-course setting. Enjoy convenient access to some of Central Florida's most sought-after amenities, including Interlachen Country Club, Park Avenue, Downtown Winter Park, Winter Park Village, Rollins College, Central Park, shopping, dining, parks, and cultural attractions. Interlachen's 18-hole championship golf course provides a beautiful backdrop just beyond the property, while Winter Park's renowned Park Avenue district offers upscale shopping, restaurants, galleries and entertainment nearby. An excellent opportunity for builders, investors, renovators or buyers looking to create their own Winter Park residence in an established setting surrounded by golf, dining, shopping and recreation.

5218 Lake Howell Road, Winter Park

5 Beds ⋅ 7 Baths ⋅ J Kronenberger Sub SubDv. ⋅ 32789 Zip Code

Pre-Construction. To be built. A rare convergence of timeless French Country architecture, brand-new custom construction, and coveted access to the Winter Park Chain of Lakes. Thoughtfully designed and being built by FG Schaub Custom Homes, this exceptional property offers the character of a timeless estate with the amenities and craftsmanship expected in a luxury new construction home. The residence will feature five bedrooms, a dedicated office, five full bathrooms, and two half bathrooms, with beautifully appointed living spaces designed for both refined entertaining and comfortable everyday living. The striking exterior showcases classic French Country influences, stone accents, decorative brick detailing, crisp stucco, expansive windows, and multiple gabled rooflines, creating an elegant and welcoming architectural presence. Outdoor living is equally impressive, with a private pool and spa, covered outdoor living area with roll away screens, and a full summer kitchen creating a resort-style retreat. A brand-new private boathouse, included with the property, is positioned directly on the canal and provides access to the Winter Park Chain of Lakes, offering the opportunity to enjoy boating, water sports, fishing, and so much more. Final plans, specifications and finishes are subject to change.

825 Palmer Avenue, Winter Park

5 Beds ⋅ 5 Baths ⋅ Conwill Estates SubDv. ⋅ 32789 Zip Code

Under Construction. Set within Winter Park’s highly sought-after Tree Streets, this exceptional new home delivers a sophisticated blend of architectural presence, refined interiors, and effortless indoor-outdoor living. A striking façade creates an unforgettable first impression, while a marble mosaic entry introduces the artistry and attention to detail found throughout the home. The main living space is designed to feel both impressive and inviting, centered around a dramatic electric fireplace wrapped in fluted stone. Expansive sliding glass doors fill the room with natural light and create a seamless connection to the outdoor entertaining areas. Open to the living room, the chef’s kitchen is a true statement, pairing richly veined Calacatta Gioia countertops with custom cabinetry, a built-in refrigerator, and a full suite of Thermador appliances. A generous walk-in pantry provides abundant storage and preparation space while maintaining the kitchen’s clean, elevated aesthetic.The first-floor primary suite offers a private retreat with vaulted ceilings and direct access to the backyard. Its spa-inspired bathroom is a sanctuary of beautifully selected marble tile and a serene, sophisticated color palette. A freestanding soaking tub, oversized walk-in shower, dual vanities, and thoughtfully curated finishes create an atmosphere reminiscent of a luxury resort. Also located on the main level is a versatile secondary bedroom that could serve beautifully as a private home office or guest suite, along with a well-appointed powder bath and a combined laundry and mudroom designed for everyday convenience. Upstairs, three additional guest suites provide comfort and privacy, while a spacious loft offers flexibility as a second living room, media space, or playroom. A second laundry room adds another layer of functionality to the thoughtfully planned layout. Outside, the home continues to impress with a covered lanai and full summer kitchen, creating the perfect setting for year-round entertaining. A marble pool deck surrounds the sparkling pool and spa, while the spacious backyard offers room to relax, gather, and enjoy the Central Florida lifestyle in complete comfort. The location is what really sets this home apart. New construction opportunities are becoming increasingly rare within the up-and-coming Tree Streets, making this residence an especially compelling offering. Just a short walk from the Winter Park YMCA, Phelps Park, and Interlachen Country Club, the home places recreation and everyday conveniences close at hand. Hop on your golf cart and arrive to Park Avenue's boutiques, cafes, and restaurants within minutes. A home of this caliber in such a coveted location is a rare find and it won’t remain available for long.

1773 Walnut Avenue, Winter Park

4 Beds ⋅ 5 Baths ⋅ Maitland Shores First Add SubDv. ⋅ 32789 Zip Code

Virtually Staged. Brand new Roof and HVAC systems in 2025 and all new windows 2026. Discover the allure of 952 Moss Ln, a stunning residence in the heart of Winter Park that seamlessly blends elegance and modern comfort. This captivating 4-bedroom, 4-bathroom home exudes warmth and sophistication, creating an inviting haven for discerning buyers. Sunlight floods every room, highlighting the home’s refined details and creating a luminous, welcoming atmosphere. Step inside to find luxurious plank flooring flowing through the entryway, family room, and guest bedrooms, complemented by polished marble in the formal living room and opulent primary suite. The interior showcases meticulous craftsmanship with recessed lighting, custom cabinetry, and coffered ceilings that add architectural charm. The heart of the home is a gourmet chef’s kitchen, a culinary dream featuring sleek custom cabinetry, a stylish farmhouse sink, a practical pot filler, and top-of-the-line appliances, perfect for both everyday meals and grand entertaining. Outside, a covered lanai invites relaxation. The sparkling pool, featuring a tranquil waterfall, soothing hot tub, and private pool bath creates a private oasis perfect for unwinding or hosting gatherings. The meticulously landscaped backyard, framed by lush greenery, offers a serene retreat for outdoor enjoyment. Soaring vaulted ceilings enhance the airy, open feel throughout the home. Located near the esteemed Rollins College and vibrant Park Avenue, this property is nestled in a charming neighborhood, offering both prestige and access to Winter Park’s finest dining, shopping, and cultural attractions. With a paved parking area, a two-car garage, and dual-zone AC for year-round comfort, this exquisite home is as practical as it is beautiful. Don’t miss the opportunity to own this Winter Park masterpiece, where timeless elegance meets modern luxury. Schedule a showing today and step into a lifestyle of comfort, sophistication, and unparalleled charm at 952 Moss Ln; this true gem is ready to become your forever home.

952 Moss Lane, Winter Park

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