Refine Search
Map
Sort by
$899,000
4 Beds ⋅ 3 Baths ⋅ Greenview At Winter Pines SubDv. ⋅ 32792 Zip Code
Discover elevated living in this stunning 4 bedroom, 2.5 bathroom pool home, perfectly situated overlooking a tranquil pond and Winter Park 18 hole golf course. Surrounded by a lush tropical backyard oasis, this residence blends modern sophistication with effortless comfort, creating a serene retreat that’s ideal for that perfect start to the morning with a cup of coffee or a relaxing wind down at sunset with a glass of wine. Inside, vaulted wood-trimmed ceilings and a wood-burning fireplace set a warm, inviting tone across 2,455 sq. ft. of thoughtfully designed space. The kitchen features contemporary cabinetry paired with quartz and butcher block wood countertops and a designer tile backsplash. Stainless steel appliances, including a beverage refrigerator, add a professional touch, while a built-in banquette provides seating for six—perfect for entertaining and everyday living. The primary suite offers wood floors, a walk-in closet, and a spa-like bath with dual floating vanity, soaking tub, and seamless glass shower. Enjoy outdoor living at its finest with pergola-covered sitting areas, outdoor shower, fire pit, and sparkling pool. Situated on a private tree-lined cul-de-sac, this home is located in a prime location just minutes from Cady Way Trail, Cady Way pool & courts, Winter Park Pines Golf Course, Crosby Center for Health and Wellbeing, Ward Park, Showalter Athletic Complex, Advent Health Winter Park Hospital and less than 10 minutes to Historic Park Avenue fine dining and shopping. Don’t miss your chance to own this rare Winter Park gem—schedule your showing today! ROOF - 2016 HVAC - 2023(2) PLUMBING - 2020 ELECTRICAL - 2021 WATER HEATER - 2020

1648 Cypress Point Lane, Winter Park
$755,000
4 Beds ⋅ 2 Baths ⋅ Greenview At Winter Pines SubDv. ⋅ 32792 Zip Code
Fully updated 4 bed/2 bath Winter Park Pines home ready for a new owner! Tucked away at the end of a quiet cul-de-sac, this fully renovated home offers the perfect blend of modern luxury and serene surroundings. The brand new kitchen and bathrooms showcase quartz countertops, elegant gold fixtures, and custom details, complemented by new engineered wood flooring, interior laundry, and new windows and sliding doors that fill the space with natural light. Additional upgrades include new doors, trim, soffits, fresh interior and exterior paint, and a beautiful paver patio. Outside, enjoy all-new landscaping with fresh sod and a new irrigation system. Major improvements provide peace of mind, including a NEW ROOF (2025), garage door (2025), electric panel (2024), and a NEW HVAC system (2026). Sitting at the end of the cul-de-sac and backing up to the scenic Cady Way trail, ideal for biking, walking, and running, the property provides both privacy and an active lifestyle right outside your door. This home is zoned for highly rated Winter Park schools: Brookshire Elementary, Glenridge Middle, and Winter Park High School. There is an optional HOA in the Winter Park Pines community.

1317 Medinah Court, Winter Park
$750,000
4 Beds ⋅ 2 Baths ⋅ Greenview At Winter Pines SubDv. ⋅ 32792 Zip Code
The home you’ve been waiting for—an exceptional Winter Park residence offering a private pool and golf views. Situated at 1712 Golfside, this property welcomes you with a picturesque oak-lined street, a paver driveway, and timeless architectural character. Every element has been designed to deliver a sophisticated blend of comfort, style, and effortless living. This beautifully reimagined four-bedroom, two-bath home offers a modern open-concept layout featuring a wood burning fireplace and a stunning NEW kitchen. Custom cabinetry, stainless steel appliances, and an oversized quartz island with extra storage create a seamless space for gatherings and everyday enjoyment. Laminate flooring flows throughout the home, enhancing its clean aesthetic, while French doors extend the living space outdoors for a natural connection between indoor relaxation and poolside entertaining. The primary suite is a private retreat featuring a flexible office, nursery, or sitting area; a spacious walk-in closet with custom built-ins; and an elegantly modern en-suite bath with warm tones, a walk-in shower, and refined fixtures. Additional bedrooms offer generous space, plantation shutters, and well-appointed closets, contributing to the home’s balanced and thoughtful layout. Outdoors, the residence continues to impress with a NEWLY RESURFACED, HEATED POOL and spa, accessible from multiple rooms for effortless flow. A covered patio, mature landscaping, fenced yard and expansive pool deck create an ideal setting for morning coffee, quiet moments overlooking the chipping green, or hosting guests in a serene, resort-like environment. This premier location provides rare proximity near Winter Park Pines Golf Club, Cady Way Trail, pool, playground, tennis and pickleball courts, Ward Park, and A-rated schools (Brookshire Elementary, Glenridge Middle, Winter Park High), this home is equally close to Rollins, Baldwin Park, Park Avenue, UCF, and Full Sail. Also conveniently nearby are AdventHealth Winter Park, Crosby Wellness, and everyday shopping, where convenience meets connection. Recent upgrades include a 2022 ROOF, plumbing and electrical improvements, and extensive interior updates completed in 2024, including new flooring and a full kitchen renovation. A transferable home warranty adds an additional layer of assurance. 1712 Golfside delivers a refined living experience in one of Winter Park’s most desirable settings, offering the perfect balance of luxury, comfort, and everyday ease.

1712 Golfside Drive, Winter Park
$700,000
4 Beds ⋅ 2 Baths ⋅ Greenview At Winter Pines SubDv. ⋅ 32792 Zip Code
MULTIPLE OFFERS. The Sellers are calling for highest and best offer submissions by Monday, September 15th at 5:00 PM. Golfside living, beautifully reimagined. From the moment you step inside, your eyes are drawn to serene water and golf course views — a daily reminder of why this address is so special. This 4-bedroom, 2-bath retreat in Winter Park Pines marries timeless charm with thoughtful modern updates — from the warmth of a wood-burning fireplace to a dream kitchen dressed in quartz, honeycomb tile, and designer lighting. A versatile dining or flex space invites effortless entertaining or the perfect work-from-home setting. The Florida room, bathed in natural light, creates a seamless connection between indoor comfort and the picturesque landscape beyond — a space to linger over morning coffee or unwind at sunset. The primary suite feels like a private sanctuary with peaceful views of the water and rolling fairways. Its en-suite bath, fully reimagined in 2023, offers dual vanities, shiplap accents, and a glass walk-in shower with rainfall and handheld features — a retreat designed for pure exhale. Three additional bedrooms, well-appointed with ceramic flooring and ceiling fans, provide both comfort and flexibility. A second fully renovated bath shines with brushed gold fixtures, quartz vanity, and carefully curated tile work. Step outside to the brick paver patio with motorized retractable awning, where mornings glow and evenings linger against a backdrop of water and golf course greens. A city-permitted fenced side yard adds storage for a boat, camper, or weekend toys. This home’s updates bring peace of mind: new roof (2024), dual hybrid water heater (2024), garbage disposal (2025), plumbing upgrades (2020–2025), all-new ductwork and insulation (2022), new garage door motor and springs (2025), plus a serviced HVAC system every 6 months. Ideally located near Winter Park Pines Golf Club, Cady Way Trail, pool, playground, tennis and pickleball courts, Ward Park, and A-rated schools (Brookshire Elementary, Glenridge Middle, Winter Park High), this home is equally close to Rollins, UCF, and Full Sail. With Park Avenue, AdventHealth Winter Park, Crosby Wellness, and everyday shopping minutes away, where convenience meets connection. Practical and picturesque. Light-filled and lifestyle-rich. A Winter Park home where every detail — and every view — feels like home.

1729 Golfside Drive, Winter Park
$699,450
4 Beds ⋅ 2 Baths ⋅ Greenview At Winter Pines SubDv. ⋅ 32792 Zip Code
**Multiple offers received*** Please submit highest and best by 10/20/2025 at 4:00 pm This beautifully maintained golf course home offers effortless living in an established Winter Park neighborhood. As you drive along the charming tree-lined streets, the home greets you with impeccable landscaping and timeless curb appeal. Step inside the foyer and discover a bright, open floor plan that seamlessly connects the dining area, kitchen, and living room. Soft natural finishes create a breezy, relaxed feel, while the cozy fireplace anchors the living space, which is perfect for gathering with loved ones. The kitchen is both stylish and functional, featuring stainless steel appliances, stone countertops, a farmhouse sink, and refinished cabinetry. The stylish island provides casual dine-in seating, and the custom pantry and laundry room offer exceptional storage, plus a convenient folding counter and hanging space. Your private primary suite is tucked away to the left of the kitchen, offering serene views and sliding doors that open to the screened lanai overlooking lush, mature landscaping. The walk-in closet provides generous storage, and the updated ensuite bath includes a walk-in shower with both handheld and fixed showerheads. A split floor plan offers three additional bedrooms and an updated guest bath with a tub and glass enclosure perfect for guests. Relax on the screened lanai and enjoy peaceful golf course views and privacy. The brand-new roof provides peace of mind, and the widened paver driveway offers both style and convenience. The garage is equipped with a workbench and built-in shelving for all your storage needs, plus an additional shed and fenced side yard create more outdoor space to enjoy. Located within the Winter Park school district, this home offers the perfect blend of privacy and convenience — just 8 minutes from Lake Baldwin Park, 10 minutes to Corrine Drive’s shopping and dining, 12 minutes to Park Avenue, and 20 minutes to Downtown Orlando.

1346 Golfside Drive, Winter Park
$649,000
4 Beds ⋅ 2 Baths ⋅ Greenview At Winter Pines SubDv. ⋅ 32792 Zip Code
POOL HOME, nestled along the 14th fairway of Winter Park Pines Golf Course (WP18). A peaceful retreat with no rear neighbors—ideal for tranquility and privacy. Offering 1,936 square feet, four bedrooms, two bathrooms and an inside utility room, this is a hard-to-find gem in Winter Park. Perfectly situated in a tree-lined community overlooking the golf course. Upon entering, you are greeted by a spacious foyer that leads into a formal living room and then transitions into a formal dining area. The updated kitchen includes a cozy breakfast nook. The inviting family room features vaulted ceilings, beams and a fireplace creating a welcoming atmosphere for gatherings and relaxation. The primary suite boasts his-and-her closets, enhancing functionality. This home is zoned for Brookshire Elementary, Glenridge Middle, and Winter Park High School. Recent updates include AC (2014), Windows (2020), New Roof (2025), New Electrical Panel (2025), and Re-pipe (2026). WELCOME HOME!

1523 Golfside Drive, Winter Park
$455,500
3 Beds ⋅ 2 Baths ⋅ Greenview At Winter Pines SubDv. ⋅ 32792 Zip Code
This property is currently under contract.

1317 Medinah Court, Winter Park