Refine Search
Map
Sort by
$339,000
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. Zoned for Seminole County Schools (A Rated school zone 2025/2026)! 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
$1,149,900
5 Beds ⋅ 5 Baths ⋅ Lake Florence Preserve SubDv. ⋅ 32792 Zip Code
Located within an intimate gated community of just 28 homes and only a short drive to Downtown Winter Park, this exceptional former model home by K. Hovnanian Homes showcases over $200,000 in builder and custom upgrades with luxury finishes and thoughtful design throughout. Residents enjoy access to a private community dock, perfect for launching a canoe or paddleboard or simply relaxing while enjoying sunset views over the water. This stunning Michelson floorplan offers the perfect blend of elegance, comfort, and functionality with spacious living areas designed for both everyday living and entertaining. Upon entry, you’re welcomed by a private office, formal dining room with custom accent features, recessed lighting throughout, beautiful wood-look tile flooring, and designer details at every turn. The open-concept family room features built-in speakers that continue throughout the main living spaces, upstairs, and outdoor lanai area, creating a seamless entertainment experience throughout the home. The gourmet kitchen is beautifully appointed with quartz countertops, 42” cabinetry, stainless steel appliances, gas cooktop, oversized island, modern backsplash, butler’s pantry with wine fridge, and an incredible walk-in pantry with custom built-in shelving. Massive 12-foot triple sliding glass doors open to the resort-style backyard featuring a beautiful open pool, custom fire pit, pergola seating area, pre-wire for a gas grill, and a backyard perfect for relaxing or entertaining. The first floor also includes a guest suite with a full bath and direct pool access, a mudroom, a coat closet, a convenient half bath, and an oversized three-car tandem garage with overhead storage. Upstairs, a beautiful wood tread staircase leads to an expansive loft and bonus room area along with spacious secondary bedrooms, all featuring walk-in closets. A Jack-and-Jill bathroom with dual sinks, additional full bath, oversized linen closets, and a large laundry room with sink and extensive cabinetry provide exceptional functionality and storage. The luxurious owner’s retreat is a true sanctuary featuring tray ceilings, built-in speakers, a stunning accent wall, coffee bar area, spa-inspired bath with an oversized walk-in shower, abundant storage, and an enormous walk-in closet with multiple sections. Additional highlights include a brand-new A/C unit and countless high-end finishes throughout. Ideally located near top-rated schools, shopping, dining, and major roadways, this meticulously maintained home offers elevated Florida living in one of the area’s most desirable gated communities.

1448 Lake Florence Way, Winter Park
$639,000
3 Beds ⋅ 2 Baths ⋅ Lawndale SubDv. ⋅ 32789 Zip Code
A timeless blend of historic charm and modern luxury awaits in this beautifully restored 1927 Florida bungalow, nestled in the highly sought-after and peaceful neighborhood of Orwin Manor in Winter Park. Rich in character and thoughtfully updated throughout, this exceptional residence seamlessly combines the elegance of its original architecture with the comfort and sophistication of modern living. Upon entering, you are welcomed by an inviting foyer featuring new tile flooring and refined vertical shiplap detailing, setting the tone for the home’s timeless design. Custom transitions lead into the spacious living room, where original hardwood floors, a cozy fireplace, and smart lighting create a warm and inviting atmosphere ideal for both entertaining and everyday living. The formal dining room comfortably accommodates gatherings of eight and is highlighted by a stunning Serena & Lily chandelier, creating the perfect setting for memorable dinners and celebrations. Just beyond, the fully renovated chef’s kitchen serves as the heart of the home. Updated in 2020, it features elegant Calacatta countertops, an oversized island, premium Samsung appliances, and stylish West Elm lighting. An adjacent eat-in dining space offers a more casual setting and opens directly to the beautifully paved backyard, perfect for outdoor dining and entertaining. The home’s accommodations are equally impressive, including a serene primary suite complete with dual closets and a beautifully appointed bathroom featuring sleek matte finishes. Additional living spaces include a versatile recreation room and a well-appointed guest bedroom, each designed with both comfort and functionality in mind. A private attic provides valuable additional storage space. Every detail of the home has been carefully considered to enhance both aesthetics and practicality, including smart exterior lighting, a durable vinyl privacy fence, low-maintenance landscaping tailored to Florida living, and an updated Carrier HVAC system with a smart thermostat for year-round comfort. Preserving the integrity of the home’s historic character, original woodwork, including baseboards and casings, has been thoughtfully maintained, while curated paint selections and Trex exterior staircases add lasting beauty and durability. Ideally located just minutes from Park Avenue, College Park, and major thoroughfares, this remarkable property offers an exceptional combination of tranquility, convenience, and community. More than just a home, it is a rare opportunity to own a beautifully preserved piece of Winter Park history where timeless charm and contemporary elegance exist in perfect harmony. New roof 2026***

1707 Harmon Avenue, Winter Park
$695,000
4 Beds ⋅ 2 Baths ⋅ Kenilworth Estates 1st Add SubDv. ⋅ 32792 Zip Code
Virtually Staged. This move-in-ready classic ranch-style pool home offers a relaxed 60’s retro vibe with vaulted ceilings, 4 bedrooms, 2 full bathrooms, and light-filled living spaces. Newer manufactured wood flooring flows throughout the main living spaces, complementing the spacious layout that includes a formal living room, dining area, breakfast nook, and a large free-flowing kitchen designed for both everyday living and entertaining. The kitchen features an open space concept, island, solid wood cabinets, granite countertops, over-range hood, and stainless-steel appliances. All four bedrooms are positioned just off the main hallway, creating a practical and functional layout. The 4th bedroom features French doors and offers exceptional flexibility for use as a home office, creative studio, workout space, or playroom, with a view of the pool and backyard. The primary bedroom includes an ensuite with a tiled shower. Additional features include an indoor laundry area, two-car carport with 2 storage rooms, and a large lot that adds to the home’s overall sense of space and privacy. Situated on a quiet street with limited through traffic, this home offers a peaceful setting while remaining close to everything Winter Park has to offer. The private, fully fenced backyard is a standout feature, offering a beautifully landscaped setting with a sparkling pool, Tiki Bar and plenty of space for outdoor entertaining or relaxing. Whether enjoying a quiet morning coffee, relaxing with a good book, or unwinding with a glass of wine in the gazebo, this outdoor space is designed to embrace the Florida lifestyle. Bonus features include a well-water irrigation system and newly sodded yard. Recent updates provide added peace of mind, including a roof installed in 2015, along with a new HVAC heat pump system installed 2026 with (10-year Warranty) and water heater installed in 2026. The home has been well maintained both inside and out, offering true move-in-ready convenience. Located in the sought-after Brookshire Elementary, Glenridge Middle, and Winter Park High School zones, the home is also close to Rollins College, Full Sail University, AdventHealth Winter Park, and the Orlando VA Medical Center. Outdoor enthusiasts will appreciate nearby Cady Way Trail, Blue Jacket Park, and Lake Baldwin, along with close proximity to Lake Berry and the neighborhood boat ramp and fishing dock. Buyer should verify any access rights or neighborhood use details.

2215 Woodcrest Drive, Winter Park
$2,500,000
5 Beds ⋅ 6 Baths ⋅ Osceola Shores Sec 03 SubDv. ⋅ 32789 Zip Code
Sophisticated Lakeside Living in the Heart of Winter Park! Experience the pinnacle of Florida luxury in this meticulously renovated estate, perfectly situated within walking distance of the world-class dining and boutiques of Park Avenue, views of Lake Osceola with easy lake access, with a coveted Winter Park location and top notch schools. This 5-bedroom, 4-full and 2-half-bath pool home residence offers an enviable blend of timeless architecture and modern refinement. The interior has been updated and maintained to the highest standards. The home’s open-concept floor plan is anchored by rich, newer solid wood flooring and elegant plantation shutters throughout. At the heart of the home, the chef’s kitchen is a culinary masterpiece featuring, pristine quartz countertops, high-end stainless steel Bosch appliances, natural gas range, double ovens, and a walk-in pantry. A sophisticated entertainer’s bar area off the kitchen is equipped with a 100+ bottle dual-zone wine cooler, beverage cooler, ice maker, and service sink. This area is open to the kitchen an living areas for easy entertaining or catering. The newly reimagined primary retreat is a spa-like sanctuary, showcasing white marble tile, a frameless glass shower with dual rainfall heads, a deep garden soaking tub, double vanity areas with new quartz counter tops, new mirrors and lighting and a bespoke walk-in closet. The primary walk in closet was just updated with a top of the line shelving and storage system for easy organization. The home's floor plan is thoughtfully designed for flexibility, featuring a second primary suite on the main level. Back upstairs, you will find three additional guest bedrooms and two additional full bathrooms, a versatile bonus/flex room over the garage and a private balcony offering serene lake views. The bonus room has endless possibilities and can be used as a recreation room, movie theatre, exercise room, play room, or in-law/nanny quarters as the second back staircase could be a private entry. Outdoor Oasis & Infrastructure Designed for seamless indoor-outdoor living, the rear grounds feature a covered lanai over looking the pool. The covered lanai offers a living and dining area, a newly built-in outdoor kitchen with a professional grill, and a paver-lined patio surrounding a sparkling pool and gas fire pit gazebo sitting area on the other side of pool area. Plenty of yard space to throw the football, practice soccer skills or throw the frisbee with fido!! Exceptional Features Include: Mechanical Integrity: Roof replaced in 2020; updated A/C systems (2016/2019); Rinnai tankless natural gas water heater, brand new primary bathroom, all bathrooms have been refreshed, recently updated kitchen, newer solid wood floors throughout. Storage & Utility: 3-car garage with extended bays for extra storage, oversized closets throughout, and two convenient staircases. Cozy Accents: 2 fireplaces with one being wood-burning and one gas. Three distinct breakfast/dining areas within the kitchen plus formal dining. This is more than a home; it is an invitation to the quintessential Winter Park lifestyle you have been dreaming of living!

450 Lakewood Drive, Winter Park
$569,900
3 Beds ⋅ 2 Baths ⋅ Orwin Manor Westminster Sec SubDv. ⋅ 32789 Zip Code
In the sought-after Orwin Manor neighborhood, this beautifully updated one-story residence offers a seamless blend of comfort, style and convenience. Featuring three bedrooms and two baths, the home showcases an open-concept floor plan enhanced by engineered wood flooring that extends throughout every room, creating a cohesive and inviting living environment. The kitchen is thoughtfully updated with quartz countertops, refreshed cabinetry, newer appliances and a charming breakfast nook, ideal for casual dining. The living spaces flow effortlessly to a wonderful enclosed porch, providing additional year-round enjoyment, with direct access to an open brick-paver patio complete with a firepit, all set in a fully fenced backyard ideal for entertaining or relaxing in privacy. Both baths have been tastefully updated, and a new roof installed in 2021 that adds to the home’s overall appeal and peace of mind. Ideally just minutes from vibrant shopping and dining of downtown Winter Park and College Park, with convenient access to major roadways and the AdventHealth Orlando campus, this home offers exceptional accessibility to all metro Orlando has to offer. Whether as a primary residence or an investment opportunity, this property presents an exceptional offering in a prime, established location.

1741 Westchester Avenue, Winter Park
$1,049,000
5 Beds ⋅ 3 Baths ⋅ Parklando SubDv. ⋅ 32789 Zip Code
Welcome to this beautifully updated Winter Park home, perfectly positioned on a desirable corner lot and zoned for Audubon Park K-8 and Winter Park High School. With 5 bedrooms and 3 full baths, this spacious residence offers the ideal blend of functionality and style for modern living. Step inside to an open, light filled floor plan featuring luxury vinyl floors and a cozy wood burning fireplace that anchors the main living space. The renovated kitchen is thoughtfully designed with both everyday living and entertaining in mind, flowing seamlessly into the dining and living areas. A dedicated office provides the perfect work from home setup or quiet retreat, while the flexible layout offers plenty of room for guests, growing families, or multi generational living. Outside, enjoy a private backyard with a charming fire pit and rock gathering are deal for relaxing evenings or hosting friends. The oversized lot also offers ample space to add a pool and create your own backyard oasis. Additional highlights include a 2-car garage, roof replaced in 2018, home repiped in 2019, and updated AC for peace of mind. This is a rare opportunity to own a move-in ready home in one of Winter Park’s most sought after neighborhoods, walking distance to the Audubon Park Garden District with amazing dining, and shopping.

2702 Parkland Drive, Winter Park