Winter Park

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

BIG HOUSE. BIG KITCHEN. BIG FAMILY LIVING — FULLY RENOVATED IN WINTER PARK PINES. Currently the largest home on the market in Winter Park Pines under $900,000, this fully renovated 5-bedroom, 4-bath family home checks all the boxes. At the heart of the home is a brand-new designer kitchen anchored by a massive 9' x 5' double-waterfall island—the kind of kitchen where family memories are made. Two large skylights flood the kitchen and adjoining eating area with natural light, while extensive cabinetry and a custom range hood give the space a polished designer feel. And when company comes over? Hide the mess. The incredible 11-foot butler's pantry practically functions as a second kitchen, complete with its own sink, full-size refrigerator space, extensive cabinetry, countertops, and loads of storage. Party prep, appliances, groceries, and dirty dishes can stay tucked away while the main kitchen stays beautiful. Then there’s the primary suite. At approximately 13' x 22', this bedroom is large enough for its own sitting room, reading area, or private lounge. Add the oversized 7' x 8' walk-in closet, and you have a true owner's retreat. But the primary bathroom may steal the show. You might want to cancel the spa membership. Imagine ending the day in a six-foot freestanding soaking tub beneath a skylight, framed by a dramatic fluted marble backdrop. Add an oversized shower with dual showerheads, double vanity, heated smart toilet, and designer finishes, and you have a bathroom straight out of a magazine. Near the primary suite is another bedroom with its own ensuite bath—perfect for a home office, nursery, gym, guest room, or multigenerational living. Then send the kids to the other side of the house. The east wing features three large bedrooms and two baths, giving the younger members of the household a kingdom of their own where toys, homework, friends, and the occasional mayhem can stay comfortably contained. At the front of the home, the formal living room is filled with natural sunlight and offers a peaceful place to sit and unwind. When it’s time to gather everyone together, the separate 22-foot family room features a dramatic 10-foot linear fireplace and connects directly to the rear porch, gazebo, and backyard. Birthdays, holidays, Sunday dinners, graduation parties—this home gives you the space to bring everyone together without everyone sitting on top of each other. Outside, enjoy newly installed Zoysia grass, a private putting green, shaded relaxation areas, porch, and gazebo—perfect for entertaining, playing, or enjoying the Florida lifestyle. And this isn't simply a cosmetic renovation. Major improvements completed in 2026 include a new roof, electrical system, plumbing, and water heater. The HVAC system was installed in 2019. Enjoy convenient access to Winter Park Pines Golf Course, neighborhood walking paths, the community pool, major medical centers, and everything that makes Winter Park such a desirable place to live. Five bedrooms. Four baths. Separate bedroom wings. A magazine-worthy primary bath. A massive kitchen island. A second-kitchen-style pantry. Multiple living spaces. A putting green. And room for the entire family to actually live. This is a rare home giving a large family room to spread out, gather together, and truly enjoy it. If you've been searching Winter Park for space without sacrificing style, location, or modern finishes, 724 Monmouth Way deserves to be at the top of your list

724 Monmouth Way, Winter Park

$1,600,000

3 Beds ⋅ 3 Baths ⋅ Albert Lee Ridge Annex SubDv. ⋅ 32789 Zip Code

WELCOME TO LAKEFRONT LUXURY ON LAKE BELL. This exceptional custom residence brings together refined craftsmanship and design, and an extraordinary waterfront setting in the heart of Winter Park. Built in 2025 by Accent Homes & Development, this beautifully appointed home offers 2,733 square feet of living space, with 3 bedrooms and 2.5 baths. From the moment you enter, expansive windows draw you toward the water, filling the home with natural light and creating a seamless connection between the elegant interiors and the lake beyond. Warm wood flooring flows throughout the main living areas, while a dramatic floor-to-ceiling fluted electric fireplace serves as a stunning architectural centerpiece, beautifully separating the living room from the formal dining area. At the heart of the home is a spectacular gourmet kitchen designed for both everyday living and effortless entertaining. Overlooking the lake, it features custom cabinetry, an oversized island, and an exceptional suite of premium appliances, including a 48-inch SUB-ZERO Classic French-door refrigerator, WOLF induction cooktop, WOLF wall oven and microwave, ELICA stainless steel under-cabinet hood, and BRISAS under-counter French-door wine cooler. Every detail reflects a thoughtful blend of luxury, functionality, and timeless style. Upstairs, the serene primary suite captures beautiful lake views and offers a spacious walk-in closet. Two additional bedrooms share a beautifully appointed Jack-and-Jill bath, with both bedrooms opening to a private balcony overlooking the tranquil surroundings. The true centerpiece of this property is its extraordinary waterfront lifestyle. Step outside to your own private covered dock on Lake Bell and enjoy direct access to a beautiful 36-acre, spring-fed ski lake. Lake Bell offers an exceptional setting for boating, water skiing, jet skiing, paddleboarding, kayaking, fishing, and swimming. Whether you're heading out on the water or simply relaxing dockside at sunset, every day feels like a getaway. With no neighbors directly across the lake, the property enjoys an uncommon sense of privacy, peacefulness, and expansive water views. Ideally located just 2 miles from I-4, this residence offers the best of Winter Park at your doorstep. Enjoy the boutiques, acclaimed restaurants, and timeless charm of Park Avenue, along with Winter Park Village, Rollins College, the Winter Park Farmers’ Market, Mead Botanical Garden, Kraft Azalea Garden, the Winter Park Chain of Lakes, museums, galleries, and historic neighborhoods—all just minutes away. A rare opportunity to own a newer built, custom lakefront residence with a private covered dock on one of Winter Park’s beautiful spring-fed lakes. Beautiful, serene, and designed for the way you want to live—this is Lakefront living at its finest.

2207 Kindel Avenue, Winter Park

$3,265,000

5 Beds ⋅ 6 Baths ⋅ Green Oaks Rep 02 SubDv. ⋅ 32789 Zip Code

One of the most coveted neighborhoods in all of Winter Park, this exceptional custom-built residence offers a rare combination of timeless design, modern sophistication, and an unbeatable location. Completed in 2017 and first sold in 2018, this 5-bedroom, 5.5-bath home has been meticulously maintained by its original owner and enhanced with high-end designer finishes. Much of the interior was thoughtfully reimagined by renowned designer Ted Maines, resulting in a sophisticated yet timeless aesthetic throughout. Perfectly positioned on a prime oversized corner lot, this remarkable residence blends transitional architecture with modern elegance. Expansive sliding glass doors fill the open-concept living spaces with natural light while creating a seamless connection between the indoors and outdoors. The main living area flows effortlessly from the formal living room and spacious dining area into the gourmet kitchen, complete with custom cabinetry, Carrara marble surfaces, and premium Sub-Zero and Wolf appliances. A refined yet inviting family room with a fireplace provides the perfect setting for everyday living and entertaining. The private first-floor primary suite offers direct access to the lanai and heated saltwater pool and is complemented by a spa-inspired bath with a steam shower and custom his-and-her walk-in closets. A secondary ground-floor bedroom provides exceptional flexibility for guests, multigenerational living, or a private home office. Upstairs, a spacious loft with a custom dry bar leads to a versatile media room. Three additional en-suite bedrooms complete the second level. Recent enhancements include a whole-house generator supported by a 250-gallon buried propane tank, new pool solar equipment, a newly added semi-circular driveway that enhances both curb appeal and functionality, two newer A/C units, and a new 2026 A/C system featuring re-engineered, high-efficiency ductwork designed to provide optimal climate control throughout the home. The outdoor living space is equally impressive, featuring a heated saltwater pool and spa with a cascading waterfall, elegant stone decking, an outdoor shower, ambient lighting, and a covered summer kitchen—perfect for year-round entertaining. A rare three-car garage completes this exceptional property. All of this is just moments from the shops, dining, parks, and unmistakable charm of downtown Winter Park

1761 Legion Drive, Winter Park

$425,000

3 Beds ⋅ 2 Baths ⋅ Albert Lee Ridge SubDv. ⋅ 32789 Zip Code

Welcome home to this adorable and beautifully updated 3-bedroom, 2-bathroom home in the heart of Winter Park! From the moment you arrive, the cheerful teal front door adds the perfect pop of color and sets the tone for the charm you’ll find throughout. Step inside to the inviting living room, where the home’s original hardwood floors immediately make an impression. Just beyond, the formal dining room and updated kitchen create a comfortable flow for both everyday living and entertaining. The kitchen features newer 2024 appliances, granite countertops, and plenty of character, blending modern convenience with the timeless feel of the home. French doors open from the living area to what may be the showstopper of the property - a massive, newly fenced backyard offering an incredible amount of space for entertaining, gardening, pets, play, or simply enjoying the outdoors. And for something truly special, the backyard features a custom treehouse built directly into the tree, creating a one-of-a-kind feature you won’t find in just any home. All three bedrooms are thoughtfully positioned down the hallway, with the primary bedroom tucked away at the back for added privacy with its own ensuite bathroom with a generously sized shower. The thoughtful updates and classic details make this home feel both move-in ready and full of personality. And then there’s the location! Enjoy easy access to I-4, making commutes and exploring Central Florida a breeze, while being just minutes from the shopping, dining, and entertainment of Winter Park Village and Park Avenue. With amazing shopping and everyday conveniences right around the corner, this home puts the best of Winter Park within easy reach. Charming, updated, full of character, and sitting on an incredible backyard — this is a Winter Park home you won’t want to miss!

2126 Albert Lee Parkway, Winter Park

$1,950,000

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

$2,699,000

5 Beds ⋅ 5 Baths ⋅ Comstock Park SubDv. ⋅ 32789 Zip Code

A DISTINCTIVE WINTER PARK RESIDENCE IN AN EXCEPTIONAL LOCATION. Set along a quiet brick street in one of Winter Park’s most established and desirable residential enclaves, this substantial custom home offers more than 4,400 square feet of living space in a setting surrounded by some of the area’s most architecturally notable residences. Originally built in 2015, the home has been thoughtfully and significantly enhanced by its current owners. The main living level was reconfigured to create a more open and functional flow, while the kitchen was completely renovated and wide-plank oak flooring was installed throughout both levels. The result is an interior that feels current and refined while remaining entirely appropriate to the home’s distinctive Winter Park character. Both HVAC systems have also been recently replaced. One of the residence’s most compelling qualities is the transition from its dramatic, old-world exterior presence through intimate courtyard and covered patio spaces into a beautifully updated interior. Soaring vaulted ceilings, exposed beams and generous room proportions create a sense of scale and architectural character rarely found in newer construction. The floor plan is equally impressive, with two bedroom suites on the main level, including a private primary retreat, while the second floor offers an oversized family-room loft, additional bedrooms and baths, and an abundance of storage. Indoor and outdoor living come together particularly well at the rear of the home, where the main living spaces open naturally to a large covered terrace and pool. The result is a true extension of the interior living environment and an ideal setting for year-round entertaining, relaxed gatherings and the Florida lifestyle Winter Park is known for. Rarely does a residence combine this degree of scale, architectural individuality, recent renovation and location so successfully. Zoned for top-rated public schools and near elite private schools, with easy access to Phelps Park, YMCA, ICC, WPRC and Park Avenue shops and restaurants!A sophisticated and highly livable custom home in one of Central Florida’s most coveted communities.

1597 Oakhurst Avenue, Winter Park

$189,900

2 Beds ⋅ 2 Baths ⋅ Stratford A Winter Park Condo SubDv. ⋅ 32792 Zip Code

One or more photos was virtually staged. This 2 Bedroom, 2 Bath, 953 SF Winter Park condo in the amazing Stratford community offers a comfortable, functional floor plan complemented by fresh interior paint, updated flooring, and a 2026 HVAC system. The spacious living area features a ceiling fan and sliding glass doors that bring in natural light and open to a covered balcony, creating an easy extension of the indoor living space. The adjacent dining area provides flexibility for everyday meals or additional living space. The kitchen features wood cabinetry, generous counter space, tile flooring, and stainless steel refrigerator, while an in-unit laundry closet adds everyday convenience. Bedrooms feature updated flooring, neutral finishes, ceiling fans, and ample natural light. A large walk-in closet with extensive shelving and storage helps keep everything organized, while the bathroom includes a tiled walk-in shower and vanity storage. Freshly touched up throughout and offering a practical layout with comfortable living spaces, this Winter Park condo is ready for its next chapter.

222 Lewfield Circle, Winter Park

$1,350,000

6 Beds ⋅ 4 Baths ⋅ Waters Edge At Hawks Crest SubDv. ⋅ 32792 Zip Code

Welcome to an exceptional opportunity in Waters Edge at Hawks Crest, one of Winter Park's premier gated, resort-style communities. Positioned on a desirable premium lot with beautiful water views, this impressive Kerrville II by Meritage Homes combines sophisticated design, generous living spaces, and an incredible outdoor lifestyle. Offering 6 bedrooms, 4.5 bathrooms, and a 3-car garage, this thoughtfully designed residence provides the flexibility today's buyers are looking for. The light-filled interior features an open and inviting layout with upgraded finishes throughout, creating the perfect setting for both everyday living and entertaining. At the center of the home, the gourmet kitchen is designed to impress with premium cabinetry, quartz countertops, a large center island, and high-end appliances. The kitchen opens seamlessly to the main living and dining spaces, making it easy to gather with family and friends. The outdoor living area truly sets this home apart. Step through to the extended lanai and enjoy your own private Florida retreat featuring a heated saltwater, self-cleaning pool and spa, outdoor kitchen, and an impressive screened enclosure enhanced with color-changing lighting for a dramatic evening atmosphere. Solar panels add an additional energy-efficient benefit to the home. The first floor offers exceptional versatility with formal living and dining spaces along with a private guest suite featuring its own en-suite bathroom and convenient access toward the pool area—ideal for guests, extended family, or multi-generational living. Upstairs, the owner's retreat provides a peaceful escape with views overlooking the pool and water. The spa-inspired primary bathroom, upscale finishes, and generous walk-in closets complete the space. Additional bedrooms and flexible living areas offer endless possibilities for a media room, home office, fitness space, playroom, or additional guest accommodations. The 3-car garage includes convenient overhead storage shelving, providing even more functionality and organization. Residents of Hawks Crest enjoy access to outstanding amenities, including a resort-style community pool, clubhouse, fitness center, playground, putting green, and a private dock on Lake Howell. Spend your weekends kayaking, canoeing, paddleboarding, fishing, or simply enjoying the lakefront setting. Ideally located in Winter Park with convenient access to Park Avenue, shopping, dining, entertainment, and cultural attractions, this home offers the perfect combination of luxury, lifestyle, location, and flexibility. Schedule your private showing today and experience everything this exceptional Hawks Crest residence has to offer.

1117 Wading Waters Circle, Winter Park

$1,829,000

4 Beds ⋅ 4 Baths ⋅ Lake Knowles Terrace 2nd Add SubDv. ⋅ 32789 Zip Code

Under Construction. Welcome to your next chapter in one of Central Florida’s most desirable locations! This stunning new-construction home offers 4 bedrooms, 3.5 bathrooms, 2,706 square feet of living space, and a 2-car garage, thoughtfully designed with an open-concept layout that brings style, functionality, and modern living together. Set on a spacious 7,561-square-foot lot, the home is designed for effortless indoor-outdoor living and includes a pool, creating the perfect setting for relaxing, entertaining, and enjoying the Florida lifestyle. The location is just as impressive. Enjoy convenient access to highly regarded schools, Winter Park’s charming downtown, shopping and dining, I-4, and Orlando International Airport. Nearby favorites include Winter Park High School, Maitland Middle School, Lakemont Elementary, Lake Highland, Trinity Preparatory, Winter Park Village, Publix, and local dining and coffee spots. Modern new construction, a desirable Winter Park location, a spacious lot, and a pool—1550 Palm Ave is a rare opportunity to call this sought-after area home. Renderings are artistic interpretations. Features and finishes may vary from final construction.

1550 Palm Avenue, Winter Park

$3,600,000

4 Beds ⋅ 5 Baths ⋅ Detmar Terrace Winter Park SubDv. ⋅ 32789 Zip Code

Tucked away in the heart of Winter Park, this custom-built residence seamlessly blends modern luxury with the comfort of everyday living. Thoughtfully designed with exceptional attention to detail, the home offers clean, contemporary interiors balanced by beautiful architectural elements, and abundant natural light. The main level offers two bedrooms and three full bathrooms, including a primary suite with a versatile bonus room behind French doors—perfect for a private office, gym, or additional bedroom. The ensuite features two walk-in closets, a double sink vanity, a large rainfall shower, and a soaking tub. The open-concept floorplan features a beautifully appointed kitchen with high-end appliances and custom cabinetry, flowing seamlessly with the dining area and the spacious living room, where a gas fireplace creates a welcoming gathering space. Architectural light wood ceiling beams, plantation shutters, and expansive glass sliders frame beautiful views of the outdoor living area. Upstairs, two additional bedrooms each feature private ensuite baths and balconies, complemented by a kitchenette and additional living space. This flexible layout is ideal for multigenerational living, guests, live-in staff, or simply creating a private retreat within the home. Designed for effortless indoor-outdoor living, the entire downstairs opens to a private backyard oasis featuring a sparkling saltwater pool, lush bamboo backdrop, summer kitchen, gas fireplace, and outdoor shower. The covered lanai is equipped with automatic screens, creating an inviting and comfortable space to enjoy the outdoors year-round. Beyond its sophisticated design, the home offers exceptional functionality, including an oversized two-car garage pre-wired for EV charging, whole-home surround sound, hurricane-impact windows, a whole-house Generac generator, indoor built-in sprinkler system, dual laundry rooms, and enhanced insulation for exceptional peace and quiet. The entire first floor is completely wheelchair accessible. Tastefully furnished and offered with all furnishings, this exceptional residence presents a rare combination of refined design, thoughtful functionality, and classic Winter Park charm. Ideally located just one mile from Park Avenue and minutes from Winter Park’s renowned restaurants, shops, hospitals, schools, and scenic Lake Osceola, this is a home designed for both elevated living and everyday comfort.

276 Detmar Drive, Winter Park

$450,000

5 Beds ⋅ 4 Baths ⋅ Ridge High 1st Add SubDv. ⋅ 32792 Zip Code

Welcome to 2181 Linden Road, where modern updates meet the everyday convenience of Winter Park living. Thoughtfully renovated and designed with flexibility in mind, this home offers a versatile layout, contemporary finishes, and a private separate-entry suite that adds valuable space for guests, a home office, or additional living arrangements. With no HOA, the property offers added flexibility rarely found in this sought-after area. The location is a standout. Enjoy easy access to Winter Park’s renowned Park Avenue, with its boutiques, restaurants, cafés, galleries, and local events, while nearby Winter Park Village adds even more shopping, dining, entertainment, and everyday conveniences. Outdoor enthusiasts will appreciate close access to the Cross Seminole Trail, Lake Baldwin Park, the Winter Park Chain of Lakes, scenic parks, and recreational opportunities. Downtown Orlando, major employment centers, Advent Health Winter Park, Rollins College, Full Sail University, SR-436, SR-426, and I-4 are also conveniently accessible. Winter Park continues to invest in its future, with ongoing improvements to Park Avenue, expanded infrastructure and streetscape enhancements, and a citywide Parks & Recreation Master Plan focused on improving parks, trails, open spaces, recreation, and community facilities for years to come. This is more than a renovated home it is an opportunity to enjoy the lifestyle, connectivity, character, and continued growth that make Winter Park one of Central Florida’s most desirable places to call home.

2181 Linden Road, Winter Park

$660,000

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

$4,299,000

Justamere Camp Rep SubDv. ⋅ 32789 Zip Code

Fly In. Unwind. Build Your Dream on Lake Killarney. Bring your seaplane and envision the lakefront estate of your dreams on one of Winter Park’s rarest offerings. Tucked away on a private peninsula surrounded by multi-million-dollar homes, this extraordinary property spans approximately 432 feet of shoreline along the spring-fed, crystal-clear waters of Lake Killarney. With 1.514 buildable acres across two combined lots (2401 & 2403 Euston Ave), you'll have the space—and the freedom—to design an architectural masterpiece or a serene retreat that blends seamlessly with the natural beauty of this exclusive setting. Lake Killarney is a hidden 234-acre gem, beloved for its tranquility, paddleboarding and watersports, abundant wildlife, and lakeside dining. Locals savor moments like scenic seaplane lunches at Hillstone and cozy evenings around fire pits under starlit skies. With no public access, the lake offers unmatched privacy, and its pristine waters are maintained year-round by a thoughtful system of two drainage wells. Just minutes away, enjoy the vibrant lifestyle Winter Park is known for—Rollins College, Park Avenue, Winter Park Village, Whole Foods, the Farmers Market, and a rich cultural scene are all at your fingertips. Whether you’re dreaming of a peaceful sanctuary or a showstopping entertainer’s paradise, this property offers the ultimate trifecta: land, luxury, and lifestyle.

2403 Euston Road, Winter Park

$660,000

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

$1,495,000

3 Beds ⋅ 3 Baths ⋅ Charmont SubDv. ⋅ 32789 Zip Code

A wonderful opportunity to build your dream home on one of Winter Park’s most idyllic streets. Situated on a quaint, one-way brick street with a charming park at its center, this exceptional 12,581-square-foot deep lot offers a rare combination of space, character, and location. Currently featuring a 3-bedroom, 2.5-baths, plus office home with 2,080 square feet, the property offers the flexibility to live in or rent the existing home while you finalize your plans and prepare to build. Ideally located within the highly sought-after “A” school district of Audubon K-8 and Winter Park High School, this property places you just minutes from downtown Orlando, Orlando Health, AdventHealth, and the Dr. Phillips Center for the Performing Arts. Enjoy easy access to the vibrant restaurants and shops along Corrine Drive, as well as the boutiques, dining, and charm of Park Avenue. A rare opportunity to create your ideal Winter Park residence in an extraordinary setting surrounded by convenience, character, and everything this coveted area has to offer.

150 E Reading Way, Winter Park

$475,000

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

Welcome to this charming 2 bedroom, 2 bath home, with light and bright open floor plan, spacious rooms and many updates and upgrades. Roof was replaced (2019), new A/C (8/26), fully renovated kitchen with quartz counters, cabinetry, and stainless appliances. Pella double pane windows (2020), new French doors and interior doors, and new soffits and gutters in 2025. Enjoy outdoor living in the lanai overlooking a large fenced backyard with native landscaping. This highly desired neighborhood offers excellent schools, quiet streets, community pool, hiking and biking trails, and nearby public golf course. Live minutes from Advent Hospital, city conveniences, downtown Park Avenue shops and restaurants. Also easy access to neighboring towns, Orlando and airports. This is a perfect starter home or downsize home for those want all the comforts and privacy of a home, neighborhood and community in smaller space and are not ready for an apartment and high HOA fees.

2824 Prince John Road, Winter Park

$1,875,000

3 Beds ⋅ 3 Baths ⋅ Charmont SubDv. ⋅ 32789 Zip Code

Set along the brick-lined streets of Charmont, one of Winter Park’s most coveted and established neighborhoods, 1661 Laurel Road presents a rare opportunity to own a home in an exceptional location just three houses from Lake Virginia. From the front yard, enjoy beautiful lake views and the timeless character of a neighborhood defined by mature trees, gracious homes, and a true sense of place. The current owners have cherished this property since 1972, and after more than five decades, the home is ready for its next chapter. Situated on an impressive 0.43-acre corner lot (18,802 square feet), the property offers flexibility that is increasingly difficult to find in Winter Park. The existing home can be thoughtfully remodeled and the floor plan reimagined while preserving the architectural charm and character that make the property special. Or, for those looking to create something entirely their own, the generous lot offers the potential to build a new home in one of Winter Park’s most desirable settings. Inside, a welcoming foyer introduces a floor plan filled with opportunity. To the right, the grand living room features abundant windows and natural light, beautiful proportions, and a wood-burning fireplace, with the space extending into a bright sunroom overlooking the grounds. A hallway off the living room leads to two bedrooms, each with its own ensuite bathroom. To the left of the foyer, a third bedroom offers a dedicated bathroom and walk-in closet. Straight ahead, the dining room features charming corner cabinetry and leads into the existing kitchen. Beyond the dining room, an additional sunroom and sitting area presents one of the home's many opportunities for transformation. Envision opening this space to create a more expansive kitchen with room for a built-in breakfast banquette, coffee bar, and functional drop zone—a gathering space designed around the way today's families live while retaining the home's original charm. A breezeway connects the main house to the two-car garage, while the space above offers a separate one-bedroom, one-bath apartment. Ideal for visiting guests, a private playroom or teen retreat, an office, or potential rental income, this additional living space adds another layer of flexibility to the property. Additional features include an irrigation well and 2018 HVAC system. Beyond the property itself, the location is what makes 1661 Laurel Road truly special. Enjoy Park Avenue, where Winter Park's beloved restaurants, boutiques, galleries, cafés, and cultural institutions create one of Central Florida's most distinctive lifestyles. Rollins College, Hannibal Square, Central Park, Mead Botanical Garden, and the Winter Park Chain of Lakes are all close by, while the neighborhood's tree-canopied streets offer a peaceful retreat just minutes from the energy of downtown. Zoned for Audubon Park K-8 and Winter Park High School, this is an opportunity to put down roots in one of Winter Park's most sought-after locations. Whether you envision restoring and reimagining the existing home or creating a new residence from the ground up, the possibilities at 1661 Laurel Road are truly exceptional. Some properties are defined by their finishes; others are defined by their location, land, history, and potential. This one offers all four.

1661 Laurel Road, Winter Park

$589,900

3 Beds ⋅ 2 Baths ⋅ Elizabeth Heights Sub SubDv. ⋅ 32789 Zip Code

Welcome to a beautifully renovated 3-bedroom, 2-bath residence offering approximately 1,700 square feet of thoughtfully designed living space in the heart of Winter Park. Step inside to a fresh, inviting interior where timeless travertine flooring complements a beautifully updated kitchen featuring new cabinetry, new appliances, and a spacious new pantry. Both bathrooms have been tastefully renovated, while new lighting and ceiling fans throughout add a polished finishing touch. Thoughtfully added storage provides both style and functionality for everyday living. Ideally situated near some of Winter Park’s favorite restaurants, coffee shops, shopping, museums, and local attractions, this home provides exceptional convenience with easy access to major roadways and hospitals. Beautifully refreshed and move-in ready, this home combines modern updates, comfortable living, and an exceptional Winter Park location.

1313 S Denning Drive, Winter Park

$675,000

Winter Park Village SubDv. ⋅ 32789 Zip Code

An opportunity to build new in an established Winter Park neighborhood. The existing home remains on the property and is offered for its land value only, allowing a buyer to design from the ground up on a street where redevelopment is already underway. Within a half mile, seven custom single-family homes are in their final phase of construction, most starting near $1.5 million. Border Drive itself is a mix of longtime homes and newer builds, shaded by mature trees and free of through traffic. Once the site is prepared, the parcel supports a custom plan with room to work in a pool, covered lanai and summer kitchen. Bring your own builder, or ask for an introduction to builders already working in the area. Park Avenue shops and restaurants, Rollins College, the Farmers Market and the chain of lakes are all a short drive away. Property sold as is. The buyer is to verify setbacks, utilities, impact fees, demolition requirements and permitted building dimensions with the City of Winter Park.

1416 Border Drive, Winter Park

$675,000

3 Beds ⋅ 1 Baths ⋅ Winter Park Village SubDv. ⋅ 32789 Zip Code

An opportunity to build new in an established Winter Park neighborhood. The existing home remains on the property and is offered for its land value only, allowing a buyer to design from the ground up on a street where redevelopment is already underway. Within a half mile, seven custom single-family homes are in their final phase of construction, most starting near $1.5 million. Border Drive itself is a mix of longtime homes and newer builds, shaded by mature trees and free of through traffic. Once the site is prepared, the parcel supports a custom plan with room to work in a pool, covered lanai and summer kitchen. Bring your own builder, or ask for an introduction to builders already working in the area. Park Avenue shops and restaurants, Rollins College, the Farmers Market and the chain of lakes are all a short drive away. Property sold as is. The buyer is to verify setbacks, utilities, impact fees, demolition requirements and permitted building dimensions with the City of Winter Park.

1416 Border Drive, Winter Park

Downtown Winter Park

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