Refine Search
Sort by
$860,000
4 Beds 2 Baths 32792 Zip Code
Rare opportunity to own an established daycare operating from two structures on the same parcel, offered together with the real estate. The business currently provides immediate income for a hands-on owner or family-run operation. One structure is currently utilized for daycare operations, while the second structure is a single-family home that offers excellent potential for future daycare expansion (subject to licensing and approvals)—a unique value-add opportunity for growing operators. The property is already configured for childcare use with existing operations in place, making this an ideal turn-key opportunity for families looking to step into business ownership or operators seeking to expand their footprint. Sale includes real estate. Business goodwill, licensing, and operations may be included or negotiated separately. Convenient location with strong demand for childcare services. Please do not disturb staff or business operations. Showings by appointment only.

1521 Heron Wood Place, Winter Park

$2,100,000
3 Beds 5 Baths 147 Interlachen Place SubDv. 32789 Zip Code
Welcome to 147 Interlachen Place, Enjoy Winter Park's most desirable location! One block from Historic Park Avenue/Central Park. Spacious, bright and all on ONE FLOOR. The buildings second floor offers privacy and easy access. The Southwest corner provides direct natural light throughout the day. Private elevator access with secured underground parking. This beautiful home offers a short walk to everything Winter Park, a pedestrian village of delight! Natural light fills the central courtyard which features an iron water fountain. Private pool with heated spa and outdoor grilling and entertaining area. Interior features include fireplaces in living room, 2 Southwest facing covered outdoor walkout balconies, accessed by living room, den, master bedroom and one directly over looking the pool. Master bathroom includes separate tub and shower, dual closets, split vanities and plenty of storage space. 4 full bath- 1 half bath (5). Two specified parking spaces also have large storage closets with security gate and elevator access to your floor. K-8 Audubon School district! Unit / building “horseshoe” configuration provides no neighbors on any of the 4 sides, courtyard interior, Private Luxury Living all on ONE floor!

147 S Interlachen Avenue Unit 202, Winter Park

$1,380,000
4 Beds 4 Baths Sylvan Heights SubDv. 32789 Zip Code
Welcome to 1751 Goodrich Ave, a beautifully designed residence in the heart of Winter Park! This 4-bedroom, 3.5-bath home showcases thoughtful contemporary architecture with 10' ceilings on both floors, and an open-concept layout that effortlessly blends style and function. With large double paned windows throughout, this home is drenched with an abundance of natural light. High-end finishes continue through the home with a level 5 finish on all walls, spray foam insulation, solid-wood doors, designer shades on every window, and custom closet systems. The showstopping chef-inspired kitchen was designed to entertain with an expansive island, seating 6, and premium finishes- including custom cabinetry, quartz countertops, soft close cabinets and drawers, a concealed Bosh dishwasher, a 48" Thermidor 6-burner gas range, and a Viking Refrigerator. The kitchen seamlessly flows into the living room and dinning space, and also offers easy access for indoor/outdoor entertaining with the telescoping sliding glass door. Outside, you will find the extended patio with plenty of room for hosting friends and family under the bistro-lighting while cooking at the summer kitchen (grill, fridge, range hood). Back inside, you will find a laundry room, half bathroom, and downstairs bedroom with an ensuite offering flexibility to the first floor. Upstairs, you are greeted with a small loft space, 2 bedrooms with a Jack-and-Jill bathroom, and an exquisite primary suite. The primary suite is a true retreat with a large balcony, his and her walk-in closets, and a spacious primary ensuite, featuring a beautiful soaking tub, designer tile, quartz countertops, and great natural light. All upstairs bedrooms are also equipped with motorized black-out shades. This residence is modern, refined, and impeccably curated, offering elevated indoor-outdoor living just minutes from Park Avenue, AdventHealth Winter Park, Rollins College, museums, dining, shopping, and all that Winter Park has to offer! Reach out to schedule your private tour today.

1751 Goodrich Avenue, Winter Park

$544,900
3 Beds 2 Baths Winter Park Pines Merrie Oaks SubDv. 32792 Zip Code
330 Elkhorn Ct is a beautifully renovated home located in the highly desired Winter Park Pines community. Freshly updated with a 2025 electric panel, 2025 A/C system, and a 2024 roof, offering modern efficiency, peace of mind, and big-ticket upgrades already taken care of! Inside, you’ll find a bright, open layout with wide-plank flooring, recessed lighting, and a modern neutral color palette that feels clean and inviting. The kitchen has been thoughtfully updated with shaker-style cabinetry, sleek countertops, stainless steel appliances, and designer finishes—including a farmhouse sink and gold hardware/fixtures that add a high-end touch. The bedrooms offer comfortable space with updated finishes throughout, while the oversized backyard provides plenty of room to relax, entertain, garden, or create your ideal outdoor setup. Conveniently located near shopping, dining, parks, and major roadways—and zoned for top-rated schools including Winter Park High School—this home is a standout opportunity in one of the area’s most sought-after neighborhoods.

330 Elkhorn Court, Winter Park

$460,000
3 Beds 2 Baths Howell Estates 1st Add SubDv. 32792 Zip Code
PRICE REDUCED!! Welcome to your dream home! This beautifully renovated single-story residence features 3 spacious bedrooms and 2 baths, all set on an expansive .42-acre lot in the desirable Howell Estates community. Brand New Roof (2024) Replumbed (2024) New HVAC System, Gourmet Kitchen: Brand new upgraded white cabinets, stunning quartz countertops, and new stainless steel appliances. Luxurious Bathrooms: Both completely renovated, featuring modern finishes Oversized Bedrooms: Including a primary suite with his-and-hers closets and an ensuite bath with a gorgeous walk-in shower. In the Family Room: Spacious layout with a cozy wood-burning fireplace, Oversized Garage: Perfect for larger vehicles, including SUVs. The backyard has a: New Fence, New Pergola and New Extended Porch. This home is move-in ready and waiting for your family to create lasting memories. Don’t miss out on this exceptional opportunity in Winter Park!

1052 Manchester Circle, Winter Park

$2,500,000
32792 Zip Code
Looking for the next location of your current or future business? There is no better place than this! Located in the heart of Winter Park and zoned for C-3, this space is right next to popular foot traffic places such as Costco and Full Sail University, as well as several apartments and shopping centers which would greatly increase the chance of profit! An amazing thing about this deal is the two in one package it has, having two facilities! The front building is massive, offering a giant open space with several office rooms and bathrooms. The second building behind the front building has even more office spaces, bathrooms, and most importantly can be leased or rented! There is no need to worry about parking, the parking space can fit several cars!

3425 Forsyth Road, Winter Park

$255,000
2 Beds 2 Baths Windward Square Sec 2 SubDv. 32792 Zip Code
Virtually Staged. ALL PLAY and NO WORK! Imagine coming home to a space where weekends are made for relaxing, entertaining, and enjoying the best of Florida living. This single-story, two-bedroom, two-bath townhome offers an effortless lifestyle in a location that puts everything within reach. Vaulted ceilings create an open, airy feel in the spacious living and dining area, while sliding glass doors lead to a private, fenced backyard with a large concrete patio?perfect for morning coffee, weekend barbecues, or unwinding after a long day. With no rear neighbors and views of the community green space, you?ll enjoy added privacy and tranquility. The kitchen is designed for everyday ease, featuring ample cabinetry, a breakfast bar, and all appliances included, making move-in simple. Retreat to the oversized primary suite with a walk-in closet and direct patio access, creating a true indoor-outdoor flow. The second bedroom offers flexibility for guests, a home office, or creative space. Step outside your front door and enjoy resort-style amenities, including three swimming pools, tennis courts, a clubhouse, and a playground—all with low HOA fees. With parking for three vehicles, convenience is built right in. Located close to shopping, dining, major roadways, and just minutes from Winter Park’s Park Avenue, this home delivers both comfort and connection. Owner-occupant only community—ideal for those looking to put down roots and enjoy a true neighborhood feel. Live more. Maintain less. Welcome home.

2651 Cayman Way, Winter Park

$1,750,000
4 Beds 3 Baths Sylvan Heights SubDv. 32789 Zip Code
Under Construction. NEW CONSTRUCTION – Under Construction. Welcome to Winter Park! This stunning modern residence is meticulously designed and ideally located near everything. This beautifully crafted home features 4 bedrooms, 2.5 bathrooms, and 2,350 square feet of living space, plus an additional 1,247 square feet of terraces and lanai. The open-concept kitchen showcases quartz countertops, custom cabinetry, and stainless steel appliances, perfect for both everyday living and entertaining. Step outside to the private lanai, where you can enjoy a summer kitchen, pool, and lushly landscaped backyard, creating an ideal indoor-outdoor lifestyle. From the moment you enter, the home is filled with warm natural light and high-quality finishes throughout, creating a welcoming atmosphere. The primary bedroom is conveniently located on the first floor, offering privacy and comfort along with an inviting, functional layout. The second floor features three additional bedrooms, two bathrooms, and two expansive terraces, perfect for relaxation or entertaining. Located just minutes ( 1.25 Miles ) from Park Avenue Restaurants and shopping district, 15 min from Downtown Orlando, and an array of fine dining, boutique shopping, museums, and local cafés, this exceptional home offers modern luxury in an unbeatable location.

1840 Anzle Avenue, Winter Park

$182,900
2 Beds 2 Baths Stratford A Winter Park Condo SubDv. 32792 Zip Code
INVESTOR - MOTIVATED SELLER - PRICE ADJUSTED! Wonderful! Exceptional Winter Park location! Amenities include 2 pools, lighted tennis courts, fitness center, car care facilities & clubhouse, enjoy the simple life in this 2 bedroom, 2 bath, ground floor unit. Sip your morning coffee while admiring the garden landscaping from your screen enclosed patio. Host a BBQ with family and friends at the community clubhouse or enjoy shopping at the many neighborhood retail and grocery outlets nearby. The quaint restaurants, coffee houses, golf courses, and farmers markets of Winter Park and Baldwin Park are within biking distance. There is always something to see and do at this prime location. Recent upgrades include: new electric panel (2024), new washer/dryer in unit (2024), new dishwasher (2023), refrigerator (2020).

205 Lewfield Circle Unit 205, Winter Park

$1,449,999
5 Beds 4 Baths Lawndale SubDv. 32789 Zip Code
BRAND NEW CONSTRUCTION COMPLETED APRIL 2026, MOVE-IN READY. 2-year builders' warranty! This 3,164 sqft home at 1523 Miller Ave, Winter Park, FL 32789 combines modern design, high-end finishes, and an unbeatable central location. Featuring 5 bedrooms, 4 full bathrooms, and a private salt-water pool, the home is designed for both everyday comfort and effortless entertaining. The open L-shaped living, kitchen, and dining area is filled with natural light and anchored by a 4-panel grand pocket slider that fully retracts, opening the entire living space to the covered patio for true indoor-outdoor living. The chef’s kitchen overlooks the main living area and flows seamlessly outside to a fully equipped outdoor kitchen with grill, sink, and fridge, complemented by a spacious seating area and pool—ideal for hosting year-round. Additional highlights include a shingle roof with metal accents, a pergola accenting the front of the garage, and clean architectural lines that elevate the curb appeal. The floor plan offers flexibility with generous bedroom sizes and well-appointed full baths, while the backyard retreat centers around the sparkling salt-water pool. Location is a major advantage—2 minutes to I-4, 4 minutes to Mills Avenue, 5 minutes to Park Avenue, 10 minutes to Downtown Orlando, and approximately 20 minutes to Disney, placing dining, shopping, nightlife, and major employers all within easy reach. A rare opportunity to own a brand-new construction home in one of Winter Park’s most connected neighborhoods.

1523 Miller Avenue, Winter Park

$499,000
4 Beds 2 Baths Winter Woods Unit 01 SubDv. 32792 Zip Code
PRICE REDUCED!!! ROOF 4 yrs. old, newer A/C, In-ground Pool. Enclosed Patio — a beautifully maintained turnkey home nestled in the heart of Winter Park, one of Central Florida’s most sought-after communities. Surrounded by renowned golf courses, top-rated Seminole County schools, lush parks, and family-friendly neighborhoods, this exceptional residence offers the perfect blend of comfort, convenience, and the elevated Winter Park lifestyle buyers are searching for. This spacious 4-bedroom + office home is completely move-in ready and vacant — just bring your furniture and clothes and start living! From the moment you walk through the front door, you’ll love the bright open-concept layout filled with natural light, updated finishes, granite countertops, modern appliances, and an inviting wood-burning fireplace that creates the perfect family gathering space. Designed for entertaining and Florida living, the oversized Florida room/lanai overlooks a stunning private pool and beautifully landscaped fenced backyard, creating the ultimate indoor-outdoor experience. Whether hosting weekend BBQs, pool parties, holiday gatherings, or simply relaxing after work, this home was built for making memories. Additional highlights include: • 2,092 square feet of living space • 4 bedrooms plus dedicated office/bonus room • Large open kitchen with granite countertops and abundant cabinet space • Spacious primary suite with pool views • Huge covered Florida room perfect for entertaining • Private in-ground pool • Full irrigation system and landscaped yard • Wood-burning fireplace • NO HOA • Attached 2-car garage plus additional parking • Fully fenced backyard for privacy and pets • Move-in ready condition Located in the highly desirable Winter Woods/Lake Howell area, this home is centrally positioned near major highways including SR-417, I-4, Howell Branch Road, and SR-436, making commuting to Downtown Orlando, Winter Park Village, UCF, Orlando International Airport, beaches, shopping, dining, and all Central Florida attractions incredibly convenient. Winter Park is known for its charm, tree-lined streets, upscale dining, boutique shopping, beautiful golf communities, and strong sense of community. Families love the area for its excellent schools, nearby parks, recreational amenities, and safe neighborhood atmosphere. This is more than just a home — it’s a lifestyle opportunity in one of Florida’s premier communities.

2217 Sussex Road, Winter Park

$630,000
5 Beds 3 Baths Glencoe Sub SubDv. 32789 Zip Code
SELLER MOTIVATED!! Potential of an extra one percent for closing costs, just ask your agent!! A FULLY MODERNIZED 5-bedroom, 3-bathroom home offering Modern style, flexibility, and comfort and its own ATTACHED 2bed/1 Bath IN-LAW SUITE!!! Step inside to an open and airy layout featuring Luxury vinyl plank flooring, fresh neutral paint, and large windows that fill the home with natural light. The upgraded kitchen is a true showstopper — boasting shaker cabinets, quartz countertops, subway tile backsplash, and stainless steel appliances with stylish hardware accents. Located just a 10 minute walk to Lake Killarney and a 3 minute walk to Killarney Elementary School! What is even more fantastic is the distance to I-4 is literally just 2 minutes away for fast and convenient travel to and from downtown Orlando and just 10 minutes from Park Avenue Winter Park!! So many restaurants, parks, local shops and family activities, Especially during the holidays!! Come see this home with potential income and your own private 3/2 as well. This home includes a versatile 2-bedroom, 1-bath in-law suite with its own private entrance, perfect for extended family, guests, or rental potential. Enjoy extra living space in the spacious Florida room, ideal for entertaining, relaxing, or creating the perfect indoor-outdoor flow. With its thoughtful upgrades and multi-generational layout, this home blends functionality with timeless design — truly move-in ready and waiting for you to make it your own!

2612 Roxbury Road, Winter Park

$925,000
2 Beds 2 Baths Killarney Circle SubDv. 32789 Zip Code
Nestled on the shores of private, skiable Lake Killarney, this beautifully updated and absolutely adorable 2-bedroom, 2-bath home offers a rare opportunity to enjoy true lakefront living without the upkeep of a large estate. Perfect as a full-time residence, a weekend lake escape, a snowbird retreat, or even an income-producing short-term rental (as previously used by the current owners), this charming property delivers the ultimate blend of convenience, recreation, and Winter Park lifestyle. Wake up to serene water views, spend your days boating across crystal-clear Lake Killarney, and end each evening with breathtaking sunsets on the water. From your private dock, you can cruise straight over to Hillstone for happy hour or pull up to Trader Joe’s for a quick grocery run—the kind of effortless, magical living that only this lake can offer. Located just minutes from Park Avenue’s boutique shops, fine dining, and cultural attractions, this home feels worlds away while keeping you close to everything you love. Whether you're wanting to downsize and have low maintenance, a seasonal resident seeking a warm-weather sanctuary, or a local looking for the perfect weekend getaway to store your boat, this home delivers a lifestyle unlike anything else in Winter Park. A unique location, a turn-key home, and an unmatched lake experience; this Lake Killarney gem is a must-see and you won’t want to miss it.

560 Ololu Drive, Winter Park

$290,000
2 Beds 1 Baths Lake Killarney Condo SubDv. 32789 Zip Code
Welcome to Lake Killarney Living ... Where Winter Park charm meets everyday convenience. Furniture negotiable, offering added flexibility for buyers or investors. Discover this beautifully appointed 2-bedroom, 1-bath condo in the highly sought-after Lake Killarney Condo Community, perfectly positioned just steps from Winter Park Village, dining, shopping, and the peaceful waters of Lake Killarney. Inside, you’ll find a bright, natural light–filled living space with an intimate, inviting feel. The efficient galley kitchen flows seamlessly into the living and dining area, making the home feel larger than its square footage. A rare bonus for condo living, the home includes a separate laundry room, offering added convenience and additional storage. Step outside to your private patio space, perfect for morning coffee, quiet evenings, or creating your own cozy outdoor retreat. There’s even room for a foosball table, making it a great spot to unwind, entertain, or simply grab a Coke and smile as you enjoy the Florida breeze. Residents enjoy an impressive list of community amenities, including a sparkling private pool, lush green spaces, and access to Lake Killarney’s private community dock, ideal for launching kayaks and paddleboards, fishing, or taking in serene lakefront views. Enjoy evening sunset strolls, weekend boating, or a relaxing afternoon by the pool. The community also offers convenient on-site laundry facilities, beautifully maintained grounds, and a welcoming neighborhood atmosphere. With strong rental appeal, an unbeatable location, and timeless Winter Park charm, 151 N Orlando Ave #115 is an ideal choice for first-time buyers, downsizers, or investors seeking long-term value in one of Central Florida’s most desirable lakefront communities. Schedule your private showing today and experience the lifestyle waiting for you at Lake Killarney.

151 N Orlando Avenue Unit #115, Winter Park

$2,195,000
5 Beds 4 Baths Lugano Terrace SubDv. 32789 Zip Code
Located in highly desirable Lugano Terrace just steps from the shores of Lake Knowles, this stunning all new interiors, 5-bedroom, 3.5-bath brick home effortlessly blends timeless charm with extensive modern updates. Set on a beautifully oversized landscaped lot with a roundabout driveway. Winter Park’s most sought-after neighborhoods adjacent to the Vias, Winter Park Racquet Club and Dommerich Elementary. Inside, wide-plank engineered white pine flooring flows throughout, complementing vaulted ceilings, wood-burning fireplace in the living room, and a spacious open layout ideal for entertaining. The informal dining room overlooks the private backyard and resurfaced PebbleTec pool, while the chef’s kitchen impresses with dual islands, quartz countertops and full-height quartz backsplash, custom hood, Thermador appliances including a 48” six-burner gas range and French door refrigerator. The gorgeous, light filled family room showcases gas fireplace and a built-in bar with wine fridge. The expansive upstairs primary suite is a luxurious retreat, featuring a spa-like bath with a dual-entry shower with Infrared sauna, soaking tub, dual vanities with LED mirrors, expanded closets, and a sitting area. Also upstairs is a flexible loft or library space, an office/nursery with a private balcony, and a bonus exercise room or third closet. Three spacious bedrooms are located downstairs, including a second primary or guest suite with its own en-suite bath and pool access. Notable upgrades include a new roof (2021), PEX plumbing and water heater (2025), updated electrical panels, new propane tank, new AC supply grills and a new second AC system (2025). Additional features include Level 4 smooth drywall, custom trim and moldings, 8’ metal front and double back doors, custom wood interior doors, upgraded light switches and plugs, all-new designer light fixtures ( Regina Andrew, Visual Comfort, etc. ), fireplace surrounds, and custom metal and wood staircase. Black interior and exterior Anderson windows: Dual Pane Low-E Smart Sun Standard Argon Fill Simulated Divided Light (SDL). Outside, enjoy a fully fenced and gated backyard with turf and paver landscaping, updated pool coping, and a covered porch ideal for entertaining, new exterior paint and gas lanterns. The 2-car garage includes custom paneled doors, painted floor and workshop area. Located within walking distance to top-rated Dommerich Elementary, Maitland Middle, and Winter Park High, and just minutes from Park Avenue and the Winter Park Racquet Club and Interlachen Country Club, this home offers exceptional quality, location, and lifestyle. NEW April 2026 Black Steel doors windows with low e-dual pane glass ($150k value!).

1885 Temple Drive, Winter Park

$3,390,000
5 Beds 7 Baths Forest Hills SubDv. 32789 Zip Code
Nestled just moments from the boutiques and cafés on Park Avenue, this newly completed masterpiece redefines Winter Park luxury living. Perfectly positioned on an expansive 0.30-acre lot, this residence captures attention from the moment you arrive, with its striking architectural details, a sweeping driveway, and detached garage that together set a tone of timeless sophistication. Inside, soaring 20-foot ceilings welcome you into a grand foyer framed by curved archways and exceptional millwork. The living room is a true showpiece, centered around a statement fireplace with built-in shelving and subtle LED underlighting that accentuates every detail. The chef’s kitchen is a work of art, showcasing quartz countertops, exquisite custom cabinetry, integrated LED lighting, a Wolf appliance suite, and a charming breakfast nook. The formal dining room captivates, with stunning coffered ceilings floor to ceiling windows, and an atmosphere perfectly suited for elegant entertainment. The primary suite is a private sanctuary, offering dual vanities with floating mirrors, a freestanding soaking tub, a walk-in rain shower, and a spacious custom closet. Each additional bedroom has been thoughtfully designed with generous proportions and its own en-suite bath, blending comfort with sophistication. Upstairs, a loft and secondary laundry area provide convenience and versatility, while the main level includes a full mudroom and butler’s pantry with an additional washer and dryer, tailored for effortless living. The outdoor living space rivals the most luxurious resorts. A covered lanai with retractable screens seamlessly extends the interior’s sophistication outdoors, offering a year-round retreat for dining or lounging. The expansive pool deck unfolds around a sparkling pool and integrated spa, complemented by a dedicated pool bath connected to the detached garage. From the curved archways to the meticulous millwork and layered LED lighting throughout, every inch of this home reflects the builder’s attention to detail and commitment to craftsmanship. It is more than a home, it is a statement of style, presence, and precision in the heart of Winter Park’s most coveted location.

1751 Glencoe Road, Winter Park

$630,000
5 Beds 3 Baths Glencoe Sub SubDv. 32789 Zip Code
SELLER MOTIVATED!! Potential of an extra one percent for closing costs, just ask your agent!! Come view this NEXTGEN Home FULLY MODERNIZED 5-bedroom, 3-bathroom home offering flexibility, and comfort that Includes an Attached 2 Bed/1 Bath IN- LAW SUITE!! Step inside to an open and airy layout featuring Luxury plank flooring, fresh neutral paint, and large windows that fill the home with natural light. The upgraded kitchen is a true showstopper — boasting shaker cabinets, quartz countertops, subway tile backsplash, and stainless steel appliances with stylish hardware accents. Located just a 10 minute walk to Lake Killarney and a 3 minute walk to Killarney Elementary School! What is even more fantastic is the distance to I-4 is literally just 2 minutes away for fast and convenient travel to and from downtown Orlando and just 10 minutes from Park Avenue Winter Park!! So many restaurants, parks, local shops and family activities, Especially during the holidays!! Come see this home with potential income and your own private 3/2 as well. This home includes a versatile 2-bedroom, 1-bath in-law suite with its own private entrance, perfect for extended family, guests, or rental potential. Enjoy extra living space in the spacious Florida room, ideal for entertaining, relaxing, or creating the perfect indoor-outdoor flow. With its thoughtful upgrades and multi-generational layout, this home blends functionality with timeless design — truly move-in ready and waiting for you to make it your own!

2612 Roxbury Road, Winter Park

$109,500
1 Beds 1 Baths Winter Park Woods Condo SubDv. 32792 Zip Code
This 1 bedroom, 1 bath condo at 311 Scottsdale Sq, Winter Park, FL 32792 is leased to a reliable long-term tenant paying $1,450 / month. Located on the first floor in the established Winter Park Woods community, this unit features an open-concept layout as soon as you walk in. The HOA includes water, access to two community pools, a playground, and tennis courts. Winter Park Woods is also zoned for highly rated schools in Florida, which helps with both property value and long-term rental demand. The location is a major plus. This condo sits in the heart of Winter Park / Winter Park Pines / Goldenrod area, close to Full Sail University, UCF, AdventHealth, Orlando International Airport, and main highways for easy commuting. You’re just minutes from shopping, grocery stores, restaurants, gyms, parks, and Winter Park’s retail corridors. You also have quick access to downtown Winter Park, Orlando, and major job centers, which keeps rental demand very strong in this area.

311 Scottsdale Square Unit 311, Winter Park

$6,495,000
5 Beds 7 Baths Osceola Place SubDv. 32789 Zip Code
Exquisite new construction with 5 Bedrooms 6.5 Baths and a 3 car garage, in the Heart of Winter Park perfectly positioned on an oversized lot just steps from Park Avenue’s renowned shops, fine dining, and the iconic Winter Park 9-hole golf course, this extraordinary custom residence is a showcase of timeless design and modern luxury. Conceived by acclaimed architect Dan Delong of Origins Residential Design and brought to life by Sean Wulff of Native Homes, every detail has been thoughtfully curated to impress even the most discerning buyer. The expansive floor plan encompasses 5 bedrooms, 6 full baths, and 1 half bath, blending sophistication and comfort across multiple living spaces. Highlights include a dramatic great room, inviting family room, private study, downstairs guest suite, a full bar featuring a 56-bottle wine refrigerator, and an upstairs game room ideal for both everyday living and elegant entertaining. A grand entry reveals the great room with soaring floor-to-ceiling windows and elegant Italian porcelain tile, all overlooking the serene pool and patio. The chef’s kitchen seamlessly connects to the family room and features Canadian-crafted European-style cabinetry, Wolf, Sub-Zero & Fisher & Paykel appliances (dual ovens, dual dishwashers, built-in coffee maker, wine cooler, and beverage center), quartzite countertops, a large island with bar seating, hidden walk-in pantry, plus whole house water softener and filtration systems for premium convenience. The first-floor primary suite is a true retreat with spa-inspired amenities and a custom-built walk-in closet complete with cabinetry and a spacious island. Also on the main level: a private guest suite and dedicated home office/study. Upstairs, a generous game room and three additional en suite bedrooms provide comfort and privacy for family and guests alike. Designed for seamless indoor-outdoor living, the residence boasts two covered lanais finished in Turkish Marble, disappearing screens, a summer kitchen with Urban Bonfire Cabinetry, refrigerator, and ice maker, along with a freestanding fire pit and lush tropical landscaping. The saltwater pool with sun shelf and heated gas spa ensures year-round enjoyment. Built to the highest standards, the home features R-14 block walls with core 500 insulation, open cell foam insulation in attic, Andersen windows, a flat concrete tile roof, and tongue-and-groove ceilings on all lanais. Additional luxuries include: Select European white oak wood floors and Italian porcelain flooring throughout 12’ ceilings on the main level, 10’ ceilings upstairs Cutting-edge construction for efficiency and durability

550 Palmer Avenue, Winter Park

$8,950,000
7 Beds 11 Baths Windsong-Preserve Point SubDv. 32789 Zip Code
In the exclusive community of Windsong on Lake Berry, this magnificent 1.6-acre gated Mediterranean estate is a private oasis. With over 11,000 square feet of living area and a beautifully landscaped lakefront lot, this residence offers an exceptional blend of elegance, charm and privacy rarely found in Winter Park. The home features seven spacious bedrooms and nine full and two half baths. Entertain in the all-glass conservatory, dedicated theater room with motorized seating and a fully equipped game room. Modern conveniences throughout including gas-powered generators, an elevator and dumbwaiter. Two above-garage apartments provide ideal accommodations for guests and family. Outdoors, enjoy an expansive covered lanai, infinity edge pool and spa, boat dock with jet ski lift, and a summer kitchen complete with wood-burning fireplace, gas grill, refrigerator and icemaker, all overlooking the beautifully landscaped yard and lake. With its private gated entrance, this home is a one-of-a-kind opportunity to enjoy all the amenities Winter Park and Windsong have to offer.

1120 Preserve Point Drive, Winter Park

$3,650,000
5 Beds 5 Baths Charmont SubDv. 32789 Zip Code
Under Construction. Step into a world where the timeless charm of Old Winter Park meets the pinnacle of modern luxury designed by Winter Park Design and masterfully crafted by renowned builder Vimaro Homes. Nestled on one of Winter Park’s most coveted tree-lined streets, this stately home immediately commands attention with its double-entry driveway, framed by manicured landscaping and a sense of grandeur like no other. Inside, the home unfolds across more than 3,600 square feet of impeccably designed living space, with every room telling a story of quality, craftsmanship, and comfort. Rich herringbone hardwood floors stretch throughout the residence, complemented by bespoke millwork, and soaring ceilings. At the core of the home, the designer chef’s kitchen is a true showpiece, crafted for culinary excellence and effortless entertaining. Outfitted with top-of-the-line stainless steel appliances, custom cabinetry with designer hardware, and striking quartz countertops, the space is as functional as it is beautiful. A large island provides a natural gathering place, while an adjacent walk-in pantry offers seamless storage and prep. The primary suite is a retreat unto itself; a serene oasis tucked away for ultimate privacy. The spa-inspired en-suite bathroom rivals the finest resorts, featuring a soaking tub, walk-in shower with rainfall fixtures, designer lighting, dual vanities with custom cabinetry, and luxurious stone finishes throughout. A large, custom walk-in closet completes this elegant retreat. Beyond the main living areas, this home offers unique and thoughtfully designed spaces that elevate everyday living including a dedicated home office, a spacious loft, and a grand 3rd floor bonus room. Outdoors, a resort-style pool, covered lanai, and fully equipped summer kitchen create a private haven for year-round entertaining under the Florida sun. For the car enthusiast, this home offers a perfect fusion of elegance and functionality with a stately porte-cochere, a detached garage connected to the home by a breezeway, and an expansive motor court ideal for guest parking or showcasing a prized collection. Every element of this home speaks to impeccable taste and thoughtful design, from the curated finishes and luxury fixtures to the breathtaking architecture and designer lighting. Located just moments from Park Avenue, Rollins College, and Winter Park’s finest shopping and dining, you are truly in the heart of it all. More than a residence, this is a rare architectural masterpiece by Vimaro offering an unmatched lifestyle in the heart of one of Central Florida’s most coveted neighborhoods.

207 E Kings Way, Winter Park

$3,235,000
5 Beds 6 Baths Forest Hills SubDv. 32789 Zip Code
This stunning new contemporary residence, a five-bedroom, five-and-a-half bath home by the renowned Rex-Tibbs Development, a custom builder for over 40 years, continues to set the standard for luxury living. Perfectly situated on a premium, quiet, charming brick street, the home blends clean architectural lines with timeless finishes and thoughtful design details. An elegant foyer immediately introduces the home’s refined aesthetic, offering a direct line of sight to the gorgeous herringbone white oak floors in the great room and the sparkling pool just beyond the full glass doors. Anchored by a sleek linear gas fireplace with custom built-ins and floating shelves, the great room provides an inviting yet sophisticated gathering space. The open-concept chef’s kitchen is a showpiece in both form and function. Outfitted with Wolf and Sub-Zero appliances, it boasts an eight-burner range with one-and-a-half ovens, an oversized Sub-Zero French door refrigerator with a freezer drawer, a built-in microwave drawer, and a walk-in pantry featuring a wine and beverage tower. Marble counters in all baths continue the home’s commitment to refined finishes. The main level primary suite is a serene retreat with a spa-inspired bath featuring a large glass-enclosed shower, separate soaking tub framed by dramatic four-by-ten-foot porcelain slabs, a custom walk-in closet, and a private water closet. A flexible fifth bedroom with an ensuite bath offers the perfect option for an office or den. A striking glass-railed staircase leads to the second level, where a spacious lounge area opens to a private covered patio. Three additional ensuite bedrooms, each with custom closet systems, complete the upstairs living quarters. Designed for indoor-outdoor living, the expansive covered lanai includes a summer kitchen with a grill, hood vent, refrigerator, sink, and a dedicated half bath. Overlooking lush landscaping with tropical Clusia hedges and Foxtail palms, the brand-new pool is finished with designer tile that lends a stylish, resort-quality flair. Additional highlights include a spacious storage closet under the staircase, oversized two-car garage, 500-gallon propane tank for easy generator connection, stone paver driveway and durable metal roof. Wonderfully located in a picturesque neighborhood, the property is just minutes from the boutiques and dining of Park Avenue, top-rated public and private schools and offers convenient access to downtown Orlando, the attractions, as well as area airports. A rare opportunity to own a newly constructed home of such quality and craftsmanship in one of Winter Park’s most sought-after neighborhoods.

1821 Englewood Road, Winter Park

$475,000
3 Beds 2 Baths Winter Park Pines SubDv. 32792 Zip Code
PRIME LOCATION! Beautiful 3 Bedroom 2 Bathroom home is located in sought after Winter Park Pines with NO HOA and NO CDD. It is situated on a Corner Lot (0.22 Acre) and is a super short distance to the High Rated schools in Winter Park. The interior is extremely well kept with engineered wood floors, crown molding, and a beautiful glass entry door. There is a captivating white-washed stone fireplace and built in shelving for an elegant look in the Family Room. The kitchen has stainless steel appliances, wood cabinets with under cabinet lighting, and bar top seating. Primary Bedroom has a walk-in closet and a glass door shower with tile walls and built-in niches. The Primary bathroom has private access to the screened patio (Florida Room) and spacious backyard. The gated fence opens extra wide for boat, RV or your trailer entry. This entry is very convenient to back any trailer size. For outdoor activities, you just step out of the house and go on a Cady Way Trail for biking, skating, and walking activities. For tennis lovers there are very well kept tennis courts where sport enthusiasts practice their skills in pickleball. Right next to the tennis courts is a playground that offers cozy shaded areas with slopes, swings, and climbing walls. Publix, Costco, Walmart and the post office are all located nearby. For evening promenade the downtown Winter Park, located just a few miles away, offers unique restaurants, cozy coffee shops and bars. To see this amazing 3 bedroom home for sale in Winter Park, call today and schedule a showing! NOTE: Roof - July 2023. HVAC - 2015. No HOA, NO CDD.

346 S Ranger Boulevard, Winter Park

$142,500
1 Beds 1 Baths Parkview Village SubDv. 32792 Zip Code
PRICE IMPROVEMENT!! What better value! Accepting offers. Clean, Crisp and Fresh! Welcome home! NEWLY RENOVATED BATHROOM on deck. Is Winter Park your destination or desire? Investment Potential, Student Sanctuary or just a long-awaited life. Centrally located at your fingertips. Location, Lifestyle, Luxurious Zip Code, Friends, Culture and Community. Discover an unparalleled opportunity to own a piece of prime real estate in the heart of Winter Park, Florida. This beautifully appointed condo apartment is located within a vibrant, amenity-rich HOA community offering a perfect blend of convenience and value. Whether you're a first-time buyer, a savvy investor seeking strong rental return, a student prioritizing location and community or a loving and supportive parent wanting to be closer to your excelling child, this unit checks every box, all at an exceptional, reasonable price point. The very best luxury boutiques, fine dining, sidewalk cafes, and vibrant art festivals. Instant access to top tier schools and hospitals. Directly across from Full Sail University, minutes to Rollins College, UCF, Valencia College and major medical centers like AdventHealth and Orlando Health facilities, making it ideal for any resident, and or faculty. Transportation is easily accessible to Downtown Orlando where the famous Lake Eola Park is, Winter Springs, Oviedo, The Orlando International Airport, Cady Way Trail, biking, hiking, swimming, volleyball, pickleball, tennis and painting at The Crealde School of Art. There's just so much within reach. Explore local gatherings, social events and community connections. For all investors, strong rental income potential and appreciation value. There's low maintenance and worry-free ownership opportunities. Let's build a portfolio together or get you owning immediately. Let's get your private tour scheduled.

3019 Antique Oaks Circle Unit 124, Winter Park

$399,900
4 Beds 2 Baths Eastbrook Sub Unit 05 SubDv. 32792 Zip Code
This beautifully renovated Winter Park home feels warm, inviting, and easy to love. Bright natural light highlights a brand-new kitchen with modern appliances, a waterfall countertop, and soft wood finishes. Both bathrooms have been transformed with elegant marble look tile and spa style showers. You’ll fall in love with the large private backyard, perfect for summer barbecues, outdoor entertaining, play space, or even adding your own backyard oasis. All of this with no HOA and close to top rated Winter Park schools, popular dining, shopping, and parks. This move-in ready home offers lifestyle, comfort, and value you have to see in person, so schedule your showing today before it’s gone!

1849 Viburnum Lane, Winter Park