Winter Park Homes For Sale & Real Estate - 416 homes

Remarks: Charming Downtown Winter Park Pied-à-Terre – Steps from Park Avenue! Welcome to Whispering Waters, a beautifully maintained mid-century community nestled on the shores of Lake Osceola. This light-filled corner studio offers a rare opportunity to own a piece of Winter Park’s most coveted location—just steps from Park Avenue, Central Park, and all the cultural charm the city has to offer. Located on the second floor, this spacious studio boasts an updated kitchenette, generous storage, and abundant natural light. Enjoy secure garage access, mail and package delivery to your door, and a relaxing retreat with sunrise views, osprey sightings, and even rocket launches visible from the community patios. Community Amenities: Sparkling pool, Club room for social gatherings, Peaceful outdoor patios overlooking Lake Osceola and Professional on-site management. Location Highlights include being one block to Park Avenue’s boutiques, cafes, and fine dining. Close to The Alfond Inn, museums, and galleries. Walkable to SunRail & Amtrak station. Moments from the Winter Park Farmers’ Market. This is a rare opportunity to own a stylish, low-maintenance home in the heart of downtown Winter Park where ELECTRIC, GAS, WATER, SEWER and TRASH are included in condo fee. Whether you're looking for a weekend retreat or full-time residence, this pied-à-terre is truly one-of-a-kind. Call today for your private viewing of this condo.

Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)

Listing Agent: Mary Colton (407-222-7388)

Remarks: Quiet Living in the Desirable Lazy Oaks Community of Winter Park. Welcome to the peaceful, well-established community of Lazy Oaks in highly sought-after Winter Park. This hidden gem offers beautifully landscaped grounds, meticulous maintenance, and the added benefit of a low HOA. This lovingly maintained 2-bedroom, 2-bath home features a spacious, thoughtfully designed floor plan with an attached garage. The home is ideally located near top-rated schools, shopping, dining, and provides convenient access to major highways. Inside, you’ll find a neutral color palette complemented by ceramic tile and wood laminate flooring throughout. The efficient kitchen boasts gleaming white countertops, rich wood cabinetry, and a large pantry for ample storage. The expansive great room offers flexible space for both dining and living areas, complete with a cozy wood-burning fireplace—perfect for relaxing or entertaining. Sliding glass doors open to a large, screened private lanai, ideal for morning coffee or evening unwinding. The spacious primary suite features an en suite bath with dual sinks, a large vanity, walk-in shower, and a generous closet. A split-bedroom layout provides added privacy, with a secondary bedroom and additional full bath. Additional highlight: HVAC replaced in 2021. Don’t miss this opportunity to make your home in one of Winter Park’s most charming and convenient communities!

Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)

Listing Agent: Mindy Machock (407-461-1866)

Remarks: Welcome to 1562 Arbor Park Drive, a beautifully maintained four-bedroom, two-and-a-half-bath residence tucked along a charming brick street in the heart of Winter Park. This move-in-ready home combines elevated finishes, abundant natural light, a flexible split-bedroom floor plan, and an exceptional location near the shopping, dining, and cultural attractions that make Winter Park one of Central Florida’s most desirable communities. At the center of the home is a completely redesigned kitchen that is both stylish and highly functional. New cabinetry, quartz countertops, stainless steel appliances, generous storage, and an oversized island with bar seating create an inviting setting for everyday meals and entertaining. A beautiful picture window frames views of the lush backyard and fills the kitchen with natural light. The open living spaces flow seamlessly together over wood-look tile flooring, while fresh interior paint, updated fixtures, and an electric fireplace add warmth and a polished contemporary feel. Privately positioned on one side of the home, the expansive primary suite feels like a retreat of its own. The suite includes a custom designed walk-in closet and a beautifully designed bathroom with separate vanities, a freestanding soaking tub, an oversized walk-in shower, and a private water closet. Three additional bedrooms are located on the opposite side of the home, providing separation and flexibility for family members or overnight guests. The outdoor setting is equally impressive. The enormous, fully fenced backyard has been lovingly maintained and features mature greenery, privacy, and plenty of room for entertaining, recreation, gardening, pets, or a future outdoor living retreat. Bonus: there is additional parking on the west side of the home that is accessible from the backyard - perfect for hosting or entertaining! A cobblestone driveway enhances the home’s curb appeal, while notable improvements include replacement of the HVAC system and ductwork in 2016, numerous plumbing updates, and extensive interior renovations. Enjoy a location that places the best of Winter Park within easy reach. The home is conveniently located near the Winter Park YMCA, Lakemont Elementary School, Phelps Park, Rollins College, and the Winter Park Chain of Lakes -  not to mention all of the boutiques, restaurants, museums, & cafés, and community events of historic Park Avenue. Baldwin Park, Winter Park Village, and Audubon Park are also just minutes away, offering even more options for dining, shopping, entertainment, and outdoor recreation. This is an exceptional opportunity to enjoy a gorgeous, fully updated home in the highly desirable in-town Winter Park address. Schedule your private showing and experience the lifestyle, location, and thoughtful design of 1562 Arbor Park Drive.

Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)

Listing Agent: Abby Greenberg (407-484-2689)

Remarks: Discover the potential of this 2-bedroom, 2-bath end-unit condominium located in the desirable Wrenwood Condominium community in Winter Park, Florida. Offering 1,058 square feet of living space, this home presents an excellent opportunity for buyers seeking affordability, convenience, and the chance to add their own personal style. Inside, you'll find ceramic tile flooring throughout, knockdown ceilings, and a functional floor plan designed for comfortable everyday living. All kitchen appliances are included, making your transition even easier. The end-unit location provides additional privacy and natural light while offering pleasant views of the community pool. Built with solid concrete block construction, this condominium offers durability and low-maintenance ownership. The bathrooms could benefit from updating, providing the perfect opportunity for the next owner to customize the home to their own taste and preferences. Whether you're a first-time homebuyer, downsizing, looking for a seasonal residence, or seeking an investment property, this home offers tremendous potential and value. Wrenwood Condominium allows up to two pets, with a maximum weight of 25 pounds each, making it a great option for pet lovers. Conveniently located near shopping, dining, entertainment, major highways, and everything Winter Park and the greater Orlando area have to offer. Don't miss this opportunity to own an affordable Winter Park condominium and create the home you've always envisioned.

Listing is courtesy of: HOME BUYER HELPER REAL ESTATE LLC (407-342-2664)

Listing Agent: Ada Sanchez (407-342-2664)

Remarks: Discover a unique opportunity in the heart of Winter Park, just moments from Lake Killarney. This versatile property offers exceptional potential for multigenerational living, a primary residence with additional income, or a strategic investment. The home features a flexible layout designed to adapt to a variety of needs, with bright living spaces, natural light throughout, and comfortable areas ideal for both everyday living and entertaining. Its design allows for privacy and functionality, making it an attractive option for homeowners and investors alike. Enjoy a spacious outdoor setting surrounded by mature landscaping, perfect for relaxing or hosting gatherings. Recent upgrades add even more value and peace of mind, including solar panels that will be fully paid off at closing, as well as a newer roof and updated air conditioning system, offering efficiency and long-term savings. Ideally located just minutes from Park Avenue, Rollins College, and a wide variety of shopping, dining, and entertainment options. With easy access to major roadways, commuting throughout Central Florida is both quick and convenient. A rare opportunity to own a property with flexibility, location, and strong long-term value in one of the area’s most desirable communities. Schedule your private showing today.

Listing is courtesy of: AROD PARTNERS REALTY (407-627-7621)

Listing Agent: Suheil Flores (407-693-3060)

Remarks: On a picturesque brick street in Winter Park, this beautifully designed modern traditional pool home blends timeless architecture with thoughtful, high-end finishes throughout. Built in 2015 and offering over 3,100 square feet, the home features four bedrooms, three full baths, and a flexible three-story layout designed for everyday living and effortless entertaining. A welcoming front porch leads into a bright foyer highlighted by custom millwork and warm wood flooring, setting the tone for the home’s clean, curated style. The open-concept main living space flows seamlessly from the dining area into a spacious family room and a chef’s kitchen designed to impress. Anchored by a generous marble island with seating, the kitchen features Viking stainless steel appliances, a gas cooktop, honed granite perimeter countertops, custom cabinetry with upper and under-cabinet lighting, and stylish tile backsplash. A wet bar with wine refrigerator adds to the home’s entertaining appeal. The first floor also includes a versatile office or playroom with custom built-ins, a functional mudroom/drop zone and abundant storage throughout. Upstairs, the primary suite offers a peaceful retreat with natural light and a spa-inspired bath featuring dual vanities, a soaking tub and a glass-enclosed shower. Secondary bedrooms are well-sized and thoughtfully designed, while the third-floor bonus suite with full bath provides ideal space for guests, a home office or additional living. Outdoor living is equally inviting, with a covered back porch equipped with remote-controlled phantom screens overlooking a private, professionally landscaped yard with artificial turf and a low-maintenance pool, ideal for year-round enjoyment. Additional features include two HVAC systems with Nest thermostats, hardwood flooring on the main level, and designer finishes throughout. Zoned for sought-after schools including Dommerich Elementary, Maitland Middle and Winter Park High. This is a rare opportunity to own a move-in ready home that balances style, function and location in one of Winter Park’s desirable settings.

Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)

Listing Agent: Audra Wilks (407-252-8582)

Remarks: Virtually Staged. Conveniently located just minutes from I-4, downtown Orlando, and Winter Park, this versatile home offers the perfect blend of comfort, flexibility, and location. The upper level features two bedrooms and one full bath, while the lower level includes one bedroom and one full bath. Each floor has its own private entrance and full kitchen, making it ideal for multi-generational living, rental income, a guest suite, or added privacy. Situated on a beautiful, tree-lined dead-end street, the property offers a peaceful setting while remaining close to shopping, dining, and entertainment. Inside, you'll find contemporary fixtures, stylish finishes, updated appliances, and an abundance of natural light throughout. The spacious backyard and inviting seating area provide the perfect space to relax or entertain family and friends. Major updates include a recently replaced roof, HVAC system, and electrical panel, offering added peace of mind. Some photos have been virtually staged to help showcase the home's layout and potential.

Listing is courtesy of: SIMPLE FEE LISTINGS LLC (734-674-6608)

Listing Agent: Randall Wolber, Jr (734-674-6608)

Remarks: Nestled within the gated community of Hawks Crest, this meticulously maintained two-story residence showcases over $70,000 in luxurious builder upgrades, blending timeless design, modern comfort, and effortless Florida Living. This stunning home presents an exceptional opportunity to enjoy one of Winter Park's most desirable lifestyle communities. A welcoming entry opens to light-filled interiors where soaring ceilings, elegant finishes and a thoughtfully designed open-concept floor plan create a seamless flow throughout the home. Luxurious white ceramic tile spans the entire first floor, enhancing the home's bright and airy feel while providing both beauty and durability. The gourmet kitchen serves as the centerpiece of the home, featuring upgraded cabinetry, quartz countertops, stainless steel appliances, abundant storage and an expansive peninsula with bar seating. Spacious living areas and generously sized bedrooms provide comfort and flexibility for a variety of lifestyles. Upstairs, plush carpeting creates a warm and inviting retreat, while the primary suite offers a private sanctuary complete with a large walk-in closet and a spa-inspired bath. Additional bedrooms provide ample space for family, guests, a home office or a fitness room. Sliding glass doors extend the living space to a covered lanai, creating an inviting setting for outdoor dining, morning coffee or relaxed evenings enjoying Florida's year-round climate. Residents of Hawks Crest enjoy an exceptional collection of resort-style amenities, including a clubhouse, state-of-the-art fitness center, community pool, playgrounds, dog park, scenic trails and private access to Lake Howell. The community is also conveniently located near local favorites, including Kelly's Ice Cream, Foxtail Coffee and Park Maitland Preschool. Ideally situated just minutes from Park Avenue, downtown Maitland, major highways, and top-rated schools, this exceptional home offers effortless access to Central Florida's finest shopping, dining and cultural attractions. Despite its convenient location, the community maintains a sense of privacy and tranquility.

Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)

Listing Agent: Harif Hazera Llc (407-953-9098)

Remarks: Virtually Staged. Welcome to this virtually staged contemporary townhome in the desirable 400 West community, home to just nine residences and steps away from lively Park Avenue. Enter through the private garage or the charming front path, and you'll find a bright and open main floor that perfectly balances comfort and modern style. The main floor features a stylish mix of finishes, including large-format porcelain tiles, level 4 drywall, tall baseboards, and designer lighting. The centerpiece is a sleek kitchen equipped with glossy white cabinetry, chic chrome pulls, quartz countertops, and top-quality stainless-steel appliances. The garage, with alley access, includes a storage closet and built-in shelving for added convenience. On the second level, discover two spacious primary suites with modern LVP flooring and large windows that let in plenty of natural light. The en-suite bathrooms are designed with porcelain tiles, frameless glass showers, wall-to-wall mirrors, and matte white vanities. The primary bath offers a double-sink vanity, a private water closet, and a spacious walk-in closet. A conveniently situated laundry room features a Samsung washer and dryer with overhead storage. The third level has two more bedrooms, each with walk-in closets, connected by a shared Jack-and-Jill bath, making it ideal for guests, a home office, or a workout space. Don’t miss the chance to check out this fantastic home in a prime location where luxury meets practicality!

Listing is courtesy of: RE/MAX EXCLUSIVE COLLECTION (407-447-2829)

Listing Agent: Kim Griffin (407-314-5033)

Remarks: Nested on a spacious, tree lined lot just steps from Lake Killarney, 2361 Roxbury Road offers a rare opportunity to create your dream home in one of Winter Park’s most convenient locations. Ideally situated just off Fairbanks Avenue with quick access to I-4 , this 3 bedroom, 2 bath residence features 1723 square feet of living space, solid plaster walls and mid century character. Built in 1951, the home showcases an original pine paneled ceiling in the living room, adding warmth and architectural charm. Two large, new Anderson windows fill the room with natural light and highlight the pool view. New Anderson exterior doors improve the homes security and efficiency. The expansive Florida room provides flexible space for entertaining or future updates. Major improvements include a resurfaced Gunite pool in pebble finish (2024), exterior paint (2024), new paver driveway (2024), roof (2020) and HVAC system (2019). The garage has been enclosed and currently serves as storage and utility space. Outside you’ll find a fully fenced backyard with plenty of room to enjoy the Florida lifestyle. Located on a large lot with sidewalks and mature trees, this home presents an excellent opportunity for buyers looking to personalize a property in a desirable Winter Park location. The septic system was pumped in 2026, providing peace of mind. Bring vision and make this home your own!

Listing is courtesy of: ANNE ROGERS REALTY GROUP INC (407-649-4141)

Listing Agent: Arden Magee (407-276-1698)

Remarks: 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!

Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)

Listing Agent: Vonda Fields (321-438-6906)

Remarks: One or more photo(s) has been virtually staged. **This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buy-down that reduces the buyer's interest rate and monthly payment.** This luxurious Modern Style home epitomizes maintenance-free living, featuring a premium, state of the art solar system YOU OWN OUTRIGHT, nearly eliminating your cost of electricity. Ask to see the bill. The premium solar system is PAID OFF with a TRANSFERABLE WARRANTY by manufacturer. This off-grid solar system comes with a WHOLE HOUSE BATTERY BACKUP, keeping your lights on when the power goes out. This home already comes wired for electric vehicles with room to expand. Excess power generated is sold back to the power company through the NET METERING program, resulting in credits back to the owners at the end of the year. The solar system also has two power monitoring systems for tracking your energy usage & production, conveniently controlled by your phone and computer. Hawks Crest is your home to community, where residents enjoy gated access into a landscaped resort atmosphere, featuring water fountains throughout, with an abundance of amenities. The clubhouse features a resort pool & kiddie pool, a fitness center, with sidewalks & playgrounds, along with the community’s private dock access to Lake Howell with a canoe/kayak launch. Now imagine, relaxing and enjoying park and pond views from your expansive lanai, soaking in the serene sunsets & manicured landscaping, all from the comfort of your spacious, 4-bedroom 3.5 bath home, including a loft upstairs, all conveniently located just a short distance from the resort clubhouse. Owners can relax and unwind while management handles all landscaping around your home, truly providing you a maintenance-free living lifestyle. Additional upgrades with this home include, commercial grade luxurious vinyl wide-plank flooring, two power monitoring systems, a whole-house water softener & filter system, and two HVAC units, all designed for comfort, convenience, and a very clean home, where you can relax. Nestled in this spacious home, you’ll find 20-foot-high ceilings with awe-inspiring views of the illuminated pond fountain, creating a serene view & relaxing atmosphere you’ll enjoy, even from the kitchen sink. Your chandelier can be lowered 20-feet to the floor for easy maintenance & cleaning, using a winch lift system in the attic.(Rated up to 200 lbs). And even watch the rockets launch at The Cape from the front yard. Uniquely designed, this home was built to withstand extreme weather, featuring a concrete/granite tile roofing system, steel reinforcement, concrete-filled block walls & slab, all anchoring to the foundation, uniquely tying everything together. Meticulously maintained by the owners, this home comes with a complete set of blueprints, along with many photos & videos taken of the home during the building process. Owners even have documents for all equipment & appliances. And the premium solar system comes with a transferable warranty that will keep the lights on when the power is out. This home features a split floor-plan, with a primary bedroom on both the first and second floors. Spanning 2,589 sq.ft., this home offers an additional 540 sq.ft. of screened-in lanai, providing a private outdoor oasis where you’ll find owners enjoying the tranquility of Florida sunsets. Schedule a showing for your buyers today! And…***Remember to see the list of the owners’ upgrades***.

Listing is courtesy of: BHHS FLORIDA REALTY (352-729-7325)

Listing Agent: Rod Chevalier (352-729-1818)

Remarks: Charming Pool Home in Prime Winter Park Location Welcome to 2758 Banchory Road — a true gem nestled in the heart of the desirable Winter Park Pines community. This beautifully maintained 3-bedroom, 2-bath ranch-style home offers the ideal combination of comfort, privacy, and location. With a private swimming pool, lush landscaping, and no direct front neighbors on a quiet cul-de-sac street, this home is perfect for families or anyone seeking tranquility just minutes from city conveniences. Property Highlights Spacious backyard featuring a private pool—perfect for Florida living and entertaining. Fully fenced yard with a storage shed and dedicated area for pets or gardening. Open-concept layout with natural light, mature trees, and charming curb appeal. Located steps from the Cady Way Trail, ideal for biking, jogging, or weekend strolls. Unbeatable Location Just minutes to Downtown Winter Park with boutiques, restaurants, Rollins College, and Park Avenue. Close to Winter Pines Golf Club, Cady Way Park, and public tennis courts. Easy access to Baldwin Park, Full Sail University, Advent Health Winter Park, and the 417 expressway. Top-Rated School Zone Located within the Orange County Public Schools district, this home is zoned for: Aloma Elementary School (PK–5) ~ 0.7 miles Glenridge Middle School (6–8) ~ 1.6 miles Winter Park High School (9–12) ~ 0.6 miles Highly rated with International Baccalaureate (IB) and Advanced Placement (AP) programs Private schools nearby include Trinity Prep, Geneva School, Chesterton Academy, and St. Margaret Mary K–8. Why You’ll Love It Relax and entertain year-round with your private pool and covered patio. Walkable to trails and parks, bikeable to schools, and 10 minutes to Park Avenue. Family-friendly neighborhood with strong community feel and no HOA. A rare combination of location, schools, and lifestyle opportunities. “Solar panel debt is $70k and must be assumed by Buyer". Whether you’re relocating, downsizing, or looking for the perfect place to raise a family, this Winter Park beauty has it all. Schedule your private tour today!

Listing is courtesy of: MR VARGAS PROPERTY MANAGEMENT LLC (407-557-2150)

Listing Agent: Erwin Vargas (407-338-3382)

Remarks: New Price! This beautifully updated 2-story condo offers the perfect blend of style and affordability. Featuring a fresh kitchen, renovated bathroom, and new flooring throughout, this move-in-ready home includes an in-unit washer/dryer for ultimate convenience. As a desirable end unit, you’ll enjoy extra privacy and a peaceful view of the adjacent conservation area. Relax on your private patio, complete with additional outdoor storage. Bonus: Your HOA dues cover water and trash service! This Winter Park steal won’t last—schedule your showing today.

Listing is courtesy of: BUSBY REALTY LLC (407-529-6952)

Listing Agent: Chad Busby (407-529-6952)

Remarks: Now offered out an exceptional new price, the seller has thoughtfully repositioned this home to encourage serious buyer interest – seller is actively moving. This remarkable home represents one of the best opportunities in today’s Winter Park luxury market, featuring exquisite finishes, modern design, and an unmatched lifestyle just moments from Park Avenue. Built in 2018, this custom-designed 4-bedroom, 3.5-bath residence offers 2,843 square feet of thoughtfully crafted living space, just a short walk from Park Avenue and the historic Winter Park Golf Course. Distinctive architectural details—including shiplap ceilings in the living room and kitchen, decorative ceiling treatments, and a dramatic tile staircase feature illuminated by natural light—create a home that is both elegant and inviting. At the heart of the home is a chef-inspired kitchen featuring Wolf and Sub-Zero appliances, custom cabinetry, Kohler fixtures, and an open-concept layout that flows effortlessly into the living and dining spaces, making it ideal for everyday living and entertaining alike. The primary suite serves as a peaceful retreat with a spa-inspired marble bathroom, while the upstairs bonus room offers flexible space for a media room, home office, or playroom. Outside, enjoy your own backyard oasis complete with a sparkling pool and spa combo—perfect for relaxing or hosting family and friends. Located just minutes from Park Avenue’s renowned restaurants, boutiques, and year-round events, this home delivers one of Central Florida’s most sought-after lifestyles. Schedule your private showing today.

Listing is courtesy of: FLORIDA CAPITAL REALTY (786-953-5870)

Listing Agent: Jacob Theisen (407-908-1735)

Remarks: Under contract-accepting backup offers. BACK ON MARKET. Picture yourself unwinding in your private 0.41-acre yard, taking a dip in the pool, flipping through a good book, or hosting friends on a sunny afternoon. From there, stroll over to the Winter Park Racquet Club for tennis, pickleball, or lunch (kids are covered—there’s a sidewalk the whole way), or head to the deeded lake access launch for a day of kayaking on the Winter Park Chain of Lakes. Welcome to 2299 Via Tuscany, an opportunity priced 4-bedroom, 3.5-bath home to get into the coveted Winter Park Vias while adding your final touches to personalize this home while prioritizing location, schools, privacy and connectivity. With 3,986 square feet on a 0.40-acre lot, it offers the perfect blend of luxury and comfort, featuring a super spacious kitchen, a new architectural shingle roof (2023), Pebble Tec-style pool finish, and lush landscaping. Inside, enjoy solid hardwood and modern tile floors, soaring ceilings, and two wood-burning fireplaces. The chef’s kitchen shines with SubZero refrigeration and a Viking 6-burner gas cooktop. The main floor offers a private primary suite, a guest suite, and a study/library with built-ins, while upstairs you’ll find two more bedrooms and a full bath. Modern perks include zoned A/C, a new EV charger, and epoxy-coated floors in the 2-car garage. Close to parks, the Racquet Club, and downtown Winter Park’s shops, dining, and culture, this home suits families and active lifestyles alike. Deeded lake access through the Maitland Shores Lakefront Preservation Association gives you a private ramp for kayaks, canoes, and more, plus easy access to schools, trails, and green spaces—a perfect mix of charm, amenities, and location.

Listing is courtesy of: CORCORAN PREMIER REALTY (407-965-1155)

Listing Agent: Vincent Scarlatos (407-718-2378)

Remarks: Discover this well maintained 3 bedroom, 2 bathroom home offering 1,676 sq ft of comfortable living space. The home features a spacious layout with inviting living and dining areas that flow seamlessly into the kitchen, creating a great setup for everyday living and entertaining. The primary suite includes a private bathroom and generous closet space, while the additional bedrooms provide flexibility for family, guests, or a home office. Step outside to your own private backyard retreat featuring a pool and fully fenced yard, perfect for relaxing, entertaining, and enjoying the Florida lifestyle. Located in a quiet residential neighborhood, this move-in ready home is easy to show and ready for its next owner.

Listing is courtesy of: SOVEREIGN REAL ESTATE GROUP (305-662-1502)

Listing Agent: Raul Pino (305-662-1502)

Remarks: Under contract-accepting backup offers. Tucked away on a quiet dead-end street just off Lake Killarney, this solid block 1960's ranch at 2611 Lotafun Avenue offers over 1,800 SF of living space with room to make it your own. Featuring 3 bedrooms and 2 full baths, this home boasts a charming front living room with a wood-burning fireplace, PLUS a spacious family room/sunroom with its own fireplace — perfect for cozy nights or entertaining. The primary bedroom features an en suite bath, while the hall bath charms with original tilework. Step outside to your private pool, set on a generous 0.24-acre lot with a backyard shed for extra storage. Additional highlights include an attached 2-car garage with bonus storage room, interior laundry, and a 2022 roof. All new electrical was just installed in June 2026 by Skolfield Homes, giving buyers peace of mind on one of the big-ticket items. Enjoy the tranquility of this established neighborhood while staying close to major roadways, shopping, and dining. Homes with this much character and potential in Winter Park don't come around often — bring your vision and make this one shine!

Listing is courtesy of: KELLY PRICE & COMPANY LLC (407-645-4321)

Listing Agent: Kelly Price (407-645-4321)

Remarks: Rare Waterfront Opportunity in Winter Park! Discover your own slice of Florida paradise with this waterfront gem offering 94 feet of direct canal frontage on Lake Bell for under $600,000. Tucked away in a peaceful, private setting, yet just minutes from Winter Park’s famed Park Ave, Winter Park Village, College Park and Downtown Orlando with numerous shopping and dining options making this property the perfect blend of seclusion and convenience. Built in 1957, this classic Florida ranch features 3 bedrooms and 2 bathrooms within 1,837 SF of living space. Major updates include a new roof in 2024 and HVAC in 2019. Step inside off the covered front porch to find spacious living and dining areas highlighted by charming built-in features and abundant natural light. At the heart of the home, the kitchen offers easy access to a generous walk-in pantry/utility room/laundry area. The adjoining family room opens to a covered back porch overlooking the expansive backyard and tranquil canal. Situated on a .40-acre lot, the property extends beyond the canal, creating a natural wooded buffer that enhances privacy and provides a serene backdrop. Whether you envision a pool, outdoor kitchen, garden, or entertaining space, the backyard offers endless possibilities to create your dream outdoor oasis (subject to municipal review and approvals). Lake Bell is a 36-acre spring-fed ski lake with an average depth of 12 feet, ideal for boating, skiing, kayaking, paddle boarding and enjoying the Florida lifestyle. Fishing enthusiasts will also appreciate the lake’s reputation for largemouth bass and bluegill. Other notable exterior highlights include fenced in backyard, covered front entry, two rear porches and 1-car carport. The home is on septic that has been well maintained and serviced annually. The location also offers quick access to Interstate 4 and close proximity to area hospitals, parks and cultural centers. Don’t miss this exceptional opportunity to own waterfront property in Winter Park/3789 at an incredible value!

Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)

Listing Agent: Bryan Douglas (407-492-6740)

Remarks: Under contract-accepting backup offers. Welcome home to carefree lakefront living in the heart of Winter Park, where everyday life is complemented by breathtaking sunsets over beautiful Lake Killarney and one of Central Florida's most walkable locations. Nestled within the Chateaux Du Lac lakefront community, this beautifully updated second-floor condominium offers 2 bedrooms, 2 bathrooms, and an inviting open floor plan designed for comfortable everyday living. Stepping inside, plantation shutters throughout the home create a timeless look while allowing natural light to fill the space. The spacious living and dining areas flow seamlessly together, making entertaining both easy and enjoyable. The updated kitchen is sure to impress with quartz countertops, a center island, modern subway tile backsplash, stainless steel appliances, and recessed lighting that completes the contemporary design. The owner's suite provides a relaxing retreat complete with an updated ensuite bathroom featuring stunning floor-to-ceiling herringbone-style subway tile, an overhead rain showerhead, and modern finishes. The guest bedroom is generously sized and offers a large walk-in closet, while the second bathroom has been beautifully updated to match with the same designer tilework and rain showerhead. Sliding glass doors lead out to your private balcony, creating the perfect place to enjoy your morning coffee or unwind in the evening after a day on the lake. A brand-new water heater installed in 2026 provides added peace of mind. Residents of Chateaux Du Lac enjoy an exceptional lakefront lifestyle with access to a heated swimming pool, clubhouse, community deck overlooking Lake Killarney, private boat ramp, BBQ grilling area, saunas, kayak and paddleboard storage, and updated on-site laundry facilities. Whether you enjoy boating, skiing, paddleboarding, fishing, or simply taking in spectacular sunset views, this amenity-rich community offers everything you need to embrace the Florida lifestyle. Perfectly positioned just moments from Park Avenue, you'll enjoy easy access to locally owned restaurants, boutique shopping, cafés, Trader Joe's, the Winter Park Village, movie theater, farmers markets, and the nationally recognized Winter Park Sidewalk Art Festival. With convenient access to I-4, commuting throughout the Orlando area is effortless while still enjoying the charm and elegance that make Winter Park one of the area's most desirable communities. Schedule your showing today!

Listing is courtesy of: MAVREALTY (727-314-3942)

Listing Agent: Robert Kirkwood, Iv (321-297-6489)