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$228,000
1 Beds ⋅ 1 Baths ⋅ Karolina On Killarney SubDv. ⋅ 32789 Zip Code
This cozy 1-bedroom, 1-bath bungalow is your ticket into one of Winter Park’s most desirable neighborhoods—just steps from beautiful Lake Killarney and surrounded by some of the city’s best dining, shopping, and entertainment. Whether you’re looking for a charming personal retreat, a smart investment, or a renovation project with serious upside, this property delivers with its unbeatable location and potential. Sitting on one of the larger lots on the street and with no HOA to restrict your vision. What makes this opportunity truly special is the walkable lifestyle—Trader Joe’s, Winter Park Village, Park Avenue, Dubsdread Golf Course, and a full menu of local restaurants and shops are all just minutes away. Quick access to I-4 puts downtown Orlando, nearby attractions, and work commutes easily within reach, yet you’re tucked away in a serene, scenic pocket of town where lake breezes and neighborhood charm still reign. Homes in this area are rarely available at this price, making it a golden chance to get into a sought-after location and bring your dream renovation to life. Don’t miss the opportunity to own a slice of Winter Park with character, convenience, and curb appeal just waiting to be unlocked. Please allow up to 72 hours for a response. DO NOT SUBMIT OFFERS SITE UNSEEN!

1979 Staunton Avenue, Winter Park
$965,000
3 Beds ⋅ 4 Baths ⋅ Mondrian/Winter Park Twnhms SubDv. ⋅ 32789 Zip Code
Don’t miss out on the final new construction unit available - act fast! Discover unparalleled luxury at Mondrian Winter Park, where contemporary design meets the tranquil beauty of Lake Killarney. We are excited to share that this is the LAST corner unit of a highly coveted floor plan in our exclusive community of just 30 modern townhomes along the serene shoreline. Each residence features exquisite finishes, stunning storefront-style windows, and soaring ceilings just shy of 11 feet, allowing natural light to fill the interiors. This brand-new townhome combines contemporary aesthetics with charming brownstone elements, showcasing a unique layout designed for convenience and privacy. The main living space is beautifully situated on the second level, allowing for a seamless flow between the modern kitchen, dining room, and great room. Retreat to the stylish primary bedroom located at the back of the home, where you’ll find a spa-inspired bathroom complete with two walk-in closets, a cozy sitting area, designer tile, a frameless glass shower, and a private water closet—all thoughtfully crafted for ultimate comfort. Our smart split bedroom design includes two additional bedrooms with en suites on the first level, delivering ample space and flexibility for your lifestyle. A full-size laundry room adds to the functionality and elegance of your new home. Step onto the rooftop oasis featuring an outdoor kitchen, a pergola, a hot tub spa, and breathtaking open sky views, creating the perfect setting for relaxation and entertainment. Nestled in picturesque Winter Park, just north of downtown Orlando, residents can enjoy lakeside living with access to a private boat slip, community kayaks, and a beautiful lakefront pavilion. Whether you’re in search of serene relaxation or vibrant entertainment, this prime location offers proximity to top-tier dining, shopping, and recreational amenities for a lifestyle of unmatched convenience and luxury. Seize this incredible opportunity before it’s gone—your dream home on Lake Killarney awaits!

1760 Mondrian Circle, Winter Park
$325,000
3 Beds ⋅ 3 Baths ⋅ Winter Park Gardens Condo SubDv. ⋅ 32789 Zip Code
CLICK ON VIRTUAL TOUR to get an overview of the complex. HUGE PRICE REDUCTION!!!!......Discover a RARE opportunity to own a 3 BEDROOM 2.5 BATH unit at beautiful Winter Park Gardens. One of only seven 3 BEDROOM units so infrequently available. Located on the second floor. Enjoy stunning floor to ceiling views of lush landscaping, walking paths, pond, and the expansive 8.1-acre gardens in your tropical sunroom. Located in a vibrant 55+ community that welcomes younger owners, this prime location is within walking distance of Rollins College, Orange Ave, Mead Gardens, and downtown Park Ave. Don’t miss out on the serene, sought-after lifestyle Winter Park Gardens offers—call today to make it yours!

700 Melrose Ave Unit C22, Winter Park
$800,000
3 Beds ⋅ 4 Baths ⋅ Lake Knowles Terrace Add 02 SubDv. ⋅ 32789 Zip Code
Fantastic Lake Knowles Terrace community close to The Via's, Downtown Winter Park and I-4 road access. Lots of possibilities to restore this 1940 classic home or create your own brand new structure . This property offers so much potential in Winter Park's premier and sought after location. Call today for your private tour !!

1823 Sunset Drive, Winter Park
$675,000
2 Beds ⋅ 2 Baths ⋅ Lake Knowles Terrace SubDv. ⋅ 32789 Zip Code
Attention builders and investors! Here’s your chance to own a prime property in the coveted Tree Streets of Winter Park, one of Central Florida’s most desirable neighborhoods. Whether you’re looking for immediate rental income or planning to build your dream home in the future, this opportunity is not to be missed! Tucked away just minutes from Phelps Park, the Winter Park YMCA, Lake Knowles, and top-rated Lakemont Elementary, this home is ideally located for both convenience and lifestyle. Enjoy peaceful neighborhood strolls, bike rides to the boutiques and cafés of Park Avenue, or weekend outings at the Winter Park Farmers’ Market. Living here means being immersed in the charm and culture that makes Winter Park so special—historic homes, scenic lakes, a vibrant arts scene, and a strong sense of community. Step inside to find a well-maintained home full of character. Original hardwood floors bring warmth and timeless appeal to the living areas and bedrooms. A versatile bonus room offers endless possibilities—use it as a home office, playroom, gym, or cozy den. Outside, the backyard is made for Florida living, with a screened-in patio perfect for al fresco dining and a spacious yard ideal for gardening, entertaining, or weekend fun. Whether you're investing, living in, or planning to build new, this property offers exceptional potential in a premier location. Don’t miss your chance to become part of the Winter Park lifestyle!

1511 Chestnut Avenue, Winter Park
$530,000
2 Beds ⋅ 1 Baths ⋅ Winter Park Village SubDv. ⋅ 32789 Zip Code
Investor / Builder special!! Prime land opportunity located just minutes from Park Avenue. Don't miss your chance to build your custom home in this highly desirable area, surrounded by multi-million dollar homes. Value is in the land. Schedule your showing today!

2525 Lafayette Avenue, Winter Park
$850,000
3 Beds ⋅ 3 Baths ⋅ Charmont SubDv. ⋅ 32789 Zip Code
The true value of this property lies in its expansive 10,675 sq ft lot, nestled among multi-million dollar homes. Whether you're looking to build your dream home or expand upon the existing structure, this is a rare opportunity in a highly sought-after location. A full set of building plans are attached to this listing as well as survey. The existing home is a charming 3-bedroom, 3.5-bath residence featuring a beautifully remodeled kitchen with quartz countertops and new cabinetry. Refinished wood floors run through much of the home, complementing the open floor plan and enhancing its timeless appeal. Recent upgrades include new windows and doors throughout, and a roof that's just two years old. One of the full baths has also been beautifully renovated. Don’t miss the chance to secure a valuable piece of land in a premier setting with a move-in-ready home full of potential. Seller is related to listing broker. Dining area chandelier does not convey.

251 Glenridge Way, Winter Park
$1,825,000
4 Beds ⋅ 4 Baths ⋅ Woodmere Terrace Rep SubDv. ⋅ 32789 Zip Code
A rare gem in the heart of the Vias – Nestled in one of Winter Park’s most sought-after neighborhoods, this beautifully designed home is the epitome of comfort, luxury, and convenience. Located just minutes from Park Avenue, top-rated schools, and the best dining and shopping in Central Florida, this property offers an unbeatable lifestyle in a truly prime location. Inside, the home impresses with an open-concept first floor that’s tailor-made for entertaining. The seamless flow between the spacious living room, dining area, and chef’s kitchen makes it easy to host gatherings of any size—from intimate dinners to lively celebrations. Natural light pours in through large windows, highlighting designer finishes and a thoughtful floor plan that blends elegance with everyday functionality. With four oversized bedrooms and four full bathrooms, there's ample space for everyone to spread out comfortably. The private office on the main level is perfect for working from home, while upstairs, a versatile loft offers flex space that can be used as a playroom, reading nook, or creative studio. The true showstopper is the expansive theater room, offering endless possibilities—use it as a media lounge, game room, fitness center, or whatever your lifestyle demands. Step outside to your resort-inspired backyard oasis, featuring a sparkling pool and spa, lush, professionally landscaped grounds, and a covered patio that’s perfect for summer BBQs and year-round outdoor living. Whether you're relaxing with family or entertaining guests, this outdoor space delivers the feel of a luxury getaway right at home. Don’t miss your chance to own a home that offers exceptional space, stylish design, and one of the most desirable locations in Winter Park.

1665 Temple Drive, Winter Park
$795,000
4 Beds ⋅ 2 Baths ⋅ Conwill Estates SubDv. ⋅ 32789 Zip Code
MULTIPLE OFFERS RECEIVED. HIGHEST AND BEST DUE BY WEDNESDAY 5PM. Exceptional opportunity to custom build your home in highly desirable Winter Park neighborhood on a beautiful street. Excellent schools, parks, YMCA, shopping, Park Avenue and more nearby. This property is being sold as a teardown.

1773 Walnut Avenue, Winter Park
$1,335,000
3 Beds ⋅ 3 Baths ⋅ Lyman Ave Villas 1 SubDv. ⋅ 32789 Zip Code
Presenting a stunning and fully furnished END UNIT Townhome, one block off Park Ave! This is 1 of only 8 townhomes built in 2014 by David Weekly, and the only one on the market with incredible Florida outdoor living space. This unit is a gem, with the most privacy and largest side yard of all 8. The location is AMAZING, you can see Park Avenue from your front porch! SO many upgrades, you won't need to do a thing but move in and enjoy walking up to your favorite stores, restaurants, and of course the famous Winter Park Farmer's Market on Saturday mornings! Nothing has been overlooked in this gorgeous residence, so let's take a tour! Entering through the solid wood door, you are greeted with beautiful wood floors and custom window shutters. To your left is a bedroom and/or office with an easy access en-suite full bathroom. Down the hall your eye will be drawn to the breathtaking kitchen with an oversized island, high-end 42" white cabinets with a coffee rubbed stain, GE Monogram appliances, including a natural gas range, and a cozy place for your coffee bar! Looking further you will find the large dining area with a gorgeous crystal chandelier with matching pendants lights over the island. The side bar area pulls your eye into the new custom-built backlit wine room under the stairs! The open concept space invites you into the living room with plenty of room for friends and family to gather. Heading up the stairs you will find a custom-built bookcase before entering into the primary suite. There is so much natural light flowing through the windows from the southern and eastern exposure of this cozy corner bedroom. The primary bathroom has double sinks and a private water closet. Next, we come to the custom-built laundry room, with storage cabinets for days! Coming out of the laundry room we find the 3rd bedroom in the home, a quiet room tucked away for children or guests, and this also has a full bathroom including a comfy tub. Now let's head back downstairs and step out to the OVER 1300 SQ FT OF FENCED-IN FRONT AND BACK OUTDOOR LIVING SPACE! The builder definitely took all of your outdoor needs into consideration when designing this space. The covered brick paver patio with an electric screen boasts a built-in summer kitchen with a gas grill, granite countertops, a wet sink, and storage. There is also a mounted TV on the wall to watch your favorite teams play this fall! Out in the yard is recently installed pet-friendly artificial turf and an area for cornhole or Bocce ball, all inside a fully-fenced yard! The 2-car garage behind the home is accessed by a secured gated entrance. The garage floor has been fitted with custom SwissTrax tiles. Up above the garage is a floored and insulated 200 sq foot storage room that is large enough to stand up and walk around in, and this is climate controlled with a new (2023) mini-split AC (no more need for that expensive storage unit for the Christmas decorations)! Other features include interior paint (2024), new carpet and ceiling fans (2024), new SONOS system, new cabinet hardware, an upgraded whole house security system with cameras, a new (2024) tankless on-demand hot water heater, new (2023) LG washer and dryer, and upgraded landscaping with new uplighting and Mexican stones. The HOA fees cover building insurance, landscaping, watering, pest control with termite bond, roof and gate maintenance. This nearly new townhome right next to Park Avenue is more than just a home, it's a lifestyle!

242 W Lyman Avenue, Winter Park
$2,285,000
4 Beds ⋅ 5 Baths ⋅ Kenilworth Shores Sec 02 SubDv. ⋅ 32789 Zip Code
An elegant and well-kept home located in a quiet neighborhood next to Windsong. It combines a cozy interior design with functionality and light-filled open floor plans. Energy-saving features include double-panel windows with Low-E coating, foam-injected block walls, insulated interior walls and floors, tankless water heaters, tile roof, and a paver driveway. The first floor ceilings peak at 12 feet, delivering a voluminous feel to the living areas and primary rooms; while upstairs, an equally impressive height of 10 feet is maintained throughout the second floor, accommodating bedrooms, making them cosy and comfortable retreats. Making the house great for entertaining are two 10' tall disappearing sliding glass walls in the Great Room that connect indoors and outdoors seamlessly. The kitchen includes a Thermador pro stainless steel appliance package enhanced by granite countertops, custom-made & finished cabinets along with an outdoor kitchen on the lanai equipped with a built-in grill & linear fireplace, and a pool with deck and pergola, all contributing towards luxurious alfresco dining. The clever layout of this property consists of both master & guest suites along with study/office space on the first floor, while there are an extra 2 bedroom suites plus a bonus/media room upstairs, enhancing its versatility. This confluence of style makes this home both luxurious as well as eco-friendly. This property brilliantly integrates cosmopolitan living while retaining the warmth of home at every corner.

521 S Phelps Avenue, Winter Park
$2,500,000
4 Beds ⋅ 5 Baths ⋅ Sylvan Lake Shores SubDv. ⋅ 32789 Zip Code
Under Construction. Brand-new, meticulously crafted residence built by renowned builder LUIH Homes offering 3,138 square feet of thoughtfully designed living space. As you arrive, the home's stunning architectural façade and detached two-car garage make a striking first impression. Inside, every detail has been carefully curated to offer both sophistication and functionality. Soaring ceilings and expansive windows flood the home with natural light, while engineered hardwood flooring and elegant designer lighting add warmth and refinement throughout. The heart of the home is an impressive open-concept living area anchored by a chef’s kitchen featuring custom cabinetry, quartz countertops, top-of-the line Thermador appliances, a walk-in pantry, and an oversized center island. The adjacent dining and living spaces offer seamless flow, highlighted by stunning finishes and built-in features that enhance both comfort and convenience. The luxurious primary suite features a spa-like ensuite bath featuring a freestanding soaking tub, oversized glass-enclosed shower, dual vanities with quartz countertops, and a large walk-in closet. Secondary bedrooms are equally spacious, with ample closet space and access to beautifully appointed bathrooms with premium fixtures and finishes. Step outside to a private backyard oasis offering a large, covered patio with a summer kitchen, a sparkling pool, and a spacious backyard. The detached garage provides added flexibility, ideal for vehicle storage, a workshop, or potential future guest house. Jump on your golf cart and within minutes you’re transported to Park Ave, with its amazing shops, fine dining, and everything else that Winter Park features. Schedule your private showing today and experience the epitome of luxury Winter Park living.

185 Sylvan Boulevard, Winter Park
$599,000
3 Beds ⋅ 2 Baths ⋅ Killarney Estates SubDv. ⋅ 32789 Zip Code
Step into timeless elegance with this beautiful 2-story, 3-bed, 2-bath historic home located in one of Winter Park’s most coveted neighborhoods. Built in 1935, this classic residence boasts stunning architectural details throughout—including solid wood floors, 10-inch baseboards, two cozy wood-burning fireplaces, and ornate trim surrounding the windows and doors. The generous living room opens effortlessly to the dining area, creating an inviting space that’s perfect for entertaining. The sleek, updated kitchen offers ample counter space and generous storage, making it as functional as it is stylish. Upstairs, all three bedrooms feature warm solid wood floors, with the primary suite offering serene views of Lake Killarney—a perfect spot to unwind at the end of the day. On the first floor, a versatile bonus room can easily serve as a fourth bedroom, home office, or playful retreat. Additional conveniences include an indoor laundry room and a spacious, screened-in back porch overlooking a fenced backyard—ideal for gatherings or enjoying Florida’s beautiful weather year-round. Situated on a desirable corner lot, the home offers extra yard space and enhanced curb appeal. Roof replaced in 2020. A detached garage/workshop equipped with electrical, plumbing and AC sits at the rear of the property with access from Dallas Avenue. A separate long front driveway provides ample parking for guests, or even a boat. Best of all, there’s no HOA to limit your lifestyle or creativity. Just a short walk to Park Avenue, Winter Park Village, and a vibrant array of shops and restaurants, this is a truly unique opportunity to own a piece of local history. Don’t miss your chance to call this historic gem home!

490 Shoreview Avenue, Winter Park
$1,650,000
4 Beds ⋅ 6 Baths ⋅ Fontainebleau SubDv. ⋅ 32789 Zip Code
This Beautiful Winter Park Home is located between the "Vias" and "Tree Streets" for convenient access to highly coveted schools, Interlachen Country Club, Winter Park Racquet Club, YMCA and everything you love about Winter Park. Spacious and well proportioned rooms distinguish this beautiful home through its balance of both large, open spaces for casual indoor/outdoor entertaining and more formal spaces for living and dining. The large great room with stacking sliding doors flows to the adjacent screened lanai and pool area complete with "Summer Kitchen" and motorized retractable screens. Also open to the great room you'll find a well appointed kitchen complete with solid wood cabinetry, quartz counter tops, stainless double wall ovens, drawer microwave, glass cooktop with exhaust hood, dishwasher and french door refrigerator. Extending the kitchen, and adjacent to the great room, is a complete bar area with wine refrigerator, beverage refrigerator, storage and plenty of space for casual seating or eating. To keep everything in its place, there is a conveniently located "mud room/drop zone" adjacent to the kitchen. Turning to the more formal spaces on the ground level, you'll find a large entry foyer flanked by living and dining rooms. Off the entry hall is a lovely half bath/powder room and a full en-suite second primary bedroom with a full bath that opens to the pool area. Upstairs you find a large loft area from which you access the bedroom suites, laundry room and bonus room. The Primary Suite is spacious and private with an large walk-in closet and en-suite bathroom offering a garden tub, walk-in shower, private water closet and split vanities. Bedroom #3 is en-suite with a walk-in closet and tub/shower. Bedroom #4 offers a walk-in closet and an en-suite bathroom complete with walk-in shower. Upstairs you'll also enjoy the convenience of a spacious laundry room with utility sink, cabinetry, laundry bins and space to fold and hang as needed. As if that's not enough, there is a bonus room complete with half bath and closet that makes a fantastic workout space, home office or 5th bedroom. Outside you'll enjoy the large screened lanai and pool area that opens to the backyard. The backyard is complete with low maintenance artificial turf that provides year round green space. Your kids will be the envy of the neighborhood with the custom "tree house" retreat - allowing them a safe and secure escape for exploring their imagination and creativity. Large Two Car Garage. Privacy Driveway Gate. Roof new in 2023. A/C new in 2023. Water Heater new in 2023. Pool new in 2020. All measurements are approximate and Buyer is responsible to verify dimensions.

2339 Lafayette Avenue, Winter Park
$489,020
2 Beds ⋅ 2 Baths ⋅ Winter Park SubDv. ⋅ 32789 Zip Code
Here is the opportunity to own this beautiful remodeled bungalow in the desirable town of Winter Park. This meticulously maintained two-bedroom, 1.5-bath home is just steps from Hannibal Square and Park Avenue. Enjoy the convenience of Rollins College, shopping, dining and vibrant nightlife, all within short distance. Enter inside this charming bungalow to discover a newly updated kitchen that features granite countertops, stainless steel appliances and a center island. The enclosed Florida room is off the kitchen and is where you will entertain or just relax, as it provides sun all day. The fully fenced yard creates a delightful retreat, and the turf grass requires no maintenance but provides a year-round manicured look. In 2023, significant enhancements were made, including addition of a new rear deck and a new front porch, further enhancing the overall charm and appeal of the property. The roof was updated in December 2023, and the air conditioning unit was replaced in 2019, the air-conditioning compressor in 2022, and the water heater in 2019.

674 Douglas Avenue, Winter Park
$849,900
3 Beds ⋅ 2 Baths ⋅ Conwill Estates SubDv. ⋅ 32789 Zip Code
Welcome to this stunning, fully renovated 3-bedroom, 2-bath residence nestled in the highly sought-after Winter Park community. This meticulously upgraded home blends style, comfort, and functionality in an open-concept layout that includes spacious living, dining and kitchen areas adorned with elegant wood flooring and crown molding throughout. The custom-designed kitchen is a chef’s dream, featuring Quartz countertops, a 5-person breakfast bar, soft-close cabinets with ample storage, built-in pantry, matching wood floating shelves, recessed dimmable lighting, under-cabinet LED lighting, stainless steel appliances including a gas stove and exterior vented range hood, elegant backsplash and premium finishes. The Florida room, a gorgeous new addition, fills the space with natural light and opens to a spacious backyard oasis, complete with a refreshing pool, surrounding deck and shade awning ideal for relaxing and entertaining. A shed house equipped with electricity and a workbench provides additional storage. The beautiful garden includes a dedicated gardener's bench, mango and lime trees for fresh produce, a fully fenced enclosure with mature hedges for enhanced privacy and landscape lighting that transforms the space into a magical evening retreat. Additional highlights include hurricane-rated windows, plantation shutters, new fans throughout, newer AC and integrated central dehumidifier(2023), AC ducts (2023), tankless gas water heater (2024) and new refrigerator (2024). Other features include built-in surround sound speakers in the living room, sunroom, and pool area, NEST thermostat, ADT alarm system, circular brick-paved driveway and a well irrigation system for cost-effective lawn care and low utility bills. A 5-minute walk to the neighboring YMCA gym and Phelps Park and conveniently located near Park Ave, Winter Park Racquet Club, Winter Park Golf Club and Rollins College, as well as top-rated schools. Don't miss this opportunity to own a home where thoughtful, high quality upgrades meet elegant living in one of Winter Park’s most desirable neighborhoods.

1791 Spruce Avenue, Winter Park
$343,000
4 Beds ⋅ 2 Baths ⋅ Dubsdread Heights SubDv. ⋅ 32789 Zip Code
One or more photo(s) has been virtually staged. **Seller is motivated and encourages all serious offers—bring your buyers!** Welcome to your cozy Winter Park retreat! This charming 4-bedroom, 2-bath home blends comfort and convenience in one perfect package. Nestled on a spacious lot with a large backyard—ideal for entertaining, gardening, or playing fetch—this home also features a unique drive-through garage, perfect for weekend projects or extra parking flexibility. Step inside to find a warm and inviting layout filled with natural light and space for the whole family. Plus, enjoy peace of mind knowing the roof is only 4 years old—one less thing to worry about! Located just minutes from I-4 and surrounded by popular shopping centers, dining, and more, you'll love how easy it is to get anywhere you need to go. Don’t miss your chance to own a piece of Winter Park charm—schedule your showing today! <iframe src="https://my.matterport.com/show/?m=n9WcP2miBTq&brand=0&mls=1&" width="640" height="360" style="border: 0;" allow="fullscreen"></iframe>

657 Overspin Drive, Winter Park
$725,000
3 Beds ⋅ 2 Baths ⋅ Sylvan Lake Shores SubDv. ⋅ 32789 Zip Code
Charming Cottage in the Heart of Winter Park. Step into a world of timeless charm with this delightful 3-bedroom, 2-bath cottage that exudes warmth and character at every turn. Boasting nearly 1,700 square feet, this enchanting home features a thoughtfully designed split plan, providing both privacy and functionality. The moment you approach, you’ll be captivated by its amazing curb appeal, nestled on a picturesque .15-acre parcel adorned with low-maintenance landscaping. Inside, discover an adorable eat-in kitchen that beckons for casual gatherings, where memories are made over delicious meals. High vaulted ceilings create an airy ambiance, amplifying the sense of space and light throughout the home. Generous closets ensure great storage, while the convenient inside laundry room adds to the ease of everyday living. The 3 outdoor sitting areas allow for great relaxation spots and fabulous entertaining areas in the fresh air. Recent updates include a new roof (2022), AC system (2017), and a new electrical panel (2019). Plantation Shutters throughout. Whether you choose to move in, renovate, or envision a brand-new dream home, the possibilities are endless. Located just a 5-minute drive or a leisurely 25-minute stroll from Winter Park's fabulous Park Avenue, you’ll find yourself immersed in a vibrant community filled with delightful shops, art galleries, and exquisite dining options, all complemented by the natural beauty of Central Park. With top-rated Winter Park schools nearby and nestled on one of the most charming brick streets in the 32789 area, this cottage offers the perfect blend of lifestyle and location. Don’t miss this rare opportunity to make this adorable cottage your own or use the ample lot to build the home of your dreams.

1570 Grove Terrace, Winter Park
$995,000
4 Beds ⋅ 3 Baths ⋅ V H Musselwhites Sub SubDv. ⋅ 32789 Zip Code
WELCOME to 1821 WINDSOR DR in WINTER PARK, FLORIDA! This is a ONCE IN A LIFETIME OPPORTUNITY to own this BEAUTIFUL CUSTOM-BUILT MASTERPIECE of a HOME in ONE OF THE MOST DESIRED LOCATIONS in TOWN! When you buy this Home, you aren’t just purchasing a NEWLY BUILT CUSTOM HOME FULL OF LUXURIOUS UPGRADES and ARCHITECTURAL FEATURES; you are also buying into the LIFESTYLE that others DREAM OF LIVING in the LAKEMONT AREA of WINTER PARK! The A RATED LAKEMONT ELEMENTARY SCHOOL is just beyond your backyard! Phelps Park is also only ¼ mile away! The INFAMOUS PARK AVE is LESS THAN A MILE AND A HALF AWAY. There are over 175 LOCAL SHOPPES and RESTAURANTS in the immediate area of PARK AVE, mixed in with NUMEROUS PARKS AND GREEN SPACE! The RENOWNED ROLLINS COLLEGE is also LESS THAN A MILE AND A HALF AWAY! You will LIVE, WORK and PLAY in the MIDDLE of THE PLACE TO BE in TOWN! YOU CANNOT PICK A BETTER LOCATION to LIVE IN if you are wanting the WINTER PARK LIFESTYLE! The Home itself was Built in 2017! The CURRENT OWNERS are the ORIGINAL OWNERS and have IMMACULATELY MAINTAINED THIS HOME! This Home has a STATE-OF-THE-ART PHOTOVOLTAIC SOLAR SYSTEM that is PAID OFF and WILL CONVEY WITH THE HOUSE so the NEW OWNER WILL HAVE MINIMAL POWER COSTS and TOP OF THE LINE SOLAR ENERGY! Structural Upgrades that are above and beyond are: Architectural Features such as the Roof Shape and the Design of the Exterior Walls that are meant to withstand the strongest of hurricane winds. The home is also built up on one extra layer of Cinderblock to avoid any flooding risk! You will notice as soon as you pull up to the house, there is a BEAUTIFUL CURB APPEAL that is emphasized by the mature, but low maintenance landscaping. Walking into the house, your attention is immediately drawn to the BEAUTIFUL WOOD LOOK PORCELAIN TILE that is THROUGHOUT THE ENTIRE MAIN LIVING AREA and BEDROOMS! The house opens up into a very large and modern floor plan! The Main Living Area is a very large area that includes the Living/Family Room, an Oversized Gourmet Kitchen and a nice sized dining room! This entire space is punctuated by lots of perfectly placed windows for tons of natural light, warmth and comfort! The Kitchen has High-End Quartzite Countertops, an oversized island and Custom Walnut Soft-Close Cabinets! Stainless Steel Appliances, recess lighting and under cabinet lights top off what is already a DREAM KITCHEN! The PRIMARY SUITE is OVERSIZED with large windows and lots of space! The Primary Bathroom is the size of a Primary Bathroom you would expect in a home of twice its size! There is a HUGE OVERSIZED CUSTOM SHOWER with MULTIPLE SHOWER HEADS include a RAIN SHOWER HEAD and enough space for you and your significant other to comfortably shower at the same time! There is also an elegant garden tub if you prefer to bathe in relaxation! Lots of floor space, lots of counter space and well-designed dual vanities make the primary bathroom feel like its own little slice of heaven! There is also a very large, custom closet that has built-in “his & her” shelving. All secondary bedrooms are also a very healthy size!! Out back, you can enjoy the birds, plants and the nice Florida weather on your covered lanai that is over 250 square feet and has an OUTDOOR KITCHEN with a built-in refrigerator, and a built-in grill! Many species of plants in the natural backyard attract all sorts of birds to your home as well! Don't Miss This Opportunity! It's a One-of-a-Kind Home! Book your appointment today!

1821 Windsor Drive, Winter Park
$480,000
3 Beds ⋅ 3 Baths ⋅ Indiana Place Condo SubDv. ⋅ 32789 Zip Code
Tucked away on a quiet street blocks from the cultural heartbeat of Winter Park is this 3-bedroom, 2.5-bath townhouse-style condo that offers a balance of comfort, convenience, and charm. With nearly 1,600 square feet of thoughtful space, the two-story home lives large, featuring an open-concept main floor with high ceilings, ceramic tile throughout, a spacious kitchen with granite counters and pantry, and a cozy living area complete with fireplace, built-ins—perfect for stashing your favorite reads, and French doors that provide natural light and flow out to your private patio. Upstairs, the spacious primary suite features a walk-out balcony, updated bathroom with an elegant shower, dual sinks, and a large walk-in closet, while two additional bedrooms give you flexibility for guests, family, or even a quiet home office. Recent updates like brand-new carpet, a 2018 A/C system, and a 2025 water heater offer peace of mind, and the attached two-car garage adds that rare, practical bonus. But what really makes this spot sing is its unbeatable location—you're less than two miles mile from Park Avenue’s boutiques and brunch spots, a quick ride to Rollins College, and just minutes to Mead Gardens, Leu Gardens, the Orlando Science Center, Winter Park Village, AdventHealth Hospital, College Park, I-4, and the SunRail Station for an easy commute downtown. Whether you're strolling to the Saturday Farmers' Market or grabbing coffee before class at Rollins, this place lets you be in the middle of it all—without sacrificing space or comfort. HOA fees are low, leasing is allowed, and pets are welcome. It’s easy living in one of Central Florida’s most beloved neighborhoods—where everything just feels...right.

1545 Indiana Avenue Unit B, Winter Park
$4,599,000
5 Beds ⋅ 7 Baths ⋅ Robert Dhu Macdonald Park SubDv. ⋅ 32789 Zip Code
Welcome to Lincoln! This new construction single family home has been meticulously crafted and constructed by Wooten Built, a locally established, award-winning developer and luxury home Builder. Location! Location! Location! Lincoln Circle is a quiet street next to Park Avenue restaurants and shopping. Easily walk to Winter Park shops, restaurants, and the Winter Park Golf Course. This bespoke home includes premium features, appliances, fixtures and finishes as follows: Elevator, Wolf/Sub-Zero appliances, wine cooler tower, built-in coffee maker, Lutron RA3 Automation, wired for security with plenty of camera drops, whole-house audio pre-wire featuring Sonos speakers and 5.1 surround, first floor primary bedroom with ensuite washer/dryer, additional guest suite first floor, 11’4” first floor ceilings and custom 10’ solid core DOORS, wet bar, large vaulted upstairs living room, large flex-space upstairs bonus room, trey ceilings, huge front entry window and door system, two 10’x10’ full-view garage doors, circular driveway, full-house natural gas generator, heated pool with spa and fire & water bowls, plenty of pool deck space, and exquisite landscaping. Smart glass covers the large ~14’ x 10’ front entry system… Choose frosted for privacy or transparent/thru-view at the press of a button! A 6’ masonry-stucco wall encompasses the property. The rear cabana/pergola houses the summer kitchen, pool bar, pool-bath and outdoor shower. Enjoy two fireplaces!: a 100” linear electric fireplace in living room and a 60” linear natural gas fireplace by the pool deck. Inquire with agent for more information.

985 Lincoln Circle, Winter Park
$475,000
Capens Add SubDv. ⋅ 32789 Zip Code
Great opportunity for a R-2 lot in heart of downtown Winter Park - opportunity to purchase adjacent lot at 631 Symonds and combine

621 Symonds Avenue, Winter Park
$475,000
Capens Add SubDv. ⋅ 32789 Zip Code
Great R-2 lot in the heart of downtown Winter Park - lot next door 621 Symonds also available for purchase and opportunity to combine.

631 Symonds Avenue, Winter Park
$275,000
2 Beds ⋅ 1 Baths ⋅ Dubsdread Heights SubDv. ⋅ 32789 Zip Code
Great Opportunity in Prime Location! Price adjustment below appraised value. Located just off the Fairbanks Avenue exit from I-4, this charming 2-bedroom, 1-bath fixer-upper sits on a generous 7,000 sq ft lot in a quiet, convenient neighborhood. With original hardwood floors in the living area and bedrooms, this home is full of character and ready for your personal touch. The enclosed front porch has been vented for A/C, creating a light-filled sunroom and entry foyer—perfect for a relaxing morning coffee or casual sitting area. The garage has been converted into a functional bonus room/office space and a large laundry but could easily be restored to a traditional garage if desired. The kitchen offers space for a small dining table, and the original tiled bathroom remains in great condition, preserving the home’s vintage charm. Many of the windows have been updated, enhancing both aesthetics and energy efficiency. The large backyard features a concrete pad with existing electrical service, ideal for a future shed, workshop, or outdoor living area. Recent major updates make this home even more attractive: New Central A/C installed in May 2023. $10,000 in crawl space improvements (vapor barrier, dehumidifiers, drainage matting, and new access door), with a transferable service plan. Whether you're looking to renovate, invest, or build new, this property offers flexible options in a rapidly appreciating area. Tear down and build your dream home, or restore this cottage to its former charm—the choice is yours. Don’t miss out—schedule your showing today!

849 Driver Avenue, Winter Park
$493,000
3 Beds ⋅ 2 Baths ⋅ Lake Forest Park SubDv. ⋅ 32789 Zip Code
Charming Mid-Century Ranch in Prime Winter Park Location – Steps from Blue Jacket Park. Ideally situated in the heart of Winter Park and just a stone’s throw from Baldwin Park’s beloved Blue Jacket Park, this tastefully updated 3 BEDROOM, PLUS OFFICE, 1.5 BATHROOM home blends timeless character with modern touches. Enjoy a freshly painted interior, stainless steel appliances, indoor laundry, and a newly landscaped backyard perfect for entertaining or relaxing in privacy. There's even a bonus office/flex space just off the dining room — ideal for working from home. Whether you're looking to move right in or explore the opportunity to build your dream home like several neighbors have done, the possibilities here are endless. The owner is willing to REPLACE THE ROOF prior to closing, offering peace of mind for future homeowners. Enjoy unbeatable proximity to Leu Gardens, Downtown Winter Park, and countless parks, restaurants, and boutique shops. Plus, you're just minutes from major highways, Downtown Orlando, and Orlando International Airport, making this location as convenient as it is desirable. Call to schedule your private showing today!

2327 Mulbry Drive, Winter Park
$1,545,000
4 Beds ⋅ 4 Baths ⋅ Lake Monte Sub SubDv. ⋅ 32789 Zip Code
Stunning contemporary home in Winter Park is close to Park Avenue and all of the wonderful restaurants, shops and the historic farmer's market. This luxurious home exudes a crisp, pristine setting with modern living spaces and a well-designed, stylish living environment. Off the foyer entry is a home office or bonus room as well as a powder bath. The beautiful dining room is open to an elegant living room and dreamy modern fireplace. The kitchen is perfect for entertaining with "LG Snowstorm Quartz" kitchen countertops, wine fridge, Thermador gas range and appliances. The first floor Primary Suite has a huge walk-in closet with laundry. Enter the bathroom to see the uniquely stylish soaking tub and shower and dual vanity. Upstairs find 3 spacious bedrooms, all with walk-in closets, a large loft, laundry room and 2 additional bathrooms. The outdoor patio sports a remote screen to access the sparkling pool and spa. Fenced-in property gives privacy and a sense of calm, particularly on the deck and Pergola in the back yard. Zoned for A-rated Brookshire Elementary, Glenridge Middle, and Winter Park High School. MORE PICTURES FRIDAY!

1831 Mizell Avenue, Winter Park
$749,000
3 Beds ⋅ 3 Baths ⋅ Henkel Add SubDv. ⋅ 32789 Zip Code
Like new and totally turn-key! Built by award-winning Winter Park Custom Homes, coastal modern residence offers thoughtful design, high-end finishes, and an unbeatable location in Winter Park's coveted 32789 ZIP code. 3-bedroom, 2.5-bath home combines privacy with convenience. Minutes from Park Avenue, downtown Orlando and major local destinations. The home features authentic reclaimed European oak wood flooring throughout, 10-foot ceilings, and abundant natural light from a premium window and door package that frames garden and yard views. Open-concept floor plan flows through the main living area into a chef’s kitchen with marble countertops, backsplash, center island, Thermador gas range, walnut cabinetry, and custom millwork. Solid core 8’ doors, LED lighting, and a centralized On-Q AV closet with surround sound wiring. Recent updates include new Rejuvenation hardware throughout, freshly painted cabinets in the kitchen, laundry, mudroom and guest bath, a canopy installation at the kitchen entry, added storage solutions in the laundry and garage, interior painting and more. New grass and fence with gates installed. The primary suite features a spa-style bath with a large walk-in shower and soaking tub, and a generous walk-in closet. Additional features include custom window treatments, updated light fixtures, and mounted TVs in the living room and primary bedroom. Two more bedrooms upstairs with nicely sized closets and beautiful marble bathroom and shower/soaking tub. Built with long-term efficiency in mind, the home includes block construction, a concrete flat tile roof, spray foam insulation, Low-E glass, and custom metal Bahama shutters. The exterior has also been updated with new sod and fencing. Private garage, guest parking, security system and underground utilities. Close to highways, shopping, schools. Park Maitland, Lake Highland and public schools. No HOA! This home offers a rare opportunity to own a low-maintenance, design-forward residence in a prime Winter Park location with no detail overlooked. Furnishings can also be included upon request at a separate price. Move right in!

1429 Indiana Avenue, Winter Park
$920,000
3 Beds ⋅ 4 Baths ⋅ Mondrian/Winder Park Twnhms SubDv. ⋅ 32789 Zip Code
Act quickly—only three units remain! We are excited to introduce a beautiful, brand-new modern brownstone located in the heart of Winter Park, with access to Lake Killarney. Nestled in an exclusive community of 30 contemporary townhomes, each residence is thoughtfully designed with exquisite finishes, expansive storefront-style windows, and 11-foot ceilings that welcome an abundance of natural light. This impressive 3-bedroom, 3.5-bath home comes packed with luxurious features that truly elevate its value. The unique layout places the main living space on the second level, seamlessly connecting a modern kitchen, dining room, and great room, perfect for entertaining. Also on this level, you'll find a spacious primary bedroom suite at the rear of the home, offering serene lake views from both the bedroom and spa-inspired bath. This retreat is complete with two generous walk-in closets, a cozy sitting area, and a beautifully designed bath featuring luxurious tile, a frameless glass shower, and a private water closet for added privacy. On the first level, our advantageous split-bedroom design includes two additional suite-style bedrooms, offering flexibility and space to accommodate your lifestyle. Convenience abounds, thanks to a full-size laundry room complete with a front-loading washer and dryer, making this home both elegant and functional. Ascend to the rooftop oasis, where you'll discover an outdoor kitchen, a pergola, a hot tub, and breathtaking views, creating the perfect atmosphere for relaxation and entertaining. Situated in the picturesque Winter Park, just north of downtown Orlando, residents enjoy lakeside living with access to a private boat slips, and a charming lakefront pavilion. Here, you’re moments away from outstanding dining, shopping, and recreational options, ensuring a lifestyle of unmatched convenience and luxury. Additional highlights include high-end level four drywall finishing throughout the home, designer-selected lighting fixtures that provide a striking ambiance, and custom closet systems designed for optimal organization and style. The durable Mohawk engineered flooring in a chic gray tone adds both beauty and warmth to each room. Enjoy cooking with a Samsung appliance package, featuring a natural gas cooktop and a tankless water heater for ultimate efficiency. The kitchen boasts luxurious quartz countertops and a stunning waterfall-edge island—ideal for culinary adventures and gatherings with friends. Finally, unwind on the level three composite decking, perfect for outdoor gatherings in the fresh air. Your oversized two-car garage comes with an epoxy-painted floor and a 220V EV outlet for added convenience and eco-friendly charging options. Welcome to your dream home, where every detail has been meticulously crafted to enhance your lifestyle, perfectly blending comfort, style, and sustainability. Live the life you’ve always wanted in our exceptional townhome!

1764 Mondrian Circle, Winter Park
$672,000
3 Beds ⋅ 2 Baths ⋅ Park West Condo SubDv. ⋅ 32789 Zip Code
Welcome to Park West — an exclusive, gated enclave ideally situated just moments from the vibrant heart of downtown Winter Park. This impeccably maintained 3-bedroom, 2-bathroom residence with a versatile den offers an exceptional combination of elegance, comfort, and convenience. The den, currently utilized as a private home office, can easily serve as a third bedroom to accommodate your needs. The open-concept living and dining areas are highlighted by a traditional decorative fireplace, providing a warm and inviting ambiance for everyday living or entertaining. The spacious primary suite features a private en-suite bath with a walk-in shower and an expansive walk-in closet, while the second bedroom is located adjacent to the hallway bath, which includes a tub/shower combination. A dedicated laundry room with built-in shelving and generous storage is a rare and valuable amenity in condominium living. Residents of Park West enjoy access to an array of premier community features, including a clubhouse, swimming pool, and tennis/pickleball courts — all within the privacy and security of a gated setting. Best of all, this exceptional property is just a short stroll to the boutiques and dining of Park Avenue, world-class museums, Central Park, the SunRail station, and the Winter Park Golf Course. This is a rare opportunity to own a spacious, well-appointed condo in one of Winter Parks most sought-after neighborhoods.

300 Carolina Avenue Unit 304, Winter Park
$420,000
4 Beds ⋅ 2 Baths ⋅ Lawndale SubDv. ⋅ 32789 Zip Code
Your Opportunity is Here! Renovate this duplex and begin renting both sides or live in one and rent the other! Fenced yard, septic tank and large carport.

1618 Indiana Avenue, Winter Park