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$715,000
4 Beds ⋅ 4 Baths ⋅ Swoope Park SubDv. ⋅ 32789 Zip Code
Located within the private enclave of 400 West—an exclusive 9-residence community just steps from Park Avenue—this contemporary townhome offers a rare blend of quality construction, refined interiors & exceptional walkability. From the moment you step inside—whether through the private garage or along the garden-style front path—you’re met with a bright open-concept main floor that blends comfort, functionality & clean design. Clean-lined finishes include large-format porcelain tile, level 5 drywall, tall contemporary baseboards & designer lighting that elevate the functionality & style of the main floor. The kitchen anchors the space w/ flat-panel high-gloss white cabinetry, sleek chrome pulls, quartz counters & a suite of stainless-steel appliances including a Whirlpool French door refrigerator w/ bottom freezer, LG slide-in range w/ glass cooktop & built-in microwave & Frigidaire dishwasher. A newly installed pull-down faucet, deep undermount double bowl sink, generous cabinet storage & motorized Lutron-enabled window shades on the front-facing living room window & entry door provide functional use & elevate the design. A stylish powder bath, under-stair storage & direct access to the garage complete the main floor. The rear-entry garage features alleyway access, a storage closet & built-ins for added convenience. Upstairs, two primary-sized suites span the second level, each w/ engineered wood flooring & floor-to-ceiling windows or glass doors that fill the rooms w/ natural light. Spa-inspired en-suite bathrooms feature large-format porcelain tile, frameless glass shower enclosures, wall-to-wall mirrors, matte white vanities, solid surface counters, undermount sinks & chrome fixtures. The primary bath includes an extended double-sink vanity, private water closet & a built-in shower bench & storage niche. Beyond the bath is a spacious walk-in closet. A full laundry room is also located on this level, featuring a Samsung washer & dryer set w/ overhead storage. The third level offers two additional bedrooms or flex rooms—each w/ walk-in closets—connected by a shared Jack-&-Jill bath, making this space ideal for guest suites, a home office, gym or creative studio. Recent upgrades include a full interior repaint (2025), blackout shades, Pico-controlled Lutron motorized shades, professionally cleaned carpet, tile & grout. Smart home features include a Nest thermostat & Ring doorbell. Systems & mechanicals upgrades include a newer Trane HVAC condenser (2023), Whirlpool fridge (2018), Samsung washer/dryer (2022) & recently replaced garbage disposal & kitchen faucet (2024). The HVAC system was fully serviced in 2025 & all fans, lighting, drains & toilets have been checked & are in excellent working order. Built in 2014 w/ concrete block construction on both floors, level 5 drywall & a metal roof, this fee-simple townhome offers low-maintenance peace of mind. HOA dues of $400/month include exterior maintenance & landscaping. Guest parking is available on-site as well as along Swoope. This home delivers the rare combination of timeless quality & modern convenience. Thoughtfully designed across three levels, it offers flexibility, privacy & low-maintenance living—all in a quiet 9-residence community where everything Winter Park has to offer is just steps away. Whether you’re looking for a full-time residence or a lock-&-leave lifestyle, this is an exceptional opportunity to own a turnkey property in the heart of Winter Park.

438 W Swoope Avenue, Winter Park
$2,650,000
6 Beds ⋅ 5 Baths ⋅ Palmer Park SubDv. ⋅ 32789 Zip Code
Step into elevated Winter Park living with this exceptional Mediterranean-inspired estate. Built in 2020, every inch of this home was thoughtfully crafted with timeless architecture and sophisticated, high-end finishes. From the rounded stone entry feature and custom iron double doors to the soaring ceilings and designer lighting, this home instantly impresses. The spacious great room opens to a wall of glass folding doors that reveal a private backyard retreat—featuring a heated pool and spa, lush landscaping, and an expansive lanai with summer kitchen. The home is serviced by natural gas, seamlessly supporting modern comfort and efficiency. The kitchen is truly the heart of the home, boasting dual oversized islands, WOLF appliances, fully custom cabinetry, two dishwashers, a double oven and a massive walk-in pantry. A nearby sunken bar offers the perfect spot for entertaining. Downstairs includes two well-appointed bedrooms, one with its own en suite—ideal for guests or multigenerational living. The detached casita includes a full bath and is pre-plumbed for a kitchenette and washer/dryer, offering endless potential as a guest suite, gym, or studio. Upstairs, the primary suite is a sanctuary: a double-sided fireplace, private balcony overlooking the pool, two generous walk-in closets (one with a secondary laundry hookup), and a spa-worthy bath complete with a sauna and a massive multi-head shower. A bonus loft with wet bar and two additional bedrooms round out the second floor. Located just minutes from Park Avenue and zoned for top-rated public schools including Winter Park High, a community known for both academic and extracurricular excellence (some say there’s championship energy in the air), this home offers a rare blend of luxury, lifestyle, and location.

575 Palmer Avenue, Winter Park
$1,300,000
4 Beds ⋅ 3 Baths ⋅ Dixie Terrace SubDv. ⋅ 32789 Zip Code
One or more photo(s) has been virtually staged. As you enter this renovated 4-bedroom, 2.5-bathroom home within the city limits of Winter Park, you're immediately welcomed by a bright, open living and dining area anchored by a stunning wet bar, complete with sink, cabinetry, ice maker, and floating shelves. All completed with light modern porcelain tile flooring. To your right, the kitchen makes a bold statement with dramatic 4.5-inch thick countertops, waterfall-edge island, oversized farm sink, and high-end appliances including a Thermador induction stove and Whirlpool double oven, microwave, dishwasher, and fridge/freezer. Custom soft-close cabinetry blends seamlessly into the open layout, offering style and serious storage. Just beyond the hurricane rated sliding glass doors, you'll find a covered lanai and spacious yard with a mix of grass and artificial turf, ideal for entertaining, relaxing, or adding a future pool. The primary suite is tucked away on the left side of the home, offering peace and privacy. It features soft lighting, remote-controlled shades, and two walk-in closets with built-ins. The spa-like en-suite bathroom combines wood and stone textures, a floating dual-sink vanity, and a large walk-in rain shower, all designed with modern feel. Two additional bedrooms and a full bathroom are located down the same hallway, separated from the main living space by modern barn doors, perfect for creating a private wing for family or guests. On the opposite side of the home, a fourth bedroom makes a perfect office or guest suite. A nearby half bath opens to the outside, making it an ideal future pool bath. The laundry room is equipped with LG Signature washer and dryer, a drying closet, sink, and built-in storage. Adjacent to the laundry area is a stylish mudroom with custom built-ins to keep everything organized. Both the attached 2-car garage and carport make parking effortless. The garage is climate-controlled with a split AC unit and finished with sleek epoxy flooring, perfect for a gym, workshop, or additional storage. The garage is also equipped with EV charging capabilities. Set on a generous 0.33-acre corner lot, this property offers extra outdoor space, privacy, and potential, whether for a future pool, garden, or entertaining area. Additional upgrades include a whole-house Generac generator, a tankless water heater with softener and filtration system, hurricane-rated windows and sliding doors, new roof (2021), updated plumbing and electrical (2022), and two new AC systems (2022). Non-textured walls and ceilings, smart lighting, and clean, minimalist finishes round out the home’s modern aesthetic. Every detail of this home has been carefully curated to deliver a lifestyle of comfort, style, and function, a true modern retreat in the heart of Winter Park. This home is located just a short drive away from Park Avenue and its many restaurants and other businesses. Conveniently located close to major highways for easy commuting, schedule your private tour today.

1371 Lyndale Boulevard, Winter Park
$1,277,000
3 Beds ⋅ 4 Baths ⋅ Parklando SubDv. ⋅ 32789 Zip Code
Welcome to a truly exceptional residence nestled on a quiet, tree-lined street in one of Winter Park’s most desirable neighborhoods. This custom-built gem offers a blend of elegance, craftsmanship, and resort-style comfort, featuring 3 bedrooms, 3.5 baths, and 2,595 square feet of thoughtfully designed living space. As you enter, you'll be immediately drawn to the tranquil, resort-like ambiance created by the centerpiece of the home: a screened-in courtyard with a heated saltwater pool and spa, perfect for relaxing or entertaining year-round. Adjacent to this serene space is a private guest casita complete with a full bath and separate entrance, ideal for in-laws, visitors, or an independent-minded teen. Step into the main house, and you will be immediately captivated by the 15-foot Frank Lloyd Wright-inspired rock wall in the stunning Living Room. The 12-foot ceilings give the space a seemingly endless light and airy feel. Overlooking the great room is a fully equipped chef-inspired kitchen where creating meals will be a breeze with an abundance of cabinets, gleaming quartz counter tops, a large prep island,14 foot breakfast bar and newer top-of-the-line LG SS appliances, and a GE Profile cook top — ensuring that entertaining and meal prep are effortless. There is also a large dining room that can fit more than a large dinner party or family holiday gathering. Also, tucked away on the opposite side of the first floor is a guest suite, featuring a spa-inspired bath with beautiful cabinetry, exquisite tile work, and a large walk-in shower. Plus, the large laundry room with an abundance of storage and a utility sink to round out the main floor of this stunning home. Upstairs is the elegant private owner’s retreat, which also enjoys a quiet sitting area and an expansive custom walk-in closet. The spa-like bath will not disappoint with its large soaking tub, separate stall shower, and dual sinks with contemporary cabinetry and elegant tile throughout. Additional amenities include a large 2-car garage with an EV 30 amp outlet, plus an oversized over 300 square foot separate flex space that would make an excellent home office, home gym, or craft/hobby space. The home features tons of storage space, custom automated blinds with remotes, blackout blinds, a new AC unit, new lighting, new exterior paint, and a tankless water heater. This remarkable home is flooded with natural light and ambiance, with many floor-to-ceiling windows, while exuding a warm and cozy atmosphere. Zoned for some of the best public schools in the area, including Audubon K-8 and Winter Park HS, and conveniently located near Audubon Park/Corrine Drive shopping and restaurants, and of course easy access to Winter Park's Park Ave with its fine restaurants and shopping, and also close proximity to Blue Jacket Park/Baldwin Park, Downtown Orlando, Leu Gardens, the Mills 50 District and Rollins College. Don't miss your opportunity to own this exquisite Winter Park retreat, a perfect blend of luxury, privacy, and location. Florida living at its finest!

2728 Eastern Parkway, Winter Park
$940,000
4 Beds ⋅ 3 Baths ⋅ Karolina On Killarney SubDv. ⋅ 32789 Zip Code
Biscayne Bay, a recent Parade of Homes winner, is one of the latest custom builds by the trusted team at Konkol Custom Homes—and it’s ready for its very first owner. Set in a prime Winter Park location, this two-story home offers clean lines, high-end finishes, and a layout that fits real life. With just over 2,600 square feet under air, the home features 4 bedrooms and 3 full bathrooms. The 4th bedroom is located downstairs and works beautifully as a dedicated office. Upstairs, a spacious bonus room offers flexibility for a home gym, theater, large office, or guest suite. Throughout the home, you’ll find wide-plank white oak flooring, matching stair treads, tall baseboards, and cohesive, streamlined trim details. The kitchen is crisp and functional, with white cabinetry, quartz counters, tile backsplash, and well-chosen finishes. The primary suite includes a walk-in closet system and a bathroom that checks all the boxes—soaking tub, oversized shower, and double vanities. Out back, enjoy a generous covered porch, landscaping that offers privacy with a natural bamboo hedge, and a future-ready pool plan already in place. High style, low maintenance living—all just five minutes from Park Avenue, walkable to Lake Killarney, close to Dubsdread, and under 2 miles to AdventHealth. Biscayne Bay is a polished, move-in ready opportunity in the heart of Winter Park.

1840 Biscayne Drive, Winter Park
$775,000
2 Beds ⋅ 2 Baths ⋅ Cloisters Condo SubDv. ⋅ 32789 Zip Code
Welcome to The Cloisters—a prestigious lakefront community nestled in the heart of Winter Park, perfectly positioned between the timeless charm of Park Avenue and the serene beauty of Lake Osceola. This fully furnished second-floor residence has been meticulously redesigned and renovated to maximize both space and style, offering the comfort of a thoughtfully designed home, enhanced by luxurious, designer-selected finishes throughout. Step inside to discover a beautifully appointed interior featuring high-end touches. The kitchen is a true showpiece, boasting custom wood cabinetry with artistic wood detailing, granite countertops, full counter-to-cabinet backsplashes, and top-tier appliances including a Wolf cooktop and oven, Fisher & Paykel dishwasher, Liebherr wine cooler, and Sub-Zero refrigerator. The expansive kitchen island comfortably seats four, with a sleek, integrated extension that effortlessly accommodates up to seven—perfect for entertaining in style. The open-concept living area flows seamlessly to a spacious private balcony, offering tranquil views of the heated pool, putting green, lush landscaping, and the shimmering waters of Lake Osceola—ideal for a morning coffee or year-round entertaining. The primary suite is a serene retreat, featuring blackout blinds, a Sleep Number smart bed with dual temperature controls, and custom floor-to-ceiling built-ins with integrated lighting, display shelving, and a dedicated vanity area. Additional built-in cabinetry lines the hallway leading to the en-suite bathroom, providing ample space for jewelry, shoes, and wardrobe essentials. The second bedroom is designed for versatility, with a wall-to-wall built-in home office setup overlooking a beautiful resort-style view, along with its own matching floor-to-ceiling built-ins for display and storage. Both bathrooms have been tastefully reimagined with new vanities, granite countertops, upgraded shower enclosures and hardware, and stylish lighting and mirrors. The primary bath includes additional custom built-ins for optimal storage and organization. Throughout the home, fresh paint and luxury vinyl flooring create a clean, modern aesthetic. Additional features include an in-unit washer and dryer tucked behind a custom wood door, a built-in safe, and a new A/C unit installed in 2024. The residence also includes a deeded covered-parking space and a private storage unit. The Cloisters community offers a wealth of amenities, including an onsite property manager, ample guest parking, elevators, a heated pool, onsite laundry facilities, a putting green, private lake access, a dock, and boat slips available via resident lottery. Residents also enjoy two fitness centers with one dry sauna and a recently updated clubhouse with a full kitchen and bath—ideal for private gatherings. Just a short stroll from the boutiques, restaurants, and cultural attractions of Park Avenue, and Rollins College, this fully renovated, turnkey residence presents a rare opportunity to enjoy the ultimate blend of location, luxury, and lifestyle. Realtor/owner is a licensed Florida real estate broker.

100 S Interlachen Avenue Unit 204D, Winter Park
$725,000
4 Beds ⋅ 2 Baths ⋅ Capens Add SubDv. ⋅ 32789 Zip Code
Under contract-accepting backup offers. Stop the car! Develop your dream project on this hard to find R-3 lot! Adjacent 75x100 R-3 vacant lot (TAX ID 06-22-30-1168-02-023) on the south side to be purchased simultaneously, for a total of 75x200 or 15,000sq/ft. Next to the proposed Winter Park Commons project, walk to Winter Park Village, Hannibal Square, WP9 and Park Ave for top shopping, dining and entertainment. Don’t miss this unique opportunity! PROPERTY SOLD AS-IS. VALUE IS IN THE LAND. NO REPAIRS.

770 W Webster Avenue, Winter Park
$1,575,000
4 Beds ⋅ 4 Baths ⋅ Sylvan Lake Shores SubDv. ⋅ 32789 Zip Code
Beautiful Sylvan Lake Shores Mediterranean home. Ideally located in quintessential Old Winter Park with its tree lined, brick streets that surround Lake Mizell. This 4 bedroom 3 ½ bath, plus office home features timeless architectural features such as classic wide molding, repeated archways and a custom ironwork stairway. The soaring 10 foot ceilings accentuate the classic feel of this elegant home. The designer inspired kitchen features custom cabinets and spacious pantry. The spa like master suite is located on the first floor and has an en-suite bath and custom designed closet. Just recently completed, the luxurious master bath has an inviting soaking tub and separate, relaxing rain shower. The executive office is located on the first floor. Up the custom staircase are three bedrooms including a private guest room with its own en-suite bath. The open floor plan is perfect for entertaining with multiple, solid wood French doors surrounding the welcoming back yard pool with cooling fountains. Outside, a custom awning shades the patio as you relax by the pool. There is a convenient pool bath as well. This bright and sunny home is in a prime location of Winter Park with an easy walk or bike to Park Avenue with its upscale restaurants, stores and Rollins College. Excellent Winter Park Schools. This amazing move in ready home is an excellent opportunity to live in the heart of Winter Park and enjoy Central Florida living.

1394 Grove Terrace, Winter Park
$3,975,000
4 Beds ⋅ 6 Baths ⋅ Cloister Grove Sub SubDv. ⋅ 32789 Zip Code
In the heart of Winter Park, 1150 Via Salerno is a newly completed Mediterranean-minimalist residence that blends architectural refinement with organic warmth. Now offered at a compelling new price, the home presents a rare opportunity to experience architecturally distinctive new construction in the Vias neighborhood. Conceived, developed & designed by Steve & Jodie Konold of Scout & Co., the 3,850-sf residence offers 4 beds & 5.5 baths, w/ a layout thoughtfully arranged to provide the intentional privacy of a luxury retreat. Beyond its terraced walkway—envisioned in collaboration w/ architect Cynde Norris—French antique gates open to a native-planted entry garden, creating a soft transition to the interior. A glass foyer featuring a woven rattan chandelier, sourced & designed in London, leads to a sculptural stairwell positioned just off the main living spaces. The great room includes soaring ceilings, a sleek, custom plaster fireplace & walls of glass doors & windows. Ten-inch baseboards meet level 5 drywall in a clean reveal, paired w/ micro-crete flooring on the main level & wide-plank European oak upstairs. The kitchen is appointed w/ a Thermador dual-fuel range, matching plaster hood, full refrigerator & freezer columns & a large island with seating topped in honed black quartzite. The surrounding cabinetry features hand-carved V-groove panels w/ soft-close hardware & integrated pullout storage. Caesarstone surfaces line the perimeter while steel-and-glass open shelving w/ a sculptural black sconce balances the composition. A vintage chandelier from Prize Home & Garden sourced in Round Top completes the room. The main floor primary suite is accessed through antique doors that open to a light-filled gallery overlooking the rear courtyard & pool. The primary bath features an extended vanity w/ dual sinks, matte black fixtures, a freestanding tub, walk-in shower w/ built-in bench & separate water closet. On the mezzanine level, the powder bath makes a dramatic statement w/ a floating black quartzite trough sink paired w/ a handwoven mirror. Across the hall, the laundry room blends beauty w/ utility w/ custom cabinetry, matching quartzite surfaces, matte black fixtures & a side-by-side front-load washer & dryer. A nearby bedroom suite is marked by an antique door entry. Each guest bedroom features an en-suite bath introduced by a hand-painted tile threshold, complemented by designer lighting, distinctive mirrors & continuous European oak flooring. The rooftop terrace is accessed from the second-floor hallway. The detached casita opens to the pool courtyard through accordion glass doors on two walls & includes a woven rattan chandelier & a full bath—ideal as a studio, gym or office. Other outdoor spaces include 2 garden courtyards, a heated saltwater pool & a newly constructed outdoor kitchen designed to accommodate a built-in grill & Big Green Egg. A spacious gravel courtyard is ideal for dining or relaxing and is enveloped by mature bamboo that creates exceptional privacy. Additional features include a lower-level two-car garage, storage closet, 3 HVAC systems, Rinnai tankless water heater, Sierra Pacific windows, customized closets, solid core doors, 6” round gutters & a Barcelona barrel tile roof. Thoughtfully designed & beautifully executed, 1150 Via Salerno offers a refined lifestyle within one of Winter Park’s most exclusive enclaves.

1150 Via Salerno, Winter Park
$1,725,000
5 Beds ⋅ 5 Baths ⋅ Kenilworth Shores Sec 06 SubDv. ⋅ 32789 Zip Code
WINTER PARK FIVE BEDROOM POOL HOME - Discover luxurious living in the heart of Winter Park! Crafted with exquisite attention to detail, this 5-bedroom, 4.5-bathroom pool residence showcases absolute perfection and modern elegance. Built in 2018 by David Weekley Homes, the property boasts a captivating stone façade and a private backyard oasis featuring a saltwater, heated pool and spa with water feature, and ambient lighting — an entertainer’s dream. Inside, soaring ceilings, gleaming wood floors, expansive picture windows, and an abundance of natural light create an inviting and sophisticated atmosphere. The gourmet kitchen is a chef’s paradise, with white maple cabinetry, Quartz countertops, a breakfast island, and stainless-steel gas appliances. The open floor plan seamlessly connects the kitchen, great room, and outdoor living spaces, perfect for hosting friends and family. Located on the first-floor, the spacious primary suite includes a spa-inspired bathroom, while a dedicated home office and guest suite offer comfort and versatility. Upstairs, discover three additional bedrooms, two full bathrooms, and a versatile loft space. Step outside to the wrap-around porch overlooking meticulously landscaped gardens, creating a serene and private outdoor retreat. Located just minutes from Park Avenue, Rollins College, and Advent Health Winter Park, this exceptional residence offers convenient access to top shopping, dining, and cultural attractions. Zoned for the highly sought-after Brookshire School District, this is your chance to experience elevated living in one of Winter Park’s most coveted neighborhoods. Schedule your private showing today and make this exquisite property your new home.

617 Worthington Drive, Winter Park
$2,575,000
5 Beds ⋅ 6 Baths ⋅ Fontainebleau SubDv. ⋅ 32789 Zip Code
Discover luxury living in this custom Austin Homes 5 bedroom, 5 and one half bath transitional style home that offers a blend of modern and traditional elements coupled with a highly desirable Winter Park location. This residence boasts a sought-after open floor plan with 12-foot ceilings, wide plank wood flooring and truly exceptional detailed finishes throughout. You will feel instantly at home as you pass through the fully enclosed front yard and enter through the double door entrance from the covered wrap-around front porch. The open-concept design seamlessly connect the dining room and family rooms as you make your way to the kitchen area complete with Wolf & Sub-Zero stainless-steel appliances, double islands, Wellborn custom cabinetry, and private Butler's Pantry with new washer/dryer. The gourmet kitchen opens to the spacious family room where you will find a built-in fireplace with custom millwork, recessed lighting, and beautiful French doors that open fully to the outside entertainment/living area. The split floor plan is perfect for the family and as you find your way throughout the remainder of the home, you will be impressed by the designer window treatments, plantation shutters, built-in speaker system, high-quality upgraded light fixtures, and private pool bath. The main floor includes a spacious primary retreat with a large walk-in closet and private French doors leading to the pool area. The spa-like bathroom includes a stand-along soaking tub, dual sink with stone counters and generous walk-in shower. The formal dining room and en-suite guest bedroom complete the first level. Upstairs are 3 spacious bedroom suites with full baths, a generous bonus/media room with built-in desk, and a second upstairs laundry room with hook ups. You will enjoy Florida living while relaxing on your covered lanai complete with retractable screens and summer kitchen overlooking the saltwater sparkling pool/spa with new pool heater and fully enclosed kid friendly yard. Upgrades include: Control 4, new electronic driveway entry gate, whole house interior and exterior painting, Jeld Wen solid core interior doors, hardwood floors throughout the first floor & bonus room, custom closet systems in all closets, rare 3-car garage, vinyl insulated windows, core fill & block walls, high density spray foam insulation in ceilings, R13 in frame walls, Carrier 15-Seer AC dual systems with UV filtration, and two Rinnai gas tankless water heaters, whole house water filtration. This pristine residence is situated on an oversized corner lot and it truly timeless, move-in ready, and only ½ mile to the Winter Park Raquet Club and 2 miles to famed Park Avenue to enjoy incredible dining and boutique shopping. Call now for your private tour!

1341 Place Picardy, Winter Park
$3,600,000
5 Beds ⋅ 7 Baths ⋅ Forest Hills SubDv. ⋅ 32789 Zip Code
Discover premier Winter Park luxury real estate at 1820 Glencoe Road—a stunning Dutch West Indies–inspired custom home built by FG Schaub Custom Homes. Ideally located minutes from Park Avenue, Rollins College, and downtown Winter Park, this residence offers the perfect blend of coastal architecture and modern Florida luxury living. With 4,055 sqft. of thoughtfully designed space, this Winter Park pool home features 5 bedrooms, 5 full bathrooms, 2 half baths, and a private home office. A grand entryway opens to a bright, open-concept interior with expansive Andersen windows that enhance indoor-outdoor flow—an essential feature for Florida homes. The chef’s kitchen is a standout, equipped with Wolf and Sub-Zero appliances, custom cabinetry, quartz countertops, and an oversized island ideal for entertaining. The great room offers seamless living with a wet bar, wine column, and elegant tiled electric fireplace. The first-floor primary suite serves as a private retreat with a spa-style bathroom that includes dual vanities, a soaking tub, glass-enclosed walk-in shower, towel warmer, and custom walk-in closet. A guest suite with a walk-in closet and en-suite bathroom, dining area, and main laundry room complete the first level. Upstairs, you’ll find a dedicated office, activity room, powder bath, secondary stackable laundry, and 3 spacious ensuite bedrooms—each with generous walk-in closets and ceiling fans. Designed for year-round indoor-outdoor living, the transitional room features a full summer kitchen with grill, hood vent, refrigerator, retractable screen, mini-split A/C, and an additional powder bath. Step into your private backyard oasis with a resort-style pool, spa, fire pit, outdoor shower, Travertine pool deck, and lush tropical landscaping—perfect for relaxing or entertaining. Additional features include security cameras, surround sound, an oversized 2-car garage with EV charging port, epoxy floors, LED lighting, a paver driveway with extra parking, standing seam metal roof, privacy fencing, and professional landscaping. Located in one of Winter Park’s most desirable neighborhoods and zoned for Audubon K-8 / Winter Park High School. Schedule your private tour today. **Builder is offering up to $30,000 in buyer incentives toward window treatments with an acceptable offer.**

1820 Glencoe Road, Winter Park
$425,000
2 Beds ⋅ 2 Baths ⋅ Lake Virginia Condo SubDv. ⋅ 32789 Zip Code
Welcome to this newly updated 2-bedroom, 2-bath condo ideally situated just steps down from shops, dining, and cultural attractions of Park Ave and Rollins College. Freshly painted and featuring brand-new flooring throughout, this home offers a perfect blend of comfort, convenience, and modern style. The spacious open layout includes a bright living area that opens to a lovely screened-in lanai—perfect for enjoying your morning coffee or relaxing after a day on the lake. The primary suite boasts a generous walk-in closet and an en suite bath, providing a private and relaxing retreat. Located in the highly sought after Lake Virginia Condominiums, residents enjoy resort style amenities, including a lakefront pool and hot tub, boat dock, fitness center, kayak storage, fire pit, bike storage, elevator access, and reserved covered parking. Don’t miss this rare opportunity to own a modernized lakefront unit in one of Winter Park’s most desirable locations! Residents also have the option to reserve the clubhouse, which features a kitchen, comfortable seating, and direct access to the pool area—making it the perfect venue for gatherings, celebrations, or special events. A poolside guest suite is available to rent for additional visitors. Whether you're looking for a permanent residence, a seasonal getaway, or a smart investment opportunity, this move-in-ready condo offers the very best of Florida living.

690 Osceola Ave Unit 410, Winter Park
$1,800,000
5 Beds ⋅ 6 Baths ⋅ Lake Knowles Terrace Add 02 SubDv. ⋅ 32789 Zip Code
Welcome to this beautifully crafted 5 bedroom, 5.1 bathroom traditional single-family home offering over 4,100 SF of living space. Ideally located on a tree-lined street with Winter Park’s signature brick roads, this home sits in one of the area’s most sought-after neighborhoods. Just minutes from the Winter Park Racquet Club in the Vias, Park Avenue shops and dining, YMCA, top hospitals, and excellent public and private schools, it offers the best of Winter Park living. A charming front porch leads into a thoughtfully designed interior that blends classic style with modern functionality. To the right of the foyer is a private office with built-in shelving and glass pocket door, while the left opens to a formal dining room with a tray ceiling, chandelier, and ambient lighting. The spacious living room features a gas fireplace, beamed ceiling, crown molding, and built-in shelving, with French doors that open to the screened lanai for seamless indoor-outdoor living. The chef’s kitchen offers ample cabinetry, expansive countertops, a center island with secondary sink, walk-in pantry, and a breakfast nook with more French doors to the lanai. On the main floor, the primary suite includes a spa-inspired bath with double vanities, garden tub, and multiple closets. A guest suite also on the first floor includes a private bath, beverage fridge, and coffee station. A full laundry room and butler’s pantry with wine fridge complete the first level. Upstairs features a large loft with built-in cabinetry, under-cabinet lighting, and a beverage fridge. A built-in desk and cabinets line the hallway for study or work space. Two bedrooms share a Jack and Jill bath, and a third has access to a nearby full bath. A second laundry room, currently used as an office, adds flexibility. Step outside to a private backyard oasis with a screened lanai, sparkling pool, outdoor kitchen, mature landscaping, and full pool bathroom. With a new roof (2023), commercial grade water heater (2022), fresh exterior paint (2024) and many upgrades, this home offers turnkey living in one of Winter Park’s finest communities.

1355 Hibiscus Avenue, Winter Park
$1,270,000
4 Beds ⋅ 4 Baths ⋅ Fontainebleau SubDv. ⋅ 32789 Zip Code
Seller is including a premium home warranty giving buyers peace of mind with coverage on HVAC, plumbing, appliances & more so you can move in with confidence! Experience the charm and elegance of Winter Park living in this beautifully designed 4-bedroom, 3.5-bath home offering 3,604 square feet of thoughtfully crafted space. Built in 2014, this residence combines timeless architectural character with modern functionality, all nestled on a quiet, tree-lined street in one of Central Florida’s most sought-after neighborhoods. From the moment you enter, you’re welcomed by warm natural light, an open and inviting layout, and high-quality finishes throughout. Enjoy a spacious chef’s kitchen, generous living and dining areas, and a private primary suite perfect for both entertaining and relaxing. The detached two-car garage and charming outdoor space add to the home’s appeal and functionality. This home features a spacious primary master suite located on the first floor, offering privacy, convenience, and ease of living. Located just minutes from the heart of Park Avenue, you’re steps from some of Winter Park’s most beloved spots—fine dining, boutique shopping, museums, and local cafés. Nearby favorites include The Ravenous Pig, Hillstone, Boca, Ava MediterrAegean, and the world-renowned Winter Park Farmers’ Market. With easy access to I-4, 17-92, and Semoran Blvd, commuting to downtown Orlando, Maitland, or the airport is a breeze. Call to set your appointment to view this lovely home!

2401 Lafayette Avenue, Winter Park
$916,000
3 Beds ⋅ 3 Baths ⋅ Kenilworth Shores Sec 06 SubDv. ⋅ 32789 Zip Code
Nestled in the heart of Winter Park in one of the area’s most sought-after neighborhoods, this professionally designed and fully renovated 3-bedroom, 2.5-bathroom home offers luxurious living with timeless modern style. Step inside to an open-concept layout featuring a gourmet kitchen outfitted with custom cabinetry, stunning quartz countertops, GE Café appliances, a Thermador drawer-style microwave, Brizo faucets, a coordinating pot filler above the stove, and designer light fixtures—perfect for both entertaining and everyday living. Adjacent to the kitchen, a custom wine and coffee bar with floating shelves seamlessly blends style and functionality. For dog lovers the home even includes a whimsical “Doggie Bistro,” complete with its own pot filler, making it a breeze to refill water bowls! This meticulously maintained single-story home offers abundant storage, including generous bedroom closets, attic access, and garage overhead storage. Additional space is available in the backyard shed and the oversized two-car garage with built-in storage. Bathrooms have been completely remodeled with premium finishes, high-end vanities, and designer fixtures that combine elegance and functionality. The powder room near the main living space adds the perfect touch of sophistication and convenience. The front living room features a wood-burning fireplace and a large picture window that fills the space with natural light. Step outside to your private, fully fenced backyard, shaded by a canopy of fragrant jasmine and serenaded by the sounds of local peacocks. With ample space for relaxing or entertaining, the yard also offers a perfect canvas for a future pool. No detail has been overlooked. Recent upgrades include: New roof (2019), new A/C unit (2023), Blow-in insulation, sprinkler system, home water softener, PGT energy-efficient windows (2019), custom pergola with screen, original refinished hardwood floors throughout the main living spaces and bedrooms. Garage auto carpet to create multi-use space. Located just minutes from downtown Winter Park, top-rated schools, award-winning restaurants, scenic parks, and the popular Cady Way Trail, this home offers the best of Central Florida living. With easy access to downtown Orlando, major highways (408, 417, I-4), Disney attractions, and Orlando International Airport. The neighborhood continues to evolve, with many homes being replaced by larger custom homes valued at over $3 million. This is a rare opportunity to own a turn-key home in a highly desirable community!

609 Langholm Drive, Winter Park
$705,000
3 Beds ⋅ 2 Baths ⋅ Charmont SubDv. ⋅ 32789 Zip Code
Unlock the potential of this charming 3-bedroom, 2-bathroom home—ideal for renovation or building your custom dream residence. Nestled among a mix of beautifully preserved historic homes and stunning new construction, this property is located in one of Central Florida’s most sought-after neighborhoods. The home features classic terracotta tile flooring, two cozy wood-burning fireplaces—one in the inviting living room and another in the spacious primary suite—and a detached workshop perfect for hobbies or additional storage. Enjoy the best of both convenience and lifestyle just minutes from vibrant Park Avenue’s boutiques and restaurants, Downtown Orlando, Baldwin Park, and an array of local parks and recreation. Don’t miss this rare opportunity to create something truly special in the heart of Olde Winter Park!

1840 Laurel Road, Winter Park
$1,000,000
4 Beds ⋅ 4 Baths ⋅ Winter Park Village SubDv. ⋅ 32789 Zip Code
Welcome to 2607 Lafayette Avenue – a stunning custom-built residence nestled in one of Winter Park’s most desirable neighborhoods. This beautifully crafted home offers 4 spacious bedrooms, 3.5 bathrooms, and 2,770 square feet of refined living space designed for modern comfort and effortless entertaining. Step inside to discover an open-concept layout that seamlessly connects the kitchen, dining, and living areas. The kitchen features brand-new appliances, quartz countertops, shaker-style cabinetry, a classic subway tile backsplash, and a large island ideal for gathering. Elegant new light fixtures and a built-in wet bar elevate the space with a touch of sophistication. The first-floor primary suite is a serene retreat, offering two closets and a well-appointed en-suite bathroom complete with a soaking tub and separate walk-in shower. Upstairs, a spacious loft opens to a walk-out balcony and is accompanied by three additional bedrooms and two full bathrooms – perfect for family and guests. Storage is abundant with three walk-in closets, a double closet, and a convenient under-stair space. Additional highlights include a two-car garage with an epoxy floor, a screened patio for year-round enjoyment, and a fenced backyard oasis ideal for relaxation or entertaining. Freshly painted and surrounded by all-new professional landscaping with an irrigation system, this home offers exceptional curb appeal. Located just minutes from Park Avenue’s shopping and dining, Rollins College, the Winter Park Chain of Lakes, and zoned for A-rated Dommerich Elementary, Maitland Middle, and Winter Park High School—this property blends luxury, location, and lifestyle.

2607 Lafayette Avenue, Winter Park
$1,300,000
4 Beds ⋅ 4 Baths ⋅ Comstock Park SubDv. ⋅ 32789 Zip Code
**DON'T LET THIS OPPORTUNITY PASS YOU BY, BACK ON MARKET DUE TO BUYERS FINANCING.** Luxurious Retreat in the Heart of Winter Park’s Premier Neighborhood – Minutes from Park Ave! Discover timeless elegance in this stunning 4-bedroom, 3.5-bathroom home offering 2,953 square feet of thoughtfully designed living space. Nestled on tree-lined streets in one of Winter Park’s most coveted areas, surrounded by multi-million-dollar estates and just moments from the Winter Park Chain of Lakes, this home defines luxury living. Step through the impressive cut beveled glass double front doors into an interior filled with natural light, featuring hardwood floors, crown molding, recessed lighting, and blinds and Roman shades throughout. Formal living and dining rooms provide an elegant backdrop for entertaining, while the fireplace in the family room adds a cozy touch. Sliding French doors and two sets of large sliders seamlessly extend the living space to the private pool area. A sunroom (added in 2024) with a mini split system offers additional space to relax and unwind. Enjoy modern upgrades including a monitored security system, intercom system, reverse osmosis water filtration, and a water softener system. The gourmet kitchen is a chef’s dream with custom wood cabinetry, wavy tiled backsplash, granite countertops, stainless appliances including a newer refrigerator (2024) and newer dishwasher (2022), a gas stove, and two pantries, including a walk-in pantry. The breakfast nook and breakfast bar with seating for three creates plenty of space for gathering. Retreat to the luxurious primary suite with wood floors, a large walk-in closet, and a spa-like ensuite bathroom featuring double split vanities, a garden soaking tub, a large tiled shower, and a private water closet. Enjoy your own private backyard paradise on a .26-acre lot with a resort-style in-ground pool (2021), waterfall feature, sun shelf, lush landscaping, and irrigation system. An electronic front gate provides peace of mind for security as you're guided to a paved driveway and parking pad with a 2-car garage to complete this exceptional property. All this in a highly sought-after location, just minutes from Park Avenue’s high end shops and fine dining restaurants, Rollins College/Dinky Dock public boat ramp, Winter Park 9 Golf Club, Winter Park Racquet Club, Interlachen Country Club, Winter Park YMCA and WP Phelps Park and playground and so much more! Don’t miss your chance to own a piece of Winter Park’s finest! Schedule your private tour today. (Roof: 2019, HVAC 2017, Mini Splits (2) 2024, Electrical 2004, Plumbing 2004)

1420 Palmer Avenue, Winter Park
$1,400,000
5 Beds ⋅ 4 Baths ⋅ Waterbridge SubDv. ⋅ 32789 Zip Code
This 5 bedroom, 4 full bathroom one story refreshed ranch estate boasts nearly 4,200 sq ft and features 3 fireplaces, double primary suites, and sprawls out on an oversized .36 acre lot, overlooking an open air salt water & solar heated pool. Updates & upgrades include: full roof replacement with transferable warranty (2023), new windows with transferable warranty (2023), 4 newer ACs (2 are 2023 & 2 are 2017), pool resurfaced with new waterline tiles and stacked stone (2023), pool salt cell replaced with 3 year warranty (2025), new carpet in bedrooms (2025), fresh sod in the backyard (2025), new turf in atrium (2025), exterior paint (2023), plantation shutters throughout, tile floors (2016), closets by design. The kitchen has undergone a full remodel & is the heart of the home. It features quartz countertops, a 10' quartz peninsula, a Bosch cooktop, Bosch oven with a top built-in microwave, a GE cafe smudge proof fridge and a farmers sink. The kitchen opens up to the family room, with a stacked stone feature wall and built-in shelving, all surrounding the cozy wood burning fireplace. The primary bedroom is split on one side of the home, offering privacy, is oversized and features a seating area with it's own wood burning fireplace. The ensuite primary bathroom has been remodeled with dual sinks, a deep soaking tub and a separate shower stall with floor to ceiling tile & glass frame. The second primary bedroom, which would function perfectly as an in-law or nanny suite, is split on the other side of the home and features it's own AC & water heater, with an ensuite bathroom. The additional 3 bedrooms can also be found on this side of the home, 2 of which share a jack n jill bathroom, and the final & 5th bedroom, measuring 25X12, has enough room for double office spaces or could be utilized as an office & work out space. While the home features a formal living, formal dining, family room & dining nook, there is also a secondary living space, off the secondary primary suite, complete with a wet bar, wine chiller and an electric fireplace. It's the perfect flex room and could serve as a separate in-law living area or a game room. The pool is a show stopper and has been resurfaced, including the install of new waterline tiles and stacked stone. With a sun shelf & bubbler, this pool offers resort style relaxation and is surrounded by a resealed paver deck. The side yard is ample space to play and has been freshly sodded. Zoned Winter Park High, Glenridge Middle & Brookshire Elementary, and just minutes from Advent Health Winter Park Hospital, the East End Market, which serves as a hub of market & culinary delights, and less than 4 miles from the popular Park Avenue, where you can enjoy acclaimed eateries and some of Orlando's best shopping, the location is highly desirable. Move right in, everything has been done.

1327 Bridgeport 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
$1,318,000
3 Beds ⋅ 3 Baths ⋅ Jenkins Add SubDv. ⋅ 32789 Zip Code
Welcome home to this one-of-a-kind, single-story Tuscan-style retreat nestled on an oversized lot in the heart of highly coveted Winter Park. From the moment you arrive, the round circular paver driveway and beautifully landscaped exterior set the tone for the warmth and elegance that awaits inside. Enter through custom wrought-iron gates into a private covered and screened in courtyard lanai, where a tongue-and-groove wood ceiling and a fully equipped gas summer kitchen create the perfect backdrop for effortless outdoor entertaining and everyday relaxation. Designed with character and comfort in mind, this thoughtfully updated home features exposed brick, wood-beamed ceilings, Italian porcelain tile, engineered wood flooring, and two sleek accordion glass doors that invite the outdoors in, creating a seamless indoor-outdoor lifestyle. The chef-inspired kitchen is the heart of the home, boasting quartz countertops, a mosaic backsplash, custom cabinetry, double sinks, a skylight, and newer stainless steel appliances—including a gas cooktop and wine fridge. The kitchen flows effortlessly into the dining and living areas, anchored by a Vermont Castings wood-burning stove with catalytic combustor framed in brick. Just steps away, a spacious butler’s pantry and laundry room lead to the attached air-conditioned two-car garage with epoxy floors, perfect for a home gym, storage, or EV charging. The split floor plan ensures ultimate privacy for the master suite, which overlooks the lush backyard and nearby park. French doors lead to a large walk-in closet and a newly renovated en-suite bath with dual vanities, a soaking tub, and a spa-style walk-in shower. The master also offers private access to the central courtyard. A detached third bedroom with its own full bath and newer flooring is ideal as a guest suite, home office, or income-producing rental space. In the rear of the property, a second, detached 20-foot-wide garage—also air-conditioned with epoxy flooring—is accessible through a separate gated driveway and offers even more space for collectibles or hobbies. The fully fenced backyard, rich with mature landscaping and orange trees, has room to add a pool and offers direct private access to Phelps Park with tennis, pickleball, basketball courts, a playground, and green space. Enhanced with a 5.7 kW solar panel array that doubles as the lanai roof, a brand-new 18 SEER York HVAC system, foam roof deck insulation, and extra wall soundproofing, this home is as energy-efficient as it is luxurious. Complete with a multi-zone irrigation system and landscape lighting, this truly special property offers the perfect blend of timeless charm, modern comfort, and an unbeatable Winter Park location. Perfectly situated on the iconic, tree-lined Palmer Avenue, this home offers unbeatable walkability—just a short stroll to Phelps Park and mere minutes from the boutiques and dining of Park Avenue, Interlachen Country Club, and the Winter Park Racquet Club- set up your private showing today.

1741 Palmer 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
$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
$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
$234,000
2 Beds ⋅ 1 Baths ⋅ Lake Killarney Condo SubDv. ⋅ 32789 Zip Code
One or more photo(s) has been virtually staged. Investors Dream with Minimal Lease Restrictions! Back on Market. Buyer financing fell through. Welcome to the Lake Killarney Condo Community! This two-bedroom, one-bathroom condo features sold surface countertops in the kitchen, complete bathroom renovation with updated fixtures, newer floors in some rooms, washer/dryer hookups, newer kitchen appliances, and a complete interior fresh coat of paint. Central heat/air was also added by the current owner to the screened in patio/balcony, including a closed off air duct to the balcony/patio, should you want to enclose the area. With a partial lake view from the patio, all you have to do to embrace nature is step outside your front door. This unit includes 1 parking space and visitor parking as well. Other amenities include the community pool, which overlooks Lake Killarney, a private loading dock for the boating expert in you, shuffleboard courts, grilling stations, and scenic outdoor seating areas, perfect for picnics, romantic sunsets, and daily meditation. HOA options for boat parking and dedicated kayak storage based upon availability. Located next door to Trader Joe’s and across from Winter Park Village, this condo offers convenient access to premier shopping, dining, and entertainment. Take a boat ride to Hillstone for happy hour or a delicious meal, relax in the pool while watching the sunset, or read a book under one of the park trees. Book your showing today and begin your ultimate lake life living!

151 N Orlando Avenue Unit 204, Winter Park
$2,495,000
4 Beds ⋅ 5 Baths ⋅ Robert Dhu Macdonald Park SubDv. ⋅ 32789 Zip Code
Now offered at $2,495,000—an outstanding value for a thoughtfully designed pool home on a spacious lot in Winter Park’s most sought after neighborhoods. Located in the heart of the “Golden Triangle”—the core residential district just a short walk from Park Avenue’s world-class shopping and dining—940 Lincoln Circle is a beautifully renovated West Indies/Key West-style home that blends architectural charm, comfortable elegance, and thoughtful functionality on an oversized .33-acre lot. With 4 bedrooms and 4.5 bathrooms across 3,551 square feet, this home lives primarily as a one-story layout, enhanced by a private upstairs suite with bedroom, full bath, and bonus room—accessible from both inside and a separate outdoor entry. Ideal for multigenerational living, guests, or private work/living quarters, this flexible plan is rarely available in such a prime location. A gated front porch and covered entry open into the foyer and an expansive formal living room with vaulted wood-paneled ceilings and gas fireplace. The space flows easily into the dining area and kitchen, which overlook the screened porch and backyard oasis. The kitchen is appointed with marble countertops, custom cabinetry, gas cooktop, cabinet-paneled Sub-Zero refrigerator/freezer, double ovens, and a walk-in pantry. A custom wine room—perfect for entertaining—sits just off the main living space. A nearby den (or optional fourth bedroom with closet) is paired with a bright enclosed Florida room currently used as a home office with rose garden views. This wing connects to a full bath and a secondary bedroom at the front of the home. A stylish powder bath is conveniently tucked away for guests. The private primary suite is positioned at the rear of the property and features a soft entry, dual custom closets, outdoor access, and a beautifully appointed bathroom with dual vanities, glass-enclosed shower, soaking tub, and private water closet. Upstairs, a second guest suite with bonus/flex room and full bath is ideal for visitors, a gym, or studio. At the rear of the home, a welcoming family room with fireplace opens to the covered lanai and kitchen, offering ideal indoor-outdoor flow. The backyard is a fully fenced retreat with lush landscaping, renovated saltwater pool with new equipment, and mature trees surrounding multiple hardscape patios and garden paths. A well-appointed full bathroom with exterior access off the screened patio offers convenient functionality for pool use, gardening, or even dog washing—enhancing the home’s seamless indoor-outdoor lifestyle. The outdoor kitchen includes a Blaze grill, Fire Magic refrigerator, Blackstone griddle, stainless sink, storage cabinetry, and vent hood—creating a true resort-style environment. The oversized two-car garage features epoxy floors, built-in storage, and space for larger vehicles. Additional highlights include two Rinnai tankless water heaters, 2024 Trane condenser, 2019 Mitsubishi mini-split, full-house Generac generator with transfer switch, motorized shades by The Shade Store, and a well-appointed laundry room with built-in cabinetry, utility sink, and yard access. A rare opportunity in Winter Park’s most walkable and desirable neighborhood.

940 Lincoln Circle, Winter Park
$3,200,000
6 Beds ⋅ 6 Baths ⋅ Windsong Lakeside Sec 01 43/70 SubDv. ⋅ 32789 Zip Code
**This stunning estate just became an unbeatable opportunity--luxury living at a dramatically reduced price! Don't miss your chance to own this exceptional home in the highly coveted Windsong community with access to the gorgeous Winter Park chain of lakes. Prepare to be impressed as you enter this almost 6,000 square foot home adorned with custom high-end features throughout, plus a fabulous guest apartment with a full bathroom and kitchenette fully renovated to be enjoyed as a private poker/bourbon room. This exceptional residence has been converted to a full Smart Home with integrated controls for lighting, audio/video, security system with cameras, intercom, thermostat and sun shade. The beautiful chef's kitchen boasts a brand new 48” Sub-Zero refrigerator, and all new Wolf appliances including double 30” electric ovens, microwave, gas cooktop, hood insert, and warming drawer. For added convenience, a fully appointed Butler's pantry is adjacent to the kitchen. Retreat to the stunning first floor owner's suite featuring a newly installed electric fireplace, sitting area, a walk-in closet with custom cabinetry, a separate office/home gym and a spa-inspired bathroom with a jetted tub and steam shower. Just outside, step into your own personal wellness retreat with a new Polar Monkey brand cold plunge and a four-person sauna. Also, guests will enjoy the convenience of another private first floor bedroom suite. Upstairs are the additional three spacious bedrooms and bathrooms, a huge loft area, and hidden stairs leading to a generous air conditioned storage room, great for a home theater. The outside oasis greets you with a fully reimagined expansive covered lanai with an outdoor kitchen complete with a 60" Fire Magic grill, 60" Fire Magic vent hood, Summit refrigerator, and stainless steel cabinets. Relax by the sparkling saltwater pool with its sun shelf, retractable screen, and travertine deck surrounded by lush tropical landscaping and artificial turf for carefree living. The extensive renovations to this luxury estate continue with the installation of a new roof, new gutters with leaf guards, freshly painted exterior, new wood trellis, all new saltwater pool equipment, and epoxy garage flooring with added custom cabinets. Embrace this luxury lifestyle with exclusive access to the Windsong Residence Club overlooking the Winter Park Chain of Lakes, with amenities including lake access, community pools, splash park, playground, and use of the pontoon boat. This home may be purchased fully furnished. Don't miss the opportunity to own this spectacular home in one of Winter Park's most sought after neighborhoods with its top-rated schools, and proximity to shopping and dining on Park Avenue in picturesque downtown Winter Park!

141 S Phelps Avenue, Winter Park
$718,500
3 Beds ⋅ 3 Baths ⋅ Quarters At Winter Park Condo Ph 2 SubDv. ⋅ 32789 Zip Code
One or more photo(s) has been virtually staged. A rare (and low-maintenance!) gem, this 3 bed/2.5 bath home is located just around the corner from Park Avenue and Rollins College. Tucked away in the most perfect location, this 2-story Winter Park condo was stripped down to the studs and completely remodeled in 2007 with all new plumbing, electrical, ductwork, flooring, appliances, and natural gas line, plus (2) newer HVAC systems installed in Nov. 2022. The gated front courtyard was designed by a landscape architect, where foliage, a potted herb garden, wooden bench, and fountain create a tranquil welcome for your guests. Enter to a spacious dining room flooded with natural light through the bank of French doors that open to the courtyard. A built-in dry bar, complete with 2 wine refrigerators, makes this a perfect space for entertaining, while oak wood flooring throughout the home adds warmth and charm. The stylish chef’s kitchen has cool concrete counters, custom cabinetry, and dual-fuel 6-burner Wolf range, plus a cozy dinette with a built-in terrazzo-topped table and banquette. A breakfast bar provides extra seating, and the living room beyond includes a clean-burning bioethanol fireplace and soaring windows with views of the interior screened 2-story courtyard. Upstairs, the private primary retreat offers multiple closets, a balcony overlooking the interior courtyard, and an en-suite bath featuring a large walk-in shower with body sprays, a towel warmer, and a laundry room with built-in storage. At the opposite end, the front-facing bedroom can double as an office, with a custom built-in desk and shelving along one wall, plus a screened balcony that overlooks the front courtyard, perfect for sipping your morning coffee or tea. A 3rd bedroom, 2nd full bathroom, linen closet, and quaint sitting area/nook complete the second floor. A private alleyway behind the building provides access to the oversized 2-car garage with a custom built-in workbench and sink, and 2 dedicated storage units. Walk to the Rollins, Park Avenue, the Winter Park Tennis Center, Azalea Lane Playground, or through the brand new Seven Oaks Park on your way to the shops and eateries along Orange Avenue. The ideal blend of sophistication and practicality, this condo is simply perfect for those seeking an effortless lifestyle in the heart of Winter Park.

1130 Washington Avenue Unit 11-C, 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