Winter Park Homes For Sale & Real Estate - 437 homes

Remarks: Step into elevated Florida living with this stunning brand-new residence, where modern design meets lasting quality. Constructed with solid block and steel framing for superior durability, this home is quietly nestled on a cul-de-sac in one of Winter Park’s most up-and-coming areas—without the restrictions of an HOA. Just moments from Interlachen Country Club and the charming Lakemont Heights neighborhood, the location offers both prestige and convenience. From the moment you enter through the impressive double doors, you’re welcomed by a light-filled, open-concept design. Soaring 10-foot ceilings and elegant 8-foot doors create an airy, expansive feel, while abundant natural light highlights the home’s sleek, contemporary finishes. At the heart of the home, the chef-inspired kitchen truly shines. Outfitted with luxurious quartz countertops, stainless steel appliances, and a custom LED-lit wine display, it’s designed to impress. The seamless flow into the living and dining spaces—along with views of the backyard—makes it perfect for entertaining or everyday connection. The primary suite is a private sanctuary, offering a spa-like escape with dual vanities, a spacious dual-entry shower, and a freestanding soaking tub designed for relaxation. With three additional bedrooms, a dedicated office, and 3.5 beautifully appointed bathrooms, this thoughtfully designed single-story home provides nearly 2,500 square feet of flexible living space. Outdoors, your personal retreat awaits. Enjoy year-round Florida living on the covered lanai, complete with a built-in summer kitchen and a custom-designed pool—ideal for hosting or unwinding. The fully fenced yard features new vinyl fencing, fresh sod, and an automated sprinkler system for effortless maintenance. Perfectly positioned near Phelps Park, the Winter Park YMCA, Lakemont Elementary, and an array of top-tier shopping and dining destinations, this home delivers the ideal blend of privacy, craftsmanship, and everyday luxury.

Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)

Listing Agent: Nick Mckee (407-913-0171)

Remarks: Virtually Staged. **Price Improvement** Welcome home to this beautifully updated two-story end-unit, ideally located just steps from Michelin-star dining, local boutiques, and the vibrant East End Market. On weekends, enjoy leisurely strolls to the area’s popular farmers markets and neighborhood events. Situated in the heart of Winter Park, this residence offers the perfect blend of lifestyle, convenience, and charm in one of Orlando’s most sought-after communities. Designed for both everyday comfort and effortless entertaining, the first floor features an open-concept kitchen and living area filled with abundant natural light, along with a convenient half bath—ideal for hosting guests. Upstairs, the spacious primary suite boasts a private ensuite bathroom, walk-in closet, and a newly refinished balcony—perfect for morning coffee or evening cocktails. Two additional bedrooms provide generous space and share access to a second balcony, creating a seamless indoor-outdoor living experience. Recent upgrades include a new dishwasher and smart refrigerator (2022), new water heater (2025), refinished front balcony (2025), new roof, and new carpet upstairs (2026). Updated light fixtures and primary bedroom flooring within the last five years add a modern touch throughout. The $400 monthly HOA fee includes landscaping and insurance, offering low-maintenance living and added peace of mind. Zoned for some of Orlando’s top-rated schools and walking distance from the new Audubon Park K-8 School, this home presents a rare opportunity to enjoy the very best of Winter Park living. Don’t miss your chance to call this exceptional property home.

Listing is courtesy of: ALL REAL ESTATE & INVESTMENTS (407-917-8206)

Listing Agent: Courtney Dietch (407-952-3779)

Remarks: One or more photo(s) has been virtually staged. PRICE IMPROVEMENT! NO HOA! Experience refined living in this renovated custom designed home on a corner lot in one of the area’s most peaceful and private neighborhoods. Tucked away at the end of a quiet dead-end street, this residence offers an exceptional blend of craftsmanship, sophistication, and modern comfort. With soaring 10-foot ceilings throughout and a stately wood-burning fireplace which sets a welcoming feeling in the family room. The fully reimagined chef’s kitchen is a true showpiece, featuring solid maple cabinetry, quartz countertops, programmable Bosch stainless steel range and refrigerator and a striking brick backsplash—an elevated space designed for both culinary creativity and effortless entertaining. All three bathrooms have been luxuriously renovated, and new carpeting adds a soft, refined touch throughout all four bedrooms. French doors from the master suite, formal living room, and family room open to a breathtaking screened-in pool retreat. Surrounded by lush tropical landscaping, this private oasis has been thoughtfully upgraded with a new pool pump, a conversion to a sparkling saltwater system, and a beautifully refinished pool deck. An outdoor shower with both hot and cold water adds a resort-level convenience, perfect after a swim or a day in the sun. Every major system has been meticulously updated for peace of mind, including a new programmable HVAC system, a complete replumb of the entire home, all new ductwork, and an upgraded water heater. Additional enhancements—such as fresh interior and exterior paint, a new garage door opener in the over-sized garage, irrigation system and refreshed landscaping — ensure a truly turnkey experience. With its luxurious finishes and meticulous improvements, this residence is ready for the next family to make it their own. This property is located just 2 miles to AdventHealth Winter Park Hospital, less than 10 minutes to Park Ave, and zoned for top-rated schools: Dommerich Elementary, Maitland Middle, and Winter Park High School. Just minutes from Winter Park’s boutiques, acclaimed restaurants, and the cultural charm of Park Avenue, this home offers a rare opportunity to enjoy elevated living in a setting that’s both secluded and connected. A truly private sanctuary designed for comfort, style, and the best of Florida living.

Listing is courtesy of: FLORIDA REALTY INVESTMENTS (407-207-2220)

Listing Agent: Kathy Summers (407-832-6986)

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

Listing is courtesy of: CREEGAN GROUP (407-622-1111)

Listing Agent: Chris Creegan (407-622-1111)

Remarks: Move right in and enjoy low-maintenance living in the desirable Hidden Oaks community of Winter Park. This meticulous maintained and nicely updated 2-bedroom, 2.5-bath townhome-style condo features two spacious primary suites, each with its own private en-suite bathroom, offering a flexible floor plan and exceptional functionality. The open and inviting layout includes an oversized great room, 12-inch ceramic tile flooring, and a well-appointed kitchen with maple cabinetry, Corian countertops, flat-top range, stainless steel refrigerator, and new microwave. The washer and dryer are included, making this home truly move-in ready. Both bathrooms have been tastefully updated, maple cabinetry, one with granite & one with Corian countertops for a cohesive, modern look. Enjoy outdoor living on the private rear patio, complete with space for grilling and an additional storage closet. Hidden Oaks is a beautifully maintained community featuring mature landscaping, a community pool, and a convenient Winter Park location near shopping, dining, entertainment, major employers, and highly rated Winter Park schools. The monthly condo fee includes water, sewer, trash, exterior maintenance, grounds maintenance, and community amenities, creating an easy lock-and-leave lifestyle. Conveniently located near Full Sail University, the University of Central Florida, Downtown Winter Park, and major roadways, this home offers an excellent opportunity for owner-occupants, those seeking a second home, or buyers looking for a long-term investment property. Don't miss the chance to own a well-maintained and move-in-ready home in one of Winter Park's most convenient locations.

Listing is courtesy of: MAINFRAME REAL ESTATE (407-513-4257)

Listing Agent: Alie Gattis (407-760-1488)

Remarks: Nestled within the highly sought-after Kenilworth Shores neighborhood, this extraordinary new construction home represents a rare opportunity to own one of Winter Park's finest new builds. Thoughtfully designed with an exceptional floor plan and uncompromising level of craftsmanship, detail, and finishes. This home is located just minutes from everything Winter Park has to offer. Step through the front doors into a breathtaking two-story foyer where soaring ceilings, and a statement chandelier create an unforgettable first impression. Designed for both everyday living and effortless entertaining, the floor plan is one of the home's most desirable features. Rare for Winter Park, the residence offers a luxurious primary suite, private guest suite, and dedicated office all on the main level. The expansive living room serves as the heart of the home, showcasing extensive custom trim work, an electric fireplace, and bespoke built-in cabinetry with LED underlighting. Walls of glass create a seamless connection to the outdoor living spaces while filling the home with natural light. The chef's kitchen is a true showpiece, designed to satisfy even the most discerning culinary enthusiast, featuring stunning Calacatta quartz countertops, custom cabinetry, a paneled built-in refrigerator, and a complete suite of Thermador appliances. Adjacent to the kitchen, the formal dining room creates an elegant setting for entertaining, featuring a custom dry bar complete with a wine refrigerator. Privately tucked away, the primary suite serves as a true retreat, featuring sliding glass doors leading directly to the backyard oasis, creating a seamless indoor-outdoor connection. The spa-inspired primary bath features marble mosaic tile, floating mirrors above dual vanities, a freestanding soaking tub, an oversized walk-in shower, and a generous walk-in closet. The upper level continues the home's thoughtful design with a spacious loft, accompanied by three generously sized bedrooms. Outdoor living is equally impressive, a covered lanai creates the perfect setting for year-round entertaining and is fully equipped with a summer kitchen. The beautifully designed backyard retreat showcases a sparkling pool and spa surrounded by lush green space, offering the ideal balance of recreation, relaxation, and privacy. Perfectly positioned in the heart of Winter Park, residents enjoy tree-lined streets while remaining just a golf-cart ride from the boutiques, award-winning restaurants, and cafés, of Park Avenue. The home is also conveniently located near Winter Park High School, Advent Health Winter Park, and the beloved Cady Way Park, where tennis courts, soccer fields, baseball fields, walking trails create one of Central Florida's most desirable active lifestyles. Don't miss out on this amazing new home!

Listing is courtesy of: ONE LUXURY INTERNATIONAL LLC (407-312-8003)

Listing Agent: Christopher Christensen (407-312-8003)

Remarks: Completely reimagined and professionally renovated, this stunning Winter Park POOL home offers approximately 1,950 square feet of thoughtfully designed living space with a rare 4-bedroom, 3-full bathroom floor plan, a 2-car garage, and an exceptional blend of style, function, and quality craftsmanship. At the heart of the home is a show-stopping open-concept kitchen featuring custom shaker cabinetry, quartz countertops, a dramatic oversized center island, designer lighting, a custom range hood, and a striking tile feature wall that creates a true focal point for the home. Warm wood accents, curated finishes, and seamless flow into the living and dining spaces make this home ideal for both everyday living and entertaining. The split-bedroom floor plan provides privacy and flexibility, with the primary suite situated on one side of the home and the secondary bedrooms located on the opposite side. All three bathrooms have been completely gutted and beautifully remodeled with high-end finishes and timeless design selections. Luxury vinyl plank flooring extends throughout the home, creating a cohesive and modern aesthetic. Major improvements include a NEW roof (2026), NEW AC system, NEW windows, NEW electrical, NEW water heater, RESURFACED POOL, updated lighting throughout, inside laundry room, and extensive interior renovations that allow buyers to enjoy the benefits of a truly move-in-ready home. Situated in the highly desirable Winter Park Pines area, residents enjoy convenient access to Park Avenue, Downtown Winter Park, Cady Way Trail, Rollins College, Full Sail University, UCF, shopping, dining, major roadways, and Orlando International Airport. Combining designer finishes, an open modern layout, a private pool, and an unbeatable location, this is a rare opportunity to own a fully renovated home in one of Central Florida's most sought-after communities. Schedule your private showing today.

Listing is courtesy of: RE/MAX TOWN & COUNTRY REALTY (407-695-2066)

Listing Agent: Belinda Gonzales (321-277-8994)

Remarks: Welcome to Winter Park Pines, one of Winter Park's most desirable and established neighborhoods! Situated on nearly a quarter-acre lot, this beautifully maintained home with fresh interior paint combines modern updates, everyday comfort, and an unbeatable location. The stunning recently updated kitchen serves as the heart of the home, featuring stylish finishes and an inviting space for cooking, entertaining, and gathering. Throughout the home, you'll find attractive flooring with no carpet, offering both a clean, modern look and easy maintenance. Major improvements provide peace of mind, including a new roof and complete re-plumbing completed in 2023. The spacious lot offers plenty of room to enjoy outdoor living, gardening, pets, or future possibilities. Location is everything, and this home delivers. Just steps from Cady Way Pool and the popular Cady Way Trail, you'll enjoy easy access to recreation, fitness, and outdoor activities. Residents also love the convenient proximity to restaurants, shopping, parks, golf, and the charm of Downtown Winter Park. Best of all, there is no HOA, providing added flexibility and freedom. With significant recent updates, a generous lot, and a prime location in highly sought-after Winter Park Pines, this move-in-ready home is a wonderful opportunity to enjoy the very best of Winter Park living.

Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)

Listing Agent: Jonathan Cole (407-928-9516)

Remarks: LOCATION LOCATION LOCATION. Discover exceptional new construction in the heart of Winter Park. Completed in 2025, this stunning Mediterranean-inspired residence offers 5 bedrooms, 4 bathrooms, and nearly 2,900 square feet of thoughtfully designed living space. Situated on a charming, tree-lined street, the home combines timeless elegance with modern luxury. The open-concept floor plan features 10-foot ceilings, 8-foot doors, luxury vinyl plank flooring throughout, and an expansive great room with an electric fireplace. The gourmet kitchen is designed to impress with quartz countertops, custom cabinetry, stainless steel appliances, a large center island, and abundant storage. A unique under-stair wine cellar adds character and sophistication, while a first-floor guest suite provides privacy and flexibility. Upstairs, the spacious primary suite overlooks the backyard and pool area and includes a spa-inspired bathroom with dual vanities, a soaking tub, walk-in shower, and generous walk-in closet. Three additional bedrooms comfortable accommodations, including a Jack-and-Jill layout and a private In-suite bedroom. A conveniently located upstairs laundry room completes the second level. Step outside to your private outdoor retreat featuring a beautifully landscaped backyard, sparkling in-ground pool, covered lanai, and summer kitchen with built-in grill—perfect for entertaining year-round. Ideally located just minutes from Winter Park’s renowned shopping, dining, parks, and cultural attractions, this exceptional home offers the rare opportunity to enjoy the benefits of brand-new construction in one of Central Florida’s most sought-after communities. Schedule your private showing today.

Listing is courtesy of: KARDOSH REALTY (407-499-4466)

Listing Agent: Gilson Rodrigues (407-989-2033)

Remarks: Positioned as one of the best values currently available in Winter Park, this exceptional residence designed by renowned architect Gary Hancock is a masterclass in craftsmanship, architecture, and timeless elegance. From the moment you arrive, the home commands attention with a breathtaking facade defined by graceful archways and refined architectural symmetry. Every exterior line and material selection has been intentionally chosen to create a presence that feels both bold and enduring, setting this residence apart as something truly exceptional. Inside, the home unfolds into a light-filled interior where design and livability coexist seamlessly. Ten-foot ceilings, level 5 drywall, and an abundance of expansive windows allow natural light to pour into every space, illuminating the impeccable finishes and creating an airy, sophisticated atmosphere throughout. Upgraded designer light fixtures add warmth and character, while the open-concept layout is anchored by a stunning living area centered around a refined fireplace, offering a natural gathering space that feels both intimate and grand. Flowing effortlessly from the living room, the dining area opens through elegant doors to the outdoor entertaining spaces, beautifully blending indoor and outdoor living. At the heart of the home, the chefs kitchen is as visually striking as it is thoughtfully designed. Custom cabinetry, sleek quartz countertops, a paneled refrigerator, and a premium induction range, reflect the builders uncompromising commitment to quality, performance, and clean modern design. The primary suite is a private retreat, highlighted by a spa-inspired bath with a freestanding soaking tub, an expansive walk-in shower, and a beautifully designed walk-in closet with direct access to the laundry room for effortless everyday living. Each secondary bedroom continues the theme of elevated design, offering generous proportions, abundant natural light, and elegantly appointed en-suite baths that ensure comfort and privacy for family and guests alike. Outdoors, the home reveals another level of thoughtful craftsmanship. A covered patio with a fully equipped summer kitchen overlooks a sparkling pool and expansive backyard, creating a setting equally suited for quiet evenings or lively gatherings. What truly defines this residence is the extraordinary level of craftsmanship throughout. No detail has been overlooked, no finish treated as an afterthought, and no design decision made without intention. This is a home that feels as impressive in its execution as it does in its presence.

Listing is courtesy of: ONE LUXURY INTERNATIONAL LLC (407-312-8003)

Listing Agent: Julie Christensen (407-592-2055)

Remarks: Virtually Staged. OUTSTANDING RENOVATION in a FANTASTIC LOCATION! Peace, Quiet & GOLF COURSE LIVING! This rare opportunity places you along the 13TH tee & offers tranquil backyard views of the 16TH fairway of the Winter Park Pines Golf Course (WP18)! Tree-lined street welcomes you to this completely renovated Floor to Ceiling ONE STORY beauty offers Serendipity LW Wood & porcelain tile flooring throughout. Updates include (but definitely not limited to) BRAND new kitchen with Stainless Steel Appliances, new cabinets & quartz countertops. Formal living & dining rooms PLUS Family room with vaulted ceilings featuring a new electric fireplace for amazing ambiance and sliding doors inviting you to new brick pavered 31x 11 screened porch overlooking newly refinished sparkling pool & golf course (no rear or side neighbors!!) Bedroom wing of home offers a large inside laundry room, beautiful guest/pool bath with dual sinks & shower/tub and 2 fresh guest bedrooms. THE PRIMARY SUITE has been thoughtfully remodeled with sliding doors to pool, AMAZING primary bath with oversized work-of-art shower with dual shower heads, dual vanity, separate water closet & HUGE walk-in closet! Extras include: NEW double paned windows & 3 sliding doors to pool/patio, crown molding, NEW roof November 2024, oversized 2 car garage, NEW landscaping, all NEW ceiling fans & light fixtures, NO HOA!! Zoned for Brookshire Elementary, Glenridge Middle & Winter Park High. WELCOME HOME!

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

Listing Agent: Catherine D'Amico (407-252-3210)

Remarks: Exquisite new construction in the heart of Winter Park, this LUIH Luxury Homes residence distinguishes itself through refined design, thoughtful efficiency, and an elevated level of craftsmanship. From the moment you enter, the home reveals itself with deliberate intention, clean architectural lines and a light-filled, open-concept layout create an effortless flow throughout. The main living space is both sophisticated and inviting, anchored by a sleek electric fireplace and expansive pocketing glass doors that gracefully blur the line between indoor and outdoor living. At the heart of the home, the chef’s kitchen is as striking as it is functional. Adorned with Calacatta quartz countertops and a full suite of premium Thermador appliances, it is designed to accommodate both everyday living and elegant entertaining. The kitchen transitions seamlessly into the dining area, while a walk-in pantry, generously sized mudroom / laundry space, and wine cellar add layers of convenience and luxury rarely found in homes at this price point. The primary bedroom suite offers a true sanctuary with direct access to a secluded outdoor patio that provides a serene extension of the space. The spa-inspired bath showcases a freestanding soaking tub, dual vanities, and an expansive walk-in shower. Upstairs, four additional bedrooms offer generous proportions and versatility, ideal for guests, family, or tailored uses such as a home office or fitness studio. Designed for year-round enjoyment, the outdoor living experience is equally captivating. A sprawling covered lanai features a fully equipped summer kitchen with grill, sink, and beverage refrigerator, overlooking a meticulously designed backyard complete with a resort-style pool and spa, perfect for both intimate evenings and grand entertaining. All of this is ideally located just moments from the boutiques and dining of Park Avenue, with convenient access to Phelps Park and the Winter Park YMCA, placing you at the center of one of Central Florida’s most desirable lifestyles.

Listing is courtesy of: ONE LUXURY INTERNATIONAL LLC (407-312-8003)

Listing Agent: Christopher Christensen (407-312-8003)

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

Listing is courtesy of: ONE LUXURY INTERNATIONAL LLC (407-312-8003)

Listing Agent: Julie Christensen (407-592-2055)

Remarks: "Price Improvement" This charming two-story home situated on a serene conservation lot within the highly sought-after Trinity Bay community in Winter Park. The inviting entrance showcases a covered portico with decorative beams and brick accents. Inside, the spacious living room boasts soaring cathedral ceilings, distinctive round-top windows, and a cozy wood-burning fireplace. A second-story loft overlooks the living area, creating an open and airy feel. Tile flooring graces the foyer, formal dining room, and kitchen, while the eat-in kitchen includes a bright breakfast nook enveloped by bay windows for abundant natural light. The private backyard oasis features a large screened porch, mature shade trees for natural privacy, an automatic irrigation system, and beautifully established landscaping that minimizes maintenance. Residents enjoy an exceptional lifestyle without leaving the neighborhood. Relax by the community pool, take leisurely strolls through the park, or visit the nearby playground. The community also provides direct access to the pristine waters of Lake Burkett (approximately 75 acres) and the connected Lake Martha chain (approximately 30 acres), ideal for boating, fishing, and recreation. The water heater was replaced in 2025, the AC was replaced in late 2021, and the roof in 2017. Trinity Bay is conveniently located adjacent to Trinity Preparatory School, the location is zoned for highly rated Seminole County public schools and offers easy access to major roadways, including SR 417, as well as proximity to the University of Central Florida (UCF), Full Sail University, premier shopping, and fine dining. This well-maintained residence offers a rare combination of character, comfort, and community amenities in a prime Winter Park location.

Listing is courtesy of: MNT INTERNATIONAL (844-668-7589)

Listing Agent: Mostafa Boulhanna (407-536-1484)

Remarks: Under contract-accepting backup offers. Tucked away along the tree-lined streets of the desirable Lost Creek community, this beautifully updated two-story residence is truly move-in ready. Major updates include a new roof in 2022 and a new water heater in 2026, offering peace of mind for years to come. Ideally situated in sought-after Winter Park, this exceptional home also includes exclusive creek-to-lake access leading to the sparkling waters of Lake Howell—perfect for enjoying Florida’s outdoor lifestyle while remaining close to premier amenities and entertainment. Step inside to soaring ceilings and an abundance of natural light that fill the spacious great room, creating an open and airy atmosphere. The gourmet kitchen flows seamlessly into a sunny breakfast nook and overlooks the inviting family room, complete with a cozy wood-burning fireplace—ideal for both everyday living and entertaining. The primary suite serves as a peaceful retreat with relaxing views of the sparkling pool. The ensuite bathroom features an oversized vanity with framed mirror, a garden soaking tub, and a beautifully tiled walk-in shower. Upstairs, an expansive open loft offers versatile living space perfect for a media room, home gym, office, or guest lounge. Two additional generously sized bedrooms and a full bathroom complete the second floor. Step outside to your own private backyard oasis featuring a screened-in pool and ample green space beyond—perfect for holiday cookouts, family gatherings, or simply relaxing outdoors. Conveniently located near premier dining, shopping, medical centers, and recreation, this home is just minutes from Oviedo on the Park, Park Avenue, and Waterford Lakes Town Center. Major employers including Siemens, Lockheed Martin, and UCF are all within easy reach, along with quick access to SR-417 for effortless trips to Orlando’s attractions, beaches, and beyond. Zoned for highly rated Seminole County schools: Red Bug Elementary, Tuscawilla Middle, and Lake Howell High School.

Listing is courtesy of: COLDWELL BANKER REALTY (407-647-1211)

Listing Agent: Shirley Jones (407-719-9180)

Remarks: Welcome to this beautiful pool home in the heart of Winter Park, offering the freedom of NO HOA and situated on an oversized lot with a spacious enclosed lanai—perfect for year-round Florida living. This thoughtfully designed split floor plan provides added privacy, with the primary suite tucked away from the secondary bedrooms. The recently updated kitchen serves as the heart of the home & major updates include a 2023 HVAC system, 2019 water heater, and a newer roof, providing peace of mind for years to come. With plenty of outdoor space and endless potential to customize and add value, this home is a rare opportunity in one of Central Florida's most sought-after locations.

Listing is courtesy of: LIFESTYLE INTERNATIONAL REALTY (305-809-8085)

Listing Agent: Jasmin Cabral (305-699-8099)

Remarks: On the first floor within The Cloisters, this three-bedroom, two-bath residence offers 1,734 square feet of renovated living space in one of Winter Park’s accessible lakefront communities. An oversized tiled patio, partially covered and ideal for outdoor dining or morning coffee, extends the living space and enhances everyday functionality. Renovated in 2021 by Charles Clayton Construction, an award-winning luxury homebuilder, the residence features updated flooring, kitchen, baths, lighting and laundry. Wood flooring flows through the foyer, dining and living areas, while ceramic tile is installed in the bedrooms, and decorative tile in the baths. The kitchen is appointed with high-end appliances and custom solid wood cabinetry, designed for daily living and entertaining. The primary suite offers abundant natural light, a built-in closet and an en-suite bath with dual sinks, walk-in shower and a window providing natural illumination. A hall bath includes a tub-shower combination and additional storage. A sunroom off the third bedroom provides flexible space for a private office, den or reading room. The residence includes one assigned covered carport space and a dedicated climate-controlled storage unit on site. Two blocks from Park Avenue, residents enjoy convenient access to dining, shopping and cultural amenities in a lakefront community setting. The property presents an opportunity for full-time living, luxury downsizing or a lock-and-leave lifestyle in the heart of Winter Park.

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

Listing Agent: Drew Henner (407-406-0662)

Remarks: Experience lakefront living in the heart of Winter Park. One of only two residences in The Cloisters with soaring 9-foot ceilings, this first-floor, three-bedroom, two-bath home offers a rare blend of privacy, scale and panoramic Lake Osceola views. Just two blocks from Park Avenue and adjacent to the Alfond Inn, this condominium lives like a private residence with unmatched access to boutique shopping, fine dining and cultural landmarks. Designed for elegant everyday living and entertaining, the open floor plan showcases a chef’s kitchen with granite countertops, solid wood cabinetry, and an island for prep and serving. The spacious dining and living areas are enhanced by hardwood flooring, crown molding and a marble-trimmed wood-burning fireplace. More than 20 feet of sliding glass doors open to an expansive, L-shaped terrace that brings in natural light and offers breathtaking lake vistas. The oversized primary suite offers serene lake views and includes an en-suite bath with dual vanities, built-in closets and a walk-in shower. Additional features include a rare laundry and utility room with a full-size washer, dryer and sink, updated electrical and plumbing, and upgraded water heater and HVAC system. Just two blocks from Park Avenue, this residence places you in the heart of downtown Winter Park’s sought-after lifestyle. Enjoy effortless access to fine dining, boutique shopping, world-class museums, Rollins College and year-round cultural events, all in an accessible, lakefront setting. Whether going to the Saturday farmers market, dining alfresco along the avenue or taking in the scenic views of Lake Osceola from your private residence, this property offers a seamless blend of luxury and urban elegance.

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

Listing Agent: Drew Henner (407-406-0662)

Remarks: This charming one story condo is located in the desirable Cedarwood Village. This unique home boasts an open layout that is different from many others in the community. The home showcases engineered hardwood floors, skylights and wonderful natural light. The kitchen provides ample cabinet space, granite counters, built-in wine rack and beautiful custom tile work. The kitchen overlooks the dining and living room combo. The living room has 2 skylights and flows right into the delightful Florida room. The Florida room boasts wonderful built-in shelving and a glass door giving access to the backyard. The primary bedroom showcases wonderful built-in cabinets, 2 closets and an ensuite bathroom with a granite counter vanity. The primary bedroom also looks into the Florida room but can be shut off for privacy with a sliding door. The second bedroom is at the front of the home and has access to the guest bathroom with a granite counter vanity. Two assigned parking spaces are directly in front of the home. To top it all off, this home is in close proximity to several restaurants and shops and is an easy drive to downtown Winter Park.

Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)

Listing Agent: Beth Logullo (772-633-0670)

Remarks: Charming, Fully Renovated Pool Home in Sought-After Winter Park. Welcome to this beautifully updated pool home, ideally located in desirable Winter Park—just minutes from premier shopping, dining, and entertainment, with easy access to major roadways for a seamless commute. From the moment you step inside, you’re greeted by a warm, modern aesthetic that blends comfort with style. To the right, a spacious step-down living room offers abundant natural light and lovely views of the front yard. To the left, the formal dining room flows effortlessly into the heart of the home—a stunning, fully renovated kitchen and inviting family room overlooking the private pool and patio. The kitchen is designed to impress, featuring solid wood cabinetry, stainless steel appliances, sleek modern lighting, ample counter space, and a center island perfect for gathering. The adjoining family room is anchored by a stylish electric fireplace, creating a cozy ambiance while offering serene views of the outdoor living area. This home features a desirable split-bedroom floor plan, providing privacy and flexibility. The primary suite is tucked away on one side, while two additional bedrooms and a full bathroom are located on the opposite wing—ideal for family or guests. Extensive upgrades provide peace of mind and modern appeal, including a newer roof (2021), a newer AC (2019) fully renovated kitchen and bathrooms, 5-inch baseboards, knockdown ceiling texture, textured walls, luxury vinyl plank flooring throughout, fresh interior and exterior paint, and updated electrical and plumbing fixtures. Step outside to your private oasis—a fully fenced backyard with a screened-in pool enclosure and lanai, perfect for relaxing or entertaining year-round in true Florida style. This move-in-ready gem truly has it all. Don’t miss your opportunity—schedule your private showing today!

Listing is courtesy of: COLDWELL BANKER REALTY (407-333-8088)

Listing Agent: Tony Nicolas (630-514-9342)