Winter Park Homes For Sale & Real Estate - 444 homes

Remarks: This home sits at the end of a cul-de-sac with an attractive courtyard entry to the 2 car garage. The Kitchen has been updated with new cabinets and tile flooring and the baths all have tile flooring. The Primary Bedroom has Luxury Vinyl Flooring. The screened porch overlooks a spacious fenced backyard that includes a block building (summer cottage) with electric and plumbing that is currently being used for storage. The Roof was replaced in 2022 and the yard has a sprinkler system. Make an appointment to see today!!

Listing is courtesy of: RE/MAX 200 REALTY (407-629-6330)

Listing Agent: Diane Gerry Pa (407-405-5550)

Remarks: Welcome to your private slice of paradise, perfectly positioned on a charming brick-lined street in the heart of historic Winter Park. This custom-built estate exudes casual elegance from the moment you step through the grand double door entry, where soaring 12-foot ceilings, rich architectural details, and exceptional craftsmanship immediately set the tone. Thoughtfully designed with a well-balanced and highly functional floor plan, the home offers a seamless blend of formal and informal living spaces ideal for both everyday living and elevated entertaining. At the heart of the home, the pristine chef’s kitchen opens effortlessly to the family room and is outfitted with a built-in Thermador French door refrigerator, custom lighted cabinetry, granite countertops, a six-burner gas range with pot filler, double ovens with warming drawer, and an oversized island designed for gathering. A beautifully appointed butler’s pantry with wine fridge and wet bar creates the perfect transition to the formal dining space. Tucked away for privacy, a dedicated home office or library offers a quiet retreat for work or study. The first-floor primary suite is a true sanctuary, featuring intricate ceiling detail, expansive windows, and private French door access to the outdoor living space. The spa-inspired primary bath includes a jetted tub, dual vanities, and two oversized walk-in closets. Upstairs, three generously sized secondary bedrooms and two additional baths—including a private en suite—provide comfortable accommodations, while a charming Juliet balcony offers picturesque views of the tree-lined street below. Step outside to an exceptional outdoor living experience designed for year-round enjoyment. The covered lanai features a fully equipped summer kitchen with built-in grill, custom copper hood, and beverage fridge for the warmest Florida days. The saltwater pool creates a resort-style setting, surrounded by lush landscaping and enhanced by upgraded lighting and smart technology. This meticulously maintained home has been extensively upgraded, including new HVAC systems for both levels, on-demand water heater, whole-house surge protection, updated LED lighting with dimmer controls, smart home integrations for pool, irrigation, security, and climate, as well as complete interior and exterior repainting with premium finishes. High-end reclaimed maple and beech wood flooring has been installed and is complemented by refined architectural details such as curved archways, custom millwork, and elevated designer fixtures. Additional highlights include a newly created wine room, epoxy-coated garage flooring, central vacuum system, and enhanced exterior features with added awnings and detailed craftsmanship. Situated on a gorgeous lot with added privacy and with garage doors thoughtfully positioned away from the street, this home offers both presence and practicality. Just a short stroll to Lake Mizell and minutes from the renowned dining, shopping, and cultural experiences of Park Avenue, this exceptional property combines timeless design, modern upgrades, and an unbeatable location.

Listing is courtesy of: ORANGE SLICE PROPERTIES (863-632-9765)

Listing Agent: Liz Jones (407-619-6345)

Remarks: Great opportunity to own this 3 bedrooms, 2 bathrooms single-story, ground level, end unit condo located within the quaint community of Cedarwood Village with a desirable Winter Park address! This light and bright home features vaulted ceilings in the living room, creating an open and airy feel. The kitchen offers an eat-in space, stainless steel appliances, a convenient pass through to the living room, and a laundry closet with washer and dryer included. Enjoy seamless indoor-outdoor living with sliding glass doors leading to a private rear screened-in lanai, plus an additional front patio just off the kitchen. Recent upgrades include new luxury vinyl flooring, a new roof (2023), new A/C ducts and insulation (2023), and full re-plumbing (2021), providing peace of mind for years to come. Two reserved parking spaces are located directly in front of the condo for added convenience. Community amenities include a pool, tennis court, and clubhouse. Ideally located near shopping and dining, Rollins College, Full Sail University, UCF, and major thoroughfares for easy commuting. This move-in ready condo offers comfort, convenience, and value in an unbeatable location!

Listing is courtesy of: URBANISTA BROKERS (407-619-7272)

Listing Agent: Anna Lohr (321-277-4797)

Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Welcome to this aesthetic custom luxury home in an unbeatable Winter Park location.From the moment you arrive, the custom landscaping and automated lighting make a statement, day or night.At the center of the home, the chef's kitchen is both a showpiece and a performance space. A commanding 48-inch Z-Line gas range with 8 Italian-made brass burners anchors the room, complemented by Café luxury appliances, a stainless steel refrigerator, quartz countertops, and custom cabinetry. The walk-in pantry with floating shelves and under-shelf lighting adds both beauty and function. An indoor wine bar with built-in cabinetry and wine refrigerator enhances the entertaining experience, while an upstairs beverage station keeps every level equally equipped.The primary suite is a full spa experience. The glass enclosed shower features a rain head, body jets, and handheld fixtures. A soaking tub, dual vanities with quartz counters, and a generously proportioned walk-in closet complete the retreat. Imported aged brass designer light fixtures are included in the sale. Philips Hue smart lighting synchronizes every indoor and outdoor light in one app, and a smart security camera system with fingerprint keypad entry completes the tech package. The outdoor living experience rivals the interior. A covered lanai with a fully equipped summer kitchen, including a built-in grill, dedicated refrigerator, and generous prep space, flows into a landscaped courtyard designed with an Italian villa, Mediterranean feel. As evening falls, intentional landscape lighting transforms the grounds into an intimate setting perfect for al fresco dinners, fireside gatherings, or projecting the big game under the stars. Walk to pickleball courts, athletic fields, and a premier wellness facility. Park Avenue's celebrated boutiques and dining are just minutes away. New construction of this caliber is increasingly rare in Winter Park. Schedule your private showing today. The furniture and décor, curated by a professional design team, are negotiable, making it possible to move in with the full look already in place.

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

Listing Agent: Norma Gonsalves (407-451-9533)

Remarks: Under contract-accepting backup offers. Experience lakeside living in Winter Park, FL with this custom LAKEFRONT PROPERTY on the shores of Lake Killarney, a 234 acre PRIVATE LAKE. There are a limited number of lakefront properties within the City, especially on skiable lakes, so this home presents a unique opportunity. Boasting an EXPANSIVE DOCK, one that’s grander than current building standards allow (but is grandfathered in), this backyard provides an ideal place to launch your water adventures, soak up scenic sunsets, and travel by lake to Hillstone for a meal. The CUSTOM POOL is waiting to be enjoyed! It features a custom waterfall, grotto, built-in seating/table and adjacent koi pond, all with a lake view. Recent updates to the home include: shingled roof (2018), DOUBLE PANE WINDOWS (2015), and HVAC (2016). Travertine and tile floors cover the entire home, there is no carpet. The back family room has multiple French doors and offers an expansive view of the lake. Fireplaces are featured in both the office and living room. The convenience of 632 Country Club is unmatched. It is approximately .6 miles from grocery shopping like Whole Foods and Publix or the Winter Park Village - a vast outdoor mall featuring a 20-screen Regal Cinema, Ruth's Chris Steakhouse and Bar Italia, to name a few. For everyday errands like HomeGoods, or workouts at LA Fitness, there is an even closer shopping plaza. An Interstate 4 (I-4) onramp is approximately 2 miles away. Winter Park is bursting with Old Florida charm and was named #38 historic world destinations in 2008 by National Geographic Magazine. At its heart is Park Avenue, famed for its cobblestoned and tree-lined streets with over 140 boutiques, museums, a train station, and world-class dining. 632 Country Club is approximately 1.5 miles from luxurious Park Avenue and 5 miles from downtown Orlando.

Listing is courtesy of: KELLER WILLIAMS ADVANTAGE REALTY (407-977-7600)

Listing Agent: Kristin Duncan (407-274-5911)

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

Listing is courtesy of: RE/MAX INNOVATION (407-281-1053)

Listing Agent: Ronald Trotter (321-331-1585)

Remarks: A MUST SEE! Beautifully remodeled 3 bedroom 2 bath home. Third bedroom has its own separate entrance as well. Large foyer and living room. Kitchen has beautiful 40 inch cabinets and granite counter tops. Septic system was just replaced in September. Close to everything.

Listing is courtesy of: SAVVY AVENUE, LLC (888-490-1268)

Listing Agent: Moe Mossa (888-490-1268)

Remarks: NEW ROOF AND SOLAR PAID OFF AT CLOSING!!! Located in desirable Winter Park, this POOL home offers exceptional value. This spacious 5-bedroom plus den area, 3.5-bathroom house has a beautiful pond view from the front door. 3 car garage space and 6 car driveway give you plenty of space for storage and parking. 3,111 square feet of comfortable living space plus a gorgeous screened-in pool with spa. The home features high ceilings that create an open, airy feel throughout. The kitchen showcases elegant granite counters and modern stainless steel appliances. Hard flooring flows through the main living areas, offering both style and easy maintenance. Solar panels on the home save you hundreds each month on electricity. SELLER WILL PAY OFF SOLAR PANELS AT CLOSING! Step outside to your private backyard oasis with a screened-in pool and jacuzzi spa, ideal for year-round Florida living. The fully vinyl fenced yard provides privacy and security for families and pets. This move-in ready property means you can start enjoying your new home immediately. The location offers incredible convenience with easy access to Winter Park shopping, restaurants, and world-famous theme parks. Major roads are nearby, making commuting simple whether you work locally or need to travel throughout Central Florida. The gated community adds security and peace of mind. Winter Park is known for its charming downtown area, excellent schools, and beautiful parks. This neighborhood combines suburban tranquility with urban accessibility, giving you the best of both worlds. Schedule your showing today!

Listing is courtesy of: REAL BROKER, LLC (855-450-0442)

Listing Agent: Kathy Williams (407-230-7305)

Remarks: Under contract-accepting backup offers. Back on the market—an exceptional opportunity in Winter Park. Now offered below appraised value, this residence has been thoughtfully refreshed with new carpet, interior paint, and thoughtful enhancements. Presented for the first time, this beautifully appointed 2014 David Weekley home is tucked away on a large corner lot within a rare cul-de-sac in the heart of Winter Park, zoned for Dommerich Elementary and Winter Park schools. Featuring 5 bedrooms and 5 bathrooms, the home is designed for both refined living and effortless entertaining, this home includes a private office and expansive bonus spaces. A standout feature of this property is its exceptional and highly sought-after parking flexibility. In addition to the 3-car garage, a newly added driveway (2024) provides additional space for guests and everyday convenience. Beyond that, a gated parking area—discreetly tucked behind an accessible double gate—offers secure storage for a boat, jet skis, or additional vehicles, eliminating the need for off-site storage and enhancing both lifestyle and practicality. Inside, the home showcases a curated collection of upgrades, including custom built-ins throughout the living spaces, office, flex areas, and dining room; custom built closets in every room; and a thoughtfully redesigned pantry with pull-out shelving. Unique touches such as under-stair storage with a hidden “secret door,” custom barn doors, and a LaCantina slider elevate both function and design. Outside is an entertainer’s paradise. There is a covered custom-built summer kitchen with metal roof featuring a built-in LP Grill, Primo Kamodo Smoker, stainless steel storage drawers and cabinets, counter storage ice bucket and plenty of island space for dining. The large pool and adjoining hot tub provide ample space for hours of fun and entertainment. The backyard putting green adds a fun distinctive, resort-style touch. Additional enhancements include brand new luxurious Berber carpet, attic flooring, overhead garage storage, plantation shutters, landscape lighting, updated exterior paint and interior paint, a tankless gas water heater, updated designer lighting through the home and multiple bathroom updates. The roof was replaced in 2021 for added peace of mind. The kitchen is a cooks dream with abundant storage, ample counter space and two ovens. A GE Monogram Dual Fuel Range was added to the kitchen in 2023. The 2021 dining room renovation introduces a custom bar, added storage and striking raw-edge floating shelves—perfectly blending modern sophistication with everyday livability. With its prime location, elevated finishes, and rare combination of luxury and utility—particularly its unmatched parking and storage capabilities, this move-in-ready Winter Park home is truly a standout offering! Inspection report available upon request.

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

Listing Agent: Sarah Tomlinson (407-721-7823)

Remarks: Under Construction. NEW CONSTRUCTION!!! Welcome to Winter Park Grove — Winter Park’s newest community by SGC Construction! This stunning new Mid-Century Modern–inspired home is designed to impress with its architectural flair, meticulous craftsmanship, and luxurious finishes. Perfectly located near all the shopping, dining, and entertainment Winter Park is famous for, this home combines convenience, style, and comfort. Step onto the inviting front porch and through the elegant entryway to discover a spacious, open floor plan filled with natural light. Just off the foyer, you’ll find a flexible fourth bedroom or private study with a full bath—ideal for a home office or serene guest suite. The heart of the home is the gourmet kitchen, featuring quartz countertops, custom cabinetry, and a premium Bosch appliance package including a 36" gas cooktop. The kitchen flows seamlessly into the living and dining areas—perfect for entertaining or family gatherings. Enjoy Florida living at its finest on the covered lanai, overlooking your sparkling pool and lushly landscaped backyard—your own private retreat. The first-floor primary suite offers a spa-inspired bath with dual vanities, a freestanding soaking tub, and a spacious walk-in closet with custom shelving. A convenient laundry area is thoughtfully located just off the suite. Upstairs, a large bonus room with a closet offers versatility as a fifth bedroom, game room, or home office. Two additional bedrooms feature walk-in closets and share a beautifully appointed bath with dual sinks. An upstairs laundry room with a sink and plenty of natural light adds everyday convenience. The photos shown are of the same model in another location. Finishes will vary. Located near top-rated schools, local parks, and all that Winter Park has to offer — this home truly has it all. Schedule your private showing today before this exceptional new build is gone!

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

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

Remarks: Welcome to easy, light-filled living in this beautifully maintained 3-bedroom, 2.5-bath corner townhome in the gated Grayson Square community. Freshly painted and designed for comfort, the open living and dining spaces feel bright and inviting, flowing effortlessly to a covered lanai—perfect for relaxing evenings or casual gatherings. The kitchen offers a clean, modern look with stainless steel appliances, quartz countertops, and plenty of cabinet space for storage and organization. Upstairs, the owner’s suite provides a private retreat with a walk-in closet and a spacious ensuite bath featuring dual vanities and a glass-enclosed shower. A two-car garage with epoxy flooring and an in-unit washer and dryer add everyday convenience. Residents also enjoy access to a resort-style pool with cabana, along with high-speed fiber-optic internet and streaming services included. Located just minutes from downtown Winter Park, with easy access to major roadways, shopping, dining, and everyday essentials, this home offers a great balance of comfort, convenience, and low-maintenance living.HABLO ESPANOL

Listing is courtesy of: LPT REALTY, LLC (877-366-2213)

Listing Agent: Denise Del Castillo (321-960-3110)

Remarks: Under contract-accepting backup offers. Positioned as one of the best values currently available for new construction in Winter Park, this exceptional residence by Hamilton Homes seamlessly blends timeless character with the ease and efficiency of modern living. From the moment you arrive, the home makes a lasting impression with its inviting front porch and classic gas lantern, setting a tone that feels both warm and refined. Inside, the home unfolds into a light-filled, thoughtfully designed interior where every detail has been carefully considered. Just off the entry, a versatile space behind double doors offers the perfect setting for a private home office or an additional bedroom, complemented by a full bath nearby for added convenience. White oak engineered hardwood flooring runs throughout, creating a cohesive and elevated feel, while subtle gold accents at key transitions add a layer of understated sophistication. Designed for both functionality and everyday ease, the main living areas flow effortlessly together. The kitchen serves as the heart of the home, featuring stainless steel appliances, a gas range, abundant cabinetry, and a spacious walk-in pantry. It opens seamlessly to the living and dining areas, creating an ideal environment for both casual living and entertaining. Just beyond, French doors lead to a covered lanai and an oversized backyard, offering a natural extension of the indoor living space. A well-appointed mudroom provides a practical drop zone and connects directly to the oversized two-car garage, enhancing daily convenience. Upstairs, the home continues to impress with a thoughtfully arranged layout that prioritizes both privacy and comfort. The primary suite is a true retreat, offering generous proportions, dual vanities, a large walk-in shower, and custom built-in closet systems. Each additional bedroom is equally well-designed, with all closets throughout the home fully finished for optimal organization. Located in a desirable Winter Park setting, This property is in the heart of it all, 2 miles to AdventHealth Winter Park Hospital, less than 10 minutes to Park Ave, and zoned for top-rated schools such as Dommerich Elementary, Maitland Middle, and Winter Park High. This is a rare opportunity to own a brand new home that delivers both character and quality, all while standing out as one of the most compelling values in today’s Winter Park market.

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

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

Remarks: One or more photo(s) has been virtually staged. Step into refined lakeside living at the exclusive Lake Killarney Townhomes, where contemporary elegance meets everyday convenience. This ultra-private corner unit boasts one of the community’s most desirable floor plans—perfectly positioned in a peaceful enclave just steps from the vibrant heart of Winter Park Village and mere minutes from I4, offering seamless access to downtown Orlando and beyond. Designed for the modern lifestyle, this stunning residence features an open-concept layout with soaring ceilings, oversized windows, and luxury finishes throughout. The sleek chef’s kitchen anchors the space, showcasing dramatic gray cabinetry, a bold black center island, and a high-end Samsung appliance package, complete with a natural gas cooktop and built-in wall oven. Quartz countertops and a full-height backsplash give a seamless, refined look, while a spacious walk-in pantry adds everyday convenience. Upstairs, three generously sized bedrooms each pair with a spa inspired bathroom deliver elevated comfort. Each bath is thoughtfully designed with floating vanities, designer porcelain tile, and custom closet systems—bringing a boutique hotel aesthetic to your personal retreat. Enjoy quiet mornings or golden-hour gatherings on the expansive private terrace, framed by glass railings and pre-plumbed for a future summer or cocktail kitchen—perfect for effortless indoor-outdoor entertaining. Residents enjoy exclusive access to lakefront pavilion, and an array of watersport amenities including kayak, paddleboard, and canoe storage. With everything Winter Park has to offer just moments away, this location offers the perfect blend of serenity and connectivity.

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

Listing Agent: Brandon Geers (941-928-5152)

Remarks: Under contract-accepting backup offers. Experience elevated living in this rare fifth-floor corner residence, perfectly positioned just one block from the iconic Park Avenue in the heart of Winter Park. With sweeping views of the downtown skyline and abundant natural light from multiple exposures, this residence offers an exceptional blend of comfort, elegance, and location. The thoughtfully updated kitchen features custom shaker cabinetry, granite countertops, and stainless-steel appliances, seamlessly connecting to the spacious living and dining areas. A charming sunroom provides the perfect setting for morning coffee, reading, or enjoying the city views. The generously sized primary suite offers a peaceful retreat, complete with an updated bath and a large walk-in closet with custom built-ins. The second bedroom has been thoughtfully opened to create a stylish office or den, ideal for working from home or relaxing with guests. Refined interior details include crown molding, bamboo flooring, and abundant natural light throughout, creating a warm and sophisticated atmosphere. Residents enjoy the security and convenience of a well-maintained mid-rise building featuring secure key entry, guest call box access, and a welcoming lobby. Perfectly suited for a lock-and-leave lifestyle, this residence is just steps from Park Avenue’s boutiques, acclaimed restaurants, museums, cafés, and the Winter Park Golf Course. Additional features include: • Private storage unit • Covered carport parking space • Guest parking and community pool. An exceptional opportunity to enjoy refined living in one of Central Florida’s most desirable locations. Please note: NO RENTALS, NO PETS.

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

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

Remarks: One of the best patio views in this community. Enjoy easy living in this cozy, open-concept first-floor condo located in a desirable Winter Park community. Step out onto your newly screened-in patio and take in the peaceful, park-like setting — a relaxing extension of your living space and the perfect spot for morning coffee or evening unwinding. Recent 2025 improvements include a new A/C system, water heater, freshly painted interior, new screened porch, and new toilet — giving you move-in-ready comfort and peace of mind. The kitchen comes fully equipped with range, dishwasher, refrigerator, and microwave. A stackable washer and dryer are conveniently located in the bedroom, and an additional community laundry room with two washers and dryers is available free of charge. Stratford residents enjoy an amenity-rich lifestyle including: • Two sparkling pools • Tennis courts • 24/7 fitness center • Clubhouse available for private gatherings • Pet station *Planned social events for residents. The HOA adds tremendous value by covering water, trash removal, internet, pest control, exterior maintenance, grounds care, and common areas — simplifying ownership and monthly budgeting. Located in a prime Winter Park area with easy access to 408, Semoran Blvd., 417, I-4, and State Road 50. Just minutes from shopping, dining, grocery stores, and within 20 minutes of UCF, Full Sail University, Rollins College, and Park Avenue. With its thoughtful updates, first-floor convenience, and exceptional community amenities, this condo offers more than just a home — it delivers an above-average lifestyle in one of Central Florida’s most desirable locations.

Listing is courtesy of: WATSON REALTY CORP (407-332-6000)

Listing Agent: Barbara Coy (407-497-1777)

Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Beautifully renovated pool home in the highly desirable Eastbrook community of Winter Park, featuring major recent upgrades including a new AC system, windows, doors, and flooring throughout the home. This move-in ready 3-bedroom, 2-bath residence sits on an oversized 0.30-acre corner lot in a quiet cul-de-sac with no HOA. The home offers a bright open-concept layout with abundant natural light and a seamless flow between the living, dining, and kitchen areas—ideal for both everyday living and entertaining. The updated kitchen features modern cabinetry, stainless steel appliances, and generous counter space. Both bathrooms have been tastefully renovated, and the spacious bedrooms provide comfort and flexibility. Step outside to a private backyard with a sparkling pool and plenty of outdoor space perfect for relaxing or hosting gatherings. Additional highlights include a 1-car garage, roof replaced in 2016, updated electrical, and a newer water heater (2021). Located within the top-rated Seminole County school district and just minutes from Park Avenue, Rollins College, shopping, dining, museums, and Winter Park Hospital. A fantastic opportunity to own a beautifully updated home in one of Central Florida’s most desirable locations.

Listing is courtesy of: SERHANT (786-296-8626)

Listing Agent: Julimar Barreiro Pastrana (407-590-8604)

Remarks: Designer-Curated Coastal Renovation with Exceptional Lakefront Vistas! This sophisticated reimagining was taken down to original framework and meticulously rebuilt with elevated design and superior finishes throughout. The result is an expansive openness illuminated with natural light and accented by European oak wide-plank flooring, Level 5 smooth-finish walls and ceilings, architectural recessed lighting, and custom-tailored interior doors with modern glass knob hardware. With two walls of glass, the main living space extends to a generous wraparound balcony set among lush treetops and endless lake views—the perfect backdrop for morning coffee, sunset cocktails, and open-air entertaining. A restored floor-to-ceiling brick fireplace is a dramatic centerpiece, pairing modern simplicity with timeless appeal, that adds warmth and ambiance. The striking kitchen blends clean lines with elevated finishes. Crafted maple cabinetry rises to the ceiling, complemented by sleek hardware and under-cabinet lighting that softly highlights a dimensional subway tile backsplash for added depth and texture. Crisp quartz countertops provide a seamless surface, while a suite of premium Jenn Air appliances delivers both statement-making design and top-tier performance. A large peninsula offers generous seating and gathering space—ideal for casual dining or entertaining—and incorporates a discreetly integrated pet station, a thoughtful detail that enhances daily living. Open to the surrounding spaces, the entire space feels cohesive, inviting, and effortlessly functional. The primary suite is thoughtfully planned to provide a calm and comfortable retreat, featuring truly custom closet cabinetry for streamlined storage. Expansive windows frame serene lake views and a lush green backdrop, creating a tranquil, ever-changing setting—wake to soft morning light shimmering across the water and unwind in the evening with a sense of quiet ease. Also designed with intention and precision, the primary bath maximizes space with more custom cabinetry for additional clothing storage, a streamlined vanity with quartz counter, integrated laundry cabinet, and glass-enclosed shower—all executed in a refined palette that feels both elevated and livable. The inviting second bedroom is enhanced by a built-in closet offering a polished and highly functional storage solution. Equally well considered, the second bath features quartz counters and lots of custom cabinetry for a clean, detailed look. A seamless glass shower is complimented by a strategically placed frosted entry panel offering privacy without sacrificing natural light, while a full-width mirror amplifies the sense of space. The third bedroom offers a thoughtfully designed double desk, a customized closet for added style and function and sliding glass doors to the balcony for natural light and an outdoor connection. New laundry room is both functional and refined, featuring folding counter, abundant cabinetry, and a dedicated hanging area with a built-in bench & storage drawer. Custom integrated doors discreetly conceal mechanicals. The residence also includes assigned covered parking. Residents of The Cloisters enjoy a lakefront lifestyle with dock access, boat slips, along with/ other amenities including a fitness center, and renovated clubhouse w/ kitchen, putting green and pool—all supported by a professional on-site management and beautifully maintained grounds.

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

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

Remarks: Welcome to this beautifully maintained 2-bedroom, 2-bathroom condo in the heart of Winter Park! Perfectly positioned for both convenience and lifestyle, this home offers quick access to the 408 Expressway and is just minutes from Downtown Orlando, making daily commutes effortless. Step inside to discover a bright and inviting interior featuring upgraded light fixtures, and an abundance of natural light that enhances the open feel of the space. The thoughtfully designed layout includes generously sized bedrooms and a spacious living area ideal for both relaxing and entertaining. The kitchen is highlighted by a breakfast bar with new granite countertops, creating a functional and stylish focal point. This unit can be sold fully furnished, offering a true turnkey opportunity for homeowners or investors alike. All appliances are included, making for a seamless move-in experience from day one. Location is everything—and this one delivers. Just minutes from Full Sail University, University of Central Florida, and Valencia College, this property is ideally situated for strong rental potential. Plus, enjoy being within easy reach of world-famous attractions like Walt Disney World and the beautiful shores of Cocoa Beach. Whether you’re searching for a primary residence, vacation getaway, or investment property, this Winter Park gem offers the perfect blend of comfort, location, and value.

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

Listing Agent: Uzi Husain (407-719-6576)

Remarks: This property located in a peaceful community IN WINTER PARK. and easy access to FL I-4 , short drive distance to Rollins College, UCF, Valencia college, Hospitals, shopping center, restaurants and Orlando Theme Park. This unit located on the second floor, it has 3 bedrooms 2, bathrooms, open floor plan. The community amenities include a large pool with lounge chairs, playground and gazebo. This property can be leased. You must see for any possibilities come and check for yourself. Registered owner is brother of the realtor. SELLER MIGHT HOLD FIRST MORTGAGE WITH A GOOD DOWN PAYMENT.

Listing is courtesy of: PRIMESTATE REALTY, INC. (407-850-9494)

Listing Agent: Hoover Yap (407-342-9395)

Remarks: 3 bedrooms PLUS an office (or 4th bedroom) AND a "flex space". Easy access to all of Winter Park, UCF, and south Seminole County from this convenient, central location! If you've been searching for a spacious pool home with plenty of space for playing, entertaining, or even working from home -- you've found it here! When you walk in, you'll appreciate the intuitive flow of living space into the kitchen, with built-in eating space. Off of the kitchen, you'll find a bonus space (perfect for an office or home gym) as well as a large indoor laundry room/mudroom, and the converted garage which is ideal for a playroom or secondary living space. On the other side of the home, 2 secondary bedrooms, an oversized hall bathroom, and a primary with en suite bath. There are additional touches that go a long way, too, including the custom plantation shutters throughout the home and updated countertops in the kitchen. Much of your time will be spent in the backyard, enjoying a fenced in pool, screened porch, new custom shed (2025), and fully fenced yard with turf play area. Systems in the home have been well maintained: roof (2017), HVAC (2017), tankless gas water heater (2018), and brand new electrical updates (2026). The home was also re-plumbed in 2008.

Listing is courtesy of: MILLER GRANT AND COMPANY (407-399-6031)

Listing Agent: Courtney Pelfrey (407-454-0538)