Courtesy: COLDWELL BANKER RESIDENTIAL RE
407-647-1211
Modern Elegance Meets Custom Craftsmanship in the Heart of Winter Park with easy access to major highways! Welcome to your dream home — a custom-built Winter Park masterpiece blending modern luxury with thoughtful design. With over 2,500 sq/ft of stunning living space, this 4-bedroom, 3-bathroom home was built to impress and designed to entertain. Step inside and be captivated by the seamless open layout, drenched in natural light from oversized windows. The living room features a striking electric fireplace and built-in JBL speakers — perfect for cozy nights in or lively gatherings. Custom woodwork accents the walls, adding warmth and character to every corner. The heart of the home is the chef-inspired kitchen, boasting gleaming quartz countertops, premium stainless steel appliances, and a spacious butler’s pantry. Whether you're hosting dinner parties or making weeknight meals, this kitchen is both functional and fabulous. Upstairs, the luxurious primary suite is a private retreat, complete with its own sound system, generous space, and serene ambiance. The remaining bedrooms — thoughtfully positioned down the hall — are ideal for family or guests, and a versatile loft offers the perfect space for game nights, a home office, or a relaxing lounge. Don't miss the downstairs guest suite, perfect for multi-generational living or a private home office. Outside, your personal oasis awaits. A spacious backyard invites weekend barbecues, and a custom gazebo sets the scene for memorable evenings under the stars. Additional highlights include a conveniently located laundry room near the bedrooms, modern finishes throughout, and smart, stylish details in every room, check out our 3D tour! Located conveniently close to I-4 and downtown, his is more than a home — it’s a lifestyle. Come see the perfect blend of elegance, comfort, and design. Call today to schedule your private showing!
Courtesy: IAD FLORIDA LLC
407-720-0020
This 2 bedroom, 1.5 bathroom condo features a townhome style layout with spacious living areas. Recent enhancements include the removal of dated laminate to reveal ceramic tile flooring throughout the main level, installation of stylish luxury vinyl plank on the upper level, new carpeting on the staircase and landing, and a full interior repaint. In addition, the sliding glass doors were professionally serviced, including roller replacement, track repairs, and installation of new locks to ensure smooth, secure operation. Deluxe vinyl fencing was installed throughout the community by the HOA replacing the older wooden fencing. The fencing was replaced with the vinyl after the listing photos were taken, please view the video to see the replacement vinyl fencing. Enjoy convenient features including an in-unit washer and dryer combo, storage under the stairs, and a large carport with an attached storage shed. The spacious primary bedroom opens to a large screened-in balcony. Ideally located just 15 minutes or less to UCF, Rollins College, Valencia East, and Full Sail University, and only 20 minutes to Orlando International Airport. Whether you’re a first-time home buyer, student, investor, or looking to make your move into Winter Park, this home offers affordability, convenience, and plenty of potential!
Courtesy: RE/MAX EXCLUSIVE COLLECTION
407-447-2829
Under Construction. New Construction – Modern Luxury Meets Urban Living at Winter Park's Newest Neighborhood, Winter Park Grove! Step into the future of refined living with this stunning new construction pool home, situated in the vibrant heart of Winter Park. Just minutes from the eclectic energy of Park Avenue, this modern masterpiece offers the perfect blend of sophistication, style, and convenience — all within walking or biking distance to top restaurants, cafés, boutique shops, and entertainment spots. Designed for both everyday comfort and elevated entertaining, the open-concept floor plan showcases thoughtful design and top-tier finishes throughout. Luxury details abound, including engineered wood floors with an elegant herringbone pattern in the foyer, smooth finish Level 4 drywall throughout, and an electric fireplace that adds a cozy glow to the spacious great room, featuring LED mood lighting in the coffered ceiling. The expansive gourmet kitchen is a chef’s dream, with cabinets reaching to the ceiling for ample storage and featuring premium Thermador appliances, including a 36” gas cooktop, wall oven, built-in microwave, French door refrigerator, and a wine fridge — all accented by sleek cabinetry and contemporary details. A beautiful dry bar off the kitchen provides additional space for coffee, wine, or entertaining. With four spacious bedroom suites, including a luxurious primary suite on the main level, a second bedroom suite on the first floor offers versatility as an office or guest retreat. Upstairs, two additional suites are joined by a flexible bonus room — perfect for a home office, gym, second living area, or even a fifth bedroom. Step outside to your private outdoor retreat, featuring a covered lanai, automatic roll-down screens, a fully equipped summer kitchen (grill, sink, and refrigerator drawers), and a sparkling pool with travertine decking — perfect for Florida’s year-round entertaining. The elegant exterior features outdoor lighting, lush landscaping and a generator, Making sure you are always ready for storm season! Don't miss your chance to own this beautifully crafted home in one of Orlando’s most sought-after neighborhoods. Schedule your private showing today and discover why this new build is the epitome of Winter Park luxury.
Courtesy: RE/MAX EXCLUSIVE COLLECTION
407-447-2829
Under Construction. NEW CONSTRUCTION!!! Welcome to Winter Park Grove — Winter Park’s newest community! 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. 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!
Courtesy: CREATIVE HOMES OF ORLANDO
407-205-8637
**** Ground floor 2 bed 2 bath condo in a nice quiet community *** move-in ready with granite tops, upgraded plumbing, on-demand water heater, vinyl plank flooring throughout. One of the best priced units available on MLS. Well maintained community and roof replaced within past two years. Owner is Listing Agent, Broker and Realtor so an efficient sale can be expected. All offers to be on FAR/BAR As-Is and within 10K of Listing price to be considered and responded to. Offers to include $3000 escrow deposit and pre-approval or proof of funds.
Courtesy: PREMIER SOTHEBY'S INTL. REALTY
407-644-3295
In the exclusive community of Windsong on Lake Berry, this magnificent 1.6-acre gated Mediterranean estate is a private oasis. With over 11,000 square feet of living area and a beautifully landscaped lakefront lot, this residence offers an exceptional blend of elegance, charm and privacy rarely found in Winter Park. The home features seven spacious bedrooms and nine full and two half baths. Entertain in the all-glass conservatory, dedicated theater room with motorized seating and a fully equipped game room. Modern conveniences throughout including gas-powered generators, an elevator and dumbwaiter. Two above-garage apartments provide ideal accommodations for guests and family. Outdoors, enjoy an expansive covered lanai, infinity edge pool and spa, boat dock with jet ski lift, and a summer kitchen complete with wood-burning fireplace, gas grill, refrigerator and icemaker, all overlooking the beautifully landscaped yard and lake. With its private gated entrance, this home is a one-of-a-kind opportunity to enjoy all the amenities Winter Park and Windsong have to offer.
Courtesy: PR REAL ESTATE SERVICES
407-447-9500
PRICED TO SELL!!! This is the largest floorplan in the community. Two bedrooms, two bathrooms, and a loft that you can use as a third bedroom, home office, or gym. Welcome to the established and well-maintained community of Cedarwood Village, located in highly desirable Winter Park! TREE-LINED STREETS lead you to this two-story, 2-bedroom, 2-bath BLOCK-CONSTRUCTED condominium offering 1,669 square feet of interior living space, this includes an enclosed lanai (under air), for extra living space. The open living and dining area features VAULTED CEILINGS, two skylights, creating a bright and inviting space. From here, enjoy serene views of the enclosed lanai and lush green space beyond. A WET BAR adds a perfect touch for entertaining. Upstairs the loft has a skylight, ceiling fan and is carpeted. The kitchen is thoughtfully designed with a space for a charming eat-in nook that overlooks your PRIVATE COURTYARD and is accessible through sliding glass doors—perfect for morning coffee or outdoor dining. For added convenience, the laundry closet with a WASHER AND DRYER is tucked right into the kitchen. The primary suite is a peaceful retreat, with a beautifully en-suite bathroom with a brand-new vanity with granite, featuring both a WALK-IN closet, and a shower enclosure and the lanai under air, is accessible through sliding glass doors. The spacious second bedroom also features a walk-in closet and attached access to the second bathroom, offering privacy while still serving guests comfortably. Additionally, this home is located across from green space, has two designated parking spaces, and a private mailbox. Re-roofed and new skylights were installed in 2020; entire complex was recently painted. Upgrades include newer AC, and a beautiful master bathroom cabinet and sink —providing comfort and style. With low HOA dues, residents enjoy access to a sparkling community pool, clubhouse, tennis and basketball courts, pickleball, a FENCED DOG RUN, and a pet walk with waste stations. Monthly fees also cover roof and exterior building maintenance, pest control, and landscaping. This ideal Winter Park location is just minutes to Park Avenue, UCF, Rollins College, Full Sail University, shopping, restaurants, entertainment, and medical facilities.
Courtesy: CAMERON REALTY GROUP LLC
321-947-0424
NEW REDUCED PRICE BELOW MARKET IN DESIRABLE TANGLEWOOD WINTER PARK COMMUNITY WITH NO HOA! ALLOWS SHORT TERM RENTALS (STR). LOW TAX DISTRICT. This is probably the closet you can get to Winter Park (Park Ave) without having to pay the Winter Park taxes or conform to their restrictions! This property has been extremely well maintained and would be an amazing home for a new family. ROOF IS 2023! All systems have been updated or serviced. Property features include 4 BEDROOMS, 2 BATHROOMS, 1,725 TOTAL SQFT, ATTACHED IN-LAW SUITE WITH ITS' OWN ENTRY, HUGE BACK YARD WITH LOT SITTING ON APPROX. 10,000 SQFT, TILE THROUGHOUT, STAINLESS APPLIANCES INCLUDED, FENCED, AND MORE. Seller is willing to give $5,000 credit towards the buyer's closing costs or buying down their interest rate (inquire about conditions). *More than one of the photos has been virtually staged.
Courtesy: THE AGENCY FL
407-335-4119
Nestled on a quiet cul-de-sac in the heart of Winter Park, this canal-front residence offers the perfect balance of elegance and lifestyle. With direct access to Lake Killarney, the home invites days filled with boating, fishing, and entertaining poolside. Offering a total of 4,798 heated square feet, the property includes the main residence with 3,798 square feet plus a 1,000-square-foot detached guest house with a private entrance, kitchen, living area, bedroom, and full bath—ideal as an in-law suite or private retreat for guests. Inside the main home, the living space unfolds across a single story with soaring ceilings, custom built-ins, and expansive gathering areas. Throughout the home, custom 8-foot doors imported from Italy enhance the refined architectural appeal. The gourmet kitchen is a chef’s delight, featuring a gas cooktop, built-in oven, 42” cabinetry, and generous counter space for entertaining. A gas fireplace anchors the family room, while Italian-imported French doors open seamlessly to the screened pool, patio, and expansive backyard. The oversized primary suite feels like a private retreat with its spa-inspired bath, oversized walk-in closet, and tranquil views of the pool and canal. Four additional bedrooms provide exceptional flexibility and comfort for family or guests. Designed for true waterfront living, the oversized garage features an extra-tall, boat-ready garage door, allowing you to store your boat with ease and launch directly into Lake Killarney via your private ramp. Front and rear garage access adds unmatched convenience for boating enthusiasts. Zoned A/C, natural gas, and thoughtful updates ensure modern comfort throughout. All personal property is negotiable. Located just minutes from Park Avenue, Rollins College, and downtown Orlando, this exceptional home offers privacy, convenience, and a rare lakefront lifestyle unique to Winter Park.
Courtesy: REALCOM REAL ESTATE SERVICES INC
407-621-6856
PRICE REDUCTION! \Highly Desirable Winter Park Lakefront Community on Skiable Lake Killarney. Enjoy Peaceful Water Views and Million-Dollar Sunsets on Lakefront Deck! Private Community Ramp, Heated Pool, Men's and Women's Saunas! Don't miss this 2 Bedroom 2 Bath Beautifully Renovated Unit. New Kitchen Cabinets and Quartz Counters, Stainless Steel Appliances, Raised Ceiling with Lighting, Kitchen Island/Bar! Enjoy the Ease of Luxury Vinyl Plank Flooring, Crown and Wide Floor Moldings, Plantation Shutters, Upgraded Energy Saving Windows and Sliding Glass Door. Modernized Master Bath with Raised Vanity, Open Layout with Spacious Shower with Seat and Barn Door Privacy Door. Guest Bath also Updated with New Raised Vanity and Shower. Second Bedroom Walk-in Organized Closet. New Master Bedroom Carpet in 2025, New Water Heater in 8/2025 A/C replaced 4-5 years ago. Sit on Covered Patio and enjoy Pool Views and Landscaped Vistas. Walk to Shopping, Restaurants, Movies, Trader Joe's. Minutes from Park Avenue and Farmer's Market. Centrally located, close to I-4. One of Winter Park's "Best Kept Secrets"! Make an Appointment to view today!
Courtesy: CHARLES RUTENBERG REALTY ORLANDO
407-622-2122
PRICE IMPROVEMENT! INCREDIBLE OPPORTUNITY! 5.75% ASSUMABLE MORTGAGE Interest Rate Available, making it an excellent opportunity for qualified Buyers. Welcome to 1422 Tierra Circle, beautifully refreshed immaculate pool home located in the well-established community of Casa Aloma, featuring 4 bedrooms, 2 full bathrooms and open floor plan. You will notice the enhanced curb appeal from the moment you arrive with newly painted exterior and driveway along with lush landscaping, creating a warm and inviting first impression. Many wonderful upgrades include a newer roof (2020), new electrical panel (2025), HVAC system (2022), HVAC/ air ducts cleaned and sanitized (2025), screened backyard patio (2023), new pavers and exterior shutters for added curb appeal, updated light fixtures, beautiful new front exterior door, new pool pump and luxury vinyl and carpet flooring (2022). The spacious living room flows into a versatile bonus area, both with excellent backyard pool views from the large window and sliding doors, allowing natural sunlight in. The bonus area is currently used as a playroom and ideal for an office space, library, bar or reading nook, leading to the kitchen. The kitchen is a chef’s delight, with stainless steel appliances, a gas stove and granite countertops, overlooking the dining room and sliding doors that open to the spacious screened patio and fenced backyard paradise. The large primary suite offers a peaceful retreat with double his-and-her closets and private ensuite bath, while three additional bedrooms provide flexibility for family, guests, or work-from-home needs. Step outside and enjoy true Florida living in your private backyard paradise, with a spacious screened patio, freshly painted pool deck, sparkling pool and an abundance of fruit trees, including limes, avocados, bananas, guavas, and mangos, perfect for entertaining or simply relaxing in the sunshine while enjoying fresh produce right at home. EXCELLENT LOCATION zoned for top-rated schools, minutes away from AdventHealth, Full Sail University, FL-436, and endless shopping and restaurants nearby. Come take a tour of this immaculate 4 bedrooms, 2 bathrooms immaculate pool home today!
Courtesy: PREMIER SOTHEBY'S INTL. REALTY
407-644-3295
Nestled in the heart of downtown Winter Park, this beautifully maintained 1920s traditional residence captures the essence of Old Florida charm while offering the comfort of modern amenities. From the moment you arrive, the wraparound porch and circular drive create a welcoming first impression, setting the tone for the timeless character found throughout. Step inside to a gracious foyer accented by a cozy fireplace, leading into the spacious formal living room with its own gas fireplace and the elegant formal dining room. Gorgeous heart-of-pine floors run throughout the first floor, adding warmth and authenticity. The kitchen has been thoughtfully updated with top-of-the-line Thermador and Sub-Zero appliances, including a 72-bottle Sub-Zero wine tower and refrigerated drawers, making it as functional as it is beautiful. Open to the family room, complete with rich woodwork and a third gas fireplace, this space is ideal for gathering and entertaining. The primary suite is conveniently located on the first floor and features an updated ensuite bath. Upstairs, three additional bedrooms and two renovated baths provide comfortable accommodations for family and guests. A charming “sleeping room,” now used as a light-filled office, overlooks picturesque New England Avenue. Adding to the property’s appeal is a detached two-story guest house offering a full bedroom, full bath, sitting area, and kitchen—perfect for extended stays or as a private retreat. Outdoor living is equally inviting, with a back porch for grilling, a separate patio for lounging and mature landscaping that enhances the home’s curb appeal. Architectural details available for adding an oversize two-car garage, if desired. Perfectly positioned on the same block as The Alfond Inn and just two short blocks from the renowned Park Avenue district, this home offers not just refined living, but a downtown walkable lifestyle that is truly unmatched. Park Avenue is the cultural heart of Winter Park—a tree-lined promenade alive with award-winning restaurants, boutique shopping, art galleries and historic landmarks. Residents enjoy a vibrant calendar of events, from the Winter Park Farmers’ Market and seasonal art festivals to beloved holiday parades and outdoor movies under the stars. Here, every day is an invitation to experience the best of Central Florida living—whether it’s sipping coffee at a charming café, strolling to or after dinner surrounded by beautiful ambience, or embracing the timeless traditions that make Winter Park so treasured.
Courtesy: JOHN SADRI & COMPANY
407-619-9999
A Rare Live/Work Opportunity! Work from home or utilize the space as an office, retail, daycare, or other permitted use. This fully renovated property includes two adjoining parcels: the main lot with the building, plus a vacant lot (50' x 155') offering future expansion potential for an additional structure, subject to zoning and county regulations. With a sought-after Winter Park address, the property spans over half an acre and features flexible commercial and residential zoning—perfect for a business, residence, or a true live/work hub. Modern finishes and an impressive aesthetic are showcased throughout. Highlights include a 2-car garage, security system with cameras, versatile interiors with 3 private offices (rooms), living and conference room, 2 bathrooms (one full, the second convertible back to full), kitchen, reception area, and a dedicated studio space. Furnishings are available with the sale. Owner financing may be an option. This unique and adaptable property, with excellent accessibility and prime location, presents outstanding potential for multiple uses and future expansion, including: * Entrepreneurs running a business from home * Contractors or service-based businesses needing office + parking and workspace * Medical/Dental or Professional Office * Retail, Daycare, or School * Residential or potential Airbnb conversion * Audio/Video production studio Location Highlights: * 15 minutes to UCF, Full Sail University & Downtown Winter Park * 25 minutes to Downtown Orlando * Quick access to Hwy 417 & I-4
Courtesy: ONE LUXURY INTERNATIONAL LLC
407-312-8003
Under Construction. Step into a world where the timeless charm of Old Winter Park meets the pinnacle of modern luxury designed by Winter Park Design and masterfully crafted by renowned builder Vimaro Homes. Nestled on one of Winter Park’s most coveted tree-lined streets, this stately home immediately commands attention with its double-entry driveway, framed by manicured landscaping and a sense of grandeur like no other. Inside, the home unfolds across more than 3,600 square feet of impeccably designed living space, with every room telling a story of quality, craftsmanship, and comfort. Rich herringbone hardwood floors stretch throughout the residence, complemented by bespoke millwork, and soaring ceilings. At the core of the home, the designer chef’s kitchen is a true showpiece, crafted for culinary excellence and effortless entertaining. Outfitted with top-of-the-line stainless steel appliances, custom cabinetry with designer hardware, and striking quartz countertops, the space is as functional as it is beautiful. A large island provides a natural gathering place, while an adjacent walk-in pantry offers seamless storage and prep. The primary suite is a retreat unto itself; a serene oasis tucked away for ultimate privacy. The spa-inspired en-suite bathroom rivals the finest resorts, featuring a soaking tub, walk-in shower with rainfall fixtures, designer lighting, dual vanities with custom cabinetry, and luxurious stone finishes throughout. A large, custom walk-in closet completes this elegant retreat. Beyond the main living areas, this home offers unique and thoughtfully designed spaces that elevate everyday living including a dedicated home office, a spacious loft, and a grand 3rd floor bonus room. Outdoors, a resort-style pool, covered lanai, and fully equipped summer kitchen create a private haven for year-round entertaining under the Florida sun. For the car enthusiast, this home offers a perfect fusion of elegance and functionality with a stately porte-cochere, a detached garage connected to the home by a breezeway, and an expansive motor court ideal for guest parking or showcasing a prized collection. Every element of this home speaks to impeccable taste and thoughtful design, from the curated finishes and luxury fixtures to the breathtaking architecture and designer lighting. Located just moments from Park Avenue, Rollins College, and Winter Park’s finest shopping and dining, you are truly in the heart of it all. More than a residence, this is a rare architectural masterpiece by Vimaro offering an unmatched lifestyle in the heart of one of Central Florida’s most coveted neighborhoods.
Courtesy: KELLER WILLIAMS REALTY AT THE PARKS
407-629-4420
Don't miss this exceptional opportunity to invest in a 1-bedroom, 1-bathroom condo in the heart of Winter Park. Centrally located near Baldwin Park, Full Sail University, the University of Central Florida (UCF), Downtown Winter Park, and Orlando International Airport, this property offers unmatched convenience.
Courtesy: FANNIE HILLMAN & ASSOCIATES
407-644-1234
Welcome to this stunning SINGLE STORY five-bedroom home with high ceilings, in one of Winter Park’s most desirable neighborhoods, where charming restorations and luxury new builds create a vibrant community feel. Designed with both beauty and comfort in mind, this open-concept home offers bright, welcoming living spaces and thoughtful upgrades throughout. Completely rebuilt in 2014 and tons of upgrades completed in 2025. The home sits on a 1/3-acre lot with 5 bedrooms and 3 ½ baths plus an office and features a 4-way split plan with privacy for all. Upon entering, you're greeted by an open floor plan with marble foyer and white oak engineered wood flooring. The Owners' Retreat is a true sanctuary, featuring newly sanded and smoothed walls with luxe finish, automatic Hunter Douglas shades and an artful chandelier. The brand-new spa-inspired bathroom (2025) showcases the best in design and function which includes Kohler Bask heated surface tub, private toilet room with heated seat, auto lid and integrated bidet. The primary bath also has a new expanded shower, a new double sink vanity and Kohler champagne brass fixtures. The Family/Gathering space with an open chef's kitchen includes a stainless gas range, French door refrigerator, waterfall Quartzite counters and touchless kitchen and bar champagne faucets. The great room has a modern electric fireplace and leads to a screened porch and overlooks the salt water pool and large fenced backyard. Black metal remote controlled gate leads to the large 2 car detached garage with a side entry for grocery and package drop off. Home has updated cameras and security with touch screen keypad. Smart home technology Lutron lighting to schedule and control lights with mobile or Google home. Redesigned Laundry and 1/2 bath with beautiful designer wallpaper and tile and Samsung washer/dryer integrated single unit. Ideally located in one of Winter Park's coveted neighborhoods, with easy access to Park Av, Phelps Park, YMCA and Rollins College. Excellent schools, Lakemont Elem, Maitland Middle and Winter Park High. This is a rare offering of a newer one-story home, that is move in ready in the heart of Winter Park. A Must See!
Courtesy: PREMIER SOTHEBY'S INTL. REALTY
407-644-3295
This stunning new contemporary residence, a five-bedroom, five-and-a-half bath home by the renowned Rex-Tibbs Development, a custom builder for over 40 years, continues to set the standard for luxury living. Perfectly situated on a premium, quiet, charming brick street, the home blends clean architectural lines with timeless finishes and thoughtful design details. An elegant foyer immediately introduces the home’s refined aesthetic, offering a direct line of sight to the gorgeous herringbone white oak floors in the great room and the sparkling pool just beyond the full glass doors. Anchored by a sleek linear gas fireplace with custom built-ins and floating shelves, the great room provides an inviting yet sophisticated gathering space. The open-concept chef’s kitchen is a showpiece in both form and function. Outfitted with Wolf and Sub-Zero appliances, it boasts an eight-burner range with one-and-a-half ovens, an oversized Sub-Zero French door refrigerator with a freezer drawer, a built-in microwave drawer, and a walk-in pantry featuring a wine and beverage tower. Marble counters in all baths continue the home’s commitment to refined finishes. The main level primary suite is a serene retreat with a spa-inspired bath featuring a large glass-enclosed shower, separate soaking tub framed by dramatic four-by-ten-foot porcelain slabs, a custom walk-in closet, and a private water closet. A flexible fifth bedroom with an ensuite bath offers the perfect option for an office or den. A striking glass-railed staircase leads to the second level, where a spacious lounge area opens to a private covered patio. Three additional ensuite bedrooms, each with custom closet systems, complete the upstairs living quarters. Designed for indoor-outdoor living, the expansive covered lanai includes a summer kitchen with a grill, hood vent, refrigerator, sink, and a dedicated half bath. Overlooking lush landscaping with tropical Clusia hedges and Foxtail palms, the brand-new pool is finished with designer tile that lends a stylish, resort-quality flair. Additional highlights include a spacious storage closet under the staircase, oversized two-car garage, 500-gallon propane tank for easy generator connection, stone paver driveway and durable metal roof. Wonderfully located in a picturesque neighborhood, the property is just minutes from the boutiques and dining of Park Avenue, top-rated public and private schools and offers convenient access to downtown Orlando, the attractions, as well as area airports. A rare opportunity to own a newly constructed home of such quality and craftsmanship in one of Winter Park’s most sought-after neighborhoods.
Courtesy: THE FLORIDA PROPERTY SHOP SALE
352-346-7857
Welcome home to this beautiful 2-bedroom, 1-bath gem in the heart of Winter Park! Nestled on the ground floor of the Lake Killarney Condominiums, Unit 101 offers a seamless blend of comfort, style, and lakeside living. Bright & open layout that flows from the living space into a modern kitchen with a large center island — perfect for entertaining or casual family meals. Granite countertops, stainless steel appliances, self-closing cabinets, and stylish finishes that reflect quality and fresh design. Newer insulated windows including large sliding doors bring energy efficiency to this to this immaculate home. Gorgeous views and spectacular sunsets over Lake Killarney you can enjoy from the lakefront pool, picnic & shuffleboard areas. Access to lake amenities including a community boat ramp and dock. Fishing, boating, relaxing by the water—this is everything you’ve dreamed of. Prime location: just minutes from Winter Park Village. Literally right next door to Trader Joe’s! Very convenient to Whole Foods, great dining, boutique shopping, and more. Commuting is a breeze with easy access to major roads This condo delivers more than just a home — it offers a lifestyle. If you value charm, ease, and access to nature plus city conveniences, this is the perfect pick. Whether you’re starting out, downsizing, or just wanting a beautiful place to come home to. * SELLER MOTIVATED * some photos virtually staged*
Courtesy: FANNIE HILLMAN & ASSOCIATES
407-644-1234
Introducing a rare opportunity to own a brand-new, luxury modern townhome just steps from Park Avenue in the heart of Winter Park. This stunning two-story, all-block construction residence offers the perfect blend of design, quality, and location—within walking distance to Hannibal Square, Rollins College, upscale dining, boutique shopping, and more. Inside, soaring 13-foot ceilings, custom wood flooring, Pella double-pane windows, and an abundance of natural light set the tone for sophisticated living. The chef’s kitchen is a showstopper, featuring flat-panel cabinetry, Quartz countertops, a Wolf gas cooktop, and Sub-Zero appliances. Every inch is thoughtfully designed, with recessed lighting, level 4 smooth wall finishes, and prewiring for surround sound, cameras, and a full security system. Upstairs, enjoy two guest suites, a spacious laundry room, and a luxurious primary suite with an oversized walk-in closet and spa-inspired bath. The townhome also includes a two-car garage with insulated steel doors and a rare 40x11’ private fenced side yard. This is exclusive Winter Park living at its finest—DM to schedule your private showing.
Courtesy: COMPASS FLORIDA LLC
407-203-9441
One or more photo(s) has been virtually staged. Set within the serene gated community of Hawks Crest in Winter Park, this beautifully designed single-story home combines modern comfort with resort-style living. Featuring 4 bedrooms, 2 baths, and 1,920 sq. ft. of thoughtfully crafted space, it’s the perfect blend of style and function. Inside, an open-concept layout creates seamless flow between the spacious family room, dining area, and gourmet kitchen—ideal for entertaining and everyday living. The kitchen offers granite countertops, large island seating, and stainless-steel appliances. The private owner’s suite is a relaxing retreat with a walk-in closet and spa-inspired bath, while three additional bedrooms provide flexibility for family, guests, or a home office. Step outside to a covered patio and low-maintenance yard designed for year-round Florida living, and pond view. Hawks Crest residents enjoy exclusive amenities including a clubhouse with fitness center, resort-style pool, splash pad, dog park, playgrounds, and private access to Lake Howell for kayaking and paddle boarding. The neighborhood is also minutes from local favorites like Kelly’s Ice Cream and Foxtail Coffee, with downtown Maitland, Park Avenue, and top-rated schools just minutes away. This home delivers not just a place to live, but a lifestyle defined by convenience, community, and charm. Don’t miss your chance to own in one of Winter Park’s most desirable neighborhoods—schedule your private showing today.
Courtesy: IMPERIAL REALTY OF FLORIDA INC
407-346-4746
PRIME LOCATION! Beautiful 3 Bedroom 2 Bathroom home is located in sought after Winter Park Pines with NO HOA and NO CDD. It is situated on a Corner Lot (0.22 Acre) and is a super short distance to the High Rated schools in Winter Park. The interior is extremely well kept with engineered wood floors, crown molding, and a beautiful glass entry door. There is a captivating white-washed stone fireplace and built in shelving for an elegant look in the Family Room. The kitchen has stainless steel appliances, wood cabinets with under cabinet lighting, and bar top seating. Primary Bedroom has a walk-in closet and a glass door shower with tile walls and built-in niches. The Primary bathroom has private access to the screened patio (Florida Room) and spacious backyard. The gated fence opens extra wide for boat, RV or your trailer entry. This entry is very convenient to back any trailer size. For outdoor activities, you just step out of the house and go on a Cady Way Trail for biking, skating, and walking activities. For tennis lovers there are very well kept tennis courts where sport enthusiasts practice their skills in pickleball. Right next to the tennis courts is a playground that offers cozy shaded areas with slopes, swings, and climbing walls. Publix, Costco, Walmart and the post office are all located nearby. For evening promenade the downtown Winter Park, located just a few miles away, offers unique restaurants, cozy coffee shops and bars. To see this amazing 3 bedroom home for sale in Winter Park, call today and schedule a showing! NOTE: Roof - July 2023. HVAC - 2015. No HOA, NO CDD.
Courtesy: PREMIER SOTHEBY'S INTL. REALTY
407-644-3295
Welcome to The Cloisters, one of Winter Park’s established lakefront communities, ideally between Park Avenue and Lake Osceola. This top-floor residence, rarely available in the building, offers a turnkey lifestyle with exceptional updates and peaceful water views. The home’s oversized screened balcony, complete with a custom awning, creates an uncommon open-air retreat that overlooks the community’s heated pool, putting green, manicured gardens and Lake Osceola. Unlike many residences in the community, this property retains its original open balcony design, offering outdoor living rarely found in this floor plan. Inside, every surface has been thoughtfully remodeled. The kitchen features solid wood cabinetry, granite countertops and refined finishes. Both baths are fully updated, including a new tub with glass enclosure in the guest bath and a walk-in shower with frameless glass in the primary suite. Tile flooring, custom vanities and designer fixtures complete each space. Engineered hardwood flooring runs throughout the main living areas, with plush carpet in the bedrooms for added comfort. The primary suite includes custom built-ins, dual closets and a built-in desk with additional cabinetry, delivering elegance and function. The second bedroom offers flexibility as a guest room or study and features optional shared access from the primary suite for additional privacy. Additional highlights include a covered and assigned parking space equipped with one of the building’s few electric vehicle charging stations, ample guest parking and access to a community dock with boat slips available through a resident lottery system. The Cloisters has successfully completed all required Milestone Inspections and the Structural Integrity Reserve Study, ensuring peace of mind for future residents and affirming the association’s commitment to long-term stewardship. Amenities include two fitness centers with dry saunas and a newly renovated clubhouse with kitchen and a partial bath for use as a powder room, ideal for hosting private events. Ideally positioned just steps from the dining, shopping and cultural energy of Park Avenue and in proximity to Rollins College, this original-owner residence offers a compelling blend of lifestyle, location and enduring design.
Courtesy: COMPASS FLORIDA LLC
407-203-9441
Nestled on the shores of private, skiable Lake Killarney, this beautifully updated and absolutely adorable 2-bedroom, 2-bath home offers a rare opportunity to enjoy true lakefront living without the upkeep of a large estate. Perfect as a full-time residence, a weekend lake escape, a snowbird retreat, or even an income-producing short-term rental (as previously used by the current owners), this charming property delivers the ultimate blend of convenience, recreation, and Winter Park lifestyle. Wake up to serene water views, spend your days boating across crystal-clear Lake Killarney, and end each evening with breathtaking sunsets on the water. From your private dock, you can cruise straight over to Hillstone for happy hour or pull up to Trader Joe’s for a quick grocery run—the kind of effortless, magical living that only this lake can offer. Located just minutes from Park Avenue’s boutique shops, fine dining, and cultural attractions, this home feels worlds away while keeping you close to everything you love. Whether you're wanting to downsize and have low maintenance, a seasonal resident seeking a warm-weather sanctuary, or a local looking for the perfect weekend getaway to store your boat, this home delivers a lifestyle unlike anything else in Winter Park. A unique location, a turn-key home, and an unmatched lake experience; this Lake Killarney gem is a must-see and you won’t want to miss it.
Courtesy: COMPASS FLORIDA LLC
407-203-9441
Welcome to this stunning townhome in the heart of Winter Park, built by award-winning Osprey Custom Home Builders. This residence combines timeless design, coastal aesthetic, certified greb construction, energy efficiency, and modern smart-home conveniences. Featuring 3 bedrooms, 2.5 baths, and an open-concept layout, the home is filled with designer finishes and thoughtful details throughout. The first floor offers inviting living and dining areas with plank-style tile floors, surround sound speakers, and high ceilings. The gourmet kitchen is equipped with maple cabinetry, a generous island with waterfall quartz countertops, Samsung stainless steel appliances, a bar, pantry, and walk-in closet. From the kitchen, triple sliders open to a private walled courtyard, perfect for outdoor dining and entertaining, and an oversized 2-car garage. Upstairs, the spacious primary suite includes a luxurious glass-enclosed walk-in shower, double vanity, and large custom walk-in closet. Two additional bedrooms, also with custom closet built-ins, share a well-appointed bath with high-end finishes. An oversized laundry room completes the second floor. Smart Home features include a WiFi-enabled garage and thermostat, central smart-home hub, and central vacuum system with a built-in kitchen dustpan. Other upgraded features include designer moldings, solid doors, and Andersen windows. Designed with comfort, convenience, and sustainability in mind, this home is in immaculate condition and move-in ready. Ideally located just minutes from Park Avenue, Rollins College, Mills 50, Ivanhoe, Trader Joe’s, Whole Foods, Advent Health, and Downtown Orlando, this property offers easy access to fine dining, shopping, and Central Florida attractions. Don’t miss the opportunity to enjoy luxury, convenience, and modern efficiency in one of Winter Park’s most desirable townhome communities. Schedule your private showing today!
Courtesy: AUTHENTIC REAL ESTATE TEAM
407-440-1010
Modern luxury meets Winter Park charm — fully renovated 4BR/2BA with $20K seller credit with full price purchase! This beautifully reimagined 4-bedroom, 2-bath home has undergone a complete transformation. Every detail thoughtfully designed and executed. From brand-new plumbing, electrical, and HVAC systems, to a stunning new floor plan created by an international architect, this home blends modern functionality with timeless charm. Step inside and be greeted by an open concept living space filled with natural light. A striking oversized window frames the outdoors like a work of art, while the preserved original stone fireplace adds warmth and character to the living and dining area. The brand-new kitchen flows seamlessly into the space, making it perfect for gatherings and family moments. Designed for today’s lifestyle, the home now features a private office, ideal for remote work or study, and a newly added bedroom that expands comfort and flexibility. The dedicated laundry room and thoughtful storage solutions bring convenience to daily living. Outside, the enclosed porch invites you to enjoy Florida evenings year-round, whether it’s sipping a glass of wine or hosting friends in a cozy, bug-free setting. Nestled on a quaint, family-friendly street just steps from a neighborhood school, this home offers both peace and practicality. It is also located within the highly desirable Winter Park school district, with access to top-rated public schools—making it an ideal choice for families seeking both quality of life and excellent education opportunities. The surrounding area, while rich in tradition, is experiencing a wave of new builds and renovations—making this not only a beautiful place to live, but also a smart investment in one of Winter Park’s most desirable and appreciating communities. Added Bonus: With a full-price purchase, the seller will contribute $20,000 towards your closing costs or to buy down points on your interest rate—your choice! This makes an already stunning home an even more incredible opportunity. Don’t miss the chance to make this fully renovated Winter Park gem yours. Schedule your private tour today and experience the perfect blend of comfort, style, and location.
Winter Park is located in Florida. Winter Park, Florida has a population of 29,672. Winter Park is less family-centric than the surrounding county with 27.95% of the households containing married families with children. The county average for households married with children is 31.51%.
The median household income in Winter Park, Florida is $88,688. The median household income for the surrounding county is $65,784 compared to the national median of $69,021. The median age of people living in Winter Park is 45.3 years.
The average high temperature in July is 92 degrees, with an average low temperature in January of 49.4 degrees. The average rainfall is approximately 51.9 inches per year, with 0 inches of snow per year.
