Winter Park Homes For Sale & Real Estate - 409 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: One or more photo(s) has been virtually staged. MILLIONAIRE LIFESTYLE HIDDEN GEM • LAKE ACCESS • 2 BED / 2 BATH CONDO ON LAKE KILLARNEY • PRIME WINTER PARK LOCATION • LOW HOA Outstanding Opportunity to live the Florida Lifestyle in your private walkable Lakefront Enclave. Includes Direct Lake Access, Private Dock, Loungers and seating, Picnic areas and landscaping, Boat Slip, and a Private Pool & Clubhouse overlooking Lake Killarney. You will love Paddle Boarding, Kayaking and Boating just steps from your door. Beautifully updated 2-bedroom, 2-bathroom condo located on the shores of Lake Killarney in highly desirable Winter Park. This immaculate home offers tranquil lakeside living and unbeatable convenience, minutes from Trader Joe’s, Park Avenue, Rollins College, and Downtown Orlando. The condo is upgraded throughout with New AC & Water Heater, Fresh New Interior Paint, New Lighting, New Ceiling Fans & Window Blinds, Updated Door Hardware, Primary Bathroom Renovation featuring new tile, modern vanity, and LED mirror, Upgraded Exterior Doors & Windows. Open-concept kitchen with dark wood cabinetry, granite countertops, a built-in wine rack, and breakfast bar, flows into the spacious living area and private balcony. Enjoy two private patio spaces front and rear, overlooking the courtyard, perfect for relaxing and entertaining. With only one neighbor to the side and one below, this unit offers enhanced privacy. Split-Bedroom Design, Two large bedrooms, each with walk-in closets. Primary suite includes a private exterior entrance and a fully renovated bathroom with walk-in shower. Second bathroom includes a tub/shower combo and tile flooring. Enhance your life living minutes from Park Avenue (shopping, dining, events), Rollins College (3 miles), Winter Park Village, I4 for easy commuting, Downtown Orlando, Orlando International Airport, Disney, and Universal (20–30 mins). Low HOA Includes Water & Trash, Cable & Internet, Lake Access & Dock, Pool & Clubhouse, and Designated Parking.

Listing is courtesy of: THE ANDERSON GROUP & CO PL (407-960-5657)

Listing Agent: Alison Maltby (407-325-1483)

Remarks: Under contract-accepting backup offers. Located in the highly desirable Casa Aloma neighborhood of Winter Park, this updated 3-bedroom, 2-bath, 2,083 sq ft home offers unique architectural appeal paired with thoughtful modern enhancements. Built in 1969, the home features concrete block construction on a concrete foundation, providing durability and peace of mind. Situated on a corner lot with updated landscaping, the property offers excellent curb appeal and outdoor functionality. Inside, the home has seen numerous recent updates, including new quartz kitchen countertops (2025), updated bathrooms, and updated walls and flooring throughout. The bonus room provides flexibility for use as an additional bedroom, home office, or secondary living area. Major system improvements include PEX plumbing, a newly installed 17 SEER AC system, a new water heater, electrical updates completed in 2008, and a metal roof installed in 2013 over 1x12 tongue-and-groove decking, offering exceptional strength and longevity. The home is protected by an active termite bond, with Sentricon installed in 2025. The backyard is highlighted by a 15’ x 30’ in-ground pool, a new vinyl fence (2023), and a five-zone in-ground sprinkler system with a programmable timer. The property is located in Flood Zone X (no flood insurance required) and has no HOA. Enjoy an excellent location known for top-rated schools, just minutes from AdventHealth, Full Sail University, FL-436, and an abundance of shopping and dining options. Do not miss the opportunity to purchase a well-maintained home with proven rental income and long-term investment potential.

Listing is courtesy of: SOUTHERN LAND & HOMES (850-973-2200)

Listing Agent: Benjamin Jones (850-673-7888)

Remarks: Tucked behind towering hedges on a coveted brick-lined street, this estate sits on an approximately ½-acre corner lot and has been enhanced with thoughtful improvements, delivering a rare combination of modern functionality, Old World charm, and a fabulous lifestyle. Notable updates include newer HVAC systems (2020 and 2025), a tankless gas water heater, a fully renovated laundry room with new LG stackable washer and dryer, newer kitchen appliances, new copper gutters and downspouts, fresh exterior paint (2025), a newly designed primary bathroom, and much more. The main residence spans over 3,600+ SF with an attached 2-car garage and is complemented by a detached, fully equipped 700+ SF studio apartment located above an additional 2-car garage, as well as an air-conditioned outdoor bar. With two dwellings, a four-car garage, expansive outdoor entertaining space on ½ acre, and surrounded by tall podocarpus hedges, this home is a true private compound. This is not just a home—it’s a destination! Enter the main residence into a dramatic living space featuring 12-foot ceilings, a 30-foot span, a gas fireplace, and walls of windows and doors. With a rear southern exposure, natural light pours in through five sets of French doors, offering views of the brick-paver pool deck and lush, fenced grounds beyond. The family room flows seamlessly into the open kitchen, elevated by newer luxury appliances including a Sub-Zero refrigerator, Wolf gas range, and dual Miele dishwashers. At the center, a copper-topped island anchors the space, complemented by a wood-stained beadboard ceiling and a spacious dinette for casual dining. Just beyond the kitchen, a large dining room and adjacent den (currently used as a library & office) offers flexible living options. A side entrance opens to a covered porch overlooking a generous side yard framed by tall privacy hedges—ideal for a dog run or discreet boat storage. Downstairs, three additional bedrooms feature vaulted ceilings and access to three well-appointed full baths, creating a functional layout for family and guests. Privately positioned upstairs, the expansive primary suite offers a quiet retreat, highlighted by a recent full-scale luxury bathroom renovation with elegant custom finishes. Features include a large glass shower with three showerheads, dual vanities, a Toto washlet, designer mood lighting, and custom cabinetry with linen storage. French doors from both the bedroom and bath open to a covered balcony overlooking the backyard and pool, while three custom walk-in closets create a true dressing room experience with additional flexible space for an office or hobby room. Designed for entertaining, the outdoor living is equally impressive. A sprawling lawn surrounds the large saltwater pool and expansive paver patio for lounging and dining. A covered, air-conditioned bar is outfitted with custom cabinetry, exquisite lighting, a copper sink, dishwasher, wine fridge, and beverage fridge—all secured by an electronic storm shutter. The extended bar seamlessly serves the adjacent tent-covered lounge area, complete with a pool bath and outdoor shower. The detached studio apartment, positioned above the second 2-car garage, features a private entry along with a full kitchen and bath, making it ideal for extended stays or flexible living arrangements. Located just minutes from vibrant Park Avenue, this distinctive Winter Park compound blends curated finishes, meaningful upgrades, and exceptional privacy.

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

Listing Agent: Marystuart Day (407-620-8683)

Remarks: Charming 2-bed home in Winter Park located in the Golfview subdivision offering approximately 1,150 square feet of living space on a 6,414 square foot lot. Built in 1946, this single family residence features a functional layout with a blend of original character and updated interior finishes. The home includes original pine flooring in the main living areas, ceramic tile in the kitchen and dining spaces, and strong natural light from multiple window exposures. The kitchen has been updated with white cabinetry, granite countertops, and a mix of stainless steel and black appliances. The bathroom features updated finishes including a modern vanity and shower. Additional features include a covered front porch, one car attached garage with laundry area, central air conditioning with updated ductwork, and a fenced backyard with deck space suitable for outdoor use. The property is connected to public water and sewer and offers practical living with no HOA. Located near Dubsdread Golf Course and within close proximity to AdventHealth, College Park, and Downtown Orlando. Easy access to I-4 and surrounding roadways supports convenient travel to employment, dining, and retail centers. This property is suitable for a primary residence or investment opportunity in a well located Winter Park area.

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

Listing Agent: Tyler Gibson Llc (877-366-2213)

Remarks: Under contract-accepting backup offers. Rare No-HOA home with NEW ROOF 2022 and dedicated HOME OFFICE/FLEX SPACE! This move-in-ready 3-bedroom, 2-bathroom residence offers 1,366 sq ft of smart living plus an bonus room perfect for remote work, creative studio, or guests—functionality of four spaces without the 4-bedroom price premium.Enjoy zero HOA restrictions, significant monthly savings, and peace of mind with a 3-year-old roof (transferable documentation included). Features include updated flooring throughout (no carpet), fully fenced backyard, and 2-car garage. Zoned for desirable Seminole County schools (Eastbrook Elementary/Lake Howell High) with quick access to SR-436, shopping, and downtown Winter Park. Ideal for remote professionals, small families, or savvy buyers seeking low-maintenance ownership with room to work and grow. Quick closing available. Schedule today!

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

Listing Agent: Fernando Perez De Armas (407-837-7144)

Remarks: Tucked along one of Winter Park’s charming brick streets and positioned directly across from Lake Sylvan, this recently renovated residence unfolds like a quiet design story, one where character, craftsmanship and modern ease are aligned. From the moment you arrive, the home’s inviting curb appeal and reimagined cottage gardens set the tone, offering a sense of arrival that feels timeless and effortlessly refined. Inside, light pours through expansive picture windows, illuminating marble floors that flow seamlessly through the living room, dining area and kitchen. Every space has been thoughtfully curated by New York City–based interior designer Paulette Pascarella, where classic architecture is elevated by contemporary finishes and a restrained, sophisticated palette. The new kitchen serves as a centerpiece and a gathering space, featuring custom cabinetry, quartz countertops with a full-height backsplash and a high-end appliance suite anchored by a Bertazzoni refrigerator, equally suited for everyday living or intimate entertaining. Just beyond, the family room or den introduces warmth and texture with beautiful wood floors and custom built-ins designed for function and form. Motorized shades by The Shade Store, lighting by Visual Comfort and Currey, and hardware details by Buster + Punch are layered throughout the home, complemented by exquisite textile selections from Brunschwig, Schumacher, Thibaut, and Cowtan & Tout, each detail quietly reinforcing the level of thought and design intention behind the renovation. The second floor is a serene retreat and allows for elevated view of Lake Sylvan. The primary suite with soaring ceilings offers a generous window framing treetop views. The spa-inspired bath features a large glass-enclosed shower and a custom built-in dressing area, creating a private sanctuary that feels removed from the everyday. Two additional bedrooms, one with an en-suite bath, complete the upper level, offering flexibility for guests, work-from-home needs or extended stays. Outdoors, the grounds have been thoughtfully reimagined to evoke a cottage garden feel, providing a peaceful backdrop for morning coffee or evening strolls along the brick-lined street. The location is equally compelling, in a neighborhood known for its winding roads and timeless charm, just minutes from shopping, dining and cultural offerings of Park Avenue. Offering a lock-and-leave lifestyle, this home lives beautifully as a primary residence or as a second or third home and presents a compelling alternative to condominium or townhome living, where privacy, design and a desired Winter Park setting come together in one exceptional offering. There is potential for a third bedroom suite by converting the den/family room on the first floor as it is adjacent to a full bath.

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

Listing Agent: Mick Night (407-629-4446)

Remarks: Under contract-accepting backup offers. Back in market for Buyer finance .A great living in Winter Park. This 2-bedroom, 2-bath Furnished condo in The Colonies offers an excellent opportunity for investors or first-time buyers. Recently updated with new flooring and new painting the unit is ready for a new owner. The location is a major draw, just minutes from Full Sail University,Sam Wearhouse, Valencia College, UCF, Park Avenue, Downtown Orlando, and Orlando International Airport. With highly rated Winter Park schools, and shopping, dining, and cultural attractions nearby,. A rare chance to own in Winter Park at a great price, this condo combines strong value with a prime location.

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

Listing Agent: Amin Abraham (407-230-0803)

Remarks: Just steps from the charm and energy of Park Avenue, this exceptional Winter Park residence was completely rebuilt in 2018 by renowned custom builder Posada Homes, member of the elite Master Custom Builders Council. Offering a rare blend of modern design, crisp architectural lines, and timeless elegance, on an expansive 0.39-acre lot along one of Winter Park's most picturesque tree-lined streets. The home immediately captivates with its refined architecture and beautifully manicured grounds. Inside, sunlight streams through expansive windows, illuminating hardwood flooring, intricate millwork, and thoughtfully curated finishes that reflect the craftsmanship of a true custom build. Just off the foyer, a hidden wine room provides a sophisticated surprise, perfect for those who love to entertain. At the center of the home is the chef's kitchen designed for both beauty and functionality. Outfitted with premium Thermador appliances, sleek quartz countertops, a generous center island, and custom cabinetry, the kitchen flows effortlessly into the expansive great room where high ceilings, designer lighting, and elegant architectural details create an atmosphere that is both inviting and refined. Tucked away for privacy, the primary suite is positioned just off a luxurious family room featuring custom built-ins and a gas fireplace. The primary suite itself is a true sanctuary, complete with a sitting area, private coffee bar, and a spa-inspired bath featuring dual vanities, a soaking tub, and an oversized walk-in shower. Rarely found in Winter Park, all bedrooms are conveniently located on one level, including two primary suites. The home offers seamless livability without sacrificing architectural interest or sophistication. Upstairs, a private office, half bath, and bonus room provide the perfect space for work, media, recreation, or relaxation. Outdoors, the home transforms into a private resort-style retreat. A covered lanai overlooks the sparkling pool and expansive grounds, creating the ideal setting for entertaining or quiet evenings at home. Adding even more flexibility, a 252-square-foot detached studio currently functions as a gym but could easily become a summer kitchen cabana, guest retreat, or art studio. Located within walking distance of Park Avenue's boutiques, restaurants, and cafés, and just moments from Rollins College and the Winter Park Chain of Lakes, this residence embodies luxury living at its finest. Don't miss this rare opportunity to own one of Winter Park's most outstanding homes.

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

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

Remarks: Under contract-accepting backup offers. Move right into this beautifully two-bedroom, two-bath condominium located in desirable East Winter Park. The thoughtfully designed floor plan offers two spacious bedrooms, and bathrooms—one featuring a tub and the other a shower—providing comfort and privacy. The light-filled great room showcases attractive laminate wood flooring and sliding glass doors that open to a private, screened-in porch overlooking a sunny, landscaped courtyard—perfect for relaxing. Recent upgrades include a new AC system (May 2021), a new roof (2022), exterior paint 2025, updated bathrooms, upgraded laminate wood flooring throughout. The primary bathroom has been enhanced with a luxurious walk-in shower featuring upgraded stone and tile finishes. This unit is quietly situated in a private location within the well-maintained Wrenwood Condominiums community, offering assigned parking directly in front of the unit and access to a sparkling community swimming pool. Ideally located in East Winter Park, this community offers easy access to Park Avenue shopping and dining, Winter Park Village, Full Sail University, and nearby parks and lakes. Enjoy a vibrant lifestyle with museums, farmers markets, scenic walking areas, and the renowned Winter Park Chain of Lakes just minutes away, all while remaining close to major roadways and downtown Orlando. Schedule your private showing today.

Listing is courtesy of: SUNSHINE BROKERAGE, LLC (407-509-7961)

Listing Agent: Sonny Manku (407-509-7961)

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: One or more photo(s) has been virtually staged. Set on a prized corner lot in Winter Parks sought after Orwin Manor Neighborhood, 1651 Westchester Ave is a timeless classic with Cape Cod inspired architecture that has been meticulously reimagined with today’s luxury finishes while preserving its original charm. Refinished Original Pine hardwood flooring and a beautifully updated fireplace welcome you into the main living space, while the showpiece kitchen delivers true chef-level design with new Custom European Cabinetry, Quartz Countertops with a Waterfall Island, Porcelain Tile floors, premium lighting, under counter Kitchen Aid Ice Maker and a top-tier appliance suite including Wolf Gas Range-top, Wolf Built-in Oven & Microwave and Bosch Refrigerator and Dishwasher. The primary suite is a serene retreat with a newly redesigned spa style bath with frameless walk-in shower, soaking tub, new double sink vanity and lighting—plus a walk-in closet with California Closet built-in’s and a versatile bonus room ideal for a sitting area, nursery, or additional laundry space. Outdoors, enjoy resort-style living under the expansive 26’ x 24’ covered Lanai featuring vaulted tongue-and-groove ceilings, tile flooring, a striking stone gas fireplace with RealFyre burners, stainless mantle, perfect for effortless entertaining. There is even enough room to customize the outdoor space with your own Pool Oasis. Recent improvements include Roof 2020, New HVAC System, New Double-Pane windows, 4-panel slider & front door, fresh interior/exterior paint, new custom shades, privacy bamboo landscaping, privacy fencing and an extended paver driveway. The attached Garage offers dedicated storage space and a bonus room with mini-split system which could offer space for home gym or office. Just minutes from Park Avenue’s acclaimed dining and shopping, top Winter Park amenities, Advent Health Medical Campus and quick access to key corridors for an easy downtown Orlando commute, this is 32789 living at its most refined—classic architecture, modern systems, and elevated indoor-outdoor lifestyle in one of Winter Park’s most sought-after neighborhoods.

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

Listing Agent: Shawn Layton (321-514-8055)

Remarks: Welcome to 2889 Rouen Avenue, Fresh exterior paint and move-in-ready 3-bedroom, 2-bath residence offering approximately 1,140 square feet of comfortable living space. This home features a bright and functional layout, well-sized bedrooms, and a large fenced yard with plenty of room to enjoy the outdoors. Brand New water heater. Brand new Roof is underway. Conveniently located near Rollins College, Park Avenue, Full Sail University, shopping, dining, and I-4, and zoned for Dommerich, this property offers an outstanding opportunity in a sought-after location. see private remarks and showing time for direct seller’s contact.

Listing is courtesy of: HELLOSOLD LLC (954-778-5300)

Listing Agent: Dan Farber (954-778-5300)

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: Offering the comfort and feel of a single-family home with the convenience of townhome living, this beautifully maintained two-story residence features 3 bedrooms, 2.5 baths, and a private courtyard conveniently located in Winter Park. Sliding glass doors throughout the home fill the interior with natural light and create a seamless connection to your private outdoor courtyard. Inside, the spacious layout is complemented by low-maintenance tile flooring throughout and a cozy wood-burning fireplace, adding warmth and character to the main living area. The kitchen is well-appointed with granite countertops, stainless steel appliances, and a newer refrigerator, while the generously sized bedrooms provide comfortable retreats. The primary suite features two closets and an ensuite bath with dual sinks. Major system updates provide exceptional peace of mind, including a brand-new roof and HVAC system installed in January 2026, along with fresh exterior paint, newer gutters (approximately three years old), and a newer fence. The washer and dryer convey, making this home truly move-in ready. The community offers an exceptionally low HOA fee of under $200 per month, adding to the home’s overall value. Ideally located with easy access to Winter Park, Maitland, Full Sail University, UCF, Rollins College, and Valencia College, as well as nearby shopping, dining, and major roadways. With its spacious design, private outdoor space, and proven rental history, this property presents an outstanding opportunity as either a primary residence or investment. Reach out to schedule your private showing now!

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

Listing Agent: Jill Healey (407-797-1420)

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: Well-maintained 2-bedroom, 2-bath home with 1,199 sq ft in a desirable Winter Park 32792 location offering a fenced backyard, low HOA, and a flexible bonus space ideal for a home office, study, or hobby area. The functional split-bedroom layout provides privacy, while the open living and dining areas create a comfortable space for everyday living or entertaining. The kitchen offers ample cabinetry and counter space, flowing seamlessly to the main living area plus upgraded appliances. The primary suite includes a private bath and generous closet space, while the secondary bedroom and full bath provide flexibility for guests, office use, or additional living needs. Enjoy outdoor living in the fully fenced yard—ideal for relaxing, gardening, or pets. Additional highlights include driveway parking, interior laundry, and low-maintenance living. -- NEW ROOF IN PROCESS -- Prime location with convenient access to major corridors and top destinations: ˜ 3 mi to Full Sail University, ˜ 5 mi to UCF, ˜ 4 mi to AdventHealth Winter Park, and ˜ 6 mi to Park Avenue and Downtown Winter Park. Nearby shopping, dining, and grocery options are within minutes, with quick connectivity to SR-436, University Blvd, and SR-417 for commuting throughout Central Florida. An excellent opportunity to own in Winter Park with space, privacy, and strong location value.

Listing is courtesy of: WEMERT GROUP REALTY LLC (407-743-8356)

Listing Agent: Jenny Wemert (407-809-1193)

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: Welcome to this beautifully updated Winter Park home, perfectly positioned on a desirable corner lot and zoned for Audubon Park K-8 and Winter Park High School. With 5 bedrooms and 3 full baths, this spacious residence offers the ideal blend of functionality and style for modern living. Step inside to an open, light filled floor plan featuring luxury vinyl floors and a cozy wood burning fireplace that anchors the main living space. The renovated kitchen is thoughtfully designed with both everyday living and entertaining in mind, flowing seamlessly into the dining and living areas. A dedicated office provides the perfect work from home setup or quiet retreat, while the flexible layout offers plenty of room for guests, growing families, or multi generational living. Outside, enjoy a private backyard with a charming fire pit and rock gathering are deal for relaxing evenings or hosting friends. The oversized lot also offers ample space to add a pool and create your own backyard oasis. Additional highlights include a 2-car garage, roof replaced in 2018, home repiped in 2019, and updated AC for peace of mind. This is a rare opportunity to own a move-in ready home in one of Winter Park’s most sought after neighborhoods, walking distance to the Audubon Park Garden District with amazing dining, and shopping.

Listing is courtesy of: NORDQUIST & COMPANY INC (407-694-0996)

Listing Agent: Elizabeth Nordquist (407-694-0996)

Remarks: Under contract-accepting backup offers. Newly built in the heart of Winter Park, this warm modern-industrial residence offers 4 bedrooms, 3.5 baths and 3,031 heated square feet of thoughtfully designed living space (3,674 total including a two-car garage). Soaring 12’8” ceilings downstairs and 10’ ceilings upstairs create volume and light throughout. Oversized black grid windows flood the home with natural light and offer water views from the second level. Designer LED ambient lighting is integrated throughout — including illuminated floating stair treads and custom feature shelving — creating a dramatic yet inviting atmosphere. The kitchen is both refined and functional, featuring an oversized island, premium appliances, expansive prep space, and a generous walk-in pantry. The open layout flows seamlessly into the living and dining areas, anchored by a striking fireplace feature wall and wide-plank wood flooring. The primary suite offers a spa-level retreat with a dedicated wet area and freestanding soaking tub, delivering a luxurious, architectural bathroom experience. Designed for entertaining, the outdoor living space includes a private pool and a fully equipped summer kitchen — ideal for Florida living year-round. Additional features include: • Spray foam insulation for superior efficiency • Deeded access to a private boat ramp on Lake Killarney • No HOA dues Located in one of Central Florida’s most desirable neighborhoods, this home is just a short walk or drive to Park Avenue dining, shopping, and entertainment. A rare opportunity to own new construction with architectural character in Winter Park.

Listing is courtesy of: CLASSIC HOMES (407-493-8553)

Listing Agent: Randy Lazarus (407-247-9337)