Homes for Sale Near Glenridge Middle in Winter Park - 71 homes

Remarks: **Welcome to Four Seasons — Where Winter Park Living Meets Modern Convenience**This sharp 2-bedroom, 1.5-bath townhome puts you right in the heart of one of Central Florida's most coveted zip codes. With 1,219 square feet of updated, move-in-ready living space, it's the perfect low-maintenance home base for a busy professional who wants style, comfort, and location all in one.The renovated kitchen features granite countertops, wood cabinetry, and all the essentials for weeknight cooking or weekend entertaining. A flexible dining area doubles effortlessly as a home office — because your lifestyle demands options. The living room opens to a private, shaded patio with pavers that offers a quiet escape after a long day.Both bedrooms are generously sized with ample closet space. Practical upgrades are already done for you: newer HVAC and water heater, and updated fixtures throughout.Four Seasons residents enjoy three pools, a fitness center, tennis courts, and tree-lined walkways — resort-style amenities without the resort price tag. Step outside the community and you're minutes from Park Avenue's best restaurants and boutiques, Aloma Avenue shopping, and major corridors including SR 436, 417, and 408.This is Winter Park without the compromise. Schedule your private showing today.

Listing is courtesy of: EXP REALTY LLC (888-883-8509)

Listing Agent: Ginny Adkins Llc (407-288-6497)

Remarks: Situated in the heart of Winter Park, this custom-built Mediterranean-style estate offers an exquisite living experience that marries timeless architecture with modern innovation. A dramatic grand foyer introduces a residence where every finish has been meticulously curated, from Turkish travertine stone and rich wood flooring to Brizo hardware in Brilliance Polished Gold. At the heart of the home, the chef’s kitchen blends elegance and function with gleaming stainless steel appliances, crisp white cabinetry, granite countertops, and a well-appointed Butler’s pantry with a dedicated bar, creating a sophisticated setting for effortless entertaining. Integrated smart features further elevate daily living, including an intercom system for seamless communication, electronic blackout curtains for instant privacy and ambiance, and thoughtful, layered lighting throughout. The magazine-worthy primary bath—featured in Florida Home—feels like a private spa retreat, with floor-to-ceiling back-lit mirrors, a self-cleaning smart toilet with bidet, a custom Barclay soaking tub with black matte exterior, and Calcutta gold marble countertops and backsplash. These luxe finishes are anchored by an oversized chevron pattern tile by Crossville in Ice White, a throwback diamond-pattern shower floor, and a sculptural Kuzco LED chandelier that completes the space with dramatic flair. Expansive living areas open to resort-inspired outdoor spaces where a heated saltwater pool and spa, private mini-golf green, and a summer kitchen with tongue-and-groove wood ceiling create a true indoor-outdoor sanctuary. Velux solar-powered skylights with acoustic rain sensors that automatically close at the first sign of rain, a Mosquito NIX misting system, comprehensive surveillance, and electronic private gated access provide both comfort and peace of mind. Natural gas service and a dedicated hook-up for a whole-house generator underscore the home’s emphasis on performance and preparedness. Crafted for those who expect uncompromising quality, this Winter Park residence is more than a home—it is a refined sanctuary where architectural presence, rich materiality, and thoughtful technology converge in one coveted address.

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

Listing Agent: Robyn Brehne-Glass (407-474-4038)

Remarks: Virtually Staged. Move-in ready Sylvan Heights Mid-Century Bungalow, with no renovations needed. As you approach, you will notice the wonderfully cared for home with mature landscaping and a unique style. A charming, three-bedroom two-bath home has updated Kitchen and Bathrooms, there is even a large formal dining space with a built-in serving bar and wine fridge. The floors were upgraded with engineered hardwood throughout with tile in both bathrooms. Situated on a larger lot with a fully fenced in backyard that also has a 12x15 brick patio and room to add a swimming pool if desired. Sylvan Heights is one of Winter Park's Primer residential communities, that is close to Advent Health's Winter Park Hospital and top-Rated Rollins College. Just a short bike ride to Park Avenue in Downtown Winter Park with tons of shops and restaurants so you won’t have to go far for fun. Also, just minutes to downtown Orlando, and all of the Central Florida attractions so get the guest room ready for visitors... Sound like a home you would like to see. Schedule a private showing today.

Listing is courtesy of: SUMMERPARK HOMES REALTY LLC (407-603-6320)

Listing Agent: Buddy Jerome, Iii (407-579-9356)

Remarks: Winter Park lakefront home! A rare opportunity to own a thoughtfully renovated mid century lakefront residence in Winter Park. This three bedroom four bath home offers stunning views, high ceilings and abundant natural light. The open layout flows effortlessly for everyday living and gatherings with friends and family. As you walk through the front door, you will be drawn to the large living area and a wall of windows and doors leading to the lake. The island kitchen is a cook's dream with abundant workspace and welcoming island seating. Imagine waking up every morning to yet another amazing view- The primary suite is spacious and private with newer bath and large walk- in closet. Nicely appointed secondary bedrooms and updated baths. In addition to the main living area, there is a separate oversized family room with a full bath adjacent. This home is a perfect blend of classic architecture and carefully designed updates. Other features include two car garage with "glass" overhead doors and mini-split HVAC, metal roof, generous closets & storage throughout and recently installed sod. What makes this house truly special is the setting on Lake Spier- a ski lake tucked away in a secluded part of Old Winter Park . There are no homes across the lake- so spending time on the patio and dock offers an expansive view of water and trees and a remarkable sense of privacy. Inside and out, every space feels connected to the natural beauty. Great location to enjoy Winter Park living. Ideally situated near top rated schools - Baldwin Park, Glenridge and Winter Park High School. Enjoy close proximity to walking trails, restaurants and shopping. This home is truly special!

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

Listing Agent: Nicole Seybold (407-808-9374)

Remarks: A PRIVATE RESORT-STYLE SANCTUARY IN THE HEART OF WINTER PARK 5 Bedrooms | 4 Bathrooms | 3,400+ SF | Saltwater Pool & Spa | Smart Home | Minutes to Park Avenue Welcome to a rare offering where luxury, tranquility, and architectural sophistication converge. Nestled within one of Winter Park's most desirable neighborhoods and just minutes from the boutiques, fine dining, and cultural attractions of Park Avenue, this custom Mid-Century Modern residence delivers an extraordinary lifestyle defined by elegance, wellness, and privacy. Thoughtfully designed with a Zen-inspired aesthetic, the home seamlessly blends clean architectural lines with warm natural elements to create a living experience that feels refined and restorative. From the moment you arrive, an atmosphere of calm surrounds you, offering a peaceful escape while remaining moments from everything Winter Park has. Inside, soaring 10-foot ceilings, expansive walls of glass, and wide-plank engineered hardwood flooring create bright, open living spaces filled with natural light. A stunning semi-floating steel staircase with solid whiteoak treads serves as a dramatic architectural focal point, while designer Restoration Hardware lighting adds warmth and sophistication throughout. The main living area was designed for entertaining and everyday luxury. A sleek Dimplex fireplace anchors the great room, complemented by a custom wine bar. At the heart of the home, the chef's kitchen showcases a waterfall island, premium quartz countertops, striking marble backsplash, double-stacked cabinetry, and a custom pantry. High-end Samsung smart appliances, including a Family Hub refrigerator, WiFi-enabled convection wall oven, Flex Duo cooking system, and 36-inch Bluetooth cooktop, complete this exceptional culinary space. A first-floor guest suite and full bath provide flexibility for visitors, a private office, fitness studio, or wellness retreat. The finished two-car garage features epoxy flooring and a modern glass garage door. Upstairs, the primary suite serves as a private sanctuary. The spa-inspired bath features a freestanding soaking tub, expansive dual-entry shower wrapped in marble, semi-frameless glass enclosure, dual vanities, and a custom walk-in closet. Beyond the walls of the home lies your own private paradise. Professionally designed by Exotic Landscape Company, the resort-caliber outdoor living experience evokes the serenity of a luxury Balinese retreat. The newly constructed saltwater pool and spa showcase glass tile finishes, mini-pebble surfaces, travertine coping, LED lighting, therapy jets, a cascading waterfall, and smartphone-controlled OmniLogic automation. A custom outdoor stone shower, yoga platform, lush tropical landscaping, and curated hardscapes create an environment dedicated to relaxation and wellness. Additional features include Eufy smart lock technology, Arlo video doorbell, Google Nest thermostat, WiFi-enabled irrigation, smart garage controls, Quality Edge Vesta steel plank siding, and an expanded driveway. Located nearby highly regarded Winter Park schools and less than ten minutes from Park Avenue, this exceptional residence offers a rare opportunity to own a home that feels more like a private luxury resort. More than a home, this is a sanctuary. A place to unwind, recharge, and experience the very best of Winter Park living.

Listing is courtesy of: SIMPLICITY: A RE BROKERAGE CO (407-920-6020)

Listing Agent: Robert Sassos (407-920-6020)

Remarks: Residing among the treelined streets of Winter Park, this stunning, contemporary pool home, designed and built by renowned Phil Kean, truly captures the essence of luxury living. Showcasing his signature aesthetic, the home emphasizes sleek architectural lines, refined finishes, and a seamless connection between indoor and outdoor spaces. Expansive walls of glass flood the interior with natural light and create a striking façade that embodies its contemporary elegance. The main living areas are designed for both entertaining and everyday living. A dramatic two-story living room is anchored by designer furnishings, which extend throughout the home, while the spacious dining area comfortably accommodates large gatherings. The adjacent family room continues the modern aesthetic with a built-in media wall, sleek fireplace, textured design elements, and a triple sliding door connecting the indoor and outdoor spaces. Ready for any caliber of chef, the kitchen boasts Thermador appliances, along with extensive cabinetry and countertop space, soft-close drawers, a waterfall edge island, generously sized pantry, and reverse osmosis water filtration. A private home theater on the main level offers a true cinematic experience with surround sound, custom seating, and blackout shades, along with a stylish wet bar, providing additional space for entertaining. The home’s Crestron automation system is discreetly integrated, allowing full control of lighting, climate, and technology from a single interface. Upstairs, a striking floating staircase leads to a gallery-style landing overlooking the living space below. For those exhausting days, you can instead take a ride on the elevator. The expansive primary suite features a sitting area, a custom closet, and terrace access. The spa-inspired primary bath includes dual rain showers with body sprays, a soaking tub, and dual vanities with elegant finishes. Additional second-floor amenities include a fitness room with steam shower and sauna, an additional en-suite bedroom, one of the two laundry rooms, and access to an upper-level terrace overlooking the landscaped grounds and pool. Two en-suite guest bedrooms are conveniently tucked away on the first floor for maximum privacy. Offering four bedrooms, five full bathrooms, and two half baths, the home delivers both comfort and sophistication at every turn. Thoughtfully integrated automated shades provide effortless privacy, while the advanced air purification systems and whole-home water softener complement the home's advanced smart features. This residence is offered fully furnished with curated Restoration Hardware pieces, including custom-selected furniture, lighting, rugs, and artwork that enhance its cohesive design. Outdoor living is equally impressive, with covered lanai spaces enhanced by automated roll-down screens, designer furnishings, a summer kitchen with gas grill and ventilation, and tranquil poolside views. The property also includes a split, three-car garage with a large driveway protected by a gated entrance. Completing this extraordinary dwelling is its location in the heart of Winter Park. This lakeside residence sits minutes from Park Ave Shopping, Rollins College, AdventHealth, multiple Botanical Gardens and Museums, well-rated grade schools, and highway access. Schedule your private showing today and experience the Winter Park lifestyle firsthand.

Listing is courtesy of: BERKSHIRE HATHAWAY HOMESERVICES RESULTS REALTY (407-203-0007)

Listing Agent: Joseph Doher (407-203-0007)

Remarks: Welcome to 1750 Carollee Lane, where timeless charm meets modern luxury. Set on a homesite with desirable southern exposure in the heart of Winter Park, this four-bedroom, 3.5-bath, custom pool and spa residence offers more than 3,200 square feet of thoughtfully updated living space near Park Avenue, the Chain of Lakes and top-rated schools. The fully renovated 2025 kitchen serves as the centerpiece of the home, featuring quartzite countertops, a custom wood hood, Zellige-style backsplash, induction cooktop, oversized workstation sink and an expansive island designed for gathering and entertaining. The first-floor primary suite offers a private retreat with a completely reimagined spa-inspired bath showcasing marble flooring, quartzite surfaces, custom solid wood cabinetry, a freestanding soaking tub and upgraded walk-in shower. Designed for comfort and entertaining, the home also features a dedicated office and an upstairs loft with a custom dry bar and beverage refrigerator. Outdoors, the backyard lives like a private resort-style oasis, complete with a saltwater pool and spa, sun shelf, travertine decking, electronic roll-down screens and a fully equipped outdoor kitchen designed for year-round enjoyment. Lush new backyard landscaping completed in May 2026, including enhanced privacy elements, creates an intimate outdoor setting rarely found this close to the heart of Winter Park. Additional highlights include updated irrigation supported by a private well, a new downstairs HVAC system and a home warranty provided for the buyer at closing. Move-in ready and impeccably maintained, this residence offers refined living in one of Winter Park’s desirable settings.

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

Listing Agent: Michelle Hochfelder (407-221-5073)

Remarks: Under contract-accepting backup offers. Virtually Staged. Located in the highly desirable Winter Park area, 1944 Natalen Rd offers the perfect balance of tranquility, convenience, and lifestyle. This property enjoys deeded access to serene Lake Berry while being just minutes from top-rated schools, the vibrant dining and boutique shopping of both Baldwin Park and downtown Winter Park, and everyday conveniences including nearby grocery stores and the renowned Winter Park Farmers’ Market. Residents will appreciate exceptional healthcare access with both AdventHealth Winter Park and the Orlando VA Medical Center at Lake Baldwin close by. Centrally located with easy access to UCF, Orlando International Airport, and Central Florida’s world-famous theme parks and attractions, this home provides an ideal combination of peaceful living and connectivity to everything Orlando has to offer.

Listing is courtesy of: EMPIRE NETWORK REALTY (407-440-3798)

Listing Agent: Trevor Thomas (407-337-8738)

Remarks: Under contract-accepting backup offers. Built for long-term ownership rather than short-term resale, this custom-built Brookshire Heights residence offers a rare combination of thoughtful design, exceptional construction quality, and nearly 4,000 square feet of living space in one of Winter Park's most beloved neighborhoods. Unlike many homes that have been renovated or recently built for resale, 2465 Banchory Road was designed from the ground up with intention, combining timeless architecture, functional luxury, and quality craftsmanship throughout. Set on one of the most beautiful streets in Winter Park, where evening walks feel like something out of a storybook and the Cady Way Trail is just steps from your front door, this home offers the lifestyle buyers dream about and the quality they rarely find. A grand mahogany front door welcomes you inside, where soaring ceilings, oversized interior and exterior doors, and spacious living areas create a sense of elegance and comfort from the moment you enter. The thoughtfully designed floor plan offers nearly 4,000 square feet of living space, including four bedrooms, four full en-suite bathrooms, and a dedicated pool bath. One of the home's most unique features is its dual primary suites, with one located on the first floor and another upstairs. This flexible layout is ideal for multigenerational living, long-term guests, private retreats, or evolving lifestyle needs. Two additional bedrooms each feature their own private en-suite bathroom, while a generous upstairs flex space offers endless possibilities as a media room, playroom, home office, gym, or potential fifth bedroom. The kitchen was designed for both everyday living and entertaining, featuring premium cabinetry, a gas cooktop, double ovens, a built-in coffee system, and a built-in steamer. Every detail was selected to combine beauty, functionality, and convenience. Step outside to a resort-style backyard where the pool becomes the centerpiece of outdoor living. The dark pebble finish, sun shelf with bubblers, color lighting, natural gas heater, automated controls, and expansive outdoor entertaining space create an experience that feels more like a private resort than a backyard. Beyond what you can see, the home's construction quality truly sets it apart. Dual 19-SEER HVAC systems with independent WiFi controls, natural gas service, insulated floor systems between levels, a whole-home instant hot water system, insulated low-E windows, and a hurricane-rated insulated garage door reflect the level of planning and investment rarely found in today's market. These are the kinds of features that enhance comfort, efficiency, and long-term value for years to come. Perfectly positioned for the Winter Park lifestyle, you'll enjoy easy access to Cady Way Park, tennis and pickleball courts, playgrounds, Park Avenue's boutiques and dining, Rollins College, Full Sail University, UCF, AdventHealth Winter Park, and Orlando International Airport. Zoned for top-rated Winter Park schools. This is more than a beautiful home. It is a true custom residence built with intention, designed for living well, and positioned in one of Winter Park's most desirable neighborhoods.

Listing is courtesy of: EXP REALTY LLC (888-883-8509)

Listing Agent: Melissa Johnson (407-681-4393)

Remarks: Attention Students & Parents! Updated First-Floor Corner Condo directly across the street from the Full Sail campus! Why rent when you can buy! 2 Bed | 2 Bath | 1,105 Sq. Ft., an updated first-floor northwest corner condo. -Brand-New Kitchen Appliances: Convection oven, refrigerator, dishwasher, and microwave -Interior Laundry Room with new LG stackable washer & dryer -New Air Conditioning System -Updated Kitchen Cabinets -Updated Plumbing & Electrical -New Ceiling Fans Throughout -Fresh Interior Paint -New Carpet in Bedrooms Community Features: Private screened patio Community pool and hot tub Beautifully maintained grounds Pet-friendly and fenced dog park Winter Park School District, zoned for A-rated schools, approximately 1 mile away.

Listing is courtesy of: FLATFEE.COM (954-965-3990)

Listing Agent: Cliff Glansen

Remarks: Under contract-accepting backup offers. Experience the pinnacle of the Winter Park lifestyle in this enchanting historic cottage, offering an unbeatable, highly walkable location just a 2-minute stroll from the pristine campus of Rollins College, a 4-minute walk to the neighborhood coffee shop, and approximately 11 minutes on foot to the boutique shops, world-class dining, and scenic shores of the Winter Park Chain of Lakes along Park Avenue. Families will secure unparalleled long-term educational value with zoning for highly rated schools including Audubon Park K-8 and Winter Park High School. Stepping inside, the home's authentic character is immediately felt, anchored by beautiful real heart of pine wood flooring that flows seamlessly throughout the entire 1,739-square-foot livable layout. The private primary suite serves as a true retreat, complete with a walk-in closet and a sunlit office/flex space ideal for a remote work setup. The home also features an indoor wood-burning fire pit, adding warmth and character to the living space. Natural gas is available on-site, adding efficiency and flexibility for future upgrades, and the home benefits from a new roof installed in 2023. Situated on a rare, sweeping 9,525-square-foot lot that holds substantial land value on its own, the property offers a massive backyard oasis with ample space for a future pool and endless possibilities for outdoor living. A detached garage provides valuable storage and presents excellent potential for conversion into an accessory dwelling unit (ADU), guest house, home office, or income-producing space, subject to buyer verification and local regulations. Adding even more flexibility, an incredible attic space/storage within the home offers the opportunity to create a unique bonus room, studio, office, or creative retreat. Whether you're seeking a charming historic residence, a highly walkable lifestyle, or a property with exceptional long-term upside, this rare Winter Park offering combines character, location, land value, and future potential in a way that is increasingly difficult to find.

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

Listing Agent: Justin Jodha (689-250-8606)

Remarks: GREAT HOME & GREAT VALUE — add your TLC and DIY and you could have instant equity. Thoughtful floor plan with two living spaces and a screened-in porch. Located in desirable Winter Park, 3 blocks from parks, cycling trails, and a public pool, plus minutes from Park Avenue’s shops and restaurants. Enjoy top-rated schools and a lovely, walkable neighborhood. Zoned for BROOKSHIRE ELEMENTARY. New roof (12/2021), New water heater (12/2021), Re-piped (1/2022, no polybutylene), New garage door and opener (2/2022), New AC evaporator coil (6/2022) and New French drain system (6/2023). The home has an irrigation system and New gutters (2/2022). OWNER FINANCING available for owners or flippers. All dimensions must be independently verified by the buyer.

Listing is courtesy of: VIA PROPERTIES LLC (321-229-6085)

Listing Agent: Donna Peebles (321-229-6085)

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: 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. Welcome to this beautifully updated four-bedroom, two-bathroom pool home offering 1,813 square feet of thoughtfully designed living space in one of Winter Park’s most desirable locations. Perfectly positioned on a spacious lot backing up to the scenic Cady Way Trail, this residence seamlessly blends modern updates, timeless charm, and exceptional outdoor living. Inside, the versatile floor plan includes a dedicated den, office, or playroom, ideal for today’s flexible lifestyle needs. Engineered hardwood flooring flows throughout the home and is complemented by recessed lighting, crown molding, plantation shutters, ceiling fans, and elegant French doors that add warmth and character to every space. A spacious laundry/utility room offers additional storage and convenience, complete with a washer and dryer replaced in 2024. The beautifully remodeled kitchen, updated in 2020, serves as the heart of the home and showcases white shaker-style cabinetry, sleek black granite countertops, matte grey stainless steel appliances, a striking herringbone tile backsplash, and a charming exposed wood beam feature that adds architectural interest. A breakfast bar with seating for three creates the perfect gathering space for casual dining and entertaining, while the spacious dining room easily accommodates sit-down meals and larger gatherings. The private primary suite offers a relaxing retreat featuring a shiplap accent wall, ceiling fan, and an updated ensuite bathroom remodeled in 2020 with a single vanity and beautifully tiled shower with a glass partition. The secondary bedrooms are generously sized and share an updated hall bathroom featuring a tiled tub and shower combination along with a contemporary single vanity. Step outside into your own backyard oasis where a screened, heated, salt-generated pool installed in 2022 creates the ultimate setting for year-round enjoyment. The fully fenced backyard, updated in 2022, offers privacy and plenty of room for pets, play, and entertaining while overlooking the picturesque Cady Way Trail. A private gate provides direct access to the trail, allowing for convenient access to Brookshire Elementary and nearby community amenities. Additional exterior highlights include a spacious two-car carport, whole-house generator hookup, and two included storage sheds providing excellent functionality and additional storage space. This exceptional location places you just minutes from some of Central Florida’s most sought-after amenities including the Winter Park Pines Golf Course, the Cady Way Trail, and the popular Cady Way recreational amenities featuring a community pool, playground, beach volleyball courts, tennis courts, and pickleball courts. Conveniently located near University of Central Florida, Rollins College, and Full Sail University, this home also offers quick access to AdventHealth Winter Park and the Crosby Wellness Center, both less than five minutes away, while Orlando International Airport is approximately 25 minutes from home. Zoned for top-rated Brookshire Elementary, Glenridge Middle School, and Winter Park High School, this property offers an incredible opportunity to enjoy the very best of Winter Park living. ROOF - 2014 HVAC - 2023 ELECTRICAL - 2021(new panel)

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

Listing Agent: Amy Turner (407-803-3885)

Remarks: 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!

Listing is courtesy of: IAD FLORIDA LLC (407-720-0020)

Listing Agent: Karen Salter (352-227-0451)

Remarks: Under contract-accepting backup offers. ***MUST SEE WINTER PARK POOL HOME*** Explore the virtual tours to fully appreciate the beauty of this completely renovated 3 bedroom/2 bath solid block pool home nestled in the highly desirable Kenilworth Shores community in Winter Park. This move-in-ready home features an open layout with vaulted ceilings and an abundance of natural light, highlighted by a large free-flowing kitchen with all the amenities... new stainless-steel GE appliances, elegant quartz countertops, sturdy oversized soft-close shaker cabinets and two large built-in wall pantries. The open living area includes a cozy formal dining room with additional countertop seating, and a picturesque sliding glass door opens to an extra-large 40 x 12 outdoor covered porch that provides additional casual outdoor living space. The spacious primary bedroom has a vaulted ceiling and his/her closets, with private access to the backyard covered porch, and features a fully renovated en-suite bath. The secondary bathroom has been tastefully upgraded, as well. Freshly painted inside and out, this immaculate home has new waterproof LVP flooring throughout, new light fixtures and ceiling fans, and stylish window shade coverings on every window. With an indoor laundry room and a two-car carport, this worry-free home features a new AC unit installed in 2025, a new electrical panel and updated plumbing, and a roof that was replaced in 2018. Setting this home apart is your private outdoor private backyard oasis, showcasing a gorgeous 32 ft long/10 ft deep in- ground pool plus a unique outdoor kitchen . . . perfect for family gatherings or hosting a Bar-b-que pool party . . . and with a generously sized 10’ x 18’ shed with full electric providing additional storage solutions or living options, this fully fenced-in backyard is truly a tranquil outdoor haven. Zoned for excellent Winter Park schools, this home is located four blocks from Winter Park High and less than a mile from Brookshire Elementary and Glenridge Middle. It comes with deeded access to the boat ramp and fishing dock at Lake Berry. Blue Jacket Park and Cady Way Park are just down the street, showcasing great bike trails for walking and jogging. The well-known shopping and restaurants of downtown Park Avenue and Baldwin Park are just minutes away. Rollins College, UCF, Full Sail University, and Winter Pines Golf Course are all close by. And Advent Health/Winter Park Hospital is less than a mile down the street. This is a quiet, family-friendly community known for its tranquility and peaceful living. Don’t miss this opportunity to make this wonderful home your very own. Schedule your showing today.

Listing is courtesy of: JAMIESON PROPERTIES, INC. (407-876-2730)

Listing Agent: Joseph Cosgrove (407-470-0892)

Remarks: Beautifully renovated solid block home on a quiet street in highly desirable Winter Park Pines! This property features fresh exterior paint, updated lighting, a newly paved courtyard, and a bright open floor plan. The stunning kitchen offers modern cabinetry, quartz countertops, and brand-new stainless steel appliances, flowing seamlessly into the dining and family rooms. The sun-drenched Florida room is lined with windows that brighten the entire living space. Complete with a dry bar and its own mini-split AC unit, it offers flexible space for entertaining, relaxing, or creating your dream retreat. The split floor plan includes three generously sized bedrooms and three full renovated bathrooms, with a private primary suite with walk-in closet off the family room and the additional bedrooms and bath located on the opposite side of the home. The attached two-car garage offers excellent potential to be converted into a fourth bedroom, utilizing the existing full bathroom to create a private mother-in-law suite or guest quarters. Additional upgrades include new flooring, trim, doors, fixtures, and fresh interior paint. Create your own outdoor oasis with a newly paved patio and large fenced backyard with room for a pool. Ideally located near downtown Winter Park, Park Avenue shopping and dining, Cady Way Trail, and zoned for top-rated schools. Schedule your showing today!

Listing is courtesy of: SOTERA LIVING (407-725-9660)

Listing Agent: Lianna Dangelo (321-446-3509)

Remarks: One or more photo(s) has been virtually staged. Stunning Two-Floor Home in Coveted Winter Park School District Immaculately maintained and truly move-in ready, this unique two-story residence features distinct living quarters with private entrances to both levels. The main floor offers a spacious split-bedroom layout with three bedrooms and two full baths, including a primary suite with an en-suite bathroom and generous walk-in closet. The fully equipped kitchen boasts newer appliances and opens to a bright living area. The expansive 800 sq. ft. upper level functions as a self-contained living unit, ideal for multi-generational arrangements, home offices, or rental income potential. This versatile space includes one bedroom, a full bathroom, a private balcony, and a full open-concept living and dining area complete with a full-size refrigerator and stove. Located in the highly rated Winter Park School District, this home offers the perfect blend of top-tier education and Central Florida lifestyle. Residents enjoy easy access to world-class entertainment, situated just 26 miles (approx. 35 minutes) from Walt Disney World. Additional features include a large two-car garage with washer/dryer hookups, ample driveway parking, fresh interior paint, and a brand-new roof with a transferrable warranty. All major systems are well-maintained and in excellent working condition.

Listing is courtesy of: MID-STATE PROPERTIES PSL LLC (561-843-9537)

Listing Agent: Stacy Morano (561-843-9537)

Remarks: Under contract-accepting backup offers. **$30,000 Price Improvement!! Welcome to your beautifully updated slice of the Florida Dream here in Winter Park! Perfectly positioned on a desirable corner lot, this thoughtfully renovated home blends modern design, comfort, and functionality - minutes away from Advent Health, Park Avenue, and Schools! From the moment you step inside, you’ll notice the extensive tile flooring, upgraded lighting, and stylish finishes throughout. The heart of the home is the stunning RENOVATED KITCHEN featuring QUARTZ countertops, rich NAVY cabinetry, stainless steel appliances, and a gorgeous wine & coffee bar complete with a built-in WINE FRIDGE—perfect for entertaining or slow Florida mornings at home. Need space to work or unwind? The dedicated OFFICE with MODERN BARN DOORS creates the ideal work-from-home setup, while the additional BONUS ROOM offers endless flexibility as a playroom, reading retreat, media space, or hobby room. Down the hall, the spacious and serene Primary Suite invites you to unwind in the renovated, spa-inspired rain showerhead for a relaxing start or finish to your day. The 2nd bedroom has been dubbed the "Hotel Room" by guests because of its larger size and additional sitting area. This space is perfect for MULTIGENERATIONAL LIVING, whether they are coming home for the summer, guests visiting Central Florida on vacation, or extended family needing a space of their own! The 3rd bedroom is across the hall from the Primary and features laminate flooring, so you truly have 3 dedicated bedrooms PLUS an office! Practical upgrades set this home apart from others in the community, including CUSTOM BLINDS Throughout & 5 1/4 INCH BASEBOARDS in the main living areas, an indoor, heated & cooled LAUNDRY ROOM, Replaced A/C (Inside 2020, Outside 2019), NEW ROOF (2022), PVC REPIPE (2018), NEW SEWER, NEWLY FENCED BACKYARD (2022), WIFI Garage Opener (2020)a storage shed, and a NEW (2021) COVERED & SCREENED LANAI with waterproof and weatherproof interlocking flooring, designed for year-round indoor/outdoor living enjoyment. This move-in-ready abode delivers the perfect balance of style and everyday living! Whether you’re hosting friends, working remotely, or simply enjoying the Florida lifestyle, this remarkable gem is located blocks away from Cady Way Trail and Ward Park, and just minutes from the award-winning restaurants on Park Avenue, and in the Baldwin Park & Mills50 shopping districts! Don't sleep on this one, call and schedule your private showing today!

Listing is courtesy of: PALM CIRCLE REALTY (352-988-4975)

Listing Agent: Kasey Hilyard, Pllc (407-488-9879)