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TANTUM ADD - O6424685 - 922 N PENNSYLVANIA AVE, WINTER PARK, FL 32789 Just Added on 07/14/2026 11:12AM
$1,995,000 | Single Family Home 4 bedrooms, 4.0 bathroom, 2 car garage
Truly a Rare Winter Park Offering. Perfectly positioned along the dogleg of the fourth fairway of the historic Winter Park 9-Hole Golf Course, this beautifully renovated four-bedroom, four-bath Mediterranean residence seamlessly blends timeless architectural character with sophisticated modern living. Rich in charm and thoughtfully updated throughout, the home welcomes you with an elegant living room featuring a gas fireplace, classic built-in shelving, and abundant natural light. At the heart of the home is a stunning chef's kitchen, complete with custom floor-to-ceiling cabinetry, premium Thermador appliances, a charming breakfast nook, and an inviting bar with wine refrigeration that flows effortlessly into the formal dining room—ideal for entertaining. A distinguished first-floor office offers an exceptional work-from-home environment, showcasing a breathtaking custom wall of built-in shelving, cabinetry, and an integrated desk. This versatile space also serves beautifully as a library or den. Upstairs, all four bedrooms provide privacy and comfort. The luxurious primary suite features two separate closets, a spacious spa-inspired bath with a soaking tub overlooking the golf course, and a private covered balcony perfect for enjoying peaceful morning coffee or evening sunsets. A generously sized secondary suite offers exceptional flexibility with its own custom walk-in closet, ensuite bath, and private rear staircase, making it ideal for guests, multigenerational living, or a secluded retreat. Two additional bedrooms and a well-appointed full bath complete the second level. Designed to embrace Florida's indoor-outdoor lifestyle, the home offers a screened porch accessible from both the dining room and breakfast nook, creating an inviting space for year-round entertaining. Two additional open patios provide the perfect setting to relax while enjoying picturesque golf course views and the tranquil surroundings. Perhaps the home's greatest luxury is its exceptional location. Just steps from the boutiques, acclaimed restaurants, sidewalk cafés, and vibrant atmosphere of Park Avenue, this residence offers an unmatched Winter Park lifestyle. Convenient access to downtown Orlando, major hospitals, world-renowned attractions, and both Orlando International and Orlando Executive airports makes everyday living as effortless as it is elegant. This is a rare opportunity to own a beautifully updated Mediterranean home in one of Winter Park's most coveted and walkable locations.
This listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY
MONDRIAN/WINTER PARK TWNHMS - O6422941 - 1778 MONDRIAN CIR, WINTER PARK, FL 32789 1 Day on yellowkey
$1,339,000 | Townhouse 3 bedrooms, 3.5 bathroom, 2 car garage
Luxury waterfront living in Winter Park. Perfectly positioned on a premium corner homesite overlooking beautiful Lake Killarney, this exceptional contemporary townhome offers 3 bedrooms, 3.5 bathrooms, and nearly 2,400 square feet of thoughtfully designed living space with spectacular water views, abundant natural light, and the low-maintenance lifestyle today’s buyers desire.A dramatic 17-foot foyer welcomes you into an expansive open-concept living area where soaring 11-foot ceilings and walls of floor-to-ceiling glass showcase breathtaking lake vistas and create an effortless connection between the indoor and outdoor living spaces. The spacious great room flows seamlessly into the dining area and kitchen, creating an ideal setting for both everyday living and entertaining. The chef’s kitchen is beautifully appointed with premium Wolf and Sub-Zero appliances, double-stacked soft-close cabinetry, stone countertops, a large center island with seating, a generous walk-in pantry, new designer RH lighting throughout, and motorized window shades. Just beyond, the covered rear lanai provides the perfect place to enjoy morning coffee, evening cocktails, or simply relax while overlooking the peaceful shoreline. Upstairs, the luxurious primary suite serves as a private retreat featuring expansive waterfront windows, dual walk-in closets, and a spa-inspired bath with an oversized frameless glass shower, a long single vanity with dual sinks, ample storage, and a private water closet. A spacious loft provides the perfect flex space for a home office, media room, or reading lounge. Step outside to the second-floor balcony complete with an outdoor kitchen, where elevated views of Lake Killarney create an unforgettable backdrop for entertaining. Two additional bedrooms, including one with an en-suite bath, provide comfort and privacy for family and guests, while the upstairs laundry room is thoughtfully positioned between the primary and secondary bedrooms. Additional features include engineered hardwood flooring, porcelain tile, high-end contemporary finishes throughout, abundant storage, a two-car attached garage with an epoxy floor, EV charging station, garage door opener, and a tankless gas water heater. Residents of Mondrian at Winter Park enjoy beautifully maintained grounds, private roads, reclaimed irrigation, a community dock, and lake access to one of Central Florida’s most desirable ski lakes. The HOA also includes cable television, high-speed internet, exterior grounds maintenance, and pest control, making for truly effortless ownership. Combining exceptional waterfront views, sophisticated contemporary design, premium finishes, an ideal floor plan, and one of Winter Park’s most convenient locations, this is a rare opportunity to own one of the community’s most desirable lakefront residences. Just minutes from Park Avenue, Winter Park Village, AdventHealth, Rollins College, Interstate 4, and Downtown Orlando, this home offers the perfect balance of luxury, convenience, and low-maintenance living. Schedule your private showing today and discover everything this exceptional Lake Killarney residence has to offer.
This listing is courtesy of: KELLY PRICE & COMPANY LLC
WINTER PARK - O6423842 - 462 W LYMAN AVE, WINTER PARK, FL 32789 1 Day on yellowkey
$1,595,000 | Single Family Home 3 bedrooms, 2.5 bathroom, 2 car garage
Nestled in the heart of Winter Park's vibrant Hannibal Square, this exceptional one-story residence, completed in 2022, offers the perfect blend of contemporary design, refined finishes, and an unbeatable walkable lifestyle. Thoughtfully designed with three bedrooms, two and one-half baths, and an open-concept floor plan, the home showcases clean architectural lines, soaring ceilings, and walls of glass that fill the interior with natural light while framing views of the beautifully landscaped grounds. The chef's kitchen serves as the centerpiece of the home, featuring premium Wolf and Sub-Zero appliances, custom cabinetry, a center island with seating, and workspace for everyday living and entertaining. The adjoining dining area flows seamlessly into the spacious great room, where custom-built library shelving creates a striking focal point and adds warmth and character to the modern design. Beautiful polished concrete floors extend throughout the residence, providing a cohesive and sophisticated aesthetic. Designed with privacy in mind, the split-bedroom floor plan places the primary suite in its own secluded wing. This spacious retreat offers direct access to the covered rear patio and features a beautiful bath with dual vanities, an oversized walk-in shower, private water closet, and an impressive custom walk-in closet measuring approximately 11 by 9 feet. Conveniently accessible from both the primary bath and laundry room, the thoughtfully designed closet enhances everyday functionality. On the opposite side of the home, two additional guest bedrooms are connected by a well-appointed Jack-and-Jill bath, while a stylish powder bath is ideally located for visitors. Outdoor living is equally inviting with a covered patio with a privacy bamboo hedge that create a peaceful backdrop for relaxing or entertaining. An attached two-car garage completes this beautifully appointed residence. Perfectly positioned just steps from the acclaimed restaurants, wine bars, coffee shops, and boutiques of Hannibal Square, this home offers one of Winter Park's most desirable lifestyles. Stroll to the renowned shopping, dining, galleries, and sidewalk cafés of Park Avenue, enjoy nearby Central Park and community events, or take advantage of the close proximity to Rollins College, the Winter Park Farmers' Market, and major roadways providing convenient access throughout Central Florida. This is a rare opportunity to enjoy nearly new construction in one of Winter Park's most sought-after neighborhoods, where modern luxury and exceptional walkability come together.
GLENMOOR - O6424511 - 4437 GLENMOOR CT, WINTER PARK, FL 32792 1 Day on yellowkey
$539,000 | Single Family Home 3 bedrooms, 2.0 bathroom, 2 car garage
Beautiful meticulously maintained 3-bedroom, 2-bath split floor plan home situated on a desirable corner lot in the established Glenmoor community. Move-in ready, this home features vaulted ceilings with exposed wood beams, a floor-to-ceiling brick fireplace, carpet, and fresh interior paint. The kitchen offers contemporary cabinetry, Silestone countertops, a skylight, stainless steel range, microwave, and refrigerator, and opens to the spacious eating area. A formal dining room provides additional entertaining space. The private primary suite features a walk-in closet, en-suite bath with double vanities and a walk-in shower. The Flex room is currently being used as a 4th bedroom/office with high ceilings and lots of natural light. Leading out you will find a fully fenced backyard retreat with a brick paver patio, tropical landscaping and a gazebo—ideal for outdoor entertaining. Additional features include a two-car garage, inside laundry room with washer and dryer, 12' x 20' storage shed, and a secondary driveway with parking for up to four additional vehicles, boat, or RV. No HOA! Conveniently located near SR 417, Full Sail University, Rollins College, UCF, shopping, dining, parks, and top-rated Winter Park schools. New roof 2024, new gutters 2024, fresh exterior paint 2025, new exterior lighting 2025.
This listing is courtesy of: TAL BUSIDAN PA
EASTBROOK SUB UNIT 16 - O6424677 - 2223 CONIFER AVE, WINTER PARK, FL 32792 1 Day on yellowkey
$435,000 | Single Family Home 3 bedrooms, 2.0 bathroom, 2 car garage
Virtually Staged. Welcome to 2223 Conifer Ave, recently enhanced with a new roof, fresh interior paint, and fresh exterior paint. The kitchen features all stainless steel appliances and an accent backsplash. A walk in closet is included in the primary bedroom, complemented by double sinks in the primary bathroom. Outside, an in ground pool and a covered patio in the back yard, all within a fenced in backyard. Perfectly updated and designed for comfort and enjoyment, this home awaits.. Included 100-Day Home Warranty with buyer activation
This listing is courtesy of: OPENDOOR BROKERAGE LLC
WRENWOOD UNIT 3 3RD ADD - O6424623 - 5225 ALBERT DR, WINTER PARK, FL 32792 1 Day on yellowkey
$435,000 | Single Family Home 3 bedrooms, 2.5 bathroom, 2 car garage
Move-in-ready Winter Park gem in top-rated Seminole County schools! This 3BR/2BA home features a private split-bedroom layout. The home features laminated wood flooring in all the bedrooms and beutiful tile in the kitchen and bathrooms. Both bathrooms feature newly updated toilets. The expansive eat-in kitchen is a chef's delight, boasting premium granite countertops, solid light maple cabinets with elegant glass upper doors, and a breakfast bar opening to the large family room. Enjoy total peace of mind with extensive 2023 upgrades, including a BRAND NEW ROOF, new electrical panel, new energy-efficient windows, new French doors, and a new garage door for the 2-car garage.The HVAC system was manufactured in 2019 and installed in 2020 Step outside to a massive, fully fenced backyard featuring a large covered lanai with a brand-new aluminum frame and fresh screens—perfect for outdoor entertaining. Truly a turnkey property optimized for insurance savings and modern comfort. Schedule your tour today!
This listing is courtesy of: PREMIUM PROPERTIES R.E SERVICE
WINTER PARK WOODS CONDO - O6424619 - 263 SCOTTSDALE SQ #263, WINTER PARK, FL 32792 1 Day on yellowkey
$80,000 | Condo 2 bedrooms, 2.0 bathroom
Great location for homeowner or investor. Located close to FullSail and UCF and major roads, shopping, eating and more. Don't hesitate to see this one before it is gone!
This listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO
EASTBROOK SUB - S5153456 - 885 CARNATION DR, WINTER PARK, FL 32792 2 Days on yellowkey
$375,000 | Single Family Home 4 bedrooms, 2.0 bathroom, 2 car garage
Beautifully updated 4-bedroom, 2-bath pool home in Winter Park offering modern upgrades and flexible living space. The home features new tile flooring throughout, a fully renovated kitchen with a stunning waterfall quartz island, and two beautifully remodeled bathrooms. The garage has been updated with new flooring and a new garage door. Major improvements include a new roof (2024), new A/C (2023), complete home repipe (2022), updated electrical panel, and pavers in both the front and back of the home. The swimming pool was resurfaced with new tile in 2023 and is approximately 12 feet deep, creating the perfect backyard retreat.
This listing is courtesy of: RADIUS REALTY GROUP LLC
SWOOPE PARK - O6423105 - 436 W SWOOPE AVE, WINTER PARK, FL 32789 2 Days on yellowkey
$719,900 | Townhouse 4 bedrooms, 3.5 bathroom, 2 car garage
Virtually Staged. Welcome to this virtually staged contemporary townhome in the desirable 400 West community, home to just nine residences and steps away from lively Park Avenue. Enter through the private garage or the charming front path, and you'll find a bright and open main floor that perfectly balances comfort and modern style. The main floor features a stylish mix of finishes, including large-format porcelain tiles, level 4 drywall, tall baseboards, and designer lighting. The centerpiece is a sleek kitchen equipped with glossy white cabinetry, chic chrome pulls, quartz countertops, and top-quality stainless-steel appliances. The garage, with alley access, includes a storage closet and built-in shelving for added convenience. On the second level, discover two spacious primary suites with modern LVP flooring and large windows that let in plenty of natural light. The en-suite bathrooms are designed with porcelain tiles, frameless glass showers, wall-to-wall mirrors, and matte white vanities. The primary bath offers a double-sink vanity, a private water closet, and a spacious walk-in closet. A conveniently situated laundry room features a Samsung washer and dryer with overhead storage. The third level has two more bedrooms, each with walk-in closets, connected by a shared Jack-and-Jill bath, making it ideal for guests, a home office, or a workout space. Don’t miss the chance to check out this fantastic home in a prime location where luxury meets practicality!
This listing is courtesy of: RE/MAX EXCLUSIVE COLLECTION
TROTTERS REP - O6424399 - 786 MCINTYRE AVE, WINTER PARK, FL 32789 2 Days on yellowkey
$625,000 | Townhouse 3 bedrooms, 2.5 bathroom, 2 car garage
Virtually Staged. Welcome to 786 McIntyre Avenue, Winter Park, FL 32789—a serene retreat perched on a picturesque tree-lined brick street in one of Winter Park's most desirable neighborhoods. Just a short stroll from Rollins College and the renowned shops, restaurants, and charm of Park Avenue, this exceptional single-family townhome offers the perfect blend of comfort, style, and location—with no HOA! A charming driveway leads to the attached two-car garage and private front entrance. Inside, you'll be welcomed by a bright, airy interior featuring soaring ceilings, dramatic high windows, abundant natural light, and a cozy wood-burning fireplace. The spacious living room is surrounded by two private patios, creating a seamless connection between indoor and outdoor living. The updated kitchen boasts modern cabinetry, an open breakfast bar, and a cheerful eat-in dining area with direct access to one of the patios. The formal dining room, currently used as a home office, opens to the second patio, making it the perfect setting for al fresco dining or entertaining. Upstairs, the impressive 23' x 12' primary suite offers a peaceful retreat, complete with a spacious 20' x 8' ensuite bathroom. Two additional guest bedrooms share a convenient Jack-and-Jill bathroom, providing comfort and privacy for family or visitors. Meticulously maintained, this home features numerous recent updates, including a new HVAC system (2025) and beautiful wood shutters throughout. Located in the highly sought-after Audubon K-8 and Winter Park High School districts, this exceptional home combines timeless character, modern updates, and an unbeatable location. WELCOME HOME!
This listing is courtesy of: FANNIE HILLMAN & ASSOCIATES
WINTER PARK WOODS CONDO - O6424296 - 303 SCOTTSDALE SQ #303, WINTER PARK, FL 32792 4 Days on yellowkey
KILLARNEY ESTATES - O6417337 - 1298 BEACHVIEW AVE, WINTER PARK, FL 32789 4 Days on yellowkey
$1,375,000 | Single Family Home 1 bedrooms, 1.0 bathroom
Under contract-accepting backup offers. Versatile Live/Work (0-1) zoned parcel in Winter Park's prestigious 32789 ZIP code. This 0.43-acre lot offers flexibility for residential, office, or mixed-use development. Part of a four-lot portfolio that includes three direct lakefront parcels on Lake Killarney - available together or individually. Steps from Winter Park Village, Park Avenue, and Rollins College.
This listing is courtesy of: PREMIER SOTHEBYS INT'L REALTY
CONWILL ESTATES - O6422700 - 1750 WALNUT AVE, WINTER PARK, FL 32789 4 Days on yellowkey
$2,195,000 | Single Family Home 4 bedrooms, 4.5 bathroom, 2 car garage
Positioned in one of Winter Park's most desirable neighborhoods, this exceptional French Mediterranean residence is just moments from Phelps Park, the Winter Park YMCA, Lakemont Elementary, and Interlachen Country Club. Built by MichaelCharles Homes with interiors by Wolfe-Rizor Interiors, the home pairs timeless architecture with refined contemporary design, abundant natural light, and exceptional craftsmanship. The thoughtfully designed floor plan offers 4 bedrooms, 4 full bathrooms, and 1 half bathroom. The first-floor primary suite features a spa-inspired bathroom and an expansive custom walk-in closet with dedicated his-and-her wardrobe areas. A flexible adjoining room is ideal as a private office, nursery, fitness room, or optional fifth bedroom. On the opposite wing of the home, the private guest suite includes a full bathroom and walk-in closet. At the heart of the home, the chef's kitchen showcases a large center island, custom cabinetry, and premium finishes. Oversized glass doors open to a covered lanai with outdoor dining, grilling space, and a resort-style pool. Framed by mature Japanese maple trees, the backyard offers exceptional privacy and a spacious lawn for recreation or entertaining. Situated on a quiet, oak-lined street, this custom-built home reflects the quality in every detail, presenting a rare opportunity to own an exceptional residence in the heart of Winter Park.
This listing is courtesy of: PALMANO GROUP RE BROKERAGE LLC
FAIRSHORES PLACE - O6423829 - 2803 RIDDLE DR, WINTER PARK, FL 32789 4 Days on yellowkey
$589,000 | Single Family Home 3 bedrooms, 2.5 bathroom, 2 car garage
Welcome to 2803 Riddle Drive, where thoughtful updates, timeless charm, and an exceptional Winter Park location come together to create the perfect place to call home. Situated on an oversized lot, this beautifully maintained three-bedroom, two-and-a-half-bath residence offers a spacious floor plan, a two-car garage, and a sparkling private pool designed for year-round Florida living. Step inside to discover a bright, inviting interior featuring fresh paint throughout, brand-new carpeting, and all-new designer light fixtures. The functional layout provides comfortable living spaces for everyday living while offering the ideal setting for entertaining family and friends. Large windows fill the home with natural light, creating a warm and welcoming atmosphere. Step outside to your own private backyard retreat. The oversized, fully fenced yard offers endless possibilities for relaxing, entertaining, gardening, or enjoying sunny Florida afternoons by the pool. A storage shed provides additional space for lawn equipment, tools, or seasonal items, making the backyard as functional as it is enjoyable. Thoughtfully maintained over the years, the home also features a newer roof, newer HVAC system, fresh interior paint, new carpeting, and updated light fixtures, giving the next owner added peace of mind and the opportunity to move right in. Conveniently located just minutes from beautiful Lake Killarney, the shops and restaurants of Park Avenue, and premier shopping and dining throughout Winter Park, this home also offers quick access to i4 and 408, making commuting throughout Central Florida simple and convenient. For investors or buyers seeking future rental potential, the property has been consistently leased since 2017, generating $2,800 per month in rental income, demonstrating its strong desirability and investment appeal. Offering the perfect blend of modern updates, outdoor living, and an unbeatable location, 2803 Riddle Drive is truly move-in ready and waiting for its next owner to call it home.
This listing is courtesy of: CORCORAN PREMIER REALTY
CEDARWOOD VILLAGE 1 - O6418973 - 2450 GRAND TETON CIR #2450, WINTER PARK, FL 32792 4 Days on yellowkey
$255,000 | Condo 3 bedrooms, 2.0 bathroom
Rare end units like this don't come around often! Welcome to 2450 Grand Teton Circle, tucked away in the well-maintained, established community of Cedarwood Village in Winter Park. This 3-bedroom, 2-bath home is filled with natural light thanks to its end-unit location, and the open layout makes it easy to relax, entertain and enjoy everyday living. The spacious living and dining areas flow together nicely, while the kitchen offers plenty of room to cook, gather, and stay connected with family and friends. Over the past several years, this home has been thoughtfully updated, giving the next owner peace of mind. Major improvements include a new roof, skylights, HVAC system, water heater, kitchen appliances, washer and dryer, updated LED lighting, and fresh interior paint. Both bathrooms have been beautifully remodeled, the home has been replumbed by the HOA, and the primary closet has been enhanced with custom shelving. Additional updates include new flooring in the secondary bedrooms, updated window blinds, and thoughtful finishing touches throughout. The private screened lanai has been transformed into a cozy outdoor retreat with fresh paint, a ceiling fan, new screens and screen door, string lighting, and decorative greenery—making it the perfect place to enjoy your morning coffee or unwind after a long day. Life here is easy. Cedarwood Village is a beautifully maintained, established community featuring a community pool and Clubhouse for your special events, tennis courts, and pickleball courts. The HOA has also recently repainted the exterior of the buildings, helping keep the neighborhood looking fresh and inviting. Best of all, this home is value priced, giving you an incredible opportunity to own in desirable Winter Park without the premium price tag. You're just minutes from Winter Park's shopping and dining, Full Sail University, UCF, major employers, and convenient access to SR-417 and downtown Orlando. If you've been looking for a move-in-ready home in a fantastic location with years of thoughtful updates already completed, this rare end unit is definitely worth a look!
KENILWORTH SHORES SEC 07 - O6420140 - 2010 SUMMERFIELD RD, WINTER PARK, FL 32792 4 Days on yellowkey
$594,500 | Single Family Home 3 bedrooms, 2.0 bathroom , 1 car carport
Living in the City of Winter Park is quite afforadable with this beautifully maintained property that offers the perfect blend of comfort and convenience. Cathedral ceiling add to the spacious feeling of this floor plan with luxury vinyl flooring and ceramic tile. The new stainless steel appliance package in kitchen stands out next to the white cabinetry and granite counter tops. Separate family room plus Florida Room, inside utility with full size washer/dryer and 2nd side by side refrigerator plus an office/exercise room with an energy efficient mini split and entry from the carport. The spacious primary bedroom includes a private bath featuring maple cabinets with ample vanity storage and a roomy walk-in shower. The guest bath is complete with a tub/shower combination. The exterior features a spacious backyard enclosed by white vinyl fencing, a storage shed, sprinkler system on a separate well and a 1-car carport with additional parking for up to 3 vehicles, ensuring plenty of space for guests. This property boasts fantastic curb appeal, beautifully landscaped with a freshly installed, vibrant green front lawn that greets you the moment you arrive. Best of all, you are walking distance to Winter Park High School and just minutes from local dining and shopping. The AC system was replaced 2017. The roof and elecrtical panel were replaced in 2019, and the home was replumbed in 2019. Don't miss the opportunity to make this fantastic property your own! Buyer/buyer's agent to verify all schools and room measurements. Appliances convey as is. Brio Management LLC, Seller, is owned by 2 Florida Licensed Real Estate Brokers.
WINTER WOODS UNIT 01 - O6423782 - 2189 SUSSEX RD, WINTER PARK, FL 32792 5 Days on yellowkey FORECLOSURE
$375,000 | Single Family Home 4 bedrooms, 2.5 bathroom, 2 car garage
**MULTIPLE OFFERS - SUBMIT YOUR HIGHEST AND BEST BY 5PM ON MONDAY 7/13** Bank-owned opportunity in Winter Park near Interlachen Country Club, Park Avenue, Full Sail, Rollins, and UCF. Set in Winter Woods, one of the area’s established neighborhoods, this 4/2.5 two-story home sits on a fenced lot w/pool and offers 1,776 sqft, block and brick construction, a 2-car garage, and a primary bedroom with a walk-in closet and private balcony overlooking the pool. The home needs a full renovation, including a new roof. Flooring, kitchen, and HVAC, and the property is priced accordingly. Optional HOA and flood zone X help keep carrying costs simple. Sold As-Is by the REO seller. Cash or renovation financing only.
This listing is courtesy of: PROPERTY LOGIC RE
SUBURBAN HOMES FIRST ADD - O6423739 - 4965 ORANGE AVE, WINTER PARK, FL 32792 5 Days on yellowkey
$379,900 | Single Family Home 4 bedrooms, 2.0 bathroom , 1 car carport
Updated Winter Park home with major improvements already completed and no HOA! Located at 4965 Orange Ave., this move-in ready property offers a desirable Central Florida location with convenient access to shopping, dining, parks, major roadways, and everything the Winter Park area has to offer. Recent updates include a NEW Roof, Dual-pane, Energy-efficient Windows, 2 NEW A/C systems, fresh interior and exterior paint, upgraded baseboards, Beautifully Remodeled Bathrooms, and terrazzo & ceramic tile flooring throughout (no carpet!!). The galley-style kitchen features stainless steel appliances, a decorative backsplash, and an efficient layout designed for everyday functionality. Both bathrooms have been beautifully refreshed, while the durable flooring and fresh finishes create a clean, cohesive feel throughout the home. Outside, the large fenced yard provides excellent outdoor space for entertaining, gardening, pets, or future possibilities. The attached carport includes a convenient storage and laundry room for added practicality. With no HOA, updated major systems, energy-efficient windows, and a centrally located Winter Park address, this home is an excellent opportunity for buyers searching for an updated home in Winter Park, FL with modern improvements, low-maintenance features, and easy access to the Greater Orlando area.
This listing is courtesy of: RE/MAX TOWN & COUNTRY REALTY
KAWILLA CREST - O6422937 - 1908 CYRIL CT, WINTER PARK, FL 32792 5 Days on yellowkey
$639,000 | Single Family Home 4 bedrooms, 2.5 bathroom, 2 car garage
Welcome to this gorgeous 4-bedroom, 3-bathroom WINTER PARK home that perfectly blends elegance, comfort, and functionality. From the moment you step inside, you'll be impressed by the soaring 12–14-foot ceilings, beautiful CROWN MOLDINGS, and classic PLANTATION SHUTTERS that add timeless charm throughout. Designed with an exceptional flow, this home features formal living and dining rooms, along with a spacious family room centered around a charming fireplace, creating a warm and inviting space for relaxing or gathering with family and friends. The family room seamlessly connects to the heart of the home—a stunning CUSTOM chef's kitchen equipped with high-end appliances, thoughtfully designed cabinet organizers, and abundant workspace, making it a dream for cooking and entertaining. The desirable split floor plan offers both privacy and flexibility, with two bedrooms located in the right wing and two in the left, including a spacious primary suite. Every detail has been carefully considered to create a warm, inviting atmosphere that's ideal for everyday living and hosting guests. Step outside to your private backyard oasis, where a large swimming pool and spacious outdoor living area create the perfect setting for entertaining, weekend gatherings, or simply relaxing. The fully fenced yard provides both privacy and plenty of room to enjoy Florida living year-round. Additional highlights include a **NEW ROOF**installed in 2021**,** NEW LUXURY VYNIL PLANKS FLOORING** in 4 rooms, brand NEW interior painting offering added value and peace of mind for the next owner. This exceptional Winter Park home is a true showstopper that offers luxury, comfort, and timeless appeal. Don't miss the opportunity to make it yours!
This listing is courtesy of: COLDWELL BANKER REALTY
LAKE FOREST PARK - O6422550 - 2905 PARKLAND DR, WINTER PARK, FL 32789 6 Days on yellowkey
$3,395,000 | Single Family Home 6 bedrooms, 7.0 bathroom, 3 car garage
Come tour this brand new, elaborately finished luxury home in Winter Park! Designed and constructed by a well-established, award-winning custom home builder, no expense has been spared. This home is truly a leader in its class! Located just a short walk to the esteemed Audobon K-8 school, East End market, restaurants, shopping, Blue Jacket Park, Baldwin Park. Just a short drive to Park Avenue restaurants and shopping. As you pull up to this vast estate home, the dimensional architectural detail on the home on a huge lot boasts a commanding presence. The 12 foot ceilings on the first floor and 10 foot ceilings on the second floor give the home a voluminous feel throughout. The first floor features a huge master suite with an accessible washer and dryer off the giant walk-in closet, plus an additional full guest suite and separate office. The gourmet kitchen features luxury custom cabinets, an accent island with exotic granite counter tops. Thermador appliances outfit the main kitchen as follows: Large 30” refrigerator and 30” freezer towers, 48” dual oven gas range with ornamental hood, dishwasher and microwave drawer. Flanking the main kitchen is a spacious Butler’s pantry with its own sink, refrigerator and dishwasher. Just off the Butler’s pantry is both a mudroom just inside the garage, and additional air-conditioned storage room. Over the garage is a separate bonus/flex room with its own full bath and closet. Upstairs is a huge loft living area plus three full bedroom suites and laundry room. The home is ornamented with expensive fit and finishes as follows: extensive architectural ceiling detail with cove lighting, lighting fixtures, plumbing fixtures, hardware, tile, level 5 smooth drywall finishes, designer wallpaper, and more! Designed with energy efficiency in mind, Natural gas fuels two tankless water heaters, the kitchen range, summer kitchen grill and pool/spa heater. Elaborate landscaping provides beautiful accents and plenty of privacy in the rear outdoor living area. Outdoor living includes a huge covered lanai with retractable screens, summer kitchen, and heated salt-water swimming pool with integrated spa and pool deck, plus outdoor shower and separate pool bath. 10' tall pocket sliding glass doors can open the great-room wall completely to integrate your indoor and outdoor entertaining. Great fortune comes to those who TAKE IMMEDIATE ACTION when opportunity presents itself! Come tour your magnificent new luxury home today!
This listing is courtesy of: UNITED REAL ESTATE PREFERRED
ORANGE GROVE SUB - O6421927 - 1754 TAYLOR AVE, WINTER PARK, FL 32789 6 Days on yellowkey
$2,569,999 | Single Family Home 5 bedrooms, 4.5 bathroom, 2 car garage
Under Construction. Experience the very best of Winter Park living with this stunning new construction home, where sophisticated design, luxury finishes, and an incredible location come together on a quiet tree-lined street. Ideally positioned just a short golf cart ride from Park Avenue, the YMCA, and Interlachen Country Club, this home offers the perfect combination of privacy, convenience, and refined Winter Park living. From the moment you step inside, an impressive foyer greets you, showcasing intricate marble mosaic tile that sets the tone for the craftsmanship found throughout. The open-concept floor plan flows effortlessly into the main living spaces, where the spacious living room serves as the centerpiece of the home with elegant archways, custom shelving with LED underlighting, warm wood beam accents, and a stunning stone-wrapped fireplace creating the perfect balance of sophistication and comfort. Designed for both everyday living and entertaining, the dining room features a beautiful dry bar complete with a wine refrigerator, while the chef’s kitchen is truly the heart of the home. Outfitted with Calacatta quartz countertops, a paneled built-in refrigerator, a full suite of Thermador appliances, and a spacious walk-in pantry, every detail has been thoughtfully selected to deliver both style and functionality. The first-floor primary suite provides a private retreat with generous proportions and a spa-inspired bathroom featuring marble mosaic tile, dual vanities, a freestanding soaking tub, an expansive walk-in shower, and a large walk-in closet. A rare additional first-floor guest suite adds incredible flexibility for family and visitors. Upstairs, the home continues to impress with a spacious loft, a conveniently located laundry room, and three additional bedrooms, offering plenty of room for everyone. Step outside and experience your personal outdoor oasis with a spacious covered lanai featuring a full summer kitchen overlooking the sparkling pool and spa. The oversized backyard provides an abundance of green space, creating the perfect setting for relaxing, entertaining, or enjoying time with family. Additional highlights include impact-rated windows and doors, premium finishes throughout, and an unbeatable location surrounded by some of Winter Park’s most desirable amenities. This is a rare opportunity to own a brand-new home combining thoughtful design, exceptional craftsmanship, and one of Central Florida’s most sought-after lifestyles.
This listing is courtesy of: ONE LUXURY INTERNATIONAL LLC
CORONATION ADD - O6423106 - 3360 ROYAL ST, WINTER PARK, FL 32792 6 Days on yellowkey
$179,900 | Half Duplex 2 bedrooms, 2.0 bathroom
Handyman/Investor/Landlord special will need full rehab, will need everything. Nice end unit on dead end street, huge culdesac lot. tenant occupied. Please do not disturb tenant. Cash only. Quick close two weeks. $5,000 non refundable deposit. No inspection contingency. Tenant has been in property since 1992. No HOA. Tenant lease through 2/28/2027. Rehabbed retail value $270,000.
This listing is courtesy of: SAND DOLLAR REALTY GROUP INC
CANTON AVE COTTAGES 1 - O6422949 - 439 N CAPEN AVE, WINTER PARK, FL 32789 7 Days on yellowkey
$849,000 | Single Family Home 3 bedrooms, 2.5 bathroom, 2 car garage
Under contract-accepting backup offers. Life is simply better when everything is just around the corner. Perfectly positioned in the heart of Winter Park, this beautifully maintained David Weekley home offers the rare opportunity to enjoy one of Central Florida's most desirable lifestyles. Located just four blocks from Park Avenue and one block from Winter Park Village, you'll also enjoy close proximity to Hannibal Square, Central Park, Publix, the Winter Park Farmers' Market, acclaimed restaurants, boutique shopping, museums, cafés, and everyday conveniences. Built in 2017, this thoughtfully designed home blends timeless architecture with modern luxury across a spacious and functional floor plan. The first floor features three generously sized bedrooms and two full bathrooms, including a private primary suite complete with a spa-inspired bath and an expansive walk-in closet. Upstairs, the home's open-concept living spaces are designed for both everyday comfort and effortless entertaining. Natural light fills the expansive living and dining areas, while the chef's kitchen serves as the centerpiece of the home. Featuring premium Jenn-Air stainless steel appliances, a natural gas cooktop, generous cabinetry, beautiful countertops, and a large center island, it's a space equally suited for hosting friends or preparing a quiet dinner at home. Sliding glass doors extend the living area to an oversized balcony with Trex decking, creating an inviting outdoor retreat for morning coffee, evening cocktails, or dining under the stars. Built with quality and efficiency in mind, the home includes double-pane windows, great insulation, and a gas tankless water heater. The homeowners association further enhances the low-maintenance lifestyle by providing lawn and shrub care, irrigation water, and maintenance of the community perimeter wall, allowing you to spend more time enjoying your home and less time maintaining it. More than just a beautiful residence, this home offers an exceptional opportunity to experience the very best of Winter Park. Enjoy dinner on Park Avenue, spend Saturday mornings at the Farmers' Market, explore the boutiques of Hannibal Square, relax in nearby parks, or meet friends for coffee, all just moments from your front door. This is a home where luxury, convenience, and one of Winter Park's most sought-after locations come together beautifully.
This listing is courtesy of: COMPASS FLORIDA LLC
WATERFALL COVE OF WINTER PARK - O6422568 - 1695 LEE RD #B108, WINTER PARK, FL 32789 7 Days on yellowkey
$89,999 | Condo 1 bedrooms, 1.0 bathroom
This charming 1bedroom, 1bathroom condo is a fantastic opportunity for both homeowners and investors. Located in a desirable area close to shopping, restaurants, and everyday conveniences, it offers comfort, convenience, and excellent value. The kitchen comes fully equipped with a refrigerator, stove, dishwasher, and microwave, and the unit also includes a washer and dryer for added convenience. Step outside onto your private outdoor balcony, the perfect spot to enjoy your morning coffee or unwind after a long day. Residents have access to a beautiful community swimming pool, creating a relaxing atmosphere to enjoy year-round. Whether you're looking for a place to call home or a great investment property, this condo has everything you need in an ideal location.
This listing is courtesy of: LOKATION
LAKE KNOWLES TERRACE ADD 02 - O6421690 - 1823 SUNSET DR, WINTER PARK, FL 32789 7 Days on yellowkey
$2,549,000 | Single Family Home 5 bedrooms, 4.5 bathroom, 2 car garage
Under Construction. Nestled along a quiet street in Winter Park’s coveted Tree Streets, this stunning coastal farmhouse new build delivers the perfect combination of timeless architecture, luxury finishes, and an unbeatable location. From the moment you arrive, the home captivates with its warm and inviting facade, charming architectural details, and exceptional curb appeal. Step inside to an impressive open layout where natural light, designer finishes, and meticulous craftsmanship set the tone. The spacious living room serves as the heart of the home, showcasing a sleek electric fireplace, custom built-in bookshelves with LED accent lighting, and expansive pocketed glass sliding doors that create a seamless connection to the outdoor living space. The chef’s kitchen is a true centerpiece, beautifully appointed with Taj Mahal countertops, custom cabinetry with LED underlighting, a premium Thermador appliance package, and a hidden walk-in pantry that blends functionality with luxury. Flowing effortlessly from the kitchen, the dining area offers the perfect setting for hosting, complete with a custom dry bar, additional cabinetry, and a dedicated wine fridge. Designed with a highly desirable layout rarely found in Winter Park, the first-floor features both the primary suite and an additional guest suite. The primary retreat offers generous proportions, beautiful natural light, and private sliders opening directly to its own lanai. The spa-inspired bathroom provides a true escape with marble mosaic flooring, dual vanities, and an elegant wet room featuring a spacious walk-in shower and freestanding soaking tub. Completing the suite is an expansive walk-in closet with its own stackable washer and dryer for ultimate convenience. Upstairs, a spacious loft creates an additional living area accompanied by a full laundry room and three generously sized bedrooms, providing flexibility for family, guests, or additional workspace. Step outside and experience Florida living at its finest. The covered lanai is designed for year-round enjoyment with a fully equipped summer kitchen overlooking the sparkling pool and spa, along with additional green space perfect for relaxing or entertaining. Located in the heart of Winter Park’s iconic Tree Streets, this residence offers one of the area’s most desirable lifestyles. Enjoy the ability to walk to Phelps Park while being just minutes from the Winter Park YMCA, Park Avenue’s renowned shopping and dining, and everything that makes this community one of Central Florida’s most sought-after destinations. Don’t miss this rare opportunity to own a brand-new construction residence in Winter Park’s highly coveted Tree Streets!
CARVER TOWN FIRST ADD - S5152493 - 730 W SWOOPE AVE, WINTER PARK, FL 32789 8 Days on yellowkey
$839,000 Increased | Single Family Home 5 bedrooms, 3.0 bathroom
Virtually Staged. Stylish Mid-Century Modern gem in the heart of Winter Park, minutes from Park Ave! Fully renovated corner lot home featuring 5 beds/3 baths, 2,132 SF of CBS block construction. Prime location just 3 blocks from iconic Park Avenue, minutes from Winter Park Village, Rollins College, Publix, Trader Joe's, Whole Foods & AdventHealth. Zoned for top-rated Lakemont Elementary, Maitland Middle & Winter Park High. Currently operating as a fully occupied income-producing PadSplit co-living property generating up to $5,664/month gross at full occupancy — ideal for investors seeking turnkey cash flow. New 4-ton A/C (2025), permitted renovation, modern kitchen with convection oven, dishwasher, range & refrigerator, updated bathrooms, luxury finishes throughout. On-site laundry, high-speed WiFi, driveway & street parking. Corner lot with abundant natural light, north exposure, open floor plan. No HOA. No CDD. No flood insurance required. Walking distance to WP9 Golf Course, SunRail station & Central Park. Interested in living in the home yourself? Contact listing agent to discuss options.
This listing is courtesy of: AROD PARTNERS REALTY
CHATEAUX DU LAC - O6422691 - 1500 GAY RD #18D, WINTER PARK, FL 32789 8 Days on yellowkey
$275,000 | Condo 2 bedrooms, 2.0 bathroom
Welcome home to carefree lakefront living in the heart of Winter Park, where everyday life is complemented by breathtaking sunsets over beautiful Lake Killarney and one of Central Florida's most walkable locations. Nestled within the Chateaux Du Lac lakefront community, this beautifully updated second-floor condominium offers 2 bedrooms, 2 bathrooms, and an inviting open floor plan designed for comfortable everyday living. Stepping inside, plantation shutters throughout the home create a timeless look while allowing natural light to fill the space. The spacious living and dining areas flow seamlessly together, making entertaining both easy and enjoyable. The updated kitchen is sure to impress with quartz countertops, a center island, modern subway tile backsplash, stainless steel appliances, and recessed lighting that completes the contemporary design. The owner's suite provides a relaxing retreat complete with an updated ensuite bathroom featuring stunning floor-to-ceiling herringbone-style subway tile, an overhead rain showerhead, and modern finishes. The guest bedroom is generously sized and offers a large walk-in closet, while the second bathroom has been beautifully updated to match with the same designer tilework and rain showerhead. Sliding glass doors lead out to your private balcony, creating the perfect place to enjoy your morning coffee or unwind in the evening after a day on the lake. A brand-new water heater installed in 2026 provides added peace of mind. Residents of Chateaux Du Lac enjoy an exceptional lakefront lifestyle with access to a heated swimming pool, clubhouse, community deck overlooking Lake Killarney, private boat ramp, BBQ grilling area, saunas, kayak and paddleboard storage, and updated on-site laundry facilities. Whether you enjoy boating, skiing, paddleboarding, fishing, or simply taking in spectacular sunset views, this amenity-rich community offers everything you need to embrace the Florida lifestyle. Perfectly positioned just moments from Park Avenue, you'll enjoy easy access to locally owned restaurants, boutique shopping, cafés, Trader Joe's, the Winter Park Village, movie theater, farmers markets, and the nationally recognized Winter Park Sidewalk Art Festival. With convenient access to I-4, commuting throughout the Orlando area is effortless while still enjoying the charm and elegance that make Winter Park one of the area's most desirable communities. Schedule your showing today!
This listing is courtesy of: MAVREALTY
GARDEN LAKE ESTATES UNIT 1 - S5153086 - 3621 HAWTHORNE LN, WINTER PARK, FL 32792 8 Days on yellowkey
$415,000 | Single Family Home 3 bedrooms, 2.0 bathroom, 2 car garage
Discover the perfect place to call home! This beautiful 4-bedroom, 2-bath residence offers a spacious layout, a 2-car garage, and the freedom of no HOA. Conveniently located near top-rated schools, shopping, dinning and major highways, it provides the ideal balance of comfort, convenience, and value. Whether you're a first time homebuyer or looking to upgrade, this home is an excellent opportunity you won't want to miss.
This listing is courtesy of: AXEN REALTY, LLC
ALOMA PARK - O6422583 - 5781 SHALE CT, WINTER PARK, FL 32792 8 Days on yellowkey
$320,000 | Half Duplex 2 bedrooms, 2.0 bathroom, 1 car garage
**This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.** Welcome to 5781 Shale Court in Winter Park, a 2-bedroom, 2-bath home designed for comfortable everyday living. This one-story residence offers a practical layout with space for relaxing, dining, and hosting guests. The two-bedroom configuration provides flexibility for residents, visitors, a home office, or a hobby room, while two full bathrooms add convenience for daily routines. Outdoor living includes a covered and screened patio, creating a comfortable space to enjoy fresh air, outdoor dining, or quiet downtime while staying shaded and protected from the elements. Located in Winter Park, the home is close to shopping, dining, parks, schools, and everyday conveniences. The area offers access to nearby destinations such as Winter Park Village, Park Avenue, local recreation, and major roadways connecting to Maitland, Orlando, and surrounding Central Florida communities.
This listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS
MEAD GARDEN - R4911491 - 1250 S DENNING DR #109, WINTER PARK, FL 32789 8 Days on yellowkey
$190,000 | Condo 1 bedrooms, 1.0 bathroom
Welcome to this beautifully updated one-bedroom, one-bath condo in the heart of Winter Park. Thoughtfully maintained and move-in ready, this inviting home offers a bright, clean interior with tasteful finishes and a functional layout designed for comfortable, low-maintenance living. A spacious screened porch overlooks a serene courtyard, creating the perfect spot to enjoy your morning coffee or unwind at the end of the day. Perfectly situated, this home is nestled between two beautiful parks—Mead Botanical Garden, just steps away, and Seven Oaks Park—offering easy access to nature, walking paths, and green space. You're also just minutes from Rollins College, the boutiques and restaurants of Park Avenue, AdventHealth Winter Park, and the vibrant Mills 50 District. Outdoor enthusiasts will appreciate the nearby Cady Way Trail, Orlando Urban Trail, Dinky Line Trail, and Baldwin Park, all just a short bike ride away. With convenient access to Orlando Avenue (US-17/92), I-4, and both the Winter Park and AdventHealth SunRail stations, commuting throughout Central Florida is effortless. Located in the desirable Mead Garden Condominiums community with a sparkling pool and beautifully maintained grounds, this charming condo offers an exceptional blend of comfort, convenience, and the best of the Winter Park lifestyle.
This listing is courtesy of: FAIRBANKS REALTY
LAZY OAKS CONDO - O6422366 - 5184 LAZY OAKS DR, WINTER PARK, FL 32792 10 Days on yellowkey
$280,000 | Condo 2 bedrooms, 2.0 bathroom, 1 car garage
Charming two-bedroom, two-bath condominium available in Winter Park. The reserve is fully funded, and monthly condominium fees are low. A comfortable foyer welcomes you inside, leading down the hallway to the second bedroom at the front of the home, where a large window overlooks the front green space. The kitchen opens to a bright, inviting space with skylights that bring natural light into the combined living and dining area. A fireplace adds warmth to the room, while sliding glass doors lead to a private screened enclosure overlooking additional green space at the rear of the property. Ideally positioned within the home, the kitchen features all-new appliances and an oversized pantry with spice shelving for easy organization. The primary bedroom offers an inviting entrance with closet space upon entry. Sliding glass doors fill the room with soft natural light, creating a calm and peaceful atmosphere. The primary bath includes a double vanity and additional deep closet space. From the bedroom, step out to the screened enclosure and enjoy quiet moments in the Florida breeze. Lazy Oaks Condominium is a charming, peaceful community in Winter Park. Conveniently located near shopping, restaurants, schools, and universities, it offers an inviting place to relax and call home.
This listing is courtesy of: PAINE-ANDERSON PROPERTIES, INC
JUSTAMERE CAMP REP - O6422197 - 2611 LOTAFUN AVE, WINTER PARK, FL 32789 10 Days on yellowkey
$449,000 | Single Family Home 3 bedrooms, 2.0 bathroom, 2 car garage
Tucked away on a quiet dead-end street just off Lake Killarney, this solid block 1960's ranch at 2611 Lotafun Avenue offers over 1,800 SF of living space with room to make it your own. Featuring 3 bedrooms and 2 full baths, this home boasts a charming front living room with a wood-burning fireplace, PLUS a spacious family room/sunroom with its own fireplace — perfect for cozy nights or entertaining. The primary bedroom features an en suite bath, while the hall bath charms with original tilework. Step outside to your private pool, set on a generous 0.24-acre lot with a backyard shed for extra storage. Additional highlights include an attached 2-car garage with bonus storage room, interior laundry, and a 2022 roof. All new electrical was just installed in June 2026 by Skolfield Homes, giving buyers peace of mind on one of the big-ticket items. Enjoy the tranquility of this established neighborhood while staying close to major roadways, shopping, and dining. Homes with this much character and potential in Winter Park don't come around often — bring your vision and make this one shine!
LAKE WAUNATTA VILLAGE - TB8525179 - 7500 WAUNATTA CT, WINTER PARK, FL 32792 11 Days on yellowkey
$299,900 | Single Family Home 3 bedrooms, 2.0 bathroom, 2 car garage
Multiple OFFERS.. highest and best due by 10pm Sunday July 5th, Seller to review offers on Monday. Seller is a corporation and has never occupied the home. Seller does not disclose. It is Buyer and Buyers brokers responsibility to verify all information. Seller chooses Mainstay National Title. 5 day inspection period max. Closing date on or before 45 days from effective date. All appliances stay in home but not warranted by seller. SOLD AS-IS. See offer instructions. AC 10/2020. WH and Roof ages unknown.
This listing is courtesy of: FUTURE HOME REALTY INC
WINTER PARK PINES - O6422168 - 729 MONMOUTH WAY, WINTER PARK, FL 32792 11 Days on yellowkey
$799,000 | Single Family Home 4 bedrooms, 3.0 bathroom, 2 car garage
Under contract-accepting backup offers. Completely reimagined with an extensive top-to-bottom renovation, this stunning four-bedroom, three-bathroom pool home offers over 2,300 square feet of beautifully curated living space in one of Winter Park's most desirable locations. Every detail was thoughtfully selected to blend timeless design with modern functionality, creating a truly move-in-ready home. Inside, large wood-look plank tile flooring installed throughout in 2024 creates a seamless flow, complemented by recessed lighting, plantation shutters, all-new designer lighting and ceiling fans, and energy-efficient windows replaced in 2024. A cozy wood-burning fireplace provides character to the beautiful living space while French doors installed in 2024 provide effortless access to the outdoor living space. Additional upgrades completed in 2024 include blown-in insulation and a gas tankless water heater. The showstopping kitchen was completely remodeled in 2024 and is designed to impress. Custom hardwood cabinetry accented with elegant gold hardware is paired with luxurious quartz countertops and a dramatic full-height quartz backsplash. A large center island with seating for four, a black farmhouse sink, pot filler, and abundant prep space make this kitchen equally suited for everyday living and entertaining. Split from the secondary bedrooms for added privacy, the spacious primary suite is a peaceful retreat featuring French doors leading directly to the pool, a dedicated makeup vanity, walk-in closet, and a beautifully renovated ensuite bathroom with a double vanity and an oversized tiled shower enclosed by frameless glass. All three bathrooms were tastefully remodeled in 2024 with timeless, high-end finishes. The oversized laundry room is as functional as it is attractive, offering built-in cabinetry for exceptional storage along with an included washer and dryer. Step outside to your own private backyard oasis situated on a beautifully landscaped .26-acre lot. The screened in-ground pool was resurfaced with mini pebble finishes in 2025, while a custom flagstone outdoor shower with a decorative rock bed creates a true resort-inspired atmosphere. Additional exterior improvements completed in 2024 include new exterior doors, gutters, French drains, and an updated two-car garage featuring epoxy flooring along with new torsion springs and rollers. Ideally located just minutes from UCF, Rollins College, Full Sail University, AdventHealth Winter Park, the Crosby Wellness Center, Winter Park Pines Golf Club, and the Cady Way Trail, residents also enjoy access to Cady Way Park with its community pool, playground, beach volleyball courts, tennis courts, and pickleball courts. Zoned for highly rated Aloma Elementary, Glenridge Middle School, and Winter Park High School, this exceptional home combines a remarkable renovation with an unbeatable Winter Park lifestyle. ROOF - 2024 HVAC - 2024 ELECTRICAL - 2024 PLUMBING - 2024 TANKLESS WATER HEATER - 2024
This listing is courtesy of: KELLER WILLIAMS WINTER PARK
SPRINGVIEW - O6422142 - 1189 LAZY HOLLOW PL, WINTER PARK, FL 32792 11 Days on yellowkey
$450,000 | Single Family Home 4 bedrooms, 2.0 bathroom, 2 car garage
Welcome to your own private backyard oasis in the heart of Winter Park! This beautifully maintained two-story home offers 4 bedrooms, 2 bathrooms, and the perfect blend of comfort, style, and outdoor living. With no HOA, a fully fenced backyard, and a sparkling pool, this home delivers the Florida lifestyle buyers have been searching for. From the moment you arrive, you'll appreciate the pride of ownership throughout. The home features a 2022 metal roof, 2021 gutters, 2020 insulation, a 2019 A/C, and a new garage door and opener installed in 2023, giving buyers peace of mind for years to come. Inside, the home has been refreshed with fresh interior paint, updated door hardware throughout, updated kitchen hardware, and tasteful finishes that create a bright and welcoming atmosphere. Just beyond the living spaces, the screened patio provides the perfect transition to your backyard oasis. The backyard is truly the highlight of the home, featuring a pool resurfaced in 2024, a replaced pool pump motor, an expansive patio, a pergola, and a built-in sound system that conveys with the home, creating the perfect setting for relaxing or entertaining family and friends. The generous, fully fenced backyard offers plenty of space for pets, play, gardening, and enjoying the outdoors. Move-in ready and loaded with valuable updates, this exceptional Winter Park pool home offers comfort, functionality, and an unbeatable outdoor lifestyle. Conveniently located near shopping, dining, parks, and major roadways, this is one you won't want to miss!
This listing is courtesy of: KELLER WILLIAMS CLASSIC
COUNTRY LANE - O6418472 - 1612 LAWNDALE CIR, WINTER PARK, FL 32792 12 Days on yellowkey
$439,000 | Single Family Home 3 bedrooms, 2.0 bathroom, 2 car garage
A RARE OPPORTUNITY!! Houses on Lake Florence rarely become available! In desirable Country Lane in Winter Park, this 3 bed, 2 bath home is ready for you!! Updated kitchen with white cabinets, marble-look solid surface countertops, fresh tile. Primary bedroom has laminate floor and updated shower & countertops.
This listing is courtesy of: TOP VALUE PROPERTIES LLC
CEDARWOOD VILLAGE - O6421422 - 2305 SUN VALLEY CIR, WINTER PARK, FL 32792, WINTER PARK, FL 32792 12 Days on yellowkey
$279,900 | Condo 2 bedrooms, 2.0 bathroom
Beautifully renovated 2 bedroom, 2 bathroom condo at 2305 Sun Valley in Winter Park, offering a fresh modern design and thoughtful updates throughout. The fully redesigned kitchen features sleek cabinetry, quartz countertops, GE stainless steel appliances, a marble tile backsplash, abundant storage, recessed lighting, and a clean open feel that connects seamlessly to the main living areas. Wood-look porcelain tile flooring runs throughout the home, creating a cohesive, attractive, and low-maintenance finish. The spacious living area features vaulted ceilings, skylights, updated ceiling fans, and sliding glass doors that fill the space with natural light and lead to a covered screened patio overlooking green space. The primary suite includes an updated double vanity and a beautifully redesigned bathroom with a separate tub and newly installed shower. The second bathroom also offers an updated vanity and clean neutral finishes. Additional highlights include a 2021 AC, 2021 water heater, updated fixtures, generous natural light, and a screened outdoor living space ideal for relaxing and enjoying Florida’s indoor-outdoor lifestyle. This move-in ready Winter Park condo combines modern style, comfort, and everyday functionality. Residents enjoy access to a sparkling community pool, clubhouse, tennis and pickleball, and a pet walk with waste stations. Monthly fees also include roof and exterior building maintenance, exterior pest control, and landscaping, adding convenience and long-term value.The location is hard to beat, just minutes from Park Avenue, UCF, Rollins College, Full Sail University, shopping, dining, entertainment, and nearby medical facilities.
This listing is courtesy of: MARKET CONNECT REALTY LLC
WINTER PARK WOODS CONDO - O6421977 - 252 SCOTTSDALE SQ #252, WINTER PARK, FL 32792 12 Days on yellowkey
$85,000 | Condo 2 bedrooms, 1.5 bathroom
GLENMOOR - O6421887 - 7509 GLENMOOR LN, WINTER PARK, FL 32792 12 Days on yellowkey
$499,500 | Single Family Home 3 bedrooms, 2.0 bathroom, 2 car garage
Welcome to this charming home nestled at the end of a quiet cul-de-sac in the desirable Glenmoor community. Featuring 2,067 sq ft of inviting living space, this property offers a perfect blend of comfort and convenience. The open floor plan includes an eat-in kitchen and a spacious family room, ideal for entertaining. Relax in the living room with a cozy wood-burning fireplace. Enjoy outdoor living with a sparkling pool, raised gardens galore, and a fenced yard backing to a tranquil retention pond — no rear neighbors! The home boasts a large driveway, a 2-car garage, and a dedicated RV power hookup. Recent updates include all new vinyl windows to be installed in the enclosed lanai and remodeled bathrooms. This home is situated in a prime location with top-rated schools, close to dining, shopping, and entertainment options, including Winter Park, Baldwin Park, and easy access to highways 408 and I-4. Commuting is a breeze — just 25 minutes to Orlando International Airport, 20 minutes to Downtown Orlando, and within an hour of Cocoa Beach, Disney World, and Universal Studios. Schedule your private tour today and make this fantastic Orlando area home yours!
This listing is courtesy of: RE/MAX PRIME PROPERTIES
WINTER PARK PINES - O6421873 - 722 S RANGER BLVD, WINTER PARK, FL 32792 12 Days on yellowkey
$825,000 | Single Family Home 4 bedrooms, 3.0 bathroom, 2 car garage
Impeccably Renovated Turn-Key Oasis with a Resort-Style Backyard! No HOA with yard large enough for possible ADU. Welcome home to this meticulously updated 4-bedroom, 3-bathroom residence where true pride of ownership shines through every detail. Absolutely turn-key and loaded with premium updates throughout, such as new electrical panel, newer water heater, new pool pavers, upgraded engineered floors throughout & much more! This home offers the perfect blend of modern luxury and effortless entertaining.The heart of the home seamlessly connects to the outdoors with a brilliant kitchen pass-through window, serving an enormous covered patio. Step into your own private, tranquil backyard oasis featuring a freshly resurfaced pool surrounded by stunning new pavers & large Perolga. Whether you are hosting a summer barbecue or rinsing off in your convenient outdoor shower after a swim, this backyard is built for Florida living at its finest. Property is zoned for highly rated schools with convenient location just moments away from Cady Way Park & trails, Rollins, UCF, & Full Sail Colleges, just 4 miles from vibrant dining(Park Ave) & premier shopping.
STRATFORD A WINTER PARK CONDO - O6420915 - 283 LEWFIELD CIR #283, WINTER PARK, FL 32792 12 Days on yellowkey
$142,500 | Condo 1 bedrooms, 1.0 bathroom
Under contract-accepting backup offers. Seller may consider buyer concessions if made in an offer ~ Recently UPDATED and ready for its next owner, this light-filled FIRST FLOOR condo unit offers LOW MAINTENANCE LIVING in the desirable Stratford community of Winter Park – with a monthly HOA that's lower than many comparable communities! Step inside through the semi-private INTERIOR ENTRY to an OPEN CONCEPT floor plan featuring updated bathroom finishes, WOOD LAMINATE & TILE FLOORING throughout, and a spacious living and dining area designed for everyday comfort and easy entertaining. The kitchen is equipped with STAINLESS STEEL APPLIANCES, breakfast bar seating, and a seamless connection to the main living spaces. A convenient IN-UNIT LAUNDRY closet adds to the home's functionality, while sliding glass doors lead out to a SCREENED LANAI overlooking a large green space for the perfect spot to enjoy your morning coffee or unwind at the end of the day. Stratford is a beautifully maintained community offering a park-like setting complete with a COMMUNITY POOL and peaceful surroundings thanks to the mature trees, making it easy to enjoy the Florida lifestyle without the upkeep of a single-family home. Ideally located at the corner of Lake Howell Road and Howell Branch Road with quick access to SR 436, you will appreciate being just minutes from abundant shopping, dining, medical services, parks, and everyday conveniences. Whether you are searching for your first home, a seasonal retreat, or an investment opportunity, this well-maintained Winter Park condo is one you won't want to miss. Call today to schedule a tour!
This listing is courtesy of: WEMERT GROUP REALTY LLC
WINTER WOODS - O6421731 - 1956 JAPONICA RD, WINTER PARK, FL 32792 13 Days on yellowkey
$549,000 | Single Family Home 3 bedrooms, 2.0 bathroom, 2 car garage
Welcome home to this beautifully updated 3-bedroom, 2-bath move-in ready home living on a spacious quarter-acre lot in one of Winter Park’s established neighborhoods. From the moment you arrive, you’ll appreciate the home’s inviting curb appeal with refreshed landscaping, and gutters. Inside, the open, light-filled layout features luxury vinyl plank flooring and tile throughout, creating a cohesive and modern feel that’s both beautiful and easy to maintain.The heart of the home is the thoughtfully renovated kitchen, complete with quartz countertops, soft-close cabinetry, Whirlpool and KitchenAid stainless steel appliances - including an induction stove top and double ovens. Major home features have recently been updated giving buyers confidence and peace of mind. The roof was replaced in 2020, the HVAC system in 2023, the water heater in 2019, and windows plus the sliding glass door were replaced in 2025 to improve energy efficiency and comfort. Step outside to your own private backyard retreat. The fully fenced yard offers exceptional space for pets, play, gardening, or even a future pool. An oversized extended paver patio creates the perfect setting for outdoor dining, entertaining friends, or simply relaxing on a Florida evening.
This listing is courtesy of: PROPLOGIK REALTY INC
CEDARWOOD VILLAGE 1 - O6421135 - 2372 SUN VALLEY CIR #2372, WINTER PARK, FL 32792 13 Days on yellowkey
$285,000 | Condo 2 bedrooms, 2.0 bathroom
Welcome to this beautifully updated condo, ideally nestled between Winter Park and Maitland. This inviting home features a versatile upstairs loft overlooking the living and dining areas—perfect for a home office, fitness space, craft room, or additional guest accommodations. The bright, cheerful eat-in kitchen is both stylish and functional, showcasing quartz countertops, a glass tile backsplash, abundant cabinetry, a pull-out spice rack, trash/recycling cabinet, and a built-in storage unit. Sliding glass doors open to the private front courtyard, filling the space with natural light. Conveniently located laundry area, complete with washer and dryer, is tucked within the kitchen. The spacious living room features a cozy wood-burning fireplace and flows seamlessly into the dining area beneath soaring vaulted ceilings accented by skylights. Sliding glass doors lead to a screened lanai with a slate tile floor and a storage closet—an ideal spot to relax and enjoy Florida living. The primary suite also opens directly to the lanai and offers a beautifully renovated en-suite bath with a luxurious walk-in shower, updated vanity, linen cabinet, and a custom walk-in closet with built-in organizers. The front bedroom also includes a generous walk-in closet. Enjoy added privacy with a picturesque, tree-lined green space across the street rather than neighboring condos directly in front. Two dedicated parking spaces are conveniently located just outside your door. Cedarwood Village offers an exceptional location directly across from Casselberry Commons Shopping Plaza and is just minutes from Full Sail University, UCF, and Rollins College. Residents enjoy a community swimming pool, tennis courts with pickleball lines, and designated dog-walking areas. Additional highlights include a new roof and skylights installed in 2020. Monthly HOA fees cover exterior maintenance, lawn care, and community amenities, making this the perfect opportunity to enjoy carefree living in one of the area's most desirable communities.
CONWILL ESTATES - O6420928 - 1622 ARBOR PARK DR, WINTER PARK, FL 32789 13 Days on yellowkey
$695,000 | Single Family Home 3 bedrooms, 1.5 bathroom , 1 car carport
Exceptional opportunity to build new or renovate and expand on this desirable lot in Winter Park. Situated on a charming tree lined street and in a neighborhood that is experiencing a great deal of new development. The existing 1950s residence features parquet wood flooring and open living and dining spaces, which overlooks the backyard and open wooden deck. With generous space to work with, there are great possibilities to create your own custom residence. The property is zoned for long-established schools - Lakemont Elementary, which is just down the street from the property, as well as Maitland Middle and Winter Park High. Plus, ideally located within a short stroll to the Winter Park Y, Phelps Park, and minutes to downtown Park Ave's shopping and dining! Property is being sold AS IS.
QUARTERS AT WINTER PARK CONDO - O6421299 - 1122 WASHINGTON AVE #7B, WINTER PARK, FL 32789 13 Days on yellowkey
$575,000 | Townhouse 2 bedrooms, 2.5 bathroom, 2 car garage
Completely reimagined in 2025, this stunning 2-bedroom, 2.5-bath townhome offers the perfect blend of modern luxury and an unbeatable Winter Park location. Just minutes from Rollins College, Park Avenue, boutique shopping, award-winning dining, and everything that makes Winter Park so desirable, this move-in-ready home has been thoughtfully renovated from top to bottom with timeless, designer-selected finishes. The heart of the home is the beautifully redesigned kitchen featuring Sarah Sherman Samuel cabinetry and hardware, gorgeous marble countertops, a custom marble ledge, and all-new appliances. Throughout the home, you'll find new flooring, smooth-finished walls, fresh interior paint, recessed lighting with dimmers, updated electrical, new interior doors and hardware, and new baseboards, creating a clean, sophisticated aesthetic. Upstairs, both spacious bedrooms feature beautifully updated en-suite bathrooms, while the primary suite includes a custom marble-top vanity and a thoughtfully designed built-in closet system. Every bathroom has been fully renovated with high-end finishes that elevate the home's overall design. Step outside to your own private outdoor retreat featuring a large covered patio with low-maintenance turf—perfect for entertaining, relaxing, or enjoying your morning coffee year-round. Major mechanical updates provide added peace of mind, including a 2023 air handler, 2024 water heater, all-new A/C ductwork, and added attic insulation for improved energy efficiency. With nearly every surface and major system thoughtfully updated, this exceptional Winter Park townhome offers luxurious, turnkey living in one of Central Florida's most sought-after neighborhoods.
This listing is courtesy of: ALL REAL ESTATE & INVESTMENTS
WATERFALL COVE - O6420863 - 1695 LEE RD #A116, WINTER PARK, FL 32789 13 Days on yellowkey
$135,000 | Condo 3 bedrooms, 2.0 bathroom
Welcome to this charming first-floor 3-bedroom, 2-bath condominium located in the beautiful city of Winter Park! Featuring laminate flooring throughout the main living areas, this inviting home offers an open-concept layout with a combined living and dining room that overlooks the kitchen, creating the perfect space for everyday living and entertaining. Each bedroom is equipped with a ceiling fan for added comfort, while the private rear patio provides a peaceful outdoor retreat complete with a bench—ideal for relaxing and enjoying Florida's beautiful weather. Whether you're searching for a primary residence, a seasonal getaway, or an investment opportunity, this condo offers exceptional value. HOA dues include pest control, basic cable, basic internet, exterior maintenance, and additional storage, providing convenience and peace of mind. Residents also enjoy access to community amenities including a swimming pool, playground, and clubhouse, all in a desirable Winter Park location close to shopping, dining, parks, and major roadways. Don't miss the opportunity to make this wonderful property your own!
This listing is courtesy of: REAL BROKER, LLC
KAROLINA ON KILLARNEY - O6421199 - 1960 BISCAYNE DR, WINTER PARK, FL 32789 14 Days on yellowkey
$300,000 | Single Family Home 2 bedrooms, 1.0 bathroom
Perfect Property for Builder or Investor Nestled in the sought-after Karolina on Killarney neighborhood, this classic 1935 bungalow offers timeless character and an exceptional opportunity to create your dream home in one of Central Florida's most desirable locations. Situated on a generous lot, this 2-bedroom, 1-bath residence features approximately 1,408 square feet of living space with a flexible floor plan ready for your personal vision. Original architectural details provide a warm foundation for renovation, restoration, or expansion, while the spacious backyard offers ample room for outdoor entertaining, gardening, or future additions. Whether you're a homeowner looking to customize a historic property or an investor seeking your next project, this home presents outstanding value in a neighborhood surrounded by beautifully updated residences. Ideally located just minutes from Park Avenue's renowned dining, boutique shopping, museums, and year-round events, you'll also enjoy convenient access to Downtown Orlando, College Park, Winter Park Village, major hospitals, and top commuter routes. With no HOA and a prime location in the heart of Winter Park, opportunities like this are increasingly rare. Bring your imagination and unlock the incredible potential this charming property has to offer!
CHARMONT - O6420387 - 341 E READING WAY, WINTER PARK, FL 32789 14 Days on yellowkey
$1,695,000 | Single Family Home 4 bedrooms, 4.0 bathroom, 2 car garage
Virtually Staged. A rare opportunity to live on a quiet one-way street overlooking a park in the heart of Winter Park. Built in 2007 and meticulously maintained, this exceptional 4-bedroom, 4-bath pool home with a dedicated office offers timeless design, thoughtful updates, and an unbeatable location. A welcoming covered front porch provides the perfect spot to enjoy your morning coffee. Inside, soaring ceilings, extensive moldings, travertine and hardwood floors, and abundant natural light create an elegant first impression. Just off the foyer, French doors open to a private office, ideal for working from home. A secondary bedroom and full bath with a walk-in shower are conveniently located on the main level. The spacious kitchen flows seamlessly into the family room and features granite countertops, solid wood soft-close cabinetry, a gas cooktop, wall oven, breakfast bar, wet bar, walk-in pantry, and a sunny breakfast nook overlooking the lanai and pool. The adjoining family room is anchored by a gas fireplace and French doors leading outdoors. The covered lanai showcases a tongue-and-groove ceiling and remote-controlled screens, creating the perfect setting for year-round entertaining. The generous first-floor primary suite offers space for a sitting area and features two custom walk-in closets, dual vanities, a soaking tub, separate shower, and private water closet. A beautiful wrought-iron staircase leads upstairs to two generous en-suite bedrooms and a cozy loft. The private backyard is designed for relaxation and entertaining, featuring a saltwater pool and spa surrounded by lush landscaping. Additional highlights include two newer HVAC systems (2022 and 2023), a gas water heater (2022), central vacuum system, built-in Home Team pest defense system, and plantation shutters throughout. Located within the highly sought-after Audubon K-8 and Winter Park High School districts, this exceptional home is ideally situated between Park Avenue and Corrine Drive, with downtown Orlando just minutes away.
GLENCOE SUBDIVISION - O6418164 - 2361 ROXBURY RD, WINTER PARK, FL 32789 14 Days on yellowkey
$599,000 | Single Family Home 3 bedrooms, 2.0 bathroom
Nested on a spacious, tree lined lot just steps from Lake Killarney, 2361 Roxbury Road offers a rare opportunity to create your dream home in one of Winter Park’s most convenient locations. Ideally situated just off Fairbanks Avenue with quick access to I-4 , this 3 bedroom, 2 bath residence features 1723 square feet of living space, solid plaster walls and mid century character. Built in 1951, the home showcases an original pine paneled ceiling in the living room, adding warmth and architectural charm. Two large, new Anderson windows fill the room with natural light and highlight the pool view. New Anderson exterior doors improve the homes security and efficiency. The expansive Florida room provides flexible space for entertaining or future updates. Major improvements include a resurfaced Gunite pool in pebble finish (2024), exterior paint (2024), new paver driveway (2024), roof (2020) and HVAC system (2019). The garage has been enclosed and currently serves as storage and utility space. Outside you’ll find a fully fenced backyard with plenty of room to enjoy the Florida lifestyle. Located on a large lot with sidewalks and mature trees, this home presents an excellent opportunity for buyers looking to personalize a property in a desirable Winter Park location. The septic system was pumped in 2026, providing peace of mind. Bring vision and make this home your own!
This listing is courtesy of: ANNE ROGERS REALTY GROUP INC
SUBURBAN HOMES - O6420961 - 4887 N MAGNOLIA AVE, WINTER PARK, FL 32792 15 Days on yellowkey
$495,000 | Single Family Home 4 bedrooms, 3.0 bathroom , 1 car carport
Under contract-accepting backup offers. Experience the Florida lifestyle in this beautifully updated 4-bedroom, 3-bath Winter Park pool home! From the renovated bathrooms and spacious family room to the all-new flooring and fresh paint, this move-in-ready home offers comfort, style, and room to entertain. Step through the new French doors into your private backyard oasis featuring a sparkling pool with new pavers, a new pool pump (2026), and a child safety fence for added peace of mind. The homes roof was replaced in 2016 and other updates include HVAC system with ductwork, water heater, all-new windows, an updated utility room, a new garage door with remote, plus an extended driveway for spacious parking. Conveniently located near shopping, dining, and downtown Orlando. This home is zoned for highly rated Lake Monte Elementary, Maitland Middle, and Winter Park High School. Don't miss this exceptional opportunity to own a beautifully updated home in one of Central Florida's most desirable communities.
This listing is courtesy of: LUXE PROPERTIES