Winter Park Schools and Nearby Homes for Sale and Rent

Please click on one of the below schools to see properties that are marked as being nearby those schools in the MLS.

Elementary Schools


Middle Schools

High Schools





Newest Winter Park Homes by School

  • 922 N PENNSYLVANIA AVE, WINTER PARK, FL - MLS# O6424685

    Winter Park High - O6424685 - 922 N PENNSYLVANIA AVE, WINTER PARK, FL 32789
    Just Added on 07/14/2026 11:12AM

    $1,995,000 | Single Family Home | 4 beds | 4.0 baths | 2 gar

    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.

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    Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY

  • 1778 MONDRIAN CIR, WINTER PARK, FL - MLS# O6422941

    Edgewater High - O6422941 - 1778 MONDRIAN CIR, WINTER PARK, FL 32789
    1 Day on yellowkey

    $1,339,000 | Townhouse | 3 beds | 3.5 baths | 2 gar

    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.

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    Listing is courtesy of: KELLY PRICE & COMPANY LLC

  • 344 STARLING RD, WINTER PARK, FL - MLS# O6424771

    Edgewater High - O6424771 - 344 STARLING RD, WINTER PARK, FL 32789
    1 Day on yellowkey

    $4,500 | Single Family Home | 3 beds | 3.0 baths

    For Rent – Beautifully Updated Home Near Lake Killarney! Located just minutes from Downtown Winter Park, Park Avenue, I-4, and Maitland, this beautifully updated home offers convenient access to nearby shops and dining. The 3-bedroom, 3-full-bath layout features open living spaces and modern finishes throughout. LVP flooring flows through the entire home, complemented by fresh paint, abundant natural light, and designer fixtures. The kitchen boasts a large island and nicely appointed stainless steel appliances, perfect for everyday living and entertaining alike. The primary bedroom offers plenty of space and direct access to the covered patio. Its en suite bath is a true spa retreat, featuring a floating vanity, luxurious soaking tub, walk-in shower, and an expansive walk-in closet. Two comfortably sized guest bedrooms share an updated hall bath. Situated on a spacious quarter-acre lot, the home includes a large fenced backyard with a deck, ideal for outdoor entertaining and relaxation. Lawncare is included. Available August 1, 2026. Rent is $4,500/month with a $5,000 security deposit. Pets will be considered and are subject to owner approval; a $500 non-refundable pet deposit is required. Application fee is $50 per adult. Schedule your showing today!

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    Listing is courtesy of: KELLY PRICE & COMPANY LLC

  • 462 W LYMAN AVE, WINTER PARK, FL - MLS# O6423842

    Winter Park High - O6423842 - 462 W LYMAN AVE, WINTER PARK, FL 32789
    1 Day on yellowkey

    $1,595,000 | Single Family Home | 3 beds | 2.5 baths | 2 gar

    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.

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    Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY

  • 263 SCOTTSDALE SQ #263, WINTER PARK, FL - MLS# O6424619

    Winter Park High - O6424619 - 263 SCOTTSDALE SQ #263, WINTER PARK, FL 32792
    1 Day on yellowkey

    $80,000 | Condo | 2 beds | 2.0 baths

    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!

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    Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO

  • 436 W SWOOPE AVE, WINTER PARK, FL - MLS# O6423105

    Winter Park High - O6423105 - 436 W SWOOPE AVE, WINTER PARK, FL 32789
    3 Days on yellowkey

    $719,900 | Townhouse | 4 beds | 3.5 baths | 2 gar

    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!

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    Listing is courtesy of: RE/MAX EXCLUSIVE COLLECTION

  • 786 MCINTYRE AVE, WINTER PARK, FL - MLS# O6424399

    Winter Park High - O6424399 - 786 MCINTYRE AVE, WINTER PARK, FL 32789
    3 Days on yellowkey

    $625,000 | Townhouse | 3 beds | 2.5 baths | 2 gar

    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!

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    Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES

  • 303 SCOTTSDALE SQ #303, WINTER PARK, FL - MLS# O6424296

    Winter Park High - O6424296 - 303 SCOTTSDALE SQ #303, WINTER PARK, FL 32792
    5 Days on yellowkey

    $80,000 | Condo | 2 beds | 2.0 baths

    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!

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    Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO

  • 1830 STAUNTON AVE, WINTER PARK, FL - MLS# O6424087

    Edgewater High - O6424087 - 1830 STAUNTON AVE, WINTER PARK, FL 32789
    5 Days on yellowkey

    $3,200 | Single Family Home | 2 beds | 2.5 baths | 1 car

    STYLISH, STUNNING AND RENOVATED TO THE NINES. This 3-bedroom, 2.5-bath Winter Park home has great access to Interstate-4 and both Winter Park and Orlando downtown areas. With all interior spaces updated, this fantastic home is almost totally rebuilt with brand new electrical, plumbing, heating and air, ductwork, roof, flooring and Energy Star doors and windows. In addition to the 3 upstairs bedrooms, the downstairs has a bonus room which is perfect for a den or playroom and a convenient interior laundry room. The lot is 6,750 sqft and is fenced and gated (electronic with remotes) offering a nice new patio of clay pavers, a carport, and large backyard. This 1,774 sqft of living space is perfect for the tenant who wants quality, style and convenient location. This one is MOVE IN READY AND WAITING FOR YOU. There is a $99 for each adult application fee and once approved the first & last month’s rent will be due along with the security deposit and any applicable pet fee and deposit.

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    Listing is courtesy of: COLDWELL BANKER REALTY

  • 1298 BEACHVIEW AVE, WINTER PARK, FL - MLS# O6417337

    Edgewater High - O6417337 - 1298 BEACHVIEW AVE, WINTER PARK, FL 32789
    5 Days on yellowkey

    $1,375,000 | Single Family Home | 1 beds | 1.0 baths

    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.

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    Listing is courtesy of: PREMIER SOTHEBYS INT'L REALTY

  • 1750 WALNUT AVE, WINTER PARK, FL - MLS# O6422700

    Winter Park High - O6422700 - 1750 WALNUT AVE, WINTER PARK, FL 32789
    5 Days on yellowkey

    $2,195,000 | Single Family Home | 4 beds | 4.5 baths | 2 gar

    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.

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    Listing is courtesy of: PALMANO GROUP RE BROKERAGE LLC

  • 2803 RIDDLE DR, WINTER PARK, FL - MLS# O6423829

    Edgewater High - O6423829 - 2803 RIDDLE DR, WINTER PARK, FL 32789
    5 Days on yellowkey

    $589,000 | Single Family Home | 3 beds | 2.5 baths | 2 gar

    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.

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    Listing is courtesy of: CORCORAN PREMIER REALTY

  • 2450 GRAND TETON CIR #2450, WINTER PARK, FL - MLS# O6418973

    Lake Howell High - O6418973 - 2450 GRAND TETON CIR #2450, WINTER PARK, FL 32792
    5 Days on yellowkey

    $255,000 | Condo | 3 beds | 2.0 baths

    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!

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    Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO

  • 2010 SUMMERFIELD RD, WINTER PARK, FL - MLS# O6420140

    Winter Park High - O6420140 - 2010 SUMMERFIELD RD, WINTER PARK, FL 32792
    5 Days on yellowkey

    $594,500 | Single Family Home | 3 beds | 2.0 baths | 1 car

    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.

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    Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO

  • 2189 SUSSEX RD, WINTER PARK, FL - MLS# O6423782

    Lake Howell High - O6423782 - 2189 SUSSEX RD, WINTER PARK, FL 32792
    6 Days on yellowkey
    FORECLOSURE

    $375,000 | Single Family Home | 4 beds | 2.5 baths | 2 gar

    **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.

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    Listing is courtesy of: PROPERTY LOGIC RE

  • 4965 ORANGE AVE, WINTER PARK, FL - MLS# O6423739

    Winter Park High - O6423739 - 4965 ORANGE AVE, WINTER PARK, FL 32792
    6 Days on yellowkey

    $379,900 | Single Family Home | 4 beds | 2.0 baths | 1 car

    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.

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    Listing is courtesy of: RE/MAX TOWN & COUNTRY REALTY

  • 1000 S SEMORAN BLVD #715, WINTER PARK, FL - MLS# S5153133

    Winter Park High - S5153133 - 1000 S SEMORAN BLVD #715, WINTER PARK, FL 32792
    6 Days on yellowkey

    $1,200 | Condo | 1 beds | 1.0 baths

    Enjoy comfortable living in the highly sought-after Winter Park area! Close to shopping, dining, and major roadways, this well-located rental provides exceptional value in one of Central Florida's most desirable communities. This first-floor condo is ideally located just steps from the community pool and on-site laundry facilities, offering convenience and easy access to everyday amenities. Don't miss this opportunity to make it your next home.

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    Listing is courtesy of: LPT REALTY, LLC

  • 508 DUNBLANE DR, WINTER PARK, FL - MLS# O6423719

    Winter Park High - O6423719 - 508 DUNBLANE DR, WINTER PARK, FL 32792
    6 Days on yellowkey

    $2,900 | Single Family Home | 3 beds | 2.0 baths | 1 car

    Wonderful 3 bedroom, 2 bath rental in the heart of Winter Park. Location is amazing! Central to Rollins College, UCF, Winter Park Schools, Baldwin Park, and more! Be sure to schedule a private showing.

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    Listing is courtesy of: COMPASS FLORIDA LLC

  • 3131 LOWNDES DR, WINTER PARK, FL - MLS# O6423443

    Winter Park High - O6423443 - 3131 LOWNDES DR, WINTER PARK, FL 32792
    7 Days on yellowkey

    $3,995 | Single Family Home | 4 beds | 2.0 baths

    Occupied until July 31 2026. [August 1st 2026 house will be available for in-person showings and Vacant on SentriKey.] Beautiful 4 Bedroom Furnished House with a Pool! This home has an Eat-In Updated Kitchen. There are 3 bedrooms and a bathroom on one side and a large master suite on the other side with a fireplace. The master bathroom has an extra large walk-in shower with a double mirrored dressing area. There is a family room/ FLex Space/ Office Area with a Roku TV, Desk, and Wi-Fi. There is no garage. It has 2 sheds for storage in the back. The neighborhood is nice and quiet. It is conveniently located near Hospitals, Businesses, Restaurants, Schools and Shopping.

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    Listing is courtesy of: A +ROI PROPERTY

  • 2905 PARKLAND DR, WINTER PARK, FL - MLS# O6422550

    Winter Park High - O6422550 - 2905 PARKLAND DR, WINTER PARK, FL 32789
    7 Days on yellowkey

    $3,395,000 | Single Family Home | 6 beds | 7.0 baths | 3 gar

    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!

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    Listing is courtesy of: UNITED REAL ESTATE PREFERRED

  • 1754 TAYLOR AVE, WINTER PARK, FL - MLS# O6421927

    Winter Park High - O6421927 - 1754 TAYLOR AVE, WINTER PARK, FL 32789
    7 Days on yellowkey

    $2,569,999 | Single Family Home | 5 beds | 4.5 baths | 2 gar

    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.

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    Listing is courtesy of: ONE LUXURY INTERNATIONAL LLC

  • 439 N CAPEN AVE, WINTER PARK, FL - MLS# O6422949

    Winter Park High - O6422949 - 439 N CAPEN AVE, WINTER PARK, FL 32789
    8 Days on yellowkey

    $849,000 | Single Family Home | 3 beds | 2.5 baths | 2 gar

    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.

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    Listing is courtesy of: COMPASS FLORIDA LLC

  • 1823 SUNSET DR, WINTER PARK, FL - MLS# O6421690

    Winter Park High - O6421690 - 1823 SUNSET DR, WINTER PARK, FL 32789
    8 Days on yellowkey

    $2,549,000 | Single Family Home | 5 beds | 4.5 baths | 2 gar

    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!

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    Listing is courtesy of: ONE LUXURY INTERNATIONAL LLC

  • 730 W SWOOPE AVE, WINTER PARK, FL - MLS# S5152493

    Winter Park High - S5152493 - 730 W SWOOPE AVE, WINTER PARK, FL 32789
    9 Days on yellowkey

    $839,000 Increased | Single Family Home | 5 beds | 3.0 baths

    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.

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    Listing is courtesy of: AROD PARTNERS REALTY

  • 1500 GAY RD #18D, WINTER PARK, FL - MLS# O6422691

    Edgewater High - O6422691 - 1500 GAY RD #18D, WINTER PARK, FL 32789
    9 Days on yellowkey

    $275,000 | Condo | 2 beds | 2.0 baths

    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!

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    Listing is courtesy of: MAVREALTY

  • WINTER PARK, FL - MLS# O6422736

    Lake Howell High - WINTER PARK, FL 32792
    9 Days on yellowkey

    $2,325 | Townhouse | 3 beds | 2.5 baths | 1 gar

    MOVE-IN SPECIAL-$230 OFF THE 1ST MONTH'S RENT!!!! Welcome home to this beautiful 3-bedroom, 2.5-bath end-unit townhome with a one-car garage, located in the highly desirable gated community of Vistas at Lake Howell in Winter Park. This rare rental opportunity offers a spacious and inviting floor plan with a large living room featuring laminate flooring and a built-in entertainment center. The fully equipped kitchen includes stainless steel appliances, solid-surface countertops, and solid wood cabinetry. All bedrooms are located upstairs for added privacy. The spacious primary suite features a large walk-in closet. The versatile third bedroom can serve as a traditional bedroom, home office, guest room, or flex space to suit your lifestyle. The upstairs laundry closet adds everyday convenience by keeping everything on one level. All Keller Williams residents are enrolled in the Resident Benefits Package (RBP). The RBP includes HVAC air filter delivery, renters' insurance, credit building to help boost your credit score with timely rent payments, $1M Identity Protection, utility concierge service to make utility connections a breeze during your move-in, our best-in-class resident rewards program, and much more. More details are available upon application. Renters' insurance is required, and proof of coverage must be provided. Conveniently located near shopping, dining, Full Sail University, Rollins College, and UCF, with easy access to SR 408, SR 417, SR 426 (Aloma Avenue), and SR 436 (Semoran Boulevard), making commuting throughout Central Florida quick and convenient. This exceptional townhome won't last long!

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    Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS

  • 3621 HAWTHORNE LN, WINTER PARK, FL - MLS# S5153086

    Lake Howell High - S5153086 - 3621 HAWTHORNE LN, WINTER PARK, FL 32792
    9 Days on yellowkey

    $415,000 | Single Family Home | 3 beds | 2.0 baths | 2 gar

    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.

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    Listing is courtesy of: AXEN REALTY, LLC

  • 5781 SHALE CT, WINTER PARK, FL - MLS# O6422583

    Lake Howell High - O6422583 - 5781 SHALE CT, WINTER PARK, FL 32792
    9 Days on yellowkey

    $320,000 | Half Duplex | 2 beds | 2.0 baths | 1 gar

    **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.

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    Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS

  • 1250 S DENNING DR #109, WINTER PARK, FL - MLS# R4911491

    Winter Park High - R4911491 - 1250 S DENNING DR #109, WINTER PARK, FL 32789
    9 Days on yellowkey

    $190,000 | Condo | 1 beds | 1.0 baths

    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.

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    Listing is courtesy of: FAIRBANKS REALTY

  • 660 OSCEOLA AVE #101, WINTER PARK, FL - MLS# O6420593

    Winter Park High - O6420593 - 660 OSCEOLA AVE #101, WINTER PARK, FL 32789
    9 Days on yellowkey

    $9,500 | Condo | 3 beds | 3.5 baths

    Experience the best of Winter Park waterfront living in this beautifully updated ground-floor residence at Perle du Lac, ideally located just a short stroll from the boutiques, restaurants, and cafés of Park Avenue. Even more rare, this exceptional residence includes a private covered boat slip on the pristine waters of Lake Virginia, offering direct access to the renowned Winter Park Chain of Lakes. Offering just over 2,700 square feet of thoughtfully designed living space, the home features freshly painted interiors, hardwood and travertine flooring, and elegant custom millwork throughout. The gourmet kitchen is equipped with custom cabinetry, hardwood countertops, and premium Sub Zero, Wolf, Dacor, and Bosch appliances. A versatile library with custom built ins provides the perfect space for a home office, reading room, or additional living area. The spacious primary suite is a peaceful retreat featuring picturesque lake views and a spa inspired bath with dual vanities, a soaking tub, walk in shower, private water closet, and a generous walk in closet. Two additional bedrooms, two full bathrooms, a powder room, and a dedicated laundry room are thoughtfully situated on the opposite side of the residence, offering exceptional privacy for family and guests. Just off the living room, a covered lakeside patio provides the perfect setting for morning coffee or evening sunsets overlooking Lake Virginia. From here, enjoy easy access to your private covered boat slip, making it effortless to spend the day exploring the Winter Park Chain of Lakes. Additional highlights include two assigned garage parking spaces, a private storage room, and access to Perle du Lac's exceptional amenities, including a heated pool, hot tub, beautifully landscaped grounds, and double gated security. Combining the convenience of a walkable Park Avenue lifestyle with the luxury of private lakefront boating, this residence offers one of Winter Park's most desirable living experiences.

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    Listing is courtesy of: CORCORAN PREMIER REALTY

  • 641 S LAKEMONT AVE, WINTER PARK, FL - MLS# O6420696

    Winter Park High - O6420696 - 641 S LAKEMONT AVE, WINTER PARK, FL 32792
    9 Days on yellowkey

    $2,250 | Single Family Home | 3 beds | 2.0 baths | 1 car

    Welcome home to this charming, move-in-ready residence in the heart of Winter Park! Ideally located near top-rated public schools, shopping, dining, and healthcare facilities, this beautifully updated 3-bedroom, 2-bath home offers approximately 1,450 square feet of comfortable living space. The remodeled kitchen features modern cabinetry, updated appliances, and plenty of space for cooking and gathering. Both bathrooms have been tastefully renovated with stylish fixtures and finishes. Tile flooring extends throughout the main living areas, while the bedrooms feature durable vinyl flooring for added comfort and easy maintenance. Additional highlights include a spacious laundry room, a large tiled Florida room that provides flexible living space, and a fully fenced backyard—perfect for pets, outdoor entertaining, or simply relaxing. Call today for a showing!

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    Listing is courtesy of: WEICHERT REALTORS HALLMARK PROPERTIES

  • 5184 LAZY OAKS DR, WINTER PARK, FL - MLS# O6422366

    Lake Howell High - O6422366 - 5184 LAZY OAKS DR, WINTER PARK, FL 32792
    11 Days on yellowkey

    $280,000 | Condo | 2 beds | 2.0 baths | 1 gar

    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.

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    Listing is courtesy of: PAINE-ANDERSON PROPERTIES, INC

  • 2611 LOTAFUN AVE, WINTER PARK, FL - MLS# O6422197

    Edgewater High - O6422197 - 2611 LOTAFUN AVE, WINTER PARK, FL 32789
    11 Days on yellowkey

    $449,000 | Single Family Home | 3 beds | 2.0 baths | 2 gar

    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!

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    Listing is courtesy of: KELLY PRICE & COMPANY LLC

  • 2942 ANTIQUE OAKS CIR #86, WINTER PARK, FL - MLS# O6422284

    Winter Park High - O6422284 - 2942 ANTIQUE OAKS CIR #86, WINTER PARK, FL 32792
    12 Days on yellowkey

    $1,400 | Condo | 1 beds | 1.0 baths

    Welcome home to this beautiful, bright, and well maintained rental in Winter Park. Enjoy a comfortable layout, plenty of natural light, and a warm, inviting feel from the moment you walk in. Conveniently located near shopping, dining, UCF, Full Sail University, and major highways. This is a place you'll love coming home to. Schedule your showing today!

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    Listing is courtesy of: EMPIRE NETWORK REALTY

  • 729 MONMOUTH WAY, WINTER PARK, FL - MLS# O6422168

    Winter Park High - O6422168 - 729 MONMOUTH WAY, WINTER PARK, FL 32792
    12 Days on yellowkey

    $799,000 | Single Family Home | 4 beds | 3.0 baths | 2 gar

    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

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    Listing is courtesy of: KELLER WILLIAMS WINTER PARK

  • 1189 LAZY HOLLOW PL, WINTER PARK, FL - MLS# O6422142

    Lake Howell High - O6422142 - 1189 LAZY HOLLOW PL, WINTER PARK, FL 32792
    12 Days on yellowkey

    $450,000 | Single Family Home | 4 beds | 2.0 baths | 2 gar

    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!

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    Listing is courtesy of: KELLER WILLIAMS CLASSIC