32789 Zip Code FL Florida Style Homes for Sale

2 Beds ⋅ 1 Baths ⋅ Dubsdread Heights SubDv. ⋅ 32789 Zip Code

Roof 2018 | HVAC 2020| Set on a deep, tree-canopied lot in one of Winter Park's most desirable established neighborhoods, this charming single-story concrete-block home blends timeless character with everyday convenience. A grand oak shades the front lawn, helping cool the home and lower energy costs, while durable masonry construction, a dimensional-shingle roof, and a full-length driveway leading to a covered carport deliver lasting value and practical, protected parking with an attached workshop & storage room. A generous screened front porch offers a breezy, bug-free spot for morning coffee or evening relaxation before you step inside to a spacious living room featuring gleaming refinished hardwood floors and a wood-burning fireplace framed by a classic white mantel with fluted columns. A large picture window floods the room with natural light, and a graceful curved archway, one of the home's most distinctive architectural details, leads you deeper into the thoughtfully connected floor plan. The kitchen is efficiently designed with cabinetry lining both walls for ample storage, laminate counters, under-cabinet lighting, and a full stainless-steel appliance suite. A double sink offers plenty of room to work and a large window overlooks the lush backyard, with a rear door providing easy access for grilling and entertaining. The adjacent, light-filled dining room offers flexible space that works well for family meals, a home office, or a quiet reading nook. Two comfortable bedrooms feature hardwood floors, ceiling fans with lights, and built-in closets, one with built-in shelving, while the bright corner primary enjoys windows on two walls for excellent light and cross-ventilation. A full bathroom is finished with a tiled tub-and-shower combination, a wood vanity, and a frosted privacy window that brings in daylight while maintaining seclusion. Out back, a large, fully fenced yard framed by mature oaks, palms, and established privacy hedges creates a secluded, park-like retreat with ample room to garden, play, entertain, or add a pool. Just minutes from historic Park Avenue, residents enjoy boutique shopping, award-winning restaurants, sidewalk cafés, museums, and year-round community events, with nearby College Park adding popular dining, breweries, and specialty shops. Outdoor recreation abounds with Dubsdread Golf Course, Mead Botanical Garden, Kraft Azalea Garden, and numerous parks close by, plus easy access to Winter Park's scenic chain of lakes and walking trails, all without requiring waterfront ownership. Commuting is effortless thanks to convenient access to Interstate 4, Fairbanks Avenue, Lee Road, SR 426, and SR 436, providing quick connections throughout Central Florida. Downtown Orlando, the Orlando Health and AdventHealth medical campuses, and major employment centers are all within easy reach. With excellent shopping, grocery stores, entertainment, and cultural attractions nearby, this sought-after location offers the perfect balance of quiet residential living and close proximity to everything Central Florida has to offer. This listing is for a single home and lot at 846 Driver Ave, but the owner would also consider selling the adjacent home next door to the North at 844 Driver Ave. If you are interested in purchasing both homes simultaneously, contact listing agent for more details.

846 Driver Avenue, Winter Park

$525,000

3 Beds ⋅ 4 Baths ⋅ Quarters At Winter Park Condo SubDv. ⋅ 32789 Zip Code

Beneath mature oak trees in The Quarters at Winter Park, this townhome-style condominium presents a rare opportunity to own a spacious, architecturally distinctive residence in one of Winter Park's most established communities. Priced to reflect its as-is condition, the home offers exceptional potential for a buyer ready to personalize the space. A gated brick courtyard and covered front porch lead to light-filled living and dining areas featuring engineered hardwood flooring and a wrought-iron staircase. The kitchen offers granite countertops, a gas range and opens to the family room, where a gas fireplace and skylight create a welcoming gathering space. A private screened courtyard connects the residence to the detached two-car garage. Upstairs, the primary suite spans more than 300 square feet and features a custom walk-in closet and dual-sink en-suite bath. Two additional bedrooms include one with a private en-suite bath and another with access to a balcony overlooking the tree-lined street. Ideally just minutes from Park Avenue, Rollins College and Seven Oaks Park, this residence offers the opportunity to renovate and customize a home in one of Winter Park's most sought-after communities. Sold as is, with an inspection report available upon request.

1134 Washington Avenue Unit 13C, Winter Park

$775,000

4 Beds ⋅ 3 Baths ⋅ Conwill Estates SubDv. ⋅ 32789 Zip Code

Welcome to 1562 Arbor Park Drive, a beautifully maintained four-bedroom, two-and-a-half-bath residence tucked along a charming brick street in the heart of Winter Park. This move-in-ready home combines elevated finishes, abundant natural light, a flexible split-bedroom floor plan, and an exceptional location near the shopping, dining, and cultural attractions that make Winter Park one of Central Florida’s most desirable communities. At the center of the home is a completely redesigned kitchen that is both stylish and highly functional. New cabinetry, quartz countertops, stainless steel appliances, generous storage, and an oversized island with bar seating create an inviting setting for everyday meals and entertaining. A beautiful picture window frames views of the lush backyard and fills the kitchen with natural light. The open living spaces flow seamlessly together over wood-look tile flooring, while fresh interior paint, updated fixtures, and an electric fireplace add warmth and a polished contemporary feel. Privately positioned on one side of the home, the expansive primary suite feels like a retreat of its own. The suite includes a custom designed walk-in closet and a beautifully designed bathroom with separate vanities, a freestanding soaking tub, an oversized walk-in shower, and a private water closet. Three additional bedrooms are located on the opposite side of the home, providing separation and flexibility for family members or overnight guests. The outdoor setting is equally impressive. The enormous, fully fenced backyard has been lovingly maintained and features mature greenery, privacy, and plenty of room for entertaining, recreation, gardening, pets, or a future outdoor living retreat. Bonus: there is additional parking on the west side of the home that is accessible from the backyard - perfect for hosting or entertaining! A cobblestone driveway enhances the home’s curb appeal, while notable improvements include replacement of the HVAC system and ductwork in 2016, numerous plumbing updates, and extensive interior renovations. Enjoy a location that places the best of Winter Park within easy reach. The home is conveniently located near the Winter Park YMCA, Lakemont Elementary School, Phelps Park, Rollins College, and the Winter Park Chain of Lakes - not to mention all of the boutiques, restaurants, museums, & cafés, and community events of historic Park Avenue. Baldwin Park, Winter Park Village, and Audubon Park are also just minutes away, offering even more options for dining, shopping, entertainment, and outdoor recreation. This is an exceptional opportunity to enjoy a gorgeous, fully updated home in the highly desirable in-town Winter Park address. Schedule your private showing and experience the lifestyle, location, and thoughtful design of 1562 Arbor Park Drive.

1562 Arbor Park Drive, Winter Park

$569,000

3 Beds ⋅ 3 Baths ⋅ Fairshores Place SubDv. ⋅ 32789 Zip Code

Life in Winter Park is about more than just where you live—it's about how you live. At 2803 Riddle Drive, that lifestyle comes together with an inviting open floor plan, a private full fenced backyard with a pool designed for year-round enjoyment, and a location that's just minutes from everything that makes Winter Park one of Central Florida's most desirable communities. The heart of the home is a bright, open living space where the kitchen, dining, and living areas flow effortlessly together around a wood-burning fireplace. Filled with natural light and designed for connection, it's a space that feels equally suited for lively gatherings, holiday celebrations, or quiet evenings at home. Step outside and discover what truly sets this property apart. A sparkling private pool and a fully fenced quarter-acre yard that creates an outdoor retreat that's increasingly hard to find. Whether you're entertaining friends, watching children or pets play, or simply enjoying a peaceful morning by the pool, this backyard offers the space and privacy to enjoy Florida living the way it was meant to be. Thoughtful updates—including a new roof (2022), HVAC system (2022), fresh interior paint, and updated lighting—provide peace of mind while leaving opportunities for the next owner to make the home uniquely their own. Ideally located just minutes from Park Avenue's dining and boutiques, Lake Killarney, Hillstone, College Park and major commuter routes, this home offers exceptional convenience without sacrificing the character and charm that make Winter Park so special. With a private pool, two-car garage, generous outdoor space, and an open floor plan that truly lives for entertaining, 2803 Riddle Drive offers a rare opportunity to enjoy the Winter Park lifestyle at an exceptional value.

2803 Riddle Drive, Winter Park

$699,900

3 Beds ⋅ 3 Baths ⋅ Magnolia Gardens Sub SubDv. ⋅ 32789 Zip Code

**NEW CONSTRUCTION QUALITY | WALKABLE WINTER PARK | DESIGNER SMART HOME** This is not a remodel — it's a complete architectural transformation completed in September 2022. Taken to the slab and studs, this Winter Park residence was entirely rebuilt with new roof trusses, all-new electrical, new AC system (inside and out), tankless water heater, new plumbing, and smart irrigation — delivering true new construction quality in an established neighborhood. Located steps from Winter Park Village, Park Avenue, Whole Foods, Starbucks, Publix, cinema, restaurants, and more. Arrive home to a grand 51' custom driveway flanked by mature Italian cypress trees, sculptural landscaping, and elegant iron railing — pulling directly to your covered front porch entry. No garage means no wasted space — just a clean, architectural arrival experience designed to impress. Inside, light-filled interiors with soaring 6" baseboards, full custom tile flooring, and an abundance of natural light create a gallery-like aesthetic that feels curated, not cookie-cutter. Custom liner windows in the dining room and primary suite flood the home with natural light while adding unmistakable architectural character. **The Kitchen:** - Designer floating shelves - Smart range and under-counter built-in microwave - Under-cabinet and island LED lighting - Decorative pendants and ambient lighting throughout **The Primary Suite:** A private retreat with ceiling-mounted rain shower and spa-like finishes designed to decompress after a walkable night out on Park Avenue. **Smart Home Ready:** - New AC system (inside and out) with smart thermostat - Tankless water heater and fully new plumbing - Smart lock entry - Google Nest doorbell with two-way audio - Smart soffit exterior lighting - Weather-monitored smart irrigation **Out Back:** A fully private PVC-fenced backyard sanctuary — spacious enough for pets, entertaining, and room to roam. A covered porcelain tile patio plus a separate fire pit slab make this an outdoor living extension you'll actually use year-round in the Florida lifestyle. Over 300 sq ft of additional space was added to accommodate two additional bathrooms, interior laundry, and a layout built for real life — including a new stacked washer and dryer. Properties combining true gut-renovation quality, luxury designer touches, smart technology, and this rare walkable Winter Park address don't last. Move-in ready — and built to last for decades.

860 N Denning Drive, Winter Park

$750,000

3 Beds ⋅ 2 Baths ⋅ Park West Condo SubDv. ⋅ 32789 Zip Code

Virtually Staged. Welcome to Park West Condominiums — one of Winter Park’s most coveted and rarely available condominium communities, ideally located just one block from the boutiques, dining, and charm of Park Avenue. This unique 4th floor residence offers an exceptional combination of space, privacy, and potential. Featuring 3 bedrooms and 2 bathrooms, the expansive floor plan has been enlarged by enclosing two patios, creating generous living spaces rarely found in condominium living. Vaulted ceilings, skylights, and abundant natural light enhance the open, airy feel throughout the home, while the top-floor location provides remarkable tranquility and privacy. The spacious kitchen offers ample counter space, a breakfast bar, and excellent cabinet space, while the living area is anchored by a fireplace — another uncommon feature in condo living. Large bedrooms, a sizable in-unit laundry room with extensive storage, and an oversized attic provide an extraordinary amount of storage seldom seen in comparable properties. The primary suite features vaulted ceilings, a walk-in closet, and a spacious bathroom layout. For maximum flexibility, the second bedroom, featuring a bright Sun Room alcove, connects to the primary bedroom so it could also be utilized as a private den. Recent unit improvements include a NEW HVAC system, a NEW Water Heater, and Plumbing updates. A reserved covered parking space is included, along with plentiful guest parking for visitors. Residents of Park West enjoy a secure gated entrance, community pool, tennis court, on-site community manager, and beautifully maintained grounds with extensive recent community improvements completed. Association fees include water, sewer, and trash service, creating a truly low-maintenance “lock-and-leave” lifestyle ideal for travelers or seasonal residents. While this condo presents an exciting opportunity for personalization, the location, floor plan, and features make this an exceptional offering with tremendous potential. Opportunities in Park West are exceedingly rare — this is your chance to create something truly special in the heart of Winter Park.

300 Carolina Avenue Unit 402C, Winter Park

$589,000

3 Beds ⋅ 2 Baths ⋅ Winter Park Village SubDv. ⋅ 32789 Zip Code

Tremendous value in the land. Well cared for vintage Winter Park home that has 3 BEDROOM and two bath rooms. Potential to remodel, improve and expand or simply tear down to build a new custom home. However, this home is move in ready! There is not an HOA. 1343 total square feet and 1186 heated square feet. Newer DUAL-PANE WINDOWS! New HVAC system in NOvember 2025. Home was replumbed in 2024. SEPTIC PUMP OUT, OCT 2025. No carpeting instead there is SOLID FLOORING THROUGHOUT: WOOD PARQUET, TILE, LUXURY VINYL PLANK. The kitchen has been updated with SOLID WOOD KITCHEN CABINETS + GRANITE COUNTER TOPS and newer MATCHING APPLIANCES. The home has INDOOR WASHER/DRYER and a working fireplace. The back yard is FULLY FENCED. Local top rated CITY OF WINTER PARK SCHOOLS. And CITY OF WINTER PARK UTILITIES. The land, the lot have a fantastic upside. BOTH NEXT DOOR (WEST SIDE) AND REAR (NORTH SIDE) NEIGHBORING LOTS HAVE BEEN EMPTY FOR SEVERAL YEARS. This is a great investment and the property itself offers excellent rental income. Think "down the road" value + immediate return value.

1319 Bessmor Road, Winter Park

$225,000

2 Beds ⋅ 3 Baths ⋅ Sandlewood Creek Condo Ph 04 SubDv. ⋅ 32789 Zip Code

One or more photo(s) has been virtually staged. Welcome to one of the most affordable opportunities to own in the highly sought-after Winter Park High School district. This well-maintained community is tucked into a beautiful setting and is extremely convenient to everything that makes Winter Park one of Central Florida's top lifestyle destinations. This end-unit two bedroom / two-and-a-half bath condo in Sandlewood Creek combines a hip retro-classic style with comfort, functionality, and peace of mind with a long list of recent improvements. Solid knotty-pine wood accent paneling is featured throughout and compliments the freshly painted walls in designer colors. The kitchen has been partially renovated and has a nice clean and modern vibe, complemented by granite countertops and updated bathrooms for a clean, modern feel. The roof was replaced in 2021. Major system upgrades include an A/C (2019) and a brand-new water heater (2026), while the entire interior has just been freshly painted, carpets professionally cleaned, and a final detailed cleaning completed—making this home truly move-in ready. Whether you're looking for a primary residence, a low-maintenance lifestyle, or a smart investment in one of Central Florida’s most consistently in-demand areas, this property checks all the boxes. Enjoy easy living in a quiet, established community just minutes from everything that makes Winter Park special—top-rated schools, dining, shopping, and parks. Pre-approved for FHA financing and recent updates that your insurance company will like - this is a rare opportunity in this market. Don't miss it!. Sellers have this priced to sell, so don't delay. Call today to make your appointment for your private viewing.

Winter Park

$2,032,850

4 Beds ⋅ 4 Baths ⋅ Park Grove W/125 Lot 10 Blk D SubDv. ⋅ 32789 Zip Code

A rare offering in the highly sought-after Park Grove neighborhood, this expertly redesigned 4-bedroom residence blends elevated design with effortless everyday living. Originally renovated by award-winning interior designer John McClain and recognized with first-place honors in 2020, the home reflects a refined balance of style and functionality.??Ideally located just moments from Park Avenue and Winter Park Village, this single-story home offers an inviting, open flow with curated architectural details throughout. The main living space is anchored by rich hardwood floors, a marble-tiled fireplace, and expansive sliding glass doors that fill the home with natural light while creating a seamless connection to the outdoor living areas.??The kitchen serves as the heart of the home, featuring gourmet gas appliances, an inviting dining space, and a beautifully integrated wine station. It is perfect for both daily living and entertaining.??Designed for true indoor-outdoor living, the home opens to a private backyard retreat complete with a resort-style pool, lush landscaping, and multiple areas for gathering or relaxing.??The primary suite offers a serene escape with a spacious walk-in closet, spa-inspired bath, and freestanding soaking tub. A separate guest suite provides comfort and privacy, while an additional flex space offers versatility for a home office or additional living area.??This home has been completely improved with major system upgrades, including a new roof, updated HVAC systems, new windows and doors, a whole-house generator, whole-home water filtration system, and an integrated Sonos audio and security system, providing both comfort and peace of mind.??Park Grove is a neighborhood where homes seldom come on the market, because once you’re here, you won’t want to leave.

872 Granville Drive, Winter Park

$1,200,000

3 Beds ⋅ 2 Baths ⋅ Cloisters Condo SubDv. ⋅ 32789 Zip Code

Experience lakefront living in the heart of Winter Park. One of only two residences in The Cloisters with soaring 9-foot ceilings, this first-floor, three-bedroom, two-bath home offers a rare blend of privacy, scale and panoramic Lake Osceola views. Just two blocks from Park Avenue and adjacent to the Alfond Inn, this condominium lives like a private residence with unmatched access to boutique shopping, fine dining and cultural landmarks. Designed for elegant everyday living and entertaining, the open floor plan showcases a chef’s kitchen with granite countertops, solid wood cabinetry, and an island for prep and serving. The spacious dining and living areas are enhanced by hardwood flooring, crown molding and a marble-trimmed wood-burning fireplace. More than 20 feet of sliding glass doors open to an expansive, L-shaped terrace that brings in natural light and offers breathtaking lake vistas. The oversized primary suite offers serene lake views and includes an en-suite bath with dual vanities, built-in closets and a walk-in shower. Additional features include a rare laundry and utility room with a full-size washer, dryer and sink, updated electrical and plumbing, and upgraded water heater and HVAC system. Just two blocks from Park Avenue, this residence places you in the heart of downtown Winter Park’s sought-after lifestyle. Enjoy effortless access to fine dining, boutique shopping, world-class museums, Rollins College and year-round cultural events, all in an accessible, lakefront setting. Whether going to the Saturday farmers market, dining alfresco along the avenue or taking in the scenic views of Lake Osceola from your private residence, this property offers a seamless blend of luxury and urban elegance.

106 S Interlachen Avenue Unit 118, Winter Park

$2,000,000

3 Beds ⋅ 3 Baths ⋅ Sevilla SubDv. ⋅ 32789 Zip Code

Once closed, call LA for Effective sales price. Totally traditional luxury single-story home is located in the desirable Sevilla neighborhood in Winter Park. Sitting high and dry on approximately a half-acre beautifully landscaped lot. Original home was mostly gutted down to the studs in 2011-2012 and COMPLETELY re-done. Multi-generational potential as this home has a complete attached guesthouse. Interior layout boasts formal living with bay window and tall ceilings, dining room with antiqued mirror set into extensive moldings and trim, plus a library/den with a tongue and groove wood vaulted ceiling and a wall of bookshelves and built-ins. The spacious family room with a white-washed brick, wood-burning fireplace wall and vaulted ceiling is all open to the breakfast area and kitchen. The gourmet kitchen features custom inset cabinet drawers and doors, white marble slab backsplashes, Kohler farmhouse sink and a large island with a deep prep sink. The kitchen is a chef’s delight with a 48-inch Viking gas range, Viking warming drawer, Jenn-Air refrigerator, wine refrigerator and a Bosch dishwasher. The kitchen also has amazing storage and two large pantries. There are a total of four bedrooms (the 4th is currently the living room of the in-law suite suite) and three full baths. Throughout the home are beautiful real ¾-inch-thick and 5-inch-wide plank walnut floors, beam and coffered ceilings, French doors, oversized picture windows and designer accents lighting. French doors off the family room open to seamlessly blend indoor and outdoor living, leading to a covered lanai with travertine stone tile overlooking a resort and entertaining backyard. Huge swimming pool and a 30-by-15-foot pergola with Bistro lighting, which is a wonderful spot to relax, dine and play, all on a tiny pebble surface, like an Italian driveway! French garden fountain, rose garden and synthetic turf for pets make the backyard a haven. The home’s floor plan offers a desirable layout with huge primary bedroom with a generously sized un-suite bath with dual sink counters, amazing Roman walk-in shower, jetted tub with bubblers and two large walk-in closets. Guest wing features a spacious bedroom and bath and the West Wing is a full In-law apartment, including a bedroom, handicapped bath, full kitchen and its living room (which would be easy to be converted back into the 4th bedroom - plans available). Imagine having a wonderful space for in-laws or an adult family member that needs space of their own. Just a short drive or bike ride from Park Avenue, this open and inviting home has easy access to downtown Winter Park, AdventHealth, downtown Orlando and is zoned for A-rated schools. Surround sound through most of the house and CAT 6 wiring throughout. Recent additional remodeling and updating have taken place including all new windows, paint inside and out, as well as a new roof and gutters in 2022. A detailed list of all renovations is available upon request.

1624 Barcelona Way, Winter Park

$475,000

3 Beds ⋅ 3 Baths ⋅ Orange Terrace SubDv. ⋅ 32789 Zip Code

What a great location - Ready for move in before the holidays! Don’t miss this impeccable classic Florida ranch, 3/2 with hardwood floors, PLUS bonus bath in utility! Large sunny living room with wood burning fireplace, dining room, renovated kitchen with granite counters and wood cabinetry. Large bedrooms with great closets and good storage. Updated hall bathrooms with tub/shower and pedestal sink and primary suite bath with stall shower. Lovely landscaped fenced yard with screened porch and large gazebo for entertaining! 2 car garage, plus workbench and large utility room with access to rear and side yard. Perfectly located in Winter Park near Lake Killarney with easy access to I-4, College Park, Maitland and Downtown Orlando. Bonus - Walk to E-Tennis for those tennis and pickleball enthusiasts!

260 Orange Terrace Drive, Winter Park

$1,700,000

4 Beds ⋅ 3 Baths ⋅ Comstock Park SubDv. ⋅ 32789 Zip Code

Don’t miss the opportunity to live in one of Winter Park’s most desirable neighborhoods. Nestled on a charming, tree-lined brick street, this meticulously updated 4-bedroom, 3-bath home exudes elegance and style, offering ample space for family comfort as well as areas to relax and entertain. This impressive property has been fully renovated and is truly move-in ready. From the moment you arrive, you'll be captivated by the charming exterior and lush landscaping on a spacious .32acre lot. Inside, you'll find a bright, sophisticated home featuring beautiful hardwood floors throughout, tons of windows accented with plantation shutters, and exquisite handcrafted details. The front family room features a wood-burning fireplace, creating a comfortable space for binge-watching Netflix or Sunday NFL games, unwinding with a good book, sharing wine with friends, or hosting elegant dinner parties in the dining area. The light and bright chef’s kitchen is a culinary dream that offers a generous layout with abundant wood cabinetry, gleaming granite and gorgeous wood countertops, a large prep island with seating for four, state-of-the-art Thermador stainless steel appliances including a 6-burner professional oven, and an inviting sitting nook, capped off by a dramatic cathedral ceiling and windows that overlook the lush back yard. On one side of the home are three generously sized bedrooms with ample closet space and two full bathrooms with gorgeous custom tile and flooring. On the other side of the home awaits a true retreat: the private Primary Suite, a sanctuary equipped with a spacious bedroom, sitting area, walk-in custom closet, and a luxurious spa-inspired bath with stunning porcelain tile flooring, a large dual sink vanity, an oversized walk-in shower, and a separate water closet. Step outside to experience the quintessential Florida lifestyle in the private backyard oasis, complete with a beautiful sparkling saltwater pool, a spacious patio, and professionally landscaped grounds — ideal for entertaining year-round. Additional features include a convenient laundry/mudroom with storage for backpacks and gear, abundant closet space, a water softener, and a two-car garage with storage cabinets and shelves. Improvements include updated electrical, plumbing, and ductwork, plus a brand new tile roof (2023). This remarkable property is located close to Winter Park’s renowned Park Avenue shopping, premier restaurants, the area’s top-rated schools, and also close to Interlachen Country Club and the Winter Park Racquet Club. This exceptional property won’t last. See for yourself why this gorgeous house should be the place you call home. Schedule your showing today.

1571 Lasbury Avenue, Winter Park

$840,000

2 Beds ⋅ 2 Baths ⋅ Cloisters Condo SubDv. ⋅ 32789 Zip Code

Welcome to The Cloisters, one of Winter Park’s established lakefront communities, ideally between Park Avenue and Lake Osceola. This top-floor residence, rarely available in the building, offers a turnkey lifestyle with exceptional updates and peaceful water views. The home’s oversized screened balcony, complete with a custom awning, creates an uncommon open-air retreat that overlooks the community’s heated pool, putting green, manicured gardens and Lake Osceola. Unlike many residences in the community, this property retains its original open balcony design, offering outdoor living rarely found in this floor plan. Inside, every surface has been thoughtfully remodeled. The kitchen features solid wood cabinetry, granite countertops and refined finishes. Both baths are fully updated, including a new tub with glass enclosure in the guest bath and a walk-in shower with frameless glass in the primary suite. Tile flooring, custom vanities and designer fixtures complete each space. Engineered hardwood flooring runs throughout the main living areas, with plush carpet in the bedrooms for added comfort. The primary suite includes custom built-ins, dual closets and a built-in desk with additional cabinetry, delivering elegance and function. The second bedroom offers flexibility as a guest room or study and features optional shared access from the primary suite for additional privacy. Additional highlights include a covered and assigned parking space equipped with one of the building’s few electric vehicle charging stations, ample guest parking and access to a community dock with boat slips available through a resident lottery system. The Cloisters has successfully completed all required Milestone Inspections and the Structural Integrity Reserve Study, ensuring peace of mind for future residents and affirming the association’s commitment to long-term stewardship. Amenities include two fitness centers with dry saunas and a newly renovated clubhouse with kitchen and a partial bath for use as a powder room, ideal for hosting private events. Ideally positioned just steps from the dining, shopping and cultural energy of Park Avenue and in proximity to Rollins College, this original-owner residence offers a compelling blend of lifestyle, location and enduring design.

100 S Interlachen Avenue Unit 503, Winter Park

$5,125,000

5 Beds ⋅ 6 Baths ⋅ J Kronenberger Sub SubDv. ⋅ 32789 Zip Code

This stunning private residence is on an oversized lot featuring a private sports pad, kids playground and sparkling pool. Encompassing over 6,700 square feet of expansive .55-acre lot, this home boast five spacious bedrooms, one office, 5.5 baths and a dedicated movie room, recording studio and a fully equipped gym with a private sauna. Ideally just moments from serene Lake Maitland and the charming Azalea Park, this home offers natural beauty and prime location. The chef's kitchen is designed for function and style with dual oversized islands, ideal for entertaining and everyday living. Spacious, inviting and thoughtfully designed, this oversized family room is the heart of the home-ideal for everything from cozy movie nights to lively holiday parties featuring expansive square footage, the room comfortably accommodates large groups, with plenty of space for multiple seating areas and a bar area. Oversized windows flood the space with natural light while the high ceilings and an open layout enhance the airy welcoming feel. Whether you are hosting extended family or entertaining friends, this room is built for connection, comfort and lasting memories. The private recording studio can be turned into a private mother-in-law suite or a kids playroom. The luxurious primary suite retreat to your own private oasis featuring a cozy fireplace, direct access to a serene private porch and a one-of-a-kind walk-in closet designed for style and functionality. The oversized en-suite bath boasts a steam shower, creating a spa-like experience right at home. Two additional en-suite bedrooms upstairs, each with walk in closets. Thoughtfully designed for convenience, this home features a spacious mud room off the garage which is ideal for busy households. Enjoy the ultimate convenience with two separate laundry rooms, one’s downstairs for easy access and a second upstairs near the bedrooms, making laundry day effortless and efficient. Ideally near Winter Park Racquet Club, Interlachen Country Club and accessible to Park Avenue, this exceptional residence also offers an extraordinary residence with a luxurious functionality and a premier location.

1240 Harding Street, Winter Park

$2,798,000

4 Beds ⋅ 3 Baths ⋅ Palmer Park SubDv. ⋅ 32789 Zip Code

Stunning canal-front home, Winter Park Chain of Lakes. Welcome to this exceptional one-story residence in the heart of Winter Park, offering direct access to the desired Winter Park Chain of Lakes via the Venetian Canal. Built in 2018, this meticulously maintained home features four bedrooms, three baths, and 3,258 square feet of elegant living space designed for comfort and entertaining. The open floor plan showcases a large gourmet kitchen outfitted with custom cabinetry and generous counter space. Ideal for hosting gatherings or enjoying quiet evenings at home. Expansive windows throughout the home offer beautiful, tranquil views of the canal and lush, mature landscaping. Large screened-in lanai complete with a fully equipped summer kitchen and fireplace overlooking the canal and private boathouse.

1074 Mckean Circle, Winter Park

$164,000

2 Beds ⋅ 1 Baths ⋅ Lakeside Manor Apts Condo SubDv. ⋅ 32789 Zip Code

Welcome to life on Lake Killarney, one of Winter Park’s most sought-after lakefront communities! This charming 2-bedroom, 1-bathroom condo offers an unbeatable location and resort-style amenities—perfect for those seeking the true Florida lifestyle.Enjoy direct access to Lake Killarney, where residents can take advantage of boat slips available at a low cost on a first-come, first-serve basis, as well as a private boat launch, a brand-new dock with covered over-water seating, a lakeside pool, and a clubhouse. The beautifully manicured green spaces and quiet courtyard areas create a peaceful, community-oriented atmosphere.Inside, this move-in ready unit has been freshly painted throughout and features new carpeting. The kitchen has been tastefully refreshed and offers plenty of cabinet space. An assigned parking space is located just steps from the unit, and there's an on-site laundry facility plus a private storage unit for added convenience.Tucked away yet close to it all, you’re just minutes from the shops and restaurants of Winter Park, with easy access to I-4 and other major roadways. Residents love living here—units don’t come available often, so don’t miss your chance to call this lakeside gem home!

2500 Lee Rd Unit 219, Winter Park

$1,050,000

3 Beds ⋅ 2 Baths ⋅ Charmont SubDv. ⋅ 32789 Zip Code

Incredible location in the heart of Winter Park, situated on an oversized lot, on a brick street, close to Park Avenue.

2250 Forrest Road, Winter Park

$775,000

2 Beds ⋅ 2 Baths ⋅ Cloisters Condo SubDv. ⋅ 32789 Zip Code

Welcome to The Cloisters—a prestigious lakefront community nestled in the heart of Winter Park, perfectly positioned between the timeless charm of Park Avenue and the serene beauty of Lake Osceola. This fully furnished second-floor residence has been meticulously redesigned and renovated to maximize both space and style, offering the comfort of a thoughtfully designed home, enhanced by luxurious, designer-selected finishes throughout. Step inside to discover a beautifully appointed interior featuring high-end touches. The kitchen is a true showpiece, boasting custom wood cabinetry with artistic wood detailing, granite countertops, full counter-to-cabinet backsplashes, and top-tier appliances including a Wolf cooktop and oven, Fisher & Paykel dishwasher, Liebherr wine cooler, and Sub-Zero refrigerator. The expansive kitchen island comfortably seats four, with a sleek, integrated extension that effortlessly accommodates up to seven—perfect for entertaining in style. The open-concept living area flows seamlessly to a spacious private balcony, offering tranquil views of the heated pool, putting green, lush landscaping, and the shimmering waters of Lake Osceola—ideal for a morning coffee or year-round entertaining. The primary suite is a serene retreat, featuring blackout blinds, a Sleep Number smart bed with dual temperature controls, and custom floor-to-ceiling built-ins with integrated lighting, display shelving, and a dedicated vanity area. Additional built-in cabinetry lines the hallway leading to the en-suite bathroom, providing ample space for jewelry, shoes, and wardrobe essentials. The second bedroom is designed for versatility, with a wall-to-wall built-in home office setup overlooking a beautiful resort-style view, along with its own matching floor-to-ceiling built-ins for display and storage. Both bathrooms have been tastefully reimagined with new vanities, granite countertops, upgraded shower enclosures and hardware, and stylish lighting and mirrors. The primary bath includes additional custom built-ins for optimal storage and organization. Throughout the home, fresh paint and luxury vinyl flooring create a clean, modern aesthetic. Additional features include an in-unit washer and dryer tucked behind a custom wood door, a built-in safe, and a new A/C unit installed in 2024. The residence also includes a deeded covered-parking space and a private storage unit. The Cloisters community offers a wealth of amenities, including an onsite property manager, ample guest parking, elevators, a heated pool, onsite laundry facilities, a putting green, private lake access, a dock, and boat slips available via resident lottery. Residents also enjoy two fitness centers with one dry sauna and a recently updated clubhouse with a full kitchen and bath—ideal for private gatherings. Just a short stroll from the boutiques, restaurants, and cultural attractions of Park Avenue, and Rollins College, this fully renovated, turnkey residence presents a rare opportunity to enjoy the ultimate blend of location, luxury, and lifestyle. Realtor/owner is a licensed Florida real estate broker.

100 S Interlachen Avenue Unit 204D, Winter Park

$725,000

4 Beds ⋅ 2 Baths ⋅ Capens Add SubDv. ⋅ 32789 Zip Code

Under contract-accepting backup offers. Stop the car! Develop your dream project on this hard to find R-3 lot! Adjacent 75x100 R-3 vacant lot (TAX ID 06-22-30-1168-02-023) on the south side to be purchased simultaneously, for a total of 75x200 or 15,000sq/ft. Next to the proposed Winter Park Commons project, walk to Winter Park Village, Hannibal Square, WP9 and Park Ave for top shopping, dining and entertainment. Don’t miss this unique opportunity! PROPERTY SOLD AS-IS. VALUE IS IN THE LAND. NO REPAIRS.

770 W Webster Avenue, Winter Park

$750,000

2 Beds ⋅ 2 Baths ⋅ Osceola Summit SubDv. ⋅ 32789 Zip Code

Location, location, location! Whether you're ready to build your dream home or simply want to enjoy life in Central Florida’s most prestigious neighborhood at an unbeatable value, this delightful mid-century 2-bedroom, 2-bathroom home offers endless possibilities. Lot size is approximately 130 ft X 78 ft. Perfectly positioned just minutes from Park Avenue, Rollins College, and Lake Osceola, this home places you at the center of luxury Winter Park living—enjoy boutique shopping, fine dining, scenic strolls, or morning paddle boarding just steps from your door. Inside, you'll find a bright and open floor plan filled with natural light and timeless charm. A front den/office with white tile flooring and timeless tongue and groove ceiling offers you space that is not only stylish but functional—ideal for working from home or relaxing with a book. The open living/dining area features stylish wood flooring, large windows, and a ceiling fan for year-round comfort. This unique layout offers 2 primary suites offering plenty of privacy. Head to the fully fenced back yard and concrete patio which provides a private retreat for entertaining or relaxing outdoors. You will find yourself in the heart of it all with close proximity shops, restaurants, schools, universities and major airports. An added hidden bonus is your access to Lake Osceola through 2 parks and walkway ramp, where you can enjoy a beautiful sunset or paddle board/kayak ride. With vintage character, and incredible location with lake access at the end of the street, this Winter Park gem is not to be missed!

311 Cortland Avenue, Winter Park

$480,000

3 Beds ⋅ 3 Baths ⋅ Indiana Place Condo SubDv. ⋅ 32789 Zip Code

Tucked away on a quiet street blocks from the cultural heartbeat of Winter Park is this 3-bedroom, 2.5-bath townhouse-style condo that offers a balance of comfort, convenience, and charm. With nearly 1,600 square feet of thoughtful space, the two-story home lives large, featuring an open-concept main floor with high ceilings, ceramic tile throughout, a spacious kitchen with granite counters and pantry, and a cozy living area complete with fireplace, built-ins—perfect for stashing your favorite reads, and French doors that provide natural light and flow out to your private patio. Upstairs, the spacious primary suite features a walk-out balcony, updated bathroom with an elegant shower, dual sinks, and a large walk-in closet, while two additional bedrooms give you flexibility for guests, family, or even a quiet home office. Recent updates like brand-new carpet, a 2018 A/C system, and a 2025 water heater offer peace of mind, and the attached two-car garage adds that rare, practical bonus. But what really makes this spot sing is its unbeatable location—you're less than two miles mile from Park Avenue’s boutiques and brunch spots, a quick ride to Rollins College, and just minutes to Mead Gardens, Leu Gardens, the Orlando Science Center, Winter Park Village, AdventHealth Hospital, College Park, I-4, and the SunRail Station for an easy commute downtown. Whether you're strolling to the Saturday Farmers' Market or grabbing coffee before class at Rollins, this place lets you be in the middle of it all—without sacrificing space or comfort. HOA fees are low, leasing is allowed, and pets are welcome. It’s easy living in one of Central Florida’s most beloved neighborhoods—where everything just feels...right.

1545 Indiana Avenue Unit B, Winter Park

$749,000

3 Beds ⋅ 3 Baths ⋅ Henkel Add SubDv. ⋅ 32789 Zip Code

Like new and totally turn-key! Built by award-winning Winter Park Custom Homes, coastal modern residence offers thoughtful design, high-end finishes, and an unbeatable location in Winter Park's coveted 32789 ZIP code. 3-bedroom, 2.5-bath home combines privacy with convenience. Minutes from Park Avenue, downtown Orlando and major local destinations. The home features authentic reclaimed European oak wood flooring throughout, 10-foot ceilings, and abundant natural light from a premium window and door package that frames garden and yard views. Open-concept floor plan flows through the main living area into a chef’s kitchen with marble countertops, backsplash, center island, Thermador gas range, walnut cabinetry, and custom millwork. Solid core 8’ doors, LED lighting, and a centralized On-Q AV closet with surround sound wiring. Recent updates include new Rejuvenation hardware throughout, freshly painted cabinets in the kitchen, laundry, mudroom and guest bath, a canopy installation at the kitchen entry, added storage solutions in the laundry and garage, interior painting and more. New grass and fence with gates installed. The primary suite features a spa-style bath with a large walk-in shower and soaking tub, and a generous walk-in closet. Additional features include custom window treatments, updated light fixtures, and mounted TVs in the living room and primary bedroom. Two more bedrooms upstairs with nicely sized closets and beautiful marble bathroom and shower/soaking tub. Built with long-term efficiency in mind, the home includes block construction, a concrete flat tile roof, spray foam insulation, Low-E glass, and custom metal Bahama shutters. The exterior has also been updated with new sod and fencing. Private garage, guest parking, security system and underground utilities. Close to highways, shopping, schools. Park Maitland, Lake Highland and public schools. No HOA! This home offers a rare opportunity to own a low-maintenance, design-forward residence in a prime Winter Park location with no detail overlooked. Furnishings can also be included upon request at a separate price. Move right in!

1429 Indiana Avenue, Winter Park

$780,000

2 Beds ⋅ 2 Baths ⋅ Cloisters Condo SubDv. ⋅ 32789 Zip Code

Experience unparalleled sophistication and tranquility with this extraordinary two-bedroom, two-bath condominium, boasting one of the rare and coveted water views in The Cloisters. Nestled on the serene shores of Lake Osceola, this residence offers a unique opportunity to enjoy stunning lake vistas that are available in only a small number of units within the complex. Spanning 1,351 square feet, this haven of light and serenity is designed to accentuate its breathtaking views. The primary suite is a harmonious retreat featuring an en-suite bath, a spacious dressing area with ample closet space, and potential for an added washer and dryer, ensuring both comfort and convenience. The separate kitchen opens to a generous living and dining area, offering picturesque views of glistening Lake Osceola – perfect for intimate gatherings or quiet evenings at home. More than just a place to call home, this condominium is a gateway to a lifestyle of elegance and ease. Exclusive amenities such as covered parking with a dedicated space conveniently close to the elevator, enhance the living experience. Additionally, boat docks, a gym, and an elegant community room within the complex provide leisure options. Managed expertly by FirstService Residential, this property promises a seamless and harmonious living experience. Located just steps from the vibrant shopping and dining of Park Avenue, the charm of Winter Park Village, nearby fitness centers, and the intellectual allure of Rollins College, this home places you at the center of Winter Park's most coveted attractions. Embrace the rare opportunity to own a unit with one of the most desirable water views in The Cloisters. Schedule your private viewing today and discover how this exceptional residence can become your canvas for an extraordinary life.

106 S Interlachen Avenue Unit 317, Winter Park

$765,000

3 Beds ⋅ 3 Baths ⋅ Canton Ave Cottages 1 SubDv. ⋅ 32789 Zip Code

BACK ON MARKET WITH NEW PRICE DUE TO BUYERS CASH PURCHASE DEFAULT!!!Rare find in the heart of Historic West Winter Park - Newer 2017 solid built David Weekley home now available! This modern designed chic home offers energy efficient features with luxury design. Walk into the home and be impressed by the voluminous ceilings and 8' door frames adorned with ceiling crown molding. This unique home design offers ultimate privacy with all bedrooms on the lower floor while the living/entertaining space is upstairs. Windows throughout the home filtrate a natural light that compliment the wooden floors. Upstairs you'll find the living space large and inviting. The chef's kitchen is spacious with abundant cabinetry and offers all stainless-steel Jenn Air appliances. The commercial style gas cooktop offers a wall mounted kettle water feature along with a flat surface griddle and is topped with a deco canopy range hood. The built-in bottom mount refrigerator is complimented alongside the programmable electric oven and convection/microwave. Center kitchen island doubles as dining space with room for four or there's room for a dining table. Solid wood cabinets are topped with glass doors to display stylish dinnerware. Dual pantry sliders with pull out drawers adjoin the wine refrigerator (Jenn Air of course) with additional cabinets. The Great Room's sliding glass doors welcomes you outside to the expansive maintenance free Hardee board deck. The deck is pre-plumbed for both water and gas to complete your grilling needs. The luxurious primary bedroom offers a tray ceiling and large walk-in closet. Venture into the impeccable primary bath and enjoy the huge walk in shower with built-in bench seat and overhead rain and wall mount shower heads. The additional two bedrooms share a bathroom accessible by each side but has a separate door to shower and toilet. The downstairs enormous laundry room is complete with a sink and additional cabinets. You'll find the garage oversized and can be described as 2.5 car size with epoxy coated flooring and an EV charger. Water Softner system stays - easy to use! There's an additional parking pad for your guests. The home is completely fenced and has energy efficient dual tankless gas water heaters and is prewired for 5.1 Surround sound audio. Best part of this small brick paved urban planned community - HOA pays for landscaping maintenance, plant replacement, mulch and sprinkler repair and you're connected to a natural gas utility service. Walk to the best shopping and dining available in Central Florida - Park Ave. and Winter Park Village. The Sunrail and Amtrak train depot is only 6 blocks away with Rollins College right around the corner. Easy commute to Downtown Orlando, Full Sail University and the Orlando International Airport. Best value in 32789 zip code!!! Call today for your showing.

441 N Capen Avenue, Winter Park

$1,186,200

5 Beds ⋅ 4 Baths ⋅ Timberlane SubDv. ⋅ 32789 Zip Code

This home is the perfect blend of resort luxury and farmhouse charm, with high-end finishes and features that cater to both relaxation and entertaining. From the resort-style backyard with a magnificent Saltwater Pool, lovely green space around the koi pond to the HGTV-worthy Interior with an entertainer’s dream kitchen, this has it all. The spacious split-bedroom floor plan, luxurious primary suite, and thoughtfully designed storage make it both stunning and practical. The large lanai with fireplace and full wet bar, beautifully landscaped fenced in yard, pond, green space and even storage for your boat, outdoor toys or dog run—every detail seems meticulously planned to maximize comfort and style. It’s clear that this home was built for the love of hosting, relaxing, and living life to the fullest. 5 Bedroom, 4 Bath, Pool Home with 2-Car Garage (NEW Genie Garage Door Opener). Long pavered driveway with plenty of room for all of your vehicles. You can't help fall in love with this Fully Renovated Florida Ranch Home. Walk into the impeccable warm and welcoming split Bedroom floor plan that offers a spacious Primary Bedroom in the rear of the home with beautifully updated Primary Bath. Double Vanity, Granite countertop, Chocolate Brown Cabinets, Tiled Walk-in Shower with Frameless Glass Doors. Two closets in Primary, one walk-in and one reach-in closet. Both front bedrooms are En-Suites. Bedrooms 4 and 5 share hall bathroom with tub and shower. If you are a chef or just a foodie you won’t want to leave this Ultimate Gourmet Kitchen. Zline 6-Burner, Griddle, Professional grade gas range with double electric oven and Zline wall mounted range hood. Dishwasher, two stainless steel farm sinks, wall-mount pot filler, microwave oven and French Door Refrigerator. White Shaker Soft Close, Kitchen Cabinets with Black hardware and high-end granite countertops, adorned by Designer Stone Backsplash. Behind the custom-built barn doors is the laundry closet and pantry. The large 7.9 x 5.3 Island seats 6 comfortably. This Dining Room is meant for entertaining. Seats 10-12 comfortably with sideboard, bar hutch and more. Open the French doors and instantly double your hosting space. Living Room is warm and cozy with wood burning fireplace, built-ins, LED recessed lighting. Flooring throughout is porcelain wood-look tile. Looking for a home with storage, this home has custom built-in cabinets in 2 bedrooms and hallway. You'll be amazed how much you can store. If you enjoy outdoor living and entertaining, you’ll never want to leave home. Step outside to a spacious covered lanai with tongue and groove ceiling, wood plank flooring, fireplace, TV and surround sound speakers. Full wet bar, lower stone encased with granite tops. Porch Swing. Fence has double gate on left side of home so you can easily pull your boat, RV or extend this into more garage area. Enjoy the mature Florida landscape as you sit by the pool and bar enjoying your favorite team on the TV with your friends. Pool remarcited and tiled in 2022. New pool equipment 2023, Pool Shed is to the right of the house behind the bar to hold all of your pool supplies. New HVAC 2023. Compressor 2020. Roof was replaced in 2018, house was replumbed and rewired in 2020. All Double Pane Aluminum Windows throughout home.

2105 Fosgate Drive, Winter Park

$575,000

2 Beds ⋅ 1 Baths ⋅ Dixie Terrace SubDv. ⋅ 32789 Zip Code

This charming “old Florida” bungalow in the heart of Winter Park offers the perfect blend of comfort and convenience, nestled in a prime location on a brick lined street just moments from world-class shopping and dining on famous Park Avenue. In addition, it is a short walk to both The Winter Park Village and Whole Foods. The warm and inviting interior of this home exudes character with original hardwood flooring in the spacious living room as well as both bedrooms. The hall bathroom has been updated with a new vanity, granite countertop, and marble tile. The well-appointed kitchen has Italian travertine flooring, Shaker-style 42" wood cabinets, granite countertops with an under-mount sink bowl, and beautiful stainless-steel appliances. Just off the kitchen is a cozy dining room which is perfect for family gatherings. New roof in (2021) and a 1 car garage! The property is zoned for top rated Lakemont Elementary, Maitland Middle, and Winter Park High School. Surrounded by Muti-Million Dollar homes this is a rare opportunity to move in now and wait for future appreciation, add on, or maximize the value of the land and build your dream home. The homes proximity to The Winter Park Cultural Corridor which includes Rollins College, The Morse Museum, The Scenic Boat Tour, and The Farmer’s Market make this a most sought-after location. Schedule your private showing today!

1230 N Denning Drive, Winter Park

$362,500

1 Beds ⋅ 1 Baths ⋅ Phillips Circle Rep SubDv. ⋅ 32789 Zip Code

Priced to sell!! Motivated Seller. Outstanding structural integrity, no big assessments ahead! Whispering Waters passed its structural integrity inspection and reserves study with flying colors—earning compliments for the quality and care of the buildings. This is a very well-managed community, and the $1,054 monthly HOA covers nearly everything, including electricity! The only exception is cable and internet, making this an incredible value with true peace of mind. Tucked away just two blocks from Park Avenue, this one bedroom, one bathroom corner unit places you in the heart of downtown Winter Park—steps from acclaimed restaurants, charming shops, and the iconic boat tour on Lake Osceola. Situated on the second floor of Building 6 with convenient elevator access, this light filled condo has brand new carpet in the living areas and bedroom, creating a fresh and cozy feel. The kitchen features granite countertops, a built-in oven, glass cooktop, stainless steel refrigerator, and recently painted blue, solid wood cabinetry that adds a fun pop of color to the space. A dedicated dining area is located just off the kitchen and includes sliding glass doors that open to a small private balcony overlooking Morse Blvd—perfect for enjoying your morning coffee. Off the living room, an enclosed sunroom offers bonus living space with abundant natural light, motorized custom blinds, and upgraded windows for improved energy efficiency and sound insulation. The oversized bedroom offers space for a sitting area and features motorized shades for added comfort and privacy. A convenient door allows you to close off the bedroom —ideal for when guests are visiting and need access to the bathroom without entering the bedroom. The unit also comes with one assigned parking space in the garage, additional storage, and the peace of mind that HOA covers electric, water, sewer, trash, building insurance, pool maintenance, landscaping, and on-site management. Whispering Waters is a lakefront community on beautiful Lake Osceola, with water access available to residents—bring your kayak, soak in the serene views, or enjoy a sunset by the water. Whether you're seeking a full-time residence or a part-time getaway, this home offers effortless, low-maintenance living—just lock and leave. Bonus: Since the current owner is under 55, the next buyer can be too (only 85% of residents need to meet the 55+ age requirement). Call today to schedule your private showing!

311 E Morse Boulevard Unit 6-7, Winter Park

$540,000

2 Beds ⋅ 2 Baths ⋅ Cloisters Condo SubDv. ⋅ 32789 Zip Code

Situated in a prime location, this condominium presents an excellent opportunity for customization and renovation. Sold as-is, this residence offers a spacious layout with ample potential to reimagine its interiors to suit modern living. Positioned within The Cloisters sought-after community, residents enjoy access to desirable amenities and a convenient setting near shopping, dining, and local attractions. A rare chance to transform and tailor a space to individual preferences.

100 S Interlachen Avenue Unit 415, Winter Park

$4,500,000

6 Beds ⋅ 6 Baths ⋅ Killarney Point SubDv. ⋅ 32789 Zip Code

"The Point House" on lake Killarney. Rarely available oasis, this spectacular lake front residence is positioned on a peninsula with .90 acres and over 440+ feet of lake frontage with unobstructed lake views to the south, west and east. Constructed in 2012, this home features 6,000 living square footage (3,977 on the 1st level / 1,950 on the 2nd level), 4,000 sq. ft. of outdoor space, elevator, infinity pool, boat house and tennis court. Main level offers 35 x 32 great room w/kitchen and dining, a separate dining area, 36 x 20 family room with bar/wine room, 4 bedrooms/ 3.5 baths, laundry room and 4 multi slider panel doors that open to wrap around patio with outdoor kitchen. 2nd floor offers a 2nd laundry room, lofted library, guest bedroom and primary bedroom with suite/lounge/built in wet bar and additional 4 multi slide panel doors that open to a wrap around balcony. Experience the serenity and tranquility of old Florida under the majestic cypress trees beaming with wildlife/eagles/beavers and the ever changing landscape from sunrise to sunset.

2118 Lake Drive, Winter Park

$835,000

4 Beds ⋅ 2 Baths ⋅ Kenilworth Shores Sec 06 SubDv. ⋅ 32789 Zip Code

Completely remodeled, coastal-inspired home is located in the highly sought-after Winter Park neighborhood of Kenilworth Shores in Winter Park 32789. Minutes from the world-renowned Park Avenue and upscale shopping, dining, parks, community events, Sunrail and more lifestyle. The home is zoned for some of Winter Park's most desirable schools, including Brookshire Elementary, Glenridge Middle, and Winter Park High School. This home is a true gem, meticulously and completely remodeled for a coastal feel that blends modern elegance with comfort. Featuring 4 spacious bedrooms + office, the residence is designed to impress. The entry showcases a custom, German-made solid front door that opens into a bright, airy living space with engineered wood floors throughout. The raised ceilings enhance the sense of openness, complemented by beautiful wood beams that add character to the home. A shiplap-clad eat-in area creates a charming focal point, while the kitchen is equipped with premium Badger Woodworks self-closing cabinetry, gorgeous granite countertops, and new appliances including espresso bar and wine fridge. No detail has been overlooked in this home, with recent upgrades including a new HVAC system and ductwork in 2024, as well as completely updated plumbing, windows, and light fixtures. Replumbed with Pex piping in 2015. The walls have been professionally retextured, and the home also offers the convenience of an interior laundry room and brand new barn door. Outside, the covered porch provides the perfect space for entertaining, with the hot tub conveys for relaxation. The outdoor bar showcases a custom millwork bar with a grill, kegerator, and fountain, ideal for hosting gatherings. A shed on a concrete slab and a workshop area in the garage offer ample storage and workspace. The property is fully fenced, ensuring privacy and security. 625 Worthington home is located in the heart of Winter Park, home to Rollins College, one of America's top-ranked liberal arts colleges. With its prime location, luxury finishes, and family-friendly neighborhood, this home offers an exceptional living experience in one of Central Florida’s most desirable areas. With the neighborhood rapidly evolving, many homes around this property are being torn down to make way for new, custom-built estates, including expansive 4,000 square foot homes valued at over $3 million.

625 Worthington Drive, Winter Park

$685,000

2 Beds ⋅ 2 Baths ⋅ Cloisters Condo SubDv. ⋅ 32789 Zip Code

Experience a lifestyle of refined sophistication and effortless tranquility at The Cloisters Condominium, ideally between Park Avenue and the serene shores of Lake Osceola. This exquisitely remodeled residence offers a seamless blend of timeless elegance and thoughtful design. Set on the second floor, this sun-drenched retreat is bathed in natural light from its northeast-facing sunroom, where expansive windows frame picturesque views of the lush gardens and pool, creating an inviting ambiance throughout the living space. Rich wood floors flow gracefully through the open layout, enhancing the home’s warm and sophisticated character. The primary suite is a private haven, featuring custom-built cabinetry and drawers, a dressing area with abundant closet space and a beautifully updated en-suite bath. A dedicated laundry closet with a built-in washer and dryer adds everyday convenience. The second bedroom offers a custom-built office setup and dual access from the hall and living area, providing effortless versatility as a bedroom, sitting room or private study. The Cloisters offers an array of exclusive amenities designed to elevate everyday living. Guest parking is immediately below the unit in the forward parking circle, as well as along Morse Boulevard, ensuring seamless accessibility for visitors. Additional perks include an assigned covered parking space near the elevator, a dock with boat slips available for lease, two well-appointed fitness rooms, and a beautifully redesigned community space featuring a newly remodeled kitchen and bath. Just steps from the vibrant energy of Park Avenue, this exceptional home provides unparalleled access to fine dining, boutique shopping, cultural attractions, fitness centers and the distinguished Rollins College. Every detail has been carefully curated to create an extraordinary living experience in the heart of Winter Park. Seize this rare opportunity to own a desirable residence at The Cloisters, schedule your private tour today and embrace a home where elegance meets effortless living.

100 S Interlachen Avenue Unit 203, Winter Park

$675,000

4 Beds ⋅ 3 Baths ⋅ Carver Town First Add SubDv. ⋅ 32789 Zip Code

This stunning property in historic Winter Park offers an excellent price point and is ideally situated near Park Avenue’s shops and restaurants, Rollins College, Winter Park Village, Winter Park Farmer's Market, and Hannibal Square. Completely renovated in 2021, this 4 bedroom, 3 bathroom home has been thoughtfully appointed with double primary suites, each with ensuite bathrooms and large closets. Split from these primary suites are 2 additional ample sized bedrooms and a full bathroom. The open floor plan boasts contemporary updates throughout, including light wood-like tile floors, LED recessed lighting and fresh paint. The kitchen is a chef's dream, featuring quartz countertops, a designer tile backsplash, stainless steel appliances, and a 5-burner gas stove complete with a pot filler. The primary ensuite bathroom is a luxurious retreat, showcasing dual vanities, an oversized tiled shower with multiple shower heads, and a built-in bench. The bathrooms are bright and fresh with contemporary black and white tile accents. Enjoy an expansive back yard with a large paved patio, perfect for entertaining. This home can also serve as an excellent investment opportunity for your Rollins student! Schedule your private showing today! HVAC - 2017 ROOF - 2021

678 Depugh Street, Winter Park

$500,000

3 Beds ⋅ 1 Baths ⋅ Lake Monte Sub SubDv. ⋅ 32789 Zip Code

HUGE PRICE ADJUSTMENT...NEARLY $100K!! Owner Is Highly Motivated and Ready To Work With You! This charming Winter Park Bungalow is centrally located in a highly desired area of Winter Park (32789) and is Ready for Immediate Occupancy! Featuring 3 full bedrooms, one bathroom, nearly 1,150 sqft of living area, a covered carport and storage rooms. Beautifully updated and maintained throughout the years with vintage style hardwood flooring which flows throughout. The renovated kitchen is sure to impress with modern 42-inch cabinets, granite countertops, stainless steel appliances and update hardware and finishes. The freshly painted interior and exterior makes this home feel “like new” again. Newer paddle fans and lighting fixtures have been added throughout the interior. This is the ideal opportunity for an investor looking to build new, a first-time home buyer or even a downsizing buyer. Setback nicely on a quiet, tree-lined street with a very spacious fenced back yard area that offers plenty of room for an outdoor living area, new pool and/or an additional dwelling or storage. Simply traditional Winter Park at its best! Conveniently located just moments from Winter Park shopping and fine dining, multiple grocery stores, beautiful parks, gyms, entertainment, hospitals, as well as A+ rated Winter Parks schools. Come and see for yourself before its gone! Act Now!

1810 Hollywood Avenue, Winter Park

$329,900

2 Beds ⋅ 1 Baths ⋅ Village Condo SubDv. ⋅ 32789 Zip Code

One or more photo(s) has been virtually staged. Location.... Location.... Location.... First Floor Condo situated in the heart of Winter Park and walking distance to Park Avenue, Rollins College, Winter Park Village and Sun Rail. The condo has been recently renovated with new appliances, led lighting, wood, tile, and stone finishes and there are NO units above this one. You have access to a "new" private deck just right outside the unit back door to just relax and enjoy a quiet evening. No Condominium Assessments and All Major Building Components/Projects (Roof, Fencing, Driveway, Landscaping, Lighting, Painting) have been completed Within the Last 7 Years! This home is "wireless" from the doorbell to the electrical switches and ceiling lights which can be dimmed for a relaxing mood. It is set up on a Google Home Platform and can be controlled remotely. A nest thermostat, doorbell and a state of the art wireless Blue ADT alarm system that is self-monitored with backup capabilities to ensure notifications of events. There is a new all-in-one washer/dryer for a one-time load and done. The unlimited hot water system maintains constant temperature based on your convenient and easy dial setting and comfort. The kitchen has modern track lighting and granite counters. Custom white plantation shutters and crown molding throughout the home. There is one assigned parking space with ample parking for another vehicle and guest parking. The location in Winter Park is ideal and is located near the police and fire station. This home has everything you need to enjoy the Winter Park lifestyle and cultural events.

500 N Pennsylvania Avenue Unit E, Winter Park

$520,000

2 Beds ⋅ 1 Baths ⋅ Cloisters Condo SubDv. ⋅ 32789 Zip Code

Welcome to The Cloisters Condominiums, a sanctuary nestled between the serene Winter Park Chain of Lakes and the vibrant Park Avenue. This sophisticated condominium embodies the essence of Winter Park living, offering a perfect blend of elegance and convenience. As a resident, you'll enjoy a sought-after address that places you in the heart of this charming locale. This refined fourth-floor residence spans over 900 square feet and features two spacious bedrooms and one full bath. The moment you enter, you are greeted by a charming foyer that seamlessly connects to a well-appointed kitchen. Here, you will find stainless steel appliances, ample counter space, and abundant cabinetry, making it a dream for any culinary enthusiast. The inviting living area extends an open invitation to relax on the oversized balcony, covered in lush astroturf, where you can unwind while taking in the tranquil, scenic views. The Cloisters offers an array of amenities designed for the connoisseur of life. Enjoy leisurely days by the heated pool, surrounded by meticulously maintained grounds, or entertain in the social room. For boating enthusiasts, a boat dock with eight slips provides direct access to the picturesque Lake Osceola. Golfers can refine their skills on the private putting green. This exceptional home is just a short stroll from Park Avenue, where you can explore an array of dining and shopping options. Whether you prefer to meander through Hannibal Square or embark on a serene boat ride along the Winter Park Chain of Lakes, this location offers a lifestyle of sophistication and convenience. Notable features include European white oak wide-plank flooring, Carrera marble porcelain tile in the bath, new Kohler bath fixtures, designer light fixtures throughout, plantation shutters, and a Lutron system for select lights, all combining to create a harmonious living space. For the discerning buyer, The Cloisters offers a unique opportunity to experience the art of living in a serene yet connected environment. This is more than just a home – it's a statement of refined living. The condominium fee covers cable TV, common area taxes, an escrow reserves fund, building insurance, internet, maintenance (grounds, exterior, repairs, pool), a condominium association manager, sewer, trash collection, and water, ensuring a maintenance-free lifestyle.

100 S Interlachen Avenue Unit 410, Winter Park

$1,730,000

4 Beds ⋅ 4 Baths ⋅ Fontainebleau SubDv. ⋅ 32789 Zip Code

Presenting an extraordinary custom traditional home crafted by esteemed builder George Driscoll. Situated on Place Vendome, this remarkable property impresses from the moment you arrive. The bricked drive seamlessly continuing into the garage sets the stage for timeless elegance. Boasting four bedrooms and three and a half baths, including a pool bath, this spacious home offers refined living. Spanning approximately 4,049 square feet under air, this residence provides ample space for comfort and relaxation. As the first and only owners, meticulous care and attention to detail are evident throughout. Step through the inviting entryway and experience the artistry of this exceptional home. The primary living spaces, including the family room and living room, exude warmth and sophistication, setting the stage for memorable gatherings. Adjacent to the garage, a mudroom and laundry room combination connects the kitchen, featuring Wolf, Sub-Zero, and Bosch appliances, as well as a dinette and breakfast bar, creating a seamless flow for everyday living. Retreat to the luxurious primary suite, complete with an updated bath and a spacious walk-in closet. From the primary bed, enjoy enchanting views of the pool, creating a serene sanctuary for relaxation. An elegant office space provides a tranquil setting for work or study. Ascend to the second floor, where a versatile living space beckons. Here, a wet bar complements the entertainment possibilities, while a hidden doorway leads to a hallway connecting the areas near the wet bar to the exclusive theater room, enhancing the cinematic experience. Three additional bedrooms offer comfort and privacy, with two bedrooms conveniently sharing a Jack and Jill bath. All bedroom closets are thoughtfully built out to optimize storage and organization. Stepping outside, the motorized screen-enclosed lanai invites you to embrace the Florida lifestyle. The resurfaced heated pool, adorned with beautiful stone accents, includes an integrated jacuzzi for ultimate relaxation. The fully fenced yard provides an expansive and secure space for pets to roam freely. This exceptional property offers an exquisite place to call home with convenient access to the Winter Park Racquet Club, Park Avenue, Maitland, and the picturesque Chain of Lakes.

1350 Place Vendome, Winter Park

$375,000

3 Beds ⋅ 2 Baths ⋅ Glencoe Sub SubDv. ⋅ 32789 Zip Code

Welcome to this charming 3-bedroom, 2-bathroom home located at 2541 Roxbury Road in the heart of Winter Park, FL. This beautifully maintained property features abundant natural light, highlighting the spacious living areas. The kitchen offers stainless steel appliances, and ample storage, making it perfect for both everyday living and entertaining. The master suite offers a tranquil retreat with an en-suite bathroom and walk-in closet. Enjoy outdoor living in the private, fenced backyard with a patio area ideal for relaxing or hosting gatherings and perfect for your lovable pets. NO HOA! Featuring a pavered front porch and a long driveway, this home offers plenty of space perfect for parking your toys and more. Conveniently located near top-rated schools, shopping, dining, entertainment, hospitals, I4, downtown Orlando, Winter Park Village, Park Ave, Mills50, College Park and just a quick step to Lake Killarney this home provides easy access to everything Winter Park has to offer. Don’t miss the opportunity to make this wonderful property your new home.

2541 Roxbury Rd, Winter Park

$190,000

2 Beds ⋅ 1 Baths ⋅ Aragon Condo SubDv. ⋅ 32789 Zip Code

Welcome to this inviting first-floor unit in the desirable Aragon Condo community, located in the heart of Winter Park. This charming two-bedroom, one-bath condominium features a newly remodeled bath, fresh paint, and all-new luxury vinyl plank flooring throughout, making it ready for its new owner. The galley-style kitchen seamlessly flows into the open living and dining space, perfect for entertaining or relaxing. Both bedrooms offer built-in closets, providing ample storage space. Additionally, there is a hall closet ideal for linens or extra storage. The unit includes a cozy front patio area, perfect for enjoying your morning coffee or evening unwind. Residents of Aragon Condo enjoy a range of amenities, including a central courtyard, sparkling pool, communal laundry facilities, and both assigned and guest parking. This prime location is convenient to multiple shopping centers and is just across the street from a variety of restaurants, quick-serve options, grocery stores, and retail shops. Experience sophisticated living in a community that embodies the art of the home, offering both tranquility and convenience. This condominium is not just a home, it is a haven for those who appreciate the finer things in life.

851 Miles Avenue Unit 3, Winter Park

$330,000

2 Beds ⋅ 1 Baths ⋅ Karolina On Killarney SubDv. ⋅ 32789 Zip Code

Cute, clean, and convenient, located in Winter Park just off of Fairbanks near I-4. This lovely home features a remodeled kitchen and bath, refinished original wood floors, new doors, ceiling fans. Spacious living room and eat-in kitchen with plenty of storage. One car garage has laundry hook up. Oversized, fenced yard. Roomy porches at the back and front of home. Winter Park shopping and entertainment all just minutes away! New roof in 2022.

1987 Karolina Avenue, Winter Park

$445,000

2 Beds ⋅ 1 Baths ⋅ Carver Town SubDv. ⋅ 32789 Zip Code

Discover the charm of easy downtown living in this thoughtfully remodeled two-bedroom home located in the vibrant heart of Winter Park. This delightful residence features an expansive study, which can easily be transformed into a third bedroom, offering flexibility to suit your needs. In 2019, this home underwent a comprehensive renovation, which included updates to the flooring, fresh paint throughout, and the installation of modern, energy-efficient windows. The HVAC system and insulation were completely replaced, ensuring comfort year-round. The heart of the home, the kitchen, was fully remodeled with contemporary fixtures and fittings, alongside a redesigned bath and a convenient interior washer/dryer setup. Step outside into the fenced backyard, where fresh landscaping creates a serene environment perfect for relaxation or hosting gatherings under the Florida sun. The property's prime location places you just a short stroll from the boutique shops of Park Avenue, the cultural charm of Hannibal Square, the trendy spots in Winter Park Village, and the esteemed Rollins College. Ideal for those who value the blend of modern updates and prime location, this home offers an excellent opportunity to enjoy the best of downtown Winter Park living without the luxury price tag.

678 W Webster Avenue, Winter Park

$290,000

2 Beds ⋅ 1 Baths ⋅ Village Condos SubDv. ⋅ 32789 Zip Code

Step into comfort and convenience with this delightful upstairs residence in the highly sought-after Village Condominiums. Positioned perfectly in a neighborly setting, this gem is only a short, pleasant walk from Park Avenue and the lively Winter Park Village, ensuring you're never far from boutique shopping, dining, and entertainment. Unit G offers a tranquil, inviting atmosphere with its exclusive upper-level location and limited sharing of space, promoting a private and serene living environment. You'll appreciate the ease of access to major routes such as I-4 and 17/92, which make commuting straightforward and stress-free. Inside, each room is bathed in natural light through charming plantation shutters. Warm laminate flooring and elegant crown molding enhance the welcoming ambiance. Everyday conveniences are covered with an in-unit washer and dryer and a kitchen equipped with stainless steel appliances, granite countertops, and a practical breakfast bar. A closet pantry keeps essentials organized and within easy reach. The two bedrooms are crafted with individual character, the main bedroom features a spacious walk-in closet, while the second bedroom offers direct access to the communal patios—a collection of cozy spots perfect for socializing, enjoying the outdoors, or unwinding in the quaint courtyard seating areas. Living in Village Condominiums means embracing an effortless lifestyle where everything you need is just a stroll away. Whether it's exploring Hannibal Square, picking up groceries at Whole Foods, playing a round at Winter Park Golf Course, or enjoying a leisurely day of shopping and dining, this location truly has it all. Discover your urban sanctuary at Village Condominiums, where comfort meets convenience in a friendly community setting. Welcome to your new home, where every day feels like a walk in the park.

500 N Pennsylvania Avenue Unit G, Winter Park

$350,000

2 Beds ⋅ 2 Baths ⋅ Fairbanks Shores 4th Add SubDv. ⋅ 32789 Zip Code

Welcome to your own peaceful paradise! Step into this charming, partially-renovated, pool home and discover the ultimate oasis in Florida living. Boasting 2 bedrooms and 2 full bathrooms, this home invites you to experience privacy and quiet living at every turn. With fresh interior paint, recently renovated bathrooms, an updated kitchen, and spacious living and dining areas, entertaining has never been easier. Take your enjoyment outdoors with a modern heated pool, perfect for cooling off on those sunny summer days. And when you need a break from the sun, retreat to the tranquility of the large, fully enclosed sunroom with eco-friendly windows and screens for year-round enjoyment. This property offers more than just relaxation—it's practical too. With a one-car garage and expanded driveway with brick pavers, there is ample parking. Built with solid concrete block structure and hurricane shutters on all windows, you'll have peace of mind year-round, no matter the weather conditions. No HOA makes this property ideal for pet owners and garden enthusiasts alike. Let your furry friends roam freely in the fenced yard on nearly 1/5th of an acre lot, while you take advantage of the ample outdoor space. Conveniently located in the highly sought-after Winter Park suburb of Orlando, this home puts you just minutes away from I-4, downtown Orlando, the Kia Center, Camping World Stadium, College Park, and Universal Studios theme park. Don't miss your chance to experience the epitome of Florida living—schedule your showing today!

2877 Euston Road, Winter Park

$525,000

1 Beds ⋅ 1 Baths ⋅ Whispering Waters Apartments Condo A SubDv. ⋅ 32789 Zip Code

This remarkable condo exudes grace and elegance with a distinct style that lends itself to the downtown Winter Park Living. Completely renovated ( to the studs) in 2022. Gorgeous kitchen with oversized island, counter seating, high end Bosch appliances, gorgeous cabinetry, luminescent quartz counters, refined lighting and unique materials. Beautiful bath with top of the line fixtures. Primary bedroom has two closets and a separate niche for office or reading. New flooring, new windows, new doors, new plumbing, new electrical, new ac, new washer and dryer. The oversized dining room also offers a lot of options to incorporate office or second seating area. New doors open to inviting screen porch. Whispering waters offers underground parking ( one dedicated space) , storage, a sunny pool, and lakefront patio area. Best of all this fabulous turn key property is a short stroll to famed Park avenue shops and Restaurants. Please note that condo fee includes all utilities .

311 E Morse Boulevard Unit 6-8, Winter Park

$835,000

3 Beds ⋅ 3 Baths ⋅ Conwill Estates SubDv. ⋅ 32789 Zip Code

Incredible opportunity to own over a quarter of an acre pool home in the heart of Winter Park. Walking distance to Phelps Park, Winter Park YMCA, and Lakemont Elementary. and less than 10 minutes to Park Avenue. This charming 3 bedroom 3 bathroom ranch home on a quiet tree lined street boasts over 2000 sq ft of living space with stunning windows and charming features throughout. Upon entering the home you are greeted by a spacious living room and dining area. An elongated kitchen sits at the heart of the home equipped with stainless steel appliances and solid wood cabinets. Another large living space off the kitchen area welcomes you with custom built in shelves, a charming wood burning fireplace and a timeless crafted window overlooking the crystal blue pool and mature landscaped backyard views. A large screened in patio provides year round outdoor space for you to enjoy. The backyard oasis is immaculate with fruit trees, lush landscaping and an incredible pool with heated spa for you to live your best Florida life. Upgrades include a brand new pool heater and regulator, a freshly refinished pool and stunning pavers around the pool and main driveway. Home was repiped with pex in 2003. The Hvac is 2015. The skylight and flat roof is 2016. Main roof is 2003.

1771 Chestnut Avenue, Winter Park

$312,000

1 Beds ⋅ 1 Baths ⋅ Virginia Heights Condo SubDv. ⋅ 32789 Zip Code

Nestled in the heart of Winter Park, Florida, 1312 S. Pennsylvania exudes a sense of cozy charm and great privacy. This standalone one-bedroom, one-bathroom condo offers a cozy retreat filled with natural light that dances through the windows. Property has been beautifully kept with thoughtfully updated finishes. There is a fun private patio perfect for that first cup of coffee for the day. The house is a part of a condo association but is detached from other units with a personal carport belonging to the residence. Perfectly situated just steps away from the lively pulse of highly desired Winter Park, you'll find yourself immersed in the vibrant energy of all the city has to offer. From the prestigious Rollins College to the upscale boutiques and dining options on Park Avenue, the lively community of Baldwin Park, and the serene beauty of Mead Gardens, every convenience and attraction is within reach. This is one not to be missed, it will go fast. Reach out for your private showing today.

1312 S Pennsylvania Avenue Unit 1, Winter Park

$256,000

2 Beds ⋅ 2 Baths ⋅ Mead Garden SubDv. ⋅ 32789 Zip Code

Stunning Winter Park first floor condo of 2 bedrooms and 2 baths. Open floor plan with laminate flooring and tile throughout – no carpet. New double paned and low-e windows. New Quartz kitchen countertops to complement new stainless steel sink and appliances including dishwasher, range and refrigerator. Freshly painted. Sit out and relax on your covered screened back porch which is facing the lovely garden or take a dip in the heated community pool just steps away. Laundry facility is next to the pool. Dedicated bike storage, as well as a 3 cubit feet storage area for each unit. Roof for the whole complex is less than 2 years old. Ample parking spaces. Condo fee is $375.00 per month for such perfect carefree living! Great location close to Orange Avenue, Park Avenue, Mead Garden, Rollins College, Publix, Trader Joe's, Winter Park Village, Winter Park Library, Saturday Winter Park Farmer's Market, and all downtown Winter Park has to offer. Zoned for great school district of Audubon Park K-8 and Winter Park High School. No dogs allowed except domestic cats. These first-floor units are hard to come by. Where can you find a first-floor condo unit in the heart of Winter Park for $262,000.00? Don’t wait!

1250 S Denning Drive Unit 111, Winter Park

$615,000

2 Beds ⋅ 3 Baths ⋅ Villa Del Seis Condo SubDv. ⋅ 32789 Zip Code

Welcome to **Villa del Seis**, a charming group of 6 condos in the heart of **Winter Park!** Unwind in your 2 bedroom condo with access to Lake Virginia!! The views are breathtaking!! Relax in the sun while fishing or entertaining lakeside from your community dock.!! This light and bright **end unit town home** is a must see. The living room has a cozy **wood burning fireplace** and two-story ceiling with a skylight and French doors that lead out to the back lanai. The Dining room opens to the living room and overlooks this charming **outdoor oasis**. There is an **attached one-car garage** plus **extra parking** for guests. Enjoy a wonderful large master suite with **remolded bath** plus private second bedroom suite. Walk to Park Avenue's fabulous restaurants, wine shops, boutiques, Saturday's Farmers' market, Rollins College, The Alfond Inn and Spa, Mead Gardens, and Sunrail Station!! Location, location, location!! The Lush landscaping is the responsibility of the Association as well as the exterior maintenance of your unit making it easy to enjoy as a **primary or secondary residence**. This gem of a property will not last long! Schedule a private showing today!

670 Osceola Avenue Unit 670, Winter Park

$525,900

4 Beds ⋅ 2 Baths ⋅ Lake Forest Park SubDv. ⋅ 32789 Zip Code

INVESTMENT OPPORTUNITY! - Amazing lot in the desirable Winter Park community of Lake Forest Park. Renovate and Add to the existing structure or start over with a new home build! Original home featured 3 Bedrooms and 1 Bath. Garage Apt. add on features two additional rooms with full bath. .21 Acre lot contains plenty of space for a larger home or pool. This incredible Winter Park Location, across the St. from Lake Forest, is near many other lots that have been repurposed with new high value homes built on them. Walk to Corrine Drive for lunch or skip over to Park Avenue on your bike. The quaint Lake Forest Park neighborhood features beautiful mature landscaping with towering oaks and foliage throughout. Don't miss out on this amazing opportunity to own your piece of historic Winter Park.

2228 Howard Drive, Winter Park

$500,000

5 Beds ⋅ 5 Baths ⋅ Glencoe Sub SubDv. ⋅ 32789 Zip Code

Discover the allure of Winter Park living with this charming 5edroom, 5-bathroom home, 50K priced below appraisal for exceptional value. Offering a cozy and classic style, this residence presents a canvas ripe for your personal touch. With over 2800 square feet of living space, the possibilities are endless. This Winter Park gem boasts two separate suites, each with private entrances, ideal for versatile use as a home office, teenager's retreat, or even your own private art studio. Complete with kitchenettes and private baths, these suites provide flexibility to accommodate your unique lifestyle needs. Rest easy knowing the home's foundation is solid, featuring a newer roof and septic tanks that bring peace of mind. Whether you envision a multi-generational living arrangement or seek lucrative rental opportunities, this property offers endless potential. Step outside to the screened enclosed covered patio and soak in the serene views of the expansive backyard. Situated near quaint shopping and dining destinations, as well as convenient access to Interstate, shopping, dining, and local attractions, this home epitomizes the quintessential Winter Park lifestyle. Experience the best of Florida living in this inviting abode with endless possibilities.

2500 Euston Road, Winter Park

$500,000

4 Beds ⋅ 2 Baths ⋅ Howell Forest SubDv. ⋅ 32789 Zip Code

Nestled in the serene and sought-after Hills of Winter Park, this expansive split-plan residence offers a unique opportunity to infuse your style into a home brimming with possibilities. As you step through its welcoming entrance, you are greeted by a generous living room that seamlessly transitions into an inviting dining area, perfect for hosting memorable gatherings. At the heart of this home lies the kitchen, opening gracefully into the family room. This space is a blank canvas for culinary creativity, equipped with ample storage, awaiting your custom touch. The adjoining family room, a haven for relaxation and family time, leads to three well-proportioned guest bedrooms. Each bedroom boasts considerable closet space and shares access to an updated full bathroom, echoing a sense of comfort and convenience. The primary suite, a sanctuary of tranquility, features a full bath and double closets. This masterful space connects to additional flex space, ideal for an office, nursery, or the creation of an expansive primary suite tailored to your desires. Step outside to discover the screened-in porch, a versatile area with indoor/outdoor carpeting, offering an idyllic setting for alfresco entertainment or quiet evenings under the stars. The substantial backyard, adorned with majestic trees and a charming deck area, presents a picturesque backdrop for outdoor activities or future landscaping projects. This home's location further enhances its appeal, zoned for the esteemed Dommerich Elementary, Maitland Middle, and Winter Park High schools. A residence not just offering a place to live, but a canvas for creating the home of your dreams. Your journey to personalize and complete this delightful Winter Park gem starts here.

2949 Lolissa Lane, Winter Park

$2,150,000

5 Beds ⋅ 6 Baths ⋅ Fremar SubDv. ⋅ 32789 Zip Code

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1875 Grinnell Terrace, Winter Park

$450,000

2 Beds ⋅ 2 Baths ⋅ Sylvan Heights SubDv. ⋅ 32789 Zip Code

Investor's opportunity in desirable Sylvan Heights! Zoned R-1A, this 6,592 Sq ft. lot is waiting for you to bring your vision to life! The structure on the lot is gutted; electric, utilities, cable and phone are connected. The Value is in the land

1840 Anzle Avenue, Winter Park

$140,000

1 Beds ⋅ 1 Baths ⋅ Waterfall Cove At Winter Park SubDv. ⋅ 32789 Zip Code

Spacious FIRST FLOOR condo in sought-after Winter Park! This 1 bedroom, 1 bath condo features a fully furnished kitchen, spacious living room, and sunny dining room. The primary bedroom includes a walk-in closet. For added convenience, a washer and dryer is located inside the condo. Just off the living room is a private outdoor patio with access to a community green space. Waterfall Cove features a community pool and playground, as well as internet and cable included. Within a mile of the community - easily walkable or bikeable - are fantastic Winter Park shopping and dining destinations including Ravaudage Winter Park, Whole Foods, Nordstrom Rack, and more. Also nearby is the recently renovated Winter Park Village. Traveling throughout Central Florida is easy with convenient access to I-4. Perfect investment opportunity as this outstanding condo is leased!

1695 Lee Road Unit D109, Winter Park

$660,000

2 Beds ⋅ 2 Baths ⋅ Cloisters Condo SubDv. ⋅ 32789 Zip Code

Introducing a splendid opportunity in downtown Winter Park living! This remodeled 2-bedroom, 2-bath condominium offers a prime location on the serene shores of Lake Osceola. With 1,143 square feet of living space, this unit exudes a light and airy feel, accentuated by warm-toned floors and an abundance of natural light. Notable features include two remodeled baths, with a walk-in shower in the master suite and a shower-tub combo in the hall bath, both elegantly enclosed in glass. The master bedroom boasts an en-suite bath, a dressing area with ample closet space, and even potential for adding a washer and dryer for added convenience. The separate kitchen, with the possibility for a simple cosmetic remodel, opens to a generous living and dining area, ideal for hosting guests or simply relaxing with tranquil views. Step outside to the oversized balcony, cocooned in privacy by mature landscaping, and enjoy vistas over the pool, lush greens, and the shimmering lake just around the corner. This condominium offers more than just comfortable living; it's a gateway to a lifestyle of luxury and convenience. Covered parking, an elevator, and proximity to daily amenities enhance the overall experience. Within the complex, you'll discover an array of amenities, including boat docks for water enthusiasts, a well-equipped gym for fitness enthusiasts, and an elegant community room for gatherings. Expertly managed by FirstService, this home promises a harmonious living experience. It's mere steps from the renowned shopping and dining on Park Avenue. Plus, you'll find the charm of Winter Park Village, nearby fitness centers, and the intellectual allure of Rollins College all within this vibrant community. Don't miss your chance to create lasting memories in this sophisticated Winter Park condominium. Contact us now to schedule your private viewing, and request the floor plan to discover how this exceptional unit can be your ideal home. Room Feature: Linen Closet In Bath (Primary Bedroom).

106 S Interlachen Avenue Unit 416, Winter Park

$472,500

4 Beds ⋅ 3 Baths ⋅ Albert Lee Ridge First Add SubDv. ⋅ 32789 Zip Code

LOCATION LOCATION LOCATION! Two minutes to I-4 for easy commute. Gorgeous open concept recently renovated cozy and charming 4 bedroom/3 bath in sought after city of Winter Park. Upgraded modern kitchen featuring white shaker style cabinets to ceiling with crown molding including brass hardware, soft close doors/drawers, built in large pantry with pull out drawers, cabinet enclosed counter depth French drawer refrigerator, all new appliances, oversized single trough stainless steel sink with brass faucet, modern quartz countertops and expanded backsplash to ceiling. Engineered hardwood throughout with spacious family room featuring a wood burning fireplace open to the main living areas. Additional formal sitting area/flex space with room for a large dining room table featuring modern light fixture.Master bath features marble subway tile to ceiling with custom shower niche and seamless glass shower enclosure. Hall bathroom features custom vanity with plenty of storage, quartz countertop with undermount porcelain sink and upgraded Kohler toilet. Fourth bedroom is split from additional bedrooms and has an attached full bath with new separate tankless hot water heater and oversized walk-in closet. Spacious car port with privacy fence and pavers to allow additional parking. Two large outdoor storage areas. Large backyard with endless potential with covered back porch and additional uncovered patio for entertaining. Fully fenced in backyard.No HOA. Close to Downtown Winter Park and tons of shopping, dining, and entertainment options close by.

2337 Albert Lee Pkwy, Winter Park

$1,025,000

4 Beds ⋅ 3 Baths ⋅ Winter Park Village SubDv. ⋅ 32789 Zip Code

One or more photo(s) has been virtually staged. NOW COMPLETE AND MOVE IN READY!!!!! New construction in Winter Park just east of the Vias...Custom Built by Main Street Builders. ONE STORY 4 Bedrooms/3 Bath POOL HOME, Open Concept Kitchen/Dining/Family Room, 10 ft Ceilings, Custom features include White Shaker Style Cabinets with Stackers to the Ceiling, Quartz C-tops, Large Island, Gas Cooking, Stainless Steel Appliances, Tile Wood Plank Floors, 8 ft. Doors, Sand Finish Stucco, MARBLE Pool Coping and deck, Tongue and Grove Porch Ceilings, Vinyl 6' Fence, 7.25" Baseboards, Custom Exterior Bahama Shutters and much more.

2417 Lafayette Avenue, Winter Park

$679,000

2 Beds ⋅ 3 Baths ⋅ Villa Del Seis Condo SubDv. ⋅ 32789 Zip Code

Introducing Villa del Seis: a collection of six meticulously crafted condominiums in the heart of Winter Park. This two-bedroom gem offers access to the picturesque Lake Virginia with a community dock. Nestled at the end of the building, this end unit welcomes an abundance of natural light, highlighting its charm. A wood-burning fireplace graces the living room, creating a cozy ambiance. French doors open to a rear porch and garden, merging indoor and outdoor living seamlessly. The dining room and living area are perfectly proportioned for comfort. An attached one-car garage and guest parking enhance convenience. The master retreat on the second floor boasts an en-suite bath and a walk-in closet. The second bedroom is equally impressive with its own en-suite bath. A powder bath downstairs adds a touch of practicality. The soaring vaulted ceiling in the living room accentuates the sense of spaciousness. New flooring throughout the home adds a fresh touch, while the remodeled kitchen, designer light fixtures, and custom built-in shelving in the dining room elevate the aesthetic. At the front entry, a window seat built-in invites relaxation. Situated near the famed Park Avenue shops and dining, this residence provides the epitome of downtown Winter Park living. Experience the perfect blend of modern comfort and classic elegance in this exceptional offering. Contact us now to secure your place in Villa del Seis and make Winter Park your new home.

674 Osceola Avenue Unit 674, Winter Park

$325,000

3 Beds ⋅ 2 Baths ⋅ Lake Bell Terrace SubDv. ⋅ 32789 Zip Code

Established neighborhood minutes from downtown. Roof new in 2017 and Electric upgrade in 2022 so there shouldn't be any big expense to a new buyer. This would be a good first home or good rental.

Winter Park

$1,089,000

3 Beds ⋅ 3 Baths ⋅ Maitland Shores First Add SubDv. ⋅ 32789 Zip Code

WONDERFUL OPPORTUNITY TO OWN THIS NEWLY UPDATED 3 BEDROOM, 3 BATH HOME IN A HIGHLY DESIRABLE WINTER PARK NEIGHBORHOOD. Zoned for top rated Schools. Waterfront home with 43 feet of canal frontage with stunning views. Located on Howell Creek Canal with direct access to Lake Maitland and The Winter Park Chain of Lakes. Ideal for many water sports, skiing, wake boarding, wave runners. This home has all new top notch modern interior finishes. Porcelain wood plank tile flooring throughout the entire home (no carpet) Chef kitchen with custom cabinets, Huge Island, New stone Quartzite countertops and full backsplash, All new GE Cafe' appliances, Double oven with Induction cooktop, French door refrigerator, and double door dishwasher. Both bathrooms have been completely updated. All new ceiling fans and new LED lighting throughout. 2 car garage with fully update 3rd bathroom, NEW INSULATED GARAGE OVERHEAD DOOR'S, NEW OPENER'S, NEW MINI SPLIT A/C IN GARAGE. New ROOF, NEW TRANE A/C, ALL NEW PELLA WINDOWS THROUGHOUT INCLUDING GARAGE AND MUCH MORE...The tranquil backyard with a water view is great for BBQ's and enjoying family and guests.

2600 Venetian Way, Winter Park

$768,000

3 Beds ⋅ 4 Baths ⋅ Sorensen Heights SubDv. ⋅ 32789 Zip Code

Are you looking for style, space, and comfort in the heart of luxurious Winter Park? Come see this Sorensen Fletcher mid-century modern pool home, strategically located just minutes from Park Ave. Spanning well over 3,000 sq ft, this architectural gem boasts timeless design and abundant living space, providing the ideal setting for luxurious living and entertaining. Spacious Layout: This home offers a well-designed floor plan with 3 bedrooms and 3.5 bathrooms, including two bonus rooms that can be used as additional bedrooms, an office, or a nursery – perfect for accommodating a growing family or hosting guests. Abundant Natural Light throughout: The living room and Florida room are highlighted by ceiling-to-floor windows, allowing natural light to flood the interiors and create a seamless connection with the lush outdoor surroundings. Enjoy the warmth of the fireplace during cozy evenings. Upgraded Kitchen: The kitchen is a host/hostesses dream, featuring modern appliances and a stylish design that will inspire culinary creativity just off the Formal Dining Room and Bar Room. Entertain in style with a formal dining room overlooking a serene side patio, ideal for intimate gatherings. Additionally, a dedicated bar room adds a touch of sophistication to your entertainment space. Luxurious Main Suite: The main suite is a private retreat with a bonus room that can be utilized as a dressing room, home office, or nursery, providing versatility to suit your lifestyle. Step outside to your oversized pool. Mother-in-Law Suite: Offering comfort and privacy, the mother-in-law suite features a bedroom and a separate living room, making it perfect for guests or multigenerational living. Enchanting Outdoor Living: Step outside to your own paradise featuring an enormous pool, expansive outside entertaining area, and multiple enclaves for intimate gatherings and solitude. A fountain, pond, and an adorable red bridge add to the charm of the outdoor space. Garage and Storage: The property includes a 2-car garage and an exterior storage building, ensuring ample space for vehicles and storage needs. Lush Landscaping: The landscaped grounds are a testament to elegance and care, showcasing mature showpiece palms, staghorns, crape myrtles, and a variety of other plantings that enhance the property's curb appeal. Nearby Attractions: Residents will appreciate the convenience of being just minutes away from the vibrant Park Avenue, Rollins College, and Winter Park Hospital. This Sorensen Fletcher mid-century modern home is a rare find, offering the perfect balance of timeless charm, modern amenities, and an enviable location. Don't miss the opportunity to make this masterpiece your own! Contact us for a private showing today.

412 Fletcher Place, Winter Park

$1,675,000

3 Beds ⋅ 3 Baths ⋅ Virginia Heights Rep SubDv. ⋅ 32789 Zip Code

Under contract-accepting backup offers. Nestled in the lush tree canopy and natural beauty of old Winter Park, this beautiful 3-bedroom, 3-bath pool home on a nearly ½ acre lot is just a short stroll from Rollins College and Park Avenue. Fully updated and surrounded by gorgeous landscaping and trees for maximum privacy, the home features a full office that could easily be converted into a 4th bedroom. Enter through large, double wooden glass doors into an attractive foyer that opens into a spacious family room complete with a gas fireplace and custom built-ins. A formal dining room is located to the right of the foyer. A large open kitchen spotlights custom cabinetry, granite countertops, an island, stainless steel appliances, a GE Monogram refrigerator, a built-in desk, panty, and large eat in area. Perfect for entertaining friends and family, the kitchen and family room overlook a private, oversized, fenced-in backyard, summer kitchen and pool that serve as the central focus point of the home. The outdoor kitchen and screened lanai lead to the large saltwater swimming pool and spa. Previous owners utilized a basketball pad in the far left of the backyard. With a very desirable split plan layout, the spacious primary suite is located on one wing with a separate sitting area with high ceilings and an oversized walk-in closet with custom shelving. The large primary bathroom has a walk-in shower, a separate soaking tub for relaxing after a long day, and dual sinks. The home's other wing includes the office with built-ins, a secret closet, and a separate bathroom. Two well-sized bedrooms share the other bathroom on this wing. Other features include a dedicated laundry room with ample cabinets and a large 3 car garage with a 50-amp electric car charger outlet. A rare find in Winter Park, the home also includes a full home natural gas generator, solar panels for the pool, plantation shutters throughout, updated plumbing, high ceilings, a tankless hot water heater, surround sound and cat 5 wiring throughout except for the 2 guest bedrooms. Located in the highly desirable Audubon K-8 school district, this home is in a great location just steps from lakes and downtown Winter Park.

1306 Richmond Road, Winter Park

$299,000

2 Beds ⋅ 1 Baths ⋅ Roclair SubDv. ⋅ 32789 Zip Code

LOCATION is key when searching for a place to call home. This charming 2BD/1BA FLORIDA STYLE home is in need of some TLC. *** NEW ROOF 2018 *** Perfect STARTER HOME or INVESTMENT property and NO HOA! Open floor plan with enclosed Florida room off the kitchen providing relaxing views of the spacious backyard. Private WORKSHOP is tucked in the back of the property with power, creating a flex space or home office. Just at the end of the street, you can enjoy the DUBSDREAD GOLF COURSE & CLUB HOUSE, just steps from the front door. Enjoy the convenience of being only minutes away from downtown WINTER PARK & COLLEGE PARK. Experience this growing community that offers streets filled with shops, restaurants, holiday festivals, farmers markets, and much more. You are also only 3 miles away from the NEW CITY PARK AT THE PACKING DISTRICT which has already broken ground. The NEW CITY COMMUNITY PARK will offer 66 ACRES of recreational green space which includes: Dog Parks, Playgrounds, Walking & Biking Trails, and a Tennis Center for all ages. This is just to name a few great things that are ahead for this community. Easy accessibility to major highways, theme parks, beaches, and airports. AGENTS *** Please review offer instructions and additional details!!!

26 Stymie Place, Winter Park

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3 Beds ⋅ 3 Baths ⋅ Fairshores Place SubDv. ⋅ 32789 Zip Code

Charming Winter Park Pool Home! This fantastic three bedroom, two and one-half bath home has been completely renovated inside and out with high-end finishes. New Tile floors throughout with beautiful inlay in the foyer, granite counters and cabinets in the kitchen and bathrooms, stainless steel appliances, freshly painted inside and out, all new windows throughout home with blinds. Hot water heater, plumbing, roof and HVAC all replaced in 2013. Great open floor plan with rooms that flow seamlessly. Family Room offers a wood burning fireplace, bar and sliding doors that lead to the patio and new marcited pool. Nice fenced yard, oversized lot and two car garage. All this with a Winter Park address! Do not miss this one!

2803 Riddle Drive, Winter Park

32789 Zip Code Florida Style Real Estate & Homes

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