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$185,000
2 Beds ⋅ 3 Baths ⋅ Hidden Oaks Condo Ph 10 SubDv. ⋅ 32792 Zip Code
This charming 2-bedroom, 2.5-bathroom townhome style condo offers the perfect blend of comfort and convenience. Enjoy the peace of mind that comes with a new AC (2025), a new roof (2021), newer water heater (2019) and new refrigerator and dishwasher ensuring your home is both energy-efficient and well-maintained. The entire first floor features ceramic tile, while the upstairs boasts beautiful laminate wood flooring—no carpet here! Both bedrooms are located upstairs, each with its own ensuite bathroom and additional storage above the mirrors. Downstairs, you'll find ample space for entertaining or simply relaxing, enhanced by the convenience of a wet bar. Located just minutes from UCF and Full Sail University, this condo is perfect for anyone looking to enjoy the vibrant local community without the long commute! With shopping, dining, and recreational activities nearby, you'll have everything you need right at your fingertips. Don’t miss out on this fantastic opportunity—schedule a showing today!

7450 Wynnewood Square Unit 189, Winter Park
$429,900
4 Beds ⋅ 2 Baths ⋅ Garden Lake Estates Unit 3 SubDv. ⋅ 32792 Zip Code
Oversized corner lot in quiet neighborhood with highly desired Seminole County schools. Well-built block on slab four bedroom home with split floor plan. Enclosed large Florida room. Shed. Existing irrigation well (but pump not working--no warranty on well). Double gate to back yard for parking RV/toys (back left). Roof 2018; water heater 2018; HVAC 2017; CPVC plumbing.

1401 Aster Court, Winter Park
$1,600,000
4 Beds ⋅ 4 Baths ⋅ Killarney Estates SubDv. ⋅ 32789 Zip Code
This home is an adorable 4 Bed 3.5 Bath Home in the heart of Winter Park. You will feel right at home the moment you step in. lovely kitchen showcases gorgeous cabinets, stainless steel appliances, ample amount of cabinetry and counter space, and a breakfast bar, great for entertaining family and friends. Open floor plan. Home features a separate dining area off the kitchen. Spacious living space and bedrooms. Spend your evenings and weekends relaxing on the beautiful lakefront of Lake Killarney, enjoying the incredible sunsets under the shade of huge cypress trees OR poolside in the private fenced in backyard.

250 Killarney, Winter Park
$1,995,000
4 Beds ⋅ 4 Baths ⋅ Tantum Add SubDv. ⋅ 32789 Zip Code
Truly a rare Winter Park offering. Perfectly positioned along the dogleg of the fourth fairway of the historic Winter Park 9-Hole Golf Course, this beautifully renovated four-bedroom, four-bath Mediterranean residence seamlessly blends timeless architectural character with sophisticated modern living. Rich in charm and thoughtfully updated throughout, the home welcomes you with an elegant living room featuring a gas fireplace, classic built-in shelving and abundant natural light. At the heart of the home is a stunning chef's kitchen, complete with custom floor-to-ceiling cabinetry, premium Thermador appliances, a charming breakfast nook and an inviting bar with wine refrigeration that flows effortlessly into the formal dining room, ideal for entertaining. A distinguished first-floor office offers an exceptional work-from-home environment, showcasing a breathtaking custom wall of built-in shelving, cabinetry and an integrated desk. This versatile space also serves beautifully as a library or den. Upstairs, all four bedrooms provide privacy and comfort. The luxurious primary suite features two separate closets, a spacious spa-inspired bath with a soaking tub overlooking the golf course and a private covered balcony perfect for enjoying peaceful morning coffee or evening sunsets. A generously sized secondary suite offers exceptional flexibility with its own custom walk-in closet, en suite bath and private rear staircase, making it ideal for guests, multigenerational living or a secluded retreat. Two additional bedrooms and a well-appointed full bath complete the second level. Updated features include smart house lighting, cabinet and shelving accent lighting, custom built-ins and much more. Designed to embrace Florida's indoor-outdoor lifestyle, the home offers a screened porch accessible from both the dining room and breakfast nook, creating an inviting space for year-round entertaining. Two additional open patios provide the perfect setting to relax while enjoying picturesque golf course views and the tranquil surroundings. Perhaps the home's greatest luxury is its exceptional location. Just steps from the boutiques, acclaimed restaurants, sidewalk cafés and vibrant atmosphere of Park Avenue, this residence offers an unmatched Winter Park lifestyle. Convenient access to downtown Orlando, major hospitals, world-renowned attractions and both Orlando International and Orlando Executive airports makes everyday living as effortless as it is elegant. This is a rare opportunity to own a beautifully updated Mediterranean home in one of Winter Park's most coveted and locations.

922 N Pennsylvania Avenue, Winter Park
$1,595,000
3 Beds ⋅ 3 Baths ⋅ Winter Park SubDv. ⋅ 32789 Zip Code
In the heart of Winter Park's vibrant Hannibal Square, this exceptional one-story residence, completed in 2022, offers the ideal blend of contemporary design, refined finishes and an unbeatable accessible lifestyle. Thoughtfully designed with three bedrooms, two and one-half baths, and an open-concept floor plan, the home showcases clean architectural lines, soaring ceilings and walls of glass that fill the interior with natural light while framing views of the beautifully landscaped grounds. The chef's kitchen serves as the centerpiece of the home, featuring premium Wolf and Sub-Zero appliances, custom cabinetry, a center island with seating, and workspace for everyday living and entertaining. The adjoining dining area flows seamlessly into the spacious great room, where custom-built library shelving creates a striking focal point and adds warmth and character to the modern design. Beautiful polished concrete floors extend throughout the residence, providing a cohesive and sophisticated aesthetic. Designed with privacy in mind, the split-bedroom floor plan places the primary suite in its own secluded wing. This spacious retreat offers direct access to the covered rear patio and features a beautiful bath with dual vanities, an oversized walk-in shower, private water closet, and an impressive custom walk-in closet measuring approximately 11 by 9 feet. Conveniently accessible from the primary bath and laundry room, the thoughtfully designed closet enhances everyday functionality. On opposite side of the home, two additional guest bedrooms are connected by a well-appointed Jack-and-Jill bath, while a stylish powder bath is ideally located for visitors. Outdoor living is equally inviting with a covered patio with a privacy bamboo hedge that creates a peaceful backdrop for relaxing or entertaining. An attached two-car garage completes this beautifully appointed residence. Ideally near the acclaimed restaurants, wine bars, coffee shops, and boutiques of Hannibal Square, this home offers one of Winter Park's desirable lifestyles. Visit the renowned shopping, dining, galleries and sidewalk cafés of Park Avenue, enjoy nearby Central Park and community events, or take advantage of the proximity to Rollins College, the Winter Park Farmers' Market and major roadways providing convenient access throughout Central Florida. This is a rare opportunity to enjoy nearly new construction in one of Winter Park's sought-after neighborhoods, where modern luxury and exceptional accessibility come together.

462 W Lyman Avenue, Winter Park
$4,250,000
4 Beds ⋅ 6 Baths ⋅ Alexander Place SubDv. ⋅ 32789 Zip Code
Envisioned by acclaimed architect Phil Kean and originally commissioned as the International Showcase Home for the National Association of Home Builders, this award-winning contemporary estate is a masterclass in modern design. Tucked away on a prestigious cul-de-sac between Lake Osceola and the iconic Alfond Inn, the residence offers unparalleled privacy just two blocks from Park Avenue's world-class amenities. A striking entryway with 10-foot mahogany doors reveals a secluded courtyard oasis, featuring a sparkling pool framed by lush Signature landscaping. Inside, expansive living spaces with soaring 14-foot ceilings and a dramatic 40-foot gallery wall flow seamlessly to the outdoors, creating an effortless connection between interior elegance and open-air entertaining. The sleek, state-of-the-art kitchen is curated with premium Monogram, JennAir, and Gaggenau appliances, complemented by a sophisticated wet bar and an intimate media lounge. Ascend the floating staircase or private elevator to the primary sanctuary, which exclusively commands the entire second level. This lavish retreat features a spa-inspired bath with a smart-controlled shower, an oversized marble vanity, and three private terraces. The estate is further elevated by a first-floor guest suite, an executive office, a fitness studio with an en-suite steam shower, and a versatile poolside casita. Integrated smart home technology, automatic Lutron shades, whole-house generator and a three car garage provide ultimate modern convenience. Every element of this residence reflects intentional design, innovation, and timeless elegance, embodying the pinnacle of world-class Winter Park living.

229 Alexander Place, Winter Park
$385,000
4 Beds ⋅ 2 Baths ⋅ Eastbrook Sub SubDv. ⋅ 32792 Zip Code
Beautifully updated 4-bedroom, 2-bath pool home in Winter Park offering modern upgrades and flexible living space. The home features new tile flooring throughout, a fully renovated kitchen with a stunning waterfall quartz island, and two beautifully remodeled bathrooms. The garage has been updated with new flooring and a new garage door. Major improvements include a new roof (2024), new A/C (2023), complete home repipe (2022), updated electrical panel, and pavers in both the front and back of the home. The swimming pool was resurfaced with new tile in 2023 and is approximately 12 feet deep, creating the perfect backyard retreat.

885 Carnation Drive, Winter Park
$719,900
4 Beds ⋅ 4 Baths ⋅ Swoope Park SubDv. ⋅ 32789 Zip Code
Virtually Staged. Welcome to this virtually staged contemporary townhome in the desirable 400 West community, home to just nine residences and steps away from lively Park Avenue. Enter through the private garage or the charming front path, and you'll find a bright and open main floor that perfectly balances comfort and modern style. The main floor features a stylish mix of finishes, including large-format porcelain tiles, level 4 drywall, tall baseboards, and designer lighting. The centerpiece is a sleek kitchen equipped with glossy white cabinetry, chic chrome pulls, quartz countertops, and top-quality stainless-steel appliances. The garage, with alley access, includes a storage closet and built-in shelving for added convenience. On the second level, discover two spacious primary suites with modern LVP flooring and large windows that let in plenty of natural light. The en-suite bathrooms are designed with porcelain tiles, frameless glass showers, wall-to-wall mirrors, and matte white vanities. The primary bath offers a double-sink vanity, a private water closet, and a spacious walk-in closet. A conveniently situated laundry room features a Samsung washer and dryer with overhead storage. The third level has two more bedrooms, each with walk-in closets, connected by a shared Jack-and-Jill bath, making it ideal for guests, a home office, or a workout space. Don’t miss the chance to check out this fantastic home in a prime location where luxury meets practicality!

436 W Swoope Avenue, Winter Park
$1,500,000
5 Beds ⋅ 5 Baths ⋅ Park Manor First Add SubDv. ⋅ 32792 Zip Code
Virtually Staged. Built in 2021 by David Weekley Homes, this thoughtfully designed 5-bedroom, 4.5-bath residence delivers 3,109 square feet of refined, light-filled living in one of Central Florida's most desirable locations. The sought-after Easterley floorplan opens into a bright, open-concept layout where soaring ceilings and abundant natural light set an effortlessly elegant tone, with generous room to gather, work, and unwind. At the heart of the home, a gourmet kitchen anchors the space with quartz countertops, a gas range, premium GE appliances, and a walk-in pantry—equally suited to weeknight dinners and lively entertaining. The first-floor primary suite offers a private retreat with a spa-inspired bath featuring a walk-in shower and a separate soaking tub, while four additional bedrooms provide flexible space for guests, a home office, or a playroom. Already plumbed and wired for a pool, the backyard is primed to become your own private oasis—simply add the design you've always envisioned. The location is exceptional. The home is zoned for top-rated schools, is just a short walk to the Winter Park YMCA, moments from Interlachen Country Club, and less than a mile from AdventHealth Winter Park—an unbeatable commute for those in the medical field. Park Avenue's upscale shopping and dining is just two miles away, with Baldwin Park's shops, restaurants, and lakeside trails only three miles from your door. Best of all: NO HOA. Modern construction, an unmatched address, and true Winter Park living—all in one.

777 Halifax Avenue, Winter Park
$255,000
3 Beds ⋅ 2 Baths ⋅ Cedarwood Village 1 SubDv. ⋅ 32792 Zip Code
Rare end units like this don't come around often! Welcome to 2450 Grand Teton Circle, tucked away in the well-maintained, established community of Cedarwood Village in Winter Park. This 3-bedroom, 2-bath home is filled with natural light thanks to its end-unit location, and the open layout makes it easy to relax, entertain and enjoy everyday living. The spacious living and dining areas flow together nicely, while the kitchen offers plenty of room to cook, gather, and stay connected with family and friends. Over the past several years, this home has been thoughtfully updated, giving the next owner peace of mind. Major improvements include a new roof, skylights, HVAC system, water heater, kitchen appliances, washer and dryer, updated LED lighting, and fresh interior paint. Both bathrooms have been beautifully remodeled, the home has been replumbed by the HOA, and the primary closet has been enhanced with custom shelving. Additional updates include new flooring in the secondary bedrooms, updated window blinds, and thoughtful finishing touches throughout. The private screened lanai has been transformed into a cozy outdoor retreat with fresh paint, a ceiling fan, new screens and screen door, string lighting, and decorative greenery—making it the perfect place to enjoy your morning coffee or unwind after a long day. Life here is easy. Cedarwood Village is a beautifully maintained, established community featuring a community pool and Clubhouse for your special events, tennis courts, and pickleball courts. The HOA has also recently repainted the exterior of the buildings, helping keep the neighborhood looking fresh and inviting. Best of all, this home is value priced, giving you an incredible opportunity to own in desirable Winter Park without the premium price tag. You're just minutes from Winter Park's shopping and dining, Full Sail University, UCF, major employers, and convenient access to SR-417 and downtown Orlando. If you've been looking for a move-in-ready home in a fantastic location with years of thoughtful updates already completed, this rare end unit is definitely worth a look!

2450 Grand Teton Circle Unit 2450, Winter Park
$379,900
4 Beds ⋅ 2 Baths ⋅ Suburban Homes First Add SubDv. ⋅ 32792 Zip Code
Updated 4/2 with New Roof, New AC (x2), and New Dual-pane Windows | No HOA | Top-Rated Winter Park School Zone ... Welcome to low-maintenance Winter Park living at 4965 Orange Ave in 32792 with no HOA constraints or fees. Nestled on a quiet lot zoned for top-rated Orange County Public Schools Lakemont Elementary, Maitland Middle, and Winter Park High School, this move-in ready four-bedroom single-family home offers major high-ticket capital improvements already completed. Upgrades include a NEW Roof, two NEW A/C systems for dual-zone energy efficiency, NEW dual-pane insulated windows, fresh interior and exterior paint, and modern fixtures throughout. The carpet-free interior boasts easy-to-clean polished terrazzo and modern ceramic tile flooring, an updated galley kitchen with stainless steel appliances and solid wood cabinets, and two thoughtfully remodeled bathrooms. Designed with incredible layout versatility, the split four-bedroom floor plan includes direct exterior access through sliding glass doors, making it exceptionally well-suited for a multi-generational setup, in-law suite, private guest retreat, or dedicated home office. Outside, the expansive fully fenced backyard provides ample room for pets, outdoor entertaining, or a future pool, while the attached carport offers covered parking and a dedicated laundry utility storage room. Enjoy an unbeatable Central Florida location just minutes from Park Avenue dining, boutique shopping, local parks, and major Orlando commute routes.

4965 Orange Avenue, Winter Park
$320,000
2 Beds ⋅ 2 Baths ⋅ Aloma Park SubDv. ⋅ 32792 Zip Code
**This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.** Welcome to 5781 Shale Court in Winter Park, a 2-bedroom, 2-bath home designed for comfortable everyday living. This one-story residence offers a practical layout with space for relaxing, dining, and hosting guests. The two-bedroom configuration provides flexibility for residents, visitors, a home office, or a hobby room, while two full bathrooms add convenience for daily routines. Outdoor living includes a covered and screened patio, creating a comfortable space to enjoy fresh air, outdoor dining, or quiet downtime while staying shaded and protected from the elements. Located in Winter Park, the home is close to shopping, dining, parks, schools, and everyday conveniences. The area offers access to nearby destinations such as Winter Park Village, Park Avenue, local recreation, and major roadways connecting to Maitland, Orlando, and surrounding Central Florida communities.

5781 Shale Court, Winter Park
$88,999
1 Beds ⋅ 1 Baths ⋅ Waterfall Cove Of Winter Park SubDv. ⋅ 32789 Zip Code
This charming 1bedroom, 1bathroom condo is a fantastic opportunity for both homeowners and investors. Located in a desirable area close to shopping, restaurants, and everyday conveniences, it offers comfort, convenience, and excellent value. The kitchen comes fully equipped with a refrigerator, stove, dishwasher, and microwave, and the unit also includes a washer and dryer for added convenience. Step outside onto your private outdoor balcony, the perfect spot to enjoy your morning coffee or unwind after a long day. Residents have access to a beautiful community swimming pool, creating a relaxing atmosphere to enjoy year-round. Whether you're looking for a place to call home or a great investment property, this condo has everything you need in an ideal location.

1695 Lee Road Unit B108, Winter Park
$279,900
2 Beds ⋅ 2 Baths ⋅ Cedarwood Village SubDv. ⋅ 32792 Zip Code
Beautifully renovated 2 bedroom, 2 bathroom condo at 2305 Sun Valley in Winter Park, offering a fresh modern design and thoughtful updates throughout. The fully redesigned kitchen features sleek cabinetry, quartz countertops, GE stainless steel appliances, a marble tile backsplash, abundant storage, recessed lighting, and a clean open feel that connects seamlessly to the main living areas. Wood-look porcelain tile flooring runs throughout the home, creating a cohesive, attractive, and low-maintenance finish. The spacious living area features vaulted ceilings, skylights, updated ceiling fans, and sliding glass doors that fill the space with natural light and lead to a covered screened patio overlooking green space. The primary suite includes an updated double vanity and a beautifully redesigned bathroom with a separate tub and newly installed shower. The second bathroom also offers an updated vanity and clean neutral finishes. Additional highlights include a 2021 AC, 2021 water heater, updated fixtures, generous natural light, and a screened outdoor living space ideal for relaxing and enjoying Florida’s indoor-outdoor lifestyle. This move-in ready Winter Park condo combines modern style, comfort, and everyday functionality. Residents enjoy access to a sparkling community pool, clubhouse, tennis and pickleball, and a pet walk with waste stations. Monthly fees also include roof and exterior building maintenance, exterior pest control, and landscaping, adding convenience and long-term value.The location is hard to beat, just minutes from Park Avenue, UCF, Rollins College, Full Sail University, shopping, dining, entertainment, and nearby medical facilities.

2305 Sun Valley Cir, Winter Park, Fl 32792, Winter Park
$85,000
2 Beds ⋅ 2 Baths ⋅ Winter Park Woods Condo SubDv. ⋅ 32792 Zip Code
Great location for homeowner or investor. Located close to FullSail and UCF and major roads, shopping, eating and more. Don't hesitate to see this one before it is gone!

252 Scottsdale Sq Unit 252, Winter Park
$799,900
4 Beds ⋅ 3 Baths ⋅ Winter Park Pines SubDv. ⋅ 32792 Zip Code
JUST REDUCED! Impeccably Renovated Turn-Key Oasis with a Resort-Style Backyard! No HOA with yard large enough for possible ADU. Welcome home to this meticulously updated 4-bedroom, 3-bathroom residence where true pride of ownership shines through every detail. Absolutely turn-key and loaded with premium updates throughout, such as new electrical panel, newer water heater, new pool pavers, upgraded engineered floors throughout & much more! This home offers the perfect blend of modern luxury and effortless entertaining.The heart of the home seamlessly connects to the outdoors with a brilliant kitchen pass-through window, serving an enormous covered patio. Step into your own private, tranquil backyard oasis featuring a freshly resurfaced pool surrounded by stunning new pavers & large Perolga. Whether you are hosting a summer barbecue or rinsing off in your convenient outdoor shower after a swim, this backyard is built for Florida living at its finest. Property is zoned for highly rated schools with convenient location just moments away from Cady Way Park & trails, Rollins, UCF, & Full Sail Colleges, just 4 miles from vibrant dining(Park Ave) & premier shopping.

722 S Ranger Boulevard, Winter Park
$285,000
2 Beds ⋅ 2 Baths ⋅ Cedarwood Village 1 SubDv. ⋅ 32792 Zip Code
Welcome to this beautifully updated condo, ideally nestled between Winter Park and Maitland. This inviting home features a versatile upstairs loft overlooking the living and dining areas—perfect for a home office, fitness space, craft room, or additional guest accommodations. The bright, cheerful eat-in kitchen is both stylish and functional, showcasing quartz countertops, a glass tile backsplash, abundant cabinetry, a pull-out spice rack, trash/recycling cabinet, and a built-in storage unit. Sliding glass doors open to the private front courtyard, filling the space with natural light. Conveniently located laundry area, complete with washer and dryer, is tucked within the kitchen. The spacious living room features a cozy wood-burning fireplace and flows seamlessly into the dining area beneath soaring vaulted ceilings accented by skylights. Sliding glass doors lead to a screened lanai with a slate tile floor and a storage closet—an ideal spot to relax and enjoy Florida living. The primary suite also opens directly to the lanai and offers a beautifully renovated en-suite bath with a luxurious walk-in shower, updated vanity, linen cabinet, and a custom walk-in closet with built-in organizers. The front bedroom also includes a generous walk-in closet. Enjoy added privacy with a picturesque, tree-lined green space across the street rather than neighboring condos directly in front. Two dedicated parking spaces are conveniently located just outside your door. Cedarwood Village offers an exceptional location directly across from Casselberry Commons Shopping Plaza and is just minutes from Full Sail University, UCF, and Rollins College. Residents enjoy a community swimming pool, tennis courts with pickleball lines, and designated dog-walking areas. Additional highlights include a new roof and skylights installed in 2020. Monthly HOA fees cover exterior maintenance, lawn care, and community amenities, making this the perfect opportunity to enjoy carefree living in one of the area's most desirable communities.

2372 Sun Valley Circle Unit 2372, Winter Park
$135,000
3 Beds ⋅ 2 Baths ⋅ Waterfall Cove SubDv. ⋅ 32789 Zip Code
Welcome to this charming first-floor 3-bedroom, 2-bath condominium located in the beautiful city of Winter Park! Featuring laminate flooring throughout the main living areas, this inviting home offers an open-concept layout with a combined living and dining room that overlooks the kitchen, creating the perfect space for everyday living and entertaining. Each bedroom is equipped with a ceiling fan for added comfort, while the private rear patio provides a peaceful outdoor retreat complete with a bench—ideal for relaxing and enjoying Florida's beautiful weather. Whether you're searching for a primary residence, a seasonal getaway, or an investment opportunity, this condo offers exceptional value. HOA dues include pest control, basic cable, basic internet, exterior maintenance, and additional storage, providing convenience and peace of mind. Residents also enjoy access to community amenities including a swimming pool, playground, and clubhouse, all in a desirable Winter Park location close to shopping, dining, parks, and major roadways. Don't miss the opportunity to make this wonderful property your own!

1695 Lee Road Unit A116, Winter Park
$1,625,000
4 Beds ⋅ 4 Baths ⋅ Charmont SubDv. ⋅ 32789 Zip Code
Virtually Staged. A rare opportunity to live on a quiet one-way street overlooking a park in the heart of Winter Park. Built in 2007 and meticulously maintained, this exceptional 4-bedroom, 4-bath pool home with a dedicated office offers timeless design, thoughtful updates, and an unbeatable location. A welcoming covered front porch provides the perfect spot to enjoy your morning coffee. Inside, soaring ceilings, extensive moldings, travertine and hardwood floors, and abundant natural light create an elegant first impression. Just off the foyer, French doors open to a private office, ideal for working from home. A secondary bedroom and full bath with a walk-in shower are conveniently located on the main level. The spacious kitchen flows seamlessly into the family room and features granite countertops, solid wood soft-close cabinetry, a gas cooktop, wall oven, breakfast bar, wet bar, walk-in pantry, and a sunny breakfast nook overlooking the lanai and pool. The adjoining family room is anchored by a gas fireplace and French doors leading outdoors. The covered lanai showcases a tongue-and-groove ceiling and remote-controlled screens, creating the perfect setting for year-round entertaining. The generous first-floor primary suite offers space for a sitting area and features two custom walk-in closets, dual vanities, a soaking tub, separate shower, and private water closet. A beautiful wrought-iron staircase leads upstairs to two generous en-suite bedrooms and a cozy loft. The private backyard is designed for relaxation and entertaining, featuring a saltwater pool and spa surrounded by lush landscaping. Additional highlights include two newer HVAC systems (2022 and 2023), a gas water heater (2022), central vacuum system, built-in Home Team pest defense system, and plantation shutters throughout. Located within the highly sought-after Audubon K-8 and Winter Park High School districts, this exceptional home is ideally situated between Park Avenue and Corrine Drive, with downtown Orlando just minutes away.

341 E Reading Way, Winter Park
$138,000
1 Beds ⋅ 1 Baths ⋅ Golfside Villas Condo SubDv. ⋅ 32792 Zip Code
Great for INVESTORS!..instant rent upon closing, start collecting the day after closing!!..Also can be great Spacious Other units currently available in same complex Great starter home../ ONE bedroom condo in Golfside Villas located in the heart of Winter Park. Great location for travel to Winter Park, Full Sail, UCF and/or the airport. Low HOA fees that cover all exterior items, along with pool and other amenities. Water and sewer is though HOA fees , nice bonus for tenants. This condo home is investment property with a long term tenant but can be ready for an owner occupant Current tenant is under market rent… opportunity to make some changes here. Schedule a showing today!

1000 S Semoran Boulevard Unit 408, Winter Park
$138,000
1 Beds ⋅ 1 Baths ⋅ Golfside Villas Condo SubDv. ⋅ 32792 Zip Code
Great for INVESTORS!..instant rent upon closing, start collecting the day after closing!!..Also can be great Spacious Other units currently available in same complex Great starter home../ ONE bedroom condo in Golfside Villas located in the heart of Winter Park. Great location for travel to Winter Park, Full Sail, UCF and/or the airport. Low HOA fees that cover all exterior items, along with pool and other amenities. Water and sewer is though HOA fees , nice bonus for tenants. This condo home is investment property with a long term tenant but can be ready for an owner occupant Current tenant is under market rent… opportunity to make some changes here. Schedule a showing today!

1000 S Semoran Boulevard Unit 404, Winter Park
$138,000
1 Beds ⋅ 1 Baths ⋅ Golfside Villas Condo SubDv. ⋅ 32792 Zip Code
Virtually Staged. Great for INVESTORS!..instant rent upon closing, start collecting the day after closing!!..Also can be great Spacious Other units currently available in same complex Great starter home../ ONE bedroom condo in Golfside Villas located in the heart of Winter Park. Great location for travel to Winter Park, Full Sail, UCF and/or the airport. Low HOA fees that cover all exterior items, along with pool and other amenities. Water and sewer is though HOA fees , nice bonus for tenants. This condo home is investment property with a long term tenant but can be ready for an owner occupant Current tenant is under market rent… opportunity to make some changes here. Schedule a showing today!

1000 S Semoran Boulevard Unit 306, Winter Park
$439,900
3 Beds ⋅ 1 Baths ⋅ Pines SubDv. ⋅ 32789 Zip Code
Seller is highly motivated. Competitively priced for a quick sale. Don't miss your opportunity to own this beautiful home! First time on the market in over 60 years! Filled with decades of cherished family memories, this beloved home is ready for its next chapter. Located in the highly desirable Winter Park 32789 ZIP code, 2041 Jewell Avenue offers an unbeatable location just minutes from Dubsdread Golf Course, College Park, and downtown Winter Park, with quick access to I-4, making commuting throughout Central Florida a breeze. Lovingly maintained and thoughtfully updated over the years, the home features a 2024 roof, central air conditioning, and a large, wheelchair-accessible walk-in shower, providing enhanced comfort and accessibility. The spacious, fully fenced backyard offers plenty of room to relax, entertain, garden, or play. Situated on a quiet dead-end street, you'll enjoy minimal traffic and a peaceful neighborhood setting. The original fourth bedroom has been converted into a generous laundry room, adding convenience and extra storage while offering flexibility for future customization if desired. Whether you're looking to move right in, renovate, or create your dream home in one of Central Florida's most sought-after neighborhoods, this property presents an exceptional opportunity. Now it's your turn to create a lifetime of memories and make this treasured home your own.

2041 Jewell Avenue, Winter Park
$425,000
1 Beds ⋅ 1 Baths ⋅ Knowles Manor North Condo SubDv. ⋅ 32789 Zip Code
LOCATION! LOCATION! LOCATION! Welcome to Knowles Manor...a charming 11 unit condo perched on quiet brick street in the heart of Olde Winter Park...just steps from the Winter Park 9 golf course, Casa Feliz, and the boutiques, restaurants, and vibrant lifestyle of Park Avenue, this location is hard to beat. This delightful first-floor residence is the perfect place to call home or an ideal pied-a'-terre for seasonal living. Inside you'll find easy maintenance tile flooring throughout, a full kitchen and bath, abundant closet space, and an adorable screened rear porch-perfect for relaxing with your morning coffee or unwinding at the end of the day. Additional highlights include a quaint community patio, one assigned parking space steps from your front door, a new HVAC system installed in 2021, and a new roof 2025. Whether you are looking for a full time residence, a weekend retreat, or a low maintenance Winter Park getaway, this charming condo is ready to welcome you home. HOA $217 per month!! Welcome Home!

644 N Knowles Avenue Unit 3, Winter Park
$5,600,000
5 Beds ⋅ 6 Baths ⋅ Maitland Shores First Add SubDv. ⋅ 32789 Zip Code
This elegant transitional French Provincial residence was the feature home in the Orlando Museum of Art's 2022 "mystery home tour" and is located on a large, elevated corner lot in a quiet and secluded area in the Via’s of Winter Park. This residence has been significantly enhanced inside and out by the current owner. The home features 5,200 square feet of living space and 800+ square feet of outdoor space with 5 bedrooms, 5 bathrooms ensuite, 1 half bathroom, 3 car garage, pool, patio and professionally landscaped yard and lighting. Upon entry, you are welcomed through the exquisite foyer where you instantly notice the craftsmanship and expert care that went into the custom carpentry and crown molding details throughout. To the left of the foyer is an elegant and intimate parlor with grass cloth wallpaper, a gas vented fireplace and built-in bookshelves. To the right of the foyer is the formal dining room with beautiful hand painted wallpaper and an adjacent butler’s pantry. Past the foyer you are led to a spacious and grand formal living room with 6 new French iron doors that flow out to a covered brick porch and picturesque back yard & pool. Designed with entertainment in mind, the adjoining chef’s kitchen includes newly painted custom cabinetry, a Sub-Zero/Wolf appliance package, a grand center island and a walk-in pantry. Built in desk and casual dining area all open to the adjoining beamed ceiling family room with gas vented fireplace and additional French doors that lead to street side patio with new awnings. First floor master retreat overlooks the pool & yard and features 14-foot wood beam vaulted ceilings. The oversized master bath with double custom lacquered vanities made in Palm Beach, mosaic marble shower and a Waterworks free standing tub, brushed brass fixtures, and walk in closet. The second-floor features nine-foot ceilings with four bedrooms (one which was converted to a beautiful women’s dressing room) and four ensuite bathrooms, covered balcony adjoining two bedrooms, two built in desks and bookshelves for office/study time and large media room with big screen tv and wet-bar. There are also two laundry rooms, one upstairs and one downstairs. Attic space inside the home and inside the garage. Recent upgrades include slate roof/swooped decorative copper roof with chimney caps, complete chimney rebuild, nine iron French doors, white oak tongue and grove hardwood floors, renovated master bath and two ensuite baths, two new HVAC home units and a new garage mini-split air conditioner. This home offers boat access to the Winter Park chain of lakes and is within short distance of the Winter Park Racquet Club. It’s also a bike ride away and a short drive to the Interlachen Country Club and Park Avenue shopping and dining district. The property is zoned for Dommerich Elementary, Maitland Middle School, and Winter Park High School. One or more rooms virtually staged

2228 Azalea Place, Winter Park
$499,000
2 Beds ⋅ 1 Baths ⋅ Seville Park SubDv. ⋅ 32789 Zip Code
Charming renovated bungalow on a brick street in the heart of Winter Park! Recently updated with new finishes and appliances throughout. Huge back yard with plenty of potential space for ADU! Move in ready, no HOA, and just a short stroll from Rollins College and beautiful Park Avenue. A rare must see opportunity!

981 Aragon Avenue, Winter Park
$1,025,000
3 Beds ⋅ 3 Baths ⋅ Virginia Heights Rep SubDv. ⋅ 32789 Zip Code
Georgetown-style 'Brownstown' in the Heart of Winter Park, walking distance to Downtown, PLUS deeded Lake Access to Lake Virginia! This spacious property has 3 bedrooms, 3 full baths, 2434 sq ft, 10' ceilings custom details throughout and natural lighting. Foyer with slate flooring, enjoy the double-sided gas fireplace in the Living & Dining areas, beautiful wood floors, crown molding, plantation shutters, a butler bar with custom cabinetry & wine refrigerator. Cooking inspired Kitchen with a lengthy granite island and sitting bar overlooks the Family room. Upgraded stainless appliances, including gas cooktop with griddle, microwave/convection oven, hanging pot rack with lighting, and soft close cabinets with pullouts. French doors to the covered 'English Garden' courtyard with pavers & stainless grill for entertaining. Guest suite or home office with a custom closet and full bath overlooks brick street, Pennsylvania Ave. Large laundry room near the garage with granite countertops, cabinets & utility sink, plus washer & dryer. Upstairs is a spacious Primary bedroom with French doors to a private covered balcony; also, 2 large walk-in closets with closet systems, Jacuzzi tub, huge walk-in shower, dual vanities with granite countertops & more. An additional ensuite bedroom, more wood floors, plus a built-in dehumidifier. Attached 2-car, rear alley access garage, plus an additional side parking pad. Walk to Park Ave. for dining, shopping, WP Tennis Center, outdoor park & Rollins College. Neighborhood Lake Virginia access for paddleboard & kayak launching to the Winter Park Chain of Lakes. Top schools, Audubon K-8 seconds away, and WPHS. NEW TPO membrane roof w/ metal coping March 2026. HOA maintains: landscaping, irrigation, building maintenance & outdoor lighting. Won't last!

1138 S Pennsylvania Avenue, Winter Park
$1,099,000
4 Beds ⋅ 3 Baths ⋅ Northwood Terrace SubDv. ⋅ 32789 Zip Code
Reinvented from the ground up for modern living while honoring its 1953 mid-century modern roots, this 4-bedroom, 3-bath Winter Park home blends authentic MCM character with all-new finishes and systems. An open living, dining, and kitchen core opens to a light-filled sitting area, with white oak floors and designer lighting and ceiling fans throughout. The kitchen stuns with Taj Mahal quartzite counters and KitchenAid stainless appliances. Out back, an expanded patio overlooks a private, fenced yard built for gathering. Everything is new: roof, windows, 200-amp electrical, plumbing with new water heater, HVAC ductwork, and Nest thermostat. Best of all, you can live it on foot: walk to East End Market, Kelly's Homemade Ice Cream, Redlight Redlight, Sushi Lola's, and top-rated Audubon Park K-8. Zoned for Winter Park High, and minutes to Park Avenue and Rollins College. A turnkey classic in one of Winter Park's most established, walkable neighborhoods.

3006 Northwood Boulevard, Winter Park
$579,900
3 Beds ⋅ 2 Baths ⋅ Albert Lee Ridge Add 02 SubDv. ⋅ 32789 Zip Code
Rare Waterfront Opportunity in Winter Park! Discover your own slice of Florida paradise with this waterfront gem offering 94 feet of direct canal frontage on Lake Bell for under $600,000. Tucked away in a peaceful, private setting, yet just minutes from Winter Park’s famed Park Ave, Winter Park Village, College Park and Downtown Orlando with numerous shopping and dining options making this property the perfect blend of seclusion and convenience. Built in 1957, this classic Florida ranch features 3 bedrooms and 2 bathrooms within 1,837 SF of living space. Major updates include a new roof in 2024 and HVAC in 2019. Step inside off the covered front porch to find spacious living and dining areas highlighted by charming built-in features and abundant natural light. At the heart of the home, the kitchen offers easy access to a generous walk-in pantry/utility room/laundry area. The adjoining family room opens to a covered back porch overlooking the expansive backyard and tranquil canal. Situated on a .40-acre lot, the property extends beyond the canal, creating a natural wooded buffer that enhances privacy and provides a serene backdrop. Whether you envision a pool, outdoor kitchen, garden, or entertaining space, the backyard offers endless possibilities to create your dream outdoor oasis (subject to municipal review and approvals). Lake Bell is a 36-acre spring-fed ski lake with an average depth of 12 feet, ideal for boating, skiing, kayaking, paddle boarding and enjoying the Florida lifestyle. Fishing enthusiasts will also appreciate the lake’s reputation for largemouth bass and bluegill. Other notable exterior highlights include fenced in backyard, covered front entry, two rear porches and 1-car carport. The home is on septic that has been well maintained and serviced annually. The location also offers quick access to Interstate 4 and close proximity to area hospitals, parks and cultural centers. Don’t miss this exceptional opportunity to own waterfront property in Winter Park/3789 at an incredible value!

1003 Lake Bell Drive, Winter Park
$459,900
3 Beds ⋅ 2 Baths ⋅ Orange Terrace SubDv. ⋅ 32789 Zip Code
Beautifully renovated three-bedroom, two-bath home in desirable Winter Park 32789. Extensively updated throughout, this move-in-ready home offers the perfect blend of modern style, comfort and convenience. Filled with natural light, this home features a stunning renovated kitchen with an open pass-through breakfast bar and seating, ideal for entertaining and everyday living, a large stainless sink beneath a window and plenty of stunning quartz countertop space. Both baths have been tastefully remodeled, and nearly every aspect of the home has been thoughtfully updated to create a fresh, contemporary feel. Major improvements provide added peace of mind, including a new roof in October 2023, an HVAC system in 2023 and a water heater in 2024. Enjoy the convenience of a large covered carport with built-in storage, plus a huge backyard with endless possibilities for gardening, pets, play or future expansion. An additional storage shed, added in 2018, offers even more space for tools, hobbies and outdoor equipment. Ideally located with quick access to Interstate 4 and 17-92 and just minutes from Park Avenue, Winter Park Village, College Park and Downtown Orlando, you'll enjoy some of Central Florida's finest shopping, dining, entertainment and cultural attractions right at your fingertips. Best of all, no HOA. Combining extensive renovations, major system updates, an oversized backyard and an unbeatable location, this exceptional Winter Park home is truly move-in ready and waiting for its next owner. Call to schedule your appointment today!

259 Orange Terrace Drive, Winter Park