Homesinorlando.forsale Search Results

$375,000

Come build your dream home on this oversized single family corner lot (62.5 by 141.5) in Winter Park Florida with amazing views of Dubsdread Golf Course hole 6. Located just a short drive or walk away from all your favorite shops and restaurants (Agave Azul, Publix, Tap Room, Black Bean Deli) Convenient access to I-4 making it easy to get around the greater Orlando area. Less than a minute drive to Park Maitland School and zoned Princeton Elementary School. The existing single family structure is being offered as is and the owner has no previous information on the home. Demolition date is now scheduled for 4/24/2025. 20k impact fee credit/verify exact when pulling new permit

2 Beds ⋅ 1 Baths ⋅ Olympia Heights Annex SubDv. ⋅ 32789 Zip Code

Come build your dream home on this oversized single family corner lot (62.5 by 141.5) in Winter Park Florida with amazing views of Dubsdread Golf Course hole 6. Located just a short drive or walk away from all your favorite shops and restaurants (Agave Azul, Publix, Tap Room, Black Bean Deli) Convenient access to I-4 making it easy to get around the greater Orlando area. Less than a minute drive to Park Maitland School and zoned Princeton Elementary School. The existing single family structure is being offered as is and the owner has no previous information on the home. Demolition date is now scheduled for 4/24/2025. 20k impact fee credit/verify exact when pulling new permit

2259 Minnesota Avenue, Winter Park

$2,594,550

Experience modern elegance in this stunning Lake Sylvan estate with breathtaking lake views and seamless indoor-outdoor living. The open-concept design features a gourmet kitchen (renovated 2023) with quartzite countertops, a wet bar, and luxe appliances. French doors, a custom gas fireplace, and designer lighting add refined charm to the living room. Step outside to nearly 1500 sqft of additional living space on the lake featuring a heated pool, spa, covered patio with gas fireplace, summer kitchen and lakeside firepit. With three bedrooms and a versatile office (easily a fourth), this home adapts to your needs. The first-floor primary suite opens to the pool, while an upstairs primary suite has dual custom closets, a spa-like bath, and a private flex space. Upgrades include a new roof with gutters and gutter guards (2022), new water heaters (2023), interior paint (2021) exterior paint (2023), water filtration, system, dual propane tanks, security system, plantation shutters, and three AC units. The above garage attic is accessible by staircase and can easily be enclosed to make a 5th bedroom, game room or flex space. This lakefront sanctuary offers privacy, sophistication, and modern convenience plus is located just minutes from Park Avenue's charming shops and restaurants. Don’t miss the opportunity to make this lake front home yours. Schedule your private showing today!

3 Beds ⋅ 3 Baths ⋅ Sylvan Lake Shores SubDv. ⋅ 32789 Zip Code

Experience modern elegance in this stunning Lake Sylvan estate with breathtaking lake views and seamless indoor-outdoor living. The open-concept design features a gourmet kitchen (renovated 2023) with quartzite countertops, a wet bar, and luxe appliances. French doors, a custom gas fireplace, and designer lighting add refined charm to the living room. Step outside to nearly 1500 sqft of additional living space on the lake featuring a heated pool, spa, covered patio with gas fireplace, summer kitchen and lakeside firepit. With three bedrooms and a versatile office (easily a fourth), this home adapts to your needs. The first-floor primary suite opens to the pool, while an upstairs primary suite has dual custom closets, a spa-like bath, and a private flex space. Upgrades include a new roof with gutters and gutter guards (2022), new water heaters (2023), interior paint (2021) exterior paint (2023), water filtration, system, dual propane tanks, security system, plantation shutters, and three AC units. The above garage attic is accessible by staircase and can easily be enclosed to make a 5th bedroom, game room or flex space. This lakefront sanctuary offers privacy, sophistication, and modern convenience plus is located just minutes from Park Avenue's charming shops and restaurants. Don’t miss the opportunity to make this lake front home yours. Schedule your private showing today!

254 Sylvan Boulevard, Winter Park

$520,000

Under contract. Listing agent is the owner.

3 Beds ⋅ 2 Baths ⋅ Orange Grove Sub SubDv. ⋅ 32789 Zip Code

Under contract. Listing agent is the owner.

1810 Taylor Ave, Winter Park

$362,500

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!

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

$850,000

Stunning fully remodeled Winter Park bungalow featuring a 500 square foot detached guest house. This charming residence is perfectly positioned on a rare oversized .41-acre double lot and has been completely transformed, offering a harmonious blend of modern luxury and timeless elegance. The main house features 4 bedrooms and 2.5 baths while the guest house features a living room, bedroom, kitchenette, and a full bathroom. Step inside and you are immediately greeted by a bright, spacious open floor plan. Designed for effortless entertaining, this home features a sleek modern wet bar complete with an under counter ice maker, additional dishwasher, and wine fridge! The gourmet kitchen is a true masterpiece, featuring top-of-the-line stainless steel appliances, upgraded countertops, a walk-in pantry, a large butcher block center island, tile backsplash, and loads of custom cabinetry. There is even a pass-through window to a bar area on the covered lanai. The luxurious primary suite provides a serene escape, designed as a private retreat where you can unwind in ultimate comfort. It boasts an impressive closet and a spa-inspired en-suite bath, complete with a freestanding soaking tub, dual vanities, and a spacious walk-in shower. Outside, the home continues to impress with its private backyard oasis provided by the rare double lot. A sparkling screened in pool, set against lush landscaping, serves as the centerpiece of the expansive patio area. In addition, the beautifully landscaped yard holds a custom fire pit, elevated covered wooden lanai and garden boxes to create the perfect setting for relaxation and gatherings. There is also a spacious covered deck, and a large storage shed. Last but not least, your guest will love the privacy provided by the detached guest house overlooking the pool. Jump on your golf cart and within minutes you’re transported to Park Ave, with its amazing shops, fine dining, and everything else that Winter Park has to offer. Don't miss the opportunity to make this unique Winter Park home yours!

5 Beds ⋅ 4 Baths ⋅ Temple Terrace SubDv. ⋅ 32789 Zip Code

Stunning fully remodeled Winter Park bungalow featuring a 500 square foot detached guest house. This charming residence is perfectly positioned on a rare oversized .41-acre double lot and has been completely transformed, offering a harmonious blend of modern luxury and timeless elegance. The main house features 4 bedrooms and 2.5 baths while the guest house features a living room, bedroom, kitchenette, and a full bathroom. Step inside and you are immediately greeted by a bright, spacious open floor plan. Designed for effortless entertaining, this home features a sleek modern wet bar complete with an under counter ice maker, additional dishwasher, and wine fridge! The gourmet kitchen is a true masterpiece, featuring top-of-the-line stainless steel appliances, upgraded countertops, a walk-in pantry, a large butcher block center island, tile backsplash, and loads of custom cabinetry. There is even a pass-through window to a bar area on the covered lanai. The luxurious primary suite provides a serene escape, designed as a private retreat where you can unwind in ultimate comfort. It boasts an impressive closet and a spa-inspired en-suite bath, complete with a freestanding soaking tub, dual vanities, and a spacious walk-in shower. Outside, the home continues to impress with its private backyard oasis provided by the rare double lot. A sparkling screened in pool, set against lush landscaping, serves as the centerpiece of the expansive patio area. In addition, the beautifully landscaped yard holds a custom fire pit, elevated covered wooden lanai and garden boxes to create the perfect setting for relaxation and gatherings. There is also a spacious covered deck, and a large storage shed. Last but not least, your guest will love the privacy provided by the detached guest house overlooking the pool. Jump on your golf cart and within minutes you’re transported to Park Ave, with its amazing shops, fine dining, and everything else that Winter Park has to offer. Don't miss the opportunity to make this unique Winter Park home yours!

1832 Magnolia Avenue, Winter Park

$2,910,000

Set on a sprawling half-acre, surrounded by meticulously manicured landscaping, this custom-built traditional estate exemplifies refined luxury, modern convenience, and an unparalleled lifestyle. The red brick façade, covered porches with glass doors, and gated side porte-cochere set a timeless tone, while two-story fluted columns add stately elegance. Inside, classic architectural details merge with modern design, highlighted by two-story coffered ceilings, intricate millwork, and expansive windows and French doors that flood the home with natural light. Thoughtfully designed for both entertaining and everyday living, the gourmet kitchen includes a 6-burner Viking gas cooktop, double dishwashers and sinks, a paneled refrigerator and separate full-sized freezer, a walk-in pantry, and an oversized island with breakfast bar seating. The first floor features a private primary retreat, two powder rooms, a workstation/mudroom accessible off the porte-cochere, and one of two laundry rooms. Upstairs offers three spacious bedroom suites with walk-in closets, a versatile bonus room, and a second laundry room. Embrace the Florida lifestyle from a two-story covered brick patio with a built-in gas grill, overlooking the private, fenced-in backyard oasis and breathtaking saltwater pool and heated spa, all elevated by a three-tier fountain and fire pit area, and wrapped in lush landscaping; this outdoor space is truly magical and not easily replicated in Winter Park! A circular driveway provides ample parking, while a gated side drive leads to an oversized, detached three-car garage with a bonus room above—ideal for a gym or studio. This particularly grand, wide street in the City of Winter Park is something truly special. Ideally located near Baldwin Park, Corrine Drive, and Park Avenue, and zoned for highly regarded Audubon K-8, this estate is more than a home—it’s a statement in timeless elegance. *Ask for a list of improvements, the floorplan and click on the virtual tour!

4 Beds ⋅ 6 Baths ⋅ Stonehurst Estates SubDv. ⋅ 32789 Zip Code

Set on a sprawling half-acre, surrounded by meticulously manicured landscaping, this custom-built traditional estate exemplifies refined luxury, modern convenience, and an unparalleled lifestyle. The red brick façade, covered porches with glass doors, and gated side porte-cochere set a timeless tone, while two-story fluted columns add stately elegance. Inside, classic architectural details merge with modern design, highlighted by two-story coffered ceilings, intricate millwork, and expansive windows and French doors that flood the home with natural light. Thoughtfully designed for both entertaining and everyday living, the gourmet kitchen includes a 6-burner Viking gas cooktop, double dishwashers and sinks, a paneled refrigerator and separate full-sized freezer, a walk-in pantry, and an oversized island with breakfast bar seating. The first floor features a private primary retreat, two powder rooms, a workstation/mudroom accessible off the porte-cochere, and one of two laundry rooms. Upstairs offers three spacious bedroom suites with walk-in closets, a versatile bonus room, and a second laundry room. Embrace the Florida lifestyle from a two-story covered brick patio with a built-in gas grill, overlooking the private, fenced-in backyard oasis and breathtaking saltwater pool and heated spa, all elevated by a three-tier fountain and fire pit area, and wrapped in lush landscaping; this outdoor space is truly magical and not easily replicated in Winter Park! A circular driveway provides ample parking, while a gated side drive leads to an oversized, detached three-car garage with a bonus room above—ideal for a gym or studio. This particularly grand, wide street in the City of Winter Park is something truly special. Ideally located near Baldwin Park, Corrine Drive, and Park Avenue, and zoned for highly regarded Audubon K-8, this estate is more than a home—it’s a statement in timeless elegance. *Ask for a list of improvements, the floorplan and click on the virtual tour!

1911 Stonehurst Road, Winter Park

$540,000

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.

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

$1,395,000

Under contract-accepting backup offers. AMAZING opportunity to build your new home in this phenomenal neighborhood! The existing home is a tear-down and the value of the property lies in the expansive 13,441 sf (.31 Acre) lot. With this tremendous 100 ft wide lot, the property affords any new buyer ample space to build their dream home. Plus, the locale is ideal...Tucked away on a charming, quiet brick street, the property is an easy stroll to Phelps Park and the Y. Plus, you are a short ride to Downtown Park Avenue's shops and restaurants. This is an opportunity not to be missed! SOLD AS-IS.

Comstock Park SubDv. ⋅ 32789 Zip Code

Under contract-accepting backup offers. AMAZING opportunity to build your new home in this phenomenal neighborhood! The existing home is a tear-down and the value of the property lies in the expansive 13,441 sf (.31 Acre) lot. With this tremendous 100 ft wide lot, the property affords any new buyer ample space to build their dream home. Plus, the locale is ideal...Tucked away on a charming, quiet brick street, the property is an easy stroll to Phelps Park and the Y. Plus, you are a short ride to Downtown Park Avenue's shops and restaurants. This is an opportunity not to be missed! SOLD AS-IS.

1560 Lakehurst Avenue, Winter Park

$825,000

Discover modern living at its finest in this stunning contemporary home in the heart of Winter Park! Built in 2020, this spacious four-bedroom, 2.5-bath residence offers over 2,500 square feet of beautifully designed living space ideal for families of all sizes. The first floor features a bright, open-concept kitchen with sleek finishes, a large island and ample storage, seamlessly flowing into a spacious living area, and ideal for family gatherings and entertaining. Upstairs, the luxurious primary suite offers a private retreat with a large en-suite bath, while three additional bedrooms provide plenty of space for guests, or a home office. At top of the stairs, you'll find a versatile loft space, ideal for a playroom, media area or additional lounge. Step outside to enjoy the expansive backyard, complete with a large privacy fence, offering plenty of space for families and pets to play or to host outdoor gatherings. This home is in a prime location, only a short distance to Dubsdread Golf Course. It’s also just minutes from Park Avenue, College Park and downtown Orlando, offering easy access to dining, shopping and entertainment. Plus, with quick access to Interstate 4, commuting anywhere in Central Florida is effortless. This home is a rare find. Don’t miss your chance to make it yours, schedule your showing today.

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

Discover modern living at its finest in this stunning contemporary home in the heart of Winter Park! Built in 2020, this spacious four-bedroom, 2.5-bath residence offers over 2,500 square feet of beautifully designed living space ideal for families of all sizes. The first floor features a bright, open-concept kitchen with sleek finishes, a large island and ample storage, seamlessly flowing into a spacious living area, and ideal for family gatherings and entertaining. Upstairs, the luxurious primary suite offers a private retreat with a large en-suite bath, while three additional bedrooms provide plenty of space for guests, or a home office. At top of the stairs, you'll find a versatile loft space, ideal for a playroom, media area or additional lounge. Step outside to enjoy the expansive backyard, complete with a large privacy fence, offering plenty of space for families and pets to play or to host outdoor gatherings. This home is in a prime location, only a short distance to Dubsdread Golf Course. It’s also just minutes from Park Avenue, College Park and downtown Orlando, offering easy access to dining, shopping and entertainment. Plus, with quick access to Interstate 4, commuting anywhere in Central Florida is effortless. This home is a rare find. Don’t miss your chance to make it yours, schedule your showing today.

705 Baffie Avenue, Winter Park

$412,000

Location, Location, Location - downtown Winter Park condo for under $500K! This dramatic 2 bedroom - 2 Bath ground floor unit is located on corner of Swoop and Interlachen, steps from the Winter Park 9 Golf Course and Park Avenue! Beautiful views, glassed in porch overlooking stunning landscape. This unit offers high ceilings, open, updated kitchen to living areas, sunroom (enclosed porch) large primary suite and guest room. Two full baths. Large utility room. Designer lighting. Open floor plan, light and bright! A/C 2018. The charming Andalucia complex, which consists of only 20 units, offers access to a lovely covered patio downstairs, an elevator, courtyard, and a community laundry room. The community also provides a private storage room for this unit. The roof was replaced in 2024. The exterior was painted, and new gates were installed in 2018. One covered parking space is included. Additional guest parking is available in the rear. The condo fee covers water, sewer, Spectrum WiFi and cable TV, landscaping and exterior maintenance, garbage, insurance on the exterior building, and reserves. Please note: No pets or rentals allowed. Call today for your private viewing of this special unit.

2 Beds ⋅ 2 Baths ⋅ Andalucia Apts SubDv. ⋅ 32789 Zip Code

Location, Location, Location - downtown Winter Park condo for under $500K! This dramatic 2 bedroom - 2 Bath ground floor unit is located on corner of Swoop and Interlachen, steps from the Winter Park 9 Golf Course and Park Avenue! Beautiful views, glassed in porch overlooking stunning landscape. This unit offers high ceilings, open, updated kitchen to living areas, sunroom (enclosed porch) large primary suite and guest room. Two full baths. Large utility room. Designer lighting. Open floor plan, light and bright! A/C 2018. The charming Andalucia complex, which consists of only 20 units, offers access to a lovely covered patio downstairs, an elevator, courtyard, and a community laundry room. The community also provides a private storage room for this unit. The roof was replaced in 2024. The exterior was painted, and new gates were installed in 2018. One covered parking space is included. Additional guest parking is available in the rear. The condo fee covers water, sewer, Spectrum WiFi and cable TV, landscaping and exterior maintenance, garbage, insurance on the exterior building, and reserves. Please note: No pets or rentals allowed. Call today for your private viewing of this special unit.

535 N Interlachen Avenue Unit 107, Winter Park

$3,200,000

Located in the heart of Winter Park this exquisite modern residence built by Vimaro Homes features almost 5,000 square feet of luxury living space. As you step through the glass front doors, you’re immediately greeted by the grandeur of the marble entry floors and custom archways, setting the tone for the exceptional finishes throughout this stunning home. From the gorgeous wood floors laid in a herring bone pattern, to the designer light fixtures, arched doorways, and beautiful mill work, no expense was spared in the construction of this remarkable residence. The chef’s kitchen features exquisite custom cabinetry, marble countertops, a massive butler’s pantry, top of the line appliances including a ILVE Nostalgie range, and a wine cellar. The great room features a wall of glass that opens to the spacious covered lanai blending the indoor and outdoor spaces. The primary bedroom suite overlooks the private back yard and features a spa bath that would rival even the most prominent spas. Last but not least there is a massive walk in closet with separate his and hers sections, and a washer and dryer. Additional features include a first-floor game room, home office, formal dining room, a second floor loft area, 4 additional bedrooms, and second floor laundry room. Situated on a spacious lot, this property features a circular driveway, and a large, fenced yard with mature landscaping, perfect for outdoor activities and entertaining. The highlight of this home is the inviting pool, providing a refreshing oasis for those hot summer days. Jump on your golf cart and within minutes you’re transported to Park Ave, with its amazing shops, fine dining, and everything else that Winter Park has to offer. Don’t miss your opportunity to own this stunning Winter Park home crafted by renowned builder Vimaro Homes.

5 Beds ⋅ 5 Baths ⋅ Kenilworth Shores Sec 01 SubDv. ⋅ 32789 Zip Code

Located in the heart of Winter Park this exquisite modern residence built by Vimaro Homes features almost 5,000 square feet of luxury living space. As you step through the glass front doors, you’re immediately greeted by the grandeur of the marble entry floors and custom archways, setting the tone for the exceptional finishes throughout this stunning home. From the gorgeous wood floors laid in a herring bone pattern, to the designer light fixtures, arched doorways, and beautiful mill work, no expense was spared in the construction of this remarkable residence. The chef’s kitchen features exquisite custom cabinetry, marble countertops, a massive butler’s pantry, top of the line appliances including a ILVE Nostalgie range, and a wine cellar. The great room features a wall of glass that opens to the spacious covered lanai blending the indoor and outdoor spaces. The primary bedroom suite overlooks the private back yard and features a spa bath that would rival even the most prominent spas. Last but not least there is a massive walk in closet with separate his and hers sections, and a washer and dryer. Additional features include a first-floor game room, home office, formal dining room, a second floor loft area, 4 additional bedrooms, and second floor laundry room. Situated on a spacious lot, this property features a circular driveway, and a large, fenced yard with mature landscaping, perfect for outdoor activities and entertaining. The highlight of this home is the inviting pool, providing a refreshing oasis for those hot summer days. Jump on your golf cart and within minutes you’re transported to Park Ave, with its amazing shops, fine dining, and everything else that Winter Park has to offer. Don’t miss your opportunity to own this stunning Winter Park home crafted by renowned builder Vimaro Homes.

1833 Loch Berry Road, Winter Park

$1,305,000

Back on the market at no fault of the seller. Step into the charm of old Florida with this stunning historic home in the heart of Winter Park's exclusive Sevilla neighborhood. Built in 1973 by Charles Clayton, this beautifully preserved residence seamlessly blends timeless elegance with modern comforts. Featuring original hardwood floors, intricate crown molding, and a cozy wood-burning fireplace, every detail reflects meticulous craftsmanship and a timeless aesthetic. The updated gourmet kitchen boasts high-end appliances while maintaining its classic appeal. Nestled on a tree-lined brick street, the home sits on a lushly landscaped lot with a spacious backyard, including a 64,000 gallon custom pool, perfect for enjoying Florida's warm evenings. Just minutes from Park Avenue's boutiques, restaurants, and within walking distance of A-rated schools, this rare gem offers the perfect blend of history, luxury, and location. Don't miss your chance to own a piece of Winter Park's rich heritage!

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

Back on the market at no fault of the seller. Step into the charm of old Florida with this stunning historic home in the heart of Winter Park's exclusive Sevilla neighborhood. Built in 1973 by Charles Clayton, this beautifully preserved residence seamlessly blends timeless elegance with modern comforts. Featuring original hardwood floors, intricate crown molding, and a cozy wood-burning fireplace, every detail reflects meticulous craftsmanship and a timeless aesthetic. The updated gourmet kitchen boasts high-end appliances while maintaining its classic appeal. Nestled on a tree-lined brick street, the home sits on a lushly landscaped lot with a spacious backyard, including a 64,000 gallon custom pool, perfect for enjoying Florida's warm evenings. Just minutes from Park Avenue's boutiques, restaurants, and within walking distance of A-rated schools, this rare gem offers the perfect blend of history, luxury, and location. Don't miss your chance to own a piece of Winter Park's rich heritage!

1600 Barcelona Way, Winter Park

$580,000

Discover the perfect blend of classic charm and modern potential in this delightful single-family home with endless possibilities, nestled in a prime Winter Park location! This inviting fully fenced home features a comfortable layout with 3 bedrooms and 1 bathroom in the main living area. An exciting attached addition has a separate entrance leading to a spacious 4th bedroom and 2nd bathroom, providing incredible flexibility for your lifestyle. Imagine the possibilities: a private in-law suite, a dedicated home office, or a fantastic game/play room – the choice is yours! This blank slate is ready for your personal touches and creative vision, allowing you to transform it into your dream home. Step inside to find a light-filled interior boasting higher ceilings in the living and dining rooms, creating an airy and welcoming atmosphere.Natural sunlight streams through the windows, highlighting the durable and updated laminate flooring – no carpet here! The kitchen is equipped with newer appliances and classic wood cabinets, ready for your culinary adventures. Recent updates include a new AC unit (2024) ensuring year-round comfort, and a roof that’s only 10 years old, providing peace of mind. Outside, a generously sized, fully fenced yard offers the perfect setting for gatherings, barbecues, and outdoor enjoyment. Don't miss this incredible opportunity to own a versatile and well-located home, walking distance to Baldwin Park, access to top-rated schools, premier shopping, and major roadways. This is your opportunity to own a piece of Winter Park paradise, combining a sought-after location with versatile living options. Don't miss out and schedule your private tour today!

4 Beds ⋅ 2 Baths ⋅ Northwood Terrace SubDv. ⋅ 32789 Zip Code

Discover the perfect blend of classic charm and modern potential in this delightful single-family home with endless possibilities, nestled in a prime Winter Park location! This inviting fully fenced home features a comfortable layout with 3 bedrooms and 1 bathroom in the main living area. An exciting attached addition has a separate entrance leading to a spacious 4th bedroom and 2nd bathroom, providing incredible flexibility for your lifestyle. Imagine the possibilities: a private in-law suite, a dedicated home office, or a fantastic game/play room – the choice is yours! This blank slate is ready for your personal touches and creative vision, allowing you to transform it into your dream home. Step inside to find a light-filled interior boasting higher ceilings in the living and dining rooms, creating an airy and welcoming atmosphere.Natural sunlight streams through the windows, highlighting the durable and updated laminate flooring – no carpet here! The kitchen is equipped with newer appliances and classic wood cabinets, ready for your culinary adventures. Recent updates include a new AC unit (2024) ensuring year-round comfort, and a roof that’s only 10 years old, providing peace of mind. Outside, a generously sized, fully fenced yard offers the perfect setting for gatherings, barbecues, and outdoor enjoyment. Don't miss this incredible opportunity to own a versatile and well-located home, walking distance to Baldwin Park, access to top-rated schools, premier shopping, and major roadways. This is your opportunity to own a piece of Winter Park paradise, combining a sought-after location with versatile living options. Don't miss out and schedule your private tour today!

3006 Northwood Boulevard, Winter Park

$1,850,000

This Mediterranean-style, Windsong pool home is sure to check every box, with a 3-car garage, screened rear patio, heated spa and pool, and an ideal, 3-way split-bedroom floorplan on the 1st floor. The large kitchen sits at the heart of the home with a dinette showcasing pool views, an island with a gas cooktop, and a breakfast bar overlooking the sunny family room. Separate living and dining rooms off the foyer offer flexibility and additional space to entertain with ease. To the left of the foyer, enjoy a large, private office with a storage closet. Just past the office, the Primary Suite is situated on one end of the home for optimal privacy and features his and hers walk-in closets, a renovated bathroom, and access to the screened rear patio. At the other end of the home, a secondary bedroom with a full en-suite bathroom makes a great guest or in-law suite, while 2 additional bedrooms, a full hall bath, storage closet, and spacious laundry room complete the 1st floor. Upstairs, the private bonus room, complete with a walk-in closet and full en-suite bathroom, makes a perfect 5th bedroom. French doors from the family room, living room, and Primary bedroom all lead to a screened rear patio that overlooks a fully-fenced backyard where lush landscaping wraps around the resort-style heated pool and spa with water features. In addition to the massive driveway and expanded parking pad, the oversized 3-car garage provides extra parking and storage space. As one of the most coveted neighborhoods in Winter Park, Windsong offers countless amenities, including private lake access for residents. This premium location is just steps from Baldwin Park, East End Market, the Corrine Drive corridor, and minutes from downtown Park Avenue.

5 Beds ⋅ 5 Baths ⋅ Windsong Elizabeths Walk 43/81 SubDv. ⋅ 32789 Zip Code

This Mediterranean-style, Windsong pool home is sure to check every box, with a 3-car garage, screened rear patio, heated spa and pool, and an ideal, 3-way split-bedroom floorplan on the 1st floor. The large kitchen sits at the heart of the home with a dinette showcasing pool views, an island with a gas cooktop, and a breakfast bar overlooking the sunny family room. Separate living and dining rooms off the foyer offer flexibility and additional space to entertain with ease. To the left of the foyer, enjoy a large, private office with a storage closet. Just past the office, the Primary Suite is situated on one end of the home for optimal privacy and features his and hers walk-in closets, a renovated bathroom, and access to the screened rear patio. At the other end of the home, a secondary bedroom with a full en-suite bathroom makes a great guest or in-law suite, while 2 additional bedrooms, a full hall bath, storage closet, and spacious laundry room complete the 1st floor. Upstairs, the private bonus room, complete with a walk-in closet and full en-suite bathroom, makes a perfect 5th bedroom. French doors from the family room, living room, and Primary bedroom all lead to a screened rear patio that overlooks a fully-fenced backyard where lush landscaping wraps around the resort-style heated pool and spa with water features. In addition to the massive driveway and expanded parking pad, the oversized 3-car garage provides extra parking and storage space. As one of the most coveted neighborhoods in Winter Park, Windsong offers countless amenities, including private lake access for residents. This premium location is just steps from Baldwin Park, East End Market, the Corrine Drive corridor, and minutes from downtown Park Avenue.

1627 Elizabeths Walk, Winter Park

$602,500

This beautifully updated 3 bedroom, 3 bath home offers a perfect blend of rustic charm and modern convenience in a highly desirable location. The open floor plan is warm and inviting, with stylish finishes and thoughtful updates that make it truly move-in ready. Each bedroom features its own ensuite bath and a spacious walk-in closet, with both upstairs suites offering the flexibility to serve as a primary retreat. Recent improvements include a brand new hot water heater, new refrigerator, an added mini-split in the garage for enhanced comfort, a water softener system, and a recently replaced A/C. The fenced backyard has been upgraded to turf for easy maintenance, complemented by a private deck—perfect for relaxing or entertaining. Two balconies, including one with a view of the Rollins College baseball field, provide additional peaceful retreats. The attached two-car garage offers both convenience and extra security. Located within walking distance of Park Avenue, Rollins College, and Hannibal Square, this home provides easy access to shopping, dining, and entertainment while maintaining a quiet and private feel. A rare opportunity in an unbeatable location—don’t miss it!

3 Beds ⋅ 3 Baths ⋅ Arbors/Aragon SubDv. ⋅ 32789 Zip Code

This beautifully updated 3 bedroom, 3 bath home offers a perfect blend of rustic charm and modern convenience in a highly desirable location. The open floor plan is warm and inviting, with stylish finishes and thoughtful updates that make it truly move-in ready. Each bedroom features its own ensuite bath and a spacious walk-in closet, with both upstairs suites offering the flexibility to serve as a primary retreat. Recent improvements include a brand new hot water heater, new refrigerator, an added mini-split in the garage for enhanced comfort, a water softener system, and a recently replaced A/C. The fenced backyard has been upgraded to turf for easy maintenance, complemented by a private deck—perfect for relaxing or entertaining. Two balconies, including one with a view of the Rollins College baseball field, provide additional peaceful retreats. The attached two-car garage offers both convenience and extra security. Located within walking distance of Park Avenue, Rollins College, and Hannibal Square, this home provides easy access to shopping, dining, and entertainment while maintaining a quiet and private feel. A rare opportunity in an unbeatable location—don’t miss it!

777 S Denning Drive Unit B, Winter Park

$478,000

FSBO

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

FSBO

2877 Euston Road, Winter Park

$1,500,000

Nestled in the heart of Winter Park, this stunning 4-bedroom, 3-bathroom pool home offers the perfect balance of elegance and convenience. Just minutes from shopping, fantastic dining, popular Phelps Park, the YMCA, the renowned Interlachen Country Club, and the lively Park Avenue, this location has it all. As you approach, a charming front porch shaded by majestic oak trees welcomes you home. Step inside to discover a beautifully designed main floor, featuring a formal dining room, a versatile office space, and a kitchen that effortlessly flows into the family room. The kitchen is every chef’s dream, with gorgeous granite countertops, premium stainless steel appliances, a large breakfast bar, and a cozy breakfast nook. From here, enjoy stunning views of the lagoon-style pool, making meal prep a breeze. The family room, complete with custom built-in shelving and French doors, opens up to a screened-in lanai, offering the perfect space for relaxation or entertaining. The spacious primary suite on the main floor is a true sanctuary, featuring a walk-in closet, a luxurious soaking tub, dual sinks, and a spacious shower. Large windows provide beautiful views of the pool and tranquil backyard. A generously sized laundry room, a full bathroom, and a flexible room complete the main floor. The flexible room, conveniently located just off the kitchen, could serve as a guest room or playroom. Upstairs, you'll find three spacious bedrooms and a Jack and Jill bathroom with a soaking tub, separate shower, and dual sinks. The third bedroom can easily function as a bonus room, depending on your needs. Entertain in style in the private, peaceful backyard, where the lagoon-style pool and spa with a rock feature and waterfall from the spa create a serene ambiance. The screened-in lanai is the perfect spot to sip your morning coffee or unwind with a glass of wine while enjoying nature’s beauty. Plus, with top-rated Winter Park Schools, this home offers everything you need!

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

Nestled in the heart of Winter Park, this stunning 4-bedroom, 3-bathroom pool home offers the perfect balance of elegance and convenience. Just minutes from shopping, fantastic dining, popular Phelps Park, the YMCA, the renowned Interlachen Country Club, and the lively Park Avenue, this location has it all. As you approach, a charming front porch shaded by majestic oak trees welcomes you home. Step inside to discover a beautifully designed main floor, featuring a formal dining room, a versatile office space, and a kitchen that effortlessly flows into the family room. The kitchen is every chef’s dream, with gorgeous granite countertops, premium stainless steel appliances, a large breakfast bar, and a cozy breakfast nook. From here, enjoy stunning views of the lagoon-style pool, making meal prep a breeze. The family room, complete with custom built-in shelving and French doors, opens up to a screened-in lanai, offering the perfect space for relaxation or entertaining. The spacious primary suite on the main floor is a true sanctuary, featuring a walk-in closet, a luxurious soaking tub, dual sinks, and a spacious shower. Large windows provide beautiful views of the pool and tranquil backyard. A generously sized laundry room, a full bathroom, and a flexible room complete the main floor. The flexible room, conveniently located just off the kitchen, could serve as a guest room or playroom. Upstairs, you'll find three spacious bedrooms and a Jack and Jill bathroom with a soaking tub, separate shower, and dual sinks. The third bedroom can easily function as a bonus room, depending on your needs. Entertain in style in the private, peaceful backyard, where the lagoon-style pool and spa with a rock feature and waterfall from the spa create a serene ambiance. The screened-in lanai is the perfect spot to sip your morning coffee or unwind with a glass of wine while enjoying nature’s beauty. Plus, with top-rated Winter Park Schools, this home offers everything you need!

1741 Pine Avenue, Winter Park

$1,800,000

Under Construction. Modern elegance and timeless sophistication define 1682 Arbor Park Dr, a meticulously crafted new construction home in the heart of Winter Park, FL. Spanning 2,950 square feet, this 4-bedroom, 3.5-bathroom residence also features a dedicated office and a conditioned attic that can be used as a fifth bedroom, offering flexible living space to accommodate a variety of needs. The gourmet kitchen is a standout feature, boasting Thermador appliances, custom cabinetry, and an expansive island, making it ideal for both daily use and entertaining. Included appliances are a 36” gas range, microwave drawer, 36” refrigerator, and dishwasher. Flowing effortlessly into the living and dining areas, the home is bathed in natural light, enhancing its modern yet warm aesthetic. The primary suite, located on the second floor, offers a spa-like retreat with dual vanities, a soaking tub, and a walk-in shower. Also on the second floor are bedrooms three, four, and a conditioned attic space, which serves as an optional fifth bedroom. The first floor includes bedroom two and a dedicated office, offering privacy and convenience. The outdoor living spaces have been thoughtfully curated to provide the ultimate in relaxation and entertainment, featuring a private pool surrounded by lush, manicured landscaping. A separate, elegantly appointed pool cabana further enhances the home’s allure, creating an idyllic space for leisure or hosting guests in style. Located just moments from Park Avenue, this home offers unrivaled access to Winter Park’s finest boutique shopping, gourmet dining, and the vibrant lifestyle for which the area is known. Utilities include electricity, water, sewer, and gas connection. 1682 Arbor Park Dr is a rare opportunity to experience the pinnacle of luxury living, where modern sophistication and timeless charm come together to create an exceptional residence. Please note: Images shown are renderings and are for illustrative purposes only. Final construction details, finishes, and features may vary.

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

Under Construction. Modern elegance and timeless sophistication define 1682 Arbor Park Dr, a meticulously crafted new construction home in the heart of Winter Park, FL. Spanning 2,950 square feet, this 4-bedroom, 3.5-bathroom residence also features a dedicated office and a conditioned attic that can be used as a fifth bedroom, offering flexible living space to accommodate a variety of needs. The gourmet kitchen is a standout feature, boasting Thermador appliances, custom cabinetry, and an expansive island, making it ideal for both daily use and entertaining. Included appliances are a 36” gas range, microwave drawer, 36” refrigerator, and dishwasher. Flowing effortlessly into the living and dining areas, the home is bathed in natural light, enhancing its modern yet warm aesthetic. The primary suite, located on the second floor, offers a spa-like retreat with dual vanities, a soaking tub, and a walk-in shower. Also on the second floor are bedrooms three, four, and a conditioned attic space, which serves as an optional fifth bedroom. The first floor includes bedroom two and a dedicated office, offering privacy and convenience. The outdoor living spaces have been thoughtfully curated to provide the ultimate in relaxation and entertainment, featuring a private pool surrounded by lush, manicured landscaping. A separate, elegantly appointed pool cabana further enhances the home’s allure, creating an idyllic space for leisure or hosting guests in style. Located just moments from Park Avenue, this home offers unrivaled access to Winter Park’s finest boutique shopping, gourmet dining, and the vibrant lifestyle for which the area is known. Utilities include electricity, water, sewer, and gas connection. 1682 Arbor Park Dr is a rare opportunity to experience the pinnacle of luxury living, where modern sophistication and timeless charm come together to create an exceptional residence. Please note: Images shown are renderings and are for illustrative purposes only. Final construction details, finishes, and features may vary.

1682 Arbor Park Drive, Winter Park

$939,000

Top floor direct lakefront view of this Renovated condominium. Professional pictures coming.

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

Top floor direct lakefront view of this Renovated condominium. Professional pictures coming.

100 S Interlachen Avenue Unit 502D, Winter Park

$130,000

SPECIAL FINANCING AVAILABLE! First Horizon Home Start w/ Diversity Grant available for this home while funds last. This grant funds up to 100% LTV, no PMI, Minimum borrower contribution of $500, and diversity grant of $8,000 (with no repayment) for an affordable home in a prime location? This budget-friendly 2-bedroom, 1-bath condo is move-in ready! Freshly painted ceilings, walls, trim, doors, and even a refreshed bathtub and tile give the space a bright and updated feel. Step out onto the shaded back deck, where a beautiful tree provides the perfect spot to unwind and enjoy Florida’s amazing weather or take a short walk to the community pool and club house. You can’t beat this location! With easy access to I-4, commuting is a breeze—whether you're heading to downtown Orlando, the beaches on either coast, two international airports, or world-famous attractions like Disney, Universal, SeaWorld, Legoland, and more. Don’t miss out on this opportunity! Call today to schedule your showing.

2 Beds ⋅ 1 Baths ⋅ Waterfall Cove SubDv. ⋅ 32789 Zip Code

SPECIAL FINANCING AVAILABLE! First Horizon Home Start w/ Diversity Grant available for this home while funds last. This grant funds up to 100% LTV, no PMI, Minimum borrower contribution of $500, and diversity grant of $8,000 (with no repayment) for an affordable home in a prime location? This budget-friendly 2-bedroom, 1-bath condo is move-in ready! Freshly painted ceilings, walls, trim, doors, and even a refreshed bathtub and tile give the space a bright and updated feel. Step out onto the shaded back deck, where a beautiful tree provides the perfect spot to unwind and enjoy Florida’s amazing weather or take a short walk to the community pool and club house. You can’t beat this location! With easy access to I-4, commuting is a breeze—whether you're heading to downtown Orlando, the beaches on either coast, two international airports, or world-famous attractions like Disney, Universal, SeaWorld, Legoland, and more. Don’t miss out on this opportunity! Call today to schedule your showing.

1695 Lee Road Unit E205, Winter Park

$3,550,000

This single-story home offers serene lakefront living with approximately 95 feet of prime water frontage on beautiful Lake Osceola. Whether you enjoy watersports, boating, or simply relaxing by the water, this property can provide the true joy of lakefront living. The grandfathered boat dock provides a rare opportunity for transformation, perfect for customizing your ideal lakeside retreat. The home boasts breathtaking lake views from the primary retreat, family room, dining room, and Florida room, providing a seamless connection to nature. Upon entering, you're greeted by a spacious living room that flows effortlessly into the family room. Adjacent to the living room is a formal dining room, ideal for entertaining guests. The expansive primary retreat has dual closets. Across from the primary, a generously sized bedroom features its own ensuite bathroom. The kitchen, located off the dining room, also captures stunning views of the lake, making it a delightful space. An additional bedroom with an ensuite bathroom provides privacy and comfort, while a half bath is conveniently located near this bedroom. A second half bathroom is situated in the garage. A recent update includes a new roof installed in 2022. The property spans .61 acres, providing plenty of room for future development. Located on one of Winter Park's most beautiful streets, this home is just a short walk from the charming shops and restaurants of Park Avenue and Rollins College. Experience the best of lakeside living and the vibrant Winter Park community from this stunning property. Opportunity awaits the buyer of this gorgeous property!

3 Beds ⋅ 5 Baths ⋅ Osceola Shores Sec 03 SubDv. ⋅ 32789 Zip Code

This single-story home offers serene lakefront living with approximately 95 feet of prime water frontage on beautiful Lake Osceola. Whether you enjoy watersports, boating, or simply relaxing by the water, this property can provide the true joy of lakefront living. The grandfathered boat dock provides a rare opportunity for transformation, perfect for customizing your ideal lakeside retreat. The home boasts breathtaking lake views from the primary retreat, family room, dining room, and Florida room, providing a seamless connection to nature. Upon entering, you're greeted by a spacious living room that flows effortlessly into the family room. Adjacent to the living room is a formal dining room, ideal for entertaining guests. The expansive primary retreat has dual closets. Across from the primary, a generously sized bedroom features its own ensuite bathroom. The kitchen, located off the dining room, also captures stunning views of the lake, making it a delightful space. An additional bedroom with an ensuite bathroom provides privacy and comfort, while a half bath is conveniently located near this bedroom. A second half bathroom is situated in the garage. A recent update includes a new roof installed in 2022. The property spans .61 acres, providing plenty of room for future development. Located on one of Winter Park's most beautiful streets, this home is just a short walk from the charming shops and restaurants of Park Avenue and Rollins College. Experience the best of lakeside living and the vibrant Winter Park community from this stunning property. Opportunity awaits the buyer of this gorgeous property!

443 Lakewood Drive, Winter Park

$205,000

This property located in a peaceful community IN WINTER PARK. and easy access to FL I-4 , short drive distance to Rollins College, UCF, Valencia college, Hospitals, shopping center, restaurants and Orlando Theme Park. This unit located on the second floor, it has 3 bedrooms 2, bathrooms, open floor plan. The community amenities include a large pool with lounge chairs, playground and gazebo. This property can be leased. You must see for any possibilities come and check for yourself. Registered owner is brother of the realtor. SELLER MIGHT HOLD FIRST MORTGAGE WITH A GOOD DOWN PAYMENT.

3 Beds ⋅ 2 Baths ⋅ Waterfall Cove At Winter Park SubDv. ⋅ 32789 Zip Code

This property located in a peaceful community IN WINTER PARK. and easy access to FL I-4 , short drive distance to Rollins College, UCF, Valencia college, Hospitals, shopping center, restaurants and Orlando Theme Park. This unit located on the second floor, it has 3 bedrooms 2, bathrooms, open floor plan. The community amenities include a large pool with lounge chairs, playground and gazebo. This property can be leased. You must see for any possibilities come and check for yourself. Registered owner is brother of the realtor. SELLER MIGHT HOLD FIRST MORTGAGE WITH A GOOD DOWN PAYMENT.

1695 Lee Road Unit C202, Winter Park

$367,500

One or more photo(s) has been virtually staged. An awesome home for young professionals or family or great rental for an Investor! Fantastic location! Welcome to this charming 3-bedroom, 2-bathroom Winter Park home. The combination of original wood floors and plaster walls keep the integrity of the home. An updated kitchen with gorgeous cabinets and granite countertops with space for 3 bar stools and NEW APPLIANCES adds a perfect blend of charm and modern convenience. The interior has been freshly painted. The bathroom was renovated to maintain the character of the home. The large living room is filled with light, and the additional versatile family room can be used as a home office, dining room, or exercise space. There are two nice sized bedrooms on the main floor and the upstairs bonus room includes a bedroom an ensuite bathroom and air conditioned attic space for storage. It could also be a great man cave, office or teenager private space. The beautiful totally fenced treed backyard and one-car garage with a workshop area and its own toilet, along with a carport, add to the home's appeal. The seller is offering a two year home warranty! Conveniently located near I-4, Park Avenue, Winter Park Village, Dubsdread Golf Course, restaurants and shopping and downtown Orlando

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

One or more photo(s) has been virtually staged. An awesome home for young professionals or family or great rental for an Investor! Fantastic location! Welcome to this charming 3-bedroom, 2-bathroom Winter Park home. The combination of original wood floors and plaster walls keep the integrity of the home. An updated kitchen with gorgeous cabinets and granite countertops with space for 3 bar stools and NEW APPLIANCES adds a perfect blend of charm and modern convenience. The interior has been freshly painted. The bathroom was renovated to maintain the character of the home. The large living room is filled with light, and the additional versatile family room can be used as a home office, dining room, or exercise space. There are two nice sized bedrooms on the main floor and the upstairs bonus room includes a bedroom an ensuite bathroom and air conditioned attic space for storage. It could also be a great man cave, office or teenager private space. The beautiful totally fenced treed backyard and one-car garage with a workshop area and its own toilet, along with a carport, add to the home's appeal. The seller is offering a two year home warranty! Conveniently located near I-4, Park Avenue, Winter Park Village, Dubsdread Golf Course, restaurants and shopping and downtown Orlando

1975 Staunton Avenue, Winter Park

$4,100,000

Welcome home to this one-of-a-kind custom-designed and built home by Ferrarini Custom Homes, Inc. in February 2024. This singular mid-century modern home is like no other in Winter Park. Boasting an ideal location just steps from Phelps Park as well as only 1.5 miles from Park Avenue makes it the ideal home for the most discerning buyer. Custom features abound in this stunning 4582 sq. ft. masterpiece, including white oak floors, beams, and wood details in most rooms, 5 BRs, and 4.5 BAs. The first floor features a primary suite and guest suite as well as an office, great room, dedicated bar, dining area, and exquisite kitchen with a secret pass-through door to the scullery. The second level boasts three generously sized bedrooms and two baths. Cable wire railing, stone, wood inlay details, custom front door, oversized lanai with summer kitchen, outdoor fireplace, huge pool with firepit and separate firepit conversation area, the list goes on and on... This unique lot is a rare find in Winter Park - oversized in both width and depth with dimensions of 155’ deep and 143’ wide. The interior features over 6600 square feet under roof and a 4-car garage with a work-bench area included. The outdoor area features a 34-foot patio with a built-in gas grill, gas fireplace, and large-format porcelain pavers. The remote screen provides you with ease of access to your custom-designed pool with pebbletec, an outdoor shower, and a firepit nestled amongst the landscaping. The rear yard is completely irrigated and includes a well for irrigation to keep water expenses down significantly. The custom-designed pool is large for Winter Park, featuring a lounging shelf as well as a 10’ fire feature and swim-out. The massive deck is adorned with wood-like porcelain pavers with a porcelain coping. Smart home features in this home include wireless controls for audio, a/c, garage doors, pool equipment, lighting, and exterior cameras. Additionally there is upgraded spray foam insulation, gas appliances (water heaters, fireplaces, washer, range), and an elevation featuring Cultured stone, Hardi Siding, and a Jeldwyn 10’ front entry door. Herringbone pavers lead you from the cobblestone street to the magnificent front entry. Buyers will enjoy the extensive landscaping and privacy hedges. The landscaping is mature for a brand-new home! Privacy abounds everywhere in this home. Custom landscape lighting adds to the estate feel of this home. The gourmet kitchen features all Wolf and Sub-zero appliances, which include a Wolf range, Wolf 2cd oven, steam oven, Sharp microwave, Cove dishwasher with custom wood panel, a Sub-zero Refrigerator with custom panel, and a Sub-zero Freezer also with a custom panel. Disguised between the refrigerator and freezer is a secret hidden door to the scullery. Exotic countertops abound throughout the house. Quartzite like you have never seen before is evident in the kitchen and bar. Antolini Italian marble that was specially treated with “Zerocare Plus” can be found on the kitchen counters and kitchen backsplash. Custom cabinetry throughout the house, featuring white oak. Additional appliances include 3 beverage refrigerators, 1 wine refrigerator, ice maker, and a secondary 36” refrigerator. Every detail has been thought-out and implemented for you in this breathtaking home! Do not wait - the work has been done for you with NO waiting time for new construction. This elegant home will not last!

5 Beds ⋅ 5 Baths ⋅ Lake Knowles Terrace SubDv. ⋅ 32789 Zip Code

Welcome home to this one-of-a-kind custom-designed and built home by Ferrarini Custom Homes, Inc. in February 2024. This singular mid-century modern home is like no other in Winter Park. Boasting an ideal location just steps from Phelps Park as well as only 1.5 miles from Park Avenue makes it the ideal home for the most discerning buyer. Custom features abound in this stunning 4582 sq. ft. masterpiece, including white oak floors, beams, and wood details in most rooms, 5 BRs, and 4.5 BAs. The first floor features a primary suite and guest suite as well as an office, great room, dedicated bar, dining area, and exquisite kitchen with a secret pass-through door to the scullery. The second level boasts three generously sized bedrooms and two baths. Cable wire railing, stone, wood inlay details, custom front door, oversized lanai with summer kitchen, outdoor fireplace, huge pool with firepit and separate firepit conversation area, the list goes on and on... This unique lot is a rare find in Winter Park - oversized in both width and depth with dimensions of 155’ deep and 143’ wide. The interior features over 6600 square feet under roof and a 4-car garage with a work-bench area included. The outdoor area features a 34-foot patio with a built-in gas grill, gas fireplace, and large-format porcelain pavers. The remote screen provides you with ease of access to your custom-designed pool with pebbletec, an outdoor shower, and a firepit nestled amongst the landscaping. The rear yard is completely irrigated and includes a well for irrigation to keep water expenses down significantly. The custom-designed pool is large for Winter Park, featuring a lounging shelf as well as a 10’ fire feature and swim-out. The massive deck is adorned with wood-like porcelain pavers with a porcelain coping. Smart home features in this home include wireless controls for audio, a/c, garage doors, pool equipment, lighting, and exterior cameras. Additionally there is upgraded spray foam insulation, gas appliances (water heaters, fireplaces, washer, range), and an elevation featuring Cultured stone, Hardi Siding, and a Jeldwyn 10’ front entry door. Herringbone pavers lead you from the cobblestone street to the magnificent front entry. Buyers will enjoy the extensive landscaping and privacy hedges. The landscaping is mature for a brand-new home! Privacy abounds everywhere in this home. Custom landscape lighting adds to the estate feel of this home. The gourmet kitchen features all Wolf and Sub-zero appliances, which include a Wolf range, Wolf 2cd oven, steam oven, Sharp microwave, Cove dishwasher with custom wood panel, a Sub-zero Refrigerator with custom panel, and a Sub-zero Freezer also with a custom panel. Disguised between the refrigerator and freezer is a secret hidden door to the scullery. Exotic countertops abound throughout the house. Quartzite like you have never seen before is evident in the kitchen and bar. Antolini Italian marble that was specially treated with “Zerocare Plus” can be found on the kitchen counters and kitchen backsplash. Custom cabinetry throughout the house, featuring white oak. Additional appliances include 3 beverage refrigerators, 1 wine refrigerator, ice maker, and a secondary 36” refrigerator. Every detail has been thought-out and implemented for you in this breathtaking home! Do not wait - the work has been done for you with NO waiting time for new construction. This elegant home will not last!

1691 Chestnut Avenue, Winter Park

$4,500,000

"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.

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

$640,000

Welcome to this beautifully designed home in Winter Park! This residence features an open floor plan, modern finishes, and a spacious two-car garage. The home includes tile flooring throughout the living areas, quartz countertops, upgraded light fixtures, and premium appliances. $64,900 in recent upgrades add tremendous value, including a $30,000 lanai, plantation shutters, custom blinds on sliding doors, a storage shed, privacy fencing, upgraded switches and dimmers, and custom cabinetry. The laundry room includes a butcher block folding table for added convenience. With a 2023 roof, HVAC, electrical, and plumbing systems, this home is ready for immediate occupancy. Located just minutes from Park Avenue, offering a variety of shopping, dining, and entertainment options in Winter Park. Contact us today to schedule a showing!

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

Welcome to this beautifully designed home in Winter Park! This residence features an open floor plan, modern finishes, and a spacious two-car garage. The home includes tile flooring throughout the living areas, quartz countertops, upgraded light fixtures, and premium appliances. $64,900 in recent upgrades add tremendous value, including a $30,000 lanai, plantation shutters, custom blinds on sliding doors, a storage shed, privacy fencing, upgraded switches and dimmers, and custom cabinetry. The laundry room includes a butcher block folding table for added convenience. With a 2023 roof, HVAC, electrical, and plumbing systems, this home is ready for immediate occupancy. Located just minutes from Park Avenue, offering a variety of shopping, dining, and entertainment options in Winter Park. Contact us today to schedule a showing!

2739 Riddle Drive, Winter Park

$2,800,000

Discover the pinnacle of luxury and privacy in this stunning Villa Siena penthouse residence, perfectly positioned in the charming brick-lined streets of Winter Park. While nestled in the heart of the city's vibrant dining, shopping, and cultural scene, this exclusive retreat offers unparalleled tranquility and seclusion. Designed for those who appreciate sophistication, this secured building boasts lavish amenities that extend your living space beyond the walls of your penthouse. Host guests in the elegant resident lounge, complete with a bar for entertaining, marvel at rocket launches from the spectacular rooftop terrace, or take advantage of the private conference room, ideal for high-level meetings or remote work. Stay active in the state-of-the-art exercise room, offering convenience and wellness steps from your front door. With private, secured covered parking and concierge-level service, every detail has been designed to elevate your lifestyle. Inside, refined elegance meets cutting-edge technology—custom millwork, exquisite tile work, and smart-home automation blend seamlessly with high-end video conferencing capabilities. Expansive living spaces, soaring ceilings, and generous room sizes create an inviting atmosphere, while every bedroom features a spa-like ensuite and a private balcony to take in the beauty of Winter Park. Enjoy world-class restaurants, boutique shopping, and lively events at the park, all just steps from your front door. With the nearby train station providing effortless access to Orlando and even Miami, your next adventure is always within reach. This penthouse is a rare opportunity—luxury, location, and lifestyle converge in perfect harmony. Schedule your private tour today!

3 Beds ⋅ 4 Baths ⋅ Trovillion Condo SubDv. ⋅ 32789 Zip Code

Discover the pinnacle of luxury and privacy in this stunning Villa Siena penthouse residence, perfectly positioned in the charming brick-lined streets of Winter Park. While nestled in the heart of the city's vibrant dining, shopping, and cultural scene, this exclusive retreat offers unparalleled tranquility and seclusion. Designed for those who appreciate sophistication, this secured building boasts lavish amenities that extend your living space beyond the walls of your penthouse. Host guests in the elegant resident lounge, complete with a bar for entertaining, marvel at rocket launches from the spectacular rooftop terrace, or take advantage of the private conference room, ideal for high-level meetings or remote work. Stay active in the state-of-the-art exercise room, offering convenience and wellness steps from your front door. With private, secured covered parking and concierge-level service, every detail has been designed to elevate your lifestyle. Inside, refined elegance meets cutting-edge technology—custom millwork, exquisite tile work, and smart-home automation blend seamlessly with high-end video conferencing capabilities. Expansive living spaces, soaring ceilings, and generous room sizes create an inviting atmosphere, while every bedroom features a spa-like ensuite and a private balcony to take in the beauty of Winter Park. Enjoy world-class restaurants, boutique shopping, and lively events at the park, all just steps from your front door. With the nearby train station providing effortless access to Orlando and even Miami, your next adventure is always within reach. This penthouse is a rare opportunity—luxury, location, and lifestyle converge in perfect harmony. Schedule your private tour today!

315 E New England Avenue Unit 30, Winter Park

$5,400,000

Extraordinary Waterfront Neoclassical Italian Estate situated on a prime .72-acre corner lot in one of Winter Park's most sought-after locations. This 7,916 SF property includes a main residence of over 7,100 SF, a detached guest house, and a poolside catering suite. The private covered boat dock is located just steps away, across the street, in the historic Kraft Azalea Garden, providing direct lake access with boat and personal watercraft storage on Lake Maitland, without the upkeep of a waterfront backyard. Inside, fresh neutral interiors and beautiful landscaping frame elegant arrival and living spaces. The thoughtful layout offers 5 bedrooms and 5 full plus 4 half baths, including a 550 SF guest house. Expansive entertaining areas flow seamlessly into a private courtyard with a heated pool and spa, covered dining, an outdoor grill, a wood-burning fireplace, and multiple terraces. Highlights include a grand primary suite with dual bathrooms and closets, a two-story wardrobe with an office in one of the primary closets, an impressive entertainment room, and a gourmet kitchen outfitted with Viking appliances, a newly replaced double oven, and a trash compactor. For large-scale entertaining, the detached pool house doubles as a catering suite with prep sink, refrigerator, and wall-to-wall storage. Built by renowned builder Charles Clayton and designed by Marc-Michaels, the home is a masterpiece of solid block construction and timeless detail featuring imported Parisian fireplaces, solid marble columns, both marble and travertine floors, and Venetian plaster walls. A new barrel tile roof (2023) adds lasting value and peace of mind. Ideally located across from Kraft Azalea Garden and near Rollins College, the estate offers a rare combination of waterfront tranquility and walkable access to Park Avenue’s world-class dining, boutiques, and museums. The Winter Park Racquet Club is also just a short golf cart ride away. A rare opportunity to acquire a legacy property with major aesthetic updates already completed and future equity positioned for growth.

5 Beds ⋅ 9 Baths ⋅ J Kronenberger Sub SubDv. ⋅ 32789 Zip Code

Extraordinary Waterfront Neoclassical Italian Estate situated on a prime .72-acre corner lot in one of Winter Park's most sought-after locations. This 7,916 SF property includes a main residence of over 7,100 SF, a detached guest house, and a poolside catering suite. The private covered boat dock is located just steps away, across the street, in the historic Kraft Azalea Garden, providing direct lake access with boat and personal watercraft storage on Lake Maitland, without the upkeep of a waterfront backyard. Inside, fresh neutral interiors and beautiful landscaping frame elegant arrival and living spaces. The thoughtful layout offers 5 bedrooms and 5 full plus 4 half baths, including a 550 SF guest house. Expansive entertaining areas flow seamlessly into a private courtyard with a heated pool and spa, covered dining, an outdoor grill, a wood-burning fireplace, and multiple terraces. Highlights include a grand primary suite with dual bathrooms and closets, a two-story wardrobe with an office in one of the primary closets, an impressive entertainment room, and a gourmet kitchen outfitted with Viking appliances, a newly replaced double oven, and a trash compactor. For large-scale entertaining, the detached pool house doubles as a catering suite with prep sink, refrigerator, and wall-to-wall storage. Built by renowned builder Charles Clayton and designed by Marc-Michaels, the home is a masterpiece of solid block construction and timeless detail featuring imported Parisian fireplaces, solid marble columns, both marble and travertine floors, and Venetian plaster walls. A new barrel tile roof (2023) adds lasting value and peace of mind. Ideally located across from Kraft Azalea Garden and near Rollins College, the estate offers a rare combination of waterfront tranquility and walkable access to Park Avenue’s world-class dining, boutiques, and museums. The Winter Park Racquet Club is also just a short golf cart ride away. A rare opportunity to acquire a legacy property with major aesthetic updates already completed and future equity positioned for growth.

1400 Alabama Drive, Winter Park

$535,000

Welcome to your dream home nestled in the highly sought-after College Park district of Winter Park! This charming residence seamlessly blends history with modern upgrades, offering a perfect balance of comfort and convenience. Step inside to discover a beautifully updated kitchen featuring elegant granite countertops, ideal for both casual meals and entertaining guests. The home now boasts 1,795 heated square feet, thanks to a thoughtful garage conversion. The previous owner transformed the garage into a spacious primary bedroom with an en-suite bath, complete with central air conditioning and an additional mini-split AC unit for added comfort. The home also features an electronic gate access carport, ensuring secure and easy parking, while the expansive, fully fenced backyard provides a private oasis for relaxation or gatherings. Imagine enjoying your morning coffee or hosting weekend barbecues in this serene outdoor space. Location is everything, and this home delivers! Just a stone's throw away from Trader Joe's, you'll have easy access to popular shopping and dining options. Plus, with its proximity to downtown Orlando and local attractions, you'll never be far from the vibrant lifestyle that this area offers. Don't miss the opportunity to own a piece of history with all the modern comforts you desire. Schedule your showing today and experience the charm and convenience of this exceptional College Park home!

4 Beds ⋅ 2 Baths ⋅ Orwin Manor Stratford Sec SubDv. ⋅ 32789 Zip Code

Welcome to your dream home nestled in the highly sought-after College Park district of Winter Park! This charming residence seamlessly blends history with modern upgrades, offering a perfect balance of comfort and convenience. Step inside to discover a beautifully updated kitchen featuring elegant granite countertops, ideal for both casual meals and entertaining guests. The home now boasts 1,795 heated square feet, thanks to a thoughtful garage conversion. The previous owner transformed the garage into a spacious primary bedroom with an en-suite bath, complete with central air conditioning and an additional mini-split AC unit for added comfort. The home also features an electronic gate access carport, ensuring secure and easy parking, while the expansive, fully fenced backyard provides a private oasis for relaxation or gatherings. Imagine enjoying your morning coffee or hosting weekend barbecues in this serene outdoor space. Location is everything, and this home delivers! Just a stone's throw away from Trader Joe's, you'll have easy access to popular shopping and dining options. Plus, with its proximity to downtown Orlando and local attractions, you'll never be far from the vibrant lifestyle that this area offers. Don't miss the opportunity to own a piece of history with all the modern comforts you desire. Schedule your showing today and experience the charm and convenience of this exceptional College Park home!

1531 Norfolk Avenue, Winter Park

$260,000

This spacious 2-bedroom, 2-bathroom condo awaits you in a vibrant community. The mid-century modern complex offers the convenience of a community pool, on-site laundry, and picturesque pond views while being centrally located near Downtown Orlando, Downtown Winter Park, and Mead Gardens. Embrace a comfortable and active lifestyle in this desirable residence

2 Beds ⋅ 2 Baths ⋅ Winter Park Gardens Condo SubDv. ⋅ 32789 Zip Code

This spacious 2-bedroom, 2-bathroom condo awaits you in a vibrant community. The mid-century modern complex offers the convenience of a community pool, on-site laundry, and picturesque pond views while being centrally located near Downtown Orlando, Downtown Winter Park, and Mead Gardens. Embrace a comfortable and active lifestyle in this desirable residence

700 Melrose Avenue Unit B-4, Winter Park